JP2007534636A5 - - Google Patents
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- Publication number
- JP2007534636A5 JP2007534636A5 JP2006539980A JP2006539980A JP2007534636A5 JP 2007534636 A5 JP2007534636 A5 JP 2007534636A5 JP 2006539980 A JP2006539980 A JP 2006539980A JP 2006539980 A JP2006539980 A JP 2006539980A JP 2007534636 A5 JP2007534636 A5 JP 2007534636A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- compound
- hcv
- alkoxy
- cycloalkyl
- 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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- 150000001875 compounds Chemical class 0.000 claims 59
- 125000000217 alkyl group Chemical group 0.000 claims 55
- 125000003545 alkoxy group Chemical group 0.000 claims 27
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 16
- 125000003118 aryl group Chemical group 0.000 claims 16
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 15
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 14
- 125000002877 alkyl aryl group Chemical group 0.000 claims 13
- 230000000694 effects Effects 0.000 claims 12
- -1 cyano, amino Chemical group 0.000 claims 11
- 229910052736 halogen Inorganic materials 0.000 claims 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 11
- 239000003795 chemical substances by application Substances 0.000 claims 10
- 150000002367 halogens Chemical class 0.000 claims 10
- 125000005843 halogen group Chemical group 0.000 claims 9
- 239000008194 pharmaceutical composition Substances 0.000 claims 9
- 125000000623 heterocyclic group Chemical group 0.000 claims 8
- 108010050904 Interferons Proteins 0.000 claims 7
- 102000014150 Interferons Human genes 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- 229940079322 interferon Drugs 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 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
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 102000012479 Serine Proteases Human genes 0.000 claims 5
- 108010022999 Serine Proteases Proteins 0.000 claims 5
- 125000003342 alkenyl group Chemical group 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 238000007306 functionalization reaction Methods 0.000 claims 5
- 125000001424 substituent group Chemical group 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
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 208000015181 infectious disease Diseases 0.000 claims 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 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 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- 125000005248 alkyl aryloxy group Chemical group 0.000 claims 3
- 150000001408 amides Chemical class 0.000 claims 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims 3
- 125000004104 aryloxy group Chemical group 0.000 claims 3
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 3
- AWJUIBRHMBBTKR-UHFFFAOYSA-N iso-quinoline Chemical group C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000002950 monocyclic group Chemical group 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
- 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
- 125000005907 alkyl ester group Chemical group 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
- 239000003184 complementary RNA Substances 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 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
- 230000002401 inhibitory effect Effects 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
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 239000002777 nucleoside Substances 0.000 claims 2
- 229960000888 rimantadine Drugs 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 2
- 229920002554 vinyl polymer Polymers 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 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
- 125000000041 C6-C10 aryl 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
- 125000004171 alkoxy aryl group Chemical group 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
- 125000004367 cycloalkylaryl group Chemical group 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
- 239000000203 mixture Substances 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
- 0 C**(*1C2)C2(C2)C2C1(C(*C)=O)NC([C@@](CC1(CC1)C1)N1C([C@](*)NS)=O)=O Chemical compound C**(*1C2)C2(C2)C2C1(C(*C)=O)NC([C@@](CC1(CC1)C1)N1C([C@](*)NS)=O)=O 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51912403P | 2003-11-12 | 2003-11-12 | |
| PCT/US2004/038165 WO2005046712A1 (en) | 2003-11-12 | 2004-11-12 | Hepatitis c virus inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007534636A JP2007534636A (ja) | 2007-11-29 |
| JP2007534636A5 true JP2007534636A5 (enExample) | 2008-01-17 |
| JP4675331B2 JP4675331B2 (ja) | 2011-04-20 |
Family
ID=34590359
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006539980A Expired - Fee Related JP4675331B2 (ja) | 2003-11-12 | 2004-11-12 | Ｃ型肝炎ウイルスインヒビター |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7132504B2 (enExample) |
| EP (1) | EP1687018B1 (enExample) |
| JP (1) | JP4675331B2 (enExample) |
| AT (1) | ATE542826T1 (enExample) |
| ES (1) | ES2380934T3 (enExample) |
| IS (1) | IS8448A (enExample) |
| NO (1) | NO20062267L (enExample) |
| WO (1) | WO2005046712A1 (enExample) |
Families Citing this family (141)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ335276A (en) | 1996-10-18 | 2000-09-29 | Vertex Pharma | Inhibitors of serine proteases, particularly hepatitis C virus (HCV) NS3 (Non Structural Protein 3) protease |
| SV2003000617A (es) | 2000-08-31 | 2003-01-13 | Lilly Co Eli | Inhibidores de la proteasa peptidomimetica ref. x-14912m |
| 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 |
| CL2004001161A1 (es) * | 2003-05-21 | 2005-04-08 | Boehringer Ingelheim Int | Compuestos describe compuestos derivados de quinolina; composicion farmaceutica; y su uso para tratar una enfermedad causada por el virus de la hepatitis c. |
