Tryptamine sulfonamides as 5-HT6 antagonists
AssigneeMerck Sharp & Dohme Corp.
InventorsAlexander Pasternak, Michael J. Szymonifka
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Abstract
Novel compounds of the structural formula (I) are antagonists of the 5-HT6 receptor and are useful in the treatment, prevention and suppression of diseases mediated by the 5-HT6 receptor. The compounds of the present invention are useful in the treatment of obesity, diabetes, metabolic disorder, cognitive disorders, age related cognitive disorder, depression, mania, bipolar disorders, schizophrenia, anxiety, generalized anxiety disorder, panic disorder, and obsessive compulsive disorder, epilepsy, convulsions, migraine, substance withdrawal from substances including but not limited to opiates, nicotine, tobacco products, alcohol, benzodiazepines, sedatives, and the like, sleep disorders, attention deficit/hyperactivity disorder, and Alzheimer's disease.
Claims15
A compound of structural formula I:
- or a pharmaceutically acceptable salt thereof, wherein:
- X is selected from the group consisting of:
- (1) —O—,
- (2) —NH—,
- (3) —S—,
- (4) —SO2—,
- (5) —CH2—,
- (6) —CHF—,
- (7) —CF2—,
- (8) —CH(OH)—,
- (9) —CO—,
- (10) —NHCO—,
- (11) —CONH—, and
- (12) —CO2—;
- R1 is selected from the group consisting of:
- (1) -hydrogen, and
- (2) —C1-3alkyl;
- R2 is selected from the group consisting of:
- (1) —C1-6alkyl,
- (2) —C3-7cycloalkyl,
- (3) —C2-6cycloheteroalkyl,
- (4) phenyl,
- (5) naphthyl, and
- (6) heteroaryl,
- wherein each alkyl, cycloalkyl, cycloheteroalkyl, phenyl, naphthyl and heteroaryl is unsubstituted or substituted with 1, 2 or 3 substituents selected from —C1-6alkyl, —C3-7cycloalkyl, halogen, —CF3, —OCF3, —CN, —SO2R7, —CO2R8, phenyl, —C2-6cycloheteroalkyl, —OR7, —SR7, —CONHR8, —NHSO2R7, and —NHCOR7;
- R3 and R4 are each independently selected from the group consisting of:
- (1) hydrogen,
- (2) halogen,
- (3) —C1-6alkyl,
- (4) —OC1-6alkyl,
- (5) —CN,
- (6) —OR7,
- (7) —SO2R7,
- (8) —SR7,
- (9) —N(R8)2,
- (10) —CONHR8,
- (11) —NHSO2R7, and
- (12) —NHCOR7,
- wherein each alkyl is unsubstituted or substituted on each carbon with 1, 2 or 3 substituents selected from halogen, —C1-6alkyl, —C3-7cycloalkyl, —CF3, —OCF3, —CN, —SO2R7, —CO2R8, phenyl, —C2-6cycloheteroalkyl, —OR7, —SR7, —CONHR8, —NHSO2R7, and —NHCOR7;
- R5 is selected from the group consisting of:
- (1) —C1-6alkyl,
- (2) —C1-6alkenyl,
- (3) phenyl, and
- (4) benzyl,
- wherein each alkyl, alkenyl, phenyl and benzyl is unsubstituted or substituted on each carbon with 1, 2 or 3 substituents selected from:
- halogen, —C1-6alkyl, —C3-7cycloalkyl, —CF3, —OCF3, —CN, —SO2R7, —CO2R8, phenyl, —C2-6cycloheteroalkyl, —OR7, —SR7, —CONHR8, —NHSO2R7, and —NHCOR7;
- R6 is selected from the group consisting of:
- (1) hydrogen, and
- (2) —C1-4alkyl;
- R7 is selected from the group consisting of:
- (1) —C1-6alkyl, and
- (2) —C3-6cycloalkyl;
- and
- R8 is selected from the group consisting of:
- (1) hydrogen,
- (2) —C1-6alkyl, and
- (3) —C3-6cycloalkyl.
Dependencies are inferred from the claim text.