JP2004537541A5 - - Google Patents
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- Publication number
- JP2004537541A5 JP2004537541A5 JP2003508914A JP2003508914A JP2004537541A5 JP 2004537541 A5 JP2004537541 A5 JP 2004537541A5 JP 2003508914 A JP2003508914 A JP 2003508914A JP 2003508914 A JP2003508914 A JP 2003508914A JP 2004537541 A5 JP2004537541 A5 JP 2004537541A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- independently
- phenyl
- trifluoromethyl
- halo
- 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.)
- Granted
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 35
- 125000000217 alkyl group Chemical group 0.000 claims 30
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 20
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 19
- 150000001875 compounds Chemical class 0.000 claims 17
- 125000005843 halogen group Chemical group 0.000 claims 16
- 125000003545 alkoxy group Chemical group 0.000 claims 15
- -1 amino, hydroxy Chemical group 0.000 claims 13
- 125000004076 pyridyl group Chemical group 0.000 claims 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 6
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims 6
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 6
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 5
- 125000001475 halogen functional group Chemical group 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 4
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 3
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- DYMRYCZRMAHYKE-UHFFFAOYSA-N n-diazonitramide Chemical compound [O-][N+](=O)N=[N+]=[N-] DYMRYCZRMAHYKE-UHFFFAOYSA-N 0.000 claims 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims 3
- 125000004434 sulfur atom Chemical group 0.000 claims 3
- 150000001408 amides Chemical class 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- QCGPNKGBXUZKRV-UHFFFAOYSA-N 3-chloro-1-methyl-5-[(2-phenylbenzoyl)amino]indole-2-carboxylic acid Chemical compound C=1C=C2N(C)C(C(O)=O)=C(Cl)C2=CC=1NC(=O)C1=CC=CC=C1C1=CC=CC=C1 QCGPNKGBXUZKRV-UHFFFAOYSA-N 0.000 claims 1
- UATDNHVWCBSEJH-UHFFFAOYSA-N 3-chloro-1-methyl-n-[2-oxo-1-phenyl-2-(prop-2-ynylamino)ethyl]-5-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]indole-2-carboxamide Chemical compound ClC=1C2=CC(NC(=O)C=3C(=CC=CC=3)C=3C=CC(=CC=3)C(F)(F)F)=CC=C2N(C)C=1C(=O)NC(C(=O)NCC#C)C1=CC=CC=C1 UATDNHVWCBSEJH-UHFFFAOYSA-N 0.000 claims 1
- OLQQRYRTLUMYCV-UHFFFAOYSA-N 3-chloro-1-methyl-n-[2-oxo-1-phenyl-2-(propan-2-ylamino)ethyl]-5-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]indole-2-carboxamide Chemical compound C=1C=CC=CC=1C(C(=O)NC(C)C)NC(=O)C(N(C1=CC=2)C)=C(Cl)C1=CC=2NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 OLQQRYRTLUMYCV-UHFFFAOYSA-N 0.000 claims 1
- KXRBCMNXDPKVMV-UHFFFAOYSA-N 3-chloro-1-methyl-n-[2-oxo-1-phenyl-2-(propylamino)ethyl]-5-[(2-phenylbenzoyl)amino]indole-2-carboxamide Chemical compound C=1C=CC=CC=1C(C(=O)NCCC)NC(=O)C(N(C1=CC=2)C)=C(Cl)C1=CC=2NC(=O)C1=CC=CC=C1C1=CC=CC=C1 KXRBCMNXDPKVMV-UHFFFAOYSA-N 0.000 claims 1
- UWMUBZILFCWRDQ-UHFFFAOYSA-N 3-chloro-1-methyl-n-[2-oxo-1-phenyl-2-(propylamino)ethyl]-5-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]indole-2-carboxamide Chemical compound C=1C=CC=CC=1C(C(=O)NCCC)NC(=O)C(N(C1=CC=2)C)=C(Cl)C1=CC=2NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 UWMUBZILFCWRDQ-UHFFFAOYSA-N 0.000 claims 1
- AXCIWLZUECZEOD-UHFFFAOYSA-N 3-chloro-n-[2-(ethylamino)-2-oxo-1-phenylethyl]-1-methyl-5-[methyl-[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]indole-2-carboxamide Chemical compound C=1C=CC=CC=1C(C(=O)NCC)NC(=O)C(N(C1=CC=2)C)=C(Cl)C1=CC=2N(C)C(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 AXCIWLZUECZEOD-UHFFFAOYSA-N 0.000 claims 1
- FRGXWGKYTCWIOT-UHFFFAOYSA-N C=1C=CC=CC=1C(C(=O)NC(C)C)NC(=O)C(N(C1=CC=2)C)=C(Cl)C1=CC=2N(C)C(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 Chemical compound C=1C=CC=CC=1C(C(=O)NC(C)C)NC(=O)C(N(C1=CC=2)C)=C(Cl)C1=CC=2N(C)C(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 FRGXWGKYTCWIOT-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 150000001540 azides Chemical class 0.000 claims 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 150000001602 bicycloalkyls Chemical group 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30164401P | 2001-06-28 | 2001-06-28 | |
| PCT/IB2002/001876 WO2003002533A1 (en) | 2001-06-28 | 2002-05-24 | Triamide-substituted indoles, benzofuranes and benzothiophenes as inhibitors of microsomal triglyceride transfer protein (mtp) and/or apolipoprotein b (apo b) secretion |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004537541A JP2004537541A (ja) | 2004-12-16 |
| JP2004537541A5 true JP2004537541A5 (enExample) | 2005-08-18 |
| JP4139325B2 JP4139325B2 (ja) | 2008-08-27 |
Family
ID=23164253
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003508914A Expired - Lifetime JP4139325B2 (ja) | 2001-06-28 | 2002-05-24 | ミクロソーム・トリグリセリド・トランスファータンパク質（ｍｔｐ）及び／又はアポリポタンパク質ｂ（ａｐｏｂ）分泌の阻害剤としてのトリアミド置換インドール、ベンゾフラン及びベンゾチオフェン |
Country Status (46)
Families Citing this family (61)
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| PT3551622T (pt) | 2016-12-09 | 2020-11-12 | Vertex Pharma | Modulador do regulador da condutância transmembrana da fibrose quística, composições farmacêuticas, métodos de tratamento e processo de fabrico do modulador |
| US11253509B2 (en) | 2017-06-08 | 2022-02-22 | Vertex Pharmaceuticals Incorporated | Methods of treatment for cystic fibrosis |
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| US12029718B2 (en) | 2021-11-09 | 2024-07-09 | Cct Sciences, Llc | Process for production of essentially pure delta-9-tetrahydrocannabinol |
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