HU178015B - Process for preparing new 5-methyl-isoxazola-4-carboxylic acid-/4-trifluoromethyl/-anilide - Google Patents
Process for preparing new 5-methyl-isoxazola-4-carboxylic acid-/4-trifluoromethyl/-anilide Download PDFInfo
- Publication number
- HU178015B HU178015B HU79HO2201A HUHO002201A HU178015B HU 178015 B HU178015 B HU 178015B HU 79HO2201 A HU79HO2201 A HU 79HO2201A HU HO002201 A HUHO002201 A HU HO002201A HU 178015 B HU178015 B HU 178015B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- trifluoromethyl
- anilide
- compound
- carboxylic acid
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims description 39
- VQBXUKGMJCPBMF-UHFFFAOYSA-N 5-methyl-1,2-oxazole-4-carboxylic acid Chemical compound CC=1ON=CC=1C(O)=O VQBXUKGMJCPBMF-UHFFFAOYSA-N 0.000 claims description 21
- 150000003931 anilides Chemical class 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 15
- ODGIMMLDVSWADK-UHFFFAOYSA-N 4-trifluoromethylaniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1 ODGIMMLDVSWADK-UHFFFAOYSA-N 0.000 claims description 14
- -1 methoxy, ethoxy Chemical group 0.000 claims description 12
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- 239000003826 tablet Substances 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000004580 weight loss Effects 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
- 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
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Immunology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Lubricants (AREA)
- Chemical And Physical Treatments For Wood And The Like (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782854439 DE2854439A1 (de) | 1978-12-16 | 1978-12-16 | Ein isoxazolderivat, verfahren zu seiner herstellung, diese verbindung enthaltende mittel und verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU178015B true HU178015B (en) | 1982-02-28 |
Family
ID=6057414
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU79HO2201A HU178015B (en) | 1978-12-16 | 1979-12-14 | Process for preparing new 5-methyl-isoxazola-4-carboxylic acid-/4-trifluoromethyl/-anilide |
Country Status (25)
| Country | Link |
|---|---|
| US (2) | US4284786A (en, 2012) |
| EP (1) | EP0013376B1 (en, 2012) |
| JP (1) | JPS5583767A (en, 2012) |
| AR (2) | AR222680A1 (en, 2012) |
| AT (1) | ATE1067T1 (en, 2012) |
| AU (1) | AU529341B2 (en, 2012) |
| BG (1) | BG60764B2 (en, 2012) |
| CA (1) | CA1129867A (en, 2012) |
| DE (2) | DE2854439A1 (en, 2012) |
| DK (1) | DK149886C (en, 2012) |
| EG (1) | EG13926A (en, 2012) |
| ES (2) | ES486750A1 (en, 2012) |
| FI (1) | FI64154C (en, 2012) |
| GR (1) | GR72731B (en, 2012) |
| HU (1) | HU178015B (en, 2012) |
| IE (1) | IE49126B1 (en, 2012) |
| IL (1) | IL58951A (en, 2012) |
| LU (1) | LU90466I2 (en, 2012) |
| MX (2) | MX6174E (en, 2012) |
| NL (1) | NL990037I2 (en, 2012) |
| NO (1) | NO148925C (en, 2012) |
| NZ (1) | NZ192400A (en, 2012) |
| PH (1) | PH16627A (en, 2012) |
| PT (1) | PT70596A (en, 2012) |
| ZA (1) | ZA796793B (en, 2012) |
Families Citing this family (61)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3247454A1 (de) * | 1982-12-22 | 1984-06-28 | Laboratorios Bago S.A., Buenos Aires | Substituierte 3-phenyl-5-methyl-isoxazol-4-carboxy-anilide, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| FR2538806B1 (fr) * | 1982-12-30 | 1986-02-21 | Bago Sa Labor | Composes phenyl-3 methyl isoxazole-5 carboxy-4 anilides substitues, actifs therapeutiquement contre l'inflammation et la douleur |
