SK285216B6 - Spôsob prípravy kryštalickej formy N-(4-trifluórmetylfenyl)-5- metyl-izoxazol-4-karboxamidu - Google Patents
Spôsob prípravy kryštalickej formy N-(4-trifluórmetylfenyl)-5- metyl-izoxazol-4-karboxamidu Download PDFInfo
- Publication number
- SK285216B6 SK285216B6 SK1521-2001A SK15212001A SK285216B6 SK 285216 B6 SK285216 B6 SK 285216B6 SK 15212001 A SK15212001 A SK 15212001A SK 285216 B6 SK285216 B6 SK 285216B6
- Authority
- SK
- Slovakia
- Prior art keywords
- modification
- organic solvent
- formula
- water
- temperature
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 239000013078 crystal Substances 0.000 title abstract description 24
- 238000012986 modification Methods 0.000 claims abstract description 57
- 230000004048 modification Effects 0.000 claims abstract description 57
- 150000001875 compounds Chemical class 0.000 claims abstract description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000003960 organic solvent Substances 0.000 claims abstract description 27
- 239000000203 mixture Substances 0.000 claims abstract description 25
- 238000009835 boiling Methods 0.000 claims abstract description 9
- 238000002425 crystallisation Methods 0.000 claims abstract description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 39
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 238000002441 X-ray diffraction Methods 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 6
- 230000008025 crystallization Effects 0.000 claims description 5
- 238000004090 dissolution Methods 0.000 claims description 5
- 229910017488 Cu K Inorganic materials 0.000 claims description 4
- 229910017541 Cu-K Inorganic materials 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 239000000725 suspension Substances 0.000 claims description 4
- 238000005169 Debye-Scherrer Methods 0.000 claims description 3
- 230000005540 biological transmission Effects 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000011148 porous material Substances 0.000 claims description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 3
- 239000007900 aqueous suspension Substances 0.000 claims description 2
- 230000005855 radiation Effects 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims 1
- 238000007865 diluting Methods 0.000 claims 1
- 239000000706 filtrate Substances 0.000 claims 1
- 239000011874 heated mixture Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 20
- VHOGYURTWQBHIL-UHFFFAOYSA-N leflunomide Chemical compound O1N=CC(C(=O)NC=2C=CC(=CC=2)C(F)(F)F)=C1C VHOGYURTWQBHIL-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 229960000681 leflunomide Drugs 0.000 description 3
- QBPXGTUBZXXKJO-UHFFFAOYSA-N 1,2-oxazole-4-carboxamide Chemical compound NC(=O)C=1C=NOC=1 QBPXGTUBZXXKJO-UHFFFAOYSA-N 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- 230000005260 alpha ray Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/14—Decongestants or antiallergics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic 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
Landscapes
- 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19734438A DE19734438A1 (de) | 1997-08-08 | 1997-08-08 | Kristallform von N-(4-Trifluormethylphenyl)-5-methyl-isoxazole-4-carboxamid |
| DE1997156093 DE19756093A1 (de) | 1997-12-17 | 1997-12-17 | Verfahren zur Herstellung einer Kristallform von N-(4-Trifluormethylphenyl)-5-methyl-isoxazole-4-carboxamid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK285216B6 true SK285216B6 (sk) | 2006-09-07 |
Family
ID=26038983
