[go: up one dir, main page]
More Web Proxy on the site http://driver.im/

KR850000430A - 1,2,4-트리아졸-3-온 항우울증제의 제조방법 - Google Patents

1,2,4-트리아졸-3-온 항우울증제의 제조방법

Info

Publication number
KR850000430A
KR850000430A KR1019840003692A KR840003692A KR850000430A KR 850000430 A KR850000430 A KR 850000430A KR 1019840003692 A KR1019840003692 A KR 1019840003692A KR 840003692 A KR840003692 A KR 840003692A KR 850000430 A KR850000430 A KR 850000430A
Authority
KR
South Korea
Prior art keywords
compound
formula
propyl
piperazinyl
ethyl
Prior art date
Application number
KR1019840003692A
Other languages
English (en)
Other versions
KR890000637B1 (ko
Inventor
주니어 데이비스 엘. 템플 (외 1)
Original Assignee
아이삭 자아코브스키
브리스톨-마이어즈 컴페니
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 아이삭 자아코브스키, 브리스톨-마이어즈 컴페니 filed Critical 아이삭 자아코브스키
Publication of KR850000430A publication Critical patent/KR850000430A/ko
Application granted granted Critical
Publication of KR890000637B1 publication Critical patent/KR890000637B1/ko

Links

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
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • 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
    • A61P25/24—Antidepressants
    • 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
    • A61P25/26—Psychostimulants, e.g. nicotine, cocaine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C265/00—Derivatives of isocyanic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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
    • C07D241/20—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
    • C07D249/12—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
    • C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/06—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals
    • C07D295/067—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/15—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Psychiatry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pain & Pain Management (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Quinoline Compounds (AREA)

Abstract

내용 없음.

Description

1,2,4-트리아졸-3-온 항우울증제의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (27)

