103181-66-4

Upstream product

• 156-57-0 2-mercaptoethylamine hydrochloride 
• 96803-64-4 2-(2-methoxythiophenoxy)acetaldehyde diethyl acetal 

Downstream Products

• 103182-25-8 3α-chloroacetyl-2-(o-methoxyphenylthio)methyl-thiazolidine 

Relevant academic research and scientific papers

N-Acyl-2-substituted-1,3-thiazolidines, a New Class of Non-narcotic Antitussive Agents: Studies Leading to the Discovery of Ethyl 2--β-oxothiazolidine-3-propanoate

The synthesis of a novel class of antitussive agents is described.The compounds were examined for antitussive activity in guinea pig after cough induction by electrical or chemical stimulation.Ethyl 2--β-oxothiazolidine-3-propanoate (BBR 2173, moguisteine, 7) and other structurally related compounds showed a significant level of activity, comparable to that of codeine and dextromethorphan.The compounds presented in this paper are characterized by the N-acyl-2-substituted-1,3-thiazolidine moiety, which is a novel entry in the field of antitussive agents.The serendipitous discovery of the role played by the thiazolidine moiety in the determining the antitussive effect promoted extensive investigations on these structures.This optimization process on N-acyl-2-substituted-1,3-thiazolidines led to the initial identification of 2--3--1,3-thiazolidine (18a) as an interesting lead compound.The careful study of the rapid and very complicated metabolism of 18a provided further insights for the design of newer related derivatives.The observation that the metabolic oxidation on the lateral chain's sulfur of 18a to sulfoxide maintained the antitussive properties suggested the introduction of isosteric functional groups with respect to the sulfoxide moiety.Subsequent structural modifications showed that hydrolyzable malonic residues in the 3-position of the thiazolidine ring were able to assure high antitussive activity.This optimization ultimately led to the selection of moguisteine (7) as the most effective and safest representative of the series.Moguisteine is completely devoid of unwanted side effects (such as sedation and addiction), and its activity was demonstrated also in clinical studies.

2-sulphinyl-acetyl-1,3-thiazolidines, their preparation and pharmaceutical compositions

Thiazolidines of formula I STR1 wherein R is H, C1 -C4 -alkyl, allyl or propargyl; X is O, CH2, S; R1 is C1 -C6 -linear or branched alkyl, phenyl, benzyl, or a group of formula CH2 --CH2 --O--(CH2 --CH2 --O)n --Ra wherein n is zero or an integer from 1 to 3 and Ra is H, benzyl or C1 -C6 -linear or branched alkyl. Compounds I are endowed with favourable therapeutical properties for pathologies of the respiratory system.

Antitussive and mucus regulating 2-substituted thiazolidines

2-Substituted thiazolidines compounds having formula I STR1 wherein X is a CH2, O or S, R is hydroxy or an acyloxy, alkyloxy, alkenyloxy or alkinyloxy group, R1 is hydrogen or a group of formula STR2 R2 is hydrogen or a free or esterified carboxy group, Ra and Rb are hydrogen or methyl, p is zero or 1, R3 is a C1 -C2 alkylsulphonyl group, a phenyl or p-Cl phenyl, p-methylsulphonyl group or an acyl group; are useful as mucus regulating, antitussive and antibronchospastic agents.

2-Sulphinyl-acetyl-1,3-thiazolidines, their preparation and pharmaceutical compositions

Thiazolidines of formula I - wherein R is H, C1-C4-alkyl, allyl or propargyl;, - X is O, CH2, S;, - R1 is C1-C6-linear or branched alkyl, phenyl, benzyl, or a group of formula CH2-CH2-O-(CH2-CH2-O)n-Ra, wherein n is zero or an integer from 1 to 3 and Ra is H, benzyl or C1-C6-linear or branched alkyl. Compounds I are endowed with favourable therapeuti-cal properties for pathologies of the respiratory system.