CA2548753A1 - 4-substituted carbovir and abacavir-derivatives as well as related compounds with hiv and hcv antiviral activity - Google Patents
4-substituted carbovir and abacavir-derivatives as well as related compounds with hiv and hcv antiviral activity Download PDFInfo
- Publication number
- CA2548753A1 CA2548753A1 CA002548753A CA2548753A CA2548753A1 CA 2548753 A1 CA2548753 A1 CA 2548753A1 CA 002548753 A CA002548753 A CA 002548753A CA 2548753 A CA2548753 A CA 2548753A CA 2548753 A1 CA2548753 A1 CA 2548753A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- pharmaceutically acceptable
- formula
- solvate
- acceptable salt
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract 35
- XSSYCIGJYCVRRK-RQJHMYQMSA-N (-)-carbovir Chemical class C1=NC=2C(=O)NC(N)=NC=2N1[C@@H]1C[C@H](CO)C=C1 XSSYCIGJYCVRRK-RQJHMYQMSA-N 0.000 title 1
- 230000000840 anti-viral effect Effects 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract 17
- 239000012453 solvate Substances 0.000 claims abstract 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract 11
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical group O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims abstract 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 8
- RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical group CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 claims abstract 8
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 7
- 125000000304 alkynyl group Chemical group 0.000 claims abstract 7
- PZOUSPYUWWUPPK-UHFFFAOYSA-N 4-methyl-1h-indole Chemical compound CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims abstract 6
- PEHVGBZKEYRQSX-UHFFFAOYSA-N 7-deaza-adenine Chemical group NC1=NC=NC2=C1C=CN2 PEHVGBZKEYRQSX-UHFFFAOYSA-N 0.000 claims abstract 6
- LOSIULRWFAEMFL-UHFFFAOYSA-N 7-deazaguanine Chemical group O=C1NC(N)=NC2=C1CC=N2 LOSIULRWFAEMFL-UHFFFAOYSA-N 0.000 claims abstract 6
- FDGQSTZJBFJUBT-UHFFFAOYSA-N hypoxanthine Chemical compound O=C1NC=NC2=C1NC=N2 FDGQSTZJBFJUBT-UHFFFAOYSA-N 0.000 claims abstract 6
- DRAVOWXCEBXPTN-UHFFFAOYSA-N isoguanine Chemical compound NC1=NC(=O)NC2=C1NC=N2 DRAVOWXCEBXPTN-UHFFFAOYSA-N 0.000 claims abstract 6
- WYWHKKSPHMUBEB-UHFFFAOYSA-N tioguanine Chemical compound N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 claims abstract 6
- 230000000694 effects Effects 0.000 claims abstract 5
- 208000015181 infectious disease Diseases 0.000 claims abstract 5
- 229930024421 Adenine Natural products 0.000 claims abstract 4
- 229960000643 adenine Drugs 0.000 claims abstract 4
- GFFGJBXGBJISGV-UHFFFAOYSA-N adenyl group Chemical group N1=CN=C2N=CNC2=C1N GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract 4
- 229940113082 thymine Drugs 0.000 claims abstract 4
- 229940035893 uracil Drugs 0.000 claims abstract 4
- QUKPALAWEPMWOS-UHFFFAOYSA-N 1h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=NC=C2C=NNC2=N1 QUKPALAWEPMWOS-UHFFFAOYSA-N 0.000 claims abstract 3
