Patent US3928307A successfully refreshed from Google Patents.
US3928307A
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P-Glu-D-Phe-Trp-Ser-Tyr-D-Phee-Leu-Arg-Pro-Gly-NH2 and intermediates
Assignee: Wyeth LLC
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Filing: 1974-11-04
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Granted: 1975-12-23
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Expires: 1994-11-04
Abstract
Abstract D-Phe2-D-Phe6-LRF, is described as well as its synthesis by solid phase techniques and novel intermediates formed by such synthesis. The novel decapeptide exhibits anti-ovulatory activity in mammals.
Inventors
- 👤 Theodore J Foell
- 👤 John P Yardley
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 14:21
CPC Classifications
C; C07; C07K; C07K7/00; C07K7/04; C07K7/23; A; A61; A61K; A61K38/00; Y; Y10; Y10S; Y10S930/00; Y10S930/01; Y10S930/13; Y10S930/28
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
153 words
A COMPOUND SELECTED FROM THE GROUP CONSISTING OF L-PGLU-D-PHE-L-TRP-L-SER-L-TYR-D-PHE-L-LEU-L-LEU-L-ARGL-PRO-GLY-NH2 AND R4-L-P-GLU-D-PHE-L-TRP-L-SER(R3)-LTYR(R2)-D-PHE-L-LEU-L-ARG-(NG-R1)-L-PRO -GLY-R AND ITS NON-TOXIC SALTS: WHEREIN R IS SELECTED FROM THE CLASS CONSISTING OF NH2, OH, O-(LOWER)ALKYL AND O-BENZYL; R1 IS SELECTED FROM THE CLASS CONSISTING OF HYDROGEN AND A PROTECTING GROUP FOR THE NB, NW AND NW'' NITROGEN ATOMS OF ARGININE SELECTED FROM NITRO, TOSYL, BENZYLOXYCARBONYL AND ADAMANTYLOXYCARBONYL; R2 IS SELECTED FROM THE CLASS CONSISTING OF HYDROGEN AND A PROTECTING GROUP FOR THE PHENOLIC HYDROXYL GROUP OF TYROSINE SELECTED FROM TERT-BUTYL, TETRAHYDROPYRANYL, TRITYL, BENZYL, 2,6-DICHLOROBENZYL, BENZYLOXYCARBONYL AND 4BROMOBENZYLOXYCARBONYL; R3 IS SELECTED FROM THE CLASS CONSISTING OF HYDROGEN AND A PROTECTING GROUP FOR THE ALCOHOLIC HYDROXYL GROUP OF SERINE AND IS SELECTED FROM ACETYL, BENZOYL, TETRAHYDROPYRANYL, TERT-BUTYL, TRITYL, 2,6-DICHLOROBENZYL, BENZYL AND BENZYLOXYCARBONYL; R4 IS SELECTED FROM THE CLASS CONSISTING OF HYDROGEN AND AN A-AMINO PROTECTING GROUP, WITH THE PROVISO THAT AT LEAST ONE OF R1, R2 AND R3 IS A PROTECTING GROUP.
Claim 2
Dependent Claim
153 words
A COMPOUND SELECTED FROM THE GROUP CONSISTING OF L-PGLU-D-PHE-L-TRP-L-SER-L-TYR-D-PHE-L-LEU-L-LEU-L-ARGL-PRO-GLY-NH2 AND R4-L-P-GLU-D-PHE-L-TRP-L-SER(R3)-LTYR(R2)-D-PHE-L-LEU-L-ARG-(NG-R1)-L-PRO -GLY-R AND ITS NON-TOXIC SALTS: WHEREIN R IS SELECTED FROM THE CLASS CONSISTING OF NH2, OH, O-(LOWER)ALKYL AND O-BENZYL; R1 IS SELECTED FROM THE CLASS CONSISTING OF HYDROGEN AND A PROTECTING GROUP FOR THE NB, NW AND NW'' NITROGEN ATOMS OF ARGININE SELECTED FROM NITRO, TOSYL, BENZYLOXYCARBONYL AND ADAMANTYLOXYCARBONYL; R2 IS SELECTED FROM THE CLASS CONSISTING OF HYDROGEN AND A PROTECTING GROUP FOR THE PHENOLIC HYDROXYL GROUP OF TYROSINE SELECTED FROM TERT-BUTYL, TETRAHYDROPYRANYL, TRITYL, BENZYL, 2,6-DICHLOROBENZYL, BENZYLOXYCARBONYL AND 4BROMOBENZYLOXYCARBONYL; R3 IS SELECTED FROM THE CLASS CONSISTING OF HYDROGEN AND A PROTECTING GROUP FOR THE ALCOHOLIC HYDROXYL GROUP OF SERINE AND IS SELECTED FROM ACETYL, BENZOYL, TETRAHYDROPYRANYL, TERT-BUTYL, TRITYL, 2,6-DICHLOROBENZYL, BENZYL AND BENZYLOXYCARBONYL; R4 IS SELECTED FROM THE CLASS CONSISTING OF HYDROGEN AND AN A-AMINO PROTECTING GROUP, WITH THE PROVISO THAT AT LEAST ONE OF R1, R2 AND R3 IS A PROTECTING GROUP.
