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US 3,940,380 AGranted
P-Glu-D-Phe-Trp-Ser-Tyr-2-Me.Ala-Leu-Arg-Pro-NH.sub.2 and intermediates
AssigneeAmerican Home Products Corporation
InventorVictor M. Garsky
Life of this patent
Estimating the term…
Abstract
D-Phe.sup.2 -2-Me.Ala.sup. 6 -LRF, is described as well as its synthesis by solid phase techniques and novel intermediates formed by such synthesis. The novel decapeptide possess anti-ovulatory activity in mammals.
Claims8
A compound selected from the group consisting of
- L-p-Glu-D-Phe-L-Trp-L-Ser-L-Tyr-2-Me.sup.. Ala-L-Leu-L-Arg-L-Pro-Gly-NH.sub.2
- and
- R.sup.4 -L-p-Glu-D-Phe-L-Trp-L-Ser(R.sup.3)-L-Tyr(R.sup.2)-2-Me.sup.. Ala-L-Leu-L-Arg(N.sup.G -R.sup.1)-L-Pro-Gly-R
- and its non-toxic salts;
- wherein
- R is selected from the class consisting of NH.sub.2, OH, O-(lower)alkyl and O-benzyl;
- R.sup.1 is selected from the class consisting of hydrogen and a protecting group for the N.sup..delta., N.sup..omega. and N.sup..omega..sup.' nitrogen atoms of arginine selected from nitro, tosyl, benzyloxycarbonyl and adamantyloxycarbonyl;
- R.sup.2 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;
- R.sup.3 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;
- R.sup.4 is selected from the class consisting of hydrogen and an .alpha.-amino protecting group, with the proviso that at least one of R.sup.1, R.sup.2 and R.sup.3 is a protecting group.
7 more elements
A compound of the formula:
- R.sup.4 -L-p-Glu-D-Phe-L-Trp-L-Ser(R.sup.3)-L-Tyr(R.sup.2)-2-Me.sup.. Ala-L-Leu-L-Arg-(N.sup.G -R.sup.1)-L-Pro-Gly-A
- wherein:
- R.sup.1 is selected from the class consisting of hydrogen and a protecting group for the N.sup..delta., N.sup..omega. and N.sup..omega..sup.' nitrogen atoms of arginine selected from nitro, tosyl, benzyloxycarbonyl and adamantyloxycarbonyl;
- R.sup.2 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;
- R.sup.3 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;
- R.sup.4 is selected from the class consisting of hydrogen and an .alpha.-amino protecting group;
- and A is selected from the class consisting of ##EQU4## and ##EQU5## wherein said polystyrene resin is cross linked through the phenyl group on each second carbon atom of the alkyl chain of said polystyrene.
4 more elements
Dependencies are inferred from the claim text.