- XQCZBXHVTFVIFE-UHFFFAOYSA-N 2-amino-4-hydroxypyrimidine Chemical class NC1=NC=CC(O)=N1 XQCZBXHVTFVIFE-UHFFFAOYSA-N 0.000 claims abstract 3
- MWBWWFOAEOYUST-UHFFFAOYSA-N 2-aminopurine Chemical compound NC1=NC=C2N=CNC2=N1 MWBWWFOAEOYUST-UHFFFAOYSA-N 0.000 claims abstract 3
- HCGYMSSYSAKGPK-UHFFFAOYSA-N 2-nitro-1h-indole Chemical compound C1=CC=C2NC([N+](=O)[O-])=CC2=C1 HCGYMSSYSAKGPK-UHFFFAOYSA-N 0.000 claims abstract 3
- FTBBGQKRYUTLMP-UHFFFAOYSA-N 2-nitro-1h-pyrrole Chemical compound [O-][N+](=O)C1=CC=CN1 FTBBGQKRYUTLMP-UHFFFAOYSA-N 0.000 claims abstract 3
- OVONXEQGWXGFJD-UHFFFAOYSA-N 4-sulfanylidene-1h-pyrimidin-2-one Chemical compound SC=1C=CNC(=O)N=1 OVONXEQGWXGFJD-UHFFFAOYSA-N 0.000 claims abstract 3
- NBAKTGXDIBVZOO-UHFFFAOYSA-N 5,6-dihydrothymine Chemical compound CC1CNC(=O)NC1=O NBAKTGXDIBVZOO-UHFFFAOYSA-N 0.000 claims abstract 3
- GSPMCUUYNASDHM-UHFFFAOYSA-N 5-methyl-4-sulfanylidene-1h-pyrimidin-2-one Chemical compound CC1=CNC(=O)N=C1S GSPMCUUYNASDHM-UHFFFAOYSA-N 0.000 claims abstract 3
- BXJHWYVXLGLDMZ-UHFFFAOYSA-N 6-O-methylguanine Chemical compound COC1=NC(N)=NC2=C1NC=N2 BXJHWYVXLGLDMZ-UHFFFAOYSA-N 0.000 claims abstract 3
- QNNARSZPGNJZIX-UHFFFAOYSA-N 6-amino-5-prop-1-ynyl-1h-pyrimidin-2-one Chemical compound CC#CC1=CNC(=O)N=C1N QNNARSZPGNJZIX-UHFFFAOYSA-N 0.000 claims abstract 3
- CKOMXBHMKXXTNW-UHFFFAOYSA-N 6-methyladenine Chemical compound CNC1=NC=NC2=C1N=CN2 CKOMXBHMKXXTNW-UHFFFAOYSA-N 0.000 claims abstract 3
- LHCPRYRLDOSKHK-UHFFFAOYSA-N 7-deaza-8-aza-adenine Chemical compound NC1=NC=NC2=C1C=NN2 LHCPRYRLDOSKHK-UHFFFAOYSA-N 0.000 claims abstract 3
- 229960005508 8-azaguanine Drugs 0.000 claims abstract 3
- MSSXOMSJDRHRMC-UHFFFAOYSA-N 9H-purine-2,6-diamine Chemical compound NC1=NC(N)=C2NC=NC2=N1 MSSXOMSJDRHRMC-UHFFFAOYSA-N 0.000 claims abstract 3
- UGQMRVRMYYASKQ-UHFFFAOYSA-N Hypoxanthine nucleoside Natural products OC1C(O)C(CO)OC1N1C(NC=NC2=O)=C2N=C1 UGQMRVRMYYASKQ-UHFFFAOYSA-N 0.000 claims abstract 3
- 229930010555 Inosine Natural products 0.000 claims abstract 3
- UGQMRVRMYYASKQ-KQYNXXCUSA-N Inosine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC(O)=C2N=C1 UGQMRVRMYYASKQ-KQYNXXCUSA-N 0.000 claims abstract 3
- MRWXACSTFXYYMV-UHFFFAOYSA-N Nebularine Natural products OC1C(O)C(CO)OC1N1C2=NC=NC=C2N=C1 MRWXACSTFXYYMV-UHFFFAOYSA-N 0.000 claims abstract 3
- NWUTZAVMDAGNIG-UHFFFAOYSA-N O(4)-methylthymine Chemical compound COC=1NC(=O)N=CC=1C NWUTZAVMDAGNIG-UHFFFAOYSA-N 0.000 claims abstract 3
- 229930185560 Pseudouridine Natural products 0.000 claims abstract 3
- PTJWIQPHWPFNBW-UHFFFAOYSA-N Pseudouridine C Natural products OC1C(O)C(CO)OC1C1=CNC(=O)NC1=O PTJWIQPHWPFNBW-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims abstract 3
- WGDUUQDYDIIBKT-UHFFFAOYSA-N beta-Pseudouridine Natural products OC1OC(CN2C=CC(=O)NC2=O)C(O)C1O WGDUUQDYDIIBKT-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 3
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims abstract 3
- 229960003786 inosine Drugs 0.000 claims abstract 3
