Method for the total synthesis of cyclosporins, novel cyclosporins and novel intermediates and methods for their production
AssigneeSandoz Ltd.
InventorRoland Wenger
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Abstract
A method for the total synthesis of cyclosporins, in particular Cyclosporin A, cyclosporins produced in accordance with the method of the invention and novel intermediates, in particular novel [1S, 2R, 3R]- and [1R, 2S, 3S]-1-nitrilo-1-carbonyl-3-methyl-2-oxy-heptanes and -hept-5-enes, employed in the method of the invention.
Claims8
A compound of formula III
- wherein --x--y-- is --CH.sub.2 --CH.sub.2 -- or --CH.dbd.CH--,
- R.sub.1 is hydrogen or methyl,
- X.sub.1 is hydroxy or a carboxy protecting group suitable for peptide synthesis or a carboxy activating group suitable for peptide synthesis,
- X.sub.2 is hydrogen or an N-protecting group suitable for peptide synthesis, and
- X.sub.3 is hydrogen or an O-protecting group suitable for peptide synthesis or
- (X.sub.2 +X.sub.3) is a protecting group suitable for peptide synthesis bridging the 2-N and 3-O functions or
- (X.sub.2 +R.sub.1) is a divalent N-protecting group suitable for peptide synthesis,
- and wherein the positions 2, 3 and 4 have the configuration S,R and R or R,S and S respectively.
A compound according to claim 1 of formula III ##STR43## wherein --x--y--, R.sub.1, X.sub.1, X.sub.2, and X.sub.3 are as defined in claim 25, with the proviso that at least one of X.sub.1, X.sub.2, X.sub.3, X.sub.2 +X.sub.3 or X.sub.2 +R.sub.1 is a protecting group suitable for peptide synthesis.
A compound according to claim 1, wherein R.sub.1 and --x--y-- have the meanings given in claim 8, with the proviso that, when R.sub.1 is methyl and --x--y-- is --CH.sub.2 --CH.sub.2 -- or --CH.dbd.CH--, the positions 2, 3 and 4 have the configuration R,S and S respectively.
Dependencies are inferred from the claim text.