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.

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 present invention provides compounds including curcuminoids and analogs thereof, as well as methods of making the same. In various aspects, the method of making the compounds is free of added solvents.

The present invention provides processes for the preparation of 3, 5-Dihydroxy-4-isopropyl-trans-stilbene or a salt or solvate thereof and novel intermediates used therein. In some embodiments the 3, 5-Dihydroxy-4-isopropyl-trans-stilbene is prepared from (E)-2-chloro-2-isopropyl-5-styrylcyclohexane-1,3-dione. Also disclosed are crystal forms of 3, 5-Dihydroxy-4-isopropyl-trans-stilbene or a salt or solvate thereof and pharmaceutical compositions comprising same.

The present invention provides processes for the preparation of 3, 5-Dihydroxy-4-isopropyl-trans-stilbene or a salt or solvate thereof and novel intermediates used therein. In some embodiments the 3, 5-Dihydroxy-4-isopropyl-trans-stilbene is prepared from (E)-2-chloro-2-isopropyl-5-styrylcyclohexane-1,3-dione. Also disclosed are crystal forms of 3, 5-Dihydroxy-4-isopropyl-trans-stilbene or a salt or solvate thereof and pharmaceutical compositions comprising same.

Provided is a method for producing (alkyl)arene compounds represented by Formulae 3-1, 3-2, and 3-3 by the Friedel-Crafts alkylation reaction of alkyl halide compounds and arene compounds using organic phosphine compounds as a catalyst. ##STR00001##

Provided is a method for producing (alkyl)arene compounds represented by Formulae 3-1, 3-2, and 3-3 by the Friedel-Crafts alkylation reaction of alkyl halide compounds and arene compounds using organic phosphine compounds as a catalyst. ##STR00001##

A quinone derivative is represented by general formula (1), (2), or (3). In general formulae (1), (2), and (3), R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.11, R.sup.12, R.sup.13, R.sup.14, R.sup.21, R.sup.22, R.sup.23, and R.sup.24 each represent, independently of one another, a hydrogen atom, a cyano group, a halogen atom, an optionally substituted alkyl group having a carbon number of 1-6, or an optionally substituted alkoxy group having a carbon number of 1-6. R.sup.5, R.sup.6, R.sup.15, R.sup.16, R.sup.25, and R.sup.26 each represent, independently of one another, an optionally substituted alkyl group having a carbon number of 1-6, an optionally substituted alkoxy group having a carbon number of 1-6, an optionally substituted aryl group having a carbon number of 6-14, an optionally substituted aralkyl group having a carbon number of 7-12, or an optionally substituted cycloalkyl group having a carbon number of 3-10.

##STR00001##

A quinone derivative is represented by general formula (1), (2), or (3). In general formulae (1), (2), and (3), R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.11, R.sup.12, R.sup.13, R.sup.14, R.sup.21, R.sup.22, R.sup.23, and R.sup.24 each represent, independently of one another, a hydrogen atom, a cyano group, a halogen atom, an optionally substituted alkyl group having a carbon number of 1-6, or an optionally substituted alkoxy group having a carbon number of 1-6. R.sup.5, R.sup.6, R.sup.15, R.sup.16, R.sup.25, and R.sup.26 each represent, independently of one another, an optionally substituted alkyl group having a carbon number of 1-6, an optionally substituted alkoxy group having a carbon number of 1-6, an optionally substituted aryl group having a carbon number of 6-14, an optionally substituted aralkyl group having a carbon number of 7-12, or an optionally substituted cycloalkyl group having a carbon number of 3-10.

##STR00001##

A quinone derivative is represented by general formula (1). In general formula (1), at least one of R.sup.1-R.sup.3 and at least one of R.sup.4-R.sup.6 each represent, independently of one another, an alkyl group having 4 to 10 carbon atoms or an alkyl group having 2 to 5 carbon atoms that has an aryl group having 6 to 14 carbon atoms. All other of R.sup.1-R.sup.3 and all other of R.sup.4-R.sup.6 each represent, independently of one another, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 14 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms.

##STR00001##