JP2007515405A5 - - Google Patents
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- Publication number
- JP2007515405A5 JP2007515405A5 JP2006541549A JP2006541549A JP2007515405A5 JP 2007515405 A5 JP2007515405 A5 JP 2007515405A5 JP 2006541549 A JP2006541549 A JP 2006541549A JP 2006541549 A JP2006541549 A JP 2006541549A JP 2007515405 A5 JP2007515405 A5 JP 2007515405A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- compound
- hcv
- alkoxy
- aryl
- 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
- 150000001875 compounds Chemical class 0.000 claims 51
- 125000000217 alkyl group Chemical group 0.000 claims 46
- 125000003545 alkoxy group Chemical group 0.000 claims 21
- -1 cyano, amino Chemical group 0.000 claims 15
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 14
- 230000000694 effects Effects 0.000 claims 12
- 125000005843 halogen group Chemical group 0.000 claims 12
- 125000003118 aryl group Chemical group 0.000 claims 11
- 229910052736 halogen Inorganic materials 0.000 claims 11
- 150000002367 halogens Chemical class 0.000 claims 10
- 239000003795 chemical substances by application Substances 0.000 claims 9
- 239000008194 pharmaceutical composition Substances 0.000 claims 9
- 125000001424 substituent group Chemical group 0.000 claims 9
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 8
- 125000000623 heterocyclic group Chemical group 0.000 claims 8
- 108010050904 Interferons Proteins 0.000 claims 7
- 102000014150 Interferons Human genes 0.000 claims 7
- 229940079322 interferon Drugs 0.000 claims 7
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 6
- 108010047761 Interferon-alpha Proteins 0.000 claims 6
- 102000006992 Interferon-alpha Human genes 0.000 claims 6
- 125000002877 alkyl aryl group Chemical group 0.000 claims 6
- 150000001408 amides Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 208000015181 infectious disease Diseases 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 102000012479 Serine Proteases Human genes 0.000 claims 5
- 108010022999 Serine Proteases Proteins 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 125000002252 acyl group Chemical group 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 4
- 125000002950 monocyclic group Chemical group 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 3
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 3
- 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 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000005248 alkyl aryloxy group Chemical group 0.000 claims 3
- 125000005907 alkyl ester group Chemical group 0.000 claims 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims 3
- 125000004104 aryloxy group Chemical group 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 230000002401 inhibitory effect Effects 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims 3
- 239000000651 prodrug Substances 0.000 claims 3
- 229940002612 prodrug Drugs 0.000 claims 3
- 229960000329 ribavirin Drugs 0.000 claims 3
- 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 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- 239000011593 sulfur Substances 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 2
- 108091032973 (ribonucleotides)n+m Proteins 0.000 claims 2
- UBCHPRBFMUDMNC-UHFFFAOYSA-N 1-(1-adamantyl)ethanamine Chemical compound C1C(C2)CC3CC2CC1(C(N)C)C3 UBCHPRBFMUDMNC-UHFFFAOYSA-N 0.000 claims 2
- 108020005544 Antisense RNA Proteins 0.000 claims 2
- 229940124186 Dehydrogenase inhibitor Drugs 0.000 claims 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- HAEJPQIATWHALX-KQYNXXCUSA-N ITP Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@H]1N1C(N=CNC2=O)=C2N=C1 HAEJPQIATWHALX-KQYNXXCUSA-N 0.000 claims 2
- 101710200424 Inosine-5'-monophosphate dehydrogenase Proteins 0.000 claims 2
- 102100040018 Interferon alpha-2 Human genes 0.000 claims 2
- 108010079944 Interferon-alpha2b Proteins 0.000 claims 2
- 102000013462 Interleukin-12 Human genes 0.000 claims 2
- 108010065805 Interleukin-12 Proteins 0.000 claims 2
- 102000000588 Interleukin-2 Human genes 0.000 claims 2
- 108010002350 Interleukin-2 Proteins 0.000 claims 2
- 102000004889 Interleukin-6 Human genes 0.000 claims 2
- 108090001005 Interleukin-6 Proteins 0.000 claims 2
- 102000005741 Metalloproteases Human genes 0.000 claims 2
- 108010006035 Metalloproteases Proteins 0.000 claims 2
- 108060004795 Methyltransferase Proteins 0.000 claims 2
- 101800001019 Non-structural protein 4B Proteins 0.000 claims 2
- 101800001014 Non-structural protein 5A Proteins 0.000 claims 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical group N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