| DE3534440A1 (de) * | 1985-09-27 | 1987-04-02 | Hoechst Ag | Arzneimittel gegen chronische graft-versus-host-krankheiten sowie gegen autoimmunerkrankungen, insbesondere systemischen lupus erythematodes |
| US5268382A (en) * | 1985-09-27 | 1993-12-07 | Hoechst Aktiengesellschaft | Medicaments to combat autoimmune diseases, in particular systemic lupus erythematosus |
| US4935434A (en) * | 1988-01-26 | 1990-06-19 | Bristol-Myers Company | Antiarthritic isoxazole-4-carboxamides |
| FR2662692B1 (fr) * | 1990-05-30 | 1995-04-28 | Novapharme | Derives heterocycliques doues d'activite anticonvulsivante, procede de preparation et composition pharmaceutique. |
| US5258397A (en) * | 1988-11-30 | 1993-11-02 | Novapharme | 3-Isoxazoyl derivatives endowed with anticonvulsant activity, procedure for their preparation and their pharmaceutical compositions |
| DD297328A5 (de) * | 1989-08-18 | 1992-01-09 | �������@���������k���Kk�� | 5-methyl-isoxalol-4-carbonsaeureanilide und 2 hydroxyethyliden-cyanoessigsaeureanilide zur behandlung von augenerkrankungen |
| 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 |
| US5108999A (en) * | 1990-02-02 | 1992-04-28 | Syntex (U.S.A.) Inc. | 4-isoxazolecarboxamide derivatives |
| US5001124A (en) * | 1990-02-02 | 1991-03-19 | Syntex (U.S.A.) Inc. | 4-isoxazolecarboxamide derivatives |
| EP0527736B1 (de) * | 1990-05-18 | 1997-04-16 | Hoechst Aktiengesellschaft | Isoxazol-4-carbonsäureamide und hydroxyalkyliden-cyanessigsäureamide, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US6133301A (en) * | 1991-08-22 | 2000-10-17 | Aventis Pharma Deutschland Gmbh | Pharmaceuticals for the treatment of rejection reactions in organ transplantations |
| DE4127737A1 (de) | 1991-08-22 | 1993-02-25 | Hoechst Ag | Arzneimittel zur behandlung von abstossungsreaktionen bei organverpflanzungen |
| DE59407412D1 (de) * | 1993-01-08 | 1999-01-21 | Hoechst Ag | Verwendung von Leflunomid zur Hemmung von Interleukin 1 alpha |
| ES2124800T3 (es) * | 1993-01-08 | 1999-02-16 | Hoechst Ag | Empleo de leflunomida para la inhibicion de interleuquina 1 beta. |
| EP0607777B1 (de) * | 1993-01-08 | 1998-12-09 | Hoechst Aktiengesellschaft | Verwendung von Leflunomid zur Hemmung von Interleukin 8 |
| EP0607776B1 (de) * | 1993-01-08 | 1998-12-09 | Hoechst Aktiengesellschaft | Verwendung von Leflunomid zur Hemmung von Tumornekrosefaktor alpha |
| TW314467B (en, 2012) * | 1993-03-31 | 1997-09-01 | Hoechst Ag | |
| DE4323636A1 (de) * | 1993-07-15 | 1995-01-19 | Hoechst Ag | Arzneistoffzubereitungen aus umhüllten, schwerstwasserlöslichen Arzneistoffen für Inhalationsarzneiformen und Verfahren zu ihrer Herstellung |
| LT3589B (en) | 1993-11-30 | 1995-12-27 | Hoechst Ag | Using of known combination for treatment of rejection reaction by transplantation of organs |
| US6335356B1 (en) | 1994-01-07 | 2002-01-01 | Sugen, Inc. | Method of treating a patient by parenteral administration of a lipophilic compound |
| US5700823A (en) * | 1994-01-07 | 1997-12-23 | Sugen, Inc. | Treatment of platelet derived growth factor related disorders such as cancers |
| US5610173A (en) * | 1994-01-07 | 1997-03-11 | Sugen, Inc. | Formulations for lipophilic compounds |
| US5519042A (en) * | 1994-01-13 | 1996-05-21 | Hoechst Aktiengesellschaft | Method of treating hyperproliferative vascular disease |
| US5624946A (en) * | 1994-07-05 | 1997-04-29 | Williams; James | Use of leflunomide to control and reverse chronic allograft rejection |
