CA2473461A1 - Amino alcohol derivative or phosphonic acid derivative and medicinal composition containing these - Google Patents

Amino alcohol derivative or phosphonic acid derivative and medicinal composition containing these Download PDF

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CA2473461A1
CA2473461A1 CA002473461A CA2473461A CA2473461A1 CA 2473461 A1 CA2473461 A1 CA 2473461A1 CA 002473461 A CA002473461 A CA 002473461A CA 2473461 A CA2473461 A CA 2473461A CA 2473461 A1 CA2473461 A1 CA 2473461A1
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methyl
amino
pharmacologically acceptable
ynyl
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CA2473461C (en
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Takahide Nishi
Takaichi Shimozato
Futoshi Nara
Shojiro Miyazaki
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Sankyo Co Ltd
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Abstract

The present invention relates to amino alcohol derivatives or phosphonic acid derivatives having excellent immunosuppressive activity, pharmacologically acceptable salts thereof or pharmacologically acceptable esters thereof, and to pharmaceutical compositions comprising said compounds as an active ingredient:

(see formula I) [wherein, R1 and R 2 each represent a hydrogen atom, or a protecting group of the amino group;
R3 represents a hydrogen atom, or a protecting group of the hydroxyl group;
R4 represents a lower alkyl group;
n represents an integer of from 1 to 6;
X represents an oxygen atom or a nitrogen atom unsubstituted or substituted with a lower alkyl group or the like;
Y represents an ethylene group;
Z represents a C1-C10 alkylene group;
R5 represents an aryl group, or an aryl group substituted with substituents;
R6 and R7 each represents a hydrogen atom;
provided that when R5 represents a hydrogen atom, then Z
represents a group other than a single bond or a straight chain C1-C20 alkylene group].

Claims (131)

1. A compound of general formula (I):
< I M G > (I) [wherein, R1 and R2 are the same or different and each represents a hydrogen atom, a lower alkyl group, or a protecting group of the amino group;
R3 represents a hydrogen atom, a lower alkyl group, or a protecting group of the hydroxyl group;
R4 represents a lower alkyl group;
n represents an integer of from 1 to 6;
X represents an oxygen atom or a group of formula -N-D
(wherein D represents a hydrogen atom, a C6-C10 aryl group, a lower alkylsulfonyl group, a C6-C10 arylsulfonyl group, or a group selected from Substituent group (a));
Y represents an ethylene group, a vinylene group, an ethynylene group, a group of formula: -E-CH2- (wherein E
represents a carbonyl group or a group of formula: -CH(OH)-), a C6-C10 arylene group, or a C6-C10 arylene group substituted with from 1 to 3 substituents selected from Substituent group (a) ;
Z represents a single bond, a C1-C10 alkylene group, a C1-C10 alkylene group substituted with from 1 to 3 substituents selected from Substituent group (a) and Substituent group (b), a C1-C10 alkylene group which has an oxygen atom or a sulfur atom in said carbon chain or at the end of said carbon chain, or a C1-C10 alkylene group substituted with from 1 to 3 substituents selected from the group consisting of Substituent group (a) and Substituent group (b) which has an oxygen atom or a sulfur atom in said carbon chain or at the end of said carbon chain;
R5 represents a hydrogen atom, a C3-C10 cycloalkyl group, a C6-C10 aryl group, a 5- to 7-membered heterocyclic group containing from 1 to 3 heteroatoms selected from the group consisting of a sulfur atom, an oxygen atom, and a nitrogen atom, a C3-C10 cycloalkyl group substituted with from 1 to 3 substituents selected from the group consisting of Substituent group (a) and Substituent group (b), a C6-C10 aryl group substituted with from 1 to 3 substituents selected from the group consisting of Substituent group (a) and Substituent group (b), or a 5- to 7-membered heterocyclic group containing from 1 to 3 heteroatoms selected from the group consisting of a sulfur atom, an oxygen atom, and a nitrogen atom in which said heterocyclic group is substituted with from 1 to 3 substituents selected from Substituent group (a) and Substituent group (b);
R6 and R7 are the same or different and each represents a hydrogen atom or a group selected from Substituent group (a);
Substituent group (a) represents the group consisting of a halogen atom, a lower alkyl group, a halogeno lower alkyl group, a lower alkoxy group, a lower alkylthio group, a carboxyl group, a lower alkoxycarbonyl group, a hydroxyl group, a lower aliphatic acyl group, an amino group, a mono-lower alkylamino group, a di-lower alkylamino group, a lower aliphatic acylamino group, a cyano group, and a nitro group;
and Substituent group (b) represents the group consisting of a C3-C10 cycloalkyl group, a C6-C10 aryl group, a 5- to 7-membered heterocyclic group containing from 1 to 3 heteroatoms selected from the group consisting of a sulfur atom, an oxygen atom, and a nitrogen atom, a C3-C10 cycloalkyl group substituted with from 1 to 3 substituents selected from Substituent group (a), a C6-C10 aryl group substituted with from 1 to 3 substituents selected from Substituent group (a), and a 5- to 7-membered heterocyclic group containing from 1 to 3 heteroatoms selected from the group consisting of a sulfur atom, an oxygen atom, and a nitrogen atom in which said heterocyclic group is substituted with from 1 to 3 substituents selected from Substituent group (a);

provided that when R5 represents a hydrogen atom, then Z
represents a branched chain C1-C10 alkylene group, a C1-C10 alkylene group substituted with from 1 to 3 substituents selected from the group consisting of Substituent group (a) and Substituent group (b), a C1-C10 alkylene group which has an oxygen atom or a sulfur atom in said carbon chain or at the end of said carbon chain, or a C1-C10 alkylene group substituted with from 1 to 3 substituents selected from the group consisting of Substituent group (a) and Substituent group (b) which has an oxygen atom or a sulfur atom in said carbon chain or at the end of said carbon chain], a pharmacologically acceptable salt thereof, or a pharmacologically acceptable ester thereof.
2. A compound according to claim 1 wherein said compound of formula (I) has the formula (Ia), a pharmacologically acceptable salt thereof, or a pharmacologically acceptable ester thereof:
(Ia)
3. A compound according to claim 1 wherein said compound of formula (I) has the formula (Ib), a pharmacologically acceptable salt thereof, or a pharmacologically acceptable ester thereof:
4. A pharmacologically acceptable ester of the compound of formula (I) according to claim 1 wherein said compound of formula (I) has the formula (II):
< I M G > (II) [wherein, R10 and R11 are the same or different and each represents a hydrogen atom or a protecting group of phosphoric acid]
or a pharmacologically acceptable salt thereof.
5. A pharmacologically acceptable ester of the compound of formula (II) according to claim 4 wherein said ester of formula (II) has the formula (IIa):
(IIa) or a pharmacologically acceptable salt thereof.
6. A pharmacologically acceptable ester of the compound of formula (II) according to claim 4 wherein said ester of formula (II) has the formula (IIb):
(IIb) [wherein, R10 and R11 are the same or different and each represents a hydrogen atom or a protecting group of phosphoric acid]
or a pharmacologically acceptable salt thereof.
7. A compound of general formula (III):
(III) [wherein, R1 and R2 are the same or different and each represents a hydrogen atom, a lower alkyl group, or a protecting group of the amino group;
R4 represents a lower alkyl group;
n represents an integer of from 1 to 6;
X represents an oxygen atom or a group of formula: =N-D
(wherein D represents a hydrogen atom, a C6-C10 aryl group, a lower alkylsulfonyl group, a C6-C10 arylsulfonyl group, or a group selected from Substituent group (a));
Y represents an ethylene group, a vinylene group, an ethynylene group, a group of formula: -E-CH2- (wherein E
represents a carbonyl group or a group of formula: -CH(OH)-), a C6-C10 arylene group, or a C6-C10 arylene group substituted with from 1 to 3 substituents selected from Substituent group (a) ;
Z represents a single bond, a C1-C10 alkylene group, a C1-C10 alkylene group substituted with from 1 to 3 substituents selected from the group consisting of Substituent group (a) and Substituent group (b), a C1-C10 alkylene group which has an oxygen atom or a sulfur atom in said carbon chain or at the end of said carbon chain, or a C1-C10 alkylene group substituted with from 1 to 3 substituents selected from the group consisting of Substituent group (a) and Substituent group (b) which has an oxygen atom or a sulfur atom in said carbon chain or at the end of said carbon chain:
R5 represents a hydrogen atom, a C3-C10 cycloalkyl group, a C6-C10 aryl group, a 5- to 7-membered heterocyclic group containing from 1 to 3 heteroatoms selected from the group consisting of a sulfur atom, an oxygen atom, and a nitrogen atom, a C3-C10 cycloalkyl group substituted with from 1 to 3 substituents selected from the group consisting of Substituent group (a) and Substituent group (b), a C6-C10 aryl group substituted with from 1 to 3 substituents selected from the group consisting of Substituent group (a) and Substituent group (b), or a 5- to 7-membered heterocyclic group containing from 1 to 3 heteroatoms selected from the group consisting of a sulfur atom, an oxygen atom, and a nitrogen atom in which said heterocyclic group is substituted with from 1 to 3 substituents selected from the group consisting of Substituent group (a) and Substituent group (b);
R6 and R7 are the same or different and each represents a hydrogen atom or a group selected from Substituent group (a);
R10 and R11 are the same or different and each represents a hydrogen atom or a protecting group of phosphoric acid;
Substituent group (a) represents the group consisting of a halogen atom, a lower alkyl group, a halogeno lower alkyl group, a lower alkoxy group, a lower alkylthio group, a carboxyl group, a lower alkoxycarbonyl group, a hydroxyl group, a lower aliphatic acyl group, an amino group, a mono-lower alkylamino group, a di-lower alkylamino group, a lower aliphatic acylamino group, a cyano group, and a nitro group;
and Substituent group (b) represents the group consisting of a C3-C10 cycloalkyl group, a C6-C10 aryl group, a 5- to 7-membered heterocyclic group containing from 1 to 3 heteroatoms selected from the group consisting of a sulfur atom, an oxygen atom, and a nitrogen atom, a C3-C10 cycloalkyl group substituted with from 1 to 3 substituents selected from Substituent group (a), a C6-C10 aryl group substituted with from 1 to 3 substituents selected from Substituent group (a), and a 5- to 7-membered heterocyclic group containing from 1 to 3 heteroatoms selected from the group consisting of a sulfur atom, an oxygen atom, and a nitrogen atom in which said heterocyclic group is substituted with from 1 to 3 substituents selected from Substituent group (a);
provided that when R5 represents a hydrogen atom, then Z

represents a branched chain C1-C10 alkylene group, a C1-C10 alkylene group substituted with from 1 to 3 substituents selected from the group consisting of Substituent group (a) and Substituent group (b), a C1-C10 alkylene group which has an oxygen atom or a sulfur atom in said carbon chain or at the end of said carbon chain, or a C1-C10 alkylene group substituted with from 1 to 3 substituents selected from the group consisting of Substituent group (a) and Substituent group (b) and has an oxygen atom or a sulfur atom in said carbon chain or at the end of said carbon chain], a pharmacologically acceptable salt thereof, or a pharmacologically acceptable ester thereof.
8. A compound according to claim 7 wherein said compound of formula (III) has the formula (IIIa), a pharmacologically acceptable salt thereof, or a pharmacologically acceptable ester thereof:

