MX2007003371A - Derivados de carbazol y ciclopentaindol para tratar infeccion con virus de hepatitis c. - Google Patents
Derivados de carbazol y ciclopentaindol para tratar infeccion con virus de hepatitis c.Info
- Publication number
- MX2007003371A MX2007003371A MX2007003371A MX2007003371A MX2007003371A MX 2007003371 A MX2007003371 A MX 2007003371A MX 2007003371 A MX2007003371 A MX 2007003371A MX 2007003371 A MX2007003371 A MX 2007003371A MX 2007003371 A MX2007003371 A MX 2007003371A
- Authority
- MX
- Mexico
- Prior art keywords
- carbon atoms
- tetrahydro
- carboxylic acid
- cyclopenta
- indole
- Prior art date
Links
- 208000015181 infectious disease Diseases 0.000 title claims description 8
- 241000711549 Hepacivirus C Species 0.000 title description 20
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 title description 6
- HFGUJIUXLNDRAF-UHFFFAOYSA-N cyclopenta[g]indole Chemical class C1=CC2=CC=CC2=C2N=CC=C21 HFGUJIUXLNDRAF-UHFFFAOYSA-N 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 92
- 208000005176 Hepatitis C Diseases 0.000 claims abstract description 15
- 241000124008 Mammalia Species 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 180
- 125000000217 alkyl group Chemical group 0.000 claims description 62
- -1 furanylmethyl Chemical group 0.000 claims description 40
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 30
- 210000004027 cell Anatomy 0.000 claims description 28
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 125000003342 alkenyl group Chemical group 0.000 claims description 23
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 18
- 125000000304 alkynyl group Chemical group 0.000 claims description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 13
- 239000003981 vehicle Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 101800001554 RNA-directed RNA polymerase Proteins 0.000 claims description 7
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
- 230000002265 prevention Effects 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 5
- 150000001721 carbon Chemical group 0.000 claims description 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 5
- 230000005764 inhibitory process Effects 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- WGENBJJKSVMSGJ-UHFFFAOYSA-N 2-(5-cyano-1-propyl-2,3,4,9-tetrahydrocarbazol-1-yl)acetic acid Chemical compound N1C2=CC=CC(C#N)=C2C2=C1C(CCC)(CC(O)=O)CCC2 WGENBJJKSVMSGJ-UHFFFAOYSA-N 0.000 claims description 4
- NQNDJICKBDRTND-UHFFFAOYSA-N 2-(5-cyano-8-fluoro-1-propyl-2,3,4,9-tetrahydrocarbazol-1-yl)acetic acid Chemical compound N1C2=C(F)C=CC(C#N)=C2C2=C1C(CCC)(CC(O)=O)CCC2 NQNDJICKBDRTND-UHFFFAOYSA-N 0.000 claims description 4
- SGWDODVGBXFOHX-UHFFFAOYSA-N 2-(8-carbamoyl-5-cyano-1-propyl-2,3,4,9-tetrahydrocarbazol-1-yl)acetic acid Chemical compound N1C2=C(C(N)=O)C=CC(C#N)=C2C2=C1C(CCC)(CC(O)=O)CCC2 SGWDODVGBXFOHX-UHFFFAOYSA-N 0.000 claims description 4
- WXVDJFVBOHMICQ-UHFFFAOYSA-N 5,8-dichloro-1-propyl-2,3,4,9-tetrahydrocarbazole-1-carboxylic acid Chemical compound N1C2=C(Cl)C=CC(Cl)=C2C2=C1C(CCC)(C(O)=O)CCC2 WXVDJFVBOHMICQ-UHFFFAOYSA-N 0.000 claims description 4