  1. (a) 다음 구조식(X')의 화합물을 다음 구조식(VII) 또는 (Xlll)의 알킬화제 또는 후술하는 A'가 라디칼 (b)이고 B'가 라디칼(c)일 경우에는 다음 구조식(XVI)의 피페라진과 반응시켜 다음 구조식(XI)의 화합물을 얻고, (b) 이 구조식(XI)의 화합물의 염이 필요한 경우에는 구조식(XI)의 화합물을 약리학적으로 허용되는 그의 염으로 전환시여는 것이 특징인 구조식(XI)의 1,2,3-트리아졸-3-은 항우울증제 및 그의 염의 제조방법.
    위 각 구조식에서, n은 2-4의 정수이고, R2는 수소 또는 저급 알킬(C-4)이며, X1은 산소 또는 직접 결합쇄이고, Y는 수소, 할로겐, 저급 알킬(C1-4) 또는 CF3(단, Y가 수소일 때, n은 2가 될 수 없고, R2는 에틸이 될 수 없으며, X1은 산소가 될 수 없고, 후술하는 Z는 모노 할로겐 치환체를 가진 페닐이 될 수 없다)이며, A'는 수소 또는 다음의 피페라지닐 라디칼(a),(Z는 후술하는 바와 같다) 또는 라디칼 (b), -(CH2)3-X":(X"는 할로겐, 황산기, 인산기, 메실산기, 바람직하게는 토실산기와 같은 이틸기이다)이고, B'는 수소 또는 다음의 라디칼 (c),(Y,X1및 n은 앞에서 정의한 바와 같다)이며, R1은 n이 2-4일 때 수소 또는 알톡시이고, n이 3-4일 때 역시 수소이고, X는 할로겐, 바람직하게는 염소 또는 취소, 또는 황산기, 인선기, 토실산기 또는 메틸산기와 같은 이탈기이며, X'는 X의 정의와 같고, X"는 앞의 정의와 같으며, Z는 벤질 또는 다음의 라디칼 중에서 선정되는 라디칼이다.
    위 라디칼에 있어서, R3는 수소 또는 할로겐, R4는 수소 또는 CF3, R5는 수소, 할로겐 또는 시아노, R6은 수소 또는 할로겐이다.
  2. 제1항에 있어서, (a)단계의 반응이 (1) 염화 p-톨루엔술포닐과 다음 구조식(XIV)의 알코올을 반응시켜 다음 구조식(XV)의 토실산염을 얻는 단계와, (2)이 토실산염(XV)을 다음 구조식(XVI)의 치환피페라진과 반응시켜 상기 구조식(XI)의 화합물을 얻는 2단계 반응으로 구성된 것이 특징인 방법.
    위 각 식에서, Y,X1,n,R2및 Z는 제1항에 정의한 바와 같다.
  3. 제1항에 있어서, (a) 단계의 반응이 다음 구조식(XIII)의 트리아졸론을 다음 구조식(XIII)의 피파라지닐프로필-X'로 일킬화시켜 상기 구조식(XI)의 화합물을 얻는 것이 특징인 방법.
    위 각 구조식에서, Y1,X1,n,R2,X' 및 Z는 제1항에서 정의한 바와 같다.
  4. (a) 히드라진을 1-(할로페닐)-4-(3-할로프로필)피페라진으로 알킬화시켜 다음 구조식(III)의 1-(할로페닐)-4-(3-히드라지노-프로필)피페라진을 얻고, 이어서 (b) 구조식(III)화합물을 고온 아래 불활성 반응용매 중에서 N-에톡시카로보닐티오프로피온아미드,
    로 축합시키는 것이 특징인 다음 구조식(II)의 1,2,3-트리아졸론 화합물의 제조방법.
