Patents Represented by Attorney Frederik W. Stonner
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Patent number: 4518585Abstract: Aqueous acidic disinfecting and sterilizing compositions containing hydrogen peroxide, a surfactant and an aqueous alcoholic mixture of a tertiary amine and a fatty acid alkanolamide are non-irritating, have in-use stability and are effective for cold and warm sterilization.Type: GrantFiled: November 20, 1979Date of Patent: May 21, 1985Assignee: Sterling Drug Inc.Inventors: Donald F. Greene, Virginia L. Urban
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Patent number: 4495353Abstract: The invention relates to a process for substituting for a halogen atom attached to the nuclear carbon atom of an aromatic ring, a substituent of the formula -O-R wherein R represents alkyl, alkenyl, alkynyl or benzyl, which process comprises reacting the halogen-substituted aromatic compound with an alcoholate of the formula M.sup.n+ [O--R].sub.n.sup..crclbar. wherein M is an alkali metal atom or alkaline earth metal atom, n is the valency of M, and R is as defined above, in the presence of an active catalyst mixture comprising (i) a formic acid ester of an organic alcohol having the formula R.sup.2 --O--CO--H wherein R.sup.2 is as defined for R above; and (ii) a cuprous salt; in a liquid medium which is a solvent for the catalyst mixture and in which the halogen-substituted aromatic compound is at least partially soluble, under substantially anhydrous conditions and a non-oxidizing atmosphere. The invention further relates to a catalyst used in the above process.Type: GrantFiled: June 13, 1983Date of Patent: January 22, 1985Assignee: Sterling Drug Inc.Inventor: Robert J. Bryant
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Patent number: 4422955Abstract: The invention relates to a process for substituting for a halogen atom attached to the nuclear carbon atom of an aromatic ring, a substituent of the formula --O--R wherein R represents alkyl, alkenyl, alkynyl or benzyl, which process comprises reacting the halogen-substituted aromatic compound with an alcoholate of the formula M.sup.n+ [O--R].sub.n.sup..crclbar. wherein M is an alkali metal atom or alkaline earth metal atom, n is the valency of M, and R is as defined above, in the presence of an active catalyst mixture comprising (i) a formic acid ester of an organic alcohol having the formula R.sup.2 --O--CO--H wherein R.sup.2 is as defined for R above; and (ii) a cuprous salt; in a liquid medium which is a solvent for the catalyst mixture and in which the halogen-substituted aromatic compound is at least partially soluble, under substantially anhydrous conditions and a non-oxidizing atmosphere. The invention further relates to a catalyst used in the above process.Type: GrantFiled: December 4, 1981Date of Patent: December 27, 1983Assignee: Sterling Drug Inc.Inventor: Robert J. Bryant
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Patent number: 4405795Abstract: 2-Benzylideneglutaraldehydes of the formula ##STR1## where R.sup.1, R.sup.2 and R.sup.3 independently are hydrogen or a substituent selected from the group consisting of halo, lower-alkyl, phenyl, carboxy, lower-alkoxycarbonyl, phenoxycarbonyl, aminocarbonyl, hydroxysulfonyl, nitro, cyano, hydroxy, loweralkoxy and phenoxy, a method of use thereof as disinfectants, disinfectant compositions comprising them, and 2,6-dialkoxy-3-(.alpha.-alkoxybenzyl)tetrahydropyrans of the formula ##STR2## where R.sup.1, R.sup.2 and R.sup.3 are as defined above and R.sup.4 and R.sup.5 independently are alkyl of one to four carbon atoms, which are intermediates for their preparation are disclosed.Type: GrantFiled: June 7, 1982Date of Patent: September 20, 1983Assignee: Sterling Drug Inc.Inventors: Wolfgang Munzenmaier, Heinz Eggensperger, Helmut H. Ehlers, Wolfgang Beilfuss, Lothar Bucklers, Hans-Peter Harke
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Patent number: 4404191Abstract: A method is provided for inactivating viruses on animate and inanimate surfaces which comprises contacting the locus of said viruses with an antivirally effective amount of a salt of peroxymonosulfuric acid.Type: GrantFiled: November 18, 1981Date of Patent: September 13, 1983Assignee: Sterling Drug Inc.Inventors: Jutta Sporkenbach, Heinz Eggensperger, Lothar Bucklers, Helmut H. Ehlers, Ulrich Eigener, Hans-Peter Harke
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Patent number: 4402853Abstract: A stable succinyl peroxide composition comprising in solid particulate form a mixture of succinyl peroxide, a water-soluble dehydrating agent which is unreactive to succinyl peroxide, e.g., magnesium or sodium sulfate, and water, the water being bound to the dehydrating agent as water of hydration; and a method of preparation thereof comprising mixing a paste of succinyl peroxide in water with a water soluble dehydrating agent, the dehydrating agent being mixed with the succinyl peroxide paste in an amount and for a time sufficient to bind all of the water in the paste and provide a dry mixture.Type: GrantFiled: April 5, 1982Date of Patent: September 6, 1983Assignee: Sterling Drug Inc.Inventors: Peter Brocklehurst, Angus S. Ferguson
