RO78870B - Process for preparing mercaptoacylproline derivatives - Google Patents

Process for preparing mercaptoacylproline derivatives

Info

Publication number
RO78870B
RO78870B RO98428A RO9842879A RO78870B RO 78870 B RO78870 B RO 78870B RO 98428 A RO98428 A RO 98428A RO 9842879 A RO9842879 A RO 9842879A RO 78870 B RO78870 B RO 78870B
Authority
RO
Romania
Prior art keywords
general formula
derivatives
defined above
mercaptoacylproline
preparing
Prior art date
Application number
RO98428A
Other languages
Romanian (ro)
Other versions
RO78870A (en
Inventor
Miguel A. Ondetti
John Krapcho
Original Assignee
E.R. Squib & Sons Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by E.R. Squib & Sons Inc filed Critical E.R. Squib & Sons Inc
Publication of RO78870A publication Critical patent/RO78870A/en
Publication of RO78870B publication Critical patent/RO78870B/en

Links

Classifications

    • 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
    • C07D207/12—Oxygen or sulfur atoms
    • 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
    • C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member 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
    • 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
    • A61P9/12—Antihypertensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00—Thiocarboxylic acids
    • 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

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Cardiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pyrrole Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Peptides Or Proteins (AREA)

Abstract

Procedeu de preparare a unor derivati de mercaptoacilproline, cu formula generala I:(vezi formula) în care grupa XR1 este situata în pozitia 3 sau 4 din inelul prolinei, X reprezinta oxigen sau sulf, R reprezinta hidrogen sau o grupa alchil cu 1...4 atomi de carbon sau o grupa fenil, eventual substituita cu halogen, metil sau metoxi, R2 reprezinta hidrogen sau alchil inferior, R3 reprezinta alcanoil cu 1...4 atomi de carbon sau benzoil, caracterizat prin aceea ca se aduce în reactie o prolina, cu formula generala II: (vezi formula) în care R, R1 si X au semnificatiile aratate mai sus, cu un acid cu formula generala III: ( vezi formula) în care R2 si R3 au semnificatiile aratate mai sus, reactantii fiind luati în raport molar de circa 1 :1 la temperatura de circa +5 degree C, în prezenta unui agent de cuplare ales dintre diciclohexilcarbodiimida si anhidrida acidului, folosit în reactie, apoi produsul de reactie este eventual supus hidrolize în vederea obtinerii mercaptoderivatului în mod cunoscut.A process for the preparation of mercaptoacylprolines derivatives of general formula I wherein XR1 is located in the 3 or 4 position of the proline ring, X represents oxygen or sulfur, R represents hydrogen or a C1-6 alkyl group. Or a phenyl group optionally substituted by halogen, methyl or methoxy, R2 represents hydrogen or lower alkyl, R3 represents alkanoyl of 1-4 carbon atoms or benzoyl, characterized in that a proline of general formula II wherein R, R 1 and X are as defined above, with an acid of general formula III wherein R 2 and R 3 are as defined above, the reactants being taken up in a molar ratio of about 1: 1 to about +5 ° C, in the presence of a coupling agent selected from dicyclohexylcarbodiimide and the acid anhydride used in the reaction, then the reaction product is optionally hydrolysed to obtain mercaptoderivative in a known way.

RO98428A 1978-08-11 1979-08-10 Process for preparing mercaptoacylproline derivatives RO78870B (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US93288378A 1978-08-11 1978-08-11
KR1019790002731A KR830002450B1 (en) 1978-08-11 1979-08-10 Method for preparing mercaptoacyl derivative of substituted proline

Publications (2)

Publication Number Publication Date
RO78870A RO78870A (en) 1982-07-06
RO78870B true RO78870B (en) 1985-01-30

Family

ID=26626596

Family Applications (1)

Application Number Title Priority Date Filing Date
RO98428A RO78870B (en) 1978-08-11 1979-08-10 Process for preparing mercaptoacylproline derivatives

Country Status (30)

