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US 6,294,566 B1Granted
Imidazoline derivatives and uses thereof
AssigneeSynaptic Pharmaceutical Corporation
InventorsWai C. Wong, Yoon T. Jeon, Charles Gluchowski
Life of this patent
Estimating the term…
Abstract
This invention is directed to novel imidazole and imidazoline derivatives which are selective agonists for cloned human α2 adrenergic receptors. This invention is also related to the use of these compounds for the treatment of any disease where modulation of the α2 receptors may be useful. The invention further provides for a pharmaceutical composition comprising a therapeutically effective amount of the above-defined compounds and a pharmaceutically acceptable carrier.
Claims18
A compound having the structure:
- wherein X is CR7;
- wherein Y is CO or CR3R5;
- wherein each R2 is independently H;
- F;
- Cl;
- Br;
- I;
- —NO2;
- —CN;
- straight chained or branched C1-C4 alkyl, C1-C4 monofluoroalkyl, or C1-C4 polyfluoroalkyl;
- straight chained or branched C1-C4 alkoxy;
- —OH;
- —(CH2)qOH;
- —COR4;
- CO2R4;
- CONHR4;
- phenyl;
- or benzyl;
- wherein each R3 is independently H;
- straight chained or branched C1-C4 alkyl, C1-C4 monofluoroalkyl, C1-C4 polyfluoroalkyl;
- straight chained or branched C1-C4 alkoxy;
- —(CH2)qOH;
- —OH;
- ═N—OR4;
- —COR4;
- —CO2R4;
- —CONHR4;
- phenyl;
- or benzyl;
- wherein each R4 is independently H;
- straight chained or branched C1-C4 alkyl, C1-C4 monofluoroalkyl, or C1-C4 polyfluoroalkyl;
- or phenyl;
- wherein each R5 is independently H;
- straight chained or branched C1-C4 alkyl, C1-C4 monofluoroalkyl, or C1-C4 polyfluoroalkyl;
- wherein each R7 is independently H;
- —CN;
- straight chained or branched C1-C4 alkyl, C1-C4 monofluoroalkyl, or C1-C4 polyfluoroalkyl;
- straight chained or branched C1-C4 alkoxy;
- —OH;
- —(CH2)qOH;
- —COR4;
- —CO2R4;
- —CONHR4;
- phenyl;
- or benzyl;
- wherein m and n are each independently 0, 1, 2 or 3, provided that m+n is 2 or 3;
- wherein each p is independently 0, 1 or 2;
- wherein each q is independently 0, 1, 2 or 3;
- and
- wherein the compound is the (+) enantiomer;
- or a pharmaceutically acceptable salt thereof.
48 more elements
A compound having the structure:
- wherein X is CR7;
- wherein Y is CO or CR3R5;
- wherein each R2 is independently H;
- F;
- Cl;
- Br;
- I;
- —NO2;
- —CN;
- straight chained or branched C1-C4 alkyl, C1-C4 monofluoroalkyl, or C1-C4 polyfluoroalkyl;
- straight chained or branched C114 C4 alkoxy;
- —OH;
- —(CH2)qOH;
- —COR4;
- —CO2R4;
- CONHR4;
- phenyl;
- or benzyl;
- wherein each R3 is independently H;
- straight chained or branched C1-C4 alkyl, C1-C4 monofluoroalkyl, or C1-C4 polyfluoroalkyl;
- straight chained or branched C1-C4 alkoxy;
- —(CH2)qOH;
- —OH;
- ═N—OR4;
- —COR4;
- —CO2R4;
- —CONHR4;
- phenyl;
- or benzyl;
- wherein each R4 is independently H;
- straight chained or branched C1-C4 alkyl, C1-C4 monofluoroalkyl, or C1-C4 polyfluoroalkyl;
- or phenyl;
- wherein each R5 is independently H;
- straight chained or branched C1-C4 alkyl, C1-C4 monofluoroalkyl, or C1-C4 polyfluoroalkyl;
- wherein each R7 is independently H;
- —CN;
- straight chained or branched C1-C4 alkyl, C1-C4 monofluoroalkyl, or C1-C4 polyfluoroalkyl;
- straight chained or branched C1-C4 alkoxy;
- —OH;
- —(CH2)qOH;
- —COR4;
- —CO2R4;
- —CONHR4;
- phenyl;
- or benzyl;
- wherein m and n are each independently 0, 1, 2 or 3, provided that m+n is 2 or 3;
- wherein each p is independently 0, 1 or 2;
- wherein each q is independently 0, 1, 2 or 3;
- and
- wherein the compound is the (−) enantiomer;
- or a pharmaceutically acceptable salt thereof.
