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EP0225746A2 Expired / Lapsed EP ⏱️ 0.0 years remaining

Therapeutic decapeptides

Assignee: Tulane University
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Filing: 1986-11-14
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Granted: —
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Expires: 2006-11-14
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Abstract

Abstract A decapeptide of the formula: A 9 , wherein each A 1 , A2, and A3, independently, is D-β-Nal, D-p-X-Phe (where X is halogen, H, NH 2 , NO 2 , OH, or C 1-3 alkyl), D-Trp, D-benzothienyl (2)-Ala, or D-benzothienyl (1)-Ala; A4 is p-X-Phe (where X is halogen, H, NH 2 , N0 2 , or C 1-3 alkyl), Tyr, Lys, Arg, Leu, Trp, or Nal; A 5 is D-Lys, D-Tyr, D-Arg, D-Phe, D-β-Nal, D-Trp, D-homo-Arg, D-diethyl-homo-Arg, D-p-X-Phe (where X is halogen, H, NH 2 , N0 2 , or C 1-3 alkyl), or D-Lys-ε-NH-R (where R is H, a branched or straight chain C 1 -C 10 akyl group, or an aryl group); A 6 is Leu, β-Nal, p-X-Phe (where X is halogen, H, NH 2 , N0 2 , OH, C 2 F 5 , C 1-3 alkyl), or Trp; A 7 is Arg, Lys, or Lys-e-NH-R (where R is H, a branched or straight chain C 1 -C 6 alkyl group, or an aryl group); As is Pro; and A 9 is D-Ala, D-Ala-NH 2 , Ala-NH 2 , aminoisobutyric acid amide, or Gly-NH 2 ; provided that at least one of A 2 or A3 must be D-Phe or D-Tyr, and provided further that when A4 is Lys or Arg, A 5 must not be D-Arg, D-Lys, D-homo-Arg, D-diethyl-homo-Arg, or D-Lys-ε-NH-R, or a pharmaceutically acceptable salt thereof, can be used to inhibit the release of sex hormones in the treatment or prophylaxis of various sex hormone-released conditions. They may also be used as female contraceptives.

Inventors

  • 👤 David H. Coy
  • 👤 Jacques-Pierre Moreau

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-11-05 12:30
CPC Classifications
C; C07; C07K; C07K7/00; C07K7/04; C07K7/23; A; A61; A61K; A61K38/00

