FIELD: organic chemistry, pharmacy.
SUBSTANCE: invention relates to group of novel derivatives of 4,5-dihydro-1H-pyrazole and their stereoisomers that are strong antagonists of cannabinoid (CB1) receptors. These compounds are useful in treatment of some diseases associated with cannabinoid system disorders. Compounds have the general formula (I) 
wherein R represents phenyl or thienyl substituted with halogen atom, or R represents pyridyl; R1 represents phenyl that can be substituted with 1-2 substitutes chosen from halogen atom and trifluoromethyl group; R2 represents hydrogen atom; R3 represents hydrogen atom or branched or direct (C1-C4)-alkyl group; R4 represents branched or direct (C2-C4)-alkyl group that is substituted with hydroxy-, amino-, monoalkylamino-, dialkylamino-, methoxy-, acetoxy-, aminooxy-group or one fluorine atom, or R4 represents branched or direct (C1-C8)-alkoxy-group that can be substituted with amino-group, monoalkylamino-group or dialkylamino-group, or R4 represents (C4-C8)-nonaromatic heterocyclic or (C4-C8)-nonaromatic heterocycloalkyl-alkyl group that comprise 1-2 heteroatoms chosen from nitrogen (N) and oxygen (O) atom that can be substituted with (C1-C3)-alkyl group, or R4 represents hydroxy-group or imidazolylalkyl group or pyridylmethyl group; or if R represents hydrogen atom or methyl then R4 can represent group -NR6R7 wherein R6 represents hydrogen atom and R7 represents (C2-C4)-trifluoroalkyl; or R3 and R4 in common with nitrogen atom to which they are bound form saturated or unsaturated monocyclic or bicyclic heterocyclic group comprising 4-10 atoms in cycle that comprises 1-2 heteroatoms chosen from N and O, or group -SO2 wherein indicated group can be substituted with (C1-C4)-alkyl, hydroxy-group, hydroxyalkyl, pyridyl, amino-, monoalkylamino-, dialkylamino-group, monoalkylaminoalkyl, dialkylaminoalkyl or piperidyl group; R5 represents phenyl group substituted with 1-3 substitutes Y wherein Y represents halogen atom, trifluoromethyl group or (C1-C3)-alkyl, or R5 represents branched or direct (C1-C8)-alkyl. Also, invention relates to pharmaceutical compositions containing one or some these compounds as an active component.
EFFECT: valuable biological and medicinal properties of compounds and pharmaceutical compositions.
5 cl, 4 tbl, 92 ex
| Title | Year | Author | Number |
|---|---|---|---|
| DERIVATIVES OF 4,5-DIHYDRO-1H-PYRAZOLE POSSESSING CB-ANTAGONISTIC ACTIVITY | 2002 |
|
RU2281941C2 |
| DERIVATIVES OF 4,5-DIHYDRO-1H-PYRAZOLE POSSESSING STRONG CB1-ANTAGONISTIC ACTIVITY | 2002 |
|
RU2286988C2 |
| DERIVATIVES OF 4,5-DIHYDRO-1H-PYRAZOLE ELICITING CB1-ANTAGONISTIC ACTIVITY | 2001 |
|
RU2245878C2 |
| 1,3,5-TRISUBSTITUTED DERIVATIVES OF 4,5-DIHYDRO-1H-PYRAZOLE, POSSESSING CB-ANTAGONISTIC ACTIVITY | 2005 |
|
RU2360904C2 |
| IMIDAZOLINE DERIVATIVES HAVING CB-ANTAGONIST ACTIVITY | 2005 |
|
RU2357958C2 |
| DERIVATIVES OF 1H-IMIDAZOLE POSSESSING CB-AGONISTIC, PARTIAL CB-AGONISTIC OR CB-ANTAGONISTIC ACTIVITY | 2002 |
|
RU2299200C2 |
| DERIVATIVES OF THIAZOLE POSSESSING ANTAGONISTIC, AGONISTIC OR PARTIALLY AGONISTIC CB-ACTIVITY | 2003 |
|
RU2301804C2 |
| AZOLOPYRIMIDINES AS CANNABINOID 1 RECEPTOR INHIBITORS | 2007 |
|
RU2424242C2 |
| DERIVATIVES OF 1H-1,2,4-TRIAZOLE-3-CARBOXAMIDEAS LIGANDS OF RECEPTOR CANNABINOIDS | 2003 |
|
RU2325382C2 |
| THIAZOL DERIVATIVES AS CANNABINOID RECEPTOR MODULATORS | 2004 |
|
RU2348620C2 |
