78364-19-9

Usage

Chemical class

Ergot alkaloids

Main use

Prevention of migraine headaches

Mechanism of action

Constricts blood vessels in the brain

Other uses

Treatment of cluster headaches and reducing frequency and severity of certain types of migraines

Form available

Oral tablets

Precautions

Should be supervised by a healthcare professional due to potential side effects and interactions with other medications.

Upstream product

• 106-47-8 4-chloro-aniline 
• 78364-23-5 4-Methoxymethylen-3,4-dihydro-1H-2-benzopyran-1,3-dion 
• 703-59-3 homophthalic anhydride 
• 89-51-0 Homophthalic acid 
• 78364-11-1 4-[1-(4-Chloro-phenylamino)-meth-(Z)-ylidene]-isochroman-1,3-dione 

Downstream Products

• 133096-54-5 2-(4-Chloro-phenyl)-N-hydroxy-1-oxo-1,2-dihydro-isoquinoline-4-carboxamidine 
• 133096-47-6 2-(4-Chloro-phenyl)-1-oxo-1,2-dihydro-isoquinoline-4-carbonitrile 
• 133096-40-9 2-(4-Chloro-phenyl)-1-oxo-1,2-dihydro-isoquinoline-4-carboxylic acid amide 

Relevant academic research and scientific papers

Syntheses of Fluorescent Dyes, 11. - Rearrangement of Alkoxymethylene- and Aminomethylenehomophthalic Anhydrides into Isocoumarins and Isoquinolinones, resp.

Homophthalic acid (1) and its anhydride (3,4-dihydro-1H-2-benzopyran-1,3-dione, 2) react with trimethoxymethane in acetic acid anhydride to give 4-methoxymethylenehomophthalic anhydride (3a).This is converted into the enamines 4a-i by reaction with primary or secondary amines and ureas, respectively. 4b,d-i may also be obtained directly from 2 by reaction with a mixture of trimethoxymethane and the corresponding amine (or urea).In alkaline methanol 3a and similarly 4h suffer ring opening to give 5 and 6, respectively. - Treatment of 3a with aqueous sodium hydroxide and subsequent acidification furnishes by a rearrangement reaction the isocoumarin-4-carboxylic acid (7a) together with some of its decarboxylation product 7b, probably via an open ring intermediate of type A.Better yields of 7a are obtained by rearrangement performed in concentrated hydrochloric acid. - Similarly, compounds 4 rearrange to form the isoquinoline-4-carboxylic acids 8a-d. - Starting from homophthalic acid (1), these rearrangements offer a straightforward route to obtain fluorescent isocoumarin as well as isoquinolinone derivatives.