RU2224753C2 - Кристаллическая форма 2n-(4-фторметилфенил)-5-метил-изоксазол-4-карбоксамида и способы получения кристаллических форм 1 и 2 указанного карбоксамида - Google Patents
Кристаллическая форма 2n-(4-фторметилфенил)-5-метил-изоксазол-4-карбоксамида и способы получения кристаллических форм 1 и 2 указанного карбоксамида Download PDFInfo
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- RU2224753C2 RU2224753C2 RU98115390/04A RU98115390A RU2224753C2 RU 2224753 C2 RU2224753 C2 RU 2224753C2 RU 98115390/04 A RU98115390/04 A RU 98115390/04A RU 98115390 A RU98115390 A RU 98115390A RU 2224753 C2 RU2224753 C2 RU 2224753C2
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- organic solvent
- water
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- 238000000034 method Methods 0.000 title claims abstract 19
- 150000003857 carboxamides Chemical class 0.000 title abstract 2
- 239000003960 organic solvent Substances 0.000 claims abstract 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract 14
- 239000000203 mixture Substances 0.000 claims abstract 12
- 150000001875 compounds Chemical class 0.000 claims abstract 11
- 238000002425 crystallisation Methods 0.000 claims abstract 4
- 230000008025 crystallization Effects 0.000 claims abstract 4
- 238000012986 modification Methods 0.000 claims abstract 3
- 230000004048 modification Effects 0.000 claims abstract 3
- 229910052799 carbon Inorganic materials 0.000 claims abstract 2
- 238000010438 heat treatment Methods 0.000 claims abstract 2
- OOCZQVHUVDWLER-UHFFFAOYSA-N n-[4-(fluoromethyl)phenyl]-5-methyl-1,2-oxazole-4-carboxamide Chemical compound O1N=CC(C(=O)NC=2C=CC(CF)=CC=2)=C1C OOCZQVHUVDWLER-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000000725 suspension Substances 0.000 claims abstract 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 12
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- 239000000243 solution Substances 0.000 claims 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 3
- 238000005169 Debye-Scherrer Methods 0.000 claims 2
- 239000007900 aqueous suspension Substances 0.000 claims 2
- 238000010790 dilution Methods 0.000 claims 2
- 239000012895 dilution Substances 0.000 claims 2
- 239000011148 porous material Substances 0.000 claims 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 2
- 230000005855 radiation Effects 0.000 claims 2
- -1 aliphatic alcohols Chemical class 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 239000011874 heated mixture Substances 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract 2
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Classifications
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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
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A61P11/06—Antiasthmatics
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Diabetes (AREA)
- Pulmonology (AREA)
- Endocrinology (AREA)
- Rheumatology (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Physical Education & Sports Medicine (AREA)
- Hematology (AREA)
- Ophthalmology & Optometry (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Neurosurgery (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Biomedical Technology (AREA)
