JP2013544812A5 - - Google Patents
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- Publication number
- JP2013544812A5 JP2013544812A5 JP2013537808A JP2013537808A JP2013544812A5 JP 2013544812 A5 JP2013544812 A5 JP 2013544812A5 JP 2013537808 A JP2013537808 A JP 2013537808A JP 2013537808 A JP2013537808 A JP 2013537808A JP 2013544812 A5 JP2013544812 A5 JP 2013544812A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- cycloalkyl
- optionally substituted
- hydrogen
- nhc
- 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 295
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 76
- 229910052739 hydrogen Inorganic materials 0.000 claims description 72
- 239000001257 hydrogen Substances 0.000 claims description 72
- 150000001875 compounds Chemical class 0.000 claims description 61
- 125000005843 halogen group Chemical group 0.000 claims description 44
- 125000001072 heteroaryl group Chemical group 0.000 claims description 42
- 125000000623 heterocyclic group Chemical group 0.000 claims description 41
- 125000003545 alkoxy group Chemical group 0.000 claims description 40
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 33
- 150000002431 hydrogen Chemical class 0.000 claims description 30
- 239000002777 nucleoside Substances 0.000 claims description 30
- 150000003833 nucleoside derivatives Chemical class 0.000 claims description 30
- 229910052799 carbon Inorganic materials 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 102000014150 Interferons Human genes 0.000 claims description 20
- 108010050904 Interferons Proteins 0.000 claims description 20
- 229940047124 interferons Drugs 0.000 claims description 20
- 239000003814 drug Substances 0.000 claims description 19
- 239000008194 pharmaceutical composition Substances 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 229940124597 therapeutic agent Drugs 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
- 241000124008 Mammalia Species 0.000 claims description 15
- -1 —NHCH 3 Chemical group 0.000 claims description 15
- 208000010710 hepatitis C virus infection Diseases 0.000 claims description 11
- 229940124771 HCV-NS3 protease inhibitor Drugs 0.000 claims description 10
- 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 10
- 108700008776 hepatitis C virus NS-5 Proteins 0.000 claims description 10
- 239000003112 inhibitor Substances 0.000 claims description 10
- 229960000329 ribavirin Drugs 0.000 claims description 10
- 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 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 150000001721 carbon Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000006413 ring segment Chemical group 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- 241000711549 Hepacivirus C Species 0.000 claims description 6
- 230000002401 inhibitory effect Effects 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 230000010076 replication Effects 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 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
- DYEXGZBLHUAIJJ-UHFFFAOYSA-N 1-(2,2-dimethylcyclopropyl)-2-methylpyrrolidine Chemical compound CC1CCCN1C1C(C)(C)C1 DYEXGZBLHUAIJJ-UHFFFAOYSA-N 0.000 claims description 2
