JP2005515172A5 - - Google Patents
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- Publication number
- JP2005515172A5 JP2005515172A5 JP2003540176A JP2003540176A JP2005515172A5 JP 2005515172 A5 JP2005515172 A5 JP 2005515172A5 JP 2003540176 A JP2003540176 A JP 2003540176A JP 2003540176 A JP2003540176 A JP 2003540176A JP 2005515172 A5 JP2005515172 A5 JP 2005515172A5
- Authority
- JP
- Japan
- Prior art keywords
- tert
- pyrrolidine
- rel
- carboxylic acid
- isobutyl
- 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.)
- Ceased
Links
- -1 methoxy, ethoxy Chemical group 0.000 claims 31
- 125000000217 alkyl group Chemical group 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 14
- 229910052739 hydrogen Inorganic materials 0.000 claims 13
- 125000003118 aryl group Chemical group 0.000 claims 11
- 125000001072 heteroaryl group Chemical group 0.000 claims 11
- 239000001257 hydrogen Substances 0.000 claims 10
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 10
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims 5
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 5
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 5
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Chemical compound OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 208000015181 infectious disease Diseases 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 125000004043 oxo group Chemical group O=* 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims 2
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- YCYHUIIAAJRRSG-UEOVABOPSA-N (2s,4r,5r)-1-(4-tert-butyl-3-methoxybenzoyl)-2-(2-methylpropyl)-4-pyrazin-2-yl-5-pyridin-2-ylpyrrolidine-2-carboxylic acid Chemical compound C1=C(C(C)(C)C)C(OC)=CC(C(=O)N2[C@](C[C@H]([C@@H]2C=2N=CC=CC=2)C=2N=CC=NC=2)(CC(C)C)C(O)=O)=C1 YCYHUIIAAJRRSG-UEOVABOPSA-N 0.000 claims 1
- AGUARUUPGVWKAL-ROQFYEMFSA-N (2s,4s,5r)-1-(4-tert-butyl-3-methoxybenzoyl)-2-(2-methylpropyl)-4-pyrazin-2-yl-5-thiophen-2-ylpyrrolidine-2-carboxylic acid Chemical compound C1=C(C(C)(C)C)C(OC)=CC(C(=O)N2[C@](C[C@@H]([C@@H]2C=2SC=CC=2)C=2N=CC=NC=2)(CC(C)C)C(O)=O)=C1 AGUARUUPGVWKAL-ROQFYEMFSA-N 0.000 claims 1
- SCSFDIAEMPZBQC-RFQXOUTQSA-N (2s,4s,5r)-1-(4-tert-butyl-3-methoxybenzoyl)-2-(2-methylpropyl)-5-phenyl-4-pyrazin-2-ylpyrrolidine-2-carboxylic acid Chemical compound C1=C(C(C)(C)C)C(OC)=CC(C(=O)N2[C@](C[C@@H]([C@@H]2C=2C=CC=CC=2)C=2N=CC=NC=2)(CC(C)C)C(O)=O)=C1 SCSFDIAEMPZBQC-RFQXOUTQSA-N 0.000 claims 1
- VPXHSJQVCNOHGG-ODKNZVMVSA-N (2s,4s,5r)-1-(4-tert-butyl-3-methoxybenzoyl)-5-[4-(dimethylamino)phenyl]-2-(2-methylpropyl)-4-pyrazin-2-ylpyrrolidine-2-carboxylic acid Chemical compound C1=C(C(C)(C)C)C(OC)=CC(C(=O)N2[C@](C[C@@H]([C@@H]2C=2C=CC(=CC=2)N(C)C)C=2N=CC=NC=2)(CC(C)C)C(O)=O)=C1 VPXHSJQVCNOHGG-ODKNZVMVSA-N 0.000 claims 1
