Patents Assigned to McNeil Laboratories, Incorporated
  • Patent number: 4243667
    Abstract: 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: Grant
    Filed: January 30, 1979
    Date of Patent: January 6, 1981
    Assignee: McNeil Laboratories, Incorporated
    Inventor: Chris R. Rasmussen
  • Patent number: 4211867
    Abstract: 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: Grant
    Filed: August 29, 1977
    Date of Patent: July 8, 1980
    Assignee: McNeil Laboratories, Incorporated
    Inventor: Chris R. Rasmussen
  • Patent number: 4210590
    Abstract: 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: Grant
    Filed: January 6, 1978
    Date of Patent: July 1, 1980
    Assignee: McNeil Laboratories, Incorporated
    Inventors: Bruce E. Maryanoff, David F. McComsey
  • Patent number: 4174401
    Abstract: 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: Grant
    Filed: July 13, 1977
    Date of Patent: November 13, 1979
    Assignee: McNeil Laboratories, Incorporated
    Inventor: Chris R. Rasmussen
  • Patent number: 4125537
    Abstract: 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: Grant
    Filed: February 7, 1977
    Date of Patent: November 14, 1978
    Assignee: McNeil Laboratories, Incorporated
    Inventor: Richard J. Carmosin
  • Patent number: 4123538
    Abstract: 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: Grant
    Filed: August 30, 1977
    Date of Patent: October 31, 1978
    Assignee: McNeil Laboratories, Incorporated
    Inventor: Michael J. Umen
  • Patent number: 4119639
    Abstract: 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: Grant
    Filed: June 27, 1977
    Date of Patent: October 10, 1978
    Assignee: McNeil Laboratories, Incorporated
    Inventor: John Robert Carson
  • Patent number: 4111954
    Abstract: 1-Methylpyrrole-2-acetonitrile is prepared by the reduction of .alpha.-imino-1-loweralkylpyrrole-2-acetonitrile using hydrogen sulfide as the reducing agent.
    Type: Grant
    Filed: April 20, 1977
    Date of Patent: September 5, 1978
    Assignee: McNeil Laboratories, Incorporated
    Inventors: John Robert Carson, Richard J. Carmosin, Anthony T. Stefanski
  • Patent number: 4101659
    Abstract: Benzhydryl derivatives of guanidine (Formula I) having blood sugar lowering activity; pharmaceutical hypoglycemic compositions thereof and methods of administering same to hyperglycemic individuals.
    Type: Grant
    Filed: August 29, 1977
    Date of Patent: July 18, 1978
    Assignee: McNeil Laboratories, Incorporated
    Inventor: Chris Royce Rasmussen
  • Patent number: 4093811
    Abstract: 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: Grant
    Filed: June 3, 1976
    Date of Patent: June 6, 1978
    Assignee: McNeil Laboratories, Incorporated
    Inventor: Chris Royce Rasmussen
  • Patent number: 4070368
    Abstract: 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: Grant
    Filed: June 17, 1974
    Date of Patent: January 24, 1978
    Assignee: McNeil Laboratories, Incorporated
    Inventor: John Robert Carson
  • Patent number: 4059583
    Abstract: Substituted thioindoles and their sulfoxide and sulfone derivatives, useful as cardiac rate lowering agents and for other pharmacological properties, and precursors therefor.
    Type: Grant
    Filed: October 13, 1976
    Date of Patent: November 22, 1977
    Assignee: McNeil Laboratories, Incorporated
    Inventors: David Fred McComsey, Michael John Zelesko
  • Patent number: 4048191
    Abstract: Halo-substituted 1-loweralkyl-5-aroylpyrrole-2-acetic acid compounds, useful for their anti-inflammatory activity.
    Type: Grant
    Filed: June 27, 1975
    Date of Patent: September 13, 1977
    Assignee: McNeil Laboratories, Incorporated
    Inventor: John Robert Carson
  • Patent number: 4046763
    Abstract: 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: Grant
    Filed: November 17, 1972
    Date of Patent: September 6, 1977
    Assignee: McNeil Laboratories, Incorporated
    Inventors: Norman Schwartz, Richard J. Mohrbacher
  • Patent number: 4046909
    Abstract: 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: Grant
    Filed: July 16, 1975
    Date of Patent: September 6, 1977
    Assignee: McNeil Laboratories, Incorporated
    Inventors: Chris Royce Rasmussen, Joseph Francis Gardocki, James Nelson Plampin
  • Patent number: 4031079
    Abstract: 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: Grant
    Filed: June 23, 1976
    Date of Patent: June 21, 1977
    Assignee: McNeil Laboratories, Incorporated
    Inventors: Richard J. Mohrbacher, Philip P. Grous
  • Patent number: 4025517
    Abstract: 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: Grant
    Filed: June 7, 1976
    Date of Patent: May 24, 1977
    Assignee: McNeil Laboratories, Incorporated
    Inventor: Chris Royce Rasmussen
  • Patent number: 4022767
    Abstract: 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: Grant
    Filed: June 23, 1976
    Date of Patent: May 10, 1977
    Assignee: McNeil Laboratories, Incorporated
    Inventors: Richard J. Mohrbacher, Philip P. Grous
  • Patent number: 4020055
    Abstract: 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: Grant
    Filed: June 23, 1976
    Date of Patent: April 26, 1977
    Assignee: McNeil Laboratories, Incorporated
    Inventors: Richard J. Mohrbacher, Philip P. Grous
  • Patent number: 4002610
    Abstract: 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: Grant
    Filed: September 22, 1975
    Date of Patent: January 11, 1977
    Assignee: McNeil Laboratories, Incorporated
    Inventors: Richard J. Mohrbacher, Philip P. Grous