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Patent number: 4379137Abstract: The invention is a synergistic disinfecting and preserving composition comprising in admixture a polymeric quaternary ammonium compound and a 3-isothiazolone derivative, and a method of use thereof, for protecting aqueous systems against contamination by deleterious microorganisms.Type: GrantFiled: July 28, 1980Date of Patent: April 5, 1983Assignee: Sterling Drug Inc.Inventors: Helmut H. Ehlers, Heinz Eggensperger, Lothar Bucklers, Ulrich Eigener, Karl-Heinz Diehl, Norbert Weigand
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Patent number: 4376094Abstract: Disclosed is a method of disinfecting and a method for destroying bacteria and fungi employing certain 2-substituted glutaraldehydes having the formulas ##STR1## wherein R.sup.1 is selected from the group consisting of alkyl having from one to twelve carbon atoms, lower-alkoxyalkyl having from two to twelve carbon atoms, cycloalkyl having from three to twelve ring carbon atoms, and alkyl-substituted cycloalkyl having from three to eight ring carbon atoms and a total of from four to ten carbon atoms, and R.sup.3 is alkyl having from one to four carbon atoms.Type: GrantFiled: August 21, 1981Date of Patent: March 8, 1983Assignee: Sterling Drug Inc.Inventors: Wolfgang Munzenmaier, Heinz Eggensperger, Helmut H. Ehlers, Wolfgang Beilfuss, Lothar Bucklers, Hans-Peter Harke
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Patent number: 4371547Abstract: 2-Benzylideneglutaraldehydes of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 independently are hydrogen or a substituent selected from the group consisting of halo, lower-alkyl, phenyl, carboxy, lower-alkoxycarbonyl, phenoxycarbonyl, aminocarbonyl, hydroxysulfonyl, nitro, cyano, hydroxy, lower-alkoxy and phenoxy, a method of use thereof as disinfectants, disinfectant compositions comprising them, and 2,6-dialkoxy-3-(.alpha.-alkoxybenzyl)tetrahydropyrans of the formula ##STR2## where R.sup.1, R.sup.2 and R.sup.3 are as defined above and R.sup.4 and R.sup.5 independently are alkyl of one to four carbon atoms, which are intermediates for their preparation are disclosed.Type: GrantFiled: August 21, 1981Date of Patent: February 1, 1983Assignee: Sterling Drug Inc.Inventors: Wolfgang Munzenmaier, Heinz Eggensperger, Helmut H. Ehlers, Wolfgang Beilfuss, Lothar Bucklers, Hans-Peter Harke
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Patent number: 4301283Abstract: A process for preparing 2-oxo-dihydrobenzo[d][1,3]oxazines (also named 1,4-dihydro-2H-3,1-benzoxazin-2-ones) which process comprises treating a suspension or solution of a 2-carbamoyl-benzyl alcohol in a substantially water-immiscible organic medium with aqueous alkaline hypochlorite or hypobromite having a pH of at least 11 in the presence of a phase transfer catalyst; and conversion of the 2-oxo-dihydrobenzo[d][1,3]oxazines to corresponding 2-amino-benzyl alcohols which are useful as intermediates in the production of dyes, pharmaceuticals and herbicides.Type: GrantFiled: September 10, 1980Date of Patent: November 17, 1981Assignee: Sterling Drug Inc.Inventors: John G. Thorpe, Peter G. Urben
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Patent number: 4299749Abstract: The invention relates to a stable aqueous self-stripping floor cleaning, coating and polishing composition containing a low molecular weight alkali-soluble acrylic type addition-polymer, a fugitive plasticizer, tributoxyethyl phosphate, tetrasodium ethylenediaminetetraacetate, an anionic or nonionic fluorocarbon surfactant, a dimethylpolysiloxane antifoaming agent, 1,2-benzothiazolin-3-one, an alkali metal bicarbonate, water and ammonia to pH 9 to 9.7; and optionally formaldehyde, caprolactam and a styrene-maleic anhydride copolymer, the composition having a solids content of from 5 to 15% by weight.Type: GrantFiled: October 16, 1980Date of Patent: November 10, 1981Assignee: Sterling Drug Inc.Inventors: Francis L. McCarthy, Thomas H. Bach
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Patent number: 4259383Abstract: A disinfecting tissue comprising an absorbent material having incorporated therein a disinfecting agent selected from (a) organic percarboxylic acids; (b) mixtures of a hydrogen peroxide donor with an organic carboxylic acid anhydride or a acyloxy-benzoic or -benzenesulfonic acid; and (c) a carboxylic acid amide; as defined in the specification. The disinfectant tissues are useful for the disinfection of the skin, hands, and inanimate surfaces.Type: GrantFiled: June 26, 1979Date of Patent: March 31, 1981Assignee: Sterling Drug Inc.Inventors: Heinz Eggensperger, Dieter Rehn, Wolfgang Beilfuss, Helmut Nolte
