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US 5,684,018 AGranted
Acyloxyisopropyl carbamates as prodrugs for amine drugs
AssigneeMerck & Co., Inc.
InventorJose Alexander
Life of this patent
Estimating the term…
Abstract
This invention relates to novel acyloxyisopropyl carbamates as bioreversible prodrug moieties for amino drugs and to methods of synthesizng these compounds.
Claims12
A compound of the formula
- R.sub.2 R.sub.3 N(CO)-O-C(CH.sub.3).sub.2 -O-(CO)-R.sub.1 ;
- wherein
- R.sub.2 R.sub.3 N represents a primary or secondary amine pharmaceutical;
- and R.sup.2 and R.sup.3 are the same or different or may be combined to form a cyclic secondary amine;
- and
- R.sub.1 is C.sub.1-20 alkyl, C.sub.2-20 alkenyl, C.sub.2-20 alkynyl, aryl, C.sub.7-10 aralkyl, C.sub.3-8 cycloalkyl, C.sub.3-10 cycloalkenyl, C.sub.2-20 carboxylalkyl, carboxy C.sub.5-20 cycloalkyl, C.sub.2-20 haloalkyl, C.sub.1-5 alkoxycarbonyl C.sub.2-10 alkyl, C.sub.2-20 alkylsulfoxide, C.sub.2-20 carbamyl substituted alkyl or C.sub.2-20 carbamyl substituted aralkyl, and saturated or unsaturated mono- or polyheterocyclics having from 1 to 3 rings having one or more hetero atoms.
3 more elements
A compound of the formula:
- X-O-(CO)-O-C(CH.sub.3).sub.2 -O-(CO)-R.sub.1
- wherein
- X is phenyl substituted with one or more of the substituents selected from the group consisting of nitro, halo, cyano, C.sub.1-6 alkylsulfonyl, C.sub.1-6 alkylsulfenyl, trihalomethyl, trihalomethylthio, trihalomethylsulfonyl and trihalomethylsulfenyl or a radical selected from the group consisting of C.sub.1-5 polyhaloalkyl and C.sub.2-12 alkylsulfonylalkyl;
- and
- R.sub.1 is C.sub.1-20 alkyl, C.sub.2-20 alkenyl, C.sub.2-20 alkynyl, aryl, C.sub.7-10 aralkyl, C.sub.3-8 cycloalkyl, C.sub.3-10 cycloalkenyl, C.sub.2-20 carboxylalkyl, carboxy C.sub.5-20 cycloalkyl, C.sub.2-20 haloalkyl, C.sub.1-5 alkoxycarbonyl C.sub.2-10 alkyl, C.sub.2-20 alkylsulfoxide, C.sub.2-20 carbamyl substituted alkyl or C.sub.2-20 carbamyl substituted aralkyl, and saturated or unsaturated mono- or polyheterocyclics having from 1 to 3 rings having one or more hetero atoms.
2 more elements
Dependencies are inferred from the claim text.