JP2010535799A5 - - Google Patents
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- Publication number
- JP2010535799A5 JP2010535799A5 JP2010520272A JP2010520272A JP2010535799A5 JP 2010535799 A5 JP2010535799 A5 JP 2010535799A5 JP 2010520272 A JP2010520272 A JP 2010520272A JP 2010520272 A JP2010520272 A JP 2010520272A JP 2010535799 A5 JP2010535799 A5 JP 2010535799A5
- Authority
- JP
- Japan
- Prior art keywords
- methoxy
- cyclohexyl
- indolo
- benzazepine
- sulfonyl
- 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
- -1 pyrrolopyridinyl Chemical group 0.000 claims 47
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 43
- FRUWAONHRDGSAL-UHFFFAOYSA-N 7h-indolo[2,1-a][2]benzazepine-10-carboxylic acid Chemical compound C1=CCN2C3=CC(C(=O)O)=CC=C3C=C2C2=CC=CC=C21 FRUWAONHRDGSAL-UHFFFAOYSA-N 0.000 claims 41
- 125000000217 alkyl group Chemical group 0.000 claims 36
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 34
- HJHICYAWGPPIND-UHFFFAOYSA-N 7h-indolo[2,1-a][2]benzazepine-10-carboxamide Chemical compound C1=CCN2C3=CC(C(=O)N)=CC=C3C=C2C2=CC=CC=C21 HJHICYAWGPPIND-UHFFFAOYSA-N 0.000 claims 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 24
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 19
- 229910052739 hydrogen Inorganic materials 0.000 claims 16
- 239000001257 hydrogen Substances 0.000 claims 16
- 150000001875 compounds Chemical class 0.000 claims 13
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 12
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 12
- 125000003545 alkoxy group Chemical group 0.000 claims 11
- 125000001424 substituent group Chemical group 0.000 claims 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 10
- 125000002393 azetidinyl group Chemical group 0.000 claims 8
- 125000002757 morpholinyl group Chemical group 0.000 claims 8
- 125000004193 piperazinyl group Chemical group 0.000 claims 8
- 125000003386 piperidinyl group Chemical group 0.000 claims 8
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 8
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 8
- 125000003282 alkyl amino group Chemical group 0.000 claims 7
- 125000004663 dialkyl amino group Chemical group 0.000 claims 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 7
- 125000001475 halogen functional group Chemical group 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 6
- QRKIDYBDEVJLFN-UHFFFAOYSA-N 5h-indolo[2,1-a][2]benzazepine-10-carboxamide Chemical compound C1C=CN2C3=CC(C(=O)N)=CC=C3C=C2C2=CC=CC=C21 QRKIDYBDEVJLFN-UHFFFAOYSA-N 0.000 claims 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 5
- 125000001188 haloalkyl group Chemical group 0.000 claims 5
- 125000004076 pyridyl group Chemical group 0.000 claims 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims 2
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims 2
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- OTDWHDOTZWWCFA-UHFFFAOYSA-N 12-azapentacyclo[10.7.0.02,7.08,10.013,18]nonadeca-1(19),2,4,6,8,10,13,15,17-nonaene-9-carboxamide Chemical compound C=1N2C3=CC=CC=C3C=C2C2=CC=CC=C2C2=C(C(=O)N)C2=1 OTDWHDOTZWWCFA-UHFFFAOYSA-N 0.000 claims 1
