Patents by Inventor Rodney Ian Fryer
Rodney Ian 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).
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Patent number: 4111934Abstract: Novel 1,5-benzodiazepin-4-one derivatives, bearing between the 1,2-positions a triazolo ring, as disclosed. These 1,2-triazolo-1,5-benzodiazepin-4-ones are useful as muscle-relaxant, anti-convulsant and sedative agents.Type: GrantFiled: December 15, 1977Date of Patent: September 5, 1978Assignee: Hoffmann-La Roche Inc.Inventors: Rodney Ian Fryer, Leo Henryk Sternbach, Armin Walser
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Patent number: 4111931Abstract: The present invention concerns compounds of the formula ##STR1## wherein X is hydrogen or halogen; R.sub.1 is hydrogen, halogen or trifluoromethyl; R.sub.2 is hydrogen or lower alkyl; and R.sub.3 is hydrogen, --COO lower alkyl or CON(R.sub.4).sub.2 wherein R.sub.2 is lower alkyl or hydrogen and may be differentand the pharmaceutically acceptable salts thereof.Also provided are methods for the preparation of these compounds as well as pharmaceutical formulations which contain the active compounds of this invention. The compounds of the formula illustrated above are useful as anxiolytics, anticonvulsants, muscle relaxants and sedative agents.Type: GrantFiled: February 1, 1978Date of Patent: September 5, 1978Assignee: Hoffmann-La Roche Inc.Inventors: Armin Walser, Rodney Ian Fryer
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Patent number: 4083948Abstract: An improved radioimmunoassay for benzodiazepines such as diazepam, chlordiazepoxide, oxazepam, demoxepam and metabolites thereof is disclosed. Such immunoassay employs novel .sup.125 I-labelled 4'-hydroxy derivatives of these compounds as tracer.Type: GrantFiled: April 4, 1977Date of Patent: April 11, 1978Assignee: Hoffmann-La Roche, Inc.Inventors: Raymond Vincent Davis, Rodney Ian Fryer
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Patent number: 4080323Abstract: The present invention concerns compounds of the formula ##STR1## wherein X is hydrogen or halogen; R.sub.1 is hydrogen, halogen or trifluoromethyl; R.sub.2 is hydrogen or lower alkyl; and R.sub.3 is hydrogen, --COO lower alkyl or CON(R.sub.4).sub.2 wherein R.sub.4 is lower alkyl or hydrogen and may be differentAnd the pharmaceutically acceptable salts thereof.Also provided are methods for the preparation of these compounds as well as pharmaceutical formulations which contain the active compounds of this invention. The compounds of the formula illustrated above are useful as anxiolytics, anticonvulsants, muscle relaxants and sedative agents.Type: GrantFiled: March 7, 1977Date of Patent: March 21, 1978Assignee: Hoffmann-La Roche Inc.Inventors: Armin Walser, Rodney Ian Fryer
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Patent number: 4049666Abstract: Tricyclic benzodiazepine derivatives (A) bearing a hydroxylower alkyl substituent in the 1-position and a heterocyclic ring joined between positions 4 and 5 of the benzodiazepine moiety are described. The heterocyclic ring will contain the nitrogen atom appearing at position 4 of the benzodiazepine ring as well as the hetero atom, which may be either oxygen or nitrogen, attached to the carbon atom at the 5-position of the benzodiazepine ring. A bearing an oxygen atom in the new heterocyclic ring may be formed from the corresponding 4,5-unsaturated benzodiazepines by treatment with an epoxide compound in the presence of an acid catalyst. A bearing either a nitrogen or an oxygen atom in the new heterocyclic ring may be prepared by cyclization of the corresponding open compound. A are useful as sedative, muscle relaxant and anti-convulsant agents.Type: GrantFiled: April 12, 1976Date of Patent: September 20, 1977Assignee: Hoffman-La Roche Inc.Inventors: Michael Edward Derieg, James Valentine Earley, Rodney Ian Fryer, Leo Henryk Sternbach
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Patent number: 4049667Abstract: Tricyclic benzodiazepine derivatives ("A") bearing a hydroxylower alkyl substituent in the 1-position and a heterocyclic ring joined between positions 4 and 5 of the benzodiazepine moiety are described. The heterocyclic ring will contain the nitrogen atom appearing at position 4 of the benzodiazepine ring as well as the hetero atom, which may be either oxygen or nitrogen, attached to the carbon atom at the 5-position of the benzodiazepine ring. "A" bearing an oxygen atom in the new heterocyclic ring may be formed from the corresponding 4,5-unsaturated benzodiazepines by treatment with an epoxide compound in the presence of an acid catalyst. "A" bearing either a nitrogen or an oxygen atom in the new heterocyclic ring may be prepared by cyclization of the corresponding open compound. "A" are useful as sedative, muscle relaxant and anti-convulsant agents.Type: GrantFiled: April 12, 1976Date of Patent: September 20, 1977Assignee: Hoffmann-La Roche Inc.Inventors: Michael Edward Derieg, James Valentine Earley, Rodney Ian Fryer, Leo Henryk Sternbach
