Methods of preparing unsaturated compounds or analogs through dehydrogenation of corresponding saturated compounds and/or hydrogenation of aromatic compounds are disclosed.

The present invention relates to a 4-(2-amino-tetrahydronaphthaleneyl)pyrimidine derivative, a preparation method thereof, and a pharmaceutical composition for the prevention or treatment of cancer comprising the same as an active ingredient. The 4-(2-amino-tetrahydronaphthaleneyl)pyrimidine derivative, the optical isomer thereof, or the pharmaceutically acceptable salt thereof of the present invention is very effective in suppressing anaplastic lymphoma kinase (ALK) activity and as a result it can improve the effectiveness of treatment on cancer cells having anaplastic lymphoma kinase (ALK) fusion proteins such as EML4-ALK and NPM-ALK, so that it can be effectively used as a pharmaceutical composition for preventing or treating cancer.

The present invention relates to a 4-(2-amino-tetrahydronaphthaleneyl)pyrimidine derivative, a preparation method thereof, and a pharmaceutical composition for the prevention or treatment of cancer comprising the same as an active ingredient. The 4-(2-amino-tetrahydronaphthaleneyl)pyrimidine derivative, the optical isomer thereof, or the pharmaceutically acceptable salt thereof of the present invention is very effective in suppressing anaplastic lymphoma kinase (ALK) activity and as a result it can improve the effectiveness of treatment on cancer cells having anaplastic lymphoma kinase (ALK) fusion proteins such as EML4-ALK and NPM-ALK, so that it can be effectively used as a pharmaceutical composition for preventing or treating cancer.

The present invention provides an industrial method for producing 1,4-dimethylnaphthalene with a small content of 1,3-dimethylnaphthalene. In this method for producing 1,4-dimethylnaphthalene, 5-phenyl-2-hexene is cyclized in the presence of acid catalysts to prepare crude 1,4-dimethyl-1,2,3,4-tetrahydronaphthalene, the crude 1,4-dimethyl-1,2,3,4-tetrahydronaphthalene is dehydrogenized to obtain a crude 1,4-dimethylnaphthalene, and the crude 1,4-dimethylnaphthalene is purified by distillation. In this method, the concentration of 1,3-dimethyl-1,2,3,4-tetrahydronaphthalene in 1,4-dimethyl-1,2,3,4-tetrahydronaphthalene is 1.0% or less with respect to the 1,4-dimethyl-1,2,3,4-tetrahydronaphthalene.

The present invention provides an industrial method for producing 1,4-dimethylnaphthalene with a small content of 1,3-dimethylnaphthalene. In this method for producing 1,4-dimethylnaphthalene, 5-phenyl-2-hexene is cyclized in the presence of acid catalysts to prepare crude 1,4-dimethyl-1,2,3,4-tetrahydronaphthalene, the crude 1,4-dimethyl-1,2,3,4-tetrahydronaphthalene is dehydrogenized to obtain a crude 1,4-dimethylnaphthalene, and the crude 1,4-dimethylnaphthalene is purified by distillation. In this method, the concentration of 1,3-dimethyl-1,2,3,4-tetrahydronaphthalene in 1,4-dimethyl-1,2,3,4-tetrahydronaphthalene is 1.0% or less with respect to the 1,4-dimethyl-1,2,3,4-tetrahydronaphthalene.

By the control of the cyclization of 5-phenyl-2-hexene at a predetermined temperature, 1,4-dimethyltetralin is efficiently produced. The present invention provides a method for producing 1,4-dimethyitetralin, including a step of cyclizing 5-phenyl-2-hexene under reflux of solvents in the presence of acid catalysts.

Disclosed are methods of preparing unsaturated carbocyclic compounds through dehydrogenation of corresponding saturated carbocyclic compounds.

Disclosed are methods of preparing unsaturated carbocyclic compounds through dehydrogenation of corresponding saturated carbocyclic compounds.

The present disclosure relates generally to derivatives of polygodial and methods of use thereof. In some aspects, the present disclosure relates to using polygodial derivatives to treat cancer or other hyperproliferative diseases.

The present disclosure relates generally to derivatives of polygodial and methods of use thereof. In some aspects, the present disclosure relates to using polygodial derivatives to treat cancer or other hyperproliferative diseases.