KR860003240A - 1,2,4- 트리아졸로- 카바메이트의 제조방법 - Google Patents

1,2,4- 트리아졸로- 카바메이트의 제조방법 Download PDF

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KR860003240A
KR860003240A KR1019850007921A KR850007921A KR860003240A KR 860003240 A KR860003240 A KR 860003240A KR 1019850007921 A KR1019850007921 A KR 1019850007921A KR 850007921 A KR850007921 A KR 850007921A KR 860003240 A KR860003240 A KR 860003240A
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methyl
formula
prepared
carbon atoms
triazole
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베버 칼-하인츠 (외 8)
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디이터 라우딘 루돌프 호프만
베링거 잉겔하임 케이지
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Publication of KR860003240A publication Critical patent/KR860003240A/ko

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    • 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
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • 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
    • A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
    • 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
    • A61P25/20—Hypnotics; Sedatives
    • 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, ***e
    • 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
    • A61P25/28—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
    • 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
    • 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
    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond

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  • Engineering & Computer Science (AREA)
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  • Orthopedic Medicine & Surgery (AREA)
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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

내용 없음

Description

1,2,4-트리아졸로-카바메이트의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (10)

  1. 일반식(Ⅱ)의 화합물을, 임의로는 염기를 첨가하여, 일반식(Ⅲ)의 할로카보닐아미드와 반응시키거나 일반식(Ⅳ)의 할로카보네이트와 반응시킨 다음, 이어서 일반식(Ⅴ)의 1급 또는 2급과 아민과 반응시키거나; 일반식(Ⅵ)의 카바미드산 에스테르와 반응시키거나; R3가 수소인 화합물을 제조하는 경우에는 일반식(Ⅶ)의 이소시아네이트와 반응시키고, 임의로는 염형성시킴을 특징으로 하여 일반식(Ⅰ)의 화합물 또는 생리학적으로 무독한 이의 산 부가염을 제조하는 방법.
    상기식에서, R1은 수소, 탄소수 1 내지 8의 직쇄 또는 측쇄 알킬, 3원 내지 6원의 카보사이클릭환, 벤질 또는 펜에틸이고; R2는 할로겐, 메틸, 메톡시 또는 트리플루오로메틸로 일-또는 이-치환될 수 있는 페닐 또는 피리디닐 그룹이며; R3및 R4는 동일하거나 상이하며, 수소, 탄소수 1 내지 6의 직쇄 또는 측쇄 알킬, 탄소수 3 내지 6의 사이클로알킬이거나, 할로겐, 메톡시, 트리플루오로메틸 또는 탄소수 1 내지 6의 직쇄 또는 측쇄 알킬로 임의 치환된 아릴 또는 헤테로아릴그룹이거나, R3및 R4가 질소원자와 함께 탄소수 1 내지 4의 직쇄 또는 측쇄 알킬그룹 하나 이상으로 임의 치환된 5원 또는 6원의 포화환일 수 있고[여기서, 5원 도는 6원환은 추가의 헤테로원자로서 질소, 산소 또는 황을 함유할 수 있으며, 질소를 함유하는 경우에는 탄소수 1 내지 4의 알킬그룹 또는 탄소수 1 내지 3의 하이드록시알킬그룹으로 치환될 수 있다]; X는 할로겐, 바람직하게는 염소이며; R5는 이탈그룹으로서 적절한 알킬 또는 아릴 그룹이다.
  2. 제1항에 있어서, 일반식(Ⅱ)의 화합물을 염기와 반응시켜 이의 염으로 전환시킨 다음, 일반식(Ⅲ),(Ⅳ) 또는 (Ⅵ)의 화합물과 반응시키는 방법.
  3. 제1항에 있어서, R1이 메틸 또는 에틸그룹이고; R2는 염소-치환된 페닐 또는 피리디닐그룹이며; R3는 수소, 또는 메틸 또는 에틸 그룹이고; R4는 탄소수 1 내지 4의 저급 알킬그룹이거나, 또는 R3와 R4가 질소원자와 함께 N-메틸치환된 피페라지닐그룹을 형성하는 일반식(Ⅰ)의 화합물을 제조하는 방법.
  4. 제1항에 있어서, 4-(5-클로로피리딘-2-일)-3-메틸-5-[(4-메틸피페라지닐)카보닐]옥시-1,2,4-트리아졸을 제조하는 방법.
  5. 제1항에 있어서, 4-(5-클로로피리딘-2-일)-3-메틸-5-[N-3급-부틸아미노카보닐]옥시-1,2,4-트리아졸을 제조하는 방법.
  6. 제1항에 있어서, 4-(4-클로로페닐)-3-에틸-5-[(4-메틸피페라지닐)카보닐]옥시-1,2,4-트리아졸을 제조하는 방법.
  7. 제1항에 있어서, 4-(5-클로로피리딘-2-일)-3-메틸-5-[N-디에틸아미노카보닐]옥시-1,2,4-트리아졸을 제조하는 방법.
  8. 제1항에 있어서, 4-(5-클로로피리딘-2-일)-3-메틸-5-[N-메틸아미노카보닐]옥시-1,2,4-트리아졸을 제조하는 방법.
  9. 제1항에 있어서, 4-(5-클로로피리딘-2-일)-3-메틸-5-[N,N-디메틸아미노카보닐]옥시-1,2,4-트리아졸을 제조하는 방법.
  10. 제1항에 있어서, 4-(4-클로로페닐)-3-메틸-5-[(4-메틸피페라지닐)카보닐]옥시-1,2,4-트리아졸을 제조하는 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019850007921A 1984-10-27 1985-10-26 1,2,4- 트리아졸로- 카바메이트의 제조방법 KR860003240A (ko)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19843439450 DE3439450A1 (de) 1984-10-27 1984-10-27 1,2,4-triazolo-carbamate und ihre saeureadditionssalze, verfahren zu ihrer herstellung und arzneimittel
DEP3439450.8 1984-10-27