| DK0787491T3 (da) * | 1994-10-17 | 2000-10-16 | Aventis Pharma Ltd | Middel til forebyggelse og behandling af allergiske sygdomme af type I |
| US5721277A (en) * | 1995-04-21 | 1998-02-24 | Sugen, Inc. | Compounds and methods for inhibiting hyper-proliferative cell growth |
| US6331555B1 (en) | 1995-06-01 | 2001-12-18 | University Of California | Treatment of platelet derived growth factor related disorders such as cancers |
| DE19539638A1 (de) * | 1995-10-25 | 1997-04-30 | Hoechst Ag | Die Verwendung von Isoxazol- und Crotonsäureamidderivaten zur Behandlung von Krebserkrankungen |
| DE19702988A1 (de) * | 1997-01-28 | 1998-07-30 | Hoechst Ag | Isoxazol- und Crotonsäureamidderivate und deren Verwendung als Arzneimittel und Diagnostika |
| US6316479B1 (en) | 1997-05-19 | 2001-11-13 | Sugen, Inc. | Isoxazole-4-carboxamide compounds active against protein tryosine kinase related disorders |
| DE59800287D1 (de) * | 1997-08-08 | 2000-11-09 | Aventis Pharma Gmbh | Kristallform von 5-Methylisoxazol-4-carbonsäure-(4-trifluormethyl)-anilid |
| US7691890B2 (en) | 1998-03-11 | 2010-04-06 | James W. Williams | Anti-viral uses of leflunomide products |
| US20050255071A1 (en) * | 1998-12-10 | 2005-11-17 | Aventis Pharma Deutschland Gmbh | Preparation having improved therapeutic breadth comprising nucleotide synthesis inhibitors |
| DE19908527C2 (de) | 1999-02-26 | 2001-08-30 | Aventis Pharma Gmbh | Verfahren zur Kristallisation von N-(4-Trifluormethylphenyl)-5-methyl-isoxazol-4-carboxamid |
| US6566395B1 (en) | 1999-05-25 | 2003-05-20 | Biomedicines, Inc. | Methods of treating proliferative disorders |
| DE19960443C2 (de) * | 1999-12-15 | 2002-05-08 | Aventis Pharma Gmbh | Verfahren zur Auffindung von Nukleotidsyntheseinhibitoren mit weniger Nebenwirkungen |
| YU45102A (sh) * | 1999-12-16 | 2006-01-16 | Teva Pharmaceutical Industries Ltd. | Novi kristalni oblik leflunomida i novi postupci za njegovo dobijanje |
| YU61602A (sh) * | 2000-02-15 | 2006-01-16 | Teva Pharmaceutical Industries Ltd. | Postupak za dobijanje leflunomida |
| EP1473035A1 (en) * | 2000-02-15 | 2004-11-03 | Teva Pharmaceutical Industries Ltd. | Leflunomide of high purity |
| US20020077485A1 (en) * | 2000-08-14 | 2002-06-20 | Ilya Avrutov | Micronized leflunomide |
| 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 |
| ES2305287T3 (es) | 2001-04-05 | 2008-11-01 | Aventis Pharmaceuticals Inc. | Uso de (4'-trifluorometifenil)-amida del acido (z)-ciano-3-hidroxi-but-2-enoico para tratar la esclerosis multiple. |
| US20030139606A1 (en) * | 2001-11-09 | 2003-07-24 | Ray Anup Kumar | Process for preparing 5-methylisoxazole-4-carboxylic- (4'-trifluoromethyl)-anilide |
| US20050158371A1 (en) * | 2002-02-12 | 2005-07-21 | Sumitomo Pharmaceuticals Co., Ltd. | Novel external agent |
| EP2583678A3 (en) | 2004-06-24 | 2013-11-13 | Novartis Vaccines and Diagnostics, Inc. | Small molecule immunopotentiators and assays for their detection |
| US20060024376A1 (en) * | 2004-07-30 | 2006-02-02 | The University Of Chicago | Methods and compositions for reducing toxicity associated with leflunomide treatment |
| CN101242831A (zh) * | 2005-08-31 | 2008-08-13 | 兴和株式会社 | 类风湿性关节炎的预防和/或治疗方法 |
| WO2008093246A2 (en) | 2007-02-02 | 2008-08-07 | Vegenics Limited | Vegf receptor antagonist for treating organ transplant alloimmunity and arteriosclerosis |
| CN101817797B (zh) * | 2009-02-26 | 2013-04-10 | 江苏亚邦爱普森药业有限公司 | 高纯度3-甲基-n-[4-(三氟甲基)苯基]-4-异噁唑甲酰胺的合成方法 |
| US9138309B2 (en) | 2010-02-05 | 2015-09-22 | Allergan, Inc. | Porous materials, methods of making and uses |
