Patents by Inventor Rodney I. Fryer

Rodney I. Fryer has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).

  • Patent number: 4549988
    Abstract: There is presented 3H-2-benzazepines and 4,5-dihydro-3H-2-benzazepines of the formula ##STR1## wherein X is hydrogen, chloro or bromo, Y is hydrogen, fluoro or chloro with the proviso that X and Y cannot both be hydrogen and R.sub.1 is selected from the group consisting of hydrogen, bromo, chloro, iodo, a radical of the formula ##STR2## and a radical of the formula ##STR3## wherein R.sub.2 is hydrogen, phthalimido, lower alkyl, hydroxy, amino, monoalkylamino and dialkylamino and R.sub.3 is hydroxy, phthalimido or amino with the proviso that where R.sub.1 is other than hydrogen then the bonding at the 4,5-position is unsaturated,and the pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: June 29, 1983
    Date of Patent: October 29, 1985
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Rodney I. Fryer, Eugene J. Trybulski, Armin Walser
  • Patent number: 4548750
    Abstract: There is presented a compound of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of hydrogen, lower alkyl, chloro, bromo, alkoxy, hydroxy, lower alkyl substituted thio and NR.sub.4 R.sub.5 wherein R.sub.4 and R.sub.5 are hydrogen, lower alkyl and di-substituted lower alkylamino lower alkyl; R.sub.2 is selected from the group consisting of hydrogen, lower alkyl and amino; R.sub.3 is selected from the group consisting of hydrogen, acyloxy and hydroxy; X is halogen and Y is hydrogen or halogen and the N-oxides thereof when R.sub.3 is hydrogenand the pharmaceutically acceptable salts thereof.The pyrimido[4,5-d][2]benzazepines are useful as anxiolytic and sedative agents.Also presented are processes and intermediates in the production of the above pyrimido[4,5-d][2]benzazepines.
    Type: Grant
    Filed: October 17, 1983
    Date of Patent: October 22, 1985
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Rodney I. Fryer, Eugene J. Trybulski, Armin Walser
  • Patent number: 4547581
    Abstract: There is presented compounds of the formula ##STR1## wherein A is selected from the group consisting of ##STR2## R.sub.1 is selected from the group consisting of hydrogen, chlorine, bromine, lower alkyl, the group NR.sub.4 R.sub.5, the group --CH.sub.2 --CO--R.sub.7, the group --NH(CH.sub.2).sub.m NR.sub.8 R.sub.9, hydroxy, lower alkoxy, mercapto and lower alkyl mercapto; R.sub.2 is selected from the group consisting of hydrogen, amino and di-lower alkyl amino; R.sub.3 is selected from the group consisting of hydrogen, lower acyloxy and hydroxy; X is selected from the group consisting of hydrogen, halogen, trifluoromethyl, ethyl, .alpha.-hydroxy ethyl and acetyl; Y is hydrogen or halogen; R.sub.4 and R.sub.5 are hydrogen or lower alkyl or together with their co-bonded nitrogen atom form a five to seven membered heterocyclic group; R.sub.7 is selected from the group consisting of hydroxy lower alkoxy and NR.sub.8 R.sub.9 ; R.sub.8 and R.sub.
    Type: Grant
    Filed: August 23, 1984
    Date of Patent: October 15, 1985
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Rodney I. Fryer, Norman W. Gilman, Eugene J. Trybulski, Armin Walser
  • Patent number: 4546183
    Abstract: There is presented compounds of the formula ##STR1## wherein A is selected from the group consisting of ##STR2## R.sub.1 is selected from the group consisting of hydrogen, chlorine, bromine, lower alkyl, the group NR.sub.4 R.sub.5, the group --CH.sub.2 --CO--R.sub.7, the group --NH(CH.sub.2).sub.m NR.sub.8 R.sub.9, hydroxy, lower alkoxy, mercapto and lower alkyl mercapto; R.sub.2 is selected from the group consisting of hydrogen, amino and di-lower alkyl amino; R.sub.3 is selected from the group consisting of hydrogen, lower acyloxy and hydroxy; X is selected from the group consisting of hydrogen, halogen, trifluoromethyl, ethyl, .alpha.-hydroxy ethyl and acetyl; Y is hydrogen or halogen; R.sub.4 and R.sub.5 are hydrogen or lower alkyl or together with their co-bonded nitrogen atom form a five to seven membered heterocyclic group; R.sub.7 is selected from the group consisting of hydroxy lower alkoxy and NR.sub.8 R.sub.9 ; R.sub.8 and R.sub.