Country Link
JP (2) JPS5527199A (en)
KR (1) KR830002450B1 (en)
AR (1) AR229081A1 (en)
AT (1) AT379589B (en)
AU (1) AU530690B2 (en)
BE (1) BE878191A (en)
CA (1) CA1144930A (en)
CH (1) CH642064A5 (en)
CS (1) CS228118B2 (en)
DD (1) DD145749A5 (en)
DE (1) DE2932021C2 (en)
DK (1) DK154553C (en)
ES (1) ES483311A1 (en)
FI (1) FI69834C (en)
FR (1) FR2435469A1 (en)
GB (1) GB2028327B (en)
GR (1) GR72420B (en)
IE (1) IE48802B1 (en)
IN (1) IN152712B (en)
IT (1) IT1117782B (en)
LU (2) LU81593A1 (en)
NL (2) NL193374C (en)
NZ (1) NZ191036A (en)
PH (1) PH15030A (en)
PT (1) PT70049A (en)
RO (1) RO78870B (en)
SE (1) SE447477B (en)
SU (1) SU1066460A3 (en)
YU (1) YU41876B (en)
ZA (1) ZA793633B (en)

Families Citing this family (45)

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Publication number Priority date Publication date Assignee Title
US4483861A (en) * 1978-10-31 1984-11-20 Santen Pharmaceutical Co., Ltd. Antihypertensive sulfur-containing compounds
CA1132985A (en) * 1978-12-22 1982-10-05 John Krapcho Ketal and thioketal derivatives of mercaptoacyl prolines
US4347371A (en) * 1978-12-30 1982-08-31 Santen Pharmaceutical Co., Ltd. Disulfide compounds
US4234489A (en) * 1979-06-25 1980-11-18 E. R. Squibb & Sons, Inc. Pyroglutamic acid derivatives and analogs
US4288368A (en) * 1979-07-30 1981-09-08 E. R. Squibb & Sons, Inc. Dithioacylproline derivatives
US4291040A (en) * 1979-10-22 1981-09-22 E. R. Squibb & Sons, Inc. Mercaptoacyl derivatives of 4-disubstituted prolines and 4-substituted dehydroprolines
US4692458A (en) * 1980-03-05 1987-09-08 University Of Miami Anti-hypertensive agents
AU542211B2 (en) * 1980-03-07 1985-02-14 Gruppo Lepetit S.P.A. Mercaptocycloalkyl carbonyl prolines
GB2070586A (en) * 1980-03-21 1981-09-09 Squibb & Sons Inc Derivatives of Proline or Pipecolic Acid
US4284624A (en) 1980-05-02 1981-08-18 E. R. Squibb & Sons, Inc. Mixed disulfides
US4578474A (en) * 1980-06-23 1986-03-25 E. R. Squibb & Sons, Inc. Imido, amido and amino derivatives of mercaptoacyl prolines and pipecolic acids
US4390695A (en) * 1980-06-23 1983-06-28 E. R. Squibb & Sons, Inc. Imido, amido and amino derivatives of mercaptoacyl prolines and pipecolic acids
US4316905A (en) * 1980-07-01 1982-02-23 E. R. Squibb & Sons, Inc. Mercaptoacyl derivatives of various 4-substituted prolines
US4332726A (en) * 1980-08-25 1982-06-01 E. R. Squibb & Sons, Inc. Purification of mercaptoacyl amino acids
US4307110A (en) * 1980-09-12 1981-12-22 E. R. Squibb & Sons, Inc. Mercaptoacyl derivatives of 3-substituted proline derivatives
US4311705A (en) * 1980-10-06 1982-01-19 E. R. Squibb & Sons, Inc. Carboxyalkanoyl and hydroxycarbamoylalkanoyl derivatives of substituted prolines
US4312809A (en) 1980-10-31 1982-01-26 E. R. Squibb & Sons, Inc. Lactam derivatives of mercaptoacylamino acids
US4462943A (en) * 1980-11-24 1984-07-31 E. R. Squibb & Sons, Inc. Carboxyalkyl amino acid derivatives of various substituted prolines
US4384123A (en) * 1980-12-04 1983-05-17 E. R. Squibb & Sons, Inc. Phosphinylalkanoyl substituted prolines
US4337201A (en) * 1980-12-04 1982-06-29 E. R. Squibb & Sons, Inc. Phosphinylalkanoyl substituted prolines