- Urology & Nephrology (AREA)
- Reproductive Health (AREA)
- Dermatology (AREA)
- Orthopedic Medicine & Surgery (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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19734438.0 | 1997-08-08 | ||
| DE19734438A DE19734438A1 (de) | 1997-08-08 | 1997-08-08 | Kristallform von N-(4-Trifluormethylphenyl)-5-methyl-isoxazole-4-carboxamid |
| DE19756093.8 | 1997-12-17 | ||
| DE1997156093 DE19756093A1 (de) | 1997-12-17 | 1997-12-17 | Verfahren zur Herstellung einer Kristallform von N-(4-Trifluormethylphenyl)-5-methyl-isoxazole-4-carboxamid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU98115390A RU98115390A (ru) | 2000-08-20 |
| RU2224753C2 true RU2224753C2 (ru) | 2004-02-27 |
Family
ID=26038983
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU98115390/04A RU2224753C2 (ru) | 1997-08-08 | 1998-08-07 | Кристаллическая форма 2n-(4-фторметилфенил)-5-метил-изоксазол-4-карбоксамида и способы получения кристаллических форм 1 и 2 указанного карбоксамида |
Country Status (28)
| Country | Link |
|---|---|
| US (5) | US6060494A (https=) |
| EP (2) | EP0903345B1 (https=) |
| JP (2) | JPH11124372A (https=) |
| KR (2) | KR100544041B1 (https=) |
| CN (2) | CN1089759C (https=) |
| AR (1) | AR015418A1 (https=) |
| AT (2) | ATE196764T1 (https=) |
| AU (1) | AU752764B2 (https=) |
| BR (1) | BR9806568A (https=) |
| CA (1) | CA2245267C (https=) |
| CZ (3) | CZ301426B6 (https=) |
| DE (2) | DE59801792D1 (https=) |
| DK (2) | DK0987256T3 (https=) |
| ES (2) | ES2150808T3 (https=) |
| GR (1) | GR3034814T3 (https=) |
| HK (1) | HK1049481B (https=) |
| HU (2) | HU229232B1 (https=) |
| ID (1) | ID20667A (https=) |
| IL (1) | IL125671A (https=) |
| NO (1) | NO310871B1 (https=) |
| NZ (1) | NZ331270A (https=) |
| PL (1) | PL192126B1 (https=) |
| PT (2) | PT987256E (https=) |
| RU (1) | RU2224753C2 (https=) |
| SK (2) | SK285216B6 (https=) |
| TR (2) | TR199801513A2 (https=) |
| TW (1) | TW593288B (https=) |
| UA (1) | UA54411C2 (https=) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE196764T1 (de) * | 1997-08-08 | 2000-10-15 | Aventis Pharma Gmbh | Kristallform von 5-methylisoxazol-4-carbonsäure- (4-trifluormethyl)-anilid |
| DE19908527C2 (de) | 1999-02-26 | 2001-08-30 | Aventis Pharma Gmbh | Verfahren zur Kristallisation von N-(4-Trifluormethylphenyl)-5-methyl-isoxazol-4-carboxamid |
| CN1411373A (zh) * | 1999-12-16 | 2003-04-16 | 特瓦制药工业有限公司 | 制备来氟米特的新方法和新晶形的来氟米特 |
| CA2400290A1 (en) * | 2000-02-15 | 2001-08-23 | Teva Pharmaceutical Industries Ltd. | A method for synthesizing leflunomide |
| CA2429426A1 (en) * | 2000-11-17 | 2002-05-23 | Takeda Chemical Industries, Ltd. | Isoxazole derivatives |
| GB0123571D0 (en) | 2001-04-05 | 2001-11-21 | Aventis Pharm Prod Inc | Use of (Z)-2-cyano-3-hydroxy-but-2-enoic acid-(4'-trifluoromethylphenyl)-amide for treating multiple sclerosis |
| US7429593B2 (en) | 2001-09-14 | 2008-09-30 | Shionogi & Co., Ltd. | Utilities of amide compounds |
| AU2003207055A1 (en) * | 2002-02-12 | 2003-09-04 | Sumitomo Pharmaceuticals Co., Ltd. | Novel drugs for external use |
| US20050158371A1 (en) * | 2002-02-12 | 2005-07-21 | Sumitomo Pharmaceuticals Co., Ltd. | Novel external agent |
