219921-68-3

Usage

Uses

Used in Pharmaceutical Industry:
5-AMINO-2-(1-PYRROLIDINYL)BENZONITRILE is used as a key intermediate in the synthesis of antidiabetic drugs, specifically repaglinide and other related benzoic acid derivatives. Repaglinide is a meglitinide analog that helps to lower blood sugar levels in patients with type 2 diabetes by stimulating the release of insulin from the pancreas. 5-AMINO-2-(1-PYRROLIDINYL)BENZONITRILE's ability to form stable and active intermediates in the synthesis process makes it an essential reagent in the development of these medications.
Additionally, 5-AMINO-2-(1-PYRROLIDINYL)BENZONITRILE may also be used as a building block in the synthesis of other pharmaceutical compounds, such as antidepressants, anti-inflammatory agents, and analgesics. Its versatility in forming various chemical bonds and its compatibility with different functional groups make it a valuable asset in the field of medicinal chemistry.

InChI:InChI=1/C11H13N3/c12-8-9-7-10(13)3-4-11(9)14-5-1-2-6-14/h3-4,7H,1-2,5-6,13H2

Upstream product

• 17615-42-8 1-pyrrolidino-4-nitro-2-cyanobenzene 
• 16588-02-6 4-chloro-3-cyanonitrobenzene 

Downstream Products

• 219921-69-4 5-chloro-2-pyrrolidino-benzonitrile 
• 219921-67-2 1-(5-chloro-2-pyrrolidino-phenyl)-ethylamine 
• 1027958-07-1 1-(5-chloro-2-pyrrolidin-1-yl-phenyl)-ethylideneamine 
• 83894-71-7 methyl 4-<2-<<1-<5-chloro-2-(1-pyrrolidinyl)phenyl>ethyl>amino>-2-oxoethyl>-benzoate 
• 288250-73-7 1-(4-chlorophenyl)-N-(3-cyano-4-pyrrolidinophenyl)-5-methylpyrazole-4-carboxamide 
• 288250-72-6 N-(3-cyano-4-pyrrolidinophenyl)-1-(4-fluorophenyl)-5-methylpyrazole-4-carboxamide 

Relevant academic research and scientific papers

AMIDE COMPOUNDS AND MEDICINAL USE THEREOF

The present invention relates to a compound of the formula wherein R1 is substituted aryl, heteroaryl and the like, R2 and R3 are hydrogen, alkyl, halogen, hydroxyl group and the like, Q is N, CH and the like, W is hydrogen, alkyl, hydroxycarbonylalkyl and the like, X is halogen, cyano, nitro, amino and the like, X' is hydrogen, halogen, cyano, nitro, and Y is alkyl, hydroxyl group, alkoxy, mercapto and the like and a salt thereof, and a medicine containing the said compound. The compound of the present invention shows a superior inhibitory effect on activated lymphocytes proliferation and is useful as an agent for the prophylaxis or treatment of various autoimmune diseases.

Repaglinide and related hypoglycemic benzoic acid derivatives

The structure-activity relationships in two series of hypoglycemic benzoic acid derivatives (5, 6) were investigated. Series 5 resulted from meglitinide (3) when the 2-methoxy was replaced by an alkyleneimino residue. Maximum activity was observed with the cis-3,5-dimethylpiperidino (5h) and the octamethyleneimino (5l) residues. Series 6 resulted from the meglitinide analogon 4 bearing an inversed amido function when the 2-methoxy, the 5- fluoro, and the α-methyl residue were replaced by a 2-piperidino, a 5- hydrogen, and a larger α-alkyl residue, respectively. An alkoxy residue ortho to the carboxy group further increased activity and duration of action in the rat. The most active racemic compound, 6al (R4 = isobutyl; R = ethoxy), turned out to be 12 times more active than the sulfonylurea (SU) glibenclamide (1). Activity was found to reside predominantly in the (S)- enantiomers. Compared with the SUs 1 and 2 (glimepiride), the most active enantiomer, (S)-6al (AG-EE 623 ZW; repaglinide; ED50 = 10 μg/kg po), is 25 and 18 times more active. Repaglinide turned out to be a useful therapeutic for type 2 diabetic patients; approval was granted recently by the FDA and the EMEA. From investigations on the pharmacophoric groups in compounds of type 5 and 6, it was concluded that in addition to the two already known - the acidic group (COOH; S02NH) and the amidic spacer (CONH; NHCO) - the ortho residue R1 (alkyleneimino; alkoxy; oxo) must be regarded as a third one. A general pharmacophore model suitable for hypoglycemic benzoic acid derivatives, SUs, and sulfonamides is proposed (Figure 6). Furthermore, from superpositions of low-energy conformations (LECs) of 1, 2, and (S)-6al, it was concluded that a common binding conformation (LEC II; Figure 10B) may exist and that differences in binding to the SU receptor and in the mechanism of insulin release between repaglinide and the two SUs may be due to specific hydrophobic differences.