- MOXSHYPJVULGBJ-UHFFFAOYSA-N 13-cyclohexyl-3-methoxy-6-[2-(3-methyl-3,8-diazabicyclo[3.2.1]octane-8-carbonyl)phenyl]-n-propan-2-ylsulfonyl-7h-indolo[2,1-a][2]benzazepine-10-carboxamide Chemical compound C12=CC=C(C(=O)NS(=O)(=O)C(C)C)C=C2N2CC(C=3C(=CC=CC=3)C(=O)N3C4CCC3CN(C)C4)=CC3=CC(OC)=CC=C3C2=C1C1CCCCC1 MOXSHYPJVULGBJ-UHFFFAOYSA-N 0.000 claims 1
- 208000005176 Hepatitis C Diseases 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 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
- 125000005433 dihydrobenzodioxinyl group Chemical group O1C(COC2=C1C=CC=C2)* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 208000010710 hepatitis C virus infection Diseases 0.000 claims 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US95481307P | 2007-08-09 | 2007-08-09 | |
| US60/954,813 | 2007-08-09 | ||
| PCT/US2008/072295 WO2009023487A1 (en) | 2007-08-09 | 2008-08-06 | Tetracyclic compounds for the treatment of hepatitis c |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010535799A JP2010535799A (ja) | 2010-11-25 |
| JP2010535799A5 true JP2010535799A5 (enExample) | 2011-09-22 |
| JP5406837B2 JP5406837B2 (ja) | 2014-02-05 |
Family
ID=40002880
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010520272A Expired - Fee Related JP5406837B2 (ja) | 2007-08-09 | 2008-08-06 | Ｃ型肝炎を治療するための四環系化合物 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7642251B2 (enExample) |
| EP (1) | EP2178878B1 (enExample) |
| JP (1) | JP5406837B2 (enExample) |
| CN (1) | CN101821268B (enExample) |
| AT (1) | ATE551343T1 (enExample) |
| ES (1) | ES2383247T3 (enExample) |
| WO (1) | WO2009023487A1 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1688420A4 (en) * | 2003-11-19 | 2008-10-22 | Japan Tobacco Inc | 5-5 LOW-CONDENSED HETEROCYCLIC COMPOUND AND THEIR USE AS HCV POLYMERASE INHIBITOR |
| US20070049593A1 (en) | 2004-02-24 | 2007-03-01 | Japan Tobacco Inc. | Tetracyclic fused heterocyclic compound and use thereof as HCV polymerase inhibitor |
| US7659263B2 (en) | 2004-11-12 | 2010-02-09 | Japan Tobacco Inc. | Thienopyrrole compound and use thereof as HCV polymerase inhibitor |
| US8143243B2 (en) * | 2007-08-09 | 2012-03-27 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| AU2007361468A1 (en) * | 2007-11-20 | 2009-05-28 | Bristol-Myers Squibb Company | Cyclopropyl fused indolobenzazepine HCV NS5B inhibitors |
| US8129367B2 (en) * | 2007-11-21 | 2012-03-06 | Bristol-Myers Squibb Company | Compounds for the treatment of Hepatitis C |
| ATE531373T1 (de) | 2008-03-27 | 2011-11-15 | Bristol Myers Squibb Co | Aromatische heterocyclische kondensierte indolobenzadiazepin-hcv-ns5b-inhibitoren |
| US8133884B2 (en) * | 2008-05-06 | 2012-03-13 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US8143244B2 (en) * | 2009-02-26 | 2012-03-27 | Bristol-Myers Squibb Company | Cyclopropyl fused indolobenzazepine HCV NS5B inhibitors |
| CN102427729B (zh) | 2009-03-27 | 2014-09-03 | 默沙东公司 | 丙型肝炎病毒复制的抑制剂 |
| US20190127365A1 (en) | 2017-11-01 | 2019-05-02 | Merck Sharp & Dohme Corp. | Inhibitors of hepatitis c virus replication |
| EP2621279B1 (en) | 2010-09-29 | 2018-04-04 | Merck Sharp & Dohme Corp. | Fused tetracycle derivatives and methods of use thereof for the treatment of viral diseases |
| WO2012122716A1 (en) | 2011-03-17 | 2012-09-20 | Merck Sharp & Dohme Corp. | Tetracyclic xanthene derivatives and methods of use thereof for treatment of viral diseases |
