GB1033906A - Process for the production of a new tetrapeptide - Google Patents

Process for the production of a new tetrapeptide

Info

Publication number
GB1033906A
GB1033906A GB2408/66A GB240866A GB1033906A GB 1033906 A GB1033906 A GB 1033906A GB 2408/66 A GB2408/66 A GB 2408/66A GB 240866 A GB240866 A GB 240866A GB 1033906 A GB1033906 A GB 1033906A
Authority
GB
United Kingdom
Prior art keywords
tos
cbo
cys
ile
reacting
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
GB2408/66A
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.)
Novartis AG
Original Assignee
JR Geigy AG
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 CH386362A external-priority patent/CH440310A/en
Application filed by JR Geigy AG filed Critical JR Geigy AG
Publication of GB1033906A publication Critical patent/GB1033906A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/04—Linear peptides containing only normal peptide links
    • C07K7/16—Oxytocins; Vasopressins; Related 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)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

The tetrapeptide S-Bz-N-Tos-Cys-Tyr-Ile-Ser-OMe and the corresponding azide (where Bz = benzyl and Tos = tosyl) is prepared by reacting a reactive functional derivative of CBO-IleOH (CBO = carbobenzoxy) with HSerO-Alkyl or -O-Aralkyl to give the ester of CBO-Ile-SerOH, reacting this with catalytically activated H2, condensing it with S-Bz-N-Tos-Cys-TyrOH in the presence of carbodiimide to give SBz-N-Tos-Cys-Tyr-Ile-SerOH ester, e.g. methyl ester, reacting this with NH2NH2 to give the hydrazide then reacting this with HNO2; or by reacting a functional derivative of CBO-IleOH with an N2-protected serine hydrazide, treating the CBO-Ile-Ser-NHNH2-N2 derivative with activated H2, condensing the product with S-Bz-N-Tos-Cys-TyrOH in the presence of carbodiimide to give SB2-N-Tos-Cys-Tyr-Ile-SerNHNH2-N2 derivative and converting this into the free hydrazide by acid solvolysis before reaction with HNO2.
GB2408/66A 1962-03-30 1963-03-22 Process for the production of a new tetrapeptide Expired GB1033906A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH386362A CH440310A (en) 1962-03-30 1962-03-30 Process for the preparation of a new nonapeptide amide
CH1201062 1962-10-12

Publications (1)

Publication Number Publication Date
GB1033906A true GB1033906A (en) 1966-06-22

Family

ID=25694033

Family Applications (3)

Application Number Title Priority Date Filing Date
GB2408/66A Expired GB1033906A (en) 1962-03-30 1963-03-22 Process for the production of a new tetrapeptide
GB2407/66A Expired GB1033905A (en) 1962-03-30 1963-03-22 Process for the production of a new pentapeptide
GB11375/63A Expired GB1033904A (en) 1962-03-30 1963-03-22 Process for the production of a new nonapeptidamide

Family Applications After (2)

Application Number Title Priority Date Filing Date
GB2407/66A Expired GB1033905A (en) 1962-03-30 1963-03-22 Process for the production of a new pentapeptide
GB11375/63A Expired GB1033904A (en) 1962-03-30 1963-03-22 Process for the production of a new nonapeptidamide

Country Status (5)

Country Link
BE (1) BE630332A (en)
ES (1) ES286566A1 (en)
FR (1) FR3565M (en)
GB (3) GB1033906A (en)
SE (1) SE322229B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4018912A (en) * 1975-07-28 1977-04-19 Ayerst Mckenna And Harrison Ltd. Tripeptide derivatives with central nervous system activity and preparation thereof

Also Published As

Publication number Publication date
BE630332A (en) 1963-10-21
GB1033905A (en) 1966-06-22
ES286566A1 (en) 1963-11-16
FR3565M (en) 1965-09-27
SE322229B (en) 1970-04-06
GB1033904A (en) 1966-06-22

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