This disclosure relates to modulators of liver receptor homologue 1 (LRH-1) and methods of managing disease and conditions related thereto. In certain embodiments, modulators are derivatives of hexahydropentalene. In certain embodiments, this disclosure relates to methods of treating or preventing cancer, diabetes, or cardiovascular disease by administering an effective amount of a hexahydropentalene derivative disclosed herein.

A refining method according to the present invention is a refining method for crystallizing a compound with at least one crystal form, including setting, as a target wavelength and a target temperature, a specific infrared wavelength and a specific temperature at which a specific crystal form precipitates from a solution of the compound dissolved in a solvent, and using an infrared radiation apparatus capable of emitting infrared radiation including the target wavelength to evaporate the solvent and precipitate the specific crystal form while irradiating the solution with infrared radiation including the target wavelength and adjusting a temperature of the solution to the target temperature.

A refining method according to the present invention is a refining method for crystallizing a compound with at least one crystal form, including setting, as a target wavelength and a target temperature, a specific infrared wavelength and a specific temperature at which a specific crystal form precipitates from a solution of the compound dissolved in a solvent, and using an infrared radiation apparatus capable of emitting infrared radiation including the target wavelength to evaporate the solvent and precipitate the specific crystal form while irradiating the solution with infrared radiation including the target wavelength and adjusting a temperature of the solution to the target temperature.

A refining method according to the present invention is a refining method for crystallizing a compound with at least one crystal form, including setting, as a target wavelength and a target concentration, a specific infrared wavelength and a specific concentration at which a specific crystal form precipitates from a solution of the compound dissolved in a solvent, and using an infrared radiation apparatus capable of emitting infrared radiation including the target wavelength to evaporate the solvent and precipitate the specific crystal form while irradiating a solution of the compound dissolved in the solvent at the target concentration with infrared radiation including the target wavelength.

A refining method according to the present invention is a refining method for crystallizing a compound with at least one crystal form, including setting, as a target wavelength and a target concentration, a specific infrared wavelength and a specific concentration at which a specific crystal form precipitates from a solution of the compound dissolved in a solvent, and using an infrared radiation apparatus capable of emitting infrared radiation including the target wavelength to evaporate the solvent and precipitate the specific crystal form while irradiating a solution of the compound dissolved in the solvent at the target concentration with infrared radiation including the target wavelength.

This disclosure relates to modulators of liver receptor homologue 1 (LRH-1) and methods of managing disease and conditions related thereto. In certain embodiments, modulators are derivatives of hexahydropentalene. In certain embodiments, this disclosure relates to methods of treating or preventing cancer, diabetes, or cardiovascular disease by administering an effective amount of a hexahydropentalene derivative disclosed herein.

A refining method according to the present invention is a refining method for crystallizing a compound with at least one crystal form, including: setting, as a target wavelength, a specific infrared wavelength at which a specific crystal form precipitates from a solution of the compound dissolved in a solvent; and using an infrared radiation apparatus capable of emitting infrared radiation including the target wavelength to evaporate the solvent and precipitate the specific crystal form while irradiating the solution with infrared radiation including the target wavelength. The specific infrared wavelength is preferably set as the target wavelength based on an infrared absorption spectrum of the crystal form and the dissolution rate of the compound in the solvent.

A refining method according to the present invention is a refining method for crystallizing a compound with at least one crystal form, including: setting, as a target wavelength, a specific infrared wavelength at which a specific crystal form precipitates from a solution of the compound dissolved in a solvent; and using an infrared radiation apparatus capable of emitting infrared radiation including the target wavelength to evaporate the solvent and precipitate the specific crystal form while irradiating the solution with infrared radiation including the target wavelength. The specific infrared wavelength is preferably set as the target wavelength based on an infrared absorption spectrum of the crystal form and the dissolution rate of the compound in the solvent.

This disclosure relates to modulators of liver receptor homologue 1 (LRH-1) and methods of managing disease and conditions related thereto. In certain embodiments, modulators are derivatives of hexahydropentalene. In certain embodiments, this disclosure relates to methods of treating or preventing cancer, diabetes, or cardiovascular disease by administering an effective amount of a hexahydropentalene derivative disclosed herein.

The invention belongs to the pharmaceutical manufacturing field, which relates to a novel process for the preparation of substituted phenylacetic acids derivatives, especially relates to the preparation of 2-(4-(2-oxocyclopentyl)phenyl)propanoic acid. The process for the preparation of the precursor form of loxoprofen which use 1,4-di-halobenzyl compounds or disubstituted benzyl compounds as starting material, is through the substitution reaction of cyclopentanone groups or its precursor compounds.

##STR00001##

Wherein X is halogen, L.sub.1 is a suitable leaving group selected from halogen, OH, OMs, OTs, OTf and the like; L.sub.2 is a suitable leaving group selected from halogen, CN, OH, CH.sub.2OH, CHO, CH.sub.3NO.sub.2, ester group, NR.sub.4R.sub.5, OTf, OTs, OMs, CCR.sub.6, CCR.sub.7 and the like, wherein R.sub.4, R.sub.5, R.sub.6, R.sub.7 are short chain alkyl groups; Z is cyclopentanone group and its precursor form selected from

##STR00002##

and the like; R.sub.3 is short chain alkyl groups. L.sub.3 is a suitable leaving group selected from halogen, OH, OMs, OTs, OT.sub.f and the like, or organometallic groups. The invention also include the detailed procedure to convert the precursor compounds of cyclopentanone group to cyclopentanone, followed by the transformation of the precursor compounds of loxoprofen to loxoprofen.