AU2009244409A1 - 7H-indolo[2,1-a] [2] benzazepine-10-carboxylic acid derivatives for the treatment of Hepatitis C - Google Patents
7H-indolo[2,1-a] [2] benzazepine-10-carboxylic acid derivatives for the treatment of Hepatitis C Download PDFInfo
- Publication number
- AU2009244409A1 AU2009244409A1 AU2009244409A AU2009244409A AU2009244409A1 AU 2009244409 A1 AU2009244409 A1 AU 2009244409A1 AU 2009244409 A AU2009244409 A AU 2009244409A AU 2009244409 A AU2009244409 A AU 2009244409A AU 2009244409 A1 AU2009244409 A1 AU 2009244409A1
- Authority
- AU
- Australia
- Prior art keywords
- solvent
- mmol
- alkyl
- cyclohexyl
- indolo
- 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.)
- Abandoned
Links
- 208000005176 Hepatitis C Diseases 0.000 title claims description 4
- FRUWAONHRDGSAL-UHFFFAOYSA-N 7h-indolo[2,1-a][2]benzazepine-10-carboxylic acid Chemical class C1=CCN2C3=CC(C(=O)O)=CC=C3C=C2C2=CC=CC=C21 FRUWAONHRDGSAL-UHFFFAOYSA-N 0.000 title description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 275
- 150000001875 compounds Chemical class 0.000 claims description 197
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 191
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 178
- -1 pyridinonyl Chemical group 0.000 claims description 164
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 142
- 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 101
- 125000000217 alkyl group Chemical group 0.000 claims description 100
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 99
- 229910052757 nitrogen Inorganic materials 0.000 claims description 57
- 238000000034 method Methods 0.000 claims description 55
- 239000001257 hydrogen Substances 0.000 claims description 54
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 37
- 125000001424 substituent group Chemical group 0.000 claims description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 28
- 150000002431 hydrogen Chemical group 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 25
- 125000003282 alkyl amino group Chemical group 0.000 claims description 18
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 125000004193 piperazinyl group Chemical group 0.000 claims description 17
- 125000003386 piperidinyl group Chemical group 0.000 claims description 16
- 125000002757 morpholinyl group Chemical group 0.000 claims description 13
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 12
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000002393 azetidinyl group Chemical group 0.000 claims description 11
- 108700008776 hepatitis C virus NS-5 Proteins 0.000 claims description 11
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 102000014150 Interferons Human genes 0.000 claims description 9
- 108010050904 Interferons Proteins 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 9
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 9
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 9
- 125000002883 imidazolyl group Chemical group 0.000 claims description 7
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 7
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
- 229930182912 cyclosporin Natural products 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000001475 halogen functional group Chemical group 0.000 claims description 6
- 230000008901 benefit Effects 0.000 claims description 5
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 5
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
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- 101800001019 Non-structural protein 4B Proteins 0.000 claims description 4
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- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 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 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 4
- 229910003844 NSO2 Inorganic materials 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 3
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 125000004043 oxo group Chemical group O=* 0.000 claims description 3
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 125000001425 triazolyl group Chemical group 0.000 claims description 3
- 101100440696 Caenorhabditis elegans cor-1 gene Proteins 0.000 claims description 2
- MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 claims description 2
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- 229940047124 interferons Drugs 0.000 claims 2
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- 239000003475 metalloproteinase inhibitor Substances 0.000 claims 2
- 239000003001 serine protease inhibitor Substances 0.000 claims 2
- 230000001225 therapeutic effect Effects 0.000 claims 2
- 208000010710 hepatitis C virus infection Diseases 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 537
- 239000002904 solvent Substances 0.000 description 509
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 307
- 238000006243 chemical reaction Methods 0.000 description 218
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- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 162
- 239000000047 product Substances 0.000 description 157
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 155
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 154
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 142
- 239000007787 solid Substances 0.000 description 140
- 239000000243 solution Substances 0.000 description 124
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 114
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 104
- 239000005695 Ammonium acetate Substances 0.000 description 104
- 235000019257 ammonium acetate Nutrition 0.000 description 104
- 229940043376 ammonium acetate Drugs 0.000 description 104
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 103
- 230000014759 maintenance of location Effects 0.000 description 101
- 238000005481 NMR spectroscopy Methods 0.000 description 93
- IMBBXSASDSZJSX-UHFFFAOYSA-N 4-Carboxypyrazole Chemical compound OC(=O)C=1C=NNC=1 IMBBXSASDSZJSX-UHFFFAOYSA-N 0.000 description 92
