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)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Ophthalmology & Optometry (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Neurology (AREA)
- Oncology (AREA)
- Biomedical Technology (AREA)
- Communicable Diseases (AREA)
- Neurosurgery (AREA)
- Reproductive Health (AREA)
- Pain & Pain Management (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Dermatology (AREA)
- Urology & Nephrology (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 (no) |
| EP (2) | EP0903345B1 (no) |
| JP (2) | JPH11124372A (no) |
| KR (2) | KR100544041B1 (no) |
| CN (2) | CN1089759C (no) |
| AR (1) | AR015418A1 (no) |
| AT (2) | ATE207065T1 (no) |
| AU (1) | AU752764B2 (no) |
| BR (1) | BR9806568A (no) |
| CA (1) | CA2245267C (no) |
| CZ (3) | CZ292943B6 (no) |
| DE (2) | DE59801792D1 (no) |
| DK (2) | DK0903345T3 (no) |
| ES (2) | ES2166205T3 (no) |
| GR (1) | GR3034814T3 (no) |
| HK (2) | HK1017681A1 (no) |
| HU (2) | HU229232B1 (no) |
| ID (1) | ID20667A (no) |
| IL (1) | IL125671A (no) |
| NO (1) | NO310871B1 (no) |
| NZ (1) | NZ331270A (no) |
| PL (1) | PL192126B1 (no) |
| PT (2) | PT903345E (no) |
| RU (1) | RU2224753C2 (no) |
| SK (2) | SK285216B6 (no) |
| TR (2) | TR200600582A1 (no) |
| TW (1) | TW593288B (no) |
| UA (1) | UA54411C2 (no) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0903345B1 (de) * | 1997-08-08 | 2000-10-04 | Aventis Pharma Deutschland 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 |
| AU779931B2 (en) * | 1999-12-16 | 2005-02-17 | Teva Pharmaceutical Industries Ltd. | Novel processes for making- and a new crystalline form of- leflunomide |
| ES2237553T3 (es) * | 2000-02-15 | 2005-08-01 | Teva Pharmaceutical Industries Ltd. | Procedimiento para la sintesis de leflunomida. |
| WO2002040458A1 (fr) * | 2000-11-17 | 2002-05-23 | Takeda Chemical Industries, Ltd. | Derives d'isoxazole |
| 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 |
| WO2003068239A1 (fr) * | 2002-02-12 | 2003-08-21 | Sumitomo Pharmaceuticals Co., Ltd. | Nouveaux medicaments d'usage externe |
| US20050158371A1 (en) * | 2002-02-12 | 2005-07-21 | Sumitomo Pharmaceuticals Co., Ltd. | Novel external agent |
| ES2232332T3 (es) * | 2003-03-12 | 2007-08-16 | Teva Pharmaceutical Industries Ltd | Composiciones farmaceuticas estables de desloratadina. |
| 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 |
| 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 |
| UY31695A (es) * | 2008-03-10 | 2009-11-10 | Takeda Pharmaceutical | Cristal de compuestos de bencimidazol |
| CN104666238B (zh) | 2009-09-18 | 2018-04-06 | 赛诺菲 | 稳定性提高的(z)‑2‑氰基‑3‑羟基‑丁‑2‑烯酸‑(4’‑三氟甲基苯基)‑酰胺片剂制剂 |
| 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 (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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. | |
| ES448386A1 (es) * | 1975-06-05 | 1978-04-16 | Hoechst Ag | Procedimiento para la preparacion de anilidas de acido 5-me-til-isoxazol-4-carboxilico. |
| 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 |
| DK0527736T3 (da) * | 1990-05-18 | 1997-10-20 | Hoechst Ag | Isoxazol-4-carboxylsyreamider og hydroxyalkyliden-cyanoacetamider, lægemidler indeholdende disse forbindelser og anvendelsen af disse lægemidler. |
| 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. |
| ATE174219T1 (de) * | 1993-01-08 | 1998-12-15 | Hoechst Ag | Verwendung von leflunomid zur hemmung von tumornekrosefaktor alpha |
| ATE174220T1 (de) * | 1993-01-08 | 1998-12-15 | Hoechst Ag | Verwendung von leflunomid zur hemmung von interleukin 8 |
| TW314467B (no) * | 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 |
| ATE194912T1 (de) * | 1994-10-17 | 2000-08-15 | Aventis Pharma Ltd | Mittel zur vorsorge und heilung von typ i allergischen krankheiten |
| AR001982A1 (es) * | 1995-02-06 | 1998-01-07 | Smithkline Beecham Plc | Clorhidrato de paroxetina anhidratado, y procedimiento para su preparacion |
| 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 |
| EP0903345B1 (de) * | 1997-08-08 | 2000-10-04 | Aventis Pharma Deutschland 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 |
| AU779931B2 (en) * | 1999-12-16 | 2005-02-17 | Teva Pharmaceutical Industries Ltd. | Novel processes for making- and a new crystalline form of- leflunomide |
| ES2237553T3 (es) * | 2000-02-15 | 2005-08-01 | Teva Pharmaceutical Industries Ltd. | Procedimiento para la sintesis de leflunomida. |
