Patents Assigned to A. H. Robins Company, Incorporated
  • Patent number: 4886794
    Abstract: 4-[(.alpha.,.alpha.-Diaryl)-hydroxymethyl]-1-piperidinylalkylcyclic carbamate derivatives having the formula: ##STR1## wherein; R is hydrogen, loweralkyl, cycloalkyl, phenyl and substituted phenyl;Ar and Ar.sup.1 are phenyl, substituted phenyl or pyridinyl;alk is a straight or branched hydrocarbon chain;R.sup.1 is loweralkyl substituted for hydrogen on a ring carbon.The compounds are useful antihistamines and in controlling allergic response.
    Type: Grant
    Filed: June 3, 1988
    Date of Patent: December 12, 1989
    Assignee: A. H. Robins Company, Incorporated
    Inventor: David A. Walsh
  • Patent number: 4882330
    Abstract: 1-Aryloxy-4-[(4-aryl)-1-piperazinyl]-2-butanols of the formula: ##STR1## wherein Ar is selected fro ##STR2## or 2, 3 or 4-pyridyl); X and X' are selected from the group of hydrogen, loweralkyl, loweralkoxy, halogen, trifluoromethyl, nitro, acetylamino, phenyl or ##STR3## acetyl, cyano, aminocarbonyl, carboxy, or loweralkyl carboxylic acid ester; Y, Y', Y" are selected from the same group as X and X' except phenyl and substituted phenyl are excluded; Z and Z' are selected from hydrogen, loweralkyl or loweralkoxy and the pharmaceutically acceptable salt thereof are employed in a method of inhibiting or combatting allergic response associated with anaphylactic sensitivity in animals and humans.
    Type: Grant
    Filed: April 6, 1989
    Date of Patent: November 21, 1989
    Assignee: A. H. Robins Company, Incorporated
    Inventors: David A. Walsh, John M. Yanni
  • Patent number: 4877794
    Abstract: 2-Alkoxy-N-(1-azabicyclo[2.2.2]oct-3-yl) benzamides and thiobenzamides having the formula ##STR1## wherein X is oxygen or sulphur; R.sub.1 is loweralkyl; and R.sub.2 is hydrogen, halo, 4,5-benzo, alkoxy or Am wherein Am is amino, methylamino or dimethylamino, and n is 1 or 2, and the pharmaceutically acceptable acid addition salts thereof have antischizophrenic activity.
    Type: Grant
    Filed: September 6, 1988
    Date of Patent: October 31, 1989
    Assignee: A. H. Robins Company, Incorporated
    Inventors: Robert J. Naylor, Brenda Naylor
  • Patent number: 4873251
    Abstract: Imidazoheterocyclic compounds having the formula: ##STR1## wherein the A ring is pyridine in any of its four positions; B is carbonyl, thioxomethyl or hydroxymethylene; Z is hydrogen, halogen, loweralkyl, hydroxy, loweralkoxy, di-loweralkylamino or nitro; Ar is phenyl, pyrido, thienyl or furanyl; and W forms a wide combination of groups with B, including acids, esters, alcohols, amides and ketones. The compounds have CNS activity in a method for treating a living animal body as muscle relaxants, anticonvulsants and antianxiety agents.
    Type: Grant
    Filed: July 5, 1988
    Date of Patent: October 10, 1989
    Assignee: A. H. Robins Company, Incorporated
    Inventors: Bruce E. Tomczuk, Deborah S. Sutherland
  • Patent number: 4871737
    Abstract: A novel method of controlling epilepsy, muscle tension, muscular spasticity, and anxiety in living animal bodies by administering compounds of the formula: ##STR1## wherein: R.sup.1 is hydrogen, loweralkyl or a pharmaceutically acceptable cation;R.sup.2 and R.sup.3, same or different, are hydrogen, loweralkyl, aryl, cycloalkyl, loweralkenyl, 1-adamantyl, heterocyclicaminoalkyl, diloweralkylaminoloweralkyl, or R.sup.2 with R.sup.3 and adjacent nitrogen may form a heterocyclic ring structure; and the pharmaceutical acceptable acid salts, and tautomeric isomers thereof; and novel pharmaceutical compositions therefor are disclosed.
