FIELD: chemistry.
SUBSTANCE: invention relates to salt of 1-[[(3S)-3-methyl-6-(4,4,4-trifluorobutoxy)-3,4-dihydronaphthalen-2-yl]methyl]azetidine-3-carboxylic acid, where the salt is mono (4-hydroxybenzoate). Invention relates to crystalline form A of mono (4-hydroxybenzoate)1-[[(3S)-3-methyl-6-(4,4,4-trifluorobutoxy)-3,4-dihydronaphthalen-2-yl]methyl]azetidine-3-carboxylic acid, containing diffraction peaks on the powder X-ray diffraction pattern at diffraction angles (2θ) equal to at least 6.9 ± 0.2 degrees, 12.8 ± 0.2 degrees, 13.9 ± 0.2 degrees and 24.7 ± 0.2 degrees. Invention also relates to a pharmaceutical composition having S1P5 receptor agonist activity, containing a pharmaceutically effective amount of the compound according to the invention and a pharmaceutically acceptable carrier. Method of producing crystalline form A mono(4-hydroxybenzoate) 1-[[(3S)-3-methyl-6-(4,4,4-trifluorobutoxy)-3,4-dihydronaphthalen-2-yl]methyl]azetidine-3-carboxylic acid according to the invention includes a stage of mixing crystal D 1-[[(3S)-3-methyl-6-(4,4,4-trifluorobutoxy)-3,4-dihydronaphthalen-2-yl]methyl]azetidine-3-carboxylic acid, containing diffraction peaks on the powder X-ray diffraction pattern at diffraction angles (2θ) (given in the claims), and 4-hydroxybenzoic acid; adding acetonitrile to the obtained mixture at room temperature; stirring the obtained mixture during the night; filtration of suspended crystals and drying of crystals at 50 °C at reduced pressure for 3 hours.
EFFECT: mono(4-hydroxybenzoate) 1-[[(3S)-3-methyl-6-(4,4,4-trifluorobutoxy)-3,4-dihydronaphthalen-2-yl]methyl]azetidine-3-carboxylic acid for use for preventing and/or treating S1P5 mediated disease.
17 cl, 29 dwg, 18 tbl, 25 ex
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