- MRWXACSTFXYYMV-FDDDBJFASA-N nebularine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC=C2N=C1 MRWXACSTFXYYMV-FDDDBJFASA-N 0.000 claims abstract 3
- PTJWIQPHWPFNBW-GBNDHIKLSA-N pseudouridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1C1=CNC(=O)NC1=O PTJWIQPHWPFNBW-GBNDHIKLSA-N 0.000 claims abstract 3
- HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical compound SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 0.000 claims abstract 3
- 229960003087 tioguanine Drugs 0.000 claims abstract 3
- 150000003852 triazoles Chemical class 0.000 claims abstract 3
- 241001465754 Metazoa Species 0.000 claims 15
- 239000008194 pharmaceutical composition Substances 0.000 claims 8
- 230000002401 inhibitory effect Effects 0.000 claims 7
- 238000000034 method Methods 0.000 claims 7
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical group NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 6
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical group O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 claims 6
- OIVLITBTBDPEFK-UHFFFAOYSA-N 5,6-dihydrouracil Chemical compound O=C1CCNC(=O)N1 OIVLITBTBDPEFK-UHFFFAOYSA-N 0.000 claims 4
- 208000036142 Viral infection Diseases 0.000 claims 4
- 230000002265 prevention Effects 0.000 claims 4
- 208000024891 symptom Diseases 0.000 claims 4
- 230000009385 viral infection Effects 0.000 claims 4
- 229940104302 cytosine Drugs 0.000 claims 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims 3
- RYYIULNRIVUMTQ-UHFFFAOYSA-N 6-chloroguanine Chemical compound NC1=NC(Cl)=C2N=CNC2=N1 RYYIULNRIVUMTQ-UHFFFAOYSA-N 0.000 claims 2
- 108060004795 Methyltransferase Proteins 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 230000003612 virological effect Effects 0.000 claims 2
- 208000030507 AIDS Diseases 0.000 claims 1
- 102000004190 Enzymes Human genes 0.000 claims 1
- 108090000790 Enzymes Proteins 0.000 claims 1
- 229940099797 HIV integrase inhibitor Drugs 0.000 claims 1
- 229940122440 HIV protease inhibitor Drugs 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
- 229960005475 antiinfective agent Drugs 0.000 claims 1
- 239000004599 antimicrobial Substances 0.000 claims 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
- 239000003084 hiv integrase inhibitor Substances 0.000 claims 1
- 239000004030 hiv protease inhibitor Substances 0.000 claims 1
- 239000002955 immunomodulating agent Substances 0.000 claims 1
- 229940121354 immunomodulator Drugs 0.000 claims 1
- 230000002584 immunomodulator Effects 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 238000013160 medical therapy Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 229940042402 non-nucleoside reverse transcriptase inhibitor Drugs 0.000 claims 1
- 239000002726 nonnucleoside reverse transcriptase inhibitor Substances 0.000 claims 1
- 239000003419 rna directed dna polymerase inhibitor Substances 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- NOIRDLRUNWIUMX-UHFFFAOYSA-N 2-amino-3,7-dihydropurin-6-one;6-amino-1h-pyrimidin-2-one Chemical group NC=1C=CNC(=O)N=1.O=C1NC(N)=NC2=C1NC=N2 NOIRDLRUNWIUMX-UHFFFAOYSA-N 0.000 abstract 1
