The present invention provides a process of producing a trifluoromcthoxylated aryl or trifluoromothoxylated heteroaryl having the structure: ##STR00001##
wherein
A is an aryl or heteroaryl, each with or without substitution; and
R.sub.1 is —H, -(alkyl), -(alkenyl), -(alkynyl), -(aryl), -(heteroaryl), -(alkylaryl), -(alkylheteroaryl), —NH-(alkyl), —N(alkyl).sub.2, —NH-(alkenyl), —NH-(alkynyl) —NH-(aryl), —NH-(heteroaryl), —O-(alkyl), —O-(alkenyl), —O-(alkynyl), —O-(aryl), —O-(heteroaryl), —S-(alkyl), —S-(alkenyl), —S-(alkynyl), —S-(aryl), or —S-(heteroaryl), comprising:
(a) reacting a compound having the structure: ##STR00002##
with a trifluoromethylating agent in the presence of a base in a first suitable solvent under conditions to produce a compound having the structure: ##STR00003##
and
(b) maintaining the compound produced in step (a) in a second suitable solvent under conditions sufficient to produce the trifluoromethoxylated aryl or trifluormethoxylated heteroaryl having the structure: ##STR00004##

The present invention provides a process of producing a trifluoromcthoxylated aryl or trifluoromothoxylated heteroaryl having the structure: ##STR00001##
wherein
A is an aryl or heteroaryl, each with or without substitution; and
R.sub.1 is —H, -(alkyl), -(alkenyl), -(alkynyl), -(aryl), -(heteroaryl), -(alkylaryl), -(alkylheteroaryl), —NH-(alkyl), —N(alkyl).sub.2, —NH-(alkenyl), —NH-(alkynyl) —NH-(aryl), —NH-(heteroaryl), —O-(alkyl), —O-(alkenyl), —O-(alkynyl), —O-(aryl), —O-(heteroaryl), —S-(alkyl), —S-(alkenyl), —S-(alkynyl), —S-(aryl), or —S-(heteroaryl), comprising:
(a) reacting a compound having the structure: ##STR00002##
with a trifluoromethylating agent in the presence of a base in a first suitable solvent under conditions to produce a compound having the structure: ##STR00003##
and
(b) maintaining the compound produced in step (a) in a second suitable solvent under conditions sufficient to produce the trifluoromethoxylated aryl or trifluormethoxylated heteroaryl having the structure: ##STR00004##

The present invention provides a process of producing a trifluoromcthoxylated aryl or trifluoromothoxylated heteroaryl having the structure: ##STR00001##
wherein
A is an aryl or heteroaryl, each with or without substitution; and
R.sub.1 is —H, -(alkyl), -(alkenyl), -(alkynyl), -(aryl), -(heteroaryl), -(alkylaryl), -(alkylheteroaryl), —NH-(alkyl), —N(alkyl).sub.2, —NH-(alkenyl), —NH-(alkynyl) —NH-(aryl), —NH-(heteroaryl), —O-(alkyl), —O-(alkenyl), —O-(alkynyl), —O-(aryl), —O-(heteroaryl), —S-(alkyl), —S-(alkenyl), —S-(alkynyl), —S-(aryl), or —S-(heteroaryl), comprising:
(a) reacting a compound having the structure: ##STR00002##
with a trifluoromethylating agent in the presence of a base in a first suitable solvent under conditions to produce a compound having the structure: ##STR00003##
and
(b) maintaining the compound produced in step (a) in a second suitable solvent under conditions sufficient to produce the trifluoromethoxylated aryl or trifluormethoxylated heteroaryl having the structure: ##STR00004##

