EA017075B1 - Мезилат, гидраты и полиморфные формы этиламида 5-(2,4-дигидрокси-5-изопропилфенил)-4-(4-морфолин-4-илметилфенил)изоксазол-3-карбоновой кислоты и препараты, содержащие эти формы - Google Patents
Мезилат, гидраты и полиморфные формы этиламида 5-(2,4-дигидрокси-5-изопропилфенил)-4-(4-морфолин-4-илметилфенил)изоксазол-3-карбоновой кислоты и препараты, содержащие эти формы Download PDFInfo
- Publication number
- EA017075B1 EA017075B1 EA200901141A EA200901141A EA017075B1 EA 017075 B1 EA017075 B1 EA 017075B1 EA 200901141 A EA200901141 A EA 200901141A EA 200901141 A EA200901141 A EA 200901141A EA 017075 B1 EA017075 B1 EA 017075B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- isoxazole
- isopropylphenyl
- dihydroxy
- carboxylic acid
- ylmethylphenyl
- Prior art date
Links
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 title abstract description 18
- NDAZATDQFDPQBD-UHFFFAOYSA-N luminespib Chemical compound CCNC(=O)C1=NOC(C=2C(=CC(O)=C(C(C)C)C=2)O)=C1C(C=C1)=CC=C1CN1CCOCC1 NDAZATDQFDPQBD-UHFFFAOYSA-N 0.000 title abstract description 13
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- ZMAQNODASNQSRR-UHFFFAOYSA-N 5-(2,4-dihydroxy-5-propan-2-ylphenyl)-N-ethyl-4-[4-(morpholin-4-ylmethyl)phenyl]-1,2-oxazole-3-carboxamide methanesulfonic acid Chemical compound CS(O)(=O)=O.CCNC(=O)C1=NOC(C=2C(=CC(O)=C(C(C)C)C=2)O)=C1C(C=C1)=CC=C1CN1CCOCC1 ZMAQNODASNQSRR-UHFFFAOYSA-N 0.000 claims description 32
- 238000002441 X-ray diffraction Methods 0.000 claims description 23
- -1 2,4-dihydroxy-5-isopropylphenyl Chemical group 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 14
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- UXYRXGFUANQKTA-UHFFFAOYSA-N 1,2-oxazole-3-carboxylic acid Chemical compound OC(=O)C=1C=CON=1 UXYRXGFUANQKTA-UHFFFAOYSA-N 0.000 claims description 2
- VJZBSHKIQOPPRU-UHFFFAOYSA-N 5-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[4-(morpholin-4-ylmethyl)phenyl]-1,2-oxazole-3-carboxylic acid Chemical compound C1=C(O)C(C(C)C)=CC(C2=C(C(C(O)=O)=NO2)C=2C=CC(CN3CCOCC3)=CC=2)=C1O VJZBSHKIQOPPRU-UHFFFAOYSA-N 0.000 claims description 2
- ATWDUWYFCBVNET-UHFFFAOYSA-N ethylammonium methanesulfonate Chemical compound CC[NH3+].CS([O-])(=O)=O ATWDUWYFCBVNET-UHFFFAOYSA-N 0.000 claims description 2
- YKPOEQPMIKYMJJ-UHFFFAOYSA-N 5-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[4-(morpholin-4-ylmethyl)phenyl]-1,2-oxazole-3-carboxylic acid ethanamine methanesulfonic acid Chemical compound CCN.CS(O)(=O)=O.C1=C(O)C(C(C)C)=CC(C2=C(C(C(O)=O)=NO2)C=2C=CC(CN3CCOCC3)=CC=2)=C1O YKPOEQPMIKYMJJ-UHFFFAOYSA-N 0.000 claims 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- 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
- C07D295/14—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/155—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members 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
- C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07103346 | 2007-03-01 | ||
| PCT/EP2008/052443 WO2008104595A1 (en) | 2007-03-01 | 2008-02-28 | Acid addition salts, hydrates and polymorphs of 5-(2,4-dihydroxy-5-isopropyl-phenyl)-4-(4-morpholin-4-ylmethyl-phenyl)-isoxazole-3-carboxylic acid ethylamide and formulations comprising these forms |
Publications (2)
| Publication Number | Publication Date |
|---|---|
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| EA200901141A EA017075B1 (ru) | 2007-03-01 | 2008-02-28 | Мезилат, гидраты и полиморфные формы этиламида 5-(2,4-дигидрокси-5-изопропилфенил)-4-(4-морфолин-4-илметилфенил)изоксазол-3-карбоновой кислоты и препараты, содержащие эти формы |
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| EA032217B1 (ru) * | 2015-07-31 | 2019-04-30 | Ле Лаборатуар Сервье | Новое сочетание 3-[(3-{[4-(4-морфолинилметил)-1h-пиррол-2-ил]метилен}-2-оксо-2,3-дигидро-1h-индол-5-ил)метил]-1,3-тиазолидин-2,4-диона и ингибитора тирозинкиназы egfr |
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| TW200922595A (en) * | 2007-10-12 | 2009-06-01 | Novartis Ag | Organic compounds |
| TWI450898B (zh) * | 2008-07-04 | 2014-09-01 | Sigma Tau Res Switzerland Sa | 具有抗腫瘤活性之芳基異唑化合物 |
| US8309578B2 (en) | 2008-11-25 | 2012-11-13 | Nerviano Medical Sciences S.R.L. | Bicyclic pyrazole and isoxazole derivatives as antitumor and antineurodegenerative agents |
| WO2011089234A2 (en) * | 2010-01-21 | 2011-07-28 | Aprea Ab | Method and composition |
| CN102753546A (zh) * | 2010-02-17 | 2012-10-24 | 日东制药株式会社 | 新型5-元杂环衍生物及其制备方法 |
| KR20120031854A (ko) | 2010-09-27 | 2012-04-04 | 한국전자통신연구원 | 시간 및 주파수 특징을 이용하는 음악 음원 분리 장치 및 방법 |
| WO2013015661A2 (en) * | 2011-07-28 | 2013-01-31 | Ildong Pharm Co.,Ltd. | Novel prodrugs of 5-(2,4-dihydroxy-5-isopropylphenyl)-n-ethyl-4-(5-methyl1-1,2,4-oxadiazol-3-yl)isoxazole-3-carboxamide |
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| WO2004072051A1 (en) * | 2003-02-11 | 2004-08-26 | Vernalis (Cambridge) Limited | Isoxazole compounds as inhibitors of heat shock proteins |
| US20060070405A1 (en) * | 2004-10-06 | 2006-04-06 | Anheuser-Busch, Inc. | Method for the production of amber glass with reduced sulfur-containing emissions |
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| WO2010069458A1 (de) | 2008-12-17 | 2010-06-24 | Merck Patent Gmbh | Hexahalochromat(lll)-komplexe |
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| EA032217B1 (ru) * | 2015-07-31 | 2019-04-30 | Ле Лаборатуар Сервье | Новое сочетание 3-[(3-{[4-(4-морфолинилметил)-1h-пиррол-2-ил]метилен}-2-оксо-2,3-дигидро-1h-индол-5-ил)метил]-1,3-тиазолидин-2,4-диона и ингибитора тирозинкиназы egfr |
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