KR850002270A - 항우울증 작용을 가진 1,2,4-트리아졸론 화합물의 제조 방법 - Google Patents

항우울증 작용을 가진 1,2,4-트리아졸론 화합물의 제조 방법 Download PDF

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KR850002270A
KR850002270A KR1019840006041A KR840006041A KR850002270A KR 850002270 A KR850002270 A KR 850002270A KR 1019840006041 A KR1019840006041 A KR 1019840006041A KR 840006041 A KR840006041 A KR 840006041A KR 850002270 A KR850002270 A KR 850002270A
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compound
formula
hydrogen
pharmaceutically acceptable
chlorophenyl
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KR1019840006041A
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KR880002624B1 (ko
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이. 개맨즈 리차드 (외 2)
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아이삭 자아코브스키
브리스톨-마이어즈 컴페니
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    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • 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
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Psychiatry (AREA)
  • Medicinal Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Pain & Pain Management (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

내용 없음

Description

항우울증 작용을 가진 1,2,4－트리아졸론 화합물의 제조 방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (8)

  1. (a) 히드라진을 적합한 반응 조건 하에 다음 구조식(Ⅵ)의 적절히 보호된 젖산 에스테르와 반응시켜 다음 구조식 (Ⅴ)의 히드라지드 중간체를 얻고,
    (b) 이 히드라지드 중간체(Ⅴ)를 적합한 반응 조건하에 다음 구조식(Ⅶ)의 화합물과 반응시켜서 다음구조식(Ⅳ)의 화합물을 얻고,
    (c) 이 화합물(Ⅳ)를 환화 조건하에 환류시켜 다음 구조식(Ⅲ)의 화합물을 얻고,
    (d) 이 화합물(Ⅲ)을 1－(3－클로로프로필)－4－(3－클로로페닐) 피페라진으로 알킬화시킨 다음 묽은산을 사용하여 보호기 P를 분리시켜서 다음 구조식(Ⅰ)에서 R가 수소인 화합물을 얻고,
    (e) 이 구조식(Ⅰ)에서 R가 수소가 아닌 화합물을 얻고자 하는 경우에는 R가 수소인 구조식(Ⅰ)의 화합물을 알킬화 조건하에 화합물 RX(여기서, R는 수소가 아님)와 반응시켜 구조식(Ⅰ)의 화합물(여기서, R은 수소가 아님)을 얻은 다음.
    (f) 구조식(Ⅰ)화합물의 제약상 허용되는 염을 얻고자 하는 경우에는 구조식(Ⅰ)이 화합물 [R가 수소인 것은 (d)에서 얻은 것, 또는 R가 수소가 아닌 것은 (e)에서 얻은 것]을 적당한 유기산 또는 무기산과 용액 중에서 접촉 반응시켜 구조식(Ⅰ)화합물의 제약상 허용되는 염을 얻는 것이 특징인 다음 구조식(Ⅰ)의 1,2,4－트리아졸론 화합물 또는 이것의 제약상 허용되는 염의 제조 방법.
    위 각 구조식에서, R는 수소, 저급(C1－C4)알킬, 저급 아실, 페닐－저급 알킬 또는 페닐－저급 아실이고, n은 2－4이며, Y는 할로겐 또는 트리플루오로메틸이고, Z는 수소 또는(여기서, R1은 수소, 할로겐, 저급 알콕시 또는 트리플루오로메틸이다.)이며, P는 산에 불안정한 보호기(바람직하게는 메톡시메틸모핵), 저급(C1－C4)알킬 또는 알킬페닐이다.
  2. 제1항에 있어서, R가 수소인 방법.
  3. 제1항에 있어서, Y가 3－클로로인 방법.
  4. 제1항에 있어서, R가 벤질인 방법.
  5. 제1항에 있어서, Z가 페닐옥시인 방법.
  6. 제2항에 있어서, Y가 3－클로로인 방법.
  7. 제1항에 있어서, 구조식(Ⅰ)의 화합물이 2－[3－[4－(3－클로로페닐)－1－피페라지닐]프로필]－5－(1－히드록시에틸)－2,4－디히드로－4－(2－펜옥시에틸)－3H－1,2,4－트리아졸－3은 또는 이것의 제약상 허용되는 산부가염인 방법.
  8. 제1항에 있어서, 구조식(Ⅰ)의 화합물이 2－[3－[4－(3－클로로페닐)－1－피페라지닐]프로필]－4－에틸－5－(1－히드록시에틸)－2H－1,2,4－트리아졸－3(4H)－온 또는 이것의 제약상 허용되는 산부가염인 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019840006041A 1983-09-30 1984-09-29 항우울증 작용을 가진 1,2,4-트리아졸론 화합물 및 그 제조방법 KR880002624B1 (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US06/538,027 US4613600A (en) 1983-09-30 1983-09-30 Antidepressant 1,2,4-triazolone compounds
US538027 1983-09-30
US538,027 1983-09-30