    Type: Grant
    Filed: March 16, 1989
    Date of Patent: October 3, 1989
    Assignee: A. H. Robins Company, Incorporated
    Inventors: Chandler R. Taylor, Jr., Harold F. Stauffer, Jr.
  • Patent number: 4870189
    Abstract: A novel process is described for preparing azetidine and 2 or 3 methyl and ethyl azetidine free bases by reacting primary arylmethylamine having suitable bulk providing substituents attached to the methyl carbon and an appropriate propane derivative having leaving groups in the one and three position in hot organic solvent containing a non-nucleophilic base and an amount of water sufficient to promote azetidine ring formation to give N-protected-azetidines and deprotecting by hydrogenolysis under acidic conditions to give an acid salt of the azetidines and thereafter flashing off vaporized azetidine from a hot, agitated strong base solution or slurry and condensing to give the liquid azetidine free bases.
    Type: Grant
    Filed: January 28, 1987
    Date of Patent: September 26, 1989
    Assignee: A. H. Robins Company, Incorporated
    Inventors: Young S. Lo, Dwight A. Shamblee, David H. Causey, Richard P. Mays
  • Patent number: 4870181
    Abstract: A process for the preparation of 2-alkoxy-N-(1-azabicyclo[2.2.2]octan-3-yl)aminobenzamides, which are gastric pharmaceuticals in monogastric animals having the formula: ##STR1## wherein R is hydrogen or loweralkyl, R.sup.1 is loweralkyl,R.sup.2 is hydrogen, halo or loweralkoxy,Am is amino, methylamino or dimethylaminois disclosed wherein in the initial step an appropriate monoprotonated 3-aminoquinuclidine strong acid salt and an appropriate amino benzoic acid all in a 50-90 vol. % pyridine in water solution are reacted in the presence of N,N'-dialkylcarbodiimide. The free base may be obtained by conventional procedures from the mixtures with minimal purification effort.
    Type: Grant
    Filed: February 4, 1985
    Date of Patent: September 26, 1989
    Assignee: A. H. Robins Company, Incorporated
    Inventor: Young S. Lo
  • Patent number: 4863919
    Abstract: A pharmaceutical method for improving memory or correcting memory deficiency is disclosed, utilizing compounds having the formula: ##STR1## wherein n.sup.1, n.sup.2, n.sup.3, and n.sup.4 =0 to 3; R.sup.1, R.sup.2, R.sup.3 , and R.sup.4 =H, loweralkyl or phenyl; R.sup.5 =H or loweralkyl; X=0 or S; Ar=phenyl, substituted phenyl, pyridinyl, furanyl, thienyl, methoxy-1H-benzotriazolyl, indolinyl, methoxyindolinyl, methoxypyrimidinyl, amino-methoxypyrimadinyl, 1,3-benzodioxolyl, or naphthalenyl; the optical isomers; and the pharmaceutically acceptable acid addition salts, hydrates and alcoholates thereof. The dosage effective for this use is from about 10 to 1000 nanograms/kg.
    Type: Grant
    Filed: February 1, 1988
    Date of Patent: September 5, 1989
    Assignee: A. H. Robins Company, Incorporated
    Inventor: William L. Smith
  • Patent number: 4857553
    Abstract: A method for the treatment of emesis in a mammal, which method comprises administering to said mammal an emesis inhibiting amount of a compound which depletes serotonin in the brain of mammals; among which are compounds having the formula: ##STR1## wherein, R is selected from hydrogen, loweralkyl, trifluoromethyl, carboxyl, or loweralkoxycarbonyl; R.sup.1 and R.sup.2 are hydrogen or loweralkyl; Z is trifluoromethyl or halogen; the optical isomers and pharmaceutically acceptable salts thereof; two of the preferred compounds of the invention are fenfluramine and norfenfluramine.