    위 각 구조식에서, R는 페닐환의 제2,3 또는 4위치에 결합된 할로겐이다.
  5. 제1항 있어서, 구조식(XI)의 화합물이 2-[3-[4-(3-클로로페닐)-1-피페라지닐]프로필]-5-에틸-2,4-디히드로-4-(3-펜옥시프로필)-3H-1,2,4-트리아졸-3-온인 방법.
  6. 제1항에 있어서, 구조식(XI)의 화합물이 2-[3-[4-(3-클로로페닐)-1-피페라지닐]프로필]-5-에틸-2,4-디히드로-4-(4-펜옥시부틸)-3H-1,2,4-트리아졸-3-온인 방법.
  7. 제1항에 있어서, 구조식(XI)의 화합물이 2-[3-[4-(3-클로로페닐)-1-피페라지닐]프로필]-5-에틸-2,4-디히드로-4-[2-[2-메톡시 펜옥시(에틸]-3H-1,2,4-트리아졸-3-온인 방법.
  8. 제1항에 있어서, 구조식(IX)의 화합물이 2-[3-[4-(3-클로로페닐)-1-피페라지닐]프로필]-5-(1,1-디메틸에틸)-2,4-디히드로-4-(2-펜옥시에틸)-3H-1,2,4-트리아졸-3-온인 방법.
  9. 제1항에 있어서, 구조식(XI)의 화합물이 2-[3-[4-(3-클로로페닐)-1-피페라지닐)프로필]-5-에틸-2,4-디히드로-4-[2-(4-메톡시펜옥시)에틸]-3H-1,2,4-트리아졸-3-온인 방법.
  10. 제1항에 있어서, 구조식(XI)의 화합물이 2-[3-[4-(3-클로로페닐)-1-피페라지닐)프로필]-5-에틸-2,4-디히드로-4-[2-(3-트리플루오로메틸)펜옥시]에틸]-3H-1,2,4 -트리아졸-3-온인 방법.
  11. 제1항에 있어서, 구조식(XI)의 화합물이 4-[3-(3-클로로펜옥시)프로필]-2-[3-[4-(3-클로로페닐)-1-피페라지닐]프로필]-5-에틸-3,4-디히드로-3H-1,2,4-트리아졸-3-온인 방법.
  12. 제1항에 있어서, 구조식(XI)의 화합물이 4-[2-(3-클로로펜옥시)프로필-2-[3-[4-(3-클로로페닐)-1-피페라지닐)프로필]-5-에틸-2,4-디히드로-3H-1,2,4-트리아졸-3-온인 방법.
  13. 제1항에 있어서, 구조식(IX)의 화합물이 2-[3-[4-(3-클로로페닐)-1-피페라지닐]프로필]-5-에틸-2,4-디히드로-4-[3-[3-(트리플루오로메틸)펜옥시]프로필]-3H-1,2,4-트리아졸-3-온인 방법.
  14. 제1항에 있어서, 구조식(XI)의 화합물이 2-[3-[4-(3-클로로페닐)-1-피페라지닐]프로필]-5-에틸-2,4-디히드로-4-(3-페닐부틸)-3H-1,2,4-트리아졸-3-온인 방법.
  15. 제1항에 있어서, 구조식(XI)의 화합물이 2-[3-[4-(3-클로로페닐)-1-피페라지닐]프로필]-5-에틸-2,4-디히드로-4-(4-페닐부틸)-3H-1,2,4-트리아졸-3-온인 방법.
  16. 제1항에 있어서, 구조식(XI)의 화합물이 2-[3-[4-(3-클로로페닐)-1-피페라지닐]프로필]-2,4-디히드로-4-(2-펜옥시에틸) -3H-1,2,4-트리아졸-3-온인 방법.
  17. 제1항에 있어서, 구조식(XI)의 화합물이 2-[3-[4-(3-클로로페닐)-1-피페라지닐]프로필]-2,4-디히드로-4-[2-(3-클로로펜옥시)에틸]-3H-1,2,4-트리아졸-3-온인 방법.
