CA2445875A1 - Pentapeptide compounds and uses related thereto - Google Patents

Pentapeptide compounds and uses related thereto Download PDF

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Publication number
CA2445875A1
CA2445875A1 CA002445875A CA2445875A CA2445875A1 CA 2445875 A1 CA2445875 A1 CA 2445875A1 CA 002445875 A CA002445875 A CA 002445875A CA 2445875 A CA2445875 A CA 2445875A CA 2445875 A1 CA2445875 A1 CA 2445875A1
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Prior art keywords
solvate
compound
pharmaceutically acceptable
acceptable salt
lower alkyl
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CA002445875A
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CA2445875C (en
Inventor
Svetlana Doronina
Peter D. Senter
Brian E. Toki
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Seagen Inc
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
    • C07K5/0202—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-X-X-C(=0)-, X being an optionally substituted carbon atom or a heteroatom, e.g. beta-amino acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/68—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment
    • A61K47/6801—Drug-antibody or immunoglobulin conjugates defined by the pharmacologically or therapeutically active agent
    • A61K47/6803—Drugs conjugated to an antibody or immunoglobulin, e.g. cisplatin-antibody conjugates
    • A61K47/6811—Drugs conjugated to an antibody or immunoglobulin, e.g. cisplatin-antibody conjugates the drug being a protein or peptide, e.g. transferrin or bleomycin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
    • C07K5/0205—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-(X)3-C(=0)-, e.g. statine or derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides

Abstract

Pentapeptide compounds are disclosed. The compounds have biological activity, e.g., cytotoxicity. Prodrugs having targeting groups and pentapeptide moieties, as well as precursors thereof are also disclosed. For example, precursors having a reactive linker that can serve as a reaction site for joining to a targeting agent, e.g., an antibody, as disclosed.

Claims (94)

