Patents Represented by Attorney Robert E. Carnahan
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Patent number: 4096183Abstract: Styrylamidines are prepared by treating styrylsulfonylamidines with base. The styrylamidines are effective in the prevention of aggregation of blood platelets and as analgesics. Compounds of the invention are also useful as anticonvulsants, diuretics and antihypertensive agents. The styrylsulfonylamidines of the invention which serve as precursors to the styrylamidines also have analgesic properties. Illustrative of the styrylamidines of the present invention are 4-amino-N-(4-aminostyryl)benzamidine and N-(3,4-dichlorostyryl)acetamidine. An example of a styrylsulfonylamidine is N-(styrylsulfonyl)acetamidine.Type: GrantFiled: August 19, 1977Date of Patent: June 20, 1978Assignee: Mead Johnson & CompanyInventors: William L. Matier, William T. Comer
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Patent number: 4096277Abstract: A mucolytic process is disclosed which comprises contacting N-(2-hydroxyethyl)mercaptoacetamidobenzamides or mercaptoacylamidobenzoic acids, mercaptoacetylsulfanilic acids and alkanoylthio derivatives thereof with mucus. Illustrative of compounds useful in the mucolytic process of the present invention are 4-(2-mercaptoacetamido)-benzoic acid and N-(2-mercaptoacetyl)sulfanilic acid.Type: GrantFiled: October 18, 1976Date of Patent: June 20, 1978Assignee: Mead Johnson & CompanyInventors: Tellis Alexander Martin, William Timmey Comer
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Patent number: 4094981Abstract: Novel 10-imidoylphenoxazines and 10-imidoylacridans are prepared by reacting a phenoxazine or acridan having optional substituents selected from the group consisting of trifluoromethyl, halogen, dihalogen, alkyl or alkoxy with an imidoyl halide prepared in situ from amides and lactams. Illustrative embodiments are 10-(5-methyl-1-pyrrolin-2-yl)phenoxazine and 9,9-dimethyl-10-(5-methyl-1-pyrrolin-2-yl)acridan. The imidoylphenoxazines and imidoylacridan products are generally useful as smooth muscle relaxants.Type: GrantFiled: July 1, 1977Date of Patent: June 13, 1978Assignee: Mead Johnson & CompanyInventors: Yao Hua Wu, Walter G. Lobeck, Jr.
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Patent number: 4093741Abstract: A new class of arylsulfonylcarbamoyl-1,3-cyclohexanediones and arylsulfonylcarbamoyl-1,3-dicarbonylacyclic compounds are disclosed. These substances have hypoglycemic or hyperglycemic properties and are of value in controlling abnormal blood sugar levels. The arylsulfonylcarbamoyl derivatives of 1,3-dicarbonylalicyclic and acyclic compounds are prepared by reacting an arylsulfonylisocyanate with a 1,3-dicarbonylalicyclic or acyclic reactant. Typical embodiments are 2-(N-p-chlorobenzenesulfonylcarbamoyl)-5,5-dimethylcyclohexane-1,3-dione and 5-(1-ethylpropyl)-2-(N-p-chlorobenzenesulfonylcarbamoyl)-1,3-cyclohexanedi one.Type: GrantFiled: October 20, 1976Date of Patent: June 6, 1978Assignee: Mead Johnson & CompanyInventor: Frederick A. Grunwald
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Patent number: 4093739Abstract: N-[3-(mercaptoacetylamino)benzoyl]glycine, alkali metal and amine salts thereof are potent topically effective mucolytic agents.Type: GrantFiled: June 15, 1977Date of Patent: June 6, 1978Assignee: Mead Johnson & CompanyInventor: Tellis Alexander Martin
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Patent number: 4080500Abstract: A series of 2,6-diamino-4-tertiary-amino-pyridine 1-oxides is disclosed. Substituents in the 4-position include diethylamino, pyrrolidinyl, piperidino, morpholino, thiomorpholino, and N-methyl-piperazino. Novel oxadiazolones such as 5-amino-7-(1-piperidinyl)-2H-[1,2,4]-oxadiazolo[2,3-a]pyridine-2-one which are useful in the preparation of the pyridine 1-oxides are also disclosed. The compounds of this invention lower blood pressure in normotensive and hypertensive mammals and are particularly useful in the treatment of hypertensive conditions in mammals. 2,6-Diamino-4-(1-piperidinyl)pyridine 1-oxide is a representative embodiment of the invention.Type: GrantFiled: February 28, 1977Date of Patent: March 21, 1978Assignee: Mead Johnson & CompanyInventors: John E. Lawson, Ronald D. Dennis
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Patent number: 4077959Abstract: Novel amidine compounds selected from the group consisting of bis-pyrrolinyl derivatives of phenothiazines, phenoxazines and acridans are obtained by reacting a phenothiazine, phenoxazine or acridan with a pyrrolidinone in the presence of phosphorus oxychloride. The phenothiazine, phenoxazine, or acridan can also be alkylated with 2-chloro-1-(1-pyrrolin-2-yl)-2-pyrroline to provide compounds of the invention. Typical examples of bis-pyrrolinyl derivatives are 2-methoxy-10-[5-methyl-1-(5-methyl-1-pyrrolin-2-yl)-2-pyrrolin-2yl]phenoth iazine, 10-[1-(1-pyrrolin-2-yl)-2-pyrrolin-2-yl]phenoxazine, and 9,9-dimethyl-10-[5-methyl-1-(5-methyl-1-pyrrolin-2-yl)-2-pyrrolin-2-yl]acr idan. The amidine compounds are useful as diuretics, smooth muscle relaxants and antithrombogenic agents.Type: GrantFiled: December 15, 1975Date of Patent: March 7, 1978Assignee: Mead Johnson & CompanyInventors: Yao Hua Wu, Walter G. Lobeck, Jr.
