FIELD: chemistry.
SUBSTANCE: invention relates to organic chemistry, namely to a heterocyclic compound of formula (I), where Z – CH or N; I) wherein, when Z is CH, then R1 is selected from -H and -C1-3alkyl; Y is -C (Ra)2-, wherein each Ra is independently selected from -H, -F, -CH3, -OH and -N(Rb)2; R2 is selected from A) phenyl, unsubstituted or substituted with one substituent Rc, wherein Rc is selected from halogen, -CN, -CO2Rb, -CONH2, -SO2CH3, -C(Rb)2OH, -CH2NH2, -CH2CONH2, -CH2CO2C1-3alkyl, -NHCONH2, -NHCONH-oxetane, -CONH-oxetane, 
and 
; B) six-membered monocyclic heteroaromatic ring containing one or two nitrogen atoms, unsubstituted or substituted with one or two substituents each independently selected from halogen, -C1-3alkyl, -C1-3haloalkyl, -CN, -OH, -C(Rb)2OH, -CH2NH2, -C(Rb)2CN, -C(Rb)2CONH2, -OCH2CONH2, -OC1-3alkyl, -OCH2C(Rb)2OH, -OCH2cyclopropyl, -OC1-3haloalkyl, -CO2H, -CON(Rb)2, -N(Rb)2, -NHCH2CF3, -NHCH(CH3)2, -NHCH2CH2N(CH3)2, -NHCH2CH2OH, -NH-cyclopropyl, -NHCOCH3, morpholinyl, pyrrolidin-3-ol and azetidin-3-ol; C) five-membered monocyclic heteroaromatic ring containing two, three or four nitrogen atoms, unsubstituted or substituted with one or two substituents each independently selected from halogen,-C1-3alkyl, -C1-3haloalkyl, -C(Rb)2OH, -N(Rb)2, -NO2, -CN, -CH2CN, -OC1-3alkyl, -CH2OCH3, -CH2CH2OH, -CH2NH2, -CH2CONH2, -CO2C1-3alkyl, -CO2H, -CONH2, -NHCOCH3 and cyclopropyl; and D) five- or six-membered ring selected from: 1,2-dihydropyridin-2-one, thiazole or 1,2-oxazole, unsubstituted or substituted with one or two substituents each independently selected from -CH3 and -NH2; R3 is phenyl or pyridine, each of which is substituted with one or two substituents each independently selected from -halogen, -C1-3alkyl, -OC1-3alkyl, -O-cyclopropyl, -O-oxetane, -C1-3haloalkyl, -C1-3Ogaloalkyl, -CN, -CH2OH, -SO2CH3 and -N(CH3)2; R4 is selected from -C1-3alkyl and -C1-3haloalkyl; and each Rb is -H or -CH3; II) wherein, when Z is N, then R1 is H; Y is -CH2-; R2 is selected from A) phenyl substituted with one substituent Rd, wherein Rd is selected from -CN, -CONH2 and -CO2C1-3alkyl; B) six-membered monocyclic heteroaromatic ring containing one or two nitrogen atoms unsubstituted or substituted with a substituent selected from -CN, -OC1-3alkyl, -CONH2, -NHCH2CH2OH, -N(Rb)2 and -NH-cyclopropyl; C) five-membered monocyclic heteroaromatic ring containing two or three nitrogen atoms, unsubstituted or substituted with one or two substituents, each selected from -C1-3alkyl, -C1-3haloalkyl, -CH2ORb, -N(Rb)2, -NO2, -CO2CH3, -CO2N(Rb)2 and cyclopropyl; and D) 1,2-oxazole optionally substituted with one or two Rb; R3 is phenyl substituted with one substituent selected from -Cl, -OC1-3alkyl and -OC1-3haloalkyl; R4 is -C1-3alkyl; and each Rb is independently selected from -H and -CH3. Invention also relates to particular compounds, a method for modulating PDE4 enzyme activity and a method for treating Alzheimer's disease, Parkinson's disease and cognitive disorders. 
Formula (I).
EFFECT: novel heterocyclic compounds possessing useful biological activity are obtained.
42 cl, 410 ex
| Title | Year | Author | Number |
|---|---|---|---|
| SUBSTITUTED PYRIDINE AND PYRAZINE COMPOUNDS AS PDE4 INHIBITORS | 2014 |
|
RU2802185C2 |
| SUBSTITUTED [1,2,4]TRIAZOLO[1,5-A]PYRIMIDINE-7-YL COMPOUNDS AS THE INHIBITORS OF PDE2 | 2015 |
|
RU2659070C9 |
| POLYHETEROCYCLIC COMPOUNDS AND USE THEREOF AS METABOTROPIC GLUTAMATE RECEPTOR ANTAGONISTS | 2005 |
|
RU2381226C2 |
| TRIAZOLO-PYRIMIDINE COMPOUNDS AND THEIR USE | 2019 |
|
RU2802866C2 |
| BICYCLIC KETONES AND METHODS OF THEIR USE | 2018 |
|
RU2797922C2 |
| USE OF 1H-PYRAZOLO[4,3-B]PYRIDINES AS PDE1 INHIBITORS | 2017 |
|
RU2759380C2 |
| SPIRO COMPOUNDS AS ANTAGONISTS OF MELANOCORTIN 4 RECEPTORS AND THEIR USE | 2021 |
|
RU2813541C1 |
| PESTICIDE COMPOSITIONS AND RELATED METHODS | 2013 |
|
RU2654327C2 |
| PYRIDOPYRIMIDINONE DERIVATIVES AND USE THEREOF AS AROMATIC HYDROCARBON RECEPTOR MODULATORS | 2021 |
|
RU2818954C1 |
| AZOLE DERIVATIVES | 2012 |
|
RU2622639C2 |
