CA2577413A1 - Carbazole and cyclopentaindole derivatives to treat infection with hepatitis c virus - Google Patents
Carbazole and cyclopentaindole derivatives to treat infection with hepatitis c virus Download PDFInfo
- Publication number
- CA2577413A1 CA2577413A1 CA002577413A CA2577413A CA2577413A1 CA 2577413 A1 CA2577413 A1 CA 2577413A1 CA 002577413 A CA002577413 A CA 002577413A CA 2577413 A CA2577413 A CA 2577413A CA 2577413 A1 CA2577413 A1 CA 2577413A1
- Authority
- CA
- Canada
- Prior art keywords
- carbon atoms
- tetrahydro
- carboxylic acid
- indole
- cyclopenta
- 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
- 208000015181 infectious disease Diseases 0.000 title claims description 6
- 241000711549 Hepacivirus C Species 0.000 title description 24
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 title description 7
- HFGUJIUXLNDRAF-UHFFFAOYSA-N cyclopenta[g]indole Chemical class C1=CC2=CC=CC2=C2N=CC=C21 HFGUJIUXLNDRAF-UHFFFAOYSA-N 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 96
- 238000000034 method Methods 0.000 claims abstract description 24
- 208000005176 Hepatitis C Diseases 0.000 claims abstract description 14
- 241000124008 Mammalia Species 0.000 claims abstract description 7
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 188
- 125000000217 alkyl group Chemical group 0.000 claims description 58
- -1 furanylmethyl Chemical group 0.000 claims description 39
- 125000003118 aryl group Chemical group 0.000 claims description 31
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 30
- 210000004027 cell Anatomy 0.000 claims description 29
- 239000008194 pharmaceutical composition Substances 0.000 claims description 27
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 23
- 125000003342 alkenyl group Chemical group 0.000 claims description 22
- 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 14
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 101800001554 RNA-directed RNA polymerase Proteins 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 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 description 7
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 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 description 5
- 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 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 5
- 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 5
- 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 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 5
- 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 description 5
- 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 5
- 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 5
- 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 5
- 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 description 5
- PJSPQZHMSYHQHW-UHFFFAOYSA-N 8-bromo-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(Br)=C2C2=C1C(CCCC)(C(O)=O)CC2 PJSPQZHMSYHQHW-UHFFFAOYSA-N 0.000 claims description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 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 description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000002102 aryl alkyloxo group Chemical group 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
- 208000010710 hepatitis C virus infection Diseases 0.000 claims description 4
- 229910052740 iodine Inorganic materials 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
- 230000001580 bacterial effect Effects 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 6
- 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
- 102000004163 DNA-directed RNA polymerases Human genes 0.000 claims 1
- 108090000626 DNA-directed RNA polymerases Proteins 0.000 claims 1
- 210000004962 mammalian cell Anatomy 0.000 claims 1
- 208000036142 Viral infection Diseases 0.000 abstract description 6
- 230000009385 viral infection Effects 0.000 abstract description 6
- 238000006467 substitution reaction Methods 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 14
- 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 13
- 239000002953 phosphate buffered saline Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
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- 229920001213 Polysorbate 20 Polymers 0.000 description 7
- 239000003814 drug Substances 0.000 description 7
