JP4220776B2 - 化合物 - Google Patents
化合物 Download PDFInfo
- Publication number
- JP4220776B2 JP4220776B2 JP2002532442A JP2002532442A JP4220776B2 JP 4220776 B2 JP4220776 B2 JP 4220776B2 JP 2002532442 A JP2002532442 A JP 2002532442A JP 2002532442 A JP2002532442 A JP 2002532442A JP 4220776 B2 JP4220776 B2 JP 4220776B2
- Authority
- JP
- Japan
- Prior art keywords
- dihydro
- indolidino
- indole
- carboxylic acid
- dioxol
- 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.)
- Expired - Fee Related
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 102
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 239000012453 solvate Substances 0.000 claims abstract description 6
- -1 benzylaminomethyl Chemical group 0.000 claims description 36
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 6
- PHBUUDUSOMMZRA-UHFFFAOYSA-N diethyl indole-1,2-dicarboxylate Chemical compound C1=CC=C2N(C(=O)OCC)C(C(=O)OCC)=CC2=C1 PHBUUDUSOMMZRA-UHFFFAOYSA-N 0.000 claims description 5
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- OEXNQFWEJRSZBW-UHFFFAOYSA-N ethyl indole-1-carboxylate Chemical compound C1=CC=C2N(C(=O)OCC)C=CC2=C1 OEXNQFWEJRSZBW-UHFFFAOYSA-N 0.000 claims 17
- UTWGRMYWDUMKNY-UHFFFAOYSA-N indole-1-carboxylic acid Chemical compound C1=CC=C2N(C(=O)O)C=CC2=C1 UTWGRMYWDUMKNY-UHFFFAOYSA-N 0.000 claims 7
- QQXQAEWRSVZPJM-UHFFFAOYSA-N ethyl 1h-indole-2-carboxylate Chemical compound C1=CC=C2NC(C(=O)OCC)=CC2=C1 QQXQAEWRSVZPJM-UHFFFAOYSA-N 0.000 claims 4
- 150000001408 amides Chemical class 0.000 claims 3
- HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 claims 2
- YFODDBVTSDYZFJ-UHFFFAOYSA-N N-(2-morpholin-4-ylethyl)indole-1-carboxamide Chemical compound N1(CCOCC1)CCNC(=O)N1C=CC2=CC=CC=C12 YFODDBVTSDYZFJ-UHFFFAOYSA-N 0.000 claims 2
- PRGHLUQEEISYBM-UHFFFAOYSA-N N-(pyridin-2-ylmethyl)indole-1-carboxamide Chemical compound N1=C(C=CC=C1)CNC(=O)N1C=CC2=CC=CC=C12 PRGHLUQEEISYBM-UHFFFAOYSA-N 0.000 claims 2
- NYHMJWAWKYZADY-UHFFFAOYSA-N N-[(3,4-dimethoxyphenyl)methyl]indole-1-carboxamide Chemical compound COC=1C=C(CNC(=O)N2C=CC3=CC=CC=C23)C=CC=1OC NYHMJWAWKYZADY-UHFFFAOYSA-N 0.000 claims 2
- OPGNJKHSEKBZPJ-UHFFFAOYSA-N 2-[[10-(1,3-benzodioxol-5-yl)-9,10-dihydro-4h-indolizino[6,7-b]indole-3-carbonyl]-methylamino]acetic acid Chemical compound C1=C2OCOC2=CC(C2N3C=CC(=C3CC=3C4=CC=CC=C4NC=32)C(=O)N(CC(O)=O)C)=C1 OPGNJKHSEKBZPJ-UHFFFAOYSA-N 0.000 claims 1
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- VACNKXRTJBJAKY-UHFFFAOYSA-N N-(2-aminoethyl)indole-1-carboxamide Chemical compound NCCNC(=O)N1C=CC2=CC=CC=C12 VACNKXRTJBJAKY-UHFFFAOYSA-N 0.000 claims 1
- WCHUPFUYSCFGKJ-UHFFFAOYSA-N dimethyl indole-1,2-dicarboxylate Chemical compound C1=CC=C2N(C(=O)OC)C(C(=O)OC)=CC2=C1 WCHUPFUYSCFGKJ-UHFFFAOYSA-N 0.000 claims 1
- 125000000593 indol-1-yl group Chemical group [H]C1=C([H])C([H])=C2N([*])C([H])=C([H])C2=C1[H] 0.000 claims 1
- KTTZHDQDBQPZQP-UHFFFAOYSA-N indole-1,2-dicarboxylic acid Chemical compound C1=CC=C2N(C(O)=O)C(C(=O)O)=CC2=C1 KTTZHDQDBQPZQP-UHFFFAOYSA-N 0.000 claims 1
- PAUPUUZSICTYGB-UHFFFAOYSA-N indole-1-carbonitrile Chemical compound C1=CC=C2N(C#N)C=CC2=C1 PAUPUUZSICTYGB-UHFFFAOYSA-N 0.000 claims 1
- SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 claims 1
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- 238000000034 method Methods 0.000 description 32
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- 125000001072 heteroaryl group Chemical group 0.000 description 24
- 125000000217 alkyl group Chemical group 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 17
