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: 4376074
    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
  • Patent number: 4371468
    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. As 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 16, 1981
    Date of Patent: February 1, 1983
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Armin Walser, Rodney I. Fryer
  • Patent number: 4368157
    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. As 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: January 11, 1983
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Armin Walser, Rodney I. Fryer
  • Patent number: 4368158
    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. As 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: January 11, 1983
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Armin Walser, Rodney I. Fryer
  • Patent number: 4368159
    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. As 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 13, 1981
    Date of Patent: January 11, 1983
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Armin Walser, Rodney I. Fryer
  • Patent number: 4354973
    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 akyl, 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## 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 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: July 23, 1981
    Date of Patent: October 19, 1982
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Rodney I. Fryer, Eugene J. Trybulski, Armin Walser
  • Patent number: 4349476
    Abstract: This invention is directed toward pharmacologically active compound of the formula ##STR1## wherein A is ##STR2## R.sub.1 is selected from the group consisting of hydrogen, lower alkyl, hydroxy lower alkyl, acyloxy lower alkyl, phenyl, alkoxy lower alkyl, halo lower alkyl, amino lower alkyl, substituted amino lower alkyl, substituted phenyl, pyridyl, aralkyl and the groups ##STR3## wherein R is hydrogen or lower alkyl and ROOC where R is lower alkyl; R.sub.2 is selected from the group consisting of hydrogen, lower alkyl, hydroxy lower alkyl, acyloxy lower alkyl, alkoxy lower alkyl, halo lower alkyl, amino or substituted amino lower alkyl, amino, cyano, cyano lower alkyl, substituted amino, chloro, bromo and iodo, the group --COOR where R is hydrogen or lower alkyl, the group ##STR4## where R is hydrogen or lower alkyl, or derivatives thereof, e.g., the group R--C.dbd.
    Type: Grant
    Filed: March 12, 1981
    Date of Patent: September 14, 1982
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Armin Walser, Rodney I. Fryer
  • Patent number: 4349477
    Abstract: This invention is directed toward pharmacologically active compound of the formula ##STR1## wherein A is ##STR2## R.sub.1 is selected from the group consisting of hydrogen, lower alkyl, hydroxy lower alkyl, acyloxy lower alkyl, phenyl, alkoxy lower alkyl, halo lower alkyl, amino lower alkyl, substituted amino lower alkyl, substituted phenyl, pyridyl, aralkyl and the groups ##STR3## wherein R is hydrogen or lower alkyl and ROOC where R is lower alkyl; R.sub.2 is selected from the group consisting of hydrogen, lower alkyl, hydroxy lower alkyl, acyloxy lower alkyl, alkoxy lower alkyl, halo lower alkyl, amino or substituted amino lower alkyl, amino, cyano, cyano lower alkyl, substituted amino, chloro, bromo and iodo, the group --COOR where R is hydrogen or lower alkyl, the group ##STR4## where R is hydrogen or lower alkyl, or derivatives thereof, e.g., the group R--C.dbd.
    Type: Grant
    Filed: March 12, 1981
    Date of Patent: September 14, 1982
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Armin Walser, Rodney I. Fryer
  • Patent number: 4349475
    Abstract: This invention is directed toward pharmacologically active compound of the formula ##STR1## wherein A is ##STR2## R.sub.1 is selected from the group consisting of hydrogen, lower alkyl, hydroxy lower alkyl, acyloxy lower alkyl, phenyl, alkoxy lower alkyl, halo lower alkyl, amino lower alkyl, substituted amino lower alkyl, substituted phenyl, pyridyl, aralkyl and the groups ##STR3## wherein R is hydrogen or lower alkyl and ROOC where R is lower alkyl; R.sub.2 is selected from the group consisting of hydrogen, lower alkyl, hydroxy lower alkyl, acyloxy lower alkyl, alkoxy lower alkyl, halo lower alkyl, amino or substituted amino lower alkyl, amino, cyano, cyano lower alkyl, substituted amino, chloro, bromo and iodo, the group --COOR where R is hydrogen or lower alkyl, the group ##STR4## where R is hydrogen or lower alkyl, or derivatives thereof, e.g., the group R--C.dbd.
