Patents Assigned to McNeil Laboratories, Incorporated
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Patent number: 4243667Abstract: Novel 2-benzhydrylimino-1,3-diazacarbocyclic compounds of the formula ##STR1## wherein R' and R" independently are selected from the group consisting of hydrogen and methyl, X and Y independently are selected from the group consisting of hydrogen, lower alkoxy, lower alkyl and halo, and n is an integer of from 2 to 4, inclusive; and their acid addition salts are disclosed. Compounds have antisecretory properties. Certain of the compounds also have hypoglycemic properties.Type: GrantFiled: January 30, 1979Date of Patent: January 6, 1981Assignee: McNeil Laboratories, IncorporatedInventor: Chris R. Rasmussen
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Patent number: 4211867Abstract: 5-, 6- or 7-Membered fully saturated 1-azacarbocyclic-2-ylidene derivatives of guanidine having anti-secretory and hypoglycemic activities, and further useful for treatment of cardiovascular disease states.Type: GrantFiled: August 29, 1977Date of Patent: July 8, 1980Assignee: McNeil Laboratories, IncorporatedInventor: Chris R. Rasmussen
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Patent number: 4210590Abstract: A method for reducing indole compounds to the corresponding indoline compounds substantially free of undesirable side reactions is described. The method involves contacting an indole compound with a borane complex reagent in the presence of trifluoroacetic acid. The method is rapidly and readily carried out and provides an excellent method for preparing certain indoline compounds from the corresponding indole compounds. A novel dioxyborane useful as a borane reagent is also disclosed.Type: GrantFiled: January 6, 1978Date of Patent: July 1, 1980Assignee: McNeil Laboratories, IncorporatedInventors: Bruce E. Maryanoff, David F. McComsey
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Patent number: 4174401Abstract: Novel 2-benzhydrylimino-1,3-diazacarbocyclic compounds of the formula ##STR1## wherein R' and R" independently are selected from the group consisting of hydrogen and methyl, X and Y independently are selected from the group consisting of hydrogen, lower alkoxy, lower alkyl and halo, and n is an integer of from 2 to 4, inclusive; and their acid addition salts are disclosed. Compounds have antisecretory properties. Certain of the compounds also have hypoglycemic properties.Type: GrantFiled: July 13, 1977Date of Patent: November 13, 1979Assignee: McNeil Laboratories, IncorporatedInventor: Chris R. Rasmussen
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Patent number: 4125537Abstract: Loweralkyl 1-loweralkyl-pyrrole-2-glyoxylates are reduced by the base-catalyzed action of hydrogen sulfide under pressure of at least 30 p.s.i. to loweralkyl 1-loweralkyl-pyrrole-2-acetates.Type: GrantFiled: February 7, 1977Date of Patent: November 14, 1978Assignee: McNeil Laboratories, IncorporatedInventor: Richard J. Carmosin
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Patent number: 4123538Abstract: Novel (2-amino-2-oxoethoxy)acetic acid compounds and antisecretory compositions and methods employing (2-amino-2-oxoethoxy)acetic acid compounds are disclosed. The (2-amino-2-oxoethoxy)acetic acid compounds are also useful as cardiotonic agents and as calcium binding agents; certain of the compounds are also useful for their calcium transport properties. Novel 4-substituted 3,5-morpholinediones intermediates in the preparation of certain of the (2-amino-2-oxoethoxy)acetic acid compounds and further useful as antisecretory agents are also disclosed.Type: GrantFiled: August 30, 1977Date of Patent: October 31, 1978Assignee: McNeil Laboratories, IncorporatedInventor: Michael J. Umen
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Patent number: 4119639Abstract: The interaction of a 2-aryldithiolanium cation with an appropriate pyrrole-2-acetic acid derivative to give a 5-[2-aryl-2-(1,3-dithiolanyl)]pyrrole-2-acetic acid derivative which is then converted to the corresponding 5-aroylpyrrole-2-acetic acid derivative.Type: GrantFiled: June 27, 1977Date of Patent: October 10, 1978Assignee: McNeil Laboratories, IncorporatedInventor: John Robert Carson
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Patent number: 4111954Abstract: 1-Methylpyrrole-2-acetonitrile is prepared by the reduction of .alpha.-imino-1-loweralkylpyrrole-2-acetonitrile using hydrogen sulfide as the reducing agent.Type: GrantFiled: April 20, 1977Date of Patent: September 5, 1978Assignee: McNeil Laboratories, IncorporatedInventors: John Robert Carson, Richard J. Carmosin, Anthony T. Stefanski
