HUP0301865A2 - Eljárás leflunomid szintézisére - Google Patents
Eljárás leflunomid szintéziséreInfo
- Publication number
- HUP0301865A2 HUP0301865A2 HU0301865A HUP0301865A HUP0301865A2 HU P0301865 A2 HUP0301865 A2 HU P0301865A2 HU 0301865 A HU0301865 A HU 0301865A HU P0301865 A HUP0301865 A HU P0301865A HU P0301865 A2 HUP0301865 A2 HU P0301865A2
- Authority
- HU
- Hungary
- Prior art keywords
- leflunomide
- trifluoromethylaniline
- methylisoxazole
- carboxamide
- synthesizing
- Prior art date
Links
- 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 title abstract 5
- 229960000681 leflunomide Drugs 0.000 title abstract 5
- 238000000034 method Methods 0.000 title abstract 3
- 230000002194 synthesizing effect Effects 0.000 title 1
- ODGIMMLDVSWADK-UHFFFAOYSA-N 4-trifluoromethylaniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1 ODGIMMLDVSWADK-UHFFFAOYSA-N 0.000 abstract 1
- VQBXUKGMJCPBMF-UHFFFAOYSA-N 5-methyl-1,2-oxazole-4-carboxylic acid Chemical compound CC=1ON=CC=1C(O)=O VQBXUKGMJCPBMF-UHFFFAOYSA-N 0.000 abstract 1
- MIOYDAUCMWWNRH-UHFFFAOYSA-N 5-methyl-n-(4-methylphenyl)-1,2-oxazole-4-carboxamide Chemical compound O1N=CC(C(=O)NC=2C=CC(C)=CC=2)=C1C MIOYDAUCMWWNRH-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000012535 impurity Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- UTNUDOFZCWSZMS-YFHOEESVSA-N teriflunomide Chemical compound C\C(O)=C(/C#N)C(=O)NC1=CC=C(C(F)(F)F)C=C1 UTNUDOFZCWSZMS-YFHOEESVSA-N 0.000 abstract 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
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
-
- 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
- A61P11/02—Nasal agents, e.g. decongestants
-
- 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
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- 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
- 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
- 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
- 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
- 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
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Diabetes (AREA)
- Pulmonology (AREA)
- Epidemiology (AREA)
- Rheumatology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Transplantation (AREA)
- Dermatology (AREA)
- Ophthalmology & Optometry (AREA)
- Endocrinology (AREA)
- Pain & Pain Management (AREA)
- Otolaryngology (AREA)
- Emergency Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (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)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
A találmány tárgya eljárás (I) képletű leflunomid szintézisére 5-metil-izoxazol-4- karbonsavból és 4-trifluor-metil-anilinből. Atalálmány szerinti leflunomid-előállítási eljárás képes kiküszöbölniaz ismert módszerekkel előállított leflunomidban gyakran előfordulószennyeződéseket, mint pl. N-(4-trifluormetil-fenil)-2-ciano-3-hidroxi-krotonamid, 5-metil-N-(4-metil-fenil)-izoxazol-4-karboxamid ésN-(4-trifluor-metil-anilin-fenil)-3-metil-izoxazol-4-karboxamid. Atalálmány vonatkozik az igen tiszta leflunomidot tartalmazógyógyszerkészítményekre is. Ó
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US18263500P | 2000-02-15 | 2000-02-15 | |
