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KR940014301A - Phenyl Acetate Derivatives, Methods for Making the Same and Uses thereof - Google Patents

Phenyl Acetate Derivatives, Methods for Making the Same and Uses thereof Download PDF

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KR940014301A
KR940014301A KR1019930027558A KR930027558A KR940014301A KR 940014301 A KR940014301 A KR 940014301A KR 1019930027558 A KR1019930027558 A KR 1019930027558A KR 930027558 A KR930027558 A KR 930027558A KR 940014301 A KR940014301 A KR 940014301A
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acid
methyl
ethyl
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derivative
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KR100196240B1 (en
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호세 아르투스 수로카 후안
라페카스 하네 로렌소
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산티아고 오예르 다우레야
프로데스파르마, 에스. 에이.
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/02—Formation of carboxyl groups in compounds containing amino groups, e.g. by oxidation of amino alcohols
    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/40—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to carbon atoms of at least one six-membered aromatic ring and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/42—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to carbon atoms of at least one six-membered aromatic ring and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton with carboxyl groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by saturated carbon chains

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
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Abstract

본 발명은 페닐아세트산 유도체, 이의 제조방법 및 상응하는 용도에 관한 것이다. 이들 유도체는 일반식(Ⅲ)으로 나타낼 수 있다.The present invention relates to phenylacetic acid derivatives, methods for their preparation and corresponding uses. These derivatives can be represented by general formula (III).

상기식에서, R1, R2및 R3은 동일하거나 상이하며, 메틸, 에틸 또는 프로필 라디칼이거나, 또는 R2와 R3은 -(R2- R3)-으로 나타낸 바와 같이 함께 결합하여 -(CH2)n- 라디칼(여기서, n은 4 또는 5이다)을 형성한다.Wherein R 1 , R 2 and R 3 are the same or different and are methyl, ethyl or propyl radicals, or R 2 and R 3 are bonded together as represented by-(R 2 -R 3 )--( CH 2 ) n -to form a radical where n is 4 or 5.

본 발명의 방법은 디클로펜악 염과 일반식 X-CH2-COO-CR1R2R3의 상응하는 알킬 할로아세테이트(여기서, X는 Cl 또는 Br이다)를 균질한 매질속에서 반응시킴을 포함한다. 본 발명의 유도체를 무수 매질속에서 산으로 처리함으로써 [2-(2,6-디클로로아닐리노)페닐]아세톡시아세트산을 제조하는데 사용한다. 당해 유도체는 진통제 또는 소염체로서의 치료 활성을 갖는다.The process of the invention reacts a diclofenac salt with the corresponding alkyl haloacetate of the general formula X-CH 2 -COO-CR 1 R 2 R 3 , wherein X is Cl or Br in a homogeneous medium. Include. The derivatives of the invention are used to prepare [2- (2,6-dichloroanilino) phenyl] acetoxyacetic acid by treating with an acid in anhydrous medium. The derivative has therapeutic activity as an analgesic or anti-inflammatory agent.

Description

페닐아세트산 유도체, 이의 제조방법 및 이의 용도Phenyl Acetate Derivatives, Methods for Making the Same and Uses thereof

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음As this is a public information case, the full text was not included.

Claims (14)

