# US 8,785,663 B2 · Polymorphic forms of Lubiprostone

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- Number: US 8,785,663 B2
- Document ID: US8785663B2
- Status: Granted
- Kind: B2
- Application number: 13/575,680
- Filed: 2011-01-28
- Published: 2013-04-18
- Granted: 2014-07-22
- Earliest claimed: 2010-01-28
- Applicants: Alfredo Paul Ceccarelli; Kiran Kumar Kothakonda
- Inventors: Alfredo Paul Ceccarelli; Kiran Kumar Kothakonda
- Web page: https://patentgrep.com/patent/US8785663B2

## CPC

- C07D 311/94: condensed with rings other than six-membered or with ring systems containing such rings
- A61K 31/558: having heterocyclic rings containing oxygen as the only ring hetero atom, e.g. thromboxanes
- A61P 1/10: Laxatives
- C07C 405/00: Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins {; Analogues or derivatives thereof}
- C07B 2200/13: Crystalline forms, e.g. polymorphs
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

There is provided a crystalline form of Lubiprostone, termed APO-II and methods for making APO-II. APO-II is a polymorphic form of Lubiprostone.

## Claims

### Claim 1

A crystalline form of Lubiprostone having an X-ray powder diffraction pattern acquired using CuKα radiation comprising peaks, in terms of 2-theta, at approximately 8.98, 13.53, 18.06 and 22.74.

### Claim 2 (depends on 1)

The crystalline form of Lubiprostone of claim 1 wherein the X-ray powder diffraction pattern further comprises a peak, in terms of 2-theta, at approximately 20.80.

### Claim 3 (depends on 2)

The crystalline form of Lubiprostone of claim 2 having a 1% KBr FTIR spectrum comprising peaks, in terms of cm−1, at approximately 3470, 2938, 1738, 1710, 1473, 1383, 1313, 1210, 1159, 979, 891, 793, 726 and 580.

### Claim 4 (depends on 2)

The crystalline form of Lubiprostone of claim 2 having a FTIR spectrum substantially as shown in FIG. 2.

### Claim 5 (depends on 2)

The crystalline form of Lubiprostone of claim 2 having a DSC thermogram comprising an endothermic peak with a peak onset temperature of approximately 76° C. and a peak maximum of approximately 77° C.

### Claim 6 (depends on 2)

The crystalline form of Lubiprostone of claim 2 having a DSC thermogram substantially as shown in FIG. 3.

### Claim 7 (depends on 1)

The crystalline form of Lubiprostone of claim 1 wherein the X-ray powder diffraction pattern further comprises a peak, in terms of 2-theta, at approximately 20.57.

### Claim 8 (depends on 7)

The crystalline form of Lubiprostone of claim 7 having a 1% KBr FTIR spectrum comprising peaks, in terms of cm−1, at approximately 3470, 2938, 1738, 1710, 1473, 1383, 1313, 1210, 1159, 979, 891, 793, 726 and 580.

### Claim 9 (depends on 7)

The crystalline form of Lubiprostone of claim 7 having a FTIR spectrum substantially as shown in FIG. 2.

### Claim 10 (depends on 7)

The crystalline form of Lubiprostone of claim 7 having a DSC thermogram comprising an endothermic peak with a peak onset temperature of approximately 76° C. and a peak maximum of approximately 77° C.

### Claim 11 (depends on 7)

The crystalline form of Lubiprostone of claim 7 having a DSC thermogram substantially as shown in FIG. 3.

### Claim 12 (depends on 1)

The crystalline form of Lubiprostone of claim 1 having a 1% KBr FTIR spectrum comprising peaks, in terms of cm−1, at approximately 3470, 2938, 1738, 1710, 1473, 1383, 1313, 1210, 1159, 979, 891, 793, 726 and 580.

### Claim 13 (depends on 1)

The crystalline form of Lubiprostone of claim 1 having a FTIR spectrum substantially as shown in FIG. 2.

### Claim 14 (depends on 1)

The crystalline form of Lubiprostone of claim 1 having a DSC thermogram comprising an endothermic peak with a peak onset temperature of approximately 76° C. and a peak maximum of approximately 77° C.

### Claim 15 (depends on 1)

The crystalline form of Lubiprostone of claim 1 having a DSC thermogram substantially as shown in FIG. 3.

### Claim 16

A crystalline form of Lubiprostone having an X-ray powder diffraction pattern acquired using CuKα radiation substantially as shown in FIG. 1.

### Claim 17 (depends on 16)

The crystalline form of Lubiprostone of claim 16 having a 1% KBr FTIR spectrum comprising peaks, in terms of cm−1, at approximately 3470, 2938, 1738, 1710, 1473, 1383, 1313, 1210, 1159, 979, 891, 793, 726 and 580.

### Claim 18 (depends on 16)

The crystalline form of Lubiprostone of claim 16 having a FTIR spectrum substantially as shown in FIG. 2.

### Claim 19 (depends on 16)

The crystalline form of Lubiprostone of claim 16 having a DSC thermogram comprising an endothermic peak with a peak onset temperature of approximately 76° C. and a peak maximum of approximately 77° C.

### Claim 20 (depends on 16)

The crystalline form of Lubiprostone of claim 16 having a DSC thermogram substantially as shown in FIG. 3.