# US 9,433,606 B2 · Solid forms comprising (+)-2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione, compositions thereof, and uses thereof

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- Number: US 9,433,606 B2
- Document ID: US9433606B2
- Status: Granted
- Kind: B2
- Application number: 14/670,336
- Filed: 2015-03-26
- Published: 2015-07-16
- Granted: 2016-09-06
- Earliest claimed: 2002-03-20
- Assignees: Celgene Corporation
- Applicants: Celgene Corporation
- Inventors: George W. Muller; Peter H. Schafer; Hon-Wah Man; Chuansheng Ge; Jean Xu
- Web page: https://patentgrep.com/patent/US9433606B2

## CPC

- A61K 31/4035: Isoindoles, e.g. phthalimide
- A61K 9/2054: {Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose}
- A61K 9/4866: {Organic macromolecular compounds}
- A61P 17/06: Antipsoriatics
- C07C 317/28: with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
- C07D 209/48: with oxygen atoms in positions 1 and 3, e.g. phthalimide
- C07B 2200/07: Optical isomers
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

Solid forms comprising (+)-2-[1-(3-Ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione, compositions comprising the solid forms, methods of making the solid forms and methods of their use are disclosed. The methods include methods of treating and/or preventing disorders ameliorated by the reduction of levels of TNF-α or the inhibition of PDE4.

## Claims

### Claim 1

A method of treating sarcoidosis, the method comprising administering to a patient having sarcoidosis a therapeutically effective amount of a Form B crystal form of the compound of Formula (I):
which is enantiomerically pure, and which has an X-ray powder diffraction pattern comprising peaks at about 10.1, 13.5, 20.7, and 26.9 degrees 2θ.

### Claim 2 (depends on 1)

The method of claim 1, wherein the crystal form has an X-ray powder diffraction pattern further comprising peaks at about 12.4, 15.7, 18.1, and 24.7 degrees 2θ.

### Claim 3 (depends on 2)

The method of claim 2, wherein the crystal form has an X-ray powder diffraction pattern further comprising peaks at about 16.3, 22.5, 26.2, and 29.1 degrees 2θ.

### Claim 4 (depends on 1)

The method of claim 1, wherein the crystal form has an X-ray powder diffraction pattern matching the pattern depicted in FIG. 5.

### Claim 5 (depends on 1)

The method of claim 1, wherein the crystal form has a differential scanning calorimetry plot comprising an endothermic event with an onset temperature of about 154° C.

### Claim 6 (depends on 1)

The method of claim 1, wherein the crystal form has a differential scanning calorimetry plot matching the plot depicted in FIG. 6.

### Claim 7 (depends on 1)

The method of claim 1, wherein the crystal form has a thermal gravimetric analysis plot comprising a mass loss of less than about 1% when heated from about 25° C. to about 140° C.

### Claim 8 (depends on 7)

The method of claim 7, wherein the mass loss is about 0.25%.

### Claim 9 (depends on 1)

The method of claim 1, wherein the crystal form has a thermal gravimetric analysis plot matching the plot depicted in FIG. 7.

### Claim 10 (depends on 1)

The method of claim 1, wherein the crystal form exhibits a mass increase of less than about 1% when subjected to an increase in relative humidity from about 0% to about 95% relative humidity.

### Claim 11 (depends on 10)

The method of claim 10, wherein the mass increase is about 0.6%.

### Claim 12 (depends on 1)

The method of claim 1, wherein the crystal form has a moisture sorption isotherm plot matching the plot depicted in FIG. 8.

### Claim 13 (depends on 1)

The method of claim 1, wherein the crystal form is stable upon exposure to about 40° C. and about 75% relative humidity for about 4 weeks.

### Claim 14 (depends on 1)

The method of claim 1, wherein the sarcoidosis is pulmonary sarcoidosis.

### Claim 15 (depends on 1)

The method of claim 1, wherein the sarcoidosis is cutaneous sarcoidosis.