    Type: Grant
    Filed: August 23, 1984
    Date of Patent: October 8, 1985
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Rodney I. Fryer, Norman W. Gilman, Eugene J. Trybulski, Armin Walser
  • Patent number: 4481142
    Abstract: There is presented compounds of the formula ##STR1## wherein A is selected from the group consisting of ##STR2## R.sub.1 is selected from the group consisting of hydrogen, chlorine, bromine, lower alkyl, the group NR.sub.4 R.sub.5, the group --CH.sub.2 --CO--R.sub.7, the group--NH(CH.sub.2).sub.m NR.sub.8 R.sub.9, hydroxy, lower alkoxy, mercapto and lower alkyl mercapto; R.sub.2 is selected from the group consisting of hydrogen, amino and dilower alkyl amino; R.sub.3 is selected from the group consisting of hydrogen, lower acyloxy and hydroxy; X is selected from the group consisting of hydrogen, halogen, trifluoromethyl, ethyl, .alpha.-hydroxy ethyl and acetyl; Y is hydrogen or halogen; R.sub.4 and R.sub.5 are hydrogen or lower alkyl or together with their co-bonded nitrogen atom form a five to seven membered heterocyclic group; R.sub.7 is selected from the group consisting of hydroxy lower alkoxy and NR.sub.8 R.sub.9 ; R.sub.8 and R.sub.
    Type: Grant
    Filed: October 27, 1982
    Date of Patent: November 6, 1984
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Rodney I. Fryer, Norman W. Gilman, Eugene J. Trybulski, Armin Walser
  • Patent number: 4460781
    Abstract: There are presented compounds of the formula ##STR1## wherein R.sub.1 is hydrogen or lower alkyl; R.sub.6 is halo and R.sub.5 is hydrogen or halo; and compounds of the formulas ##STR2## wherein R.sub.2 and R.sub.3 are selected from the group consisting of hydrogen, lower alkyl, C.sub.2 to C.sub.7 carboxylic acids, hydroxy C.sub.2 to C.sub.7 alkyl, C.sub.2 to C.sub.7 carboxylic acid esters and amides and the group COR.sub.11 wherein R.sub.11 and is selected from the group consisting of alkoxy, amino or mono-lower alkyl amino; R.sub.35 is hydrogen or lower alkyl; R.sub.5 is hydrogen or halo; and R.sub.7 is methyl or chloromethyl, all of which are useful in the preparation of pyrazolobenzazepines.
    Type: Grant
    Filed: January 5, 1983
    Date of Patent: July 17, 1984
    Assignee: Hoffmann-La Roche Inc.
    Inventors: George F. Field, Rodney I. Fryer, Eugene J. Trybulski, Armin Walser
  • Patent number: 4440685
    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 with 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 or 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.
    Type: Grant
    Filed: June 16, 1983
    Date of Patent: April 3, 1984
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Armin Walser, Rodney I. Fryer
  • Patent number: 4436662
    Abstract: The present invention relates to compounds of the formula ##STR1## wherein R.sub.1 and R.sub.3 are selected from the group consisting of hydrogen, lower alkyl, hydroxy, lower alkoxy or acyloxy and R.sub.2 and R.sub.4 are hydrogen or R.sub.1 and R.sub.2 and/or R.sub.3 and R.sub.4 taken together are oxo groups with the proviso that at least one oxo group is present; R is selected from the group consisting of hydrogen, lower alkyl, C.sub.2 to C.sub.7 carboxylic acids and the esters and amides thereof, hydroxy C.sub.2 to C.sub.7 alkyl and amino C.sub.2 to C.sub.7 alkyl or mono- or di-lower alkyl amino C.sub.2 to C.sub.7 alkyl; R.sub.5 is halogen or hydrogen; and R.sub.6 is halogen with the proviso that when R.sub.1 or R.sub.3 is hydroxy, lower alkoxy or acyloxy, then R is lower alkyl or hydrogen and the N-oxides and the pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: March 31, 1983
    Date of Patent: March 13, 1984
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Rodney I. Fryer, Eugene J. Trybulski, Armin Walser
  • Patent number: 4431823
    Abstract: The present invention relates to compounds of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of hydrogen, lower alkyl, C.sub.3 to C.sub.7 alkenyl or alkynyl, hydroxymethyl, the ##STR2## wherein R.sub.11 is hydrogen, hydroxy, alkoxy, amino and mono- or di-lower alkylamino; and R.sub.3 is selected from the group consisting of hydrogen, lower alkyl, C.sub.3 to C.sub.7 alkenyl or alkynyl, hydroxymethyl, the ##STR3## wherein R.sub.11 is hydrogen, hydroxy, trihalomethyl, alkoxy, amino and mono- or di-lower alkylamino; R.sub.2 is selected from the group consisting of hydrogen, lower alkyl, C.sub.3 to C.sub.7 alkenyl or alkynyl, the ##STR4## C.sub.2 to C.sub.7 carboxylic acids and the esters and amides thereof, hydroxy C.sub.2 to C.sub.7 alkyl and amino or mono- or di-lower alkyl amino C.sub.2 to C.sub.7 alkyl; R.sub.4 is selected from the group consisting of hydrogen, acyloxy, straight chain lower alkoxy and hydroxy; R.sub.5 is halogen or hydrogen; R.sub.
