DE602004019815D1 - 4'-substituierte carbovir- und abacavir-derivate sowie verwandte verbindungen mit hiv- und hcv-antiviraler wirkung - Google Patents
4'-substituierte carbovir- und abacavir-derivate sowie verwandte verbindungen mit hiv- und hcv-antiviraler wirkungInfo
- Publication number
- DE602004019815D1 DE602004019815D1 DE602004019815T DE602004019815T DE602004019815D1 DE 602004019815 D1 DE602004019815 D1 DE 602004019815D1 DE 602004019815 T DE602004019815 T DE 602004019815T DE 602004019815 T DE602004019815 T DE 602004019815T DE 602004019815 D1 DE602004019815 D1 DE 602004019815D1
- Authority
- DE
- Germany
- Prior art keywords
- sup
- alkyl
- carbovir
- abacavir
- hiv
- 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.)
- Active
Links
- 150000001875 compounds Chemical class 0.000 title abstract 4
- 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
- MCGSCOLBFJQGHM-SCZZXKLOSA-N abacavir Chemical class C=12N=CN([C@H]3C=C[C@@H](CO)C3)C2=NC(N)=NC=1NC1CC1 MCGSCOLBFJQGHM-SCZZXKLOSA-N 0.000 title 1
- 230000000840 anti-viral effect Effects 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N 4-methyl-1h-indole Chemical compound CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 abstract 2
- PEHVGBZKEYRQSX-UHFFFAOYSA-N 7-deaza-adenine Chemical group NC1=NC=NC2=C1C=CN2 PEHVGBZKEYRQSX-UHFFFAOYSA-N 0.000 abstract 2
- LOSIULRWFAEMFL-UHFFFAOYSA-N 7-deazaguanine Chemical group O=C1NC(N)=NC2=C1CC=N2 LOSIULRWFAEMFL-UHFFFAOYSA-N 0.000 abstract 2
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical group O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000000304 alkynyl group Chemical group 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- FDGQSTZJBFJUBT-UHFFFAOYSA-N hypoxanthine Chemical compound O=C1NC=NC2=C1NC=N2 FDGQSTZJBFJUBT-UHFFFAOYSA-N 0.000 abstract 2
- DRAVOWXCEBXPTN-UHFFFAOYSA-N isoguanine Chemical compound NC1=NC(=O)NC2=C1NC=N2 DRAVOWXCEBXPTN-UHFFFAOYSA-N 0.000 abstract 2
- RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical group CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 abstract 2
- WYWHKKSPHMUBEB-UHFFFAOYSA-N tioguanine Chemical compound N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 abstract 2
- QUKPALAWEPMWOS-UHFFFAOYSA-N 1h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=NC=C2C=NNC2=N1 QUKPALAWEPMWOS-UHFFFAOYSA-N 0.000 abstract 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
- XQCZBXHVTFVIFE-UHFFFAOYSA-N 2-amino-4-hydroxypyrimidine Chemical class NC1=NC=CC(O)=N1 XQCZBXHVTFVIFE-UHFFFAOYSA-N 0.000 abstract 1
- MWBWWFOAEOYUST-UHFFFAOYSA-N 2-aminopurine Chemical compound NC1=NC=C2N=CNC2=N1 MWBWWFOAEOYUST-UHFFFAOYSA-N 0.000 abstract 1
- HCGYMSSYSAKGPK-UHFFFAOYSA-N 2-nitro-1h-indole Chemical compound C1=CC=C2NC([N+](=O)[O-])=CC2=C1 HCGYMSSYSAKGPK-UHFFFAOYSA-N 0.000 abstract 1
- FTBBGQKRYUTLMP-UHFFFAOYSA-N 2-nitro-1h-pyrrole Chemical compound [O-][N+](=O)C1=CC=CN1 FTBBGQKRYUTLMP-UHFFFAOYSA-N 0.000 abstract 1
- OVONXEQGWXGFJD-UHFFFAOYSA-N 4-sulfanylidene-1h-pyrimidin-2-one Chemical compound SC=1C=CNC(=O)N=1 OVONXEQGWXGFJD-UHFFFAOYSA-N 0.000 abstract 1
- NBAKTGXDIBVZOO-UHFFFAOYSA-N 5,6-dihydrothymine Chemical compound CC1CNC(=O)NC1=O NBAKTGXDIBVZOO-UHFFFAOYSA-N 0.000 abstract 1
- GSPMCUUYNASDHM-UHFFFAOYSA-N 5-methyl-4-sulfanylidene-1h-pyrimidin-2-one Chemical compound CC1=CNC(=O)N=C1S GSPMCUUYNASDHM-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
- LHCPRYRLDOSKHK-UHFFFAOYSA-N 7-deaza-8-aza-adenine Chemical compound NC1=NC=NC2=C1C=NN2 LHCPRYRLDOSKHK-UHFFFAOYSA-N 0.000 abstract 1
- 229960005508 8-azaguanine Drugs 0.000 abstract 1
- MSSXOMSJDRHRMC-UHFFFAOYSA-N 9H-purine-2,6-diamine Chemical compound NC1=NC(N)=C2NC=NC2=N1 MSSXOMSJDRHRMC-UHFFFAOYSA-N 0.000 abstract 1
