Synthesis of 1, 5-Benzothiazepine Derivatives. IV. Resolution of dl-cis-3-Acetoxy-5-[2-(dimethylamino)ethyl]-2, 3-dihydro-2-(p-methoxyphenyl)-1, 5-benzothiazepin-4(5H)-one Hydrochloride

Inoue, Hirozumi; Takeo, Satoshi; Kawazu, Mitsutaka; Kugita, Hiroshi

doi:10.1248/yakushi1947.93.6_729

Cited by 34 publications

(8 citation statements)

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“…10 Enantiomers can be successfully converted to benzenesulfonic salts without any racemization. Inoue et al 11 reported on the resolution of the optical isomer of diltiazem.…”

Section: Preparation Synthesis and Characterizationmentioning

confidence: 99%

Chiral Cardiovascular Drugs

Ranade¹,

Somberg

2005

American Journal of Therapeutics

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Stereochemistry in drug molecules is rapidly becoming an important aspect in drug research, design, and development. Recently, individual stereoisomers of drug molecules with asymmetric centers such as fexofenadine, cetirizine, verapamil, fluoxetine, levalbutarol, and amphetamine, for example, have been separated and developed as individual drugs. These stereoisomers have different therapeutic activity, and each isomer has contributed differently with respect to its formulation's pharmacologic activity, side effects, and toxicity. The present overview discusses chirality among a select group of cardiovascular drugs, their stereochemical synthesis/preparation, isolation techniques using chiral chromatography, methods for confirmation of their enantiomeric purity, pharmacodynamics, and pharmacokinetics. Chirality has been visualized as an important factor in cardiovascular research. It is also becoming evident in other areas of therapeutics.

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“…10 Enantiomers can be successfully converted to benzenesulfonic salts without any racemization. Inoue et al 11 reported on the resolution of the optical isomer of diltiazem.…”

Section: Preparation Synthesis and Characterizationmentioning

confidence: 99%

Chiral Cardiovascular Drugs

Ranade¹,

Somberg

2005

American Journal of Therapeutics

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“…1 and 2, is a typical calcium channel blocker and is used clinically as an effective antianginal and antihypertensive agent in more than 100 countries (1). Many methods have been investigated for the synthesis of this optically active medicine (2)(3)(4)(5)(6)(7)(8)(9)(10)(11). On a commercial basis, the standard process of nine chemical synthetic steps had been used for a long time.…”

Section: Diltiazemmentioning

confidence: 99%

Diltiazem Synthesis, Microbial Asymmetric Reduction

Nishida

Shibatani

2010

Encyclopedia of Industrial Biotechnology

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“…Owing to the huge amount of literaterature data, in this paragraph we included only the most adequate selected examples to illustrate some procedures used for this purpose which means that not all papers published on this topic are included and discussed. The first synthesis of (+)-diltiazem was achieved by Inoue et al 44 Utilization of optically active 3-phenylglycidates have been published by several research groups. [45][46][47][48] Racemic nitrocarboxylic acid 49 or aminocarboxylic acid 50 intermediates were optically resolved via distereomeric salt formation.…”

Section: Synthesis and Bioactivities Of Optically Active 3-amino-23-mentioning

confidence: 99%