UA76425C2 - Oxygenated esters of 4-iodophenylamino benzhydroxamic acids, crystalline form (variants), pharmaceutical composition on their basis - Google Patents
Oxygenated esters of 4-iodophenylamino benzhydroxamic acids, crystalline form (variants), pharmaceutical composition on their basis Download PDFInfo
- Publication number
- UA76425C2 UA76425C2 UA2003021455A UA2003021455A UA76425C2 UA 76425 C2 UA76425 C2 UA 76425C2 UA 2003021455 A UA2003021455 A UA 2003021455A UA 2003021455 A UA2003021455 A UA 2003021455A UA 76425 C2 UA76425 C2 UA 76425C2
- Authority
- UA
- Ukraine
- Prior art keywords
- benzamide
- fluoro
- iodophenylamino
- difluoro
- chloro
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title abstract description 51
- 239000008194 pharmaceutical composition Substances 0.000 title abstract description 10
- QAMBBWKIAJFFRF-UHFFFAOYSA-N n-hydroxy-2-(4-iodoanilino)benzamide Chemical class ONC(=O)C1=CC=CC=C1NC1=CC=C(I)C=C1 QAMBBWKIAJFFRF-UHFFFAOYSA-N 0.000 title abstract description 4
- 238000000034 method Methods 0.000 abstract description 76
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1257
- -1 iodophenylamino Chemical group 0.000 description 381
- 238000005481 NMR spectroscopy Methods 0.000 description 166
- 150000001875 compounds Chemical class 0.000 description 147
- 239000000243 solution Substances 0.000 description 147
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 137
- 239000007787 solid Substances 0.000 description 96
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 87
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 83
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 79
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 75
- 229910001868 water Inorganic materials 0.000 description 74
- 239000000203 mixture Substances 0.000 description 73
- 239000011541 reaction mixture Substances 0.000 description 71
- 238000000921 elemental analysis Methods 0.000 description 65
- 238000002360 preparation method Methods 0.000 description 63
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 58
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 55
- 239000000843 powder Substances 0.000 description 53
- 230000005855 radiation Effects 0.000 description 49
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 47
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 47
- 229910052739 hydrogen Inorganic materials 0.000 description 47
- 239000001257 hydrogen Substances 0.000 description 47
- 235000019439 ethyl acetate Nutrition 0.000 description 46
- 229940093499 ethyl acetate Drugs 0.000 description 46
- 125000000217 alkyl group Chemical group 0.000 description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
- 238000002441 X-ray diffraction Methods 0.000 description 35
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
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- NNDGPYMAAAEHHF-UHFFFAOYSA-N 2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=CC=C1C(N)=O NNDGPYMAAAEHHF-UHFFFAOYSA-N 0.000 description 23
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- YXJKFEHSDJWXFA-UHFFFAOYSA-N 3,4-difluoro-2-(2-fluoro-4-iodoanilino)benzamide Chemical compound NC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F YXJKFEHSDJWXFA-UHFFFAOYSA-N 0.000 description 18
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 18
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 16
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- XXYNZSATHOXXBJ-UHFFFAOYSA-N 4-hydroxyisoindole-1,3-dione Chemical compound OC1=CC=CC2=C1C(=O)NC2=O XXYNZSATHOXXBJ-UHFFFAOYSA-N 0.000 description 12
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- 150000003668 tyrosines Chemical class 0.000 description 1
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- GBABOYUKABKIAF-GHYRFKGUSA-N vinorelbine Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-GHYRFKGUSA-N 0.000 description 1
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Classifications
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C229/54—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C229/56—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring with amino and carboxyl groups bound in ortho-position
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
- C07C259/10—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to carbon atoms of six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/16—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Neurology (AREA)
- Dermatology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
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- Biomedical Technology (AREA)
- Orthopedic Medicine & Surgery (AREA)
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- Physical Education & Sports Medicine (AREA)
- Urology & Nephrology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Virology (AREA)
