131007-28-8

Upstream product

• 131031-24-8 ethyl 6-cyclohexyl-3,4-dihydro-4-oxo-1H-2-benzothiopyran-1-carboxylate 
• 131030-48-3 ethyl 4'-cyclohexylmandelate 
• 131030-56-3 ethyl α-carboxymethylthio-4-cyclohexylphenylacetate 
• 131030-50-7 ethyl α-chloro-4-cyclohexylphenylacetate 

Downstream Products

• 131007-47-1 N-<4-(diethoxyphosphorylmethyl)phenyl>-6-cyclohexyl-3,4-dihydro-4-oxo-1H-2-benzothiopyran-1-carboxamide 

Relevant academic research and scientific papers

Synthesis of novel 2-benzothiopyran and 3-benzothiepin derivatives and their stimulatory effect on bone formation

In a search for therapeutic agents for the treatment of osteoporosis and bone fracture, we found that 2-benzothiopyran-1-carboxamide derivatives 1, derived from ipriflavone as a lead compound, increase cellular alkaline phosphatase activity in cultures of rat bone marrow stromal cells. Further modification of 1 has led to the discovery of more potent 3-benzothiepin-2- carboxamide derivatives 2. Of these, 3-benzothiepin derivatives bearing a 4- (dialkoxyphosphorylmethyl)phenyl group on the 2-carboxamide moiety such as 2h and 2q exhibited significant improvement of activity compared to ipriflavone. Asymmetric synthesis of 2h and 2q revealed that the (-)-isomers possessed activities superior to those of the (+)-isomers. Further evaluation of these compounds using the mouse osteoblastic cell line MC3T3-E1 revealed that (-)- 2q enhanced the effect of bone morphogenetic protein. In addition, application of a sustained-release agent containing 2q increased the area of newly formed bone in a rat skull defect model. Based on these findings, (-)- 2q was selected for further investigation as a new drug stimulating bone formation. Synthesis and structure-activity relationships for this novel series of 2-benzothiopyran and 3-benzothiepin derivatives are detailed.

Sulfur-containing heterocyclic compounds useful for the treatment of osteoporosis, and their production

The present invention provides a sulfur-containing heterocyclic compound of the formula (I) STR1 wherein ring A is a benzene ring which may be substituted; R is a hydrogen atom or a hydrocarbon group which may be substituted; B is a carboxyl group which may be esterified or amidated; X is --CH(OH)-- or --CO--; k is 0 or 1; and k' is 0, 1 or 2 or a pharmaceutically acceptable salt thereof. Also, it provides a process for producing the compound (I) or a salt thereof and a pharmaceutical preparation for use in the treatment of osteoporosis comprising the compound (I) or salt thereof. The compounds (I) and salts thereof show excellent bone resorption inhibitory activity.