Patent US4228155A successfully refreshed from Google Patents.
US4228155A
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Synthetic peptides having pituitary growth hormone releasing activity
Assignee: SmithKline Beecham Corp
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Filing: 1979-03-30
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Granted: 1980-10-14
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Expires: 1999-03-30
Abstract
Abstract Novel pentapeptides having the following amino acid sequence X-Y-Z-E-G-J-L wherein X is selected from a group consisting of --NH 2 , --NHCH 3 , and --N(CH 3 ) 2 ; Y is selected from a group consisting of tyrosine, D-tyrosine, tryptophan, D-tryptophan, phenylalanine, and D-phenylalanine; Z and E are independently selected from a group consisting of D-tyrosine, D-tryptophan, and D-phenylalanine; G is selected from a group consisting of lysine and arginine; J is selected from a group consisting of glycine, alanine, valine, leucine, isoleucine, proline, hydroxyproline, serine, threonine, cysteine, and methionine; and L is a C-terminal functional group selected from a group consisting of amide, amide lower alkyl, amide di(lower alkyl), lower alkoxy, hydroxy, and carboxy and the lower ester derivatives thereof; and the pharmaceutically acceptable salts thereof. These peptides act directly on the pituitary to release growth hormone therefrom.
Inventors
- 👤 Frank A. Momany
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 14:40
CPC Classifications
C; C07; C07K; C07K5/00; C07K5/04; C07K5/08; C07K5/0802; C07K5/0812; C07K14/00; C07K14/435; C07K14/575; C07K14/60; C07K5/10; C07K5/1024; A; A61; A61K; A61K38/00; Y; Y10; Y10S; Y10S930/00; Y10S930/01; Y10S930/12
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
100 words
A peptide having a formula X-Y-D-Phe-D-Phe-Lys-Met-L and the pharmaceutically acceptable non-toxic acid addition salts, thereof wherein X is selected from a group consisting of --NH 2 , --NHCH 3 , and --N(CH 3 ) 2 ; Y is selected from a group consisting of Trp and D-Trp; and L is selected from a group consisting of --CONH 2 , --CONHR, --CONR 1 R 2 , --CH 2 OR, --CH 2 OH, --COOH, and --COOR, wherein each R, R 1 , and R 2 is independently selected from a group consisting of straight and branch alkyl groups containing 1-6 carbon atoms.
Claim 2
Dependent Claim
100 words
A peptide having a formula X-Y-D-Phe-D-Phe-Lys-Met-L and the pharmaceutically acceptable non-toxic acid addition salts, thereof wherein X is selected from a group consisting of --NH 2 , --NHCH 3 , and --N(CH 3 ) 2 ; Y is selected from a group consisting of Trp and D-Trp; and L is selected from a group consisting of --CONH 2 , --CONHR, --CONR 1 R 2 , --CH 2 OR, --CH 2 OH, --COOH, and --COOR, wherein each R, R 1 , and R 2 is independently selected from a group consisting of straight and branch alkyl groups containing 1-6 carbon atoms.
Claim 3
Dependent Claim
9 words
The peptide of claim 1 wherein Y is Trp.
Claim 4
Dependent Claim
9 words
The peptide of claim 1 wherein Y is D-Trp.
Claim 5
Dependent Claim
10 words
The peptide of claim 1 of the formula H.sub.2 N-D-Trp-D-Phe-D-Phe-Lys-Met-CONH.sub.2.
Claim 6
Dependent Claim
10 words
The peptide of claim 1 of the formula N.sub.2 N-Trp-D-Phe-D-Phe-Lys-Met-CONH.sub.2.
Claim 7
Dependent Claim
30 words
The peptide of claim 2-3 or 1 wherein each R, R 1 , and R 2 is independently selected from the group consisting of alkyl groups containing 1-2 carbon atoms.
Claim 8
Dependent Claim
13 words
The peptide of claim 2-3 or 1 wherein L is --CONH 2 .
Claim 9
Dependent Claim
21 words
A method of releasing growth hormone from a pituitary comprising contacting said pituitary with the peptide of claim 2-5 or 1.
Claim 10
Dependent Claim
27 words
A method of releasing growth hormone from a pituitary comprising contacting said pituitary with the peptide of claim 2-3 or 1 wherein L is --CONH 2 .
Claim 11
Dependent Claim
18 words
A compound of the formula Boc-D-Trp-D-Phe-D-Phe-Lys(Z)-Met-® wherein Z is benzyloxycarbonyl; Boc is t-butyloxycarbonyl; and ® is benzhydrylamine resin.
Claim 12
Dependent Claim
18 words
A compound of the formula Boc-D-Trp-D-Phe-D-Phe-Lys(Z)-Met-® wherein Z is benzyloxycarbonyl; Boc is t-butyloxycarbonyl; and ® is benzhydrylamine resin.
Claim 13
Dependent Claim
18 words
A compound of the formula Boc-Trp-D-Phe-D-Phe-Lys(Z)-Met-® wherein Z is benzyloxycarbonyl; Boc is t-butoxycarbonyl; and ® is benzhydrylamine resin.
Claim 14
Dependent Claim
18 words
A compound of the formula Boc-Trp-D-Phe-D-Phe-Lys(Z)-Met-® wherein Z is benzyloxycarbonyl; Boc is t-butoxycarbonyl; and ® is benzhydrylamine resin.
References Cited (Backward Citations)
US3479333A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-10-14 | 1984-04-14 | 1984-10-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-10-14 | 1988-04-14 | 1988-10-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-10-14 | 1992-04-14 | 1992-10-14 | $7700.00 | Window Closed / Lapsed |