- RLGMYBRQNGBSED-LXHIVTORSA-N (2s,4s,5r)-1-(4-tert-butylbenzoyl)-2-(2-methylpropyl)-4-pyrazin-2-yl-5-(1,3-thiazol-5-yl)pyrrolidine-2-carboxylic acid Chemical compound N1([C@H]([C@H](C[C@@]1(CC(C)C)C(O)=O)C=1N=CC=NC=1)C=1SC=NC=1)C(=O)C1=CC=C(C(C)(C)C)C=C1 RLGMYBRQNGBSED-LXHIVTORSA-N 0.000 claims 1
- GNSGYACMPIKXRD-UQEHLFEPSA-N (2s,4s,5r)-1-(4-tert-butylbenzoyl)-2-(2-methylpropyl)-5-(3-phenylphenyl)-4-pyrazin-2-ylpyrrolidine-2-carboxylic acid Chemical compound N1([C@H]([C@H](C[C@@]1(CC(C)C)C(O)=O)C=1N=CC=NC=1)C=1C=C(C=CC=1)C=1C=CC=CC=1)C(=O)C1=CC=C(C(C)(C)C)C=C1 GNSGYACMPIKXRD-UQEHLFEPSA-N 0.000 claims 1
- WCIJZKBEXNTWDT-QVNGGLPSSA-N (2s,4s,5r)-1-(4-tert-butylbenzoyl)-2-(2-methylpropyl)-5-phenyl-4-pyrazin-2-ylpyrrolidine-2-carboxylic acid Chemical compound N1([C@H]([C@H](C[C@@]1(CC(C)C)C(O)=O)C=1N=CC=NC=1)C=1C=CC=CC=1)C(=O)C1=CC=C(C(C)(C)C)C=C1 WCIJZKBEXNTWDT-QVNGGLPSSA-N 0.000 claims 1
- QZUFUCKBIUIAOE-LNGZGTQPSA-N (2s,4s,5r)-1-(4-tert-butylbenzoyl)-5-[4-(dimethylamino)phenyl]-2-(2-methylpropyl)-4-pyrazin-2-ylpyrrolidine-2-carboxylic acid Chemical compound N1([C@H]([C@H](C[C@@]1(CC(C)C)C(O)=O)C=1N=CC=NC=1)C=1C=CC(=CC=1)N(C)C)C(=O)C1=CC=C(C(C)(C)C)C=C1 QZUFUCKBIUIAOE-LNGZGTQPSA-N 0.000 claims 1
- QMJBTQJLHQUYEH-COVQPCOOSA-N (2s,4s,5s)-1-(4-tert-butyl-3-methoxybenzoyl)-2-(2-methylpropyl)-5-propan-2-yl-4-pyrazin-2-ylpyrrolidine-2-carboxylic acid Chemical compound C1=C(C(C)(C)C)C(OC)=CC(C(=O)N2[C@](C[C@@H]([C@@H]2C(C)C)C=2N=CC=NC=2)(CC(C)C)C(O)=O)=C1 QMJBTQJLHQUYEH-COVQPCOOSA-N 0.000 claims 1
- BUZOXXIITIRFRK-IAKTWSEQSA-N (2s,4s,5s)-1-(4-tert-butyl-3-methoxybenzoyl)-5-methyl-2-(2-methylpropyl)-4-pyrazin-2-ylpyrrolidine-2-carboxylic acid Chemical compound C1=C(C(C)(C)C)C(OC)=CC(C(=O)N2[C@](C[C@@H]([C@@H]2C)C=2N=CC=NC=2)(CC(C)C)C(O)=O)=C1 BUZOXXIITIRFRK-IAKTWSEQSA-N 0.000 claims 1
- 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 claims 1
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 claims 1
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 claims 1
- OSKSSSYNGLGGPQ-UHFFFAOYSA-N 1-(2-chloro-1,3-thiazol-5-yl)pyrrolidine-2-carboxylic acid Chemical compound OC(=O)C1CCCN1C1=CN=C(Cl)S1 OSKSSSYNGLGGPQ-UHFFFAOYSA-N 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000006186 oral dosage form Substances 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 1
- 125000006513 pyridinyl methyl group Chemical group 0.000 claims 1
- VLJNHYLEOZPXFW-UHFFFAOYSA-N pyrrolidine-2-carboxamide Chemical compound NC(=O)C1CCCN1 VLJNHYLEOZPXFW-UHFFFAOYSA-N 0.000 claims 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0126440A GB0126440D0 (en) | 2001-11-02 | 2001-11-02 | Compounds |
