AU2005286727A1 - 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
- AU2005286727A1 AU2005286727A1 AU2005286727A AU2005286727A AU2005286727A1 AU 2005286727 A1 AU2005286727 A1 AU 2005286727A1 AU 2005286727 A AU2005286727 A AU 2005286727A AU 2005286727 A AU2005286727 A AU 2005286727A AU 2005286727 A1 AU2005286727 A1 AU 2005286727A1
- Authority
- AU
- Australia
- Prior art keywords
- carbon atoms
- tetrahydro
- carboxylic acid
- cyclopenta
- indole
- 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
- 125000004432 carbon atom Chemical group C* 0.000 claims description 182
- 150000001875 compounds Chemical class 0.000 claims description 100
- 125000000217 alkyl group Chemical group 0.000 claims description 61
- -1 furanylmethyl Chemical group 0.000 claims description 40
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 30
- 210000004027 cell Anatomy 0.000 claims description 28
- 239000008194 pharmaceutical composition Substances 0.000 claims description 27
- 125000003342 alkenyl group Chemical group 0.000 claims description 23
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 23
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 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 17
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 208000005176 Hepatitis C Diseases 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
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 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 8
- 101800001554 RNA-directed RNA polymerase Proteins 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
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 230000002265 prevention Effects 0.000 claims description 7
- 241000124008 Mammalia Species 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
- 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
- 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
- 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
- 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
- 125000004644 alkyl sulfinyl group Chemical group 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
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 5
- 125000001316 cycloalkyl alkyl group Chemical group 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 4
- 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 4
- 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 4
- 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 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
- 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 description 4
- 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
- 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 4
- 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 4
- 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 4
- 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 4
- 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 4
- 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 4
- 239000002253 acid Substances 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
- 239000003937 drug carrier Substances 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
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 4
- 125000001984 thiazolidinyl group Chemical group 0.000 claims description 4
- 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 3
- 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 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 description 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 description 3
- 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 3
- 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 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 description 3
- 230000001580 bacterial effect Effects 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 210000004962 mammalian cell Anatomy 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 5
