Patents Assigned to A. H. Robins Company, Inc.
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Patent number: 5063235Abstract: Novel compounds of the formula: ##STR1## are disclosed wherein Ar and Ar.sup.1 are phenyl, sustituted phenyl or pyridinyl, "alk" is a C.sub.1 -C.sub.12 straight or branched hydrocarbon chain, and R is H, loweralkylcarbonyl, arylcarbonyl, or aminocarbonyl where the amino is unsubstituted or substituted by one or two groups selected from loweralkyl or aryl. The compounds of this invention are useful in the treatment of allergic disorders.Type: GrantFiled: April 30, 1990Date of Patent: November 5, 1991Assignee: A. H. Robins Company, Inc.Inventor: David A. Walsh
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Patent number: 5061720Abstract: Disclosed are novel substituted 4-thiazolidinone derivatives having cyclooxygenase and 5-lipoxygenase inhibiting properties and which are topical antiinflammatory agents for inflammed conditions of the skin having the formula: ##STR1## wherein R is hydrogen or loweralkyl; R.sup.1 is loweralkyl or aryl; X is --(CH.sub.2)-aryl, --O--(CH.sub.2).sub.0-3 -aryl, --C(O)(CH.sub.2).sub.0-3 -aryl, --CH(OH)--(CH.sub.2).sub.0-3 -aryl or 3,4 ##STR2## (to form naphthyl ring); aryl is phenyl, substituted phenyl, or 2,3 or 4 pyridyl; W is oxygen; Q is -(alk.sup.1).sub.0-1 --(O).sub.0-1 --(B).sub.0-1 --(alk.sup.2).sub.0-1 --[C(O)Z].sub.0-1 ; B is ##STR3## Z is OR.sup.3 or NR.sup.4 R.sup.5 where R.sup.3 is hydrogen, loweralkyl, or a pharmaceutically acceptable metal cation, R.sup.4 and R.sup.5 are hydrogen or loweralkyl; alk.sup.1 and alk.sup.Type: GrantFiled: September 13, 1989Date of Patent: October 29, 1991Assignee: A. H. Robins Company, Inc.Inventors: David A. Walsh, Ibrahim M. Uwaydah
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Patent number: 4960896Abstract: A process for the preparation of 5-halo-2-hydroxynicotinic acids having the formula: ##STR1## wherein X is chlorine or bromine, Y and Z are selected from hydrogen, loweralkyl or loweralkyl, is described wherein a corresponding 2-hydroxynicotinic acid is halogenated with alkali-metal hypohalite in a strongly alkaline solution pH 12 and above. Certain aspects of the isolation of the product are directed to avoiding replacement of the carboxy group with halogen.Type: GrantFiled: November 13, 1987Date of Patent: October 2, 1990Assignee: A. H. Robins Company, Inc.Inventor: Young S. Lo
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Patent number: 4960776Abstract: Novel 4-aryl-N-[2-(dialkylamino and heterocyclicamino)alkyl]-1-piperazinecarboxamides of the formula: ##STR1## wherein B is oxygen or sulfur; Ar is selected from ##STR2## or 2, 3 or 4-pyridyl; X is selected from hydrogen, halogen, loweralkyl, loweralkoxy, amino, dimethylamino, nitro, trifluoromethyl, cyano, acetyl, acetylamino, aminocarbonyl, carboxy or loweralkylcarboxylic acid ester; Y is selected from hydrogen, halogen, loweralkyl, loweralkoxy, nitro, trifluoromethyl, cyano, acetylamino, aminocarbonyl, carboxy or loweralkyl carboxylic acid ester; Z is selected from hydrogen, loweralkyl or loweralkoxy; Q is selected from ##STR3## m is 1 to 3 inclusive; n is zero or 1; p is zero to 3 inclusive; R.sup.1, R.sup.2 and R.sup.3 are loweralkyl and may be the same or different, or R.sup.1 and R.sup.2 taken together with the adjacent nitrogen atom may be form a heterocyclic residue; and the pharmaceutically acceptable salts thereof are disclosed.Type: GrantFiled: January 28, 1987Date of Patent: October 2, 1990Assignee: A. H. Robins Company, Inc.Inventors: David A. Walsh, Albert D. Cale, Jr.
