US4224199A
Expired / Lapsed
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Somatostatin analogs having a substituted tryptophyl residue in position eight
Assignee: Individual
•
Filing: 1979-04-09
•
Granted: 1980-09-23
•
Expires: 1999-04-09
Abstract
Abstract Tetradecapeptides of the formula ##STR1## in which A represents L, D or DL 5- or 6- fluoro-, bromo-,chloro- or iodotryptophyl, or a therapeutically acceptable acid addition salt thereof, their preparation and intermediates for their preparation are disclosed. The tetradecapeptides are useful for inhibiting the release of growth hormone. Compositions and methods for their use also are disclosed.
Inventors
- 👤 Chester A. Meyers
- 👤 David H. Coy
- 👤 Andrew V. Schally
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 07:09
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; Y10S930/16
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
30 words
A tetradecapeptide of the formula ##STR7## in which A represents L, D or DL 5- or 6- fluoro-, bromo-, chloro- or iodo-tryptophyl, or a therapeutically acceptable acid addition salt thereof.
Claim 2
Dependent Claim
30 words
A tetradecapeptide of the formula ##STR7## in which A represents L, D or DL 5- or 6- fluoro-, bromo-, chloro- or iodo-tryptophyl, or a therapeutically acceptable acid addition salt thereof.
Claim 3
Dependent Claim
28 words
A tetradecapeptide of the formula ##STR8## in which A represents L or D 5- or 6- fluoro- or bromo- tryptophyl, or a therapeutically acceptable acid addition salt thereof.
Claim 4
Dependent Claim
28 words
A tetradecapeptide of the formula ##STR8## in which A represents L or D 5- or 6- fluoro- or bromo- tryptophyl, or a therapeutically acceptable acid addition salt thereof.
Claim 5
Dependent Claim
10 words
The tetradecapeptide of claim 2 which is cyclic[3-14-disulfide] of L-alanyl-glycyl-L-cysteinyl-L-lysyl-L-asparaginyl-L-phenylalanyl-L-phenylalanyl-L-5-bromotryptophyl-L-lysyl-L-threonyl-L-phenylalanyl-L-threonyl-L-seryl-L-cysteine.
Claim 6
Dependent Claim
11 words
The tetradecapeptide of claim 2 which is cyclic[3-14 disulfide] of L-alanylglycyl-L-cysteinyl-L-lysyl-L-asparaginyl-L-phenylalanyl-L-phenylalanyl-D-5-bromotryptophyl-L-lysyl-L-threonyl-L-phenylalanyl-L-threonyl-L-seryl-L-cysteine.
Claim 7
Dependent Claim
11 words
The tetradecapeptide of claim 2 which is cyclic[3-14 disulfide] of L-alanyl-glycyl-L-cysteinyl-L-lysyl-L-asparaginyl-L-phenylalanyl-L-phenylalanylL-6-fluorotryptophyl-L-lysyl-L-threonyl-L-phenylalanyl-L-threonyl-L-seryl-cysteine.
Claim 8
Dependent Claim
11 words
The tetradecapeptide of claim 2 which is cyclic[3-14 disulfide] of L-alanyl-glycyl-L-cysteinyl-L-lysyl-L-asparaginyl-L-phenylalanyl-L-phenylalanyl-D-6-fluoro-tryptophyl-L-lysyl-L-threonyl-L-phenylalanyl-L-threonyl-L-seryl-L-cysteine.
Claim 9
Dependent Claim
11 words
The tetradecapeptide of claim 2 which is cyclic[3-14 disulfide] of L-alanyl-glycyl-L-cysteinyl-L-lysyl-L-asparaginyl-L-phenylalanyl-L-phenylalanyl-L-5-fluorotryptophyl-L-lysyl-L-threonyl-L-phenylalanyl-L-threonyl-L-seryl-L-cysteine.
Claim 10
Dependent Claim
11 words
The tetradecapeptide of claim 2 which is cyclic[3-14 disulfide] of L-alanyl-glycyl-L-cysteinyl-L-lysyl-L-asparaginyl-phenylalanyl-L-phenylalanyl-D-5-fluorotryptophyl-L-lysyl-L-threonyl-L-phenylalanyl-L-threonyl-L-seryl-L-cysteine.
Claim 11
Dependent Claim
11 words
The tetradecapeptide of claim 1 which is cyclic[3-14 disulfide] of L-alanyl-glycyl-L-cysteinyl-L-lysyl-L-asparaginyl-L-phenylalanyl-L-phenylalanyl-DL-5-bromotryptophyl-L-lysyl-L-threonyl-L-phenylalanyl-L-threonyl-L-seryl-L-cysteine.
