US 11,225,500 B2 · Synthesis of 1:1:1 co-crystal of 1-cyano-2-(4-cyclopropyl-benzyl)-4-(β-D-glucopyranos-1-yl)-benzene, L-proline and water

Abstract

The invention relates to a process for the manufacture of the crystalline compound according to formula (I) comprising the steps (a) deacetylating the final intermediate (FI), (b) forming the crystalline compound according to formula (I) by reacting the deacetylated final intermediate of step (a) with L-proline and water and isolating the final reaction product; processes of manufacturing intermediates thereof; process intermediates and their uses in the processes according to the present invention.

Claims11

Dependent claims

A process for the manufacture of final intermediate (FI) comprising the steps:

(a) reacting intermediate I1, wherein X is I, with at least one metalation agent, and subsequently adding the reaction product of such metalation to intermediate I2, wherein PG is a protection group, to yield intermediate I3;
(b) methylating intermediate I3 to yield intermediate I4;
(c) reducing intermediate I4 with a reduction agent to yield intermediate I5;
and
(d) acetylating intermediate I5 to yield final intermediate FI;
wherein the intermediates I3, I4 and I5 are not isolated and/or purified before performing steps (b), (c) and/or (d), respectively:

3 more elements

Dependencies are inferred from the claim text.

Facts

Application

16/771,717Filed 17 Dec 2018

Priority

EP 1720831519 Dec 2017

Published

US 2021/0139520 A113 May 2021

Granted

18 Jan 2022

Term ends

Not estimatedThe source records don’t support an estimate.

Classification12 codes

C07D 309/10
With hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals,…:…
C07H 1/00
Processes for the preparation of sugar derivatives
C07C 69/614
Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety: of…
C07C 255/50
Having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton: to carbon atoms of non-condensed six-membered…

Synthesis of 1:1:1 co-crystal of 1-cyano-2-(4-cyclopropyl-benzyl)-4-(β-D-glucopyranos-1-yl)-benzene, L-proline and water

Life of this patent

Synthesis of 1:1:1 co-crystal of 1-cyano-2-(4-cyclopropyl-benzyl)-4-(β-D-glucopyranos-1-yl)-benzene, L-proline and water

Life of this patent

Abstract

Claims11