KR860002484A - 방향족-1,4-옥스아제핀온 및 티온의 제조방법 - Google Patents

방향족-1,4-옥스아제핀온 및 티온의 제조방법 Download PDF

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KR860002484A
KR860002484A KR1019850006808A KR850006808A KR860002484A KR 860002484 A KR860002484 A KR 860002484A KR 1019850006808 A KR1019850006808 A KR 1019850006808A KR 850006808 A KR850006808 A KR 850006808A KR 860002484 A KR860002484 A KR 860002484A
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compound
dimethylamino
lower alkyl
formula
acid addition
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KR1019850006808A
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KR900003852B1 (ko
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섹 로(외 1) 영
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원본 미기재
에이. 에이치. 로빈스 캄파니, 인코포레이티드
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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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/80—Acids; Esters in position 3
    • 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
    • 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D267/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D267/02—Seven-membered rings
    • C07D267/08—Seven-membered rings having the hetero atoms in positions 1 and 4
    • C07D267/12—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
    • C07D267/14—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with one six-membered ring

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  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Pyridine Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

내용 없음

Description

방향족-1,4-옥스아제핀온 및 티온의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (16)

  1. (1) (a) 알칸을아민 또는 보호되거나 비보호된 2급 아민 작용기를 갖는 알칸올아민을 비친핵성 알칼리 금속 강염기와 반응시킨 다음, 이 반응생성물을 방향족 화합물과 반응시키고, 2급아민 작용기가 보호된 경우에는 보호기를 제거하여 일반식(Ⅱ)의 화합물을 생성하거나, (b) R3가 알칼리 금속이온인 방향족 화합물을 탈수제 또는 축합제의 존재하에 알칸올아민과 반응시켜 일반식(Ⅲ)의 화합물을 생성하는 조건을 이용하여 일반식(Ⅴ)의 방향족 화합물을 일반식(Ⅳ)의 알칸올아민 화합물과 반응시킨 다음;
  2. (2) 단계(1)에서 생성된 화합물을 폐환시켜 일반식(Ia)의 화합물을 생성하고;
  3. (3) 목적하는 바에 따라 임의로는 단계(2)에서 생성된 화합물을 황화제와 반응시켜 일반식(Ib)의 화합물을 생성함을 특징으로 하는 일반식(Ⅰ)의 화합물, 또는 약제학적으로 허용 가능한 이의 산부가염을 제조하는 방법.
  6. 상기식에서, A는 벤젠, 나프탈렌, 피리딘 또는 퀴놀린으로부터 선택된 방향족 환이고, 이들 환은 할로겐, 저급 알킬, 저급 알콕시, 디저급-알킬아미노, 니트로 또는 트리플루오로메틸로부터 선택된 1 또는 2개의 Y 라디칼로 임의 치환되고〔단, 일반식(a)(b) 및 (Ⅰ)에서 상기 방향족 환들은 옥스아제핀 잔기와 함께 2개의 탄소원자를 공유한다〕; B는 산소 또는 황이며; R은 수소, 저급 알킬, 사이클로알킬 또는 페닐-저급알킬(여기서, 페닐은 할로겐, 저급알킬, 저급알콕시, 니트로 또는 트리플루오로 메틸로부터 선택된 1 또는 2개의 라이칼로 임의 치환될 수 있다)이고; n은 1,2 또는 3이며; R4및 R5는 수소 또는 C1-C5저급 알킬이고; Z는 -NR1R2, 1H-피라졸-1-일, 1H-이미다졸-1-일, 1H-이미다졸-2-일 또는 4,5-디하이드로 1H-이미다졸-2-일이다(상기는 Z에 대한 정의에서, R1및 R2는 저급 알킬, 사이클로알킬 또는 페닐-저급 알킬(여기서, 페닐은 할로겐, 저급 알킬, 저급알콕시, 니트로, 트리플루오로메틸 또는 시아노로 부터 선택된 1 또는 2개의 라디칼로 임의 치환될 수 있다)이거나, 인접한 질소원자와 함께 1-아세티디닐, 1-피롤리디닐, 2,5-디메틸피롤리딘-1-일, 2-메틸-피롤리딘-1-일, 1-피페리디닐, 4-치환된 피페리딘-1-일, 4-〔비스(4-플루오로페닐)메틸〕-피페리딘-1-일, 4-모르폴리닐, 1-피페라지닐, 4-치환된 피페라진-1-일, 1,2,3,6-테트라하이드로피리딘-1-일, 2,5-디하이드로-1H-피롤-1-일 또는 1H-피롤-1-일로부터 선택된 헤테로사이클릭잔기를 형성할 수 있고; R3는 수소 알칼리 금속 또는 에스테르화 그룹이며; R6는 수소 또는 아민보호그룹이다.
  7. 제1항에 있어서, 2-〔2-(디메틸아미노)메틸〕-2,3-디하이드로-4-메틸피리도 〔3,2-b〕-1,4-옥스-아제핀-5(4H)-온 또는 약제학적으로 허용가능한 이의 산부가염을 제조하는 방법.
  8. 제1항에 있어서, 2-〔2-(디메틸아미노)에틸〕-2,3-디하이드로-4-메틸-1,4-옥스아제피노〔6,7-C〕퀴놀린-5(4H)-온 또는 약제학적으로 허용가능한 이의 산부가염을 제조하는 방법.
  9. 제1항에 있어서, 2-〔2-(디메틸아미노)에틸〕-2,3-디하이드로피리도 〔3,2-f〕-1,4-옥스아제핀-5(4H)-온 또는 약제학적으로 허용가능한 이의 산부가염을 제조하는 방법.
  10. 제1항에 있어서, 2-〔2-(디메틸아미노)에틸〕-2,3-디하이드로피리도 〔3,2-f〕-1,4-옥스아제핀-5(4H)-더온 또는 약제학적으로 허용가능한 이의 산부가염을 제조하는 방법.
  11. 제1항에 있어서, 2-〔(디메틸아미노)에틸〕-2,3-디하이드로-4-메틸피리도-
  12. 〔3,2-f〕-1,4-옥스-아제핀-5(4H)-티온 또는 약제학적으로 허용가능한 이의 산부가염을 제조하는 방법.
  13. 제1항에 있어서, 단계(1)의 (a)에서 생성된 중간체가 2-〔2-(1-아미노-4-디메틸아미노-2-부틸옥시)〕-3-피리딘카복실산 또는 이의 알칼리 금속염인 방법.
  14. 제1항에 있어서, 단계(1)의 (b)에서 생성된 중간체가 2-클로로-N-〔4-(디메틸아미노)-2-하이드록시-부틸〕-3-피리딘카복스아미드 또는 이의 산 부가염인 방법.
  15. 제1항에 있어서, 단계(1)의 (b)에서 생성된 중간체가 2-클로로-N-〔3-(디메틸아미노)-2-하이드록시-프로필〕-N-메틸-3-피리딘카복스아미드 또는 이의 산부가염인 방법.
  16. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019850006808A 1984-09-19 1985-09-18 방향족-1,4-옥스아제핀-온 및 -티온, 및 이의 제법 KR900003852B1 (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US652,017 1984-09-19
US06/652,017 US4610819A (en) 1984-09-19 1984-09-19 Process for the preparation of aromatic-1,4-oxazepinones and thiones
US652017 1984-09-19

