KR970701177A - Acetate Amide Derivatives and Methods for Making the Same (AMIDE DERIVATIVES AND PROCESS FOR THE PREPARATION THEREOF) - Google Patents

Acetate Amide Derivatives and Methods for Making the Same (AMIDE DERIVATIVES AND PROCESS FOR THE PREPARATION THEREOF)

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KR970701177A
KR970701177A KR1019960704569A KR19960704569A KR970701177A KR 970701177 A KR970701177 A KR 970701177A KR 1019960704569 A KR1019960704569 A KR 1019960704569A KR 19960704569 A KR19960704569 A KR 19960704569A KR 970701177 A KR970701177 A KR 970701177A
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formula
compound
pharmaceutically acceptable
piperazin
acetamide
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라이터 요제프네
부다이 졸탄
타카츠 가보르네
메제이 티보르
블라스코 가보르
시미그 기울라
에지드 안드라스
이. 비지 스질베스즈터
페케테 마르톤
스제메레디 카탈린
가이에르타이안 이스트반
각살라이 이스트반
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사바 키스; 아틸라 만디
에지스 지오기스제르기아르 알티.
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Publication of KR970701177A publication Critical patent/KR970701177A/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems 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 carbon atoms of the ring system
    • C07D219/08—Nitrogen atoms
    • 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
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    • 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
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems 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 carbon atoms of the ring system
    • C07D219/08—Nitrogen atoms
    • C07D219/10—Nitrogen atoms attached in position 9
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

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  • Health & Medical Sciences (AREA)
  • Neurosurgery (AREA)
  • Engineering & Computer Science (AREA)
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  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)

Abstract

본 발명은 신규한 아세트산 유도체, 그것의 제조방법, 및 상기 유도체를 포함하는 제약학적 조성물에 관한 것이고, 상기 아세트산 아미드 유도체를 질병 치료용으로 및 질병 치료에 적당한 제약학적 조성물의 제조용으로 사용하는 방법에 관한 것이다. 본 발명에 따른 신규한 조성물은 화학식(I)에 의해 특성화될 수 있고, 상기 식에서 R은 수소를 나타내고, B는 아릴, 아르알킬 또는 헤테로아릴 치환기를 선택적으로 함유하는 피페라지노, 8-아자스피로[4,5]데칸-7,9-디온-8-일 또는 2-(1,2,4-트리아졸로[4,3-a]피리딜-3(2H)-온-2-일)를 나타내며, 상기 조성물은 중요한 제약학적 특성을 갖고, 알츠하이머병의 치료에 적당하다.The present invention relates to a novel acetic acid derivative, a method for preparing the same, and a pharmaceutical composition comprising the derivative, wherein the acetic acid amide derivative is used for treating a disease and for preparing a pharmaceutical composition suitable for treating a disease. It is about. The novel compositions according to the invention can be characterized by formula (I), in which R represents hydrogen, B is piperazino, 8-azaspiro, optionally containing aryl, aralkyl or heteroaryl substituents [4,5] decane-7,9-dione-8-yl or 2- (1,2,4-triazolo [4,3-a] pyridyl-3 (2H) -one-2-yl) The composition has important pharmaceutical properties and is suitable for the treatment of Alzheimer's disease.

Description

아세트산 아미드 유도체 및 그것의 제조방법(AMIDE DERIVATIVES AND PROCESS FOR THE PREPARATION THEREOF)Acetic Acid Amide Derivatives and Methods for Making the Same (AMIDE DERIVATIVES AND PROCESS FOR THE PREPARATION THEREOF)

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

Claims (21)