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Patent number: 4257952Abstract: 3-(Substituted-amino)-1,2,3,4-tetrahydrocarbazoles are prepared by reacting appropriate 4-substituted-aminocyclohexanones with a phenylhydrazine, by reacting a 3-(sulfonyloxy)-1,2,3,4-tetrahydrocarbazole with an appropriate substituted amine, or by reduction of an appropriate 3-(acylamino)-1,2,3,4-tetrahydrocarbazole. The 3-(substituted-amino)-1,2,3,4-tetrahydrocarbazoles of this invention have analgetic and psychotropic activities. Moreover, certain of these compounds also have antihistaminic activity.Type: GrantFiled: June 6, 1979Date of Patent: March 24, 1981Assignee: Sterling Drug Inc.Inventor: Aram Mooradian
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Patent number: 4224335Abstract: There are disclosed novel 3-amino(and substituted amino)-hydroxy (and dihydroxy)-1,2,3,4-tetrahydrocarbazoles having positive inotropic activity and methods and compositions for the use thereof in treating the failing heart in mammals afflicted with congestive heart failure.Type: GrantFiled: January 23, 1976Date of Patent: September 23, 1980Assignee: Sterling Drug Inc.Inventor: Aram Mooradian
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Patent number: 4221660Abstract: A method for disinfecting an aqueous system which comprises contacting the system with a solid aromatic percarboxylic acid having solubility in water not greater than about 1 weight-percent in a weight-percent amount in excess of said solubility in water; and a method for disinfecting materials with said aqueous system.Type: GrantFiled: January 29, 1979Date of Patent: September 9, 1980Assignee: Sterling Drug Inc.Inventors: Heinz Eggensperger, Wolfgang Beilfuss, Wolfgang Zerling
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Patent number: 4205185Abstract: A process for the preparation of racemic 4-hydroxyphenylglycine, in which phenol, glyoxylic acid (or a salt thereof) and ammonia are reacted together to produce the desired 4-hydroxyphenylglycine.Type: GrantFiled: August 31, 1978Date of Patent: May 27, 1980Assignee: Sterling Drug Inc.Inventors: Michael J. Elton, Arthur Jackson, John W. Harrison
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Patent number: 4204875Abstract: A method for preventing shrinkage of alkaline aqueous hydraulic cementitious mixtures during setting and hardening which comprises incorporating in the mixtures a monopersulfate salt, or a monopersulfate salt together with at least one peroxygen compound other than the monopersulfate salt; and hydraulic cement compositions for preparing such alkaline aqueous hydraulic cementitious mixtures. The monopersulfate salt, or monopersulfate salt together with at least one peroxygen compound other than monopersulfate salt, generates sufficient oxygen gas during setting and hardening of the alkaline aqueous hydraulic cementitious mixture to provide controlled expansion of the mixture.Type: GrantFiled: June 22, 1977Date of Patent: May 27, 1980Assignee: Sterling Drug Inc.Inventor: Miklos Szalavitz
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Patent number: 4178375Abstract: A method for preventing or retarding the growth of bacteria and fungi in a material which comprises treating the material with N,N'-methylenebis-(oxazolidines) and -(tetrahydro-1,3-oxazines), and certain novel N,N'-methylenebis-(oxazolidines).Type: GrantFiled: August 17, 1978Date of Patent: December 11, 1979Assignee: Sterling Drug Inc.Inventors: Heinz Eggensperger, Karl-Heinz Diehl
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Patent number: 4174402Abstract: A method for inhibiting the symptoms induced by SRS-A released in a mammal susceptible to said SRS-A which comprises administering to said mammal an amount effective for inhibiting said symptoms of a compound selected from the group consisting of 9-benzoyl-12,3,4,-tetrahydrocarbazole-3-carboxylic acid, 9-benzoyl-6-methoxy-1,2,3,4-tetrahydrocarbazole-3-carboxylic acid, 9-benzoyl-1,2,3,4-tetrahydrocarbazole-4-carboxylic acid, 9-(4-toluoyl)-1,2,3,4-tetrahydrocarbazole-4-carboxylic acid, 9-benzoyl-6-methoxy-1,2,3,4-tetrahydrocarbazole-4-carboxylic acid and 9-benzoyl-6-methyl-1,2,3,4-tetrahydrocarbazole-4-carboxylic acid; or a pharmaceutically acceptable salt of said compound.Type: GrantFiled: August 17, 1978Date of Patent: November 13, 1979Assignee: Sterling Drug Inc.Inventor: Zigurd E. Mielens
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Patent number: 4172834Abstract: 3-(Substituted-amino)-1,2,3,4-tetrahydrocarbazoles are prepared by reacting appropriate 4-substituted-aminocyclohexanones with a phenylhydrazine, by reacting a 3-(sulfonyloxy)-1,2,3,4-tetrahydrocarbazole with an appropriate substituted amine, or by reduction of an appropriate 3-(acylamino)-1,2,3,4-tetrahydrocarbazole. The 3-(substituted-amino)-1,2,3,4-tetrahydrocarbazoles of this invention have analgetic and psychotropic activities. Moreover, certain of these compounds also have antihistaminic activity.Type: GrantFiled: June 6, 1977Date of Patent: October 30, 1979Assignee: Sterling Drug Inc.Inventor: Aram Mooradian