- 241000700605 Viruses Species 0.000 abstract 1
- 230000002458 infectious effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- 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
-
- 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
-
- 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
-
- 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
- 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
- C07D473/16—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two nitrogen atoms
-
- 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
- C07H19/06—Pyrimidine radicals
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Virology (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53225603P | 2003-12-22 | 2003-12-22 | |
| US60/532,256 | 2003-12-22 | ||
| PCT/US2004/043571 WO2005063751A1 (en) | 2003-12-22 | 2004-12-22 | 4’-substituted carbovir-and abacavir-derivatives as well as related compounds with hiv and hcv antiviral activity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2548753A1 true CA2548753A1 (en) | 2005-07-14 |
Family
ID=34738778
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002548753A Abandoned CA2548753A1 (en) | 2003-12-22 | 2004-12-22 | 4-substituted carbovir and abacavir-derivatives as well as related compounds with hiv and hcv antiviral activity |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US20080287471A1 (https=) |
| EP (1) | EP1706405B1 (https=) |
| JP (1) | JP2007515495A (https=) |
| KR (1) | KR20060127906A (https=) |
| CN (1) | CN1906196A (https=) |
| AT (1) | ATE424400T1 (https=) |
| AU (1) | AU2004309418B2 (https=) |
| BR (1) | BRPI0417988A (https=) |
| CA (1) | CA2548753A1 (https=) |
| DE (1) | DE602004019815D1 (https=) |
| MX (1) | MXPA06006899A (https=) |
| NZ (1) | NZ547907A (https=) |
| WO (1) | WO2005063751A1 (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10204821A1 (de) * | 2002-02-01 | 2003-08-14 | Obe Ohnmacht & Baumgaertner | Federscharnier |
| EP2359833A1 (en) | 2003-04-25 | 2011-08-24 | Gilead Sciences, Inc. | Antiviral phosphonate analogs |
| WO2005063751A1 (en) * | 2003-12-22 | 2005-07-14 | Gilead Sciences, Inc. | 4’-substituted carbovir-and abacavir-derivatives as well as related compounds with hiv and hcv antiviral activity |
| ME03423B (me) | 2004-07-27 | 2020-01-20 | Gilead Sciences Inc | Fosfonatni analozi jedinjenja hiv inhibitora |
| MX2008016518A (es) | 2006-06-22 | 2009-01-19 | Anadys Pharmaceuticals Inc | Profarmacos de 5-amino-3-(3'-desoxi-beta-d-ribofuranosil)-tiazolo[ 4,5-d]pirimidin-2,7-dion. |
| EP2085397A1 (en) * | 2008-01-21 | 2009-08-05 | Esteve Quimica, S.A. | Crystalline form of abacavir |
| UA103329C2 (ru) | 2008-07-08 | 2013-10-10 | Гилиад Сайенсиз, Инк. | Соли соединений-ингибиторов вич |
| US8760000B2 (en) | 2010-11-19 | 2014-06-24 | Honeywell International Inc. | Mixed signal conversion, isolation, and transmission for aerospace multi-channel data and power interface systems |
