GB1243035A - New hypocalcaemic peptides and processes for their manufacture - Google Patents

New hypocalcaemic peptides and processes for their manufacture

Info

Publication number
GB1243035A
GB1243035A GB52391/68A GB5239168A GB1243035A GB 1243035 A GB1243035 A GB 1243035A GB 52391/68 A GB52391/68 A GB 52391/68A GB 5239168 A GB5239168 A GB 5239168A GB 1243035 A GB1243035 A GB 1243035A
Authority
GB
United Kingdom
Prior art keywords
tbu
asn
ser
leu
phe
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
GB52391/68A
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
Ciba 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 CH1566167A external-priority patent/CH517074A/en
Priority claimed from CH176368A external-priority patent/CH529105A/en
Priority claimed from CH699968A external-priority patent/CH498805A/en
Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG
Publication of GB1243035A publication Critical patent/GB1243035A/en
Expired legal-status Critical Current

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
    • C07K5/06104—Dipeptides with the first amino acid being acidic
    • C07K5/06113—Asp- or Asn-amino acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
    • C07K1/06—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents
    • C07K1/061—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents using protecting groups
    • C07K1/067—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents using protecting groups for sulfur-containing functions
    • 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
    • C07K14/585—Calcitonins
    • 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
    • C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala
    • 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
    • C07K5/1016—Tetrapeptides with the first amino acid being neutral and aromatic or cycloaliphatic
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Biophysics (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Analytical Chemistry (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