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US (1) US4732900A (ko)
EP (1) EP0180115A3 (ko)
JP (1) JPS61103876A (ko)
KR (1) KR860003240A (ko)
AU (1) AU576393B2 (ko)
CA (1) CA1244030A (ko)
CS (2) CS255877B2 (ko)
DD (1) DD236928A5 (ko)
DE (1) DE3439450A1 (ko)
DK (1) DK491385A (ko)
ES (2) ES8701738A1 (ko)
FI (1) FI854178L (ko)
GR (1) GR852581B (ko)
HU (1) HU193351B (ko)
IL (1) IL76823A0 (ko)
NO (1) NO854276L (ko)
NZ (1) NZ213969A (ko)
PH (1) PH22446A (ko)
PL (2) PL255940A1 (ko)
PT (1) PT81370B (ko)
SU (2) SU1436873A3 (ko)
ZA (1) ZA858195B (ko)

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Publication number Priority date Publication date Assignee Title
JP2784921B2 (ja) * 1988-03-23 1998-08-13 武田薬品工業株式会社 カルバメート化合物
US5100906A (en) * 1990-04-19 1992-03-31 Merrell Dow Pharmaceuticals Inc. 5-aryl-4-alkyl-3h-1,2,4-triazole-3-thiones useful as memory enhancers
US5331002A (en) * 1990-04-19 1994-07-19 Merrell Dow Pharmaceuticals Inc. 5-aryl-4-alkyl-3H-1,2,4-triazole-3-thiones useful as memory enhancers
US5728834A (en) * 1996-11-14 1998-03-17 Wyckoff Chemical Company, Inc. Process for preparation of 4-aryl-1,2,4-triazol-3-ones
US20050288347A1 (en) * 2004-03-26 2005-12-29 Hodge Carl N Certain triazole-based compounds, compositions, and uses thereof
JP2008526887A (ja) * 2005-01-10 2008-07-24 ユニバーシティ オブ コネチカット カンナビノイド受容体に作用する新規なヘテロピロール類似体
US8853205B2 (en) 2005-01-10 2014-10-07 University Of Connecticut Heteropyrrole analogs acting on cannabinoid receptors
US10053444B2 (en) 2009-02-19 2018-08-21 University Of Connecticut Cannabinergic nitrate esters and related analogs
CA3125847A1 (en) 2020-07-27 2022-01-27 Makscientific, Llc Process for making biologically active compounds and intermediates thereof
CN115991698B (zh) * 2022-11-03 2024-03-29 广东中科药物研究有限公司 一种杂环化合物及其制备方法与应用

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GB681376A (en) * 1949-11-23 1952-10-22 Geigy Ag J R Manufacture of heterocyclic carbamic acid derivatives and their use as agents for combating pests
NL7112373A (ko) * 1970-09-25 1972-03-28
US4209515A (en) * 1974-06-14 1980-06-24 Ciba-Geigy Corporation Triazole derivatives
US4160839A (en) * 1976-03-01 1979-07-10 Gulf Oil Corporation Carbamyltriazole insecticides
JPS59199681A (ja) * 1983-04-26 1984-11-12 Ube Ind Ltd １，２，４−トリアゾ−ル−３−カルボン酸アミド類の製造法
FI850994L (fi) * 1984-03-16 1985-09-17 Ciba Geigy Ag Foerfarande foer framstaellning av nya 1,2,4-triazacykloalkadienderivat.
US4610717A (en) * 1985-11-26 1986-09-09 Shell Oil Company Certain 5-(R-oxy)-1-phenyl or (3-(trifluoromethyl)phenyl)triazoles, useful for controlling undesired plant growth

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PL264492A1 (en) 1987-11-30
PT81370A (de) 1985-11-01
PH22446A (en) 1988-09-12
AU4909485A (en) 1986-05-01
ES554373A0 (es) 1987-04-01
IL76823A0 (en) 1986-02-28
ZA858195B (en) 1987-06-24
GR852581B (ko) 1986-02-26
FI854178A0 (fi) 1985-10-25
CS255877B2 (en) 1988-03-15
AU576393B2 (en) 1988-08-25
EP0180115A3 (de) 1987-01-21
DD236928A5 (de) 1986-06-25
JPS61103876A (ja) 1986-05-22
DE3439450A1 (de) 1986-05-07
SU1436873A3 (ru) 1988-11-07
NZ213969A (en) 1987-11-27
DK491385A (da) 1986-04-28
ES548206A0 (es) 1986-12-01
PL255940A1 (en) 1987-07-13
EP0180115A2 (de) 1986-05-07
DK491385D0 (da) 1985-10-25
HUT40091A (en) 1986-11-28
SU1429934A3 (ru) 1988-10-07
ES8701738A1 (es) 1986-12-01
FI854178L (fi) 1986-04-28
PT81370B (de) 1987-08-20
HU193351B (en) 1987-09-28
NO854276L (no) 1986-04-28
ES8704468A1 (es) 1987-04-01
CS255897B2 (en) 1988-03-15
CA1244030A (en) 1988-11-01
US4732900A (en) 1988-03-22

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