The present disclosure relates to HIF-2? inhibitors and methods of making and using them for treating cancer. Certain compounds were potent in HIF-2? scintillation proximity assay, luciferase assay, and VEGF ELISA assay, and led to tumor size reduction and regression in 786-O xenograft bearing mice in vivo.

A composition comprising a fuel and at least one compound characterized by Formula I:

##STR00001##

wherein X is carbon, oxygen, or sulfur; R.sup.1 and R.sup.2 each independently are hydrogen, a C.sub.1 to C.sub.20 alkyl, or a C.sub.6 to C.sub.10 aryl; R.sup.3 and R.sup.3 each independently are hydrogen or a C.sub.1 to C.sub.4 alkyl; R.sup.4 and R.sup.4 each independently are hydrogen, a C.sub.1 to C.sub.4 alkyl, a C.sub.4 to C.sub.10 cycloalkyl, or a C.sub.6 to C.sub.10 aryl; R.sup.5 and R.sup.5 each independently are a C.sub.4 to C.sub.10 alkyl; R.sup.6 and R.sup.6 each independently are hydrogen or a C.sub.1 to C.sub.6 alkyl; and R.sup.7 and R.sup.7 each independently are hydrogen or a C.sub.1 to C.sub.4 alkyl; and wherein the compound of Formula I when subjected to GC-MS using electron ionization at greater than about 70 eV produces at least one ion having a mass-to-charge ratio of from 300 to 600.

A composition comprising a fuel and at least one compound characterized by Formula I:

##STR00001##

wherein X is carbon, oxygen, or sulfur; R.sup.1 and R.sup.2 each independently are hydrogen, a C.sub.1 to C.sub.20 alkyl, or a C.sub.6 to C.sub.10 aryl; R.sup.3 and R.sup.3 each independently are hydrogen or a C.sub.1 to C.sub.4 alkyl; R.sup.4 and R.sup.4 each independently are hydrogen, a C.sub.1 to C.sub.4 alkyl, a C.sub.4 to C.sub.10 cycloalkyl, or a C.sub.6 to C.sub.10 aryl; R.sup.5 and R.sup.5 each independently are a C.sub.4 to C.sub.10 alkyl; R.sup.6 and R.sup.6 each independently are hydrogen or a C.sub.1 to C.sub.6 alkyl; and R.sup.7 and R.sup.7 each independently are hydrogen or a C.sub.1 to C.sub.4 alkyl; and wherein the compound of Formula I when subjected to GC-MS using electron ionization at greater than about 70 eV produces at least one ion having a mass-to-charge ratio of from 300 to 600.

A composition comprising a fuel and at least one compound characterized by Formula I: ##STR00001##
wherein X is carbon, oxygen, or sulfur; R.sup.1 and R.sup.2 each independently are hydrogen, a C.sub.1 to C.sub.20 alkyl, or a C.sub.6 to C.sub.10 aryl; R.sup.3 and R.sup.3 each independently are hydrogen or a C.sub.1 to C.sub.4 alkyl; R.sup.4 and R.sup.4 each independently are hydrogen, a C.sub.1 to C.sub.4 alkyl, a C.sub.4 to C.sub.10 cycloalkyl, or a C.sub.6 to C.sub.10 aryl; R.sup.5 and R.sup.5 each independently are a C.sub.4 to C.sub.10 alkyl; R.sup.6 and R.sup.6 each independently are hydrogen or a C.sub.1 to C.sub.6 alkyl; and R.sup.7 and R.sup.7 each independently are hydrogen or a C.sub.1 to C.sub.4 alkyl; and wherein the compound of Formula I when subjected to GC-MS using electron ionization at greater than about 70 eV produces at least one ion having a mass-to-charge ratio of from 300 to 600.