Claims Analysis

Total Claims: 9
Claim 1
Independent Claim 298 words
A process for the preparation of a decapeptide of the formula: N-Ac-A 1 -A 2 -A 3 -Ser-A 4 -A 5 -A 6 -A 7 -A 8 - A 9 , wherein each A 1 , A 2 , and A 3 , independently, is D- β -Nal, D-p-X-Phe (where X is halogen, H, NH 2 , NO 2 , OH, or C l-3 alkyl), D-Trp, D-benzothienyl (2)-Ala, or D-benzothienyl (1)-Ala: A4 is p-X-Phe (where X is halogen, H, NH 2 , NO 2 , or C 1-3 alkyl), Tyr, Lys, Arg, Leu, Trp, or Nal; A 5 is D-Lys, D-Tyr, D-Arg, D-Phe, β -Nal, D- β -Nal, D-Trp, D-homo-Arg, D-diethyl-homo-Arg, D-p-X-Phe (where X is halogen, H, NH 2 , NO 2 , or C 1-3 alkyl) or D-Lys- ε -NH-R (where R is H, a branched or straight chain C 1 -C 10 alkyl group, or an aryl group); A 6 is Leu, β -Nal, p-X-Phe (where X is halogen, H, NH 2 , NO 2 , OH, C 2 F 5 , or C 1-3 alkyl), or Trp; A is Arg, Lys, or Lys- ε -NH-R (where R is H, a branched or straight chain C 1 -C 10 alkyl group, or an aryl group); A- is Pro; and A is D-Ala, D-Ala-NH 2 , Ala-NH 2 , aminoisobutyric acid amide, or Gly-NH 2 ; provided that at least one of A 2 or A3 must be D-Phe or D-Tyr, and provided further that when A4 is Lys or Arg, A 5 must not be D-Lys, D-Arg, D-homo-Arg, D-diethyl-homo-Arg, or D-Lys- ε - NH-R, or a pharmaceutically acceptable salt thereof; the process comprising liberating free decapeptide (or a salt) from a corresponding substrate-bound decapeptide and optionally thereafter forming a salt or the free base as appropriate.
Claim 2
Dependent Claim 298 words
A process for the preparation of a decapeptide of the formula: N-Ac-A 1 -A 2 -A 3 -Ser-A 4 -A 5 -A 6 -A 7 -A 8 - A 9 , wherein each A 1 , A 2 , and A 3 , independently, is D- β -Nal, D-p-X-Phe (where X is halogen, H, NH 2 , NO 2 , OH, or C l-3 alkyl), D-Trp, D-benzothienyl (2)-Ala, or D-benzothienyl (1)-Ala: A4 is p-X-Phe (where X is halogen, H, NH 2 , NO 2 , or C 1-3 alkyl), Tyr, Lys, Arg, Leu, Trp, or Nal; A 5 is D-Lys, D-Tyr, D-Arg, D-Phe, β -Nal, D- β -Nal, D-Trp, D-homo-Arg, D-diethyl-homo-Arg, D-p-X-Phe (where X is halogen, H, NH 2 , NO 2 , or C 1-3 alkyl) or D-Lys- ε -NH-R (where R is H, a branched or straight chain C 1 -C 10 alkyl group, or an aryl group); A 6 is Leu, β -Nal, p-X-Phe (where X is halogen, H, NH 2 , NO 2 , OH, C 2 F 5 , or C 1-3 alkyl), or Trp; A is Arg, Lys, or Lys- ε -NH-R (where R is H, a branched or straight chain C 1 -C 10 alkyl group, or an aryl group); A- is Pro; and A is D-Ala, D-Ala-NH 2 , Ala-NH 2 , aminoisobutyric acid amide, or Gly-NH 2 ; provided that at least one of A 2 or A3 must be D-Phe or D-Tyr, and provided further that when A4 is Lys or Arg, A 5 must not be D-Lys, D-Arg, D-homo-Arg, D-diethyl-homo-Arg, or D-Lys- ε - NH-R, or a pharmaceutically acceptable salt thereof; the process comprising liberating free decapeptide (or a salt) from a corresponding substrate-bound decapeptide and optionally thereafter forming a salt or the free base as appropriate.
Claim 3
Dependent Claim 12 words
A process as claimed in claim 1 wherein A 3 is D-Phe.
Claim 4
Dependent Claim 13 words
A process as claimed in claim 1 or 2 wherein A is D-Phe.
Claim 5
Dependent Claim 17 words
A process as claimed in claim 1, 2 or 3 wherein A 6 is p-X- P he.
Claim 6
Dependent Claim 280 words
A process as claimed in claim 1 wherein A 1 is D- β -Nal, A 2 is D-p-Cl-Phe, A 3 is D-Phe, A is Tyr, A 5 is D-Arg, A 6 is Phe, A 7 is Arg, A8 is Pro, and A 9 is D -Ala; or wherein A 1 is D- β -Nal, A 2 is D-Phe, A3 is D -Phe, A4 is T yr, A 5 is D - Ar g, A 6 is Phe , A 7 is Arg, A 8 is Pro, and A 9 is D-Ala; or wherein A 1 is wherein is D- β -Nal, A 2 is D - P he, A3 is D - P he, A4 is T yr, A5 is D -Lys (isopropyl), A 6 is Phe, A 7 is Lys (isopropyl), A 8 is Pro, and A 9 is Ala-NH 2 ; or wherein A 1 is D- β -Nal, A 2 is D-Phe, A3 is D -Ph e , A4 is Ph e, A 5 is D -Arg, A 6 is Leu, A 7 is Arg, A 8 is Pro, and A 9 is D -Ala; or wherein A 1 is D- β -Nal, A 2 is D - P he, A3 is D - P h e , A4 is Tyr, A 5 is D-Lys (isopropyl), A 6 is Phe, A is Arg, A 8 is P ro, and A 9 is D-Ala-NH2; or wherein H 1 is D- β -Nal, A 2 is D -p-Cl-Phe, A3 is D - T yr, A4 is Ph e , A is D -Arg, A 6 is Leu, A is Arg, A 8 is Pro, and A 9 is D-Ala.
Claim 7
Dependent Claim 43 words
A process as claimed in any one of claims 1 to 5, wherein the substrate bound decapeptide is prepared by first coupling an A 9 residue to a substrate to form an intermediate peptide and subsequently coupling further residues to the intermediate peptide.
Claim 8
Dependent Claim 18 words
A process as claimed in any one of claims 1 to 6 wherein the substrate comprises a resin.
Claim 9
Dependent Claim 14 words
A process as claimed in claim 7, wherein the resin is a benzhydrylamine resin.

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