25905-77-5 Usage
Description
Minaprine dihydrochloride is a synthetic central nervous system (CNS) drug that functions as a muscle relaxant for skeletal muscles. It is synthesized through analog synthesis and CYP2D6 enzyme kinetic analyses, and is commonly known by the brand name Cantor, manufactured by Sanofi.
Uses
Used in Pharmaceutical Industry:
Minaprine dihydrochloride is used as a muscle relaxant for skeletal muscles, helping to alleviate muscle spasms and pain. It is particularly beneficial for conditions such as muscle strains, sprains, and other musculoskeletal disorders.
Used in Central Nervous System Applications:
Minaprine dihydrochloride is used as a central nervous system drug, targeting the brain and spinal cord to provide relief from muscle tension and pain. Its action on the CNS helps to reduce the reflexes that cause muscle contractions, leading to a more relaxed and comfortable state for the patient.
Originator
Cantor,Clin Midy,France,1979
Manufacturing Process
(a) Preparation of the free base: A mixture comprising 0.1 mol (20.4 g) of 3-chloro-4-methyl-6-phenylpyridazine and 0.2 mol (26.2 g) of N-(2-aminoethyl)-morpholine in 100 ml of n-butanol, with a pinch of copper powder, was heatedunder reflux for 12 hours. At the end of this time, the hot solution was pouredinto 200 ml of cold water. The resulting mixture was filtered through asintered glass filter and the precipitate washed with ether. The filtrate and theether washings were placed in a separating funnel and extracted with two 150ml portions of ether. The ethereal layer was then extracted with about 250 mlof N sulfuric acid.The acid solution was made alkaline with a 10% aqueous solution of sodiumcarbonate, and left to crystallize overnight.The solution was filtered, yielding the colorless needles which wererecrystallized from isopropanol. The yield was 15 g (53%).(b) Preparation of the hydrochloride: The base was dissolved in the smallestamount possible of anhydrous acetone. Double that volume of anhydrousether was added, and a stream of hydrogen chloride gas was passed throughthe solution. The hydrochloride salt obtained was recrystallized from absolutealcohol. The yield after recrystallization was 17 g (90%).
Therapeutic Function
Antidepressant
Check Digit Verification of cas no
The CAS Registry Mumber 25905-77-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,5,9,0 and 5 respectively; the second part has 2 digits, 7 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 25905-77:
(7*2)+(6*5)+(5*9)+(4*0)+(3*5)+(2*7)+(1*7)=125
125 % 10 = 5
So 25905-77-5 is a valid CAS Registry Number.
InChI:InChI=1/C17H22N4O/c1-14-13-16(15-5-3-2-4-6-15)19-20-17(14)18-7-8-21-9-11-22-12-10-21/h2-6,13H,7-12H2,1H3,(H,18,20)
25905-77-5Relevant articles and documents
Diazines VII. A new synthetic route to the pyridazine antidepressant, minaprine using directed ortho metalation and Suzuki cross coupling reactions
Turck, A.,Ple, N.,Mojovic, L.,Queguiner, G.
, p. 488 - 492 (2007/10/02)
A new synthetic route has been developed for minaprine.The synthesis is based upon two reactions recently studied on pyridazine: metalation and cross coupling with transition metals.Some different routes have been tested starting from 3,6-dichloropyridazine.The best results were obtained by coupling phenylboronic acid with 3-chloro-6-methoxypyridazine then by metalating 3-methoxy-6-phenylpyridazine and reacting the lithio derivatives with methyl iodide. 3-Methoxy-4-methyl-6-phenylpyridazine was obtained.After hydrolysis of the ether moiety, chlorination and substitution by the amine, minaprine was obtained with an overall yield of 36percent.Keywords - pyridazine / metalation / cross-coupling
