CONIVAPTAN
- CAS No.
- 210101-16-9
- Chemical Name:
- CONIVAPTAN
- Synonyms
- 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
- Molecular Formula:
- C32H26N4O2
- Molecular Weight:
- 498.583
- MOL File:
- 210101-16-9.mol
- MSDS File:
- SDS
- Modify Date:
- 2023/5/15 10:43:30
CONIVAPTAN Chemical Properties,Uses,Production
Description
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).
Synthesis
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.
CONIVAPTAN Preparation Products And Raw materials
Raw materials
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| Pharma Affiliates | 172-5066494 | Haryana, India | 6761 | 58 | Inquiry |
| Pharmaffiliates Analytics and Synthetics P. Ltd | +91-172-5066494 | Haryana, India | 6773 | 58 | Inquiry |
| career henan chemical co | +86-0371-86658258 +8613203830695 | China | 29826 | 58 | Inquiry |
| TargetMol Chemicals Inc. | +1-781-999-5354 +1-00000000000 | United States | 19892 | 58 | Inquiry |
| Sinoway Industrial co., ltd. | 0592-5800732; +8613806035118 | China | 992 | 58 | Inquiry |
| Wuhan Topule Biopharmaceutical Co., Ltd | +8618327326525 | China | 8474 | 58 | Inquiry |
| LEAPCHEM CO., LTD. | +86-852-30606658 | China | 43348 | 58 | Inquiry |
| Shaanxi Cuikang Pharmaceutical Technology Co., Ltd | +86-19164747840 +86-13119157289 | China | 2969 | 58 | Inquiry |
| Wuhan Jingkang en Biomedical Technology Co., Ltd | +8613720134139 | China | 4692 | 58 | Inquiry |
| Amadis Chemical Company Limited | 571-89925085 | China | 131980 | 58 | Inquiry |
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