Publications (2)

Publication Number Publication Date
KR850002270A true KR850002270A (ko) 1985-05-10
KR880002624B1 KR880002624B1 (ko) 1988-12-07

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Country Status (25)

Country Link
US (1) US4613600A (ko)
JP (1) JPS60100560A (ko)
KR (1) KR880002624B1 (ko)
AT (1) AT387963B (ko)
AU (1) AU561460B2 (ko)
BE (1) BE900714A (ko)
CA (1) CA1237723A (ko)
CH (1) CH661924A5 (ko)
CY (1) CY1541A (ko)
DE (1) DE3435745C2 (ko)
DK (1) DK169546B1 (ko)
ES (1) ES536286A0 (ko)
FI (1) FI83310C (ko)
FR (1) FR2552759B1 (ko)
GB (1) GB2147297B (ko)
GR (1) GR80475B (ko)
HK (1) HK37391A (ko)
IE (1) IE58084B1 (ko)
IT (1) IT1178522B (ko)
LU (1) LU85561A1 (ko)
MY (1) MY102123A (ko)
NL (1) NL8402946A (ko)
SE (1) SE465928B (ko)
YU (1) YU45667B (ko)
ZA (1) ZA847589B (ko)

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YU44721B (en) * 1983-11-30 1990-12-31 Bristol Myers Co Process for obtaining 4-(2-phenoxyethyl)-1,2,4-triazolone
CA1331757C (en) * 1988-02-29 1994-08-30 Janssen Pharmaceutica Naamloze Vennootschap 5-lipoxygenase inhibiting 4-(4-phenyl-1-piperazinyl)phenols
US5504086A (en) * 1989-10-17 1996-04-02 Ellinwood, Jr.; Everett H. Intraoral dosing method of administering trifluorobenzodiazepines, propoxyphene, and nefazodone
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
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
ES2262515T3 (es) 1999-04-09 2006-12-01 Sepracor Inc. R-hidroxinefazodona.
JP2002541192A (ja) 1999-04-09 2002-12-03 セプラコール， インク． Ｓ−ヒドロキシネファゾドン
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US9072660B2 (en) 2011-09-09 2015-07-07 The Board Of Trustees Of The Leland Stanford Junior University Topical itraconazole formulations and uses thereof

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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
US4338317A (en) * 1981-03-16 1982-07-06 Mead Johnson & Company Phenoxyethyl-1,2,4,-triazol-3-one antidepressants

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HK37391A (en) 1991-05-24
DK468284D0 (da) 1984-09-28
FR2552759B1 (fr) 1988-10-07
FI83310B (fi) 1991-03-15
DE3435745C2 (de) 1994-11-03
BE900714A (fr) 1985-03-28
CY1541A (en) 1991-03-22
US4613600A (en) 1986-09-23
FI843779A0 (fi) 1984-09-26
JPH0542435B2 (ko) 1993-06-28
CH661924A5 (de) 1987-08-31
ES8601966A1 (es) 1985-11-16
AU561460B2 (en) 1987-05-07
MY102123A (en) 1992-03-31
IT1178522B (it) 1987-09-09
ES536286A0 (es) 1985-11-16
ATA310884A (de) 1988-09-15
FI843779L (fi) 1985-03-31
AT387963B (de) 1989-04-10
LU85561A1 (fr) 1985-06-04
FR2552759A1 (fr) 1985-04-05
NL8402946A (nl) 1985-04-16
SE8404869D0 (sv) 1984-09-28
IE842476L (en) 1985-03-30
FI83310C (fi) 1991-06-25
GR80475B (en) 1985-01-31
DE3435745A1 (de) 1985-04-11
KR880002624B1 (ko) 1988-12-07
GB8424535D0 (en) 1984-11-07
GB2147297B (en) 1987-04-15
SE465928B (sv) 1991-11-18
JPS60100560A (ja) 1985-06-04
IE58084B1 (en) 1993-06-30
IT8422922A0 (it) 1984-09-28
DK169546B1 (da) 1994-11-28
YU45667B (sh) 1992-07-20
SE8404869L (sv) 1985-03-31
ZA847589B (en) 1985-05-29
CA1237723A (en) 1988-06-07
DK468284A (da) 1985-03-31
GB2147297A (en) 1985-05-09
AU3364884A (en) 1985-04-04
YU172184A (en) 1986-10-31

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