JP2007534662A5 - - Google Patents
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- Publication number
- JP2007534662A5 JP2007534662A5 JP2006549804A JP2006549804A JP2007534662A5 JP 2007534662 A5 JP2007534662 A5 JP 2007534662A5 JP 2006549804 A JP2006549804 A JP 2006549804A JP 2006549804 A JP2006549804 A JP 2006549804A JP 2007534662 A5 JP2007534662 A5 JP 2007534662A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- cycloalkyl
- optionally
- het
- group
- 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 206
- 125000000753 cycloalkyl group Chemical group 0.000 claims 79
- 150000001875 compounds Chemical class 0.000 claims 35
- 229910052736 halogen Inorganic materials 0.000 claims 33
- 150000002367 halogens Chemical class 0.000 claims 33
- 125000001424 substituent group Chemical group 0.000 claims 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 19
- 229910052760 oxygen Inorganic materials 0.000 claims 19
- 125000003118 aryl group Chemical group 0.000 claims 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims 16
- 229910052717 sulfur Inorganic materials 0.000 claims 16
- 125000000304 alkynyl group Chemical group 0.000 claims 15
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 14
- -1 optionally Chemical group 0.000 claims 14
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 13
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 13
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 10
- 125000003342 alkenyl group Chemical group 0.000 claims 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 10
- 229910052794 bromium Inorganic materials 0.000 claims 10
- 229910052801 chlorine Inorganic materials 0.000 claims 10
- 239000000460 chlorine Substances 0.000 claims 10
- 229910052731 fluorine Inorganic materials 0.000 claims 10
- 239000011737 fluorine Substances 0.000 claims 10
- 239000003112 inhibitor Substances 0.000 claims 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 10
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 9
- 229920006395 saturated elastomer Polymers 0.000 claims 9
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 8
- 125000004104 aryloxy group Chemical group 0.000 claims 7
- 125000005842 heteroatom Chemical group 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 6
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 6
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- 125000002947 alkylene group Chemical group 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 4
- 150000002148 esters Chemical class 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 4
- 239000003443 antiviral agent Substances 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 229940079322 interferon Drugs 0.000 claims 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 3
- 125000005647 linker group Chemical group 0.000 claims 3
- 125000002950 monocyclic group Chemical group 0.000 claims 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 2
- 125000006017 1-propenyl group Chemical group 0.000 claims 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- 108020004684 Internal Ribosome Entry Sites Proteins 0.000 claims 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 239000002955 immunomodulating agent Substances 0.000 claims 2
- 229940121354 immunomodulator Drugs 0.000 claims 2
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims 2
- 125000001041 indolyl group Chemical group 0.000 claims 2
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000003226 pyrazolyl 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
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 2
- 125000005958 tetrahydrothienyl group Chemical group 0.000 claims 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 125000001425 triazolyl group Chemical group 0.000 claims 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
- 208000005176 Hepatitis C Diseases 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 108060004795 Methyltransferase Proteins 0.000 claims 1
- 108091005804 Peptidases Proteins 0.000 claims 1
