213915-20-9

Upstream product

• 120-47-8 Ethyl 4-hydroxybenzoate 
• 3587-60-8 Benzyloxymethyl chloride 
• 137058-17-4 Methyl cis/trans-4-methoxycyclohexanecarboxylate 
• 94-30-4 ethyl 4-methoxybenzoate 

Downstream Products

• 223677-08-5 1-Hydroxymethyl-4-methoxy-cyclohexanecarboxylic acid ((S)-1-methylcarbamoyl-2-phenyl-ethyl)-amide 

Relevant academic research and scientific papers

Certain cyclic thio substituted acylaminoacid amide derivatives

Disclosed are compound of formula I wherein R represents hydrogen, lower alkyl, cycloalkyl, bicycloalkyl, adamantyl, aryl, biaryl, or mono- or di-(cycloalkyl, aryl or biaryl)-lower alkyl, di-(lower alkyl or aryl-lower alkyl)amino-lower alkyl, or (piperidino, morpholino, pyrrolidino)-lower alkyl; R1 represents hydrogen, lower alkyl, cycloalkyl, aryl, biaryl, or (cycloalkyl, aryl or biaryl)-lower alkyl; R2 represents hydrogen, lower alkyl, lower alkoxy, aryl-lower alkyl, aryl-lower alkoxy, amino, mono- or di-(lower alkyl or aryl-lower alkyl)-amino, acylamino, or (lower alkyl or aryl-lower alkyl)-(thio, sulfinyl or sulfonyl); R3 represents hydrogen, lower alkyl, cycloalkyl, aryl-lower alkyl, cycloalkyl-lower alkyl, or C2-C7-alkyl interrupted by S, SO, SO2, O or N-R5; R4 represents hydrogen or acyl; R5 represents hydrogen, lower alkyl, aryl-lower alkyl, acyl, or (lower alkyl, aryl or aryl-lower alkyl)-sulfonyl; A together with the carbon to which it is attached forms a ring and represents a bivalent radical of the formula (CH2)P which may be interrupted by S, SO, SO2, O, or N-R5; n represents an integer from zero to four; p represents an integer from 2 to 6; any pharmaceutically acceptable salts thereof; and disulfides corresponding to said compounds of formula I wherein R4 is hydrogen; methods for preparation thereof; pharmaceutical compositions comprising said compounds; and a method of inhibiting matrix-degrading metalloproteinases in mammals using such compounds.

Design and synthesis of thiol containing inhibitors of matrix metalloproteinases

A series of thiol containing derivatives was prepared. Several of these compounds were found to inhibit matrix metalloproteinases 1, 3, and 9 with selectivity towards 3 and 9. Compounds 15, 20 and 22 were administered to rats orally at 75 μmol/kg. Drug levels of compounds 20 and 22 in the plasma were found to exceed the IC50 values for MMP 3 and 9 four hours after administration.