- BGJZMLAKAFRASM-UHFFFAOYSA-N 5-cyano-1-(cyclobutylmethyl)-8-fluoro-2,3,4,9-tetrahydrocarbazole-1-carboxylic acid Chemical compound C1CCC(C2=C(C#N)C=CC(F)=C2N2)=C2C1(C(=O)O)CC1CCC1 BGJZMLAKAFRASM-UHFFFAOYSA-N 0.000 claims description 4
- KRFGICBRUITTJH-UHFFFAOYSA-N 5-cyano-8-fluoro-1-propyl-2,3,4,9-tetrahydrocarbazole-1-carboxylic acid Chemical compound N1C2=C(F)C=CC(C#N)=C2C2=C1C(CCC)(C(O)=O)CCC2 KRFGICBRUITTJH-UHFFFAOYSA-N 0.000 claims description 4
- MODPSKZFBZNESH-UHFFFAOYSA-N 5-cyano-8-methyl-1-propyl-2,3,4,9-tetrahydrocarbazole-1-carboxylic acid Chemical compound N1C2=C(C)C=CC(C#N)=C2C2=C1C(CCC)(C(O)=O)CCC2 MODPSKZFBZNESH-UHFFFAOYSA-N 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 4
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 4
- 125000001984 thiazolidinyl group Chemical group 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 3
- 230000001580 bacterial effect Effects 0.000 claims description 2
- 210000004962 mammalian cell Anatomy 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 6
- AFDTUDKFSMWIAU-UHFFFAOYSA-N 2-(5,7-difluoro-1-propyl-2,3,4,9-tetrahydrocarbazol-1-yl)acetic acid Chemical compound N1C2=CC(F)=CC(F)=C2C2=C1C(CCC)(CC(O)=O)CCC2 AFDTUDKFSMWIAU-UHFFFAOYSA-N 0.000 claims 3
- KKRITWOLVWDFFN-UHFFFAOYSA-N 2-(5,8-dicyano-1-propyl-2,3,4,9-tetrahydrocarbazol-1-yl)acetic acid Chemical compound N1C2=C(C#N)C=CC(C#N)=C2C2=C1C(CCC)(CC(O)=O)CCC2 KKRITWOLVWDFFN-UHFFFAOYSA-N 0.000 claims 3
- NDKUXQXILLYKKZ-UHFFFAOYSA-N 3-butyl-5,8-dichloro-2,4-dihydro-1h-cyclopenta[b]indole-3-carboxylic acid Chemical compound N1C2=C(Cl)C=CC(Cl)=C2C2=C1C(CCCC)(C(O)=O)CC2 NDKUXQXILLYKKZ-UHFFFAOYSA-N 0.000 claims 3
- VUCHCGKNUOLUQK-UHFFFAOYSA-N 3-butyl-7-fluoro-5-methyl-2,4-dihydro-1h-cyclopenta[b]indole-3-carboxylic acid Chemical compound N1C2=C(C)C=C(F)C=C2C2=C1C(CCCC)(C(O)=O)CC2 VUCHCGKNUOLUQK-UHFFFAOYSA-N 0.000 claims 3
- ROLZHTZWLHLZCQ-UHFFFAOYSA-N 3-butyl-8-cyano-5-fluoro-2,4-dihydro-1h-cyclopenta[b]indole-3-carboxylic acid Chemical compound N1C2=C(F)C=CC(C#N)=C2C2=C1C(CCCC)(C(O)=O)CC2 ROLZHTZWLHLZCQ-UHFFFAOYSA-N 0.000 claims 3
- VQOPOVBNNLJNSI-UHFFFAOYSA-N 3-butyl-8-cyano-5-methyl-2,4-dihydro-1h-cyclopenta[b]indole-3-carboxylic acid Chemical compound N1C2=C(C)C=CC(C#N)=C2C2=C1C(CCCC)(C(O)=O)CC2 VQOPOVBNNLJNSI-UHFFFAOYSA-N 0.000 claims 3
- TVSMABGYTPMGPU-UHFFFAOYSA-N 5,8-dichloro-1-ethyl-2,3,4,9-tetrahydrocarbazole-1-carboxylic acid Chemical compound N1C2=C(Cl)C=CC(Cl)=C2C2=C1C(CC)(C(O)=O)CCC2 TVSMABGYTPMGPU-UHFFFAOYSA-N 0.000 claims 3
- UVKVBHPKFLJUCF-UHFFFAOYSA-N 5,8-dichloro-3-prop-2-enyl-2,4-dihydro-1h-cyclopenta[b]indole-3-carboxylic acid Chemical compound N1C2=C(Cl)C=CC(Cl)=C2C2=C1C(C(=O)O)(CC=C)CC2 UVKVBHPKFLJUCF-UHFFFAOYSA-N 0.000 claims 3
- ZEBPOFKSMDBBIP-UHFFFAOYSA-N 5,8-dichloro-3-propyl-2,4-dihydro-1h-cyclopenta[b]indole-3-carboxylic acid Chemical compound N1C2=C(Cl)C=CC(Cl)=C2C2=C1C(CCC)(C(O)=O)CC2 ZEBPOFKSMDBBIP-UHFFFAOYSA-N 0.000 claims 3
- GGMQIOLVDVZJEY-UHFFFAOYSA-N 8-bromo-3-butyl-5-fluoro-2,4-dihydro-1h-cyclopenta[b]indole-3-carboxylic acid Chemical compound N1C2=C(F)C=CC(Br)=C2C2=C1C(CCCC)(C(O)=O)CC2 GGMQIOLVDVZJEY-UHFFFAOYSA-N 0.000 claims 3