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KR860002484A true KR860002484A (ko) 1986-04-26
KR900003852B1 KR900003852B1 (ko) 1990-06-02

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US (1) US4610819A (ko)
EP (1) EP0175570A3 (ko)
JP (1) JPS6178789A (ko)
KR (1) KR900003852B1 (ko)
AU (2) AU586440B2 (ko)
CA (1) CA1277983C (ko)
DK (1) DK423485A (ko)
ES (1) ES8802305A1 (ko)
FI (1) FI853585L (ko)
GR (1) GR852247B (ko)
HU (2) HU194245B (ko)
IL (1) IL76243A (ko)
IN (1) IN162290B (ko)
NO (1) NO853665L (ko)
NZ (1) NZ213523A (ko)
PH (2) PH22955A (ko)
PL (2) PL150760B1 (ko)
PT (1) PT81157B (ko)
YU (2) YU142785A (ko)
ZA (1) ZA856527B (ko)

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Publication number Priority date Publication date Assignee Title
US4746655A (en) * 1987-06-10 1988-05-24 A. H. Robins Company, Incorporated Fused aromatic-spiropiperidine oxazepinones(and thiones)
GB8727385D0 (en) * 1987-11-23 1987-12-23 Lundbeck & Co As H Heterocyclic compounds
WO2019173761A1 (en) 2018-03-09 2019-09-12 The United States Of America, As Represented By The Secretary, Department Of Health And Human Services C-abl tyrosine kinase inhibitory compound embodiments and methods of making and using the same

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US3794639A (en) * 1966-03-10 1974-02-26 Squibb & Sons Inc Benzoxazepines and benzothiazepines
ZA836994B (en) * 1982-09-30 1984-05-30 Robins Co Inc A H Fused aromatic oxazepinones and sulfur analogs thereof
DE3382028D1 (de) * 1982-09-30 1991-01-10 Robins Co Inc A H Kondensierte aromatische oxazepinone und sulphuranaloge, ihrer herstellung und verwendung als histamin-antagonist.

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NZ213523A (en) 1989-08-29
ES8802305A1 (es) 1987-03-16
JPS6178789A (ja) 1986-04-22
ES547084A0 (es) 1987-03-16
PH22955A (en) 1989-02-03
PH23204A (en) 1989-06-06
AU586440B2 (en) 1989-07-13
ZA856527B (en) 1986-04-30
FI853585L (fi) 1986-03-20
HUT42070A (en) 1987-06-29
PL147855B1 (en) 1989-08-31
IN162290B (ko) 1988-04-23
IL76243A (en) 1990-07-26
AU4767385A (en) 1986-03-27
YU142785A (en) 1988-02-29
KR900003852B1 (ko) 1990-06-02
HU195485B (en) 1988-05-30
PT81157A (en) 1985-10-01
FI853585A0 (fi) 1985-09-18
IL76243A0 (en) 1986-01-31
HU194245B (en) 1988-01-28
PL255423A1 (en) 1987-05-18
EP0175570A3 (en) 1988-07-20
PL150760B1 (en) 1990-06-30
CA1277983C (en) 1990-12-18
YU144187A (en) 1988-10-31
EP0175570A2 (en) 1986-03-26
DK423485A (da) 1986-03-20
US4610819A (en) 1986-09-09
HUT40426A (en) 1986-12-28
GR852247B (ko) 1986-01-17
NO853665L (no) 1986-03-20
DK423485D0 (da) 1985-09-18
AU4004789A (en) 1989-12-07
PT81157B (pt) 1987-10-20

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