| MY148123A (en) | 2003-09-05 | 2013-02-28 | Vertex Pharma | Inhibitors of serine proteases, particularly hcv ns3-ns4a protease |
| EP1673385B1 (en) | 2003-09-22 | 2011-03-02 | Boehringer Ingelheim International GmbH | Macrocyclic peptides active against the hepatitis c virus |
| US7491794B2 (en) * | 2003-10-14 | 2009-02-17 | Intermune, Inc. | Macrocyclic compounds as inhibitors of viral replication |
| US7132504B2 (en) | 2003-11-12 | 2006-11-07 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US7135462B2 (en) | 2003-11-20 | 2006-11-14 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US7309708B2 (en) | 2003-11-20 | 2007-12-18 | Birstol-Myers Squibb Company | Hepatitis C virus inhibitors |
| WO2005070955A1 (en) * | 2004-01-21 | 2005-08-04 | Boehringer Ingelheim International Gmbh | Macrocyclic peptides active against the hepatitis c virus |
| JP4914348B2 (ja) * | 2004-06-28 | 2012-04-11 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｃ型肝炎インヒビターペプチド類似体 |
| JP4914355B2 (ja) * | 2004-07-20 | 2012-04-11 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｃ型肝炎インヒビターペプチド類似体 |
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| MY141025A (en) | 2004-10-29 | 2010-02-25 | Vertex Pharma | Dose forms |
| 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 |
| US7592336B2 (en) | 2005-05-10 | 2009-09-22 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| DK1907000T4 (da) | 2005-06-08 | 2020-03-30 | The President And Fellows Of Harvard College | Fremgangsmåder og sammensætninger til behandling af persisterende HIV-infektioner ved hæmning af reaktionsvejen for programmeret celledød 1 (PD-1). |
| 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 |
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| EP2305696A3 (en) | 2005-07-25 | 2011-10-12 | Intermune, Inc. | Macrocyclic inhibitors of Hepatitis C virus replication |
| US8278322B2 (en) | 2005-08-01 | 2012-10-02 | Merck Sharp & Dohme Corp. | HCV NS3 protease inhibitors |
| CA2618682C (en) | 2005-08-12 | 2011-06-21 | Boehringer Ingelheim International Gmbh | Viral polymerase inhibitors |
| US7964624B1 (en) | 2005-08-26 | 2011-06-21 | Vertex Pharmaceuticals Incorporated | Inhibitors of serine proteases |
| 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 |
| EA200801050A1 (ru) | 2005-10-11 | 2008-12-30 | Интермьюн, Инк. | Соединения и способы ингибирования репликации вирусного гепатита с |
| US7772183B2 (en) | 2005-10-12 | 2010-08-10 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US7741281B2 (en) | 2005-11-03 | 2010-06-22 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| 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 |
| JP2009531315A (ja) | 2006-03-16 | 2009-09-03 | バーテックス ファーマシューティカルズ インコーポレイテッド | 重水素化ｃ型肝炎プロテアーゼインヒビター |
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| US7728148B2 (en) * | 2006-06-06 | 2010-06-01 | Enanta Pharmaceuticals, Inc. | Acyclic oximyl hepatitis C protease inhibitors |
| US20080187516A1 (en) * | 2006-06-06 | 2008-08-07 | Ying Sun | Acyclic oximyl hepatitis c protease inhibitors |
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| UY30437A1 (es) * | 2006-06-26 | 2008-01-31 | Enanta Pharm Inc | Quinoxalinil macroceclicos inhibidores de serina proteasa del virus de la hepatitis c |
| RU2008152171A (ru) | 2006-07-05 | 2010-08-10 | Интермьюн, Инк. (Us) | Новые ингибиторы вирусной репликации гепатита с |
| WO2008008776A2 (en) | 2006-07-11 | 2008-01-17 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
| ES2448494T3 (es) | 2006-07-13 | 2014-03-14 | Achillion Pharmaceuticals, Inc. | Péptidos de 4-amino-4-oxobutanoilo en calidad de inhibidores de la replicación viral |
| US7635683B2 (en) * | 2006-08-04 | 2009-12-22 | Enanta Pharmaceuticals, Inc. | Quinoxalinyl tripeptide hepatitis C virus inhibitors |
| US20090035267A1 (en) * | 2007-07-31 | 2009-02-05 | Moore Joel D | Acyclic, pyridazinone-derived hepatitis c serine protease inhibitors |
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| EP1886685A1 (en) | 2006-08-11 | 2008-02-13 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods, uses and compositions for modulating replication of hcv through the farnesoid x receptor (fxr) activation or inhibition |
| WO2008019477A1 (en) | 2006-08-17 | 2008-02-21 | Boehringer Ingelheim International Gmbh | Viral polymerase inhibitors |
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| US8138164B2 (en) | 2006-10-24 | 2012-03-20 | Merck Sharp & Dohme Corp. | HCV NS3 protease inhibitors |
| CN101583372A (zh) * | 2006-10-24 | 2009-11-18 | 默克公司 | Hcv ns3蛋白酶抑制剂 |
| JP5268927B2 (ja) | 2006-10-27 | 2013-08-21 | メルク・シャープ・アンド・ドーム・コーポレーション | Ｈｃｖｎｓ３プロテアーゼ阻害剤 |
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| US8343477B2 (en) | 2006-11-01 | 2013-01-01 | Bristol-Myers Squibb Company | Inhibitors of hepatitis C virus |
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| US7763584B2 (en) | 2006-11-16 | 2010-07-27 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US7888464B2 (en) | 2006-11-16 | 2011-02-15 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8003604B2 (en) | 2006-11-16 | 2011-08-23 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
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2004
- 2004-11-10 US US10/985,106 patent/US7132504B2/en not_active Expired - Lifetime
- 2004-11-12 JP JP2006539980A patent/JP4675331B2/ja not_active Expired - Fee Related
- 2004-11-12 AT AT04811049T patent/ATE542826T1/de active
- 2004-11-12 EP EP04811049A patent/EP1687018B1/en not_active Expired - Lifetime
- 2004-11-12 ES ES04811049T patent/ES2380934T3/es not_active Expired - Lifetime
- 2004-11-12 WO PCT/US2004/038165 patent/WO2005046712A1/en not_active Ceased
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2006
- 2006-05-10 IS IS8448A patent/IS8448A/is unknown
- 2006-05-19 NO NO20062267A patent/NO20062267L/no not_active Application Discontinuation
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