JP2013538235A5 - - Google Patents
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- Publication number
- JP2013538235A5 JP2013538235A5 JP2013529408A JP2013529408A JP2013538235A5 JP 2013538235 A5 JP2013538235 A5 JP 2013538235A5 JP 2013529408 A JP2013529408 A JP 2013529408A JP 2013529408 A JP2013529408 A JP 2013529408A JP 2013538235 A5 JP2013538235 A5 JP 2013538235A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- cycloalkenyl
- cycloalkyl
- alkyl
- alkenyl
- 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
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- -1 substituted Chemical class 0.000 claims 164
- 125000000753 cycloalkyl group Chemical group 0.000 claims 68
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 64
- 125000005842 heteroatom Chemical group 0.000 claims 64
- 229910052717 sulfur Inorganic materials 0.000 claims 64
- 125000000217 alkyl group Chemical group 0.000 claims 60
- 229910052757 nitrogen Inorganic materials 0.000 claims 58
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 55
- 125000001072 heteroaryl group Chemical group 0.000 claims 54
- 229910052760 oxygen Inorganic materials 0.000 claims 44
- 229910052739 hydrogen Inorganic materials 0.000 claims 34
- 239000001257 hydrogen Substances 0.000 claims 34
- 125000003118 aryl group Chemical group 0.000 claims 29
- 125000003107 substituted aryl group Chemical group 0.000 claims 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 23
- 125000000304 alkynyl group Chemical group 0.000 claims 23
- 125000000623 heterocyclic group Chemical group 0.000 claims 22
- 125000005843 halogen group Chemical group 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 13
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 12
- 229910052799 carbon Inorganic materials 0.000 claims 12
- 150000002431 hydrogen Chemical class 0.000 claims 11
- 239000008194 pharmaceutical composition Substances 0.000 claims 11
- 229910052736 halogen Inorganic materials 0.000 claims 9
- 150000002367 halogens Chemical class 0.000 claims 9
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 6
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 6
- 125000004450 alkenylene group Chemical group 0.000 claims 6
- 125000002947 alkylene group Chemical group 0.000 claims 6
- 125000004419 alkynylene group Chemical group 0.000 claims 6
- 229910052805 deuterium Inorganic materials 0.000 claims 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
- 239000003795 chemical substances by application Substances 0.000 claims 5
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 5
- 239000003937 drug carrier Substances 0.000 claims 5
- 150000002148 esters Chemical class 0.000 claims 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims 5
- 239000000651 prodrug Substances 0.000 claims 5
- 229940002612 prodrug Drugs 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 5
- 229920002554 vinyl polymer Polymers 0.000 claims 5
- 229940079322 interferon Drugs 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 241000711549 Hepacivirus C Species 0.000 claims 3
- 208000005176 Hepatitis C Diseases 0.000 claims 3
- 241000700605 Viruses Species 0.000 claims 3
- 125000005724 cycloalkenylene group Chemical group 0.000 claims 3
- 125000002993 cycloalkylene group Chemical group 0.000 claims 3
- 230000002401 inhibitory effect Effects 0.000 claims 3
- 102000014150 Interferons Human genes 0.000 claims 2
- 108010050904 Interferons Proteins 0.000 claims 2
- 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 2
- 208000036142 Viral infection Diseases 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 239000003112 inhibitor Substances 0.000 claims 2
- 229960000329 ribavirin Drugs 0.000 claims 2