- DODHZNAXGLNLGI-UHFFFAOYSA-N 1-cyclopropyl-2-methylpyrrolidine Chemical compound CC1CCCN1C1CC1 DODHZNAXGLNLGI-UHFFFAOYSA-N 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- KOBDKUVEIRTGAJ-UHFFFAOYSA-N methyl 2-methylpyrrolidine-1-carboxylate Chemical compound COC(=O)N1CCCC1C KOBDKUVEIRTGAJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 description 7
- 0 CC**(*C)C(**)C(*(CCC1)[C@@]1C1=*C(c(cc2)ccc2-c2ccc(*(C)C(C3=CC=C(*(CC4)CC*4C(*C)=O)I(C)=C3)=O)cc2)=C*1C)=O Chemical compound CC**(*C)C(**)C(*(CCC1)[C@@]1C1=*C(c(cc2)ccc2-c2ccc(*(C)C(C3=CC=C(*(CC4)CC*4C(*C)=O)I(C)=C3)=O)cc2)=C*1C)=O 0.000 description 6
- BQUJMOCJNLYVAV-NMHGFXMVSA-N CC(C)[C@@H](C(N(CCC1)C1c1nc(-c(cc2)ccc2-c(c(OC(F)(F)F)c2)cc(Cl)c2NC(c(cc2)cnc2N(CC2)[C@H](C)CN2C(c2c[nH]cn2)=O)=O)c[nH]1)=O)NC(OC)=O Chemical compound CC(C)[C@@H](C(N(CCC1)C1c1nc(-c(cc2)ccc2-c(c(OC(F)(F)F)c2)cc(Cl)c2NC(c(cc2)cnc2N(CC2)[C@H](C)CN2C(c2c[nH]cn2)=O)=O)c[nH]1)=O)NC(OC)=O BQUJMOCJNLYVAV-NMHGFXMVSA-N 0.000 description 1
- KUHMLERCNDMMDA-LQEVUUGDSA-N CC(C)[C@@H](C(N(CCC1)[C@@H]1c1nc(-c(cc2)ccc2-c(c(C(F)(F)F)c2)cc(F)c2NC(c(cc2)cnc2N(CC2)[C@H](C)CN2C([C@@H]2C(C)(C)C2)=O)=O)c[nH]1)=O)NC(OC)=O Chemical compound CC(C)[C@@H](C(N(CCC1)[C@@H]1c1nc(-c(cc2)ccc2-c(c(C(F)(F)F)c2)cc(F)c2NC(c(cc2)cnc2N(CC2)[C@H](C)CN2C([C@@H]2C(C)(C)C2)=O)=O)c[nH]1)=O)NC(OC)=O KUHMLERCNDMMDA-LQEVUUGDSA-N 0.000 description 1
- QESKXMHWUZEWCA-AKGSCHIQSA-N CC(C)[C@@H](C(N(CCC1)[C@@H]1c1nc(-c(cc2)ccc2-c(c(NC(F)(F)F)c2)cc(Cl)c2NC(c(cc2)cnc2N(CC2)[C@H](C)CN2C([C@@H]2C(C)(C)C2)=[U])=O)c[nH]1)=O)NC(OC)=O Chemical compound CC(C)[C@@H](C(N(CCC1)[C@@H]1c1nc(-c(cc2)ccc2-c(c(NC(F)(F)F)c2)cc(Cl)c2NC(c(cc2)cnc2N(CC2)[C@H](C)CN2C([C@@H]2C(C)(C)C2)=[U])=O)c[nH]1)=O)NC(OC)=O QESKXMHWUZEWCA-AKGSCHIQSA-N 0.000 description 1
- GFYYLFBIILMAEZ-VLHAJMFKSA-N CC(C)[C@@H](C(N(CCC1)[C@@H]1c1nc(-c(cc2)ccc2-c(c([U]C(F)(F)F)c2)cc(F)c2NC(c(cc2)cnc2N(C[C@@H]2C)[C@H](C)CN2C([C@@H]2C(C)(C)C2)=O)=O)c[nH]1)=O)NC(OC)=O Chemical compound CC(C)[C@@H](C(N(CCC1)[C@@H]1c1nc(-c(cc2)ccc2-c(c([U]C(F)(F)F)c2)cc(F)c2NC(c(cc2)cnc2N(C[C@@H]2C)[C@H](C)CN2C([C@@H]2C(C)(C)C2)=O)=O)c[nH]1)=O)NC(OC)=O GFYYLFBIILMAEZ-VLHAJMFKSA-N 0.000 description 1
- MARWFYFKAALXOO-ZBDRNGKCSA-N CC(C)[C@@H](C(N(CCC1)[C@@H]1c1nc(-c(cc2)ccc2-c(c([U]C(F)(F)F)c2)cc(F)c2NC(c(cc2)cnc2N(C[C@@H]2C)[C@H](C)CN2C(c2c[nH]cn2)=O)=O)c[nH]1)=O)NC(OC)=O Chemical compound CC(C)[C@@H](C(N(CCC1)[C@@H]1c1nc(-c(cc2)ccc2-c(c([U]C(F)(F)F)c2)cc(F)c2NC(c(cc2)cnc2N(C[C@@H]2C)[C@H](C)CN2C(c2c[nH]cn2)=O)=O)c[nH]1)=O)NC(OC)=O MARWFYFKAALXOO-ZBDRNGKCSA-N 0.000 description 1
- SWHWQCWIEKSFRM-ASZBYZQXSA-N CC(C)[C@@H](C(N(CCC1)[C@@H]1c1nc(-c(cc2)ccc2-c(ccc(NC(c(cc2)cnc2N(C[C@@H]2C)[C@H](C)CN2C([C@@H]2C(C)(C)C2)=O)=O)c2)c2O[Cl]=[IH])c[nH]1)=N)NC(OC)=[U] Chemical compound CC(C)[C@@H](C(N(CCC1)[C@@H]1c1nc(-c(cc2)ccc2-c(ccc(NC(c(cc2)cnc2N(C[C@@H]2C)[C@H](C)CN2C([C@@H]2C(C)(C)C2)=O)=O)c2)c2O[Cl]=[IH])c[nH]1)=N)NC(OC)=[U] SWHWQCWIEKSFRM-ASZBYZQXSA-N 0.000 description 1
