CA2470255A1 - N4-acylcytosine nucleosides for treatment of viral infections - Google Patents
N4-acylcytosine nucleosides for treatment of viral infections Download PDFInfo
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- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
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- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/06—Pyrimidine radicals
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
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- A—HUMAN NECESSITIES
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/18—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one nitrogen atom, e.g. guanine
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
- C07D473/34—Nitrogen atom attached in position 6, e.g. adenine
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
Abstract
The present invention is directed to a method and composition of treating or preventing viral infections, in particular, human immunodeficiency virus (HIV) and hepatitis B virus (HBV) infections, in human patients or other animals hosts, comprising the administration of N4-acyl-2',3'-dideoxy-cytidine of formula (I) or N4-acyl-2',3'-didehydro-2',3' dideoxy-cytidine (II), and pharmaceutically acceptable salts, prodrugs, and other derivatives thereof:
(see formula I)(see formula II)
(see formula I)(see formula II)
Claims (17)
1. A compound of formula (I) or (II):
or a pharmaceutically acceptable salt or prodrug thereof, wherein i) X is O, S, NR5, CH2, CHF or CF2;
ii) Y is CH2, CHF or CF2;
iii) R1 is chosen from hydrogen, halogen (F, Cl, Br, I), alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, CN, CF3, N3, NO2, aryl, heteroaryl and acyl;
iv) R2 is chosen from alkenyl, alkynyl, cycloalkyl, aminoalkyl, hydroxyalkyl, haloalkyl, thioalkyl, aryl, heteroaryl, and C6H4R6 where R6 is chosen from halogen (F, Cl, Br, I), CN, CF3, N3, NO2, alkyl, haloalkyl, aminoalkyl, alkoxy, thioalkyl, alkenyl, alkynyl, and aryl;
v) R3 and R3' are chosen independently from H, halogen (F, Cl, Br, I), CN, CF3, N3, NO2, alkyl, alkenyl, and alkynyl;
vi) R4 is H, phosphate, carbonyl substituted with alkyl, alkenyl, alkynyl, aryl, or other pharmaceutically acceptable leaving group, which, when administered in vivo, is capable of providing a compound wherein R3 and R3' are H or phosphate, sulfonate ester, a lipid, an amino acid, a peptide, or cholesterol; and vii) R5 is H, acyl, alkyl, alkenyl, alkynyl, or cycloalkyl.
or a pharmaceutically acceptable salt or prodrug thereof, wherein i) X is O, S, NR5, CH2, CHF or CF2;
ii) Y is CH2, CHF or CF2;
iii) R1 is chosen from hydrogen, halogen (F, Cl, Br, I), alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, CN, CF3, N3, NO2, aryl, heteroaryl and acyl;
iv) R2 is chosen from alkenyl, alkynyl, cycloalkyl, aminoalkyl, hydroxyalkyl, haloalkyl, thioalkyl, aryl, heteroaryl, and C6H4R6 where R6 is chosen from halogen (F, Cl, Br, I), CN, CF3, N3, NO2, alkyl, haloalkyl, aminoalkyl, alkoxy, thioalkyl, alkenyl, alkynyl, and aryl;
v) R3 and R3' are chosen independently from H, halogen (F, Cl, Br, I), CN, CF3, N3, NO2, alkyl, alkenyl, and alkynyl;
vi) R4 is H, phosphate, carbonyl substituted with alkyl, alkenyl, alkynyl, aryl, or other pharmaceutically acceptable leaving group, which, when administered in vivo, is capable of providing a compound wherein R3 and R3' are H or phosphate, sulfonate ester, a lipid, an amino acid, a peptide, or cholesterol; and vii) R5 is H, acyl, alkyl, alkenyl, alkynyl, or cycloalkyl.
2. A pharmaceutical composition that includes an effective HIV or HBV
treatment amount of a compound of claim 1 in a pharmaceutically acceptable carrier or diluent.
treatment amount of a compound of claim 1 in a pharmaceutically acceptable carrier or diluent.
3. A method for the treatment of a host infected with HIV that includes administering an effective amount of a compound of claim 1 or 17 in a pharmaceutically acceptable carrier.