- BELKQACUXXVKGU-UHFFFAOYSA-N 8-bromo-3-butyl-5-methyl-2,4-dihydro-1h-cyclopenta[b]indole-3-carboxylic acid Chemical compound N1C2=C(C)C=CC(Br)=C2C2=C1C(CCCC)(C(O)=O)CC2 BELKQACUXXVKGU-UHFFFAOYSA-N 0.000 claims 3
- AVGMUKWZKNEEGD-UHFFFAOYSA-N 8-bromo-5-fluoro-3-propyl-2,4-dihydro-1h-cyclopenta[b]indole-3-carboxylic acid Chemical compound N1C2=C(F)C=CC(Br)=C2C2=C1C(CCC)(C(O)=O)CC2 AVGMUKWZKNEEGD-UHFFFAOYSA-N 0.000 claims 3
- YTYSTPUXYCVFKA-UHFFFAOYSA-N 8-bromo-5-methyl-3-propyl-2,4-dihydro-1h-cyclopenta[b]indole-3-carboxylic acid Chemical compound N1C2=C(C)C=CC(Br)=C2C2=C1C(CCC)(C(O)=O)CC2 YTYSTPUXYCVFKA-UHFFFAOYSA-N 0.000 claims 3
- SOOIMQWGGBSTMX-UHFFFAOYSA-N 8-bromo-7-fluoro-5-methyl-3-propyl-2,4-dihydro-1h-cyclopenta[b]indole-3-carboxylic acid Chemical compound N1C2=C(C)C=C(F)C(Br)=C2C2=C1C(CCC)(C(O)=O)CC2 SOOIMQWGGBSTMX-UHFFFAOYSA-N 0.000 claims 3
- UJIFIPSJPHVBSG-UHFFFAOYSA-N 8-chloro-1-propyl-5-(trifluoromethyl)-2,3,4,9-tetrahydrocarbazole-1-carboxylic acid Chemical compound N1C2=C(Cl)C=CC(C(F)(F)F)=C2C2=C1C(CCC)(C(O)=O)CCC2 UJIFIPSJPHVBSG-UHFFFAOYSA-N 0.000 claims 3
- GBRSGCDWLVKGNZ-UHFFFAOYSA-N 8-cyano-5-fluoro-3-prop-2-enyl-2,4-dihydro-1h-cyclopenta[b]indole-3-carboxylic acid Chemical compound N1C2=C(F)C=CC(C#N)=C2C2=C1C(C(=O)O)(CC=C)CC2 GBRSGCDWLVKGNZ-UHFFFAOYSA-N 0.000 claims 3
- CYFCIXPSJVHSMX-UHFFFAOYSA-N 8-cyano-5-fluoro-3-propyl-2,4-dihydro-1h-cyclopenta[b]indole-3-carboxylic acid Chemical compound N1C2=C(F)C=CC(C#N)=C2C2=C1C(CCC)(C(O)=O)CC2 CYFCIXPSJVHSMX-UHFFFAOYSA-N 0.000 claims 3
- VYYVCKMHOOZGSL-UHFFFAOYSA-N 8-cyano-5-methyl-3-prop-2-enyl-2,4-dihydro-1h-cyclopenta[b]indole-3-carboxylic acid Chemical compound CC1=CC=C(C#N)C2=C1NC1=C2CCC1(C(O)=O)CC=C VYYVCKMHOOZGSL-UHFFFAOYSA-N 0.000 claims 3
- YBEFUBSZGDRNEE-UHFFFAOYSA-N 8-cyano-7-fluoro-5-methyl-3-prop-2-enyl-2,4-dihydro-1h-cyclopenta[b]indole-3-carboxylic acid Chemical compound CC1=CC(F)=C(C#N)C2=C1NC1=C2CCC1(C(O)=O)CC=C YBEFUBSZGDRNEE-UHFFFAOYSA-N 0.000 claims 3
- NNMAGWLGRCCEIE-UHFFFAOYSA-N 8-cyano-7-fluoro-5-methyl-3-propyl-2,4-dihydro-1h-cyclopenta[b]indole-3-carboxylic acid Chemical compound N1C2=C(C)C=C(F)C(C#N)=C2C2=C1C(CCC)(C(O)=O)CC2 NNMAGWLGRCCEIE-UHFFFAOYSA-N 0.000 claims 3
- PJCITKIXTABVGF-UHFFFAOYSA-N 3-butyl-8-cyano-7-fluoro-5-methyl-2,4-dihydro-1h-cyclopenta[b]indole-3-carboxylic acid Chemical compound N1C2=C(C)C=C(F)C(C#N)=C2C2=C1C(CCCC)(C(O)=O)CC2 PJCITKIXTABVGF-UHFFFAOYSA-N 0.000 claims 2
- GXCUYACJTXNSGX-UHFFFAOYSA-N 8-cyano-5-methyl-3-propyl-2,4-dihydro-1h-cyclopenta[b]indole-3-carboxylic acid Chemical compound N1C2=C(C)C=CC(C#N)=C2C2=C1C(CCC)(C(O)=O)CC2 GXCUYACJTXNSGX-UHFFFAOYSA-N 0.000 claims 2
- DQVZOYWZDJGZJY-UHFFFAOYSA-N 1,2,3,3a-tetrahydrocyclopenta[b]indole-3-carboxylic acid Chemical compound C1CC(C2N=C3C=CC=CC3=C21)C(=O)O DQVZOYWZDJGZJY-UHFFFAOYSA-N 0.000 claims 1
- 102000004163 DNA-directed RNA polymerases Human genes 0.000 claims 1
- 108090000626 DNA-directed RNA polymerases Proteins 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 20
- 208000036142 Viral infection Diseases 0.000 abstract description 5
- 230000009385 viral infection Effects 0.000 abstract description 5
- 238000006467 substitution reaction Methods 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 description 22
