Patents by Inventor Albert D. Cale, Jr.

Albert D. Cale, Jr. 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: 4379151
    Abstract: 3-Phenoxyazetidines having the formula: ##STR1## wherein R is hydrogen, aminocarbonyl and trifluoromethyl having anorexigenic activity are disclosed.
    Type: Grant
    Filed: October 16, 1981
    Date of Patent: April 5, 1983
    Assignee: A. H. Robins Company, Inc.
    Inventor: Albert D. Cale, Jr.
  • Patent number: 4362667
    Abstract: The resolution of racemic 4-amino-N-(1-cyclohexyl-3-pyrrolidinyl)-N-methylbenzamide into the optically active (+) and (-) isomers is disclosed.
    Type: Grant
    Filed: January 21, 1981
    Date of Patent: December 7, 1982
    Assignee: A. H. Robins Company, Inc.
    Inventors: Albert D. Cale, Jr., Charles A. Leonard
  • Patent number: 4327108
    Abstract: This invention provides a novel class of 2-iminoimidazolidines which include 4-substituted derivatives such as 4-(2-chloroethyl)-1-methyl-2-methylimino-3-phenyl imidazolidine fumarate: ##STR1## This illustrated 4-substituted 2-iminoimidazolidine compound exhibits cardiovascular hypotensive, hypoglycemic (glucose tolerance, and sugar cataract) and anti-inflammatory (pleural effusion) pharmacological activities in test animals.
    Type: Grant
    Filed: May 5, 1980
    Date of Patent: April 27, 1982
    Assignee: A. H. Robins Company, Inc.
    Inventor: Albert D. Cale, Jr.
  • Patent number: 4327107
    Abstract: This invention provides a novel class of 2-iminoimidazolidines which include 4-substituted derivatives such as 4-(2-chloroethyl)-1-methyl-2-methylimino-3-phenyl imidazolidine fumarate: ##STR1## This illustrated 4-substituted 2-iminoimidazolidine compound exbibits cardiovascular hypotensive, hypoglycemic (glucose tolerance, and sugar cataract) and anti-inflammatory (pleural effusion) pharmacological activities in test animals.
    Type: Grant
    Filed: May 5, 1980
    Date of Patent: April 27, 1982
    Assignee: A. H. Robins Company, Inc.
    Inventor: Albert D. Cale, Jr.
  • Patent number: 4327098
    Abstract: This invention provides a novel class of 2-iminoimidazolidines which include 4-substituted derivatives such as 4-(2-chloroethyl)-1-methyl-2-methylimino-3-phenyl imidazolidine fumarate: ##STR1## This illustrated 4-substituted 2-iminoimidazolidine compound exhibits cardiovascular hypotensive, hypoglycemic (glucose tolerance, and sugar cataract) and anti-inflammatory (pleural effusion) pharmacological activities in test animals.
    Type: Grant
    Filed: May 5, 1980
    Date of Patent: April 27, 1982
    Assignee: A. H. Robins Company, Inc.
    Inventor: Albert D. Cale, Jr.
  • Patent number: 4296037
    Abstract: 1-Hydrocarbon-3,3-diphenyl-4-hydroxymethyl-2-pyrrolidinones and methods for making them from 4,5-dihydro-3,3-diphenyl-4-hydrocarbylaminomethylfuran-2(3H)ones are disclosed. Methods for making the 4,5-dihydro-3,3-diphenyl-4-hydrocarbylaminomethylfuran-2(3H)ones are also disclosed. The novel compounds are useful intermediates for the preparation of pharmacologically active 4-(4,4-disubstitutedpiperidinylmethyl)-3,3-diphenyl-2-pyrrolidinones.
    Type: Grant
    Filed: July 24, 1978
    Date of Patent: October 20, 1981
    Assignee: A. H. Robins Company, Incorporated
    Inventor: Albert D. Cale, Jr.
  • Patent number: 4288591
    Abstract: This invention provides a novel class of 2-iminoimidazolidines which include 4-substituted derivatives such as 4-(2-chloroethyl)-1-methyl-2-methylimino-3-phenyl imidazolidine fumarate: ##STR1## This illustrated 4-substituted 2-iminoimidazolidine compound exhibits cardiovascular hypotensive, hypoglycemic (glucose tolerance, and sugar cataract) and anti-inflammatory (pleural effusion) pharmacological activities in test animals.
    Type: Grant
    Filed: May 5, 1980
    Date of Patent: September 8, 1981
    Assignee: A. H. Robins Company, Inc.
    Inventor: Albert D. Cale, Jr.
  • Patent number: 4288447
    Abstract: This invention provides a novel class of 2-iminoimidazolidines which include 4-substituted derivatives such as 4-(2-chloroethyl)-1-methyl-2-methylimino-3-phenyl imidazolidine fumarate: ##STR1## This illustrated 4-substituted 2-iminoimidazolidine compound exhibits cardiovascular hypotensive, hypoglycemic (glucose tolerance, and sugar cataract) and anti-inflammatory (pleural effusion) pharmacological activities in test animals.
    Type: Grant
    Filed: May 5, 1980
    Date of Patent: September 8, 1981
    Assignee: A. H. Robins Company, Inc.
    Inventor: Albert D. Cale, Jr.
  • Patent number: 4282243
    Abstract: The resolution of racemic 4-amino-N-(1-cyclohexyl-3-pyrrolidinyl)-N-methylbenzamide into the optically active (+) and (-) isomers is disclosed.
    Type: Grant
    Filed: March 10, 1980
    Date of Patent: August 4, 1981
    Assignee: A. H. Robins Company, Inc.
    Inventors: Albert D. Cale, Jr., Charles A. Leonard
  • Patent number: 4282244
    Abstract: The resolution of racemic 4-amino-N-(1-cyclohexyl-3-pyrrolidinyl)-N-methylbenzamide into the optically active (+) and (-) isomers is disclosed.
    Type: Grant
    Filed: March 10, 1980
    Date of Patent: August 4, 1981
    Assignee: A. H. Robins Company, Inc.
    Inventors: Albert D. Cale, Jr., Charles A. Leonard
  • Patent number: 4279822
    Abstract: N-(1-Substituted-3-pyrrolidinyl)benzamides of the formula ##STR1## wherein R is cycloalkyl or phenyllower-alkyl; R.sup.1 is hydrogen or lower alkyl of 1 to 8 carbon atoms; R.sup.2 is acetamido, amino, methylamino, dimethylamino, benzyloxy, halogen, lower alkoxy, methylmercapto, nitro, cyano, hydroxy, sulfamoyl, bis(methylsulfonyl)amino, methylsulfonylamino, aminomethyl or acetylaminomethyl and can be the same or different; n is an integer from one to three inclusive with the proviso that when R.sup.2 is amino, nitro, halogen or lower alkoxy, n is greater than one, and pharmaceutically acceptable acid addition salts thereof are disclosed.
    Type: Grant
    Filed: December 6, 1976
    Date of Patent: July 21, 1981
    Assignee: A. H. Robins Company, Inc.
    Inventors: Albert D. Cale, Jr., Charles A. Leonard
  • Patent number: 4260606
    Abstract: This invention provides a novel class of 3-methyleneazetidines which include diphenylmethyl derivatives such as 1-isopropyl-3-diphenylmethyleneazetidine oxalate: ##STR1## This illustrated 3-methyleneazetidine compound is characterized by a combination of pharmacological properties which are indicative of utility as a mood elevating therapeutic agent for relieving the symptoms of depression in humans. The illustrated compound exhibits an ED.sub.50 (tetrabenazine-induced ptosis) of 2.18 mg/kg in mice.
    Type: Grant
    Filed: July 19, 1979
    Date of Patent: April 7, 1981
    Assignee: A. H. Robins Company, Inc.
    Inventors: Albert D. Cale, Jr., Herndon Jenkins
  • Patent number: 4247705
    Abstract: This invention provides a novel class of 2-iminoimidazolidines which include 4-substituted derivatives such as 4-(2-chloroethyl)-1-methyl-2-methylimino-3-phenyl imidazolidine fumarate: ##STR1## This illustrated 4-substituted 2-iminoimidazolidine compound exhibits cardiovascular hypotensive, hypoglycemic (glucose tolerance, and sugar cataract) and anti-inflammatory (pleural effusion) pharmacological activities in test animals.
    Type: Grant
    Filed: February 6, 1979
    Date of Patent: January 27, 1981
    Assignee: A. H. Robins Company, Inc.
    Inventor: Albert D. Cale, Jr.
  • Patent number: 4242261
    Abstract: This invention provides an improved process for producing methylene-cycloamines as exemplified by 1-isopropyl-3-diphenylmethyleneacetidine: ##STR1## In accordance with the invention process, the above illustrated methyleneazetidine compound is synthesized by (1) reacting .alpha.,.alpha.-diphenyl-.alpha.-(1-isopropyl-3-azetidinyl) acetamide with bromine and alkali metal alkoxide under modified Hofmann Rearrangement conditions to form a carbamate intermediate, and (2) heating the carbamate intermediate in an acidic medium to yield the 1-isopropyl-3-diphenylmethyleneazetidine product.This illustrated 3-methyleneazetidine compound is characterized by a combination of pharmacological properties which are indicative of utility as a mood elevating therapeutic agent for relieving the symptoms of depression in humans.
