JP2004537564A5 - - Google Patents
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- JP2004537564A5 JP2004537564A5 JP2003515500A JP2003515500A JP2004537564A5 JP 2004537564 A5 JP2004537564 A5 JP 2004537564A5 JP 2003515500 A JP2003515500 A JP 2003515500A JP 2003515500 A JP2003515500 A JP 2003515500A JP 2004537564 A5 JP2004537564 A5 JP 2004537564A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- aryl
- cycloalkyl
- het
- membered
- 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.)
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- 125000000217 alkyl group Chemical group 0.000 claims 921
- 125000003118 aryl group Chemical group 0.000 claims 786
- 125000000753 cycloalkyl group Chemical group 0.000 claims 777
- 125000000623 heterocyclic group Chemical group 0.000 claims 301
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 124
- 229910052757 nitrogen Inorganic materials 0.000 claims 124
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 112
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 90
- 125000001424 substituent group Chemical group 0.000 claims 69
- 229910052736 halogen Inorganic materials 0.000 claims 55
- 150000001875 compounds Chemical class 0.000 claims 47
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 45
- 125000001188 haloalkyl group Chemical group 0.000 claims 44
- 150000002367 halogens Chemical class 0.000 claims 43
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 33
- 125000005842 heteroatom Chemical group 0.000 claims 31
- 125000002877 alkyl aryl group Chemical group 0.000 claims 30
- 229910052760 oxygen Inorganic materials 0.000 claims 29
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 28
- 229910052717 sulfur Inorganic materials 0.000 claims 28
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 22
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 20
- 229910052739 hydrogen Inorganic materials 0.000 claims 20
- 150000003536 tetrazoles Chemical class 0.000 claims 18
- 125000003342 alkenyl group Chemical group 0.000 claims 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 14
- KWEDUNSJJZVRKR-UHFFFAOYSA-N carbononitridic azide Chemical compound [N-]=[N+]=NC#N KWEDUNSJJZVRKR-UHFFFAOYSA-N 0.000 claims 13
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 12
- -1 bicycloalkenyl Chemical group 0.000 claims 12
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims 11
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 9
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 9
- 239000000203 mixture Substances 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 229920006395 saturated elastomer Polymers 0.000 claims 8
- 229910052799 carbon Inorganic materials 0.000 claims 7
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 6
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 4
- SDQJTWBNWQABLE-UHFFFAOYSA-N 1h-quinazoline-2,4-dione Chemical compound C1=CC=C2C(=O)NC(=O)NC2=C1 SDQJTWBNWQABLE-UHFFFAOYSA-N 0.000 claims 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 4
- 239000003112 inhibitor Substances 0.000 claims 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 150000001540 azides Chemical class 0.000 claims 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims 3
- 229940091173 hydantoin Drugs 0.000 claims 3
- 229940124530 sulfonamide Drugs 0.000 claims 3
- 150000003456 sulfonamides Chemical class 0.000 claims 3
- 125000001425 triazolyl group Chemical group 0.000 claims 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 2
- 108060004795 Methyltransferase Proteins 0.000 claims 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 2
- YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 125000005189 alkyl hydroxy group Chemical group 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 239000003443 antiviral agent Substances 0.000 claims 2
- 125000003435 aroyl group Chemical group 0.000 claims 2
- 150000001602 bicycloalkyls Chemical group 0.000 claims 2
- 235000010290 biphenyl Nutrition 0.000 claims 2
- 239000004305 biphenyl Substances 0.000 claims 2
- 239000007822 coupling agent Substances 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 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
- 208000015181 infectious disease Diseases 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- 108090000790 Enzymes Proteins 0.000 claims 1
