US 12,071,418 B2
Processes for preparation of dapagliflozin or its solvates or co-crystals thereof
Uma Maheswar Rao Vasireddi, Hyderabad (IN); Sanjay Kumar Dehury, Hyderabad (IN); Madana Venkata Sudhakar Gutti, Hyderabad (IN); and Krishna Murthy Thopudurthi, Hyderabad (IN)
Assigned to LAURUS LABS LIMITED, Hyderabad (IN)
Filed by LAURUS LABS LIMITED, Hyderabad (IN)
Filed on Jul. 5, 2022, as Appl. No. 17/857,497.
Application 17/857,497 is a division of application No. 16/323,335, granted, now 11,427,555, previously published as PCT/IB2017/054860, filed on Aug. 9, 2017.
Claims priority of application No. 201641027121 (IN), filed on Aug. 9, 2016; and application No. 201741013585 (IN), filed on Apr. 17, 2017.
Prior Publication US 2022/0372010 A1, Nov. 24, 2022
Int. Cl. C07D 309/10 (2006.01)
CPC C07D 309/10 (2013.01) 23 Claims
 
1. A process for the preparation of dapagliflozin of Formula I or its solvates or co-crystals thereof,

OG Complex Work Unit Chemistry
comprising:
a) (i) reacting a compound of Formula VI with a leaving group source to form a compound of Formula VIa′, (ii) reacting the compound of Formula VIa′ with an amine source in the presence of a base and a solvent to obtain a compound of Formula VII,

OG Complex Work Unit Chemistry
wherein
X1 and Lg each independently represent a leaving group; and
R1 and R2 independently represent hydrogen, a linear or branched alkyl group, a linear or branched alkenyl group, a cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group, or R1 and R2 together with the nitrogen atom to which they are attached form a heterocyclic ring;
b) condensing the compound of Formula VII with a glucono lactone of Formula VIII in the presence of a base and a solvent to obtain a compound of Formula IX′,

OG Complex Work Unit Chemistry
wherein R1 and R2 are as defined above and wherein P1, P2, P3 and P4 each independently represent a hydroxyl protecting group;
c) converting the compound of Formula IX′ to a compound of Formula XI′ with a glycosidation reagent in the presence of methanol,

OG Complex Work Unit Chemistry
wherein P1, P2, P3, P4, R1, and R2 are as defined above; and
d) reducing the compound of Formula XI′ using a reducing agent to obtain the dapagliflozin of Formula I; and
e) optionally, adding a solvent to the dapagliflozin of Formula I to obtain a solvate thereof, or adding a co-crystal former to form a co-crystal thereof.