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AssigneeLaurus Labs Private Limited
InventorsGottumukkala V. Subbaraju, Masna Mahesh, Hindupur R. Mohan, Thatipally Suresh, Igor Ivanisevic, Mark Andres, Kyle Stephens
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The present invention provides a scalable process for the preparation of stilbenes by (i) condensing 3,5-dialkylbenzyl phosphonates with 4′-O-tetrahydropyranyl benzaldehyde to get 3,5-alkyl-4′-O-tetrahydropyranyl Stilbene and (ii) deprotecting the obtained 3,5-Dialkyl-4′-O-tetrahydropyranylstilbene to yield stilbenes. The present invention also provides a novel intermediate 3,5-Dialkyl-4′-O-tetrahydropyranyl stilbene, which is a key intermediate for the synthesis of stilbenes such as Pterostilbene and Resveratrol. The present invention also provides characteristics of various solid forms of Pterostilbene, methods for their preparation, as well as dosage forms containing the same for administration to or consumption by humans.
A compound of formula 1
A process for the preparation of the compound of formula 1, comprising the step of condensing 3,5-Dialkylbenzyl phosphonates with 4′-O-tetrahydropyranyl benzaldehyde in presence of a base.
A process for the preparation of stilbene of formula 2,
Form I Pterostilbene having x-ray powder diffraction peaks, when measured with Cu—Kα radiation, at about 16.7 and 8.3°2θ, and a melting point of about 94-96° C.
Form II Pterostilbene having x-ray powder diffraction peaks, when measured with Cu—Kα radiation, at about 5.3, 9.6, and 10.5°2θ.
Form III Pterostilbene having x-ray powder diffraction peaks, when measured with Cu—Kα radiation, at about 11.3, 13.8, 14.1, 14.9, and 15.5°2θ.
Form IV Pterostilbene having x-ray powder diffraction peaks, when measured with Cu—Kα radiation, at about 8.4, 10.0, 12.0 and 15.3°2θ.
Form V Pterostilbene having x-ray powder diffraction peaks, when measured with Cu—Kα radiation, at about 5.2, 8.1, 8.9, 10.4, 12.1, or 14.2°2θ.
X-ray amorphous Pterostilbene having substantially the same x-ray powder diffraction pattern of FIG. 9.
A t-butanol solvate of Pterostilbene having substantially the same x-ray powder diffraction pattern as FIG. 8.
Dependencies are inferred from the claim text.