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- 229910052757 nitrogen Inorganic materials 0.000 description 5
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- 238000012384 transportation and delivery Methods 0.000 description 5
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 4
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- 108060004795 Methyltransferase Proteins 0.000 description 4
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- JHZPNBKZPAWCJD-UHFFFAOYSA-N ethyl 2-oxocyclopentane-1-carboxylate Chemical compound CCOC(=O)C1CCCC1=O JHZPNBKZPAWCJD-UHFFFAOYSA-N 0.000 description 3
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
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Classifications
-
- 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)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Virology (AREA)
- Molecular Biology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US61214404P | 2004-09-23 | 2004-09-23 | |
| US60/612,144 | 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 |
|---|---|
| CA2577413A1 true CA2577413A1 (en) | 2006-03-30 |
Family
ID=35907017
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002577413A Abandoned CA2577413A1 (en) | 2004-09-23 | 2005-09-21 | Carbazole and cyclopentaindole derivatives to treat infection with hepatitis c virus |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7250441B2 (enExample) |
| 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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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2006121467A2 (en) * | 2004-11-22 | 2006-11-16 | Smithkline Beecham Corporation | Tetrahydrocarbazole derivatives for treating flaviridae viruses |
| CN101627011A (zh) | 2005-09-19 | 2010-01-13 | 爱密斯菲尔科技公司 | N-(5-氯水杨酰基)-8-氨基辛酸的二钠盐的晶形 |
| US20080182895A1 (en) * | 2006-08-25 | 2008-07-31 | Howe Anita Y M | Identification and characterization of hcv replicon variants with reduced susceptibility to hcv-796, and methods related thereto |
| CA2673254C (en) | 2006-12-22 | 2013-09-10 | Schering Corporation | 4,5-ring annulated indole derivatives for treating or preventing of hcv and related viral infections |
| MX2009006877A (es) | 2006-12-22 | 2009-09-28 | Schering Corp | Derivados indolicos con anillo unido en las posiciones 5,6 y metodos de uso de los mismos. |
| RU2009127855A (ru) | 2006-12-22 | 2011-01-27 | Шеринг Корпорейшн (US) | 4,5 циклоаннелированные производные индола для лечения или предотвращения вируса гепатита с (hcv) и родственных вирусных инфекций |
| EP2494991A1 (en) | 2007-05-04 | 2012-09-05 | Vertex Pharmaceuticals Incorporated | Combination therapy for the treatment of HCV infection |
| MX2010002316A (es) * | 2007-08-29 | 2010-03-22 | Schering Corp | Derivados tetraciclicos de indol y su uso para el tratamiento o prevencion de infecciones virales. |
| 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 |
| PE20090995A1 (es) | 2007-08-29 | 2009-08-03 | Schering Corp | Derivados indolicos 2,3-sustituidos como inhibidores del virus de la hepatitis c (vhc) |
| PE20090994A1 (es) | 2007-08-29 | 2009-08-03 | Schering Corp | Derivados de azaindol 2,3-sustituidos como agentes antivirales |
| JP5095824B2 (ja) * | 2007-10-10 | 2012-12-12 | ノバルティス アーゲー | スピロピロリジン類およびｈｃｖおよびｈｉｖ感染に対するその使用 |
| WO2009064848A1 (en) | 2007-11-16 | 2009-05-22 | Schering Corporation | 3-heterocyclic substituted indole derivatives and methods of use thereof |
| WO2009064852A1 (en) | 2007-11-16 | 2009-05-22 | Schering Corporation | 3-aminosulfonyl substituted indole derivatives and methods of use thereof |
| CN102159579B (zh) | 2008-06-13 | 2015-03-25 | 默沙东公司 | 三环吲哚衍生物及其使用方法 |
| 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 |
| CN105816453B (zh) | 2008-08-27 | 2021-03-05 | 艾尼纳制药公司 | 用于治疗自身免疫性病症和炎性病症的作为s1p1受体激动剂的经取代的三环酸衍生物 |
| CN102325753B (zh) | 2008-12-19 | 2014-09-10 | 百时美施贵宝公司 | 用作激酶抑制剂的咔唑甲酰胺化合物 |
| SG182610A1 (en) | 2010-01-27 | 2012-08-30 | Arena Pharm Inc | Processes 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 |
| CA2789480A1 (en) | 2010-03-03 | 2011-09-09 | Arena Pharmaceuticals, Inc. | Processes for the preparation of s1p1 receptor modulators and crystalline forms thereof |
| 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 |
