Patents Assigned to A. H. Robins Company, Incorporated
  • Patent number: 4571393
    Abstract: 3-Phenoxy-1-azetidinecarboxamides having the formula ##STR1## wherein R.sup.1 is selected from the group consisting of hydrogen, fluoro, loweralkyl, loweralkoxy, trifluoromethyl, acetyl or aminocarbonyl having prolonged anticonvulsant activity are disclosed.
    Type: Grant
    Filed: October 23, 1984
    Date of Patent: February 18, 1986
    Assignee: A. H. Robins Company, Incorporated
    Inventor: Lina C. Teng
  • Patent number: 4568695
    Abstract: Novel 2-amino-3-benzoylphenethylalcohols are provided having the formula: ##STR1## wherein; X is hydrogen, loweralkyl, loweralkoxy, halogen or trifluoromethyl, andY is hydrogen, loweralkyl, loweralkoxy, halogen, trifluoromethyl, --S--loweralkyl, ##STR2## The compounds exhibit anti-inflammatory activity.
    Type: Grant
    Filed: December 7, 1983
    Date of Patent: February 4, 1986
    Assignee: A. H. Robins Company, Incorporated
    Inventors: Henry W. Moran, William J. Welstead, Jr.
  • Patent number: 4560510
    Abstract: A process for preparing pyrido[1,4]benzodiazepines having antidepressant activity illustrated by the formula: ##STR1## wherein Ar is pyridinyl, thienyl or phenyl; R is alkali-metal ion, hydrogen, loweralkyl or an amine or an amine precursor on the end of a hydrocarbon chain and wherein in the process condensation of an amino-chloropyridine with an aryl(aminophenyl)methanone is accomplished with a strong non-nucleophilic base in stirrable admixture with an inert liquid carrier. Alternatively, condensation is accomplished sequentially using titanium tetrachloride first followed by non-nucleophilic base.
    Type: Grant
    Filed: April 6, 1984
    Date of Patent: December 24, 1985
    Assignee: A. H. Robins Company, Incorporated
    Inventor: Young S. Lo
  • Patent number: 4558132
    Abstract: Nitro, amino and aroylamino-N-phenylpyridinamines as chemical intermediates and/or having antidepressant activity having the formula ##STR1## wherein R.sup.3 is nitro, amino or aroylamino, and Q is hydrogen, --NR.sup.1 R.sup.2 or halogen are disclosed in a process for preparing pyrido[1,4]benzodiazepines.
    Type: Grant
    Filed: July 2, 1982
    Date of Patent: December 10, 1985
    Assignee: A. H. Robins Company, Incorporated
    Inventors: Chandler R. Taylor, Jr., Young S. Lo
  • Patent number: 4558155
    Abstract: N-(Aryloxyalkyl)-N'-(aminoalkyl)ureas and thioureas having the formula: ##STR1## wherein R.sup.1 and R.sup.2 are hydrogen, loweralkyl, cycloalkyl, phenyl or phenyllower alkyl, and R.sup.3 and R.sup.4 are hydrogen, loweralkyl, phenyl and phenylalkyl or R.sup.3 and R.sup.4 taken together with the adjacent nitrogen form a heterocyclic residue are disclosed in a method of suppressing cardiac arrhythmias.
