PL195965A1 - METHOD OF MAKING NEW DERIVATIVES OF PROLINES - Google Patents

METHOD OF MAKING NEW DERIVATIVES OF PROLINES

Info

Publication number
PL195965A1
PL195965A1 PL19596577A PL19596577A PL195965A1 PL 195965 A1 PL195965 A1 PL 195965A1 PL 19596577 A PL19596577 A PL 19596577A PL 19596577 A PL19596577 A PL 19596577A PL 195965 A1 PL195965 A1 PL 195965A1
Authority
PL
Poland
Prior art keywords
formula
acid
prolines
acylation
hydroxyl
Prior art date
Application number
PL19596577A
Other languages
Polish (pl)
Other versions
PL118161B1 (en
Inventor
Miguel A Ondetti
David 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 PL195965A1 publication Critical patent/PL195965A1/en
Publication of PL118161B1 publication Critical patent/PL118161B1/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

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>
PL1977195965A 1976-02-13 1977-02-12 Process for preparing novel derivatives of proline PL118161B1 (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
PL195965A1 true PL195965A1 (en) 1978-02-27
PL118161B1 PL118161B1 (en) 1981-09-30

Family

ID=27417986

Family Applications (1)

Application Number Title Priority Date Filing Date
PL1977195965A PL118161B1 (en) 1976-02-13 1977-02-12 Process for preparing novel derivatives of 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
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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.
ZA794723B (en) * 1978-09-11 1980-08-27 Univ Miami Anti-hypertensive agents
US4690937A (en) * 1979-08-14 1987-09-01 University Of Miami Anti-hypertensive agents
GR73585B (en) * 1978-09-11 1984-03-26 Univ Miami
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
US4347371A (en) * 1978-12-30 1982-08-31 Santen Pharmaceutical Co., Ltd. Disulfide compounds
US4410542A (en) 1978-12-30 1983-10-18 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
EP0656773B1 (en) * 1992-08-26 1997-04-02 Beiersdorf Aktiengesellschaft Use of radical catchers as immunomodulating agents in cosmetic and dermatological compositions
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
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GB9704522D0 (en) * 1997-03-05 1997-04-23 Smithkline Beecham Plc Compounds
ES2182203T3 (en) 1997-10-31 2003-03-01 Hoffmann La Roche DERIVATIVES OF D-PROLINA.
CA2457814A1 (en) * 2001-08-07 2003-02-20 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
CN104822266B (en) 2012-04-27 2017-12-05 陶氏益农公司 Pesticidal combination and relative method

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CA946836A (en) * 1970-03-18 1974-05-07 Miguel A. Ondetti Enzyme inhibitor

Also Published As

Publication number Publication date
ES455803A1 (en) 1978-06-16
ES467051A1 (en) 1978-11-01
ES467050A1 (en) 1978-11-01
DK157487C (en) 1990-06-11
MY102705A (en) 1992-09-30
NZ183130A (en) 1979-08-31
AR222783A1 (en) 1981-06-30
ES467053A1 (en) 1978-11-01
GB1576161A (en) 1980-10-01
FI66596B (en) 1984-07-31
CH624932A5 (en) 1981-08-31
AR226290A1 (en) 1982-06-30
RO69941A (en) 1980-05-15
FI770437A (en) 1977-08-14
ATA98977A (en) 1981-06-15
DE2759862C2 (en) 1989-12-07
FI66596C (en) 1987-03-18
DE2703828C2 (en) 1984-06-20
SE7701561L (en) 1977-09-23
SU747422A3 (en) 1980-07-23
NO146985C (en) 1983-01-12
BG37375A3 (en) 1985-05-15
NL7701457A (en) 1977-08-16
AU2134777A (en) 1978-07-20
NO146985B (en) 1982-10-04
SE8104660L (en) 1981-08-03
JPS52116457A (en) 1977-09-29
YU33177A (en) 1983-01-21
DE2703828A1 (en) 1977-08-18
GR69811B (en) 1982-07-13
AR214649A1 (en) 1979-07-13
SE423812B (en) 1982-06-07
FR2340932B1 (en) 1981-02-06
SE426697B (en) 1983-02-07
JPS604815B2 (en) 1985-02-06
DD129442A5 (en) 1978-01-18
IL51297A (en) 1980-03-31
FR2340932A1 (en) 1977-09-09
AU509899B2 (en) 1980-05-29
CA1101864A (en) 1981-05-26
ES467052A1 (en) 1978-11-01
BG37074A3 (en) 1985-03-15
NL168509C (en) 1982-04-16
BG37075A3 (en) 1985-03-15
PL118161B1 (en) 1981-09-30
DD129442B3 (en) 1990-01-10
DK157487B (en) 1990-01-15
PH12970A (en) 1979-10-24
IL51297A0 (en) 1977-03-31
AT365569B (en) 1982-01-25
IE44707B1 (en) 1982-03-10
IT1062293B (en) 1984-05-23
HU181965B (en) 1983-11-28
IE44707L (en) 1977-08-13
DK59677A (en) 1977-08-14
HK20281A (en) 1981-05-22
MY8200075A (en) 1982-12-31
AR222445A1 (en) 1981-05-29
CH622503A5 (en) 1981-04-15
YU40664B (en) 1986-04-30
CH624931A5 (en) 1981-08-31
KE3136A (en) 1981-07-03
NO770464L (en) 1977-08-16

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Legal Events

Date Code Title Description
LAPS Decisions on the lapse of the protection rights

Effective date: 20030125