IT1270017B - "QUANTITATIVE SYNTHESIS OF 3- (L-PIROGLUTAMIL) -L-THIAZOLIDIN-4- CARBOXYLIC ACID AND ITS DERIVATIVES" - Google Patents

"QUANTITATIVE SYNTHESIS OF 3- (L-PIROGLUTAMIL) -L-THIAZOLIDIN-4- CARBOXYLIC ACID AND ITS DERIVATIVES"

Info

Publication number
IT1270017B
IT1270017B ITMI941955A ITMI941955A IT1270017B IT 1270017 B IT1270017 B IT 1270017B IT MI941955 A ITMI941955 A IT MI941955A IT MI941955 A ITMI941955 A IT MI941955A IT 1270017 B IT1270017 B IT 1270017B
Authority
IT
Italy
Prior art keywords
thiazolidin
derivatives
carboxylic acid
piroglutamil
quantitative synthesis
Prior art date
Application number
ITMI941955A
Other languages
Italian (it)
Inventor
Stefano Poli
Ambrogio Magni
Gianettore Bocchiola
Original Assignee
Poli Ind Chimica Spa
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 Poli Ind Chimica Spa filed Critical Poli Ind Chimica Spa
Publication of ITMI941955A0 publication Critical patent/ITMI941955A0/en
Priority to ITMI941955A priority Critical patent/IT1270017B/en
Priority to CNB951953222A priority patent/CN1143863C/en
Priority to CZ97915A priority patent/CZ91597A3/en
Priority to BR9509087A priority patent/BR9509087A/en
Priority to RO97-00611A priority patent/RO115957B1/en
Priority to PL95319380A priority patent/PL181824B1/en
Priority to SK400-97A priority patent/SK40097A3/en
Priority to PCT/EP1995/003720 priority patent/WO1996010036A1/en
Priority to CO95044814A priority patent/CO4480030A1/en
Publication of ITMI941955A1 publication Critical patent/ITMI941955A1/en
Priority to BG101310A priority patent/BG63895B1/en
Application granted granted Critical
Publication of IT1270017B publication Critical patent/IT1270017B/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06139—Dipeptides with the first amino acid being heterocyclic
    • C07K5/06173—Dipeptides with the first amino acid being heterocyclic and Glp-amino acid; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Biophysics (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Pyrrole Compounds (AREA)

Abstract

L'Acido 3-(L-piroglutamil)-L-tiazolidin-4-carbossilico e i suoi derivati vengono sintetizzati con rese quantitative attraverso un processo di condensazione fra acido L-piroglutammico o suoi prodotti di sostituzione in presenza di solvente idrocarburico alifatico o aromatico o di solventi clorurati in presenza di dicicloesilcarbodimmide o similari, o per condensazione di derivati attivi di acido L-piroglutammico con derivati dell'acido tiazolidin-4-carbossilico. L'idrolisi dei gruppi protettivi dell'acido tiazolidin-4-carbossilico avviene a mezzo di catalizzatori di trasferimento di fase con rese quantitative.3- (L-pyroglutamyl) -L-thiazolidin-4-carboxylic acid and its derivatives are synthesized with quantitative yields through a process of condensation between L-pyroglutamic acid or its replacement products in the presence of an aliphatic or aromatic hydrocarbon solvent or of chlorinated solvents in the presence of dicyclohexylcarbodimide or the like, or by condensation of active derivatives of L-pyroglutamic acid with derivatives of thiazolidin-4-carboxylic acid. The hydrolysis of the protective groups of thiazolidin-4-carboxylic acid occurs by means of phase transfer catalysts with quantitative yields.