    Type: Grant
    Filed: August 3, 1982
    Date of Patent: February 14, 1984
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Rodney I. Fryer, Eugene J. Trybulski, Armin Walser
  • Patent number: 4428879
    Abstract: The present invention relates to compounds of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of hydrogen, lower alkyl, C.sub.3 to C.sub.7 alkenyl or alkynyl, hydroxymethyl, the group ##STR2## wherein R.sub.11 is hydrogen, hydroxy, alkoxy, amino and mono- or di-lower alkylamino; and R.sub.3 is selected from the group consisting of hydrogen, lower alkyl, C.sub.3 to C.sub.7 alkenyl or alkynyl, hydroxymethyl, the group ##STR3## wherein R.sub.11 is hydrogen, hydroxy, trihalomethyl, alkoxy, amino and mono- or di-lower alkylamino; R.sub.2 is selected from the group consisting of hydrogen, lower alkyl, C.sub.3 to C.sub.7 alkenyl or alkynyl, the group ##STR4## C.sub.2 to C.sub.7 carboxylic acids and the esters and amides thereof, hydroxy C.sub.2 to C.sub.7 alkyl and amino or mono- or di- lower alkyl amino C.sub.2 to C.sub.7 alkyl; R.sub.4 is selected from the group consisting of hydrogen , acyloxy, straight chain lower alkoxy and hydroxy; R.sub.5 is halogen or hydrogen; R.sub.
    Type: Grant
    Filed: August 3, 1982
    Date of Patent: January 31, 1984
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Rodney I. Fryer, Eugene J. Trybulski, Armin Walser
  • Patent number: 4428878
    Abstract: The present invention relates to compounds of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of hydrogen, lower alkyl, C.sub.3 to C.sub.7 alkenyl or alkynyl, hydroxymethyl, the group ##STR2## wherein R.sub.11 is hydrogen, hydroxy, alkoxy, amino and mono- or di-lower alkylamino; and R.sub.3 is selected from the group consisting of hydrogen, lower alkyl, C.sub.3 to C.sub.7 alkenyl or alkynyl, hydroxymethyl, the group ##STR3## wherein R.sub.11 is hydrogen, hydroxy, trihalomethyl, alkoxy, amino and mono- or di-lower alkylamino; R.sub.2 is selected from the group consisting of hydrogen, lower alkyl, C.sub.3 to C.sub.7 alkenyl or alkynyl, the group ##STR4## C.sub.2 to C.sub.7 carboxylic acids and the esters and amides thereof, hydroxy C.sub.2 to C.sub.7 alkyl and amino or mono- or di-lower alkyl amino C.sub.2 to C.sub.7 alkyl; R.sub.4 is selected from the group consisting of hydrogen, acyloxy, straight chain lower alkoxy and hydroxy; R.sub.5 is halogen or hydrogen; R.sub.
    Type: Grant
    Filed: August 3, 1982
    Date of Patent: January 31, 1984
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Rodney I. Fryer, Eugene J. Trybulski, Armin Walser
  • Patent number: 4427589
    Abstract: There is presented a compound of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of hydrogen, lower alkyl, chloro, bromo, alkoxy, hydroxy, lower alkyl substituted thio and NR.sub.4 R.sub.5 wherein R.sub.4 and R.sub.5 are hydrogen, lower alkyl and di-substituted lower alkylamino lower alkyl;R.sub.2 is selected from the group consisting of hydrogen, lower alkyl and amino;R.sub.3 is selected from the group consisting of hydrogen, acyloxy and hydroxy;X is halogen and Y is hydrogen or halogen and the N-oxides thereof when R.sub.3 is hydrogenand the pharmaceutically acceptable salts thereof.The pyrimido[4,5-d][2]benzazepines are useful as anxiolytic and sedative agents.Also presented are processes and intermediates in the production of the above pyrimido[4,5-d][2]benzazepines.
    Type: Grant
    Filed: July 23, 1981
    Date of Patent: January 24, 1984
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Rodney I. Fryer, Eugene J. Trybulski, Armin Walser
  • Patent number: 4425272
    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 with 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 or 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.