| WO2014110687A1 (en) | 2013-01-16 | 2014-07-24 | Merck Sharp & Dohme Corp. | Thiazolyl-substitued tetracyclic compounds and methods of use thereof for treatment of viral diseases |
| CN105440048A (zh) * | 2014-09-28 | 2016-03-30 | 复旦大学 | 1,3-苯并二噁茂类化合物山芝麻素及其药物用途 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT1719773E (pt) | 2004-02-24 | 2009-06-03 | Japan Tobacco Inc | Compostos heterotetracíclicos fundidos e a sua utilização como inibidores da polimerase do hcv |
| US7153848B2 (en) | 2004-08-09 | 2006-12-26 | Bristol-Myers Squibb Company | Inhibitors of HCV replication |
| CA2585084A1 (en) | 2004-10-26 | 2006-05-04 | Immacolata Conte | Tetracyclic indole derivatives as antiviral agents |
| GB0518390D0 (en) | 2005-09-09 | 2005-10-19 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
| US7399758B2 (en) * | 2005-09-12 | 2008-07-15 | Meanwell Nicholas A | Cyclopropyl fused indolobenzazepine HCV NS5B inhibitors |
| US7473688B2 (en) | 2005-09-13 | 2009-01-06 | Bristol-Myers Squibb Company | Indolobenzazepine HCV NS5B inhibitors |
| US7456165B2 (en) | 2006-02-08 | 2008-11-25 | Bristol-Myers Squibb Company | HCV NS5B inhibitors |
| GB0608928D0 (en) | 2006-05-08 | 2006-06-14 | Angeletti P Ist Richerche Bio | Therapeutic agents |
| US7456166B2 (en) | 2006-05-17 | 2008-11-25 | Bristol-Myers Squibb Company | Cyclopropyl fused indolobenzazepine HCV NS5B inhibitors |
| US7521441B2 (en) | 2006-05-22 | 2009-04-21 | Bristol-Myers Squibb Company | Cyclopropyl fused indolobenzazepine HCV NS5B inhibitors |
| ES2343914T3 (es) | 2006-05-25 | 2010-08-12 | Bristol-Myers Squibb Company | Inhibidores de ns5b de hcv de indolobenzazepina condensada con ciclopropilo. |
| WO2007140200A2 (en) | 2006-05-25 | 2007-12-06 | Bristol-Myers Squibb Company | Cyclopropyl fused indolobenzazepine hcv ns5b inhibitors |
| US7452876B2 (en) | 2006-06-08 | 2008-11-18 | Bristol-Myers Squibb Company | Cyclopropyl fused indolobenzazepine HCV NS5B inhibitors |
| US7541351B2 (en) | 2007-01-11 | 2009-06-02 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US7517872B2 (en) | 2007-02-22 | 2009-04-14 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US7541353B2 (en) | 2007-03-14 | 2009-06-02 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US7547690B2 (en) | 2007-03-14 | 2009-06-16 | Bristol-Myers Squibb Company | Compounds for the treatment of Hepatitis C |
| US7538102B2 (en) | 2007-03-14 | 2009-05-26 | Bristol-Myers Squibb Company | Compounds for the treatment of Hepatitis C |
| US7521444B2 (en) | 2007-03-14 | 2009-04-21 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US7538103B2 (en) | 2007-03-15 | 2009-05-26 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
-
2008
- 2008-08-01 US US12/184,791 patent/US7642251B2/en active Active
- 2008-08-06 EP EP08797248A patent/EP2178878B1/en not_active Not-in-force
- 2008-08-06 JP JP2010520272A patent/JP5406837B2/ja not_active Expired - Fee Related
- 2008-08-06 AT AT08797248T patent/ATE551343T1/de active
- 2008-08-06 WO PCT/US2008/072295 patent/WO2009023487A1/en not_active Ceased
- 2008-08-06 ES ES08797248T patent/ES2383247T3/es active Active
- 2008-08-06 CN CN200880110882XA patent/CN101821268B/zh not_active Expired - Fee Related
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