하기 화학식(I)의 아세트산 아미드 유도체 및 그것의 제약학적으로 수용될 수 있는 산-부가염;Acetic acid amide derivatives of formula (I) and pharmaceutically acceptable acid-addition salts thereof; 상기 식에서, R은 수소를 나타내고, B은 선택적으로 아릴, 아르알킬 또는 헤테로아릴 치환기를 함유하는 피페라지노, 8-아자스[4,5]데칸-7,9-디온-8-일 또는 2-(1,2,4-트리아졸로[4,3-a]피리딜-3-(2H)-온-2-일)을 나타낸다.Wherein R represents hydrogen and B represents piperazino, 8-aza [4,5] decane-7,9-dione-8-yl or 2, optionally containing aryl, aralkyl or heteroaryl substituents -(1,2,4-triazolo [4,3-a] pyridyl-3- (2H) -one-2-yl). B가 할로겐, 피리디일 또는 피리미디닐에 의해 선택적으로 치환되는 페닐 또는 벤질 치환기를 선택적으로 갖는 피페라지노를 나타내는 화학식(I)의 화합물 및 그것의 제약학적으로 수용될 수 있는 산-부가염.A compound of formula (I) wherein B represents piperazino optionally having a phenyl or benzyl substituent optionally substituted by halogen, pyridylyl or pyrimidinyl and pharmaceutically acceptable acid-addition salts thereof. 하기의 화학식(I)의 화합물;N-(1,2,3,4-테트라히드로아크리딘-9-일)-[(3-클로로페닐)-피페라진-1-일]-아세트아미드, N-(1,2,3,4-테트라히드로아크리딘-9-일)-2-[(N-벤질-피페라진-1-일]-아세트아미드, N-(1,2,3,4-테트라히드로아크리딘-9-일)-2-[(4-플루오로벤질)-피페라진-1-일]-아세트아미드, N-(1,2,3,4-테트라히드로아크리딘-9-일)-2-[1-(2-피리디일)-피페라진-1-일]-아세트아미드, N-(1,2,3,4-테트라히드로아크리딘-9-일)-2-[4-(2-피리디일)-피페라진-1-일]-아세트아미드, 및 그것의 제약학적으로 수용될 수 있는 산-부가염.A compound of formula (I): N- (1,2,3,4-tetrahydroacridin-9-yl)-[(3-chlorophenyl) -piperazin-1-yl] -acetamide, N- (1,2,3,4-tetrahydroacridin-9-yl) -2-[(N-benzyl-piperazin-1-yl] -acetamide, N- (1,2,3, 4-tetrahydroacridin-9-yl) -2-[(4-fluorobenzyl) -piperazin-1-yl] -acetamide, N- (1,2,3,4-tetrahydroacry Din-9-yl) -2- [1- (2-pyridylyl) -piperazin-1-yl] -acetamide, N- (1,2,3,4-tetrahydroacridin-9-yl ) -2- [4- (2-pyridylyl) -piperazin-1-yl] -acetamide, and pharmaceutically acceptable acid-addition salts thereof. 적당한 비활성인 제약학적 고체 또는 액체 담체와의 혼합물의 형태로 활성 성분으로서 화학식(I)의 화합물 또는 그것의 제약학적으로 수용될 수 있는 산-부가염을 포함하는 제약학적 조성물.A pharmaceutical composition comprising a compound of formula (I) or a pharmaceutically acceptable acid-addition salt thereof as the active ingredient in the form of a mixture with a suitable solid inert pharmaceutical solid or liquid carrier. 화학식(I)의 화합물 또는 그것의 제약학적으로 수용될 수 있는 산-부가염을 적당한 비활성인 제약학적 고체 또는 액체 담체와 혼합시키는 것으로 이루어지는 제4항에 따른 제약학적 조성물의 제조방법.A process for the preparation of a pharmaceutical composition according to claim 4, comprising mixing a compound of formula (I) or a pharmaceutically acceptable acid-addition salt thereof with a suitable inert pharmaceutical solid or liquid carrier. 알츠하이머병의 치료에 유용한 제약학적 조성물을 제조하기 위해 화학식(I)의 화합물 또는 제약학적으로 수용될 수 있는 산-부가염을 사용하는 방법.A method of using a compound of formula (I) or a pharmaceutically acceptable acid-addition salt to prepare a pharmaceutical composition useful for the treatment of Alzheimer's disease. 유효량의 화학식(I)의 화합물 또는 그것의 제약학적으로 수용될 수 있는 산-부가염을 환자에 투여시키는 것으로 이루어지는 알츠하이머병의 치료방법.A method of treating Alzheimer's disease, comprising administering to a patient an effective amount of a compound of formula (I) or a pharmaceutically acceptable acid-addition salt thereof. 