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GB1119353A - Peptides having an adrenocorticotropic hormone action and process for their manufacture - Google Patents

Peptides having an adrenocorticotropic hormone action and process for their manufacture

Info

Publication number
GB1119353A
GB1119353A GB3384665A GB3384665A GB1119353A GB 1119353 A GB1119353 A GB 1119353A GB 3384665 A GB3384665 A GB 3384665A GB 3384665 A GB3384665 A GB 3384665A GB 1119353 A GB1119353 A GB 1119353A
Authority
GB
United Kingdom
Prior art keywords
boc
lys
pro
val
otbu
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
GB3384665A
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.)
BASF Schweiz AG
Original Assignee
Ciba 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 Ciba AG filed Critical Ciba AG
Publication of GB1119353A publication Critical patent/GB1119353A/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
    • C07K5/08—Tripeptides
    • C07K5/0802—Tripeptides with the first amino acid being neutral
    • C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
    • C07K5/081—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing O or S as heteroatoms, e.g. Cys, Ser
    • 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)
  • 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)
  • Toxicology (AREA)
  • Zoology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)
  • Feeding And Watering For Cattle Raising And Animal Husbandry (AREA)

Abstract

A peptide that differs from an ACTH-active peptide containing 16-39 amino acid residues and having an N-terminal amino acid residue with L-configuration, solely in that the N-terminal amino acid residue has D-configuration, acid addition salts, complexes and amino and carboxylic acid blocked derivatives thereof are prepared by standard methods of peptide synthesis. Preferred peptides are those that differ from an (all-L)-ACTH-active peptide containing a 16-39 amino acid residue sequence (commencing at the N-terminus) of a natural corticotrophin, in which at least one of the amino acid residues in the positions 1 to 5, 17, 18 and 25 to 33 may be replaced by the residue of another natural a -amino acid or of a homologue thereof, solely in that the N-terminal amino acid residue has D-configuration. The following compounds are prepared as starting materials or as intermediates: BOC-D-Serine, BOC - D - Ser - Tyr - Ser - Met - OMe and -NHNH2; BOC - D - Ser - Tyr - Ser - Met - Glu(OtBu) - His - Phe - Arg - Try - GlyOH; BOC - D - Ser - Tyr+ - Ser - Met - Glu(OtBu) - His - Phe - Arg - Try - Gly - Lys(BOC) - Lys(BOC) - Arg - Arg - Pro - Val - Lys(BOC) - Val - Tyr - Pro - OtBu; BOC - D - alanine; BOC - D - Ala - Tyr - Ser - Met - NHNH2; BOC - D - Ala - Tyr - Ser - Met - Glu(OtBu) - His - Phe - Arg - Try - GlyOH; BOC - D - Ala - Tyr - Ser - Met - Glu(OtBu) - His - Phe - Arg - Try - Gly - Lys(BOC) - Pro - Val - Gly - Lys(BOC) - Lys(BOC) - Arg - Arg - Pro - Val - Lys(BOC) - Val - Tyr - Pro - OtBu; Z - Arg - Pro - OtBu; Z - Arg - Arg - Pro - OtBu; H-Arg - Arg - Pro -OtBu; Z - Lys(BOC) - Pro - Val - Gly - Lys(BOC) - Lys(BOC) - Arg - Arg - Pro - OtBu; H - Lys(BOC) - Pro - Val - Gly - Lys - Lys(BOC) - Arg - Arg - Pro OtBu; BOC - D - Ser - Tyr - Ser - Met - Glu(OtBu) - His - Phe - Arg - Try - Gly - Lys(BOC) - Pro - Val - Gly - Lys(BOC) - Lys(BOC) - Arg - Arg - Pro - OtBu; Z - Pro - Val - Lys(BOC) - Val - Tyr - Pro - OtBu; H - Pro - Val - Lys - Val - Tyr - Pro OtBu; Z - Orn(BOC) - OH; its p-nitrophenyl ester and its hydrophthalimide ester; Z - Orn(BOC) - Pro - Val - Lys(BOC) - Val - Tyr - Pro - OtBu; H - Orn(BOC) - Pro - Val - Lys(BOC) - Val - Tyr - Pro - OtBu; Z - Orn(BOC) - Orn(BOC) - Pro - Val - Lys(BOC) - Val - Tyr - Pro - OtBOC; H - Orn(BOC) - Orn(BOC) - Pro - Val - Lys (BOC) - Val - Tyr - Pro - OtBu; Z - Lys(BOC) - Pro - Val - Gly - Lys(BOC) - Lys (BOC) - Orn(BOC) - Orn(BOC) - Pro - Val - Lys(BOC) - Orn - Tyr - Pro OtBu; H - Lys(BOC) - Pro - Val - Gly - Lys(BOC) - Lys(BOC) - Orn(BOC) - Orn(BOC) - Pro - Val - Lys(BOC) - Val - Tyr - Pro OtBu - tosylate; BOC - D - Ser - Tyr - Ser - Met - Glu(OtBu) - His - Phe - Arg - Try - Gly - Lys(BOC) - Pro - Val - Gly - Lys - (BOC) - Lys(BOC) - Orn(BOC) - Orn(BOC) - Pro - Val - Lys(BOC) - Val - Tyr - Pro - OtBu; H - Lys(BOC) - Pro - Val - Gly - Lys(BOC) - Lys(BOC) - NH2; BOC - D - Ser - Tyr - Ser - Met - Glu(OtBu) - His - Phe - Arg - Try - Gly - Lys(BOC) - Pro - Val - Gly - Lys(BOC) - Lys(BOC) - NH2; BOC - D - Ser - Tyr - Ser - Met - Glu(OtBu) - His - Phe - Arg - Try - Gly - Lys(BOC) - Pro - Val - Gly - Lys(BOC) - Lys(BOC) - Arg - Arg - ProVal - Lys(BOC) - Val - Tyr - Pro - Asp(OtBu) - Gly - Ala - Glu(OtBu) - Asp(OtBu) - Glu(NH2) - Leu - Ala - Glu(OtBu) - Ala - Phe - Pro - Leu - Glu(OtBu) - Phe - OtBu; BOC - Tyr - Gly - Ome; H - Tyr - Gly - Ome, HCl; BOC - D - Ser - Tyr - Gly - Ome; BOC - D - Ser - Tyr - Gly - OH; BOC - D - Ser - Tyr - Gly - Met - Ome and -NHNH2; Z - Glu(OtBu) - His - Phe - Arg - Try - Gly - Lys(BOC) - Pro - Val - Gly - Lys(BOC) - Lys(BOC) - Arg - Arg - Pro - Val - Lys(BOC) - Val - Tyr - Pro - OtBu - triacetate; H - Glu(OtBu) - His - Phe - Arg - Try - Gly - Lys(BOC) - Pro - Val - Gly - Lys(BOC) Lys(BOC) - Arg - Arg - Pro - Val - Lys(BOC) - Val - Tyr - Pro - OtBu - tetra-acetate and BOC - D - Ser - Tyr - Gly - Met - Glu(OtBu) - His - Phe - Arg - Try - Gly - Lys(BOC) - Pro - Val - Gly - Lys(BOC) Lys(BOC) - Arg - Arg - Pro - Val - Lys(BOC) - Val - Tyr - Pro - OtBu. Pharmaceutical compositions comprise the peptides of the invention in admixture or in conjunction with a suitable carrier. The compositions may be formulated for enteral or parenteral administration.
GB3384665A 1964-08-13 1965-08-06 Peptides having an adrenocorticotropic hormone action and process for their manufacture Expired GB1119353A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
CH1058364A CH499497A (en) 1964-08-13 1964-08-13 ACTH active peptides
CH1550964 1964-12-02
CH303765A CH548986A (en) 1964-08-13 1965-03-04 PROCESS FOR PRODUCING NEW PEPTIDES WITH ACTH EFFECT.
CH831665 1965-06-15

