KR850007596A - Method for preparing 1,4-dihydro-4-oxonaphthyridine derivative - Google Patents

Method for preparing 1,4-dihydro-4-oxonaphthyridine derivative Download PDF

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KR850007596A
KR850007596A KR1019850002822A KR850002822A KR850007596A KR 850007596 A KR850007596 A KR 850007596A KR 1019850002822 A KR1019850002822 A KR 1019850002822A KR 850002822 A KR850002822 A KR 850002822A KR 850007596 A KR850007596 A KR 850007596A
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히로가주 나리따 (외 10)
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나까노 다다오
도야마 가가꾸 고오교오 가부시끼 가이샤
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Abstract

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Description

1,4-디하이드로-4-옥소나프티리딘 유도체의 제조방법Method for preparing 1,4-dihydro-4-oxonaphthyridine derivative

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

Claims (40)

일반식(Ⅲ 또는 Ⅴ)의 화합물 또는 그의 염을 폐환시키고, 이어서, 경우에 따라, 카복실-보호그룹을 제거함을 특징으로 하여, 일반식(Ⅰ)의 1,4-디하이드로-4-옥소나프티리딘 유도체, 또는 그의 염을 제조하는 방법.1,4-dihydro-4-oxonaphthyl of formula (I), characterized in that the compound of formula (III or V) or a salt thereof is closed, and then optionally the carboxyl-protecting group is removed Process for preparing a ridine derivative, or salt thereof. 상기식에서, R1은 수소원자 또는 카복실-보호그룹을 나타내고, R2는 치환된 또는 비치환된 아릴그룹을 나타내며, R3는 할로겐원자 또는 치환된 또는 비치환된 환상의 아미노그룹을 나타내고, R1a는 카복실-보호그룹을 나타낸다.Wherein R 1 represents a hydrogen atom or a carboxyl-protecting group, R 2 represents a substituted or unsubstituted aryl group, R 3 represents a halogen atom or a substituted or unsubstituted cyclic amino group, and R 1a represents a carboxyl-protective group. 제1항에 있어서, R2가 치환된 또는 비치환된 페닐그룹을 나타내는 일반식(Ⅰ)의 1,4-디하이드로-4-옥소나프티리딘 유도체 또는 그의 염을 제조하는 방법.The process for preparing a 1,4-dihydro-4-oxonaphthyridine derivative of formula (I) according to claim 1, wherein R 2 represents a substituted or unsubstituted phenyl group. 제2항에 있어서 R3가 1-피롤리디닐, 피페리디노, 1-피페라지닐 및 모플리노그룹으로 이루어진 그룹으로부터 선택된 비치환되거나 치환된 환상의 아미노그룹을 나타내는 일반식(Ⅰ)의 1,4-디하이드로-4-옥소나프티리딘 유도체 또는 그의 염을 제조하는 방법.The compound of formula (I) according to claim 2, wherein R 3 represents an unsubstituted or substituted cyclic amino group selected from the group consisting of 1-pyrrolidinyl, piperidino, 1-piperazinyl, and moplino groups. A process for preparing a 4-4-hydrohydrooxoxnaphthyridine derivative or salt thereof. 