RU94035759A - Способ получения 2-метил-3-трифторметиланилина, производные трифторметилпиваланилида и способ их получения - Google Patents
Способ получения 2-метил-3-трифторметиланилина, производные трифторметилпиваланилида и способ их полученияInfo
- Publication number
- RU94035759A RU94035759A RU94035759/04A RU94035759A RU94035759A RU 94035759 A RU94035759 A RU 94035759A RU 94035759/04 A RU94035759/04 A RU 94035759/04A RU 94035759 A RU94035759 A RU 94035759A RU 94035759 A RU94035759 A RU 94035759A
- Authority
- RU
- Russia
- Prior art keywords
- formula
- compound
- subjected
- methylation
- synthesis
- Prior art date
Links
- 0 CC1=*C=CCC1N Chemical compound CC1=*C=CCC1N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/45—Monoamines
- C07C211/47—Toluidines; Homologues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C233/07—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pain & Pain Management (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Объектом изобретения является способ получения 2-метил-3-трифторметиланилина формулы I, который заключается в том, что соединение формулы II подвергают метилированию и получаемый при этом продукт метилирования формулы III подвергают либо восстановлению с последующим кислотным гидролизом соединения формулы IV, либо кислотному гидролизу с последующим восстановлением соединения формулы V, или соединение формулы VI подвергают метилированию и получаемый при этом продукт метилирования формулы IV подвергают кислотному гидролизу, в случае необходимости после предварительного выделения продукта формулы IV подвергают гидролизу бромистым водородом. Другим объектом изобретения являются производные трифторметилпиваланилида общей формулы VII, являющиеся промежуточными продуктами для получения 2-метил-3-трифторметиланилина. Эти производные получают за счет того, что соединение формулы VIII подвергают метилированию.
Claims (1)
- Объектом изобретения является способ получения 2-метил-3-трифторметиланилина формулы I, который заключается в том, что соединение формулы II подвергают метилированию и получаемый при этом продукт метилирования формулы III подвергают либо восстановлению с последующим кислотным гидролизом соединения формулы IV, либо кислотному гидролизу с последующим восстановлением соединения формулы V, или соединение формулы VI подвергают метилированию и получаемый при этом продукт метилирования формулы IV подвергают кислотному гидролизу, в случае необходимости после предварительного выделения продукта формулы IV подвергают гидролизу бромистым водородом. Другим объектом изобретения являются производные трифторметилпиваланилида общей формулы VII, являющиеся промежуточными продуктами для получения 2-метил-3-трифторметиланилина. Эти производные получают за счет того, что соединение формулы VIII подвергают метилированию.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81218391A | 1991-12-20 | 1991-12-20 | |
| US07/812.183 | 1991-12-20 | ||
| US07/812,183 | 1991-12-20 | ||
| PCT/US1992/010696 WO1993013070A1 (en) | 1991-12-20 | 1992-12-16 | Process for preparing flunixin and intermediates thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU94035759A true RU94035759A (ru) | 1996-05-10 |
| RU2081105C1 RU2081105C1 (ru) | 1997-06-10 |
