MX2010011921A - Compuestos para el tratamiento de la hepatitis c. - Google Patents
Compuestos para el tratamiento de la hepatitis c.Info
- Publication number
- MX2010011921A MX2010011921A MX2010011921A MX2010011921A MX2010011921A MX 2010011921 A MX2010011921 A MX 2010011921A MX 2010011921 A MX2010011921 A MX 2010011921A MX 2010011921 A MX2010011921 A MX 2010011921A MX 2010011921 A MX2010011921 A MX 2010011921A
- Authority
- MX
- Mexico
- Prior art keywords
- alkyl
- mmol
- solvent
- cyclohexyl
- methoxy
- Prior art date
Links
- 208000006454 hepatitis Diseases 0.000 title description 6
- 231100000283 hepatitis Toxicity 0.000 title description 6
- 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 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 205
- 241000711549 Hepacivirus C Species 0.000 claims abstract description 92
- 238000000034 method Methods 0.000 claims abstract description 56
- 239000000203 mixture Substances 0.000 claims abstract description 41
- 230000000694 effects Effects 0.000 claims abstract description 23
- -1 pyridinonyl Chemical group 0.000 claims description 231
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 137
- 125000000217 alkyl group Chemical group 0.000 claims description 131
- 229910052739 hydrogen Inorganic materials 0.000 claims description 122
- 229910052757 nitrogen Inorganic materials 0.000 claims description 80
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 80
- 239000001257 hydrogen Substances 0.000 claims description 66
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 66
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 62
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 53
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 47
- 125000001424 substituent group Chemical group 0.000 claims description 38
- 150000003839 salts Chemical class 0.000 claims description 34
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 28
- 125000003282 alkyl amino group Chemical group 0.000 claims description 24
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 24
- 125000003386 piperidinyl group Chemical group 0.000 claims description 19
- 125000002757 morpholinyl group Chemical group 0.000 claims description 17
- 125000004193 piperazinyl group Chemical group 0.000 claims description 17
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 16
- 239000003112 inhibitor Substances 0.000 claims description 16
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 15
- 125000002393 azetidinyl group Chemical group 0.000 claims description 14
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 125000004076 pyridyl 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
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 10
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 9
- 102000014150 Interferons Human genes 0.000 claims description 8
- 108010050904 Interferons Proteins 0.000 claims description 8
- 125000002883 imidazolyl group Chemical group 0.000 claims description 8
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 8
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 8
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 8
- 229910003844 NSO2 Inorganic materials 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000001475 halogen functional group Chemical group 0.000 claims description 7
- 108700008776 hepatitis C virus NS-5 Proteins 0.000 claims description 7
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 7
- 101800001014 Non-structural protein 5A Proteins 0.000 claims description 6
- 230000008901 benefit Effects 0.000 claims description 6
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 6
- 229930182912 cyclosporin Natural products 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 6
- 108010006035 Metalloproteases Proteins 0.000 claims description 5
- 102000005741 Metalloproteases Human genes 0.000 claims description 5
- 108060004795 Methyltransferase Proteins 0.000 claims description 5
- 101800001019 Non-structural protein 4B Proteins 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 108010022999 Serine Proteases Proteins 0.000 claims description 4
- 102000012479 Serine Proteases Human genes 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000006254 cycloalkyl carbonyl 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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 4
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- 208000005176 Hepatitis C Diseases 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229940121649 protein inhibitor Drugs 0.000 claims 5
- 239000012268 protein inhibitor Substances 0.000 claims 5
- 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
- 229940047124 interferons Drugs 0.000 claims 2
- 229940047122 interleukins Drugs 0.000 claims 2
- 230000001225 therapeutic effect Effects 0.000 claims 2
- 229940124683 HCV polymerase inhibitor Drugs 0.000 claims 1
- 208000010710 hepatitis C virus infection Diseases 0.000 claims 1
- 239000003001 serine protease inhibitor Substances 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 550
- 239000002904 solvent Substances 0.000 description 514
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 297
- 238000006243 chemical reaction Methods 0.000 description 289
- 229910001868 water Inorganic materials 0.000 description 192
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 183
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 174
- 239000000047 product Substances 0.000 description 155
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 149
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 148
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 142
- 239000007787 solid Substances 0.000 description 141
- 230000014759 maintenance of location Effects 0.000 description 125
- 239000000243 solution Substances 0.000 description 125
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 119
- 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 105
- 239000005695 Ammonium acetate Substances 0.000 description 104
- 235000019257 ammonium acetate Nutrition 0.000 description 104
