193549-13-2

Upstream product

• 696-63-9 4-Methoxybenzenethiol 
• 60341-39-1 (E)-4-phenylbut-2-enoic acid 
• 122-78-1 phenylacetaldehyde 
• 110-89-4 piperidine 
• 154457-63-3 1-(tert-butoxycarbonyl)-2-benzylethene 
• 19812-99-8 4-benzyloxetan-2-one 

Downstream Products

• 193549-14-3 N-hydroxy-3-(4-methoxyphenylsulfanyl)-4-phenylbutyramide 

Relevant academic research and scientific papers

A novel synthesis of β-sulfinyl- and β-sulfonyl-hydroxamic acids via CsF-mediated ring opening of substituted β-lactones

The ring-opening reaction of 3-substituted β-lactones with thiols was achieved using CsF in DMF as promoter. The resulting β-sulfanyl-carboxylic acid intermediates were coupled to hydroxylamine-Wang resin and the sulfur atom was selectively oxidized to afford β-sulfinyl- and β-sulfonyl-hydroxamic acid libraries.

Substituted (aryl, heteroaryl, arylmethyl or heteroarylmethyl) hydroxamic acid compounds

This invention is directed to compounds of formula I: wherein the variables are as described herein. Compounds within the scope of the present invention possess useful properties, more particularly pharmaceutical properties. They are especially useful for inhibiting the production or physiological effects of TNF in the treatment of a patient suffering from a disease state associated with a physiologically detrimental excess of tumor necrosis factor (TNF). Compounds within the scope of the present invention also inhibit cyclic AMP phosphodiesterase, and are useful in treating a disease state associated with pathological conditions that are modulated by inhibiting cyclic AMP phosphodiesterase, such disease states including inflammatory and autoimmune diseases, in particular type IV cyclic AMP phosphodiesterase. Compounds within the scope of the present invention may also inhibit an MMP, and are useful in treating a disease state associated with pathological conditions that are modulated by inhibiting MMPs, such disease states involve tissue breakdown and those associated with a physiologically detrimental excess of TNF. The present invention is therefore also directed to the pharmaceutical use of the compounds, pharmaceutical compositions containing the compounds, intermediates leading thereto and methods for the preparation of the compounds and their intermediates.

Matrix metalloprotease inhibitors

The present invention relates to compounds of Formula I: STR1 that are matrix metalloprotease inhibitors, pharmaceutical compositions containing them, methods for their use and methods of preparing these compounds.

Matrix metalloprotease inhibitors

Compounds of the formula: wherein: n is0, 1 or 2; Y ishydroxy or XONH-, where X is hydrogen or lower alkyl; R1is hydrogen or lower alkyl; R2is hydrogen, lower alkyl, heteroalkyl, aryl, aralkyl, arylheteroalkyl, cycloalkyl, cycloalkylalkyl, heteroaryl, heteroaralkyl, heteroarylheteroalkyl, heterocyclo, heterocylo-lower alkyl, heterocyclo-lower heteroalkyl or -NR6R7, wherein: R6is hydrogen, lower alkyl, cycloalkyl or cycloalkylalkyl, aryl, heteroaryl and heteroaralkyl; R7is hydrogen, lower alkyl, cycloalkyl or cycloalkylalkyl, aryl, aralkyl, heteroaryl, heteroaralkyl, -C(O)R8, -C(O)NR8R9, -SO2NR8R9, -SO2R10, aryloxycarbonyl, or alkoxycarbonyl; or R6and R7together with the nitrogen atom to which they are attached represent a heterocyclo group; wherein R8and R9are independently hydrogen, lower alkyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, heteroaryl, heteroaralkyl or heteroalkyl; and R10is lower alkyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, heteroaryl, heteroaralkyl, heteroalkyl or heterocyclo; or R1and R2together with the carbon atom to which they are attached represent a cycloalkyl or heterocyclo group; R3ishydrogen, lower alkyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, heteroaryl, heteroaralkyl, heteroalkyl or lower alkoxy; R4ishydrogen, lower alkyl, cycloalkyl or cycloalkylalkyl; or R2and R3together with the carbons to which they are attached represent a cycloalkyl or heterocyclo group; or R3and R4together with the carbon to which they are attached represent a cycloalkyl or heterocyclo group; and R5islower alkyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, heteroaryl, or heteroaralkyl; or pharmaceutically acceptable salts or esters thereof exhibit useful pharmacological properties, in particular for use as matrix metalloprotease inhibitors, particularly for interstitial collagenases.