| US20060135547A1 (en) * | 2003-03-12 | 2006-06-22 | Toth Zoltan G | Stable pharmaceutical compositions of desloratadine and processes for preparation of polymorphic forms of desloratadine |
| WO2004080461A2 (en) * | 2003-03-12 | 2004-09-23 | TEVA Gyógyszergyár Részvénytársaság | Stable pharmaceutical compositions of desloratadine |
| JP4223428B2 (ja) * | 2004-03-31 | 2009-02-12 | 富士通メディアデバイス株式会社 | フィルタおよびその製造方法 |
| WO2007067710A1 (en) * | 2005-12-08 | 2007-06-14 | Amphora Discovery Corporation | Certain chemical entities, compositions, and methods for modulating trpv1 |
| CN101143834B (zh) * | 2006-09-15 | 2010-09-08 | 欣凯医药化工中间体（上海）有限公司 | N-(4-三氟甲基苯)-2-氰基-3-羟基丁烯酰胺钠盐的多晶型及其制备方法 |
| JP2011513202A (ja) * | 2008-03-10 | 2011-04-28 | 武田薬品工業株式会社 | ベンズイミダゾール化合物の結晶 |
| US20120172427A1 (en) | 2009-09-18 | 2012-07-05 | Sanofi | (z)-2-cyano-3-hydroxy-but-2-enoic acid-(4'-trifluoromethylphenyl)-amide tablet formulations with improved stability |
| CN103977594B (zh) * | 2014-06-03 | 2016-02-17 | 江苏九九久科技股份有限公司 | 一种结晶方法 |
| US9895370B2 (en) * | 2015-11-19 | 2018-02-20 | Pharmedix.Co., Ltd | Pharmaceutical composition for preventing or treating of cirrhosis of liver comprising G protein coupled receptor 119 ligand as an active ingredient |
| CN109180599A (zh) * | 2018-09-03 | 2019-01-11 | 深圳市新阳唯康科技有限公司 | 一种来氟米特新晶型化合物及其制备方法 |
| CN112898215B (zh) * | 2021-02-04 | 2022-11-08 | 美罗药业股份有限公司 | 一种来氟米特晶型i的制备方法 |
| CN114716388B (zh) * | 2021-11-04 | 2024-02-13 | 江苏冠军科技集团股份有限公司 | 一种磺胺-银化合物及其制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US4284786A (en) * | 1978-12-16 | 1981-08-18 | Hoechst Aktiengesellschaft | 5-Methylisoxazole-4-carboxylic-(4-trifluoromethyl)-anilide |
| US4935434A (en) * | 1988-01-26 | 1990-06-19 | Bristol-Myers Company | Antiarthritic isoxazole-4-carboxamides |
| RU2060251C1 (ru) * | 1991-07-17 | 1996-05-20 | Рон Пуленк Эгрикалчер Лтд. | Производные 5-арилизоксазола, способы их получения, гербицидная композиция и способ подавления сорняков в локусе |
Family Cites Families (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL186239B (nl) * | 1975-06-05 | Hoechst Ag | Werkwijze voor de bereiding van een geneesmiddel met antiflogistische en/of analgetische werking, alsmede werkwijze voor de bereiding van een 2-hydroxyethylideencyaanazijnzuuranilide geschikt voor toepassing bij deze werkwijze. | |
| NL178596C (nl) * | 1975-06-05 | 1986-04-16 | Hoechst Ag | Werkwijze voor het bereiden van een geneesmiddel met antiflogistische en/of analgetische werking, alsmede werkwijze voor het bereiden van daarin als geneeskrachtige verbindingen te gebruiken 5-methylisoxazool-4-carbonzuuraniliden. |
| DE2524959C2 (de) * | 1975-06-05 | 1983-02-10 | Hoechst Ag, 6000 Frankfurt | 5-Methyl-isoxazol-4-carbonsäureanilide, Verfahren zu ihrer Herstellung, diese Verbindungen enthaltende Mittel |
| DE2525959A1 (de) * | 1975-06-11 | 1977-02-10 | Focke Pfuhl Verpack Automat | Verpackung fuer zigaretten, zigarillos etc. |
| IL63968A (en) * | 1980-10-01 | 1985-10-31 | Glaxo Group Ltd | Form 2 ranitidine hydrochloride,its preparation and pharmaceutical compositions containing it |
| US5583150A (en) * | 1989-08-18 | 1996-12-10 | Alcon Laboratories, Inc. | 5-methyl-isoxazole-4-carboxylic acid anilides and 2-hydroxyethylidene-cyano acetic anilides for the treatment of ocular diseases |
