# US 2013/0158264 A1 · Polymorphs of OSI-906

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- Number: US 2013/0158264 A1
- Document ID: US20130158264A1
- Status: Published application
- Kind: A1
- Application number: 13/805,402
- Filed: 2011-06-23
- Published: 2013-06-20
- Earliest claimed: 2010-06-23
- Inventors: Arlindo L. Castelhano; David A. Enger; Jason A. Hanko; Josef A. Rechka; Jing Teng; Yonglai Yang
- Web page: https://patentgrep.com/patent/US20130158264A1

## CPC

- C07D 487/04: Ortho-condensed systems
- A61K 31/4985: Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
- A61P 35/00: Antineoplastic agents
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- 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

## Abstract

Polymorphic forms of the tyrosine kinase inhibitor OSI-906, preparation, pharmaceutical compositions, and uses thereof. The invention includes methods of treating diseases such as cancer, including cancer mediated at least in part by IGF-1 R and/or IR, with the polymorphs and compositions. This Abstract is not limiting of the invention.

## Claims

### Claim 1

Crystalline polymorph Form A of OSI-906.

### Claim 2 (depends on 1)

The polymorph Form A of claim 1, which exhibits an X-ray diffraction pattern with characteristic peaks substantially as set forth in Table 1, an X-ray diffraction pattern essentially resembling that of FIG. 2, a TGA profile substantially resembling FIG. 17, or a DSC thermogram substantially resembling that of FIG. 16.

### Claim 3 (depends on 1)

The polymorph Form A of claim 1, which exhibits an X-ray diffraction pattern comprising peaks (°2θ) at about 12.4, 12.6, 16.6, 18.5, 19.4, 20.2, and 22.

### Claim 4

(canceled)

### Claim 5 (depends on 1)

The polymorph of claim 1, present as a material comprising at least about 98% by weight Form A based on the total amount of OSI-906.

### Claim 6 (depends on 5)

The polymorph of claim 5, which is present as a material that is substantially free of amorphous OSI-906, OSI-906 hydrates, and OSI-906 solvates.

### Claim 7 (depends on 6)

The polymorph of claim 6, which is substantially free of solvent.

### Claim 8 (depends on 1)

The polymorph of claim 1, which is prepared by a process comprising: (a) preparing a slurry of OSI-906 in an alcohol; (b) heating the slurry; and (c) isolating crystalline Form A.

### Claim 9 (depends on 8)

The polymorph of claim 8, wherein the preparing a slurry in (a) further comprises adjusting pH to about 5 and the alcohol in (a) comprises isopropanol, n-propanol, n-butanol, sec-butanol, t-butanol, or iso-butanol.

### Claim 10

(canceled)

### Claim 11

Crystalline polymorph Form B of OSI-906.

### Claim 12 (depends on 11)

The polymorph Form B of OSI-906 of claim 11, which exhibits an X-ray diffraction pattern with characteristic peaks as set forth in Table 3, an X-ray diffraction pattern substantially resembling that of FIG. 3, a DSC thermogram substantially resembling that of FIG. 18, a TGA signal substantially resembling that of FIG. 19, or a 1H NMR spectrum in DMSO-d6 substantially resembling that of FIG. 31.

### Claim 13 (depends on 11)

The polymorph Form B of claim 11, which exhibits an X-ray diffraction pattern comprising peaks (°2θ) at about 10.1, 10.6, 11.2, 13.3, 15.3, 16.3, 21.8, 22.3, 22.4, 24.4, and 27.8.

### Claim 14

Crystalline polymorph Form C of OSI-906.

### Claim 15 (depends on 14)

The polymorph Form C of claim 14, which exhibits an X-ray diffraction pattern with characteristic peaks as set forth in Table 5, an X-ray diffraction pattern substantially resembling that of FIG. 4, a DSC thermogram substantially resembling that of FIG. 20, or a TGA signal substantially resembling that of FIG. 21.

### Claim 16 (depends on 14)

The polymorph Form C of claim 14, which exhibits an X-ray diffraction pattern comprising peaks (°2θ) at about 10.6, 11.2, 13.3, 15.3, 21.2, 24.3, and 25.5.

### Claim 17 (depends on 14)

The polymorph Form C of claim 14, which is present as a material comprising at least about 95% or more by weight Form C based on the total amount of OSI-906.

### Claim 18 (depends on 17)

The polymorph of claim 17, which is present as a material that is substantially free of amorphous OSI-906, OSI-906 hydrates, and OSI-906 solvated, other than polymorph Form C.

### Claim 19 (depends on 18)

The polymorph of claim 18, which is prepared by a process comprising: (a) preparing a solution of OSI-906 in an alcohol; (b) heating the solution; and (c) isolating crystalline Form C.

### Claim at position 20

20-28. (canceled)