Claim 3
Dependent Claim
10 words
A compound according to claim 1 wherein R in NH2.
Claim 4
Dependent Claim
23 words
A compound according to claim 1 wherein R is NH2, R1 is tosyl, R2 is 2,6-dichlorobenzyl, R3 is benzyl and R4 is hydrogen.
Claim 5
Dependent Claim
18 words
A compound according to claim 1 which is selected from: L-Pyroglutamyl-D-phenylalanyl-L-tryptophyl-L-seryl-L-tyrosyl-D-phenylalanyl -L-leucyl-L-arginyl-L-prolylglycinamide and its non-toxic acid addition salts.
Claim 6
Dependent Claim
127 words
A compound of the formula: R4-L-p-Glu-D-Phe-L-Trp-L-Ser(R3)-L-Tyr(R2)-D-Phe-L-Leu-L-Arg-(NG-R1)-L-Pro -Gly-A wherein: R1 is selected from the class consisting of hydrogen and a protecting group for the N , N and N nitrogen atoms of arginine selected from nitro, tosyl, benzyloxycarbonyl and adamantyloxycarbonyl; R2 is selected from the class consisting of hydrogen and a protecting group for the phenolic hydroxyl group of tyrosine selected from tert-butyl, tetrahydropyranyl, trityl, benzyl, 2, 6-dichlorobenzyl, benzyloxycarbonyl and 4-bromobenzyloxycarbonyl; R3 is selected from the class consisting of hydrogen and a protecting group for the alcoholic hydroxyl group of serine and is selected from acetyl, benzoyl, tetrahydropyranyl, tert-butyl, trityl, 2,6-dichlorobenzyl, benzyl and benzyloxycarbonyl; R4 is selected from the class consisting of hydrogen and an Alpha -amino protecting group; and A is selected from the class consisting of
Claim 7
Dependent Claim
127 words
A compound of the formula: R4-L-p-Glu-D-Phe-L-Trp-L-Ser(R3)-L-Tyr(R2)-D-Phe-L-Leu-L-Arg-(NG-R1)-L-Pro -Gly-A wherein: R1 is selected from the class consisting of hydrogen and a protecting group for the N , N and N nitrogen atoms of arginine selected from nitro, tosyl, benzyloxycarbonyl and adamantyloxycarbonyl; R2 is selected from the class consisting of hydrogen and a protecting group for the phenolic hydroxyl group of tyrosine selected from tert-butyl, tetrahydropyranyl, trityl, benzyl, 2, 6-dichlorobenzyl, benzyloxycarbonyl and 4-bromobenzyloxycarbonyl; R3 is selected from the class consisting of hydrogen and a protecting group for the alcoholic hydroxyl group of serine and is selected from acetyl, benzoyl, tetrahydropyranyl, tert-butyl, trityl, 2,6-dichlorobenzyl, benzyl and benzyloxycarbonyl; R4 is selected from the class consisting of hydrogen and an Alpha -amino protecting group; and A is selected from the class consisting of
Claim 8
Dependent Claim
27 words
A compound according to claim 5 wherein R4 is an Alpha -amino protecting group which is selected from the class consisting of tert-butyloxycarbonyl, cyclopentyloxycarbonyl, tert-amyloxycarbonyl and isobornyloxycarbonyl.
Claim 9
Dependent Claim
16 words
A compound according to claim 5 wherein A is a benzhydrilamine resin and R4 is hydrogen.
Claim 10
Dependent Claim
18 words
A compound according to claim 7 wherein R1 is tosyl, R2 is 2, 6-dichlorobenzyl and R3 is benzyl.
References Cited (Backward Citations)
US3855199A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1978-12-22 | 1979-06-23 | 1979-12-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-12-22 | 1983-06-23 | 1983-12-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-12-22 | 1987-06-23 | 1987-12-23 | $7700.00 | Window Closed / Lapsed |