- 239000004365 Protease Substances 0.000 claims 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims 1
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical group 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 1
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 claims 1
- 101800001838 Serine protease/helicase NS3 Proteins 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 1
- 241000700605 Viruses Species 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000005103 alkyl silyl group Chemical group 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 230000001143 conditioned effect Effects 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 208000010710 hepatitis C virus infection Diseases 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 230000002584 immunomodulator Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 229960000329 ribavirin Drugs 0.000 claims 1
- 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 1
- 239000011593 sulfur Substances 0.000 claims 1
- 0 C*[C@](*)(C(*(C[C@@](C1)O*)[C@@]1C1OC1*[C@]1([C@](C)C1)C(*)=O)=O)NC(**)=O Chemical compound C*[C@](*)(C(*(C[C@@](C1)O*)[C@@]1C1OC1*[C@]1([C@](C)C1)C(*)=O)=O)NC(**)=O 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53786304P | 2004-01-21 | 2004-01-21 | |
| PCT/CA2005/000055 WO2005070955A1 (en) | 2004-01-21 | 2005-01-18 | Macrocyclic peptides active against the hepatitis c virus |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007534662A JP2007534662A (ja) | 2007-11-29 |
| JP2007534662A5 true JP2007534662A5 (https=) | 2008-03-06 |
| JP4682155B2 JP4682155B2 (ja) | 2011-05-11 |
Family
ID=34807139
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006549804A Expired - Fee Related JP4682155B2 (ja) | 2004-01-21 | 2005-01-18 | C型肝炎ウイルスに対して活性な大環状ペプチド |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US7749961B2 (https=) |
| EP (1) | EP1730167B1 (https=) |
| JP (1) | JP4682155B2 (https=) |
| AR (1) | AR047444A1 (https=) |
| AT (1) | ATE495185T1 (https=) |
| CA (1) | CA2549851C (https=) |
| DE (1) | DE602005025855D1 (https=) |
| ES (1) | ES2358333T3 (https=) |
| PE (1) | PE20050764A1 (https=) |
| TW (1) | TW200528094A (https=) |
| UY (1) | UY28722A1 (https=) |
| WO (1) | WO2005070955A1 (https=) |
Families Citing this family (115)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100509388B1 (ko) | 1996-10-18 | 2005-08-23 | 버텍스 파마슈티칼스 인코포레이티드 | 세린 프로테아제, 특히 간염 c 바이러스 ns3 프로테아제의 저해제 |
| SV2003000617A (es) | 2000-08-31 | 2003-01-13 | Lilly Co Eli | Inhibidores de la proteasa peptidomimetica ref. x-14912m |
| JP2003007697A (ja) * | 2001-06-21 | 2003-01-10 | Hitachi Kokusai Electric Inc | 半導体装置の製造方法、基板処理方法および基板処理装置 |
| MY140680A (en) | 2002-05-20 | 2010-01-15 | Bristol Myers Squibb Co | Hepatitis c virus inhibitors |
| US7176208B2 (en) | 2003-04-18 | 2007-02-13 | Enanta Pharmaceuticals, Inc. | Quinoxalinyl macrocyclic hepatitis C serine protease inhibitors |
| TWI359147B (en) | 2003-09-05 | 2012-03-01 | Vertex Pharma | Inhibitors of serine proteases, particularly hcv n |
| ES2361997T3 (es) * | 2003-09-22 | 2011-06-27 | Boehringer Ingelheim International Gmbh | Péptidos macrocíclicos activos contra el virus de la hepatitis c. |
| US7491794B2 (en) * | 2003-10-14 | 2009-02-17 | Intermune, Inc. | Macrocyclic compounds as inhibitors of viral replication |
| ATE495185T1 (de) | 2004-01-21 | 2011-01-15 | Boehringer Ingelheim Int | Makrocyclische peptide mit wirkung gegen das hepatitis-c-virus |
| RU2007116265A (ru) | 2004-10-01 | 2008-11-10 | Вертекс Фармасьютикалз Инкорпорейтед (Us) | Ингибирование протеазы ns3-ns4a вируса hcv |
| MX2007004783A (es) * | 2004-10-21 | 2007-05-11 | Pfizer | Inhibidores de la proteasa del virus de la hepatitis c, y composiciones y tratamientos que los usan. |
| TW201424733A (zh) | 2004-10-29 | 2014-07-01 | Vertex Pharma | 劑量型式 |
| US7323447B2 (en) | 2005-02-08 | 2008-01-29 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| AU2006242475B2 (en) | 2005-05-02 | 2011-07-07 | Merck Sharp & Dohme Corp. | HCV NS3 protease inhibitors |
