JP2004532276A5 - - Google Patents
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- Publication number
- JP2004532276A5 JP2004532276A5 JP2003503620A JP2003503620A JP2004532276A5 JP 2004532276 A5 JP2004532276 A5 JP 2004532276A5 JP 2003503620 A JP2003503620 A JP 2003503620A JP 2003503620 A JP2003503620 A JP 2003503620A JP 2004532276 A5 JP2004532276 A5 JP 2004532276A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- alkyl
- substituted
- isopropyl
- dichlorophenylthio
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 13
- 239000001257 hydrogen Substances 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 125000001424 substituent group Chemical group 0.000 claims 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 8
- 229910052794 bromium Inorganic materials 0.000 claims 8
- 229910052801 chlorine Inorganic materials 0.000 claims 8
- 239000000460 chlorine Substances 0.000 claims 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 7
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 7
- 229910052731 fluorine Inorganic materials 0.000 claims 7
- 239000011737 fluorine Substances 0.000 claims 7
- -1 Methyl [[5- (3,5-dichlorophenylthio) -1-isopropyl-4-[(4-pyridyl) methyl] -1H-pyrazol-3-yl] methyl] carbamate Chemical class 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 5
- 125000005002 aryl methyl group Chemical group 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 241000725303 Human immunodeficiency virus Species 0.000 claims 4
- 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- VCARPLHUPPGQJK-UHFFFAOYSA-N n-azidohydroxylamine Chemical compound ONN=[N+]=[N-] VCARPLHUPPGQJK-UHFFFAOYSA-N 0.000 claims 3
- 125000003107 substituted aryl group Chemical group 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- JLRAHNOJEOLANY-UHFFFAOYSA-N 3-[[5-(3,5-dichlorophenyl)sulfanyl-3-(hydroxymethyl)-1-propan-2-ylpyrazol-4-yl]methoxymethyl]benzonitrile Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(C(C)C)N=C(CO)C=1COCC1=CC=CC(C#N)=C1 JLRAHNOJEOLANY-UHFFFAOYSA-N 0.000 claims 1
- LHSOBQYZSOZNEM-UHFFFAOYSA-N 3-chloro-5-[5-(hydroxymethyl)-2-propan-2-yl-4-(pyridin-4-ylmethyl)pyrazol-3-yl]sulfanylbenzonitrile Chemical compound C=1C(Cl)=CC(C#N)=CC=1SC=1N(C(C)C)N=C(CO)C=1CC1=CC=NC=C1 LHSOBQYZSOZNEM-UHFFFAOYSA-N 0.000 claims 1
- DBXFPTRWZRLIST-UHFFFAOYSA-N [4-[(5-bromo-2-methylpyrimidin-4-yl)methyl]-5-(3,5-dichlorophenyl)sulfanyl-1-propan-2-ylpyrazol-3-yl]methanol Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(C(C)C)N=C(CO)C=1CC1=NC(C)=NC=C1Br DBXFPTRWZRLIST-UHFFFAOYSA-N 0.000 claims 1
- HPKVLNVUKUBTGU-UHFFFAOYSA-N [5-(3,5-dichlorophenyl)sulfanyl-1-ethyl-4-(pyridin-4-ylmethyl)pyrazol-3-yl]methanol Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(CC)N=C(CO)C=1CC1=CC=NC=C1 HPKVLNVUKUBTGU-UHFFFAOYSA-N 0.000 claims 1
