ES2035798A1 - Procedimiento para la preparacion de 1-(2s)-3-mercapto-metil-1-oxopropil)-l-prolina. - Google Patents

Procedimiento para la preparacion de 1-(2s)-3-mercapto-metil-1-oxopropil)-l-prolina.

Info

Publication number
ES2035798A1
ES2035798A1 ES919102086A ES9102086A ES2035798A1 ES 2035798 A1 ES2035798 A1 ES 2035798A1 ES 919102086 A ES919102086 A ES 919102086A ES 9102086 A ES9102086 A ES 9102086A ES 2035798 A1 ES2035798 A1 ES 2035798A1
Authority
ES
Spain
Prior art keywords
proline
methyl
formula
oxopropyl
mercapto
Prior art date
Legal status (The legal status 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 status listed.)
Granted
Application number
ES919102086A
Other languages
English (en)
Other versions
ES2035798B1 (es
Inventor
Geza Schneider
Gabor Blasko
Agnes Kovacs
Gsabriella Urmos
Judit Kun
Ilma Dinnyes
Ivan Beck
Elemer Jakfalvi
Andras Dietz
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Egyt Gyogyszervegyeszeti Gyar
Original Assignee
Egyt Gyogyszervegyeszeti Gyar
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 Egyt Gyogyszervegyeszeti Gyar filed Critical Egyt Gyogyszervegyeszeti Gyar
Publication of ES2035798A1 publication Critical patent/ES2035798A1/es
Application granted granted Critical
Publication of ES2035798B1 publication Critical patent/ES2035798B1/es
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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
    • C07D207/08—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
    • 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)
  • 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)
  • Peptides Or Proteins (AREA)

Abstract

PROCEDIMIENTO PARA LA PREPARACION DE 1-[(2S)-3-MERCAPTO-METIL-1-OXOPROPIL]-L-PROLINA. NUEVO PROCEDIMIENTO PARA LA PREPARACION DE 1-[(2S)-3-MERCAPTO-2-METIL-1-OXOPROPIL]-L-PROLINA (CAPTOPRILO) DE FORMULA (I), QUE COMPRENDE LA HIDROGENACION DE 1-[(2S)-2-METIL-1-OXO-3-RODANIDO-PROPIL]-L-PROLINA DE FORMULA (II) EN UN MEDIO INERTE, EN PRESENCIA DE UN CATALIZADOR A UNA TEMPERATURA ENTRE 50 Y 120 C Y BAJO UNA PRESION DE 105 A 107 PA. EL COMPUESTO DE FORMULA (II) ARRIBA INDICADO ES NUEVO Y PUEDE PREPARARSE ACILANDO L-PROLINA CON UN DERIVADO REACTIVO ACILANTE DEL ACIDO (2S)-2-METIL-3-RODANIDOPRO-PIONICO DE FORMULA (III). EL PROCEDIMIENTO SEGUN LA INVENCION HACE POSIBLE OBTENER EL COMPUESTO DE FORMULA (I) DE MANERA SIMPLE Y CON GRAN PUREZA Y BUEN RENDIMIENTO EN GENERAL. UTILIZACION, FARMACOS CONTRA LA HIPERTENSION.
ES9102086A 1990-09-21 1991-09-20 Procedimiento para la preparacion de 1-(2s)-3-mercapto-metil-1-oxopropil)-l-prolina. Expired - Fee Related ES2035798B1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
HU905998A HU208954B (en) 1990-09-21 1990-09-21 Process for producing 1-(3-mercapto-(2s)-methyl-1-oxo-propyl)-l-prolyn

Publications (2)

Publication Number Publication Date
ES2035798A1 true ES2035798A1 (es) 1993-04-16
ES2035798B1 ES2035798B1 (es) 1994-02-16

Family

ID=10971099

Family Applications (1)

Application Number Title Priority Date Filing Date
ES9102086A Expired - Fee Related ES2035798B1 (es) 1990-09-21 1991-09-20 Procedimiento para la preparacion de 1-(2s)-3-mercapto-metil-1-oxopropil)-l-prolina.