    Type: Grant
    Filed: August 10, 1988
    Date of Patent: August 15, 1989
    Assignee: A. H. Robins Company, Incorporated
    Inventors: John W. Ward, William L. Smith
  • Patent number: 4855447
    Abstract: 2-Amino-3-aroyl-.gamma.-oxobenzenebutanoic acids and derivatives having the formula: ##STR1## wherein X is hydrogen, halogen, or loweralkyl; Y is hydrogen, halogen, loweralkyl, loweralkoxyl, nitro, or trifluoromethyl; n is 1 or 2; and R is hydrogen lower-alkyl, or a pharmaceutically acceptable cation, are disclosed having anti-inflammatory activity.
    Type: Grant
    Filed: August 8, 1988
    Date of Patent: August 8, 1989
    Assignee: A. H. Robins Company, Incorporated
    Inventor: David A. Walsh
  • Patent number: 4855448
    Abstract: 2-Amino-3-aroyl-.gamma.-oxobenzenebutanoic acids and derivatives having the formula: ##STR1## wherein X is hydrogen, halogen, or loweralkyl; Y is hydrogen, halogen, loweralkyl, loweralkoxy, nitro, or trifluoromethyl; n is 1 or 2; and R is hydrogen, loweralkyl, or a pharmaceutically acceptable cation, are disclosed having anti-inflammatory activity.
    Type: Grant
    Filed: August 8, 1988
    Date of Patent: August 8, 1989
    Assignee: A. H. Robins Company, Incorporated
    Inventor: David A. Walsh
  • Patent number: 4835164
    Abstract: Novel heterocyclicmethanols are disclosed having the formula: ##STR1## wherein Z is pyrrolidinyl, piperidinyl, homopiperidinyl or pyridinyl; R.sup.1 is hydrogen, loweralkyl or carbethoxymethyl;R.sup.2 is hydrogen, loweralkyl, cycloalkyl, phenyl or phenyl-loweralkyl;R.sup.3 is 1 or 2-naphthalenyl, 2,3-dihydroinden-4 or 5-yl, phenyl or phenyl substituted by loweralkyl, loweralkoxy, halogen, trifluoromethyl, phenyl, methylenedioxy, nitro, amino, loweralkylamino, diloweralkylamino, loweracylamino;the 1-position of 2-pyrrolidinyl, 2-piperidinyl or 2-homopiperidinyl may be substituted by an R.sup.4 loweralkyl group, or R.sup.1 may form methylene or --CH.sub.2 -C(O)-bridges with R.sup.4 ;the pharmaceutically acceptable salts and diastereomers thereof, which compounds have antiarrhythmic and/or hypotensive activity in animals.
    Type: Grant
    Filed: February 20, 1987
    Date of Patent: May 30, 1989
    Assignee: A. H. Robins Company, Incorporated
    Inventors: James R. Shanklin, Jr., Christopher P. Johnson, III
  • Patent number: 4826866
    Abstract: A novel method of controlling epilepsy, muscle tension, muscular spasticity, and anxiety in living animal bodies by administering compounds of the formula: ##STR1## wherein: R.sup.1 is hydrogen, loweralkyl or a pharmaceutically acceptable cation;R.sup.2 and R.sup.3, same or different, are hydrogen, loweralkyl, aryl, cycloalkyl, loweralkenyl, 1-adamantyl, heterocyclicaminoalkyl, diloweralkylaminoloweralkyl, or R.sup.2 with R.sup.3 and adjacent nitrogen may form a heterocyclic ring structure; and the pharmaceutical acceptable acid salts, and tautomeric isomers thereof; and novel pharmaceutical compositions therefor are disclosed.
    Type: Grant
    Filed: November 2, 1987
    Date of Patent: May 2, 1989
    Assignee: A. H. Robins Company, Incorporated
    Inventors: Chandler R. Taylor, Jr., Harold F. Stauffer, Jr.