- 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 2
- 230000009385 viral infection Effects 0.000 claims 2
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims 1
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229940124683 HCV polymerase inhibitor Drugs 0.000 claims 1
- 229940122604 HCV protease inhibitor Drugs 0.000 claims 1
- 229940121759 Helicase inhibitor Drugs 0.000 claims 1
- 102000005741 Metalloproteases Human genes 0.000 claims 1
- 108010006035 Metalloproteases Proteins 0.000 claims 1
- 108060004795 Methyltransferase Proteins 0.000 claims 1
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims 1
- 229910001573 adamantine Inorganic materials 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 claims 1
- 229960003805 amantadine Drugs 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 claims 1
- 239000003429 antifungal agent Substances 0.000 claims 1
- 229940121375 antifungal agent Drugs 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 239000003443 antiviral agent Substances 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 108700012707 hepatitis C virus NS3 Proteins 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 230000029812 viral genome replication Effects 0.000 claims 1
- 0 C*(C*(C)IC(C(OC(*)(CC1C(NC2(C(*)C2)C(*)=O)=O)CN1C(C(*)N*N=C)=O)=NC(*)=C(C)*)=*)*C(C=C*)=C Chemical compound C*(C*(C)IC(C(OC(*)(CC1C(NC2(C(*)C2)C(*)=O)=O)CN1C(C(*)N*N=C)=O)=NC(*)=C(C)*)=*)*C(C=C*)=C 0.000 description 7
- UAEPNZWRGJTJPN-UHFFFAOYSA-N CC1CCCCC1 Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 1
- OVRKATYHWPCGPZ-UHFFFAOYSA-N CC1CCOCC1 Chemical compound CC1CCOCC1 OVRKATYHWPCGPZ-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38505810P | 2010-09-21 | 2010-09-21 | |
| US61/385,058 | 2010-09-21 | ||
| US201161499994P | 2011-06-22 | 2011-06-22 | |
| US61/499,994 | 2011-06-22 | ||
| US201161504616P | 2011-07-05 | 2011-07-05 | |
| US61/504,616 | 2011-07-05 | ||
| PCT/US2011/052304 WO2012040167A1 (en) | 2010-09-21 | 2011-09-20 | Macrocyclic proline derived hcv serine protease inhibitors |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015241811A Division JP6352238B2 (ja) | 2010-09-21 | 2015-12-11 | 大環式プロリン由来ｈｃｖセリンプロテアーゼ阻害剤 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013538235A JP2013538235A (ja) | 2013-10-10 |
| JP2013538235A5 true JP2013538235A5 (OSRAM) | 2014-04-10 |
| JP5857053B2 JP5857053B2 (ja) | 2016-02-10 |
Family
ID=45817947
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013529408A Active JP5857053B2 (ja) | 2010-09-21 | 2011-09-20 | 大環式プロリン由来ｈｃｖセリンプロテアーゼ阻害剤 |
| JP2015241811A Active JP6352238B2 (ja) | 2010-09-21 | 2015-12-11 | 大環式プロリン由来ｈｃｖセリンプロテアーゼ阻害剤 |
| JP2018107455A Active JP6574023B2 (ja) | 2010-09-21 | 2018-06-05 | 大環式プロリン由来ｈｃｖセリンプロテアーゼ阻害剤 |
| JP2019148420A Pending JP2020015730A (ja) | 2010-09-21 | 2019-08-13 | 大環式プロリン由来ｈｃｖセリンプロテアーゼ阻害剤 |
| JP2021004680A Ceased JP2021063130A (ja) | 2010-09-21 | 2021-01-15 | 大環式プロリン由来ｈｃｖセリンプロテアーゼ阻害剤 |
Family Applications After (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015241811A Active JP6352238B2 (ja) | 2010-09-21 | 2015-12-11 | 大環式プロリン由来ｈｃｖセリンプロテアーゼ阻害剤 |
| JP2018107455A Active JP6574023B2 (ja) | 2010-09-21 | 2018-06-05 | 大環式プロリン由来ｈｃｖセリンプロテアーゼ阻害剤 |
| JP2019148420A Pending JP2020015730A (ja) | 2010-09-21 | 2019-08-13 | 大環式プロリン由来ｈｃｖセリンプロテアーゼ阻害剤 |
| JP2021004680A Ceased JP2021063130A (ja) | 2010-09-21 | 2021-01-15 | 大環式プロリン由来ｈｃｖセリンプロテアーゼ阻害剤 |
Country Status (43)
Families Citing this family (49)
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| CN102458444A (zh) * | 2009-05-13 | 2012-05-16 | 英安塔制药有限公司 | 用作丙型肝炎病毒抑制剂的大环化合物 |
| WO2011049908A2 (en) * | 2009-10-19 | 2011-04-28 | Enanta Pharmaceuticals, Inc. | Bismacrokyclic compounds as hepatitis c virus inhibitors |
