US4244946A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Water-soluble peptides affecting gonadal function
Assignee: Salk Institute for Biological Studies
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Filing: 1979-06-11
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Granted: 1981-01-13
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Expires: 1999-06-11
Abstract
Abstract [im-Bzl D-His6]LRF and [D-His6(im-Bzl), Pro9-NEt]LRF exhibit hydrophillicity comparable to that of LRF and act as superagonists exhibiting potencies, respectively, about 12 and more than 200 times that of LRF. The peptides or their nontoxic salts can be administered by intravenous subcutaneous, sublingual, oral, intravaginal, intranasal or rectal routes. The peptides can be used to regulate fertility in male and female mammals, including human beings.
Inventors
- 👤 Jean E. F. Rivier
- 👤 Wylie W. Vale, Jr.
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 14:52
CPC Classifications
F; F24; F24F; F24F11/00; F24F11/30; C; C07; C07K; C07K7/00; C07K7/04; C07K7/23; A; A61; A61P; A61P15/00; A61P5/00; F24F11/89; A61K; A61K38/00; F24F2110/00; F24F2110/10; Y; Y10; Y10S; Y10S930/00; Y10S930/01; Y10S930/13
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
188 words
A compound selected from the class defined by the formulae: p-Glu-His-Trp-Ser-Tyr-D-His(im-Bzl)-Leu-Arg-R and its nontoxic salts, and X 1 -p-Glu-His(X 2 )-Trp-Ser(X 3 )-Tyr(X 4 )-D-His(im-Bzl)-Leu-Arg(X.sup.5)-Pro-X 6 wherein R is selected from the group consisting of Pro-Gly-NH 2 and Pro-NH-CH 2 -CH 3 ; X 1 is either hydrogen or an α-amino protecting group; X 2 is a protecting group for the imidazole nitrogen atom selected from the group consisting of Tos, benzyl, trityl, 2,2,2-trifluoro-1-benzyloxycarbonylaminoethyl, 2,2,2-trifluoro-1tert-butyloxycarbonylaminoethyl and 2,4-dinitrothiophenyl; X 3 is a protecting group for the alcoholic hydroxyl group of Ser selected from the group consisting of acetyl, benzoyl, tetrahydropyranyl, tert-butyl, trityl, benzyl and 2,6-dichlorobenzyl; X 4 is a protecting group for the phenolic hydroxyl group of Tyr selected from the group consisting of tetrahydropyranyl, tert-butyl, trityl, benzyl, benzyloxycarbonyl, 4-bromobenzyloxycarbonyl and 2,6-dichlorobenzyl; X 5 is protecting group for the nitrogen atoms of Arg selected from the group consisting of nitro, Tos, benzyloxycarbonyl, adamantyloxycarbonyl, and BOC, or is hydrogen; and X 6 is selected from the group consisting of dimethylamine, alkylamine of 1 to 5 carbon atoms, phenethylamine, O-CH 2 -[resin support], Gly-O-CH 2 -[resin support], and Gly-NH [resin support].
Claim 2
Dependent Claim
188 words
A compound selected from the class defined by the formulae: p-Glu-His-Trp-Ser-Tyr-D-His(im-Bzl)-Leu-Arg-R and its nontoxic salts, and X 1 -p-Glu-His(X 2 )-Trp-Ser(X 3 )-Tyr(X 4 )-D-His(im-Bzl)-Leu-Arg(X.sup.5)-Pro-X 6 wherein R is selected from the group consisting of Pro-Gly-NH 2 and Pro-NH-CH 2 -CH 3 ; X 1 is either hydrogen or an α-amino protecting group; X 2 is a protecting group for the imidazole nitrogen atom selected from the group consisting of Tos, benzyl, trityl, 2,2,2-trifluoro-1-benzyloxycarbonylaminoethyl, 2,2,2-trifluoro-1tert-butyloxycarbonylaminoethyl and 2,4-dinitrothiophenyl; X 3 is a protecting group for the alcoholic hydroxyl group of Ser selected from the group consisting of acetyl, benzoyl, tetrahydropyranyl, tert-butyl, trityl, benzyl and 2,6-dichlorobenzyl; X 4 is a protecting group for the phenolic hydroxyl group of Tyr selected from the group consisting of tetrahydropyranyl, tert-butyl, trityl, benzyl, benzyloxycarbonyl, 4-bromobenzyloxycarbonyl and 2,6-dichlorobenzyl; X 5 is protecting group for the nitrogen atoms of Arg selected from the group consisting of nitro, Tos, benzyloxycarbonyl, adamantyloxycarbonyl, and BOC, or is hydrogen; and X 6 is selected from the group consisting of dimethylamine, alkylamine of 1 to 5 carbon atoms, phenethylamine, O-CH 2 -[resin support], Gly-O-CH 2 -[resin support], and Gly-NH [resin support].
Claim 3
Dependent Claim
13 words
A compound in accordance with claim 1 wherein R is Pro-Gly-NH 2 .
Claim 4
Dependent Claim
15 words
A compound in accordance with claim 1 wherein R is Pro-NH-CH 2 -CH 3 .
Claim 5
Independent Claim
52 words
A method for regulating fertility and the production of gonadotropins and sex steroids in male and female mammalians comprising administering an effective amount of a peptide having the formula: p-Glu-His-Trp-Ser-Tyr-D-His(im-Bzl)-Leu-Arg-R, wherein R is selected from the group consisting of Pro-Gly-NH 2 and Pro-NH-CH 2 -CH 3 , or a nontoxic salt thereof.
Claim 6
Independent Claim
52 words
A method for regulating fertility and the production of gonadotropins and sex steroids in male and female mammalians comprising administering an effective amount of a peptide having the formula: p-Glu-His-Trp-Ser-Tyr-D-His(im-Bzl)-Leu-Arg-R, wherein R is selected from the group consisting of Pro-Gly-NH 2 and Pro-NH-CH 2 -CH 3 , or a nontoxic salt thereof.
Claim 7
Dependent Claim
13 words
A method in accordance with claim 4 wherein R is Pro-Gly-NH 2 .
Claim 8
Dependent Claim
15 words
A method in accordance with claim 4 wherein R is Pro-NH-CH 2 -CH 3 .
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-01-13 | 1984-07-14 | 1985-01-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-01-13 | 1988-07-14 | 1989-01-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-01-13 | 1992-07-14 | 1993-01-13 | $7700.00 | Window Closed / Lapsed |