JP2005533028A5 - - Google Patents
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- Publication number
- JP2005533028A5 JP2005533028A5 JP2004506798A JP2004506798A JP2005533028A5 JP 2005533028 A5 JP2005533028 A5 JP 2005533028A5 JP 2004506798 A JP2004506798 A JP 2004506798A JP 2004506798 A JP2004506798 A JP 2004506798A JP 2005533028 A5 JP2005533028 A5 JP 2005533028A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- compound
- cycloalkyl
- optionally substituted
- pharmaceutically acceptable
- 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 56
- 125000000217 alkyl group Chemical group 0.000 claims 44
- 239000000651 prodrug Substances 0.000 claims 23
- 229940002612 prodrug Drugs 0.000 claims 23
- 150000003839 salts Chemical class 0.000 claims 23
- 239000012453 solvate Substances 0.000 claims 23
- 125000003545 alkoxy group Chemical group 0.000 claims 18
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 17
- -1 cyano, amino Chemical group 0.000 claims 13
- 229910052736 halogen Inorganic materials 0.000 claims 11
- 150000002367 halogens Chemical group 0.000 claims 11
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 11
- 239000000203 mixture Substances 0.000 claims 10
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 9
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 8
- 125000003118 aryl group Chemical group 0.000 claims 8
- 125000005843 halogen group Chemical group 0.000 claims 8
- 125000002877 alkyl aryl group Chemical group 0.000 claims 7
- 229910052799 carbon Inorganic materials 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 5
- 125000004433 nitrogen atom Chemical group N* 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
- 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
- 125000004191 (C1-C6) alkoxy group Chemical group 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
- 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
- 125000004430 oxygen atom Chemical group O* 0.000 claims 3
- 239000011593 sulfur Substances 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical group N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
- 101800001838 Serine protease/helicase NS3 Proteins 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 239000003443 antiviral agent Substances 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 239000002955 immunomodulating agent Substances 0.000 claims 2
- 229940121354 immunomodulator Drugs 0.000 claims 2
- 230000002584 immunomodulator Effects 0.000 claims 2
- 239000003112 inhibitor Substances 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
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 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
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 229940122604 HCV protease 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
- 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 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
- 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
- 150000001412 amines Chemical class 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
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 208000010710 hepatitis C virus infection Diseases 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 229940079322 interferon Drugs 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 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
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 125000004001 thioalkyl group Chemical group 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 0 C*([C@@](C(C)(C)C)C(*(C[C@@](C1)(OC(*c2c(*3)cccc2)=C3O*)I)[C@]1(*)C(*(*)[C@]1(C(CC=C)C1)C(**)=O)=O)=O)C(OC(C)(C)C)=O Chemical compound C*([C@@](C(C)(C)C)C(*(C[C@@](C1)(OC(*c2c(*3)cccc2)=C3O*)I)[C@]1(*)C(*(*)[C@]1(C(CC=C)C1)C(**)=O)=O)=O)C(OC(C)(C)C)=O 0.000 description 4
