AP902A - Furan and thiophenenecarbothioamide derivatives, their preparation and their use as inhibitors of the replication of HIV-1 and HIV-1 mutants - Google Patents
Furan and thiophenenecarbothioamide derivatives, their preparation and their use as inhibitors of the replication of HIV-1 and HIV-1 mutants Download PDFInfo
- Publication number
- AP902A AP902A APAP/P/1998/001245A AP9801245A AP902A AP 902 A AP902 A AP 902A AP 9801245 A AP9801245 A AP 9801245A AP 902 A AP902 A AP 902A
- Authority
- AP
- ARIPO
- Prior art keywords
- hiv
- methyl
- compound
- reaction mixture
- recited
- Prior art date
Links
- 241000713772 Human immunodeficiency virus 1 Species 0.000 title claims abstract description 35
- 230000010076 replication Effects 0.000 title claims abstract description 11
- 238000002360 preparation method Methods 0.000 title description 13
- 239000003112 inhibitor Substances 0.000 title description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 57
- 238000000034 method Methods 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 10
- 239000003937 drug carrier Substances 0.000 claims description 7
- 208000031886 HIV Infections Diseases 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims 6
- 238000004519 manufacturing process Methods 0.000 claims 6
- 239000000126 substance Substances 0.000 claims 6
- 102100034343 Integrase Human genes 0.000 abstract description 16
- 108010092799 RNA-directed DNA polymerase Proteins 0.000 abstract description 16
- 208000030507 AIDS Diseases 0.000 abstract description 5
- 238000000338 in vitro Methods 0.000 abstract description 3
- 230000005764 inhibitory process Effects 0.000 abstract description 3
- 201000010099 disease Diseases 0.000 abstract description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 2
- 238000001727 in vivo Methods 0.000 abstract description 2
- 238000011321 prophylaxis Methods 0.000 abstract description 2
- 208000011580 syndromic disease Diseases 0.000 abstract description 2
- 230000001225 therapeutic effect Effects 0.000 abstract description 2
- -1 ester compounds Chemical class 0.000 description 50
- 239000011541 reaction mixture Substances 0.000 description 37
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
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- 239000000243 solution Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
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- 230000000840 anti-viral effect Effects 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
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- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 3
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- 230000002939 deleterious effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
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- 239000000758 substrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
-
- 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
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Virology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- AIDS & HIV (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/565,493 US5696151A (en) | 1995-11-30 | 1995-11-30 | Compounds useful for the inhibition of the replication of HIV-1 and HIV-1 mutants |
| PCT/US1996/018394 WO1997019940A1 (en) | 1995-11-30 | 1996-11-15 | Furan- and thiophenecarbothioamide derivatives, their preparation and their use as inhibitors of the replication of hiv-1 and hiv-1 mutants |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AP9801245A0 AP9801245A0 (en) | 1998-06-30 |
| AP902A true AP902A (en) | 2000-11-23 |
Family
ID=24258853
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| APAP/P/1998/001245A AP902A (en) | 1995-11-30 | 1996-11-15 | Furan and thiophenenecarbothioamide derivatives, their preparation and their use as inhibitors of the replication of HIV-1 and HIV-1 mutants |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US5696151A (de) |
| EP (1) | EP0874839B1 (de) |
| JP (1) | JP3027771B2 (de) |
| KR (1) | KR100505841B1 (de) |
| CN (1) | CN1098847C (de) |
| AP (1) | AP902A (de) |
| AT (1) | ATE224382T1 (de) |
| AU (1) | AU704086B2 (de) |
| BR (1) | BR9611838A (de) |
| CA (1) | CA2237194C (de) |
| DE (1) | DE69623819T2 (de) |
| DK (1) | DK0874839T3 (de) |
| ES (1) | ES2183986T3 (de) |
| HU (1) | HU223660B1 (de) |
| NZ (1) | NZ324118A (de) |
| OA (1) | OA10864A (de) |
| PT (1) | PT874839E (de) |
| TW (1) | TW448169B (de) |
| WO (1) | WO1997019940A1 (de) |