    Type: Grant
    Filed: July 19, 1979
    Date of Patent: December 30, 1980
    Assignee: A. H. Robins Company, Inc.
    Inventor: Albert D. Cale, Jr.
  • Patent number: 4226861
    Abstract: N-Lower-alkyl 3-phenoxy-1-azetidinecarboxamides having the formula: ##STR1## wherein R is alkyl and R.sup.1 is hydrogen, aminocarbonyl and trifluoromethyl having central nervous system activity particularly anti-convulsant activity, are disclosed.
    Type: Grant
    Filed: April 13, 1979
    Date of Patent: October 7, 1980
    Assignee: A. H. Robins Company, Inc.
    Inventor: Albert D. Cale, Jr.
  • Patent number: 4207327
    Abstract: N-(4-Pyrazolidinyl)benzamides having the formula ##STR1## and their amino precursors are disclosed wherein R is lower alkyl, lower cycloalkyl or phenyllower-alkyl; R.sup.1 is lower alkyl, lower cycloalkyl, or phenyllower-alkyl; R.sup.2 is hydrogen, lower alkyl or phenyl; R.sup.3 is hydroxy, cyano, nitro, amino, fluoro, chloro, bromo, trifluoromethyl, lower alkyl, lower alkoxy, sulfamoyl or actamido, R.sup.3 can be the same radical or different radicals; n is an integer from zero to three inclusive, and pharmaceutically acceptable acid addition salts thereof. The compounds have anti-emetic and gastric emptying properties.
    Type: Grant
    Filed: May 22, 1979
    Date of Patent: June 10, 1980
    Assignee: A. H. Robins Company, Inc.
    Inventors: Carl D. Lunsford, Albert D. Cale, Jr.
  • Patent number: 4144245
    Abstract: 1-Hydrocarbon-3,3-diphenyl-4-hydroxymethyl-2-pyrrolidinones and methods for making them from 4,5-dihydro-3,3-diphenyl-4-hydrocarbylaminomethylfuran-2(3H)ones are disclosed. Methods for making the 4,5-dihydro-3,3-diphenyl-4-hydrocarbylaminomethylfuran-2(3H)ones are also disclosed. The novel compounds are useful intermediates for the preparation of pharmacologically active 4-(4,4-disubstitutedpiperidinylmethyl)-3,3-diphenyl-2-pyrrolidinones.
    Type: Grant
    Filed: February 3, 1978
    Date of Patent: March 13, 1979
    Assignee: A. H. Robins Company, Inc.
    Inventor: Albert D. Cale, Jr.
  • Patent number: 4143150
    Abstract: Oxanilic acid derivatives having the formula: ##STR1## are disclosed wherein R is lower-alkyl, cycloalkyl, phenylalkyl or phenyl; R.sup.1 is hydrogen, lower-alkyl or phenyl; R.sup.2 is hydrogen, lower-alkyl, or lower-alkoxy; R.sup.3 is hydrogen, fluoro, chloro or bromo; X is oxygen or sulfur; and M is hydrogen, lower-alkyl or a physiologically acceptable cation. The compounds are useful for ameliorating and controlling symptoms associated with asthma.
    Type: Grant
    Filed: August 19, 1977
    Date of Patent: March 6, 1979
    Assignee: A. H. Robins Company, Inc.
    Inventors: William J. Welstead, Jr., Albert D. Cale, Jr.
  • Patent number: 4133881
    Abstract: .alpha.-(1-R-3-Azetidinyl)-.alpha.-phenyl-.alpha.-substituted-acetamides and -acetonitriles represented by the following formula: ##STR1## wherein R represents hydrogen, lower alkyl, lower cycloalkyl or phenyllower alkyl, R.sup.1 represents phenyl or 2-pyridyl, and Y is carbamoyl or cyano having antiarrhythmic activity are disclosed. Pharmaceutically acceptable acid addition salts of the free bases and quaternary salts are included as part of the invention.
    Type: Grant
    Filed: April 27, 1977
    Date of Patent: January 9, 1979
    Assignee: A. H. Robins Company, Incorporated
    Inventors: Albert D. Cale, Jr., Herndon Jenkins
  • Patent number: 4115587
    Abstract: Novel amides of norfenfluramine having the formula ##STR1## wherein R is selected from the group consisting of alkyl and alkenyl radicals having 12 to 22 carbon atoms and compositions and methods for combating atherosclerosis and hypercholesteremia, with beneficial side effects useful for combating obesity in atherosclerotic subjects are disclosed. The compounds lower lipid values and simultaneously inhibit appetite and reduce weight gain from ingested food with minimal side effects.
    Type: Grant
    Filed: December 16, 1976
    Date of Patent: September 19, 1978
    Assignee: A. H. Robins Company, Inc.
    Inventors: Carl D. Lunsford, Albert D. Cale, Jr.