FR2090682A5 - Pyroglutamyl-histidyl-prolineamide as thyroid stimulant- - from prolineamide and tosyl -l-histidine derivs - Google Patents

Pyroglutamyl-histidyl-prolineamide as thyroid stimulant- - from prolineamide and tosyl -l-histidine derivs

Info

Publication number
FR2090682A5
FR2090682A5 FR7114673A FR7114673A FR2090682A5 FR 2090682 A5 FR2090682 A5 FR 2090682A5 FR 7114673 A FR7114673 A FR 7114673A FR 7114673 A FR7114673 A FR 7114673A FR 2090682 A5 FR2090682 A5 FR 2090682A5
Authority
FR
France
Prior art keywords
prolineamide
tosyl
pyroglutamyl
derivs
histidyl
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.)
Expired
Application number
FR7114673A
Other languages
French (fr)
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.)
Tanabe Seiyaku Co Ltd
Original Assignee
Tanabe Seiyaku Co Ltd
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 Tanabe Seiyaku Co Ltd filed Critical Tanabe Seiyaku Co Ltd
Application granted granted Critical
Publication of FR2090682A5 publication Critical patent/FR2090682A5/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • 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
    • C07K5/08—Tripeptides
    • C07K5/0821—Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp
    • C07K5/0825—Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp and Glp-amino acid; Derivatives thereof
    • 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)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Pyrrole Compounds (AREA)

Abstract

Nim-tosyl-1-histidine derivs. (II) are intermediates for the thyroid stimulant 1-pyroglutamyl-1-histidyl-1-proline-amide (I) (where X = o-nitrophenylsulphenyl, p-methoxybenzyloxycarbonyl, t-butoxy or t-amyloxycarbonyl; R = H or C2-7 alkoxycarbonyle prepd. by condensing (II) with 1-prolineamide, removing X from the alpha-amino of the resulting dipeptide, condensing with 1-pyroglutamic acid and finally removing tosyl and Y-protective groups from the resulting tripeptide. Y (protecting the NH of pyroglutamic acid) = acyl e.g. p-methoxybenzyloxycarbonyl. High yield of dipeptide result from which X is easily removed whilst leaving the tosyl group intact.
FR7114673A 1970-04-25 1971-04-23 Pyroglutamyl-histidyl-prolineamide as thyroid stimulant- - from prolineamide and tosyl -l-histidine derivs Expired FR2090682A5 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP45035524A JPS4829225B1 (en) 1970-04-25 1970-04-25

Publications (1)

Publication Number Publication Date
FR2090682A5 true FR2090682A5 (en) 1972-01-14

Family

ID=12444122

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7114673A Expired FR2090682A5 (en) 1970-04-25 1971-04-23 Pyroglutamyl-histidyl-prolineamide as thyroid stimulant- - from prolineamide and tosyl -l-histidine derivs

Country Status (4)

Country Link
JP (1) JPS4829225B1 (en)
CH (1) CH557362A (en)
DE (1) DE2119966A1 (en)
FR (1) FR2090682A5 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2181677A1 (en) * 1972-01-20 1973-12-07 Reckitt & Colmann Prod Ltd

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5225939A (en) * 1975-08-25 1977-02-26 Hitachi Ltd Ignition timing controller
JPS5234143A (en) * 1975-09-12 1977-03-15 Hitachi Ltd Depression-type ignition time adjusting device of distributor for inte rnal combustion engine
EP0749978A4 (en) * 1994-01-31 1997-10-01 Japan Tobacco Inc Method of separating and purifying trh analogs and process for producing solvates of trh analogs

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2181677A1 (en) * 1972-01-20 1973-12-07 Reckitt & Colmann Prod Ltd

Also Published As

Publication number Publication date
CH557362A (en) 1974-12-31
DE2119966A1 (en) 1971-11-25
JPS4829225B1 (en) 1973-09-08

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