KR930005973A - 1-[(2s)-3-메르캅토-메틸-1-옥소프로필]-l-프롤린의 제조방법 - Google Patents
1-[(2s)-3-메르캅토-메틸-1-옥소프로필]-l-프롤린의 제조방법 Download PDFInfo
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- KR930005973A KR930005973A KR1019910016570A KR910016570A KR930005973A KR 930005973 A KR930005973 A KR 930005973A KR 1019910016570 A KR1019910016570 A KR 1019910016570A KR 910016570 A KR910016570 A KR 910016570A KR 930005973 A KR930005973 A KR 930005973A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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Abstract
본 발명은 하기 구조식(Ⅱ)의 1-[(2S)-2-메틸-1-옥소-3-로다니도프로필]-L-프롤린을 촉매 존재하여 불활성 용매중에서, 105내지 107Pa의 압력하에 50 내지 120℃에서 수소화반응 시킴을 특징으로 하여 하기 구조식(Ⅰ)의 1-[(2S)-3-메르캅토-2-메틸-1-옥소프로필]-L-프롤린(캅토프릴)을 제조하는 신규한 방법에 관한 것이다.
상기 구조식(Ⅱ)의 화합물은 신규하고, 하기 구조식(Ⅲ)의 (2S)-2-메틸-3-로다니도프로피온산의 반응성 아실화 유도체로 L-프롤린을 아실화하여 제조할수 있다.
본 발명의 방법은 구조식(Ⅰ)의 화합물을 간단한 방법으로 고순도 및 양호한 수율로 제조할수 있다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (9)
- 하기 구조식(Ⅱ)의 1-[(2S)-2-메틸-1-옥소-3-로다니도프로필]-L-프롤린을 촉매 존재하에 불활성 용매중에서, 105내지 107Pa의 압력하에 50 내지 120℃에서 수소화반응 시킴을 특징으로 하여 하기 구조식(Ⅰ)의 1-[(2S)-3-메르캅토-2-메틸-1-옥소프로필]-L-프롤린을 제조방법.
- 제1항에 있어서, 수소화반응을 70 내지 90℃의 온도에서 수행함을 특징으로 하는 방법.
- 제1항에 있어서, 수소화반응을 (5-6)x105Pa의 압력하에서 수행함을 특징으로 하는 방법.
- 제1항에 있어서, 촉매로서 활성탄상-팔라듐을 사용함을 특징으로 하는 방법.
- 1-(2-메틸-1-옥소-3-로다니도프로필)프롤린.
- 하기 구조식(Ⅲ)의 로다니도이소부티르산의 반응성 아실화 유도체로 프롤린을 아실화함을 특징으로 하는 상기 구조식(Ⅱ)의 1-(2-메틸-1-옥소-3-로다니도프로릴) 프롤린 제조방법.
- 제6항에 있어서, 구조식(Ⅲ)의 로다니도이소부티르산의 반응성 아실화 유도체로서 하기 일반식(Ⅳ)의 혼합 무수물을 사용함을 특징으로 하는 방법.상기식에서, R은 C1-5알킬 또는 벤질기이다.
- 제6항 또는 7항에 있어서, 일반식(Ⅴ)의 혼합 무수물을 제조하는 반응 혼합물에서 구조식(Ⅲ)의 로다니도이소부티론산을 하기 일반식(Ⅳ)의 클로로포르메이트 에스테르와 반응시켜 제조한 일반식(Ⅴ)의 혼합 무수물로 프롤린을 아신화함을 특징으로 하는 방법.상기식에서 R은 제7항에서 정의한 바와 같다.