1. A compound of the formula or a pharmaceutically acceptable salt or solvate thereof wherein, independently at each location:
R1 is selected from hydrogen and lower alkyl;
R2 is selected from hydrogen and lower alkyl;
R3 is lower alkyl;
R4 is selected from lower alkyl, aryl, and -CH2-C5-7carbocycle when R5 is selected from H and methyl, or R4 and R5 together form a carbocycle of the partial formula -(CR a R b)n- wherein R a and R b are independently selected from hydrogen and lower alkyl and n is selected from 2, 3, 4, 5 and 6;
R6 is selected from hydrogen and lower alkyl;
R7 is sec-butyl or iso-butyl;
R8 is selected from hydrogen and lower alkyl; and R9 is selected from wherein:
R10 is selected from R11 is selected from hydrogen and lower alkyl;
R12 is selected from lower alkyl, halogen, and methoxy, and m is 0-5 where R12 is independently selected at each occurrence; and wherein:
R14 is selected from a direct bond, lower alkylene, arylene, and arylene(lower alkylene);
R15 is selected from hydrogen, lower alkyl and aryl;
R16 is selected from arylene(lower alkylene), lower alkylene, arylene, aryl(lower alkylene), and -(CH2OCH2)p CH2- where p is 1-5; and R17 is selected from where Y = O
or S.
2. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 1 wherein R1 is hydrogen.
3. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 1 wherein R1 and R2 are methyl.
4. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 1 wherein R3 is isopropyl.
5. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 1 wherein R4 is selected from lower alkyl, aryl, and -CH2-C5-7carbocycle and R5 is selected from H and methyl.
6. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 1 wherein R4 is selected from lower alkyl, and R5 is selected from H
and methyl.
7. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 1 wherein R4 and R5 together form a carbocycle of the partial formula -(CR a R b)n-wherein R a and R b are independently selected from hydrogen and lower alkyl and n is selected from 2, 3, 4, 5 and 6.
8. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 1 wherein R6 is lower alkyl.
9. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 1 wherein R8 is hydrogen.
10. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 1 wherein R9 is
11. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 10 wherein R10 is
12. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 10 wherein R10 is
13. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 10 wherein R14 is selected from arylene and lower alkylene; R15 is selected from lower alkyl and aryl; and R16 is lower alkylene.
14. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 1 wherein R9 is
15. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 14 wherein R10 is
16. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 14 wherein R10 is
17. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 14 wherein R14 is selected from arylene and lower alkylene; R15 is selected from lower alkyl and aryl; and R16 is lower alkylene.
18. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 1 wherein R9 is and R13 is .
19. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 18 wherein R15 is lower alkyl; and R16 is lower alkylene.
20. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 1 wherein R9 is
21. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 20 wherein R16 is selected from lower alkylene and arylene.
22. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 1 wherein R9 is
23. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 22 wherein R16 is selected from lower alkylene and arylene.
24. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 1 wherein R17 is .
25. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 1 wherein R17 is .
26. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 1 wherein R17 is .
27. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 1 wherein R17 is and Y = O or S.
28. A compound of claim 1 having the structure or a pharmaceutically acceptable salt or solvate thereof.
29. A compound of claim 1 having the structure or a pharmaceutically acceptable salt or solvate thereof.
30. A compound of claim 1 having the structure or a pharmaceutically acceptable salt or solvate thereof wherein R4 is selected from iso-propyl and sec-butyl.
31. A compound of claim 1 having the structure or a pharmaceutically acceptable salt or solvate thereof .
32. A compound of claim 1 having the structure or a pharmaceutically acceptable salt or solvate thereof .
33. A compound of the formula or a pharmaceutically acceptable salt or solvate thereof, wherein, independently at each location:
R1 is selected from hydrogen and lower alkyl;
R2 is selected from hydrogen and lower alkyl;
R3 is lower alkyl;
R4 is selected from lower alkyl, aryl, and -CH2-C5-7carbocycle when R5 is selected from H and methyl, or R4 and R5 together form a carbocycle of the partial formula -(CR a R b)n- wherein R a and R b are independently selected from hydrogen and lower alkyl and n is selected from 2, 3, 4, 5 and 6;
R6 is selected from hydrogen and lower alkyl;
R7 is sec-butyl or iso-butyl;
R8 is selected from hydrogen and lower alkyl;
R11 is selected from hydrogen and lower alkyl;
R12 is selected from lower alkyl, halogen, and methoxy, and m is 0-5 where R12 is independently selected at each occurrence; and R20 is a reactive linker group having a reactive site that allows R20 to be reacted with a targeting moiety, where R20 can be bonded to the carbon labeled "x" by either a single or double bond.
34. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 33 wherein the reactive site is selected from N hydroxysuccinimide ester, p-nitrophenyl ester, pentafluorophenyl ester, isothiocyanate, isocyanate, anhydride, acid chloride, and sulfonyl chloride.
35. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 33 wherein R20 comprises a hydrazone selected from the formulae wherein:
R14 is selected from a direct bond arylene(lower alkylene), lower alkylene and arylene;
R15 is selected from hydrogen, lower alkyl and aryl;

R16 is selected from lower alkylene, arylene(lower alkylene), arylene, and -(CH2OCH2)pCH2- where p is 1-5; and R17 is selected from wherein X is a leaving group.
36. A compound of claim 35 having the formula or a pharmaceutically acceptable salt or solvate thereof .
37. A compound of claim 35 having the formula or a pharmaceutically. acceptable salt or solvate thereof wherein R4 is selected from iso-propyl and sec-butyl, and R5 is hydrogen.
38. A compound of claim 35 having the formula or a pharmaceutically acceptable salt or solvate thereof .
39. A compound of claim 35 having the formula or a pharmaceutically acceptable salt or solvate thereof.
40. A compound of claim 33 wherein R20 comprises a hydrazone of the formula:

or a pharmaceutically acceptable salt or solvate thereof wherein R16 is selected from arylene(lower alkylene), lower alkylene, arylene, and -(CH2OCH2)pCH2- where p is 1-5, and x identifies the carbon also marked x in claim 27; and R17 is selected from < 1 M G >

wherein X is a leaving group.
41. A compound of claim 40 having the formula or a pharmaceutically acceptable salt or solvate thereof .
42. A compound of the formula or a pharmaceutically acceptable salt or solvate thereof wherein, independently at each location:
R1 is selected from hydrogen and lower alkyl;
R2 is selected from hydrogen and lower alkyl;
R3 is lower alkyl;
R4 is selected from lower alkyl, aryl, and -CH2-C5-7carbocycle when R5 is selected from H and methyl, or R4 and R5 together form a carbocycle of the partial formula -(CR a R b)n- wherein R a and R b are independently selected from hydrogen and lower alkyl and n is selected from 2, 3, 4, 5 and 6;