| US11007175B2 (en) | 2015-01-06 | 2021-05-18 | Arena Pharmaceuticals, Inc. | Methods of treating conditions related to the S1P1 receptor |
| BR112017027656B1 (pt) | 2015-06-22 | 2023-12-05 | Arena Pharmaceuticals, Inc. | Hábito cristalino de placa livre de sal de l-arginina de ácido (r)-2-(7-(4- ciclopentil-3-(trifluorometil)benzilóxi)- 1,2,3,4-tetra-hidrociclo-penta[b]indol-3- il)acético, composição farmacêutica que o compreende, seus usos e método de preparação do mesmo |
| EP3365340B1 (en) | 2015-10-19 | 2022-08-10 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| HUE060680T2 (hu) | 2015-11-19 | 2023-04-28 | Incyte Corp | Heterociklusos vegyületek mint immunmodulátorok |
| EP3394033B1 (en) | 2015-12-22 | 2020-11-25 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| WO2017192961A1 (en) | 2016-05-06 | 2017-11-09 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| TW201808902A (zh) | 2016-05-26 | 2018-03-16 | 美商英塞特公司 | 作為免疫調節劑之雜環化合物 |
| MD3472167T2 (ro) | 2016-06-20 | 2023-02-28 | Incyte Corp | Compuși heterociclici ca imunomodulatori |
| WO2018013789A1 (en) | 2016-07-14 | 2018-01-18 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| US20180057486A1 (en) | 2016-08-29 | 2018-03-01 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| EP3558963B1 (en) | 2016-12-22 | 2022-03-23 | Incyte Corporation | Bicyclic heteroaromatic compounds as immunomodulators |
| MA47123A (fr) | 2016-12-22 | 2021-03-17 | Incyte Corp | Dérivés de benzooxazole en tant qu'mmunomodulateurs |
| EP3558973B1 (en) | 2016-12-22 | 2021-09-15 | Incyte Corporation | Pyridine derivatives as immunomodulators |
| EP3558989B1 (en) | 2016-12-22 | 2021-04-14 | Incyte Corporation | Triazolo[1,5-a]pyridine derivatives as immunomodulators |
| CA3053418A1 (en) | 2017-02-16 | 2018-08-23 | Arena Pharmaceuticals, Inc. | Compounds and methods for treatment of primary biliary cholangitis |
| JP2020507610A (ja) | 2017-02-16 | 2020-03-12 | アリーナ ファーマシューティカルズ， インコーポレイテッド | 腸管外症状を伴う炎症性腸疾患の治療のための化合物および方法 |
| PL4212529T3 (pl) | 2018-03-30 | 2025-07-07 | Incyte Corporation | Związki heterocykliczne jako immunomodulatory |
| HRP20230306T1 (hr) | 2018-05-11 | 2023-05-12 | Incyte Corporation | Derivati tetrahidro-imidazo[4,5-c]piridina kao pd-l1 imunomodulatori |
| BR112020024762A2 (pt) | 2018-06-06 | 2021-03-23 | Arena Pharmaceuticals, Inc. | métodos de tratamento de condições relacionadas ao receptor s1p1 |
| 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 |
| WO2021030162A1 (en) | 2019-08-09 | 2021-02-18 | Incyte Corporation | Salts of a pd-1/pd-l1 inhibitor |
| IL291471B2 (en) | 2019-09-30 | 2025-04-01 | Incyte Corp | Pyrimido[3,2–D]pyrimidine compounds as immunomodulators |
| CR20220237A (es) | 2019-11-11 | 2022-08-05 | Incyte Corp | Sales y formas cristalinas de un inhibidor de pd-1/pd-l1 |
| AR124001A1 (es) | 2020-11-06 | 2023-02-01 | Incyte Corp | Proceso para fabricar un inhibidor pd-1 / pd-l1 y sales y formas cristalinas del mismo |
| 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 |
| 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 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| AU2005208934A1 (en) | 2004-01-29 | 2005-08-11 | Elixir Pharmaceuticals, Inc | Treating a viral disorder |
-
2005
- 2005-09-21 BR BRPI0515596-7A patent/BRPI0515596A/pt not_active IP Right Cessation
- 2005-09-21 CN CNA2005800316732A patent/CN101035528A/zh active Pending
- 2005-09-21 EP EP05815334A patent/EP1793819A2/en not_active Withdrawn
- 2005-09-21 CA CA002577413A patent/CA2577413A1/en not_active Abandoned
- 2005-09-21 JP JP2007533604A patent/JP2008514611A/ja not_active Withdrawn
- 2005-09-21 US US11/230,729 patent/US7250441B2/en not_active Expired - Fee Related
- 2005-09-21 AU AU2005286727A patent/AU2005286727A1/en not_active Abandoned
- 2005-09-21 MX MX2007003371A patent/MX2007003371A/es not_active Application Discontinuation
- 2005-09-21 WO PCT/US2005/033803 patent/WO2006034337A2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| EP1793819A2 (en) | 2007-06-13 |
| BRPI0515596A (pt) | 2008-07-29 |
| US7250441B2 (en) | 2007-07-31 |
| US20060063821A1 (en) | 2006-03-23 |
| MX2007003371A (es) | 2007-05-07 |
| WO2006034337A3 (en) | 2006-09-14 |
| CN101035528A (zh) | 2007-09-12 |
| JP2008514611A (ja) | 2008-05-08 |
| AU2005286727A1 (en) | 2006-03-30 |
| WO2006034337A2 (en) | 2006-03-30 |
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