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US 9,315,514 B2Granted
1,3-dioxanomorphides and 1,3-dioxanocodides
AssigneeRhodes Technologies
InventorHelge A. Reisch
Life of this patent
Estimating the term…
Abstract
The application is directed to compounds of Formula I and pharmaceutically acceptable salts, prodrugs, and solvates thereof, wherein G, R2-R5, and are defined as set forth in the specification. The invention is also directed to use of compounds of Formula I as synthetic intermediates or to treat disorders responsive to the modulation of one or more opiopid receptors. Certain compounds of the present invention are especially useful for treating pain.
Claims41
A compound of Formula I:
- or a pharmaceutically acceptable salt thereof, wherein:
- G is R1 or a hydroxyl protecting group PG;
- R1 is hydrogen, C1-6 alkyl, C2-4 alkenyl, C2-4 alkynyl, C3-6 cycloalkyl(C1-4)alkyl, or C6-10 aryl (C1-4)alkyl, wherein the C3-6 cycloalkyl, and C6-10 aryl, portions thereof are optionally substituted with 1, 2, or 3 substituents, each independently selected from the group consisting of hydroxy, halo, halo(C1-4)alkyl, amino, C1-4 alkylamino, di(C1-4)alkylamino, carboxy, and C1-4 alkoxycarbonyl;
- PG is selected from the group consisting of methyl, tert-butyl, benzyl, benzovl, acetyl, trimethyl silyl, tert-butyldimethyl silyl, tert-butyldiphenyl silyl, and tri-isopropyl silyl;
- R2 is
- (a) hydrogen;
- or
- (b) C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-7 cycloalkyl(C1-4)alkyl, C3-7 cycloalkenyl(C1-4)alkyl, or C6-10 aryl(C1-4)alkyl, any of which is optionally substituted with 1, 2, or 3 substituents, each independently selected from the group consisting of hydroxy, halo, halo(C1-4)alkyl, amino, C1-4 alkylamino, di(C1-4)alkylamino, carboxy, and C1-4 alkoxycarbonyl;
- R3 and R4 are each independently selected from the group consisting of hydrogen, C1-6 alkyl, C2-6 alkenyl, and C2-6 alkynyl, wherein any of which, when other than hydrogen, is optionally substituted with 1, 2, or 3 substituents, each independently selected from the group consisting of hydroxy, halo, halo(C1-4)alkyl, amino, C1-4 alkylamino, di(C1-4)alkylamino, carboxy, and C1-4 alkoxycarbonyl;
- R5 is selected from the group consisting of hydrogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-7 cycloalkyl, C3-7 cycloalkenyl, phenyl, and naphthyl wherein any of which, when other than hydrogen, is optionally substituted with 1, 2, or 3 substituents, each independently selected from the group consisting of hydroxy, halo, halo(C1-4)alkyl, amino, C1-4 alkylamino, di(C1-4)alkylamino, carboxy, and C1-4alkoxycarbonyl;
- and
- is a single bond or a double bond.
9 more elements
Dependencies are inferred from the claim text.