| MD20140044A2 (ro) | 2011-11-11 | 2014-08-31 | Pfizer Inc. | 2-Tiopirimidinone şi utilizarea lor pentru tratamentul afecţiunilor cardiovasculare |
| DK3236972T3 (en) | 2014-12-26 | 2021-10-04 | Univ Emory | Antivirale N4-hydroxycytidin-derivativer |
| AU2016257179A1 (en) | 2015-05-05 | 2017-11-02 | Pfizer Inc. | 2-thiopyrimidinones |
| SI3661937T1 (sl) | 2017-08-01 | 2021-11-30 | Gilead Sciences, Inc. | Kristalinične oblike etil((S)-((((2R,5R)-5-(6-amino-9H-purin-9-IL)-4- fluoro-2,5-dihidrofuran-2-IL)oksi)metil)(fenoksi)fosforil)-L-alaninata (GS-9131) za zdravljenje virusnih okužb |
| JP6804790B1 (ja) | 2017-12-07 | 2020-12-23 | エモリー ユニバーシティー | Ｎ４−ヒドロキシシチジンおよび誘導体ならびにそれらに関連する抗ウイルス用途 |
Family Cites Families (70)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE63869B1 (en) | 1986-11-06 | 1995-06-14 | Res Dev Foundation | Aerosols containing liposomes and method for their preparation |
| FR2611203B1 (fr) | 1987-02-20 | 1989-06-09 | Sturtz Georges | Analogues gem-diphosphoniques d'amethopterine (methotrexate) et de derives deaza-n-10 amethopterine. leur preparation et les compositions pharmaceutiques qui les contiennent |
| US5631370A (en) * | 1988-01-20 | 1997-05-20 | Regents Of The University Of Minnesota | Optically-active isomers of dideoxycarbocyclic nucleosides |
| DE4003574A1 (de) | 1990-02-07 | 1991-08-08 | Bayer Ag | Neue dipeptide, verfahren zu ihrer herstellung und ihre verwendung als renininhibitoren in arzneimitteln |
| ATE131825T1 (de) | 1990-06-13 | 1996-01-15 | Arnold Glazier | Phosphorylierte prodrugs |
| EP0465297B1 (en) | 1990-07-04 | 1996-01-31 | Merrell Dow Pharmaceuticals Inc. | 9-Purinyl phosphonic acid derivatives |
| US5177064A (en) | 1990-07-13 | 1993-01-05 | University Of Florida | Targeted drug delivery via phosphonate derivatives |
| DE4111730A1 (de) | 1991-04-10 | 1992-10-15 | Knoll Ag | Neue cytarabin-derivate, ihre herstellung und verwendung |
| EP0531597A1 (en) | 1991-09-12 | 1993-03-17 | Merrell Dow Pharmaceuticals Inc. | Novel unsaturated acyclic phosphonate derivatives of purine and pyrimidine |
| US5610294A (en) * | 1991-10-11 | 1997-03-11 | The Du Pont Merck Pharmaceutical Company | Substituted cyclic carbonyls and derivatives thereof useful as retroviral protease inhibitors |
| GB9126144D0 (en) | 1991-12-10 | 1992-02-12 | British Bio Technology | Compounds |
| FR2692265B1 (fr) | 1992-05-25 | 1996-11-08 | Centre Nat Rech Scient | Composes biologiquement actifs de type phosphotriesters. |
| JPH0680688A (ja) * | 1992-09-03 | 1994-03-22 | Asahi Breweries Ltd | ４’−メチルヌクレオシド誘導体 |
| IS2334B (is) * | 1992-09-08 | 2008-02-15 | Vertex Pharmaceuticals Inc., (A Massachusetts Corporation) | Aspartyl próteasi hemjari af nýjum flokki súlfonamíða |
| US5654286A (en) * | 1993-05-12 | 1997-08-05 | Hostetler; Karl Y. | Nucleotides for topical treatment of psoriasis, and methods for using same |
| ATE199906T1 (de) | 1993-06-29 | 2001-04-15 | Mitsubishi Chem Corp | Phosphonat-nukleotid ester-derivate |