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- HOBCGPSQZNVUSJ-UHFFFAOYSA-N 1,7-dichloro-4-methoxyisoquinoline Chemical compound ClC1=CC=C2C(OC)=CN=C(Cl)C2=C1 HOBCGPSQZNVUSJ-UHFFFAOYSA-N 0.000 description 1
- HUILUFREXDWQCP-LTTWWRRRSA-N C=CC(C1)[C@H]1C(NS(C1CC1)(=O)=O)=[U] Chemical compound C=CC(C1)[C@H]1C(NS(C1CC1)(=O)=O)=[U] HUILUFREXDWQCP-LTTWWRRRSA-N 0.000 description 1
- AZXNRUPGHDCJRG-QVQNWWHPSA-N CC(C)(C)[C@@H](C(N(C[C@@H](C1)Oc2c(cccc3C(F)(F)F)c3ncc2)C1C(N[C@H](C(C1)C1C=C)C(NS(C1CC1)(=O)=O)=O)=O)=[U])NC(OC(C)(C)C)=O Chemical compound CC(C)(C)[C@@H](C(N(C[C@@H](C1)Oc2c(cccc3C(F)(F)F)c3ncc2)C1C(N[C@H](C(C1)C1C=C)C(NS(C1CC1)(=O)=O)=O)=O)=[U])NC(OC(C)(C)C)=O AZXNRUPGHDCJRG-QVQNWWHPSA-N 0.000 description 1
- VSLWQFIBSIVIJP-MXZMCTFZSA-N CC(C)(C)[C@@H](C(N(C[C@@H](C1)Oc2c3[o]nc(C)c3nc(-c(cc3)ccc3F)c2)C1C(C)=[U])=O)NC(OC(C)(C)C)=O Chemical compound CC(C)(C)[C@@H](C(N(C[C@@H](C1)Oc2c3[o]nc(C)c3nc(-c(cc3)ccc3F)c2)C1C(C)=[U])=O)NC(OC(C)(C)C)=O VSLWQFIBSIVIJP-MXZMCTFZSA-N 0.000 description 1
- JAFWTZWRJFDLJT-PBCRRDIASA-N CC(C)(C)[C@@H](C(N(C[C@@H](C1)Oc2c3[o]nc(C)c3nc(-c3ccccc3)c2)[C@@H]1C(N[C@](C1)([C@@H]1C=C)C(NS(C1CC1)(=O)=O)=O)=O)=O)NC(OC(C)(C)C)=O Chemical compound CC(C)(C)[C@@H](C(N(C[C@@H](C1)Oc2c3[o]nc(C)c3nc(-c3ccccc3)c2)[C@@H]1C(N[C@](C1)([C@@H]1C=C)C(NS(C1CC1)(=O)=O)=O)=O)=O)NC(OC(C)(C)C)=O JAFWTZWRJFDLJT-PBCRRDIASA-N 0.000 description 1
- UUAGYGZMDRRKAC-UHFFFAOYSA-N CC(C)(c1ccccc1)OC(NC1(C(C)(C)C1)C(NC/C(/CC1(CC1)C=C)=[O]/c1c(ccc(OC)c2)c2ccn1)=O)=O Chemical compound CC(C)(c1ccccc1)OC(NC1(C(C)(C)C1)C(NC/C(/CC1(CC1)C=C)=[O]/c1c(ccc(OC)c2)c2ccn1)=O)=O UUAGYGZMDRRKAC-UHFFFAOYSA-N 0.000 description 1
- WRFAPZSTHNZMDX-UHFFFAOYSA-N CCCC(C1)C1C(C=O)NS(C1CC1)(=O)=O Chemical compound CCCC(C1)C1C(C=O)NS(C1CC1)(=O)=O WRFAPZSTHNZMDX-UHFFFAOYSA-N 0.000 description 1
- IVDQYFOTMKSIJV-UHFFFAOYSA-N CCS(C1CC1)NC(C(C1)(C(C)CCC(C(C)CC(CNC(C(C(C)(C)C)NC(NC(C)(C)C)=N)=O)Oc2c(ccc(OC)c3)c3ccn2)=O)C1C=C)=O Chemical compound CCS(C1CC1)NC(C(C1)(C(C)CCC(C(C)CC(CNC(C(C(C)(C)C)NC(NC(C)(C)C)=N)=O)Oc2c(ccc(OC)c3)c3ccn2)=O)C1C=C)=O IVDQYFOTMKSIJV-UHFFFAOYSA-N 0.000 description 1
- SYSLARHICMEYEQ-UHFFFAOYSA-N [O-][N+](C1CC1)=O Chemical compound [O-][N+](C1CC1)=O SYSLARHICMEYEQ-UHFFFAOYSA-N 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- GJTTUAJDRWKQJN-UHFFFAOYSA-N tert-butyl n-[1-[2-[[1-(cyclopropylsulfonylcarbamoyl)-2-ethenylcyclopropyl]carbamoyl]-4-hydroxypyrrolidin-1-yl]-3,3-dimethyl-1-oxobutan-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)NC(C(C)(C)C)C(=O)N1CC(O)CC1C(=O)NC1(C(=O)NS(=O)(=O)C2CC2)C(C=C)C1 GJTTUAJDRWKQJN-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38205502P | 2002-05-20 | 2002-05-20 | |
| PCT/US2003/015755 WO2003099274A1 (en) | 2002-05-20 | 2003-05-20 | Hepatitis c virus inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005533028A JP2005533028A (ja) | 2005-11-04 |
| JP2005533028A5 true JP2005533028A5 (enExample) | 2006-12-07 |
| JP4312710B2 JP4312710B2 (ja) | 2009-08-12 |
Family
ID=29584353
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004506798A Expired - Fee Related JP4312710B2 (ja) | 2002-05-20 | 2003-05-20 | Ｃ型肝炎ウイルス阻害剤 |
Country Status (33)
Families Citing this family (282)
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|---|---|---|---|---|
| US20060199773A1 (en) * | 2002-05-20 | 2006-09-07 | Sausker Justin B | Crystalline forms of (1R,2S)-N-[(1,1-dimethylethoxy)carbonyl]-3-methyl-L-valyl-(4R)-4-[(6-methoxy-1-isoquinolinyl)oxy]-L-prolyl-1-amino-N-(cyclopropylsulfonyl)-2-ethenyl-cyclopropanecarboxamide, monopotassium salt |
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| JP4733023B2 (ja) * | 2003-04-16 | 2011-07-27 | ブリストル−マイヤーズ スクイブ カンパニー | Ｃ型肝炎ウイルスの大環状イソキノリンペプチド阻害剤 |
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