RU92016592A - HIV INHIBITING BENZOLACETAMIDE DERIVATIVES - Google Patents
HIV INHIBITING BENZOLACETAMIDE DERIVATIVESInfo
- Publication number
- RU92016592A RU92016592A RU92016592/04A RU92016592A RU92016592A RU 92016592 A RU92016592 A RU 92016592A RU 92016592/04 A RU92016592/04 A RU 92016592/04A RU 92016592 A RU92016592 A RU 92016592A RU 92016592 A RU92016592 A RU 92016592A
- Authority
- RU
- Russia
- Prior art keywords
- alkyl
- hydrogen
- carbonyl
- independently
- benzolacetamide
- Prior art date
Links
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical class NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 title 1
- 241000580858 Simian-Human immunodeficiency virus Species 0.000 title 1
- 230000002401 inhibitory effect Effects 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- -1 cyano, aminomethyl Chemical group 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical group O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 229910052717 sulfur Chemical group 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- YKYIFUROKBDHCY-ONEGZZNKSA-N (E)-4-ethoxy-1,1,1-trifluorobut-3-en-2-one Chemical group CCO\C=C\C(=O)C(F)(F)F YKYIFUROKBDHCY-ONEGZZNKSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 125000005189 alkyl hydroxy group Chemical group 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drugs Drugs 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 150000002829 nitrogen Chemical group 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 150000003839 salts Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Claims (1)
фармацевтически приемлемой кислотно-аддитивной солевой формы или ее стереохимически изомерной формы, в которой R1 и R2 каждый независимо являются водородом, C1 - 6 алкилом или C3 - 6 циклоалкилом; или R1 или R2 вместе с атомом азота, к которому присоединены названные R1 и R2 могут образовывать пирролидинил, пиперидинил, морфолинил, пиперазинил или 4-C1 - 4 алкилпиперазинильную группу; X является кислородом или серой; R3 является водородом или C1 - 6 алкилом; R4, R5 и R6 каждый независимо друг от друга являются водородом, галогеном, C1 - 6 алкилом, C1 - 6 алкилокси, нитро, трифторметилом, циано, аминометилом, циано, аминометилом, карбоксилом, C1 - 4 алкилоксикарбонилом, C1 - 4 алкил-карбонилом, аминокарбонилом или гидрокси-группой; R7 представляет собой водород или галоид; а R8, R9 и R1 0 каждый независимо друг от друга являются водородом, галоидом, C1 - 6 алкилом, C1 - 6 алкокси, нитро, гидрокси, трифторметокси, 2,2,2-трифторэтокси, (трифторметил) карбонилом, аминокарбонилом, (циклопропил) карбонилом или радикалом C1 - 6 алкил-(C=Y)-, где = Y представляет собой =O, =N -OH, =N -OCH3, = N - NH2 или = N - N(CH3)2 при условии, что (I) R1 не является н-пропилом, когда R2, R3, R4, R5, R6, R7, R9 и R1 0 являются водородом, R8 представляет собой 4-этокси и X представляет собой кислород и (2) X не является серой, когда R1, R2, R3, R6, R7, R8, R9 и R1 0 представляют собой водород, а R4 и R5 представляют 3,4-диметокси-группу. Описываются новые соединения, фармацевтические композиции, содержащие названные соединения формулы (I) и процессы получения названных композиций.Compound for use as a drug, having the formula
pharmaceutically acceptable acid addition salt form or a stereochemically isomeric form thereof, wherein R 1 and R 2 each independently are hydrogen, C 1 - 6 alkyl or C 3 - 6 cycloalkyl; or R 1 or R 2 together with the nitrogen atom to which they are attached mentioned R 1 and R 2 may form a pyrrolidinyl, piperidinyl, morpholinyl, piperazinyl or 4-C 1 - 4 alkyl-piperazinyl group; X is oxygen or sulfur; R 3 is hydrogen or C 1 - 6 alkyl; R 4, R 5 and R 6 are each independently of one another are hydrogen, halogen, C 1 - 6 alkyl, C 1 - 6 alkyloxy, nitro, trifluoromethyl, cyano, aminomethyl, cyano, aminomethyl, carboxyl, C 1 - 4 alkyloxycarbonyl, C 1 - 4 alkyl-carbonyl, aminocarbonyl or hydroxy; R 7 is hydrogen or halo; and R 8, R 9 and R 1 0 are each independently of one another are hydrogen, halogen, C 1 - 6 alkyl, C 1 - 6 alkoxy, nitro, hydroxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, (trifluoromethyl) carbonyl, , aminocarbonyl, (cyclopropyl) carbonyl or C 1 - 6 alkyl- (C = Y) - radical, where = Y represents a = O, = N-OH, = N-OCH 3 , = N - NH 2 or = N - N (CH 3 ) 2 with the proviso that (I) R 1 is not n-propyl when R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 9 and R 1 0 are hydrogen, R 8 represents 4-ethoxy and X represents oxygen and (2) X is not sulfur when R 1 , R 2 , R 3 , R 6 , R 7 , R 8 , R 9 and R 1 0 are water is hydrogen, and R 4 and R 5 are 3,4-dimethoxy. Describes new compounds, pharmaceutical compositions containing the compounds of formula (I) and the processes for the preparation of these compositions.