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 11
- 239000002609 medium Substances 0.000 description 11
- 239000002953 phosphate buffered saline Substances 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 229920001213 Polysorbate 20 Polymers 0.000 description 7
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 7
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 7
- KMAKOBLIOCQGJP-UHFFFAOYSA-N indole-3-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CNC2=C1 KMAKOBLIOCQGJP-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 5
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 4
- 238000002965 ELISA Methods 0.000 description 4
- 108060004795 Methyltransferase Proteins 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
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- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 125000004663 dialkyl amino group Chemical group 0.000 description 4
- BRZYSWJRSDMWLG-CAXSIQPQSA-N geneticin Natural products O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](C(C)O)O2)N)[C@@H](N)C[C@H]1N BRZYSWJRSDMWLG-CAXSIQPQSA-N 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
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- 102000004190 Enzymes Human genes 0.000 description 3
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- 229910019142 PO4 Inorganic materials 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
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- PGAVKCOVUIYSFO-XVFCMESISA-N UTP Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@H]1N1C(=O)NC(=O)C=C1 PGAVKCOVUIYSFO-XVFCMESISA-N 0.000 description 3
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- NZNMSOFKMUBTKW-UHFFFAOYSA-M cyclohexanecarboxylate Chemical compound [O-]C(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-M 0.000 description 3
- PCDQPRRSZKQHHS-ZAKLUEHWSA-N cytidine-5'-triphosphate Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@H](O)[C@@H](O)[C@H](CO[P@](O)(=O)O[P@@](O)(=O)OP(O)(O)=O)O1 PCDQPRRSZKQHHS-ZAKLUEHWSA-N 0.000 description 3
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- HMHXLPLTOMZUKK-UHFFFAOYSA-N ethyl 2-oxo-1-prop-2-enylcyclopentane-1-carboxylate Chemical compound CCOC(=O)C1(CC=C)CCCC1=O HMHXLPLTOMZUKK-UHFFFAOYSA-N 0.000 description 3
- FGSGHBPKHFDJOP-UHFFFAOYSA-N ethyl 2-oxocyclohexane-1-carboxylate Chemical compound CCOC(=O)C1CCCCC1=O FGSGHBPKHFDJOP-UHFFFAOYSA-N 0.000 description 3
- JHZPNBKZPAWCJD-UHFFFAOYSA-N ethyl 2-oxocyclopentane-1-carboxylate Chemical compound CCOC(=O)C1CCCC1=O JHZPNBKZPAWCJD-UHFFFAOYSA-N 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
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- 208000010710 hepatitis C virus infection Diseases 0.000 description 3
- 125000005553 heteroaryloxy group Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 239000002773 nucleotide Substances 0.000 description 3
- 125000003729 nucleotide group Chemical group 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
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- 230000001105 regulatory effect Effects 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
