KR850004462A - 1,3,4,5-테트라히드로벤즈[c,d]인돌류 제조방법 - Google Patents

1,3,4,5-테트라히드로벤즈[c,d]인돌류 제조방법 Download PDF

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KR850004462A
KR850004462A KR1019840008206A KR840008206A KR850004462A KR 850004462 A KR850004462 A KR 850004462A KR 1019840008206 A KR1019840008206 A KR 1019840008206A KR 840008206 A KR840008206 A KR 840008206A KR 850004462 A KR850004462 A KR 850004462A
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compound
formula
process according
iii
acid
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KR1019840008206A
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KR910006979B1 (ko
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글라서 토마스
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하이레딘 야코비
트로폰베르케 게엠베하 운트 캄파니,카게
게르트바디케
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    • 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
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/90—Benzo [c, d] indoles; Hydrogenated benzo [c, d] indoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • 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
    • 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
    • A61P25/24—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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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

Abstract

내용 없음

Description

1,3,4,5-테트라히드로벤즈[c,d]인돌류 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (10)

  1. 일반식(Ⅱ)의 화합물을 치환체 X에 대해 파라에서 니트로화시키고, 일반식(Ⅲ)의 생성된 니트로 화합물을 일반식 R4-O-CO-CO-OR4의 옥살산 에스테르로 아실화시켜서 일반식(Ⅳ)의 화합물을 얻고, 1 이상의 단계로 이 화합물 중의 에스테르기를 가수 분해시키고, 니트로기를 환원원시킨 다음, 생성물을 환화시키고, 이어서 탈카르복실화시킴을 특징으로하는 다음 일반식(Ⅰ)의 화합물 제조방법.
    위 식에서, R1및 R2는 수소, C1-6-알킬 또는 C2-6-알케닐이거나, 질소원자와 함께 5-또는 6원 복소환고리를 형성하며, 이 고리는 1개 또는 2개의 C1-6알킬기로 임의로 치환시킬 수 있고, X는 OR3또는 SR3이고, R3은 H 또는 C1-4알킬이고, R4는 CH3또는 C2H5이다.
  2. 일반식(Ⅲ)의 화합물을 일반식(Ⅶ)의 아닐린으로 환원시키고, 이 환원생성물을 일반식(Ⅷ)의 이소니트릴으로 전환시키고, 최종적으로 강염기로 처리하여 일반식(Ⅰ)의 화합물로 환화시킴을 특징으로하는 일반식(Ⅰ)의 화합물의 제조방법.
  3. 제2항에 있어서, 일반식(Ⅶ)의 화합물을 2상계(相界)에서 일반식(Ⅷ)의 화합물로 전환시킴을 특징으로하는 방법.
  4. 제1항에 있어서, 2-아미노테르랄린(Ⅱ)을 니트로 화합물(Ⅲ)로 니트로화시키는 반응을, 무기산 또는 유기카르복실산 중에서 니트로화제로서 NaNO3중의 농질산 또는 발연 질산으로 행함을 특징으로하는 방법.
  5. 제4항에 있어서, 용매로서 황산, 질산 또는 트리플루오로 아세트산을 사용함을 특징으로하는 방법.
  6. 제5항에 있어서, 반응을 60°∼40℃의 온도에서 행함을 특징으로하는 방법.
  7. 제1항에 있어서, 화합물(Ⅲ)을 화합물(Ⅳ)로 아실화시키는 반응을, 불활성, 양성자성 또는 중성용매중에서 감염기 존재하에 디메틸 또는 디에틸 옥살레이트로 행함을 특징으로하는 방법.
  8. 제7항에 있어서, 활성화된 메틸렌기의 양성자를 제거시키기 위한 염기로서 유기금속 염기, 특히 리튬 디이소프로필아미드, n-부틸-리튬, NaH 또는 알칼리 금속 알코올레이트를 사용함을 특징으로 하는 방법.
  9. 제8항에 있어서, 중성 용매로서 디에틸 에테르, 테트라히드로푸란, 디옥산, 1,2-디케톡시에탄, 디글라임, 디메틸포름 아미드 또는 디메틸술폭시드를 사용함을 특징으로 하는 방법.
  10. 제9항에 있어서, 양성자성 용매로서 메타놀 또는 에타놀을 사용함을 특징으로하는 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019840008206A 1983-12-23 1984-12-21 1,3,4,5-테트라히드로벤즈[c,d]인돌, 이들의 제조 방법 및 이들을 유효 성분으로 하는 치료제 KR910006979B1 (ko)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3346573A DE3346573A1 (de) 1983-12-23 1983-12-23 1,3,4,5-tetrahydrobenz(c,d)indole, ein verfahren zu ihrer herstellung und ihre verwendung
DEP3346573.8 1983-12-23