제3항에 있어서, R2가 할로겐원자, 알킬그룹, 하이드록실그룹, 알콕시그룹, 시아노그룹, 아미노그룹, 아실아미노그룹 및 트리할로게노알킬그룹으로 이루어진 그룹으로부터 선택된 적어도 하나의 치환체에 의해 치환될 수 있는 페닐그룹을 나타내는 일반식(Ⅰ)의 1,4-디하이드로-4-옥소나프티리딘 유도체 또는 그의 염을 제조하는 방법.The compound of claim 3, wherein R 2 is selected from a halogen atom, an alkyl group, a hydroxyl group, an alkoxy group, a cyano group, an amino group, an acylamino group, and a trihalogenoalkyl group. A process for preparing a 1,4-dihydro-4-oxonaphthyridine derivative of formula (I) representing a phenyl group which may be substituted or a salt thereof. 제4항에 있어서, R3가 알킬, 아미노, 아미노알킬, 하이드록시알킬, 하이드록실, 알케닐, 아실, 알킬아미노, 디알킬아미노, 시아노, 옥소, 아르알킬아미노, 아실아미노, 알콕시카보닐 및 N-아실-N-알킬아미노그룹으로 이루어진 그룹으로부터 선택된 적어도 하나의 치환체에 의해 치환될 수 있는 1-피롤리디닐, 피페리디노, 1-피페라지닐 또는 모폴리노그룹을 나타내는 일반식(Ⅰ)의 1,4-디하이드로-4-옥소나프티리딘 유도체 또는 그의 염을 제조하는 방법.The compound of claim 4, wherein R 3 is alkyl, amino, aminoalkyl, hydroxyalkyl, hydroxyl, alkenyl, acyl, alkylamino, dialkylamino, cyano, oxo, aralkylamino, acylamino, alkoxycarbonyl And 1-pyrrolidinyl, piperidino, 1-piperazinyl or morpholino group which may be substituted by at least one substituent selected from the group consisting of N-acyl-N-alkylamino groups ( A process for producing the 1,4-dihydro-4-oxonaphthyridine derivative of I) or a salt thereof. 제5항의 있어서, R3가 알킬, 아미노, 하이드록시알킬, 하이드록실, 알케닐, 아실, 알킬아미노, 디알킬아미노, 알콕시카보닐 및 N-아실-N-알킬아미노그룹으로 이루어진 그룹으로부터 선택된 적어도 하나의 치환체에 의해 치환될 수 있는 1-피롤리디닐, 피페리디노, 1-피페라지닐, 또는 모폴리노그룹을 나타내는 일반식(Ⅰ)의 1,4-디하이드로-4-옥소나프티리딘 유도체 또는 그의 염을 제조하는 방법.The compound of claim 5, wherein R 3 is at least selected from the group consisting of alkyl, amino, hydroxyalkyl, hydroxyl, alkenyl, acyl, alkylamino, dialkylamino, alkoxycarbonyl and N-acyl-N-alkylamino group 1,4-dihydro-4-oxonaphthyridine of formula (I) which represents 1-pyrrolidinyl, piperidino, 1-piperazinyl, or morpholino group which may be substituted by one substituent Process for preparing derivatives or salts thereof. 제6항에 있어서, R2가 적어도 하나의 할로겐원자에 의해 치환된 페닐그룹을 나타내는 일반식(Ⅰ)의 1,4-디하이드로-4-옥소나프티리딘 유도체 또는 그의 염을 제조하는 방법.The process for producing a 1,4-dihydro-4-oxonaphthyridine derivative of formula (I) according to claim 6, wherein R 2 represents a phenyl group substituted by at least one halogen atom. 제7항에 있어서, R2가 4-플루오로페닐 또는 2,4-디플루오로페닐그룹을 나타내는 일반식(Ⅰ)의 1,4-디하이드로-4-옥소나프티리딘 유도체 또는 그의 염을 제조하는 방법.The 1,4-dihydro-4-oxonaphthyridine derivative of the general formula (I) according to claim 7, wherein R 2 represents 4-fluorophenyl or 2,4-difluorophenyl group. How to. 제2항에 있어서, R3가 아미노, 하이드록실, 알킬아미노, 디알킬아미노, 아실아미노 및 N-아실-N알킬아미노그룹으로 이루어진 그룹으로부터 선택된 적어도 하나의 치환체에 의해 치환될 수 있는 1-피롤리디닐그룹을 나타내는 일반식(Ⅰ)의 1,4-디하이드로-4-옥소나프티리딘 유도체 또는 그의 염을 제조하는 방법.The compound of claim 2, wherein R 3 is optionally substituted with at least one substituent selected from the group consisting of amino, hydroxyl, alkylamino, dialkylamino, acylamino and N-acyl-Nalkylamino groups. A method for producing a 1,4-dihydro-4-oxonaphthyridine derivative of the general formula (I) representing a rolledinyl group or a salt thereof. 