YU40664B - Process for obtaining 1-(3-mercapto-2-d-methyl-propanoyl)-l-proline - Google Patents

Process for obtaining 1-(3-mercapto-2-d-methyl-propanoyl)-l-proline

Info

Publication number
YU40664B
YU40664B YU331/77A YU33177A YU40664B YU 40664 B YU40664 B YU 40664B YU 331/77 A YU331/77 A YU 331/77A YU 33177 A YU33177 A YU 33177A YU 40664 B YU40664 B YU 40664B
Authority
YU
Yugoslavia
Prior art keywords
formula
acid
acylation
hydroxyl
compounds
Prior art date
Application number
YU331/77A
Other versions
YU33177A (en
Inventor
M A Ondetti
D W Cushman
Original Assignee
Squibb & 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
Priority claimed from US05/657,792 external-priority patent/US4046889A/en
Priority claimed from US05/751,851 external-priority patent/US4105776A/en
Application filed by Squibb & Sons Inc filed Critical Squibb & Sons Inc
Publication of YU33177A publication Critical patent/YU33177A/en
Publication of YU40664B publication Critical patent/YU40664B/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
    • C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • 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
    • C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
    • 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
    • C07C327/00—Thiocarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
    • C07C53/15—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing halogen
    • C07C53/19—Acids containing three or more carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
    • C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • 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

  • Chemical & Material Sciences (AREA)
  • 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)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyrrole Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Hydrogenated Pyridines (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

The compounds of formula I are prepared by N-acylation of a compound of formula II' by means of an acid of formula III'. In these formulae, R is a hydroxyl, NH2 or alkoxy group, R1 and R4 are each H or an alkyl, phenyl or phenylalkyl group, R2 is H or an organic substituent, R3 is H or a hydroxyl or alkyl group, m is 1, 2 or 3 and n is 0, 1 or 2. The acid of formula III' can be replaced by a functional derivative of the latter or, when n is 1, by an acrylic acid of formula R4CH=C(R1)-COOH. In the latter case, after the acylation, a thiol or thioacid R2SH is added to the double bond of the acryloyl residue. The compounds of formula I are therapeutically active in the treatment of blood hypertension (high blood pressure). <IMAGE>
YU331/77A 1976-02-13 1977-02-08 Process for obtaining 1-(3-mercapto-2-d-methyl-propanoyl)-l-proline YU40664B (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US05/657,792 US4046889A (en) 1976-02-13 1976-02-13 Azetidine-2-carboxylic acid derivatives
US69843276A 1976-06-21 1976-06-21
US05/751,851 US4105776A (en) 1976-06-21 1976-12-22 Proline derivatives and related compounds

Publications (2)

Publication Number Publication Date
YU33177A YU33177A (en) 1983-01-21
YU40664B true YU40664B (en) 1986-04-30

Family

ID=27417986

Family Applications (1)

Application Number Title Priority Date Filing Date
YU331/77A YU40664B (en) 1976-02-13 1977-02-08 Process for obtaining 1-(3-mercapto-2-d-methyl-propanoyl)-l-proline

Country Status (31)

Country Link
JP (1) JPS604815B2 (en)
AR (4) AR222445A1 (en)
AT (1) AT365569B (en)
AU (1) AU509899B2 (en)
BG (3) BG37075A3 (en)
CA (1) CA1101864A (en)
CH (3) CH622503A5 (en)
DD (1) DD129442B3 (en)
DE (2) DE2703828C2 (en)
DK (1) DK157487C (en)
ES (5) ES455803A1 (en)
FI (1) FI66596C (en)
FR (1) FR2340932A1 (en)
GB (1) GB1576161A (en)
GR (1) GR69811B (en)
HK (1) HK20281A (en)
HU (1) HU181965B (en)
IE (1) IE44707B1 (en)
IL (1) IL51297A (en)
IT (1) IT1062293B (en)
KE (1) KE3136A (en)
MY (2) MY8200075A (en)
NL (1) NL168509C (en)
NO (1) NO146985C (en)
NZ (1) NZ183130A (en)
PH (1) PH12970A (en)
PL (1) PL118161B1 (en)
RO (1) RO69941A (en)
SE (2) SE423812B (en)
SU (1) SU747422A3 (en)
YU (1) YU40664B (en)

