1092938-91-4

Upstream product

• 917956-88-8 4-hydroxy-5-[(3R)-3-hydroxy-3-(2-methylphenyl)propyl]-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide 
• 917957-11-0 BYK 405879 
• 1046469-25-3 (8S)-2,3-dimethyl-8-(2-methylphenyl)-3,6,7,8-tetrahydrochromeno[7,8-d]imidazole-5-carboxylic acid 

Downstream Products

• 1092938-94-7 methyl [(8S)-2,3-dimethyl-8-(2-methylphenyl)-3,6,7,8-tetrahydrochromeno[7,8-d]imidazol-5-yl]carbamate 
• 1092938-52-7 (8S)-2,3-dimethyl-8-(2-methylphenyl)-3,6,7,8-tetrahydrochromeno[7,8-d]imidazol-5-amine 
• 1092938-54-9 N-[(8S)-2,3-dimethyl-8-(2-methylphenyl)-3,6,7,8-tetrahydrochromeno[7,8-d]imidazol-5-yl]-cyclopropane-carboxamide 
• 1092938-50-5 1-[(8S)-2,3-dimethyl-8-(2-methylphenyl)-3,6,7,8-tetrahydrochromeno[7,8-d]imidazol-5-yl]-pyrrolidin-2-one 
• 1092938-56-1 1-[(8S)-2,3-dimethyl-8-(2-methylphenyl)-3,6,7,8-tetrahydrochromeno[7,8-d]imidazol-5-yl]-piperidin-2-one 

Relevant academic research and scientific papers

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.

Synthesis and pharmacological evaluation of 5-carboxamide-substituted tetrahydrochromeno[7,8-d]imidazoles

A fast access to novel 5-carboxamide-substituted tetrahydrochromeno[7,8-d]imidazoles 4 was developed using the readily available preclinical candidate BYK 405879 (1) as starting material. The 5-amino function was installed by the Curtius rearrangement of

PHARMACEUTICALLY ACTIVE 6-N-SUBSTITUTED BENZIMIDAZOLE DERIVATIVES

The invention provides compounds of the formula (0), in which the substituents and symbols are as defined in the description. The compounds inhibit the secretion of gastric acid.

INTERMEDIATES AND PROCESS FOR THE PRODUCTION OF 5-SUBSTITUTED TRICYCLIC BENZIMIDAZOLES

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