일반식(Ⅲ)의 페닐아세트산 유도체 및 약제학적으로 허용되는 이의 용매화물.Phenylacetic acid derivatives of general formula (III) and pharmaceutically acceptable solvates thereof. 상기식에서, R1, R2및 R3은 동일하거나 상이하며, 메틸, 에틸 또는 프로필 라디칼이거나, 또는 R2와 R3은 -(R2- R3)-으로 나타낸 바와 같이 함께 결합하여 -(CH2)n- 라디칼(여기서, n은 4 또는 5이다)을 형성하고, 단 R1, R2및 R3이 모두 CH3인 경우는 제외한다.Wherein R 1 , R 2 and R 3 are the same or different and are methyl, ethyl or propyl radicals, or R 2 and R 3 are bonded together as represented by-(R 2 -R 3 )--( CH 2 ) to form n − radicals where n is 4 or 5, except where R 1 , R 2 and R 3 are all CH 3 . 제 1 항에 있어서, R1이 메틸이고 R2및 R3이 모두 에틸인 유도체.The derivative of claim 1 wherein R 1 is methyl and R 2 and R 3 are both ethyl. 제 1 항에 있어서, R1이 메틸이고 R2및 R3이 결합하여 -(CH2)5- 라디칼을 나타내는 유도체.The derivative of claim 1, wherein R 1 is methyl and R 2 and R 3 are bonded to represent a-(CH 2 ) 5 -radical. 약제학적 조성물을 제조하기 위한, 일반식(Ⅲ)의 페닐아세트산 유도체의 용도.Use of a phenylacetic acid derivative of general formula (III) to prepare a pharmaceutical composition. 상기식에서, R1, R2및 R3은 동일하거나 상이하며, 메틸, 에틸 또는 프로필 라디칼이거나, 또는 R2와 R3은 -(R2- R3)-으로 나타낸 바와 같이 함께 결합하여 -(CH2)n- 라디칼(여기서, n은 4 또는 5이다)을 형성하고, 단 R1, R2및 R3이 모두 CH3인 경우는 제외한다.Wherein R 1 , R 2 and R 3 are the same or different and are methyl, ethyl or propyl radicals, or R 2 and R 3 are bonded together as represented by-(R 2 -R 3 )--( CH 2 ) to form n − radicals where n is 4 or 5, except where R 1 , R 2 and R 3 are all CH 3 . 제 4 항에 있어서, 약제학적 조성물이 진통제 또는 소염제인 용도.Use according to claim 4, wherein the pharmaceutical composition is an analgesic or anti-inflammatory agent. 치료적 유효량의 제 1 항 내지 제 3 항 중의 어느 한 항에 따른 일반식(Ⅲ)의 페닐아세트산 유도체(a)와 약제학적으로 허용되는 부형제(b) 적당량을 포함하는 약제학적 조성물.A pharmaceutical composition comprising a therapeutically effective amount of a phenylacetic acid derivative of formula (III) according to any one of claims 1 to 3 and an appropriate amount of a pharmaceutically acceptable excipient (b). 상기식에서, R1, R2및 R3은 동일하거나 상이하며, 메틸, 에틸 또는 프로필 라디칼이거나, 또는 R2와 R3은 -(R2- R3)-으로 나타낸 바와 같이 함께 결합하여 -(CH2)n- 라디칼(여기서, n은 4 또는 5이다)을 형성하고, 단 R1, R2및 R3이 모두 CH3인 경우는 제외한다.Wherein R 1 , R 2 and R 3 are the same or different and are methyl, ethyl or propyl radicals, or R 2 and R 3 are bonded together as represented by-(R 2 -R 3 )--( CH 2 ) to form n − radicals where n is 4 or 5, except where R 1 , R 2 and R 3 are all CH 3 . 출발 화합물이 용해될 수 있는 비양성자성 용매의 존재하에 균질한 매질중에서 반응시킴을 특징으로하여, [2-(2,6-디클로로아닐리노)페닐]아세트산의 나트륨염 또는 칼륨염을 일반식 X-CH2-COO-CR1R2R3의 상응하는 알킬 할로아세테이트(여기서, X는 염소 또는 브롬이다)와 반응시켜 일반식(Ⅲ)의 페닐아세트산 유도체 및 약제학적으로 허용되는 이의 용매화물을 제조하는 방법.The sodium or potassium salt of [2- (2,6-dichloroanilino) phenyl] acetic acid is characterized in that the starting compound is reacted in a homogeneous medium in the presence of an aprotic solvent in which it can be dissolved. Reacting with the corresponding alkyl haloacetate of -CH 2 -COO-CR 1 R 2 R 3 , wherein X is chlorine or bromine, to form a phenylacetic acid derivative of formula (III) and a pharmaceutically acceptable solvate thereof How to manufacture. 상기식에서, R1, R2및 R3은 동일하거나 상이하며, 메틸, 에틸 또는 프로필 라디칼이거나, 또는 R2와 R3은 -(R2- R3)-으로 나타낸 바와 같이 함께 결합하여 -(CH2)n- 라디칼(여기서, n은 4 또는 5이다)을 형성한다.Wherein R 1 , R 2 and R 3 are the same or different and are methyl, ethyl or propyl radicals, or R 2 and R 3 are bonded together as represented by-(R 2 -R 3 )--( CH 2 ) n -to form a radical where n is 4 or 5. 제 7 항에 있어서, 약간 과량의 알킬 할로아세테이트를 사용하여 반응시키는 방법.8. The process of claim 7, wherein the reaction is carried out using a slight excess of alkyl haloacetate. 제 7 항 또는 제 8 항에 있어서, 비양성자성 용매가 극성이 높은 용매인 방법.The method of claim 7 or 8, wherein the aprotic solvent is a highly polar solvent. 일반식(Ⅲ)의 유도체를 용매 속에서 산 또는 산의 혼합물로 처리함을 특징으로 하여, [2-(2,6-디클로로아닐리노)페닐]아세톡시아세트산을 제조하는 방법에 일반식(Ⅲ)의 페닐아세트산 유도체를 사용하는 방법.A derivative of the general formula (III) is treated with an acid or a mixture of acids in a solvent, whereby [2- (2,6-dichloroanilino) phenyl] acetoxyacetic acid is prepared. Phenylacetic acid derivatives). 상기식에서, R1, R2및 R3은 동일하거나 상이하며, 메틸, 에틸 또는 프로필 라디칼이거나, 또는 R2와 R3은 -(R2- R3)-으로 나타낸 바와 같이 함께 결합하여 -(CH2)n- 라디칼(여기서, n은 4 또는 5이다)을 형성한다.Wherein R 1 , R 2 and R 3 are the same or different and are methyl, ethyl or propyl radicals, or R 2 and R 3 are bonded together as represented by-(R 2 -R 3 )--( CH 2 ) n -to form a radical where n is 4 or 5. 제10항에 있어서, 무수 매질속에서 처리하는 방법.The method of claim 10 wherein the treatment is carried out in anhydrous medium. 제10항에 있어서, 산이 트리플루오로아세트산, 포름산, 아세트산, 황산, 염산, 메탄설폰산, p-톨루엔설폰산 또는 퍼플루오르화 수지에 결합된 설폰산인 방법.The method of claim 10 wherein the acid is trifluoroacetic acid, formic acid, acetic acid, sulfuric acid, hydrochloric acid, methanesulfonic acid, p-toluenesulfonic acid or sulfonic acid bound to a perfluorinated resin. 제10항에 있어서, 용매가 산 또는 산의 혼합물이거나, 탄화수소, 할로겐화 탄화수소, 케톤 또는 에테르형 용매인 방법.The process of claim 10 wherein the solvent is an acid or a mixture of acids, or a hydrocarbon, halogenated hydrocarbon, ketone or ether type solvent. 제10항 내지 제13항 중의 어느 한 항에 있어서, R1, R2및 R3이 모두 CH3인 방법.The method of any one of claims 10-13, wherein R 1 , R 2 and R 3 are all CH 3 . ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019930027558A 1992-12-14 1993-12-14 Method for preparing [2- (2,6- (dichloroanilino) phenyl] acetoxyacetic acid using phenylacetic acid derivative Expired - Fee Related KR100196240B1 (en)

