US4307083A
Expired / Lapsed
US
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LRF Antagonists
Assignee: Salk Institute for Biological Studies
•
Filing: 1980-05-08
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Granted: 1981-12-22
•
Expires: 2000-05-08
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: R.sub.1 -R.sub.2 -R.sub.3 -Ser-Tyr-R.sub.4 -R.sub.5 -Arg-R.sub.6 wherein R 1 is selected from the group consisting of dehydro Pro, dehydro D-Pro, Acetyl dehydro Pro and acetyl dehydro D-Pro; R 2 is selected from the group consisting of D-Phe, Phe, NαMe-Phe, His, D-His, D-Trp, Trp and NαMe-Leu; R 3 is selected from the group consisting of D-Trp, Trp D-Phe, Phe, Pro and D-His; R 4 is selected from the group consisting of Gly, D-Trp, D-Phe, imBzl-D-His and D-Tyr; R 5 is selected from the group consisting of Leu and NαMe-Leu; and R 6 is selected from the group consisting of Pro-Gly-NH 2 and Pro-NH-CH 2 -CH 3 .
Inventors
- 👤 Jean E. F. Rivier
- 👤 Catherine L. Rivier
- 👤 Wylie W. Vale, Jr.
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 22:42
CPC Classifications
C; C07; C07K; C07K7/00; C07K7/04; C07K7/23; C07K7/16; A; A61; A61K; A61K38/00; Y; Y10; Y10S; Y10S930/00; Y10S930/01; Y10S930/13
Claims Analysis
Total Claims: 30
Claim 1
Independent Claim
144 words
A method for preventing ovulation of female mammalian eggs or inhibiting the release of steroids by the gonads of a mammal comprising administering an effective amount of a peptide or a nontoxic salt thereof to a mammal, said peptide having the formula R.sub.1 -D-Phe-D-Trp-Ser-Tyr-D-Trp-R.sub.5 -Arg-R.sub.6 wherein R 1 is selected from the group consisting of dehydro Pro, dehydro D-Pro, acetyl dehydro Pro and acetyl dehydro D-Pro; R 5 is selected from the group consisting of Leu and NαMe-Leu; and R 6 is selected from the group consisting of Pro-Gly-NH 2 and Pro-NHCH 2 CH 3 , wherein D-Phe in the 2-position may be substituted by Phe, NαMe-Phe, His, D-His, D-Trp, Trp or NαMe-Leu, wherein D-Trp in the 3-position may be substituted by Trp, D-Phe, Phe, Pro or D-His; and wherein D-Trp in the 6-Position may be substituted by Gly, D-Phe, imBzl D-His or D-Tyr.
Claim 2
Independent Claim
144 words
A method for preventing ovulation of female mammalian eggs or inhibiting the release of steroids by the gonads of a mammal comprising administering an effective amount of a peptide or a nontoxic salt thereof to a mammal, said peptide having the formula R.sub.1 -D-Phe-D-Trp-Ser-Tyr-D-Trp-R.sub.5 -Arg-R.sub.6 wherein R 1 is selected from the group consisting of dehydro Pro, dehydro D-Pro, acetyl dehydro Pro and acetyl dehydro D-Pro; R 5 is selected from the group consisting of Leu and NαMe-Leu; and R 6 is selected from the group consisting of Pro-Gly-NH 2 and Pro-NHCH 2 CH 3 , wherein D-Phe in the 2-position may be substituted by Phe, NαMe-Phe, His, D-His, D-Trp, Trp or NαMe-Leu, wherein D-Trp in the 3-position may be substituted by Trp, D-Phe, Phe, Pro or D-His; and wherein D-Trp in the 6-Position may be substituted by Gly, D-Phe, imBzl D-His or D-Tyr.
Claim 3
Dependent Claim
12 words
A method in accordance with claim 1 wherein R 5 is NαMe-Leu.
Claim 4
Dependent Claim
12 words
A method in accordance with claim 1 wherein R 5 is Leu.
Claim 5
Dependent Claim
16 words
A method in accordance with claim 1 wherein R 6 is Pro-NH-CH 2 CH 3 .
Claim 6
Dependent Claim
14 words
A method in accordance with claim 1 wherein R 6 is Pro-Gly-NH 2 .
Claim 7
Dependent Claim
17 words
A method in accordance with claim 1 wherein said peptide has the formula dehydro Pro-D-Phe-D-Trp-Ser-Tyr-D-Trp-Leu-Arg-Pro-Gly-NH 2 .
Claim 8
Dependent Claim
17 words
A method in accordance with claim 1 wherein said peptide has the formula dehydro Pro-D-Phe-D-Trp-Ser-Tyr-D-Trp-NαMe-Leu-Arg-Pro-Gly-NH 2 .
Claim 9
Dependent Claim
19 words
A method in accordance with claim 1 wherein said peptide has the formula dehydro Pro-D-Phe-D-Trp-Ser-Tyr-D-Trp-Leu-Arg-Pro-NHCH 2 CH 3 .
Claim 10
Dependent Claim
20 words
A method in accordance with claim 1 wherein said peptide has the formula acetyl dehydro Pro-D-Phe-D-Trp-Ser-Tyr-D-Trp-Leu-Arg-Pro-NHCH 2 CH 3 .
Claim 11
Dependent Claim
18 words
A method in accordance with claim 1 wherein said peptide has the formula acetyl dehydro Pro-D-Phe-D-Trp-Ser-Tyr-D-Trp-NαMe-Leu-Arg-Pro-Gly-NH 2 .
Claim 12
Dependent Claim
18 words
A method in accordance with claim 1 wherein said peptide has the formula acetyl dehydro Pro-D-Phe-D-Trp-Ser-Tyr-D-Trp-Leu-Arg-Pro-Gly-NH 2 .
