KR960007560A - Novel amine derivatives, their preparation and use as antiarrhythmics - Google Patents

Novel amine derivatives, their preparation and use as antiarrhythmics Download PDF

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KR960007560A
KR960007560A KR1019940024840A KR19940024840A KR960007560A KR 960007560 A KR960007560 A KR 960007560A KR 1019940024840 A KR1019940024840 A KR 1019940024840A KR 19940024840 A KR19940024840 A KR 19940024840A KR 960007560 A KR960007560 A KR 960007560A
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정유섭
박성대
권래성
신홍섭
시게루 타나베
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김정규
주식회사 씨앤드씨 신약연구소
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
    • C07D211/14—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Abstract

본 발명은 항부정맥제로서 유용한 다음 일반식(I)의 신규한 아민 유도체 및 그의 염, 그의 제조방법 및 그의 항부정맥제로서의 용도에 관한 것이다.The present invention relates to novel amine derivatives of the general formula (I) and salts thereof, methods for their preparation and their use as antiarrhythmic agents which are useful as antiarrhythmic agents.

상기식에서,일반식또는의 그룹을 타나내고, A는 일반식의 그룹 또는 N-함유 6-원 헤테로사이클릭 그룹을 나타내며, 여기에서 R8은 저급알킬 또는 하이드록시저급알킬을 나타내고, a는 0 또는 1이며,는 5- 또는 6-원 N-함유 헤테로사이클릭 그룹이고, D는 일반식 -(CH2)m-, (CH2)m-O-, -CO- 또는 SO2의 그룹을 나타내며, R1및 R2는 독립적으로 수소, 할로겐, 저급알콕시 또는 저급알킬설포닐아미노를 나타내고, R3는 저급알킬을 나타내며, R4, R5, R6및 R7은 각각 독립적으로 수소 또는 저급알킬설포닐아미노를 나타내고, R은 니트로 또는 저급알킬설포닐아미노를 나타내며, X는 수소 또는 할로겐을 나타내고, m은 0 내지 3의 정수를 나타내고, n은 0 내지 3의 정수를 나타낸다.In the above formula, General formula or Represents a group of, A is a general formula Or a N-containing 6-membered heterocyclic group wherein R 8 represents lower alkyl or hydroxy lower alkyl, a is 0 or 1, Is a 5-or 6-membered N- containing heterocyclic group, D is the formula - (CH 2) m -, (CH 2) m -O-, represents a group of -CO- or SO 2, R 1 And R 2 independently represents hydrogen, halogen, lower alkoxy or lower alkylsulfonylamino, R 3 represents lower alkyl, and R 4 , R 5 , R 6 and R 7 are each independently hydrogen or lower alkylsulfonyl Amino represents, R represents nitro or lower alkylsulfonylamino, X represents hydrogen or halogen, m represents an integer from 0 to 3, n represents an integer from 0 to 3.

Description

신규한 아민 유도체, 그의 제조방법 및 항부정맥제로서의 용도Novel amine derivatives, their preparation and use as antiarrhythmics

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is an open matter, no full text was included.

Claims (13)