US4416831A (en) 1981-04-27 1983-11-22 E. R. Squibb & Sons, Inc. Amino and substituted amino phosphinylalkanoyl compounds
US4374131A (en) 1981-04-27 1983-02-15 E. R. Squibb & Sons, Inc. Amino and substituted amino phosphinyl-alkanoyl compounds
US4381297A (en) 1981-05-04 1983-04-26 E. R. Squibb & Sons, Inc. Substituted carbonyl phosphinyl-alkanoyl compounds
US4416833A (en) 1981-05-04 1983-11-22 E. R. Squibb & Sons, Inc. Substituted carbonyl phosphinyl-alkanoyl compounds
US4497953A (en) * 1981-06-01 1985-02-05 E. R. Squibb & Sons, Inc. Imido, amido and amino derivatives of mercaptoacyl prolines and pipecolic acids
US4377701A (en) * 1981-09-21 1983-03-22 E. R. Squibb & Sons, Inc. 4-Methylene-1-[[(alranoyl or arylcarbonyl)mercapto]acyl]proline and pipecolic acid
US4555506A (en) * 1981-12-24 1985-11-26 E. R. Squibb & Sons, Inc. Phosphorus containing compounds and use as hypotensives
US4560680A (en) * 1982-03-15 1985-12-24 E. R. Squibb & Sons, Inc. Aminoalkyl and related substituted phosphinic acid angiotensin converting enzyme inhibitors
US4452791A (en) * 1982-03-15 1984-06-05 E. R. Squibb & Sons, Inc. Aminoalkyl and related substituted phosphinic acid angiotensin converting enzyme inhibitors
US4452790A (en) * 1982-06-23 1984-06-05 E. R. Squibb & Sons, Inc. Phosphonyl hydroxyacyl amino acid derivatives as antihypertensives
US4616005A (en) * 1982-06-23 1986-10-07 E. R. Squibb & Sons, Inc. Phosphonyl hydroxyacyl amino acid derivatives as antihypertensives
US4703043A (en) * 1982-06-23 1987-10-27 E. R. Squibb & Sons, Inc. Phosphonyl hydroxyacyl amino acid derivatives as antihypertensive
US4567166A (en) * 1982-07-14 1986-01-28 E. R. Squibb & Sons, Inc. Amino and substituted amino phosphinylalkanoyl compounds useful for treating hypertension
EP0187037A3 (en) * 1984-12-21 1988-03-23 Takeda Chemical Industries, Ltd. Piperidine derivatives, their production and use
CA2021409A1 (en) * 1989-08-21 1991-02-22 Donald S. Karanewsky Phosphonate substituted amino or imino acids useful as antihypertensives
JPH05344844A (en) * 1992-06-12 1993-12-27 Suzumo Kiko Kk Method for producing roasted rice ball cracker
EP0640594A1 (en) 1993-08-23 1995-03-01 Fujirebio Inc. Hydantoin derivative as metalloprotease inhibitor
US5435286A (en) * 1994-05-02 1995-07-25 Cummins Engine Company, Inc. Ball link assembly for vehicle engine drive trains
GB0225379D0 (en) * 2002-10-31 2002-12-11 Pfizer Ltd Therapeutic proline derivatives
US7659305B2 (en) 2002-10-31 2010-02-09 Pfizer Inc. Therapeutic proline derivatives
WO2006038119A1 (en) * 2004-10-08 2006-04-13 Warner-Lambert Company Llc Stereoselective synthesis of n-protected alkoxy prolines
GB0715626D0 (en) 2007-08-10 2007-09-19 Generics Uk Ltd Crystalline form of zofenopril calcium
NZ622549A (en) * 2008-02-27 2015-10-30 Generics Uk Ltd Novel crystalline form of zofenopril calcium
US8853421B2 (en) 2008-02-27 2014-10-07 Generics [Uk] Limited Crystalline forms of zofenopril calcium
SI23949A (en) 2011-12-19 2013-06-28 Silverstone Pharma The new crystalline salts of zofenopril, the procedure for obtaining them and their use in therapy