    Type: Grant
    Filed: March 12, 1981
    Date of Patent: September 14, 1982
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Armin Walser, Rodney I. Fryer
  • Patent number: 4347364
    Abstract: This invention is directed toward pharmacologically active compound of the formula ##STR1## R.sub.1 is selected from the group consisting of hydrogen, lower alkyl, hydroxy lower alkyl, acyloxy lower alkyl, phenyl, alkoxy lower alkyl, halo lower alkyl, amino lower alkyl, substituted amino lower alkyl, substituted phenyl, pyridyl, aralkyl and the groups ##STR2## wherein R is hydrogen or lower alkyl and ROOC where R is lower alkyl; R.sub.2 is selected from the group consisting of hydrogen, lower alkyl, hydroxy lower alkyl, acyloxy lower alkyl, alkoxy lower alkyl, halo lower alkyl, amino or substituted amino lower alkyl, amino, cyano, cyano lower alkyl, substituted amino, chloro, bromo and iodo, the group--COOR where R is hydrogen or lower alkyl, the group ##STR3## where R is hydrogen or lower alkyl, or derivatives thereof, e.g., the group R--C.dbd.
    Type: Grant
    Filed: March 12, 1981
    Date of Patent: August 31, 1982
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Armin Walser, Rodney I. Fryer
  • Patent number: 4347365
    Abstract: This invention is directed toward pharmacologically active compound of the formula ##STR1## R.sub.1 is selected from the group consisting of hydrogen, lower alkyl, hydroxy lower alkyl, acyloxy lower alkyl, phenyl, alkoxy lower alkyl, halo lower alkyl, amino lower alkyl, substituted amino lower alkyl, substituted phenyl, pyridyl, aralkyl and the groups ##STR2## wherein R is hydrogen or lower alkyl and ROOC where R is lower alkyl; R.sub.2 is selected from the group consisting of hydrogen, lower alkyl, hydroxy lower alkyl, acyloxy lower alkyl, alkoxy lower alkyl, halo lower alkyl, amino or substituted amino lower alkyl, amino, cyano, cyano lower alkyl, substituted amino, chloro, bromo and iodo, the group --COOR where R is hydrogen or lower alkyl, the group ##STR3## where R is hydrogen or lower alkyl, or derivatives thereof, e.g., the group R--C.dbd.
    Type: Grant
    Filed: March 12, 1981
    Date of Patent: August 31, 1982
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Armin Walser, Rodney I. Fryer
  • Patent number: 4336388
    Abstract: There is presented compounds of formula ##STR1## wherein X and Y are hydrogen or halogen and R.sub.1 is lower alkyl or NR.sub.2 R.sub.3wherein R.sub.2 and R.sub.3 are hydrogen or lower alkyland the pharmaceutically acceptable salts thereof.Also presented are novel intermediates and a process to produce the novel end products.The compounds of formula I are useful as anxiolytic and sedative agents.
    Type: Grant
    Filed: December 15, 1980
    Date of Patent: June 22, 1982
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Rodney I. Fryer, Norman W. Gilman
  • Patent number: 4321199
    Abstract: There is presented compounds of formula ##STR1## wherein X and Y are hydrogen or halogen and R.sub.1 is lower alkyl or NR.sub.2 R.sub.3wherein R.sub.2 and R.sub.3 are hydrogen or lower alkyland the pharmaceutically acceptable salts thereof.Also presented are novel intermediates and a process to produce the novel end products.The compounds of formula I are useful as anxiolytic and sedative agents.
