JP2014532716A5 - - Google Patents
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- Publication number
- JP2014532716A5 JP2014532716A5 JP2014540112A JP2014540112A JP2014532716A5 JP 2014532716 A5 JP2014532716 A5 JP 2014532716A5 JP 2014540112 A JP2014540112 A JP 2014540112A JP 2014540112 A JP2014540112 A JP 2014540112A JP 2014532716 A5 JP2014532716 A5 JP 2014532716A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- optionally substituted
- hydrogen
- cycloalkyl
- heterocycle
- 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 199
- 150000001875 compounds Chemical class 0.000 claims description 57
- 229910052739 hydrogen Inorganic materials 0.000 claims description 57
- 239000001257 hydrogen Substances 0.000 claims description 57
- 125000000623 heterocyclic group Chemical group 0.000 claims description 46
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 36
- 125000005843 halogen group Chemical group 0.000 claims description 33
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 32
- 125000001072 heteroaryl group Chemical group 0.000 claims description 27
- 150000002431 hydrogen Chemical class 0.000 claims description 25
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- -1 —SR e Chemical group 0.000 claims description 23
- 239000008194 pharmaceutical composition Substances 0.000 claims description 20
- 239000003814 drug Substances 0.000 claims description 16
- 239000002777 nucleoside Substances 0.000 claims description 16
- 241000124008 Mammalia Species 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 229940124597 therapeutic agent Drugs 0.000 claims description 13
- 150000003833 nucleoside derivatives Chemical class 0.000 claims description 12
- 125000006413 ring segment Chemical group 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 208000010710 hepatitis C virus infection Diseases 0.000 claims description 11
- 239000003112 inhibitor Substances 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 102000014150 Interferons Human genes 0.000 claims description 8
- 108010050904 Interferons Proteins 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 8
- 229940047124 interferons Drugs 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 229940124771 HCV-NS3 protease inhibitor Drugs 0.000 claims description 6
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 6
- 108700008776 hepatitis C virus NS-5 Proteins 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 4
- 241000711549 Hepacivirus C Species 0.000 claims description 4
- 101800001014 Non-structural protein 5A Proteins 0.000 claims description 4
- 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 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 239000000134 cyclophilin inhibitor Substances 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 125000003835 nucleoside group Chemical group 0.000 claims description 4
- 229960000329 ribavirin Drugs 0.000 claims description 4
- 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 4
- 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 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 230000010076 replication Effects 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims 1
- 235000018936 Vitellaria paradoxa Nutrition 0.000 claims 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 claims 1
- 230000029812 viral genome replication Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 1
- 238000013160 medical therapy Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161555056P | 2011-11-03 | 2011-11-03 | |
| US61/555,056 | 2011-11-03 | ||
| US201261600089P | 2012-02-17 | 2012-02-17 | |
| US61/600,089 | 2012-02-17 | ||
| US201261637961P | 2012-04-25 | 2012-04-25 | |
| US61/637,961 | 2012-04-25 | ||