화학식 (I)의 화합물 및 그것의 제약학적으로 수용될 수 있는 산-부가염의 제조방법으로서,A process for preparing a compound of formula (I) and pharmaceutically acceptable acid-addition salts thereof, a) 하기 화학식(II)의할로아세트아미드 유도체를 화학식(V)의 화합물과 반응시키거나; 또는a) reacting a haloacetamide derivative of formula (II) with a compound of formula (V); or b) 하기 화학식(III)의 아미노 화합물을 화학식(IV)의 반응성 아세트산 유도체와 반응시키고; 바람직한 경우, 이와 같이 수득된 화학식(I)의 화합물을 제약학적으로 수용될 수 있는 산-부가염으로 전환시키는 단계 또는 산-부가염으로부터 화학식(I)의 염기를 방출시키는 단계를 포함하는, 화학식(I)의 화합물 및 그것의 제약학적으로 수용될 수 있는 산-부가염의 제조방법;b) reacting an amino compound of formula III with a reactive acetic acid derivative of formula IV; If desired, the compound of formula (I) thus obtained is converted to a pharmaceutically acceptable acid-addition salt or the release of a base of formula (I) from the acid-addition salt A process for preparing the compound of (I) and its pharmaceutically acceptable acid-addition salt; [상기 식(II)에서, Hlg는 염소, 브롬 또는 요오드를 나타낸다][In Formula (II), Hlg represents chlorine, bromine or iodine.] HBHB [상기 식(V)에서, B는 상기한 바와 같다[In Formula (V), B is as described above. [상기 식(IV)에서, X는 반응기이고, Hlg는 상기한 바와 같다][Wherein X is a reactor and Hlg is as described above] 제8항에 있어서, 방법 a)에서 염기성 축합제로서 유기 염기, 바람직하게는 피리딘, 피콜린, 루티딘 또는 트리에틸아민의 사용을 포함하는 것을 특징으로 하는 방법.9. Process according to claim 8, comprising the use of an organic base, preferably pyridine, picoline, lutidine or triethylamine, as the basic condensing agent in method a). 제8항에 있어서, 방법 a)에서 염기성 축합제로서 알칼리 탄산염, 바람직하게는 탄산 나트륨 또는 탄산 칼슘의 사용을 포함하는 것을 특징으로 하는 방법.9. Process according to claim 8, characterized by the use of an alkali carbonate, preferably sodium carbonate or calcium carbonate, as the basic condensing agent in method a). 제8항, 9항 또는 10항 중 어느 한 항에 있어서, 방법 a)에서 비활성 유기 용매중에서 반응을 수행하는 것을 포함하는 것을 특징으로 하는 방법.The process according to claim 8, 9 or 10, comprising performing the reaction in an inert organic solvent in process a). 제11항에 있어서, 비활성 용매로서 양성자성 용매 바람직하게는 지방족 알코올, 또는 방향족 탄화수소 또는 에테르를 사용하는 것을 포함하는 것을 특징으로 하는 방법.12. The process according to claim 11, comprising using a protic solvent, preferably an aliphatic alcohol, or an aromatic hydrocarbon or an ether as the inert solvent. 제12항에 있어서, 비활서 유기용매로서 에탄올, 이소프로판올, 벤젠, 톨루엔, 크실렌, 디에틸 에테르, 디이소프로필 에테르, 테트라히드로푸란 또는 디옥산의 사용을 포함하는 것을 특징으로 하는 방법.13. A process according to claim 12 comprising the use of ethanol, isopropanol, benzene, toluene, xylene, diethyl ether, diisopropyl ether, tetrahydrofuran or dioxane as a non-volatile organic solvent. 제8항 또는 9항 내지 13항 중 어느 한 항에 있어서, 방법 a)에서 반응을 0 내지 130℃, 바람직하게는 40 내지 90℃에서 수행하는 것을 포함하는 것을 특징으로 하는 방법.14. Process according to any of the claims 8 or 9 to 13, characterized in that the reaction in process a) is carried out at 0 to 130 ° C, preferably 40 to 90 ° C. 