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Patent number: 4032535Abstract: 6-Phenyl-S-triazolo[4,3-a][1,4]benzodiazepines bearing in the 8-position a hydroxyamino or azoxy substituent are disclosed together with processes for preparing these compounds and intermediates used in these processes. These triazolobenzodiazepines are useful as muscle relaxant, anti-convulsant and sedative agents.Type: GrantFiled: August 18, 1976Date of Patent: June 28, 1977Assignee: Hoffmann-La Roche Inc.Inventors: Rodney Ian Fryer, Armin Walser
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Patent number: 4017531Abstract: Tricyclic benzodiazepine derivatives ("A") bearing a hydroxylower alkyl substituent in the 1-position and a heterocyclic ring joined between positions 4 and 5 of the benzodiazepine moiety are described. The heterocyclic ring will contain the nitrogen atom appearing at position 4 of the benzodiazepine ring as well as the hetero atom, which may be either oxygen or nitrogen, attached to the carbon atom at the 5-position of the benzodiazepine ring. A bearing an oxygen atom in the new heterocyclic ring may be formed from the corresponding 4,5-unsaturated benzodiazepines by treatment with an epoxide compound in the presence of an acid catalyst. A bearing either a nitrogen or an oxygen atom in the new heterocyclic ring may be prepared by cyclization of the corresponding open compound. A are useful as sedative, muscle relaxant and anti-convulsant agents.Type: GrantFiled: April 12, 1976Date of Patent: April 12, 1977Assignee: Hoffmann-La Roche Inc.Inventors: Michael Edward Derieg, James Valentine Earley, Rodney Ian Fryer, Leo Henryk Sternbach
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Patent number: 4017532Abstract: Tricyclic benzodiazepine derivatives ("A") bearing a hydroxylower alkyl substituent in the 1-position and a heterocyclic ring joined between positions 4 and 5 of the benzodiazepine moiety are described. The heterocyclic ring will contain the nitrogen atom appearing at position 4 of the benzodiazepine ring as well as the hetero atom, which may be either oxygen or nitrogen, attached to the carbon atom at the 5-position of the benzodiazepine ring. "A" bearing an oxygen atom in the new heterocyclic ring may be formed from the corresponding 4,5-unsaturated benzodiazepines by treatment with an epoxide compound in the presence of an acid catalyst. "A" bearing either a nitrogen or an oxygen atom in the new heterocyclic ring may be prepared by cyclization of the corresponding open compound. "A" are useful as sedative, muscle relaxant and anti-convulsant agents.Type: GrantFiled: April 12, 1976Date of Patent: April 12, 1977Assignee: Hoffmann-La Roche Inc.Inventors: Michael Edward Derieg, James Valentine Earley, Rodney Ian Fryer, Leo Henryk Sternbach
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Patent number: 4014883Abstract: Derivatives of 7H-indolo[2,3-c]quinolin-6(5H)-one and 7H-indolo[2,3-c]quinoline, prepared, inter alia, from the corresponding 3-azido-4-phenylcarbostyrils or corresponding N-(lower alkylamino)-3-(2-fluorophenyl)-indole-2-carboxamides, are described. The end products of the invention are useful as anti-tumor agents, i.e., they inhibit the growth of transplantable tumors.Type: GrantFiled: July 16, 1975Date of Patent: March 29, 1977Assignee: Hoffmann-La Roche Inc.Inventors: Rodney Ian Fryer, Robert Ye-Fong Ning, Leo Henryk Sternbach, Armin Walser
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Patent number: 4014916Abstract: Tricyclic benzodiazepine derivatives ("A") bearing a hydroxylower alkyl substituent in the 1-position and a heterocyclic ring joined between positions 4 and 5 of the benzodiazepine moiety are described. The heterocyclic ring will contain the nitrogen atom appearing at position 4 of the benzodiazepine ring as well as the hetero atom, which may be either oxygen or nitrogen, attached to the carbon atom at the 5-position of the benzodiazepine ring. "A" bearing an oxygen atom in the new heterocyclic ring may be formed from the corresponding 4,5-unsaturated benzodiazepines by treatment with an epoxide compound in the presence of an acid catalyst. "A" bearing either a nitrogen or an oxygen atom in the new heterocyclic ring may be prepared by cyclization of the corresponding open compound. "A" are useful as sedative, muscle relaxant and anti-convulsant agents.Type: GrantFiled: April 12, 1976Date of Patent: March 29, 1977Assignee: Hoffmann-La Roche Inc.Inventors: Michael Edward Derieg, James Valentine Earley, Rodney Ian Fryer, Leo Henryk Sternbach