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Patent number: 4101659Abstract: Benzhydryl derivatives of guanidine (Formula I) having blood sugar lowering activity; pharmaceutical hypoglycemic compositions thereof and methods of administering same to hyperglycemic individuals.Type: GrantFiled: August 29, 1977Date of Patent: July 18, 1978Assignee: McNeil Laboratories, IncorporatedInventor: Chris Royce Rasmussen
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Patent number: 4093811Abstract: Novel 2-aryl-4-cyanomethyl-5-methylimidazoles useful for their ultra-violet (U.V.) absorbing properties, and certain novel precursors therefor. The species, 2-cyanomethyl-5-methyl-4-phenylimidazole, also has cerebral vasodilating activity.Type: GrantFiled: June 3, 1976Date of Patent: June 6, 1978Assignee: McNeil Laboratories, IncorporatedInventor: Chris Royce Rasmussen
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Patent number: 4070368Abstract: The compounds are of the class of 5-aroyl-pyrrole alkanoic acids and corresponding acid derivatives thereof useful as anti-inflammatory agents and as synthetic intermediates.Type: GrantFiled: June 17, 1974Date of Patent: January 24, 1978Assignee: McNeil Laboratories, IncorporatedInventor: John Robert Carson
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Patent number: 4059583Abstract: Substituted thioindoles and their sulfoxide and sulfone derivatives, useful as cardiac rate lowering agents and for other pharmacological properties, and precursors therefor.Type: GrantFiled: October 13, 1976Date of Patent: November 22, 1977Assignee: McNeil Laboratories, IncorporatedInventors: David Fred McComsey, Michael John Zelesko
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Patent number: 4048191Abstract: Halo-substituted 1-loweralkyl-5-aroylpyrrole-2-acetic acid compounds, useful for their anti-inflammatory activity.Type: GrantFiled: June 27, 1975Date of Patent: September 13, 1977Assignee: McNeil Laboratories, IncorporatedInventor: John Robert Carson
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Patent number: 4046763Abstract: The compound 2,3-diphenyl-5-ethyl-pyrazine, useful as a precursor in the synthesis of those compounds of the class of pyrazine, arylpyrazine, diphenylpyrazine, and cycloalkylpyrazine malonates, acetates, acetamides, and acetic acids, useful for their ultraviolet light absorption properties.Type: GrantFiled: November 17, 1972Date of Patent: September 6, 1977Assignee: McNeil Laboratories, IncorporatedInventors: Norman Schwartz, Richard J. Mohrbacher
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Patent number: 4046909Abstract: Compounds of the class of 1-aryl-3-pyrrolidylidene ureas, 1-aryl-3-piperidylidene ureas and 1-aryl-3-hexahydroazepinylidene ureas, useful as central nervous system (CNS) depressants.Type: GrantFiled: July 16, 1975Date of Patent: September 6, 1977Assignee: McNeil Laboratories, IncorporatedInventors: Chris Royce Rasmussen, Joseph Francis Gardocki, James Nelson Plampin
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Patent number: 4031079Abstract: Compounds of the class of 2-amino-3,4-dihydro-4-loweralkyl-5H-1,4-benzodiazepine-5-ones useful as CNS depressants and hypotensive agents.Type: GrantFiled: June 23, 1976Date of Patent: June 21, 1977Assignee: McNeil Laboratories, IncorporatedInventors: Richard J. Mohrbacher, Philip P. Grous
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Patent number: 4025517Abstract: Compounds of the class of 4-oxo-2-imidazolidinylidene ureas and 4-oxo-2-hexahydropyrimidinylidene ureas, useful as anti-secretory agents and central nervous system (CNS) depressants.Type: GrantFiled: June 7, 1976Date of Patent: May 24, 1977Assignee: McNeil Laboratories, IncorporatedInventor: Chris Royce Rasmussen
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Patent number: 4022767Abstract: Compounds of the class of 2-amino-3,4-dihydro-4-loweralkyl-5H-1,4-benzodiazepine-5-ones useful as CNS depressants and hypotensive agents.Type: GrantFiled: June 23, 1976Date of Patent: May 10, 1977Assignee: McNeil Laboratories, IncorporatedInventors: Richard J. Mohrbacher, Philip P. Grous
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Patent number: 4020055Abstract: Compounds of the class of 2-amino-3,4-dihydro-4-loweralkyl-5H-1,4-benzodiazepine-5-ones useful as CNS depressants and hypotensive agents.Type: GrantFiled: June 23, 1976Date of Patent: April 26, 1977Assignee: McNeil Laboratories, IncorporatedInventors: Richard J. Mohrbacher, Philip P. Grous
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Patent number: 4002610Abstract: Compounds of the class of 2-amino-3,4-dihydro-4-loweralkyl-5H-1,4-benzodiazepine-5-ones useful as CNS depressants and hypotensive agents.Type: GrantFiled: September 22, 1975Date of Patent: January 11, 1977Assignee: McNeil Laboratories, IncorporatedInventors: Richard J. Mohrbacher, Philip P. Grous