[9,10-DIMETHOXY-3-(2-METHYLPROPYL)-1H,2H,3H,4H,6H,7H,11BH-PYRIDO[2,1-A]ISOQUINOLIN-2-YL]METHANOL AND RELATED COMPOUNDS, COMPOSITIONS AND METHODS Russian patent published in 2020 - IPC C07D455/04 C07D471/04 A61K31/4353 A61P25/14 

FIELD: organic chemistry.

SUBSTANCE: present invention relates to a compound having structural formula (I), including its pharmaceutically acceptable salts:

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In formula (I): R¹ is a) hydrogen; b) -P(=O)(OR³)₂; c) -C(=O)alkyl, where alkyl is optionally substituted with R¹⁰ and/or R²⁰; d) -C(=O)heterocyclyl, where heterocyclyl is optionally substituted with R¹⁰ and/or R²⁰; e) -C(=O)carbocyclyl, where carbocyclyl is optionally substituted with R¹⁰ and/or R²⁰; f) -C(=O)N(R₃)alkyl, wherein alkyl is optionally substituted by R¹⁰ and/or R²⁰; g) -C(=O)N(R₃)carbocyclyl, optionally substituted carbocyclyl, wherein R¹⁰ and/or R²⁰; h) -C(=O)Oalkyl, where alkyl is optionally substituted with R¹⁰ and/or R²⁰; or i) alkyl, where alkyl is optionally substituted with R¹⁰ and/or R²⁰; and where each R³ is independently hydrogen or alkyl; each R¹⁰ independently represents halogen, haloalkyl, cyano, nitro, -OR³⁰, -N(R³⁰)₂, -C(O)OR³⁰, -C(O)N(R³⁰)₂, -N(R³⁰)S(O)_tR³¹ (where t is 1–2), -S(O)_tOR³⁰ (where t is 1–2), -S(O)_pR³⁰ (where p is 0–2 ) or, when one atom carries two groups R¹⁰, such two groups R¹⁰ can be taken together to form oxo; each R²⁰ independently represents alkyl, phenyl, benzyl, cycloalkyl, heterocyclyl or heteroaryl, or, when one atom carries two groups R²⁰, such two groups R²⁰ can be taken together to form cycloalkyl, wherein each of said alkyl, phenyl, benzyl, cycloalkyl, heterocyclyl and heteroaryl groups are optionally substituted with R¹⁰ and/or R²²; each R²² independently represents alkyl optionally substituted with R¹⁰; and each R³⁰, R³¹ and R³² independently represents hydrogen or alkyl; where alkyl denotes a straight or branched hydrocarbon chain radical having 1 to 8 carbon atoms; heterocyclyl means piperidinyl, piperazinyl, pyrrolidinyl, oxetanyl, azetidinyl, tetrahydropyranyl, 1,3-diazinal, 2,3-dihydro-1H-isoindolyl, 1,2,3,4-tetrahydroisoquinolinyl, 1,2,3,4-tetrahydroquinazolinyl, 2-oxa-5-azabicyclo[2.2.1]heptanyl, decahydropiperazino[1,2-a]azepinyl, 3,8-diazabicyclo[3.2.1]octanyl, 2,5-diazabicyclo[2.2.1]heptanyl, [pyrrolidin-1-yl]oxidanyl, imidazolidinyl, 2,3-dihydro-1,3-benzoxazolyl and morpholinyl; carbocyclyl is phenyl, cyclopropyl, cyclopentyl, cyclohexyl, bicyclo[2.2.1]heptenyl and bicyclo[2.2.1]heptanyl; cycloalkyl means cyclopropyl, cyclopentyl, cyclohexyl, bicyclo[2.2.1]heptenyl and bicyclo[2.2.1]heptanyl; and heteroaryl means pyrrolyl, pyrazolyl and tetrazolyl. What is also presented is a pharmaceutical composition based on compound of formula (I).

EFFECT: novel organic compounds which are vesicular transporter of monoamines 2 (VMAT2) inhibitors and can be useful for treating hyperkinetic disorders.

22 cl, 3 dwg, 12 tbl, 14 ex