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Patent number: 4072675Abstract: N-Phenyl amidines which have diuretic, antithrombogenic, smooth muscle relaxant, anti-inflammatory and antiarrhythmic properties have been discovered. They are prepared by reacting a substituted aniline with a carboxamide selected from the group consisting of amides and lactams in the presence of phosphorus oxychloride. Typical examples of substituted N-phenyl amidines thus obtained are 5-methyl-2-(N-phenylbenzylamino)-1-pyrroline, 2-(N-phenylbenzylamino)-1-pyrroline, 3-[(N-1-pyrrolin-2-yl-p-anisidino)methyl]indole and 4,5,6,7,8,9-hexahydro-2-(N-phenylphenethylamino)-3H-azonine. Indole substituted N-phenyl amidines can be rearranged to provide iminopyrrolidinylindoles which are useful as diuretic, antithrombogenic and smooth muscle relaxant agents. In the case of 3-[(N-1-pyrrolin-2-yl-p-anisidino)methyl]indole, the rearranged product is 3-[[2-(p-methoxyphenylimino)-1-pyrrolidinyl]methyl]indole.Type: GrantFiled: October 24, 1975Date of Patent: February 7, 1978Assignee: Mead Johnson & CompanyInventors: Yao Hua Wu, Walter G. Lobeck, Jr.
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Patent number: 4064254Abstract: The compounds are of the heterocyclic class of 2-phenethylpiperidines having an amido substituent in the ortho position of the phenethyl moiety. Substituents in the ortho position include formamido, benzamido, cinnamamido, 2-thiophenecarboxamido, alkanesulfonamido and alkanoylamido. They are useful as antiarrhythmic and/or antiserotonin agents. The novel compounds are prepared by reaction of appropriately substituted o-aminophenethylpiperidines and the carbonyl or sulfonyl halides or anhydrides. Typical embodiments of this invention are 4-methoxy-2'-[2-(1-methyl-2-piperidyl)ethyl]benzanilide and 2'-[2-(1-methyl-2-piperidyl)ethyl]cinnamanilide.Type: GrantFiled: October 21, 1976Date of Patent: December 20, 1977Assignee: Mead Johnson & CompanyInventors: Stanley J. Dykstra, Joseph L. Minielli
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Patent number: 4060615Abstract: A series of novel 4-amino or 4-hydrazino-2-(substituted piperazinyl)-6,7-dimethoxyquinazolines is disclosed having antihypertensive and phosphodiesterase inhibiting properties. Piperazinyl substituents include cycloalkenylcarbonyl, cycloalkylcarbonyl, and methylcycloalkylcarbonyl. A representative embodiment of the invention is 4-amino-2-[4-(cyclopentylcarbonyl)-1-piperazinyl]-6,7-dimethoxyquinazoline .Type: GrantFiled: February 18, 1976Date of Patent: November 29, 1977Assignee: Mead Johnson & CompanyInventors: William Lesley Matier, John David Catt
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Patent number: 4049714Abstract: N-Phenyl amidines which have diuretic, antithrombogenic, smooth muscle relaxant, anti-inflammatory and antiarrhythmic properties have been discovered. They are prepared by reacting a substituted aniline with a carboxamide selected from the group consisting of amides and lactams in the presence of phosphorus oxychloride. Typical examples of substituted N-phenyl amidines thus obtained are 5-methyl-2-(N-phenylbenzylamino)-1-pyrroline, 2-(N-phenylbenzylamino)-1-pyrroline, 3-[(N-1-pyrrolin-2-yl-p-anisidino)methyl]indole and 4,5,6,7,8,9-hexahydro-2-(N-phenylphenethylamino)-3H-azonine. Indole substituted N-phenyl amidines can be rearranged to provide iminopyrrolinidinylindoles which are useful as diuretic, antithrombogenic and smooth muscle relaxant agents. In the case of 3-[(N-1-pyrrolin-2-yl-p-anisidino)methyl]indole, the rearranged product is 3-[[2-(p-methoxyphenylimino)-1-pyrrolindinyl]methyl]indole.Type: GrantFiled: September 2, 1975Date of Patent: September 20, 1977Assignee: Mead Johnson & CompanyInventors: Yao Hua Wu, Walter G. Lobeck
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Patent number: 4044150Abstract: The sulfonamidophenethanolamine 4'-[1-hydroxy-2-[(2-phenoxyethyl)amino]ethyl]methanesulfonanilide is an antihypertensive beta-adrenergic blocking agent selectively lowering blood pressure with minimal reduction of heart rate.Type: GrantFiled: June 18, 1976Date of Patent: August 23, 1977Assignee: Mead Johnson & CompanyInventors: William E. Kreighbaum, Herbert R. Roth