R6 is selected from hydrogen and lower alkyl;
R7 is sec-butyl or iso-butyl;
R8 is selected from hydrogen and lower alkyl;
R11 is selected from hydrogen and lower alkyl;
R12 is selected from lower alkyl, halogen, and methoxy, and m is 0-5 where R12 is independently selected at each occurrence; and R20 is a reactive linker group having a reactive site that allows R20 to be reacted with a targeting moiety, where R20 can be bonded to the carbon labeled "x" by either a single or double bond.
43. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 42 wherein the reactive site is selected from N-hydroxysuccinimide ester, p-nitrophenyl ester, pentafluorophenyl ester, isothiocyanate, isocyanate, anhydride, acid chloride, and sulfonyl chloride.
44. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 42 wherein R20 comprises a hydrazone selected from the formulae wherein:

R14 is selected from a direct bond, arylene(lower alkylene), lower alkylene and arylene;

R15 is selected from hydrogen, lower alkyl and aryl;

R16 is selected from arylene(lower alkylene), lower alkylene, arylene, and -(CH2OCH2)pCH2- where p is 1-5; and R17 is selected from < 1 M G >

wherein X is a leaving group.
45. A compound of claim 44 having the formula or a pharmaceutically acceptable salt or solvate thereof.
46. A compound of claim 42 wherein R20 comprises a hydrazone of the formula:

or a pharmaceutically acceptable salt or solvate thereof wherein R16 is selected from arylene(lower alkylene), lower alkylene, arylene, and -(CH2OCH2)pCH2- where p is 1-5; and R17 is selected from < 1 M G >

where X is a leaving group.
47. A compound of the formula or a pharmaceutically acceptable salt or solvate thereof wherein, independently at each location:
R1 is selected from hydrogen and lower alkyl;
R2 is selected from hydrogen and lower alkyl;
R3 is lower alkyl;
R4 is selected from lower alkyl, aryl, and -CH2-C5-7carbocycle when R5 is selected from H and methyl, or R4 and R5 together form a carbocycle of the partial formula -(CR a R b)n- wherein R a and R b are independently selected from hydrogen and lower alkyl and n is selected from 2, 3, 4, 5 and 6;

R6 is selected from hydrogen and lower alkyl;
R7 is sec-butyl or iso-butyl;
R8 is selected from hydrogen and lower alkyl; and R20 is a reactive linker group comprising a reactive site that allows R20 to be reacted with a targeting moiety.
48. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 47 wherein the reactive site is selected from N-hydroxysuccinimide ester, p-nitrophenyl ester, pentafluorophenyl ester, isothiocyanate, isocyanate, anhydride, acid chloride, and sulfonyl chloride.
49. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 47 wherein R20 comprises a hydrazone of the formula wherein:
R14 is selected from a direct bond, arylene(lower alkylene), lower alkylene and arylene;

R15 is selected from hydrogen, lower alkyl and aryl;
R16 is selected from arylene(lower alkylene), lower alkylene, arylene, and -(CH2OCH2)pCH2- where p is 1-5; and R17 is selected from where X is a leaving group.

[Received by the International Bureau on 12 February 2003 (12.02.03):
original claim 52 amended; original claims 65-96 renumbered 63-94;
original claims 63 and 64 deleted; remaining claims unchanged; (10 pages)]
50. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 47 wherein R20 comprises a hydrazone of the formula:

wherein, R15 is selected from hydrogen, and lower alkyl, R16 is selected from arylene(lower alkylene), lower alkylene, arylene, and -(CH2OCH2)pCH2- where p is 1-5 and R17 is selected from < 1 M G > where X is a leaving group.
51. A compound of the formula or a pharmaceutically acceptable salt or solvate thereof.
52. A compound of the formula or a pharmaceutically acceptable salt or solvate thereof, wherein, independently at each location:
R1 is selected from hydrogen and lower alkyl;
R2 is selected from hydrogen and lower alkyl;

R3 is lower alkyl;

R4 is selected from lower alkyl, aryl, and -CH2-C5-7carbocycle when R5 is selected from H and methyl, or R4 and R5 together form a carbocycle of the partial formula -(CR a R b)n- wherein R a and R b are independently selected from hydrogen and lower alkyl and n is selected from 2, 3, 4, 5 and 6;