Country Status (24)

Country Link
US (1) US5202443A (es)
KR (1) KR930005973A (es)
AT (1) AT395148B (es)
AU (1) AU637719B2 (es)
CA (1) CA2051985A1 (es)
CH (1) CH683099A5 (es)
DE (1) DE4123172A1 (es)
DK (1) DK162191A (es)
ES (1) ES2035798B1 (es)
FI (1) FI914426A (es)
FR (1) FR2667065B1 (es)
GB (1) GB2248060B (es)
GR (1) GR1002173B (es)
HU (1) HU208954B (es)
IL (1) IL99535A (es)
IT (1) IT1251845B (es)
NL (1) NL9101582A (es)
NO (1) NO176141C (es)
PL (1) PL291789A1 (es)
PT (1) PT99022A (es)
RU (1) RU2026286C1 (es)
SE (1) SE501501C2 (es)
TW (1) TW203042B (es)
ZA (1) ZA917517B (es)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
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

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES8101548A1 (es) * 1979-11-21 1980-12-16 Farmaceutico Quimico Lab Procedimiento de obtencion de un derivado de prolina
ES8105280A1 (es) * 1980-04-24 1981-05-16 Inke Sa Procedimiento para la obtencion de la n-(d-3-mercapto-2-me tilpropionil) l-prolina.
ES8200340A1 (es) * 1979-12-29 1981-11-16 Egyt Gyogyszervegyeszeti Gyar Procedimiento de preparar acido 1-(3-mercapto-(2s)-metilpro-pionil)-pirrolidina-(2s)-carboxilico
ES8307222A1 (es) * 1981-05-27 1983-07-01 Crc Ricerca Chim "un procedimiento para la preparacion enantioselectiva de derivados n-sustituidos de prolina".
ES8603697A1 (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
ES8604514A1 (es) * 1985-04-10 1986-02-01 Farmhispania Procedimiento para la sintesis de la 1-(3-mercapto-2-d(-)- metilo-propanol)-2(-) prolina

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
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
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

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES8101548A1 (es) * 1979-11-21 1980-12-16 Farmaceutico Quimico Lab Procedimiento de obtencion de un derivado de prolina
ES8200340A1 (es) * 1979-12-29 1981-11-16 Egyt Gyogyszervegyeszeti Gyar Procedimiento de preparar acido 1-(3-mercapto-(2s)-metilpro-pionil)-pirrolidina-(2s)-carboxilico
ES8105280A1 (es) * 1980-04-24 1981-05-16 Inke Sa Procedimiento para la obtencion de la n-(d-3-mercapto-2-me tilpropionil) l-prolina.
ES8307222A1 (es) * 1981-05-27 1983-07-01 Crc Ricerca Chim "un procedimiento para la preparacion enantioselectiva de derivados n-sustituidos de prolina".
ES8604514A1 (es) * 1985-04-10 1986-02-01 Farmhispania Procedimiento para la sintesis de la 1-(3-mercapto-2-d(-)- metilo-propanol)-2(-) prolina
ES8603697A1 (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

Also Published As

Publication number Publication date
GR910100391A (el) 1992-09-11
CA2051985A1 (en) 1992-03-22
ITMI912520A0 (it) 1991-09-20
SE9102722L (sv) 1992-03-22
HUT62266A (en) 1993-04-28
SE501501C2 (sv) 1995-02-27
DK162191D0 (da) 1991-09-20
HU208954B (en) 1994-02-28
ATA10591A (de) 1992-02-15
GB2248060B (en) 1994-04-13
FI914426A0 (fi) 1991-09-20
DK162191A (da) 1992-03-22
NO176141B (no) 1994-10-31
FR2667065A1 (fr) 1992-03-27
GB9120150D0 (en) 1991-11-06
GR1002173B (en) 1996-03-07
HU905998D0 (en) 1991-03-28
KR930005973A (ko) 1993-04-20
NO913720L (no) 1992-03-23
CH683099A5 (de) 1994-01-14
ES2035798B1 (es) 1994-02-16
NO913720D0 (no) 1991-09-20
AU637719B2 (en) 1993-06-03
RU2026286C1 (ru) 1995-01-09
PL291789A1 (en) 1992-12-14
ZA917517B (en) 1994-08-26
NO176141C (no) 1995-02-08
FI914426A (fi) 1992-03-22
IT1251845B (it) 1995-05-26
IL99535A0 (en) 1992-08-18
PT99022A (pt) 1992-08-31
GB2248060A (en) 1992-03-25
ITMI912520A1 (it) 1993-03-20
NL9101582A (nl) 1992-04-16
AU8461191A (en) 1992-03-26
SE9102722D0 (sv) 1991-09-20
AT395148B (de) 1992-09-25
FR2667065B1 (fr) 1994-04-29
TW203042B (es) 1993-04-01
IL99535A (en) 1995-12-31
US5202443A (en) 1993-04-13
DE4123172A1 (de) 1992-04-02