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- ABPJREHLAYHTHW-UHFFFAOYSA-N pyrano[2,3-g]indole Chemical class O1C=CC=C2C3=NC=CC3=CC=C21 ABPJREHLAYHTHW-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
-
- 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
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Virology (AREA)
- Molecular Biology (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US61214404P | 2004-09-23 | 2004-09-23 | |
| PCT/US2005/033803 WO2006034337A2 (en) | 2004-09-23 | 2005-09-21 | Carbazole and cyclopentaindole derivatives to treat infection with hepatitis c virus |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2007003371A true MX2007003371A (es) | 2007-05-07 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2007003371A MX2007003371A (es) | 2004-09-23 | 2005-09-21 | Derivados de carbazol y ciclopentaindol para tratar infeccion con virus de hepatitis c. |
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|---|---|
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| EP (1) | EP1793819A2 (enExample) |
| JP (1) | JP2008514611A (enExample) |
| CN (1) | CN101035528A (enExample) |
| AU (1) | AU2005286727A1 (enExample) |
| BR (1) | BRPI0515596A (enExample) |
| CA (1) | CA2577413A1 (enExample) |
| MX (1) | MX2007003371A (enExample) |
| WO (1) | WO2006034337A2 (enExample) |
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| WO2006121467A2 (en) * | 2004-11-22 | 2006-11-16 | Smithkline Beecham Corporation | Tetrahydrocarbazole derivatives for treating flaviridae viruses |
| WO2007035718A2 (en) | 2005-09-19 | 2007-03-29 | Emisphere Technologies, Inc. | Crystalline forms of the di-sodium salt of n-(5-chlorosalicyloyl)-8-aminocaprylic acid |
| AU2007286754A1 (en) * | 2006-08-25 | 2008-02-28 | Viropharma Incorporated | Identification and characterization of HCV replicon variants with reduced susceptibility to HCV-796, and methods related thereto |
| US8268803B2 (en) | 2006-12-22 | 2012-09-18 | Merck Sharp & Dohme Corp. | 5, 6-ring annulated indole derivatives and use thereof |
| KR20090094154A (ko) | 2006-12-22 | 2009-09-03 | 쉐링 코포레이션 | Ｈｃｖ 및 관련 바이러스 감염을 치료 또는 예방하기 위한 4,5-환 환상 인돌 유도체 |
| MX2009006878A (es) | 2006-12-22 | 2009-07-07 | Schering Corp | Derivados indolicos con anillo unido en las posiciones 4,5 para tratar o prevenir infecciones virales por virus de la hepatitis c e infecciones virales relacionadas. |
| NZ580917A (en) | 2007-05-04 | 2012-06-29 | Vertex Pharma | Combinations of protease inhibitors such as VX-950 and polymerase inhibitors for the treatment of HCV infection |
| KR20100065167A (ko) | 2007-08-29 | 2010-06-15 | 쉐링 코포레이션 | 바이러스 감염 치료용 2,3-치환된 아자인돌 유도체 |
| TW200924751A (en) | 2007-08-29 | 2009-06-16 | Schering Corp | 2,3-substituted indole derivatives and methods of use thereof |
| CN101821252A (zh) | 2007-08-29 | 2010-09-01 | 先灵公司 | 取代的吲哚衍生物及其使用方法 |
| CA2697451A1 (en) * | 2007-08-29 | 2009-03-12 | Schering Corporation | Tetracyclic indole derivatives and methods of use thereof |
| CN101868452B (zh) * | 2007-10-10 | 2014-08-06 | 诺华股份有限公司 | 螺环吡咯烷类与其对抗hcv和hiv感染的应用 |
| US8765757B2 (en) | 2007-11-16 | 2014-07-01 | Merck Sharp & Dohme Corp. | 3-heterocyclic substituted indole derivatives and methods of use thereof |