9. A compound according to claim 7 wherein said compound of formula (III) has the formula (IIIb), a pharmacologically acceptable salt thereof, or a pharmacologically acceptable ester thereof:

10. A compound according to any one of claims 1 to 9 wherein R1 and R2 are the same or different and each represents a hydrogen atom, a lower aliphatic acyl group, a lower alkoxycarbonyl group, an aralkyloxycarbonyl group, or an aralkyloxycarbonyl group substituted with from 1 to 3 substituents selected from Substituent group (a), or a pharmacologically acceptable salt thereof.
11. A compound according to any one of claims 1 to 9 wherein R1 and R2 are the same or different and each represents a hydrogen atom, a lower aliphatic acyl group, or a lower alkoxycarbonyl group, or a pharmacologically acceptable salt thereof.
12. A compound according to any one of claims 1 to 9 wherein R1 and R2 are the same or different and each represents a hydrogen atom, a C1-C4 aliphatic acyl group, or a C1-C4 alkoxycarbonyl group, or a pharmacologically acceptable salt thereof.
13. A compound according to any one of claims 1 to 9 wherein R1 and R2 are the same or different and each represents a hydrogen atom, a C1-C2 aliphatic acyl group, or a C1-C2 alkoxycarbonyl group, or a pharmacologically acceptable salt thereof.
14. A compound according to any one of claims 1 to 9 wherein R1 and R2 are the same or different and each represents a hydrogen atom, an acetyl group, or a methoxycarbonyl group, or a pharmacologically acceptable salt thereof.
15. A compound according to any one of claims 1 to 9 wherein each of R1 and R2 represents a hydrogen atom, or a pharmacologically acceptable salt thereof.
16. A compound according to any one of claims 1 to 3 and 10 to 15 wherein R3 represents a hydrogen atom, a lower alkyl group, a lower aliphatic acyl group, an aromatic acyl group, an aromatic acyl group substituted with from 1 to 3 substituents selected from Substituent group (a), or a silyl group, or a pharmacologically acceptable salt thereof.
17. A compound according to any one of claims 1 to 3 and 10 to 15 wherein R3 represents a hydrogen atom or a lower alkyl group, or a pharmacologically acceptable salt thereof.
18. A compound according to any one of claims 1 to 3 and 10 to 15 wherein R3 represents a hydrogen atom or a C1-C4 alkyl group, or a pharmacologically acceptable salt thereof.
19. A compound according to any one of claims 1 to 3 and 10 to 15 wherein R3 represents a hydrogen atom, a methyl group, or an ethyl group, or a pharmacologically acceptable salt thereof.
20. A compound according to any one of claims 1 to 3 and 10 to 15 wherein R3 represents a hydrogen atom, or a pharmacologically acceptable salt thereof.
21. A compound according to any one of claims 1 to 20 wherein R4 represents a C1-C4 alkyl group, or a pharmacologically acceptable salt thereof.
22. A compound according to any one of claims 1 to 20 wherein R4 represents a C1-C2 alkyl group, or a pharmacologically acceptable salt thereof.
23. A compound according to any one of claims 1 to 20 wherein R4 represents a methyl group, or a pharmacologically acceptable salt thereof.
24. A compound according to any one of claims 1 to 23 wherein n represents an integer 2 or 3, or a pharmacologically acceptable salt thereof.
25. A compound according to any one of claims 1 to 23 wherein n represents an integer 2, or a pharmacologically acceptable salt thereof.
26. A compound according to any one of claims 1 to 25 wherein X represents an oxygen atom, or a pharmacologically acceptable salt thereof.
27. A compound according to any one of claims 1 to 25 wherein X represents a group of formula: =N-D (wherein D represents a hydrogen atom, a C1-C4 alkyl group, or a phenyl group), or a pharmacologically acceptable salt thereof.
28. A compound according to any one of claims 1 to 25 wherein X represents a group of formula: =N-CH3, or a pharmacologically acceptable salt thereof.
29. A compound according to any one of claims 1 to 28 wherein Y represents an ethylene group, an ethynylene group, a group of formula: -CO-CH2-, a group of formula: -CH(OH)-CH2-, a phenylene group, or a phenylene group substituted with from 1 to 3 substituents selected from the group consisting of a halogen atom and a lower alkyl group, or a pharmacologically acceptable salt thereof.
30. A compound according to any one of claims 1 to 28 wherein Y represents an ethylene group, an ethynylene group, a group of formula: -CO-CH2-, or a phenylene group, or a pharmacologically acceptable salt thereof.
31. A compound according to any one of claims 1 to 30 wherein Z represents a C1-C10 alkylene group or a C1-C10 alkylene group substituted with from 1 to 3 substituents selected from the group consisting of Substituent group (a) and Substituent group (b), or a pharmacologically acceptable salt thereof.
32. A compound according to any one of claims 1 to 30 wherein Z represents a C1-C6 alkylene group or a C1-C6 alkylene group substituted with from 1 to 3 hydroxyl groups, or a pharmacologically acceptable salt thereof.
33. A compound according to any one of claims 1 to 30 wherein Z represents a C1-C5 alkylene group or a C1-C5 alkylene group substituted with from 1 to 3 hydroxyl groups, or a pharmacologically acceptable salt thereof.
34. A compound according to any one of claims 1 to 30 wherein Z represents an ethylene group, a trimethylene group, a tetramethylene group, or an ethylene, trimethylene, or tetramethylene group substituted with one hydroxyl group, or a pharmacologically acceptable salt thereof.
35. A compound according to any one of claims 1 to 30 wherein Z represents an ethylene group, a trimethylene group, or a tetramethylene group, or a pharmacologically acceptable salt thereof.
36. A compound according to any one of claims 1 to 30 wherein Z represents an ethylene group or a trimethylene group, or a pharmacologically acceptable salt thereof.
37. A compound according to any one of claims 1 to 30 wherein Z represents a C1-C10 alkylene group which has an oxygen atom or a sulfur atom in said carbon chain or at the end of said carbon chain or a C1-C10 alkylene group substituted with one hydroxyl group which has an oxygen atom or a sulfur atom in said carbon chain or at the end of said carbon chain (said substituent is selected from the group consisting of a lower alkyl group and a hydroxyl group), or a pharmacologically acceptable salt thereof.
38. A compound according to any one of claims 1 to 30 wherein Z represents a C1-C10 alkylene group which has an oxygen atom or a sulfur atom in said carbon chain or at the end of said carbon chain, or a pharmacologically acceptable salt thereof.
39. A compound according to any one of claims 1 to 30 wherein Z represents a C1-C10 alkylene group which has an oxygen atom or a sulfur atom in said carbon chain or at the end of said carbon chain, or a pharmacologically acceptable salt thereof.
40. A compound according to any one of claims 1 to 30 wherein Z represents a C1-C6 alkylene group which has an oxygen atom in said carbon chain or at the end of said carbon chain, or a pharmacologically acceptable salt thereof.
41. A compound according to any one of claims 1 to 30 wherein Z represents a group of formula -O-CH2-, -O-(CH2)2-, -O-(CH2)3-, -CH2-O-, -(CH2)2-O-, or -(CH2)3-O-, or a pharmacologically acceptable salt thereof.
42. A compound according to any one of claims 1 to 30 wherein Z represents a group of formula -CH2-O- or -(CH2)2-O-, or a pharmacologically acceptable salt thereof.
43. A compound according to any one of claims 1 to 42 wherein R5 represents a hydrogen atom, or a pharmacologically acceptable salt thereof.
44. A compound according to any one of claims 1 to 42 wherein R5 represents a C3-C10 cycloalkyl group, a C6-C10 aryl group, or a C3-C10 cycloalkyl or C6-C10 aryl group substituted with from 1 to 3 substituents selected from the group consisting of a halogen atom, a lower alkyl group, a halogeno lower alkyl group, a lower alkoxy group, and a lower alkylthio group, or a pharmacologically acceptable salt thereof.
45. A compound according to any one of claims 1 to 42 wherein R5 represents a C3-C10 cycloalkyl group, a C6-C10 aryl group, or a C3-C10 cycloalkyl or C6-C10 aryl group substituted with from 1 to 3 substituents selected from the group consisting of a halogen atom, a lower alkyl group, a halogeno lower alkyl group, and a lower alkoxy group, or a pharmacologically acceptable salt thereof.
46. A compound according to any one of claims 1 to 42 wherein R5 represents a C5-C6 cycloalkyl group, a phenyl group, or a naphthyl group, or a pharmacologically acceptable salt thereof.
47. A compound according to any one of claims 1 to 42 wherein R5 represents a cyclohexyl group or a phenyl group, or a pharmacologically acceptable salt thereof.
48. A compound according to any one of claims 1 to 47 wherein R6 and R7 are the same or different and each represents a hydrogen atom, a halogen atom, a lower alkyl group, a halogeno lower alkyl group, a lower alkoxy group, or a lower alkylthio group, or a pharmacologically acceptable salt thereof.
49. A compound according to any one of claims 1 to 47 wherein each of R6 and R7 represents a hydrogen atom, or a pharmacologically acceptable salt thereof.
50. A compound according to any one of claims 4 to 15 and 21 to 49 wherein R10 and R11 are the same or different and each represents a hydrogen atom or a lower alkyl group, or a pharmacologically acceptable salt thereof.
51. A compound according to any one of claims 4 to 15 and 21 to 49 wherein R10 and R11 are the same or different and each represents a hydrogen atom or a C1-C4 alkyl group, or a pharmacologically acceptable salt thereof.
52. A compound according to any one of claims 4 to 15 and 21 to 49 wherein R10 and R11 are the same or different and each represents a hydrogen atom, a methyl group, or an ethyl group, or a pharmacologically acceptable salt thereof.
53. A compound according to any one of claims 4 to 15 and 21 to 49 wherein each of R10 and R11 represents a hydrogen atom, or a pharmacologically acceptable salt thereof.
54. A compound according to claim 1 wherein said compound is selected from the following compounds or a pharmacologically acceptable salt thereof:

2-amino-2-methyl-4-[5-(5-phenylpentyl)furan-2-yl]butan-1-ol, 2-amino-2-methyl-4-[5-(5-cyclohexylpent-1-ynyl)furan-2-yl]butan-1-ol, 2-amino-2-methyl-4-[5-(5-phenylpent-1-ynyl)furan-2-yl]butan-1-ol, 2-amino-2-methyl-4-[5-(4-cyclohexyloxybut-1-ynyl)furan-2-yl]butan-1-ol, 2-amino-2-methyl-4-[5-(5-cyclohexylpentanoyl)furan-2-yl]butan-1-ol, and 2-amino-2-methyl-4-{5-[3-(3,4-dimethylphenoxy)prop-1-ynyl]furan-2-yl}butan-1-ol.
55. A compound according to claim 1 wherein said compound is selected from the following compounds or a pharmacologically acceptable salt thereof:
2-amino-2-methyl-4-[1-methyl-5-(5-phenylpent-1-ynyl)pyrrol-2-yl]butan-1-ol, 2-amino-2-methyl-4-{1-methyl-5-[3-(4-methylphenoxy)prop-1-ynyl]pyrrol-2-yl}butan-1-ol, 2-amino-2-methyl-4-[1-methyl-5-(4-cyclohexyloxybut-1-ynyl)pyrrol-2-yl]butan-1-ol, 2-amino-2-methyl-4-{1-methyl-5-[3-(3,4-dimethylphenoxy)prop-1-ynyl]pyrrol-2-yl}butan-1-ol, 2-amino-2-methyl-4-[1-methyl-5-(5-phenylpentanoyl)pyrrol-2-yl]butan-1-ol, 2-amino-2-methyl-4-[1-methyl-5-(5-cyclohexylpentanoyl)pyrrol-2-yl]butan-1-ol, 2-amino-2-methyl-4-[1-methyl-5-(4-phenylbutanoyl)pyrrol-2-yl]butan-1-ol, 2-amino-2-methyl-4-[1-methyl-5-(4-cyclohexylbutanoyl)pyrrol-2-yl]butan-1-ol, 2-amino-2-methyl-4-[1-ethyl-5-(5-phenylpentanoyl)pyrrol-2-yl]butan-1-ol, 2-amino-2-methyl-4-[1-ethyl-5-(5-cyclohexylpentanoyl)pyrrol-2-yl]butan-1-ol, 2-amino-2-methyl-4-[1-ethyl-5-(4-phenylbutanoyl)pyrrol-2-yl]butan-1-ol, and 2-amino-2-methyl-4-[1-ethyl-5-(4-cyclohexylbutanoyl)pyrrol-2-yl]butan-1-ol.
56. A compound according to claim 4 wherein said compound is selected from the following compounds or a pharmacologically acceptable salt thereof:
mono 2-amino-2-methyl-4-[5-(5-phenylpentyl)furan-2-yl]-1-butyl phosphate, mono 2-amino-2-methyl-4-[5-(5-cyclohexylpent-1-ynyl)furan-2-yl]-1-butyl phosphate, mono 2-amino-2-methyl-4-[5-(5-phenylpent-1-ynyl)furan-2-yl]-1-butyl phosphate, mono 2-amino-2-methyl-4-[5-(4-cyclohexyloxybut-1-ynyl)furan-2-yl]-1-butyl phosphate, mono 2-amino-2-methyl-4-[5-(5-cyclohexylpentanoyl)furan-2-yl]-1-butyl phosphate, and mono 2-amino-2-methyl-4-{5-[3-(3,4-dimethylphenoxy)prop-1-ynyl]furan-2-yl}-1-butyl phosphate.
57. A compound according to claim 4 wherein said compound is selected from the following compounds or a pharmacologically acceptable salt thereof:
mono 2-amino-2-methyl-4-[1-methyl-5-(5-phenylpent-1-ynyl)pyrrol-2-yl]-1-butyl phosphate, mono 2-amino-2-methyl-4-{1-methyl-5-[3-(4-methylphenoxy)prop-1-ynyl]pyrrol-2-yl}-1-butyl phosphate, mono 2-amino-2-methyl-4-[1-methyl-5-(4-cyclohexyloxybut-1-ynyl)pyrrol-2-yl]-1-butyl phosphate, mono 2-amino-2-methyl-4-{1-methyl-5-[3-(3,4-dimethylphenoxy)prop-1-ynyl]pyrrol-2-yl}-1-butyl phosphate, mono 2-amino-2-methyl-4-[1-methyl-5-(5-phenylpentanoyl)pyrrol-2-yl]-1-butyl phosphate, mono 2-amino-2-methyl-4-[1-methyl-5-(5-cyclohexylpentanoyl)-pyrrol-2-yl]-1-butyl phosphate, mono 2-amino-2-methyl-4-[1-methyl-5-(4-phenylbutanoyl)pyrrol-2-yl]-1-butyl phosphate, mono 2-amino-2-methyl-4-[1-methyl-5-(4-cyclohexylbutanoyl)pyrrol-2-yl]-1-butyl phosphate, mono 2-amino-2-methyl-4-[1-ethyl-5-(5-phenylpentanoyl)pyrrol-2-yl]-1-butyl phosphate, mono 2-amino-2-methyl-4-[1-ethyl-5-(5-cyclohexylpentanoyl)pyrrol-2-yl]-1-butyl phosphate, mono 2-amino-2-methyl-4-[1-ethyl-5-(4-phenylbutanoyl)pyrrol-2-yl]-1-butyl phosphate, and mono 2-amino-2-methyl-4-[1-ethyl-5-(4-cyclohexylbutanoyl)pyrrol-2-yl]-1-butyl phosphate.
58. A compound according to claim 7 wherein said compound is selected from the following compounds or a pharmacologically acceptable salt thereof:
3-amino-3-methyl-5-[5-(5-phenylpentyl)furan-2-yl]pentylphosphonic acid, 3-amino-3-methyl-5-[5-(5-cyclohexylpent-1-ynyl)furan-2-yl]pentylphosphonic acid, 3-amino-3-methyl-5-[5-(5-phenylpent-1-ynyl)furan-2-yl]pentylphosphonic acid, 3-amino-3-methyl-5-[5-(4-cyclohexyloxybut-1-ynyl)furan-2-yl]pentylphosphonic acid, 3-amino-3-methyl-5-[5-(5-cyclohexylpentanoyl)furan-2-yl]pentylphosphonic acid, and 3-amino-3-methyl-5-{5-[3-(3,4-dimethylphenoxy)prop-1-ynyl]furan-2-yl}pentylphosphonic acid.
59. A compound according to claim 7 wherein said compound is selected from the following compounds or a pharmacologically acceptable salt thereof:
3-amino-3-methyl-5-[1-methyl-5-(5-phenylpent-1-ynyl)pyrrol-2-yl]pentylphosphonic acid, 3-amino-3-methyl-5-{1-methyl-5-[3-(4-methylphenoxy)prop-1-ynyl]pyrrol-2-yl}pentylphosphonic acid, 3-amino-3-methyl-5-[1-methyl-5-(4-cyclohexyloxybut-1-ynyl)pyrrol-2-yl]pentylphosphonic acid, 3-amino-3-methyl-5-{1-methyl-5-[3-(3,4-dimethylphenoxy)prop-1-ynyl]pyrrol-2-yl}pentylphosphonic acid, 3-amino-3-methyl-5-[1-methyl-5-(5-phenylpentanoyl)pyrrol-2-yl]pentylphosphonic acid, 3-amino-3-methyl-5-[1-methyl-5-(5-cyclohexylpentanoyl)pyrrol-2-yl]pentylphosphonic acid, 3-amino-3-methyl-5-[1-methyl-5-(4-phenylbutanoyl)pyrrol-2-yl]pentylphosphonic acid, 3-amino-3-methyl-5-[1-methyl-5-(4-cyclohexylbutanoyl)pyrrol-2-yl]pentylphosphonic acid, 3-amino-3-methyl-5-[1-ethyl-5-(5-phenylpentanoyl)pyrrol-2-yl]pentylphosphonic acid, 3-amino-3-methyl-5-[1-ethyl-5-(5-cyclohexylpentanoyl)pyrrol-2-yl]pentylphosphonic acid, 3-amino-3-methyl-5-[1-ethyl-5-(4-phenylbutanoyl)pyrrol-2-yl]pentylphosphonic acid, and 3-amino-3-methyl-5-(1-ethyl-5-(4-cyclohexylbutanoyl)pyrrol-2-yl]pentylphosphonic acid.
60. A pharmaceutical composition containing at least one immunosuppressant selected from the group consisting of an agent having the action of inhibiting intracellular signal transduction involved in cytokine expression of T-cells, an agent having the action of inhibiting nucleoside synthesis in immune cells, an agent having the action of inhibiting the action of cytokines on immune cells and having antirheumatic action, an alkylating agent causing cell death by breakdown of DNA
chains or blocking DNA synthesis, a metabolic antagonist inhibiting the metabolism of nucleic acids by blocking folic acid production, a protein drug having the suppression action of TNF-.alpha., a steroid hormone agent that binds to intracellular steroid receptors to form a complex which binds to reaction sites on chromosomes, resulting in the synthesis of proteins which show immunosuppressive activity, and a substance suppressing prostaglandin production and/or nonsteroidal anti-inflammatory drug antagonizing the action of prostaglandin, and at least one compound selected from the group consisting of compounds of the general formula (I):
[wherein, R1 and R2 are the same or different and each represents a hydrogen atom, a lower alkyl group, or a protecting group of the amino group;
R3 represents a hydrogen atom, a lower alkyl group, or a protecting group of the hydroxyl group;
R9 represents a lower alkyl group:
n represents an integer of from 1 to 6:
X represents a sulfur atom, an oxygen atom, or a group of formula =N-D (wherein D represents a hydrogen atom, an aryl group, a lower alkylsulfonyl group, an arylsulfonyl group, or a group selected from Substituent group (a));
Y represents an ethylene group, a vinylene group, an ethynylene group, a group of formula -E-CH2- (wherein E
represents a carbonyl group or a group of formula -CH(OH)-), a C6-C10 arylene group, or a C6-C10 arylene group substituted with from 1 to 3 substituents selected from Substituent group (a);
Z represents a single bond, a C1-C10 alkylene group, a C1-C10 alkylene group substituted with from 1 to 3 substituents selected from the group consisting of Substituent group (a) and Substituent group (b), a C1-C10 alkylene group which has an oxygen atom or a sulfur atom in said carbon chain or at the end of said carbon chain, or a C1-C10 alkylene group substituted with from 1 to 3 substituents selected from the group consisting of Substituent group (a) and Substituent group (b) which has an oxygen atom or a sulfur atom in said carbon chain or at the end of said carbon chain;
R5 represents a hydrogen atom, a C3-C10 cycloalkyl group, a C6-C10 aryl group, a 5- to 7-membered heterocyclic group containing from 1 to 3 heteroatoms selected from the group consisting of a sulfur atom, an oxygen atom, and a nitrogen atom, a C3-C10 cycloalkyl group substituted with from 1 to 3 substituents selected from the group consisting of Substituent group (a) and Substituent group (b), a C6-C10 aryl group substituted with from 1 to 3 substituents selected from the group consisting of Substituent group (a) and Substituent group (b), or a 5- to 7-membered heterocyclic group containing from 1 to 3 heteroatoms selected from the group consisting of a sulfur atom, an oxygen atom, and a nitrogen atom in which said heterocyclic group is substituted with from 1 to 3 substituents selected from the group consisting of Substituent group (a) and Substituent group (b);