R6 is selected from hydrogen and lower alkyl;
R7 is sec-butyl or iso-butyl;
R8 is selected from hydrogen and lower alkyl;
R11 is selected from hydrogen and lower alkyl; and R18 is selected from a hydroxyl protecting group and a direct bond such that OR18 represents =O.
53. A compound or pharmaceutically acceptable salt or solvate thereof of claim 52 wherein R1 is hydrogen.
54. A compound or pharmaceutically acceptable salt or solvate thereof of claim 52 wherein R1 and R2 are methyl.
55. A compound or pharmaceutically acceptable salt or solvate thereof of claim 52 wherein R3 is isopropyl.
56. A compound or pharmaceutically acceptable salt or solvate thereof of claim 52 wherein R4 is selected from lower alkyl, aryl, and -CH2-C5-7carbocycle and R5 is selected from H and methyl.
57. A compound or pharmaceutically acceptable salt or solvate thereof of claim 52 wherein R4 is selected from lower alkyl, and R5 is selected from H
and methyl.
58. A compound or pharmaceutically acceptable salt or solvate thereof of claim 52 wherein R4 and R5 together form a carbocycle of the partial formula -(CR a R b)n-wherein R a and R b are independently selected from hydrogen and lower alkyl and n is selected from 2, 3, 4, 5 and 6.
59. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 52 wherein R6 is lower alkyl.
60. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 52 wherein R8 is hydrogen.
61. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 52 wherein R11 is hydrogen.
62. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 52 wherein -OR18 is =O.
63. A compound of the formula or a pharmaceutically acceptable salt or solvate thereof wherein, independently at each location:
R1 is selected from hydrogen and lower alkyl;
R2 is selected from hydrogen and lower alkyl;
R3 is lower alkyl;
R4 is selected from lower alkyl, aryl, and -CH2-C5-7carbocycle when R5 is selected from H and methyl, or R4 and R5 together form a carbocycle of the partial formula -(CR a R b)n- wherein R a and R b are independently selected from hydrogen and lower alkyl and n is selected from 2, 3, 4, 5 and 6;
R6 is selected from hydrogen and lower alkyl;
R7 is sec-butyl or iso-butyl;
R8 is selected from hydrogen and lower alkyl; and R19 is selected from hydroxy and oxo-substituted lower alkyl.
64. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 63 wherein R1 is hydrogen.
65. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 63 wherein R1 and R2 are methyl.
66. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 63 wherein R3 is iso-propyl.
67. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 63 wherein R4 is selected from lower alkyl, aryl, and -CH2-C5-7carbocycle and R5 is selected from H and methyl.
68. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 63 wherein R4 is selected from lower alkyl, and R5 is selected from H
and methyl.
69. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 63 wherein R4 and R5 together form a carbocycle of the partial formula -(CR a R b)n-wherein R a and R b are independently selected from hydrogen and lower alkyl and n is selected from 2, 3, 4, 5 and 6.
70. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 63 wherein R6 is lower alkyl.
71. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 63 wherein R8 is hydrogen.
72. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 63 wherein R19 is oxo-substituted lower alkyl.
73. A compound of claim 63 having the structure or a pharmaceutically acceptable salt or solvate thereof.
74. A compound of the formula or a pharmaceutically acceptable salt or solvate thereof wherein, independently at each location:
R1 is selected from hydrogen and lower alkyl;
R2 is selected from hydrogen and lower alkyl;
R3 is lower alkyl;
R4 is selected from lower alkyl, aryl, and -CH2-C5-7carbocycle when R5 is selected from H and methyl, or R4 and R5 together form a carbocycle of the partial formula -(CR a R b)n- wherein R a and R b are independently selected from hydrogen and lower alkyl and n is selected from 2, 3, 4, 5 and 6;
R6 is selected from hydrogen and lower alkyl;
R7 is sec-butyl or iso-butyl;
R8 is selected from hydrogen and lower alkyl; and R9 is selected from R10 is selected from R11 is selected from hydrogen and lower alkyl;
R12 is selected from lower alkyl, halogen, and methoxy, and m is 0-5 where R12 is independently selected at each occurrence;
R14 is selected from a direct bond, arylene(lower alkylene), lower alkylene and arylene; and R15 is selected from hydrogen, lower alkyl and aryl.
75. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 74 wherein R10 is .
