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 получения

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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
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RU
Russia
Prior art keywords
formula
compound
subjected
methylation
synthesis
Prior art date
Application number
RU94035759/04A
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English (en)
Other versions
RU2081105C1 (ru
Inventor
Дж. Доран Хенри
Ie]
Дж. Кавени Дональд
Original Assignee
Шеринг Корпорейшн (US)
Шеринг Корпорейшн
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Application filed by Шеринг Корпорейшн (US), Шеринг Корпорейшн filed Critical Шеринг Корпорейшн (US)
Publication of RU94035759A publication Critical patent/RU94035759A/ru
Application granted granted Critical
Publication of RU2081105C1 publication Critical patent/RU2081105C1/ru

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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)
  • Medicinal Chemistry (AREA)
  • Pain & Pain Management (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Biomedical Technology (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)

  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.
RU9294035759A 1991-12-20 1992-12-16 Способы получения 2-метил-3-трифторметиланилина, производные трифторметилпиваланилида и способ их получения RU2081105C1 (ru)

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)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE69205842T2 (de) * 1991-12-20 1996-04-04 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
JP4240146B2 (ja) 2005-07-05 2009-03-18 萬有製薬株式会社 ４（３ｈ）−キナゾリノン誘導体の製造方法
WO2009079345A1 (en) * 2007-12-14 2009-06-25 Schering-Plough Ltd. Process for recovering flunixin from pharmaceutical compositions
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

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NL123536C (ru) * 1963-07-09
US3390172A (en) * 1964-03-27 1968-06-25 Parke Davis & Co Nu-(3-trifluoromethylphenyl)-anthranilic acids
US3337570A (en) * 1965-10-23 1967-08-22 Schering Corp Substituted nicotinic acids and method for the manufacture thereof
CH501624A (de) * 1965-10-23 1971-01-15 Scherico Ltd Verfahren zur Herstellung substituierter Nikotinsäuren
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
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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
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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
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DE69205842T2 (de) * 1991-12-20 1996-04-04 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

Also Published As

Publication number Publication date
US5484931A (en) 1996-01-16
CA2126210C (en) 1997-12-09
JPH08104675A (ja) 1996-04-23
BG62137B1 (bg) 1999-03-31
DE69205842T2 (de) 1996-04-04
JPH06511256A (ja) 1994-12-15
ATE129701T1 (de) 1995-11-15
HU9401839D0 (en) 1994-09-28
US5965735A (en) 1999-10-12
EP0619809A1 (en) 1994-10-19
AU3275793A (en) 1993-07-28
HUT67575A (en) 1995-04-28
HK185796A (en) 1996-10-11
AU659530B2 (en) 1995-05-18
EP0619809B1 (en) 1995-11-02
JP2679963B2 (ja) 1997-11-19
HU9700853D0 (en) 1997-06-30
PL175962B1 (pl) 1999-03-31
DK0619809T3 (da) 1995-12-04
RU2081105C1 (ru) 1997-06-10
KR100206629B1 (ko) 1999-07-01
HU213473B (en) 1997-06-30
ES2079242T3 (es) 1996-01-01
DE69205842D1 (de) 1995-12-07
BG98817A (bg) 1995-03-31
GR3018476T3 (en) 1996-03-31
CZ289831B6 (cs) 2002-04-17
CZ138394A3 (en) 1995-03-15
CA2126210A1 (en) 1993-06-24
WO1993013070A1 (en) 1993-07-08
CZ289634B6 (cs) 2002-03-13
SK68794A3 (en) 1995-02-08
SK280074B6 (sk) 1999-07-12
NZ246433A (en) 1995-10-26
JP2535135B2 (ja) 1996-09-18
HU217545B (hu) 2000-02-28

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