Patent ID: 6355631
Filing Date: 2002-03-12
Classification: C07D

Abstract:
A pharmaceutical composition containing as active ingredient at least one compound of formula: in whichR1 represents a radical selected fromâ€”N(R4)R5, â€”N(R4)â€”COâ€”R5, and â€”N(R4)â€”SO2R6, R2 and R3, which are identical or different, represent either A) an aromatic group selected from phenyl, naphthyl and indenyl, these aromatic groups being unsubstituted or substituted with one or more substituents selected from halogen, alkyl, alkoxy, formyl, hydroxyl, trifluoromethyl, trifluoromethoxy, â€”CO-alk, cyano, â€”COOH, COOalk, â€”CONR7R8, â€”COâ€”NHâ€”NR9R10, alkylsulfanyl, alkylsulfinyl, alkylsulfonyl, alkylsulfanylalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, hydroxyalkyl and â€”alkâ€”NR7R8 radicals; or B) a heteroaromatic group selected from benzofuryl, benzothiazolyl, benzothienyl, benzoxazolyl, chromanyl, 2,3-dihydrobenzofuryl, 2,3-dihydrobenzothienyl, furyl, imidazolyl, isochromanyl, isoquinolyl, pyrrolyl, pyridyl, pyrimidyl, quinolyl, 1,2,3,4-tetrahydroisoquinolyl, thiazolyl and thienyl rings, it being possible for these heteroaromatic groups to be unsubstituted or substituted with a substituent selected from halogen, alkyl, alkoxy, hydroxyl, trifluoromethyl, trifluoromethoxy, cyano, â€”COOH, COOalk, â€”COâ€”NHâ€”NR9R10, â€”CONR7R8, â€”alkâ€”NR9R10, alkylsulfanyl, alkylsulfinyl, alkylsulfonyl, alkylsulfanylalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl and hydroxyalkyl, R4 represents a radical selected fromâ€”C(R11)(R12)â€”Het, â€”Het, â€”(CR11)(R12)â€”Ar, Ar, cycloalkyl and norbornyl, R5 represents a radical selected from hydrogen, hydroxyalkyl, â€”alkâ€”COOalk, â€”alkâ€”CONR7R8, â€”alkâ€”NR7R8, alkoxy, Ar, Het, â€”CH2Ar, â€”CH2Het and alkyl, said radical being optionally substituted with one or more halogens, R6 represents a radical selected from hydroxyalkyl, â€”alkâ€”COOalk, â€”alkâ€”CONR7R8, â€”alkâ€”NR7R8, alkoxy, Ar, Het, â€”CH2Ar, â€”CH2Het and alkyl, optionally substituted with 1 or more halogens, R7 and R8, which are identical or different, represent a radical selected from hydrogen and alkyl, or, alternatively, R7 and R8 together form with the nitrogen atom to which they are attached a 3- or 10-membered saturated mono- or bicyclic heterocycle, optionally containing another heteroatom selected from oxygen, sulfur and nitrogen and being optionally substituted with one or more alkyl radicals, R9 and R10, which are identical or different, represent a radical selected from hydrogen, alkyl, â€”COOalk, cycloalkyl, alkylcycloalkyl, â€”alkâ€”Oâ€”alk and hydroxyalkyl or, alternatively, R9 and R10 together form with the nitrogen atom to which they are attached a 3- to 10-membered saturated or unsaturated mono- or bicyclic heterocycle, optionally containing another heteroatom selected from oxygen, sulfur and nitrogen and being optionally substituted with one or more alkyl, â€”COalk, â€”COOalk, â€”COâ€”NHalk, â€”CSâ€”NHalk, oxo, hydroxyalkyl, â€”alkâ€”Oâ€”alk or â€”COâ€”NH2 radicals, R11 represents a radical selected from hydrogen, hydroxyalkyl, â€”alkâ€”COOalk, â€”alkâ€”CONR7R8, â€”alkâ€”NR7R8, alkoxyalkyl, Ar, Het, â€”CH2Ar, â€”CH2Het and alkyl, optionally substituted with one or more halogen atoms, R12 represents a radical selected from hydrogen, hydroxyalkyl, â€”alkâ€”COOalk, â€”alkâ€”CONR7R8, â€”alkâ€”NR7R8, alkoxyalkyl and alkyl, optionally substituted with one or more halogen atoms, or alternatively R11 and R12 together form with the carbon atom to which they are attached a 3- to 10-membered saturated mono- or bicyclic ring, optionally containing another heteroatom selected from oxygen, sulfur and nitrogen and being optionally substituted with one or more alkyl radicals, Ar represents a phenyl, naphthyl or indenyl radical, these different radicals being optionally substituted with one or more halogen atoms or alkyl, alkoxy, â€”CO-alk, cyano, â€”COOH, â€”COOalk, â€”CONR13R14, â€”COâ€”NHâ€”NR15R16, alkylsulfanyl, alkylsulfinyl, alkylsulfonyl, â€”alkâ€”NR15R16, â€”NR15R16, alkylthioalkyl, formyl, CF3, OCF3, Het, â€”Oâ€”alkâ€”NHâ€”cycloalkyl, SO2NH2, hydroxyl, hydroxyalkyl, â€”NHCOalk, and NHCOOalk radicals or, on 2 adjacent carbon atoms, with dioxymethylene, Het represents a 3- or 10-membered unsaturated or saturated mono- or bicyclic heterocycle containing one or more heteroatoms selected from oxygen, sulfur and nitrogen optionally substituted with one or more halogen atoms or alkyl, alkoxy, alkoxycarbonyl, oxo or hydroxyl radicals, the nitrogen-containing heterocycles being optionally in their N-oxidized form, R13 and R14, which are identical or different, represent hydrogen or an alkyl radical or, alternatively, R13 and R14 together form with the nitrogen atom to which they are attached a 3- to 10-membered saturated mono- or bicyclic heterocycle, optionally containing another heteroatom selected from oxygen, sulfur and nitrogen and being optionally substituted with one or more alkyl radicals, R15 and R16, which are identical or different, represent hydrogen or an alkyl radical or, alternatively, R15 and R16 together form with the nitrogen atom to which they are attached a 3- to 10-membered saturated mono- or bicyclic heterocycle, optionally containing another heteroatom selected from oxygen, sulfur and nitrogen and being optionally substituted with one or more alkyl radicals, alk represents an alkyl or alkylene radical, the alkyl and alkylene radicals and portions and the alkoxy radicals and portions being in the form of straight or branched chains and containing 1 to 6 carbon atoms, and the cycloalkyl radicals containing 3 to 10 carbon atoms, the optical isomers of these compounds and their salts with a pharmaceutically acceptable inorganic or organic acid.