| WO1995002582A1 (en) * | 1993-07-14 | 1995-01-26 | Ciba-Geigy Ag | Cyclic hydrazine compounds |
| US5446137B1 (en) * | 1993-12-09 | 1998-10-06 | Behringwerke Ag | Oligonucleotides containing 4'-substituted nucleotides |
| US5493030A (en) * | 1994-02-18 | 1996-02-20 | Syntex (U.S.A.) Inc. | 5-substituted derivatives of mycophenolic acid |
| US5854227A (en) | 1994-03-04 | 1998-12-29 | Hartmann; John F. | Therapeutic derivatives of diphosphonates |
| RU2157368C2 (ru) | 1994-09-26 | 2000-10-10 | Сионоги Энд Ко., Лтд. | Производные имидазола и фармацевтическая композиция на их основе |
| WO1996014314A2 (en) | 1994-11-04 | 1996-05-17 | Gilead Sciences, Inc. | Thiepane compounds inhibiting and detecting hiv protease |
| US5747498A (en) * | 1996-05-28 | 1998-05-05 | Pfizer Inc. | Alkynyl and azido-substituted 4-anilinoquinazolines |
| JPH11508541A (ja) | 1995-06-29 | 1999-07-27 | ノボ ノルディスク アクティーゼルスカブ | 新規な置換アザ二環式化合物 |
| US5750493A (en) * | 1995-08-30 | 1998-05-12 | Raymond F. Schinazi | Method to improve the biological and antiviral activity of protease inhibitors |
| EP0852233A4 (en) | 1995-09-21 | 1999-09-15 | Nippon Shinyaku Co Ltd | CYCLOSPORIN PHOSPHATE DERIVATIVES AND MEDICINAL COMPOSITION |
| US5914332A (en) * | 1995-12-13 | 1999-06-22 | Abbott Laboratories | Retroviral protease inhibiting compounds |
| US5874577A (en) * | 1996-04-03 | 1999-02-23 | Medichem Research, Inc. | Method for the preparing 9-12-(Diethoxyphosphonomethoxy)ethyl!adenine and analogues thereof |
| CA2261619C (en) | 1996-07-26 | 2006-05-23 | Gilead Sciences, Inc. | Nucleotide analogs |
| US6194398B1 (en) | 1996-08-13 | 2001-02-27 | Mitsubishi Chemical Corporation | Phosphonate nucleotide compound |
| EP0948341A4 (en) | 1996-09-17 | 2003-05-21 | Supergen Inc | DERIVATIVES OF PHOSPHOLIPIDE MEDICINES |
| JP4118958B2 (ja) | 1996-10-09 | 2008-07-16 | ファーマセット，リミティド | テトラホスホネート二環式トリス無水物 |
| US6436989B1 (en) | 1997-12-24 | 2002-08-20 | Vertex Pharmaceuticals, Incorporated | Prodrugs of aspartyl protease inhibitors |
| US6312662B1 (en) * | 1998-03-06 | 2001-11-06 | Metabasis Therapeutics, Inc. | Prodrugs phosphorus-containing compounds |
| US6174888B1 (en) * | 1998-05-28 | 2001-01-16 | Novartis Ag | 2-amino-7-(1-substituted-2-hydroxyethyl)-3,5-dihydropyrrolo[3,2-D]pyrimidin-4-ones |
| AU4125099A (en) | 1998-06-01 | 1999-12-20 | S & T Science And Technology Inc. | Antiviral phosphorus derivatives of 4'-thio-5-ethyl-2'-deoxyuridine |
| GB9815567D0 (en) | 1998-07-18 | 1998-09-16 | Glaxo Group Ltd | Antiviral compound |
| TWI260322B (en) * | 1999-02-12 | 2006-08-21 | Vertex Pharma | Inhibitors of aspartyl protease |
| HUP0200260A3 (en) | 1999-03-05 | 2002-11-28 | Metabasis Therapeutics Inc San | Novel phosphorus-containing prodrugs, their preparation and their use |
| US6258831B1 (en) * | 1999-03-31 | 2001-07-10 | The Procter & Gamble Company | Viral treatment |
