911048-72-1

Basic information

• Product Name: 8-methoxy-2,3-dimethyl-8-phenyl-3,6,7,8-tetrahydro-chromeno[7,8-d]imidazole-5-carboxylic acid methylamide
• Synonyms: 8-methoxy-2,3-dimethyl-8-phenyl-3,6,7,8-tetrahydro-chromeno[7,8-d]imidazole-5-carboxylic acid methylamide
• CAS NO: 911048-72-1
• Molecular Weight: 365.432
• Mol File: 911048-72-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 8-methoxy-2,3-dimethyl-8-phenyl-3,6,7,8-tetrahydro-chromeno[7,8-d]imidazole-5-carboxylic acid methylamide(CAS DataBase Reference)
• NIST Chemistry Reference: 8-methoxy-2,3-dimethyl-8-phenyl-3,6,7,8-tetrahydro-chromeno[7,8-d]imidazole-5-carboxylic acid methylamide(911048-72-1)
• EPA Substance Registry System: 8-methoxy-2,3-dimethyl-8-phenyl-3,6,7,8-tetrahydro-chromeno[7,8-d]imidazole-5-carboxylic acid methylamide(911048-72-1)

Safety Data

• Hazardous Substances Data: 911048-72-1(Hazardous Substances Data)

Upstream product

• 774582-42-2 7-hydroxy-2,3-dimethyl-6-(3-oxo-3-phenyl-propyl)-3H-benzoimidazole-5-carboxylic acid ethyl ester 
• 911048-71-0 8-methoxy-2,3-dimethyl-8-phenyl-3,6,7,8-tetrahydro-chromeno[7,8-d]imidazole-5-carboxylic acid 
• 74-89-5 methylamine 

Downstream Products

• 911048-74-3 4-hydroxy-5-[(3R)-3-hydroxy-3-phenylpropyl]-N,1,2-trimethyl-1H-benzimidazole-6-carboxamide 
• 911048-73-2 7-hydroxy-2,3-dimethyl-6-(3-oxo-3-phenyl-propyl)-3H-benzoimidazole-5-carboxylic acid methylamide 

Relevant articles and documents

Tetrahydrochromenoimidazoles as potassium-competitive acid blockers (P-CABs): Structure-activity relationship of their antisecretory properties and their affinity toward the hERG channel

Potassium-competitive acid blockers (P-CABs) constitute a new therapeutic option for the treatment of acid-related diseases that are widespread and constitute a significant economical burden. Enantiomerically pure tetrahydrochromenoimidazoles were prepared using the readily available candidate 4 (BYK 405879) as starting material or the Noyori asymmetric reduction of ketones as key reaction. A comprehensive SAR regarding the influence of the 5-carboxamide and the 8-aryl residue on in vitro activity, acid-suppression in the Ghosh Schild rat, and affinity toward the hERG channel was established. In addition, efficacy and duration of the antisecretory action was examined for the most promising target compounds by 24 h pH-metry in the fistula dog and a significantly different SAR was observed as compared to the Ghosh Schild rat. Several tetrahydrochromenoimidazoles were identified that possessed a comparable profile as the candidate 4.

PROCESS FOR THE PRODUCTION OF INTERMADIATES FOR THE PREPARATION OF TRICYCLIC BENZIMIDAZOLES

The invention relates to a process for the synthesis of compounds of the formula 1-a and compounds of the formula 1-b. The compounds of the formula 1-a and the compounds of the formula 1-b, in which the substituents R1, R2, R3, and Ar have the meanings indicated in the description, are valuable intermediates for the preparation of pharmaceutically active compounds.