- PARLTOCUUHKJIH-HWVSEBKZSA-N CC(C)[C@@H](C(N(CCC1)[C@@H]1c1nc(-c(cc2)ccc2C(/C(/[U]C(F)(F)F)=C\C(\NC(c(cc2)cnc2N(C[C@@H]2C)[C@H](C)CN2C(NC)=O)=O)=C\F)=C)c[nH]1)=O)NC(OC)=O Chemical compound CC(C)[C@@H](C(N(CCC1)[C@@H]1c1nc(-c(cc2)ccc2C(/C(/[U]C(F)(F)F)=C\C(\NC(c(cc2)cnc2N(C[C@@H]2C)[C@H](C)CN2C(NC)=O)=O)=C\F)=C)c[nH]1)=O)NC(OC)=O PARLTOCUUHKJIH-HWVSEBKZSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000013160 medical therapy Methods 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41026710P | 2010-11-04 | 2010-11-04 | |
| US61/410,267 | 2010-11-04 | ||
| US201161444046P | 2011-02-17 | 2011-02-17 | |
| US61/444,046 | 2011-02-17 | ||
| US201161492267P | 2011-06-01 | 2011-06-01 | |
| US61/492,267 | 2011-06-01 | ||
| PCT/US2011/059061 WO2012061552A1 (en) | 2010-11-04 | 2011-11-03 | Novel inhibitors of hepatitis c virus |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013544812A JP2013544812A (ja) | 2013-12-19 |
| JP2013544812A5 true JP2013544812A5 (enExample) | 2014-11-06 |
| JP5891235B2 JP5891235B2 (ja) | 2016-03-22 |
Family
ID=44993923
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013537808A Expired - Fee Related JP5891235B2 (ja) | 2010-11-04 | 2011-11-03 | Ｃ型肝炎ウイルスの新規阻害剤 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US8921372B2 (enExample) |
| EP (1) | EP2635571B1 (enExample) |
| JP (1) | JP5891235B2 (enExample) |
| CN (1) | CN103189371B (enExample) |
| AR (1) | AR083757A1 (enExample) |
| CA (1) | CA2814534A1 (enExample) |
| ES (1) | ES2548286T3 (enExample) |
| TW (1) | TW201249827A (enExample) |
| WO (1) | WO2012061552A1 (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8921732B2 (en) * | 2007-06-12 | 2014-12-30 | Revolaze, LLC | High speed and high power laser scribing methods and systems |
| PL2368890T3 (pl) | 2009-06-11 | 2013-10-31 | Abbvie Bahamas Ltd | Inhibitory wirusa zapalenia wątroby C |
| US8937150B2 (en) | 2009-06-11 | 2015-01-20 | Abbvie Inc. | Anti-viral compounds |
| NZ605440A (en) | 2010-06-10 | 2014-05-30 | Abbvie Bahamas Ltd | Solid compositions comprising an hcv inhibitor |
| 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 |
| US9546160B2 (en) | 2011-05-12 | 2017-01-17 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US10201584B1 (en) | 2011-05-17 | 2019-02-12 | Abbvie Inc. | Compositions and methods for treating HCV |
| PE20141531A1 (es) | 2011-06-22 | 2014-10-23 | Purdue Pharma Lp | Antagonistas de trpv1 que incluyen sustituyentes dihidroxi y sus usos |
| BR112014010401A8 (pt) * | 2011-11-03 | 2017-12-19 | Theravance Inc | Inibidores do vírus da hepatite c rod-like que contêm o fragmento {2-[4-(bifenil-4-il)-1h-imidazo-2-il] pirrolidina-1-carbonilmetil}amina |
| US9034832B2 (en) | 2011-12-29 | 2015-05-19 | Abbvie Inc. | Solid compositions |
| US9326973B2 (en) | 2012-01-13 | 2016-05-03 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| 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 |
| WO2013165796A1 (en) * | 2012-05-03 | 2013-11-07 | Theravance, Inc. | Crystalline form of a pyridyl-piperazinyl hepatitis c virus inhibitor |
| US11484534B2 (en) | 2013-03-14 | 2022-11-01 | Abbvie Inc. | Methods for treating HCV |