하기 일반식(I)의 화합물 및 그의 염:A compound of formula (I): 상기식에서,는 일반식또는의 그룹을 타나내고, A는 일반식의 그룹 또는 N-함유 6-원 헤테로사이클릭 그룹을 나타내며, 여기에서 R8은 저급알킬 또는 하이드록시저급알킬을 나타내고, a는 0 또는 1이며,는 5- 또는 6-원 N-함유 헤테로사이클릭 그룹이고, D는 일반식 -(CH2)m-, (CH2)m-O-, -CO- 또는 SO2의 그룹을 나타내며, R1및 R2는 독립적으로 수소, 할로겐, 저급알콕시 또는 저급알킬설포닐아미노를 나타내고, R3는 저급알킬을 나타내며, R4, R5, R6및 R7은 각각 독립적으로 수소 또는 저급알킬설포닐아미노를 나타내고, R은 니트로 또는 저급알킬설포닐아미노를 나타내며, X는 수소 또는 할로겐을 나타내고, m은 0 내지 3의 정수를 나타내고, n은 0 내지 3의 정수를 나타낸다.In the above formula, Is a general formula or Represents a group of, A is a general formula Or a N-containing 6-membered heterocyclic group wherein R 8 represents lower alkyl or hydroxy lower alkyl, a is 0 or 1, Is a 5-or 6-membered N- containing heterocyclic group, D is the formula - (CH 2) m -, (CH 2) m -O-, represents a group of -CO- or SO 2, R 1 And R 2 independently represents hydrogen, halogen, lower alkoxy or lower alkylsulfonylamino, R 3 represents lower alkyl, and R 4 , R 5 , R 6 and R 7 are each independently hydrogen or lower alkylsulfonyl Amino represents, R represents nitro or lower alkylsulfonylamino, X represents hydrogen or halogen, m represents an integer from 0 to 3, n represents an integer from 0 to 3. 제1항에 있어서, A는 일반식의 그룹 또는 질소원자 1 또는 2개를 함유하는 6-원 포화 헤테로사이클릭 그룹을 나타내며, 여기에서 R8은 C1-C6저급알킬 또는 하이드록시 -C1-C6저급알킬을 나타내고, a는 0 또는 1이며,는 한개의 질소원자를 함유하는 5- 또는 6-원 헤테로사이클릭 그룹이고, R1및 R2는 각각 독립적으로 수소, 할로겐, C1-C6저급알콕시 또는 C1-C6저급알킬솔포닐아미노를 나타내고, R3는 C1-C6저급알킬을 나타내며, R4, R5, R6및 R7은 각각 독립적으로 수소 또는 C1-C6저급알킬솔포닐아미노를 나타내고, R은 니트로 또는 C1-C6저급알킬솔포닐아미노를 나타내며, m은 0 내지 2의 정수를 나타내고, n은 0 내지 2의 정수를 나타내는 화합물 및 그의 염.The method of claim 1, wherein A is a general formula Or a 6-membered saturated heterocyclic group containing 1 or 2 nitrogen atoms, wherein R 8 represents C 1 -C 6 loweralkyl or hydroxy-C 1 -C 6 loweralkyl, a Is 0 or 1, Is a 5- or 6-membered heterocyclic group containing one nitrogen atom, and R 1 and R 2 are each independently hydrogen, halogen, C 1 -C 6 lower alkoxy or C 1 -C 6 lower alkylsolfonyl Amino, R 3 represents C 1 -C 6 lower alkyl, R 4 , R 5 , R 6 and R 7 each independently represent hydrogen or C 1 -C 6 lower alkylsolfonylamino, and R is nitro Or C 1 -C 6 lower alkylsolfonylamino, m represents an integer of 0 to 2, n represents an integer of 0 to 2 and salts thereof. 제2항에 있어서, A는 일반식의 그룹 또는 피페리디닐 또는 피페라지닐 그룹을 나타내며, 여기에서 R8은 메틸, 에틸 또는 하이드록시에틸을 나타내고, a는 0 또는 1이며,는 3-피페리디닐 또는 2-피롤리디닐 그룹이며, R1및 R2는 각각 독립적으로 수소, 할로겐 또는 메틸설포닐아미노를 나타내고, R3는 메틸을 나타내며, R4, R5, R6및 R7은 각각 독립적으로 수소 또는 메틸설포닐아미노를 나타내고, R은 니트로 또는 메틸설포닐아미노를 나타내며, m은 0 내지 2의 정수를 나타내고, n은 0 내지 2의 정수를 나타내는 화합물 및 그의 염.The method of claim 2, wherein A is a general formula Or a piperidinyl or piperazinyl group wherein R 8 represents methyl, ethyl or hydroxyethyl, a is 0 or 1, and Is a 3-piperidinyl or 2-pyrrolidinyl group, R 1 and R 2 each independently represent hydrogen, halogen or methylsulfonylamino, R 3 represents methyl, and R 4 , R 5 , R 6 And R 7 each independently represents hydrogen or methylsulfonylamino, R represents nitro or methylsulfonylamino, m represents an integer of 0 to 2, n represents an integer of 0 to 2 and salts thereof . 제1항 내지 3항중의 어느 하나에 있어서,가 일반식의 그룹을 나타내고, R1및 R2가 저급알콕시를 나타내며, R은 니트로 또는 저급알킬설포닐아미노를 나타내는 화합물 및 그의 염.The method according to any one of claims 1 to 3, General formula A group represented by R 1 and R 2 represent lower alkoxy, R represents nitro or lower alkylsulfonylamino and salts thereof. 