| US6727272B1 (en) * | 2002-07-15 | 2004-04-27 | Unitech Pharmaceuticals, Inc. | Leflunomide analogs for treating rheumatoid arthritis |
-
1998
- 1998-07-31 EP EP98114373A patent/EP0903345B1/de not_active Expired - Lifetime
- 1998-07-31 AT AT99117098T patent/ATE207065T1/de active
- 1998-07-31 PT PT98114373T patent/PT903345E/pt unknown
- 1998-07-31 ES ES99117098T patent/ES2166205T3/es not_active Expired - Lifetime
- 1998-07-31 DK DK98114373T patent/DK0903345T3/da active
- 1998-07-31 DE DE59801792T patent/DE59801792D1/de not_active Expired - Lifetime
- 1998-07-31 PT PT99117098T patent/PT987256E/pt unknown
- 1998-07-31 ES ES98114373T patent/ES2150808T3/es not_active Expired - Lifetime
- 1998-07-31 EP EP99117098A patent/EP0987256B1/de not_active Expired - Lifetime
- 1998-07-31 DE DE59800287T patent/DE59800287D1/de not_active Expired - Lifetime
- 1998-07-31 AT AT98114373T patent/ATE196764T1/de active
- 1998-07-31 DK DK99117098T patent/DK0987256T3/da active
- 1998-08-05 CZ CZ19982468A patent/CZ292943B6/cs not_active IP Right Cessation
- 1998-08-05 IL IL12567198A patent/IL125671A/en not_active IP Right Cessation
- 1998-08-05 CZ CZ20032982A patent/CZ301514B6/cs not_active IP Right Cessation
- 1998-08-05 CZ CZ20032983A patent/CZ301426B6/cs not_active IP Right Cessation
- 1998-08-06 UA UA98084307A patent/UA54411C2/uk unknown
- 1998-08-06 TW TW087112927A patent/TW593288B/zh not_active IP Right Cessation
- 1998-08-06 US US09/129,783 patent/US6060494A/en not_active Expired - Lifetime
- 1998-08-06 AR ARP980103900A patent/AR015418A1/es active IP Right Grant
- 1998-08-06 NZ NZ331270A patent/NZ331270A/xx not_active IP Right Cessation
- 1998-08-06 TR TR2006/00582A patent/TR200600582A1/xx unknown
- 1998-08-06 SK SK1521-2001A patent/SK285216B6/sk not_active IP Right Cessation
- 1998-08-06 SK SK1058-98A patent/SK282641B6/sk not_active IP Right Cessation
- 1998-08-06 TR TR1998/01513A patent/TR199801513A3/tr unknown
- 1998-08-06 ID IDP981098A patent/ID20667A/id unknown
- 1998-08-07 JP JP10224015A patent/JPH11124372A/ja active Pending
- 1998-08-07 HU HU0700190A patent/HU229232B1/hu unknown
- 1998-08-07 CA CA002245267A patent/CA2245267C/en not_active Expired - Lifetime
- 1998-08-07 AU AU78870/98A patent/AU752764B2/en not_active Expired
- 1998-08-07 BR BR9806568-8A patent/BR9806568A/pt not_active Application Discontinuation
- 1998-08-07 CN CN98116235A patent/CN1089759C/zh not_active Expired - Lifetime
- 1998-08-07 KR KR1019980032110A patent/KR100544041B1/ko not_active IP Right Cessation
- 1998-08-07 HU HU9801844A patent/HU225870B1/hu unknown
- 1998-08-07 RU RU98115390/04A patent/RU2224753C2/ru active
- 1998-08-07 CN CNB021045747A patent/CN1181064C/zh not_active Expired - Lifetime
- 1998-08-07 NO NO19983632A patent/NO310871B1/no not_active IP Right Cessation
- 1998-08-07 PL PL327901A patent/PL192126B1/pl unknown
-
1999
- 1999-06-30 HK HK99102767A patent/HK1017681A1/xx not_active IP Right Cessation
- 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 IP Right Cessation
-
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 | |
| CZ297535B6 (cs) | Způsob krystalizace inhibitoru na bázi benzoxazinonu | |
| TWI687417B (zh) | 噻蟲嗪及其用途 | |
| CZ2002404A3 (cs) | Polymorfní formy torsemidu | |
| AU2009314203B2 (en) | Method for preparing a non-hydratable crystal form | |
| KR19980064286A (ko) | 다형태를 갖는 독사조신 메실레이트의 새로운 형태(제 1형) | |
| US20200399205A1 (en) | 2,2,2-trifluoroacetic acid 1-(2,4-dimethylphenyl)-2-[(3-methoxyphenyl)methylene] hydrazide polymorphs and method of making the same | |
| EP0182572B1 (en) | Novel crystalline form of benzothiazine dioxide salt | |
| JPS5815561A (ja) | ブリリアントカ−ミン６ｂの付加錯化合物の製造法 | |
| 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 | |
| US5596109A (en) | N-t-butyl-androst-3,5-diene-17β-carboxamide-3-carboxylic acid polymorph A | |
| CN116178274A (zh) | 氯比普兰硫酸盐晶型及其制备方法 | |
| AU2001278104A1 (en) | Solid forms of tin ethyl etiopurpurin and processes for producing such forms | |
| WO1996027592A1 (en) | Polymorphic b form of (e)-4-[[3-[2-(4-cyclobutyl-2-thiazolyl)ethenyl]phenyl]amino]-2,2-diethyl-4-oxobutanoic acid | |
| CZ286266B6 (cs) | Kyselina N-terc.butylandrost-3,5-dien-17beta-karboxamid-3-karboxylová v polymorfní formě a způsob její výroby |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK4A | Patent expired |
Expiry date: 20180806 |