Activated macrolactams
AssigneeAbbott Laboratories
InventorsYat S. Or, Jay R. Luly
Life of this patent
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Abstract
Activated macrolactam compounds having the formula ##STR1## wherein n is zero or one, R.sup.101 is selected from the group consisting of methyl, ethyl, allyl, propyl and cyclopropylmethyl; R.sup.102 is hydrogen, and R.sup.103 is selected from the group consisting of hydrogen, hydroxy and a protected hydroxy group or, taken together, R.sup.102 and R.sup.103 form a bond; R.sup.104 and R.sup.105 are chosen such that one is hydrogen while the other is -OS(O).sub.2 F; and R.sup.106 is selected from the group consisting of hydrogen, a protected hydroxy group, loweralkyl, alkenyl, cycloalkyl, aryl and arylalkyl, as well as processes for making such compounds and methods for their use in the preparation of C-32-modified derivatives of ascomycin or the congeners or analogs thereof.
Claims5
A compound having the formula ##STR4## wherein n is zero or one, R.sup.101 is selected from the group consisting of methyl, ethyl, allyl, propyl and cyclopropylmethyl;
- R.sup.102 is hydrogen, and R.sup.103 is selected from the group consisting of hydrogen, hydroxy and a protected hydroxy group or, taken together. R.sup.102 and R.sup.103 form a bond, wherein a protected hydroxy group is a hydroxy group which is protected by a protecting group selected from tris(C.sub.1 -C.sub.12 -loweralkyl)silyl,
- (di(aryl))(C.sub.1 -C.sub.12 -loweralkyl)silyl, tri(aryl)silyl, tri(aryl-C.sub.1 -C.sub.12 -alkyl)silyl,
- C.sub.1 -C.sub.12 -alkyl-C(O)-, aryl -C(O)-, C.sub.1 -C.sub.12 -alkyl-OC(O)-,
- -S(O).sub.2 -(C.sub.1 -C.sub.12 -loweralkyl) and -S(O).sub.2 -(aryl);
- R.sup.104 and R.sup.105 are chosen such that one is hydrogen while the other is -OS(O).sub.2 F;
- and
- R.sup.106 is selected from the group consisting of hydrogen,
- C.sub.1 -C.sub.12 -loweralkyl, C.sub.2 -C.sub.12 -alkenyl, C.sub.3 -C.sub.8 -cycloalkyl, aryl, aryl-C.sub.1 -C.sub.12 -alkyl and a hydroxy protecting group selected from tris(C.sub.1 -C.sub.12 -loweralkyl)silyl,
- (di(aryl))C.sub.1 -C.sub.12 -loweralkyl)silyl, tri(aryl)silyl, tri(aryl-C.sub.1 -C.sub.12 -alkylsilyl,
- C.sub.1 -C.sub.12 -alkyl-C(O)-, aryl -C(O)-, C.sub.1 -C.sub.12 -alkyl-OC(O)-,
- -S(O).sub.2 -(C.sub.1 -C.sub.12 -loweralkyl) and -S(O).sub.2 -(aryl;
- wherein at each occurrence aryl is independently selected from phenyl, 1-naphthyl, 2-naphthyl, fluorenyl, 1,2-dihydronaphthyl, 1,2,3,4-tetrahydronaphthyl, indanyl and indenyl and the aryl group can be unsubstituted or substituted with one, two or three substitutents independently selected from C.sub.1 -C.sub.12 -loweralkyl and halogen.
A compound of the formula ##STR5## wherein n is 0 or 1 and (a) R.sup.101 is ethyl, R.sup.102 is hydrogen, R.sup.103 is hydroxy, R.sup.104 is fluorosulfonyl, R.sup.105 is hydrogen and R.sup.106 is methyl;
- (b) R.sup.101 is allyl, R.sup.102 is hydrogen, R.sup.103 is hydroxy, R.sup.104 is fluorosulfonyl, R.sup.105 is hydrogen and R.sup.106 is methyl;
- (c) R.sup.101 is ethyl, R.sup.102 is hydrogen, R.sup.103 is tert-butyldimethylsilyloxy, R.sup.104 is fluorosulfonyl, R.sup.105 is hydrogen and R.sup.106 is methyl;
- (d) R.sup.101 is ethyl, R.sup.102 is hydrogen, R.sup.103 is triisopropylsilyloxy, R.sup.104 is fluorosulfonyl, R.sup.105 is hydrogen and R.sup.106 is methyl;
- (e) R.sup.101 is ethyl, R.sup.102 is hydrogen, R.sup.103 is hydrogen, R.sup.104 is fluorosulfonyl, R.sup.105 is hydrogen and R.sup.106 is methyl;
- (f) R.sup.101 is ethyl, R.sup.102 and R.sup.103 taken together form a bond, R.sup.104 is fluorosulfonyl, R.sup.105 is hydrogen and R.sup.106 is methyl;
- or
- (g) R.sup.101 is ethyl, R.sup.102 is hydrogen, R.sup.103 is hydroxy, R.sup.104 is hydrogen, R.sup.105 is fluorosulfonyl and R.sup.106 is methyl.
Dependencies are inferred from the claim text.