KR830010057A - Nn-(아릴티오알킬)-n'-(아미노알킬) 우레아의 제조방법 - Google Patents

Nn-(아릴티오알킬)-n'-(아미노알킬) 우레아의 제조방법 Download PDF

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KR830010057A
KR830010057A KR1019820002205A KR820002205A KR830010057A KR 830010057 A KR830010057 A KR 830010057A KR 1019820002205 A KR1019820002205 A KR 1019820002205A KR 820002205 A KR820002205 A KR 820002205A KR 830010057 A KR830010057 A KR 830010057A
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alk
general formula
hydrogen
lower alkyl
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KR890001811B1 (ko
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제이알 제임스 로버트 쉥크린
페터 죤슨 3세 크리스토퍼
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로버트 피. 울프
에이. 에이치. 로빈스 캄파니 인코포레이트드
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
    • C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
    • 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
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C317/28—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
    • C07C323/43—Y being a hetero atom
    • C07C323/44—X or Y being nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C335/04—Derivatives of thiourea
    • C07C335/06—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms
    • C07C335/08—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Furan Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

내용 없음

Description

NN-(아릴티오알킬)-N′-(아미노알킬) 우레아의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (1)

  1. 하기 방법 (a),(b),(c) 또는 (d)에 의해 하기 일반식(Ⅰ)의 N-(아릴티오알킬)-N′(아미노알킬)우레아 및 티오우레아, 그 산화 유도체, 설피닐 및 설포닐 동족체와 그 약제학적으로 허용되는 산부가염 및 수화물을 제조하는 방법.
    (Ⅰ)
    (상기식에서, Ar이 1 또는 2-나프틸, 2,3-디하이드로-1H-인덴-4(또는 5)일, 2-푸라닐, 페닐이거나 또는 저급알킬, 저급알콕시, 할로겐, 트리플루오로메틸, 니트로, 시아노,(여기서, R5및 R6는 수소 또는 저급알킬이다)중의 하나 내지 3개의 같거나 다른 라디칼에 의해 치환된 페닐이며, 또한 An은 사이에 끼어들어 B와 연결된 하나의 메틸렌그룹을 포함할 수 있으며, R1및 R2는 할로겐, 저급알킬, 사이클로알킬, 페닐 또는 페닐-저급알킬(여기서 페닐은 할로겐, 저급알킬 또는 저급 알콕시에 의해 치환될 수 있다)이며, X는 산소 또는 유황이며, B는-S,또는이며, R3및 R4는 같거나 다를수 있으며, 수소, 저급알킬, 페닐 또는 페닐-저급 알킬(여기서, 페닐은 할로겐, 저급 알킬 또는 저급 알콕시에 의해 치환될 수 있다)이거나, 또는 R3와 R4는 인접한 질소와 함께 복소환성 잔기를 이루며, alk1및 alk2는 같거나 다를수 있으며, 저급 알킬렌 또는 저급 알킬렌-저급 알킬이다).
    a) 하기 일반식(Ⅳa)의 아민을 프로톤 스폰지 존재하에 일반식 CXCI2의 화합물과 반응시켜 중간체인 하기 일반식(Ⅲ)의 화합물을 얻고 이 중간체를 하기 일반식(Ⅱa)의 아민과 반응시켜 상기 일반식(Ⅰ)의 화합물을 제조한다.
    (Ⅱa)
    (Ⅲ)
    Ar-B-alk1-NHR1(Ⅳa)
    (상기식에서,
    Ar, B, X, alk1, alk2, R1, R2, R3및 R4는 상기 정의된 바와 같으며, B는가 아니며, 단, R1이 수소일때는, P는 0이고 점선은 이소시아 네이트를 형성하는 이중결합이며, R1이 수소가 아닐때는 P는 1이고 점선은 아무 의미가 없으며, R2가 수소가 아닐때는 R3및 R4는 수소가 아니어야 하며, 또는 R2가 R3와 같고, R4는 수소이다).
    b) 하기 일반식(Ⅱb)의 알킬디아민을 1,1′-카보닐디이미다졸 또는 1,1′-티오카보닐디이다졸 및 하기 일반식(Ⅳa)의 아민과 반응시켜 하기 일반식(Ⅰb)의 화합물을 제조한다.
    (Ⅰb)
    H2N-alk2NR3R4(Ⅱb)
    Ar-B-alk'-NHR' (Ⅳa)
    (상기식에서,
    Ar, B, alk′, alk2, R1, R3,R4, 및 X는 정의된 바와 같으며, 단, R3및 R4는 절대 수소가 아니다.)
    c) 하기 일반식(Ⅳb)의 아민을 1,1′-카보닐디이미다졸 또는 1,1′-티오카보닐디이미다졸 및 하기 일반식(Ⅱb)의 알킬디아민과 반응시켜 하기 일반식(Ⅰc)의 화합물을 제조한다.
    (Ⅰc)
    R2NH-alk2-NR3R4(Ⅱb)
    Ar-B-alk'-NH2(Ⅳb)
    (상기식에서,
    Ar, B, R2, R3, R4, X, alk′ 및 alk2는 상기 정의된 바와 같다.)
    d) 하기 일반식(Ⅵ)의 화합물을 일반식 c×cl2의 화합물과 반응시켜 하기 일반식(Ⅴ)의 중간체를 얻고 이 중간체를 삼치환된 아민 및 하기 일반식(Ⅳa)의 아민과 반응시켜 하기 일반식(Ⅰd)의 화합물을 제조한다.
    Ar-B-alk'-N-C-N-alk2-N R3R4(Ⅰd)
    Ar-B-alk'-NHR' (Ⅳa)
    (Ⅴ)
    R4R3N-alk2-NHR2(Ⅵ)
    (상기식에서,
    Ar, alk1, alk2, B, X, R1, R2, R3및 R4는 상기 정의된 바와 같으며, R2, R3및 R4는 절대로 수소가 아니다).
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR8202205A 1981-05-20 1982-05-20 N-(아릴티오알킬)-n'-(아미노알킬)우레아 및 이의 제조방법 KR890001811B1 (ko)