| PCT/US2012/063181 WO2013067267A1 (en) | 2011-11-03 | 2012-11-02 | Rod -like hepatitis c virus inhibitors containing the fragement {2- [4- (bi phenyl - 4 - yl) - 1h - imidazo - 2 - yl] pyrrolidine - 1 - carbonlymethyl} amine |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016236386A Division JP2017048248A (ja) | 2011-11-03 | 2016-12-06 | フラグメント｛２−［４−（ビフェニル−４−イル）−１ｈ−イミダゾ−２−イル］ピロリジン−１−カルボニルメチル｝アミンを含む棒状ｃ型肝炎ウイルス阻害剤 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014532716A JP2014532716A (ja) | 2014-12-08 |
| JP2014532716A5 true JP2014532716A5 (enExample) | 2015-12-10 |
| JP6082747B2 JP6082747B2 (ja) | 2017-02-15 |
Family
ID=47146777
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014540112A Expired - Fee Related JP6082747B2 (ja) | 2011-11-03 | 2012-11-02 | フラグメント｛２−［４−（ビフェニル−４−イル）−１ｈ−イミダゾ−２−イル］ピロリジン−１−カルボニルメチル｝アミンを含む棒状ｃ型肝炎ウイルス阻害剤 |
| JP2016236386A Pending JP2017048248A (ja) | 2011-11-03 | 2016-12-06 | フラグメント｛２−［４−（ビフェニル−４−イル）−１ｈ−イミダゾ−２−イル］ピロリジン−１−カルボニルメチル｝アミンを含む棒状ｃ型肝炎ウイルス阻害剤 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016236386A Pending JP2017048248A (ja) | 2011-11-03 | 2016-12-06 | フラグメント｛２−［４−（ビフェニル−４−イル）−１ｈ−イミダゾ−２−イル］ピロリジン−１−カルボニルメチル｝アミンを含む棒状ｃ型肝炎ウイルス阻害剤 |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US9212168B2 (enExample) |
| EP (1) | EP2773634B1 (enExample) |
| JP (2) | JP6082747B2 (enExample) |
| KR (1) | KR20140091036A (enExample) |
| CN (1) | CN103946220B (enExample) |
| AR (1) | AR088630A1 (enExample) |
| AU (1) | AU2012332358B2 (enExample) |
| BR (1) | BR112014010401A8 (enExample) |
| CA (1) | CA2852700A1 (enExample) |
| CL (1) | CL2014001110A1 (enExample) |
| CO (1) | CO6940424A2 (enExample) |
| HK (1) | HK1200812A1 (enExample) |
| IL (1) | IL232042A (enExample) |
| MX (1) | MX347692B (enExample) |
| PH (1) | PH12014500988A1 (enExample) |
| RU (1) | RU2625787C2 (enExample) |
| SG (1) | SG11201401891RA (enExample) |
| TW (1) | TWI577672B (enExample) |
| WO (1) | WO2013067267A1 (enExample) |
| ZA (1) | ZA201403198B (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012061552A1 (en) | 2010-11-04 | 2012-05-10 | Theravance, Inc. | Novel inhibitors of hepatitis c virus |
| WO2013161913A1 (ja) | 2012-04-25 | 2013-10-31 | 武田薬品工業株式会社 | 含窒素複素環化合物 |
| JP6069492B2 (ja) * | 2012-04-25 | 2017-02-01 | セラヴァンス バイオファーマ アール＆ディー アイピー， エルエルシー | Ｃ型肝炎ウイルス阻害剤 |
| WO2013163262A1 (en) | 2012-04-25 | 2013-10-31 | Theravance, Inc. | Piperazine-piperidine compounds as hepatitis c virus inhibitors |
| EP2873669A4 (en) | 2012-07-13 | 2015-11-25 | Takeda Pharmaceutical | HETEROCYCLIC CONNECTION |
| US9834520B2 (en) | 2013-03-14 | 2017-12-05 | Takeda Pharmaceutical Company Limited | Heterocyclic compound |
| ES2950424T3 (es) | 2013-07-03 | 2023-10-09 | Takeda Pharmaceuticals Co | Compuesto de amida |
| JP6427491B2 (ja) | 2013-07-03 | 2018-11-21 | 武田薬品工業株式会社 | 複素環化合物 |
| CN104418784B (zh) * | 2013-09-04 | 2019-02-19 | 浙江九洲药业股份有限公司 | 一种抗病毒药物中间体的拆分方法 |
| CN106256819B (zh) * | 2015-06-19 | 2019-07-09 | 重庆博腾制药科技股份有限公司 | 一种(4S)-N-Boc-4-甲氧基甲基-L-脯氨酸胺盐的合成方法 |
| WO2016202232A1 (zh) * | 2015-06-19 | 2016-12-22 | 重庆博腾制药科技股份有限公司 | 一种(4S)-N-Boc-4-甲氧基甲基-L-脯氨酸胺盐的合成方法 |
| WO2017015439A1 (en) * | 2015-07-21 | 2017-01-26 | Theravance Biopharma R&D Ip, Llc | Crystalline form of a hepatitis c virus inhibitor |
| WO2017062840A1 (en) * | 2015-10-09 | 2017-04-13 | Trek Therapeutics, Pbc | Combination therapy for the treatment of hepatitis c virus |
| CN107501155A (zh) * | 2017-09-19 | 2017-12-22 | 上海泓博智源医药股份有限公司 | 一种抗病毒药物中间体的制备方法 |
| CN114369107B (zh) * | 2020-10-15 | 2025-10-03 | 鲁南制药集团股份有限公司 | 一种拉司米地坦中间体化合物 |
| CN112679407B (zh) * | 2021-03-17 | 2021-06-04 | 南京桦冠生物技术有限公司 | 一种手性5-取代脯氨酸类化合物的制备方法 |
Family Cites Families (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2299207C2 (ru) * | 2001-08-30 | 2007-05-20 | Кова Ко., Лтд. | Соединения циклического амина |
| US6867221B2 (en) | 2001-08-30 | 2005-03-15 | Kowa Co., Ltd. | Cyclic amine compounds and pharmaceutical composition containing the same |
| GB0421908D0 (en) * | 2004-10-01 | 2004-11-03 | Angeletti P Ist Richerche Bio | New uses |
| DK1940786T3 (da) | 2005-09-16 | 2010-11-08 | Arrow Therapeutics Ltd | Biphenylderivater og deres anvendelse ved behandling af hepatitis C |