- 230000005867 T cell response Effects 0.000 claims 2
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 claims 2
- 229960003805 amantadine Drugs 0.000 claims 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 2
- 239000003184 complementary RNA Substances 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 210000002443 helper t lymphocyte Anatomy 0.000 claims 2
- DOUYETYNHWVLEO-UHFFFAOYSA-N imiquimod Chemical compound C1=CC=CC2=C3N(CC(C)C)C=NC3=C(N)N=C21 DOUYETYNHWVLEO-UHFFFAOYSA-N 0.000 claims 2
- 229960002751 imiquimod Drugs 0.000 claims 2
- 230000002452 interceptive effect Effects 0.000 claims 2
- 229940117681 interleukin-12 Drugs 0.000 claims 2
- 229940100601 interleukin-6 Drugs 0.000 claims 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N iso-quinoline Chemical group C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 229960000888 rimantadine Drugs 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 2
- 229920002554 vinyl polymer Polymers 0.000 claims 2
- PIEXCQIOSMOEOU-UHFFFAOYSA-N 1-bromo-3-chloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Br)C(=O)N(Cl)C1=O PIEXCQIOSMOEOU-UHFFFAOYSA-N 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- WKWZKMNSJYUSCW-UHFFFAOYSA-N [N+](=O)([O-])[N-]O Chemical compound [N+](=O)([O-])[N-]O WKWZKMNSJYUSCW-UHFFFAOYSA-N 0.000 claims 1
- 125000004422 alkyl sulphonamide group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- MKCBRYIXFFGIKN-UHFFFAOYSA-N bicyclo[1.1.1]pentane Chemical compound C1C2CC1C2 MKCBRYIXFFGIKN-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000007306 functionalization reaction Methods 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 229940127073 nucleoside analogue Drugs 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 150000003384 small molecules Chemical class 0.000 claims 1
- 125000004001 thioalkyl group Chemical group 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US52376403P | 2003-11-20 | 2003-11-20 | |
| PCT/US2004/038967 WO2005054430A2 (en) | 2003-11-20 | 2004-11-19 | Hepatitis c virus inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007515405A JP2007515405A (ja) | 2007-06-14 |
| JP2007515405A5 true JP2007515405A5 (enExample) | 2007-12-20 |
| JP4675332B2 JP4675332B2 (ja) | 2011-04-20 |
Family
ID=34652261
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006541549A Expired - Fee Related JP4675332B2 (ja) | 2003-11-20 | 2004-11-19 | Ｃ型肝炎ウイルスインヒビター |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US7309708B2 (enExample) |
| EP (1) | EP1684745B1 (enExample) |
| JP (1) | JP4675332B2 (enExample) |
| IS (1) | IS8475A (enExample) |
| NO (1) | NO20062185L (enExample) |
| WO (1) | WO2005054430A2 (enExample) |
Families Citing this family (82)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY140680A (en) * | 2002-05-20 | 2010-01-15 | Bristol Myers Squibb Co | Hepatitis c virus inhibitors |
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| US7491794B2 (en) * | 2003-10-14 | 2009-02-17 | Intermune, Inc. | Macrocyclic compounds as inhibitors of viral replication |
| EP1856096B1 (en) | 2005-01-10 | 2010-09-01 | Bristol-Myers Squibb Company | Phenylglycinamide derivatives useful as anticoagulants |
| US7323447B2 (en) | 2005-02-08 | 2008-01-29 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US7592336B2 (en) | 2005-05-10 | 2009-09-22 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US7601686B2 (en) | 2005-07-11 | 2009-10-13 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| TWI389908B (zh) * | 2005-07-14 | 2013-03-21 | Gilead Sciences Inc | 抗病毒化合物類 |
| JP2009501546A (ja) * | 2005-07-18 | 2009-01-22 | ノバルティス アーゲー | Ｈｃｖ複製についての小動物モデル |
| KR101294467B1 (ko) * | 2005-07-25 | 2013-09-09 | 인터뮨, 인크. | Ｃ형 간염 바이러스 복제의 신규 거대고리형 억제제 |
| RU2436787C2 (ru) * | 2005-07-29 | 2011-12-20 | Тиботек Фармасьютикалз Лтд. | Макроциклические ингибиторы вируса гепатита с |
| TWI383980B (zh) * | 2005-07-29 | 2013-02-01 | Tibotec Pharm Ltd | Ｃ型肝炎病毒之大環抑制劑 |
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| TWI393723B (zh) * | 2005-07-29 | 2013-04-21 | Tibotec Pharm Ltd | Ｃ型肝炎病毒之大環抑制劑（九） |
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| AU7127298A (en) | 1997-04-14 | 1998-11-11 | Emory University | Serine protease inhibitors |
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| IT1299134B1 (it) | 1998-02-02 | 2000-02-29 | Angeletti P Ist Richerche Bio | Procedimento per la produzione di peptidi con proprieta' inibitrici della proteasi ns3 del virus hcv, peptidi cosi' ottenibili e peptidi |