| KR101894704B1 (ko) | 2010-09-21 | 2018-09-05 | 이난타 파마슈티칼스, 인코포레이티드 | 매크로사이클릭 프롤린 유도된 ｈｃｖ 세린 프로테아제 억제제 |
| US8957203B2 (en) | 2011-05-05 | 2015-02-17 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| UA119315C2 (uk) | 2012-07-03 | 2019-06-10 | Гіліад Фармассет Елелсі | Інгібітори вірусу гепатиту с |
| SI2909205T1 (sl) | 2012-10-19 | 2017-02-28 | Bristol-Myers Squibb Company | 9-metil substituiran heksadekahidrociklopropa(e)pirolo(1,2-A)(1,4)diazaciklopentadecinil karbamat derivati kot nestrukturalni 3 (NS3) proteazni inhibitorji za zdravljenje hepatitis C virusnih infekcij |
| US9643999B2 (en) | 2012-11-02 | 2017-05-09 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
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| US9580463B2 (en) | 2013-03-07 | 2017-02-28 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US20200368229A9 (en) * | 2013-03-14 | 2020-11-26 | Abbvie Inc. | Methods for Treating HCV |
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| US20180042982A1 (en) * | 2013-03-14 | 2018-02-15 | Abbvie Inc. | Methods for Treating HCV |
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| CA2925328A1 (en) * | 2013-10-25 | 2015-04-30 | Abbvie, Inc. | Methods for treating hcv |
| SG11201604482QA (en) * | 2013-12-23 | 2016-07-28 | Gilead Sciences Inc | Synthesis of a macrocyclic hcv ns3 inhibiting tripeptide |
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| US9809576B1 (en) * | 2014-07-18 | 2017-11-07 | Abbvie Inc. | Synthetic route to anti-viral agents |
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| US10059969B1 (en) | 2014-10-03 | 2018-08-28 | Abbvie Inc. | Process for the preparation of (S)-2-amino-non-8-enoic acid |
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| JP6808660B2 (ja) | 2015-07-08 | 2021-01-06 | アッヴィ・インコーポレイテッド | Ｈｃｖを処置するための方法 |
| CA2992722C (en) * | 2015-07-17 | 2023-10-17 | Abbvie Inc. | Solid pharmaceutical compositions for treating hcv |
| KR101726567B1 (ko) | 2016-07-08 | 2017-04-13 | 박공영 | 수직형 식물 재배장치 |
| AU2018215337A1 (en) | 2017-02-01 | 2019-08-22 | Abbvie Inc. | Enzymatic processes for the preparation of (±)-2-(difluoromethyl)-1-(alkoxycarbonyl)-cyclopropanecarboxylic acid and(±)-2-(vinyl)-1-(alkoxycarbonyl)-cyclopropanecarboxylic acid |
| CA2994496A1 (en) | 2017-02-14 | 2018-08-14 | Abbvie Inc. | Methods for treating hcv |
| CA2981993A1 (en) * | 2017-08-02 | 2019-02-02 | Abbvie Inc. | Methods for treating hcv |
| WO2019046569A1 (en) * | 2017-09-01 | 2019-03-07 | Abbvie Inc. | METHODS FOR THE TREATMENT OF HCV |
| CA3078939A1 (en) | 2017-10-12 | 2019-04-18 | Abbvie Inc. | Methods for treating hcv |
| CN107739319A (zh) * | 2017-10-31 | 2018-02-27 | 上海同昌生物医药科技有限公司 | 一种Glecaprevir合成中间体及其胺盐的制备方法 |
| WO2019084740A1 (zh) * | 2017-10-31 | 2019-05-09 | 上海同昌生物医药科技有限公司 | 一种Glecaprevir合成中间体及其胺盐的制备方法 |
| CN108329332A (zh) * | 2018-03-16 | 2018-07-27 | 安徽华昌高科药业有限公司 | 一种制备Glecaprevir的方法 |
| CA3136316A1 (en) | 2019-04-08 | 2020-10-15 | Abbvie Inc. | Solid pharmaceutical compositions for treating hcv |
| KR102681664B1 (ko) | 2019-06-12 | 2024-07-05 | 엘지디스플레이 주식회사 | 폴더블 디스플레이와 그 구동 방법 |
| WO2021137256A1 (en) | 2020-01-03 | 2021-07-08 | Mylan Laboratories Limited | Polymorphic forms of glecaprevir |
| US20230218644A1 (en) | 2020-04-16 | 2023-07-13 | Som Innovation Biotech, S.A. | Compounds for use in the treatment of viral infections by respiratory syndrome-related coronavirus |
| US12083099B2 (en) | 2020-10-28 | 2024-09-10 | Accencio LLC | Methods of treating symptoms of coronavirus infection with viral protease inhibitors |
| CN114085458A (zh) * | 2021-12-08 | 2022-02-25 | 宁波塑之华塑化有限公司 | 一种高强度高韧性阻燃聚丙烯复合材料及其制备方法 |
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