| GB0203900A GB0203900D0 (en) | 2002-02-19 | 2002-02-19 | Compounds |
| GB0219321A GB0219321D0 (en) | 2002-08-19 | 2002-08-19 | Compounds |
| PCT/EP2002/012176 WO2003037895A1 (en) | 2001-11-02 | 2002-10-30 | 4-(6-membered)-heteroaryl acyl pyrrolidine derivatives as hcv inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005515172A JP2005515172A (ja) | 2005-05-26 |
| JP2005515172A5 true JP2005515172A5 (https=) | 2006-01-05 |
Family
ID=27256312
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003540176A Ceased JP2005515172A (ja) | 2001-11-02 | 2002-10-30 | Ｈｃｖ阻害剤としての４−（６−員）−ヘテロアリールアシルピロリジン誘導体 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7259163B2 (https=) |
| EP (1) | EP1440069B1 (https=) |
| JP (1) | JP2005515172A (https=) |
| AR (1) | AR037182A1 (https=) |
| AT (1) | ATE370137T1 (https=) |
| DE (1) | DE60221875T2 (https=) |
| ES (1) | ES2289161T3 (https=) |
| TW (1) | TW200302823A (https=) |
| WO (1) | WO2003037895A1 (https=) |
Families Citing this family (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0211418D0 (en) * | 2002-05-17 | 2002-06-26 | Glaxo Group Ltd | Compounds |
| ES2320771T3 (es) | 2003-04-16 | 2009-05-28 | Bristol-Myers Squibb Company | Inhibidores peptidicos de isoquinolina macrociclicos del virus de la hepatitis c. |
| HRP20130971T1 (hr) | 2004-02-20 | 2013-11-08 | Boehringer Ingelheim International Gmbh | Inhibitori virusne polimeraze |
| JP2007530516A (ja) * | 2004-03-26 | 2007-11-01 | スミスクライン・ビーチャム・コーポレイション | 抗ウイルス剤として有用な４−カルボキシピラゾール誘導体 |
| GB0423672D0 (en) * | 2004-10-25 | 2004-11-24 | Glaxo Group Ltd | Compounds |
| GB0519485D0 (en) * | 2005-09-23 | 2005-11-02 | Glaxo Group Ltd | Compounds |
| GB0519478D0 (en) * | 2005-09-23 | 2005-11-02 | Glaxo Group Ltd | Compounds |
| GB0519486D0 (en) * | 2005-09-23 | 2005-11-02 | Glaxo Group Ltd | Compounds |
| WO2007039146A1 (en) * | 2005-09-23 | 2007-04-12 | Smithkline Beecham Corporation | 4-carboxy pyrazole derivatives as anti-viral agents |
| US7964580B2 (en) | 2007-03-30 | 2011-06-21 | Pharmasset, Inc. | Nucleoside phosphoramidate prodrugs |
| WO2009003009A1 (en) * | 2007-06-26 | 2008-12-31 | Enanta Pharmaceuticals, Inc. | Substituted pyrrolidine as anti-infectives |
| US8173621B2 (en) | 2008-06-11 | 2012-05-08 | Gilead Pharmasset Llc | Nucleoside cyclicphosphates |
| WO2010065668A1 (en) | 2008-12-03 | 2010-06-10 | Presidio Pharmaceuticals, Inc. | Inhibitors of hcv ns5a |
| SI2373172T1 (sl) | 2008-12-03 | 2013-12-31 | Presidio Pharmaceuticals, Inc. | Inhibitorji HCV NS5A |
