GB1064263A - Improvements in or relating to a pentacosapeptide - Google Patents

Improvements in or relating to a pentacosapeptide

Info

Publication number
GB1064263A
GB1064263A GB24840/64A GB2484064A GB1064263A GB 1064263 A GB1064263 A GB 1064263A GB 24840/64 A GB24840/64 A GB 24840/64A GB 2484064 A GB2484064 A GB 2484064A GB 1064263 A GB1064263 A GB 1064263A
Authority
GB
United Kingdom
Prior art keywords
arg
lys
tos
val
cbo
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
GB24840/64A
Inventor
Roger Boissonnas
Stephan Cuttmann
Janos Pless
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.)
Sandoz AG
Original Assignee
Sandoz 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
Application filed by Sandoz AG filed Critical Sandoz AG
Publication of GB1064263A publication Critical patent/GB1064263A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • C07K14/665—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans derived from pro-opiomelanocortin, pro-enkephalin or pro-dynorphin
    • C07K14/695—Corticotropin [ACTH]
    • 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
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
    • C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
    • C07K5/06052—Val-amino acid
    • 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)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Zoology (AREA)
  • Toxicology (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

The peptide H-Ser-Tyr-Ser-Nle-Glu-His-Phe-Arg - Try - Gly - Lys - Pro - Val - Gly - Lys - Lys-Arg - Arg - Pro - Val - Lys - Val - Tyr - Pro - Val - NH2 and its acid addition salts are prepared by hydrolysing off the protecting groups from the N-trityl-Ne -formyl derivative and optionally forming the acid addition salt. N - Tri - Ser - Tyr - Ser - Nle - Glu - His - Phe - Arg - Try - Gly - Lys (For) - Pro - Val - Gly - Lys (For) - Lys (For) - Arg - Arg - Pro - Val - Lys (For) - Val - Tyr - Pro - Val - NH2 (where For = formyl and Tri = trityl) is prepared by stepwise synthesis through the following compounds: (where CBO = carbobenzyloxy; CP = trichlorophenyl; Tos = Tosyl; and TB = t=butyl) CBO-Tyr(CBO)OCP; CBO-Lys (For)OCP; CBO-Arg(Tos)-OCP; CBO-Phe-OCP; CBO-Glu(OTB)-OCP; CBO-Try-Gly-OCP; CBO - Val - Gly - OCP; CBO - Val-OCP; CBO - Tyr (CBO) - Pro - Val - NH2; CBO - Tyr - Pro - Val - NH2; H - Tyr - Pro-Val - NH2 - HBr; CBO - Val - Tyr - Pro - Val-NH2; H - Val - Tyr - Pro - Val - NH2 - HBr; CBO - Lys (For) - Val - Tyr - Pro - Val - NH2; H - Lys (For) - Val - Tyr - Pro - Val - NH2; CBO - Arg(Tos) - ProOTB; CBO - Arg (Tos)-ProOH; H - Arg(Tos) - ProOH, HBr; CBO-Arg (Tos) - ProOH; H - Arg (Tos)-Arg (Tos) - ProOH,HBr; CBO - Lys (For) - Arg (Tos)-Arg (Tos)-ProOH; H-Lys (For)-Arg (Tos)-Arg (Tos)-ProOH; - ProOH, HBr; CBO - Lys (For) - Arg (Tos)-Arg (Tos) - ProOH; H-Lys (For)-Arg (Tos)-Arg(Tos)-ProOh, HBr; CBO - Lys (For) - Lys (For) - Arg (Tos) - Arg (Tos) - ProOH; H - Lys (For) - Lys (For) - Arg (Tos) - Arg (Tos) - ProOH, HBr; CBO - Val - Gly - Lys (For) - Lys (For)-Arg (Tos) - Arg (Tos) - ProOH; CBO - Val-Gly - Lys (For) - Lys (For) - Arg (Tos) - Arg (Tos)-Pro - Val - Lys (For) - Val - Tyr - Pro - ValNH2; H - Val - Gly - Lys (For) - Lys (For) - Arg (Tos)-Arg (Tos) - Pro - Val - Lys (For) - Val - Tyr-Pro - Val - NH2; H - Lys (For) - Pro - OTB, HAc; CBO - Try - Gly - Lys (For) - ProOTB; CBO - Arg (Tos) - Try - Gly - Lys (For) - Pro-OTB; H - Arg (Tos) - Try - Gly - Lys (For)-Pro - OTB; CBO - Phe - Arg (Tos) - Try - Gly-Lys (For) - Pro - OTB; H - Phe - Arg (Tos)-Try - Gly - Lys (For) - Pro - OTB; CBO - His-Phe - Arg (Tos) - Try - Gly - Lys (For) - Pro OTB; CBO - His - Phe - Arg (Tos) - Try - Gly-Lys (For) - ProOH; H - His - Phe - Arg (Tos)-Try - Gly - Lys (For) - ProOH; CBO - Glu-(OTB) - His - Phe - Arg (Tos) - Try - Gly - Lys (For) - ProOH; CBO - Glu (OTB) - His - Phe-Arg (Tos) - Try - Gly - Lys (For) - ProOCP; CBO - Glu (OTB) - His - Phe - Arg (Tos) - Try-Gly - Lys (For) - Lys (For) - Arg (Tos) - Arg (Tos)-Pro - Val - Lys (For) - Val - Tyr - Pro - ValNH2; H - Glu - His - Phe - Arg (Tos) - Try - Gly - Lys (For) - Lys (For) - Arg (Tos) - Arg (Tos) - Pro-Val - Lys (For) - Val - Tyr - Pro - Val - NH2; Tri - Ser - TyrOMe; Tri - Ser - Tyr - NHNH2; CBO - Ser - Nle - OMe; H - Ser - Nle - OMe, HCl; Tri - Ser - Tyr - Ser - Nle - OMe; Tri-Ser - Tyr - Ser - NleNHNH2; Tri - Ser - Tyr-Ser - Nle - N3. Tri - (2,4,5 - trichloro - phenyl)-phosphite is also prepared. Pharmaceutical compositions comprise the pentacosapeptides of the invention and a suitable inert carrier. The compositions may be in a form suitable for oral, parenteral, enteral or intranasal administration.
GB24840/64A 1963-06-28 1964-06-16 Improvements in or relating to a pentacosapeptide Expired GB1064263A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH802163A CH439316A (en) 1963-06-28 1963-06-28 Process for the production of a new polypeptide