| US8303944B2 (en) | 2006-08-11 | 2012-11-06 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| CN101558059B (zh) * | 2006-08-11 | 2014-12-03 | 百时美施贵宝公司 | 丙型肝炎病毒抑制剂 |
| US7659270B2 (en) | 2006-08-11 | 2010-02-09 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8329159B2 (en) | 2006-08-11 | 2012-12-11 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| DE102009005746A1 (de) * | 2009-01-23 | 2010-07-29 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
| UY32462A (es) * | 2009-02-23 | 2010-09-30 | Arrow Therapeutics Ltd | Derivados de bifenilo novedosos para el tratamiento de infección por virus de hepatitis c 644 |
| US8796466B2 (en) | 2009-03-30 | 2014-08-05 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| NZ619205A (en) | 2009-05-13 | 2015-04-24 | Gilead Pharmasset Llc | Antiviral compounds |
| NZ597982A (en) | 2009-09-04 | 2013-01-25 | Glaxosmithkline Llc | CHEMICAL COMPOUNDS for treating Hepatitis C virus |
| WO2011031904A1 (en) | 2009-09-11 | 2011-03-17 | Enanta Pharmaceuticals, Inc | Hepatitis c virus inhibitors |
| US8822700B2 (en) | 2009-09-11 | 2014-09-02 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| US20110274648A1 (en) | 2009-11-11 | 2011-11-10 | Bristol-Myers Squibb Company | Hepatitis C Virus Inhibitors |
| EP2512480A4 (en) | 2009-12-14 | 2013-05-15 | Enanta Pharm Inc | HEPATITIS C-VIRUS HEMMER |
| US8377980B2 (en) | 2009-12-16 | 2013-02-19 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| WO2011079327A1 (en) | 2009-12-24 | 2011-06-30 | Vertex Pharmaceuticals Incorporated | Analogues for the treatment or prevention of flavivirus infections |
| WO2011091446A1 (en) | 2010-01-22 | 2011-07-28 | Glaxosmithkline Llc | Chemical compounds |
| US8778938B2 (en) | 2010-06-04 | 2014-07-15 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| US20120195857A1 (en) | 2010-08-12 | 2012-08-02 | Bristol-Myers Squibb Company | Hepatitis C Virus Inhibitors |
| CA2809261A1 (en) | 2010-08-26 | 2012-03-01 | Rfs Pharma, Llc | Potent and selective inhibitors of hepatitis c virus |
| WO2012048421A1 (en) | 2010-10-14 | 2012-04-19 | Boehringer Ingelheim International Gmbh | Hepatitis c inhibitor compounds |
| WO2012061552A1 (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 |
-
2012
- 2012-11-02 BR BR112014010401A patent/BR112014010401A8/pt not_active IP Right Cessation
- 2012-11-02 CA CA2852700A patent/CA2852700A1/en not_active Abandoned
- 2012-11-02 CN CN201280054361.3A patent/CN103946220B/zh not_active Expired - Fee Related
- 2012-11-02 RU RU2014122340A patent/RU2625787C2/ru not_active IP Right Cessation
- 2012-11-02 WO PCT/US2012/063181 patent/WO2013067267A1/en not_active Ceased
- 2012-11-02 TW TW101140863A patent/TWI577672B/zh not_active IP Right Cessation
- 2012-11-02 JP JP2014540112A patent/JP6082747B2/ja not_active Expired - Fee Related
- 2012-11-02 PH PH1/2014/500988A patent/PH12014500988A1/en unknown
- 2012-11-02 AU AU2012332358A patent/AU2012332358B2/en not_active Ceased
- 2012-11-02 SG SG11201401891RA patent/SG11201401891RA/en unknown
- 2012-11-02 AR ARP120104114A patent/AR088630A1/es unknown
- 2012-11-02 HK HK15101128.6A patent/HK1200812A1/xx unknown
- 2012-11-02 US US13/667,197 patent/US9212168B2/en not_active Expired - Fee Related
- 2012-11-02 EP EP12783835.7A patent/EP2773634B1/en active Active
- 2012-11-02 KR KR1020147014928A patent/KR20140091036A/ko not_active Ceased
- 2012-11-02 MX MX2014005342A patent/MX347692B/es active IP Right Grant
-
2014
- 2014-04-09 IL IL232042A patent/IL232042A/en not_active IP Right Cessation
- 2014-04-28 CO CO14090226A patent/CO6940424A2/es active IP Right Grant
- 2014-04-29 CL CL2014001110A patent/CL2014001110A1/es unknown
- 2014-05-02 ZA ZA2014/03198A patent/ZA201403198B/en unknown
-
2015
- 2015-10-15 US US14/883,856 patent/US9669027B2/en not_active Expired - Fee Related
-
2016
- 2016-12-06 JP JP2016236386A patent/JP2017048248A/ja active Pending