| SG194404A1 (en) | 2008-12-23 | 2013-11-29 | Gilead Pharmasset Llc | Synthesis of purine nucleosides |
| KR20110098849A (ko) | 2008-12-23 | 2011-09-01 | 파마셋 인코포레이티드 | 뉴클레오시드 유사체 |
| PT2376088T (pt) | 2008-12-23 | 2017-05-02 | Gilead Pharmasset Llc | Fosforamidatos de nucleósidos de 2-amino-purina 6-osubstituída |
| SG174883A1 (en) | 2009-03-27 | 2011-11-28 | Presidio Pharmaceuticals Inc | Fused ring inhibitors of hepatitis c |
| US8618076B2 (en) | 2009-05-20 | 2013-12-31 | Gilead Pharmasset Llc | Nucleoside phosphoramidates |
| TWI598358B (zh) | 2009-05-20 | 2017-09-11 | 基利法瑪席特有限責任公司 | 核苷磷醯胺 |
| WO2011073376A1 (en) | 2009-12-18 | 2011-06-23 | Euroscreen S.A. | Pyrrolidine or thiazolidine carboxylic acid derivatives, pharmaceutical composition and methods for use in treating metabolic disordersas as agonists of g- protein coupled receptor 43 (gpr43) |
| PT2609923T (pt) | 2010-03-31 | 2017-08-30 | Gilead Pharmasset Llc | Processo para a cristalização de 2-(((s)- (perfluorofenoxi)(fenoxi)fosforil)amino)propanoato de (s)-isopropilo |
| UY33312A (es) | 2010-03-31 | 2011-10-31 | Pharmasset Inc | Fosforamidato de nucleosido de purina |
| CA2800509A1 (en) | 2010-05-24 | 2011-12-01 | Presidio Pharmaceuticals, Inc. | Inhibitors of hcv ns5a |
| WO2012020036A1 (en) | 2010-08-13 | 2012-02-16 | F. Hoffmann-La Roche Ag | Hepatitis c virus inhibitors |
| MX2013004655A (es) | 2010-10-26 | 2013-08-27 | Presidio Pharmaceuticals Inc | Inhibidores del virus de la hepatitis c. |
| AU2011336632B2 (en) | 2010-11-30 | 2015-09-03 | Gilead Pharmasset Llc | Compounds |
| WO2012123298A1 (en) | 2011-03-11 | 2012-09-20 | F. Hoffmann-La Roche Ag | Antiviral compounds |
| WO2012175581A1 (en) | 2011-06-24 | 2012-12-27 | F. Hoffmann-La Roche Ag | Antiviral compounds |
| PL2709613T5 (pl) | 2011-09-16 | 2020-12-14 | Gilead Pharmasset Llc | Metody leczenia hcv |
| CA2847083A1 (en) | 2011-10-10 | 2013-04-18 | F. Hoffmann-La Roche Ag | Antiviral compounds |
| US8889159B2 (en) | 2011-11-29 | 2014-11-18 | Gilead Pharmasset Llc | Compositions and methods for treating hepatitis C virus |
| JP5923181B2 (ja) | 2011-12-16 | 2016-05-24 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | Ｈｃｖｎｓ５ａの阻害剤 |
| HK1200835A1 (en) | 2011-12-20 | 2015-08-14 | Riboscience Llc | 4'-azido, 3'-fluoro substituted nucleoside derivatives as inhibitors of hcv rna replication |
| MY171577A (en) | 2011-12-20 | 2019-10-21 | Hoffmann La Roche | 2',4'-difluoro-2'-methyl substituted nucleoside derivatives as inhibitors of hcv rna replication |
| EP2817291A1 (en) | 2012-02-24 | 2014-12-31 | F. Hoffmann-La Roche AG | Antiviral compounds |
| US20140010783A1 (en) | 2012-07-06 | 2014-01-09 | Hoffmann-La Roche Inc. | Antiviral compounds |