1,243,035. Thyrocalcitons. CIBA GEIGY A.G. 5 Nov., 1968 [9 Nov., 1967; 6 Feb., 1968; 29 April, 1968; 4 May, 1968; 10 May, 1968; 21 May; 1968], No. 52391/68. Heading C2C. Compounds of the formula HCys - Ser - Asn - Leu - Ser - Thr - Cys - Val- Leu - Ala - Tyr - Try - Arg - Asn - Leu - Asn- Asn - Phe - His - .Arg - Phe - Ser - Gly - Met- Gly - Phe - Gly - Pro - Glu - Thr - Pro - OH and the corresponding compound where one or more asparaginine residues are replaced by aspartic acid residues and/or the glutamic acid residue by the glutamine residue and/or methionine residue by the valine, norvaline, leucine, isoleucine or norsleucine residue, and their salts derivatives (including esters, amides, N-acyl derivatives desamino<SP>1</SP>-peptides and Met<SP>25</SP>-sulphoxides) and complexes, are prepared in a per se conventional manner for forming polypeptides from amino acids or smaller peptide units. N-acylated peptides include N-acetyl, N- phenylthiocarbamoyl- and N-pyroglutamylpeptides and complexes are those formed with zinc phosphate, pyrophosphate, or hydroxide, gelatine, polyphloretine phosphate or polyglutamic acid. Pharmaceutical compositions containing the compounds of the invention in forms suitable for enteral and parenteral administration. The compounds are hypocalcaemic agents and compositions may contain other drugs. The following starting materials and intermediates are prepared: H-Thr(tBu)-OMe, DPC- - Ser (tBu) - Thr[tBu) - OMe, Z - Val - Leu - OMe, DPC - Ser(tBu) - Thr(tBu)NHNH 2 H - Val- Leu - OMe, HCl, TR1 - and H - Cys(TR1)- Val - Leu - OMe, DPC - Ser(tBu) - Thr(tBu)- Cys(TR1)- Val - Leu - OMe and -OH - H - Ser (tBu) - Thr(tBu) - Cys(TR1) - Val - Leu - OH, Z - Asn - Leu - OMe, H - Asn - Leu - OMe, Z and H - Ser(tBu) - Asn - Leu - OMe, BOC - Cys (TR1) - Ser(tBu) - Asn - Leu - OMe and -NHNH 2 , BOC - Cys(TR1) - Ser(tBu) - Asn- Leu - Ser(tBu) - Thr(tBu) - -Cys(TR1) - Val - Leu- OH, BOC- # Cys-Ser-(tBu)-Asn-Leu-Ser(tBu)-Thr(tBu)Cys- Val - Leu OH, H - and Z - Tyr(tBu)-Try- OMe, H - and Z - Ala - Tyr(tBu) - Try - OMe, DPC - Ser(tBu) - Ala - Tyr(tBu)Try - OMe and -NHNH 2 Z - and H - Asn - Phe - NHNHBOC, Z - and H - Asn - Asn - Phe - NHNHBOC Z- and H Asn - Asn - Phe NHNHBOC, Z - and H - Leu- Asn - Asn - Phe - NHNH - BOC, Z - and H - "Asn - Leu - Asn - Asn, Phe- NHNHBOC, Z - Arg - Asn - Leu - Asn, - Asn- Phe - NHNHBOC, HCl and - NHNH 2 HCl, Z - Phe - Ser(tBu) - OMe and - NHNH 2 Z and H - Phe - Ser(tBu) - GlyOMe, Z - and HArg - Phe - Ser(tBu) - Sly - OMe, HBr, Z - and H - His - Arg - Phe - Ser(tBu) - Gly - OMe, HHis Arg Phe - Ser(tBu) - GlyOH, HOAc, Z- and H - Arg - Asn - Leu - Asn - Asn - Phe - His- Arg - Phe - Ser(tBu) - GlyOH, HOAc, DPCSer(tBu) - Ala - Tyr(tBu) - Try - Arg - Asn - Leu- Asn - Asn - Phe - His - Arg - Phe - Ser(tBu) - -Gly- OH, Z - Sly - Phe - Gly - Pro - OtBu and - OHZ - and H - Thr(tBu) - ProNH 2 , Z - and HGlu(OtBu)Thr(tBu) - ProNH 2 , Z - and H - Gly, Phe - Sly - Pro - Glu(OtBu) - Thr(tBu) - ProNH 2 - DPC - and H - Met - Gly - Phe - Gly - Pro- Glu(OtBu) - Thr(tBu) - ProNH 2 , DPC - Ser (tBu) - Ala - Tyr(tBu) - Try - Arg - Asn - Leu, Asn - Asn - Phe - His - Arg - Phe - Ser(tBu-) Gly - OH ditosylate DPC - and H - Ser(tBu)- Ala - Tyr(tBu) - Try - Arg - Asn - Leu - Asn- Asn - Phe - His - Arg - Phe - Ser(tBu) - Gly- Met - Gly - Phe - Gly - Pro - Glu(OtBu) - Thr (tBu)ProNH 2 , BOCCys-Ser(tBu)-Asn-Leu-Ser.(tBu)-Thr(tBu)Cys Val - Leu - Ser(tBu) - Ala - Tyr(tBu) - Try- Arg- Asn - Leu - Ash - Asn - Phe - His - Arg - Phe- Ser(tBu) - Gly - Met - Gly - Phe - Gly - Pro- Glu(OtBu) - Thr(tBu) - ProNH 2 and BOC- # Cys-Ser (tBu) -Asn-Leu-Ser (tBu) - Thr (tBu) - Cys - Val - Leu - Ser(tBu) - Ala - Tyr(tBu) - Try- Arg - Asn - Leu - Ash - Asn - Phe - His - Arg- Phe - Ser(tBu) - GlyOH; BOC and H - Val- Leu - OBzl, BOC - and H - Cys(Bzl) - Val- Leu - OBzl, BOC - and H - Ser - Thr - OBzl, BOC - and H - Asn - Leu - NHNHZ, BOCSer - Ash - Leu - NHNHZ and - NHNH 2 , BOC - Ser - Ash - Leu - Ser - Thr - OBzl and - OH, H - Ser - Asn. Leu - Ser , ,; Thr OH, BOC - Cys(Bzl) - Ser - Asn - Lent - Ser - Thr OH, BOC - Cys(Bzl) - Ser - Asn - Leu - Ser - Thr- Cys(Bzl) - Val - Leu OH, BOC - Cys - Ser- Asn - Leu - Ser - Thr - Cys - Val - Left OH, BOCI I Cys-Ser-Asn-Leu-Ser-Thr-Cys Val - Left OH and BOGCys-Ser-Asn-Leu-Ser-Thr-Cys Val - Leu - Ser(tBu) - Ala - Tyr(tBu) - Try - Arg- Asn Len - Asn - Asn - Phe - His - Arg - Phe- Ser(tBu) - Gly - Met - Gly - Phe - ,- Gly - Pro- Glu(OtBu), Thr(tBu)ProNH 2 ; N - acetyl- # Cys Ser Asn - Leu - Ser - Thr - Cys - Val- Leu - OH, H - Ser - Ala - Tyr - Try - Arg - Asn- Leu - Asn - Asn - Phe - His - Arg - Phe - Ser- Oly Met - Gly - Phe - Gly - Pro - Olu - Thr- ProNH 2 diacetate; Z- and HThr(tBu) -Pro- OtBu; Z - and H - Glu(OtBu) - Thr(tBu)- Pro(OtBu), Z - and H - Gly - Phe - Gly - Pro- Glu(OtBu) - Thr(tBu) - Pro OtBu, DPC - and H - Met - Gly - Phe - Gly - Pro - Glu(OtBu)- Thr(tBu) - Pro OtBu; and BOC- # Cys-Ser(tBn)-Asn-Leu-Ser(tBn)-Thr-(tBu)-Cys- Val - Leu - Ser(tBu) - Ala - Tyr(tBu) - Try Arg- Asn - Leu - Asn - Asn - Phe - His - Arg - Phe - Ser(tBu) - Gly - Met - Gly - Phe - Gly - Pro - Olu(OtBu) - Thr(tBu) -Pro -OtBu.
GB52391/68A 1967-11-09 1968-11-05 New hypocalcaemic peptides and processes for their manufacture Expired GB1243035A (en)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
CH1566167A CH517074A (en) 1967-11-09 1967-11-09 Hypocalcaemic peptides - with anti-inflammatory activity
CH176368A CH529105A (en) 1968-02-06 1968-02-06 Preparation of hypocalcaemic peptides
CH634768 1968-04-29
CH666668 1968-05-04
CH699968A CH498805A (en) 1968-05-10 1968-05-10 Prepn. of cystine-contg. peptides - used in the synthesis of long-chain peptides
CH750968 1968-05-21
US81810969A 1969-04-24 1969-04-24