제4항에 있어서, R1및 R2가 메톡시를 나타내며, R은 니트로를 나타내고, X는 수소를 나타내는 화합물 및 그의 염.The compound and salt thereof according to claim 4, wherein R 1 and R 2 represent methoxy, R represents nitro and X represents hydrogen. 제1항 내지 3항중의 어느 하나에 있어서,가 일반식의 그룹을 나타내고, R1은 수소를 나타내며, R2는 저급알킬설포닐아미노를 나타내고, R은 니트로 또는 저급알킬설포닐아미노를 나타내는 화합물 및 그의 염.The method according to any one of claims 1 to 3, General formula And R 1 represents hydrogen, R 2 represents lower alkylsulfonylamino, R represents nitro or lower alkylsulfonylamino and salts thereof. 제6항에 있어서, R2가 메틸설포닐아미노를 나타내고, R은 니트로를 나타내며, X는 수소를 나타내는 화합물 및 그의 염.The compound and salt thereof according to claim 6, wherein R 2 represents methylsulfonylamino, R represents nitro and X represents hydrogen. 제1항에 있어서, 3-[N-(4-메탄설폰아미도펜에틸)-N-메틸아미노]-1-(4-니트로벤질)피페리딘 또는 그의 염인 화합물.The compound according to claim 1, which is 3- [N- (4-methanesulfonamidophenethyl) -N-methylamino] -1- (4-nitrobenzyl) piperidine or a salt thereof. 제1항에 있어서, 2-[N-(3,4-디메톡시펜에틸)-N-메틸아미노]메틸-1-(4-니트로벤질)피롤리딘 또는 그의 염인 화합물.The compound according to claim 1, which is 2- [N- (3,4-dimethoxyphenethyl) -N-methylamino] methyl-1- (4-nitrobenzyl) pyrrolidine or a salt thereof. (A)하기 일반식(Ⅱ)의 화합물 또는 그의 염을 하기 일반식(Ⅲ)의 화합물 또는 그의 염과 반응시켜 일반식(Ia)의 화합물 또는 그의 염을 제조하거나, (B)하기 일반식(Ⅳ)의 화합물 또는 그의 염을 하기 일반식(Ⅴ)의 화합물 또는 그의 염과 반응시켜 하기 일반식(Ib)의 화합물 또는 그의 염을 제조함을 특징으로 하여 일반식(I)의 화합물 및 그의 염을 제조하는 방법.(A) reacting a compound of formula (II) or a salt thereof with a compound of formula (III) or a salt thereof to produce a compound of formula (Ia) or a salt thereof, or (B) The compound of formula (I) and salts thereof, characterized in that the compound of formula (IV) or a salt thereof is reacted with a compound of formula (V) or a salt thereof to prepare a compound of formula (Ib) How to prepare. 상기식에서,는 일반식또는의 그룹을 나타내고, A는 일반식의 그룹 또는 N-함유 6-원 헤테로사이클릭 그룹을 나타내며, 여기에서, R8은 저급알킬 또는 하이드록시저급알킬을 나타내고, a는 0 또는 1이며,는 5- 또는 6-원 N-함유 헤테로사이클릭 그룹이고, D는 일반식 -(CH2)m-, (CH2)m-O-, -CO- 또는 SO2의 그룹을 나타내며, R1및 R2는 독립적으로 수소, 할로겐, 저급알콕시 또는 저급알킬설포닐아미노를 나타내고, R3는 저급알킬을 나타내며, R4, R5, R6및 R7은 각각 독립적으로 수소 또는 저급알킬설포닐아미노를 나타내고, R은 니트로 또는 저급알킬설포닐아미노를 나타내며, X는 수소 또는 할로겐을 나타내고, m은 0 내지 3의 정수를 나타내고, n은 0 내지 3의 정수를 나타내며, Het는 N-함유 6-원 헤테로사이클릭 그룹을 나타내고, L은 반응성 이탈그룹을 나타낸다.In the above formula, Is a general formula or Represents a group of and A is a general formula Or a N-containing 6-membered heterocyclic group wherein R 8 represents lower alkyl or hydroxy lower alkyl, a is 0 or 1, and Is a 5-or 6-membered N- containing heterocyclic group, D is the formula - (CH 2) m -, (CH 2) m -O-, represents a group of -CO- or SO 2, R 1 And R 2 independently represents hydrogen, halogen, lower alkoxy or lower alkylsulfonylamino, R 3 represents lower alkyl, and R 4 , R 5 , R 6 and R 7 are each independently hydrogen or lower alkylsulfonyl Amino, R represents nitro or lower alkylsulfonylamino, X represents hydrogen or halogen, m represents an integer from 0 to 3, n represents an integer from 0 to 3, Het is N-containing 6 -Membered heterocyclic group, and L represents reactive leaving group. 제10항에 있어서, 하기 일반식(Ⅱ)의 화합물 또는 그의 염을 하기 일반식(Ⅲ)의 화합물 또는 그의 염과 반응시켜 하기 일반식(Ia)의 화합물 또는 그의 염을 제조함을 특징으로 하여 일반식(I)의 화합물 및 그의 염을 제조하는 방법.The compound of formula (II) or a salt thereof is reacted with a compound of formula (III) or a salt thereof to prepare a compound of formula (Ia) or a salt thereof. Process for the preparation of compounds of formula (I) and salts thereof. 