AU2008293845B2 - Compounds for the treatment of hepatitis C - Google Patents
Compounds for the treatment of hepatitis C Download PDFInfo
- Publication number
- AU2008293845B2 AU2008293845B2 AU2008293845A AU2008293845A AU2008293845B2 AU 2008293845 B2 AU2008293845 B2 AU 2008293845B2 AU 2008293845 A AU2008293845 A AU 2008293845A AU 2008293845 A AU2008293845 A AU 2008293845A AU 2008293845 B2 AU2008293845 B2 AU 2008293845B2
- Authority
- AU
- Australia
- Prior art keywords
- cyclohexyl
- methoxy
- indolo
- benzazepine
- methyl
- 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.)
- Ceased
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 154
- 208000005176 Hepatitis C Diseases 0.000 title claims 2
- 238000000034 method Methods 0.000 claims abstract description 66
- 239000000203 mixture Substances 0.000 claims abstract description 33
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 335
- 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 description 310
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 268
- -1 homopiperidinyl Chemical group 0.000 claims description 228
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 178
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 117
- 125000000217 alkyl group Chemical group 0.000 claims description 107
- 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 description 94
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 70
- IMBBXSASDSZJSX-UHFFFAOYSA-N 4-Carboxypyrazole Chemical compound OC(=O)C=1C=NNC=1 IMBBXSASDSZJSX-UHFFFAOYSA-N 0.000 claims description 67
- 229910052739 hydrogen Inorganic materials 0.000 claims description 61
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 50
- 125000004497 pyrazol-5-yl group Chemical group N1N=CC=C1* 0.000 claims description 48
- 239000001257 hydrogen Substances 0.000 claims description 47
- 229910052757 nitrogen Inorganic materials 0.000 claims description 47
- 125000004193 piperazinyl group Chemical group 0.000 claims description 34
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 32
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 32
- 125000001424 substituent group Chemical group 0.000 claims description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
- 125000004494 ethyl ester group Chemical group 0.000 claims description 25
- 125000003282 alkyl amino group Chemical group 0.000 claims description 22
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 22
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 19
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 14
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000002393 azetidinyl group Chemical group 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000002757 morpholinyl group Chemical group 0.000 claims description 12
- 125000003386 piperidinyl group Chemical group 0.000 claims description 12
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 12
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 12
- 150000004702 methyl esters Chemical class 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims description 7
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 102100026456 POU domain, class 3, transcription factor 3 Human genes 0.000 claims description 5
- 101710133393 POU domain, class 3, transcription factor 3 Proteins 0.000 claims description 5
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 5
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 5
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 5
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 5
- 125000002971 oxazolyl group Chemical group 0.000 claims description 5
- 125000004043 oxo group Chemical group O=* 0.000 claims description 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 125000001425 triazolyl group Chemical group 0.000 claims description 5