| US6608027B1 (en) * | 1999-04-06 | 2003-08-19 | Boehringer Ingelheim (Canada) Ltd | Macrocyclic peptides active against the hepatitis C virus |
| CA2377278C (en) * | 1999-06-25 | 2010-03-23 | Vertex Pharmaceuticals Incorporated | Prodrugs of carbamate inhibitors of impdh |
| CA2381425A1 (en) | 1999-08-24 | 2001-03-01 | Cellgate, Inc. | Enhancing drug delivery across and into epithelial tissues using oligo arginine moieties |
| GB9920872D0 (en) | 1999-09-04 | 1999-11-10 | Glaxo Group Ltd | Benzophenones as inhibitors of reverse transcriptase |
| IL131887A0 (en) | 1999-09-14 | 2001-03-19 | Dpharm Ltd | Phospholipid prodrugs of anti-proliferative drugs |
| DE60038038T2 (de) | 1999-12-03 | 2009-02-12 | The Regents of The University of California at San Diego, La Jolla | Phosphonatverbindungen |
| WO2001046204A1 (en) | 1999-12-22 | 2001-06-28 | Merck Frosst Canada & Co. | Aromatic phosphonates as protein tyrosine phosphatase 1b (ptp-1b) inhibitors |
| WO2001064693A1 (fr) | 2000-02-29 | 2001-09-07 | Mitsubishi Pharma Corporation | Compose de nucleotide de phosphonate |
| IL153363A0 (en) | 2000-06-13 | 2003-07-06 | Shionogi & Co | Pharmaceutical compositions containing propenone derivatives |
| FR2810322B1 (fr) | 2000-06-14 | 2006-11-10 | Pasteur Institut | PRODUCTION COMBINATOIRE D'ANALOGUES DE NUCLEOTIDES ET NUCLEOTIDES (XiTP) |
| UA72612C2 (en) | 2000-07-06 | 2005-03-15 | Pyrido[2.3-d]pyrimidine and pyrimido[4.5-d]pyrimidine nucleoside analogues, prodrugs and method for inhibiting growth of neoplastic cells | |
| US6617310B2 (en) | 2000-07-19 | 2003-09-09 | Bristol-Myers Squibb Pharma Company | Phosphate esters of bis-amino acid sulfonamides containing substituted benzyl amines |
| CZ304734B6 (cs) | 2000-07-21 | 2014-09-10 | Gilead Sciences, Inc. | Způsob přípravy 9-[2-(fosfonomethoxy)propyl]adeninu a 9-[2-(fosfonomethoxy)ethyl]adeninu |
| US6420586B1 (en) | 2000-08-15 | 2002-07-16 | University Of Kansas | Amino acid-derived cyclic phosphonamides and methods of synthesizing the same |
| WO2002048165A2 (en) | 2000-12-15 | 2002-06-20 | Pharmasset Ltd. | Antiviral agents for treatment of flaviviridae infections |
| WO2002057425A2 (en) | 2001-01-22 | 2002-07-25 | Merck & Co., Inc. | Nucleoside derivatives as inhibitors of rna-dependent rna viral polymerase |
| GB0114286D0 (en) | 2001-06-12 | 2001-08-01 | Hoffmann La Roche | Nucleoside Derivatives |
| KR20020097384A (ko) * | 2001-06-20 | 2002-12-31 | 미쯔비시 도꾜 세이야꾸 가부시끼가이샤 | 기존의 약제에 내성변이를 가지는 바이러스에 유효한 약제 |
| ATE371026T1 (de) | 2001-06-20 | 2007-09-15 | Nuevolution As | Eine methode zur synthese von matrizenabhängigen molekülen |
| WO2003028737A1 (en) | 2001-08-30 | 2003-04-10 | Mitsubishi Pharma Corporation | Anti-viral agents and in-vitro method for the identification of candidates able to inhibit binding of polymerase to epsilon |
| JP2005536440A (ja) * | 2001-09-28 | 2005-12-02 | イデニクス（ケイマン）リミテツド | ４’位が修飾されたヌクレオシドを使用するフラビウイルスおよびペスチウイルスの治療のための方法および組成物 |
| AU2002343556A1 (en) | 2001-12-07 | 2003-06-23 | Eli Lilly And Company | Use of phosphonate nucleotide analogue for treating hepatitis b virus infections |