PCT/US2001/004095 WO2001060363A1 (en) | 2000-02-15 | 2001-02-08 | A method for synthesizing leflunomide |
Publications (2)
Publication Number | Publication Date |
---|---|
HUP0301865A2 true HUP0301865A2 (hu) | 2003-09-29 |
HUP0301865A3 HUP0301865A3 (en) | 2005-12-28 |
Family
ID=22669359
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HU0301865A HUP0301865A3 (en) | 2000-02-15 | 2001-02-08 | A method for synthesizing leflunomide |
Country Status (18)
Country | Link |
---|---|
US (2) | US6723855B2 (hu) |
EP (1) | EP1257270B1 (hu) |
JP (1) | JP2004500380A (hu) |
KR (1) | KR20020072312A (hu) |
AT (1) | ATE292966T1 (hu) |
AU (1) | AU2001234943A1 (hu) |
CA (1) | CA2400290A1 (hu) |
CZ (1) | CZ20023024A3 (hu) |
DE (1) | DE60110043T2 (hu) |
ES (1) | ES2237553T3 (hu) |
HR (1) | HRP20020671A2 (hu) |
HU (1) | HUP0301865A3 (hu) |
IL (1) | IL151196A0 (hu) |
PL (1) | PL366088A1 (hu) |
SK (1) | SK12992002A3 (hu) |
WO (1) | WO2001060363A1 (hu) |
YU (1) | YU61602A (hu) |
ZA (1) | ZA200206494B (hu) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE59801792D1 (de) * | 1997-08-08 | 2001-11-22 | Aventis Pharma Gmbh | Kristallform von N-(4-Trifluormethylphenyl)-5-methylisoxazol-4-carbonsäureamid |
SK8332002A3 (en) * | 1999-12-16 | 2003-04-01 | Teva Pharma | Novel processes for making- and a new crystalline form of 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 |
WO2003042193A1 (en) * | 2001-11-09 | 2003-05-22 | Geneva Pharmaceuticals, Inc. | Process for preparing 5-methylisoxazole-4-carboxylic-(4'-trifluoromethyl)-anilide |
DK1631291T3 (da) * | 2003-05-27 | 2009-11-02 | Robert P Haegerkvist | Anvendelse af tyrosinkinaseinhibitorer til behandling af diabetes |
EP1694308A1 (en) * | 2003-10-30 | 2006-08-30 | Lupin Ltd. | Stable formulations of ace inhibitors and methods for preparation thereof |
US20060024376A1 (en) * | 2004-07-30 | 2006-02-02 | The University Of Chicago | Methods and compositions for reducing toxicity associated with leflunomide treatment |
DE102005017592A1 (de) * | 2005-04-16 | 2006-10-19 | Lindner, Jürgen, Dr. med. | Darreichungsformen und Kombinationspräparate von Pyrimidinbiosyntheseinhibitoren zur Erzielung zusätzlicher Wirkungen auf das Immunsystem |
WO2007086076A2 (en) * | 2006-01-24 | 2007-08-02 | Unichem Laboratories Limited | An improved process for preparation of leflunomide |
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 |
RU2681079C2 (ru) | 2009-09-18 | 2019-03-04 | Санофи | Таблетируемый препарат (4'-трифторметилфенил)амида (z)-2-циано-3-гидрокси-бут-2-еноевой кислоты с улучшенной устойчивостью |
CN102002009B (zh) * | 2010-10-18 | 2012-11-07 | 齐鲁制药有限公司 | 一种5-甲基异恶唑-4-甲酰氯的制备方法 |
ES2870205T3 (es) * | 2015-06-17 | 2021-10-26 | Biocon Ltd | Nuevo proceso para la preparación de teriflunomida |
JOP20190207A1 (ar) * | 2017-03-14 | 2019-09-10 | Actelion Pharmaceuticals Ltd | تركيبة صيدلانية تشتمل على بونيسيمود |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2854439A1 (de) | 1978-12-16 | 1980-07-03 | Hoechst Ag | Ein isoxazolderivat, verfahren zu seiner herstellung, diese verbindung enthaltende mittel und verwendung |
GB8619432D0 (en) | 1986-08-08 | 1986-09-17 | Lilly Industries Ltd | Pharmaceutical compounds |