Claim 12
Dependent Claim
11 words
The tetradecapeptide of claim 1 which is cyclic[3-14 disulfide] of L-alanyl-glycyl-L-cysteinyl-L-lysyl-L-asparaginyl-L-phenylalanyl-L-phenylalanyl-DL-6-fluorotryptophyl-L-lysyl-L-threonyl-L-phenylalanyl-L-threonyl-L-seryl-L-cysteine.
Claim 13
Dependent Claim
11 words
The tetradecapeptide of claim 1 which is cyclic[3-14 disulfide] of L-alanyl-glycyl-L-cysteinyl-L-lysyl-L-asparaginyl-L-phenylalanyl-L-phenylalanyl-DL-5-fluorotryptophyl-L-lysyl-L-threonyl-L-phenylalanyl-L-threonyl-L-seryl-L-cysteine.
Claim 14
Dependent Claim
139 words
A peptide of the formula R 1 -Ala-Gly-Cys(R 2 )-Lys(R 3 )-Asn-Phe-Phe-A-Lys(R 3 )-Thr(R 4 )-Phe-Thr(R 4 )-Ser(R 5 )-Cys(R 2 )-X in which A represents L, D or DL 5- or 6- fluoro-, bromo-, chloro- or iodo- tryptophyl; R 1 is hydrogen or an α-amino protecting group; R 2 is hydrogen or a sulfhydryl protecting group R 3 is hydrogen or an ε-amino protecting group; R 4 and R 5 each is hydrogen or a hydroxy protecting group; and X is hydroxy or O--CH 2 --[resin], with the proviso that: when X is hydroxy, then R 1 , R 2 , R 3 , R 4 and R 5 are hydrogen; and when X is O--CH 2 --[resin], then R 1 , R 2 , R 3 , R 4 and R 5 each are other than hydrogen.
Claim 15
Dependent Claim
139 words
A peptide of the formula R 1 -Ala-Gly-Cys(R 2 )-Lys(R 3 )-Asn-Phe-Phe-A-Lys(R 3 )-Thr(R 4 )-Phe-Thr(R 4 )-Ser(R 5 )-Cys(R 2 )-X in which A represents L, D or DL 5- or 6- fluoro-, bromo-, chloro- or iodo- tryptophyl; R 1 is hydrogen or an α-amino protecting group; R 2 is hydrogen or a sulfhydryl protecting group R 3 is hydrogen or an ε-amino protecting group; R 4 and R 5 each is hydrogen or a hydroxy protecting group; and X is hydroxy or O--CH 2 --[resin], with the proviso that: when X is hydroxy, then R 1 , R 2 , R 3 , R 4 and R 5 are hydrogen; and when X is O--CH 2 --[resin], then R 1 , R 2 , R 3 , R 4 and R 5 each are other than hydrogen.
Claim 16
Dependent Claim
33 words
A peptide as claimed in claim 12 wherein A is as defined therein; R 1 , R 2 , R 3 , R 4 and R 5 are hydrogen; and X is hydroxy.
Claim 17
Dependent Claim
110 words
A peptide as claimed in claim 12 wherein A represents L, D or DL 5- or 6- fluoro- or bromo- tryptophyl; R 1 is hydrogen or t-butoxycarbonyl; R 2 is hydrogen or 4-methylbenzyl; R 3 is hydrogen or 2-chlorobenzyloxycarbonyl; R 4 and R 5 each is hydrogen or benzyl; and X is hydroxy or O-CH 2 -[polystyrene-1%-divinylbenzene resin], with the proviso that: when X is hydroxy, then R 1 , R 2 , R 3 , R 4 and R 5 are hydrogen; and when X is O-CH 2 -[polystyrene-1%-divinylbenzene resin], then R 1 , R 2 , R 3 , R 4 and R 5 are other than hydrogen.
Claim 18
Dependent Claim
41 words
A peptide as claimed in claim 12 wherein A represents L, D or DL 5- or 6- fluoro- or bromo- tryptophyl; R 1 , R 2 , R 3 , R 4 and R 5 are hydrogen; and X is hydroxy.
Claim 19
Dependent Claim
27 words
A pharmaceutical composition which comprises a compound of claim 1 or a therapeutically acceptable acid addition salt thereof and a pharmaceutically acceptable liquid or solid carrier therefor.
Claim 20
Dependent Claim
35 words
A method of treating acromegaly or of managing diabetes in a mammal, which comprises administering to said mammal an effective dose of a compound of claim 1 or a therapeutically acceptable acid addition salt thereof.
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) | 1983-09-23 | 1984-03-24 | 1984-09-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-09-23 | 1988-03-24 | 1988-09-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-09-23 | 1992-03-24 | 1992-09-23 | $7700.00 | Window Closed / Lapsed |