171722-69-3

Usage

InChI:InChI=1/C9H17NO/c1-8(2)6(7(11)10-5)9(8,3)4/h6H,1-5H3,(H,10,11)

Upstream product

• 24303-61-5 2,2,3,3-tetramethylcyclopropanecarbonyl chloride 
• 15641-58-4 2,2,3,3-tetramethylcyclopropane-1-carboxylic acid 
• 74-89-5 methylamine 

Relevant academic research and scientific papers

Pharmacokinetic analysis and antiepileptic activity of tetramethylcyclopropane analogues of valpromide

Purpose. The described structure pharmacokinetic pharmacodynamic relationships (SPPR) study explored the utilization of tetramethylcyclopropane analogues of valpromide (VPD, or tetramethylcyclopropane carboxamide derivatives of valproic acid (VPA) as new antiepileptics. Methods. The study was carried out by investigating the pharmacokinetics in dogs and pharmacodynamics (anticonvulsant activity and neurotoxicity) of the following three cyclopropane analogues of VPD: 2,2,3,3-tetramethylcyclopropane carboxamide (TMCD), N-methyl TMCD (M-TMCD) and N-[(2,2,3,3-tetramethylcyclopropyl)carbonyl]-glycinamide (TMC-GLD). Results. The three investigated compounds showed a good anticonvulsant profile in mice and rats due to the fact that they were metabolically stable VPD analogues which were not biotransformed to their non-active acid, 2,2,3,3-tetramethylcyclopropane carboxylic acid (TMCA). M-TMCD was metabolized to TMCD and TMC-GLD underwent partial biotransformation to its glycine analogue N-[(2,2,3,3-tetramethylcyclopropyl)carbonyl]-glycine (TMC-GLN). Unlike TMC-GLN, the above mentioned amides had low clearance and a relatively long half life. Conclusions. In contrast-to VPD which is biotransformed to VPA, the aforementioned cyclopropane derivatives were found. to be stable to amide-acid biotransformation. TMCD and M-TMCD show that cyclic analogues of VPD, like its aliphatic isomers, must have either two substitutions at the p position to the carbonyl, such as in the case of TMCD, or a substitution in the or and in the β positions like in the VPD isomer, valnoctamide (VCD). This paper discusses the antiepileptic potential of tetramethylcyclopropane analogues of VPD which are in animal models more potent than VPA and may be non-teratogenic and non-hepatotoxic.

Facile synthesis of amide and amine derivatives of 2,2,3,3- tetramethylcyclopropanecarboxylic acid

An efficient one-pot procedure for the synthesis of amide derivatives of 2,2,3,3-tetramethylpropanecarboxylic acid (TMCA) that involves the treating of TMCA in A/,A/-dimethylacetamide (DMAC) with thionyl chloride and stoichiometric amounts of reactant ami

Derivatives of tetramethylcyclopropane

The present invention relates to derivatives of 2,2,3,3-tetramethylcyclopropane carboxylic acid (TMCA) of general formula (I), STR1 wherein R is lower alkyl group (C1 -C6), an aryl group, an aralkyl group or an amide of general formula (II), STR2 where R1 and R2 are the same or different and may be hydrogen, a alkyl group (C1 -C6), an aryl group or an aralkyl group, and n=0-3, to their racemic mixtures and the D and L enantiomers. The invention also relates to processes for the preparation of said compounds and for pharmaceutical preparations comprising the same. The new compounds show improved activity against epilepsy.