- 제5항 내지 제8항중의 어느 한 항에 있어서, 라세미 프롤린 대신에 L-프롤린을 사용함을 특징으로 하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HU5998/90 | 1990-09-21 | ||
HU905998A HU208954B (en) | 1990-09-21 | 1990-09-21 | Process for producing 1-(3-mercapto-(2s)-methyl-1-oxo-propyl)-l-prolyn |
Publications (1)
Publication Number | Publication Date |
---|---|
KR930005973A true KR930005973A (ko) | 1993-04-20 |
Family
ID=10971099
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019910016570A KR930005973A (ko) | 1990-09-21 | 1991-09-20 | 1-[(2s)-3-메르캅토-메틸-1-옥소프로필]-l-프롤린의 제조방법 |
Country Status (24)
Country | Link |
---|---|
US (1) | US5202443A (ko) |
KR (1) | KR930005973A (ko) |
AT (1) | AT395148B (ko) |
AU (1) | AU637719B2 (ko) |
CA (1) | CA2051985A1 (ko) |
CH (1) | CH683099A5 (ko) |
DE (1) | DE4123172A1 (ko) |
DK (1) | DK162191A (ko) |
ES (1) | ES2035798B1 (ko) |
FI (1) | FI914426A (ko) |
FR (1) | FR2667065B1 (ko) |
GB (1) | GB2248060B (ko) |
GR (1) | GR1002173B (ko) |
HU (1) | HU208954B (ko) |
IL (1) | IL99535A (ko) |
IT (1) | IT1251845B (ko) |
NL (1) | NL9101582A (ko) |
NO (1) | NO176141C (ko) |
PL (1) | PL291789A1 (ko) |
PT (1) | PT99022A (ko) |
RU (1) | RU2026286C1 (ko) |
SE (1) | SE501501C2 (ko) |
TW (1) | TW203042B (ko) |
ZA (1) | ZA917517B (ko) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
HU211101B (en) * | 1992-03-13 | 1995-10-30 | Egyt Gyogyszervegyeszeti Gyar | Process for preparing 1-[/2s/-methyl-3-mercapto-propionyl]-pyrrolidine-/2s/-carboxylic acid |
US5728887A (en) * | 1996-04-10 | 1998-03-17 | E. I. Du Pont De Nemours And Company | Catalytic hydrogenolysis of organic thiocyanates and disulfides to thiols |
KR100507816B1 (ko) * | 1996-04-10 | 2006-01-27 | 이.아이,듀우판드네모아앤드캄파니 | 유기티오시아네이트및디술파이드의티올로의접촉가수소분해 |
Family Cites Families (20)
Publication number | Priority date | Publication date | Assignee | Title |
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US3998808A (en) * | 1968-05-22 | 1976-12-21 | Velsicol Chemical Corporation | Compositions of matter D-hetero-1,1-(α-thiocyanoacetyl) compounds |
US4105776A (en) * | 1976-06-21 | 1978-08-08 | E. R. Squibb & Sons, Inc. | Proline derivatives and related compounds |
US4241076A (en) * | 1978-02-21 | 1980-12-23 | E. R. Squibb & Sons, Inc. | Halogenated substituted mercaptoacylamino acids |
US4192945A (en) * | 1978-12-07 | 1980-03-11 | E. R. Squibb & Sons, Inc. | Process for preparing proline and homoproline derivatives |
US4684660A (en) * | 1979-04-02 | 1987-08-04 | E. R. Squibb & Sons, Inc. | Mercaptoacyldepeptides |
ES486217A0 (es) * | 1979-11-21 | 1980-12-16 | Farmaceutico Quimico Lab | Procedimiento de obtencion de un derivado de prolina |
HU184082B (en) * | 1979-12-29 | 1984-06-28 | Egyt Gyogyszervegyeszeti Gyar | Process for preparing 1-3-/3mercapto-/2s/-methyl-propinyl/-pyrrolidine-/2s/-carboxylic acid |
ES490841A0 (es) * | 1980-04-24 | 1981-05-16 | Inke Sa | Procedimiento para la obtencion de la n-(d-3-mercapto-2-me tilpropionil) l-prolina. |
SE8203245L (sv) * | 1981-05-27 | 1982-11-28 | Crc Ricerca Chim | Forfarande for enantioselektiv framstellning av n-substituerade prolinderivat |
JPS58124764A (ja) * | 1982-01-20 | 1983-07-25 | Kanegafuchi Chem Ind Co Ltd | 光学活性チオ−ル化合物の製造法 |
KR860001391B1 (ko) * | 1984-07-23 | 1986-09-22 | 보령제약 주식회사 | 피롤리딘 유도체의 제조방법 |
KR870001569B1 (ko) * | 1985-02-11 | 1987-09-04 | 보령제약 주식회사 | 피롤리딘 유도체의 제조방법 |
ES8604514A1 (es) * | 1985-04-10 | 1986-02-01 | Farmhispania | Procedimiento para la sintesis de la 1-(3-mercapto-2-d(-)- metilo-propanol)-2(-) prolina |
ES544509A0 (es) * | 1985-06-25 | 1986-01-01 | Inke Sa | Procedimiento para la obtencion de la 1-(n-(1-etoxicarbonil-3-fenilpropil)-l-alanil)-l-prolina |
AT395012B (de) * | 1986-06-27 | 1992-08-25 | Richter Gedeon Vegyeszet | Verfahren zur herstellung von n-(1(s)|thoxycarbonyl-3-phenyl-propyl)-(s)-alanyl-(s)prolin und von dessen saeureadditionssalzen |
US5002964A (en) * | 1988-06-15 | 1991-03-26 | Brigham & Women's Hospital | S-nitrosocaptopril compounds and the use thereof |
US5025001A (en) * | 1988-06-15 | 1991-06-18 | Brigham And Women's Hospital | S-nitroso derivatives of ACE inhibitors and the use thereof |
IL91581A (en) * | 1988-09-13 | 1993-07-08 | Sepracor Inc | Methods for preparing optically active captopril and its analogues |
US5026873A (en) * | 1989-11-06 | 1991-06-25 | E. R. Squibb & Sons, Inc. | Process for direct isolation of captopril |
HU206198B (en) * | 1990-09-21 | 1992-09-28 | Egyt Gyogyszervegyeszeti Gyar | Process for producing rhodanidoisobutyric acid |
-
1990
- 1990-09-21 HU HU905998A patent/HU208954B/hu not_active IP Right Cessation
-
1991
- 1991-01-18 AT AT0010591A patent/AT395148B/de not_active IP Right Cessation
- 1991-07-12 DE DE4123172A patent/DE4123172A1/de not_active Withdrawn
- 1991-09-17 CH CH2749/91A patent/CH683099A5/de not_active IP Right Cessation
- 1991-09-20 KR KR1019910016570A patent/KR930005973A/ko not_active Application Discontinuation
- 1991-09-20 FR FR9111605A patent/FR2667065B1/fr not_active Expired - Fee Related
- 1991-09-20 NL NL9101582A patent/NL9101582A/nl not_active Application Discontinuation
- 1991-09-20 RU SU915001836A patent/RU2026286C1/ru active
- 1991-09-20 US US07/762,688 patent/US5202443A/en not_active Expired - Fee Related
- 1991-09-20 CA CA002051985A patent/CA2051985A1/en not_active Abandoned
- 1991-09-20 PT PT99022A patent/PT99022A/pt not_active Application Discontinuation
- 1991-09-20 NO NO913720A patent/NO176141C/no unknown
- 1991-09-20 GR GR910100391A patent/GR1002173B/el unknown
- 1991-09-20 AU AU84611/91A patent/AU637719B2/en not_active Ceased
- 1991-09-20 TW TW080107464A patent/TW203042B/zh active
- 1991-09-20 FI FI914426A patent/FI914426A/fi not_active Application Discontinuation
- 1991-09-20 ZA ZA917517A patent/ZA917517B/xx unknown
- 1991-09-20 IT ITMI912520A patent/IT1251845B/it active IP Right Grant
- 1991-09-20 IL IL9953591A patent/IL99535A/en not_active IP Right Cessation
- 1991-09-20 GB GB9120150A patent/GB2248060B/en not_active Expired - Fee Related
- 1991-09-20 PL PL29178991A patent/PL291789A1/xx unknown
- 1991-09-20 DK DK162191A patent/DK162191A/da not_active IP Right Cessation
- 1991-09-20 SE SE9102722A patent/SE501501C2/sv unknown
- 1991-09-20 ES ES9102086A patent/ES2035798B1/es not_active Expired - Fee Related
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