The present disclosure provides industrially scalable methods of making (Z)-endoxifen or a salt thereof, crystalline forms of endoxifin, and compositions comprising them. The present disclosure also provides methods for treating hormone-dependent breast and hormone-dependent reproductive tract disorders.

The present disclosure provides industrially scalable methods of making (Z)-endoxifen or a salt thereof, crystalline forms of endoxifin, and compositions comprising them. The present disclosure also provides methods for treating hormone-dependent breast and hormone-dependent reproductive tract disorders.

The present invention relates to metal salts of 2-[3-[(3R)-3-[[2-chloro-3-(trifluoromethyl)phenyl]methyl-(2,2-diphenylethyl)amino]butoxy]phenyl]acetic acid which exhibit improved physical properties and stability. The invention also relates to pharmaceutical compositions including an effective amount of the metal salts, as well as methods of treating cancer including administration of a pharmaceutical composition including a salt of the invention to a subject in need thereof.

The present invention provides zuclomiphene salts, zuclomiphene binaphthyl hydrogen phosphate salt (1-A).Math.(BPA) and zuclomiphene oxalate salt (1-A).Math.(OXL), crystalline forms thereof and processes for the preparation thereof.

The present invention provides zuclomiphene salts, zuclomiphene binaphthyl hydrogen phosphate salt (1-A).Math.(BPA) and zuclomiphene oxalate salt (1-A).Math.(OXL), crystalline forms thereof and processes for the preparation thereof.

A compound of formula I

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with improved TGFβ signaling pathway inhibitory activity, improved therapeutic efficacy and improved toxicity profile, as well as two prodrugs thereof are disclosed.

Compositions comprising said TGFβ signaling pathway inhibitor and prodrugs thereof are also disclosed. Additionally, present invention discloses said compound of formula I and prodrugs thereof for use in a method of treating diseases responsive to TGFβ signaling pathway inhibition.

The present invention relates to metal salts of 2-[3-[(3R)-3-[[2-chloro-3-(trifluoromethyl)phenyl]methyl-(2,2-diphenylethyl)amino]butoxy]phenyl]acetic acid which exhibit improved physical properties and stability. The invention also relates to pharmaceutical compositions including an effective amount of the metal salts, as well as methods of treating cancer including administration of a pharmaceutical composition including a salt of the invention to a subject in need thereof.

The present invention provides novel crystalline forms of zuclomiphene citrate. Specific crystalline forms provided by the present invention include zuclomiphene citrate Forms APO-I, APO-II, APO-III, and APO-IV. Also provided are pharmaceutical compositions including the zuclomiphene citrate crystalline forms, processes for the preparation thereof and the use of these forms in the treatment of a disorder selected from the group including osteoporosis, bone fractures, loss of bone mineral density (BMD) and hot flashes in a subject suffering therefrom.

The present invention provides processes for the preparation of zuclomiphene, as well as intermediates useful in the preparation thereof. In particular, processes are provided for the carbometallation of diphenylacetylene with a compound of Formula (3) to afford either zuclomiphene or an intermediate which is converted to zuclomiphene. ##STR00001##

The present invention provides processes for the preparation of zuclomiphene, as well as intermediates useful in the preparation thereof. In particular, processes are provided for the carbometallation of diphenylacetylene with a compound of Formula (3) to afford either zuclomiphene or an intermediate which is converted to zuclomiphene. ##STR00001##