US4317815A
Expired / Lapsed
US
⏱️ 0.0 years remaining
LH-RH Antagonists
Assignee: Tulane University
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Filing: 1980-06-02
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Granted: 1982-03-02
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Expires: 2000-06-02
Abstract
Abstract Disclosed herein are peptide analogs of the luteinizing hormone releasing hormone (LH-RH) which are potent antagonist of LHRH. The analogs differ in structure from LH-RH by having different amino acid residues at positions 1, 2 and 6, and optionally at positions 3 and 10. Methods for preparing and using these analogs are described.
Inventors
- 👤 David H. Coy
- 👤 Andrew V. Schally
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 19:15
CPC Classifications
C; C07; C07K; C07K7/00; C07K7/04; C07K7/23; A; A61; A61K; A61K38/00; Y; Y10; Y10S; Y10S930/00; Y10S930/01; Y10S930/13
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
79 words
A compound of formula I X-R.sup.1 -R.sup.2 -R.sup.3 -Ser-Tyr-R.sup.4 -Leu-Arg-Pro-R.sup.5 -NH.sub.2 (I) in which X is hydrogen, lower alkanoyl, HOOC--(CH 2 ) n --CO wherein n is an integer from 2 to 6, benzoyl or the acyl portion of a D- or L- amino acid; R 1 is D-Trp, D-Phe or D-p-halo-Phe; R 2 is D-p-halo-Phe; R 3 is D-Trp; R 4 is D-Trp or D-Phe; and R 5 is Gly or D-Ala; or a therapeutically acceptable salt thereof.
Claim 2
Dependent Claim
79 words
A compound of formula I X-R.sup.1 -R.sup.2 -R.sup.3 -Ser-Tyr-R.sup.4 -Leu-Arg-Pro-R.sup.5 -NH.sub.2 (I) in which X is hydrogen, lower alkanoyl, HOOC--(CH 2 ) n --CO wherein n is an integer from 2 to 6, benzoyl or the acyl portion of a D- or L- amino acid; R 1 is D-Trp, D-Phe or D-p-halo-Phe; R 2 is D-p-halo-Phe; R 3 is D-Trp; R 4 is D-Trp or D-Phe; and R 5 is Gly or D-Ala; or a therapeutically acceptable salt thereof.
Claim 3
Dependent Claim
57 words
The compound of claim 1 in which X is hydrogen, lower alkanoyl, HOOC--(CH 2 ) n --CO wherein n is an integer from 2 to 6, benzoyl or the acyl portion of an amino acid residue of alanine, arginine, asparagine, cysteine, glutamine, glycine, histidine, isoleucine, leucine, lysine, methionine, ornithine, phenylalanine, proline, serine, threonine, tryptophan, tyrosine and valine.
Claim 4
Dependent Claim
53 words
The compound of claim 1 in which X is acetyl or HOOCCH 2 --CH 2 CO, R 1 is D-Trp, D-Phe or D-p-Cl-Phe; R 2 is D-p-Cl-Phe, D-p-Br-Phe or D-p-F-Phe; R 3 is D-Trp; R 4 is D-Trp or D-Phe; and R 5 is Gly or D-Ala; or a therapeutically acceptable salt thereof.
Claim 5
Dependent Claim
6 words
D-Phenylalanyl-D-p-chlorophenylalanyl-D-tryptophyl-L-seryl-L-tyrosyl-D-tryptophyl-L-leucyl-L-arginyl-L-prolyl-glycinamide, as claimed in claim 1.
Claim 6
Dependent Claim
1 words
N-Acetyl-D-phenylalanyl-D-p-chlorophenylalanyl-D-tryptophyl-L-seryl-L-tyrosyl-D-tryptophanyl-L-leucyl-L-arginyl-L-prolyl-glycinamide.
Claim 7
Dependent Claim
1 words
N-Acetyl-D-phenylalanyl-D-p-chlorophenylalanyl-D-tryptophyl-L-seryl-L-tyrosyl-D-tryptophanyl-L-leucyl-L-arginyl-L-prolyl-glycinamide.
Claim 8
Dependent Claim
6 words
D-Phenylalanyl-D-p-bromophenylalanyl-D-tryptophyl-L-seryl-L-tyrosyl-D-phenylalanyl-L-leucyl-L-arginyl-L-prolyl-glycinamide, as claimed in claim 1.
Claim 9
Dependent Claim
6 words
D-Phenylalanyl-D-p-chlorophenylalanyl-D-tryptophyl-L-seryl-L-tyrosyl-D-phenylalanyl-L-leucyl-L-arginyl-L-prolyl-glycinamide, as claimed in claim 1.
Claim 10
Dependent Claim
6 words
N-Succinyl-D-phenylalanyl-D-p-chlorophenylalanyl-D-tryptophyl-L-seryl-L-tyrosyl-D-phenylalanyl-L-leucyl-L-arginyl-L-rpolyl-glycinamide, as claimed in claim 1.
Claim 11
Dependent Claim
6 words
N-Acetyl-D-p-chlorophenylalanyl-D-p-chlorophenylalanyl-D-tryptophyl-L-seryl-L-tyrosyl-D-tryptophyl-L-leucyl-L-arginyl-L-prolyl-glycinamide as claimed in claim 1.
Claim 12
Dependent Claim
6 words
N-Acetyl-D-tryptophyl-D-p-chlorophenylalanyl-D-tryptophyl-L-seryl-L-tyrosyl-D-tryptophyl-L-leucyl-L-arginyl-L-prolyl-glycinamide, as claimed in claim 1.
Claim 13
Dependent Claim
6 words
N-Acetyl-D-phenylalanyl-D-p-chlorophenylalanyl-D-tryptophyl-L-seryl-L-tyrosyl-D-tryptophyl-L-leucyl-L-arginyl-L-prolyl-D-alaninamide, as claimed in claim 1.
Claim 14
Dependent Claim
36 words
A gonadotropin antagonizing pharmaceutical composition for antagonizing gonadotropin release in mammals in need thereof comprising a gonadotropin antagonizing amount of the compound of claim 1 or a therapeutically acceptable salt thereof, and a pharmaceutically acceptable carrier.
Claim 15
Dependent Claim
36 words
A method for relieving complications from the physiological availability of pituitary gonadatropins in a mammal, which comprises administering to the mammal a gonadotropin-antagonizing dose of the compound of claim 1 or a therapeutically acceptable salt thereof.
Claim 16
Dependent Claim
13 words
The method of claim 13 wherein said complications comprise the regulation of ovalation.
Claim 17
Dependent Claim
6 words
D-Phenylalanyl-D-p-fluorophenylalanyl-D-tryptophyl-L-seryl-L-tyrosyl-D-phenylalanyl-L-leucyl-L-arginyl-L-prolyl-glycinamide, as claimed in claim 1.
References Cited (Backward Citations)
US4215038A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-03-01 | 1985-08-31 | 1986-03-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-03-01 | 1989-08-31 | 1990-03-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-03-01 | 1993-08-31 | 1994-03-02 | $7700.00 | Window Closed / Lapsed |