- MSXAJIBSJLYBOY-UHFFFAOYSA-N [5-(3,5-dichlorophenyl)sulfanyl-1-propan-2-yl-4-(pyridin-4-ylmethoxymethyl)pyrazol-3-yl]methanol Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(C(C)C)N=C(CO)C=1COCC1=CC=NC=C1 MSXAJIBSJLYBOY-UHFFFAOYSA-N 0.000 claims 1
- RVAHELGGEXONEH-UHFFFAOYSA-N [5-(3,5-dichlorophenyl)sulfanyl-1-propan-2-yl-4-(pyridin-4-ylmethoxymethyl)pyrazol-3-yl]methyl carbamate Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(C(C)C)N=C(COC(N)=O)C=1COCC1=CC=NC=C1 RVAHELGGEXONEH-UHFFFAOYSA-N 0.000 claims 1
- DGHNSWWBAOTIDW-UHFFFAOYSA-N [5-(3,5-dichlorophenyl)sulfanyl-1-propan-2-yl-4-(pyridin-4-ylmethyl)pyrazol-3-yl]methanamine Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(C(C)C)N=C(CN)C=1CC1=CC=NC=C1 DGHNSWWBAOTIDW-UHFFFAOYSA-N 0.000 claims 1
- HAUURQXLCOVNLL-UHFFFAOYSA-N [5-(3,5-dichlorophenyl)sulfanyl-1-propan-2-yl-4-(pyridin-4-ylmethyl)pyrazol-3-yl]methanol Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(C(C)C)N=C(CO)C=1CC1=CC=NC=C1 HAUURQXLCOVNLL-UHFFFAOYSA-N 0.000 claims 1
- AQSLEAXCHMHJJH-UHFFFAOYSA-N [5-(3,5-dichlorophenyl)sulfanyl-1-propan-2-yl-4-(pyridin-4-ylmethyl)pyrazol-3-yl]methyl carbamate Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(C(C)C)N=C(COC(N)=O)C=1CC1=CC=NC=C1 AQSLEAXCHMHJJH-UHFFFAOYSA-N 0.000 claims 1
- QQVBJSXOXZZXDV-UHFFFAOYSA-N [5-(3,5-dichlorophenyl)sulfanyl-1-propan-2-yl-4-(pyridin-4-ylmethyl)pyrazol-3-yl]methyl n-methylcarbamate Chemical compound C=1C=NC=CC=1CC=1C(COC(=O)NC)=NN(C(C)C)C=1SC1=CC(Cl)=CC(Cl)=C1 QQVBJSXOXZZXDV-UHFFFAOYSA-N 0.000 claims 1
- LLVOEMQIEYNQGW-UHFFFAOYSA-N [5-(3,5-dichlorophenyl)sulfanyl-1-propan-2-yl-4-(pyridin-4-ylmethyl)pyrazol-3-yl]methylurea Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(C(C)C)N=C(CNC(N)=O)C=1CC1=CC=NC=C1 LLVOEMQIEYNQGW-UHFFFAOYSA-N 0.000 claims 1
- ZICBEMJXOXYDGZ-UHFFFAOYSA-N [5-(3,5-dichlorophenyl)sulfanyl-3-(hydroxymethyl)-1-propan-2-ylpyrazol-4-yl]methanol Chemical compound CC(C)N1N=C(CO)C(CO)=C1SC1=CC(Cl)=CC(Cl)=C1 ZICBEMJXOXYDGZ-UHFFFAOYSA-N 0.000 claims 1
- HLAIHUXWSCAYHM-UHFFFAOYSA-N [5-(3,5-dichlorophenyl)sulfanyl-4-[(3,4-difluorophenyl)methyl]-1-propan-2-ylpyrazol-3-yl]methanol Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(C(C)C)N=C(CO)C=1CC1=CC=C(F)C(F)=C1 HLAIHUXWSCAYHM-UHFFFAOYSA-N 0.000 claims 1
- ZZVUSIQKMJZFSY-UHFFFAOYSA-N [5-(3,5-dichlorophenyl)sulfanyl-4-[(3-methoxyphenyl)methyl]-1-propan-2-ylpyrazol-3-yl]methanol Chemical compound COC1=CC=CC(CC2=C(N(C(C)C)N=C2CO)SC=2C=C(Cl)C=C(Cl)C=2)=C1 ZZVUSIQKMJZFSY-UHFFFAOYSA-N 0.000 claims 1
- IFSIFGYRPVEASN-UHFFFAOYSA-N [5-(3,5-dichlorophenyl)sulfanyl-4-ethyl-1-propan-2-ylpyrazol-3-yl]methanol Chemical compound OCC1=NN(C(C)C)C(SC=2C=C(Cl)C=C(Cl)C=2)=C1CC IFSIFGYRPVEASN-UHFFFAOYSA-N 0.000 claims 1
- XKMLQNVIELJJRO-UHFFFAOYSA-N [5-(3,5-difluorophenyl)sulfanyl-1-propan-2-yl-4-(pyridin-4-ylmethyl)pyrazol-3-yl]methanol Chemical compound C=1C(F)=CC(F)=CC=1SC=1N(C(C)C)N=C(CO)C=1CC1=CC=NC=C1 XKMLQNVIELJJRO-UHFFFAOYSA-N 0.000 claims 1