4. A method for the treatment of a host infected with HBV that includes administering an effective amount of a compound of claim 1 or 17 in a pharmaceutically acceptable carrier.
5. A method for the treatment of a host infected with HIV that includes administering an effective amount of a compound of claim 1 or 17 in a pharmaceutically acceptable carrier in combination with another anti-HIV
agent.
agent.
6. A method for the treatment of a host infected with HBV that includes administering an effective amount of a compound of claim 1 or 17 in a pharmaceutically acceptable carrier in combination with another anti-HIV
agent.
agent.
7. A compound of claim 1 or 17 for use in the treatment of host infected with HIV.
8. A compound of claim 1 or 17 for use in the treatment of a host infected with HBV
infection.
infection.
9. The use of a compound of claim 1 or 17 in the manufacture of a medicament for the treatment of a host infected with HIV.
10. The use of a compound of claim 1 or 17 in the manufacture of a medicament for the treatment of a host infected with HBV.
11. The compound of claim 1, 7 or 8 selected from the group consisting of .beta.-D-N4-p-iodobenzoyl-2',3'-dideoxy-5-fluorocytidine, .beta.-D-N4-p-fluoro-benzoyl-2',3'-dideoxy-5-fluorocytidine, .beta.-D-N4-p-chlorobenzoyl-2',3'-dideoxy-5-fluoro-cytidine, .beta.-D N4-p-bromobenzoyl-2',3'-dideoxy-5-fluorocytidine, .beta.-D-N4-p-ethyl-benzoyl-2',3'-dideoxy-5-fluorocytidine, .beta.-D-N4-p-t-butylbenzoyl-2',3'-dideoxy-5-fluoro-cytidine.
12. The compound of claim 1, 7 or 8 selected from the group consisting of .beta.-D-N4-p-bromobenzoyl-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine, .beta.-D-N4-p-fluorobenzoyl-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine, .beta.-D-N4-p-chlorobenzoyl-2',3'-didehydro-2' 3'-dideoxy-5-fluorocytidine, .beta.-D-N4-p-iodobenzoyl-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine, .beta.-D-N4-p-ethylbenzoyl-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine, and .beta.-D-N4-p-t-butylbenzoyl-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine.
13. The method of claims 2 or 3 wherein the compound is selected from the group consisting of .beta.-D-N4-p-iodobenzoyl-2',3'-dideoxy-5-fluorocytidine, .beta.-D-N4-p-fluoro-benzoyl-2',3'-dideoxy-5-fluorocytidine, .beta.-D-N4-p-chlorobenzoyl-2',3'-dideoxy-5-fluoro-cytidine, .beta.-D-N4-p-bromobenzoyl-2',3'-dideoxy-5-fluorocytidine, .beta.-D-N4-p-ethyl-benzoyl-2',3'-dideoxy-5-fluorocytidine, .beta.-D-N4-p-t-butylbenzoyl-2',3'-dideoxy-5-fluoro-cytidine.
14. The method of claims 2 or 3 wherein the compound is selected from the group consisting of .beta.-D-N4-p-bromobenzoyl-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine, .beta.-D-N4-p-fluorobenzoyl-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine, .beta.-D-N4-p-chlorobenzoyl-2',3'-didehydro-2'3'-dideoxy-5-fluorocytidine, .beta.-D-N4-p-iodobenzoyl-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine, .beta.-D-N4-p-ethylbenzoyl-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine, and .beta.-D-N4-p-t-butylbenzoyl-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine.
15. The use of claims 9 or 10 wherein the compound is selected from the group consisting of .beta.-D-N4-p-iodobenzoyl-2',3'-dideoxy-5-fluorocytidine, .beta.-D-N4-p-fluoro-benzoyl-2',3'-dideoxy-5-fluorocytidine, .beta.-D-N4-p-chlorobenzoyl-2',3'-dideoxy-5-fluoro-cytidine, .beta.-D-N4-p-bromobenzoyl-2',3'-dideoxy-5-fluorocytidine, .beta.-D-N4-p-ethyl-benzoyl-2',3'-dideoxy-5-fluorocytidine, .beta.-D-N4-p-t-butylbenzoyl-2',3'-dideoxy-5-fluoro-cytidine.
