JP2015514807A5 - - Google Patents
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- Publication number
- JP2015514807A5 JP2015514807A5 JP2015509099A JP2015509099A JP2015514807A5 JP 2015514807 A5 JP2015514807 A5 JP 2015514807A5 JP 2015509099 A JP2015509099 A JP 2015509099A JP 2015509099 A JP2015509099 A JP 2015509099A JP 2015514807 A5 JP2015514807 A5 JP 2015514807A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- compound
- hydrogen
- optionally substituted
- pharmaceutical composition
- 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
- 125000000217 alkyl group Chemical group 0.000 claims description 80
- 150000001875 compounds Chemical class 0.000 claims description 61
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 34
- 239000002777 nucleoside Substances 0.000 claims description 28
- 239000008194 pharmaceutical composition Substances 0.000 claims description 24
- -1 -SR e Chemical group 0.000 claims description 22
- 150000003833 nucleoside derivatives Chemical class 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 239000003814 drug Substances 0.000 claims description 19
- 239000003112 inhibitor Substances 0.000 claims description 18
- 229940124597 therapeutic agent Drugs 0.000 claims description 18
- 241000124008 Mammalia Species 0.000 claims description 17
- 102000014150 Interferons Human genes 0.000 claims description 16
- 108010050904 Interferons Proteins 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 229940047124 interferons Drugs 0.000 claims description 16
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- 229940124771 HCV-NS3 protease inhibitor Drugs 0.000 claims description 10
- 108700008776 hepatitis C virus NS-5 Proteins 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 208000010710 hepatitis C virus infection Diseases 0.000 claims description 9
- 101800001014 Non-structural protein 5A Proteins 0.000 claims description 8
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims description 8
- 239000000134 cyclophilin inhibitor Substances 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 229960000329 ribavirin Drugs 0.000 claims description 8
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims description 8
- 125000003835 nucleoside group Chemical group 0.000 claims description 7
- 241000711549 Hepacivirus C Species 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 230000002401 inhibitory effect Effects 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 230000010076 replication Effects 0.000 claims description 5
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 4
- XTDKZSUYCXHXJM-UHFFFAOYSA-N 2-methoxyoxane Chemical compound COC1CCCCO1 XTDKZSUYCXHXJM-UHFFFAOYSA-N 0.000 claims description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000009472 formulation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000013160 medical therapy Methods 0.000 description 1
- 150000003527 tetrahydropyrans Chemical group 0.000 description 1
- 230000029812 viral genome replication Effects 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261637959P | 2012-04-25 | 2012-04-25 | |
| US61/637,959 | 2012-04-25 | ||
| US201361774033P | 2013-03-07 | 2013-03-07 | |
| US61/774,033 | 2013-03-07 | ||
| PCT/US2013/037920 WO2013163262A1 (en) | 2012-04-25 | 2013-04-24 | Piperazine-piperidine compounds as hepatitis c virus inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015514807A JP2015514807A (ja) | 2015-05-21 |
| JP2015514807A5 true JP2015514807A5 (cg-RX-API-DMAC10.html) | 2016-04-21 |
| JP6069491B2 JP6069491B2 (ja) | 2017-02-01 |
Family
ID=48237291
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015509099A Expired - Fee Related JP6069491B2 (ja) | 2012-04-25 | 2013-04-24 | Ｃ型肝炎ウイルス阻害剤としてのピペラジン−ピペリジン化合物 |
Country Status (17)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108794454B (zh) * | 2017-04-27 | 2023-08-15 | 广东东阳光药业股份有限公司 | 一种咪唑环化合物的制备方法 |
| CN112480084B (zh) * | 2017-11-27 | 2021-09-21 | 常州寅盛药业有限公司 | 反应路线简单的达卡他韦起始原料的合成方法 |
| EP4759807A1 (en) | 2023-08-11 | 2026-06-17 | Shenzhen Zhongge Biological Technology Co., Ltd. | Proteolysis targeting chimera compound for degrading irak4 and use thereof |