Publications (2)

Publication Number Publication Date
KR850004462A true KR850004462A (ko) 1985-07-15
KR910006979B1 KR910006979B1 (ko) 1991-09-14

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ID=6217791

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Application Number Title Priority Date Filing Date
KR1019840008206A KR910006979B1 (ko) 1983-12-23 1984-12-21 1,3,4,5-테트라히드로벤즈[c,d]인돌, 이들의 제조 방법 및 이들을 유효 성분으로 하는 치료제

Country Status (16)

Country Link
EP (1) EP0148440B1 (ko)
JP (1) JPS60156670A (ko)
KR (1) KR910006979B1 (ko)
AT (1) ATE37711T1 (ko)
AU (1) AU566758B2 (ko)
DE (2) DE3346573A1 (ko)
DK (1) DK157295C (ko)
ES (2) ES8605237A1 (ko)
FI (1) FI79299C (ko)
GR (1) GR82577B (ko)
IL (1) IL73875A (ko)
NO (1) NO162615C (ko)
NZ (1) NZ210665A (ko)
PH (1) PH23272A (ko)
PT (1) PT79750A (ko)
ZA (1) ZA8410038B (ko)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL74222A (en) * 1984-02-06 1988-07-31 Lilly Co Eli 6-substituted-4-dialkylamino tetrahydrobenz(c,d)indoles,their preparation and pharmaceutical compositions comprising them
US4983622A (en) * 1984-02-06 1991-01-08 Eli Lilly And Company 6-substituted-4-dialkylaminotetrahydrobenz(c,d)indoles
US5026869A (en) * 1984-02-06 1991-06-25 Eli Lilly And Company 6-substituted-4-dialkylaminotetrahydrobenz(c,d)indoles
CA1266482A1 (en) * 1984-05-24 1990-03-06 Carl Kaiser 6-oxygenated-1,3,4,5-tetrahydrobenz(cd)indol-4-amines
DE3525564A1 (de) * 1985-07-15 1987-02-05 Schering Ag Tricyclische verbindungen mit indolstruktur, verfahren zu ihrer herstellung und deren verwendung als arzneimittel
US4745126A (en) * 1987-03-12 1988-05-17 Eli Lilly And Company Method of treating anxiety with tetrahydrobenz[c,d]indole-6-carboxamides
DE3809155A1 (de) * 1988-03-18 1989-09-28 Bayer Ag 1,3,4,5-tetrahydrobenz-(c,d)-indole
US5204340A (en) * 1989-04-11 1993-04-20 Eli Lilly And Company Tetrahydrobenz(c,d)indole serotonin agonists
US5273975A (en) * 1989-06-09 1993-12-28 The Upjohn Company Heterocyclic amines having central nervous system activity
US5212319A (en) * 1990-02-26 1993-05-18 Eli Lilly And Company Intermediates to 4-amino-hexahydrobenz[cd]indoles and processes therefor
US5302612A (en) * 1990-02-26 1994-04-12 Eli Lilly And Company 6-substituted-hexahydrobenz[cd]indoles
US5340838A (en) * 1990-05-04 1994-08-23 Eli Lilly And Company Method of inhibiting gastric acid secretion with 2-phenylcyclopropylamines
US5258379A (en) * 1990-05-04 1993-11-02 Eli Lilly And Company Method of inhibiting gastric acid secretion with n-arylpiperazines
US5096908A (en) * 1990-05-04 1992-03-17 Eli Lilly And Company Method of inhibiting gastric acid secretion
US5229409A (en) * 1990-08-15 1993-07-20 Eli Lilly And Company 6-substituted-tetrahydrobenz[cd]indoles
US5229410A (en) * 1990-08-15 1993-07-20 Eli Lilly And Company 6-substituted-hexahydrobenz[cd]indoles
US5244912A (en) * 1991-03-28 1993-09-14 Eli Lilly And Company 6-heterocyclic-4-amino-1,3,4,5-tetrahydrobenz(cd)indoles and pharmaceutical use thereof
US5643934A (en) * 1991-03-28 1997-07-01 Eli Lilly And Company 6-heterocyclic-4-amino-1,2,2a,3,4,5-hexahydrobenz [CD]indoles
US5244911A (en) * 1991-03-28 1993-09-14 Eli Lilly And Company 6-heterocyclic-4-amino-1,2,2a,3,4,5-hexahydrobenz(cd)indoles and pharmaceutical use thereof
US5364856A (en) * 1991-03-28 1994-11-15 Eli Lilly And Company 6-heterocyclic-4-amino-1,3,4,5-tetrahydrobenz[CD]indoles
US5347013A (en) * 1991-03-28 1994-09-13 Eli Lilly And Company 6-heterocyclic-4-amino-1,2,2a,3,4,5-hexahydrobenz[cd]indoles
WO1995004056A1 (en) 1993-07-27 1995-02-09 The Upjohn Company Heterocyclic amines having central nervous system activity
TW430660B (en) * 1996-05-30 2001-04-21 Mochida Pharm Co Ltd Novel benzindole derivatives for neuron cell protection, processes for production, and the pharmaceutical compounds containing them
US7074927B2 (en) 1999-05-13 2006-07-11 Pharmacia & Upjohn Company Heterocyclic amines having central nervous system activity

