- Preparation method of conivaptan hydrochloride
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The invention discloses a preparation method of conivaptan hydrochloride. The preparation method includes: taking aniline (compound I) as a raw material which is subjected to amidation, alkylation, friedel-crafts acylation, nitro reduction, amidation, alpha-chloro, cyclization and salt-forming reaction to obtain the conivaptan hydrochloride. With the method, the aniline is taken as the raw material easy to obtain, and toxic substances of acyl chloride and the like are avoided during amidation. The entire synthesis process is small in pollution and easy to process with the brand new synthesis theory, and reaction conditions of procedures are moderate; the preparation method is moderate in reaction condition of each procedure, simple in operation, high in yield and purity, environment friendly, low in production cost and suitable in industrial production.
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- A scalable process for the synthesis of 2-methyl-1,4,5,6- tetrahydroimidazo[4,5-d][1]benzazepine monohydrate and 4-[(biphenyl-2- ylcarbonyl)amino]benzoic acid: Two new key intermediates for the synthesis of the AVP antagonist conivaptan hydrochloride
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A process for the multikilogram synthesis of the dual vasopressin-receptor antagonist, conivaptan hydrochloride, has been developed. This method relies on the introduction of operationally simple chemistry during the final stages of the process when two k
- Tsunoda, Takashi,Yamazaki, Atsuki,Mase, Toshiyasu,Sakamoto, Shuichi
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p. 593 - 598
(2012/12/25)
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- A new synthetic route to YM087, an arginine vasopressin antagonist
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A new synthesis of N-{4-[(2-methyl-4,5-dihydroimidazo[4,5-d][1]benzazepin-6(1H)-yl)carbonyl]phenyl} biphenyl-2-carboxamide monohydrochloride (1, YM087) via new imidazobenzazepine intermediates is described. This method remarkably improves the overall yiel
- Tsunoda, Takashi,Tanaka, Akihiro,Mase, Toshiyasu,Sakamoto, Shuichi
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p. 1113 - 1122
(2007/10/03)
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- Practical Synthesis of N-{4-[(2-Methyl-4,5-dihydroimidazo[4,5-d][1] benzazepin-6(1H)-yl)carbonyl]phenyl}biphenyl-2-carboxamide Monohydrochloride: An Arginine Vasopressin Antagonist
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A novel, reliable, and cost-effective synthetic route to N-{4-[(2-methyl-4,5-dihydroimidazo[4,5-d][1]benzazepin-6(1H)-yl)carbonyl] -phenyl}biphenyl-2-carboxamide monohydrochloride (1, YM087), a potent Arginine vasopressin antagonist, has been developed. Using moisture-controlled potassium carbonate, imidazole formation from α-bromoketone furnished imidazobenzazepine, avoiding potential oxazole-ring formation. Catalytic reduction of nitro imidazobenzazepine afforded the corresponding amine in high yields. Treatment of the imidazole-containing amine directly, with a carbonyl chloride, afforded the target amide circumventing protection of the imidazole.
- Tsunoda, Takashi,Yamazaki, Atsuki,Iwamoto, Hidenori,Sakamoto, Shuichi
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p. 883 - 887
(2013/09/05)
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- Condensed benzazepine derivative and pharmaceutical composition thereof
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This invention relates to nitrogen-containing aromatic 5-membered ring-condensed benzazepine derivatives represented by the general formula (I) STR1 (symbols in the formula have the following meanings; ring B: a nitrogen-containing aromatic 5-membered ring having at least 1 nitrogen atom and optionally one oxygen or sulfur atom, which may optionally have substituent(s), R1 and R2 : these may be the same or different from each other and each represents a hydrogen atom, a halogen atom, a lower alkyl group, an amino group which may optionally be substituted by lower alkyl group(s), or a lower alkoxy group, A: a single bond; a group represented by the formula n: 0 or an integer of from 1 to 3, R3 and R4 : these may be the same or different from each other and each represents a hydrogen atom, a lower alkyl group (provided that R3 and R4 may together form a lower alkylene group having 2 to 7 carbon atoms), and ring C: a benzene ring which may optionally have substituent(s)) and salts thereof; to pharmaceutical compositions which contain these compounds as an active ingredient and to intermediates which are useful in synthesizing these compounds. The compounds of this invention are useful as arginine vasopressin antagonists.
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