Crystalline form of 1-(β-D-glucopyransoyl)-4-methyl-3-[5-(4-fluorophenyl)-2- thienylmethyl]benzene hemihydrate

• US 7,943,582 B2
• Filed: 12/03/2007
• Issued: 05/17/2011
• Est. Priority Date: 12/04/2006
• Status: Active Grant

• Current Assignee: Mitsubishi Tanabe Pharma Corporation (Mitsubishi Chemical Group Corp.)
• Original Assignee: Mitsubishi Tanabe Pharma Corporation (Mitsubishi Chemical Group Corp.)
• Inventors: Kawanishi, Eiji, Nomura, Sumihiro
• Primary Examiner(s): OLSON, ERIC
• Application Number:
  US11/987,670
• Publication Number:
  US 20080146515A1
• Time in Patent Office: 1,261 Days
• Field of Search: None
• US Class Current: 514/23
• CPC Class Codes: A61K 31/7034 attached to a carbocyclic compound, e.g. phloridzin
• CPC Class Codes: A61P 13/12 of the kidneys
• CPC Class Codes: A61P 17/02 for treating wounds, ulcers, burns, scars, keloids, or the like
• CPC Class Codes: A61P 25/00 Drugs for disorders of the nervous system
• CPC Class Codes: A61P 25/28 for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
• CPC Class Codes: A61P 3/00 Drugs for disorders of the metabolism of the blood or the extracellular fluid A61P7/00
• CPC Class Codes: A61P 3/04 Anorexiants; Antiobesity agents
• CPC Class Codes: A61P 3/06 Antihyperlipidemics
• CPC Class Codes: A61P 3/10 for hyperglycaemia, e.g. antidiabetics
• CPC Class Codes: A61P 3/12 for electrolyte homeostasis
• CPC Class Codes: A61P 5/00 Drugs for disorders of the endocrine system
• CPC Class Codes: A61P 5/50 for increasing or potentiating the activity of insulin
• CPC Class Codes: A61P 9/10 for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
• CPC Class Codes: A61P 9/12 Antihypertensives
• CPC Class Codes: C07H 7/04 Carbocyclic radicals

Abstract

A novel crystal form of 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]benzene hemihydrate, and having favorable characteristics, is characterized by its x-ray powder diffraction pattern and/or by its infra-red spectrum.

Claims

1. A crystalline form of 1-(β

-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]benzene hemihydrate.

2. A crystalline form of 1-(β

-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]benzene hemihydrate of claim 1, having a powder x-ray diffraction pattern comprising the following 2θ

values measured using CuK_α

radiation;

4.36±

0.2, 13.54±

0.2, 16.00±

0.2, 19.32±

0.2, and 20.80±

0.2.

3. A crystalline form of 1-(β

-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]benzene hemihydrate of claim 1, having substantially the same X-ray diffraction pattern as set out in FIG. 1.

4. A crystalline form of 1-(β

-D-glucopyranosyl)-4-methyl-3[5-(4-fluorophenyl)-2-thienylmethyl]benzene hemihydrate of claim 1, having substantially the same IR spectrum, as set out in FIG. 2.

5. A process for the preparation of a crystalline form of 1-(β

-D-glucopyranosyl) -4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]benzene hemihydrate of claim 1, which comprises forming a solution of 1-(β

-D-glucopyranosyl)-4-methyl-3[5-(4-fluoro-phenyl) -2-thienylmethyl]benzene and crystallizing said hemihydrate from the solution by precipitation or recrystallization.

6. A pharmaceutical composition comprising an effective amount of a crystalline form of 1-(β

-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]benzene hemihydrate of claim 1 and a pharmaceutically acceptable carrier.

7. A method for treatment or delaying the progression or onset of diabetes mellitus, diabetic retinopathy, diabetic neuropathy, diabetic nephropathy, delayed wound healing, insulin resistance, hyperglycemia, hyperinsulinemia, elevated blood levels of fatty acids, elevated blood levels of glycerol, hyperlipidemia, obesity, hypertriglyceridemia, Syndrome X, diabetic complications, atherosclerosis, or hypertension, which comprises administering a therapeutically effective amount of a crystalline form of 1-(β

-D-glucopyranosyl) -4-methyl-3[5-(4-fluorophenyl)-2-thienylmethyl]benzene hemihydrate of claim 1 to a subject in need thereof.