L-proline and citric acid co-crystals of (2S, 3R, 4R, 5S,6R)-2-(3-((5-(4-fluorophenyl)thiopen-2-yl)methyl)4-methylphenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Patent metadata

Field	Value
Publication number	US-9035044-B2
Application number	US-201213466249-A
Country	US
Kind code	B2
Filing date	May 8, 2012
Priority date	May 9, 2011
Publication date	May 19, 2015
Grant date	May 19, 2015

Abstract

The present invention is directed to L-proline and citric acid co-crystals of (2S,3R,4R,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol, pharmaceutical compositions containing said co-crystals and their use in the treatment glucose-related disorders such as Type 2 diabetes mellitus and Syndrome X.

First claim

What is claimed:

1. An L-proline co-crystal of a compound of formula (I-X)

2. The L-proline co-crystal as in claim 1 , comprising the following pXRD peaks °2θ: 3.74, 9.50, 10.98, 17.78, 18.62, 21.94, 23.43 and 26.82; wherein the pXRD peaks are measured using Cu/K g λ1.54056Å radiation.

3. The L-proline co-crystal as in claim 1 , wherein the co-crystal exhibits a melting point of 188° C., as measured by DSC.

4. A citric acid co-crystal of a compound of formula (I-X)

5. The citric acid co-crystal as in claim 4 , comprising the following pXRD peaks °2θ: 4.2, 9.16, 12.39, 16.54, 17.69, 19.70, 23.63 and 25.66 wherein the pXRD peaks are measured using Cu/K α λ1.54056Å radiation.

6. The citric acid co-crystal as in claim 4 , wherein the co-crystal exhibits a melting point of about 156° C., as measured by DSC.

Assignees

• Nguyen Minh
• Collier Edwin A
• Janssen Pharmaceutica Nv

Inventors

• Nguyen Minh
• Collier Edwin A

Classifications

• A61P3/10

  for hyperglycaemia, e.g. antidiabetics · CPC title

• A61P9/10

  for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis · CPC title

• C07D409/10 Primary

  linked by a carbon chain containing aromatic rings · CPC title

• C07D207/16

  Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals · CPC title

• C07C55/22

  Tricarboxylic acids · CPC title