  • Patent number: 4824951
    Abstract: Imidazoheterocyclic compounds having the formula: ##STR1## wherein the A ring is pyridine in any of its four positions; B is carbonyl, thioxomethyl or hydroxymethylene; Z is hydrogen, halogen, loweralkyl, hydroxy, loweralkoxy, diloweralkylamino or nitro; Ar is phenyl, pyrido, thienyl or furanyl; and W forms a wide combination of groups with B, including acids, esters, alcohols, amides and ketones. The compounds have CNS activity in a method for treating a living animal body as muscle relaxants, anticonvulsants and antianxiety agents.
    Type: Grant
    Filed: July 5, 1988
    Date of Patent: April 25, 1989
    Assignee: A. H. Robins Company, Incorporated
    Inventors: Bruce E. Tomczuk, Deborah S. Sutherland
  • Patent number: 4812451
    Abstract: Novel 1-[(aminoalkyl and aminoalkylamino)carbonyl and thiocarbonyl-.alpha.,.alpha.-diaryl-pyrrolidine, piperidine and homopiperidineacetamides and acetonitriles having the formula: ##STR1## wherein; n is zero, one or two;X is oxygen or sulfur;Z is ##STR2## 10 or --(CH.sub.2); p is 0 to 5 inclusive with the proviso that when Z is ##STR3## p is at least one; Y is aminocarbonyl or cyano;Ar.sup.1 and Ar.sup.2 are 2, 3 or 4-pyrido, phenyl or substituted phenyl;R is hydrogen or loweralkyl;R.sup.1, R.sup.2 and R.sup.3 are hydrogen, cycloalkyl, loweralkyl, phenyl, substituted phenyl, phenylloweralkyl, and R.sup.2 and R.sup.3 taken with the adjacent nitrogen may form a heterocyclic residue, and diastereoisomers when possible and pharmaceutical salts; and the method and pharmaceutical compositions for treating cardiac arrhythmias therewith are disclosed.
    Type: Grant
    Filed: March 27, 1986
    Date of Patent: March 14, 1989
    Assignee: A. H. Robins Company, Incorporated
    Inventors: James R. Shanklin, Jr., James M. Wilkinson, II
  • Patent number: 4812565
    Abstract: This invention is directed to compounds having the formula: ##STR1## wherein: A represents an aromatic or heterocyclic ring having two of its carbon atoms held mutually with the oxazepine, thiazepine or diazepine moiety selected from the group consisting of benzene, naphthalene, a quinoline, a pyridine in any of its four positions, any of which rings are optionally substituted by one or two Y radicals selected from the group consisting of halo, loweralkyl, loweralkoxy, diloweralkylamino, nitro, amino, lower acylamino, trilfuoromethyl, phenyl or phenyl substituted by one to three Y' groups selected from halo, loweralkyl, loweralkoxy, diloweralkylamino, nitro, amino, loweracylamino or trifluoromethyl,E is selected from oxygen, sulfur or ##STR2## B is selected from the group consisting of loweralkyl, cycloalkyl or phenyl-loweralkyl wherein phenyl is optionally substituted by one or two radicals selected from halo, loweralkyl, loweralkoxy, nitro or trifuoromethyl,N is 1 or 2,R.sup.4 and R.sup.
    Type: Grant
    Filed: February 25, 1987
    Date of Patent: March 14, 1989
    Assignee: A. H. Robins Company, Incorporated
    Inventor: Albert D. Cale, Jr.