제9항에 있어서, R2가 할로겐원자, 알킬그룹, 하이드록실그룹, 알콕시그룹, 시아노그룹, 아미노그룹, 아실아미노그룹 및 트리-할로게노알킬그룹으로 이루어진 그룹으로부터 선택된 적어도 하나의 치환체에 의해 치환될 수 있는 페닐그룹을 나타내는 일반식(Ⅰ)의 1,4-디하이드로-4-옥소나프티리딘 유도체 또는 그의 염을 제조하는 방법,The compound of claim 9, wherein R 2 is selected from a halogen atom, an alkyl group, a hydroxyl group, an alkoxy group, a cyano group, an amino group, an acylamino group, and a tri-halogenoalkyl group. A process for preparing a 1,4-dihydro-4-oxonaphthyridine derivative of the general formula (I) representing a phenyl group which may be substituted or a salt thereof, 제10항에 있어서, R3가 아미노 또는 아실아미노그룹에 의해 치환된 1-피롤리디닐그룹을 나타내는 일반식(Ⅰ)의 1,4-디하이드로-4-옥소나프티리딘 유도체 또는 그의 염을 제조하는 방법.A 1,4-dihydro-4-oxonaphthyridine derivative of formula (I) according to claim 10, wherein R 3 represents a 1-pyrrolidinyl group substituted with an amino or acylamino group, or a salt thereof How to. 제11항에 있어서 R2가 적어도 하나의 할로겐원자에 의해 치환된 페닐그룹을 나타내는 일반식(Ⅰ)의 1,4-디하이드로-4-옥소나프티리딘 유도체 또는 그의 염을 제조하는 방법.The process for preparing a 1,4-dihydro-4-oxonaphthyridine derivative of formula (I) according to claim 11, wherein R 2 represents a phenyl group substituted with at least one halogen atom. 제12항에 있어서, R2가 4-플루오로페닐 또는 2,4-디플루오로페닐그룹을 나타내는 일반식(Ⅰ)의 1,4-디하이드로-4-옥소나프티리딘 유도체 또는 그의 염을 제조하는 방법.13. The preparation of 1,4-dihydro-4-oxonaphthyridine derivative of formula (I) according to claim 12, wherein R 2 represents 4-fluorophenyl or 2,4-difluorophenyl group. How to. 제2항에 있어서, R3가 3-아미노-1-피롤리디닐그룹을 나타내는 일반식(Ⅰ)의 1,4-디하이드로-4-옥소나프티리딘 유도체 또는 그의 염을 제조하는 방법.The process for producing a 1,4-dihydro-4-oxonaphthyridine derivative of formula (I) according to claim 2, wherein R 3 represents a 3-amino-1-pyrrolidinyl group. 제14항에 있어서, R2가 할로겐원자, 알킬그룹, 하이드록실그룹, 알콕시그룹, 시아노그룹, 아미노그룹, 아실아미노그룹 및 트리할로게노알킬그룹으로 이루어진 그룹으로부터 선택된 적어도 하나의 치환체에 의해 치환될 수 있는 페닐그룹을 나타내는 일반식(Ⅰ)의 1,4-디하이드로-4-옥소나프티리딘 유도체 또는 그의 염을 제조하는 방법.15. The compound of claim 14, wherein R 2 is selected from at least one substituent selected from the group consisting of a halogen atom, an alkyl group, a hydroxyl group, an alkoxy group, a cyano group, an amino group, an acylamino group and a trihalogenoalkyl group. A process for preparing a 1,4-dihydro-4-oxonaphthyridine derivative of formula (I) representing a phenyl group which may be substituted or a salt thereof. 제15항에 있어서, R2가 적어도 하나의 하로겐원자에 의해 치환된 페닐그룹을 나타내는 일반식(Ⅰ)의 1,4-디하이드로-4-옥소나프티리딘 유도체 또는 그의 염을 제조하는 방법.The process for producing a 1,4-dihydro-4-oxonaphthyridine derivative of formula (I) according to claim 15, wherein R 2 represents a phenyl group substituted with at least one halogen atom. 