R6 and R7 are the same or different and each represents a hydrogen atom or a group selected from Substituent group (a);
Substituent group (a) represents the group consisting of a halogen atom, a lower alkyl group, a halogeno lower alkyl group, a lower alkoxy group, a lower alkylthio group, a carboxyl group, a lower alkoxycarbonyl group, a hydroxyl group, a lower aliphatic acyl group, an amino group, a mono-lower alkylamino group, a di-lower alkylamino group, a lower aliphatic acylamino group, a cyano group, and a nitro group;
and Substituent group (b) represents the group consisting of a C3-C10 cycloalkyl group, a C6-C10 aryl group, a 5- to 7-membered heterocyclic group containing from 1 to 3 heteroatoms selected from the group consisting of a sulfur atom, an oxygen atom, and a nitrogen atom, a C3-C10 cycloalkyl group substituted with from 1 to 3 substituents selected from Substituent group (a), a C6-C10 aryl group substituted with from 1 to 3 substituents selected from Substituent group (a), and a 5- to 7-membered heterocyclic group containing from 1 to 3 heteroatoms selected from the group consisting of a sulfur atom, an oxygen atom, and a nitrogen atom in which said heterocyclic group is substituted with from 1 to 3 substituents selected from Substituent group (a);

provided that when R5 represents a hydrogen atom, then Z
represents a branched chain C1-C10 alkylene group, a C1-C10 alkylene group substituted with from 1 to 3 substituents selected from the group consisting of Substituent group (a) and Substituent group (b), a C1-C10 alkylene group which has an oxygen atom or a sulfur atom in said carbon chain or at the end of said carbon chain, or a C1-C10 alkylene group substituted with from 1 to 3 substituents selected from the group consisting of Substituent group (a) and Substituent group (b) which has an oxygen atom or a sulfur atom in said carbon chain or at the end of said carbon chain), a pharmacologically acceptable salt thereof, or a pharmacologically acceptable ester thereof.
61. A pharmaceutical composition according to claim 60 wherein said compound of general formula (I) has the general formula (Ia) shown below:

62. A pharmaceutical composition according to claim 60 wherein said compound of general formula (I) has the general formula (Ib) shown below:
63. A pharmaceutical composition according to claim 60 wherein the pharmacologically acceptable ester of the compound of formula (I) has the formula (II):
[wherein, R10 and R11 are the same or different and each represents a hydrogen atom or a protecting group of phosphoric acid]

or a pharmacologically acceptable salt thereof.
64. A pharmaceutical composition according to claim 63 wherein the ester of the compound of formula (II) has the formula (IIa):
or a pharmacologically acceptable salt thereof.
65. A pharmaceutical composition according to claim 63 wherein the ester of the compound of formula (II) has the formula (IIb) or a pharmacologically acceptable salt thereof.
66. A pharmaceutical composition containing at least one immunosuppressant selected from the group consisting of an agent having the action of inhibiting intracellular signal transduction involved in cytokine expression of T-cells, an agent having the action of inhibiting nucleoside synthesis in immune cells, an agent having the action of inhibiting the action of cytokines on immune cells and having antirheumatic action, an alkylating agent causing cell death by breakdown of DNA
chains or blocking DNA synthesis, a metabolic antagonist inhibiting the metabolism of nucleic acids by blocking folic acid production, a protein drug having the suppression action Of TNF-a, a steroid hormone agent that binds to intracellular steroid receptors to form a complex which binds to reaction sites on chromosomes, resulting in the synthesis of proteins which show immunosuppressive activity, and a substance suppressing prostaglandin production and/or nonsteroidal anti-inflammatory drug antagonizing the action of prostaglandin, and at least one compound selected from the group consisting of compounds of the general formula (III) shown below:
[wherein, R1 and R2 are the same or different and each represents a hydrogen atom, a lower alkyl group, or a protecting group of the amino group:

R4 represents a lower alkyl group;
n represents an integer of from 1 to 6;
X represents a sulfur atom, an oxygen atom or a group of formula =N-D (wherein D represents a hydrogen atom, a C6-C10 aryl group, a lower alkylsulfonyl group, a C6-C10 arylsulfonyl group, or a group selected from Substituent group (a)):
Y represents an ethylene group, a vinylene group, an ethynylene group, a group of formula -E-CH2- (wherein E
represents a carbonyl group or a group of formula -CH(OH)-), a C6-C10 arylene group, or a C6-C10 arylene group substituted with from 1 to 3 substituents selected from Substituent group (a);

Z represents a single bond, a C1-C10 alkylene group, a C1-C10 alkylene group substituted with from 1 to 3 substituents selected from the group consisting of Substituent group (a) and Substituent group (b), a C1-C10 alkylene group which has an oxygen atom or a sulfur atom in said carbon chain or at the end of said carbon chain, or a C1-C10 alkylene group substituted with from 1 to 3 substituents selected from the group consisting of Substituent group (a) and Substituent group (b) which has an oxygen atom or a sulfur atom in said carbon chain or at the end of said carbon chain;

R5 represents a hydrogen atom, a C3-C10 cycloalkyl group, a C6-C10 aryl group, a 5- to 7-membered heterocyclic group containing from 1 to 3 heteroatoms selected from the group consisting of a sulfur atom, an oxygen atom, and a nitrogen atom, a C3-C10 cycloalkyl group substituted with from 1 to 3 substituents selected from the group consisting of Substituent group (a) and Substituent group (b), a C6-C10 aryl group substituted with from 1 to 3 substituents selected from the group consisting of Substituent group (a) and Substituent group (b), or a 5- to 7-membered heterocyclic group containing from 1 to 3 heteroatoms selected from the group consisting of a sulfur atom, an oxygen atom, and a nitrogen atom in which said heterocyclic group is substituted with from 1 to 3 substituents selected from the group consisting of Substituent group (a) and Substituent group (b);

R6 and R7 are the same or different and each represents a hydrogen atom or a group selected from Substituent group (a);

R10 and R11 are the same or different and each represents a hydrogen atom or a protecting group of phosphoric acid;
Substituent group (a) represents the group consisting of a halogen atom, a lower alkyl group, a halogeno lower alkyl group, a lower alkoxy group, a lower alkylthio group, a carboxyl group, a lower alkoxycarbonyl group, a hydroxyl group, a lower aliphatic acyl group, an amino group, a mono-lower alkylamino group, a di-lower alkylamino group, a lower aliphatic acylamino group, a cyano group, and a nitro group;
and Substituent group (b) represents the group consisting of a C3-C10 cycloalkyl group, a C6-C10 aryl group, a 5- to 7-membered heterocyclic group containing from 1 to 3 heteroatoms selected from the group consisting of a sulfur atom, an oxygen atom, and a nitrogen atom, a C3-C10 cycloalkyl group substituted with from 1 to 3 substituents selected from Substituent group (a), a C6-C10 aryl group substituted with from 1 to 3 substituents selected from Substituent group (a), and a 5- to 7-membered heterocyclic group containing from 1 to 3 heteroatoms selected from the group consisting of a sulfur atom, an oxygen atom, and a nitrogen atom in which said heterocyclic group is substituted with from 1 to 3 substituents selected from Substituent group (a):

provided that when R5 represents a hydrogen atom, then Z
represents a branched chain C1-C10 alkylene group, a C1-C10 alkylene group substituted with from 1 to 3 substituents selected from the group consisting of Substituent group (a) and Substituent group (b), a C1-C10 alkylene group which has an oxygen atom or a sulfur atom in said carbon chain or at the end of said carbon chain, or a C1-C10 alkylene group substituted with from 1 to 3 substituents selected from the group consisting of Substituent group (a) and Substituent group (b) which has an oxygen atom or a sulfur atom in said carbon chain or at the end of said carbon chain], a pharmacologically acceptable salt thereof, or a pharmacologically acceptable ester thereof.
67. A pharmaceutical composition according to claim 66 wherein the compound of formula (III) has the formula (IIIa):
68. A pharmaceutical composition according to claim 66 wherein the compound of formula (III) has the formula (IIIb):