- 150000001735 carboxylic acids Chemical class 0.000 claims 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 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 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- KMAKOBLIOCQGJP-UHFFFAOYSA-N indole-3-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CNC2=C1 KMAKOBLIOCQGJP-UHFFFAOYSA-N 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 102000004163 DNA-directed RNA polymerases Human genes 0.000 claims 1
- 108090000626 DNA-directed RNA polymerases Proteins 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
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- 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
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- 229920001213 Polysorbate 20 Polymers 0.000 description 7
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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
-
- 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)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (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 |
|---|---|
| AU2005286727A1 true AU2005286727A1 (en) | 2006-03-30 |
Family
ID=35907017
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2005286727A Abandoned AU2005286727A1 (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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| WO2006121467A2 (en) * | 2004-11-22 | 2006-11-16 | Smithkline Beecham Corporation | Tetrahydrocarbazole derivatives for treating flaviridae viruses |
| JP2009508875A (ja) | 2005-09-19 | 2009-03-05 | エミスフェアー・テクノロジーズ・インク | Ｎ−（５−クロロサリチロイル）−８−アミノカプリル酸二ナトリウム塩の結晶形 |
| WO2008024763A2 (en) * | 2006-08-25 | 2008-02-28 | Wyeth | Identification and characterization of hcv replicon variants with reduced susceptibility to hcv-796, and methods related thereto |
| EP2081922B1 (en) | 2006-12-22 | 2012-02-01 | Schering Corporation | 5,6-Ring annulated indole derivatives and use thereof |
| AU2007339386B8 (en) | 2006-12-22 | 2013-12-05 | Merck Sharp & Dohme Corp. | 4, 5-ring annulated indole derivatives for treating or preventing of HCV and related viral infections |
| EP2064180B1 (en) | 2006-12-22 | 2016-07-13 | Merck Sharp & Dohme Corp. | 4,5-ring annulated indole derivatives for treating or preventing of hcv and related viral infections |
| JP2010526143A (ja) | 2007-05-04 | 2010-07-29 | バーテックス ファーマシューティカルズ インコーポレイテッド | Ｈｃｖ感染の処置のための併用療法 |
| KR20100067652A (ko) | 2007-08-29 | 2010-06-21 | 쉐링 코포레이션 | 치환된 인돌 유도체 및 이의 사용방법 |
| AU2008295483B2 (en) * | 2007-08-29 | 2013-11-21 | Merck Sharp & Dohme Corp. | Tetracyclic indole derivatives and their use for treating or preventing viral infections |
| CA2697375A1 (en) | 2007-08-29 | 2009-03-12 | Schering Corporation | 2, 3-substituted indole derivatives for treating viral infections |
| KR20100065167A (ko) | 2007-08-29 | 2010-06-15 | 쉐링 코포레이션 | 바이러스 감염 치료용 2,3-치환된 아자인돌 유도체 |
| AU2008309589B2 (en) * | 2007-10-10 | 2012-07-05 | Novartis Ag | Spiropyrrolidines and their use against HCV and HIV infection |
| CN102099351A (zh) | 2007-11-16 | 2011-06-15 | 先灵公司 | 3-杂环取代的吲哚衍生物及其使用方法 |
| WO2009064852A1 (en) | 2007-11-16 | 2009-05-22 | Schering Corporation | 3-aminosulfonyl substituted indole derivatives and methods of use thereof |
| US8901139B2 (en) | 2008-06-13 | 2014-12-02 | Merck Sharp & Dohme Corp. | Tricyclic indole derivatives and methods of use thereof |
| SI2326621T1 (sl) * | 2008-07-23 | 2016-10-28 | Arena Pharmaceuticals, Inc. | Substituirani derivati 1,2,3,4-tetrahidrociklopenta(b)indol-3-il)ocetne kisline, uporabni pri zdravljenju avtoimunskih in vnetnih motenj |
| NZ591001A (en) | 2008-08-27 | 2012-11-30 | Arena Pharm Inc | Substituted tricyclic acid derivatives as s1p1 receptor agonists useful in the treatment of autoimmune and inflammatory disorders |
| 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 |
| SG10201500639TA (en) | 2010-01-27 | 2015-03-30 | 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 |
| CN105503882B (zh) | 2010-03-03 | 2019-07-05 | 艾尼纳制药公司 | 制备s1p1受体调节剂及其晶体形式的方法 |
| 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 |
| CN116850181A (zh) | 2015-01-06 | 2023-10-10 | 艾尼纳制药公司 | 治疗与s1p1受体有关的病症的方法 |
| AU2016284162A1 (en) | 2015-06-22 | 2018-02-01 | 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(Compound1) for use in SIP1 receptor-associated disorders |
