Patents by Inventor Eugene J. Trybulski
Eugene J. Trybulski 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: 5451685Abstract: This disclosure describes novel substituted oxotremorine derivatives of formula I having nitrogen, oxygen or sulfur groups and the prodrug forms of these derivatives. The compounds have cholinergic activity. Also disclosed are methods for treating diseases of the central nervous system in mammals employing the compounds, pharmaceutical preparations containing the compounds and the processes for the production of the compounds.Type: GrantFiled: July 13, 1994Date of Patent: September 19, 1995Assignee: American Cyanamid CompanyInventors: Eugene J. Trybulski, Richard H. Kramss, Herbert Brabander
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Patent number: 5356885Abstract: This disclosure describes novel substituted oxotremorine derivatives of formula I having nitrogen, oxygen or sulfur groups and the prodrug forms of these derivatives. The compounds have cholinergic activity. Also disclosed are methods for treating diseases of the central nervous system in mammals employing the compounds, pharmaceutical preparations containing the compounds and the processes for the production of the compounds.Type: GrantFiled: April 24, 1991Date of Patent: October 18, 1994Assignee: American Cyanamid CompanyInventors: Eugene J. Trybulski, Richard H. Kramss, Herbert Brabander
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Patent number: 5346910Abstract: Maleimide derivatives of oxotremorine and their alkylthiol addition products having the general formulae: ##STR1## wherein R.sub.1 and R.sub.2 are independently alkyl, hydroxyalkyl, acyloxy, trialkylsilyloxy or R.sub.1 and R.sub.2 taken together are substituted or unsubstituted pyrrolidine or piperidine, and pharmaceutical compositions for the treatment of central cholinergic disfunction.Type: GrantFiled: June 3, 1992Date of Patent: September 13, 1994Assignee: American Cyanamid CompanyInventors: Eugene J. Trybulski, Herbert J. Brabander
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Patent number: 5128483Abstract: Compounds of the formula: ##STR1## wherein A is t-butoxy carbonyl, which compounds are useful as intermediates for preparing 1-Substituted-2-(3-amino-1-propynyl)pyrrolidine derivatives having cholinergic agonist activity.Type: GrantFiled: May 8, 1991Date of Patent: July 7, 1992Assignee: American Cyanamid CompanyInventors: Eugene J. Trybulski, Richard H. Kramss
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Patent number: 5089518Abstract: This disclosure describes novel 3 or 4 substituted oxotremorine derivatives having polar substituted oxygen or sulfur groups. The compounds have cholinergic activity. Also disclosed are methods for treating diseases of the central nervous system in mammals employing the compounds, pharmaceutical preparations containing the compounds and processes for the production of the compounds.Type: GrantFiled: August 22, 1990Date of Patent: February 18, 1992Assignee: American Cyanamid CompanyInventors: Eugene J. Trybulski, Richard H. Kramss, Herbert J. Brabander
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Patent number: 5025099Abstract: Pharmaceutical compounds and compositions which may be represented by the following structural formula: ##STR1## wherein NR'" is selected from amino, (C.sub.1 -C.sub.6) alkylamino, dialkylamino or trialkylamino, pyrrolidino or piperidino. The compounds and compositions are useful in treating central cholinergic dysfunction in mammals.Type: GrantFiled: February 2, 1990Date of Patent: June 18, 1991Assignee: American Cyanamid CompanyInventors: Eugene J. Trybulski, Herbert J. Brabander
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Patent number: 5001142Abstract: Compounds of the formula: ##STR1## pharmaceutical compositions containing the compounds and methods of using the compounds in the treatment of central cholinergic disfunction in a mammal are disclosed.Type: GrantFiled: July 19, 1989Date of Patent: March 19, 1991Assignee: American Cyanamid CompanyInventors: Eugene J. Trybulski, Richard H. Kramss
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Patent number: 4990520Abstract: Pharmaceutical compounds and compositions which may be represented by the following structural formulae: ##STR1## where R is hydrogen or lower alkyl and NR'" is amino, (C.sub.1 -C.sub.6) alkylamino, dialkylamino, or trialkylamino, pyrrolidino or piperidino. The compounds are useful in treating central cholinergic disfunction in mammals.Type: GrantFiled: February 2, 1990Date of Patent: February 5, 1991Assignee: American Cyanamid CompanyInventors: Eugene J. Trybulski, Herbert J. Brabander