- 229940043376 ammonium acetate Drugs 0.000 description 104
- 238000004128 high performance liquid chromatography Methods 0.000 description 82
- 238000010828 elution Methods 0.000 description 79
- 238000005481 NMR spectroscopy Methods 0.000 description 78
- 239000012299 nitrogen atmosphere Substances 0.000 description 74
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 74
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 69
- 239000011541 reaction mixture Substances 0.000 description 68
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 64
- 235000019439 ethyl acetate Nutrition 0.000 description 64
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 62
- 238000004458 analytical method Methods 0.000 description 61
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- 239000007788 liquid Substances 0.000 description 54
- 239000003039 volatile agent Substances 0.000 description 52
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 51
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 50
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- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 34
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
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- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 10
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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
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- 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
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- 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)
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- 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)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5074308P | 2008-05-06 | 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 |
|---|---|
| MX2010011921A true MX2010011921A (es) | 2010-11-30 |
Family
ID=40786514
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2010011921A MX2010011921A (es) | 2008-05-06 | 2009-05-05 | Compuestos para el tratamiento de la hepatitis c. |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US8133884B2 (enExample) |
| EP (1) | EP2280975B1 (enExample) |
| JP (1) | JP2011520810A (enExample) |
| KR (1) | KR20110015588A (enExample) |
| CN (1) | CN102083834A (enExample) |
| AR (1) | AR071684A1 (enExample) |
| AU (1) | AU2009244409A1 (enExample) |
| BR (1) | BRPI0915130A2 (enExample) |
| CA (1) | CA2723683A1 (enExample) |
| CL (1) | CL2009001089A1 (enExample) |
| CO (1) | CO6290645A2 (enExample) |
| EA (1) | EA201001748A1 (enExample) |
| IL (1) | IL208753A0 (enExample) |
| MX (1) | MX2010011921A (enExample) |
| NZ (1) | NZ588556A (enExample) |
| PE (1) | PE20091879A1 (enExample) |
| TW (1) | TW200951135A (enExample) |
| WO (1) | WO2009137454A1 (enExample) |
| ZA (1) | ZA201007649B (enExample) |
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 |
| AU2013217224B2 (en) | 2012-02-10 | 2017-04-06 | Lupin Limited | Antiviral compounds with a dibenzooxaheterocycle moiety |
| US9556204B2 (en) * | 2012-07-18 | 2017-01-31 | Bristol-Myers Squibb Company | 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 |
|---|---|---|---|---|
| EP1719773B1 (en) | 2004-02-24 | 2009-04-15 | Japan Tobacco, Inc. | Fused heterotetracyclic compounds and use tehreof as hcv polymerase inhibitor |
| US7153848B2 (en) | 2004-08-09 | 2006-12-26 | Bristol-Myers Squibb Company | Inhibitors of HCV replication |
| AU2005298412B2 (en) | 2004-10-26 | 2011-06-09 | Istituto Di Ricerche Di Biologia Molecolare P Angeletti Spa | 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 |
| ATE469155T1 (de) | 2006-05-25 | 2010-06-15 | Bristol Myers Squibb Co | Cyclopropyl-fusionierte indolbenzazepin-hcv-ns5b- hemmer |
| 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 |
| US7521444B2 (en) | 2007-03-14 | 2009-04-21 | 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 |
| US7541353B2 (en) | 2007-03-14 | 2009-06-02 | 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 |
| US8129367B2 (en) | 2007-11-21 | 2012-03-06 | 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 |
-
2009
- 2009-05-04 US US12/434,748 patent/US8133884B2/en active Active
- 2009-05-05 MX MX2010011921A patent/MX2010011921A/es active IP Right Grant
- 2009-05-05 CA CA2723683A patent/CA2723683A1/en not_active Abandoned
- 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 NZ NZ588556A patent/NZ588556A/en not_active IP Right Cessation
- 2009-05-05 AU AU2009244409A patent/AU2009244409A1/en not_active Abandoned
- 2009-05-05 PE PE2009000605A patent/PE20091879A1/es not_active Application Discontinuation
- 2009-05-05 WO PCT/US2009/042805 patent/WO2009137454A1/en not_active Ceased
- 2009-05-05 KR KR1020107027222A patent/KR20110015588A/ko not_active Withdrawn
- 2009-05-05 CN CN2009801263266A patent/CN102083834A/zh active Pending
- 2009-05-05 JP JP2011508593A patent/JP2011520810A/ja not_active Withdrawn
- 2009-05-05 EP EP09743440.1A patent/EP2280975B1/en not_active Ceased
- 2009-05-06 AR ARP090101641A patent/AR071684A1/es not_active Application Discontinuation
- 2009-05-06 TW TW098115001A patent/TW200951135A/zh unknown
- 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 |
|---|---|
| WO2009137454A1 (en) | 2009-11-12 |
| EP2280975A1 (en) | 2011-02-09 |
| KR20110015588A (ko) | 2011-02-16 |
| NZ588556A (en) | 2012-06-29 |
| CA2723683A1 (en) | 2009-11-12 |
| CL2009001089A1 (es) | 2011-04-29 |
| EA201001748A1 (ru) | 2011-06-30 |
| TW200951135A (en) | 2009-12-16 |
| JP2011520810A (ja) | 2011-07-21 |
| AR071684A1 (es) | 2010-07-07 |
| EP2280975B1 (en) | 2014-01-01 |
| CN102083834A (zh) | 2011-06-01 |
| AU2009244409A1 (en) | 2009-11-12 |
| PE20091879A1 (es) | 2009-12-19 |
| BRPI0915130A2 (pt) | 2019-09-24 |
| CO6290645A2 (es) | 2011-06-20 |
| ZA201007649B (en) | 2012-04-25 |
| US20090280083A1 (en) | 2009-11-12 |
| US8133884B2 (en) | 2012-03-13 |
| IL208753A0 (en) | 2010-12-30 |
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Legal Events
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| FG | Grant or registration |