TWI260222B - Anthranilic acid amides and pharmacological use thereof - Google Patents
Anthranilic acid amides and pharmacological use thereof Download PDFInfo
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- TWI260222B TWI260222B TW091132669A TW91132669A TWI260222B TW I260222 B TWI260222 B TW I260222B TW 091132669 A TW091132669 A TW 091132669A TW 91132669 A TW91132669 A TW 91132669A TW I260222 B TWI260222 B TW I260222B
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- compound
- tautomer
- oxide
- salt
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- PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical class NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 title abstract 3
- 230000000144 pharmacologic effect Effects 0.000 title description 3
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- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 21
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 230000000694 effects Effects 0.000 claims description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 claims description 11
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- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 9
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
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- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 4
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- FFAYGOGQMRPYBF-UHFFFAOYSA-N 2-[(6-methoxypyridin-3-yl)methylamino]-n-[2-methyl-3-(trifluoromethyl)phenyl]benzamide Chemical compound C1=NC(OC)=CC=C1CNC1=CC=CC=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1C FFAYGOGQMRPYBF-UHFFFAOYSA-N 0.000 claims 1
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- XINRSLKXWIYLMI-UHFFFAOYSA-N benzoic acid decan-1-amine Chemical compound OC(=O)C1=CC=CC=C1.CCCCCCCCCCN XINRSLKXWIYLMI-UHFFFAOYSA-N 0.000 claims 1
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- 229910001925 ruthenium oxide Inorganic materials 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
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- Health & Medical Sciences (AREA)
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- Bioinformatics & Cheminformatics (AREA)
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- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
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| US7307088B2 (en) * | 2002-07-09 | 2007-12-11 | Amgen Inc. | Substituted anthranilic amide derivatives and methods of use |
| US7615565B2 (en) | 2002-07-31 | 2009-11-10 | Bayer Schering Pharma Aktiengesellschaft | VEGFR-2 and VEGFR-3 inhibitory anthranilamide pyridines |
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| DE10327719A1 (de) * | 2003-06-13 | 2005-01-20 | Schering Ag | VEGFR-2 und VEGFR-3 Inhibitorische Anthranylamidpyridone |
| US7202260B2 (en) | 2003-06-13 | 2007-04-10 | Schering Ag | VEGFR-2 and VEGFR-3 inhibitory anthranilamide pyridones |
| US7129252B2 (en) * | 2003-06-16 | 2006-10-31 | Guoqing P Chen | Six membered amino-amide derivatives an angiogenisis inhibitors |
| UA89035C2 (ru) | 2003-12-03 | 2009-12-25 | Лео Фарма А/С | Эфиры гидроксамовых кислот и их фармацевтическое применение |
| EP1568368A1 (en) * | 2004-02-26 | 2005-08-31 | Schering Aktiengesellschaft | Pharmaceutical combination comprising a CDK inhibitor and a VEGF receptor inhibitor |
| EP1657241A1 (en) | 2004-11-03 | 2006-05-17 | Schering Aktiengesellschaft | Novel anthranilamide pyridinureas as VEGF receptor kinase inhibitors |
| US7906533B2 (en) | 2004-11-03 | 2011-03-15 | Bayer Schering Pharma Ag | Nicotinamide pyridinureas as vascular endothelial growth factor (VEGF) receptor kinase inhibitors |
| EP1655295A1 (en) | 2004-11-03 | 2006-05-10 | Schering Aktiengesellschaft | Anthranilamide pyridinureas as VEGF receptor kinase inhibitors |
| EP1820795A4 (en) | 2004-12-07 | 2010-10-20 | Toyama Chemical Co Ltd | NEW ANTHRANILIC ACID DERIVATIVE OR SALT FROM IT |
| US7547782B2 (en) * | 2005-09-30 | 2009-06-16 | Bristol-Myers Squibb Company | Met kinase inhibitors |
| CN101265274B (zh) * | 2007-02-16 | 2013-09-04 | 中国医学科学院药物研究所 | 嘧啶噻唑胺衍生物、及其制法和药物组合物与用途 |
| AR073216A1 (es) | 2008-08-27 | 2010-10-20 | Leo Pharma As | Derivados de piridina como receptor de vegfr-2 e inhibidores de proteina tirosina quinasa y uso farmaceutico de los mismos |
| JO3265B1 (ar) | 2008-12-09 | 2018-09-16 | Novartis Ag | مثبطات بيريديلوكسى اندولات vegf-r2 واستخدامها لعلاج المرض |
| GB201322538D0 (en) | 2013-06-21 | 2014-02-05 | Immusmol Sas | Method for detecting small molecules in a sample |
| CN107954893A (zh) * | 2017-11-28 | 2018-04-24 | 兰州纬寰生物科技有限公司 | 邻氨基苯甲酰胺衍生物及制备方法和用途 |
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| EP0850222B1 (en) * | 1996-06-29 | 2003-05-28 | Samjin Pharmaceutical Co., Ltd. | Piperazine derivatives and process for the preparation thereof |
| UA71587C2 (uk) * | 1998-11-10 | 2004-12-15 | Шерінг Акцієнгезелльшафт | Аміди антранілової кислоти та їхнє застосування як лікарських засобів |
| GB9824579D0 (en) * | 1998-11-10 | 1999-01-06 | Novartis Ag | Organic compounds |
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2002
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