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Publication number Priority date Publication date Assignee Title
FR2340092A2 (en) * 1976-02-09 1977-09-02 Roussel Uclaf Analgesic (N)-thiazolyl-quinoline carboxamides - prepd. from the corresp. quinoline carboxylic acid and (2)-amino-thiazole
AU509899B2 (en) * 1976-02-13 1980-05-29 E.R. Squibb & Sons, Inc. Proline derivatives and related compounds
US4116962A (en) * 1976-12-03 1978-09-26 E. R. Squibb & Sons, Inc. Pyrrolidine and piperidine-2-carboxylic acid derivatives
US4113715A (en) * 1977-01-17 1978-09-12 E. R. Squibb & Sons, Inc. Amino acid derivatives
US4108886A (en) * 1977-03-11 1978-08-22 E. R. Squibb & Sons, Inc. Thiopropanoylamino acid derivatives
PH15381A (en) * 1978-02-21 1982-12-17 Squibb & Sons Inc Halogen substituted mercaptoacylamino acids
US4154934A (en) * 1978-08-11 1979-05-15 E. R. Squibb & Sons, Inc. Mercaptoacylamino derivatives of heterocyclic carboxylic acids

Also Published As

Publication number Publication date
YU41876B (en) 1988-02-29
NL7906120A (en) 1980-02-13
JPH01287069A (en) 1989-11-17
IN152712B (en) 1984-03-17
FI69834B (en) 1985-12-31
DK335879A (en) 1980-02-12
IT1117782B (en) 1986-02-24
ZA793633B (en) 1980-07-30
ES483311A1 (en) 1980-04-16
NL990024I2 (en) 1999-11-01
DE2932021C2 (en) 1994-05-19
YU192379A (en) 1983-02-28
GB2028327A (en) 1980-03-05
DK154553B (en) 1988-11-28
CA1144930A (en) 1983-04-19
AT379589B (en) 1986-01-27
DE2932021A1 (en) 1980-02-21
PT70049A (en) 1979-09-01
NZ191036A (en) 1984-05-31
KR830001269A (en) 1983-04-29
FI69834C (en) 1986-05-26
NL193374B (en) 1999-04-01
AR229081A1 (en) 1983-06-15
JPH0134987B2 (en) 1989-07-21
GR72420B (en) 1983-11-03
CH642064A5 (en) 1984-03-30
BE878191A (en) 1980-02-11
IE791544L (en) 1980-02-11
NL193374C (en) 1999-08-03
PH15030A (en) 1982-05-13
SE7906722L (en) 1980-02-12
CS228118B2 (en) 1984-05-14
NL990024I1 (en) 1999-11-01
SU1066460A3 (en) 1984-01-07
KR830002450B1 (en) 1983-10-26
FR2435469B1 (en) 1983-02-11
IT7949954A0 (en) 1979-08-03
LU81593A1 (en) 1979-12-07
RO78870A (en) 1982-07-06
GB2028327B (en) 1982-11-24
FR2435469A1 (en) 1980-04-04
AU530690B2 (en) 1983-07-28
IE48802B1 (en) 1985-05-15
SE447477B (en) 1986-11-17
DD145749A5 (en) 1981-01-07
JPS5527199A (en) 1980-02-27
LU90403I2 (en) 2000-07-07
ATA541679A (en) 1985-06-15
DK154553C (en) 1989-04-17
FI792498A (en) 1980-02-12
AU4919079A (en) 1980-02-14

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