| US9205577B2 (en) * | 2010-02-05 | 2015-12-08 | Allergan, Inc. | Porogen compositions, methods of making and uses |
| US11202853B2 (en) * | 2010-05-11 | 2021-12-21 | Allergan, Inc. | Porogen compositions, methods of making and uses |
| JOP20190207A1 (ar) | 2017-03-14 | 2019-09-10 | Actelion Pharmaceuticals Ltd | تركيبة صيدلانية تشتمل على بونيسيمود |
| EP3773579A4 (en) | 2018-03-26 | 2022-03-09 | Clear Creek Bio, Inc. | Compositions and methods for inhibiting dihydroorotate dehydrogenase |
| TW202146015A (zh) | 2020-03-06 | 2021-12-16 | 瑞士商艾克泰聯製藥有限公司 | 減緩腦體積損失之方法 |
| US20210290651A1 (en) | 2020-03-20 | 2021-09-23 | Clear Creek Bio, Inc. | Methods of treating viral infections using inhibitors of nucleotide synthesis pathways |
| US11951097B2 (en) | 2021-10-11 | 2024-04-09 | Vanda Pharmaceuticals Inc. | Methods of treating multiple sclerosis |
| US12357616B2 (en) | 2021-10-11 | 2025-07-15 | Vanda Pharmaceuticals Inc. | Methods of treating multiple sclerosis |
| WO2023152290A1 (en) | 2022-02-11 | 2023-08-17 | Actelion Pharmaceuticals Ltd | Methods of slowing an increase in brain ventricular volume |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4087534A (en) * | 1974-05-22 | 1978-05-02 | David Ovadia | N-haloalkylmio urazole pesticides |
| ES448386A1 (es) * | 1975-06-05 | 1978-04-16 | Hoechst Ag | Procedimiento para la preparacion de anilidas de acido 5-me-til-isoxazol-4-carboxilico. |
| 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 |
| DE2654797A1 (de) * | 1976-12-03 | 1978-06-08 | Hoechst Ag | Verfahren zur herstellung von isoxazolderivaten |
-
1978
- 1978-12-16 DE DE19782854439 patent/DE2854439A1/de not_active Withdrawn
-
1979
- 1979-12-11 ES ES486750A patent/ES486750A1/es not_active Expired
- 1979-12-11 ES ES486758A patent/ES486758A1/es not_active Expired
- 1979-12-12 EG EG748/79A patent/EG13926A/xx active
- 1979-12-13 US US06/103,551 patent/US4284786A/en not_active Expired - Lifetime
- 1979-12-13 FI FI793899A patent/FI64154C/fi not_active IP Right Cessation
- 1979-12-13 AT AT79105142T patent/ATE1067T1/de active
- 1979-12-13 EP EP79105142A patent/EP0013376B1/de not_active Expired
- 1979-12-13 DE DE7979105142T patent/DE2962929D1/de not_active Expired
- 1979-12-13 MX MX798546U patent/MX6174E/es unknown
- 1979-12-14 DK DK534279A patent/DK149886C/da active
- 1979-12-14 GR GR60761A patent/GR72731B/el unknown
- 1979-12-14 CA CA342,109A patent/CA1129867A/en not_active Expired
- 1979-12-14 PH PH23418A patent/PH16627A/en unknown
- 1979-12-14 IL IL58951A patent/IL58951A/xx unknown
- 1979-12-14 HU HU79HO2201A patent/HU178015B/hu unknown
- 1979-12-14 IE IE2426/79A patent/IE49126B1/en active Protection Beyond IP Right Term
- 1979-12-14 AU AU53853/79A patent/AU529341B2/en not_active Expired
- 1979-12-14 JP JP16170079A patent/JPS5583767A/ja active Granted
- 1979-12-14 ZA ZA00796793A patent/ZA796793B/xx unknown
- 1979-12-14 AR AR279310A patent/AR222680A1/es active
- 1979-12-14 NO NO794094A patent/NO148925C/no unknown
- 1979-12-14 PT PT70596A patent/PT70596A/pt active IP Right Revival
- 1979-12-14 NZ NZ192400A patent/NZ192400A/xx unknown
-
1981
- 1981-03-03 US US06/239,986 patent/US4351841A/en not_active Expired - Lifetime
- 1981-05-19 AR AR285378A patent/AR226894A1/es active
-
1984
- 1984-03-12 MX MX8403A patent/MX8403A/es unknown
-
1994
- 1994-02-23 BG BG098534A patent/BG60764B2/bg unknown
-
1999
- 1999-10-27 LU LU90466C patent/LU90466I2/fr unknown
- 1999-10-29 NL NL990037C patent/NL990037I2/nl unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 |