| US9717712B2 (en) | 2013-07-02 | 2017-08-01 | Bristol-Myers Squibb Company | Combinations comprising tricyclohexadecahexaene derivatives for use in the treatment of hepatitis C virus |
| US20150023913A1 (en) | 2013-07-02 | 2015-01-22 | Bristol-Myers Squibb Company | Hepatitis C Virus Inhibitors |
| US9775831B2 (en) | 2013-07-17 | 2017-10-03 | Bristol-Myers Squibb Company | Combinations comprising biphenyl derivatives for use in the treatment of HCV |
| WO2015103490A1 (en) | 2014-01-03 | 2015-07-09 | Abbvie, Inc. | Solid antiviral dosage forms |
| US10617675B2 (en) | 2015-08-06 | 2020-04-14 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| CN105175401A (zh) * | 2015-10-16 | 2015-12-23 | 北京康立生医药技术开发有限公司 | 一种依匹哌唑的制备方法 |
| CN112409336B (zh) * | 2017-11-27 | 2021-09-14 | 常州寅盛药业有限公司 | 适于工业化生产的达卡他韦起始原料的合成方法 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US8329159B2 (en) * | 2006-08-11 | 2012-12-11 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US7745636B2 (en) | 2006-08-11 | 2010-06-29 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US7659270B2 (en) | 2006-08-11 | 2010-02-09 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| 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 |
| US7910722B2 (en) * | 2007-07-05 | 2011-03-22 | Florida State University Research Foundation | RNAi therapeutic for treatment of hepatitis C infection |
| AU2008350327B2 (en) | 2008-02-12 | 2013-09-12 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| CA2750577A1 (en) | 2008-12-03 | 2010-06-10 | Presidio Pharmaceuticals, Inc. | Inhibitors of hcv ns5a |
| WO2010096777A1 (en) | 2009-02-23 | 2010-08-26 | Presidio Pharmaceuticals, Inc. | Inhibitors of hcv ns5a |
| 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 |
| US8822700B2 (en) | 2009-09-11 | 2014-09-02 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| WO2011031934A1 (en) | 2009-09-11 | 2011-03-17 | Enanta Pharmaceuticals, Inc. | 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 |
| US8778938B2 (en) | 2010-06-04 | 2014-07-15 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| WO2012061552A1 (en) * | 2010-11-04 | 2012-05-10 | Theravance, Inc. | Novel inhibitors of hepatitis c virus |
| BR112014010401A8 (pt) | 2011-11-03 | 2017-12-19 | Theravance Inc | Inibidores do vírus da hepatite c rod-like que contêm o fragmento {2-[4-(bifenil-4-il)-1h-imidazo-2-il] pirrolidina-1-carbonilmetil}amina |
-
2011
- 2011-11-03 WO PCT/US2011/059061 patent/WO2012061552A1/en not_active Ceased
- 2011-11-03 CN CN201180053127.4A patent/CN103189371B/zh not_active Expired - Fee Related
- 2011-11-03 ES ES11784875.4T patent/ES2548286T3/es active Active
- 2011-11-03 JP JP2013537808A patent/JP5891235B2/ja not_active Expired - Fee Related
- 2011-11-03 CA CA2814534A patent/CA2814534A1/en not_active Abandoned
- 2011-11-03 US US13/288,216 patent/US8921372B2/en not_active Expired - Fee Related
- 2011-11-03 EP EP11784875.4A patent/EP2635571B1/en active Active
- 2011-11-04 TW TW100140412A patent/TW201249827A/zh unknown
- 2011-11-04 AR ARP110104114A patent/AR083757A1/es not_active Application Discontinuation
-
2014
- 2014-11-12 US US14/539,039 patent/US9260414B2/en not_active Expired - Fee Related