96254-91-0

Upstream product

• 10313-60-7 3,4-dimethoxyphenylacetyl chloride 
• 73954-34-4 N-(2,2-dimethoxy-ethyl)-3,4-dimethoxyphenylacetamide 
• 85175-59-3 3-(3-chloropropyl)-1,3-dihydro-7,8-dimethoxy-2H-3-benzazepine-2-one 
• 73942-87-7 7,8-Dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one 
• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 

Relevant academic research and scientific papers

Specific bradycardic agents. 1. Chemistry, pharmacology, and structure-activity relationships of substituted benzazepinones, a new class of compounds exerting antiischemic properties

Structural modification of the calcium-antagonist verapamil (1) by replacement of the lipophilic α-isopropylacetonitrile moiety by various heterocyclic ring systems has led to a new class of cardiovascular compounds which are characterized by a specific bradycardic activity. These agents reduce heart rate without binding to classical calcium channels or β-adrenoceptors, interacting instead specifically with structures at the sino atrial node. Therefore they have also been termed sinus node inhibition. The prototype falipamil (2) has been submitted to furthr optimization mainly hy manipulation of the phthalimidine moiety. This has resultd in a secod generation of specific bradycardic agents with increased potency and selectively and prolonged duration of action represented by the benzazepinone-derivative UL-FS 49 (4). Structure-activity relationships within this novel class of compounds have revealed a marked dependence of activity on the substitution pattern of the aromatic rings, the nature of the central nitrogen atom, and the length of the connecting alkyl chains. The crucial role of the benzazepione ring for bradycardic activity can be best explained by its special impact on the overall molecular conformation.

Benzazepine derivatives

This invention relates to benzazepine derivatives of formula I STR1 wherein A is --CH2 CH2 -- or --CH=CH--; R1 is hydrogen, chlorine, bromine, C1 -C3 alkyl, amino, C1 -C3 alkylamino, C1 -C3 dialkylamino, acylamino, hydroxy, C1 -C3 alkoxy or phenyl C1 -C3 alkoxy; R2 is hydrogen, chlorine, bromine, hydroxy, C1 -C3 alkyl, C1 -C3 alkoxy or phenyl C1 -C3 alkoxy or, together with R1, can be C1 -C3 alkylenedioxy; R3 is hydrogen, chlorine, bromine or C1 -C3 alkoxy; R4 is hydrogen, benzyl, C1 -C3 alkyl or C3 -C5 alkenyl; R5 is hydrogen, halogen, C1 -C3 alkyl or C1 -C3 alkoxy; R6 is hydrogen, C1 -C3 alkyl or C1 -C3 alkoxy or, together with R5, can be a C1 -C2 alkylenedioxy; X is an imino, optionally substituted by a benzyl or C1 -C3 alkyl, or is oxygen, sulphur, sulphinyl or sulphonyl; Y is an imino, optionally substituted by a benzyl or C1 -C3 alkyl, or is methylene or carbonyl; m and n are each independently 2, 3 or 4; and nontoxic, pharmaceutically acceptable addition salts thereof. These compounds have valuable pharmacological properties, particularly the effect of lowering heart rate and reducing the O2 requirement of the heart.