Similar Documents

Publication Publication Date Title
NL193374C (nl) Anti-hypertensieve mercaptoacylderivaten van gesubstitueerde prolinen en farmaceutische preparaten.
YU40664B (en) Process for obtaining 1-(3-mercapto-2-d-methyl-propanoyl)-l-proline
NZ247642A (en) Thioalkylacyl substituted heterocyclic compounds; pharmaceutical compositions and preparatory methods
NO20060703L (no) Fremgangsmate for fremstilling av cis-4-fluor-1-prolinderivater
NO20051757L (no) Fremgangsmate ved fremstilling av 2-azadihydroksy-bicyklo [2.2.2]-heptanderivater
EP0825983A1 (en) Process for the preparation of 2,2'-bipyrrolyl-pyrromethene (prodigiosins) derivatives
ES2035798A1 (es) Procedimiento para la preparacion de 1-(2s)-3-mercapto-metil-1-oxopropil)-l-prolina.
AU4611589A (en) Enzyme-inhibiting amino acid derivatives, a process for the preparation thereof, agents containing these, and the use thereof.
IE802603L (en) Preparation of pyrrolidine-,piperidine-,and thiazolidine¹derivatives
DK0595111T4 (da) Carbazolonderivater og fremgangsmåde til deres fremstilling
ES8205750A1 (es) Un procedimiento para la preparacion de nuevos derivados de fenetilamina.
US4482725A (en) S-Acylation products of mercaptoacyl amino acids and carboxyl group containing diuretics
AU542270B2 (en) Imidazolylalkylguanidine derivatives
DE3268574D1 (en) Process for the production of quinoline containing heterocycles, intermediates, and process for the production of the intermediates
YU153991A (sh) Postupak za dobijanje 1-[(2s)-3-merkapto-metil-1-oksopropil]-l-prolina
CA2093510A1 (en) Oxysulfonyl carbamates
DK241188A (da) Fremgangsmaade til fremstilling af alfa-(alkylphenyl)-4-(hydroxydiphenyl-methyl)-1-piperidin-butanol og mellemprodukt til brug ved fremgangsmaaden
US4217458A (en) Acylmercaptoacyl derivatives of 4,5-dihydro-1H-pyrrole-2-carboxylic acids and 1,4,5,6-tetrahydropyridine-2-carboxylic acids
GB2051806B (en) Hexahydrazepine piperidine and pyrrolidine derivatives
TH11721EX (th) กรรมวิธีสำหรับเตรียม 1-[(2s)-3-เมอร์แคพโท-2-เมธิล-1-1-ออกโซโพรพิล]-l-โพรลีน
ES8307222A1 (es) "un procedimiento para la preparacion enantioselectiva de derivados n-sustituidos de prolina".
JPS5726658A (en) 4r -4- 3-substituted carboxy-3-diazo-2-oxopropyl -2- azetidinone derivative and its preparation
ES8502096A1 (es) Un procedimiento para la preparacion de 4-amino-1,2-hidro- carbilpirazolidinas
ES8404678A1 (es) Un procedimiento para la preparacion de derivados de pirrolidina.
MY108145A (en) Process for preparing pyrrolidine carboxylic acid derivatives compositions

Legal Events

Date Code Title Description
FD1A Patent lapsed

Effective date: 20001009