KR860001788A - 인돌 유도체의 제조방법 - Google Patents

인돌 유도체의 제조방법 Download PDF

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KR860001788A
KR860001788A KR1019850005553A KR850005553A KR860001788A KR 860001788 A KR860001788 A KR 860001788A KR 1019850005553 A KR1019850005553 A KR 1019850005553A KR 850005553 A KR850005553 A KR 850005553A KR 860001788 A KR860001788 A KR 860001788A
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salt
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protected derivative
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KR1019850005553A
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KR930003759B1 (ko
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윌리암 옥스포드 알렉산더
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베리 앤소니 뉴샘
글락소그룹 리미티드
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D203/08—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring nitrogen atom
    • C07D203/14—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring nitrogen atom with carbocyclic rings directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • 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
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • 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
    • A61P25/06—Antimigraine agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/12—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
    • C07D209/16—Tryptamines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D209/24—Radicals 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 an alkyl or cycloalkyl radical attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
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  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Pain & Pain Management (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

내용 없음

Description

인동 유도체의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (7)

  1. 구조식(Ⅱ)의 화합물을 폐환시키거나; 일반식(Ⅴ)의 화합물 또는 이의 보호된 유도체를 디메틸아민과 반응시키거나; 일반식(Ⅷ)의 화합물 또는 이의 염 또는 보호된 유도체를 환원시키거나; 일반식(Ⅸ)의 화합물 또는 이의 염을 메틸아민과 반응시키거나; 일반식(Ⅸ)의 화합물을 메틸화제와 반응시키거나; 일반식(XII)의 4급 암모늄염을 탈알킬화하거나; 구조식(XIV)의 인돌을 탈수소화하거나; 구조식(Ⅰ)의 화합물의 보호된 유도체 또는 이의 염으로부터 보호그룹(들)을 제거하고; 경우에 따라 생성된 구조식(Ⅰ)의 화합물 또는 이의 염으로부터 존재하는 보호그룹을 제거하거나, 구조식(I)의 화합물 또는 이의 염을 생리학적으로 무독한 염 또는 용매화물로 전환시킴을 특징으로 하여, 구조식(Ⅰ)의 화합물 또는 이의 생리학적으로 무독한 염 또는 용매화물로 제조하는 방법.
    상기의 일반식에서, Y는 쉽게 치환될 수 있는 그룹이고, W는 환원되어 디메틸아미노 메틸그룹을 형성 할 수 있는 그룹이며, X는 이탈원자 또는 그룹이고, R12,R13및 R14는 각각 수소 또는 메틸그룹인데, 단이들중의 적어도 하나는 수소이며, R15는 메틸그룹 또는 그룹-CH2CH2R16(여기서, R16은 전자 흡인그룹이다)이고, E는 음이온이다.
  2. 제1항에 있어서, 생리학적으로 무독한 염이 유기산 또는 무기산으로 형성하 산 부가염인 방법.
  3. 제2항에 있어서, 생리학적으로 무독한 염이염산염, 브롬화수소산염, 황산염, 질산염, 인산염, 포름산염, 메실산염, 시트로산염, 벤조산염, 푸마르산염, 말레산염 또는 숙신산염인 방법.
  4. 제3항에 있어서, 생리학적으로 무독한 염이 1:1 숙신산염인 방법.
  5. 제1항에 있어서, 일반식(Ⅷ)의 화합물 또는 이의 염 또는 보호된 유도체를 환원시키는 공정이 구조식(Ⅰ)의 화합물의 아미노에틸 또는 메틸아미노에틸유도체를 적합한 환원제의 존재하에 포름알데하이드로 환원성 메틸화함을 특징으로 하는 방법.
  6. 제5항에 있어서, 환원제가 알카리 금속 또는 알카리토금속 보로하이드라이드 또는 시아노보로하이드라이드인 방벙.
  7. 제6항에 있어서, 환원제가 수소화붕소나트륨인 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019850005553A 1984-08-01 1985-08-01 인돌 유도체의 제조방법 KR930003759B1 (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB8,419,575 1984-08-01
GB8.419.575 1984-08-01
GB848419575A GB8419575D0 (en) 1984-08-01 1984-08-01 Chemical compounds

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KR860001788A true KR860001788A (ko) 1986-03-22
KR930003759B1 KR930003759B1 (ko) 1993-05-10

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US (1) US5037845A (ko)
JP (1) JPH0623197B2 (ko)
KR (1) KR930003759B1 (ko)
AT (1) AT386196B (ko)
AU (1) AU573878B2 (ko)
BE (1) BE903006A (ko)
CA (1) CA1241004A (ko)
CH (1) CH666026A5 (ko)
CZ (1) CZ280530B6 (ko)
DE (1) DE3527648A1 (ko)
DK (1) DK158942C (ko)
DO (1) DOP1989004759A (ko)
EC (1) ECSP941096A (ko)
EG (1) EG17283A (ko)
ES (6) ES8700234A1 (ko)
FI (1) FI78466C (ko)
FR (1) FR2568571B1 (ko)
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HK (1) HK33289A (ko)
HU (1) HU201738B (ko)
IE (1) IE58122B1 (ko)
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CA1241004A (en) 1988-08-23
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IL75986A (en) 1989-02-28
UA6329A1 (uk) 1994-12-29
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MX14221A (es) 1993-10-01
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ES557483A0 (es) 1988-02-16
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IE58122B1 (en) 1993-07-14
SU1498386A3 (ru) 1989-07-30
AT386196B (de) 1988-07-11
HU201738B (en) 1990-12-28
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LU86032A1 (fr) 1986-02-18
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