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ES9202523 1992-12-14
ES09202523A ES2065242B1 (en) 1992-12-14 1992-12-14 DERIVATIVES OF PHENYLACETIC ACID, PROCEDURE FOR ITS OBTAINING AND CORRESPONDING USE.

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KR940014301A true KR940014301A (en) 1994-07-18
KR100196240B1 KR100196240B1 (en) 1999-06-15

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KR (1) KR100196240B1 (en)
AU (1) AU670139B2 (en)
CA (1) CA2111169C (en)
ES (1) ES2065242B1 (en)
GR (1) GR1002048B (en)
HU (1) HUT65711A (en)
NZ (1) NZ250409A (en)
PL (2) PL175116B1 (en)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE69913133T2 (en) * 1998-04-28 2004-08-26 Russinsky Ltd. METHOD FOR PRODUCING ACECLOFENAC
WO1999062865A1 (en) * 1998-06-03 1999-12-09 Jae Chul Kim Haloethyl-2-[ (2,6-dichlorophenyl) amino] phenylacetoxyacetate derivatives and their use as an intermediate to synthesize aceclofenac
WO2005073163A1 (en) * 2004-01-30 2005-08-11 J.B.Chemicals & Pharmaceuticals Ltd. A process for the preparation of [2-(2,6-dichloro anilino) phenyl] acetoxy acetic acid

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DE3811120A1 (en) * 1988-03-31 1989-10-12 Merckle Gmbh NEOPENTYL ESTER DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS MEDICINAL PRODUCTS
ES2020146A6 (en) * 1990-05-29 1991-07-16 Prodesfarma Sa Process for obtaining 2-[(2,6-dichlorophenyl)amino]- phenylacetoxyacetic acid
ES2020145A6 (en) * 1990-05-29 1991-07-16 Prodesfarma Sa Process for obtaining esters of 2-(2,6- dichlorophenyl)amino)phenylacetoxyacetic acid

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AU670139B2 (en) 1996-07-04
AU5217793A (en) 1994-06-23
PL174822B1 (en) 1998-09-30
NZ250409A (en) 1995-07-26
HUT65711A (en) 1994-07-28
CA2111169A1 (en) 1994-06-15
PL301415A1 (en) 1994-06-27
KR100196240B1 (en) 1999-06-15
ES2065242A1 (en) 1995-02-01
CA2111169C (en) 2001-05-01
ES2065242B1 (en) 1995-10-01
GR1002048B (en) 1995-11-16
HU9303551D0 (en) 1994-04-28
GR930100500A (en) 1994-08-31
PL175116B1 (en) 1998-11-30

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