- 229930024421 Adenine Natural products 0.000 abstract 1
- UGQMRVRMYYASKQ-UHFFFAOYSA-N Hypoxanthine nucleoside Natural products OC1C(O)C(CO)OC1N1C(NC=NC2=O)=C2N=C1 UGQMRVRMYYASKQ-UHFFFAOYSA-N 0.000 abstract 1
- 229930010555 Inosine Natural products 0.000 abstract 1
- 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 abstract 1
- MRWXACSTFXYYMV-UHFFFAOYSA-N Nebularine Natural products OC1C(O)C(CO)OC1N1C2=NC=NC=C2N=C1 MRWXACSTFXYYMV-UHFFFAOYSA-N 0.000 abstract 1
- 229930185560 Pseudouridine Natural products 0.000 abstract 1
- PTJWIQPHWPFNBW-UHFFFAOYSA-N Pseudouridine C Natural products OC1C(O)C(CO)OC1C1=CNC(=O)NC1=O PTJWIQPHWPFNBW-UHFFFAOYSA-N 0.000 abstract 1
- 241000700605 Viruses Species 0.000 abstract 1
- 229960000643 adenine Drugs 0.000 abstract 1
- GFFGJBXGBJISGV-UHFFFAOYSA-N adenyl group Chemical group N1=CN=C2N=CNC2=C1N GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 abstract 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 abstract 1
- WGDUUQDYDIIBKT-UHFFFAOYSA-N beta-Pseudouridine Natural products OC1OC(CN2C=CC(=O)NC2=O)C(O)C1O WGDUUQDYDIIBKT-UHFFFAOYSA-N 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 229940104302 cytosine Drugs 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 208000015181 infectious disease Diseases 0.000 abstract 1
- 230000002458 infectious effect Effects 0.000 abstract 1
- 229960003786 inosine Drugs 0.000 abstract 1
- 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 abstract 1
- 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 abstract 1
- HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical compound SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000012453 solvate Substances 0.000 abstract 1
- 229940113082 thymine Drugs 0.000 abstract 1
- 229960003087 tioguanine Drugs 0.000 abstract 1
- 150000003852 triazoles Chemical class 0.000 abstract 1
- 229940035893 uracil Drugs 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)
- Virology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53225603P | 2003-12-22 | 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 |
|---|---|
| DE602004019815D1 true DE602004019815D1 (de) | 2009-04-16 |
Family
ID=34738778
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE602004019815T Active DE602004019815D1 (de) | 2003-12-22 | 2004-12-22 | 4'-substituierte carbovir- und abacavir-derivate sowie verwandte verbindungen mit hiv- und hcv-antiviraler wirkung |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US20080287471A1 (de) |
| EP (1) | EP1706405B1 (de) |
| JP (1) | JP2007515495A (de) |
| KR (1) | KR20060127906A (de) |
| CN (1) | CN1906196A (de) |
| AT (1) | ATE424400T1 (de) |
| AU (1) | AU2004309418B2 (de) |
| BR (1) | BRPI0417988A (de) |
| CA (1) | CA2548753A1 (de) |
| DE (1) | DE602004019815D1 (de) |
| HK (1) | HK1094892A1 (de) |
| MX (1) | MXPA06006899A (de) |
| NZ (1) | NZ547907A (de) |
| WO (1) | WO2005063751A1 (de) |
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 |
| US7429565B2 (en) | 2003-04-25 | 2008-09-30 | Gilead Sciences, Inc. | Antiviral phosphonate analogs |
| KR20060127906A (ko) * | 2003-12-22 | 2006-12-13 | 길리애드 사이언시즈, 인코포레이티드 | 4'-치환된 카보버와 아바카비어 유도체 및 ｈｉｖ와 ｈｃｖ항바이러스 활성을 갖는 관련 화합물 |
| SI2258376T1 (sl) | 2004-07-27 | 2019-04-30 | Gilead Sciences, Inc. | Analogi fosfonata spojin inhibitorjev HIV |
| BRPI0713680A2 (pt) | 2006-06-22 | 2012-10-23 | Anadys Pharmaceuticals Inc | composto, composição farmacêutica e métodos de modulação das atividades imuno da citocina, de tratamento de infecção de vìrus da hepatite c em paciente e de tratamento de desordem de proliferação relacionada em mamìfero carecido do mesmo |