| MX2010005355A (es) | 2007-11-16 | 2010-06-02 | Schering Corp | Derivados de indol sustituidos con 3-aminosulfonilo y metodos de uso de los mismos. |
| MX2010013630A (es) | 2008-06-13 | 2010-12-21 | Schering Corp | Derivados triciclicos de indol y metodos de uso de los mismos. |
| US8580841B2 (en) * | 2008-07-23 | 2013-11-12 | Arena Pharmaceuticals, Inc. | Substituted 1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid derivatives useful in the treatment of autoimmune and inflammatory disorders |
| EP2342205B1 (en) | 2008-08-27 | 2016-04-20 | Arena Pharmaceuticals, Inc. | Substituted tricyclic acid derivatives as s1p1 receptor agonists useful in the treatment of autoimmune and inflammatory disorders |
| US8084620B2 (en) | 2008-12-19 | 2011-12-27 | Bristol-Myers Squibb Company | Carbazole carboxamide compounds useful as kinase inhibitors |
| EP4148045A1 (en) | 2010-01-27 | 2023-03-15 | Arena Pharmaceuticals, Inc. | Intermediate compounds for the preparation of (r)-2-(7-(4-cyclopentyl-3- (trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b] indol-3-yl)acetic acid and salts thereof |
| ES2558087T3 (es) | 2010-03-03 | 2016-02-01 | Arena Pharmaceuticals, Inc. | Procesos para la preparación de moduladores del receptor S1P1 y formas cristalinas de los mismos |
| CN105566202B (zh) * | 2014-10-31 | 2018-06-22 | 华东师范大学 | 一种1，2，3，4-四氢环戊基吲哚衍生物及其合成方法 |
| AU2016205361C1 (en) | 2015-01-06 | 2021-04-08 | Arena Pharmaceuticals, Inc. | Methods of treating conditions related to the S1P1 receptor |
| CA3002551A1 (en) | 2015-06-22 | 2016-12-29 | Arena Pharmaceuticals, Inc. | Crystalline l-arginine salt of (r)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclo-penta[b]indol-3-yl)acetic acid(com pound 1)for use in s1p1 receptor-associated disorders |
| MA52119A (fr) | 2015-10-19 | 2018-08-29 | Ncyte Corp | Composés hétérocycliques utilisés comme immunomodulateurs |
| PT3377488T (pt) | 2015-11-19 | 2022-11-21 | Incyte Corp | Compostos heterocíclicos como imunomoduladores |
| SI3394033T1 (sl) | 2015-12-22 | 2021-03-31 | Incyte Corporation | Heterociklične spojine kot imunomodulatorji |
| WO2017192961A1 (en) | 2016-05-06 | 2017-11-09 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| EP3464279B1 (en) | 2016-05-26 | 2021-11-24 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| PL3472167T3 (pl) | 2016-06-20 | 2022-12-19 | Incyte Corporation | Związki heterocykliczne jako immunomodulatory |
| EP3484866B1 (en) | 2016-07-14 | 2022-09-07 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| ES2941716T3 (es) | 2016-08-29 | 2023-05-25 | Incyte Corp | Compuestos heterocíclicos como inmunomoduladores |
| US20180179201A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| WO2018119286A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Bicyclic heteroaromatic compounds as immunomodulators |
| KR102696516B1 (ko) | 2016-12-22 | 2024-08-22 | 인사이트 코포레이션 | 면역조절제로서의 벤조옥사졸 유도체 |
| EP3558973B1 (en) | 2016-12-22 | 2021-09-15 | Incyte Corporation | Pyridine derivatives as immunomodulators |
| CA3053418A1 (en) | 2017-02-16 | 2018-08-23 | Arena Pharmaceuticals, Inc. | Compounds and methods for treatment of primary biliary cholangitis |