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP90201857 | 1990-07-10 | ||
| EP90.201857.1 | 1990-07-10 | ||
| EP90.201.857.1 | 1990-07-10 | ||
| EP91.200646.1 | 1991-03-22 | ||
| EP91.200.646.7 | 1991-03-22 | ||
| EP91200646 | 1991-03-22 | ||
| PCT/EP1991/001254 WO1992000952A1 (en) | 1990-07-10 | 1991-07-04 | Hiv-inhibiting benzeneacetamide derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU92016592A true RU92016592A (en) | 1995-03-27 |
| RU2087465C1 RU2087465C1 (en) | 1997-08-20 |
Family
ID=26125946
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU9192016592A RU2087465C1 (en) | 1990-07-10 | 1991-07-04 | Benseneacetamide derivative, methods of preparation thereof, and pharmaceutical composition |
Country Status (42)
| Country | Link |
|---|---|
| US (2) | US5556886A (en) |
| EP (1) | EP0538301B1 (en) |
| JP (1) | JPH0819068B2 (en) |
| KR (1) | KR0183446B1 (en) |
| CN (2) | CN1028990C (en) |
| AP (1) | AP311A (en) |
| AT (1) | ATE144765T1 (en) |
| AU (1) | AU643056B2 (en) |
| BG (1) | BG61809B1 (en) |
| CA (1) | CA2084508A1 (en) |
| CZ (1) | CZ279901B6 (en) |
| DE (1) | DE69122963T2 (en) |
| DK (1) | DK0538301T3 (en) |
| DZ (1) | DZ1514A1 (en) |
| ES (1) | ES2095942T3 (en) |
| FI (1) | FI930070A (en) |
| GR (1) | GR3021829T3 (en) |
| HR (1) | HRP930485A2 (en) |
| HU (2) | HUT64013A (en) |
| IE (1) | IE75693B1 (en) |
| IL (3) | IL98756A (en) |
| LT (1) | LT3602B (en) |
| LV (1) | LV10086B (en) |
| MA (1) | MA22208A1 (en) |
| MX (1) | MX9100100A (en) |
| MY (1) | MY108580A (en) |
| NO (1) | NO303777B1 (en) |
| NZ (1) | NZ238763A (en) |
| OA (1) | OA09770A (en) |
| PH (1) | PH30977A (en) |
| PL (1) | PL167076B1 (en) |
| PT (1) | PT98259B (en) |
| RO (1) | RO112855B1 (en) |
| RU (1) | RU2087465C1 (en) |
| SG (1) | SG48829A1 (en) |
| SI (1) | SI9111204A (en) |
| SK (1) | SK279639B6 (en) |
| TN (1) | TNSN91056A1 (en) |
| TW (1) | TW204337B (en) |
| WO (1) | WO1992000952A1 (en) |
| YU (1) | YU120491A (en) |
| ZA (1) | ZA915334B (en) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69217992T2 (en) * | 1991-12-30 | 1997-06-12 | Janssen Pharmaceutica Nv | ALPHA-SUBSTITUTED PETROL METHANAMINE DERIVATIVES |
| US6177435B1 (en) | 1992-05-13 | 2001-01-23 | Glaxo Wellcome Inc. | Therapeutic combinations |
| DK0577945T3 (en) * | 1992-07-06 | 1996-09-02 | American Cyanamid Co | The herbicide intermediate o-nitrophenyl-cyclopropyl ketone and process for its preparation |
| DE69418312D1 (en) * | 1993-02-22 | 1999-06-10 | Janssen Pharmaceutica Nv | REMOVING THE RESISTANCE OF HIV-1 LINES TO ZIDOVUDINE |
| US5767310A (en) * | 1993-03-19 | 1998-06-16 | Merck & Co., Inc. | Phenoxyphenylacetic acid derivatives |
| US5686478A (en) * | 1993-07-20 | 1997-11-11 | Merck & Co. Inc. | Endothelin antagonists |
| GB9403449D0 (en) * | 1994-02-23 | 1994-04-13 | Wellcome Found | Therapeutic benzonitriles |
| GB9403408D0 (en) * | 1994-02-23 | 1994-04-13 | Wellcome Found | Therapeutic benzonitriles |
