KR900001667A - N-술파밀-프로피온아미딘 유도체의 제조방법 - Google Patents

N-술파밀-프로피온아미딘 유도체의 제조방법 Download PDF

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KR900001667A
KR900001667A KR1019890005979A KR890005979A KR900001667A KR 900001667 A KR900001667 A KR 900001667A KR 1019890005979 A KR1019890005979 A KR 1019890005979A KR 890005979 A KR890005979 A KR 890005979A KR 900001667 A KR900001667 A KR 900001667A
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sulfamil
propionamidine
formula
derivative
acid
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KR1019890005979A
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KR910002880B1 (ko
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발레스터-로데스 몬트세라트
카브레-카스텔비 프란시스코
유제니오 팔로모-니콜라우 프란시스코
카브레-카스텔비 후안
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안토니오 루이스 팔로모-콜
상트로 마르가 파라 라 앵베스티가송 소시에테 아노님
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/34—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfuric acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
    • C07C319/12—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols by reactions not involving the formation of mercapto groups
    • 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
    • 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
    • C07C335/40—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of thiourea or isothiourea groups further bound to other hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D277/38—Nitrogen atoms
    • C07D277/44—Acylated amino or imino radicals
    • C07D277/48—Acylated amino or imino radicals by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof, e.g. carbonylguanidines

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)

Abstract

내용 없음

Description

N-술파밀-프로피온아미딘 유도체의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (7)

  1. 다음의 일반식(II)을 가진 3-치환-프로피온니트릴을 다음의 일반식(III)의 옥소늄과 반응시켜 다음의 일반식(IV)의 이미도일 할라이드염을 생성시킨 다음, 다음의 일반식(V)의 술파미드와 반응시켜 다음의 일반식(I)의 화합물을 얻는 것을 특징으로하는 일반식(I)의 N-술파밀-프로피온아미딘 유도체의 제조방법.
    상기 각 일반식에서 R은 염소 또는 브롬과 같은 할로겐, 메르캅토, 메틸메르캅토, 이소티오우로늄, 5-메틸-1,3,4-티어디아졸-2-메르캅토 또는 2-구아니디노티아졸-4-메틸메르캅토로부터 선택된 기이며, X는 염소 또는 브롬원자이고, R1은 수소원자 또는 C1-C8트리알킬실릴기, 바람직하게는 트리메틸실릴, 트리에틸실릴, 디메틸-t-부틸실릴 또는 디메틸이소프로필실릴기이다.
  2. 제1항에 있어서, 3-치환된-프로피온니트릴 1.0-3.0mol을 술파미드 또는 N,N'-bit-트리메틸실리술파미드 1.0-3.0mol 존재하에, 압력 0.5-4.0kg/㎠, 온도 35℃-75℃ 바람직하게는 40℃-70℃의 밀폐계에서, 1,4-디옥산히드로클로라이드 4.0-15.0mol과 4-20 시간동안 반응시키는 것을 특징으로하는 N-술파밀-프로피온아미딘 유도체의 제조방법.
  3. 제1항에 있어서, 다음 일반식(VI)의 N-술파밀-프로피온 아미딘 용액제조를 위하여,
    (상기 일반식에서 R은 염소원자임이 바람직함) 상기 일반식(I) 화합물을 디클로로메탄 또는 클로로포름으로부터 선택된 공용매와 함께 디메틸포름아미드, 디메틸아세트아미드, 아세토니트릴 또는 그 혼합물속에서 온도 60℃-75℃으로 실릴화제, 바람직하게는 3-트리메틸실릴-2-옥사졸릴디논, 헥사메틸디실자란 또는 트리메틸실릴아세트아미드와 반응시키는 것을 특징으로하는 N-술파밀-프로피온아미딘 유도체의 제조방법.
  4. 제1항에 있어서, 과잉 염화수소, 니트릴, 술파미드 및 1,4-디옥산을 상기 방법으로 재순환시키는 것을 특징으로 하는 N-술파밀-프로피온아미딘 유도체의 제조방법.
  5. 제1항에 있어서, 일반식(II) 화합물인 3-(2-구아니디노티아졸-4-일-메틸티오)-프로피오니트릴을 황산 또는 술폰산염으로써 바람직하게는 황산염으로부터 또는 메탄술폰산, 톨루엔술폰산, 트리플루오로메탈술폰산, 벤젠술폰산 또는 페놀술폰산에 의하여 형성된 기 중에서 선택되는 것을 특징으로하는 N-술파밀-프로피온아미딘 유도체의 제조방법.
  6. 제1항에 있어서, 파모티딘의 제조를 위하여, 3-(2-구아니디노티아놀--일-메틸티오)-프로피오니트릴 트리플루오로메탄 술폰산염 일당량을 압력 0.5~4.0kg/㎠에서 1,4-디옥산히드로클로라이드 15.0당량이상과 반응시키고 35°-40°에서 술파미드 3당량 이상과 20시간동안 반응시키는 것을 특징으로 하는 N-술파밀-프로피온아미딘 유도체의 제조방법.
  7. 2-구아니디노-4-메르캅토메틸-티아졸의 1,8-디아자비시클로[5.4.0]운덱-7-엔 염을 제1항에서 기술된 R 및 X가 염소원자인 일반식(I) 또는 일반식(VI)의 N-술파밀 프로피온아미딘과 상온에서 유기염기 일당량 존재하에 S-알킬화 반응시키는 것으로 이루어진 파모티딘의 제조방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019890005979A 1988-07-18 1989-05-03 N-술파밀-프로피온아미딘 유도체의 제조방법 KR910002880B1 (ko)

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Application Number Priority Date Filing Date Title
ES8802626 1988-07-18
ES8802626A ES2008810A6 (es) 1988-07-18 1988-07-18 Procedimiento de preparacion de derivados de n-sulfamil-propionamidina.
ESE9-8802626 1988-07-18

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KR900001667A true KR900001667A (ko) 1990-02-27
KR910002880B1 KR910002880B1 (ko) 1991-05-09

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EP (1) EP0356366A1 (ko)
JP (1) JPH02124868A (ko)
KR (1) KR910002880B1 (ko)
ES (1) ES2008810A6 (ko)
PT (1) PT90795A (ko)

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US5856500A (en) * 1997-03-11 1999-01-05 Albemarle Corporation Synthesis of thiazole derivatives
US5731442A (en) * 1997-03-11 1998-03-24 Albemarle Corporation Synthesis of thiazole derivatives
CN117304076B (zh) * 2023-11-28 2024-02-20 苏州大学 一种n-磺酰基脒化合物的制备方法

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* Cited by examiner, † Cited by third party
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JPS6056143B2 (ja) * 1979-08-02 1985-12-09 山之内製薬株式会社 アミジン誘導体ならびにその製造法
HU193608B (en) * 1985-09-11 1987-11-30 Richter Gedeon Vegyeszet Process for production of new dervatives of n-sulphanol-propion-amidine
DE3644246A1 (de) * 1986-06-20 1987-12-23 Uriach & Cia Sa J Verfahren zur herstelung von 3-(((2-((aminoiminomethyl)-amino)-4-thiazolyl)-methyl)-thio)-n-(aminosulfonyl)-propanimidamid
EP0284536A1 (en) * 1987-02-20 1988-09-28 Centro Marga Para La Investigacion S.A. A process for the preparation of 3-(2-guanidinothiazol-4-yl-methylthio)propionitrile

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KR910002880B1 (ko) 1991-05-09
EP0356366A1 (en) 1990-02-28
PT90795A (pt) 1990-02-08
ES2008810A6 (es) 1989-08-01
JPH02124868A (ja) 1990-05-14

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