GB1486580A - Heptapeptides - Google Patents

Heptapeptides

Info

Publication number
GB1486580A
GB1486580A GB50494/76A GB5049476A GB1486580A GB 1486580 A GB1486580 A GB 1486580A GB 50494/76 A GB50494/76 A GB 50494/76A GB 5049476 A GB5049476 A GB 5049476A GB 1486580 A GB1486580 A GB 1486580A
Authority
GB
United Kingdom
Prior art keywords
phe
boc
lys
asn
trt
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
GB50494/76A
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.)
Wyeth Canada Inc
Original Assignee
Ayerst Mckenna and Harrison Inc
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 US423352A external-priority patent/US3917578A/en
Priority claimed from US493595A external-priority patent/US3917581A/en
Application filed by Ayerst Mckenna and Harrison Inc filed Critical Ayerst Mckenna and Harrison Inc
Publication of GB1486580A publication Critical patent/GB1486580A/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
    • C07K14/575—Hormones
    • C07K14/655—Somatostatins
    • C07K14/6555—Somatostatins at least 1 amino acid in D-form
    • 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
    • C07K5/10—Tetrapeptides
    • C07K5/1002—Tetrapeptides with the first amino acid being neutral
    • C07K5/1005—Tetrapeptides with the first amino acid being neutral and aliphatic
    • 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
    • C07K5/10—Tetrapeptides
    • C07K5/1019—Tetrapeptides with the first amino acid being basic
    • 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)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Molecular Biology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Biophysics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Biochemistry (AREA)
  • Endocrinology (AREA)
  • Toxicology (AREA)
  • Zoology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

1486580 Hexa and heptapeptides AYERST MCKENNA & HARRISON Ltd 6 Dec 1974 [10 Dec 1973 1 Aug 1974] 50494/76 Divided out of 1486578 Heading C3H Peptides of formula wherein X is OH or O(lower(C 1 -C 4 )alkyl) α is Acm or Trt R 3 is hydrogen or Boc-NH- or an acylating derivative (defined) thereof, provided that, if R 3 is Boc-NH-, Lys may be replaced by D-Lys. The peptides may be prepared by a process which comprises: the reaction of the dipeptide with an activated ester of to yield the tripeptide which is treated under moderately acidic conditions (defined) to yield which is reacted with an activated ester of to yield the tetrapeptide which, on hydrogenation in the presence of a noble metal hydrogenation catalyst, yields which is reacted with an activated ester of wherein either 8 is hydrogen and 81 is Trt, or 8 and #<SP>1</SP> together represent Chb, to yield which is reacted with an activated ester of (which is obtained by the reaction of H-Gly- O(lower alkyl) with an activated ester of CH 3 CH(R<SP>3</SP>)COOH, and hydrolysis of the resultant compound) to yield which, on reaction with hydrazine hydrate, yields which is reacted with an organic nitrite (preferably t-butyl nitrite or isoamyl nitrite) yields Peptides of the invention prepared are: Boc - Ala - Gly - Cys(Trt) - Lys(Boc) - Asn- Phe-Phe-N 3 Boc - Ala - Gly - Cys(Trt) - D - Lys(Boc) - Asn- Phe-Phe-OCH3 Boc - Ala - Gly - Cys(Trt) - D - Lys(Boc) - Asn- Phe-Phe-NHNH 2 CH 3 CH 2 CO - Gly - Cys(Trt) - Lys(Boc) - Asn- Phe-Phe-OCH 3 CH 3 CH 2 CO - Gly - Cys(Trt) - Lys(Boc) - Asn- Phe-Phe-NHNH 2 CH 3 CH 2 CO - Gly - Cys(Trt) - Lys(Boc) - Asn- Phe-Phe-N 3 . Peptides intermediates isolated are: PENTAPEPTIDES: Chb - Cys(Acm) - Lys- (Boc) - Asn - Phe - Phe - OCH 3 ; Trt and H - Cys- (Trt)-Lys(Boc)-Asn-Phe-Phe-OCH 3 ; H and Trt- Cys-D-Lys(Boc)-Asn-Phe-Phe-OCH 3 . TETRAPEPTIDES: Z and H-Lys(Boc)-Asn- Phe-Phe-OCH 3 ; Z and H-D-Lys(Boc)-Asn-Phe- Phe-OCH 3 . TRIPEPTIDES: Boc and H-Asn-Phe-Phe- OCH 3 . Dipeptide intermediates isolated are: Boc-Ala-Gly-OCH 3 , OH and OTcp; Boc and N-Phe-Phe-OCH 3 .
GB50494/76A 1973-12-10 1974-12-06 Heptapeptides Expired GB1486580A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US423352A US3917578A (en) 1973-12-10 1973-12-10 Process for producing somatostatin and intermediates
US493595A US3917581A (en) 1974-08-01 1974-08-01 Derivatives of somatostatin and process therefor

Publications (1)

Publication Number Publication Date
GB1486580A true GB1486580A (en) 1977-09-21

Family

ID=27025966

Family Applications (3)

Application Number Title Priority Date Filing Date
GB50494/76A Expired GB1486580A (en) 1973-12-10 1974-12-06 Heptapeptides
GB50493/76A Expired GB1486579A (en) 1973-12-10 1974-12-06 Heptapeptides
GB52779/74A Expired GB1486578A (en) 1973-12-10 1974-12-06 Process for preparing somatostatin and derivatives thereo

Family Applications After (2)

Application Number Title Priority Date Filing Date
GB50493/76A Expired GB1486579A (en) 1973-12-10 1974-12-06 Heptapeptides
GB52779/74A Expired GB1486578A (en) 1973-12-10 1974-12-06 Process for preparing somatostatin and derivatives thereo

Country Status (10)

Country Link
JP (1) JPS5088064A (en)
CA (1) CA1034116A (en)
CH (1) CH605680A5 (en)
CS (1) CS191922B2 (en)
DE (1) DE2458135A1 (en)
FR (1) FR2253532A1 (en)
GB (3) GB1486580A (en)
IL (1) IL46065A (en)
NL (1) NL7415916A (en)
SE (1) SE7415414L (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5712417A (en) * 1989-09-28 1998-01-27 Abbott Laboratories Inhibitors of retroviral proteases

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5712417A (en) * 1989-09-28 1998-01-27 Abbott Laboratories Inhibitors of retroviral proteases

Also Published As

Publication number Publication date
SE7415414L (en) 1975-06-11
IL46065A0 (en) 1975-02-10
CH605680A5 (en) 1978-10-13
FR2253532A1 (en) 1975-07-04
IL46065A (en) 1978-07-31
GB1486579A (en) 1977-09-21
DE2458135A1 (en) 1975-06-12
NL7415916A (en) 1975-06-12
GB1486578A (en) 1977-09-21
CA1034116A (en) 1978-07-04
JPS5088064A (en) 1975-07-15
CS191922B2 (en) 1979-07-31

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee