# US 8,785,608 B2 · Crystalline heteroaromatic fluoroglycoside hydrates, pharmaceuticals comprising these compounds and their use

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- Number: US 8,785,608 B2
- Document ID: US8785608B2
- Status: Granted
- Kind: B2
- Application number: 13/391,842
- Filed: 2010-08-26
- Published: 2012-09-20
- Granted: 2014-07-22
- Earliest claimed: 2009-08-26
- Assignees: Sanofi
- Applicants: David Rigal; Franceska Fischer; Bernd Becker; Martin Feth; Norbert Nagel; Bruno Baumgartner; Martin Bröeckelmann
- Inventors: David Rigal; Franceska Fischer; Bernd Becker; Martin Feth; Norbert Nagel; Bruno Baumgartner; Martin Bröeckelmann
- Web page: https://patentgrep.com/patent/US8785608B2

## CPC

- C07H 17/02: Heterocyclic radicals containing only nitrogen as ring hetero atoms
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The invention relates to crystalline hydrates of the formula I in which n has a value of from 2.1 to 2.5. The compound is suitable, for example, as an antidiabetic.

## Claims

### Claim 1

A crystalline hydrate of the formula I,
in which n has a value of from 2.1 to 2.5.

### Claim 2 (depends on 1)

The crystalline hydrate of the formula I as claimed in claim 1 wherein n has a value of 2.25.

### Claim 3 (depends on 1)

The crystalline hydrate of the formula I as claimed in claim 1 wherein the XRPD, measured with CuKα radiation, has a main peak of 5.8 degrees 2 theta±0.2 degrees 2 theta.

### Claim 4 (depends on 1)

The crystalline hydrate of the formula I as claimed in claim 1 wherein the XRPD, measured with CuKα radiation, has at least peaks of the following 2 theta values:
5.8, 10.3, 14.2±0.2 degrees 2 theta.

### Claim 5 (depends on 1)

The crystalline hydrate of the formula I as claimed in claim 1 wherein the XRPD, measured with CuKα radiation, has at least peaks of the following 2 theta values:
5.8, 7.1, 10.3, 14.2, 19.7±0.2 degrees 2 theta.

### Claim 6 (depends on 1)

The crystalline hydrate of the formula I as claimed in claim 1 wherein the XRPD, measured with CuKα radiation, has at least peaks of the following 2 theta values:
5.8, 7.1, 10.3, 14.2, 19.9, 19.7, 21.8±0.2 degrees 2 theta.

### Claim 7 (depends on 1)

A pharmaceutical composition comprising the crystalline hydrate of claim 1.

### Claim 8 (depends on 7)

The pharmaceutical composition of claim 7, wherein said composition is in solid form.

### Claim 9 (depends on 7)

The pharmaceutical composition of claim 7, further comprising one or more blood glucose-lowering active ingredients.

### Claim 10 (depends on 8)

The pharmaceutical composition of claim 8, further comprising one or more blood glucose-lowering active ingredients.

### Claim 11 (depends on 7)

A method of treating type 1 and type 2 diabetes in a patient in need thereof comprising administering to said patient a therapeutically effective amount of the pharmaceutical composition of claim 7.

### Claim 12 (depends on 7)

A method of lowering blood glucose in a patient in need thereof comprising administering to said patient a therapeutically effective amount of the pharmaceutical composition of claim 7.

### Claim 13 (depends on 9)

A method of treating type 1 and type 2 diabetes in a patient in need thereof comprising administering to said patient a therapeutically effective amount of the pharmaceutical composition of claim 9.

### Claim 14 (depends on 9)

A method of lowering blood glucose in a patient in need thereof comprising administering to said patient a therapeutically effective amount of the pharmaceutical composition of claim 9.

### Claim 15 (depends on 7)

A process for preparing the pharmaceutical composition of claim 7, comprising mixing the active ingredient with a pharmaceutically suitable carrier and converting this mixture into a form suitable for administration.