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Patent number: 3997591Abstract: Tricyclic benzodiazepine derivatives (A) bearing a hydroxylower alkyl substituent in the 1-position and a heterocyclic ring joined between positions 4 and 5 of the benzodiazepine moiety are described. The heterocyclic ring will contain the nitrogen atom appearing at position 4 of the benzodiazepine ring as well as the hetero atom, which may be either oxygen or nitrogen, attached to the carbon atom at the 5-position of the benzodiazepine ring. "A" bearing an oxygen atom in the new heterocyclic ring may be formed from the corresponding 4,5-unsaturated benzodiazepines by treatment with an epoxide compound in the presence of an acid catalyst. "A" bearing either a nitrogen or an oxygen atom in the new heterocyclic ring may be prepared by cyclization of the corresponding open compound. "A" are useful as sedative, muscle relaxant and anti-convulsant agents.Type: GrantFiled: April 12, 1976Date of Patent: December 14, 1976Assignee: Hoffmann-La Roche Inc.Inventors: Michael Edward Derieg, James Valentine Earley, Rodney Ian Fryer, Leo Henryk Sternbach
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Patent number: 3989681Abstract: Novel 1,4-benzodiazepin-2-ones of the formula ##SPC1##WhereinR.sub.1 is selected from the group consisting of hydrogen, lower alkyl, cycloalkyl-lower alkyl, hydroxylower alkyl, lower alkoxy-lower alkyl and di-lower alkylamino-lower alkyl;R.sub.2 signifies hydrogen or lower alkyl; R.sub.3 signifies hydrogen or halogen; R.sub.4 signifies lower alkylAnd the pharmaceutically acceptable acid addition salts thereof, are disclosed together with processes for preparing these compounds and novel intermediates used in these processes. These 7-azoxy substituted-1,4-benzodiazepin-2-ones are useful as muscle relaxant, anti-convulsant and sedative agents.Type: GrantFiled: November 28, 1973Date of Patent: November 2, 1976Assignee: Hoffmann-La Roche Inc.Inventors: Rodney Ian Fryer, Armin Walser
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Patent number: 3979410Abstract: o-nitrobenzylketones are prepared by reacting a trans-.beta.-substituted amino-2-nitrostyrene with a lower alkanoyl halide, halo-lower alkanoyl halide, phthalimido-lower alkanoyl halide, benzoyl halide or substituted benzoyl halide, and subsequently hydrolyzing the resulting product to yield the desired o-nitrobenzylketone.Type: GrantFiled: September 22, 1975Date of Patent: September 7, 1976Assignee: Hoffmann-La Roche Inc.Inventors: Rodney Ian Fryer, Edward Ernest Garcia
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Patent number: 3965151Abstract: Tricyclic benzodiazepine derivatives ("A") bearing a hydroxylower alkyl substituent in the 1-position and a heterocyclic ring joined between positions 4 and 5 of the benzodiazepine moiety are described. The heterocyclic ring will contain the nitrogen atom appearing at position 4 of the benzodiazepine ring as well as the hetero atom, which may be either oxygen or nitrogen, attached to the carbon atom at the 5-position of the benzodiazepine ring. "A" bearing an oxygen atom in the new heterocyclic ring may be formed from the corresponding 4,5-unsaturated benzodiazepines by treatment with an epoxide compound in the presence of an acid catalyst. "A" bearing either a nitrogen or an oxygen atom in the new heterocyclic ring may be prepared by cyclization of the corresponding open compound. "A" are useful as sedative, muscle relaxant and anti-convulsant agents.Type: GrantFiled: March 11, 1975Date of Patent: June 22, 1976Assignee: Hoffmann-La Roche Inc.Inventors: Michael Edward Derieg, James Valentine Earley, Rodney Ian Fryer, Leo Henryk Sternbach
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Patent number: 3931225Abstract: o-nitrobenzylketones are prepared by reacting a trans-.beta.-substituted amino-2-nitrostyrene with a lower alkanoyl halide, halo-lower alkanoyl halide, phthalimido-lower alkanoyl halide, benzoyl halide or substituted benzoyl halide, and subsequently hydrolyzing the resulting product to yield the desired o-nitrobenzylketone.Type: GrantFiled: January 21, 1974Date of Patent: January 6, 1976Assignee: Hoffmann-La Roche Inc.Inventors: Rodney Ian Fryer, Edward Ernest Garcia