226956-42-9

Basic information

• Product Name: 4-(5-chlorosulfonyl-2-ethoxybenzamido)-1-methyl-3-n-propylpyrazole-5-carboxamide
• Synonyms: 4-(5-chlorosulfonyl-2-ethoxybenzamido)-1-methyl-3-n-propylpyrazole-5-carboxamide
• CAS NO: 226956-42-9
• Molecular Weight: 428.897
• Mol File: 226956-42-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 4-(5-chlorosulfonyl-2-ethoxybenzamido)-1-methyl-3-n-propylpyrazole-5-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(5-chlorosulfonyl-2-ethoxybenzamido)-1-methyl-3-n-propylpyrazole-5-carboxamide(226956-42-9)
• EPA Substance Registry System: 4-(5-chlorosulfonyl-2-ethoxybenzamido)-1-methyl-3-n-propylpyrazole-5-carboxamide(226956-42-9)

Safety Data

• Hazardous Substances Data: 226956-42-9(Hazardous Substances Data)

Upstream product

• 42926-52-3 2-ethoxybenzoyl chloride 
• 139756-02-8 4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide 
• 139756-03-9 4-[(2-ethoxybenzoyl)amino]-1-methyl-3-propyl-1H-pyrazole-5-carboxamide 

Downstream Products

• 374776-43-9 4-(2-ethoxy-5-(4-(ethoxycarbonylmethyl)piperazinylsulfonyl)benzamido)-1-methyl-3-n-propylpyrazole-5-carboxamide 
• 139755-83-2 viagra 
• 1033861-31-2 7-chloro-1-methyl-5-[2-ethoxy-5-(chlorosulfonyl)phenyl]-3-n-propyl-1H-pyrazolo[4,3-d]pyrimidine 
• 374776-45-1 4-(2-ethoxy-5-(4-(2-ethoxycarbonylethyl)piperazinylsulfonyl)benzamido)-1-methyl-3-n-propylpyrazole-5-carboxamide 
• 374776-41-7 4-(2-ethoxy-5-(4-(3-ethoxycarbonylpropyl)piperidinylsulfonyl)benzamido)-1-methyl-3-n-propylpyrazole-5-carboxamide 
• 374776-39-3 4-(2-ethoxy-5-(4-(2-ethoxycarbonylethyl)piperidinylsulfonyl)benzamido)-1-methyl-3-n-propylpyrazole-5-carboxamide 
• 374776-37-1 4-(2-ethoxy-5-(4-(ethoxycarbonylmethyl)piperidinylsulfonyl)benzamido)-1-methyl-3-n-propylpyrazole-5-carboxamide 
• 374776-08-6 5-(2-ethoxy-5-(4-(hydroxycarbonylmethyl)piperazinylsulfonyl)phenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one 

Relevant articles and documents

Synthesis and phosphodiesterase inhibitory activity of new sildenafil analogues containing a carboxylic acid group in the 5′-sulfonamide moiety of a phenyl ring

New sildenafil analogues possessing a carboxylic acid group in the 5′-sulfonamide of the phenyl ring, 9a-l, were prepared from the readily available starting compounds 6a-b and cyclic amines 3-5 in a three-step sequence. In the enzyme assays, it has been shown that all the target compounds 9a-l proved to be more potent in inhibiting phosphodiesterase type 5 (PDE5) than sildenafil by 4-38-fold. The effect on the IC50 values were investigated by varying the alkoxy group (R) of the phenyl ring, the sulfonamide type (X), and the length of the methylene chain linking the carboxylic acid, and the results were discussed in detail. From this study, we have clearly demonstrated that introduction of a carboxylic acid group to the 5′-sulfonamide moiety of the phenyl ring greatly enhanced PDE5 inhibitory activity, probably by mimicking the phosphate group of cGMP. The piperidinyl propionic acid derivative 9i, which showed the highest PDE5 inhibitory activity and comparable to better selectivity over PDE isozymes in comparison with sildenafil, has been selected for more detailed biological investigations.

PROCESS FOR THE PREPARATION OF SILDENAFIL AND INTERMEDIATES THEREOF

The present invention discloses a process for preparing sildenafil and its intermediates having the structures outlined below: In particular, the present invention provides a process for preparing the compound of formula (I) and its intermediates, i.e. the compounds of formula (I), (II), (III) and (IV). The compound of formula (I) is obtained from the compound of formula (II); the compound (II) is obtained from the compound of formula (III) and methylpiperazine; the compound (III) is obtained by treating the compound of formula (IV) with chlorosulfonic acid; the compound (IV) is obtained though treating the compound of formula (V) in the presence of at least one selected from POX3, PX3, PX5 and their mixtures in any ratio. The process for preparing the compound of formula (I) according to the present invention reduces the side reactions in the processes of the prior art. These improvements lead to higher yields and a better industrial applicability with easier controlling of the reaction.