Family
ID=25208786
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU9294035759A RU2081105C1 (ru) | 1991-12-20 | 1992-12-16 | Способы получения 2-метил-3-трифторметиланилина, производные трифторметилпиваланилида и способ их получения |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US5484931A (ru) |
| EP (1) | EP0619809B1 (ru) |
| JP (2) | JP2535135B2 (ru) |
| KR (1) | KR100206629B1 (ru) |
| AT (1) | ATE129701T1 (ru) |
| AU (1) | AU659530B2 (ru) |
| BG (1) | BG62137B1 (ru) |
| CA (1) | CA2126210C (ru) |
| CZ (2) | CZ289634B6 (ru) |
| DE (1) | DE69205842T2 (ru) |
| DK (1) | DK0619809T3 (ru) |
| ES (1) | ES2079242T3 (ru) |
| GR (1) | GR3018476T3 (ru) |
| HK (1) | HK185796A (ru) |
| HU (2) | HU217545B (ru) |
| NZ (1) | NZ246433A (ru) |
| PL (1) | PL175962B1 (ru) |
| RU (1) | RU2081105C1 (ru) |
| SK (1) | SK280074B6 (ru) |
| WO (1) | WO1993013070A1 (ru) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE129701T1 (de) * | 1991-12-20 | 1995-11-15 | Schering Corp | Verfahren zur herstellung von flunixin und zwischenprodukten dafür. |
| JP2698306B2 (ja) * | 1993-01-18 | 1998-01-19 | セントラル硝子株式会社 | ２−メチル−３−アミノベンゾトリフロライドの製造方法 |
| FR2787445B1 (fr) * | 1998-12-17 | 2001-01-19 | Rhone Poulenc Agrochimie | Procede de preparation de para-trifluoromethylanilines polyhalogenees |
| CN101351459A (zh) | 2005-07-05 | 2009-01-21 | 万有制药株式会社 | 4(3h)-喹唑啉酮衍生物的制造方法 |
| ATE548026T1 (de) * | 2007-12-14 | 2012-03-15 | Intervet Int Bv | Verfahren zur rückgewinnung von flunixin aus pharmazeutischen zusammensetzungen |
| US20110062039A1 (en) * | 2009-09-16 | 2011-03-17 | Prokop Marigale A | Cord Management System for Appliances |
| CN102442944B (zh) * | 2011-12-14 | 2014-01-01 | 齐鲁动物保健品有限公司 | 一种氟尼辛的制备方法 |
| CN103570558A (zh) * | 2013-11-11 | 2014-02-12 | 湖北中牧安达药业有限公司 | 一种2-甲基-3-三氟甲基苯胺的合成方法 |
| CN104193674B (zh) * | 2014-08-27 | 2016-05-25 | 济南久隆医药科技有限公司 | 一种氟尼辛葡甲胺的合成方法 |
| CN107260664A (zh) * | 2017-07-28 | 2017-10-20 | 吉林省力畜达动物药业有限公司 | 一种复方氟尼辛葡甲胺注射液及其制备方法 |
| CN108586327B (zh) * | 2018-04-25 | 2020-07-14 | 济南久隆医药科技有限公司 | 一种氟尼辛的合成方法 |
| CN108911989B (zh) * | 2018-08-15 | 2020-11-03 | 济南悟通生物科技有限公司 | 一种2-甲基-3-三氟甲基苯胺的合成方法 |
| CN109206365B (zh) * | 2018-09-13 | 2019-11-26 | 龙岩台迈三略制药有限公司 | 一种氟尼辛葡甲胺的制备方法 |
| CN112394130B (zh) * | 2020-12-02 | 2021-11-02 | 济南悟通生物科技有限公司 | 2-甲基-3-三氟甲基苯胺合成工艺中杂质的分析方法 |
| CN113372264A (zh) * | 2021-06-16 | 2021-09-10 | 宁夏常晟药业有限公司 | 一种2-[2-甲基-3-(三氟甲基)苯氨基]烟酸的合成方法 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL123536C (ru) * | 1963-07-09 | |||
| US3390172A (en) * | 1964-03-27 | 1968-06-25 | Parke Davis & Co | Nu-(3-trifluoromethylphenyl)-anthranilic acids |
| CH501624A (de) * | 1965-10-23 | 1971-01-15 | Scherico Ltd | Verfahren zur Herstellung substituierter Nikotinsäuren |
| US3337570A (en) * | 1965-10-23 | 1967-08-22 | Schering Corp | Substituted nicotinic acids and method for the manufacture thereof |
| US3839344A (en) * | 1973-03-28 | 1974-10-01 | Schering Corp | N-methyl d-glucamine salt of 2(2'-methyl-3'-trifluoromethylanilino)nicotinic acid |
| US3891761A (en) * | 1973-03-28 | 1975-06-24 | Schering Corp | N-Methyl-d-glucamine salt of 2(2-methyl-3{40 -trifluoro-methylanilino) nicotinic acid in the treatment of pain |