  18. 제1항에 있어서, 구조식(XI)의 화합물이 4-[3-(3-클로로펜옥시)프로필]-2-[3-[4-(3-클로로페닐)-1-피페라지닐]프로필]-2,4-디히드로-3H-1,2,4-트리다졸-온인 방법.
  19. 제1항에 있어서, 구조식(XI)의 화합물이 2-[3-[4-(3-클로로페닐)-1-피페라지닐]프로필]-2,4-디히드로-4-[3-[3-(트리플루오로메틸)펜옥시]프로필]-3H-1,2,4-트리아졸-3-온인 방법.
  20. 제1항에 있어서, 구조식(XI)의 화합물이 2-[3-[4-(1,2-벤즈이티아졸-3-일)-1-피페라지닐]프로필]-5-에틸-2,4-디히드로-4-(2-펜옥시에틸)-3H-1,2,4-트리아졸-3-온인 방법.
  21. 제1항에 있어서, 구조식(XI)의 화합물이 2-[4-[3-[3-에틸-4,5-디히드로-5-옥소-4-(2-펜옥시에틸)-1H-1,2,4-트리아졸-1-일]프로필]-1-피페라지닐]-3-피리딘카로보니트릴인 방법.
  22. 제1항에 있어서, 구조식(XI)의 화합물이 5-에틸-2,4-디히드로-4-(2-펜옥시에틸)-2-[3-[4-(페닐메틸)-1-피페라지닐]프로필]-3H-1,2,4-트리아졸-3-온인 방법.
  23. 제1항에 있어서, 구조식(XI)의 화합물이 5-에틸-2,4-디히드로-4-(2-펜옥시에틸)-2-[3-[4-(퀴놀린-2-일)-1-피페라지닐][프로필]-3H-1,2,4-트리아졸-3-온인 방법.
  24. 제1항에 있어서, 구조식(XI)의 화합물이 2-[3-[4-(3-클로로-4-플루오로페닐) -1-피페라지닐]프로필]-5-에틸-2,4-디히드로-4-(2-펜옥시에틸)-3H-1,2,4-트리아졸-3-온인 방법.
  25. 제1항에 있어서, 구조식(XI)의 화합물이 5-에틸-2,4-디히드로-4-(2-펜옥시에틸)-2-[3-[4-[3-(트리플루오로메틸]페닐]-1-피페라지닐]프로필]-3H-1,2,4-트리아졸-3-온인 방법.
  26. 제1항에 있어서, 구조식(XI)의 화합물이 2-[3-[4-(2-클로로-6-피라지닐)-1-피페라지닐]프로필]-5-에틸-2,4-디히드로-4-(2-펜옥시에틸)-3H-1,2,4-트리아졸-1-온인 방법.
  27. 제1항에 있어서, 구조식(XI)의 화합물이 2-[3-[4-(6-클로로-2-피리디닐)-1-피페라지닐]프로필]-5-에틸-2,4-디히드로-4-(2-펜옥시에틸)-3H-1,2,4-트리아졸-3-온인 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019840003692A 1983-06-29 1984-06-28 1,2,4-트리아졸-3-온 항우울증제 및 그 제조방법 KR890000637B1 (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US06/509,266 US4487773A (en) 1981-03-16 1983-06-29 1,2,4-Triazol-3-one antidepressants
US509266 1983-06-29
US509,266 1983-06-29