상기식에서,는 일반식또는의 그룹을 나타내고, A는 일반식의 그룹 또는 N-함유 6-원 헤테로사이클릭 그룹을 나타내며, 여기에서, R8은 저급알킬 또는 하이드록시저급알킬을 나타내고, a는 0 또는 1이며,는 5- 또는 6-원 N-함유 헤테로사이클릭 그룹이고, D는 일반식 -(CH2)m-, (CH2)m-O-, -CO- 또는 SO2의 그룹을 나타내며, R1및 R2는 독립적으로 수소, 할로겐, 저급알콕시 또는 저급알킬설포닐아미노를 나타내고, R3는 저급알킬을 나타내며, R4, R5, R6및 R7은 각각 독립적으로 수소 또는 저급알킬설포닐아미노를 나타내고, R은 니트로 또는 저급알킬설포닐아미노를 나타내며, X는 수소 또는 할로겐을 나타내고, m은 0 내지 3의 정수를 나타내고, n은 0 내지 3의 정수를 나타내며, Het는 N-함유 6-원 헤테로사이클릭 그룹을 나타내고, L은 반응성 이탈그룹을 나타낸다.In the above formula, Is a general formula or Represents a group of and A is a general formula Or a N-containing 6-membered heterocyclic group wherein R 8 represents lower alkyl or hydroxy lower alkyl, a is 0 or 1, and Is a 5-or 6-membered N- containing heterocyclic group, D is the formula - (CH 2) m -, (CH 2) m -O-, represents a group of -CO- or SO 2, R 1 And R 2 independently represents hydrogen, halogen, lower alkoxy or lower alkylsulfonylamino, R 3 represents lower alkyl, and R 4 , R 5 , R 6 and R 7 are each independently hydrogen or lower alkylsulfonyl Amino, R represents nitro or lower alkylsulfonylamino, X represents hydrogen or halogen, m represents an integer from 0 to 3, n represents an integer from 0 to 3, Het is N-containing 6 -Membered heterocyclic group, and L represents reactive leaving group. 제10항에 있어서, 하기 일반식(Ⅳ)의 화합물 또는 그의 염을 하기 일반식(Ⅴ)의 화합물 또는 그의 염과 반응시켜 하기 일반식(Ib)의 화합물 또는 그의 염을 제조함을 특징으로 하여 일반식(I)의 화합물 및 그의 염을 제조하는 방법.The compound of formula (IV) or a salt thereof is reacted with a compound of formula (V) or a salt thereof to prepare a compound of formula (Ib) or a salt thereof. Process for the preparation of compounds of formula (I) and salts thereof. 상기식에서,는 일반식또는의 그룹을 나타내고, A는 일반식의 그룹 또는 N-함유 6-원 헤테로사이클릭 그룹을 나타내며, 여기에서, R8은 저급알킬 또는 하이드록시저급알킬을 나타내고, a는 0 또는 1이며,는 5- 또는 6-원 N-함유 헤테로사이클릭 그룹이고, D는 일반식 -(CH2)m-, (CH2)m-O-, -CO- 또는 SO2의 그룹을 나타내며, R1및 R2는 독립적으로 수소, 할로겐, 저급알콕시 또는 저급알킬설포닐아미노를 나타내고, R3는 저급알킬을 나타내며, R4, R5, R6및 R7은 각각 독립적으로 수소 또는 저급알킬설포닐아미노를 나타내고, R은 니트로 또는 저급알킬설포닐아미노를 나타내며, X는 수소 또는 할로겐을 나타내고, m은 0 내지 3의 정수를 나타내고, n은 0 내지 3의 정수를 나타내며, Het는 N-함유 6-원 헤테로사이클릭 그룹을 나타내고, L은 반응성 이탈그룹을 나타낸다.In the above formula, Is a general formula or Represents a group of and A is a general formula Or a N-containing 6-membered heterocyclic group wherein R 8 represents lower alkyl or hydroxy lower alkyl, a is 0 or 1, and Is a 5-or 6-membered N- containing heterocyclic group, D is the formula - (CH 2) m -, (CH 2) m -O-, represents a group of -CO- or SO 2, R 1 And R 2 independently represents hydrogen, halogen, lower alkoxy or lower alkylsulfonylamino, R 3 represents lower alkyl, and R 4 , R 5 , R 6 and R 7 are each independently hydrogen or lower alkylsulfonyl Amino, R represents nitro or lower alkylsulfonylamino, X represents hydrogen or halogen, m represents an integer from 0 to 3, n represents an integer from 0 to 3, Het is N-containing 6 -Membered heterocyclic group, and L represents reactive leaving group. 약제학적으로 허용되는 담체와 함께 제1항 내지 9항중의 어느 한 항에 따르는 일반식(I)의 화합물 또는 그의 염을 활성성분으로 함유함을 특징으로 하는 항부정맥제 조성물.An antiarrhythmic composition comprising a compound of formula (I) according to any one of claims 1 to 9 or a salt thereof as an active ingredient together with a pharmaceutically acceptable carrier. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019940024840A 1994-08-16 1994-09-29 Novel amine derivatives, their preparation and use as antiarrhythmics KR960007560A (en)

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