제18항에 있어서, 방법 b)에서 X가 히드록시, 염소, 브롬 또는 저급 알코올, 바람직하게는, 메톡시 또는 에톡시를 나타내는 화학식(IV)의 화합물을 출발 물질로 사용하는 것을 특징으로 하는 방법.19. The process according to claim 18, wherein in process b) a compound of formula (IV), wherein X represents hydroxy, chlorine, bromine or lower alcohols, preferably methoxy or ethoxy, is used as starting material . 제15항에 있어서, 반응을 비활성 유기 용매중에서 수행하는 것을 포함하는 것을 특징으로 하는 방법.The process of claim 15 comprising performing the reaction in an inert organic solvent. 제16항에 있어서, 비활성 용매로서 양성자성 용매, 바람직하게는 지방족 알코올, 방향족 탄화수소 또는 에테르의 사용을 포함하는 것을 특징으로 하는 방법.Process according to claim 16, comprising the use of a protic solvent, preferably an aliphatic alcohol, an aromatic hydrocarbon or an ether as inert solvent. 제17항에 있어서, 비활성 융기 용매로서 에탄올, 이소프로판올, 벤젠, 톨루엔, 크실렌, 디에틸 에테르, 디이소프로필 에테르, 테트라히드로푸란 또는 디옥산의 사용을 포함하는 것을 특징으로 하는 방법.18. The method of claim 17, comprising the use of ethanol, isopropanol, benzene, toluene, xylene, diethyl ether, diisopropyl ether, tetrahydrofuran or dioxane as inert raised solvent. 제8항 또는 15항 내지 18항 중 어느 한 항에 있어서, 방법 b)에서 반응을 가열하에서 수행하는 것을 포함하는 것을 특징으로 하는 방법.19. The method according to any one of claims 8 or 15 to 18, comprising carrying out the reaction under heating in method b). 제8항 내지 19항 중 어느 한 항에 있어서, 적당한 출발 물질의 사용을 포함하는 화학식(I)의 화합물의 제조방법으로서 상기 식에서 B대신에 할로겐 원자, 피리딜 및 피리미디닐에 의해 선택적으로 치환된 페닐 또는 벤질 치환기를 선택적으로 함유하는 피페라지노를 함유하는 것을 특징으로 하는 방법.20. A process according to any one of claims 8 to 19, wherein the process for the preparation of compounds of formula (I) comprising the use of suitable starting materials is optionally substituted by a halogen atom, pyridyl and pyrimidinyl instead of B in the above formula A piperazino optionally containing a substituted phenyl or benzyl substituent. 제20항에 있어서, 적당한 출발 몰질의 사용을 포함하는 하기 화합물의 제조방법; N-(1,2,3,4-테트라히드로아크리딘-9-일)-2-[(3-클로로페닐)피페라진-1-일]-아세트아미드, N-(1,2,3,4-테트라히드로아크리딘-9-일)-2-[(N-벤질)-피페라진-1-일]-아세트아미드, N-(1,2,3,4-테트라히드로아크리딘-9-일)-2-[(4-플루오로베질)-피페라진-1-일]-아세트아미드, N-(1,2,3,4-테트라히드로아크리딘-9-일)-2-[1-(2-피리디일)-피페라진-1-일]-아세트아미드, N-(1,2,3,4-테트라히드로아크리딘-9-일)-2-[4-(2-피리디일)-피페라진-1-일]-아세트아미드, 및 그것의 제약학적으로 수용될 수 있는 산-부가염.The process of claim 20 comprising the use of a suitable starting mole; N- (1,2,3,4-tetrahydroacridin-9-yl) -2-[(3-chlorophenyl) piperazin-1-yl] -acetamide, N- (1,2,3 , 4-tetrahydroacridin-9-yl) -2-[(N-benzyl) -piperazin-1-yl] -acetamide, N- (1,2,3,4-tetrahydroacridine -9-yl) -2-[(4-fluorobenzyl) -piperazin-1-yl] -acetamide, N- (1,2,3,4-tetrahydroacridin-9-yl)- 2- [1- (2-Pyridinyl) -piperazin-1-yl] -acetamide, N- (1,2,3,4-tetrahydroacridin-9-yl) -2- [4- (2-pyridylyl) -piperazin-1-yl] -acetamide, and pharmaceutically acceptable acid-addition salts thereof. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019960704569A 1994-02-23 1995-02-22 Acetate Amide Derivatives and Methods for Making the Same (AMIDE DERIVATIVES AND PROCESS FOR THE PREPARATION THEREOF) KR970701177A (en)

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