88124-26-9

Usage

Originator

Adosopine ,Menarini Group

Manufacturing Process

2 ml of acetic anhydride are added to 2.5 g of 10-amino-5,6-dihydro-11Hdibenzo[ b,e]azepine-6,11-dione (prepared from 1-aminoanthraquinone in accordance with Caronna and Palazzo-Gaz. Chim. It. 83, 533, 1953) in 50 ml of dioxane. After maintaining for 2 h under reflux, the mixture is evaporated almost to dryness under reduced pressure, the residue is then poured into water, filtered and dried to give 2.0 g of crude product. The 2.0 g of previously obtained crude product is suspended in 20 ml of N,Ndimethylformamide, and 710.0 mg of sodium methylate in 10 ml of methanol are added. After maintaining for 30 min at room temperature, 2.5 ml of methyl iodide are added, and mixture is allowed to stand for 24 h after which the mixture is poured into water, the product filtered off, dried and crystallized from ethanol, to give 5-methyl-10-acetamino-5,6-dihydro-11H-dibenzo[b,e] azepine-6,11-dione, melting point 199°-201°C.

Therapeutic Function

Urinary incontinence agent

InChI:InChI=1/C17H14N2O3/c1-10(20)18-13-8-5-7-12-15(13)16(21)11-6-3-4-9-14(11)19(2)17(12)22/h3-9H,1-2H3,(H,18,20)

Upstream product

• 108-24-7 acetic anhydride 
• 82-45-1 1-amino-9,10-anthracenedione 
• 74-88-4 methyl iodide 
• 88124-23-6 10-acetylamino-5,6-dihydro-11H-dibenzoazepin-6,11-dione 

Relevant academic research and scientific papers

Synthesis, characterization, and analytical studies of adosupine, a potential new drug for urinary incontinence

The synthesis and the spectroscopic characterization of a new potential drug for urinary incontinence, adosupine, is described. Adosupine and its potential synthesis impurities were analyzed by a new HPLC method that was developed with a C18 reversed-phase column. The analysis was made under isocratic conditions, with a mobile phase of acetonitrile:water (15:85, v/v). Resolution of all synthesis impurities was allowed. The method was also applied to stability studies of adosupine in solid state and in solution under different conditions. With the conditions used, only one degradation product was shown by HPLC analysis; it was isolated, characterized, and identified as the hydrolysis product of the lactam ring present in the adosupine structure.

Therapy of 10-amino-5,6-dihydro-11H-dibenzo(b,e)azepine-6,11-dione and derivatives as drugs for use in the treatment of urinary incontinence

Use of a 10-amino-5,6-dihydro-11H-dibenzo(b,e)azepine-6,11-dione of formula I STR1 where R represents an atom of hydrogen or a lower alkyl group, especially containing from 1 to 5 carbon atoms, as well as of a therapeutically acceptable salt of said compound, to prepare a drug for use in the treatment of urinary incontinence.