- 102000004190 Enzymes Human genes 0.000 claims 1
- 102000005741 Metalloproteases Human genes 0.000 claims 1
- 108010006035 Metalloproteases Proteins 0.000 claims 1
- 108091005804 Peptidases Proteins 0.000 claims 1
- 239000004365 Protease Substances 0.000 claims 1
- 101800001554 RNA-directed RNA polymerase Proteins 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
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy 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
- 239000000010 aprotic solvent Substances 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 239000004202 carbamide Substances 0.000 claims 1
- 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 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 229940079322 interferon Drugs 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims 1
- 230000010076 replication 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
- 239000002904 solvent Substances 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30767401P | 2001-07-25 | 2001-07-25 | |
| US33806101P | 2001-12-07 | 2001-12-07 | |
| PCT/CA2002/001128 WO2003010141A2 (en) | 2001-07-25 | 2002-07-18 | Hepatitis c virus polymerase inhibitors with a heterobicyclic structure |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009092397A Division JP2009275037A (ja) | 2001-07-25 | 2009-04-06 | ウイルスポリメラーゼインヒビター |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004537564A JP2004537564A (ja) | 2004-12-16 |
| JP2004537564A5 true JP2004537564A5 (enExample) | 2005-12-22 |
| JP4398725B2 JP4398725B2 (ja) | 2010-01-13 |
Family
ID=26975871
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003515500A Expired - Fee Related JP4398725B2 (ja) | 2001-07-25 | 2002-07-18 | ウイルスポリメラーゼインヒビター |
| JP2003515499A Expired - Fee Related JP4398241B2 (ja) | 2001-07-25 | 2002-07-18 | ウイルスポリメラーゼインヒビター |
| JP2009048600A Withdrawn JP2009120616A (ja) | 2001-07-25 | 2009-03-02 | ウイルスポリメラーゼインヒビター |
| JP2009092397A Withdrawn JP2009275037A (ja) | 2001-07-25 | 2009-04-06 | ウイルスポリメラーゼインヒビター |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003515499A Expired - Fee Related JP4398241B2 (ja) | 2001-07-25 | 2002-07-18 | ウイルスポリメラーゼインヒビター |
| JP2009048600A Withdrawn JP2009120616A (ja) | 2001-07-25 | 2009-03-02 | ウイルスポリメラーゼインヒビター |
| JP2009092397A Withdrawn JP2009275037A (ja) | 2001-07-25 | 2009-04-06 | ウイルスポリメラーゼインヒビター |
Country Status (33)
Families Citing this family (210)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6825228B2 (en) * | 2001-06-13 | 2004-11-30 | Genesoft Pharmaceuticals, Inc. | Benzothiophene compounds having antiinfective activity |
| EP2335700A1 (en) | 2001-07-25 | 2011-06-22 | Boehringer Ingelheim (Canada) Ltd. | Hepatitis C virus polymerase inhibitors with a heterobicylic structure |
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| US20050075279A1 (en) | 2002-10-25 | 2005-04-07 | Boehringer Ingelheim International Gmbh | Macrocyclic peptides active against the hepatitis C virus |
| US7098231B2 (en) * | 2003-01-22 | 2006-08-29 | Boehringer Ingelheim International Gmbh | Viral polymerase inhibitors |
| US7223785B2 (en) * | 2003-01-22 | 2007-05-29 | Boehringer Ingelheim International Gmbh | Viral polymerase inhibitors |
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| US7592352B2 (en) | 2003-05-06 | 2009-09-22 | Smithkline Beecham Corporation | Substituted thieno and furo-pyridines |
| BRPI0413234A (pt) | 2003-08-01 | 2006-10-03 | Genelabs Tech Inc | derivados de imidazola bicìclica contra flaviviridae |
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| CN103524495A (zh) * | 2005-02-11 | 2014-01-22 | 贝林格尔.英格海姆国际有限公司 | 2, 3-二取代的吲哚的制备方法 |
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- 2002-07-18 UA UA2004021313A patent/UA84256C2/ru unknown
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- 2002-07-18 WO PCT/CA2002/001127 patent/WO2003010140A2/en not_active Ceased
- 2002-07-18 RS RSP-2009/0517A patent/RS20090517A/sr unknown
- 2002-07-18 DK DK02752904T patent/DK1414797T3/da active
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2003
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2004
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2008
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2009
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