A method for detecting for the presence of H.sub.2S or HS.sup.− anion in a system, comprising contacting a sample from the system with a compound, or a protonate or salt thereof, having a structure represented by: ##STR00001## wherein Y represents an aromatic group or a substituted aromatic group; n is 1 or 2; R is independently H, alkyl, substituted alkyl, a polyether moiety, carboxyl, substituted carboxyl, carbamate, substituted carbonate, carbonyloxy, alkoxy, substituted alkoxy, haloalkyl, halogen, nitro, amino, amido, aryloxy, cyano, hydroxyl, or sulfonyl; R.sup.1 is H, substituted lower alkyl, lower alkyl, substituted aralkyl or aralkyl; R.sup.2 is selected from H, acyl, substituted aralkyl, aralkyl, phosphonyl, —SO.sub.2R.sup.3; —C(O)R.sup.5; —C(O)OR.sup.7 or —C(O)NR.sup.9R.sup.10; R.sup.3; R.sup.5; R.sup.7; R.sup.9 and R.sup.10 are each independently selected from H, substituted lower alkyl, lower alkyl, substituted aralkyl, aralkyl, substituted aryl or aryl.

A method for detecting for the presence of H.sub.2S or HS.sup.− anion in a system, comprising contacting a sample from the system with a compound, or a protonate or salt thereof, having a structure represented by: ##STR00001## wherein Y represents an aromatic group or a substituted aromatic group; n is 1 or 2; R is independently H, alkyl, substituted alkyl, a polyether moiety, carboxyl, substituted carboxyl, carbamate, substituted carbonate, carbonyloxy, alkoxy, substituted alkoxy, haloalkyl, halogen, nitro, amino, amido, aryloxy, cyano, hydroxyl, or sulfonyl; R.sup.1 is H, substituted lower alkyl, lower alkyl, substituted aralkyl or aralkyl; R.sup.2 is selected from H, acyl, substituted aralkyl, aralkyl, phosphonyl, —SO.sub.2R.sup.3; —C(O)R.sup.5; —C(O)OR.sup.7 or —C(O)NR.sup.9R.sup.10; R.sup.3; R.sup.5; R.sup.7; R.sup.9 and R.sup.10 are each independently selected from H, substituted lower alkyl, lower alkyl, substituted aralkyl, aralkyl, substituted aryl or aryl.

This invention provides, but is not limited to, novel oleanolic acid derivatives having the formula:

##STR00001##

wherein the variables are defined herein. Also provided are pharmaceutical compositions, kits and articles of manufacture comprising such compounds, methods and intermediates useful for making the compounds, and methods of using the compounds and compositions.

Hydroxybenzamide derivative compounds having β-cell protective activity against ER stress, and methods of their use in treating diabetes and other conditions and diseases associated with ER stress. In one non-limiting embodiment, the derivative is 3-hydroxy-N-(4-(trifluoromethyl)benzyl)benzamide.

Hydroxybenzamide derivative compounds having β-cell protective activity against ER stress, and methods of their use in treating diabetes and other conditions and diseases associated with ER stress. In one non-limiting embodiment, the derivative is 3-hydroxy-N-(4-(trifluoromethyl)benzyl)benzamide.

The present invention relates to the discovery that certain non-naturally occurring, non-peptide amide compounds and amide derivatives, such as oxalamides, ureas, and acrylamides, are useful flavor or taste modifiers, such as a flavoring or flavoring agents and flavor or taste enhancer, more particularly, savory (the “umami” taste of monosodium glutamate) or sweet taste modifiers, —savory or sweet flavoring agents and savory or sweet flavor enhancers, for food, beverages, and other comestible or orally administered medicinal products or compositions.

The present invention relates to the discovery that certain non-naturally occurring, non-peptide amide compounds and amide derivatives, such as oxalamides, ureas, and acrylamides, are useful flavor or taste modifiers, such as a flavoring or flavoring agents and flavor or taste enhancer, more particularly, savory (the “umami” taste of monosodium glutamate) or sweet taste modifiers, —savory or sweet flavoring agents and savory or sweet flavor enhancers, for food, beverages, and other comestible or orally administered medicinal products or compositions.