- QREAIDRGKWQLHY-UHFFFAOYSA-N [5-(3-bromo-5-chlorophenyl)sulfanyl-1-propan-2-yl-4-(pyridin-4-ylmethyl)pyrazol-3-yl]methanol Chemical compound C=1C(Cl)=CC(Br)=CC=1SC=1N(C(C)C)N=C(CO)C=1CC1=CC=NC=C1 QREAIDRGKWQLHY-UHFFFAOYSA-N 0.000 claims 1
- DGMGBAZYKZEBCN-UHFFFAOYSA-N [cyano(hydroxy)amino] thiohypofluorite Chemical compound ON(SF)C#N DGMGBAZYKZEBCN-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- XWZBFWRTWAQXAZ-UHFFFAOYSA-N n-[[5-(3,5-dichlorophenyl)sulfanyl-1-propan-2-yl-4-(pyridin-4-ylmethyl)pyrazol-3-yl]methyl]methanesulfonamide Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(C(C)C)N=C(CNS(C)(=O)=O)C=1CC1=CC=NC=C1 XWZBFWRTWAQXAZ-UHFFFAOYSA-N 0.000 claims 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0113524.3A GB0113524D0 (en) | 2001-06-04 | 2001-06-04 | Pyrazole derivatives |
| PCT/EP2002/005898 WO2002100853A1 (en) | 2001-06-04 | 2002-05-29 | Pyrazole derivatives as hiv reverse transcriptase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004532276A JP2004532276A (ja) | 2004-10-21 |
| JP2004532276A5 true JP2004532276A5 (https=) | 2005-09-15 |
| JP4088249B2 JP4088249B2 (ja) | 2008-05-21 |
Family
ID=9915841
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003503620A Expired - Fee Related JP4088249B2 (ja) | 2001-06-04 | 2002-05-29 | Ｈｉｖ逆転写酵素阻害剤としてのピラゾール誘導体 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US6538015B1 (https=) |
| EP (1) | EP1401826B1 (https=) |
| JP (1) | JP4088249B2 (https=) |
| KR (1) | KR100627532B1 (https=) |
| CN (1) | CN1249052C (https=) |
| AT (1) | ATE357439T1 (https=) |
| AU (1) | AU2002325221B2 (https=) |
| BR (1) | BR0210158A (https=) |
| CA (1) | CA2448058C (https=) |
| DE (1) | DE60219009T2 (https=) |
| DK (1) | DK1401826T3 (https=) |
| ES (1) | ES2282446T3 (https=) |
| GB (1) | GB0113524D0 (https=) |
| MX (1) | MXPA03011199A (https=) |
| PT (1) | PT1401826E (https=) |
| WO (1) | WO2002100853A1 (https=) |
| ZA (1) | ZA200308781B (https=) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200423930A (en) * | 2003-02-18 | 2004-11-16 | Hoffmann La Roche | Non-nucleoside reverse transcriptase inhibitors |
| US8022225B2 (en) | 2004-08-04 | 2011-09-20 | Taisho Pharmaceutical Co., Ltd | Triazole derivative |
| WO2006072833A1 (en) * | 2005-01-06 | 2006-07-13 | Pfizer Limited | Imidazole derivatives as enzyme reverse transcriptase modulators |
| RU2409570C2 (ru) | 2006-02-03 | 2011-01-20 | Тайсо Фармасьютикал Ко., Лтд. | Производные триазола |
| CN101415687B (zh) | 2006-02-06 | 2012-02-08 | 大正制药株式会社 | 鞘氨醇-1-磷酸结合抑制物质 |
| RU2451676C2 (ru) | 2006-08-16 | 2012-05-27 | Ф.Хоффманн-Ля Рош Аг | Ненуклеозидные ингибиторы обратной транскриптазы |
| JP2010530863A (ja) | 2007-06-22 | 2010-09-16 | エフ．ホフマン−ラ ロシュ アーゲー | 非ヌクレオシド逆転写酵素阻害剤としての尿素及びカルバマート誘導体 |
| US8048898B2 (en) | 2007-08-01 | 2011-11-01 | Taisho Pharmaceutical Co., Ltd | Inhibitor of binding of S1P1 |
| WO2009080534A1 (en) | 2007-12-21 | 2009-07-02 | F. Hoffmann-La Roche Ag | Heterocyclic antiviral compounds |