    Type: Grant
    Filed: November 13, 1984
    Date of Patent: December 10, 1985
    Assignee: A. H. Robins Company, Incorporated
    Inventors: James R. Shanklin, Jr., Christopher P. Johnson, III
  • Patent number: 4556667
    Abstract: Novel [2-[(aminopyridinyl)amino]phenyl]arylmethanones and their thioxomethyl, ketal or thioketal analogs of the formula: ##STR1## wherein; R is selected from the group consisting of hydrogen, loweralkyl, --alk.sup.1 --halo, --alk.sup.1 --NR.sup.1 --NR.sup.1 R.sup.2 or --alk.sup.1 --N.dbd.CH--OC.sub.2 H.sub.5 ;R.sup.1 and R.sup.2 are selected from the group consisting of hydrogen, loweralkyl, --C(O)O-loweralkyl or R.sup.1 and R.sup.2 taken together with the adjacent nitrogen atom may form a heterocyclic residue selected from the group consisting of 1-piperidinyl, 1-phthalimido, 1-pyrrolidinyl, 4-morpholinyl, 1-piperazinyl and 4-substituted-1-piperazinyl;B is selected from carbonyl, thioxomethyl, ketal or thioketal;Ar is selected from the group consisting of 2, 3 and 4-pyridinyl, 2 or 3-thienyl, phenyl or phenyl substituted by 1 to 3 radicals selected from halo, loweralkyl, loweralkoxy, trifluoromethyl or nitro and may be the same of different;alk.sup.
    Type: Grant
    Filed: December 9, 1983
    Date of Patent: December 3, 1985
    Assignee: A. H. Robins Company, Incorporated
    Inventor: Chandler R. Taylor, Jr.
  • Patent number: 4547514
    Abstract: Pharmaceutical compositions comprised of aryloxy-N-(aminoalkyl)-1-pyrrolidine and piperidine carboxamides and carbothioamides are provided of the formula: ##STR1## wherein Ar is selected from the group consisting of 1-naphthyl, 2-naphthyl, 2,3-dihydro-1H-inden-4-yl, 2,3-dihydro-1H-inden-5-yl, phenyl, substituted phenyl wherein the substituents are selected from lower alkyl of from 1 to 8 carbon atoms, lower alkyloxy of from 1 to 8 carbon atoms, halogen and trifluoromethyl; m and n are 1 or 2 but are never 2 at the same time; p is 1, 2, 3 or 4; R is selected from hydrogen or lower alkyl of from 1 to 3 carbon atoms; R.sup.1 and R.sup.2 are selected from hydrogen, lower alkyl of from 1 to 8 carbon atoms, phenyl, phenyl lower alkyl of from 7 to 9 carbon atoms, and cycloalkyl of from 3 to 8 carbon atoms, and R.sup.1 and R.sup.
    Type: Grant
    Filed: December 5, 1983
    Date of Patent: October 15, 1985
    Assignee: A. H. Robins Company, Incorporated
    Inventors: Pershottam P. Mathur, William L. Smith
  • Patent number: 4547518
    Abstract: N-(1-Substituted-4,5-dihydro-1H-pyrazol-4-yl)benzamides having the general formula: ##STR1## wherein R is loweralkyl, cycloalkyl or phenylloweralkyl and R.sub.1 is selected from hydroxy, cyano, nitro, amino, methylamino, dimethylamino, halo, trifluoromethyl, loweralkyl, loweralkoxy, sulfamoyl or acetamido, and when n is more than 1 up to 3, R.sub.1 can be the same or different, are disclosed as having gastrokinetic and anti-emetic utility in animals and pharmaceutical compositions therefor. A process for preparing the compounds by oxidation of 1,2-disubstituted-N-(4-pyrazolidinyl)benzamides with a metal hypochlorite is disclosed.
    Type: Grant
    Filed: April 6, 1984
    Date of Patent: October 15, 1985
    Assignee: A. H. Robins Company, Incorporated
    Inventors: Lennox B. Turnbull, John A. Donohue, Gunnar E. Jagdmann, Jr.
  • Patent number: 4503073
    Abstract: Novel 2-amino-3-(alkylthiobenzoyl)phenylacetic acids, esters and metal salts have the formula: ##STR1## wherein R is hydrogen or lower alkyl, R.sup.1 is hydrogen, lower alkyl or pharmaceutically acceptable metal cation, R.sup.2 is hydrogen, halogen, lower alkyl or lower alkoxy, Am is primary amino (--NH.sub.2), methylamino or dimethylamino. The compounds have anti-inflammatory activity; have effective analgesic activity, and inhibit blood platelet aggregation.
