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US 3,941,763 AGranted
PGlu-D-Met-Trp-Ser-Tyr-D-Ala-Leu-Arg-Pro-Gly-NH.sub.2 and intermediates
AssigneeAmerican Home Products Corporation
InventorDimitrios Sarantakis
Life of this patent
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Abstract
The synthesis of the decapeptide pGlu-D-Met-Trp-Ser-Tyr-D-Ala-Leu-Arg-Pro-Gly-NH.sub.2 by solid-phase techniques is described. The decapeptide inhibits LH release.
Claims8
A compound selected from the group consisting of
- L--P--Glu--D--Met--L--Trp--L--Ser--L--Tyr--D--Ala--L--Leu--L--Arg--L--Pro-- Gly--NH.sub.2
- and
- R.sup.4 --L--p--Glu--D--Met--L--Trp--L--Ser(R.sup.3)-- L--Tyr--(R.sup.2)-- D--Ala--L--Leu--L--Arg(N.sup.G --R.sup.1)--L--Pro--Gly--R
- or a non-toxic salt thereof;
- 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, tertbutyl, 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.
8 more elements
A compound of the formula:
- R.sup.4 --L--p--Glu--D--Met--L--Trp--L--Ser(R.sup.3)--L--Tyr(R.sup.2)-- D--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 slected from the class consisting of hydrogen and an .alpha.-amino protecting group;
- and A is selected from the class consisting of ##EQU3## 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.