- 238000011282 treatment Methods 0.000 description 16
- 239000001257 hydrogen Substances 0.000 description 15
- 229910052739 hydrogen Inorganic materials 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
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- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 12
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- 229910052760 oxygen Inorganic materials 0.000 description 10
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
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- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 7
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- 239000002253 acid Substances 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
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- TWRXJAOTZQYOKJ-UHFFFAOYSA-L magnesium chloride Substances [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 6
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- 125000001424 substituent group Chemical group 0.000 description 6
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- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 4
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- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
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- 108010043671 prostatic acid phosphatase Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
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- A—HUMAN NECESSITIES
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- A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
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- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Pulmonology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Rheumatology (AREA)
- Urology & Nephrology (AREA)
- Physical Education & Sports Medicine (AREA)
- Gynecology & Obstetrics (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Vascular Medicine (AREA)
- Reproductive Health (AREA)
- Endocrinology (AREA)
- Neurology (AREA)
- Immunology (AREA)
- Otolaryngology (AREA)
- Pain & Pain Management (AREA)
- Ophthalmology & Optometry (AREA)
- Neurosurgery (AREA)
- Pregnancy & Childbirth (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23724000P | 2000-10-02 | 2000-10-02 | |
| PCT/US2001/042173 WO2002028859A2 (en) | 2000-10-02 | 2001-09-17 | Condensed pyridoindole derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004510774A JP2004510774A (ja) | 2004-04-08 |
| JP2004510774A5 JP2004510774A5 (enExample) | 2005-04-07 |
| JP4220776B2 true JP4220776B2 (ja) | 2009-02-04 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002532442A Expired - Fee Related JP4220776B2 (ja) | 2000-10-02 | 2001-09-17 | 化合物 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6838456B2 (enExample) |
| EP (1) | EP1335917B1 (enExample) |
| JP (1) | JP4220776B2 (enExample) |
| AT (1) | ATE302776T1 (enExample) |
| AU (1) | AU2002213419A1 (enExample) |
| CA (1) | CA2423308A1 (enExample) |
| DE (1) | DE60112960T2 (enExample) |
| ES (1) | ES2248399T3 (enExample) |
| MX (1) | MXPA03002909A (enExample) |
| WO (1) | WO2002028859A2 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US8416448B2 (en) | 2007-07-19 | 2013-04-09 | Riso Kagaku Corporation | Printing apparatus |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
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| ATE335742T1 (de) * | 2001-06-21 | 2006-09-15 | Lilly Icos Llc | Carbolinderivate als pdev inhibitoren |
| PL377657A1 (pl) | 2002-12-13 | 2006-02-06 | Warner-Lambert Company Llc | Ligand Ó-2-Ű do leczenia dolegliwości dolnych dróg moczowych |
