115607-61-9

Usage

InChI:InChI=1/C21H22N2O2/c1-4-8-18(24)16-13-22-21-15(10-7-12-19(21)25-3)20(16)23-17-11-6-5-9-14(17)2/h5-7,9-13H,4,8H2,1-3H3,(H,22,23)

Upstream product

• 115607-74-4 2-[1-(2-Methoxy-phenylamino)-meth-(Z)-ylidene]-3-oxo-hexanoic acid ethyl ester 
• 115607-75-5 3-butyryl-8-methoxy-4(1H)-quinolone 
• 125500-84-7 ethyl 2-(ethoxymethylene)-3-oxohexanoate 
• 3249-68-1 ethyl butyroyl acetate 
• 95-53-4 o-toluidine 
• 90-04-0 2-methoxy-phenylamine 
• 1215-57-2 N,N'-bis(o-methylphenyl)carbodiimide 
• 115607-76-6 3-butyryl-4-chloro-8-methoxyquinoline 

Downstream Products

• 142782-09-0 1-(8-Methoxy-4-o-tolylamino-quinolin-3-yl)-butan-1-ol 

Relevant academic research and scientific papers

Phosphorus mediated cyclisation of a β-arylaminoacrylamide to a quinoline: A simple synthesis of SKandF 96067

The reversible (H+/K+)ATPase inhibitor SKandF 96067 1 was prepared in two steps from Meldrun's Acid by cyclisation of the acrylamide 4 with Ph3P/C2Cl6/Et3N. Evidence for the formation of imidoylketene imine 3 was obtained by trapping with phenyl isocyanate. Thermal degradation of an amidine such as 12 also gave SKandF 96067 1.

Reversible inhibitors of the gastric (H+/K+)-ATPase. 3. 3-Substituted-4- (phenylamino)quinolines

Previously, gastric (H+/K+)-ATPase inhibitors such as 2 have been prepared as analogues of 1a on the presumption that the 3-carbethoxy substituent plays a key role in establishing the orientation of the 4- arylamino group. In this paper we explore further the contribution made to activity by the quinoline 3-substituent. We show that, for compounds bearing such a substituent, only a particular combination of properties provides high activity, both in vitro and as inhibitors of gastric acid secretion in vivo. The ability of the substituent to affect activity by restricting rotation about the C(quin)-N bond through a combination of both a π-electron withdrawal and hydrogen bonding is supported by the current study. However, high activity is only achieved if the effect of this group on the quinoline pK(a) is kept to a minimum. 3-Acyl substituents provide an optimum combination of electronic properties. From this series, compound 17c (SK and F 96067) was shown to be a potent inhibitor of histamine-stimulated gastric acid secretion after oral dosing in the Heidenhain pouch dog and was selected for further development and evaluation in man.

4-amino-3-carbonyl substituted quinolines

This invention relates to novel substituted 4-aminoquinoline derivatives which are inhibitors of gastric acid secretion in mammals. A compound of the invention is 3-butyryl-4-(2-methylphenylamino)-8-methoxyquinoline.