69. A pharmaceutical composition according to any one of claims 60 to 68 containing a compound wherein R1 and R2 are the same or different and each represents a hydrogen atom, a lower aliphatic acyl group, a lower alkoxycarbonyl group, an aralkyloxycarbonyl group, or an aralkyloxycarbonyl group substituted with from 1 to 3 substituents selected from Substituent group (a), or a pharmacologically acceptable salt thereof.
70. A pharmaceutical composition according to any one of claims 60 to 68 containing a compound wherein R1 and R2 are the same or different and each represents a hydrogen atom, a lower aliphatic acyl group, or a lower alkoxycarbonyl group, or a pharmacologically acceptable salt thereof.
71. A pharmaceutical composition according to any one of claims 60 to 68 containing a compound wherein R1 and R2 are the same or different and each represents a hydrogen atom, a C1-C9 aliphatic acyl group, or a C1-C9 alkoxycarbonyl group, or a pharmacologically acceptable salt thereof.
72. A pharmaceutical composition according to any one of claims 60 to 68 containing a compound wherein R1 and R2 are the same or different and each represents a hydrogen atom, a C1-C2 aliphatic acyl group, or a C1-C2 alkoxycarbonyl group, or a pharmacologically acceptable salt thereof.
73. A pharmaceutical composition according to any one of claims 60 to 68 containing a compound wherein R1 and R2 are the same or different and each represents a hydrogen atom, an acetyl group, or a methoxycarbonyl group, or a pharmacologically acceptable salt thereof.
74. A pharmaceutical composition according to any one of claims 60 to 68 containing a compound wherein each of R1 and R2 represents a hydrogen atom, or a pharmacologically acceptable salt thereof.
75. A pharmaceutical composition according to any one of claims 60 to 62 and 69 to 74 containing a compound wherein R3 represents a hydrogen atom, a lower alkyl group, a lower aliphatic acyl group, an aromatic acyl group, an aromatic acyl group substituted with from 1 to 3 substituents selected from Substituent group (a), or a silyl group, or a pharmacologically acceptable salt thereof.
76. A pharmaceutical composition according to any one of claims 60 to 62 and 69 to 74 containing a compound wherein R3 represents a hydrogen atom or a lower alkyl group, or a pharmacologically acceptable salt thereof.
77. A pharmaceutical composition according to any one of claims 60 to 62 and 69 to 74 containing a compound wherein R3 represents a hydrogen atom or a C1-C4 alkyl group, or a pharmacologically acceptable salt thereof.
78. A pharmaceutical composition according to any one of claims 60 to 62 and 69 to 74 containing a compound wherein R3 represents a hydrogen atom, a methyl group, or an ethyl group, or a pharmacologically acceptable salt thereof.
79. A pharmaceutical composition according to any one of claims 60 to 62 and 69 to 74 containing a compound wherein R3 represents a hydrogen atom, or a pharmacologically acceptable salt thereof.
80. A pharmaceutical composition according to any one of claims 60 to 79 containing a compound wherein R4 represents a C1-C9 alkyl group, or a pharmacologically acceptable salt thereof.
81. A pharmaceutical composition according to any one of claims 60 to 79 containing a compound wherein R4 represents a C1-C2 alkyl group, or a pharmacologically acceptable salt thereof.
82. A pharmaceutical composition according to any one of claims 60 to 79 containing a compound wherein R9 represents a methyl group, or a pharmacologically acceptable salt thereof.
83. A pharmaceutical composition according to any one of claims 60 to 82 containing a compound wherein n represents an integer 2 or 3, or a pharmacologically acceptable salt thereof.
84. A pharmaceutical composition according to any one of claims 60 to 82 containing a compound wherein n represents an integer 2, or a pharmacologically acceptable salt thereof.
85. A pharmaceutical composition according to any one of claims 60 to 84 containing a compound wherein X represents a sulfur atom, or a pharmacologically acceptable salt thereof.
86. A pharmaceutical composition according to any one of claims 60 to 84 containing a compound wherein X represents an oxygen atom, or a pharmacologically acceptable salt thereof.
87. A pharmaceutical composition according to any one of claims 60 to 84 containing a compound wherein X represents a group of formula =N-D (wherein D represents a hydrogen atom, a C1-C4 alkyl group, or a phenyl group), or a pharmacologically acceptable salt thereof.
88. A pharmaceutical composition according to any one of claims 60 to 84 containing a compound wherein X represents a group of formula =N-CH3, or a pharmacologically acceptable salt thereof.
89. A pharmaceutical composition according to any one of claims 60 to 88 containing a compound wherein Y represents an ethylene group, an ethynylene group, a group of formula -CO-CH2-, a group of formula -CH(OH)-CH2-, a phenylene group, or a phenylene group substituted with from 1 to 3 substituents selected from the group consisting of a halogen atom and a lower alkyl group, or a pharmacologically acceptable salt thereof.
90. A pharmaceutical composition according to any one of claims 60 to 88 containing a compound wherein Y represents an ethylene group, an ethynylene group, a group of formula -CO-CH2-, or a phenylene group, or a pharmacologically acceptable salt thereof.
91. A pharmaceutical composition according to any one of claims 60 to 90 containing a compound wherein Z represents a C1-C10 alkylene group or a C1-C10 alkylene group substituted with from 1 to 3 substituents selected from the group consisting of Substituent group (a) and Substituent group (b), or a pharmacologically acceptable salt thereof.
92. A pharmaceutical composition according to any one of claims 60 to 90 containing a compound wherein Z represents a C1-C6 alkylene group or a C1-C6 alkylene group substituted with from 1 to 3 hydroxyl groups, or a pharmacologically acceptable salt thereof.
93. A pharmaceutical composition according to any one of claims 60 to 90 containing a compound wherein Z represents a C1-C5 alkylene group or a C1-C5 alkylene group substituted with from 1 to 3 hydroxyl groups, or a pharmacologically acceptable salt thereof.
94. A pharmaceutical composition according to any one of claims 60 to 90 containing a compound wherein Z represents an ethylene group, a trimethylene group, a tetramethylene group, or an ethylene, trimethylene, or tetramethylene group substituted with one hydroxyl group, or a pharmacologically acceptable salt thereof.
95. A pharmaceutical composition according to any one of claims 60 to 90 containing a compound wherein Z represents an ethylene group, a trimethylene group, or a tetramethylene group, or a pharmacologically acceptable salt thereof.
96. A pharmaceutical composition according to any one of claims 60 to 90 containing a compound wherein Z represents an ethylene group or a trimethylene group, or a pharmacologically acceptable salt thereof.
97. A pharmaceutical composition according to any one of claims 60 to 90 containing a compound wherein Z represents a C1-C10 alkylene group which has an oxygen atom or a sulfur atom in said carbon chain or at the end of said carbon chain or a C1-C10 alkylene group substituted with one hydroxyl group which has an oxygen atom or a sulfur atom in said carbon chain or at the end of said carbon chain (said substituent is selected from the group consisting of lower alkyl groups and hydroxyl groups), or a pharmacologically acceptable salt thereof.
98. A pharmaceutical composition according to any one of claims 60 to 90 containing a compound wherein Z represents a C1-C10 alkylene group which has an oxygen atom or a sulfur atom in said carbon chain or at the end of said carbon chain, or a pharmacologically acceptable salt thereof.
99. A pharmaceutical composition according to any one of claims 60 to 90 containing a compound wherein Z represents a C1-C10 alkylene group which has an oxygen atom in said carbon chain or at the end of said carbon chain, or a pharmacologically acceptable salt thereof.