76. A compound or a pharmaceutically acceptable salt or solvate thereof of claim 74 wherein R10 is .
77. A compound of claim 74 having the structure or a pharmaceutically acceptable salt or solvate thereof.
78. A compound of claim 74 having the structure or a pharmaceutically acceptable salt or solvate thereof.
79. A compound of claim 74 having the structure or a pharmaceutically acceptable salt or solvate thereof wherein R4 is iso-propyl or sec-butyl and R5 is hydrogen.
80. A composition comprising a compound or a pharmaceutically acceptable salt or solvate thereof of any one of claims 1-32 and a pharmaceutically acceptable carrier, diluent or excipient.
81. A composition comprising a compound or a pharmaceutically acceptable salt or solvate thereof of any one of claims 51, 62 or 72 and a pharmaceutically acceptable carrier, diluent or excipient.
82. A method of killing a cell, the method comprising contacting the cell with a lethal amount of the compound or a pharmaceutically acceptable salt or solvate thereof of any one of claims 1-32.
83. A method of killing a cell, the method comprising administering to the cell a lethal amount of the compound or a pharmaceutically acceptable salt or solvate thereof of any one of claims 51, 62 or 72.
84. A method of killing a cell comprising a. delivering a compound or a pharmaceutically acceptable salt or solvate thereof of any one of claims 1-32 to a cell, where the compound enters the cell, where the compound or a pharmaceutically acceptable salt or solvate thereof enters the cell;
b. cleaving mAb from the remainder of the compound or a pharmaceutically acceptable salt or solvate thereof; and c. killing the cell with the remainder of the compound or a pharmaceutically acceptable salt or solvate thereof.
85. A method of killing or inhibiting the multiplication of tumor cells or cancer cells in a human or other animal, the method comprising administering to the human or animal in need thereof a therapeutically effective amount of a compound or a pharmaceutically acceptable salt or solvate thereof of any one of claims 1-32.
86. A method of killing or inhibiting the multiplication of tumor cells or cancer cells in a human or other animal, the method comprising administering to the human or animal in need thereof a therapeutically effective amount of a compound or a pharmaceutically acceptable salt or solvate thereof of any one of claims 51, 62 or 72.
87. A method for treating cancer, comprising administering to an animal subject in need thereof an effective amount of a compound or a pharmaceutically acceptable salt or solvate of any one of claims 1-32.
88. A method for treating cancer, comprising administering to an animal subject in need thereof an effective amount of a compound or a pharmaceutically acceptable salt or solvate of any one of claims 51, 62 or 72.
89. A method for treating an autoimmune disease, comprising administering to an animal subject in need thereof an effective amount of a compound or a pharmaceutically acceptable salt or solvate of any one of claims 1-32.
90. A method for treating an autoimmune disease, comprising administering to an animal subject in need thereof an effective amount of a compound or a pharmaceutically acceptable salt or solvate of any one of claims 51, 62 or 72.
91. The method of claim 87, further comprising administering an effective amount of an anticancer agent.
92. The method of claim 88, further comprising administering an effective amount of an anticancer agent.
93. The method of claim 89, further comprising administering an effective amount of an immunosuppressant agent.
94. The method of claim 90, further comprising administering an effective amount of an immunosuppressant agent.
CA2445875A 2001-04-30 2002-04-30 Pentapeptide compounds and uses related thereto Expired - Lifetime CA2445875C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US09/845,786 US20030083263A1 (en) 2001-04-30 2001-04-30 Pentapeptide compounds and uses related thereto
US09/845,786 2001-04-30
US10/001,191 2001-11-01
US10/001,191 US6884869B2 (en) 2001-04-30 2001-11-01 Pentapeptide compounds and uses related thereto
PCT/US2002/013435 WO2002088172A2 (en) 2001-04-30 2002-04-30 Pentapeptide compounds and uses related thereto

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CA2445875A1 true CA2445875A1 (en) 2002-11-07
CA2445875C CA2445875C (en) 2012-06-26

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EP (1) EP1390393A4 (en)
JP (1) JP4095444B2 (en)
AU (1) AU2002308515C1 (en)
CA (1) CA2445875C (en)
WO (1) WO2002088172A2 (en)

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