제16항에 있어서, R2가 4-풀루오로페닐 또는 2,4-디풀루오로페닐그룹을 나타내는 일반식(Ⅰ)의 1,4-디하이드로-4-옥소나프티리딘 유도체 또는 그의 염을 제조하는 방법.17. The 1,4-dihydro-4-oxonaphthyridine derivative of the general formula (I) or a salt thereof according to claim 16, wherein R 2 represents 4- pullofluorophenyl or 2,4-difluophenyl group. How to manufacture. 제2항에 있어서, R3가 알킬, 하이드록실알킬, 알케닐, 아실 및 알콕시카보닐그룹으로 이루어진 그룹으로부터 선택된 적어도 하나의 치환체에 의해 치환될 수 있는 1-피레라지닐그룹을 나타내는 일반식(Ⅰ)의 1,4-디하이드로-4-옥소나프티리딘 유도체 또는 그의 염을 제조하는 방법.The general formula of claim 2, wherein R 3 represents a 1-pyrerazinyl group which may be substituted by at least one substituent selected from the group consisting of alkyl, hydroxylalkyl, alkenyl, acyl and alkoxycarbonyl groups ( A process for producing the 1,4-dihydro-4-oxonaphthyridine derivative of I) or a salt thereof. 제18항에 있어서, R2가 할로겐원자, 알킬그룹, 하이드록실그룹, 알콕시그룹, 시아노그룹, 아미노그룹, 아실아미노그룹 및 트리할로게노알킬그룹으로 이루어진 그룹으로부터 선택된 적어도 하나의 치환체에 의해 치환될 수 있는 페닐그룹을 나타내는 일반식(Ⅰ)의 1,4--디하이드로-4-옥소나프티리딘 유도체 또는 그의 염을 제조하는 방법.The compound of claim 18, wherein R 2 is selected from a halogen atom, an alkyl group, a hydroxyl group, an alkoxy group, a cyano group, an amino group, an acylamino group and a trihalogenoalkyl group. A process for preparing a 1,4-dihydro-4-oxonaphthyridine derivative of the general formula (I) representing a phenyl group which may be substituted or a salt thereof. 제19항에 있어서, R3가 1-피페라지닐그룹을 나타내는 일반식(Ⅰ)의 1,4-디하이드로-4-옥소나프티리딘 유도체 또는 그의 염을 제조하는 방법.20. The process for producing a 1,4-dihydro-4-oxonaphthyridine derivative of formula (I) according to claim 19, wherein R 3 represents a 1-piperazinyl group. 제20항에 있어서, R2가 적어도 하나의 할로겐원자에 의해 치환된 페닐그룹을 나타내는 일반식(Ⅰ)의 1,4-디하이드로-4-옥소나프티리딘 유도체 또는 그의 염을 제조하는 방법.The process of claim 20, wherein R 2 represents a phenyl group substituted by at least one halogen atom, or a 1,4-dihydro-4-oxonaphthyridine derivative of the general formula (I). 제16항에 있어서, R2가 4-플로오로페닐 또는 2,4-디풀루오로페닐그룹을 나타내는 일반식(Ⅰ)의 1,4-디하이드로-4-옥소나프티리딘 유도체 또는 그의 염을 제조하는 방법.The 1,4-dihydro-4-oxonaphthyridine derivative of the general formula (I) according to claim 16, wherein R 2 represents 4-fluorophenyl or 2,4-difluophenyl group. How to. 제9항에 있어서, R3가 아미노 또는 아실아미노그룹에 의해 치환된 1-피롤리디닐그룹을 나타내는 일반식(Ⅰ)의 1,4-디하이드로-4-옥소나프티리딘 유도체 또는 그의 염을 제조하는 방법.The 1,4-dihydro-4-oxonaphthyridine derivative of the general formula (I) according to claim 9, wherein R 3 represents a 1-pyrrolidinyl group substituted by an amino or acylamino group, or a salt thereof. How to. 제18항에 있어서, R3가 1-피페라지닐그룹을 나타내는 일반식(Ⅰ)의 1,4-디하이드로-4-옥소나프티리딘 유도체 또는 그의 염을 제조하는 방법.19. The process for producing a 1,4-dihydro-4-oxonaphthyridine derivative of formula (I) according to claim 18, wherein R 3 represents a 1-piperazinyl group. 