AU649421B2 (en) * | 1990-05-18 | 1994-05-26 | Sanofi-Aventis Deutschland Gmbh | Isoxazole-4-carboxamides and hydroxyalkylidene-cyanoacetamides, drugs containing these compounds and use of such drugs |
EP0607775B1 (de) * | 1993-01-08 | 1998-12-09 | Hoechst Aktiengesellschaft | Verwendung von Leflunomid zur Hemmung von Interleukin 1 beta |
US5610173A (en) | 1994-01-07 | 1997-03-11 | Sugen, Inc. | Formulations for lipophilic compounds |
DE59801792D1 (de) * | 1997-08-08 | 2001-11-22 | Aventis Pharma Gmbh | Kristallform von N-(4-Trifluormethylphenyl)-5-methylisoxazol-4-carbonsäureamid |
DE19908527C2 (de) * | 1999-02-26 | 2001-08-30 | Aventis Pharma Gmbh | Verfahren zur Kristallisation von N-(4-Trifluormethylphenyl)-5-methyl-isoxazol-4-carboxamid |
SK8332002A3 (en) * | 1999-12-16 | 2003-04-01 | Teva Pharma | Novel processes for making- and a new crystalline form of leflunomide |
-
2001
- 2001-02-08 HU HU0301865A patent/HUP0301865A3/hu unknown
- 2001-02-08 IL IL15119601A patent/IL151196A0/xx unknown
- 2001-02-08 AU AU2001234943A patent/AU2001234943A1/en not_active Abandoned
- 2001-02-08 KR KR1020027010595A patent/KR20020072312A/ko not_active Application Discontinuation
- 2001-02-08 ES ES01907127T patent/ES2237553T3/es not_active Expired - Lifetime
- 2001-02-08 US US09/779,928 patent/US6723855B2/en not_active Expired - Fee Related
- 2001-02-08 EP EP01907127A patent/EP1257270B1/en not_active Expired - Lifetime
- 2001-02-08 AT AT01907127T patent/ATE292966T1/de not_active IP Right Cessation
- 2001-02-08 PL PL01366088A patent/PL366088A1/xx not_active Application Discontinuation
- 2001-02-08 JP JP2001559460A patent/JP2004500380A/ja active Pending
- 2001-02-08 DE DE60110043T patent/DE60110043T2/de not_active Expired - Fee Related
- 2001-02-08 WO PCT/US2001/004095 patent/WO2001060363A1/en not_active Application Discontinuation
- 2001-02-08 SK SK1299-2002A patent/SK12992002A3/sk unknown
- 2001-02-08 CZ CZ20023024A patent/CZ20023024A3/cs unknown
- 2001-02-08 CA CA002400290A patent/CA2400290A1/en not_active Abandoned
- 2001-02-08 YU YU61602A patent/YU61602A/sh unknown
-
2002
- 2002-08-14 ZA ZA200206494A patent/ZA200206494B/en unknown
- 2002-08-14 HR HRP20020671 patent/HRP20020671A2/hr not_active Application Discontinuation
-
2003
- 2003-12-10 US US10/730,949 patent/US20040127532A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
SK12992002A3 (sk) | 2003-05-02 |
JP2004500380A (ja) | 2004-01-08 |
EP1257270A4 (en) | 2003-05-07 |
HRP20020671A2 (en) | 2004-12-31 |
IL151196A0 (en) | 2003-04-10 |
US20020022646A1 (en) | 2002-02-21 |
CA2400290A1 (en) | 2001-08-23 |
HUP0301865A3 (en) | 2005-12-28 |
EP1257270B1 (en) | 2005-04-13 |
ES2237553T3 (es) | 2005-08-01 |
AU2001234943A1 (en) | 2001-08-27 |
YU61602A (sh) | 2006-01-16 |
US6723855B2 (en) | 2004-04-20 |
ZA200206494B (en) | 2003-08-20 |
CZ20023024A3 (cs) | 2003-05-14 |
ATE292966T1 (de) | 2005-04-15 |
EP1257270A1 (en) | 2002-11-20 |
DE60110043D1 (de) | 2005-05-19 |
PL366088A1 (en) | 2005-01-24 |
US20040127532A1 (en) | 2004-07-01 |
WO2001060363A1 (en) | 2001-08-23 |
KR20020072312A (ko) | 2002-09-14 |
DE60110043T2 (de) | 2006-03-02 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
FA9A | Lapse of provisional patent protection due to relinquishment or protection considered relinquished |