| IL112739A0 (en) * | 1994-02-23 | 1995-05-26 | Wellcome Found | Ayrlthiobenzonitrile compounds, their preparation and pharmaceutical compositions containing them |
| US5559135A (en) * | 1994-09-14 | 1996-09-24 | Merck & Co., Inc. | Endothelin antagonists bearing pyridyl amides |
| US5538991A (en) * | 1994-09-14 | 1996-07-23 | Merck & Co., Inc. | Endothelin antagonists bearing 5-membered heterocyclic amides |
| EP0872233A1 (en) * | 1997-04-14 | 1998-10-21 | Janssen Pharmaceutica N.V. | Antiretroviral compositions with improved bioavailability |
| WO1999065871A2 (en) * | 1998-06-19 | 1999-12-23 | The Government Of The United States Of America Represented By The Secretary, Department Of Health And Human Services | Thiolesters and uses thereof |
| NZ517025A (en) | 1999-09-24 | 2003-07-25 | Janssen Pharmaceutica Nv | Antiviral compositions |
| JP4713026B2 (en) * | 2000-08-11 | 2011-06-29 | 日本たばこ産業株式会社 | Calcium receptor antagonist |
| EP1308436B1 (en) | 2000-08-11 | 2008-10-15 | Japan Tobacco Inc. | Calcium receptor antagonists |
| US7625949B2 (en) | 2004-04-23 | 2009-12-01 | Roche Palo Alto Llc | Methods for treating retroviral infections |
| JP4810529B2 (en) * | 2004-04-23 | 2011-11-09 | エフ．ホフマン−ラ ロシュ アーゲー | Non-nucleoside reverse transcriptase inhibitors |
| CN101500993A (en) * | 2006-06-08 | 2009-08-05 | 百时美施贵宝公司 | 2-aminocarbonylphenylamino-2-phenilacetamides as factor VIIa inhibitors useful as anticoagulants |
| RU2449985C2 (en) * | 2010-03-31 | 2012-05-10 | Федеральное государственное унитарное предприятие "Российский научный центр "Прикладная химия" | Method of producing n,n-dimethylacetamide |
| CN102675212B (en) * | 2012-05-09 | 2014-11-05 | 昆明理工大学 | N-substituted phenyl-2-((1H-benzimidazole-2-group) sulfydryl) amides derivatives and usage thereof |
| CN104000807B (en) * | 2014-05-28 | 2016-05-18 | 中山大学 | Phenyl-amides compound is in the application of preparing in anti-HIV-1 virus drugs |
| CN105367437B (en) * | 2015-10-12 | 2017-08-01 | 湖北文理学院 | A kind of preparation method of 2 fragrant amino acetamides |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1423430A (en) * | 1973-03-29 | 1976-02-04 | Wyeth John & Brother Ltd | Thioamides |
| US4246429A (en) * | 1978-06-23 | 1981-01-20 | Janssen Pharmaceutica, N.V. | Novel α-amino-phenylacetic acid derivatives |
| CH637828A5 (en) * | 1978-11-15 | 1983-08-31 | Koehler Franz Dr Chemie Kg | Cytostatics |
| DE69217992T2 (en) * | 1991-12-30 | 1997-06-12 | Janssen Pharmaceutica Nv | ALPHA-SUBSTITUTED PETROL METHANAMINE DERIVATIVES |
-
1991
- 1991-06-25 IE IE220891A patent/IE75693B1/en not_active IP Right Cessation
- 1991-06-26 AP APAP/P/1991/000288A patent/AP311A/en active
- 1991-06-27 NZ NZ238763A patent/NZ238763A/en unknown
- 1991-07-02 PH PH42728A patent/PH30977A/en unknown
- 1991-07-02 MY MYPI91001206A patent/MY108580A/en unknown