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US26527881A 1981-05-20 1981-05-20
US265278 1981-05-20
US34545282A 1982-02-03 1982-02-03
US345452 1982-02-03

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KR890001811B1 KR890001811B1 (ko) 1989-05-23

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EP (1) EP0066415B1 (ko)
KR (1) KR890001811B1 (ko)
AU (1) AU544976B2 (ko)
CA (1) CA1180013A (ko)
DE (1) DE3266645D1 (ko)
DK (1) DK228482A (ko)
ES (3) ES8303303A1 (ko)
FI (1) FI76557C (ko)
GR (1) GR76412B (ko)
HK (1) HK96986A (ko)
IE (1) IE53342B1 (ko)
IL (1) IL65567A (ko)
IN (1) IN155992B (ko)
NO (1) NO153848C (ko)
NZ (1) NZ200669A (ko)
PH (1) PH23473A (ko)
PT (1) PT74930B (ko)

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IL74140A (en) * 1984-04-10 1988-05-31 Robins Co Inc A H Substituted n-((amino)alkyl)-1-pyrrolidine,-1-piperidine and-1-homopiperidine-carboxamides and pharmaceutical compositions containing them
US4895840A (en) * 1987-06-10 1990-01-23 A. H. Robins Company, Incorporated N-(aryl-,aryloxy-,arylthio-arylsulfinyl-and arylsulfonyl-)alkyl-N,N'-(or n'n')alkylaminoalkyl ureas and cyanoguanidines
FR2664269B1 (fr) * 1990-07-05 1992-10-02 Roussel Uclaf Nouveaux derives n-substitues d'alpha-mercapto alkylamines, leur procede de preparation, leur application a titre de medicaments et les compositions les renfermant.
EP1216988A4 (en) * 1999-09-28 2005-04-20 Nihon Nohyaku Co Ltd THIOALKYLAMINE DERIVATIVES AND METHOD FOR THE PRODUCTION THEREOF

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US2832756A (en) * 1955-04-15 1958-04-29 Rohm & Haas Monomeric polymerizable ureido and thioureido compounds, methods for producing them and polymers thereof
FR2296406A1 (fr) * 1974-12-31 1976-07-30 Oreal Nouvelles compositions cosmetiques a base de derives sulfoxydes de la cysteamine
GB1604674A (en) * 1977-05-17 1981-12-16 Allen & Hanburys Ltd Aminoalkyl-benzene derivatives

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AU544976B2 (en) 1985-06-27
ES512329A0 (es) 1983-02-01
IE53342B1 (en) 1988-10-26
DK228482A (da) 1982-11-21
EP0066415A3 (en) 1983-09-14
NO153848B (no) 1986-02-24
EP0066415B1 (en) 1985-10-02
ES512328A0 (es) 1983-02-01
KR890001811B1 (ko) 1989-05-23
NZ200669A (en) 1985-12-13
PH23473A (en) 1989-08-07
FI76557B (fi) 1988-07-29
ES8303305A1 (es) 1983-02-01
IN155992B (ko) 1985-04-20
ES8303304A1 (es) 1983-02-01
NO821668L (no) 1982-11-22
PT74930B (en) 1983-12-07
AU8388182A (en) 1982-11-25
PT74930A (en) 1982-06-01
DE3266645D1 (de) 1985-11-07
NO153848C (no) 1986-06-04
ES512330A0 (es) 1983-02-01
FI821776A0 (fi) 1982-05-19
EP0066415A2 (en) 1982-12-08
IL65567A (en) 1985-11-29
GR76412B (ko) 1984-08-10
FI76557C (fi) 1988-11-10
ES8303303A1 (es) 1983-02-01
IL65567A0 (en) 1982-07-30
CA1180013A (en) 1984-12-27
IE821191L (en) 1982-11-20
HK96986A (en) 1986-12-19

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