| KR20150109451A (ko) | 2013-01-23 | 2015-10-01 | 에프. 호프만-라 로슈 아게 | 항바이러스성 트라이아졸 유도체 |
| PT2950786T (pt) | 2013-01-31 | 2020-03-03 | Gilead Pharmasset Llc | Formulação de combinação de dois compostos antivirais |
| CA2900319A1 (en) | 2013-03-05 | 2014-09-12 | F. Hoffmann-La Roche Ag | Antiviral compounds |
| EP2996695B1 (en) | 2013-05-16 | 2022-04-13 | Riboscience LLC | 4'-fluoro-2'-methyl substituted nucleoside derivatives |
| US20180200280A1 (en) | 2013-05-16 | 2018-07-19 | Riboscience Llc | 4'-Fluoro-2'-Methyl Substituted Nucleoside Derivatives as Inhibitors of HCV RNA Replication |
| AU2014272055A1 (en) | 2013-05-16 | 2015-12-24 | Riboscience Llc | 4'-azido, 3'-deoxy-3'-fluoro substituted nucleoside derivatives |
| EA201690473A1 (ru) | 2013-08-27 | 2017-03-31 | ГАЙЛИД ФАРМАССЕТ ЭлЭлСи | Комбинированный состав двух противовирусных соединений |
| CN105916500A (zh) | 2013-11-27 | 2016-08-31 | 欧洲筛选有限公司 | 用于治疗炎性疾病的化合物、药物组合物和方法 |
| EP3684374B1 (en) | 2017-09-21 | 2025-07-30 | Riboscience LLC | 4'-fluoro-2'-methyl substituted nucleoside derivatives as inhibitors of hcv rna replication |
| CN109678814B (zh) * | 2018-12-28 | 2021-03-23 | 浙江外国语学院 | 一种制备2-氯-1, 3-噻唑-5-甲醛的方法 |
| IL298760A (en) | 2020-06-05 | 2023-02-01 | Kinnate Biopharma Inc | Fibroblast growth factor receptor kinase inhibitors |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT395007B (de) * | 1990-03-29 | 1992-08-25 | Noe Christian | Modifizierte cyclische aminosaeuren und aus diesen synthetisierte dipeptide und verfahren zu ihrer herstellung |
| WO1993018765A1 (en) * | 1992-03-20 | 1993-09-30 | The Wellcome Foundation Limited | Indole derivatives with antiviral activity |
| EP1315698A1 (en) | 1998-04-23 | 2003-06-04 | Abbott Laboratories | Pyrrolidines as inhibitors of neuraminidases |
| US6455571B1 (en) | 1998-04-23 | 2002-09-24 | Abbott Laboratories | Inhibitors of neuraminidases |
-
2002
- 2002-10-30 ES ES02783059T patent/ES2289161T3/es not_active Expired - Lifetime
- 2002-10-30 AT AT02783059T patent/ATE370137T1/de not_active IP Right Cessation
- 2002-10-30 US US10/494,127 patent/US7259163B2/en not_active Expired - Fee Related
- 2002-10-30 EP EP02783059A patent/EP1440069B1/en not_active Expired - Lifetime
- 2002-10-30 JP JP2003540176A patent/JP2005515172A/ja not_active Ceased
- 2002-10-30 DE DE60221875T patent/DE60221875T2/de not_active Expired - Lifetime
- 2002-10-30 WO PCT/EP2002/012176 patent/WO2003037895A1/en not_active Ceased
- 2002-10-31 AR ARP020104160A patent/AR037182A1/es unknown
- 2002-10-31 TW TW091132224A patent/TW200302823A/zh unknown
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