제1항에 있어서, 7-클로로-1-(2,4-디플루오로페닐)-6-플루오로-1,4-디하이드로-4-옥소-1,8-나프티리딘-3-카복실산 또는 그의 염을 제조하는 방법.The compound of claim 1, wherein 7-chloro-1- (2,4-difluorophenyl) -6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid or Method for preparing its salts. 제1항에 있어서, 7-(3-아미노-1-피롤리디닐)-1-(2,4-디플루오로페닐)-6-플루오로-1,4-디하이드로-4-옥소-1,8-나프티리딘-3-카복실산 또는 그의 염을 제조하는 방법.The compound of claim 1, wherein 7- (3-amino-1-pyrrolidinyl) -1- (2,4-difluorophenyl) -6-fluoro-1,4-dihydro-4-oxo-1 , 8-naphthyridine-3-carboxylic acid or a salt thereof. 제1항에 있어서,1-(2,4-디플루오로페닐)-6-플루오로-1,4-디하이드로-4-옥소-7-(1-피레라지닐)-1,8-나프티리딘-3-카복실산 또는 그의 염을 제조하는 방법.The 1- (2,4-difluorophenyl) -6-fluoro-1,4-dihydro-4-oxo-7- (1-pyrerazinyl) -1, 8-naphti according to claim 1. Process for preparing lidin-3-carboxylic acid or salts thereof. 제1항 있어서, 7-(3-아미노-1-피롤리디닐)-6-플루오로-1-(4-플루오로페닐)-1,4-디하이드로-4-옥소-1,8-나프티리딘-3-카복실산 또는 그의 염을 제조하는 방법.The compound of claim 1, wherein 7- (3-amino-1-pyrrolidinyl) -6-fluoro-1- (4-fluorophenyl) -1,4-dihydro-4-oxo-1,8-naphthy Process for preparing lidin-3-carboxylic acid or salts thereof. 제1항에 있어서 폐환반응이 20˚내지 160℃의 온도에서 수행되는 방법.The method of claim 1 wherein the ring closure reaction is carried out at a temperature of 20 ° to 160 ° C. 일반식(Ⅲ)의 화합물, 또는 그의 염을 일반식 R3b-H(이때, R3b는 후술하는 바와 같이 정의된다)의 화합물, 또는 그의 염과 반응시킴을 특징으로 하여, 일반식(Ⅰb)의 1,4-디하이드로-4-옥소-나프티리딘 유도체, 또는 그의 염을 제조하는 방법.A compound of formula (III), or a salt thereof, is reacted with a compound of formula R 3b -H, wherein R 3b is defined below, or a salt thereof, wherein the compound of formula (Ib) 1,4-dihydro-4-oxo-naphthyridine derivative, or a method for producing a salt thereof. 상기식에서, R1은 수소원자 또는 카복실-보호그룹을 나타내고, R2는 치환된 또는 비치환된 아릴그룹을 나타내며, R3b는 치환된 또는 비치환된 환상의 아미노그룹을 나타내고, R3a는 할로겐 원자를 나타낸다.Wherein R 1 represents a hydrogen atom or a carboxyl-protecting group, R 2 represents a substituted or unsubstituted aryl group, R 3b represents a substituted or unsubstituted cyclic amino group, and R 3a represents a halogen Represents an atom. 제30항에 있어서, R2가 치환된 또는 비치환된 페닐그룹을 나타내는 일반식(Ⅰb)의 1,4-디하이드로-4-옥소-나프티리딘 유도체, 또는 그의 염을 제조하는 방법.31. The process of claim 30, wherein R 2 represents a 1,4-dihydro-4-oxo-naphthyridine derivative of formula (Ib) representing a substituted or unsubstituted phenyl group. 제31항에 있어서, R3b가 아미노, 하이드록실, 알킬아미노, 디알킬아미노 및 N-아실-N-알킬아미노그룹으로 이루어진 그룹으로부터 선택된 적어도 하나의 치환체에 의해 치환될수 있는 1-피롤리디닐그룹을 나타내는 일반식(Ⅰb)의 1,4-디하이드로-4-옥소-나프티리딘 유도체, 또는 그의 염을 제조하는 방법.The 1-pyrrolidinyl group of claim 31, wherein R 3b is optionally substituted by at least one substituent selected from the group consisting of amino, hydroxyl, alkylamino, dialkylamino and N-acyl-N-alkylamino groups. A method for producing a 1,4-dihydro-4-oxo-naphthyridine derivative of the general formula (Ib), or a salt thereof. 