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Patent number: 4956359Abstract: Novel 3-aryloxy and 3-arylthioazetidinecarboxamides having utility in a method of treating convulsions and epilepsy and compositions therefor are disclosed having the formula: ##STR1## wherein Z is oxygen or sulfur; B is oxygen or sulfur; Ar is pyridyl or halo-substituted-pyridyl, phenyl or substituted phenyl; R.sup.1 and R.sup.2 are selected from hydrogen, loweralkyl, aryl, allyl, substituted allyl, propargyl, cycloalkyl, loweralkylcycloalkyl, cycloalkylloweralkyl, arylloweralkyl, diloweralkylaminoloweralkyl, and R.sup.1 and R.sup.2 when taken with the adjacent nitrogen atom may form a heterocyclic radical; R.sup.3 is hydrogen, loweralkyl, aryl or arylloweralkyl, and the geometrical isomers thereof, excepting that when R.sup.3 is hydrogen, Z is oxygen, B is oxygen, and Ar is phenyl or phenyl substituted by trifluoromethyl or aminocarbonyl, then R.sup.1 and R.sup.2 cannot be a combination of hydrogen and loweralkyl, and the further exception that when R.sup.Type: GrantFiled: October 22, 1986Date of Patent: September 11, 1990Assignee: A. H. Robins Company, Inc.Inventors: Chandler R. Taylor, Jr., Albert D. Cale, Jr., Harold F. Stauffer, Jr.
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Patent number: 4898874Abstract: 3-Aryl-2,1-benzisoxazole compounds having the formula: ##STR1## wherein R.sup.1 and R.sup.2 are hydrogen or methyl;R.sup.3 and R.sup.4 are hydroxyl, loweralkoxy, amino or --OM wherein M is a pharmaceutically acceptable cation;X is hydrogen, halogen, loweralkyl or nitro;Y is selected from hydrogen, halogen, loweralkyl, loweralkoxy, nitro or trifluoromethyl;n and p are zero or one with the proviso that either n or p must be oneare disclosed, having anti-inflammatory activity and novel intermediates in the preparation thereof.Type: GrantFiled: September 15, 1986Date of Patent: February 6, 1990Assignee: A. H. Robins Company, Inc.Inventors: David A. Walsh, Ibrahim M. Uwaydah
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Patent number: 4808404Abstract: Methods and compositions are disclosed for vaccinating warm-blooded animals against coccidiosis utilizing suspensions of excysted coccidial sporozoites in physiologically balanced medium containing water-soluble polymeric stabilizers selected from gels, gelatins, polysaccharide gums, cellulose or cellulose derivatives which extend viability or storage, additional extension of viability in storage being attained when the suspensions are finely divided and the polymeric stabilizers are hardened to form microcapsules.Type: GrantFiled: January 11, 1988Date of Patent: February 28, 1989Assignee: A. H. Robins Company, Inc.Inventor: Balbir S. Bhogal
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Patent number: 4772600Abstract: 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: GrantFiled: June 9, 1986Date of Patent: September 20, 1988Assignee: A. H. Robins Company, Inc.Inventors: Bruce E. Tomczuk, Deborah S. Sutherland
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Patent number: 4727152Abstract: Chemical intermediates having the formula: ##STR1## wherein A represents an aromatic or heterocyclic ring system selected from benzene, a naphthalene, a quinoline or a pyridine in any of its four positions, any of the rings systems are optionally substituted by one or two Y radicals selected from the group consisting of halo, loweralkyl, loweralkoxy, diloweralkylamino, nitro or trifluoromethyl;R is selected from the group consisting of loweralkyl, cycloalkyl or phenylloweralkyl wherein phenyl is optionally substituted by one or two radicals selected from halo, loweralkyl, loweralkoxy, nitro or trifluoromethyl;R.sup.4 and R.sup.5 are selected from hydrogen or loweralkyl;n is 1 or 2;X is selected from chlorine, bromine, or fluorine and E is selected from sulfur, oxygen or ##STR2## and chemical intermediates having the formula: ##STR3## wherein A, R, R.sup.4, R.sup.5, E and n are as defined above and Q is selected from the group consisting of ##STR4## wherein R.sup.Type: GrantFiled: March 3, 1986Date of Patent: February 23, 1988Assignee: A. H. Robins Company, Inc.Inventor: Albert D. Cale, Jr.