ITMI941955A 1994-09-27 1994-09-27 "QUANTITATIVE SYNTHESIS OF 3- (L-PIROGLUTAMIL) -L-THIAZOLIDIN-4- CARBOXYLIC ACID AND ITS DERIVATIVES" IT1270017B (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
ITMI941955A IT1270017B (en) 1994-09-27 1994-09-27 "QUANTITATIVE SYNTHESIS OF 3- (L-PIROGLUTAMIL) -L-THIAZOLIDIN-4- CARBOXYLIC ACID AND ITS DERIVATIVES"
RO97-00611A RO115957B1 (en) 1994-09-27 1995-09-21 Process for preparing 3-(l-pyroglutamyl)-l-thiazolidine-4-carboxylic acid and derivatives thereof
CZ97915A CZ91597A3 (en) 1994-09-27 1995-09-21 Process for preparing 3-(l-pyroglutamyl)-l-thiazolidine-4-carboxylic acid
BR9509087A BR9509087A (en) 1994-09-27 1995-09-21 Process for the quantitative synthesis of 3- (1-pyroglutamyl) -1-thiazolidine-4-carboxylic acid and derivatives thereof
CNB951953222A CN1143863C (en) 1994-09-27 1995-09-21 Process for the quantitative synthesis of 3-(L-pyrolutamyl)-L-tiazolidine-4-carboxylic acid and derivatives thereof
PL95319380A PL181824B1 (en) 1994-09-27 1995-09-21 Method of quantitatively synthesising 3-(l-pyrrogutamyl)-l-thiazolydino-4-carbpxylic acid and its derivatives
SK400-97A SK40097A3 (en) 1994-09-27 1995-09-21 A process for the quantitative synthesis of 3-(l-pyroglutamyl)-l- -thiazolidine-4-carboxylic acid and derivatives thereof
PCT/EP1995/003720 WO1996010036A1 (en) 1994-09-27 1995-09-21 A process for the quantitative synthesis of 3-(l-pyroglutamyl)-l-thiazolidine-4-carboxylic acid and derivatives thereof
CO95044814A CO4480030A1 (en) 1994-09-27 1995-09-27 QUANTITATIVE SYNTHESIS OF ACID 3- (L-PIROGLUTAMIL) -L- TIAZOLIDIN-4-CARBOXILICO AND ITS DERIVATIVES
BG101310A BG63895B1 (en) 1994-09-27 1997-03-11 Method for quantitative synthesis of 3-(pyroglutamyl)-l-thiazolydine-4-carboxylic acid and its derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
ITMI941955A IT1270017B (en) 1994-09-27 1994-09-27 "QUANTITATIVE SYNTHESIS OF 3- (L-PIROGLUTAMIL) -L-THIAZOLIDIN-4- CARBOXYLIC ACID AND ITS DERIVATIVES"

Publications (3)

Publication Number Publication Date
ITMI941955A0 ITMI941955A0 (en) 1994-09-27
ITMI941955A1 ITMI941955A1 (en) 1996-03-27
IT1270017B true IT1270017B (en) 1997-04-16

Family

ID=11369599

Family Applications (1)

Application Number Title Priority Date Filing Date
ITMI941955A IT1270017B (en) 1994-09-27 1994-09-27 "QUANTITATIVE SYNTHESIS OF 3- (L-PIROGLUTAMIL) -L-THIAZOLIDIN-4- CARBOXYLIC ACID AND ITS DERIVATIVES"

Country Status (10)

Country Link
CN (1) CN1143863C (en)
BG (1) BG63895B1 (en)
BR (1) BR9509087A (en)
CO (1) CO4480030A1 (en)
CZ (1) CZ91597A3 (en)
IT (1) IT1270017B (en)
PL (1) PL181824B1 (en)
RO (1) RO115957B1 (en)
SK (1) SK40097A3 (en)
WO (1) WO1996010036A1 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108088936B (en) * 2017-12-08 2020-05-22 常州寅盛药业有限公司 Impurity obtained in preparation of pidotimod ethyl ester and quality detection method thereof
CN108715598A (en) * 2018-06-13 2018-10-30 峨眉山宏昇药业股份有限公司 A kind of preparation method of Pidotimod
CN117088939A (en) * 2022-05-11 2023-11-21 江苏吴中医药集团有限公司 Preparation method of pidotimod

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1202426B (en) * 1987-01-26 1989-02-09 Poli Ind Chimica Spa THIAZOLIDIN-4-CARBOXYLIC ACID DERIVATIVE, ITS PREPARATION AND PHARMACEUTICAL COMPOSITIONS THAT CONTAIN IT
IT1239029B (en) * 1989-10-12 1993-09-20 Poli Ind Chimica Spa PROCESS FOR THE PREPARATION OF 3- (L-PYROGLUTAMYL) -L- THIAZOLIDIN-4-CARBOXYLIC ACID AND ITS DERIVATIVES.

Also Published As

Publication number Publication date
CN1158620A (en) 1997-09-03
ITMI941955A0 (en) 1994-09-27
RO115957B1 (en) 2000-08-30
PL181824B1 (en) 2001-09-28
CN1143863C (en) 2004-03-31
BR9509087A (en) 1998-07-21
WO1996010036A1 (en) 1996-04-04
BG63895B1 (en) 2003-05-30
ITMI941955A1 (en) 1996-03-27
SK40097A3 (en) 1997-09-10
PL319380A1 (en) 1997-08-04
CZ91597A3 (en) 1997-09-17
CO4480030A1 (en) 1997-07-09
BG101310A (en) 1997-12-30

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Legal Events

Date Code Title Description
0001 Granted
TA Fee payment date (situation as of event date), data collected since 19931001

Effective date: 19970926