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US 6,686,349 B2Granted
Substituted tetracyclic pyrroloquinolone derivatives useful as phosphodiesterase inhibitors
AssigneeOrtho-McNeil Pharmaceutical, Inc.
InventorsWeiqin Jiang, Zhihua Sui
Life of this patent
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Abstract
The invention relates to novel tetracyclic pyrroloquinolone derivatives of the formula (I) or (II): wherein all variables are as herein defined, pharmaceutical compositions containing the compounds and their use for the treatment of sexual dysfunction.
Claims12
A compound of formula (I) or (II):
- wherein
- X is selected from the group consisting of O and NR6;
- R6 is selected from the group consisting of hydrogen, C1-6alkyl, C2-6alkenyl, C2-6alkynyl, haloC1-6alkyl, C3-8cycloalkyl, C3-8cycloalkylC1-3alkyl, arylC1-3alkyl and heteroarylC1-3alkyl;
- wherein the aryl part of the arylC1-3alkyl group is phenyl or phenyl substituted with one or more substituents selected from halogen, C1-6alkyl, C1-6alkoxy and methylenedioxy;
- wherein the heteroaryl part of the heteroaiylC1-3alkyl group is selected from thienyl, furyl or pyridyl wherein the thienyl, furyl or pyridyl group is optionally substituted with one or more substituents independently selected from halogen, C1-6akyl or C1-6alkoxy;
- R1 is selected from the group consisting of hydrogen and C1-3alkyl;
- alternatively R6 and R1 are taken together as C3-4alkylene or C3-4alkenylene;
- n is an integer from 0 to 1;
- R2 is selected from the group consisting of C5-C10alkyl (optionally substituted with one to three substituents independently selected from halogen, hydroxy, nitro, amino, NHRA or N(RA)2), aryl (optionally substituted with one to three substituents independently selected from RC), cycloalkyl (optionally substituted with one to three substituents independently selected from RA), heteroaryl (optionally substituted with one to three substituents independently selected from RC), and heterocycloalkyl (optionally substituted with one to three substituents independently selected from RC);
- where each RA is independently selected from the group consisting of C1-C6alkyl, aryl, C1-C6aralkyl and heteroaryl, where the aryl, aralkyl or heteroaryl may be optionally substituted with one to three RB;
- where each RB is independently selected from the group consisting of halogen, nitro, cyano, C1-C6alkyl, C1-C6alkoxy, C1-C6alkylcarbonyl, carboxyC1-C6alkyl, C1-C6alkylsulfonyl, trifluoromethyl, amino, di(C1-C6alkyl)amino, acetylamino, carboxyC1-C6alkylcarbonylamino, hydroxyC1-C6alkylamino, NHRA and N(RA)2;
- where RC is selected from the group consisting of halogen, hydroxy, nitro, cyano, —CO2RD, C1-C6alkyl, C1-C6alkoxy, trifluoromethyl, trifluoromethoxy, NRDRE and arylC1-3alkyl;
- where RD is selected from the group consisting of hydrogen and C1-6alkyl;
- and where RE is selected from the group consisting of hydrogen, C1-6alkyl, C2-7alkylcarbonyl and C1-6alkylsulfonyl;
- R3 is selected from the group consisting of hydrogen, C1-6alkyl, C1-C6alkylcarbonyl, C2-C6alkenylcarbonyl and C2-C6alkynylcarbonyl;
- m is and integer from 0 to 4;
- R4 is independently selected from the group consisting of halogen, nitro, hydroxy, C1-C6alkyl, C1-C6alkoxy, —NH2, —NHRA, —N(RA)2, —ORA, —C(O)NH2, —C(O)NHRA, —C(O)N(RA)2, —NHC(O)RA, —SO2NHRA—SO2N(RA)2, where RA is as defined above, phenyl (optionally substituted with one to three substituents independently selected from RB), heteroaryl (optionally substituted with one to three substituents independently selected from RB) and heterocycloalkyl (optionally substituted with one to three substituents independently selected from RB);
- or a pharmaceutically acceptable salts thereof.
15 more elements
Dependencies are inferred from the claim text.