| ZA (1) | ZA969490B (de) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6017947A (en) * | 1999-09-17 | 2000-01-25 | Brouwer; Walter Gerhard | Heterocyclic carbodithioperoxyimidic compounds useful for the inhibition of the replication of HIV |
| US6143780A (en) * | 1999-09-17 | 2000-11-07 | Uniroyal Chemical Company, Inc. | N-arylmethylthioanilide compounds useful for the inhibition of the replication of HIV |
| US6498254B1 (en) * | 2001-10-29 | 2002-12-24 | Uniroyal Chemical Company, Inc. | Antiretroviral compounds and compositions |
| US7064139B2 (en) * | 2001-10-29 | 2006-06-20 | Uniroyal Chemical Company, Inc. | Method for treating retroviral infections |
| DE102008015033A1 (de) | 2008-03-17 | 2009-09-24 | Aicuris Gmbh & Co. Kg | Substituierte (Pyrazolyl-carbonyl)imidazolidinone und ihre Verwendung |
| DE102008015032A1 (de) | 2008-03-17 | 2009-09-24 | Aicuris Gmbh & Co. Kg | Substituierte Pyrazolamide und ihre Verwendung |
| DE102008062863A1 (de) | 2008-12-17 | 2010-06-24 | Aicuris Gmbh & Co. Kg | Substituierte (Thiophenyl-carbonyl)imidazolidinone und ihre Verwendung |
| DE102008062878A1 (de) | 2008-12-17 | 2010-06-24 | Aicuris Gmbh & Co. Kg | Substituierte Furancarboxamide und ihre Verwendung |
| CN101987842A (zh) * | 2009-07-31 | 2011-03-23 | 上海开拓者医药发展有限公司 | 一种2-甲基噻吩衍生物的制备方法 |
| US10246420B2 (en) | 2014-07-24 | 2019-04-02 | Bayer Cropscience Aktiengesellschaft | Pyrazole derivatives |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991005761A1 (en) * | 1989-10-16 | 1991-05-02 | Uniroyal Chemical Ltd./Uniroyal Chemical Ltee | Treatment of hiv infections and compounds useful therein |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5968910A (en) * | 1994-11-30 | 1999-10-19 | Jan M. R. Balzarini | Compositions containing two or three inhibitors of different HIV reverse transcriptases |
-
1995
- 1995-11-30 US US08/565,493 patent/US5696151A/en not_active Expired - Lifetime
-
1996
- 1996-11-08 TW TW085113662A patent/TW448169B/zh not_active IP Right Cessation
- 1996-11-12 ZA ZA969490A patent/ZA969490B/xx unknown
- 1996-11-15 AT AT96942010T patent/ATE224382T1/de active
- 1996-11-15 AU AU11199/97A patent/AU704086B2/en not_active Expired
- 1996-11-15 JP JP9520533A patent/JP3027771B2/ja not_active Expired - Lifetime
- 1996-11-15 CN CN96198705A patent/CN1098847C/zh not_active Expired - Lifetime
- 1996-11-15 CA CA002237194A patent/CA2237194C/en not_active Expired - Lifetime
- 1996-11-15 EP EP96942010A patent/EP0874839B1/de not_active Expired - Lifetime
- 1996-11-15 DK DK96942010T patent/DK0874839T3/da active
- 1996-11-15 KR KR10-1998-0703958A patent/KR100505841B1/ko not_active Expired - Lifetime
- 1996-11-15 NZ NZ324118A patent/NZ324118A/xx not_active IP Right Cessation
- 1996-11-15 BR BR9611838A patent/BR9611838A/pt active Search and Examination
- 1996-11-15 ES ES96942010T patent/ES2183986T3/es not_active Expired - Lifetime
- 1996-11-15 PT PT96942010T patent/PT874839E/pt unknown
- 1996-11-15 WO PCT/US1996/018394 patent/WO1997019940A1/en not_active Ceased
- 1996-11-15 AP APAP/P/1998/001245A patent/AP902A/en active
- 1996-11-15 HU HU9901990A patent/HU223660B1/hu active IP Right Grant
- 1996-11-15 DE DE69623819T patent/DE69623819T2/de not_active Expired - Lifetime
-
1998
- 1998-05-29 OA OA9800070A patent/OA10864A/en unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991005761A1 (en) * | 1989-10-16 | 1991-05-02 | Uniroyal Chemical Ltd./Uniroyal Chemical Ltee | Treatment of hiv infections and compounds useful therein |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2237194A1 (en) | 1997-06-05 |
| ZA969490B (en) | 1997-06-02 |
| ATE224382T1 (de) | 2002-10-15 |
| JPH11504657A (ja) | 1999-04-27 |
| CN1098847C (zh) | 2003-01-15 |
| DE69623819D1 (de) | 2002-10-24 |
| KR19990071682A (ko) | 1999-09-27 |
| NZ324118A (en) | 1999-02-25 |
| OA10864A (en) | 2003-02-18 |
| CA2237194C (en) | 2006-06-13 |
| JP3027771B2 (ja) | 2000-04-04 |
| US5696151A (en) | 1997-12-09 |
| HUP9901990A2 (en) | 2000-07-28 |
| AU704086B2 (en) | 1999-04-15 |
| DE69623819T2 (de) | 2003-05-28 |
| TW448169B (en) | 2001-08-01 |
| BR9611838A (pt) | 1999-03-09 |
| HU223660B1 (hu) | 2004-11-29 |
| DK0874839T3 (da) | 2003-01-27 |
| KR100505841B1 (ko) | 2005-12-14 |
| HUP9901990A3 (en) | 2000-08-28 |
| AP9801245A0 (en) | 1998-06-30 |
| EP0874839A1 (de) | 1998-11-04 |
| ES2183986T3 (es) | 2003-04-01 |
| PT874839E (pt) | 2003-02-28 |
| AU1119997A (en) | 1997-06-19 |
| EP0874839B1 (de) | 2002-09-18 |
| WO1997019940A1 (en) | 1997-06-05 |
| CN1203596A (zh) | 1998-12-30 |
| HK1016601A1 (en) | 1999-11-05 |
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