| 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 |
| EP2295038B1 (en) * | 2009-09-11 | 2013-05-29 | AiCuris GmbH & Co. KG | Solid dispersion comprising an anti-HIV agent |
| EP2571854B1 (en) * | 2010-05-20 | 2014-11-05 | Bayer Intellectual Property GmbH | Method for manufacturing 1-alkyl-3-difluormethyl-5-hydroxypyrazoles |
| AU2011277426B2 (en) | 2010-07-15 | 2015-04-23 | Sumitomo Pharma Co., Ltd. | Pyrazole compound |
| WO2014074628A1 (en) * | 2012-11-08 | 2014-05-15 | University Of Pittsburgh-Of The Commonwealth System Of Higher Education | Compounds for treating hiv and methods for using the compounds |
| US9925190B2 (en) | 2015-02-16 | 2018-03-27 | University of Pittsburgh—of the Commonwealth System of Higher Education | Small molecules targeting HIV-1 Nef |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993015060A1 (fr) | 1992-01-22 | 1993-08-05 | Nissan Chemical Industries, Ltd. | Derive de pyrazole substitue et bactericide agrohorticole |
| US6005109A (en) | 1997-10-30 | 1999-12-21 | Pflizer Inc. | Pyrazoles and pyrazolopyrimidines having CRF antagonistic activity |
| DK0786455T3 (da) | 1994-09-26 | 2004-03-29 | Shionogi & Co | Imidazolderivater |
| US5698495A (en) | 1995-11-15 | 1997-12-16 | Zeneca Limited | Herbicidal substituted pyrazole compounds |
| GB0016787D0 (en) | 2000-07-07 | 2000-08-30 | Pfizer Ltd | Compounds useful in therapy |
| GB0024795D0 (en) * | 2000-10-10 | 2000-11-22 | Hoffmann La Roche | Pyrazole derivatives for the treatment of viral diseases |
-
2001
- 2001-06-04 GB GBGB0113524.3A patent/GB0113524D0/en not_active Ceased
-
2002
- 2002-05-24 US US10/154,585 patent/US6538015B1/en not_active Expired - Fee Related
- 2002-05-29 WO PCT/EP2002/005898 patent/WO2002100853A1/en not_active Ceased
- 2002-05-29 EP EP02758207A patent/EP1401826B1/en not_active Expired - Lifetime
- 2002-05-29 BR BR0210158-0A patent/BR0210158A/pt not_active IP Right Cessation
- 2002-05-29 PT PT02758207T patent/PT1401826E/pt unknown
- 2002-05-29 DE DE60219009T patent/DE60219009T2/de not_active Expired - Fee Related
- 2002-05-29 DK DK02758207T patent/DK1401826T3/da active
- 2002-05-29 MX MXPA03011199A patent/MXPA03011199A/es active IP Right Grant
- 2002-05-29 JP JP2003503620A patent/JP4088249B2/ja not_active Expired - Fee Related
- 2002-05-29 CA CA002448058A patent/CA2448058C/en not_active Expired - Fee Related
- 2002-05-29 KR KR1020037015833A patent/KR100627532B1/ko not_active Expired - Fee Related
- 2002-05-29 AU AU2002325221A patent/AU2002325221B2/en not_active Ceased
- 2002-05-29 AT AT02758207T patent/ATE357439T1/de not_active IP Right Cessation
- 2002-05-29 CN CNB028111974A patent/CN1249052C/zh not_active Expired - Fee Related
- 2002-05-29 ES ES02758207T patent/ES2282446T3/es not_active Expired - Lifetime
-
2003
- 2003-11-11 ZA ZA200308781A patent/ZA200308781B/en unknown
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