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US 2003/0171350 A1Published application
Sulphonamide derivatives
AssigneeEli Lilly and Company
InventorsMacKlin Brian Arnold, David Michael Bender, Andrew Hendley Fray, Winton Dennis Jones, Paul Leslie Ornstein, Richard Lee Simon, Hamideh Zarrinmayeh, Dennis Michael Zimmerman
Life of this patent
Estimating the term…
Abstract
The present invention relates to the potentiation of glutamate receptor function using certain sulphonamide derivatives. It also relates to novel sulphonamide derivatives, to processes for their preparation and to pharmaceutical compositions containing them.
Claims17
A compound of the formula:
- 59
- wherein
- one or both of Ra and Rb are selected independently from F, CF3 and —ORc wherein Rc is hydrogen or (1-4C)alkyl, and any remainder is hydrogen;
- or Ra and Rb together represent ═O or ═CH2;
- 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)alkoxycarbonyldihydrothiazolyl;
- (1-4C)alkoxycarbonyldimethyldihydrothiazolyl;
- tetrahydrothienyl;
- 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 (1-4C)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)fluoroalkyl, (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.
44 more elements
A compound selected from the group consisting of:
- 12 a 61 b 62 c 63 d 64 e 65
- and the pharmaceutically acceptable salts thereof.
Dependencies are inferred from the claim text.