Back to results
US 5,550,149 AGranted
MDR reversal agents
AssigneeAmerican Cyanamid Company
InventorsDennis Powell, Rolf Paul, William A. Hallett, Dan M. Berger, Minu D. Dutia
Life of this patent
Estimating the term…
Abstract
Compounds of the general formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are herein described, A is a straight or branched (C.sub.2 -C.sub.12)alkyl or a phenyl moiety and B is a moiety of the formula: ##STR2## The compounds are effective in potentiating the activity of chemotherapeutic anti-cancer agents by increasing the sensitivity of multi-drug resistant cells to such chemotherapeutic agents.
Claims13
A compound of the formula:
- ##STR41## wherein R.sup.2 is H, OH, O-alkyl(C.sub.1 -C.sub.4), F, Br, Cl, I, NO.sub.2, OCF.sub.3, alkyl(C.sub.1 -C.sub.6), or N(R.sup.12).sub.2 ;
- R.sup.3 is H, OH, O-alkyl(C.sub.1 -C.sub.3), straight or branched OSi--(C.sub.1 -C.sub.4)alkyl, F, Br, Cl, I, NO.sub.2, alkyl(C.sub.1 -C.sub.6), OCH.sub.2 CH.sub.2 Cl, O-alkyl(C.sub.2 -C.sub.5)-heterocycle, O-alkyl(C.sub.2 -C.sub.5)N(R.sup.12).sub.2, OSO.sub.2 CF.sub.3, OCF.sub.3, or N(R.sup.12).sub.2 ;
- or R.sup.2 and R.sup.3 taken together are methylenedioxy or ethylenedioxy;
- R.sup.4 is H, OH, O-alkyl(C.sub.1 -C.sub.4), F, Br, Cl, I, or alkyl(C.sub.1 -C.sub.3);
- R.sup.5 is H, CN, CH.sub.2 OH, CO.sub.2 (C.sub.1 -C.sub.3)alkyl, CH.sub.2 NH.sub.2, CH.sub.2 N(R.sup.12).sub.2 or alkyl(C.sub.1 -C.sub.3);
- R.sup.1 is straight or branched (C.sub.1 -C.sub.12) alkyl, cycloalkyl (C.sub.3 -C.sub.7), bicycloalkyl(C.sub.6 -C.sub.10), tricycloalkyl(C.sub.6 -C.sub.10), a heterocycle or a moiety of the formula:
- ##STR42## wherein m is an integer 0-3,
- X is H, straight or branched (C.sub.1 -C.sub.4)alkyl, I, Cl, Br, F, NO.sub.2, or N(R.sup.12).sub.2 ;
- A is straight or branched (C.sub.2 -C.sub.12)alkyl, or a moiety selected from these of the formulae:
- ##STR43## B is a moiety of the formula:
- ##STR44## n and p are integers with n=1 and p=0;
- R.sup.6 is H, alkyl(C.sub.1 -C.sub.4), or a moiety of the formula:
- ##STR45## s is an integer with s=1-3, R.sup.7 and R.sup.8 are independently H, alkyl(C.sub.1 -C.sub.4), or O-alkyl(C.sub.1 -C.sub.4);
- R.sup.9 is H, O-alkyl(C.sub.1 -C.sub.4), F, Br, Cl, I, or alkyl(C.sub.1 -C.sub.3);
- R.sup.10 is H, O-alkyl(C.sub.1 -C.sub.3), OH, F, Br, Cl, I, alkyl(C.sub.1 -C.sub.3), OCH.sub.2 CH.sub.2 Cl, O-alkyl(C.sub.2 -C.sub.5)-heterocycle, S-alkyl(C.sub.1 -C.sub.4), OSO.sub.2 CF.sub.3, OCF.sub.3, OCH.sub.2 -phenyl, NO.sub.2 or N(R.sup.12).sub.2 ;
- R.sup.11 is H, O-alkyl(C.sub.1 -C.sub.4), S-alkyl(C.sub.1 -C.sub.4), OH, F, Br, Cl, I, OCF.sub.3, OCH.sub.2 phenyl, alkyl(C.sub.1 -C.sub.3) or O-aklyl (C.sub.2 -C.sub.5)-heterocycle;
- R.sup.12 is alkyl(C.sub.1 -C.sub.4);
- heterocycle is imidazole, pyrrole, 1,2,4-triazole, oxazole, isoxazole, furan, thiophene, pyridine, pyrimidine, or thiazole;
- or a pharmaceutically acceptable salt thereof.
16 more elements
Dependencies are inferred from the claim text.