| DE59010701D1 (de) * | 1990-05-18 | 1997-05-22 | Hoechst Ag | Isoxazol-4-carbonsäureamide und hydroxyalkyliden-cyanessigsäureamide, diese verbindungen enthaltende arzneimittel und deren verwendung |
| DE4127737A1 (de) * | 1991-08-22 | 1993-02-25 | Hoechst Ag | Arzneimittel zur behandlung von abstossungsreaktionen bei organverpflanzungen |
| GB9209330D0 (en) * | 1992-04-30 | 1992-06-17 | Roussel Lab Ltd | Chemical compounds |
| ES2124800T3 (es) * | 1993-01-08 | 1999-02-16 | Hoechst Ag | Empleo de leflunomida para la inhibicion de interleuquina 1 beta. |
| DE59407414D1 (de) * | 1993-01-08 | 1999-01-21 | Hoechst Ag | Verwendung von Leflunomid zur Hemmung von Tumornekrosefaktor alpha |
| EP0607777B1 (de) * | 1993-01-08 | 1998-12-09 | Hoechst Aktiengesellschaft | Verwendung von Leflunomid zur Hemmung von Interleukin 8 |
| TW314467B (https=) * | 1993-03-31 | 1997-09-01 | Hoechst Ag | |
| GB9320299D0 (en) * | 1993-10-01 | 1993-11-17 | Roussel Lab Ltd | Isoxazole derivatives |
| US5610173A (en) * | 1994-01-07 | 1997-03-11 | Sugen, Inc. | Formulations for lipophilic compounds |
| KR100365064B1 (ko) * | 1994-10-17 | 2003-04-11 | 훽스트파마슈티칼스앤드케미칼스가부시키가이샤 | I형알레르기성질환의예방및치료제 |
| SK283608B6 (sk) * | 1995-02-06 | 2003-10-07 | Smithkline Beecham Plc | Bezvodý hydrochlorid paroxetínu, spôsob jeho výroby a použitie |
| DE19539638A1 (de) * | 1995-10-25 | 1997-04-30 | Hoechst Ag | Die Verwendung von Isoxazol- und Crotonsäureamidderivaten zur Behandlung von Krebserkrankungen |
| US6316479B1 (en) * | 1997-05-19 | 2001-11-13 | Sugen, Inc. | Isoxazole-4-carboxamide compounds active against protein tryosine kinase related disorders |
| HRP980291A2 (en) * | 1997-06-16 | 1999-04-30 | Lin-Hua Zhang | Crystalline roxifiban |
| ATE196764T1 (de) * | 1997-08-08 | 2000-10-15 | Aventis Pharma Gmbh | Kristallform von 5-methylisoxazol-4-carbonsäure- (4-trifluormethyl)-anilid |
| US6096770A (en) * | 1998-08-03 | 2000-08-01 | American Home Products Corporation | Anthranilic acid analogs |
| DE19908527C2 (de) * | 1999-02-26 | 2001-08-30 | Aventis Pharma Gmbh | Verfahren zur Kristallisation von N-(4-Trifluormethylphenyl)-5-methyl-isoxazol-4-carboxamid |
| CN1411373A (zh) * | 1999-12-16 | 2003-04-16 | 特瓦制药工业有限公司 | 制备来氟米特的新方法和新晶形的来氟米特 |
| CA2400290A1 (en) * | 2000-02-15 | 2001-08-23 | Teva Pharmaceutical Industries Ltd. | A method for synthesizing leflunomide |
| US6727272B1 (en) * | 2002-07-15 | 2004-04-27 | Unitech Pharmaceuticals, Inc. | Leflunomide analogs for treating rheumatoid arthritis |
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1998
- 1998-07-31 AT AT98114373T patent/ATE196764T1/de active
- 1998-07-31 AT AT99117098T patent/ATE207065T1/de active
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4284786A (en) * | 1978-12-16 | 1981-08-18 | Hoechst Aktiengesellschaft | 5-Methylisoxazole-4-carboxylic-(4-trifluoromethyl)-anilide |
| US4935434A (en) * | 1988-01-26 | 1990-06-19 | Bristol-Myers Company | Antiarthritic isoxazole-4-carboxamides |
| RU2060251C1 (ru) * | 1991-07-17 | 1996-05-20 | Рон Пуленк Эгрикалчер Лтд. | Производные 5-арилизоксазола, способы их получения, гербицидная композиция и способ подавления сорняков в локусе |
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