48 more elements
A compound having the structure:
- wherein X is CR7;
- wherein Y is CO or CR3R5;
- wherein each R2 is independently H;
- F;
- Cl;
- Br;
- I;
- —NO2;
- —CN;
- straight chained or branched C1-C4 alkyl, C1-C4 monofluoroalkyl, or C1-C4 polyfluoroalkyl;
- straight chained or branched C1-C4 alkoxy;
- —OH;
- —(CH2)qOH;
- —COR4;
- —CO2R4;
- —CONHR4;
- phenyl;
- or benzyl;
- wherein each R3 is independently H;
- straight chained or branched C1-C4 alkyl, C1-C4 monofluoroalkyl, or C1-C4 polyfluoroalkyl;
- straight chained or branched C1-C4 alkoxy;
- —(CH2)qOH;
- —OH;
- ═N—OR4;
- —COR4;
- —CO2R4;
- —CONHR4;
- phenyl;
- or benzyl;
- wherein each R4 is independently H;
- straight chained or branched C1-C4 alkyl, C1-C4 monofluoroalkyl, or C1-C4 polyfluoroalkyl;
- or phenyl;
- wherein each R5 is independently H;
- straight chained or branched C1-C4 alkyl, C1-C4 monofluoroalkyl, or C1-C4 polyfluoroalkyl;
- wherein each R7 is independently H;
- —CN;
- straight chained or branched C1-C4 alkyl, C1-C4 monofluoroalkyl, or C1-C4 polyfluoroalkyl;
- straight chained or branched C1-C4 alkoxy;
- —OH;
- —(CH2)qOH;
- —COR4;
- —CO2R4;
- —CONHR4;
- phenyl;
- or benzyl;
- wherein m and n are each independently 0, 1, 2 or 3, provided that m+n is 2 or 3;
- wherein each p is independently 0, 1 or 2;
- and
- wherein each q is independently 0, 1, 2 or 3;
- with the proviso that when Y is CR3R5 at least one R2 is not H;
- or a pharmaceutically acceptable salt thereof.
48 more elements
A compound having the structure:
- wherein X is CR7;
- wherein Y is CO or CR3R5;
- wherein each R2 is independently H;
- F;
- Cl;
- Br;
- I;
- —NO2;
- —CN;
- straight chained or branched C1-C4 alkyl, C1-C4 monofluoroalkyl, or C1-C4 polyfluoroalkyl;
- straight chained or branched C1-C4 alkoxy;
- —OH;
- —(CH2)qOH;
- —COR4;
- —CO2R4;
- —CONHR4;
- phenyl;
- or benzyl;
- wherein each R3 is independently H;
- straight chained or branched C1-C4 alkyl, C1-C4 monofluoroalkyl, or C1-C4 polyfluoroalkyl;
- straight chained or branched C1-C4 alkoxy;
- —(CH2)qOH;
- —OH;
- ═N—OR4;
- —COR4;
- —CO2R4;
- —CONHR4;
- phenyl;
- or benzyl;
- wherein each R4 is independently H;
- straight chained or branched C1-C4 alkyl, C1-C4 monofluoroalkyl, or C1-C4 polyfluoroalkyl;
- or phenyl;
- wherein each R5 is independently H;
- straight chained or branched C1-C4 alkyl, C1-C4 monofluoroalkyl, or C1-C4 polyfluoroalkyl;
- wherein each R7 is independently H;
- —CN;
- straight chained or branched C1-C4 alkyl, C1-C4 monofluoroalkyl, or C1-C4 polyfluoroalkyl;
- straight chained or branched C1-C4 alkoxy;
- —OH;
- —(CH2)qOH;
- —COR4;
- —CO2R4;
- —CONHR4;
- phenyl;
- or benzyl;
- wherein m and n are each independently 0, 1, 2 or 3, provided that m+n is 2 or 3;
- wherein each p is independently 0, 1 or 2;
- and
- wherein each q is independently 0, 1, 2 or 3;
- with the proviso that when Y is CR3R5, p is 1 or 2 and at least one R3 is not H;
- or a pharmaceutically acceptable salt thereof.
48 more elements
Dependencies are inferred from the claim text.