| WO2018151834A1 (en) | 2017-02-16 | 2018-08-23 | Arena Pharmaceuticals, Inc. | Compounds and methods for treatment of inflammatory bowel disease with extra-intestinal manifestations |
| EP4212529B1 (en) | 2018-03-30 | 2025-01-29 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| FI4219492T3 (fi) | 2018-05-11 | 2025-02-17 | Incyte Corp | Heterosyklisiä yhdisteitä immunomodulaattoreina |
| CA3102136A1 (en) | 2018-06-06 | 2019-12-12 | Arena Pharmaceuticals, Inc. | Methods of treating conditions related to the s1p1 receptor |
| CN119751336A (zh) | 2018-09-06 | 2025-04-04 | 艾尼纳制药公司 | 可用于治疗自身免疫性病症和炎性病症的化合物 |
| CA3150434A1 (en) | 2019-08-09 | 2021-02-18 | Incyte Corporation | Salts of a pd-1/pd-l1 inhibitor |
| AR120109A1 (es) | 2019-09-30 | 2022-02-02 | Incyte Corp | Compuestos de pirido[3,2-d]pirimidina como inmunomoduladores |
| IL292524A (en) | 2019-11-11 | 2022-06-01 | Incyte Corp | Salts and crystalline forms of a pd-1/pd-l1 inhibitor |
| US11780836B2 (en) | 2020-11-06 | 2023-10-10 | Incyte Corporation | Process of preparing a PD-1/PD-L1 inhibitor |
| WO2022099075A1 (en) | 2020-11-06 | 2022-05-12 | Incyte Corporation | Crystalline form of a pd-1/pd-l1 inhibitor |
| PE20231438A1 (es) | 2020-11-06 | 2023-09-14 | Incyte Corp | Proceso para hacer un inhibidor de pd-1/pd-l1 y sales y formas cristalinas del mismo |
| CN116854622A (zh) * | 2023-07-10 | 2023-10-10 | 青岛科技大学 | 一种多取代的2,4-二氢环戊二烯并[b]吲哚类化合物的合成方法 |
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|---|---|---|---|---|
| EP0307077A1 (en) | 1987-07-21 | 1989-03-15 | Merck Frosst Canada Inc. | Tetrahydrocarbazoles for the improvement of cyclosporin therapy |
| US5830911A (en) * | 1996-08-14 | 1998-11-03 | American Home Products Corporation | Pyranoindole and tetrahydrocarbazole inhibitors of COX-2 |
| JP4126345B2 (ja) | 1997-03-06 | 2008-07-30 | 松森 昭 | ウイルス感染症の予防・治療剤 |
| EP1734950A4 (en) | 2004-01-29 | 2010-06-16 | Elixir Pharmaceuticals Inc | TREATMENT OF A VIRUS DISEASE |
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2005
- 2005-09-21 WO PCT/US2005/033803 patent/WO2006034337A2/en not_active Ceased
- 2005-09-21 AU AU2005286727A patent/AU2005286727A1/en not_active Abandoned
- 2005-09-21 CA CA002577413A patent/CA2577413A1/en not_active Abandoned
- 2005-09-21 US US11/230,729 patent/US7250441B2/en not_active Expired - Fee Related
- 2005-09-21 CN CNA2005800316732A patent/CN101035528A/zh active Pending
- 2005-09-21 MX MX2007003371A patent/MX2007003371A/es not_active Application Discontinuation
- 2005-09-21 EP EP05815334A patent/EP1793819A2/en not_active Withdrawn
- 2005-09-21 JP JP2007533604A patent/JP2008514611A/ja not_active Withdrawn
- 2005-09-21 BR BRPI0515596-7A patent/BRPI0515596A/pt not_active IP Right Cessation
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| CN101035528A (zh) | 2007-09-12 |
| EP1793819A2 (en) | 2007-06-13 |
| WO2006034337A3 (en) | 2006-09-14 |
| US20060063821A1 (en) | 2006-03-23 |
| US7250441B2 (en) | 2007-07-31 |
| AU2005286727A1 (en) | 2006-03-30 |
| WO2006034337A2 (en) | 2006-03-30 |
| JP2008514611A (ja) | 2008-05-08 |
| CA2577413A1 (en) | 2006-03-30 |
| BRPI0515596A (pt) | 2008-07-29 |
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