EP0325044A2
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EP
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Pharmacologically active cyclic peptide
Assignee: Beecham Group PLC
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Filing: 1988-12-19
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Granted: —
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Expires: 2008-12-19
Abstract
Abstract A pharmacologically active cyclic peptide of formula (I), or a pharmaceutically acceptable salt thereof: wherein R₁ and R₂ are independently (CH₂) n NH₂ or (CH₂) n NH-C=NH.NH₂ wherein n is 3-6; R₃ is CH₂R₇ wherein R₇ is phenyl optionally substituted by one or two substituents selected from halogen, hydroxy, C₁₋₄ alkyl and C₁₋₄ alkoxy, or R₇ is C₁₋₆ alkyl; R₄, R₅ and R₆ are the same or different C₁₋₇ alkyl groups; four of X¹ to X⁶ are amide linkages and the other two are amide linkages or linkages wherein the amide bond is replaced by an enzyme stabilised linkage; provided that, when R₇ is phenyl, at least one of the three carbon atoms depicted in formula (I) attached to R₄, R₅ and R₆, is in the L-configuration.
Inventors
- 👤 Gordon Beecham Pharmaceuticals Wootton
- 👤 Eric Alfred Beecham Pharmaceuticals Watts
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-10-24 08:59
CPC Classifications
C; C07; C07K; C07K7/00; C07K7/04; C07K14/00; C07K14/435; C07K14/575; C07K14/57563; A; A61; A61P; A61P1/00; A61P1/04
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
197 words
A process for the preparation of a pharmacologically active cyclic peptide of formula (I), or a pharmaceutically acceptable salt thereof: wherein R₁ and R₂ are independently (CH₂) n NH₂ or (CH₂) n NH-C=NH.NH₂ wherein n is 3-6; R₃ is CH₂R₇ wherein R₇ is phenyl optionally substituted by one or two substituents selected from halogen, hydroxy, C₁₋₄ alkyl and C₁₋₄ alkoxy, or R₇ is C₁₋₆ alkyl; R₄, R₅ and R₆ are the same or different C₁₋₇ alkyl groups; four of X¹ to X⁶ are amide linkages and the other two are amide linkages or linkages wherein the amide bond is replaced by an enzyme stabilised linkage; provided that, when R₇ is phenyl, at least one of the three carbon atoms depicted in formula (I) attached to R₄, R₅ and R₆, is in the L-configuration; which process comprises the cyclisation of a linear peptide of formula (II); or a salt thereof: wherein Y is an optionally protected amino acid sequence corresponding to the amino acids in the desired cyclic peptide of formula (I); and Q is a leaving group; and thereafter, where necessary removing any amino acid side chain protecting groups and optionally forming a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
197 words
A process for the preparation of a pharmacologically active cyclic peptide of formula (I), or a pharmaceutically acceptable salt thereof: wherein R₁ and R₂ are independently (CH₂) n NH₂ or (CH₂) n NH-C=NH.NH₂ wherein n is 3-6; R₃ is CH₂R₇ wherein R₇ is phenyl optionally substituted by one or two substituents selected from halogen, hydroxy, C₁₋₄ alkyl and C₁₋₄ alkoxy, or R₇ is C₁₋₆ alkyl; R₄, R₅ and R₆ are the same or different C₁₋₇ alkyl groups; four of X¹ to X⁶ are amide linkages and the other two are amide linkages or linkages wherein the amide bond is replaced by an enzyme stabilised linkage; provided that, when R₇ is phenyl, at least one of the three carbon atoms depicted in formula (I) attached to R₄, R₅ and R₆, is in the L-configuration; which process comprises the cyclisation of a linear peptide of formula (II); or a salt thereof: wherein Y is an optionally protected amino acid sequence corresponding to the amino acids in the desired cyclic peptide of formula (I); and Q is a leaving group; and thereafter, where necessary removing any amino acid side chain protecting groups and optionally forming a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
44 words
A process according to claim 1 for the preparation of a cyclic peptide according to claim 1 of the formula (IA), or a pharmaceutically acceptable salt thereof: wherein one or more of the amino acids may be replaced by an equivalent other amino acid.
Claim 4
Dependent Claim
40 words
A process according to claim 2 for the preparation of cyclic peptide of formula (IA) wherein Tyr is replaced by another hydrophopic amino acid, such as leucine or phenylalanine (when one of Val, Ala or Leu is in the L-form).
Claim 5
Dependent Claim
44 words
A process according to any one of claims 1 to 3 for the preparation of a cyclic peptide wherein the Lys-Lys-Tyr (or R₁, R₂, R₃ carbon atoms) are in the L-configuration and the Leu-Ala-Val (or R₄, R₅ R₆ carbon atoms) are in the D-configuration.
Claim 6
Dependent Claim
24 words
A process according to claim 1 for the preparation of cyclo-[D-Alanyl-L-Valyl-L-Lysyl-L-Lysyl-L-Tyrosyl-L-Leucine], cyclo-[D-Alanyl-D-Valyl-L-Lysyl-L-Lysyl-L-Tyrosyl-D-Leucine], cyclo-[D-Alanyl-L-Valyl-L-Lysyl-L-Lysyl-L-Phenylalanyl-L-Leucine], cyclo-[D-Alanyl-D-Valyl-L-Lysyl-L-Lysyl-L-Leucyl-D-Leucine], or a pharmaceutically acceptable salt of any of the foregoing.
Claim 7
Dependent Claim
29 words
Use of a cyclic peptide according to any one of claims 1 to 5 in the manufacture of a medicament for use in the treatment of peptic ulcer disease.
Claim 8
Independent Claim
31 words
A method of treatment of peptic ulcer disease, which method comprises the administration of an anti-ulcer effective amount of a cyclic peptide according to any one of claims 1 to 5.
References Cited (Backward Citations)
No citation records indexed.
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