Families Citing this family (54)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4206122A (en) * 1978-04-14 1980-06-03 E. R. Squibb & Sons, Inc. Derivatives of pyrrolidinecarboxaldehyde and piperidinecarboxaldehyde and intermediates therefor
US4053651A (en) 1976-05-10 1977-10-11 E. R. Squibb & Sons, Inc. Compounds and method for alleviating angiotensin related hypertension
AU518147B2 (en) * 1976-12-03 1981-09-17 E.R. Squibb & Sons, Inc. Derivatives of thiazolidine, thiazine and morpholine carboxylic acids
US4129566A (en) * 1978-02-15 1978-12-12 E. R. Squibb & Sons, Inc. Derivatives of dehydrocyclicimino acids
US4113715A (en) * 1977-01-17 1978-09-12 E. R. Squibb & Sons, Inc. Amino acid derivatives
FR2412537A1 (en) * 1977-12-22 1979-07-20 Science Union & Cie NEW SUBSTITUTE THIOBUTYRAMIDES, THEIR METHODS OF OBTAINING AND THEIR PHARMACEUTICAL APPLICATION
CA1120400A (en) * 1977-12-27 1982-03-23 Zola P. Horovitz Method of treating hypertension and medicaments therefor
PH15381A (en) * 1978-02-21 1982-12-17 Squibb & Sons Inc Halogen substituted mercaptoacylamino acids
JPS559058A (en) * 1978-07-06 1980-01-22 Dainippon Pharmaceut Co Ltd 1-(3-mercapto-2-methylpropanoyl)prolyl amino acid derivative
CA1109475A (en) * 1978-07-27 1981-09-22 Miguel A. Ondetti Thiopropanoylamino acid derivatives
CA1144930A (en) * 1978-08-11 1983-04-19 Miguel A. Ondetti Mercaptoacyl derivatives of substituted prolines
NZ190995A (en) * 1978-09-05 1982-03-09 American Cyanamid Co Substituted omega propionyl or butyryl l-prolines and pharmaceutical compositions
NL7809120A (en) * 1978-09-07 1980-03-11 Oce Andeno B V Grubbenvorsterw PROCESS FOR THE PREPARATION OF PROLINE DERIVATIVES.
NL7809121A (en) * 1978-09-07 1980-03-11 Oce Andeno B V Grubbenvorsterw OPTICALLY ACTIVE DERIVATIVES OF MERCAPTO-ISO BUTIC ACID.
GR73585B (en) * 1978-09-11 1984-03-26 Univ Miami
US4690937A (en) * 1979-08-14 1987-09-01 University Of Miami Anti-hypertensive agents
ZA794723B (en) * 1978-09-11 1980-08-27 Univ Miami Anti-hypertensive agents
JPS5540622A (en) * 1978-09-14 1980-03-22 Santen Pharmaceut Co Ltd Hypotensive agent
US4483861A (en) * 1978-10-31 1984-11-20 Santen Pharmaceutical Co., Ltd. Antihypertensive sulfur-containing compounds
US4198515A (en) * 1978-12-08 1980-04-15 E. R. Squibb & Sons, Inc. Mercaptoacyl derivatives of 4,5-dihydro-1H-pyrrole-2-carboxylic acids and 1,4,5,6-tetrahydropyridine-2-carboxylic acids
US4410542A (en) 1978-12-30 1983-10-18 Santen Pharmaceutical Co., Ltd. Disulfide compounds
US4347371A (en) * 1978-12-30 1982-08-31 Santen Pharmaceutical Co., Ltd. Disulfide compounds
CA1138452A (en) * 1979-01-15 1982-12-28 John Krapcho Carbamate derivatives of mercaptoacyl hydroxy prolines
US4461896A (en) * 1979-02-07 1984-07-24 Norwich Eaton Pharmaceuticals, Inc. 1-[Acylthio) and (mercapto)-1-oxoalkyl]-1,2,3,4-tetrahydroquinoline-2-carboxylic acids
US4220791A (en) * 1979-03-08 1980-09-02 E. R. Squibb & Sons, Inc. Mercaptoacylpyrazolidinone carboxylic acid derivatives
ZA802420B (en) * 1979-05-18 1981-04-29 Squibb & Sons Inc Aminoacyl derivatives of mercaptoacyl amino acids
US4234489A (en) * 1979-06-25 1980-11-18 E. R. Squibb & Sons, Inc. Pyroglutamic acid derivatives and analogs
JPS5629403U (en) * 1979-08-13 1981-03-20
DE2937779A1 (en) * 1979-09-19 1981-04-09 Hoechst Ag, 6000 Frankfurt AMINO ACID DERIVATIVES AND METHOD FOR THE PRODUCTION THEREOF
GB2066240A (en) * 1979-12-10 1981-07-08 Squibb & Sons Inc Derivatives of mercaptoacyl amino acids
GB2065643B (en) * 1979-12-13 1983-08-24 Kanegafuchi Chemical Ind Optically active n-mercaptoalkanoylamino acids
JPS5683483A (en) * 1979-12-13 1981-07-08 Santen Pharmaceut Co Ltd Thiazolidine compound
US4692458A (en) * 1980-03-05 1987-09-08 University Of Miami Anti-hypertensive agents
GB2070586A (en) * 1980-03-21 1981-09-09 Squibb & Sons Inc Derivatives of Proline or Pipecolic Acid
DE3011239A1 (en) * 1980-03-22 1981-10-01 C.H. Boehringer Sohn, 6507 Ingelheim SUBSTITUTED ALKYLTHIOACYLAMINO ACIDS, METHOD FOR THE PRODUCTION THEREOF AND PHARMACEUTICAL COMPOSITIONS
SE8203245L (en) * 1981-05-27 1982-11-28 Crc Ricerca Chim PROCEDURE FOR ENANTIOSELECTIVE PREPARATION OF N-SUBSTITUTED PROLINE DERIVATIVES
KR860001391B1 (en) * 1984-07-23 1986-09-22 보령제약 주식회사 Process for the preparation of pyrolidines
JPH06740B2 (en) * 1984-08-16 1994-01-05 三菱レイヨン株式会社 Process for producing optically active carboxylic acid amide
HU196369B (en) * 1984-10-18 1988-11-28 Egyt Gyogyszervegyeszeti Gyar New process for producing n-acylized l-prolin derivatives
KR870001570B1 (en) * 1984-12-19 1987-09-04 보령제약 주식회사 Preparing process for pyrolidine derivatives
KR870001569B1 (en) * 1985-02-11 1987-09-04 보령제약 주식회사 Preparing process for pyrolidine derivatives
AT395012B (en) * 1986-06-27 1992-08-25 Richter Gedeon Vegyeszet METHOD FOR PRODUCING N- (1 (S) | THOXYCARBONYL-3-PHENYL-PROPYL) - (S) -ALANYL- (S) PROLIN AND ITS ACID ADDITION SALTS
JP2863534B2 (en) * 1988-10-24 1999-03-03 マリオン ラボラトリーズ，インコーポレイティド Pharmaceutical composition
US5026873A (en) * 1989-11-06 1991-06-25 E. R. Squibb & Sons, Inc. Process for direct isolation of captopril
DE59306051D1 (en) * 1992-08-26 1997-05-07 Beiersdorf Ag USE OF RADICAL CATCHERS AS IMMUNODULATING AGENTS IN COSMETIC AND DERMATOLOGICAL PREPARATIONS
DE4228455A1 (en) * 1992-08-26 1994-09-15 Beiersdorf Ag Cosmetic and dermatological sunscreen formulations containing thiols and / or thiol derivatives
IT1266570B1 (en) * 1993-07-30 1997-01-09 Zambon Spa DERIVATIVES OF PROPANAMIDE N-ETEROARYL SUBSTITUTES USEFUL IN THE TREATMENT OF CARDIOVASCULAR DISEASES
US7056935B2 (en) 1995-06-07 2006-06-06 Gpi Nil Holdings, Inc. Rotamase enzyme activity inhibitors
GB9704522D0 (en) * 1997-03-05 1997-04-23 Smithkline Beecham Plc Compounds
ATE224366T1 (en) * 1997-10-31 2002-10-15 Hoffmann La Roche D-PROLINE DERIVATIVES
IL159983A0 (en) * 2001-08-07 2004-06-20 Sunesis Pharmaceuticals Inc Disulfide and thiosulfonate ligands and libraries comprising these ligands
CN100361971C (en) * 2005-09-19 2008-01-16 华中师范大学 Double functional group L-proline derivative with adjustable catalytic activity and its prepn
US8653131B2 (en) 2008-08-22 2014-02-18 Baxter Healthcare S.A. Polymeric benzyl carbonate-derivatives
RU2623233C2 (en) 2012-04-27 2017-06-23 ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи Pesticidal compositions and methods related thereto

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA946836A (en) * 1970-03-18 1974-05-07 Miguel A. Ondetti Enzyme inhibitor

Also Published As

Publication number Publication date
DE2759862C2 (en) 1989-12-07
NZ183130A (en) 1979-08-31
NO146985C (en) 1983-01-12
AR222783A1 (en) 1981-06-30
HK20281A (en) 1981-05-22
GB1576161A (en) 1980-10-01
DK157487B (en) 1990-01-15
PL195965A1 (en) 1978-02-27
YU33177A (en) 1983-01-21
IE44707B1 (en) 1982-03-10
IT1062293B (en) 1984-05-23
PH12970A (en) 1979-10-24
ES467053A1 (en) 1978-11-01
FI66596C (en) 1987-03-18
DE2703828A1 (en) 1977-08-18
DE2703828C2 (en) 1984-06-20
ES467052A1 (en) 1978-11-01
CH624932A5 (en) 1981-08-31
ATA98977A (en) 1981-06-15
SE423812B (en) 1982-06-07
SE426697B (en) 1983-02-07
JPS604815B2 (en) 1985-02-06
DK59677A (en) 1977-08-14
AU509899B2 (en) 1980-05-29
SE7701561L (en) 1977-09-23
BG37074A3 (en) 1985-03-15
FR2340932A1 (en) 1977-09-09
CA1101864A (en) 1981-05-26
JPS52116457A (en) 1977-09-29
IL51297A0 (en) 1977-03-31
BG37375A3 (en) 1985-05-15
CH624931A5 (en) 1981-08-31
NO770464L (en) 1977-08-16
SE8104660L (en) 1981-08-03
IL51297A (en) 1980-03-31
AR214649A1 (en) 1979-07-13
FI770437A (en) 1977-08-14
NO146985B (en) 1982-10-04
NL168509C (en) 1982-04-16
FR2340932B1 (en) 1981-02-06
DK157487C (en) 1990-06-11
ES467051A1 (en) 1978-11-01
PL118161B1 (en) 1981-09-30
AU2134777A (en) 1978-07-20
RO69941A (en) 1980-05-15
AT365569B (en) 1982-01-25
NL7701457A (en) 1977-08-16
SU747422A3 (en) 1980-07-23
AR222445A1 (en) 1981-05-29
CH622503A5 (en) 1981-04-15
DD129442A5 (en) 1978-01-18
BG37075A3 (en) 1985-03-15
IE44707L (en) 1977-08-13
AR226290A1 (en) 1982-06-30
KE3136A (en) 1981-07-03
GR69811B (en) 1982-07-13
ES455803A1 (en) 1978-06-16
HU181965B (en) 1983-11-28
MY102705A (en) 1992-09-30
FI66596B (en) 1984-07-31
MY8200075A (en) 1982-12-31
DD129442B3 (en) 1990-01-10
ES467050A1 (en) 1978-11-01

Similar Documents

Publication Publication Date Title
YU40664B (en) Process for obtaining 1-(3-mercapto-2-d-methyl-propanoyl)-l-proline
PT944617E (en) BENZIMIDAZOLE DERIVATIVES CRYSTALS AND THEIR PRODUCTION
DK633088A (en) collagenase
NO159167C (en) NEW 1-SUBSTITUTED-5-HYDROXYMETHYL-2-MERCAPTO IMIDAZOLE DERIVATIVES AND PROCEDURES FOR PREPARING THEREOF.
ES8606336A1 (en) 2-(N-substituteguanidino)-4-hetero-arylthiazole antiulcer agents.
DK0615549T3 (en) Process for the preparation of pharmaceutically active thiazolidine or oxazolidine compounds with a yeast reductase
KR860005794A (en) Method for preparing an imidazole derivative
ATE109770T1 (en) CAFFEINEIC ACID DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM.
JPS5681578A (en) Novel thioalkyl amide derivative
ES2016017A6 (en) 1,1-dioxo-cephem-4-carbothiolic acid derivatives.
DK82583D0 (en) FURYLOXAZOLYL ACETIC ACID DERIVATIVES AND PROCEDURES FOR PREPARING THEREOF
ES8703457A1 (en) Novel thioketene derivatives and process for the preparation thereof.
DK367082A (en) CEPHALOSPORINE DERIVATIVES AND PROCEDURES FOR THEIR PREPARATION
SE8203245L (en) PROCEDURE FOR ENANTIOSELECTIVE PREPARATION OF N-SUBSTITUTED PROLINE DERIVATIVES
SE8207477D0 (en) A PROCESS FOR THE PREPARATION OF HETEROCYCLIC ACETIC ACID DERIVATIVES
FI933205A (en) Thiazolethanol derivatives, process for their preparation and their intermediates
ATE18042T1 (en) SEMICARBAZIDES, THEIR PRODUCTION AND USE.