HUMAN PROTEIN TYROSINE PHOSPHATASE INHIBITORS AND METHODS OF USE
The present disclosure relates to compounds effective as human protein tyrosine phosphatase beta (HPTP-β) inhibitors thereby regulating angiogenesis. The present disclosure further relates to compositions comprising said human protein tyrosine phosphatase beta (HPTP-β) inhibitors, and to methods for regulating angiogenesis.
1 .- 63 . (canceled)
64 . A process for preparing Compound No. 91:
comprising:
reacting an amine having the formula:
with a sulfur trioxide source.
65 . The process of claim 64 , wherein the sulfur trioxide source is sulfur trioxide pyridine.
66 . The process of claim 64 , wherein the amine is reacted with the sulfur trioxide source in the presence of a solvent.
67 . The process of claim 66 , wherein the solvent is a polar aprotic solvent.
68 . The process of claim 64 , wherein the amine
is prepared by reducing a nitro compound having the formula:
69 . The process of claim 68 , wherein the reducing occurs in the presence of a palladium catalyst and hydrogen gas.
70 . The process of claim 69 , wherein the palladium catalyst is palladium on carbon.
71 . The process of claim 68 , wherein the nitro compound
is prepared by reacting a thiophene amine having the formula:
with a methyl carbamate having the formula:
72 . The process of claim 71 , wherein the thiophene amine is reacted with the methyl carbamate in the presence of a coupling agent.
73 . The process of claim 72 , wherein the coupling agent is HOBt.
74 . The process of claim 71 , wherein the thiophene amine
is prepared by reacting a bromide having the formula:
with thiophene-2-carbothioamide.
75 . The process of claim 74 , wherein the bromide is reacted with thiophene-2-carbothioamide in the presence of a solvent.
76 . The process of claim 75 , wherein the solvent is a polar, aprotic solvent.
77 . The process of claim 76 , wherein the solvent is acetonitrile.
78 . The process of claim 74 , wherein the bromide
is prepared by reacting a diazo compound having the formula:
with a brominating agent.
79 . The process of claim 78 , wherein the brominating agent is hydrobromic acid.
80 . The process of claim 78 , wherein the diazo compound
is prepared from an acid having a formula:
81 . A compound selected from the group consisting of:
82 . The compound of claim 81 , wherein the compound is
83 . The compound of claim 81 , wherein the compound is