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1521-2001A SK285216B6 (sk) | 1997-08-08 | 1998-08-06 | Spôsob prípravy kryštalickej formy N-(4-trifluórmetylfenyl)-5- metyl-izoxazol-4-karboxamidu |
| SK1058-98A SK282641B6 (sk) | 1997-08-08 | 1998-08-06 | Kryštalická forma N-(4-trifluórmetylfenyl)-5-metyl-izoxazol-4- karboxamidu, spôsob jej prípravy, liečivo, ktoré ju obsahuje, a jej použitie |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1058-98A SK282641B6 (sk) | 1997-08-08 | 1998-08-06 | Kryštalická forma N-(4-trifluórmetylfenyl)-5-metyl-izoxazol-4- karboxamidu, spôsob jej prípravy, liečivo, ktoré ju obsahuje, a jej použitie |
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 |
Family Cites Families (29)
| 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. |
| DE2854439A1 (de) * | 1978-12-16 | 1980-07-03 | Hoechst Ag | Ein isoxazolderivat, verfahren zu seiner herstellung, diese verbindung enthaltende mittel und verwendung |
| IL63968A (en) * | 1980-10-01 | 1985-10-31 | Glaxo Group Ltd | Form 2 ranitidine hydrochloride,its preparation and pharmaceutical compositions containing it |
| US4935434A (en) * | 1988-01-26 | 1990-06-19 | Bristol-Myers Company | Antiarthritic isoxazole-4-carboxamides |
| 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 |
| GB9115377D0 (en) * | 1991-07-17 | 1991-09-04 | Rhone Poulenc Agriculture | New compositions of matter |
| 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 |
-
1998
- 1998-07-31 AT AT98114373T patent/ATE196764T1/de active
- 1998-07-31 AT AT99117098T patent/ATE207065T1/de active
- 1998-07-31 DK DK99117098T patent/DK0987256T3/da active
- 1998-07-31 ES ES98114373T patent/ES2150808T3/es not_active Expired - Lifetime
- 1998-07-31 DE DE59801792T patent/DE59801792D1/de not_active Expired - Lifetime
- 1998-07-31 DK DK98114373T patent/DK0903345T3/da active
- 1998-07-31 PT PT99117098T patent/PT987256E/pt unknown
- 1998-07-31 DE DE59800287T patent/DE59800287D1/de not_active Expired - Lifetime
- 1998-07-31 EP EP98114373A patent/EP0903345B1/de not_active Expired - Lifetime
- 1998-07-31 ES ES99117098T patent/ES2166205T3/es not_active Expired - Lifetime
- 1998-07-31 PT PT98114373T patent/PT903345E/pt unknown
- 1998-07-31 EP EP99117098A patent/EP0987256B1/de not_active Expired - Lifetime
- 1998-08-05 IL IL12567198A patent/IL125671A/en not_active IP Right Cessation
- 1998-08-05 CZ CZ20032983A patent/CZ301426B6/cs not_active IP Right Cessation
- 1998-08-05 CZ CZ20032982A patent/CZ301514B6/cs not_active IP Right Cessation
- 1998-08-05 CZ CZ19982468A patent/CZ292943B6/cs not_active IP Right Cessation
- 1998-08-06 US US09/129,783 patent/US6060494A/en not_active Expired - Lifetime
- 1998-08-06 TR TR1998/01513A patent/TR199801513A2/xx unknown
- 1998-08-06 TR TR2006/00582A patent/TR200600582A1/xx unknown
- 1998-08-06 UA UA98084307A patent/UA54411C2/uk unknown
- 1998-08-06 NZ NZ331270A patent/NZ331270A/xx not_active IP Right Cessation
- 1998-08-06 AR ARP980103900A patent/AR015418A1/es active IP Right Grant
- 1998-08-06 TW TW087112927A patent/TW593288B/zh not_active IP Right Cessation
- 1998-08-06 SK SK1521-2001A patent/SK285216B6/sk not_active IP Right Cessation
- 1998-08-06 ID IDP981098A patent/ID20667A/id unknown
- 1998-08-06 SK SK1058-98A patent/SK282641B6/sk not_active IP Right Cessation
- 1998-08-07 HU HU0700190A patent/HU229232B1/hu unknown
- 1998-08-07 KR KR1019980032110A patent/KR100544041B1/ko not_active Expired - Lifetime
- 1998-08-07 HU HU9801844A patent/HU225870B1/hu unknown
- 1998-08-07 CN CN98116235A patent/CN1089759C/zh not_active Expired - Lifetime
- 1998-08-07 RU RU98115390/04A patent/RU2224753C2/ru active