A composition comprising a fuel and at least one compound characterized by Formula I: ##STR00001##
wherein X is carbon, oxygen, or sulfur; R.sup.1 and R.sup.2 each independently are hydrogen, a C.sub.1 to C.sub.20 alkyl, or a C.sub.6 to C.sub.10 aryl; R.sup.3 and R.sup.3 each independently are hydrogen or a C.sub.1 to C.sub.4 alkyl; R.sup.4 and R.sup.4 each independently are hydrogen, a C.sub.1 to C.sub.4 alkyl, a C.sub.4 to C.sub.10 cycloalkyl, or a C.sub.6 to C.sub.10 aryl; R.sup.5 and R.sup.5 each independently are a C.sub.4 to C.sub.10 alkyl; R.sup.6 and R.sup.6 each independently are hydrogen or a C.sub.1 to C.sub.6 alkyl; and R.sup.7 and R.sup.7 each independently are hydrogen or a C.sub.1 to C.sub.4 alkyl; and wherein the compound of Formula I when subjected to GC-MS using electron ionization at greater than about 70 eV produces at least one ion having a mass-to-charge ratio of from 300 to 600.

The present disclosure relates to HIF-2 inhibitors and methods of making and using them for treating cancer. Certain compounds were potent in HIF-2 scintillation proximity assay, luciferase assay, and VEGF ELISA assay, and led to tumor size reduction and regression in 786-O xenograft bearing mice in vivo.

A method of forming a composition comprising contacting a fuel and at least one compound of Formula I: ##STR00001##
wherein X is carbon, oxygen, or sulfur; R.sup.1 and R.sup.2 each independently are hydrogen, a C.sub.1 to C.sub.20 alkyl, or a C.sub.6 to C.sub.10 aryl; R.sup.3 and R.sup.3 each independently are hydrogen or a C.sub.1 to C.sub.4 alkyl; R.sup.4 and R.sup.4 each independently are hydrogen, a C.sub.1 to C.sub.4 alkyl, a C.sub.4 to C.sub.10 cycloalkyl, or a C.sub.6 to C.sub.10 aryl; R.sup.5 and R.sup.5 each independently are a C.sub.4 to C.sub.10 alkyl; R.sup.6 and R.sup.6 each independently are hydrogen or a C.sub.1 to C.sub.6 alkyl; and R.sup.7 and R.sup.7 each independently are hydrogen or C.sub.1 to C.sub.4 alkyl; and wherein the compound of Formula I when subjected to GC-MS using electron ionization at greater than 70 eV produces at least one ion having a mass-to-charge ratio of 300 to 600.

A method of forming a composition comprising contacting a fuel and at least one compound of Formula I: ##STR00001##
wherein X is carbon, oxygen, or sulfur; R.sup.1 and R.sup.2 each independently are hydrogen, a C.sub.1 to C.sub.20 alkyl, or a C.sub.6 to C.sub.10 aryl; R.sup.3 and R.sup.3 each independently are hydrogen or a C.sub.1 to C.sub.4 alkyl; R.sup.4 and R.sup.4 each independently are hydrogen, a C.sub.1 to C.sub.4 alkyl, a C.sub.4 to C.sub.10 cycloalkyl, or a C.sub.6 to C.sub.10 aryl; R.sup.5 and R.sup.5 each independently are a C.sub.4 to C.sub.10 alkyl; R.sup.6 and R.sup.6 each independently are hydrogen or a C.sub.1 to C.sub.6 alkyl; and R.sup.7 and R.sup.7 each independently are hydrogen or C.sub.1 to C.sub.4 alkyl; and wherein the compound of Formula I when subjected to GC-MS using electron ionization at greater than 70 eV produces at least one ion having a mass-to-charge ratio of 300 to 600.

The present invention relates to substituted 2-[2-halogenalkyl-4-(phenoxy)-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds of formula I as defined in the description, and the N-oxides, and salts thereof, their preparation and intermediates for preparing them. The invention also relates to the use of these compounds for combating harmful fungi and seed coated with at least one such compound and also to compositions comprising at least one such compound.

A compound of the formula (2) ##STR00001##
wherein R.sup.3 and R.sup.4 are the same or different and are a branched hydrocarbon group having 10 to 26 carbon atoms, 42 to 100 mole % of the benzylic carbons of each R.sup.3 and R.sup.4 are quaternary, m and n are each a real number of at least zero, and 2.0m+n3.0.