  • Patent number: 4812452
    Abstract: Novel 1-[(aminoalkyl and aminoalkylamino)carbonyl and thiocarbonyl]-.alpha.,.alpha.-diaryl-pyrrolidine, piperidine and homopiperidineacetamides and acetonitriles having the formula: ##STR1## wherein; n is zero, one or two;X is oxygen or sulfur;Z is ##STR2## or --(CH.sub.2); p is 0 to 5 inclusive with the proviso that when Z is ##STR3## p is at least one; Y is aminocarbonyl or cyano;Ar.sup.1 and Ar.sup.2 are 2, 3 or 4-pyrido, phenyl or substituted phenyl;R is hydrogen or loweralkyl;R.sup.1, R.sup.2 and R.sup.3 are hydrogen, cycloalkyl, loweralkyl, phenyl, substituted phenyl, phenylloweralkyl, and R.sup.2 and R.sup.3 taken with the adjacent nitrogen may form a heterocyclic residue, and diastereoisomers when possible and pharmaceutical salts; and the method and pharmaceutical compositions for treating cardiac arrhythmias therewith are disclosed.
    Type: Grant
    Filed: March 27, 1986
    Date of Patent: March 14, 1989
    Assignee: A. H. Robins Company, Incorporated
    Inventors: James R. Shanklin, Jr., James M. Wilkinson, II
  • Patent number: 4810795
    Abstract: Aromatic azepinones and thiones having the formula ##STR1## wherein; A is benzene, naphthalene, quinoline or pyridine;B is oxygen or sulfur; ##STR2## E is oxygen, sulfur or n is 1, 2 or 3;Z is an amino or a heterocyclic nitrogen-containing radical;R is hydrogen, loweralkyl, cycloalkyl or phenyl-loweralkyl;Y is halo, loweralkyl, loweralkoxy, diloweralkylamino, nitro, amino, loweracetylamino, trifluoromethyl, phenyl or phenyl substituted by one to three Y' radicals selected from halo, loweralkyl, loweralkoxy, diloweralkylamino, nitro, amino, loweracylamino or trifluoromethyl;and having antihistaminic utility, a process for the preparation thereof and chemical intermediates therefor are disclosed.
    Type: Grant
    Filed: February 25, 1987
    Date of Patent: March 7, 1989
    Assignee: A. H. Robins Company, Incorporated
    Inventor: Albert D. Cale, Jr.
  • Patent number: 4810703
    Abstract: Novel 1-[(aminoalkyl and aminoalkylamino)carbonyl and thiocarbonyl-.alpha.,.alpha.-diaryl-pyrrolidine, piperidine and homopiperidineacetamides and acetonitriles having the formula: ##STR1## wherein; n is zero, one or two;X is oxygen or sulfur;Z is ##STR2## or --(CH.sub.2); p is 0 to 5 inclusive with the proviso that when Z is ##STR3## p is at least one; Y is aminocarbonyl or cyano;Ar.sup.1 and Ar.sup.2 are 2, 3 or 4-pyrido, phenyl or substituted phenyl;R is hydrogen or loweralkyl;R.sup.1, R.sup.2 and R.sup.3 are hydrogen, cycloalkyl, loweralkyl, phenyl, substituted phenyl, phenylloweralkyl, and R.sup.2 and R.sup.3 taken with the adjacent nitrogen may form a heterocyclic residue, and diastereoisomers when possible and pharmaceutical salts; and the method and pharmaceutical compositions for treating cardiac arrhythmias therewith are disclosed.
    Type: Grant
    Filed: July 7, 1986
    Date of Patent: March 7, 1989
    Assignee: A. H. Robins Company, Incorporated
    Inventors: James R. Shanklin, Jr., James M. Wilkinson, II
  • Patent number: 4810713
    Abstract: A method of treating allergy with substituted heterocyclic amines is disclosed wherein the active agents are expressed generally by the formula which includes certain known and certain novel compounds: ##STR1## wherein p is zero, one or two; m is one to six inclusive; A is selected from hydrogen, hydroxy or cyano; d is zero or one; Q is --CH--, --CH.sub.2 -- or ##STR2## n is zero or one and when Q is --CH-- and n is one, a double bond is formed with one of the adjacent carbons but not both at the same time, and when n and d are zero at the same time, a double bond is formed between the .alpha.
    Type: Grant
    Filed: December 20, 1985
    Date of Patent: March 7, 1989
    Assignee: A. H. Robins Company, Incorporated
    Inventors: John M. Yanni, David A. Walsh