Publications (1)

Publication Number Publication Date
GB1119353A true GB1119353A (en) 1968-07-10

Family

ID=27428551

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3384665A Expired GB1119353A (en) 1964-08-13 1965-08-06 Peptides having an adrenocorticotropic hormone action and process for their manufacture

Country Status (12)

Country Link
AT (1) AT295050B (en)
BE (2) BE668249A (en)
BR (1) BR6572122D0 (en)
CH (2) CH499497A (en)
CS (1) CS150525B2 (en)
ES (1) ES316390A1 (en)
FR (4) FR4900M (en)
GB (1) GB1119353A (en)
MY (1) MY6900354A (en)
NL (2) NL6510562A (en)
NO (1) NO124831B (en)
SE (1) SE348464B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN117106057A (en) * 2022-08-19 2023-11-24 南京汉欣医药科技有限公司 A high-purity human adrenocorticotropic hormone or its analog and its large-scale preparation method

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3503951A (en) * 1965-06-15 1970-03-31 Ciba Geigy Corp Complexes of a.c.t.h. peptides with polyglutamic and polyaspartic acid
BE758206A (en) * 1969-10-31 1971-04-29 Hoechst Ag PEPTIDES WITH ADRENOCORTICOTROPIC ACTIVITY AND MEDICINAL PRODUCTS CONTAINING IT
US4130514A (en) * 1978-02-10 1978-12-19 Armour Pharmaceutical Company Synthesis of peptides

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN117106057A (en) * 2022-08-19 2023-11-24 南京汉欣医药科技有限公司 A high-purity human adrenocorticotropic hormone or its analog and its large-scale preparation method

Also Published As

Publication number Publication date
AT295050B (en) 1971-12-27
FR4901M (en) 1967-03-13
NL6510562A (en) 1966-02-14
ES316390A1 (en) 1966-04-01
NL6510560A (en) 1966-02-14
BR6572122D0 (en) 1973-08-02
SE348464B (en) 1972-09-04
DE1493559B2 (en) 1976-01-15
FR5091M (en) 1967-05-22
CH548986A (en) 1974-05-15
CH499497A (en) 1970-11-30
CS150525B2 (en) 1973-09-04
BE668250A (en)
BE668249A (en)
MY6900354A (en) 1969-12-31
DE1493559A1 (en) 1970-10-29
NO124831B (en) 1972-06-12
FR4900M (en) 1967-03-13
FR4902M (en) 1967-03-13

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