100. A pharmaceutical composition according to any one of claims 60 to 90 containing a compound wherein Z represents a C1-C6 alkylene group which has an oxygen atom in said carbon chain or at the end of said carbon chain, or a pharmacologically acceptable salt thereof.
101. A pharmaceutical composition according to any one of claims 60 to 90 containing a compound wherein Z represents a group of formula -O-CH2-, -O-(CH2)2-, -O-(CH2)3-, -CH2-O-, -(CH2)2-O-, or -(CH2)3-O-, or a pharmacologically acceptable salt thereof.
102. A pharmaceutical composition according to any one of claims 60 to 90 containing a compound wherein Z represents a group of formula -CH2-O- or -(CH2)2-O-, or a pharmacologically acceptable salt thereof.
103. A pharmaceutical composition according to any one of claims 60 to 102 containing a compound wherein R5 represents a hydrogen atom, or a pharmacologically acceptable salt thereof.
104. A pharmaceutical composition according to any one of claims 60 to 102 containing a compound wherein R5 represents a C3-C10 cycloalkyl group, a C6-C10 aryl group, or a C3-C10 cycloalkyl or C6-C10 aryl group substituted with from 1 to 3 substituents selected from the group consisting of a halogen atom, a lower alkyl group, a halogeno lower alkyl group, a lower alkoxy group, and a lower alkylthio group, or a pharmacologically acceptable salt thereof.
105. A pharmaceutical composition according to any one of claims 60 to 102 containing a compound wherein R5 represents a C3-C10 cycloalkyl group, a C6-C10 aryl group, or a C3-C10 cycloalkyl or C6-C10 aryl group substituted with from 1 to 3 substituents selected from the group consisting of a halogen atom, a lower alkyl group, a halogeno lower alkyl group, and a lower alkoxy group, or a pharmacologically acceptable salt thereof.
106. A pharmaceutical composition according to any one of claims 60 to 102 containing a compound wherein R5 represents a C5-C6 cycloalkyl group, a phenyl group, or a naphthyl group, or a pharmacologically acceptable salt thereof.
107. A pharmaceutical composition according to any one of claims 60 to 102 containing a compound wherein R5 represents a cyclohexyl group or a phenyl group, or a pharmacologically acceptable salt thereof.
108. A pharmaceutical composition according to any one of claims 60 to 107 containing a compound wherein R6 and R7 are the same or different and each represents a hydrogen atom, a halogen atom, a lower alkyl group, a halogeno lower alkyl group, a lower alkoxy group, or a lower alkylthio group, or a pharmacologically acceptable salt thereof.
109. A pharmaceutical composition according to any one of claims 60 to 107 containing a compound wherein each of R6 and R7 represents a hydrogen atom, or a pharmacologically acceptable salt thereof.
110. A pharmaceutical composition according to any one of claims 63 to 74 and 80 to 109 containing a compound wherein R10 and R11 are the same or different and each represents a hydrogen atom or a lower alkyl group, or a pharmacologically acceptable salt thereof.
111. A pharmaceutical composition according to any one of claims 63 to 74 and 80 to 109 containing a compound wherein R10 and R11 are the same or different and each represents a hydrogen atom or a C1-C4 alkyl group, or a pharmacologically acceptable salt thereof.
112. A pharmaceutical composition according to any one of claims 63 to 74 and 80 to 109 containing a compound wherein R10 and R11 are the same or different and each represents a hydrogen atom, a methyl group or an ethyl group, or a pharmacologically acceptable salt thereof.
113. A pharmaceutical composition according to any one of claims 63 to 74 and 80 to 109 containing a compound wherein each of R10 and R11 represents a hydrogen atom, or a pharmacologically acceptable salt thereof.
114. A pharmaceutical composition according to claim 60, wherein the compound of general formula (I), or pharmacologically acceptable salt thereof, or pharmacologically acceptable ester thereof is selected from the group consisting of the compounds described below, pharmacologically acceptable salts thereof, and pharmacologically acceptable esters thereof:
2-amino-2-methyl-4-[5-(4-cyclohexylbutyl)thiophen-2-yl]butan-1-ol, 2-amino-2-methyl-4-[5-(5-cyclohexylpentyl)thiophen-2-yl]butan-1-ol, 2-amino-2-methyl-4-[5-(5-phenylpentyl)thiophen-2-yl]butan-1-ol, 2-amino-2-methyl-4-[5-(4-cyclohexyloxybutyl)thiophen-2-yl]butan-1-ol, 2-amino-2-methyl-4-{5-[4-(4-fluorophenoxy)butyl]thiophen-2-yl}butan-1-ol, 2-amino-2-methyl-4-{5-[4-(4-methoxyphenoxy)butyl]thiophen-2-yl}butan-1-ol 2-amino-2-methyl-4-[5-(4-benzyloxybutyl)thiophen-2-yl]butan-1-ol, 2-amino-2-methyl-4-[5-(4-cyclohexylbut-1-ynyl)thiophen-2-yl]butan-1-ol, 2-amino-2-methyl-4-[5-(4-phenylbut-1-ynyl)thiophen-2-yl]butan-1-ol, 2-amino-2-methyl-4-(5-(4-cyclohexylpent-1-ynyl)thiophen-2-yl]butan-1-ol, 2-amino-2-methyl-4-[5-(5-phenylpent-1-ynyl)thiophen-2-yl]butan-1-ol, 2-amino-2-methyl-4-{5-[5-(4-fluorophenyl)pent-1-ynyl]thiophen-2-yl}butan-1-ol, 2-amino-2-methyl-4-{5-[5-(4-methoxyphenyl)pent-1-ynyl]thiophen-2-yl}butan-1-ol, 2-amino-2-methyl-4-{5-[3-(4-methylphenoxy)prop-1-ynyl]thiophen-2-yl}butan-1-ol, 2-amino-2-methyl-4-{5-[3-(4-ethylphenoxy)prop-1-ynyl]thiophen-2-yl}butan-1-ol, 2-amino-2-methyl-4-{5-[3-(4-methylthiophenoxy)prop-1-ynyl]thiophen-2-yl}butan-1-ol, 2-amino-2-methyl-4-[5-(4-cyclohexyloxybut-1-ynyl)thiophen-2-yl]butan-1-ol, 2-amino-2-methyl-4-{5-[4-(4-fluorophenoxy)but-1-ynyl]thiophen-2-yl}butan-1-ol, 2-amino-2-methyl-4-{5-[4-(4-methylphenoxy)but-1-ynyl]thiophen-2-yl}butan-1-ol, 2-amino-2-methyl-4-[5-(3-cyclohexylmethoxyprop-1-ynyl)thiophen-2-yl]butan-1-ol, 2-amino-2-methyl-4-[5-(4-benzyloxybut-1-ynyl)thiophen-2-yl]butan-1-ol, 2-amino-2-methyl-4-[5-(4-cyclohexylbutanoyl)thiophen-2-yl]butan-1-ol, 2-amino-2-methyl-4-[5-(4-phenylbutanoyl)thiophen-2-yl]butan-1-ol, 2-amino-2-methyl-4-[5-(5-cyclohexylpentanoyl)thiophen-2-yl]butan-1-ol, 2-amino-2-methyl-4-[5-(5-phenylpentanoyl)thiophen-2-yl]butan-1-ol, 2-amino-2-methyl-4-{5-[5-(4-fluorophenyl)pentanoyl]thiophen-2-yl}butan-1-ol, 2-amino-2-ethyl-4-[5-(5-cyclohexylpentyl)thiophen-2-yl]butan-1-ol, 2-amino-2-ethyl-4-[5-(5-cyclohexylpent-1-ynyl)thiophen-2-yl]butan-1-ol, 2-amino-2-ethyl-4-[5-(5-cyclohexylpentanoyl)thiophen-2-yl]butan-1-ol, 2-amino-2-methyl-4-{5-[3-(4-chlorophenoxy)prop-1-ynyl]thiophen-2-yl}butan-1-ol, 2-amino-2-methyl-4-{5-[3-(3-methylphenoxy)prop-1-ynyl]thiophen-2-yl}butan-1-ol, 2-amino-2-methyl-4-{5-[3-(3,4-dimethylphenoxy)prop-1-ynyl]thiophen-2-yl}butan-1-ol, 2-amino-2-methyl-4-{5-[3-(3-methoxyphenoxy)prop-1-ynyl]thiophen-2-yl}butan-1-ol, 2-amino-2-methyl-4-{5-[3-(3,4-dimethoxyphenoxy)prop-1-ynyl]thiophen-2-yl}butan-1-ol, 2-amino-2-methyl-4-{5-[3-(3,5-dimethoxyphenoxy)prop-1-ynyl]thiophen-2-yl}butan-1-ol, 2-amino-2-methyl-4-{5-[3-(3-acetylphenoxy)prop-1-ynyl]thiophen-2-yl}butan-1-ol, and 2-amino-2-methyl-4-{5-[3-(4-acetylphenoxy)prop-1-ynyl]thiophen-2-yl}butan-1-ol.
115. A pharmaceutical composition according to claim 60, wherein the compound of general formula (I), or pharmacologically acceptable salt thereof, or pharmacologically acceptable ester thereof is selected from the group consisting of the compounds described below, pharmacologically acceptable salts thereof, and pharmacologically acceptable esters thereof:
2-amino-2-methyl-4-[5-(5-phenylpentyl)furan-2-yl]butan-1-ol, 2-amino-2-methyl-4-[5-(5-cyclohexylpent-1-ynyl)furan-2-yl]butan-1-ol, 2-amino-2-methyl-4-[5-(5-phenylpent-1-ynyl)furan-2-yl]butan-1-ol, 2-amino-2-methyl-4-[5-(4-cyclohexyloxybut-1-ynyl)furan-2-yl]butan-1-ol, 2-amino-2-methyl-4-[5-(5-cyclohexylpentanoyl)furan-2-yl]butan-1-ol, and 2-amino-2-methyl-4-{5-[3-(3,4-dimethylphenoxy)prop-1-ynyl]furan-2-yl}butan-1-ol.
116. A pharmaceutical composition according to claim 60, wherein the compound of general formula (I), or pharmacologically acceptable salt thereof, or pharmacologically acceptable ester thereof is selected from the group consisting of the compounds described below, pharmacologically acceptable salts thereof, and pharmacologically acceptable esters thereof:
2-amino-2-methyl-4-[1-methyl-5-(5-phenylpent-1-ynyl)pyrrol-2-yl]butan-1-ol, 2-amino-2-methyl-4-{1-methyl-5-[3-(4-methylphenoxy)prop-1-ynyl]pyrrol-2-yl}butan-1-ol, 2-amino-2-methyl-4-[1-methyl-5-(4-cyclohexyloxybut-1-ynyl)pyrrol-2-yl]butan-1-ol, 2-amino-2-methyl-4-{1-methyl-5-[3-(3,4-dimethylphenoxy)prop-1-ynyl]pyrrol-2-yl}butan-1-ol, 2-amino-2-methyl-4-[1-methyl-5-(5-phenylpentanoyl)pyrrol-2-yl]butan-1-ol, 2-amino-2-methyl-4-[1-methyl-5-(5-cyclhexylpentanoyl)pyrrol-2-yl]butan-1-ol, 2-amino-2-methyl-4-[1-methyl-5-(4-phenylbutanoyl)pyrrol-2-yl]butan-1-ol, 2-amino-2-methyl-4-[1-methyl-5-(4-cyclohexylbutanoyl)pyrrol-2-yl]butan-1-ol, 2-amino-2-methyl-4-[1-ethyl-5-(5-phenylpentanoyl)pyrrol-2-yl]butan-1-ol, 2-amino-2-methyl-4-[1-ethyl-5-(5-cyclohexylpentanoyl)pyrrol-2-yl]butan-1-ol, 2-amino-2-methyl-4-[1-ethyl-5-(4-phenylbutanoyl)pyrrol-2-yl]butan-1-ol, and 2-amino-2-methyl-4-[1-ethyl-5-(4-cyclohexylbutanoyl)pyrrol-2-yl]butan-1-ol.
117. A pharmaceutical composition according to claim 63, wherein the compound of general formula (II), or pharmacologically acceptable salt thereof, or pharmacologically acceptable ester thereof is selected from the group consisting of the compounds described below, pharmacologically acceptable salts thereof, and pharmacologically acceptable esters thereof:
mono 2-amino-2-methyl-4-[5-(4-cyclohexylbutyl)thiophen-2-yl]-1-butyl phosphate, mono 2-amino-2-methyl-4-[5-(5-cyclohexylpentyl)thiophen-2-yl]-1-butyl phosphate, mono 2-amino-2-methyl-4-[5-(5-phenylpentyl)thiophen-2-yl]-1-butyl phosphate, mono 2-amino-2-methyl-4-[5-(4-cyclohexyloxybutyl)thiophen-2-yl]-1-butyl phosphate, mono 2-amino-2-methyl-4-{5-[4-(4-fluorophenoxy)butyl]thiophen-2-yl}-1-butyl phosphate, mono 2-amino-2-methyl-4-{5-[4-(4-methoxyphenoxy)butyl]thiophen-2-yl}-1-butyl phosphate, mono 2-amino-2-methyl-4-[5-(4-benzyloxybutyl)thiophen-2-yl]-1-butyl phosphate, mono 2-amino-2-methyl-4-[5-(4-cyclohexylbut-1-ynyl)thiophen-2-yl]-1-butyl phosphate, mono 2-amino-2-methyl-4-[5-(4-phenylbut-1-ynyl)thiophen-2-yl]-1-butyl phosphate, mono 2-amino- 2-methyl-4-[5-(5-cyclohexylpent-1-ynyl)thiophen-2-yl]-1-butyl phosphate, mono 2-amino-2-methyl-4-[5-(5-phenylpent-1-ynyl)thiophen-2-yl]-1-butyl phosphate, mono 2-amino-2-methyl-4-{5-[5-(4-fluorophenyl)pent-1-ynyl]thiophen-2-yl}-1-butyl phosphate, mono 2-amino-2-methyl-4-{5-[5-(4-methoxyphenyl)pent-1-ynyl]thiophen-2-yl}-1-butyl phosphate, mono 2-amino-2-methyl-4-{5-[3-(4-methylphenoxy)prop-1-ynyl]thiophen-2-yl}-1-butyl phosphate, mono 2-amino-2-methyl-4-{5-[3-(4-ethylphenoxy)prop-1-ynyl]thiophen-2-yl}-1-butyl phosphate, mono 2-amino-2-methyl-4-{5-[3-(4-methylthiophenoxy)prop-1-ynyl]thiophen-2-yl}-1-butyl phosphate, mono 2-amino-2-methyl-4-[5-(4-cyclohexyloxybut-1-ynyl)thiophen-2-yl]-1-butyl phosphate, mono 2-amino-2-methyl-4-{5-[4-(4-fluorophenoxy)but-1-ynyl]thiophen-2-yl}-1-butyl phosphate, mono 2-amino-2-methyl-4-{5-[4-(4-methylphenoxy)but-1-ynyl]thiophen-2-yl}-1-butyl phosphate, mono 2-amino-2-methyl-4-[5-(3-cyclohexylmethoxy)prop-1-ynyl]thiophen-2-yl]-1-butyl phosphate, mono 2-amino-2-methyl-4-[5-(4-benzyloxybut-1-ynyl)thiophen-2-yl]-1-butyl phosphate, mono 2-amino-2-methyl-4-[5-(4-cyclohexylbutanoyl)thiophen-2-yl]-1-butyl phosphate, mono 2-amino-2-methyl-4-[5-(4-phenylbutanoyl)thiophen-2-yl]-1-butyl phosphate, mono 2-amino-2-methyl-4-[5-(5-cyclohexylpentanoyl)thiophen-2-yl]-1-butyl phosphate, mono 2-amino-2-methyl-4-[5-(5-phenylpentanoyl)thiophen-2-yl]-1-butyl phosphate, mono 2-amino-2-methyl-4-{5-[5-(4-fluorophenyl)pentanoyl]thiophen-2-yl}-1-butyl phosphate, mono 2-amino-2-ethyl-4-[5-(5-cyclohexylpentyl)thiophen-2-yl]-1-butyl phosphate, mono 2-amino-2-ethyl-4-[5-(5-cyclohexylpent-1-ynyl)thiophen-2-yl]-1-butyl phosphate, mono 2-amino-2-ethyl-4-[5-(5-cyclohexylpentanoyl)thiophen-2-yl]-1-butyl phosphate, mono 2-amino-2-methyl-4-{5-[3-(4-chlorophenoxy)prop-1-ynyl]thiophen-2-yl}-1-butyl phosphate, mono 2-amino-2-methyl-4-{5-[3-(3-methylphenoxy)prop-1-ynyl]thiophen-2-yl}-1-butyl phosphate, mono 2-amino-2-methyl-4-{5-[3-(3,4-dimethylphenoxy)prop-1-ynyl]thiophen-2-yl}-1-butyl phosphate, mono 2-amino-2-methyl-4-{5-[3-(3-methoxyphenoxyl)prop-1-ynyl]thiophen-2-yl}-1-butyl phosphate, mono 2-amino-2-methyl-4-{5-[3-(3,4-dimethoxyphenoxy)prop-1-ynyl]thiophen-2-yl}-1-butyl phosphate, mono 2-amino-2-methyl-4-{5-[3-(3,5-dimethoxyphenoxyl)prop-1-ynyl]thiophen-2-yl}-1-butyl phosphate, mono 2-amino-2-methyl-4-{5-[3-(3-acetylphenoxy)prop-1-ynyl]thiophen-2-yl}-1-butyl phosphate, and mono 2-amino-2-methyl-4-{5-[3-(4-acetylphenoxy)prop-1-ynyl]thiophen-2-yl}-1-butyl phosphate.
118. A pharmaceutical composition according to claim 63, wherein the compound of general formula (II), or pharmacologically acceptable salt thereof, or pharmacologically acceptable ester thereof is selected from the group consisting of the compounds described below, pharmacologically acceptable salts thereof, and pharmacologically acceptable esters thereof:
mono 2-amino-2-methyl-4-[5-(5-phenylpentyl)furan-2-yl]-1-butyl phosphate, mono 2-amino-2-methyl-4-[5-(5-cyclohexylpent-1-ynyl)furan-2-yl]-1-butyl phosphate, mono 2-amino-2-methyl-4-[5-(5-phenylpent-1-ynyl)furan-2-yl]-1-butyl phosphate, mono 2-amino-2-methyl-4-[5-(4-cyclohexyloxybut-1-ynyl)furan-2-yl]-1-butyl phosphate, mono 2-amino-2-methyl-4-[5-(5-cyclohexylpentanoyl)furan-2-yl]-1-butyl phosphate, and mono 2-amino-2-methyl-4-{5-[3-(3,4-dimethylphenoxy)prop-1-ynyl]furan-2-yl}-1-butyl phosphate.
119. A pharmaceutical composition according to claim 63, wherein the compound of general formula (II), or pharmacologically acceptable salt thereof, or pharmacologically acceptable ester thereof is selected from the group consisting of the compounds described below, pharmacologically acceptable salts thereof, and pharmacologically acceptable esters thereof:
mono 2-amino-2-methyl-4-[1-methyl-5-(5-phenylpent-1-ynyl)pyrrol-2-yl]-1-butyl phosphate, mono 2-amino-2-methyl-4-{1-methyl-5-[3-(4-methylphenoxy)prop-1-ynyl]pyrrol-2-yl}-1-butyl phosphate, mono 2-amino-2-methyl-4-[1-methyl-5-(4-cyclohexyloxybut-1-ynyl)pyrrol-2-yl]-1-butyl phosphate, mono 2-amino-2-methyl-4-{1-methyl-5-[3-(3,4-dimethylphenoxy)prop-1-ynyl]pyrrol-2-yl}-1-butyl phosphate, mono 2-amino-2-methyl-4-[1-methyl-5-(5-phenylpentanoyl)pyrrol-2-yl]-1-butyl phosphate, mono 2-amino-2-methyl-4-[1-methyl-5-(5-cyclohexylpentanoyl)pyrrol-2-yl]-1-butyl phosphate, mono 2-amino-2-methyl-4-[1-methyl-5-(4-phenylbutanoyl)pyrrol-2-yl]-1-butyl phosphate, mono 2-amino-2-methyl-4-[1-methyl-5-(4-cyclohexylbutanoyl)pyrrol-2-yl]-1-butyl phosphate, mono 2-amino-2-methyl-4-[1-ethyl-5-(5-phenylpentanoyl)pyrrol-2-yl]-1-butyl phosphate, mono 2-amino-2-methyl-4-[1-ethyl-5-(5-cyclohexylpentanoyl)pyrrol-2-yl]-1-butyl phosphate, mono 2-amino-2-methyl-4-[1-ethyl-5-(4-phenylbutanoyl)pyrrol-2-yl]-1-butyl phosphate, and mono 2-amino-2-methyl-4-[1-ethyl-5-(4-cyclohexylbutanoyl)pyrrol-2-yl]-1-butyl phosphate.
120. A pharmaceutical composition according to claim 66, wherein the compound of general formula (III), or pharmacologically acceptable salt thereof, or pharmacologically acceptable ester thereof is selected from the group consisting of the compounds described below, pharmacologically acceptable salts thereof, and pharmacologically acceptable esters thereof:
3-amino-3-methyl-5-[5-(4-cyclohexylbutyl)thiophen-2-yl]pentylphosphonic acid, 3-amino-3-methyl-5-[5-(5-cyclohexylpentyl)thiophen-2-yl]pentylphosphonic acid, 3-amino-3-methyl-5-[5-(5-phenylpentyl)thiophen-2-yl]pentylphosphonic acid, 3-amino-3-methyl-5-[5-(4-cyclohexyloxybutyl)thiophen-2-yl]pentylphosphonic acid, 3-amino-3-methyl-5-{5-[4-(4-fluorophenoxy)butyl]thiophen-2-yl}pentylphosphonic acid, 3-amino-3-methyl-5-{5-[4-(4-methoxyphenoxy)butyl]thiophen-2-yl}pentylphosphonic acid, 3-amino-3-methyl-5-[5-(4-benzyloxybutyl)thiophen-2-yl]pentylphosphonic acid, 3-amino-3-methyl-5-[5-(4-cyclohexylbut-1-ynyl)thiophen-2-yl]pentylphosphonic acid, 3-amino-3-methyl-5-[5-(4-phenylbut-1-ynyl)thiophen-2-yl]pentylphosphonic acid, 3-amino-3-methyl-5-[5-(5-cyclohexylpent-1-ynyl)thiophen-2-yl]pentylphosphonic acid, 3-amino-3-methyl-5-[5-(5-phenylpent-1-ynyl)thiophen-2-yl]pentylphosphonic acid, 3-amino-3-methyl-5-{5-[5-(4-fluorophenyl)pent-1-ynyl]thiophen-2-yl}pentylphosphonic acid, 3-amino-3-methyl-5-{5-[5-(4-methoxyphenyl)pent-1-ynyl]thiophen-2-yl}pentylphosphonic acid, 3-amino-3-methyl-5-{5-[3-(4-methylphenoxy)prop-1-ynyl]thiophen-2-yl}pentylphosphonic acid, 3-amino-3-methyl-5-{5-[3-(4-ethylphenoxy)prop-1-ynyl]thiophen-2-yl}pentylphosphonic acid, 3-amino-3-methyl-5-{5-[3-(4-methylthiophenoxy)prop-1-ynyl]thiophen-2-yl}pentylphosphonic acid, 3-amino-3-methyl-5-[5-(4-cyclohexyloxybut-1-ynyl)thiophen-2-yl]pentylphosphonic acid, 3-amino-3-methyl-5-{5-[4-(4-fluorophenoxy)but-1-ynyl]thiophen-2-yl}pentylphosphonic acid, 3-amino-3-methyl-5-{5-[4-(4-methylphenoxy)but-1-ynyl]thiophen-2-yl}pentylphosphonic acid, 3-amino-3-methyl-5-[5-(3-cyclohexylmethoxy)prop-1-ynyl]thiophen-2-yl]pentylphosphonic acid, 3-amino-3-methyl-5-[5-(4-benzyloxybut-1-ynyl)thiophen-2-yl]pentylphosphonic acid, 3-amino-3-methyl-5-[5-(4-cyclohexylbutanoyl)thiophen-2-yl]pentylphosphonic acid, 3-amino-3-methyl-5-[5-(4-phenylbutanoyl)thiophen-2-yl]pentylphosphonic acid, 3-amino-3-methyl-5-[5-(5-cyclohexylpentanoyl)thiophen-2-yl]pentylphosphonic acid, 3-amino-3-methyl-5-[5-(5-phenylpentanoyl)thiophen-2-yl]pentylphosphonic acid, 3-amino-3-methyl-5-{5-[5-(4-fluorophenyl)pentanoyl]thiophen-2-yl}pentylphosphonic acid, 3-amino-3-ethyl-5-[5-(5-cyclohexylpentyl)thiophen-2-yl]pentylphosphonic acid, 3-amino-3-ethyl-5-[5-(5-cyclohexylpent-1-ynyl)thiophen-2-yl]pentylphosphonic acid, 3-amino-3-ethyl-5-[5-(5-cyclohexylpentanoyl)thiophen-2-yl]pentylphosphonic acid, 3-amino-3-methyl-5-{5-[3-(4-chlorophenoxy)prop-1-ynyl]thiophen-2-yl}pentylphosphonic acid, 3-amino-3-methyl-5-{5-[3-(3-methylphenoxy)prop-1-ynyl]thiophen-2-yl}pentylphosphonic acid, 3-amino-3-methyl-5-{5-[3-(3,4-dimethylphenoxy)prop-1-ynyl]thiophen-2-yl}pentylphosphonic acid, 3-amino-3-methyl-5-{5-[3-(3-methoxyphenoxyl)prop-1-ynyl]thiophen-2-yl}pentylphosphonic acid, 3-amino-3-methyl-5-{5-[3-(3,4-dimethoxyphenoxy)prop-1-ynyl]thiophen-2-yl}pentylphosphonic acid, 3-amino-3-methyl-5-{5-[3-(3,5-dimethoxyphenoxyl)prop-1-ynyl]thiophen-2-yl}pentylphosphonic acid, 3-amino-3-methyl-5-{5-[3-(3-acetylphenoxy)prop-1-ynyl]thiophen-2-yl}pentylphosphonic acid, and 3-amino-3-methyl-5-{5-[3-(4-acetylphenoxy)prop-1-ynyl]thiophen-2-yl}pentylphosphonic acid.
121. A pharmaceutical composition according to claim 66, wherein the compound of general formula (III), or pharmacologically acceptable salt thereof, or pharmacologically acceptable ester thereof is selected from the group consisting of the compounds described below, pharmacologically acceptable salts thereof, and pharmacologically acceptable esters thereof:
3-amino-3-methyl-5-[5-(5-phenylpentyl)furan-2-yl)pentylphosphonic acid, 3-amino-3-methyl-5-[5-(5-cyclohexylpent-1-ynyl)furan-2-yl]pentylphosphonic acid, 3-amino-3-methyl-5-[5-(5-phenylpent-1-ynyl)furan-2-yl]pentylphosphonic acid, 3-amino-3-methyl-5-[5-(4-cyclohexyloxybut-1-ynyl)furan-2-yl]pentylphosphonic acid, 3-amino-3-methyl-5-[5-(5-cyclohexylpentanoyl)furan-2-yl]pentylphosphonic acid, and 3-amino-3-methyl-5-{5-[3-(3,4-dimethylphenoxy)prop-1-ynyl]furan-2-yl}pentylphosphonic acid.
122. A pharmaceutical composition according to claim 66, wherein the compound of general formula (III), or pharmacologically acceptable salt thereof, or pharmacologically acceptable ester thereof is selected from the group consisting of the compounds described below, pharmacologically acceptable salts thereof, and pharmacologically acceptable esters thereof:
3-amino-3-methyl-5-[1-methyl-5-(5-phenylpent-1-ynyl)pyrrol-2-yl]pentylphosphonic acid, 3-amino-3-methyl-5-{1-methyl-5-[3-(4-methylphenoxy)prop-1-ynyl]pyrrol-2-yl}pentylphosphonic acid, 3-amino-3-methyl-5-[1-methyl-5-(4-cyclohexyloxybut-1-ynyl)pyrrol-2-yl]pentylphosphonic acid, 3-amino-3-methyl-5-{1-methyl-5-[3-(3,4-dimethylphenoxy)prop-1-ynyl]pyrrol-2-yl}pentylphosphonic acid, 3-amino-3-methyl-5-[1-methyl-5-(5-phenylpentanoyl)pyrrol-2-yl]pentylphosphonic acid, 3-amino-3-methyl-5-[1-methyl-5-(5-cyclohexylpentanoyl)pyrrol-2-yl]pentylphosphonic acid, 3-amino-3-methyl-5-[1-methyl-5-(4-phenylbutanoyl)pyrrol-2-yl]pentylphosphonic acid, 3-amino-3-methyl-5-[1-methyl-5-(4-cyclohexylbutanoyl)pyrrol-2-yl]pentylphosphonic acid, 3-amino-3-methyl-5-[1-ethyl-5-(5-phenylpentanoyl)pyrrol-2-yl]pentylphosphonic acid, 3-amino-3-methyl-5-[1-ethyl-5-(5-cyclohexylpentanoyl)pyrrol-2-yl]pentylphosphonic acid, 3-amino-3-methyl-5-[1-ethyl-5-(4-phenylbutanoyl)pyrrol-2-yl]pentylphosphonic acid, and 3-amino-3-methyl-5-[1-ethyl-5-(4-cyclohexylbutanoyl)pyrrol-2-yl]pentylphosphonic acid.
123. A pharmaceutical composition according to any one of claims 60 to 122 wherein said composition contains at least one immunosuppressant selected from the group consisting of agents having the action of inhibiting intracellular signal transduction involved in cytokine expression of T-cells (said agents are cyclosporin A, tacrolimus, rapamycin, gusperimus, everolimus, tresperimus, anisperimus, SDZ-281-240, ABT-281, tigderimus, A-119435, or 17-ethyl-1,14-dihydroxy-12-[2-[4-(2-phenylhydrazinocarbonyloxy)-3-methoxycyclohexyl]-1-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.0 4,9]octacos-18-ene-2,3,10,16-tetrone), agents having the action of inhibiting nucleoside synthesis in immune cells (said agents are mizoribine, azathioprine, mycophenolic acid, leflunomide, merimempodib, HMR-1279, TSK-204, or SP-100030), agents having the action of inhibiting the action of cytokines on immune cells and having antirheumatic action (said agents are T-614, actarit, salazosulfapyridine, or CDC-801), alkylating agents causing cell death by breakdown of DNA
chains or blocking DNA synthesis (said alkylating agent is cyclophosphamide), metabolic antagonists inhibiting the metabolism of nucleic acids by blocking folic acid production (said metabolic antagonist is methotrexate), protein drugs having the suppression action of TNF-.alpha. (said protein drugs are remicade, enbrel, daclizumab, basiliximab, alemtuzumab, omalizumab, BMS-188667, CDP-571, inolimomab, ATM-027, or BTI-322), steroid hormone agents that bind to intracellular steroid receptors to form a complex which binds to reaction sites on chromosomes, resulting in the synthesis of proteins which show immunosuppressive activity (said steroid hormone agent is prednisolone), and substances suppressing prostaglandin production and/or nonsteroidal anti-inflammatory drugs antagonizing the action of prostaglandin (said nonsteroidal anti-inflammatory drugs are loxoprofen sodium, diclofenac sodium, meloxicam, celecoxib, or rofecoxib).
124. A pharmaceutical composition according to any one of claims 60 to 122 wherein said composition contains at least one immunosuppressant selected from the group consisting of cyclosporin A, tacrolimus, rapamycin, leflunomide, methotrexate, remicade, and enbrel.
125. A pharmaceutical composition comprising as an active ingredient a compound, a pharmacologically acceptable salt thereof or a pharmacologically acceptable ester thereof according to any one of claims 1 to 59.
126. A pharmaceutical composition according to claim 125 for the prevention or treatment of autoimmune diseases.
127. A pharmaceutical composition according to claim 126 wherein said autoimmune disease is rheumatoid arthritis.
128. A pharmaceutical composition according to claim 125 for suppression of rejection caused by transplantation of various organs.
129. A method for the prevention or treatment of autoimmune diseases in a mammal which comprises administering to said mammal an effective amount of a pharmaceutical composition according to any one of claims 60 to 125.
130. A method for the prevention or treatment of rheumatoid arthritis in a mammal which comprises administering to said mammal an effective amount of a pharmaceutical composition according to any one of claims 60 to 125.
131. A method for the prevention or treatment of rejection caused by transplantation of various organs in a mammal which comprises administering to said mammal an effective amount of a pharmaceutical composition according to any one of claims 60 to 125.
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