| EP2085397A1 (de) * | 2008-01-21 | 2009-08-05 | Esteve Quimica, S.A. | Kristalline Form von Abacavir |
| BRPI0915878A2 (pt) | 2008-07-08 | 2015-11-03 | Gilead Sciences Inc | sais ou hidratos de compostos inibidores de hiv, seu uso e composição farmacêutica que os compreende |
| 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 |
| EP2776405A1 (de) | 2011-11-11 | 2014-09-17 | Pfizer Inc | 2-thiopyrimidinone |
| BR112017013858A2 (pt) | 2014-12-26 | 2018-02-27 | Univ Emory | n4-hidroxicitidina e derivados e usos antivirais relacionados aos mesmos |
| BR112017022340A2 (pt) | 2015-05-05 | 2018-07-10 | Pfizer | 2-tiopirimidinonas |
| EP3661937B1 (de) | 2017-08-01 | 2021-07-28 | Gilead Sciences, Inc. | Kristalline formen von ethyl ((s)-((((2r,5r)-5-(6-amino-9h-purin-9-yl)-4-fluoro-2,5-dihydrofuran-2-yl)oxy)methyl)(phenoxy)phosphoryl)-l-alaninat (gs-9131) zur behandlung von viralen infektionen |
| WO2019113462A1 (en) | 2017-12-07 | 2019-06-13 | Emory University | N4-hydroxycytidine and derivatives and anti-viral uses related thereto |
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| US5631370A (en) * | 1988-01-20 | 1997-05-20 | Regents Of The University Of Minnesota | Optically-active isomers of dideoxycarbocyclic nucleosides |
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| EP1295879A4 (de) | 2000-06-13 | 2004-04-14 | Shionogi & Co | Medizinische zusammensetzungen die propenonderivate enthalten |
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| CN1527836A (zh) | 2000-12-15 | 2004-09-08 | 用于治疗黄病毒科病毒感染的抗病毒剂 | |
| EP1355916B1 (de) | 2001-01-22 | 2007-01-10 | Merck & Co., Inc. | Nukleosidderivate als inhibitoren von rna-abhängiger rna viralpolymerase |
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-
2004
- 2004-12-22 KR KR1020067014835A patent/KR20060127906A/ko not_active Application Discontinuation
- 2004-12-22 WO PCT/US2004/043571 patent/WO2005063751A1/en active Application Filing
- 2004-12-22 NZ NZ547907A patent/NZ547907A/en not_active IP Right Cessation
- 2004-12-22 CN CNA2004800409747A patent/CN1906196A/zh active Pending
- 2004-12-22 AT AT04815605T patent/ATE424400T1/de not_active IP Right Cessation
- 2004-12-22 US US10/583,573 patent/US20080287471A1/en not_active Abandoned
- 2004-12-22 EP EP04815605A patent/EP1706405B1/de not_active Not-in-force
- 2004-12-22 CA CA002548753A patent/CA2548753A1/en not_active Abandoned
- 2004-12-22 MX MXPA06006899A patent/MXPA06006899A/es active IP Right Grant
- 2004-12-22 BR BRPI0417988-9A patent/BRPI0417988A/pt not_active IP Right Cessation
- 2004-12-22 JP JP2006547446A patent/JP2007515495A/ja active Pending
- 2004-12-22 US US11/020,641 patent/US7432272B2/en not_active Expired - Fee Related
- 2004-12-22 AU AU2004309418A patent/AU2004309418B2/en not_active Ceased
- 2004-12-22 DE DE602004019815T patent/DE602004019815D1/de active Active
-
2007
- 2007-03-02 HK HK07102385.2A patent/HK1094892A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| HK1094892A1 (en) | 2007-04-13 |
| WO2005063751A1 (en) | 2005-07-14 |
| US7432272B2 (en) | 2008-10-07 |
| ATE424400T1 (de) | 2009-03-15 |
| KR20060127906A (ko) | 2006-12-13 |
| AU2004309418A1 (en) | 2005-07-14 |
| US20050222180A1 (en) | 2005-10-06 |
| CA2548753A1 (en) | 2005-07-14 |
| JP2007515495A (ja) | 2007-06-14 |
| BRPI0417988A (pt) | 2007-04-27 |
| AU2004309418B2 (en) | 2012-01-19 |
| MXPA06006899A (es) | 2006-09-04 |
| NZ547907A (en) | 2010-07-30 |
| EP1706405A1 (de) | 2006-10-04 |
| EP1706405B1 (de) | 2009-03-04 |
| US20080287471A1 (en) | 2008-11-20 |
| CN1906196A (zh) | 2007-01-31 |
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