    Type: Grant
    Filed: November 22, 1983
    Date of Patent: March 5, 1985
    Assignee: A. H. Robins Company, Incorporated
    Inventors: David A. Walsh, Dwight A. Shamblee
  • Patent number: 4500529
    Abstract: N-(Aryloxyalkyl)-N'-(aminoalkyl)ureas and thioureas having the formula: ##STR1## wherein R.sup.1 and R.sup.2 are hydrogen, loweralkyl, cycloalkyl, phenyl or phenyllower alkyl, and R.sup.3 and R.sup.4 are hydrogen, loweralkyl, phenyl and phenylalkyl or R.sup.3 and R.sup.4 taken together with the adjacent nitrogen form a heterocyclic residue are disclosed in a method of suppressing cardiac arrhythmias.
    Type: Grant
    Filed: May 9, 1983
    Date of Patent: February 19, 1985
    Assignee: A. H. Robins Company, Incorporated
    Inventors: James R. Shanklin, Jr., Christopher P. Johnson, III
  • Patent number: 4495183
    Abstract: Pyrido[1,4]benzodiazepines having antidepressant activity of the formula ##STR1## wherein Ar is 2, 3 and 4-pyridinyl, 2 or 3-thienyl, phenyl or a substituted phenyl; R is hydrogen, loweralkyl or an amine on the end of a hydrocarbon chain; Z is hydrogen, halogen, trifluoromethyl, loweralkyl, lower-alkoxy, hydroxy or nitro; and Y is hydrogen, loweralkyl, loweralkoxy or hydroxy; and the pharmaceutical salts are prepared from [2-[(aminopyridinyl)amino]phenyl]arylmethanones which also have antidepressant activity.
    Type: Grant
    Filed: January 13, 1984
    Date of Patent: January 22, 1985
    Assignee: A. H. Robins Company, Incorporated
    Inventor: Chandler R. Taylor, Jr.
  • Patent number: 4306065
    Abstract: Novel hypotensive agents are disclosed which are quinazolines substituted in the 2 and 4 position having the general formula: ##STR1## wherein Q is a secondary amine radical illustrated by loweralkanolylamino or a tertiary amine radical such as pyrrolidinyl, piperidinyl or piperazinyl, any of which may be substituted by various groups such as loweralkanolyl.
    Type: Grant
    Filed: December 19, 1979
    Date of Patent: December 15, 1981
    Assignee: A. H. Robins Company, Incorporated
    Inventor: Ying-Ho Chen
  • 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: 4192916
    Abstract: An improved process for producing defatted heparin tissue is disclosed wherein frozen heparin-bearing tissue is particulated, thawed and warmed in a heat exchanger, fermented at temperatures ranging from about 60.degree.-85.degree. F. for 5 to 12 hours and subjected to azeotropic distillation and extraction to substantially remove water and fat. Putrefaction and odor are avoided, the tissue has improved uniformity in biochemical content, is lower in fat content and is capable of high heparin yields when processed according to known procedures. The defatted tissue is exceptionally permeable to heparin recovery solutions and heparin isolation is facilitated.
    Type: Grant
    Filed: April 5, 1978
    Date of Patent: March 11, 1980
    Assignee: A. H. Robins Company, Incorporated
    Inventors: William E. Melby, Charles E. Isdale, Sr., Vernon K. Collins
  • Patent number: 4192887
    Abstract: Methods of preventing and controlling coccidiosis in ruminant animals and for improving rate of weight gain by oral administration of salinomycin or 4-methylsalinomycin are disclosed.