Publications (2)

Publication Number Publication Date
KR850000430A true KR850000430A (ko) 1985-02-27
KR890000637B1 KR890000637B1 (ko) 1989-03-22

Family

ID=24025922

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019840003692A KR890000637B1 (ko) 1983-06-29 1984-06-28 1,2,4-트리아졸-3-온 항우울증제 및 그 제조방법

Country Status (21)

Country Link
US (1) US4487773A (ko)
JP (1) JPS6036469A (ko)
KR (1) KR890000637B1 (ko)
AU (1) AU579826B2 (ko)
BE (1) BE900038A (ko)
CA (1) CA1255310A (ko)
CH (2) CH663412A5 (ko)
DE (1) DE3423898A1 (ko)
DK (1) DK316784A (ko)
ES (1) ES533753A0 (ko)
FI (1) FI842597A (ko)
FR (1) FR2551439B1 (ko)
GB (4) GB2142631B (ko)
GR (1) GR81450B (ko)
IT (1) IT1176342B (ko)
LU (1) LU85442A1 (ko)
MY (1) MY102072A (ko)
NL (1) NL8402028A (ko)
PT (1) PT78816A (ko)
SE (1) SE8403460L (ko)
ZA (1) ZA844887B (ko)

Families Citing this family (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4596884A (en) * 1983-11-30 1986-06-24 Bristol-Myers Company 4-(2-phenoxyethyl)-1,2,4-triazolone process intermediates
YU44721B (en) * 1983-11-30 1990-12-31 Bristol Myers Co Process for obtaining 4-(2-phenoxyethyl)-1,2,4-triazolone
DE3934081A1 (de) * 1989-10-12 1991-04-18 Bayer Ag Sulfonylaminocarbonyltriazolinone
US4784998A (en) * 1987-04-06 1988-11-15 Bristol-Myers Company 1,3,4-oxadiazole pyschotropic compounds
EP0350145A3 (en) * 1988-04-28 1990-07-04 Yamanouchi Pharmaceutical Co. Ltd. Pyridylthiazolidine carboxamide derivatives and their intermediates and production of both
FR2642759B1 (fr) * 1989-02-09 1991-05-17 Laboratorios Esteve Sa Derives de pyrimidyl-piperazinyl-alkyl azoles avec activite anxiolytique et/ou tranquillisante
US5243051A (en) * 1990-03-05 1993-09-07 Shionigi & Co., Ltd. Tetrahydropyridine derivatives
US5149817A (en) * 1990-03-05 1992-09-22 Shionogi & Co., Ltd. Teirahydropyridine derivatives
US5266571A (en) * 1992-01-09 1993-11-30 Amer Moh Samir Treatment of hemorrhoids with 5-HT2 antagonists
US5256664A (en) * 1992-04-28 1993-10-26 Bristol-Myers Squibb Company Antidepressant 3-halophenylpiperazinylpropyl derivatives of substituted triazolones and triazoldiones
DE4425144A1 (de) * 1994-07-15 1996-01-18 Basf Ag Triazolverbindungen und deren Verwendung
CA2160423A1 (en) * 1994-11-02 1996-05-03 Hemant N. Joshi Salts of nefazodone having improved dissolution rates
US6403593B1 (en) 1995-07-14 2002-06-11 Abbott Laboratories Triazole compounds and the use thereof
DE19728996A1 (de) 1997-07-07 1999-01-14 Basf Ag Triazolverbindungen und deren Verwendung
CA2344150A1 (en) 1998-09-18 2000-03-30 Alcon Laboratories, Inc. Serotonergic 5ht2 agonists for treating glaucoma
ES2152860B1 (es) * 1998-10-23 2001-08-16 Finaf 92 Sa Forma cristalina de la nefazodona y procedimiento para su preparacion.
ES2188344B1 (es) * 2000-11-29 2004-09-16 Laboratorios Vita, S.A. Compuestos derivados de benzotiofeno, su procedimiento de obtencion y utilizacion de los mismos.
AU2003282665A1 (en) * 2002-10-11 2004-05-04 Cytokinetics, Inc. Compounds, compositions, and methods
CA2523191A1 (en) * 2003-04-30 2004-11-18 Fmc Corporation Phenyl substituted cyclic derivatives
CA2567249A1 (en) * 2004-04-19 2006-10-05 Jds Pharmaceuticals, Llc Lithium combinations, and uses related thereto
AR049382A1 (es) * 2004-05-18 2006-07-26 Fmc Corp Derivados de la urea ciclica substituida
US20060073172A1 (en) * 2004-10-01 2006-04-06 Schneider L W Stabilized ophthalmic solution for the treatment of glaucoma and lowering intraocular pressure
CA2694621C (en) 2007-08-07 2015-01-06 Prosarix Limited Novel serotonergic modulators
WO2009149347A1 (en) * 2008-06-05 2009-12-10 President And Fellows Of Harvard College High-valent palladium fluoride complexes and uses thereof
CA2742869A1 (en) 2008-11-20 2010-05-27 President And Fellows Of Harvard College Fluorination of organic compounds
WO2010081036A2 (en) * 2009-01-09 2010-07-15 President And Fellows Of Harvard College Fluorine containing compounds and methods of use thereof
US9150516B2 (en) 2011-04-12 2015-10-06 President And Fellows Of Harvard College Fluorination of organic compounds
US9505728B2 (en) 2012-03-09 2016-11-29 Inception 2, Inc. Triazolone compounds and uses thereof
WO2014052622A1 (en) 2012-09-26 2014-04-03 President And Fellows Of Harvard College Nickel fluorinating complexes and uses thereof
AU2013363398B2 (en) 2012-12-20 2017-06-01 Tempest Therapeutics, Inc. Triazolone compounds and uses thereof
CN105142741B (zh) 2013-04-26 2016-08-17 日本卓球株式会社 乒乓球及乒乓球用热塑性树脂组合物
US9776976B2 (en) 2013-09-06 2017-10-03 Inception 2, Inc. Triazolone compounds and uses thereof
US10759764B2 (en) 2013-10-18 2020-09-01 President And Fellows Of Harvard College Fluorination of organic compounds
WO2023218251A1 (en) * 2022-05-10 2023-11-16 Clearsynth Labs Limied Novel deuterium-enriched nefazodone analogues and method for preparing thereof