- 238000004128 high performance liquid chromatography Methods 0.000 description 91
- 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 85
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 65
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- 241000711549 Hepacivirus C Species 0.000 description 47
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- 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems
-
- 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
- C07D487/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/08—Bridged systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Virology (AREA)
- Oncology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Gastroenterology & Hepatology (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5074308P | 2008-05-06 | 2008-05-06 | |
| US61/050,743 | 2008-05-06 | ||
| PCT/US2009/042805 WO2009137454A1 (en) | 2008-05-06 | 2009-05-05 | 7h-indolo[2,1-a] [2] benzazepine-10-carboxylic acid derivatives for the treatment of hepatitis c |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2009244409A1 true AU2009244409A1 (en) | 2009-11-12 |
Family
ID=40786514
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2009244409A Abandoned AU2009244409A1 (en) | 2008-05-06 | 2009-05-05 | 7H-indolo[2,1-a] [2] benzazepine-10-carboxylic acid derivatives for the treatment of Hepatitis C |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US8133884B2 (https=) |
| EP (1) | EP2280975B1 (https=) |
| JP (1) | JP2011520810A (https=) |
| KR (1) | KR20110015588A (https=) |
| CN (1) | CN102083834A (https=) |
| AR (1) | AR071684A1 (https=) |
| AU (1) | AU2009244409A1 (https=) |
| BR (1) | BRPI0915130A2 (https=) |
| CA (1) | CA2723683A1 (https=) |
| CL (1) | CL2009001089A1 (https=) |
| CO (1) | CO6290645A2 (https=) |
| EA (1) | EA201001748A1 (https=) |
| IL (1) | IL208753A0 (https=) |
| MX (1) | MX2010011921A (https=) |
| NZ (1) | NZ588556A (https=) |
| PE (1) | PE20091879A1 (https=) |
| TW (1) | TW200951135A (https=) |
| WO (1) | WO2009137454A1 (https=) |
| ZA (1) | ZA201007649B (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070049593A1 (en) | 2004-02-24 | 2007-03-01 | Japan Tobacco Inc. | Tetracyclic fused heterocyclic compound and use thereof as HCV polymerase inhibitor |
| KR20100124848A (ko) | 2008-03-27 | 2010-11-29 | 브리스톨-마이어스 스큅 컴퍼니 | 방향족 헤테로시클릭 융합된 인돌로벤자디아제핀 ｈｃｖ ｎｓ5ｂ 억제제 |
| UA103319C2 (en) | 2008-05-06 | 2013-10-10 | Глаксосмитклайн Ллк | Thiazole- and oxazole-benzene sulfonamide compounds |
| CA2822357A1 (en) | 2010-12-22 | 2012-06-28 | Abbvie Inc. | Hepatitis c inhibitors and uses thereof |
| WO2013030750A1 (en) | 2011-09-01 | 2013-03-07 | Lupin Limited | Antiviral compounds |
| CA2862755A1 (en) | 2012-02-10 | 2013-08-15 | Lupin Limited | Antiviral compounds with a dibenzooxaheterocycle moiety |
| 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 |
Family Cites Families (25)
| 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 |
| 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 |
| WO2007140200A2 (en) | 2006-05-25 | 2007-12-06 | 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 |
| 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 |
| US20090018163A1 (en) | 2007-07-11 | 2009-01-15 | Bristol-Myers Squibb Company | Substituted Heterocyclic Ethers and Their Use in CNS Disorders |
| US7642251B2 (en) | 2007-08-09 | 2010-01-05 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US7652004B2 (en) | 2007-08-09 | 2010-01-26 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US8124601B2 (en) | 2007-11-21 | 2012-02-28 | Bristol-Myers Squibb Company | Compounds for the treatment of Hepatitis C |
| US8129367B2 (en) | 2007-11-21 | 2012-03-06 | Bristol-Myers Squibb Company | Compounds for the treatment of Hepatitis C |
-
2009
- 2009-05-04 US US12/434,748 patent/US8133884B2/en active Active
- 2009-05-05 CA CA2723683A patent/CA2723683A1/en not_active Abandoned
- 2009-05-05 PE PE2009000605A patent/PE20091879A1/es not_active Application Discontinuation
- 2009-05-05 EP EP09743440.1A patent/EP2280975B1/en not_active Ceased
- 2009-05-05 AU AU2009244409A patent/AU2009244409A1/en not_active Abandoned
- 2009-05-05 CN CN2009801263266A patent/CN102083834A/zh active Pending
- 2009-05-05 NZ NZ588556A patent/NZ588556A/en not_active IP Right Cessation
- 2009-05-05 KR KR1020107027222A patent/KR20110015588A/ko not_active Withdrawn
- 2009-05-05 WO PCT/US2009/042805 patent/WO2009137454A1/en not_active Ceased
- 2009-05-05 BR BRPI0915130A patent/BRPI0915130A2/pt not_active IP Right Cessation
- 2009-05-05 EA EA201001748A patent/EA201001748A1/ru unknown
- 2009-05-05 JP JP2011508593A patent/JP2011520810A/ja not_active Withdrawn
- 2009-05-05 MX MX2010011921A patent/MX2010011921A/es active IP Right Grant
- 2009-05-06 TW TW098115001A patent/TW200951135A/zh unknown
- 2009-05-06 AR ARP090101641A patent/AR071684A1/es not_active Application Discontinuation
- 2009-05-06 CL CL2009001089A patent/CL2009001089A1/es unknown
-
2010
- 2010-10-14 IL IL208753A patent/IL208753A0/en unknown
- 2010-10-26 ZA ZA2010/07649A patent/ZA201007649B/en unknown
- 2010-10-28 CO CO10134256A patent/CO6290645A2/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP2280975A1 (en) | 2011-02-09 |
| PE20091879A1 (es) | 2009-12-19 |
| CL2009001089A1 (es) | 2011-04-29 |
| US20090280083A1 (en) | 2009-11-12 |
| CO6290645A2 (es) | 2011-06-20 |
| US8133884B2 (en) | 2012-03-13 |
| JP2011520810A (ja) | 2011-07-21 |
| CA2723683A1 (en) | 2009-11-12 |
| BRPI0915130A2 (pt) | 2019-09-24 |
| IL208753A0 (en) | 2010-12-30 |
| KR20110015588A (ko) | 2011-02-16 |
| ZA201007649B (en) | 2012-04-25 |
| EP2280975B1 (en) | 2014-01-01 |
| MX2010011921A (es) | 2010-11-30 |
| TW200951135A (en) | 2009-12-16 |
| EA201001748A1 (ru) | 2011-06-30 |
| CN102083834A (zh) | 2011-06-01 |
| WO2009137454A1 (en) | 2009-11-12 |
| AR071684A1 (es) | 2010-07-07 |
| NZ588556A (en) | 2012-06-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK4 | Application lapsed section 142(2)(d) - no continuation fee paid for the application |