US4133782A
Expired / Lapsed
US
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Somatostatin analogs with dissociated biological activities
Assignee: Salk Institute for Biological Studies
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Filing: 1977-04-07
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Granted: 1979-01-09
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Expires: 1997-04-07
Abstract
Abstract The present invention relates to peptides having dissociated biological activity in respect to the inhibition of growth hormone, insulin, and glucagon secretion. The peptides are analogs of somatostatin.
Inventors
- 👤 Wylie W. Vale, Jr.
- 👤 Jean E. F. Rivier
- 👤 Marvin R. Brown
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 04:48
CPC Classifications
C; C07; C07K; C07K14/00; C07K14/435; C07K14/575; C07K14/655; C07K14/6555; A; A61; A61K; A61K38/00; Y; Y10; Y10S; Y10S930/00; Y10S930/01; Y10S930/12; Y10S930/16
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
267 words
A peptide selected from those of the formulae: ##STR4## and the non-toxic salts thereof, wherein X 1 is selected from Asn and des-Asn; X 2 is selected from Trp and D-Trp; X 3 is selected from Ser and D-Ser; and X 4 is selected from Cys and D-Cys with the proviso that X 1 is des-Asn when X 2 is D-Trp, X 3 is Ser and X 4 is Cys; X 3 is D-Ser when X 1 is Asn and X 4 is Cys; and X 4 is D-Cys when X 1 is Asn and X 3 is Ser; R is selected from the class consisting of H and an alpha-amino protecting group; R 1 and R 7 are selected from the group consisting of H and a protecting group for Cys selected from S-p-methoxybenzyl, S-p-methylbenzyl, S-acetamidomethyl, S-trityl and S-benzyl; R 2 and R 3 are selected from the group consisting of H and a side chain amino protecting group for Lys selected from the group consisting of benzyl, chlorobenzyloxycarbonyl, benzyloxycarbonyl, tosyl, t-amyloxycarbonyl, t-butyloxycarbonyl, R 4 , R 5 and R 6 are selected from the group consisting of H and a hydroxyl protecting group selected from the group consisting of acetyl, benzoyl, tert-butyl, trityl, benzyl and benzyloxycarbonyl; with the proviso that at least one of R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 is other than hydrogen; and X 5 is selected from the group consisting of hydroxy, methoxy, esters, amides, hydrozides, -O-CH 2 -polystyrene resin support and O-CH 2 -benzyl-polystyrene resin support.
Claim 2
Dependent Claim
267 words
A peptide selected from those of the formulae: ##STR4## and the non-toxic salts thereof, wherein X 1 is selected from Asn and des-Asn; X 2 is selected from Trp and D-Trp; X 3 is selected from Ser and D-Ser; and X 4 is selected from Cys and D-Cys with the proviso that X 1 is des-Asn when X 2 is D-Trp, X 3 is Ser and X 4 is Cys; X 3 is D-Ser when X 1 is Asn and X 4 is Cys; and X 4 is D-Cys when X 1 is Asn and X 3 is Ser; R is selected from the class consisting of H and an alpha-amino protecting group; R 1 and R 7 are selected from the group consisting of H and a protecting group for Cys selected from S-p-methoxybenzyl, S-p-methylbenzyl, S-acetamidomethyl, S-trityl and S-benzyl; R 2 and R 3 are selected from the group consisting of H and a side chain amino protecting group for Lys selected from the group consisting of benzyl, chlorobenzyloxycarbonyl, benzyloxycarbonyl, tosyl, t-amyloxycarbonyl, t-butyloxycarbonyl, R 4 , R 5 and R 6 are selected from the group consisting of H and a hydroxyl protecting group selected from the group consisting of acetyl, benzoyl, tert-butyl, trityl, benzyl and benzyloxycarbonyl; with the proviso that at least one of R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 is other than hydrogen; and X 5 is selected from the group consisting of hydroxy, methoxy, esters, amides, hydrozides, -O-CH 2 -polystyrene resin support and O-CH 2 -benzyl-polystyrene resin support.
