ES316390A1 - 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
ES316390A1
ES316390A1 ES0316390A ES316390A ES316390A1 ES 316390 A1 ES316390 A1 ES 316390A1 ES 0316390 A ES0316390 A ES 0316390A ES 316390 A ES316390 A ES 316390A ES 316390 A1 ES316390 A1 ES 316390A1
Authority
ES
Spain
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
ES0316390A
Other languages
Spanish (es)
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
Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG
Publication of ES316390A1 publication Critical patent/ES316390A1/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

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.
ES0316390A 1964-08-13 1965-08-11 Peptides having an adrenocorticotropic hormone action and process for their manufacture Expired ES316390A1 (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
ES316390A1 true ES316390A1 (en) 1966-04-01

Family

ID=27428551

Family Applications (1)

Application Number Title Priority Date Filing Date
ES0316390A Expired ES316390A1 (en) 1964-08-13 1965-08-11 Peptides having an adrenocorticotropic hormone action and process for their manufacture

Country Status (12)

Country Link
AT (1) AT295050B (en)
BE (2) BE668250A (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) NL6510560A (en)
NO (1) NO124831B (en)
SE (1) SE348464B (en)

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

Also Published As

Publication number Publication date
NL6510560A (en) 1966-02-14
DE1493559B2 (en) 1976-01-15
AT295050B (en) 1971-12-27
CH548986A (en) 1974-05-15
DE1493559A1 (en) 1970-10-29
CH499497A (en) 1970-11-30
FR5091M (en) 1967-05-22
BR6572122D0 (en) 1973-08-02
NL6510562A (en) 1966-02-14
BE668250A (en)
FR4901M (en) 1967-03-13
FR4900M (en) 1967-03-13
NO124831B (en) 1972-06-12
GB1119353A (en) 1968-07-10
SE348464B (en) 1972-09-04
CS150525B2 (en) 1973-09-04
FR4902M (en) 1967-03-13
MY6900354A (en) 1969-12-31
BE668249A (en)

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