16. The use of claims 9 or 10 wherein the compound is selected from the group consisting of .beta.-D-N4-p-bromobenzoyl-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine, .beta.-D-N4-p-fluorobenzoyl-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine, .beta.-D-N4-p-chlorobenzoyl-2',3'-didehydro-2'3'-dideoxy-5-fluorocytidine, .beta.-D-N4-p-iodobenzoyl-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine, .beta.-D-N4-p-ethylbenzoyl-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine, and .beta.-D-N4-p-t-butylbenzoyl-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine.
17. A compound selected from the following, or its pharmaceutically acceptable salt or prodrug:
.beta.-D-2',3'-dideoxy-5-fluoro-N4-(4-iodobenzoyl)cytidine of the structure:
.beta.-D-2',3'-dideoxy-5-fluoro-N4-(4-fluorobenzoyl)cytidine of the structure:
.beta.-D-N4-(4-chlorobenzoyl)-2',3'-dideoxy-5-fluorocytidine of the structure:
.beta.-D-N4-(4-bromobenzoyl)-2',3'-dideoxy-5-fluorocytidine of the structure:
.beta.-D-2',3'-dideoxy-5-fluoro N4-(3-fluorobenzoyl)cytidine of the structure:
.beta.-D-N4-(3-chlorobenzoyl)-2',3'-dideoxy-5-fluorocytidine of the structure:
or a pharmaceutically acceptable salt or prodrug thereof.
In one preferred embodiment, the active compound is .beta.-D-N4-(3-bromobenzoyl)-2',3'-dideoxy-5-fluorocytidine of the structure:
.beta.-D-2',3'-dideoxy-5-fluoro-N4-(4-nitrobenzoyl)cytidine of the structure:
.beta.-D-2',3'-dideoxy-5-fluoro-N4-p-toluoylcytidine of the structure:
.beta.-D-2',3'-dideoxy-5-fluoro-N4-(m-toluoyl)cytidine of the structure:
.beta.-D-2',3'-dideoxy-N4-(4-ethylbenzoyl)-5-fluorocytidine of the structure:
.beta.-D-2',3'-dideoxy-5-fluoro-N4-(4-propylbenzoyl)cytidine of the structure:
.beta.-D-N4-(4-tert-butylbenzoyl)-2',3'-dideoxy-5-fluorocytidine of the structure:
.beta.-D-2',3'-dideoxy-5-fluoro-N4-(2-thiophenecarbonyl)cytidine of the structure:
.beta.-D-N4-(benzo-[b]-thiophene-2-carbonyl)-2',3'-dideoxy-5-fluorocytidine of the structure:
.beta.-D-N4-(cyclohexane-carbonyl)-2',3'-dideoxy-5-fluorocytidine of the structure:
.beta.-D-2',3'-didehydro-2',3'-dideoxy-5-fluoro-N4-(4-iodobenzoyl)cytidine of the structure:
.beta.-D-2',3'-didehydro-2',3'-dideoxy-5-fluoro-N4-(4-fluorobenzoyl)cytidine of the structure:
.beta.-D-N4-(4-chlorobenzoyl)-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine of the structure:
.beta.-D-N4-(4-bromobenzoyl)-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine of the structure:
.beta.-D-N4-p-anisoyl-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine of the structure:
.beta.-D-2',3'-didehydro-2',3'-dideoxy-5-fluoro-N4-(3-nitrobenzoyl)cytidine of the structure:
.beta.-D-2',3'-didehydro-2',3'-dideoxy-5-fluoro-N4-p-toluoylcytidine of the structure:
.beta.-D-2',3'-didehydro-2',3'-dideoxy-5-fluoro-N4-m-toluoylcytidine of the structure:
.beta.-D-N4-(4-t-butylbenzoyl)-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine of the structure:
or a pharmaceutically acceptable salt or prodrug thereof.
.beta.-D-N4-cyclopentanecarbonyl-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine of the structure:
or a pharmaceutically acceptable salt or prodrug thereof.