Claim 3
Dependent Claim
28 words
A peptide in accordance with formula I of claim 1 wherein X 1 is des-Asn, X 2 is D-Trp, X 3 is Ser and X 4 is Cys.
Claim 4
Dependent Claim
28 words
A peptide in accordance with formula I of claim 1 wherein X 1 is Asn, X 2 is Trp, X 3 is Ser and X 4 is D-Cys.
Claim 5
Dependent Claim
28 words
A peptide in accordance with formula I of claim 1 wherein X 1 is Asn, X 2 is D-Trp, X 3 is Ser and X 4 is D-Cys.
Claim 6
Dependent Claim
28 words
A peptide in accordance with formula I of claim 1 wherein X 1 is Asn, X 2 is Trp, X 3 is D-Ser, and X 4 is Cys.
Claim 7
Dependent Claim
28 words
A peptide in accordance with formula I of claim 1 wherein X 1 is Asn, X 2 is D-Trp, X 3 is D-Ser and X 4 is Cys.
Claim 8
Dependent Claim
28 words
A peptide in accordance with formula II of claim 1 wherein X 1 is des-Asn, X 2 is D-Trp, X 3 is Ser and X 4 is Cys.
Claim 9
Dependent Claim
28 words
A peptide in accordance with formula II of claim 1 wherein X 1 is Asn, X 2 is Trp, X 3 is Ser and X 4 is D-Cys.
Claim 10
Dependent Claim
28 words
A peptide in accordance with formula II of claim 1 wherein X 1 is Asn, X 2 is D-Trp, X 3 is Ser and X 4 is D-Cys.
Claim 11
Dependent Claim
28 words
A peptide in accordance with formula II of claim 1 wherein X 1 is Asn, X 2 is Trp, X 3 is D-Ser, and X 4 is Cys.
Claim 12
Dependent Claim
28 words
A peptide in accordance with formula II of claim 1 wherein X 1 is Asn, X 2 is D-Trp, X 3 is D-Ser and X 4 is Cys.
Claim 13
Dependent Claim
28 words
A peptide in accordance with formula III of claim 1 wherein X 1 is des-Asn, X 2 is D-Trp, X 3 is Ser and X 4 is Cys.
Claim 14
Dependent Claim
28 words
A peptide in accordance with formula III of claim 1 wherein X 1 is Asn, X 2 is Trp, X 3 is Ser and X 4 is D-Cys.
Claim 15
Dependent Claim
28 words
A peptide in accordance with formula III of claim 1 wherein X 1 is Asn, X 2 is D-Trp, X 3 is Ser and X 4 is D-Cys.
Claim 16
Dependent Claim
28 words
A peptide in accordance with formula III of claim 1 wherein X 1 is Asn, X 2 is Trp, X 3 is D-Ser, and X 4 is Cys.
Claim 17
Dependent Claim
28 words
A peptide in accordance with formula III of claim 1 wherein X 1 is Asn, X 2 is D-Trp, X 3 is D-Ser and X 4 is Cys.
Claim 18
Dependent Claim
19 words
A peptide in accordance with formula III of claim 1 wherein X 5 is -O-CH 2 -polystyrene resin support.
Claim 19
Dependent Claim
19 words
A peptide in accordance with formula III of claim 1 wherein X 5 is -O-CH 2 -benzyl-polystyrene resin support.
Claim 20
Dependent Claim
36 words
A peptide in accordance with claim 17 wherein R is t-butyloxycarbonyl, R 4 , R 5 and R 6 are benzyl. R 2 and R 3 are 2-chlorobenzyloxycarbonyl and R 1 and R 7 are S-p-methoxybenzyl.
Claim 21
Dependent Claim
12 words
A peptide in accordance with claim 1 wherein Cys 3 is D-Cys.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-01-08 | 1982-07-10 | 1983-01-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-01-08 | 1986-07-10 | 1987-01-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-01-08 | 1990-07-10 | 1991-01-09 | $7700.00 | Window Closed / Lapsed |