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 4
- 102000014150 Interferons Human genes 0.000 claims description 4
- 108010050904 Interferons Proteins 0.000 claims description 4
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 108060004795 Methyltransferase Proteins 0.000 claims description 3
- 101800001019 Non-structural protein 4B Proteins 0.000 claims description 3
- 101800001014 Non-structural protein 5A Proteins 0.000 claims description 3
- 230000008901 benefit Effects 0.000 claims description 3
- 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 description 3
- 108700008776 hepatitis C virus NS-5 Proteins 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims description 2
- RFIOZSIHFNEKFF-UHFFFAOYSA-N piperazine-1-carboxylic acid Chemical compound OC(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-N 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims 10
- DOYOPBSXEIZLRE-UHFFFAOYSA-N pyrrole-3-carboxylic acid Chemical compound OC(=O)C=1C=CNC=1 DOYOPBSXEIZLRE-UHFFFAOYSA-N 0.000 claims 6
- 239000012268 protein inhibitor Substances 0.000 claims 5
- 229940121649 protein inhibitor Drugs 0.000 claims 5
- IHCCAYCGZOLTEU-UHFFFAOYSA-N 3-furoic acid Chemical compound OC(=O)C=1C=COC=1 IHCCAYCGZOLTEU-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- 108010036941 Cyclosporins Proteins 0.000 claims 2
- 229940122750 HCV entry inhibitor Drugs 0.000 claims 2
- 102000015696 Interleukins Human genes 0.000 claims 2
- 108010063738 Interleukins Proteins 0.000 claims 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims 2
- 229930182912 cyclosporin Natural products 0.000 claims 2
- 229940047124 interferons Drugs 0.000 claims 2
- 229940047122 interleukins Drugs 0.000 claims 2
- 239000003475 metalloproteinase inhibitor Substances 0.000 claims 2
- 230000001225 therapeutic effect Effects 0.000 claims 2
- NRQHBNNTBIDSRK-YRNVUSSQSA-N (4e)-4-[(4-methoxyphenyl)methylidene]-2-methyl-1,3-oxazol-5-one Chemical compound C1=CC(OC)=CC=C1\C=C\1C(=O)OC(C)=N/1 NRQHBNNTBIDSRK-YRNVUSSQSA-N 0.000 claims 1
- 229940124683 HCV polymerase inhibitor Drugs 0.000 claims 1
- 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 208000010710 hepatitis C virus infection Diseases 0.000 claims 1
- 239000000137 peptide hydrolase inhibitor Substances 0.000 claims 1
- 239000003001 serine protease inhibitor Substances 0.000 claims 1
- 241000711549 Hepacivirus C Species 0.000 abstract description 18
- 230000000694 effects Effects 0.000 abstract description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 693
- 239000002904 solvent Substances 0.000 description 488
- 238000006243 chemical reaction Methods 0.000 description 303
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 173
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 169
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 151
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 149
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 137
- 238000005160 1H NMR spectroscopy Methods 0.000 description 134
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 128
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 125
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 121
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 114
- 239000005695 Ammonium acetate Substances 0.000 description 114
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 114
- 235000019257 ammonium acetate Nutrition 0.000 description 114
- 229940043376 ammonium acetate Drugs 0.000 description 114
- 230000014759 maintenance of location Effects 0.000 description 109
- 239000000243 solution Substances 0.000 description 105
- 239000000047 product Substances 0.000 description 97
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 95
- 239000007787 solid Substances 0.000 description 94