| MA52119A (fr) | 2015-10-19 | 2018-08-29 | Ncyte Corp | Composés hétérocycliques utilisés comme immunomodulateurs |
| MY199220A (en) | 2015-11-19 | 2023-10-20 | Incyte Corp | Heterocyclic compounds as immunomodulators |
| JP6911031B2 (ja) | 2015-12-22 | 2021-07-28 | インサイト・コーポレイションＩｎｃｙｔｅ Ｃｏｒｐｏｒａｔｉｏｎ | 免疫調節剤としての複素環化合物 |
| TW201808950A (zh) | 2016-05-06 | 2018-03-16 | 英塞特公司 | 作為免疫調節劑之雜環化合物 |
| US20170342060A1 (en) | 2016-05-26 | 2017-11-30 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| MY197280A (en) | 2016-06-20 | 2023-06-09 | Incyte Corp | Heterocyclic compounds as immunomodulators |
| EP3484866B1 (en) | 2016-07-14 | 2022-09-07 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| MA46045A (fr) | 2016-08-29 | 2021-04-28 | Incyte Corp | Composés hétérocycliques utilisés comme immunomodulateurs |
| ES2899402T3 (es) | 2016-12-22 | 2022-03-11 | Incyte Corp | Derivados de piridina como inmunomoduladores |
| MA47099A (fr) | 2016-12-22 | 2021-05-12 | Incyte Corp | Composés hétéroaromatiques bicycliques utilisés en tant qu'immunomodulateurs |
| US20180179201A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| BR112019012993A2 (pt) | 2016-12-22 | 2019-12-03 | Incyte Corporation | derivados de benzo-oxazol como imunomoduladores |
| CA3053416A1 (en) | 2017-02-16 | 2018-08-23 | Arena Pharmaceuticals, Inc. | Compounds and methods for treatment of inflammatory bowel disease with extra-intestinal manifestations |
| AU2018220521A1 (en) | 2017-02-16 | 2019-09-05 | Arena Pharmaceuticals, Inc. | Compounds and methods for treatment of primary biliary cholangitis |
| HRP20230090T1 (hr) | 2018-03-30 | 2023-03-17 | Incyte Corporation | Heterociklički spojevi kao imunomodulatori |
| HUE061503T2 (hu) | 2018-05-11 | 2023-07-28 | Incyte Corp | Tetrahidro-imidazo[4,5-C]piridin-származékok mint PD-L1 immunmodulátorok |
| WO2019236757A1 (en) | 2018-06-06 | 2019-12-12 | Arena Pharmaceuticals, Inc. | Methods of treating conditions related to the s1p1 receptor |
| US11555015B2 (en) | 2018-09-06 | 2023-01-17 | Arena Pharmaceuticals, Inc. | Compounds useful in the treatment of autoimmune and inflammatory disorders |
| US11753406B2 (en) | 2019-08-09 | 2023-09-12 | Incyte Corporation | Salts of a PD-1/PD-L1 inhibitor |
| PH12022550754A1 (en) | 2019-09-30 | 2023-08-23 | Incyte Corp | Pyrido[3,2-d]pyrimidine compounds as immunomodulators |
| AU2020385113A1 (en) | 2019-11-11 | 2022-05-19 | Incyte Corporation | Salts and crystalline forms of a PD-1/PD-L1 inhibitor |
| MX2023005362A (es) | 2020-11-06 | 2023-06-22 | Incyte Corp | Proceso para hacer un inhibidor de proteina de muerte programada 1 (pd-1)/ligando de muerte programada 1 (pd-l1) y sales y formas cristalinas del mismo. |
| WO2022099018A1 (en) | 2020-11-06 | 2022-05-12 | Incyte Corporation | Process of preparing a pd-1/pd-l1 inhibitor |
| TW202233615A (zh) | 2020-11-06 | 2022-09-01 | 美商英塞特公司 | Ｐｄ—１／ｐｄ—ｌ１抑制劑之結晶形式 |
| 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 |
| US20050256181A1 (en) * | 2004-01-29 | 2005-11-17 | Elixir Pharmaceuticals, Inc. | Treating a viral disorder |
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2005
- 2005-09-21 JP JP2007533604A patent/JP2008514611A/ja not_active Withdrawn
- 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 MX MX2007003371A patent/MX2007003371A/es not_active Application Discontinuation
- 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 BR BRPI0515596-7A patent/BRPI0515596A/pt not_active IP Right Cessation
- 2005-09-21 US US11/230,729 patent/US7250441B2/en not_active Expired - Fee Related
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|---|---|
| JP2008514611A (ja) | 2008-05-08 |
| EP1793819A2 (en) | 2007-06-13 |
| CA2577413A1 (en) | 2006-03-30 |
| CN101035528A (zh) | 2007-09-12 |
| WO2006034337A3 (en) | 2006-09-14 |
| WO2006034337A2 (en) | 2006-03-30 |
| US20060063821A1 (en) | 2006-03-23 |
| MX2007003371A (es) | 2007-05-07 |
| US7250441B2 (en) | 2007-07-31 |
| BRPI0515596A (pt) | 2008-07-29 |
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