| CN122497677A (zh) | 2023-10-20 | 2026-07-31 | 奇树医药公司 | 一种降解irak4的蛋白降解靶向嵌合体化合物及其应用 |
Family Cites Families (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007115805A2 (en) * | 2006-04-05 | 2007-10-18 | European Molecular Biology Laboratory (Embl) | Aurora kinase inhibitors |
| US8329159B2 (en) | 2006-08-11 | 2012-12-11 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8303944B2 (en) | 2006-08-11 | 2012-11-06 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US7659270B2 (en) | 2006-08-11 | 2010-02-09 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8147818B2 (en) | 2008-02-13 | 2012-04-03 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US20120040977A1 (en) | 2009-02-23 | 2012-02-16 | Presidio Pharmaceuticals, Inc. | Inhibitors of hcv ns5a |
| WO2010094977A1 (en) | 2009-02-23 | 2010-08-26 | Arrow Therapeutics Limited | Novel biphenyl compounds useful for the treatment of hepatitis c |
| US8796466B2 (en) | 2009-03-30 | 2014-08-05 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| SG176015A1 (en) | 2009-05-13 | 2011-12-29 | Gilead Sciences Inc | Antiviral compounds |
| EP2473056A4 (en) | 2009-09-04 | 2013-02-13 | Glaxosmithkline Llc | CHEMICAL COMPOUNDS |
| US8822700B2 (en) | 2009-09-11 | 2014-09-02 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| WO2011031904A1 (en) | 2009-09-11 | 2011-03-17 | Enanta Pharmaceuticals, Inc | Hepatitis c virus inhibitors |
| EP2475254A4 (en) * | 2009-09-11 | 2013-05-22 | Enanta Pharm Inc | HEPATITIS C-VIRUS HEMMER |
| US20110274648A1 (en) | 2009-11-11 | 2011-11-10 | Bristol-Myers Squibb Company | Hepatitis C Virus Inhibitors |
| US8653070B2 (en) | 2009-12-14 | 2014-02-18 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| US8377980B2 (en) | 2009-12-16 | 2013-02-19 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| CN102883718A (zh) | 2009-12-24 | 2013-01-16 | 顶点制药公司 | 用于治疗或预防黄病毒感染的类似物 |
| WO2011091446A1 (en) | 2010-01-22 | 2011-07-28 | Glaxosmithkline Llc | Chemical compounds |
| MA34147B1 (fr) | 2010-03-09 | 2013-04-03 | Merck Sharp & Dohme | Composes tricycliques fusionnes de silyle et leurs methodes d'utilisation dans le cadre du traitement de maladies virales |
| EP2575819A4 (en) | 2010-06-04 | 2013-11-27 | Enanta Pharm Inc | INHIBITORS OF HEPATITIS C VIRUS |
| US20120195857A1 (en) | 2010-08-12 | 2012-08-02 | Bristol-Myers Squibb Company | Hepatitis C Virus Inhibitors |
| WO2012048421A1 (en) | 2010-10-14 | 2012-04-19 | Boehringer Ingelheim International Gmbh | Hepatitis c inhibitor compounds |
| CA2814534A1 (en) | 2010-11-04 | 2012-05-10 | Theravance, Inc. | Novel inhibitors of hepatitis c virus |
| US8552047B2 (en) | 2011-02-07 | 2013-10-08 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| AR088630A1 (es) | 2011-11-03 | 2014-06-25 | Theravance Inc | Inhibidores del virus de la hepatitis c |
| CA2869908C (en) * | 2012-04-25 | 2018-02-20 | Theravance Biopharma R&D Ip, Llc | Hepatitis c virus inhibitors |
-
2013
- 2013-04-24 LT LTEP13720201.6T patent/LT2850075T/lt unknown
- 2013-04-24 JP JP2015509099A patent/JP6069491B2/ja not_active Expired - Fee Related
- 2013-04-24 US US13/869,199 patent/US9206159B2/en not_active Expired - Fee Related
- 2013-04-24 WO PCT/US2013/037920 patent/WO2013163262A1/en not_active Ceased
- 2013-04-24 ES ES13720201.6T patent/ES2624846T3/es active Active
- 2013-04-24 SI SI201330640A patent/SI2850075T1/sl unknown
- 2013-04-24 DK DK13720201.6T patent/DK2850075T3/en active
- 2013-04-24 RS RS20170354A patent/RS55864B1/sr unknown
- 2013-04-24 HR HRP20170471TT patent/HRP20170471T1/hr unknown
- 2013-04-24 HU HUE13720201A patent/HUE032173T2/en unknown
- 2013-04-24 PL PL13720201T patent/PL2850075T3/pl unknown
- 2013-04-24 EP EP13720201.6A patent/EP2850075B1/en active Active
- 2013-04-24 CA CA2869640A patent/CA2869640C/en not_active Expired - Fee Related
- 2013-04-24 PT PT137202016T patent/PT2850075T/pt unknown
- 2013-04-24 ME MEP-2017-85A patent/ME02682B/me unknown
- 2013-04-24 CN CN201380021717.8A patent/CN104302639B/zh not_active Expired - Fee Related
-
2017
- 2017-05-17 CY CY20171100520T patent/CY1118920T1/el unknown