| EP1066247B1 (en) | 1998-03-31 | 2006-11-22 | Vertex Pharmaceuticals Incorporated | Inhibitors of serine proteases, particularly hepatitis c virus ns3 protease |
| GB9812523D0 (en) | 1998-06-10 | 1998-08-05 | Angeletti P Ist Richerche Bio | Peptide inhibitors of hepatitis c virus ns3 protease |
| ATE298317T1 (de) | 1998-07-27 | 2005-07-15 | Angeletti P Ist Richerche Bio | Diketosäure-derivate als hemmstoffe von polymerasen |
| AR022061A1 (es) | 1998-08-10 | 2002-09-04 | Boehringer Ingelheim Ca Ltd | Peptidos inhibidores de la hepatitis c, una composicion farmaceutica que los contiene, el uso de los mismos para preparar una composicion farmaceutica, el uso de un producto intermedio para la preparacion de estos peptidos y un procedimiento para la preparacion de un peptido analogo de los mismos. |
| US6323180B1 (en) | 1998-08-10 | 2001-11-27 | Boehringer Ingelheim (Canada) Ltd | Hepatitis C inhibitor tri-peptides |
| JP2002523371A (ja) | 1998-08-21 | 2002-07-30 | バイロファーマ・インコーポレイテッド | ウイルス感染および関連疾患を治療または予防するための化合物、組成物および方法 |
| CA2343522A1 (en) | 1998-09-04 | 2000-03-16 | Viropharma Incorporated | Methods for treating or preventing viral infections and associated diseases |
| EP1115286A4 (en) | 1998-09-25 | 2003-07-23 | Viropharma Inc | METHOD FOR TREATING AND PREVENTING VIRAL INFECTIONS AND DISEASES RELATED TO THEM |
| UA74546C2 (en) | 1999-04-06 | 2006-01-16 | Boehringer Ingelheim Ca Ltd | Macrocyclic peptides having activity relative to hepatitis c virus, a pharmaceutical composition and use of the pharmaceutical composition |
| US6566365B1 (en) | 1999-11-04 | 2003-05-20 | Biochem Pharma Inc. | Method for the treatment of Flaviviridea viral infection using nucleoside analogues |
| CA2363274A1 (en) | 1999-12-27 | 2001-07-05 | Japan Tobacco Inc. | Fused-ring compounds and use thereof as drugs for hepatitis c |
| US20040034041A1 (en) | 2000-05-10 | 2004-02-19 | Dashyant Dhanak | Novel anti-infectives |
| US6448281B1 (en) | 2000-07-06 | 2002-09-10 | Boehringer Ingelheim (Canada) Ltd. | Viral polymerase inhibitors |
| GB0017676D0 (en) | 2000-07-19 | 2000-09-06 | Angeletti P Ist Richerche Bio | Inhibitors of viral polymerase |
| CA2429359A1 (en) | 2000-11-20 | 2002-08-08 | Bristol-Myers Squibb Company | Hepatitis c tripeptide inhibitors |
| US6867185B2 (en) * | 2001-12-20 | 2005-03-15 | Bristol-Myers Squibb Company | Inhibitors of hepatitis C virus |
| CA2369711A1 (en) | 2002-01-30 | 2003-07-30 | Boehringer Ingelheim (Canada) Ltd. | Macrocyclic peptides active against the hepatitis c virus |
| US6642204B2 (en) | 2002-02-01 | 2003-11-04 | Boehringer Ingelheim International Gmbh | Hepatitis C inhibitor tri-peptides |
| US7091184B2 (en) | 2002-02-01 | 2006-08-15 | Boehringer Ingelheim International Gmbh | Hepatitis C inhibitor tri-peptides |
| CA2369970A1 (en) | 2002-02-01 | 2003-08-01 | Boehringer Ingelheim (Canada) Ltd. | Hepatitis c inhibitor tri-peptides |
| CA2370396A1 (en) | 2002-02-01 | 2003-08-01 | Boehringer Ingelheim (Canada) Ltd. | Hepatitis c inhibitor tri-peptides |
| US6828301B2 (en) | 2002-02-07 | 2004-12-07 | Boehringer Ingelheim International Gmbh | Pharmaceutical compositions for hepatitis C viral protease inhibitors |
| BR0309669A (pt) * | 2002-04-23 | 2005-03-01 | Bristol Myers Squibb Co | Compostos de anilina de pirrolo-triazina úteis como inibidores de cinase |
| PL213029B1 (pl) * | 2002-05-20 | 2012-12-31 | Bristol Myers Squibb Co | Podstawiona pochodna cykloalkilowa, zawierajaca ja kompozycja oraz ich zastosowanie |
| MY140680A (en) | 2002-05-20 | 2010-01-15 | Bristol Myers Squibb Co | Hepatitis c virus inhibitors |
| DE60334205D1 (en) * | 2002-05-20 | 2010-10-28 | Bristol Myers Squibb Co | Heterocyclische sulfonamid-hepatitis-c-virus-hemmer |
| EP1506172B1 (en) * | 2002-05-20 | 2011-03-30 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
| US20040180815A1 (en) * | 2003-03-07 | 2004-09-16 | Suanne Nakajima | Pyridazinonyl macrocyclic hepatitis C serine protease inhibitors |
| US7132504B2 (en) | 2003-11-12 | 2006-11-07 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
-
2004
- 2004-11-18 US US10/992,566 patent/US7309708B2/en not_active Expired - Lifetime
- 2004-11-19 WO PCT/US2004/038967 patent/WO2005054430A2/en not_active Ceased
- 2004-11-19 EP EP04811656.0A patent/EP1684745B1/en not_active Expired - Lifetime
- 2004-11-19 JP JP2006541549A patent/JP4675332B2/ja not_active Expired - Fee Related
-
2006
- 2006-05-15 NO NO20062185A patent/NO20062185L/no not_active Application Discontinuation
- 2006-05-18 IS IS8475A patent/IS8475A/is unknown
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