    Type: Grant
    Filed: March 12, 1981
    Date of Patent: January 10, 1984
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Armin Walser, Rodney I. Fryer
  • Patent number: 4409390
    Abstract: The present invention relates to compounds of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of hydrogen, lower alkyl, C.sub.3 to C.sub.7 alkenyl or alkynyl, hydroxymethyl, the group ##STR2## wherein R.sub.11 is hydrogen, hydroxy, alkoxy, amino and mono- or di-lower alkylamino; and R.sub.3 is selected from the group consisting of hydrogen, lower alkyl, C.sub.3 to C.sub.7 alkenyl or alkynyl, hydroxymethyl, the group ##STR3## wherein R.sub.11 is hydrogen, hydroxy, trihalomethyl, alkoxy, amino and mono- or di-lower alkylamino; R.sub.2 is selected from the group consisting of hydrogen, lower alkyl, C.sub.3 to C.sub.7 alkenyl or alkynyl, the group ##STR4## C.sub.2 to C.sub.7 carboxylic acids and the esters and amides thereof, hydroxy C.sub.2 to C.sub.7 alkyl and amino or mono- or di-lower alkyl amino C.sub.2 to C.sub.7 alkyl; R.sub.4 is selected from the group consisting of hydrogen, acyloxy, straight chain lower alkoxy and hydroxy; R.sub.5 is halogen or hydrogen; R.sub.
    Type: Grant
    Filed: August 3, 1982
    Date of Patent: October 11, 1983
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Rodney I. Fryer, Eugene J. Trybulski, Armin Walser
  • Patent number: 4405518
    Abstract: The present invention relates to compounds of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of hydrogen, lower alkyl, C.sub.3 to C.sub.7 alkenyl or alkynyl, hydroxymethyl, the group ##STR2## wherein R.sub.11 is hydrogen, hydroxy, alkoxy, amino and mono- or di-lower alkylamino; and R.sub.3 is selected from the group consisting of hydrogen, lower alkyl, C.sub.3 to C.sub.7 alkenyl or alkynyl, hydroxymethyl, the group ##STR3## wherein R.sub.11 is hydrogen, hydroxy, trihalomethyl, alkoxy, amino and mono- or di-lower alkylamino; R.sub.2 is selected from the group consisting of hydrogen, lower alkyl, C.sub.3 to C.sub.7 alkenyl or alkynyl, the group ##STR4## C.sub.2 to C.sub.7 carboxylic acids and the esters and amides thereof, hydroxy C.sub.2 to C.sub.7 alkyl and amino or mono- or di-lower alkyl amino C.sub.2 to C.sub.7 alkyl; R.sub.4 is selected from the group consisting of hydrogen, acyloxy, straight chain lower alkoxy and hydroxy; R.sub.5 is halogen or hydrogen; R.sub.
    Type: Grant
    Filed: August 2, 1982
    Date of Patent: September 20, 1983
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Rodney I. Fryer, Eugene J. Trybulski, Armin Walser
  • Patent number: 4401597
    Abstract: Novel immidazobenzodiazepines 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 with 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 or 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.
    Type: Grant
    Filed: March 12, 1981
    Date of Patent: August 30, 1983
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Armin Walser, Rodney I. Fryer
  • Patent number: 4390471
    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 with 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 or 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 alkylsubstituted 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.
    Type: Grant
    Filed: March 12, 1981
    Date of Patent: June 28, 1983
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Armin Walser, Rodney I. Fryer
  • Patent number: 4379765
    Abstract: There are presented compounds of the formulas ##STR1## wherein R.sub.1 is hydrogen or lower alkyl; R.sub.2 and R.sub.3 are selected from the group consisting of hydrogen, lower alkyl, C.sub.2 to C.sub.7 carboxylic acids, hydroxy C.sub.2 to C.sub.7 alkyl, C.sub.2 to C.sub.7 carboxylic acid esters and amides and the group COR.sub.11 wherein R.sub.11 is alkoxy, amino or mono- lower alkyl amino; R.sub.6 is nitro or halo and R.sub.5 is hydrogen or halo,and the pharmaceutically acceptable salts thereof.The pyrazolobenzazepines are useful as anxiolytic and sedative agents.Also provided are processes and intermediates in the production of the above pyrazolobenzazepines.
    Type: Grant
    Filed: July 23, 1981
    Date of Patent: April 12, 1983
    Assignee: Hoffmann-La Roche Inc.
    Inventors: George F. Field, Rodney I. Fryer, Eugene J. Trybulski, Armin Walser
  • Patent number: 4377523
    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.
    Type: Grant
    Filed: March 12, 1981
    Date of Patent: March 22, 1983
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Armin Walser, Rodney I. Fryer
  • Patent number: 4376075
    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.
    Type: Grant
    Filed: March 12, 1981
    Date of Patent: March 8, 1983
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Armin Walser, Rodney I. Fryer