Publications (1)

Publication Number Publication Date
GB1243035A true GB1243035A (en) 1971-08-18

Family

ID=27561059

Family Applications (1)

Application Number Title Priority Date Filing Date
GB52391/68A Expired GB1243035A (en) 1967-11-09 1968-11-05 New hypocalcaemic peptides and processes for their manufacture

Country Status (6)

Country Link
BE (1) BE723588A (en)
CA (1) CA992958A (en)
DE (1) DE1806135A1 (en)
FR (1) FR1593126A (en)
GB (1) GB1243035A (en)
NL (1) NL6815962A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0003122A1 (en) * 1978-01-12 1979-07-25 Hoechst Aktiengesellschaft Process for the preparation of cystein-containing peptides

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NZ261052A (en) * 1992-12-31 1997-10-24 Zymogenetics Inc Calcitonin derivatives and compositions thereof
US5698672A (en) * 1995-04-04 1997-12-16 Zymogenetics, Inc. Synthetic calcitonin mimetics

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0003122A1 (en) * 1978-01-12 1979-07-25 Hoechst Aktiengesellschaft Process for the preparation of cystein-containing peptides

Also Published As

Publication number Publication date
CA992958A (en) 1976-07-13
NL6815962A (en) 1969-05-13
BE723588A (en) 1969-05-08
DE1806135A1 (en) 1969-07-17
FR1593126A (en) 1970-05-25

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