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 55
- 238000004128 high performance liquid chromatography Methods 0.000 description 53
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- 238000002953 preparative HPLC Methods 0.000 description 50
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- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-dimethylaminopyridine Substances CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 45
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 42
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 41
- CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 39
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Virology (AREA)
- General Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US95481407P | 2007-08-09 | 2007-08-09 | |
| US60/954,814 | 2007-08-09 | ||
| US4994408P | 2008-05-02 | 2008-05-02 | |
| US61/049,944 | 2008-05-02 | ||
| US12/180,994 US7652004B2 (en) | 2007-08-09 | 2008-07-28 | Compounds for the treatment of hepatitis C |
| US12/180,994 | 2008-07-28 | ||
| PCT/US2008/071881 WO2009029384A2 (en) | 2007-08-09 | 2008-08-01 | Compounds for the treatment of hepatitis c |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2008293845A1 AU2008293845A1 (en) | 2009-03-05 |
| AU2008293845B2 true AU2008293845B2 (en) | 2013-02-14 |
Family
ID=40261456
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2008293845A Ceased AU2008293845B2 (en) | 2007-08-09 | 2008-08-01 | Compounds for the treatment of hepatitis C |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US7652004B2 (https=) |
| EP (1) | EP2183252B1 (https=) |
| JP (1) | JP5465670B2 (https=) |
| KR (1) | KR20100066492A (https=) |
| CN (1) | CN101821267B (https=) |
| AR (1) | AR067897A1 (https=) |
| AU (1) | AU2008293845B2 (https=) |
| BR (1) | BRPI0814931A2 (https=) |
| CA (1) | CA2695781A1 (https=) |
| CL (1) | CL2008002353A1 (https=) |
| CO (1) | CO6251359A2 (https=) |
| EA (1) | EA015978B1 (https=) |
| MX (1) | MX2010001416A (https=) |
| NZ (1) | NZ583149A (https=) |
| PE (1) | PE20090618A1 (https=) |
| TW (1) | TW200906418A (https=) |
| WO (1) | WO2009029384A2 (https=) |
| ZA (1) | ZA201000923B (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005049622A1 (ja) * | 2003-11-19 | 2005-06-02 | Japan Tobacco Inc. | ５－５員縮合複素環化合物及びそのｈｃｖポリメラーゼ阻害剤としての用途 |
| 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 |
| KR20100108341A (ko) * | 2007-11-20 | 2010-10-06 | 브리스톨-마이어스 스큅 컴퍼니 | 시클로프로필 융합된 인돌로벤즈아제핀 ｈｃｖ ｎｓ5ｂ 억제제 |
| US8129367B2 (en) * | 2007-11-21 | 2012-03-06 | Bristol-Myers Squibb Company | Compounds for the treatment of Hepatitis C |
| KR20100124848A (ko) | 2008-03-27 | 2010-11-29 | 브리스톨-마이어스 스큅 컴퍼니 | 방향족 헤테로시클릭 융합된 인돌로벤자디아제핀 ｈｃｖ ｎｓ5ｂ 억제제 |
| US8133884B2 (en) * | 2008-05-06 | 2012-03-13 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| JP2012517468A (ja) * | 2009-02-11 | 2012-08-02 | ブリストル−マイヤーズ スクイブ カンパニー | Ｃ型肝炎治療のための化合物 |
| CA2822357A1 (en) | 2010-12-22 | 2012-06-28 | Abbvie Inc. | Hepatitis c inhibitors and uses thereof |
| CH706864B1 (de) | 2011-06-22 | 2016-03-31 | Central Glass Co Ltd | Verfahren zur Herstellung einer Pyrazol-Verbindung. |
| JP5915004B2 (ja) * | 2011-06-22 | 2016-05-11 | セントラル硝子株式会社 | ピラゾール化合物の製造方法 |
| EP3091022A3 (en) * | 2012-07-18 | 2016-12-14 | Bristol-Myers Squibb Holdings Ireland | Methods and intermediates for the preparation of (4bs,5ar)-12-cyclohexyl-n-(n,n-dimethylsulfamoyl)-3- methoxy-5a-((1r,5s)-3-methyl-3,8-diazabicyclo[3.2.1]octane-8-carbonyl)-4b,5,5a,6-tetrahydrobenzo [3,4]cyclopropa[5,6]azepino[1,2-a]indole-9-carboxamide |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007033032A1 (en) * | 2005-09-12 | 2007-03-22 | Bristol-Myers Squibb Company | Cyclopropyl fused indolobenzazepine hcv ns5b inhibitors |
| WO2007092888A2 (en) * | 2006-02-08 | 2007-08-16 | Bristol-Myers Squibb Company | Hcv ns5b inhibitors |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HRP20090250T1 (hr) | 2004-02-24 | 2009-06-30 | Japan Tobacco | Kondenzirani heterociklički spojevi i njihova upotreba kao inhibitora hcv polimeraze |
| US7153848B2 (en) * | 2004-08-09 | 2006-12-26 | Bristol-Myers Squibb Company | Inhibitors of HCV replication |
| EP1807403A2 (en) | 2004-10-26 | 2007-07-18 | Istituto di Richerche di Biologia Molecolare P. Angeletti S.p.A. | Tetracyclic indole derivatives as antiviral agents |
| GB0518390D0 (en) | 2005-09-09 | 2005-10-19 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
| US7473688B2 (en) * | 2005-09-13 | 2009-01-06 | Bristol-Myers Squibb Company | Indolobenzazepine 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 |
| JP5205370B2 (ja) * | 2006-05-25 | 2013-06-05 | ブリストル−マイヤーズ スクイブ カンパニー | シクロプロピル縮合インドロベンゾアゼピンｈｃｖｎｓ５ｂ阻害剤 |
| 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 |
| 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 |
| 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 |
| US7538103B2 (en) * | 2007-03-15 | 2009-05-26 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
-
2008
- 2008-07-28 US US12/180,994 patent/US7652004B2/en active Active
- 2008-08-01 MX MX2010001416A patent/MX2010001416A/es active IP Right Grant
- 2008-08-01 EP EP08828571.3A patent/EP2183252B1/en not_active Not-in-force
- 2008-08-01 JP JP2010520215A patent/JP5465670B2/ja not_active Expired - Fee Related
- 2008-08-01 BR BRPI0814931-3A2A patent/BRPI0814931A2/pt not_active IP Right Cessation
- 2008-08-01 CN CN2008801108622A patent/CN101821267B/zh not_active Expired - Fee Related
- 2008-08-01 CA CA2695781A patent/CA2695781A1/en not_active Abandoned
- 2008-08-01 AU AU2008293845A patent/AU2008293845B2/en not_active Ceased
- 2008-08-01 EA EA201000277A patent/EA015978B1/ru not_active IP Right Cessation
- 2008-08-01 KR KR1020107005086A patent/KR20100066492A/ko not_active Withdrawn
- 2008-08-01 NZ NZ583149A patent/NZ583149A/en not_active IP Right Cessation
- 2008-08-01 WO PCT/US2008/071881 patent/WO2009029384A2/en not_active Ceased
- 2008-08-08 TW TW097130410A patent/TW200906418A/zh unknown
- 2008-08-08 PE PE2008001327A patent/PE20090618A1/es not_active Application Discontinuation
- 2008-08-08 CL CL200802353A patent/CL2008002353A1/es unknown
- 2008-08-08 AR ARP080103488A patent/AR067897A1/es unknown
-
2010
- 2010-02-03 CO CO10011252A patent/CO6251359A2/es not_active Application Discontinuation
- 2010-02-08 ZA ZA2010/00923A patent/ZA201000923B/en unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007033032A1 (en) * | 2005-09-12 | 2007-03-22 | Bristol-Myers Squibb Company | Cyclopropyl fused indolobenzazepine hcv ns5b inhibitors |
| WO2007092888A2 (en) * | 2006-02-08 | 2007-08-16 | Bristol-Myers Squibb Company | Hcv ns5b inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| US7652004B2 (en) | 2010-01-26 |
| AR067897A1 (es) | 2009-10-28 |
| AU2008293845A1 (en) | 2009-03-05 |
| MX2010001416A (es) | 2010-03-01 |
| EA015978B1 (ru) | 2012-01-30 |
| CO6251359A2 (es) | 2011-02-21 |
| US20090074715A1 (en) | 2009-03-19 |
| WO2009029384A2 (en) | 2009-03-05 |
| JP2010535787A (ja) | 2010-11-25 |
| ZA201000923B (en) | 2011-04-28 |
| EP2183252A2 (en) | 2010-05-12 |
| EA201000277A1 (ru) | 2010-06-30 |
| PE20090618A1 (es) | 2009-05-16 |
| KR20100066492A (ko) | 2010-06-17 |
| WO2009029384A3 (en) | 2009-05-28 |
| CN101821267B (zh) | 2013-07-10 |
| EP2183252B1 (en) | 2015-01-14 |
| JP5465670B2 (ja) | 2014-04-09 |
| CL2008002353A1 (es) | 2008-10-24 |
| NZ583149A (en) | 2011-07-29 |
| CA2695781A1 (en) | 2009-03-05 |
| TW200906418A (en) | 2009-02-16 |
| CN101821267A (zh) | 2010-09-01 |
| BRPI0814931A2 (pt) | 2015-02-03 |
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| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |