137976-09-1Relevant articles and documents
Preparation method of conivaptan hydrochloride
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Paragraph 0063; 0064; 0065; 0067, (2017/08/27)
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.
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
Tsunoda, Takashi,Yamazaki, Atsuki,Iwamoto, Hidenori,Sakamoto, Shuichi
, p. 883 - 887 (2013/09/05)
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.
Orally active, nonpeptide vasopressin V2 receptor antagonists: A novel series of 1-[4-(benzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepines and related compounds
Ogawa, Hidenori,Yamashita, Hiroshi,Kondo, Kazumi,Yamamura, Yoshitaka,Miyamoto, Hisashi,Kan, Keizo,Kitano, Kazuyoshi,Tanaka, Michinori,Nakaya, Kenji,Nakamura, Shigeki,Mori, Toyoki,Tominaga, Michiaki,Yabuuchi, Youichi
, p. 3547 - 3555 (2007/10/03)
This paper describes a novel series of nonpeptide vasopressin V2 receptor antagonists. It has been demonstrated that the 1-[4- (benzoylamino)benzoyl]-2,3,4,5-1H-benzazepines and 1-[4- (benzoylamino)benzoyl]-2,3,4,5-1H-1,5-benzodiazepines show a high affinity for V2 (and V(1a)) receptors. Among the 1-[4-(benzoylamino)benzoyl]-2,3,4,5- 1H-benzazepine series, compounds with an alkylamino group on the benzazepine ring have been shown to have oral activity. A lipophilic group at the ortho position on the terminal benzoyl ring is important for both high V2 receptor affinity and oral activity. On the basis of these favorable properties, clinical testing of 31b has begun for use as an oral and iv aquaretic agent.