Patent DE-10153344-A1 (DE)
Title: Medicaments for treating e.g. epilepsy, schizophrenia, neurodegenerative diseases or especially pain, comprising new or known pyrazolo-pyrimidine or thiazolo-pyrimidine compounds
Inventor: MAUL CORINNA
IPC: C07D487/04
Filed: 2001-10-29
Abstract: Medicaments contain tetrahydro-pyrazolo (1,5-a) pyrimidine or 6,7-dihydro-5H-thiazolo (2,3-a) pyrimidine compounds (I) - (III).  New medicaments contain pyrazolo- or thiazolo-pyrimidine compounds of formula (I) - (III) or their acid or base addition salts or solvates (specifically hydrates), in the form of racemates, pure stereoisomers (specifically enantiomers or diastereomers) or stereoisomer mixtures in any ratio.  R1, R2  = H, OR9, SR10, 1-12C alkyl, cycloalkyl, cycloalkylmethyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl; provided that one of R1 and R2 = H and the other is other than H, except that if one of R1 and R2 = aryl then the other = H or 1-12C alkyl;  R3, R4  = H, 1-12C alkyl, cycloalkyl, cycloalkylmethyl, aryl or arylalkyl; provided that at least one of R3 and R4 = H; or  one of R1/R2 plus one of R3/R4  = W', the other of R1/R2 and the other of R3/R4 being H or 1-12C alkyl;  W'  = (CH2)n, CH=CHCH2, CH2CH=CH, CH=CHCH2CH2, CH2CH=CHCH2, CH2CH2CH=CH, O(CH2)m, CH2-oC6H4-CH2, -oC6H4-CH2, X-oC6H4- or -oC6H4-CH2CH2 (all with the left- and right-hand terminals bonded at the R1/R2 and R3/R4 positions respectively); or cyclopent-1-ene-3,5-diyl or cyclohexane-1,3-diyl:  n  = 3-6;  m  = 2-5;  X  = CH2, O or S;  R5  = 1-12C alkyl, cycloalkyl, cycloalkylmethyl, aryl, arylalkyl, heterocyclyl, heterocyclylalkyl or C(O)R11;  R6  = H, 1-8C alkyl, CN, halo, NO2, NH2, NHR12, NR13R14, OR15, S(O)pR16, C(O)R17 or -N=N-aryl;  R7  = H, 1-8C alkyl, CN, halo, NO2, NH2, NHR12, NR13R14, OR15, S(O)pR19, C(O)R17 or -N=N-aryl;  R8  = H, 1-8C alkyl or aryl; or  R7 + R8  = C(R21)=C(R22)-C(R23)=C(R24);  p  = 0-2;  R9, R10, R15, R16, R18, R19  = H, 1-8C alkyl, cycloalkyl, cycloalkylmethyl, aryl or arylalkyl;  R11  = H, 1-8C alkyl, cycloalkyl, cycloalkylmethyl, aryl or OR25;  R12  = alkyl or arylmethyl;  R13, R14  = alkyl; or  R13 + R14  = (CH2)h;  h  = 4 or 5;  R17  = as R9; or NH2, NHR12, NR13R14 or OR26;  R20  = as R9; or OR27;  R21 - R24  = H, halo or OR28;  R25 - R28  = H or alkyl, provided that R25 is not H if R1 = aryl and R2 = alkyl;  unless specified otherwise alkyl groups have 1-6C and cycloalkyl groups 3-8C.  Independent claims are included for:  (i) the preparation of (I) - (III);  (ii) (I) - (III) (including salts, solvates, stereoisomers etc.) as new compounds, with the exception of: 4,5,6,7-tetrahydro-2-methyl-5,7-diphenyl-pyrazolo (1,5-a) pyrimidine; 4,5,6,7-tetrahydro-2,5-dimethyl-7-phenyl-pyrazolo (1,5-a) pyrimidine; 4,5,6,7-tetrahydro-5,7-methyl-3-phenyl-pyrazolo (1,5-a) pyrimidine; 4,5,6,7-tetrahydro-2,5,7-trimethyl-pyrazolo (1,5-a) pyrimidine; 4,5,6,7-tetrahydro-5,7-dimethyl-2-phenyl-pyrazolo (1,5-a) pyrimidine; 4,5,6,7-tetrahydro-2-methyl-5,7-di-n-propyl-pyrazolo (1,5-a) pyrimidine-3-carbonitrile; 4,5,6,7-tetrahydro-5-methyl-7-(3-(trifluoromethyl)-phenyl)-pyrazolo (1,5-a) pyrimidine-3-carbonitrile; 7-(3- or 4-chlorophenyl)-4,5,6,7-tetrahydro-5-methyl-pyrazolo (1,5-a) pyrimidine-3-carbonitrile; 3,4-dihydro-2-(4-nitrophenyl)-4-phenyl-2H-pyrimido (2,1-b) benzothiazole; and 3,4-dihydro-4-(4-methylphenyl)-2-(4-nitrophenyl)-2H-pyrimido (2,1-b) benzothiazole; and  (iii) combinatorial libraries containing the new compounds as in (ii).