| US4081451A (en) * | 1975-03-20 | 1978-03-28 | Schering Corporation | Process for preparing 2-halogeno nicotinic acids |
| US4172095A (en) * | 1977-06-10 | 1979-10-23 | Schering Corporation | Novel synthesis of 3-amino-2-methylbenzotrifluoride and the intermediates thereof |
| US4132737A (en) * | 1978-02-27 | 1979-01-02 | Eli Lilly And Company | Trifluoromethyl substituted 1-aminoindanes |
| US4302599A (en) * | 1979-09-10 | 1981-11-24 | Schering Corporation | Process for nitrating anilides |
| DE3014122A1 (de) * | 1980-04-12 | 1981-10-15 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von n,n-dimethyl-n' -(2-brom-4-methyl-phenyl)-triazen |
| JPS5813194A (ja) * | 1981-07-15 | 1983-01-25 | Fujitsu Denso Ltd | ファン停止検出回路 |
| EP0225175A3 (en) * | 1985-11-28 | 1988-12-28 | FISONS plc | Dihydropyridine derivatives, processes for their preparation and pharmaceutical compositions thereof |
| DE3726891A1 (de) * | 1986-08-13 | 1988-02-18 | Central Glass Co Ltd | Neue dichlortrifluormethylnitrotoluole und deren umwandlung in aminotrifluormethyltoluole |
| US4831193A (en) * | 1987-06-19 | 1989-05-16 | Schering Corporation | Synthesis of 3-amino-2-methylbenzotrifluoride |
| ATE129701T1 (de) * | 1991-12-20 | 1995-11-15 | Schering Corp | Verfahren zur herstellung von flunixin und zwischenprodukten dafür. |
| US5248781A (en) * | 1992-09-21 | 1993-09-28 | The Trustees Of Princeton University | Preparation of substituted anilino-nicotinic acid derivatives |
-
1992
- 1992-12-16 AT AT93901398T patent/ATE129701T1/de active
- 1992-12-16 EP EP93901398A patent/EP0619809B1/en not_active Expired - Lifetime
- 1992-12-16 SK SK687-94A patent/SK280074B6/sk not_active IP Right Cessation
- 1992-12-16 DE DE69205842T patent/DE69205842T2/de not_active Expired - Lifetime
- 1992-12-16 DK DK93901398.3T patent/DK0619809T3/da active
- 1992-12-16 NZ NZ246433A patent/NZ246433A/en unknown
- 1992-12-16 CZ CZ19941383A patent/CZ289634B6/cs not_active IP Right Cessation
- 1992-12-16 ES ES93901398T patent/ES2079242T3/es not_active Expired - Lifetime
- 1992-12-16 KR KR1019940702116A patent/KR100206629B1/ko not_active IP Right Cessation
- 1992-12-16 HU HU9700853A patent/HU217545B/hu unknown
- 1992-12-16 RU RU9294035759A patent/RU2081105C1/ru active
- 1992-12-16 WO PCT/US1992/010696 patent/WO1993013070A1/en active IP Right Grant
- 1992-12-16 CA CA002126210A patent/CA2126210C/en not_active Expired - Lifetime
- 1992-12-16 PL PL92304146A patent/PL175962B1/pl unknown
- 1992-12-16 HU HU9401839A patent/HU213473B/hu unknown
- 1992-12-16 JP JP5511700A patent/JP2535135B2/ja not_active Expired - Lifetime
- 1992-12-16 AU AU32757/93A patent/AU659530B2/en not_active Expired
-
1994
- 1994-05-31 BG BG98817A patent/BG62137B1/bg unknown
- 1994-06-15 US US08/244,883 patent/US5484931A/en not_active Expired - Lifetime
-
1995
- 1995-05-23 US US08/448,152 patent/US5965735A/en not_active Expired - Lifetime
- 1995-10-11 JP JP7263173A patent/JP2679963B2/ja not_active Expired - Lifetime
- 1995-12-20 GR GR950403614T patent/GR3018476T3/el unknown
-
1996
- 1996-10-03 HK HK185796A patent/HK185796A/xx not_active IP Right Cessation
-
2000
- 2000-08-16 CZ CZ20003003A patent/CZ289831B6/cs not_active IP Right Cessation
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