- 1998-08-07 PL PL327901A patent/PL192126B1/pl unknown
- 1998-08-07 NO NO19983632A patent/NO310871B1/no not_active IP Right Cessation
- 1998-08-07 JP JP10224015A patent/JPH11124372A/ja active Pending
- 1998-08-07 CA CA002245267A patent/CA2245267C/en not_active Expired - Lifetime
- 1998-08-07 BR BR9806568-8A patent/BR9806568A/pt not_active Application Discontinuation
- 1998-08-07 AU AU78870/98A patent/AU752764B2/en not_active Expired
- 1998-08-07 CN CNB021045747A patent/CN1181064C/zh not_active Expired - Lifetime
-
1999
- 1999-10-28 US US09/428,499 patent/US6221891B1/en not_active Expired - Lifetime
-
2000
- 2000-11-10 GR GR20000402501T patent/GR3034814T3/el unknown
-
2001
- 2001-01-19 US US09/764,258 patent/US6552202B2/en not_active Expired - Lifetime
-
2002
- 2002-11-25 US US10/302,872 patent/US6900334B2/en not_active Expired - Lifetime
-
2003
- 2003-02-19 HK HK03101247.6A patent/HK1049481B/zh not_active IP Right Cessation
-
2004
- 2004-04-23 US US10/830,307 patent/US6995272B2/en not_active Expired - Lifetime
-
2005
- 2005-06-28 KR KR1020050056044A patent/KR100588254B1/ko not_active Expired - Lifetime
-
2009
- 2009-07-28 JP JP2009175137A patent/JP2009280604A/ja active Pending
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SK285216B6 (sk) | Spôsob prípravy kryštalickej formy N-(4-trifluórmetylfenyl)-5- metyl-izoxazol-4-karboxamidu | |
| RU2066324C1 (ru) | Кристаллический дигидрат азитромицина и способ его получения | |
| CZ20004637A3 (cs) | Polymorfní forma hydrogensíranu klopidogrelu | |
| CZ301778B6 (cs) | Modifikace 2-amino-4-(4-fluorbenzylamino)-1-ethoxykarbonylaminobenzenu, zpusoby jejich prípravy, jejich použití a lécivo, které je obsahuje | |
| SK284935B6 (sk) | Forma I (-)-6-chlór-4-cyklopropyletynyl-4-tri-fluórmetyl-1,4- dihydro-2H-3,1-benzoxazín-2-ónu a spôsob jej kryštalizácie | |
| HUE029324T2 (en) | Polymorphic forms of an MGLUR5 receptor antagonist | |
| SE454693B (sv) | 2-amino-3-karbetoxiamino-6-(p-fluor-bensylamino)-pyridin-maleat, forfarande for framstellning av detta och ett lekemedel med analgetisk och/eller antiflogistisk effekt | |
| AU2009314203B2 (en) | Method for preparing a non-hydratable crystal form | |
| CZ2002404A3 (cs) | Polymorfní formy torsemidu | |
| CN121591830A (zh) | 曲非奈肽的结晶形式 | |
| EP0182572B1 (en) | Novel crystalline form of benzothiazine dioxide salt | |
| KR19980064288A (ko) | 다형태를 갖는 독사조신 메실레이트의 새로운 형태(제 iii 형) | |
| JPH0230346B2 (ja) | Buririantokaamin6bnofukasakukagobutsunoseizoho | |
| DE19934295A1 (de) | Kristallmodifikation III von N-(4-(5-Dimethylamino-naphthalin-1-sulfonyl-amino)-phenyl)-3-hydroxy-2,2-dimethyl-propionamid | |
| WO2020016827A1 (en) | Purified crystalline detomidine hydrochloride monohydrate, anhydrate and free base with low amounts of iso-detomidine and other impurities by recrystallisation in water | |
| CA2531948C (en) | Crystal form of n-(4-trifluoromethylphenyl)-5-methylisoxazole-4-carboxamide | |
| AU2001278104B8 (en) | Solid forms of tin ethyl etiopurpurin and processes for producing such forms | |
| AU2001278104A1 (en) | Solid forms of tin ethyl etiopurpurin and processes for producing such forms | |
| WO2004083230A1 (en) | Novel crystalline forms of finasteride | |
| SK113894A3 (en) | N-t-butyl-androst-3,5-diene-17-beta-carboxamide-3-carboxylic acid polymorph a | |
| WO1996027592A1 (en) | Polymorphic b form of (e)-4-[[3-[2-(4-cyclobutyl-2-thiazolyl)ethenyl]phenyl]amino]-2,2-diethyl-4-oxobutanoic acid |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK4A | Patent expired |
Expiry date: 20180806 |