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1066857B (it) * 1965-12-15 1985-03-12 Acraf Derivati della s ipiazolo 4.3 a piridina e processi per la loro preparazione
IT1052119B (it) * 1972-10-16 1981-06-20 Sigma Tau Ind Farmaceuti Derivati del triazolinone e procedimento per la loro preparazione
IT1052130B (it) * 1973-10-15 1981-06-20 Sigma Tau Ind Farmaceuti Derivati del triazolinone e procedimento per la loro preparazione
US4338317A (en) * 1981-03-16 1982-07-06 Mead Johnson & Company Phenoxyethyl-1,2,4,-triazol-3-one antidepressants
US4386091A (en) * 1982-02-24 1983-05-31 Mead Johnson & Company 2-Phenoxyalkyl-1,2,4-triazol-3-one antidepressants
US4613600A (en) * 1983-09-30 1986-09-23 Mead Johnson & Company Antidepressant 1,2,4-triazolone compounds

Also Published As

Publication number Publication date
CH663412A5 (de) 1987-12-15
JPS6036469A (ja) 1985-02-25
JPH0524151B2 (ko) 1993-04-06
GB8703632D0 (en) 1987-03-25
IT1176342B (it) 1987-08-18
US4487773A (en) 1984-12-11
GB8703633D0 (en) 1987-03-25
ES8600278A1 (es) 1985-10-01
SE8403460D0 (sv) 1984-06-28
DK316784D0 (da) 1984-06-28
FI842597A0 (fi) 1984-06-27
ES533753A0 (es) 1985-10-01
GB2185021B (en) 1988-02-03
CA1255310A (en) 1989-06-06
KR890000637B1 (ko) 1989-03-22
IT8421641A0 (it) 1984-06-28
GB2185021A (en) 1987-07-08
FR2551439B1 (fr) 1989-08-25
GB2142631B (en) 1987-09-03
BE900038A (fr) 1984-12-28
GR81450B (ko) 1984-12-11
GB8703634D0 (en) 1987-03-25
FR2551439A1 (fr) 1985-03-08
GB8416435D0 (en) 1984-08-01
GB2142631A (en) 1985-01-23
GB2184447A (en) 1987-06-24
NL8402028A (nl) 1985-01-16
GB2184447B (en) 1988-02-03
DE3423898A1 (de) 1985-01-03
FI842597A (fi) 1984-12-30
CH662562A5 (de) 1987-10-15
IT8421641A1 (it) 1985-12-28
SE8403460L (sv) 1984-12-30
LU85442A1 (fr) 1985-03-26
MY102072A (en) 1992-03-31
AU2995384A (en) 1985-01-03
ZA844887B (en) 1985-02-27
PT78816A (en) 1984-07-01
DK316784A (da) 1984-12-30
GB2184446A (en) 1987-06-24
AU579826B2 (en) 1988-12-15

Similar Documents

Publication Publication Date Title
KR850000430A (ko) 1,2,4-트리아졸-3-온 항우울증제의 제조방법
RU2201924C2 (ru) Морфолиновое производное и фармацевтическая композиция на его основе
KR890006593A (ko) 아르마타제 억제4(5)- 이미다졸
KR850002270A (ko) 항우울증 작용을 가진 1,2,4-트리아졸론 화합물의 제조 방법
KR840002827A (ko) 2-[4-[(4,4-디알킬-2,6-피페리딘디온-1-일)부틸]피페라지닐] 피리미딘류의 제조
JP2002534519A (ja) ドーパミン−ｄ３−レセプター親和性を有するトリアゾール化合物
KR850002483A (ko) 1-헤테로아릴-4-[(2,5-피롤리딘디온-1-일]피페라진 유도체의 제조방법
US4404382A (en) Piperazinyl-substituted imidazoles
KR940005616A (ko) 아졸 화합물, 그의 제법 및 용도
EP0902016A3 (en) A process and intermediate compounds for the preparation of amlodipine benzene sulphonate
WO1996013499A1 (en) Apolipoprotein-b synthesis inhibitors
NO168476C (no) Analogifremgangsmaate for fremstilling av terapeutisk aktive 4-(4-(4-(4-(((2,4-difluorfenyl)-2-(1h-azolylmetyl)-1,3-dioxolan-4-yl)metoksy)fenyl)-1-piperazinyl)fenyl)triazoloner.
RU2144032C1 (ru) Гетероциклические производные, фармацевтическая композиция, способ получения фармацевтической композиции, промежуточные соединения, способы получения гетероциклических производных
KR860001098A (ko) 이소인돌리닐-알킬-피페라진류의 제조방법
US4408049A (en) Substituted piperazinyl-1,2,4-triazoles
KR840008017A (ko) 트리아졸 유도체의 제조방법
US6197972B1 (en) Triazolones as apolipoprotein-B synthesis inhibitors
RU97116580A (ru) Триазоловое соединение и его фармакологически приемлемая соль и противогрибковая композиция
US4788190A (en) 2,4,4-tri- and 2,2,4,4-tetra substituted-1,3-dioxolane antifungal, antiallergy compounds
DE3788507D1 (de) Substituierte 1H-Imidazole.
KR860004029A (ko) 이미다졸리움 염의 제조방법
KR870006009A (ko) N-비닐아졸류
RU96107877A (ru) Производные пиридазинона или их соли, способы их получения и противошоковое средство, содержащее их
US4835283A (en) 3,5-diphenyl-3-[(1H-imidazol-1-ylmethyl) or (1H-1,2,4-triazol-1-ylmethyl)]-2
ATE30911T1 (de) Hydrazinopyridazinverbindung, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel.

Legal Events

Date Code Title Description
A201 Request for examination
E902 Notification of reason for refusal
E902 Notification of reason for refusal
G160 Decision to publish patent application
E701 Decision to grant or registration of patent right
GRNT Written decision to grant
FPAY Annual fee payment

Payment date: 19930311

Year of fee payment: 5

LAPS Lapse due to unpaid annual fee