Generated: May 25, 2017
|Title:||Imidazodiazepines and processes therefor|
|Abstract:||Novel Imidazobenzodiazepines and their analogs are useful as anticonvulsants, muscle relaxant, anxiolytic and sedative agents. Preferred compounds of this class belong to the imidazo[1,5-a][1,4]diazepine series which may have a very wide variety of organic substituents. An especially preferred genus included within the purview of the invention encompasses a compound of the formula ##STR1## wherein R.sub.1 is hydrogen and lower alkyl preferably methyl; R.sub.3 and R.sub.5 are hydrogen; R.sub.4 is hydrogen, nitro and halogen, most preferably, chlorine, and in a most preferred embodiment when positioned on the fused benzo portion of the imidazobenzodiazepine is in the 8-position thereof, R.sub.6 is phenyl or halo, nitro, or lower alkyl-substituted phenyl, preferably, halo, with fluorine being the preferred halogen, the substituted fluoro being positioned in the 2-position of the phenyl moiety and R.sub.2 is hydrogen and lower alkyl.|
|Inventor(s):||Walser; Armin (West Caldwell, NJ), Fryer; Rodney I. (North Caldwell, NJ)|
|Assignee:||Hoffmann-La Roche Inc. (Nutley, NJ)|
|Filing Date:||Mar 12, 1981|
|Claims:||1. A process for producing a compound of the formula ##STR74## R.sub.1 is selected from the group consisting of hydrogen, lower alkyl, phenyl, pyridyl, tolyl, and alkoxy lower alkyl; R.sub.2 is hydrogen; R.sub.3 is selected from the group consisting of hydrogen and lower alkyl; R.sub.4 is selected from the group consisting of hydrogen, halogen, trifluoromethyl, lower alkyl, and lower alkanoyl; R.sub.6 is selected from the group consisting of phenyl, mono-halo or mono-nitro substituted phenyl, di-halo or halo-nitro substituted phenyl, pyridyl and mono-halo or mono-nitro substituted pyridyl which comprises the following steps in combination |
(a) reacting a compound selected from the group consisting of ##STR75## and R.sub.3, R.sub.4 and R.sub.6 are as above with nitromethane in the presence of a strong base;
(b) catalytically hydrogenating with Raney nickel in the presence of hydrogen the product from (a);
(c) acylating the product from (b) with an acid halide or an acid anhydride of the formulas R.sub.1 COX or (R.sub.1 CO).sub.2 O respectively wherein R.sub.1 is as above;
(d) cyclizing the product from (c) with a dehydrating agent selected from the group consisting of phosphorous pentoxide, polyphosphoric acid or an acid catalyst;
(e) dehydrogenating the cyclized product of (d) with a compound selected from the group consisting of manganese dioxide, potassium permanganate or palladium on carbon.
Drugs may be covered by multiple patents or regulatory protections. All trademarks and applicant names are the property of their respective owners or licensors. Although great care is taken in the proper and correct provision of this service, thinkBiotech LLC does not accept any responsibility for possible consequences of errors or omissions in the provided data. The data presented herein is for information purposes only. There is no warranty that the data contained herein is error free. thinkBiotech performs no independent verifification of facts as provided by public sources nor are attempts made to provide legal or investing advice. Any reliance on data provided herein is done solely at the discretion of the user. Users of this service are advised to seek professional advice and independent confirmation before considering acting on any of the provided information. thinkBiotech LLC reserves the right to amend, extend or withdraw any part or all of the offered service without notice.