제32항에 있어서, R3b가 아미노 또는 아실아미노그룹에 의해 치환된 1-피롤리디닐그룹을 나타내는 일반식(Ⅰb)의 1,4-디하이드로-4-옥소-나프티리딘 유도체, 또는 그의 염을 제조하는 방법.33. The 1,4-dihydro-4-oxo-naphthyridine derivative of formula (Ib) according to claim 32, or a salt thereof, wherein R 3b represents a 1-pyrrolidinyl group substituted with an amino or acylamino group. How to prepare. 제33항에 있어서, R2가 적어도 나하의 할로겐원자에 의해 치환된 페닐그룹을 나타내는 일반식(Ⅰb)의 1,4-디하이드로-4-옥소-나프티리딘 유도체, 또는 그의 염을 제조하는 방법.34. The method for preparing a 1,4-dihydro-4-oxo-naphthyridine derivative of formula (Ib) according to claim 33, wherein R 2 represents a phenyl group substituted by at least a halogen atom of Naha, or a salt thereof. . 제34항에 있어서, R2가 4-플루오로페닐 또는 2,4-디플루오로페닐그룹을 나타내는 일반식(Ⅰb)의 1,4-디하이드로-4-옥소-나프티리딘 유도체, 또는 그의 염을 제조하는 방법.35. The 1,4-dihydro-4-oxo-naphthyridine derivative of formula (Ib) according to claim 34, wherein R 2 represents 4-fluorophenyl or 2,4-difluorophenyl group, or a salt thereof How to prepare. 제31항에 있어서, R3b가 알킬, 하이드록실알킬, 알케닐, 아실 및 알콕시카보닐그룹으로 이루어진 그룹으로부터 선택된 적어도 하나의 치환체에 의해 치환될 수 있는 1-피페라지닐그룹을 나타내는 일반식(Ⅰb)의 1,4-디하이드로-4-옥소-나프티리딘 유도체, 또는 그의 염을 제조하는 방법.The compound of claim 31, wherein R 3b represents a 1-piperazinyl group which may be substituted by at least one substituent selected from the group consisting of alkyl, hydroxylalkyl, alkenyl, acyl and alkoxycarbonyl groups. A process for preparing the 1,4-dihydro-4-oxo-naphthyridine derivative of Ib), or a salt thereof. 제36항에 있어서, R3b가 1-피페라지닐그룹을 나타내는 일반식(Ⅰb)의 1,4-디하이드로-4-옥소-나프티리딘 유도체, 또는 그의 염을 제조하는 방법.37. The process of claim 36, wherein R 3b represents a 1-piperazinyl group, or a 1,4-dihydro-4-oxo-naphthyridine derivative of formula (Ib), or a salt thereof. 제37항에 있어서, R2가 적어도 하나의 할로겐원자에 의해 치환된 페닐그룹을 나타내는 일반식(Ⅰb)의1,4-디하이드로-4-옥소-나프티리딘 유도체, 또는 그의 염을 제조하는 방법.38. The method of claim 37, wherein R 2 represents a 1,4-dihydro-4-oxo-naphthyridine derivative of formula (Ib) representing a phenyl group substituted by at least one halogen atom, or a salt thereof. . 제38항에 있어서, R2가 4-플루오로페닐 또는 2,4-디플루오로페닐그룹을 나타내는 일반식(Ⅰb)의 1,4-디하이드로-4-옥소-나프티리딘 유도체, 또는 그의 염을 제조하는 방법.The 1,4-dihydro-4-oxo-naphthyridine derivative of formula (Ib) according to claim 38, wherein R 2 represents 4-fluorophenyl or 2,4-difluorophenyl group, or a salt thereof How to prepare. 제30항에 있어서, 반응이 0˚내지 150℃의 온도에서 이루어지는 방법.The method of claim 30, wherein the reaction is at a temperature of 0 ° to 150 ° C. 33. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
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