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EP0100218A2 Expired / Lapsed EP ⏱️ 0.0 years remaining

GnRH antagonists

Assignee: Salk Institute for Biological Studies
•
Filing: 1983-07-22
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Granted: —
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Expires: 2003-07-22
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Abstract

Abstract Peptides which inhibit the secretion of gonadotropins by the pituitary gland and inhibit the release of steroids by the gonads. Administration of an effective amount prevents ovulation of female mammalian eggs and/or the release of steroids by the gonads. The peptides have the structure: X-β-D-2NAL-R<sub>2</sub>-D-Trp-Ser-R<sub>5</sub>-R<sub>6</sub>-R<sub>7</sub>-Arg-Pro-R wherein X is hydrogen or an acyl group having 7 or less carbon atoms; R<sub>2</sub> is Cl-D-Phe, F-D-Phe, N0<sub>2</sub>-D-Phe, Cl<sub>2</sub>-D-Phe or Br-D-Phe; R<sub>5</sub> is Tyr or Cl-Phe; R<sub>6</sub> is 4-NH<sub>2</sub>-D-Phe or D-Arg; R<sub>7</sub> is Leu or N<sup>α</sup>Me-Leu; and R<sub>10</sub> is Gly-NH<sub>2</sub>, NHCH<sub>2</sub>CH<sub>3</sub> or D-Ala-NH<sub>2</sub>.

Inventors

  • 👤 Jean Edouard Frederic Rivier
  • 👤 Wylie Walker Vale, Jr.

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-11-07 01:52
CPC Classifications
C; C07; C07K; C07K7/00; C07K7/04; C07K7/06; C07K7/23; A; A61; A61K; A61K38/00; A61K38/04; A61K38/08; A61K38/09; Y; Y10; Y10S; Y10S930/00; Y10S930/01; Y10S930/13

Claims Analysis

Total Claims: 14
Claim 1
Independent Claim 90 words
A peptide having the formula:-X-β-D-2NAL-R 2 -D-Trp-Ser-R 5 -R 6 -R 7 -Arg-Pro-R 10 wherein X is hydrogen or an acyl group having 7 or less carbon atoms; R 2 is Cl-D-Phe, F'-D-Phe, NO 2 -D-Phe, Cl 2 -D- phe or Br-D-Phe; R 5 is Tyr or 2-Cl-Phe; R 6 is 4-NH2-D-Phe or D-Arg; R 7 is Leu or N α Me-Leu; and R 10 is Gly-NH 2 , NHCH 2 CH 3 D-Ala-NH 2 , Gly-OCH 3 , Gly-OCH 2 CH 3 , Gly-NHNH 2 or Sar-NH 2 .
Claim 2
Dependent Claim 90 words
A peptide having the formula:-X-β-D-2NAL-R 2 -D-Trp-Ser-R 5 -R 6 -R 7 -Arg-Pro-R 10 wherein X is hydrogen or an acyl group having 7 or less carbon atoms; R 2 is Cl-D-Phe, F'-D-Phe, NO 2 -D-Phe, Cl 2 -D- phe or Br-D-Phe; R 5 is Tyr or 2-Cl-Phe; R 6 is 4-NH2-D-Phe or D-Arg; R 7 is Leu or N α Me-Leu; and R 10 is Gly-NH 2 , NHCH 2 CH 3 D-Ala-NH 2 , Gly-OCH 3 , Gly-OCH 2 CH 3 , Gly-NHNH 2 or Sar-NH 2 .
Claim 3
Dependent Claim 76 words
A peptide or a nontoxic salt thereof, said peptide having the formula: wherein X is hydrogen or an acyl group having 7 or less carbon atoms; R 2 is Cl-D-Phr, F-I)-Phe, NO 2 -D-Phe, Cl 2 -D-Phe or Br-D-Phe; R 5 is Tyr or 2-Cl-Phe; R 6 is 4-NH 2 -D-Phe or D-Arg; R 7 is Leu or N α Me-Leu; and R 10 is Gly-NH 2 , NHCH 2 CH 3 or D-Ala-NH 2 .
Claim 4
Dependent Claim 76 words
A peptide or a nontoxic salt thereof, said peptide having the formula: wherein X is hydrogen or an acyl group having 7 or less carbon atoms; R 2 is Cl-D-Phr, F-I)-Phe, NO 2 -D-Phe, Cl 2 -D-Phe or Br-D-Phe; R 5 is Tyr or 2-Cl-Phe; R 6 is 4-NH 2 -D-Phe or D-Arg; R 7 is Leu or N α Me-Leu; and R 10 is Gly-NH 2 , NHCH 2 CH 3 or D-Ala-NH 2 .
Claim 5
Dependent Claim 17 words
A peptide in accordance with Claim 1 or Claim 2 wherein R 2 is 4-Cl-D-Phe or 4-F-D-Phe.
Claim 6
Dependent Claim 12 words
A peptide in accordance with Claim 3 wherein R 7 is Leu.
Claim 7
Dependent Claim 12 words
A peptide in accordance with Claim 4 wherein R 6 is D-Arg.
Claim 8
Dependent Claim 12 words
A peptide in accordance with Claim 5 wherein R 5 is Tyr.
Claim 9
Dependent Claim 13 words
A peptide in accordance with Claim 6 wherein X is Ac or Acr.
Claim 10
Dependent Claim 21 words
A peptide in accordance with any one of Claims 1 to 3 wherein X is Ac and R 6 is D-Arg.
Claim 11
Dependent Claim 9 words
A peptide as defined in the foregoing specific Example.
Claim 12
Dependent Claim 9 words
A peptide as defined in the foregoing specific Example.
Claim 13
Dependent Claim 18 words
A non-toxic salt of a peptide as claimed in any one of Claims 1 and 3 to 9.
Claim 14
Dependent Claim 41 words
A pharmaceutical composition for regulating the secretion of gonadotropins comprising as an active ingredient an effective amount of a peptide as defined in Claim 1, or a non-toxic salt thereof, in association with a major amount of a non-toxic pharmaceutically-acceptable diluent.

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