US4226857A
Expired / Lapsed
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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: 1980-10-07
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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 and G are independently selected from a group consisting of tyrosine, trytophan, and phenlalanine; Z and J are independently selected from a group consisting of D-tyrosine, D-tryptophan, an D-phenylalanine; E is selected from a group consisting of glycine, alanine, valine, leucine, isoleucine, proline, hydroxyproline, serine, threonine, cysteine, methionine, aspartic acid, glutamic acid, asparagine, glutamine, and histidine; 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
2026-11-03 14:08
CPC Classifications
C; C07; C07K; C07K5/00; C07K5/04; C07K5/08; C07K5/0802; C07K5/0812; A; A61; A61P; A61P5/00; C07K14/00; C07K14/435; C07K14/575; C07K14/60; C07K5/10; C07K5/1024; A61K; A61K38/00; Y; Y10; Y10S; Y10S930/00; Y10S930/01; Y10S930/12
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
138 words
A peptide having a formula X-Y-Z-E-G-J-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 and G are independently selected from a group consisting of Tyr, Trp, and Phe; Z and J are independently selected from a group consisting of D-Tyr, D-Trp, and D-Phe; E is selected from a group consisting of Gly, Ala, Val, Leu, Ile, Ser, Thr, Met, Asn, and Gln; 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 branched alkyl groups containing 1-6 carbon atoms.
Claim 2
Dependent Claim
138 words
A peptide having a formula X-Y-Z-E-G-J-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 and G are independently selected from a group consisting of Tyr, Trp, and Phe; Z and J are independently selected from a group consisting of D-Tyr, D-Trp, and D-Phe; E is selected from a group consisting of Gly, Ala, Val, Leu, Ile, Ser, Thr, Met, Asn, and Gln; 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 branched alkyl groups containing 1-6 carbon atoms.
Claim 3
Dependent Claim
28 words
The peptide of claim 1 having the formula X-Tyr-D-Trp-E-Trp-D-Phe-L wherein E is selected from the group consisting of Gly, Ala, Val, Leu, Ile, Ser, Thr, Asn, and Gln.
Claim 4
Dependent Claim
9 words
The peptide of claim 2 wherein E is Ala.
Claim 5
Dependent Claim
9 words
The peptide of claim 2 wherein E is Ser.
Claim 6
Dependent Claim
9 words
The peptide of claim 2 wherein E is Asn.
Claim 7
Dependent Claim
9 words
The peptide of claim 2 wherein E is Gln.
Claim 8
Dependent Claim
9 words
The peptide of claim 2 wherein E is Thr.
Claim 9
Dependent Claim
9 words
The peptide of claim 2 wherein E is Gly.
Claim 10
Dependent Claim
10 words
The peptide of claim 2 of the formula H.sub.2 N-Tyr-D-Trp-Ala-Trp-D-Phe-CONH.sub.2.
Claim 11
Dependent Claim
10 words
The peptide of claim 2 of the formula H.sub.2 N-Tyr-D-Trp-Ser-Trp-D-Phe-CONH.sub.2.
Claim 12
Dependent Claim
10 words
The peptide of claim 2 of the formula H.sub.2 N-Tyr-D-Trp-Ala-Trp-D-Phe-COOH.
Claim 13
Dependent Claim
30 words
The peptide of claims 2-7 or 8 wherein each R, R 1 , and R 2 is independently selected from the group consisting of alkyl groups containing 1-2 carbon atoms.
Claim 14
Dependent Claim
13 words
The peptide of claims 2-7 or 8 wherein L is --CONH 2 .
Claim 15
Dependent Claim
28 words
The peptide of claim 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 16
Dependent Claim
11 words
The peptide of claim 1 wherein L is --CONH 2 .
Claim 17
Dependent Claim
18 words
A compound of the formula Boc-Tyr(BrZ)-D-Trp-Ala-Trp-D-Phe-® wherein BrZ is p-bromobenzyloxycarbonyl; Boc is t-butyloxycarbonyl; and ® is benzhydrylamine resin.
Claim 18
Dependent Claim
18 words
A compound of the formula Boc-Tyr(BrZ)-D-Trp-Ala-Trp-D-Phe-® wherein BrZ is p-bromobenzyloxycarbonyl; Boc is t-butyloxycarbonyl; and ® is benzhydrylamine resin.
Claim 19
Dependent Claim
18 words
A compound of the formula Boc-Tyr(BrZ)-D-Trp-Ala-Trp-D-Phe-® wherein BrZ is p-bromobenzyloxycarbonyl; Boc is t-butoxycarbonyl; and ® is hydroxymethyl resin.
Claim 20
Dependent Claim
18 words
A compound of the formula Boc-Tyr(BrZ)-D-Trp-Ala-Trp-D-Phe-® wherein BrZ is p-bromobenzyloxycarbonyl; Boc is t-butoxycarbonyl; and ® is hydroxymethyl resin.
Claim 21
Dependent Claim
21 words
A compound of the formula Boc-Tyr(BrZ)-D-Trp-Ser(Bz)-Trp-D-Phe-® wherein BrZ is p-bromobenzyloxycarbonyl; Boc is t-butoxycarbonyl; Bz is benzyl; and ® is benzhydrylamine resin.
Claim 22
Dependent Claim
21 words
A compound of the formula Boc-Tyr(BrZ)-D-Trp-Ser(Bz)-Trp-D-Phe-® wherein BrZ is p-bromobenzyloxycarbonyl; Boc is t-butoxycarbonyl; Bz is benzyl; and ® is benzhydrylamine resin.
Claim 23
Independent Claim
21 words
A method of releasing growth hormone from a pituitary comprising contacting said pituitary with the peptide of claims 2-10 or 11.
Claim 24
Independent Claim
27 words
A method of releasing growth hormone from a pituitary comprising contacting said pituitary with the peptide of claims 2-7 or 8 wherein L is --CONH 2 .
Claim 25
Dependent Claim
19 words
A method of releasing growth hormone from a pituitary comprising contacting said pituitary with the peptide of claim 1.
Claim 26
Dependent Claim
25 words
A method of releasing growth hormone from a pituitary comprising contacting said pituitary with the peptide of claim 1 wherein L is --CONH 2 .
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) | 1983-10-07 | 1984-04-07 | 1984-10-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-10-07 | 1988-04-07 | 1988-10-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-10-07 | 1992-04-07 | 1992-10-07 | $7700.00 | Window Closed / Lapsed |