# US 8,785,435 B2 · Solid forms

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- Number: US 8,785,435 B2
- Document ID: US8785435B2
- Status: Granted
- Kind: B2
- Application number: 13/650,159
- Filed: 2012-10-12
- Published: 2013-07-04
- Granted: 2014-07-22
- Earliest claimed: 2011-10-20
- Assignees: Hoffmann-La Roche Inc.
- Applicants: Hoffmann-La Roche Inc.
- Inventors: Pascal Dott; Olaf Grassmann; Michael Kammerer; Joachim Manns; Urs Schwitter; Andrew Thomas; Nicole Wyttenbach
- Web page: https://patentgrep.com/patent/US8785435B2

## CPC

- C07D 413/12: linked by a chain containing hetero atoms as chain links
- A61P 9/10: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/04: Centrally acting analgesics, e.g. opioids
- A61P 25/14: for treating abnormal movements, e.g. chorea, dyskinesia
- A61P 25/16: Anti-Parkinson drugs
- A61P 25/18: Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A61P 25/20: Hypnotics; Sedatives
- A61P 25/22: Anxiolytics
- A61P 25/24: Antidepressants
- 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
- A61P 25/30: for treating abuse or dependence
- A61P 25/32: Alcohol-abuse
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The instant invention relates to novel solid forms of the compound of formula (I) as well as solvates, inclusion complexes with other suitable compounds, processes for their manufacture, pharmaceutical compositions containing these solid forms, and their use as pharmaceuticals.

## Claims

### Claim 1

A solid font of the compound of formula (I)
having an XRPD pattern comprising at least one XRPD peak in the range of angles of diffraction 2Theta of 10.3° to 13.3°, wherein the solid form is crystalline (1,1-dioxo-1λ6-thiomorpholin-4-yl)-{6-[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-pyridin-3-yl}-methanone in anhydrous polymorphic form C.

### Claim 2 (depends on 1)

The compound of claim 1, comprising crystalline 1,1-dioxo-1λ6-thiomorpholin-4-yl)-{6-[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-pyridin-3-yl}-methasone in anhydrous polymorphic form C, having an XRPD diffraction pattern comprising XRPD peaks at angles of diffraction 2Theta of approximately 17.4°, 23.4°.

### Claim 3 (depends on 1)

The compound of claim 1, having crystalline polymorphic form C, having the XRPD diffraction pattern of FIG. 3.

### Claim 4 (depends on 1)

The compound of claim 1, comprising crystalline polymorphic form C, having the FTIR spectrum of FIG. 10.

### Claim 5 (depends on 1)

The compound of claim 1, comprising crystalline polymorphic form C, having the Raman spectrum of FIG. 16.

### Claim 6 (depends on 1)

The solid form of claim 1, having a purity of at least 90% (w/w).

### Claim 7

A high-shear process for preparing a solid form of a compound of formula (I)
having an XRPD pattern comprising at least one XRPD peak in the range of angles of diffraction 2Theta of 103° to 13.3° comprising:
a) injecting a solution of an educt solid form of compound (I) in a solvent into a high-shear mixer having a rotor-stator system comprising an antisolvent;
b) agitating the rotor-stator system of the high-shear mixer to form a suspension; and
c) physically separating the solid form from the suspension.

### Claim 8

A pharmaceutical composition comprising a solid form of a compound of formula (I) the compound of formula (I)
having an XRPD pattern comprising at least one XRPD peak in the range of angles of diffraction 2Theta of 103° to 13.3°
and a pharmaceutically acceptable excipient,
wherein the solid form is crystalline (1,1-dioxo-1λ6-thiomorpholin-4-yl)-{6-[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-pyridin-3-yl}-methanone in anhydrous polymorphic form C,
wherein the pharmaceutical composition is administered in an administrative form selected from tablets, powders, and capsules.