Family Cites Families (7)

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Publication number Priority date Publication date Assignee Title
US3194811A (en) * 1963-09-05 1965-07-13 Merck & Co Inc Aroyl-benzindolyl acids
CH517732A (de) * 1969-10-24 1972-01-15 Sandoz Ag Verfahren zur Herstellung neuer Guanidin- Verbindungen
US4110339A (en) * 1977-11-25 1978-08-29 Eli Lilly And Company 4-(Di-n-propyl)amino-1,3,4,5-tetrahydrobenz[cd]indole
US4282240A (en) * 1979-11-23 1981-08-04 Merck & Co., Inc. Amino substituted tetrahydrobenzindoles
FR2522658A1 (fr) * 1982-03-05 1983-09-09 Roussel Uclaf Application a titre de medicaments de derives du trans 4-amino benz (c,d) indol-5-ol ainsi que de leurs sels, compositions les renfermant, nouveaux derives et leur procede de preparation
IL74222A (en) * 1984-02-06 1988-07-31 Lilly Co Eli 6-substituted-4-dialkylamino tetrahydrobenz(c,d)indoles,their preparation and pharmaceutical compositions comprising them
CA1266482A1 (en) * 1984-05-24 1990-03-06 Carl Kaiser 6-oxygenated-1,3,4,5-tetrahydrobenz(cd)indol-4-amines

Also Published As

Publication number Publication date
ES549978A0 (es) 1986-12-01
AU566758B2 (en) 1987-10-29
PH23272A (en) 1989-06-23
FI79299B (fi) 1989-08-31
NO844868L (no) 1985-06-24
GR82577B (en) 1985-04-23
JPH0475909B2 (ko) 1992-12-02
EP0148440A1 (de) 1985-07-17
ES8701721A1 (es) 1986-12-01
ES538290A0 (es) 1986-03-16
DE3474444D1 (en) 1988-11-10
DK157295B (da) 1989-12-04
ES8605237A1 (es) 1986-03-16
FI845070L (fi) 1985-06-24
EP0148440B1 (de) 1988-10-05
PT79750A (en) 1985-01-01
DK625584A (da) 1985-06-24
JPS60156670A (ja) 1985-08-16
FI845070A0 (fi) 1984-12-20
ZA8410038B (en) 1985-08-28
NZ210665A (en) 1988-06-30
KR910006979B1 (ko) 1991-09-14
NO162615B (no) 1989-10-16
IL73875A (en) 1988-08-31
NO162615C (no) 1990-01-24
DK625584D0 (da) 1984-12-21
DK157295C (da) 1990-05-07
IL73875A0 (en) 1985-03-31
DE3346573A1 (de) 1985-07-04
ATE37711T1 (de) 1988-10-15
FI79299C (fi) 1989-12-11
AU3690484A (en) 1985-07-04

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