Claim 13
Dependent Claim
18 words
A method in accordance with claim 1 wherein said peptide has the formula acetyl dehydro D-Pro-D-Phe-D-Trp-Ser-Tyr-D-Trp-Leu-Arg-Pro-Gly-NH 2 .
Claim 14
Dependent Claim
18 words
A method in accordance with claim 1 wherein said peptide has the formula acetyl dehydro D-Pro-D-Phe-D-Trp-Ser-Tyr-D-Trp-NαMe-Leu-Arg-Pro-Gly-NH 2 .
Claim 15
Dependent Claim
20 words
A method in accordance with claim 1 wherein said peptide has the formula acetyl dehydro D-Pro-D-Phe-Trp-Ser-Tyr-D-Trp-Leu-Arg-Pro-NHCH 2 CH 3 .
Claim 16
Dependent Claim
17 words
A method in accordance with claim 1 wherein said peptide has the formula dehydro D-Pro-D-Phe-D-Trp-Ser-Tyr-D-Trp-Leu-Arg-Pro-Gly-NH 2 .
Claim 17
Dependent Claim
17 words
A method in accordance with claim 1 wherein said peptide has the formula dehydro D-Pro-D-Phe-D-Trp-Ser-Tyr-D-Trp-NαMe-Leu-Arg-Pro-Gly-NH 2 .
Claim 18
Dependent Claim
19 words
A method in accordance with claim 1 wherein said peptide has the formula dehydro D-Pro-D-Phe-D-Trp-Ser-Tyr-D-Trp-Leu-Arg-Pro-NHCH 2 CH 3 .
Claim 19
Dependent Claim
21 words
A method in accordance with claim 1 wherein said peptide has the formula R 1 -D-Phe-D-Trp-Ser-Tyr-imBzl D-His-R 5 -Arg-R 6 .
Claim 20
Dependent Claim
109 words
A peptide having the formula R 1 -R 2 -R 3 -Ser-Tyr-R 4 -R 5 Arg-R 6 wherein R 1 is selected from the group consisting of dehydro Pro, dehydro D-Pro, acetyl dehydro Pro and acetyl dehydro D-Pro; R 2 is selected from the group consisting of D-Phe, D-His, and D-Trp; R 3 is selected from the group consisting of D-Trp, D-Phe, and D-His; R 4 is selected from the group consisting of D-Trp, D-Phe, imBzl D-His and D-Tyr; R 5 is selected from the group consisting of Leu and NαMe-Leu; and R 6 is selected from the group consisting of Pro-Gly-NH 2 and Pro-NHCH 2 CH 3 .
Claim 21
Dependent Claim
109 words
A peptide having the formula R 1 -R 2 -R 3 -Ser-Tyr-R 4 -R 5 Arg-R 6 wherein R 1 is selected from the group consisting of dehydro Pro, dehydro D-Pro, acetyl dehydro Pro and acetyl dehydro D-Pro; R 2 is selected from the group consisting of D-Phe, D-His, and D-Trp; R 3 is selected from the group consisting of D-Trp, D-Phe, and D-His; R 4 is selected from the group consisting of D-Trp, D-Phe, imBzl D-His and D-Tyr; R 5 is selected from the group consisting of Leu and NαMe-Leu; and R 6 is selected from the group consisting of Pro-Gly-NH 2 and Pro-NHCH 2 CH 3 .
Claim 22
Dependent Claim
12 words
A peptide in accordance with claim 19 wherein R 5 is NαMe-Leu.
Claim 23
Dependent Claim
14 words
A peptide in accordance with claim 19 wherein R 6 is Pro-Gly-NH 2 .
Claim 24
Dependent Claim
22 words
A peptide in accordance with claim 19 wherein R 2 is D-Phe, R 3 is D-Trp and R 4 is imBzl D-His.
Claim 25
Dependent Claim
62 words
A peptide having the formula R 1 -D-Phe-D-Trp-Ser-Tyr-D-Trp-R 5 -Arg-R 6 wherein R 1 is selected from the group consisting of dehydro Pro, dehydro D-Pro, acetyl dehydro Pro and acetyl dehydro D-Pro; R 5 is selected from the group consisting of Leu and NαMe-Leu; and R 6 is selected from the group consisting of Pro-Gly-NH 2 and Pro-NHCH 2 CH 3 .
Claim 26
Dependent Claim
62 words
A peptide having the formula R 1 -D-Phe-D-Trp-Ser-Tyr-D-Trp-R 5 -Arg-R 6 wherein R 1 is selected from the group consisting of dehydro Pro, dehydro D-Pro, acetyl dehydro Pro and acetyl dehydro D-Pro; R 5 is selected from the group consisting of Leu and NαMe-Leu; and R 6 is selected from the group consisting of Pro-Gly-NH 2 and Pro-NHCH 2 CH 3 .
Claim 27
Dependent Claim
14 words
A peptide in accordance with claim 23 wherein R 1 is acetyl dehydro Pro.
Claim 28
Dependent Claim
13 words
A peptide in accordance with claim 24 wherein R 5 is N MeLeu.
Claim 29
Dependent Claim
14 words
A peptide in accordance with claim 23 wherein R 6 is Pro-Gly-NH 2 .
Claim 30
Dependent Claim
13 words
A peptide in accordance with claim 23 wherein R 1 is dehydro Pro.
References Cited (Backward Citations)
US4072668A
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US4075191A
Cited
US3928307A
Cited
US3933782A
Cited
US4128638A
Cited
US4010125A
Cited
US4124703A
Cited
US4215038A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-12-21 | 1985-06-22 | 1985-12-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-12-21 | 1989-06-22 | 1989-12-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-12-21 | 1993-06-22 | 1993-12-22 | $7700.00 | Window Closed / Lapsed |