.beta.-D-N4-(cyclohexanecarbonyl)-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine of the structure:
.beta.-D-2',3'-dideoxy-5-fluoro-N4-(4-iodobenzoyl)cytidine of the structure:
.beta.-D-2',3'-dideoxy-5-fluoro-N4-(4-fluorobenzoyl)cytidine of the structure:
.beta.-D-N4-(4-chlorobenzoyl)-2',3'-dideoxy-5-fluorocytidine of the structure:
.beta.-D-N4-(4-bromobenzoyl)-2',3'-dideoxy-5-fluorocytidine of the structure:
.beta.-D-2',3'-dideoxy-5-fluoro N4-(3-fluorobenzoyl)cytidine of the structure:
.beta.-D-N4-(3-chlorobenzoyl)-2',3'-dideoxy-5-fluorocytidine of the structure:
or a pharmaceutically acceptable salt or prodrug thereof.
In one preferred embodiment, the active compound is .beta.-D-N4-(3-bromobenzoyl)-2',3'-dideoxy-5-fluorocytidine of the structure:
.beta.-D-2',3'-dideoxy-5-fluoro-N4-(4-nitrobenzoyl)cytidine of the structure:
.beta.-D-2',3'-dideoxy-5-fluoro-N4-p-toluoylcytidine of the structure:
.beta.-D-2',3'-dideoxy-5-fluoro-N4-(m-toluoyl)cytidine of the structure:
.beta.-D-2',3'-dideoxy-N4-(4-ethylbenzoyl)-5-fluorocytidine of the structure:
.beta.-D-2',3'-dideoxy-5-fluoro-N4-(4-propylbenzoyl)cytidine of the structure:
.beta.-D-N4-(4-tert-butylbenzoyl)-2',3'-dideoxy-5-fluorocytidine of the structure:
.beta.-D-2',3'-dideoxy-5-fluoro-N4-(2-thiophenecarbonyl)cytidine of the structure:
.beta.-D-N4-(benzo-[b]-thiophene-2-carbonyl)-2',3'-dideoxy-5-fluorocytidine of the structure:
.beta.-D-N4-(cyclohexane-carbonyl)-2',3'-dideoxy-5-fluorocytidine of the structure:
.beta.-D-2',3'-didehydro-2',3'-dideoxy-5-fluoro-N4-(4-iodobenzoyl)cytidine of the structure:
.beta.-D-2',3'-didehydro-2',3'-dideoxy-5-fluoro-N4-(4-fluorobenzoyl)cytidine of the structure:
.beta.-D-N4-(4-chlorobenzoyl)-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine of the structure:
.beta.-D-N4-(4-bromobenzoyl)-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine of the structure:
.beta.-D-N4-p-anisoyl-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine of the structure:
.beta.-D-2',3'-didehydro-2',3'-dideoxy-5-fluoro-N4-(3-nitrobenzoyl)cytidine of the structure:
.beta.-D-2',3'-didehydro-2',3'-dideoxy-5-fluoro-N4-p-toluoylcytidine of the structure:
.beta.-D-2',3'-didehydro-2',3'-dideoxy-5-fluoro-N4-m-toluoylcytidine of the structure:
.beta.-D-N4-(4-t-butylbenzoyl)-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine of the structure:
or a pharmaceutically acceptable salt or prodrug thereof.
.beta.-D-N4-cyclopentanecarbonyl-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine of the structure:
or a pharmaceutically acceptable salt or prodrug thereof.