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Patent number: 4952600Abstract: This disclosure describes novel 3 or 4 substituted oxotremorine derivatives having polar substituted oxygen or sulfur groups. The compounds have cholinergic activity. Also disclosed are methods for treating diseases of the central nervous system in mammals employing the compounds, pharmaceutical preparations containing the compounds and processes for the production of the compounds.Type: GrantFiled: February 20, 1990Date of Patent: August 28, 1990Assignee: American Cyanamid CompanyInventors: Eugene J. Trybulski, Richard H. Kramss, Herbert J. Brabander
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Patent number: 4937235Abstract: This disclosure describes novel 3 or 4 substituted oxotremorine derivatives having polar substituted oxygen or sulfur groups. The compounds have cholinergic activity. Also disclosed are methods for treating diseases of the central nervous system in mammals employing the compounds, pharmaceutical preparations containing the compounds and processes for the production of the compounds.Type: GrantFiled: January 23, 1989Date of Patent: June 26, 1990Assignee: American Cyanamid CompanyInventors: Eugene J. Trybulski, Richard H. Kramss, Herbert J. Brabander
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Patent number: 4549988Abstract: 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: GrantFiled: June 29, 1983Date of Patent: October 29, 1985Assignee: Hoffmann-La Roche Inc.Inventors: Rodney I. Fryer, Eugene J. Trybulski, Armin Walser
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Patent number: 4548750Abstract: 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: GrantFiled: October 17, 1983Date of Patent: October 22, 1985Assignee: Hoffmann-La Roche Inc.Inventors: Rodney I. Fryer, Eugene J. Trybulski, Armin Walser
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Patent number: 4547581Abstract: 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: GrantFiled: August 23, 1984Date of Patent: October 15, 1985Assignee: Hoffmann-La Roche Inc.Inventors: Rodney I. Fryer, Norman W. Gilman, Eugene J. Trybulski, Armin Walser
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Patent number: 4546183Abstract: 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: GrantFiled: August 23, 1984Date of Patent: October 8, 1985Assignee: Hoffmann-La Roche Inc.Inventors: Rodney I. Fryer, Norman W. Gilman, Eugene J. Trybulski, Armin Walser
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Patent number: 4481142Abstract: 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: GrantFiled: October 27, 1982Date of Patent: November 6, 1984Assignee: Hoffmann-La Roche Inc.Inventors: Rodney I. Fryer, Norman W. Gilman, Eugene J. Trybulski, Armin Walser
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Patent number: 4469633Abstract: Compounds of the formula ##STR1## wherein X and Y are selected from the group consisting of hydrogen, halogen and trifluoromethyl, are disclosed.The compounds are useful as intermediates in the production of 2-benzazepines, compounds of pharmacological activity.Also disclosed are other intermediates and processes for their production.Type: GrantFiled: November 23, 1981Date of Patent: September 4, 1984Assignee: Hoffmann-La Roche Inc.Inventor: Eugene J. Trybulski
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Patent number: 4460781Abstract: 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: GrantFiled: January 5, 1983Date of Patent: July 17, 1984Assignee: Hoffmann-La Roche Inc.Inventors: George F. Field, Rodney I. Fryer, Eugene J. Trybulski, Armin Walser
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Patent number: 4436662Abstract: 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: GrantFiled: March 31, 1983Date of Patent: March 13, 1984Assignee: Hoffmann-La Roche Inc.Inventors: Rodney I. Fryer, Eugene J. Trybulski, Armin Walser
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Patent number: 4431823Abstract: 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: GrantFiled: August 3, 1982Date of Patent: February 14, 1984Assignee: Hoffmann-La Roche Inc.Inventors: Rodney I. Fryer, Eugene J. Trybulski, Armin Walser
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Patent number: 4428879Abstract: 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: GrantFiled: August 3, 1982Date of Patent: January 31, 1984Assignee: Hoffmann-La Roche Inc.Inventors: Rodney I. Fryer, Eugene J. Trybulski, Armin Walser