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Patent number: 4717563Abstract: A method of controlling emesis caused by non-platinum anti-cancer drugs with 2-alkoxy-N-(1-azabicyclo[2.2.2]oct-3-yl)benzamides and thiobenzamides having the formula ##STR1## wherein X is oxygen or sulfur; R.sub.1 is loweralkyl; and R.sub.2 is selected from the group consisting of hydrogen, halo, 4,5-benzo, methylsulfonyl, loweralkoxy or Am and n is 1 or 2, and the pharmaceutically acceptable acid addition salts thereof is disclosed.Type: GrantFiled: March 5, 1986Date of Patent: January 5, 1988Assignee: A. H. Robins Company, Inc.Inventors: Reevis S. Alphin, William L. Smith, Harry R. Munson, Jr., Robert F. Boswell
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Patent number: 4705853Abstract: Aromatic azepinones and thiones having the formula ##STR1## wherein; A is benzene, naphthalene, quinoline or pyridine;B is oxygen or sulfur;E is oxygen, sulfur or ##STR2## n is 1, 2 or 3; Z is an amino or a heterocyclic nitrogen-containing radical;R is hydrogen, loweralkyl, cycloalkyl or phenylloweralkyl;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: GrantFiled: March 3, 1986Date of Patent: November 10, 1987Assignee: A. H. Robins Company, Inc.Inventor: Albert D. Cale, Jr.
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Patent number: 4698430Abstract: 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: GrantFiled: August 30, 1985Date of Patent: October 6, 1987Assignee: A. H. Robins Company, Inc.Inventors: Chandler R. Taylor, Jr., Young S. Lo
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Patent number: 4610819Abstract: A process for the preparation of 1,4-oxazepinones and thiones having the formula: ##STR1## wherein A is an aromatic ring selected from benzene, naphthalene, quinoline or pyridine; n is 1 to 3; Z is an amino radical; R is hydrogen, loweralkyl, cycloalkyl or phenylloweralkyl; and R.sup.4 and R.sup.5 are hydrogen and loweralkyl starting from chloroaromatic carboxylates and alkanolamines is disclosed.Type: GrantFiled: September 19, 1984Date of Patent: September 9, 1986Assignee: A. H. Robins Company, Inc.Inventors: Young S. Lo, Albert D. Cale, Jr.
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Patent number: 4609735Abstract: Novel 1-aryloxy-4-amino-2-butanols of the formulaArO--CH.sub.2 --CHOH--CH.sub.2 --CH.sub.2 --NR.sup.1 R.sup.2wherein AR is 1-naphythyl, 2-naphthyl, indene-4(or 5-)yl, 3-(or 5-)chloro-2-pyridyl, phenyl, monosubstituted phenyl or di-substituted phenyl, R.sup.1 is lower alkyl, phenyl, phenylalkyl, 2-hydroxymethyl-2-propyl, adamantyl or lower-cycloalkyl, R.sup.2 is hydrogen or lower alkyl, wherein R.sup.1 and R.sup.2 together with the adjacent nitrogen form a heterocyclic residue and the pharmaceutically acceptable acid addition salts thereof having local anesthetic, beta-adrenergic blocking, antihypertensive and antiarrhythmic properties are disclosed. The compounds are prepared by reacting novel 1-aryloxy-4-chloro-2-butanols with amines. Methods for the preparation of the novel 1-aryloxy-4-chloro-2-butanol intermediates are also disclosed.Type: GrantFiled: September 11, 1984Date of Patent: September 2, 1986Assignee: A. H. Robins Company, Inc.Inventors: Carl D. Lunsford, Ying-Ho Chen
