US4010149A
Expired / Lapsed
US
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Analogs of LH-RH and process for preparing the same
Assignee: Sankyo Co Ltd
•
Filing: 1975-04-07
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Granted: 1977-03-01
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Expires: 1995-04-07
Abstract
Abstract Peptides having the formula N-Acetyl-N-methylglycyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-Y-L-leucyl-L-arginyl-L-prolyl-Z wherein Y is a D-α-alkylglycine residue of the formula ##STR1## in which n is an integer of 0 through 3 inclusive and Z is ethylamino group or an ethylamino group which is substituted with 1 to 3 fluorine atoms at the 2-position and pharmaceutically acceptable salts thereof. They show luteinizing hormone-releasing hormone like activities and are prepared by reacting L-histidyl-L-tryptophyl-L-seryl(or L-seryl having a protected hydroxyl group)-L-tyrosyl(or L-tyrosyl having a protected hydroxyl group)-Y-L-leucyl-L-arginyl(or L-arginyl having a protected guanidyl group)-L-prolyl-Z wherein Y and Z are as defined above with a reactive derivative of N-Acetyl-N-methylglycine And, if a protective group is attached, then removing the protective group, and, if necessary, converting further the resultant into an acid addition salt thereof in the usual manner.
Inventors
- 👤 Yoshihiko Baba
- 👤 Yutaka Okada
- 👤 Hiroyashi Horikoshi
- 👤 Yuichiro Yabe
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 04:39
CPC Classifications
C; C07; C07K; C07K7/00; C07K7/04; C07K7/23; A; A61; A61K; A61K38/00; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55; Y10; Y10S; Y10S930/00; Y10S930/01; Y10S930/13
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
47 words
A peptide having the formula N-Acetyl-N-methylglycyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-Y-L-leucyl-L-arginyl-L-prolyl-Z wherein Y is a D-α-alkylglycine residue of the formula ##STR3##in which n is an integer of 0 through 3 inclusive and Z is ethylamino group or an ethylamino group which is substituted with 1 to 3 fluorine atoms at the 2-position.
Claim 2
Dependent Claim
47 words
A peptide having the formula N-Acetyl-N-methylglycyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-Y-L-leucyl-L-arginyl-L-prolyl-Z wherein Y is a D-α-alkylglycine residue of the formula ##STR3##in which n is an integer of 0 through 3 inclusive and Z is ethylamino group or an ethylamino group which is substituted with 1 to 3 fluorine atoms at the 2-position.
Claim 3
Dependent Claim
14 words
The peptide according to claim 1 wherein Z is ethylamino group or 2-fluoroethylamino group.
Claim 4
Dependent Claim
1 words
N-Acetyl-N-methylglycyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-alanyl-L-leucyl-L-arginyl-L-proline-ethylamide.
Claim 5
Dependent Claim
1 words
N-Acetyl-N-methylglycyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-alanyl-L-leucyl-L-arginyl-L-proline-ethylamide.
Claim 6
Dependent Claim
1 words
N-Acetyl-N-methylglycyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-alanyl-L-leucyl-L-arginyl-L-proline-2,2,2-trifluoroethylamide.
Claim 7
Dependent Claim
1 words
N-Acetyl-N-methylglycyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-alanyl-L-leucyl-L-arginyl-L-proline-2,2,2-trifluoroethylamide.
Claim 8
Dependent Claim
1 words
N-Acetyl-N-methylglycyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-norleucyl-L-leucyl-L-arginyl-L-prolineethylamide.
Claim 9
Dependent Claim
1 words
N-Acetyl-N-methylglycyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-norleucyl-L-leucyl-L-arginyl-L-prolineethylamide.
Claim 10
Dependent Claim
1 words
N-Acetyl-N-methylglycyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-norleucyl-L-leucyl-L-arginyl-L-proline-β-fluoroethylamide.
Claim 11
Dependent Claim
1 words
N-Acetyl-N-methylglycyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-norleucyl-L-leucyl-L-arginyl-L-proline-β-fluoroethylamide.
Claim 12
Dependent Claim
1 words
N-Acetyl-N-methylglycyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-norleucyl-L-leucyl-L-arginyl-L-proline-2,2,2-trifluoroethylamide.
Claim 13
Dependent Claim
1 words
N-Acetyl-N-methylglycyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-norleucyl-L-leucyl-L-arginyl-L-proline-2,2,2-trifluoroethylamide.
Claim 14
Dependent Claim
68 words
A process for preparing a peptide having the formula N-Acetyl-N-methylglycyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-Y-L-leucyl-L-arginyl-L-prolyl-Z wherein Y is D-αDα-alkylglycine residue of the formula ##STR4##in which n is an integer of 0 through 3 inclusive and Z is ethylamino group or an ethylamino group which is substituted with 1 to 3 fluorine atoms at the 2-position which comprises reacting L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-Y-L-leucyl-L-arginyl-L-prolyl-Z wherein Y and Z are as defined above with a reactive ester of N-acetyl-N-methylglycine.
Claim 15
Dependent Claim
68 words
A process for preparing a peptide having the formula N-Acetyl-N-methylglycyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-Y-L-leucyl-L-arginyl-L-prolyl-Z wherein Y is D-αDα-alkylglycine residue of the formula ##STR4##in which n is an integer of 0 through 3 inclusive and Z is ethylamino group or an ethylamino group which is substituted with 1 to 3 fluorine atoms at the 2-position which comprises reacting L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-Y-L-leucyl-L-arginyl-L-prolyl-Z wherein Y and Z are as defined above with a reactive ester of N-acetyl-N-methylglycine.
References Cited (Backward Citations)
US3855199A
Cited
US3886137A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-02-29 | 1980-08-30 | 1981-03-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-02-29 | 1984-08-30 | 1985-03-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-02-29 | 1988-08-30 | 1989-03-01 | $7700.00 | Window Closed / Lapsed |