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| BRPI0614205A2 (pt) | 2005-08-01 | 2016-11-22 | Merck & Co Inc | composto, composição farmacêutica, e, uso de composto |
| US8076365B2 (en) | 2005-08-12 | 2011-12-13 | Boehringer Ingelheim International Gmbh | Viral polymerase inhibitors |
| AR055395A1 (es) | 2005-08-26 | 2007-08-22 | Vertex Pharma | Compuestos inhibidores de la actividad de la serina proteasa ns3-ns4a del virus de la hepatitis c |
| US7964624B1 (en) | 2005-08-26 | 2011-06-21 | Vertex Pharmaceuticals Incorporated | Inhibitors of serine proteases |
| AU2006301966A1 (en) | 2005-10-11 | 2007-04-19 | Array Biopharma, Inc. | Compounds and methods for inhibiting hepatitis C viral replication |
| US7772183B2 (en) | 2005-10-12 | 2010-08-10 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
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| US7816348B2 (en) | 2006-02-03 | 2010-10-19 | Boehringer Ingelheim International Gmbh | Viral polymerase inhibitors |
| EP1991229A2 (en) | 2006-02-27 | 2008-11-19 | Vertex Pharmaceuticals Incorporated | Co-crystals and pharmaceutical compositions comprising the same |
| EP1993994A2 (en) | 2006-03-16 | 2008-11-26 | Vertex Pharmceuticals Incorporated | Deuterated hepatitis c protease inhibitors |
| GB0609492D0 (en) | 2006-05-15 | 2006-06-21 | Angeletti P Ist Richerche Bio | Therapeutic agents |
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| PE20080992A1 (es) | 2006-06-26 | 2008-08-06 | Enanta Pharm Inc | Quinoxalinil macrociclicos inhibidores de serina proteasa del virus de la hepatitis c |
| KR20090024834A (ko) * | 2006-07-05 | 2009-03-09 | 인터뮨, 인크. | C형 간염 바이러스 복제의 신규 억제제 |
| EP2049474B1 (en) | 2006-07-11 | 2015-11-04 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
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| CN101583372A (zh) | 2006-10-24 | 2009-11-18 | 默克公司 | Hcv ns3蛋白酶抑制剂 |
| JP2010507656A (ja) | 2006-10-24 | 2010-03-11 | メルク エンド カムパニー インコーポレーテッド | Hcvns3プロテアーゼ阻害剤 |
| US8138164B2 (en) | 2006-10-24 | 2012-03-20 | Merck Sharp & Dohme Corp. | HCV NS3 protease inhibitors |
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| WO2008057209A1 (en) | 2006-10-27 | 2008-05-15 | Merck & Co., Inc. | Hcv ns3 protease inhibitors |
| US8343477B2 (en) | 2006-11-01 | 2013-01-01 | Bristol-Myers Squibb Company | Inhibitors of hepatitis C virus |
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| GB0625345D0 (en) | 2006-12-20 | 2007-01-31 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
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| CN101835774B (zh) | 2007-08-30 | 2014-09-17 | 弗特克斯药品有限公司 | 共晶体和包含该共晶体的药物组合物 |
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| RU2490272C2 (ru) | 2008-02-04 | 2013-08-20 | Айденикс Фармасьютикалз, Инк. | Макроциклические ингибиторы серинпротеазы |
| EA201071034A1 (ru) | 2008-04-15 | 2011-06-30 | Интермьюн, Инк. | Новые макроциклические ингибиторы репликаций вируса гепатита с |
| US8163921B2 (en) | 2008-04-16 | 2012-04-24 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| AU2009241445A1 (en) | 2008-04-28 | 2009-11-05 | Merck Sharp & Dohme Corp. | HCV NS3 protease inhibitors |
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- 2005-01-18 ES ES05706397T patent/ES2358333T3/es not_active Expired - Lifetime
- 2005-01-18 DE DE602005025855T patent/DE602005025855D1/de not_active Expired - Lifetime
- 2005-01-18 WO PCT/CA2005/000055 patent/WO2005070955A1/en not_active Ceased
- 2005-01-19 US US11/039,698 patent/US7749961B2/en not_active Expired - Lifetime
- 2005-01-19 UY UY28722A patent/UY28722A1/es not_active Application Discontinuation
- 2005-01-19 PE PE2005000074A patent/PE20050764A1/es not_active Application Discontinuation
- 2005-01-20 TW TW094101708A patent/TW200528094A/zh unknown
- 2005-01-21 AR ARP050100220A patent/AR047444A1/es unknown
-
2009
- 2009-06-29 US US12/493,681 patent/US20090264346A1/en not_active Abandoned
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