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US 2014/0371266 A1Published application
Mono Quaternary Ammonium Salts and Methods for Modulating Neuronal Nicotinic Acetylcholine Receptors
AssigneeUniversity of Kentucky Research Foundation
InventorsPeter CROOKS, Linda P. DWOSKIN, Guangrong ZHENG, Sangeetha SUMITHRAN, Zhenfa ZHENG
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Abstract
Provided are monoquaternary ammonium compounds which are modulators of nicotinic acetylcholine receptors. Also provided are methods of using the compounds for modulating the function of a nicotinic acetylcholine receptor, and for the prevention and/or treatment of central nervous system disorders, substance use and/or abuse, and gastrointestinal tract disorders.
Claims28
A compound of Formula (I):
- wherein A1, A2, A3, A4, and A5 are independently selected from nitrogen or carbon, provided that when nitrogen is present, the nitrogen does not have an R substituent attached;
- wherein R1, R2, R3, R4, and R5 are each independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, heterocycle, substituted heterocycle, halo, cyano, and nitro, or R1 and R2 or R2 and R3 together with the carbons to which they are attached independently form a three to eight-member cycloalkane, substituted cycloalkane, cycloalkene, substituted cycloalkene, aryl, substituted aryl, heterocycle with one to three hetero atoms in the ring, or substituted heterocycle with one to three hetero atoms in the ring;
- wherein Z1 is absent or is selected from the group consisting of alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, phenylene, substituted phenylene, alkoxy, and substituted alkoxy;
- wherein Z2 is selected from the group consisting of alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, arylene, substituted arylene, heterocycle, substituted heterocycle, alkoxy, and substituted alkoxy;
- wherein Z3 is selected from is selected from hydrogen, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, heterocycle, and substituted heterocycle;
- wherein X− is an inorganic or organic anion.
3 more elements
A method for
- (a) selectively modulating the function of a nicotinic acetylcholine receptor,
- (b) preventing and/or treating a central nervous system associated disorder,
- (c) preventing and/or treating substance use and/or abuse, or
- (d) preventing and/or treating gastrointestinal tract disorders,
- comprising administering to a mammalian subject in need thereof a therapeutically effective amount of a compound of Formula (I):
- wherein A1, A2, A3, A4, and A5 are independently selected from nitrogen or carbon, provided that when nitrogen is present, the nitrogen does not have an R substituent attached;
- wherein R1, R2, R3, R4, and R5 are each independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, heterocycle, substituted heterocycle, halo, cyano, and nitro, or R1 and R2 or R2 and R3 together with the carbons to which they are attached independently form a three to eight-member cycloalkane, substituted cycloalkane, cycloalkene, substituted cycloalkene, aryl, substituted aryl, heterocycle with one to three hetero atoms in the ring, or substituted heterocycle with one to three hetero atoms in the ring;
- wherein Z1 is absent or is selected from the group consisting of alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, phenylene, substituted phenylene, alkoxy, and substituted alkoxy;
- wherein Z2 is selected from the group consisting of alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, arylene, substituted arylene, heterocycle, substituted heterocycle, alkoxy, and substituted alkoxy;
- wherein Z3 is selected from is selected from hydrogen, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, heterocycle, and substituted heterocycle;
- wherein X− is an inorganic or organic anion.
8 more elements
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24-30. (canceled)
32-40. (canceled)
42-49. (canceled)
Dependencies are inferred from the claim text.