Substituted 3-arylsulfonyl-pyrazolo[1,5-A]pyrimidines, serotonin 5-HT6 receptor antagonists and methods for the production and use thereof

A compound of the general formula 1, or a pharmaceutically acceptable salt thereof,

• wherein:
• X=S, SO, NH;
• R1 is hydrogen, —CH3, —CH2OH, an optionally substituted C2-C3alkyl, cycloalkyl, adamantyl, optionally substituted aryl or 5-6 membered optionally annelated heterocyclyl, in which a heteroatom is selected from nitrogen or oxygen, alkoxycarbonyl, carboxyl, amide group;
• R2 is hydrogen, halogen, optionally substituted C1-C3alkyl, substituted hydroxyl, substituted amino group or —(CH2)nZ group;
• R3, wherein X=NH, is hydrogen, optionally substituted C1-C3alkyl, substituted hydroxyl, optionally mono- or disubstituted amino group or saturated 6-membered azaheterocyclyl containing an additional heteroatom selected from nitrogen or oxygen;
• pyridyl, alkoxycarbonyl, carboxyl or amide group;
• or
• R3, wherein X=S, SO, is hydrogen, optionally substituted C1-C3alkyl, substituted hydroxyl, pyridyl, alkoxycarbonyl, carboxyl or amide group;
• or
• R1 and R3 independently are different substituents selected from C1-C3alkyl, or —(CH2)nZ group, and R2 is hydrogen, halogen, optionally substituted C1-C3alkyl, substituted hydroxyl;
• R4 is C1-C3alkyl;
• R5 is hydrogen, one or two halogens, C1-C3alkyl or optionally substituted hydroxyl;
• n is 0, 1, 2 or 3;
• Z, wherein X=NH, is carboxyl COOH, C1-C3alkyloxycarbonyl substituted amide group CONR10R11 or amino group NR10R11;
• R10 and R11 are optionally identical hydrogen, optionally substituted C1-C3alkyl, C3-C7cycloalkyl or optionally substituted 5-7-membered azaheterocyclyl containing 1-2 nitrogen atoms in the cycle, wherein the substituents are selected from C1-C3alkyl;
• or R10 and R11 together with the nitrogen atom to which they are attached form an optionally substituted 5-6-membered azaheterocyclyl containing 1-2 nitrogen atoms in the cycle, wherein the substituent is selected from C1-C3alkyl;
• or
• Z, wherein X=S, SO, is carboxyl COOH, C1-C3alkyloxycarbonyl substituted amide group CONR10R11 or amino group NR10R11;
• R10 and R11 are optionally identical hydrogen, optionally substituted C1-C5alkyl;
• or R10 and R11 together with the nitrogen atom to which they are attached form an optionally substituted 6-membered azaheterocyclyl containing 1-2 nitrogen atoms in the cycle, wherein the substituent is selected C1-C3alkyl;
• with the exception of the compounds wherein X=S, R3 is —(CH2)nZ group, wherein Z is amino group NR10R11 and n=0.