Thiophene compounds

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A pharmaceutical composition comprising Form M, H, P, X and ZA of Compound 1, or an amorphous form of Compound 1, wherein Compound 1 is represented by the following structural formula:

• and
• at least one pharmaceutically acceptable carrier or excipient.

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A method of preparing Form M of Compound (1) represented by the following structural formula:

• comprising stirring a mixture of Compound (1) and a solvent system that includes isopropanol, ethyl acetate, n-butyl acetate, methyl acetate, acetone, 2-butanone, or heptane, or a combination thereof at a temperature in a range of 10° C. to 47° C. to form From M of Compound (1).

A method of preparing Form H of Compound (1) represented by the following structural formula:

• Comprising stirring a solution of Compound (1) at a temperature in a range of 48° C. to 70° C. to form Form H of Compound (1).

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A method of preparing Form P of Compound (1) represented by the following structural formula:

• comprising:
• stirring a mixture of Compound (1) and a solvent system that include a solvent selected from the group consisting of dichloromethane, tetrahydrofuran (THF), and a mixture thereof at room temperature to form Form P of Compound (1).

A method of preparing Form X of Compound (1) represented by the following structural formula:

• comprising removing ethyl acetate from ethylacetate solvate G of Compound (1), wherein ethylacetate solvate G of Compound (1) is characterized as having an X-ray powder diffraction pattern with characteristic peaks expressed in 2-theta±0.2 at the following positions:
• 7.5 and 12.1, wherein the X-ray powder diffraction pattern is obtained at room temperature using Cu K alpha radiation.

A method of preparing Form ZA of Compound (1) represented by the following structural formula:

• comprising removing n-butyl acetate from n-butyl acetate solvate A of Compound (1), wherein
• n-butyl acetate solvate A of Compound (1) is characterized as having an X-ray powder diffraction pattern with characteristic peaks expressed in 2-theta±0.2 at the following positions:
• 9.7 and 16.5, wherein the X-ray powder diffraction pattern is obtained at room temperature using Cu K alpha radiation.