- 1991-07-04 DK DK91912334.9T patent/DK0538301T3/en active
- 1991-07-04 EP EP91912334A patent/EP0538301B1/en not_active Expired - Lifetime
- 1991-07-04 CA CA002084508A patent/CA2084508A1/en not_active Abandoned
- 1991-07-04 DE DE69122963T patent/DE69122963T2/en not_active Expired - Fee Related
- 1991-07-04 WO PCT/EP1991/001254 patent/WO1992000952A1/en active IP Right Grant
- 1991-07-04 HU HU9332A patent/HUT64013A/en unknown
- 1991-07-04 RO RO93-00015A patent/RO112855B1/en unknown
- 1991-07-04 AU AU82120/91A patent/AU643056B2/en not_active Ceased
- 1991-07-04 PL PL91297608A patent/PL167076B1/en unknown
- 1991-07-04 SG SG1996002190A patent/SG48829A1/en unknown
- 1991-07-04 AT AT91912334T patent/ATE144765T1/en not_active IP Right Cessation
- 1991-07-04 ES ES91912334T patent/ES2095942T3/en not_active Expired - Lifetime
- 1991-07-04 JP JP3511631A patent/JPH0819068B2/en not_active Expired - Fee Related
- 1991-07-04 KR KR1019930700032A patent/KR0183446B1/en not_active IP Right Cessation
- 1991-07-04 RU RU9192016592A patent/RU2087465C1/en active
- 1991-07-05 MX MX9100100A patent/MX9100100A/en not_active IP Right Cessation
- 1991-07-08 IL IL9875691A patent/IL98756A/en active IP Right Grant
- 1991-07-08 SK SK2102-91A patent/SK279639B6/en unknown
- 1991-07-08 MA MA22481A patent/MA22208A1/en unknown
- 1991-07-08 IL IL11192491A patent/IL111924A/en not_active IP Right Cessation
- 1991-07-08 CZ CS912102A patent/CZ279901B6/en not_active IP Right Cessation
- 1991-07-08 YU YU120491A patent/YU120491A/en unknown
- 1991-07-08 SI SI9111204A patent/SI9111204A/en unknown
- 1991-07-09 DZ DZ910091A patent/DZ1514A1/en active
- 1991-07-09 ZA ZA915334A patent/ZA915334B/en unknown
- 1991-07-09 PT PT98259A patent/PT98259B/en not_active IP Right Cessation
- 1991-07-10 CN CN91105305A patent/CN1028990C/en not_active Expired - Fee Related
- 1991-07-10 TN TNTNSN91056A patent/TNSN91056A1/en unknown
- 1991-08-09 TW TW080106282A patent/TW204337B/zh active
-
1992
- 1992-11-27 LV LVP-92-231A patent/LV10086B/en unknown
-
1993
- 1993-01-06 BG BG97265A patent/BG61809B1/en unknown
- 1993-01-07 NO NO930047A patent/NO303777B1/en not_active IP Right Cessation
- 1993-01-08 FI FI930070A patent/FI930070A/en unknown
- 1993-01-08 OA OA60329A patent/OA09770A/en unknown
- 1993-03-23 HR HR930485A patent/HRP930485A2/en not_active Application Discontinuation
- 1993-08-10 LT LTIP848A patent/LT3602B/en not_active IP Right Cessation
-
1994
- 1994-10-25 CN CN94117208A patent/CN1033142C/en not_active Expired - Fee Related
- 1994-12-07 IL IL11192494A patent/IL111924A0/en unknown
-
1995
- 1995-03-27 US US08/411,039 patent/US5556886A/en not_active Expired - Fee Related
- 1995-03-27 US US08/411,118 patent/US5684049A/en not_active Expired - Fee Related
- 1995-06-29 HU HU95P/P00536P patent/HU211873A9/en unknown
-
1996
- 1996-11-28 GR GR960403220T patent/GR3021829T3/en unknown
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