128510-20-3

Upstream product

• 67824-41-3 (R)-2-(chloromethyl)-1-methylpyrrolidine hydrochloride 
• 127061-43-2 (3R-cis)-3-(hydroxy)-1,3,4,5-tetrahydro-4-[4-methoxyphenyl)-6-(trifluoromethyl)-2H-1-benzazepin-2-one 
• 111605-09-5 (3S,4S-trans)-1,3,4,5-tetrahydro-6-(trifluoromethyl)-3-(methoxycarbonyl)-4-(4-methoxyphenyl)-2H-1-benzazepin-2-one 
• 138337-24-3 (3S,4S)-1,3,4,5-tetrahydro-6-(trifluoromethyl)-3-hydroxy-3-(methoxycarbonyl)-4-(4-methoxyphenyl)-2H-1-benzazepin-2-one 
• 3554-65-2 (R)-N-methylpyrrolidine-2-methanol 
• 111688-58-5 (3S,4S-trans)-3-carboxy-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-6-(trifluoromethyl)-2H-1-benzazepin-2-one (S)-α-methylbenzylamine salt 

Downstream Products

• 128573-84-2 Acetic acid (3R,4S)-4-(4-methoxy-phenyl)-1-((R)-1-methyl-pyrrolidin-2-ylmethyl)-2-oxo-6-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-yl ester 

Relevant academic research and scientific papers

Benzazepinone calcium channel blockers. 2. Structure-activity and drug metabolism studies leading to potent antihypertensive agents. Comparison with benzothiazepinones

As part of a program to discover potent antihypertensive analogues of diltiazem (3a), we prepared 1-benzazepin-2-ones (4). Benzazepinones competitively displace radiolabeled diltiazem, and show the same absolute stereochemical preferences at the calcium channel receptor protein. Derivatives of 4 containing a trifluoromethyl substituent in the fused aromatic ring show potent and long-acting antihypertensive activity. Studies of the metabolism of 4 lead to the metabolically stable antihypertensive calcium channel blockers 5a and 5c. Benzazepinone 5a is a longer acting and more potent antihypertensive agent than the second generation diltiazem analogue TA-3090 (3e).