| BRPI0506994A (pt) | 2004-01-22 | 2007-07-03 | Pfizer | derivados de triazol que inibem a atividade antagonista da vasopressina |
| US7501438B2 (en) * | 2006-07-07 | 2009-03-10 | Forest Laboratories Holdings Limited | Pyridoimidazole derivatives |
| EP2240481A1 (en) | 2008-01-11 | 2010-10-20 | Albany Molecular Research, Inc. | (1-azinone) -substituted pyridoindoles as mch antagonists |
| WO2010015585A1 (en) * | 2008-08-05 | 2010-02-11 | Nycomed Gmbh | 6-benzyl-2,3,4,7-tetrahydro-indolo[2,3-c]quinoline compounds |
| US8629158B2 (en) | 2009-07-01 | 2014-01-14 | Albany Molecular Research, Inc. | Azabicycloalkane-indole and azabicycloalkane-pyrrolo-pyridine MCH-1 antagonists, methods of making, and use thereof |
| WO2011003021A1 (en) * | 2009-07-01 | 2011-01-06 | Albany Molecular Research, Inc. | Azinone-substituted azabicycloalkane-indole and azabicycloalkane-pyrrolo-pyridine mch-1 antagonists, methods of making, and use thereof |
| WO2011003005A1 (en) | 2009-07-01 | 2011-01-06 | Albany Molecular Research, Inc. | Azinone-substituted azepino[b]indole and pyrido-pyrrolo-azepine mch-1 antagonists, methods of making, and use thereof |
| WO2011003012A1 (en) * | 2009-07-01 | 2011-01-06 | Albany Molecular Research, Inc. | Azinone-substituted azapolycycle mch-1 antagonists, methods of making, and use thereof |
| WO2012088124A2 (en) | 2010-12-21 | 2012-06-28 | Albany Molecular Research, Inc. | Tetrahydro-azacarboline mch-1 antagonists, methods of making, and uses thereof |
| WO2012088038A2 (en) | 2010-12-21 | 2012-06-28 | Albany Molecular Research, Inc. | Piperazinone-substituted tetrahydro-carboline mch-1 antagonists, methods of making, and uses thereof |
| US8703951B2 (en) * | 2011-07-15 | 2014-04-22 | Academia Sinica | Synthesis of 4H-benzo[D]pyrrolo[1,2-A]thiazoles and indolizino[6,7-b]indole derivatives and their use as antitumor therapeutic agents |
| CN113024553B (zh) * | 2021-03-16 | 2022-02-25 | 皖南医学院 | 三唑并四氢-β-咔啉衍生物及其制备方法和应用 |
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| US3459758A (en) * | 1967-11-09 | 1969-08-05 | Searle & Co | 9,10 - dihydro - 4h - pyrazolo(1',5':1,6)pyrido (3,4-b)indole - 2,3 - dicarboxylic acids and esters |
| GB9401090D0 (en) | 1994-01-21 | 1994-03-16 | Glaxo Lab Sa | Chemical compounds |
| GB9514465D0 (en) | 1995-07-14 | 1995-09-13 | Glaxo Lab Sa | Chemical compounds |
| GB9514473D0 (en) * | 1995-07-14 | 1995-09-13 | Glaxo Lab Sa | Chemical compounds |
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2001
- 2001-09-17 CA CA002423308A patent/CA2423308A1/en not_active Abandoned
- 2001-09-17 WO PCT/US2001/042173 patent/WO2002028859A2/en not_active Ceased
- 2001-09-17 ES ES01981802T patent/ES2248399T3/es not_active Expired - Lifetime
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US8416448B2 (en) | 2007-07-19 | 2013-04-09 | Riso Kagaku Corporation | Printing apparatus |
Also Published As
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| AU2002213419A1 (en) | 2002-04-15 |
| WO2002028859A3 (en) | 2002-09-12 |
| US20030207906A1 (en) | 2003-11-06 |
| EP1335917B1 (en) | 2005-08-24 |
| MXPA03002909A (es) | 2003-09-10 |
| US6838456B2 (en) | 2005-01-04 |
| DE60112960D1 (de) | 2005-09-29 |
| DE60112960T2 (de) | 2006-02-09 |
| ES2248399T3 (es) | 2006-03-16 |
| WO2002028859A2 (en) | 2002-04-11 |
| JP2004510774A (ja) | 2004-04-08 |
| ATE302776T1 (de) | 2005-09-15 |
| CA2423308A1 (en) | 2002-04-11 |
| EP1335917A2 (en) | 2003-08-20 |
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