.beta.-D-N4-(cyclohexanecarbonyl)-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine of the structure:
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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US34155501P | 2001-12-14 | 2001-12-14 | |
US60/341,555 | 2001-12-14 | ||
PCT/US2002/040081 WO2003063771A2 (en) | 2001-12-14 | 2002-12-13 | N4-acylcytosine nucleosides for treatment of viral iinfections |
Publications (2)
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CA2470255A1 true CA2470255A1 (en) | 2003-08-07 |
CA2470255C CA2470255C (en) | 2012-01-17 |
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CA2470255A Expired - Fee Related CA2470255C (en) | 2001-12-14 | 2002-12-13 | N4-acylcytosine nucleosides for treatment of viral infections |
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US (6) | US7105527B2 (en) |
EP (1) | EP1569652A4 (en) |
JP (1) | JP2005519916A (en) |
KR (1) | KR100978904B1 (en) |
CN (1) | CN100560073C (en) |
AU (2) | AU2002365234B2 (en) |
BR (1) | BR0214944A (en) |
CA (1) | CA2470255C (en) |
MX (1) | MXPA04005779A (en) |
WO (2) | WO2003063771A2 (en) |
Families Citing this family (41)
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US6790228B2 (en) * | 1999-12-23 | 2004-09-14 | Advanced Cardiovascular Systems, Inc. | Coating for implantable devices and a method of forming the same |
BR0110023A (en) | 2000-04-13 | 2003-12-30 | Pharmasset Ltd | Substituted 3'-or-2 'nucleoside derivatives for treatment of hepatitis virus infections |
MY164523A (en) | 2000-05-23 | 2017-12-29 | Univ Degli Studi Cagliari | Methods and compositions for treating hepatitis c virus |
EP1294735A2 (en) * | 2000-05-26 | 2003-03-26 | Novirio Pharmaceuticals Limited | Methods and compositions for treating flaviviruses and pestiviruses |
CN100560073C (en) * | 2001-12-14 | 2009-11-18 | 法玛塞特公司 | The N that is used for the treatment of viral infection 4-acyl group cytidine |
CN101172993A (en) * | 2002-06-28 | 2008-05-07 | 埃迪尼克斯(开曼)有限公司 | 2'-c-methyl-3'-o-l-valine ester ribofuranosyl cytidine for treatment of flaviviridae infections |
US7608600B2 (en) | 2002-06-28 | 2009-10-27 | Idenix Pharmaceuticals, Inc. | Modified 2′ and 3′-nucleoside prodrugs for treating Flaviviridae infections |
KR20050035194A (en) * | 2002-06-28 | 2005-04-15 | 이데닉스 (케이만) 리미티드 | 2'-c-methyl-3'-o-l-valine ester ribofuranosyl cytidine for treatment of flaviviridae infections |
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-
2002
- 2002-12-13 CN CNB028278402A patent/CN100560073C/en not_active Expired - Fee Related
- 2002-12-13 US US10/318,511 patent/US7105527B2/en not_active Expired - Fee Related
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- 2002-12-13 BR BR0214944-3A patent/BR0214944A/en not_active Application Discontinuation
- 2002-12-13 MX MXPA04005779A patent/MXPA04005779A/en active IP Right Grant
- 2002-12-13 CA CA2470255A patent/CA2470255C/en not_active Expired - Fee Related
- 2002-12-13 EP EP02804833A patent/EP1569652A4/en not_active Withdrawn
- 2002-12-13 KR KR1020047009263A patent/KR100978904B1/en not_active IP Right Cessation
- 2002-12-13 WO PCT/US2002/040081 patent/WO2003063771A2/en active Application Filing
- 2002-12-13 AU AU2002365234A patent/AU2002365234B2/en not_active Ceased
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2006
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- 2007-06-21 US US11/821,076 patent/USRE42015E1/en not_active Expired - Fee Related
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2008
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EP1569652A4 (en) | 2008-07-02 |
CA2470255C (en) | 2012-01-17 |
US8114997B2 (en) | 2012-02-14 |
WO2003063771A3 (en) | 2005-07-07 |
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KR100978904B1 (en) | 2010-08-31 |
US20120202766A1 (en) | 2012-08-09 |
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AU2002365234B2 (en) | 2009-01-29 |
US6908924B2 (en) | 2005-06-21 |
MXPA04005779A (en) | 2005-05-16 |
BR0214944A (en) | 2005-06-07 |
AU2002364730A8 (en) | 2003-06-30 |
CN1617726A (en) | 2005-05-18 |
US20090176730A1 (en) | 2009-07-09 |
AU2002364730A1 (en) | 2003-06-30 |
WO2003051306A2 (en) | 2003-06-26 |
EP1569652A2 (en) | 2005-09-07 |
US20030176319A1 (en) | 2003-09-18 |
USRE42015E1 (en) | 2010-12-28 |
WO2003051306A3 (en) | 2003-12-18 |
WO2003063771A2 (en) | 2003-08-07 |
JP2005519916A (en) | 2005-07-07 |
US7105527B2 (en) | 2006-09-12 |
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