- Vascular Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Hydrogenated Pyridines (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US21937200P | 2000-07-19 | 2000-07-19 | |
PCT/US2001/022331 WO2002006213A2 (fr) | 2000-07-19 | 2001-07-12 | Esters oxygenes d'acides 4-iodophenylamino benzhydroxamiques |
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UA76425C2 true UA76425C2 (en) | 2006-08-15 |
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UA2003021455A UA76425C2 (en) | 2000-07-19 | 2001-12-07 | Oxygenated esters of 4-iodophenylamino benzhydroxamic acids, crystalline form (variants), pharmaceutical composition on their basis |
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PT1301472E (pt) * | 2000-07-19 | 2014-05-15 | Warner Lambert Co | Ésteres oxigenados de ácidos 4-iodo fenilamino benzidroxâmicos |
IL149462A0 (en) * | 2001-05-09 | 2002-11-10 | Warner Lambert Co | Method of treating or inhibiting neutrophil chemotaxis by administering a mek inhibitor |
WO2002102232A2 (fr) * | 2001-06-14 | 2002-12-27 | The Regents Of The University Of California | Nouvelle voie de signalisation destinee a la production de douleur inflammatoire et de neuropathie |
MXPA04005527A (es) | 2002-01-23 | 2005-03-23 | Warner Lambert Co | ESTERES HIDROXIMATO DEL áCIDO N-(4-FENIL SUSTITUIDO)-ANTRANILICO. |
DOP2003000556A (es) | 2002-01-23 | 2003-10-31 | Warner Lambert Co | Esteres hidroxamato de acido n-(4-fenil-sustituido)-antranilico. |
EP2275102B1 (fr) | 2002-03-13 | 2015-07-29 | Array Biopharma, Inc. | Dérivés de benzimidazole d'alkylat N3 en tant qu'inhibiteurs de Mek |
US7235537B2 (en) * | 2002-03-13 | 2007-06-26 | Array Biopharma, Inc. | N3 alkylated benzimidazole derivatives as MEK inhibitors |
AU2003224052A1 (en) * | 2002-04-09 | 2003-10-20 | Novartis Ag | Compositions comprising mmp7 modulators for the treatment of chronic pain |
BR0316238A (pt) * | 2002-11-15 | 2005-10-11 | Warner Lambert Co | Quimioterapia de associação compreendendo um inibidor de mek e capecitabina para tratamento de câncer |
US7378233B2 (en) | 2003-04-12 | 2008-05-27 | The Johns Hopkins University | BRAF mutation T1796A in thyroid cancers |
US7144907B2 (en) | 2003-09-03 | 2006-12-05 | Array Biopharma Inc. | Heterocyclic inhibitors of MEK and methods of use thereof |
US7538120B2 (en) | 2003-09-03 | 2009-05-26 | Array Biopharma Inc. | Method of treating inflammatory diseases |
US8084645B2 (en) * | 2003-09-19 | 2011-12-27 | Chugai Seiyaku Kabushiki Kaisha | 4-phenylamino-benzaldoxime derivatives and uses thereof as mitogen-activated protein kinase kinase (MEK) inhibitors |
EP1682495A1 (fr) * | 2003-10-21 | 2006-07-26 | Warner-Lambert Company LLC | Forme polymorphe du i n /i - (r)-2,3-dihydroxy-propoxy|-3,4-difluoro-2-(2-fluoro-4-iodophenylamino)-benzamide |
US7517994B2 (en) * | 2003-11-19 | 2009-04-14 | Array Biopharma Inc. | Heterocyclic inhibitors of MEK and methods of use thereof |
US7732616B2 (en) | 2003-11-19 | 2010-06-08 | Array Biopharma Inc. | Dihydropyridine and dihydropyridazine derivatives as inhibitors of MEK and methods of use thereof |
JP5046649B2 (ja) | 2003-11-19 | 2012-10-10 | アレイ バイオファーマ、インコーポレイテッド | Mekの二環系阻害剤及びその使用方法 |
CA2546754A1 (fr) | 2003-11-21 | 2005-06-09 | Array Biopharma Inc. | Inhibiteurs de la proteine kinase akt |
UA89035C2 (ru) | 2003-12-03 | 2009-12-25 | Лео Фарма А/С | Эфиры гидроксамовых кислот и их фармацевтическое применение |
WO2005058341A2 (fr) * | 2003-12-11 | 2005-06-30 | Theravance, Inc. | Compositions a utiliser dans le traitement de maladies proliferatives cellulaires caracterisees par la presence d'une tyrosine kinase receptrice mutante |
BRPI0509580A (pt) * | 2004-03-30 | 2007-11-27 | Pfizer Prod Inc | combinações de inibidores de transdução de sinal |
US7378423B2 (en) | 2004-06-11 | 2008-05-27 | Japan Tobacco Inc. | Pyrimidine compound and medical use thereof |
RU2364596C2 (ru) | 2004-06-11 | 2009-08-20 | Джапан Тобакко Инк. | ПРОИЗВОДНЫЕ 5-АМИНО-2,4,7-ТРИОКСО-3,4,7,8-ТЕТРАГИДРО-2Н-ПИРИДО[2,3-d] ПИРИМИДИНА, ОБЛАДАЮЩИЕ ПРОТИВООПУХОЛЕВОЙ АКТИВНОСТЬЮ |
TWI361066B (en) | 2004-07-26 | 2012-04-01 | Chugai Pharmaceutical Co Ltd | 5-substituted-2-phenylamino benzamides as mek inhibitors |
JP2008510012A (ja) * | 2004-08-18 | 2008-04-03 | メルク エンド カムパニー インコーポレーテッド | 有糸分裂キネシン阻害剤 |
EP1802579B1 (fr) | 2004-10-20 | 2013-11-20 | Merck Serono SA | Dérivés de 3-arylaminopyridine |
WO2006061712A2 (fr) * | 2004-12-10 | 2006-06-15 | Pfizer Inc. | Utilisation d'inhibiteurs de mek dans le traitement d'une croissance cellulaire anormale |
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WO2006134469A1 (fr) * | 2005-06-14 | 2006-12-21 | Warner-Lambert Company Llc | Procedes de preparation d'un inhibiteur de mek |
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CA2628039A1 (fr) | 2005-11-11 | 2007-05-18 | Aeterna Zentaris Gmbh | Nouvelle pyridopyrazine et son utilisation pour la modulation de kinases |
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