    Type: Grant
    Filed: December 15, 1980
    Date of Patent: March 23, 1982
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Rodney I. Fryer, Norman W. Gilman
  • Patent number: 4307237
    Abstract: This invention is directed toward pharmacologically active compound of the formula ##STR1## wherein A is ##STR2## R.sub.1 is selected from the group consisting of hydrogen, lower alkyl, hydroxy lower alkyl, acyloxy lower alkyl, phenyl, alkoxy lower alkyl, halo lower alkyl, amino lower alkyl, substituted amino lower alkyl, substituted phenyl, pyridyl, aralkyl and the groups ##STR3## wherein R is hydrogen or lower alkyl and ROOC where R is lower alkyl; R.sub.2 is selected from the group consisting of hydrogen, lower alkyl, hydroxy lower alkyl, acyloxy lower alkyl, alkoxy lower alkyl, halo lower alkyl, amino or substituted amino lower alkyl, amino, cyano, cyano lower alkyl, substituted amino, chloro, bromo and iodo, the group --COOR where R is hydrogen or lower alkyl, the group ##STR4## where R is hydrogen or lower alkyl, or derivatives thereof, e.g., the group R--C.dbd.
    Type: Grant
    Filed: August 14, 1980
    Date of Patent: December 22, 1981
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Armin Walser, Rodney I. Fryer
  • Patent number: 4299971
    Abstract: There is presented triazolobenzazepines of the formula ##STR1## wherein R.sub.1 is hydrogen or lower alkyl and X and Y are hydrogen or halogenand the pharmaceutically acceptable salts thereof.Also disclosed are novel processes and intermediates leading to the triazolobenzazepines.The triazolobenzazepines are useful compounds having anxiolytic, sedative, muscle relaxant and anticonvulsant activity.
    Type: Grant
    Filed: July 30, 1980
    Date of Patent: November 10, 1981
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Rodney I. Fryer, Eugene J. Trybulski, Armin Walser
  • Patent number: 4280957
    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: May 15, 1978
    Date of Patent: July 28, 1981
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Armin Walser, Rodney I. Fryer
  • Patent number: 4269774
    Abstract: There is presented compounds of formula ##STR1## wherein X and Y are hydrogen or halogen and R.sub.1 is lower alkyl or NR.sub.2 R.sub.3wherein R.sub.2 and R.sub.3 are hydrogen or lower alkyland the pharmaceutically acceptable salts thereof.Also presented are novel intermediates and a process to produce the novel end products.The compounds of formula I are useful as anxiolytic and sedative agents.
    Type: Grant
    Filed: June 23, 1980
    Date of Patent: May 26, 1981
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Rodney I. Fryer, Norman W. Gilman
  • Patent number: 4260772
    Abstract: There is presented triazolobenzazepines of the formula ##STR1## wherein R.sub.1 is hydrogen or lower alkyl and X and Y are hydrogen or halogen and the pharmaceutically acceptable salts thereof.Also disclosed are novel processes and intermediates leading to the triazolobenzazepines.The triazolobenzazepines are useful compounds having anxiolytic, sedative, muscle relaxant and anticonvulsant activity.
    Type: Grant
    Filed: July 30, 1980
    Date of Patent: April 7, 1981
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Rodney I. Fryer, Eugene J. Trybulski, Armin Walser
  • Patent number: 4260773
    Abstract: There is presented triazolobenzazepines of the formula ##STR1## wherein R.sub.1 is hydrogen or lower alkyl and X and Y are hydrogen or halogen and the pharmaceutically acceptable salts thereof.Also disclosed are novel processes and intermediates leading to the triazolobenzazepines.The triazolobenzazepines are useful compounds having anxiolytic, sedative, muscle relaxant and anticonvulsant activity.
    Type: Grant
    Filed: July 30, 1980
    Date of Patent: April 7, 1981
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Rodney I. Fryer, Eugene J. Trybulski, Armin Walser
  • Patent number: 4259503
    Abstract: There is presented triazolobenzazepines of the formula ##STR1## wherein R.sub.1 is hydrogen or lower alkyl and X and Y are hydrogen or halogenand the pharmaceutically acceptable salts thereof.Also disclosed are novel processes and intermediates leading to the triazolobenzazepines.The triazolobenzazepines are useful compounds having anxiolytic, sedative, muscle relaxant and anticonvulsant activity.
    Type: Grant
    Filed: July 30, 1980
    Date of Patent: March 31, 1981
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Rodney I. Fryer, Eugene J. Trybulski, Armin Walser