Publications (1)

Publication Number Publication Date
GB1064263A true GB1064263A (en) 1967-04-05

Family

ID=4333925

Family Applications (1)

Application Number Title Priority Date Filing Date
GB24840/64A Expired GB1064263A (en) 1963-06-28 1964-06-16 Improvements in or relating to a pentacosapeptide

Country Status (9)

Country Link
AT (1) AT266332B (en)
BE (1) BE649794A (en)
CH (1) CH439316A (en)
ES (1) ES301459A1 (en)
FR (1) FR3966M (en)
GB (1) GB1064263A (en)
NL (1) NL6407156A (en)
NO (1) NO115214B (en)
OA (1) OA01252A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022206716A1 (en) * 2021-03-31 2022-10-06 张菁 Drug containing adrenocorticotropic hormone or derivative thereof and use thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022206716A1 (en) * 2021-03-31 2022-10-06 张菁 Drug containing adrenocorticotropic hormone or derivative thereof and use thereof

Also Published As

Publication number Publication date
FR3966M (en) 1966-02-28
OA01252A (en) 1969-01-25
BE649794A (en) 1964-12-28
CH439316A (en) 1967-07-15
AT266332B (en) 1968-11-11
NO115214B (en) 1968-09-02
NL6407156A (en) 1964-12-29
ES301459A1 (en) 1965-01-16

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