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US3929759A Expired / Lapsed US ⏱️ 0.0 years remaining

P-Glu-D-Phe-Trp-Ser-Tyr-D-Arg-Leu-Arg-Pro-Gly-NH{HD 2 {B and intermediates

Assignee: Wyeth LLC
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Filing: 1974-11-04
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Granted: 1975-12-30
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Expires: 1994-11-04
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Abstract

Abstract D-Phe2-D-Arg6-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

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-27 06:07
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 155 words
A COMPOUND SELECTED FROM THE GROUP COMSISTING OF L-P-GLU-D-PHE-L-TRP-L-SER-L-TYR-D-ARG-L-LEU-L-ARG-LPRO-GLY-NH2 AND R4-P-GLU-D-PHE-L-TRP-L-SER(R3)-L-TYR(R2)-D-ARG(NGR5)-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 AND R5 ARE SELECTED FROM THE CLASS CONSISTING 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 FORM 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, R3 AND R5 IS A PROTECTING GROUP.
Claim 2
Dependent Claim 155 words
A COMPOUND SELECTED FROM THE GROUP COMSISTING OF L-P-GLU-D-PHE-L-TRP-L-SER-L-TYR-D-ARG-L-LEU-L-ARG-LPRO-GLY-NH2 AND R4-P-GLU-D-PHE-L-TRP-L-SER(R3)-L-TYR(R2)-D-ARG(NGR5)-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 AND R5 ARE SELECTED FROM THE CLASS CONSISTING 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 FORM 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, R3 AND R5 IS A PROTECTING GROUP.
Claim 3
Dependent Claim 10 words
A compound according to claim 1 wherein R is NH2.
Claim 4
Dependent Claim 25 words
A compound according to claim 1 whereIn R is NH2, R1 and R5 are nitro, 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-arginyl-L -leucyl-L-arginyl-L-prolylglycinamide and its non-toxic acid addition salts.
Claim 6
Dependent Claim 128 words
A compound of the formula: R4-L-p-Glu-D-Phe-L-Trp-L-Ser(R3)-L-Tyr(R2)-D-Arg(NG-R5)-L-Leu-L-Arg(NG-R1)-L-Pro-Gly-A wherein: R1 and R5 are 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 128 words
A compound of the formula: R4-L-p-Glu-D-Phe-L-Trp-L-Ser(R3)-L-Tyr(R2)-D-Arg(NG-R5)-L-Leu-L-Arg(NG-R1)-L-Pro-Gly-A wherein: R1 and R5 are 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 19 words
A compound according to claim 7 wherein R1 and R5 are nitro, 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) 1978-12-29 1979-06-30 1979-12-30 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1982-12-29 1983-06-30 1983-12-30 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1986-12-29 1987-06-30 1987-12-30 $7700.00 Window Closed / Lapsed

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