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US 4,785,085 AGranted
Rebeccamycin analogs
AssigneeBristol-Myers Company
InventorsTakushi Kaneko, Henry S. Wong, Jacob J. Utzig
Life of this patent
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Abstract
There are disclosed analogs of the antitumor agent, rebeccamycin, which possess antineoplastic properties against mammalian, particularly experimental animal, tumor systems. The compounds of the invention are aminoalkylated derivatives of rebeccamycin produced by first reacting rebeccamycin with a strong base to obtain a reactive intermediate and then reacting the reactive intermediate with an aminoalkyl compound.
Claims11
A compound having the formula ##STR6## wherein:
- n is an integer from 1 to 6;
- A.sup.6 and A.sup.13 are selected from H and --(CH.sub.2).sub.n NR.sup.1 R.sup.2 and at least one of A.sup.6 and A.sup.13 is --(CH.sub.2).sub.n --NR.sup.1 R.sup.2 ;
- R.sup.1 and R.sup.2, independently, are selected from hydrogen, unsubstituted and substituted C.sub.1 -C.sub.6 alkyl, aralkyl having 1 to 3 carbons in the alkyl moiety and unsubstituted phenyl or phenyl substituted with 1 to 3 alkyl, alkoxy, hydroxy, halo, carboxyl, alkoxycarbonyl, and amino and mono- and di-lower-alkylamino groups in the aryl moiety, and aryl selected from unsubstituted phenyl and phenyl substituted with 1 to 3 alkyl, alkoxy, hydroxy, halo, amino, mono- and dialkylamino, nitro, carboxyl, alkoxycarbonyl, and cyano groups provided that both R.sup.1 and R.sup.2 are not each aryl and, when taken together, R.sup.1 and R.sup.2 may be selected from --(CH.sub.2).sub.4 -- and (CH.sub.2).sub.2 --R.sup.3 --(CH.sub.2).sub.2 -- to form a 5- or 6-membered ring together with the N-atom wherein R.sup.3 is selected from CH.sub.2, NH, O and S;
- X is selected from H, F, Cl, Br, C.sub.1 -C.sub.3 alkyl, OH, carboxyl, alkoxycarbonyl and alkoxy wherein the alkyl moiety is C.sub.1 -C.sub.3 alkyl, benzyloxy, amino, and mono- and dialkylamino;
- and
- R.sup.4 is selected from H and CH.sub.3 ;
- and pharmaceutically acceptable acid addition and base salts thereof.
4 more elements
A compound having the formula ##STR8## wherein:
- n is an integer from 1 to 6;
- R.sup.1 and R.sup.2, independently, are selected from hydrogen, unsubstituted and substituted C.sub.1 -C.sub.6 alkyl, aralkyl having 1 to 3 carbons in the alkyl moiety and unsubstituted phenyl or phenyl substituted with 1 to 3 alkyl, alkoxy, hydroxy, halo, carboxyl, alkoxycarbonyl, and amino and mono- and di-lower-alkylamino groups in the aryl moiety, and aryl selected from unsubstituted phenyl and phenyl substituted with 1 to 3 alkyl, alkoxy, hydroxy, halo, amino, mono- and dialkylamino, nitro, carboxyl, alkoxycarbonyl, and cyano groups provided that both R.sup.1 and R.sup.2 are not each aryl and, when taken together, R.sup.1 and R.sup.2 may be selected from --(CH.sub.2).sub.4 -- and --(CH.sub.2).sub.2 --R.sup.3 --(CH.sub.2).sub.2 -- to form a 5- or 6-membered ring together the N-atom wherein R.sup.3 L is selected from CH.sub.2, NH, O and S;
- X is selected from H, F, Cl, Br, C.sub.1 -C.sub.3 alkyl, OH, carboxyl, alkoxycarbonyl and alkoxy wherein the alkyl moiety is C.sub.1 -C.sub.3 alkyl, benzyloxy, amino, and mono- and dialkylamino;
- and
- R.sup.4 is selected from H and CH.sub.3 ;
- and pharmaceutically acceptable acid addition and base salts thereof.
3 more elements
Dependencies are inferred from the claim text.