    Type: Grant
    Filed: June 8, 1978
    Date of Patent: March 11, 1980
    Assignee: A. H. Robins Company, Incorporated
    Inventors: Grover D. Cloyd, Robert L. Miller, Donald M. Lucas
  • Patent number: 4188467
    Abstract: An improved method of tempering frozen heparin-bearing animal tissue is disclosed wherein the frozen tissue is particulated, thawed and warmed in a heat exchanger and fermented at temperatures ranging from about 60.degree.-85.degree. F. for 5-12 hours. Putrefaction and odor are avoided; the tissue has improved uniformity in biochemical content and is capable of high heparin yields when processed according to known procedures. When the tempered tissue is defatted with an azeotropic solvent, more of the fat is removed and the defatted tissue is more permeable to heparin recovery solutions and heparin isolation is facilitated.
    Type: Grant
    Filed: April 5, 1978
    Date of Patent: February 12, 1980
    Assignee: A. H. Robins Company, Incorporated
    Inventors: William E. Melby, Charles E. Isdale, Sr., Vernon K. Collins
  • Patent number: 4182774
    Abstract: Novel 2-amino-3-(5- and 6-)benzoylphenylacetic acids, esters and metal salts of the formula: ##STR1## wherein R is hydrogen or lower alkyl, R.sup.1 is hydrogen, lower-alkyl, sodium or potassium, R.sup.2 is hydrogen, halogen or lower alkoxy, X is hydrogen, lower alkyl, halogen, nitro or trifluoromethyl, Y is hydrogen, lower alkyl, halogen, nitro or trifluoromethyl, and Am is primary amino (--NH.sub.2) methylamino or dimethylamino. The compounds are prepared by hydrolysis of 4-(5- and 7-)benzoylindolin-2-ones to give the 2-amino-3-(5- and 6-)benzoylphenylacetic acids wherein amino is primary amino. The free acids are converted to the esters and metal salts. The calcium and magnesium salts are disclosed and are within the scope of the present invention. The compounds inhibit blood platelet aggregation.
    Type: Grant
    Filed: February 17, 1978
    Date of Patent: January 8, 1980
    Assignee: A. H. Robins Company, Incorporated
    Inventors: William J. Welstead, Jr., Henry W. Moran
  • Patent number: 4134977
    Abstract: An improved method for the formation of naled-containing synthetic resin shaped bodies is disclosed. A mixture of a synthetic resin, naled, and a surface porosity control component is extruded in the presence of an acid-resistant material (e.g., nickel or nickel alloys or the like). Other insecticides (e.g., carbamates) may also be included in the naled-containing mixture, if desired. The resulting extrudates are useful as pet collars or the like and are formed without substantial degradation of the naled as has been found to occur in attempts to extrude in the presence of carbon steel.
    Type: Grant
    Filed: September 26, 1977
    Date of Patent: January 16, 1979
    Assignee: A. H. Robins Company, Incorporated
    Inventor: Jack Greenberg
  • 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: 4126635
    Abstract: Novel 2-amino-3-(5- and 6-)benzoylphenylacetic acids, esters and metal salts of the formula: ##STR1## wherein R is hydrogen or lower alkyl, R.sup.1 is hydrogen, lower-alkyl, sodium or potassium, R.sup.2 is hydrogen, halogen or lower alkoxy, X is hydrogen, lower alkyl, halogen, nitro or trifluoromethyl, Y is hydrogen, lower alkyl, halogen, nitro or trifluoromethyl, and Am is primary amino (--NH.sub.2) methylamino or dimethylamino. The compounds are prepared by hydrolysis of 4-(5- and 7-)benzoylindolin-2-ones to give the 2-amino-3-(5- and 6-)benzoylphenylacetic acids wherein amino is primary amino. The free acids are converted to the esters and metal salts. The calcium and magnesium salts are disclosed and are within the scope of the present invention. The compounds have anti-inflammatory activity, are effective in lowering the cholesterol levels in hyperlipemic rats and inhibit blood platelet aggregation.
    Type: Grant
    Filed: April 15, 1977
    Date of Patent: November 21, 1978
    Assignee: A. H. Robins Company, Incorporated
    Inventors: William J. Welstead, Jr., Henry W. Moran