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CONIVAPTAN

CONIVAPTAN Struktur
210101-16-9
CAS-Nr.
210101-16-9
Englisch Name:
CONIVAPTAN
Synonyma:
CONIVAPTAN;Kaunivartan;ZINC 12503187;N-[4-(2-methyl-4,5-dihydro-3H-imidazo[4,5-d][1]benzazepine-6-carbonyl)phenyl]-2-phenylbenzamide;N-[4-[(4,5-Dihydro-2-methylimidazo[4,5-d][1]benzazepin-6(1H)-yl)carbonyl]phenyl]-[1,1'-biphenyl]-2-carboxamide;[1,1'-Biphenyl]-2-carboxamide, N-[4-[(4,5-dihydro-2-methylimidazo[4,5-d][1]benzazepin-6(1H)-yl)carbonyl]phenyl]-
CBNumber:
CB51011161
Summenformel:
C32H26N4O2
Molgewicht:
498.583
MOL-Datei:
210101-16-9.mol

CONIVAPTAN Eigenschaften

Sicherheit

CONIVAPTAN Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung

Conivaptan, a vasopressin antagonist, was discovered and developed by Yamanouchi for the treatment of hyponatraeum associated with congestive heart failure.

Definition

ChEBI: The amide resulting from the formal condensation of 4-[(biphenyl-2-ylcarbonyl)amino]benzoic acid with the benzazepine nitrogen of 2-methyl-1,4,5,6-tetrahydroimidazo[4,5-d][1]benzazepine. It is an antagonist for two of the three types of argini e vasopressin (AVP) receptors, V1a and V2. It is used as its hydrochloride salt for the treatment of hyponatraemia (low blood sodium levels) caused by syndrome of inappropriate antidiuretic hormone (SIADH).

Synthese

After looking at several different approaches to the synthesis, a convergent approach, shown in the Scheme 4, was developed for large scale synthesis. Bromination of benzazepinone 10 with pyridinium hydrobromide perbromide in chloroform followed by recrystallization gave bromide 11. Reaction of bromide 11 with ethaneimidate hydrochloride in the presence of potassium carbonate in toluene or chloroform gave the desired imidazole 12 in 69% yield. Although chlo-roform provided a slightly better yield, for large scale preparation, toluene was used to minimize halogenated solvent waste and because the quality of product was similar or better than with use of chloroform. Deprotection of the tosylate was found to be effective with heating the sulfonamide 12 in 80% sulfuric acid at 80oC. The benzazepinone product 13 was obtained in 90% yield after crystallization from acetonitrile and water mixture.
Synthesis of the coupling partner 16 required to provide conivaptan was synthesized in 95% yield from biphenyl 2- benzoic acid via sequential reaction with thionyl chloride in toluene followed by coupling with aminobenzoic acid in acetone with N,N-dimethylaniline as a base. High quality acid 16 was obtained by crystallization from DMF and water. The acid 16 was activated by converting it into acid chloride with thionyl chloride in acenonitrile, to which was added imidazo benzazepine 13 in toluene and, after recrystallization in acidic ethanol, gave conivaptan hydrochloride (III) in 90% yield.

Synthesis_210101-16-9

CONIVAPTAN Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


CONIVAPTAN Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.

Global( 39)Lieferanten
Firmenname Telefon E-Mail Land Produktkatalog Edge Rate
Biochempartner
0086-13720134139
candy@biochempartner.com CHINA 965 58
Hubei Jusheng Technology Co.,Ltd.
18871490254
linda@hubeijusheng.com CHINA 28172 58
career henan chemical co
+86-0371-86658258 +8613203830695
factory@coreychem.com China 29810 58
TargetMol Chemicals Inc.
+1-781-999-5354 +1-00000000000
marketing@targetmol.com United States 32161 58
Sinoway Industrial co., ltd.
0592-5800732; +8613806035118
xie@china-sinoway.com China 988 58
Wuhan Topule Biopharmaceutical Co., Ltd
+8618327326525
masar@topule.com China 8467 58
LEAPCHEM CO., LTD.
+86-852-30606658
market18@leapchem.com China 43340 58
Shaanxi Cuikang Pharmaceutical Technology Co., Ltd
+86-18791163155 +86-13119157289
13119157289@163.com China 2973 58
Wuhan Jingkang en Biomedical Technology Co., Ltd
+8613720134139
orders@jknbiochem.com China 5221 58
Amadis Chemical Company Limited
571-89925085
sales@amadischem.com China 131957 58

210101-16-9()Verwandte Suche:


  • CONIVAPTAN
  • N-[4-[(4,5-Dihydro-2-methylimidazo[4,5-d][1]benzazepin-6(1H)-yl)carbonyl]phenyl]-[1,1'-biphenyl]-2-carboxamide
  • N-[4-(2-methyl-4,5-dihydro-3H-imidazo[4,5-d][1]benzazepine-6-carbonyl)phenyl]-2-phenylbenzamide
  • ZINC 12503187
  • [1,1'-Biphenyl]-2-carboxamide, N-[4-[(4,5-dihydro-2-methylimidazo[4,5-d][1]benzazepin-6(1H)-yl)carbonyl]phenyl]-
  • Kaunivartan
  • 210101-16-9
  • API
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