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US 6,387,954 B1Granted
Alkenyl sulphonamide derivatives
AssigneeEli Lilly and Company
InventorsWinton Dennis Jones, Paul Leslie Ornstein, Hamideh Zarrinmayeh, Dennis Michael Zimmerman
Life of this patent
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Abstract
The present invention provides certain alkenyl sulphonamide derivatives useful for potentiating glutamate receptor function in a mammal and therefore, useful for treating a wide variety of conditions, such as psychiatric and neurological disorders.
Claims12
A compound of the formula:
- wherein
- Ra and Rb each independently represents hydrogen;
- (1-6C)alkyl;
- aryl(1-6C)alkyl;
- (2-6C)alkenyl;
- aryl(2-6C)alkenyl or aryl, or
- Ra and Rb together with the carbon atoms to which they are attached form a (4-8C) carbocyclic ring;
- R1 represents a naphthyl group or a phenyl, furyl, thienyl or pyridyl group which is unsubstituted or substituted by one or two substituents selected independently from halogen;
- nitro;
- cyano;
- hydroxyimino;
- (1-10C)alkyl;
- (2-10C)alkenyl;
- (2-10C)alkynyl;
- (3-8C)cycloalkyl;
- hydroxy(3-8C)cycloalkyl;
- oxo(3-8C)cycloalkyl;
- halo(1-10C)alkyl;
- (CH2)yX1R9 in which y is 0 or an integer of from 1 to 4, X1 represents O, S, NR10, CO, COO, OCO, CONR11, NR12CO, NR12COCOO or OCONR13, R9 represents hydrogen, (1-10C)alkyl, (3-10C)alkenyl, (3-10C)alkynyl, pyrrolidinyl, tetrahydrofuryl, morpholino or (3-8C)cycloalkyl and R10, R11, R12 and R13 each independently represents hydrogen or (1-10C)alkyl, or R9 and R10, R11, R12 or R13 together with the nitrogen atom to which they are attached form an azetidinyl, pyrrolidinyl, piperidinyl or morpholino group;
- N-(1-4C)alkylpiperazinyl;
- N-phenyl(1-4C)alkylpiperazinyl;
- thienyl;
- furyl;
- oxazolyl;
- isoxazolyl;
- pyrazolyl;
- imidazolyl;
- thiazolyl;
- pyridyl;
- pyridazinyl;
- pyrimidinyl;
- dihydrothienyl;
- dihydrofuryl;
- dihydrothiopyranyl;
- dihydropyranyl;
- dihydrothiazolyl;
- (1-4C)alkoxycarbonyidihyd rothiazolyl;
- (1-4C)alkoxycarbonyldimethyldihydrothiazolyl;
- tetrahydro-thienyl;
- tetrahydrofuryl;
- tetrahydrothiopyranyl;
- tetrahydropyranyl;
- indolyl;
- benzofuryl;
- benzothienyl;
- benzimidazolyl;
- and a group of formula R14—(La)n—X2—(Lb)m in which X2 represents a bond, O, NH, S, SO, SO2, CO, CH(OH), CONH, NHCO, NHCONH, NHCOO, COCONH, OCH2CONH or CH═CH, La and Lb each represent (14C)alkylene, one of n and m is 0 or 1 and the other is 0, and R14 represents a phenyl or heteroaromatic group which is unsubstituted or substituted by one or two of halogen, nitro, cyano, hydroxyimino, (1-10C)alkyl, (2-10C)alkenyl, (2-10C)alkynyl, (3-8C)-cycloalkyl, 4-(1,1-dioxotetrahydro-1,2-thiazinyl), halo(1-10C)alkyl, cyano(2-10C)alkenyl, phenyl, and (CH2)zX3R15 in which z is 0 or an integer of from 1 to 4, X3 represents O, S, NR16, CO, CH(OH), COO, OCO, CONR17, NR18CO, NHSO2, NHSO2NR17, NHCONH, OCONR19 or NR19COO, R15 represents hydrogen, (1-10C)alkyl, phenyl(1-4C)alkyl, (1-10C)haloalkyl, (1-4C)alkoxycarbonyl(1-4C)alkyl, (1-4C)alkylsulfonylamino(1-4C)alkyl, (N-(1-4C)alkoxycarbonyl)(1-4C)alkylsulfonylamino-(1-4C)alkyl, (3-10C)alkenyl, (3-10C)alkynyl, (3-8C)-cycloalkyl, camphoryl or an aromatic or heteroaromatic group which is unsubstituted or substituted by one or two of halogen, (1-4C)alkyl, halo(1-4C)alkyl, di(1-4C)alkylamino and (1-4C)alkoxy and R16, R17, R18 and R19 each independently represents hydrogen or (1-10C)alkyl, or R15 and R16, R17, R18 or R19 together with the nitrogen atom to which they are attached form an azetidinyl, pyrrolidinyl, piperidinyl or morpholino group;
- and
- R2 represents (1-6C)alkyl, (3-6C)cycloalkyl, (1-6C)fluoro-alkyl, (1-6C)chloroalkyl, (2-6C)alkenyl, (1-4C)alkoxy(1-4C)alkyl, phenyl which is unsubstituted or substituted by halogen, (1-4C)alkyl or (1-4C)alkoxy, or a group of formula R3R4N in which R3 and R4 each independently represents (1-4C)alkyl or, together with the nitrogen atom to which they are attached form an azetidinyl, pyrrolidinyl, piperidinyl, morpholino, piperazinyl, hexahydroazepinyl or octahydroazocinyl group;
- or a pharmaceutically acceptable salt thereof;
- with the priviso that if R1 and Ra represent phenyl and Rb represents hydrogen, then R2 is other than 4-methylphenyl and 4-bromophenyl, and with the further priviso that if R1, Ra, and Rb represent phenyl, then R2 is other than methyl.
48 more elements
Dependencies are inferred from the claim text.