| KR101016969B1 (ko) | 2001-12-21 | 2011-02-25 | 에이자이 아이엔씨. | 알콜 및 페놀의 수용성 포스포노옥시메틸 유도체를제조하는 방법 |
| JP4547911B2 (ja) | 2002-02-01 | 2010-09-22 | アリアド・ファーマシューティカルズ・インコーポレイテッド | リン含有化合物およびその用途 |
| EP1472230B1 (en) | 2002-02-08 | 2009-06-17 | Conforma Therapeutic Corporation | Ansamycins having improved pharmacological and biological properties |
| WO2003080078A1 (en) | 2002-03-18 | 2003-10-02 | Mitsubishi Pharma Corporation | Treatment of pre-core hepatitis b virus mutant infections |
| AU2003231765B9 (en) | 2002-04-26 | 2010-01-28 | Gilead Sciences, Inc. | Cellular accumulation of phosphonate analogs of HIV protease inhibitor compounds and the compounds as such |
| EA012844B1 (ru) * | 2003-02-19 | 2009-12-30 | Йельский Университет | Аналоги противовирусных нуклеозидов и способы лечения вирусных инфекций, в частности вич-инфекций |
| MXPA05011296A (es) | 2003-04-25 | 2006-01-24 | Gilead Sciences Inc | Conjugados de fosfonato inhibidores de la cinasa. |
| WO2005063751A1 (en) * | 2003-12-22 | 2005-07-14 | Gilead Sciences, Inc. | 4’-substituted carbovir-and abacavir-derivatives as well as related compounds with hiv and hcv antiviral activity |
-
2004
- 2004-12-22 WO PCT/US2004/043571 patent/WO2005063751A1/en not_active Ceased
- 2004-12-22 CN CNA2004800409747A patent/CN1906196A/zh active Pending
- 2004-12-22 US US10/583,573 patent/US20080287471A1/en not_active Abandoned
- 2004-12-22 JP JP2006547446A patent/JP2007515495A/ja active Pending
- 2004-12-22 AU AU2004309418A patent/AU2004309418B2/en not_active Ceased
- 2004-12-22 NZ NZ547907A patent/NZ547907A/en not_active IP Right Cessation
- 2004-12-22 DE DE602004019815T patent/DE602004019815D1/de not_active Expired - Lifetime
- 2004-12-22 KR KR1020067014835A patent/KR20060127906A/ko not_active Ceased
- 2004-12-22 MX MXPA06006899A patent/MXPA06006899A/es active IP Right Grant
- 2004-12-22 EP EP04815605A patent/EP1706405B1/en not_active Expired - Lifetime
- 2004-12-22 US US11/020,641 patent/US7432272B2/en not_active Expired - Fee Related
- 2004-12-22 CA CA002548753A patent/CA2548753A1/en not_active Abandoned
- 2004-12-22 BR BRPI0417988-9A patent/BRPI0417988A/pt not_active IP Right Cessation
- 2004-12-22 AT AT04815605T patent/ATE424400T1/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| US20080287471A1 (en) | 2008-11-20 |
| AU2004309418A1 (en) | 2005-07-14 |
| AU2004309418B2 (en) | 2012-01-19 |
| CN1906196A (zh) | 2007-01-31 |
| JP2007515495A (ja) | 2007-06-14 |
| NZ547907A (en) | 2010-07-30 |
| EP1706405A1 (en) | 2006-10-04 |
| ATE424400T1 (de) | 2009-03-15 |
| KR20060127906A (ko) | 2006-12-13 |
| US7432272B2 (en) | 2008-10-07 |
| MXPA06006899A (es) | 2006-09-04 |
| WO2005063751A1 (en) | 2005-07-14 |
| EP1706405B1 (en) | 2009-03-04 |
| BRPI0417988A (pt) | 2007-04-27 |
| DE602004019815D1 (de) | 2009-04-16 |
| US20050222180A1 (en) | 2005-10-06 |
| HK1094892A1 (en) | 2007-04-13 |
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