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Patent number: 4605550Abstract: There is disclosed a granular composition having particles of average particle size as determined by sieving in the range 70 to 500 microns, the said particles comprising up to 55% of active ingredient e.g. ferrous sulphate having primary particles the maximum dimension (A) of which as determined by microscopy is less than 50 microns and a particulate water soluble extender e.g. lactose having an average particle size (B) as determined by sieving in excess of 50 microns, the particles of active ingredient and water soluble extender being held in self-supporting spaced relationship by a water insoluble polymer film matrix e.g. of a polyacrylate polymer, providing the balance of the weight of the particle and being less than 50% by weight of the particle.The invention also extends to a blend convertible by pressure alone to a substantially continuous three-dimensional porous matrix substantially devoid of separate resin particles, of active ingredient/water soluble extender/resin particles, e.g.Type: GrantFiled: June 5, 1984Date of Patent: August 12, 1986Assignee: A. H. Robins Company, Inc.Inventor: Anthony J. Trill
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Patent number: 4605652Abstract: 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=O or S; Ar=phenyl, substituted phenyl, pyridinyl, furanyl, thienyl, methoxy-1H-benzotriazolyl, indolinyl, methoxyindolinyl, methoxypyrimidinyl, amino-methoxypyrimadinyl, 1,3-benzodioxolyl, or naphthalenyl, and the pharmaceutically acceptable acid addition salts, hydrates and alcoholates thereof.Type: GrantFiled: February 4, 1985Date of Patent: August 12, 1986Assignee: A. H. Robins Company, Inc.Inventor: William J. Welstead, Jr.
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Patent number: 4604404Abstract: A method is disclosed for combating Herpes simplex viruses, Types I and II, which comprises topically applying and antiviral arylsulfonic acid polymer to the animal tissue under attack. Bacterial infections are also affectively treated.Type: GrantFiled: April 3, 1985Date of Patent: August 5, 1986Assignee: A. H. Robins Company, Inc.Inventors: Harry R. Munson, Jr., Robert W. Tankersley, Jr.
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Patent number: 4594189Abstract: An improved process is disclosed for preparing 3-phenoxyazetidines which utilizes a phase transfer catalyst to add the phenoxy group to azetidine blocked in the 1-position by a diphenylmethane group and utilizes a stabilizing tertiary amine base to prevent dimerization during hydrogenolysis to remove the blocking group. The crude product containing diphenylmethane may be used without purification to prepare 3-phenoxy-1-azetidinecarboxamides.Type: GrantFiled: July 6, 1983Date of Patent: June 10, 1986Assignee: A. H. Robins Company, Inc.Inventors: Young S. Lo, Richard P. Mays
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Patent number: 4592866Abstract: Aromatic azepinones and thiones having the formula ##STR1## wherein; A is benzene, naphthalene, quinoline or pyridine;B is oxygen or sulfur;E is oxygen, sulfur or ##STR2## n is 1, 2 or 3; Z is an amino or a heterocyclic nitrogen containing radical;R is hydrogen, loweralkyl, cycloalkyl or phenylloweralkyl;and having antihistaminic utility, a process for the preparation thereof and chemical intermediates therefor are disclosed.Type: GrantFiled: June 18, 1985Date of Patent: June 3, 1986Assignee: A. H. Robins Company, Inc.Inventor: Albert D. Cale, Jr.
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Patent number: 4593034Abstract: 2-Alkoxy-N-(1-azabicyclo[2.2.2]oct-3-yl)benzamides and thiobenzamides having the formula ##STR1## wherein X is oxygen or sulfur; R.sub.1 is loweralkyl; and R.sub.2 is selected from the group consisting of hydrogen, halo, 4,5-benzo, alkoxy or Am and n is 1 or 2, and the pharmaceutically acceptable acid addition salts thereof having gastrokinetic and anti-emetic activity are disclosed.Type: GrantFiled: April 6, 1984Date of Patent: June 3, 1986Assignee: A. H. Robins Company, Inc.Inventors: Harry R. Munson, Jr., Robert F. Boswell, Jr.