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Patent number: 4035426Abstract: 1,3-bis(p-Hydroxyphenyl)cyclobutane and its monomethyl ether are estrogenic agents having antifertility action. They are prepared from R.sup.2 ethers of the monomethyl ether in which R.sup.2 is a readily cleaved hydroxl-protecting group, and from the corresponding 3-cyclobutanol compounds.Type: GrantFiled: December 4, 1975Date of Patent: July 12, 1977Assignee: Mead Johnson & CompanyInventors: John E. Lawson, Ronnie D. Dennis, Robert F. Majewski
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Patent number: 4015006Abstract: New 2-substituted-3(2H)-isoquinolones and 2-substituted-3-alkoxyisoquinolines are disclosed. They are orally active hypotensives and peripheral vasodilators with an extended duration of action. Representative embodiments of this invention are 6,7-dimethoxy-2-methyl-1-veratryl-3(2H)-isoquinolone hydrochloride, 2-allyl-6,7-dimethoxy-1-veratryl-3(2H)-isoquinolone hydrochloride, 2-cyclopropyl-6,7-dimethoxy-1-veratryl-3(2H)-isoquinolone hydrochloride, 2-amino-6,7-dimethoxy-1-veratryl-3(2H)-isoquinolone hydrochloride, and 3-ethoxy-6,7-dimethoxy-1-veratrylisoquinoline.Type: GrantFiled: September 12, 1975Date of Patent: March 29, 1977Assignee: Mead Johnson & CompanyInventors: William E. Kreighbaum, William T. Comer
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Patent number: 4000143Abstract: The compounds are of the heterocyclic class of 2-phenethylpiperidines having an amido substituent in the ortho position of the phenethyl moiety. Substituents in the ortho position include formamido, benzamido, cinnamamido, 2-thiophenecarboxamido, alkanesulfonamido and alkanoylamido. They are useful as antiarrhythmic and/or antiserotonin agents. The novel compounds are prepared by reaction of appropriately substituted o-aminophenethylpiperidines and the carbonyl or sulfonyl halides or anhydrides. Typical embodiments of this invention are 4-methoxy-2'-[2-(1-methyl-2-piperidyl)ethyl]benzanilide and 2'-[2-(1-methyl-2-piperidyl)ethyl]cinnamanilide.Type: GrantFiled: October 8, 1975Date of Patent: December 28, 1976Assignee: Mead Johnson & CompanyInventors: Stanley J. Dykstra, Joseph L. Minielli
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Patent number: 3998879Abstract: A new class of arylsulfonylcarbamoyl-1,3-cyclohexanediones and arylsulfonylcarbamoyl-1,3-dicarbonylacyclic compounds are disclosed. These substances have hypoglycemic or hyperglycemic properties and are of value in controlling abnormal blood sugar levels. The arylsulfonylcarbamoyl derivatives of 1,3-dicarbonylalicyclic and acyclic compounds are prepared by reacting an arylsulfonylisocyanate with a 1,3-dicarbonylalicyclic or acyclic reactant. Typical embodiments are 2-(N-p-chlorobenzenesulfonylcarbamoyl)-5,5-dimethylcyclohexane-1,3-dione and 5-(1-ethylpropyl)-2-(N-p-chlorobenzenesulfonylcarbamoyl)-1,3-cyclohexanedi one.Type: GrantFiled: August 15, 1975Date of Patent: December 21, 1976Assignee: Mead Johnson & CompanyInventor: Frederick A. Grunwald
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Patent number: 3995071Abstract: Soy protein having greatly reduced phytic acid and phytate complexes is prepared by aqueous extraction of defatted soy flakes, basification to a pH in excess of 10.1, and removal of insolubles. The clarified extract may be reduced in mineral and carbohydrates content by ultrafiltration. The purified aqueous extract may be advantageously used directly in the preparation of liquid dietary products without drying.Type: GrantFiled: June 23, 1975Date of Patent: November 30, 1976Assignee: Mead Johnson & CompanyInventors: Kenneth C. Goodnight, Jr., Grant H. Hartman, Jr., Robert F. Marquardt
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Patent number: 3979514Abstract: A process for interrupting pregnancy is disclosed which comprises administration to a mammal an interceptive agent selected from a group of sulfonamidoaminophenones. Illustrative of sulfonamidoaminophenone interceptive agents useful in the process of the present invention for interrupting pregnancy are 4'-(N,N-diethylalanyl)-methanesulfonanilide and 4'-[N-.alpha.,.alpha. -dimethylphenethyl)alanyl]methanesulfonanilide.Type: GrantFiled: August 26, 1974Date of Patent: September 7, 1976Assignee: Mead Johnson & CompanyInventors: Duane G. Gallo, William T. Comer
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Patent number: 3968242Abstract: A process for interrupting pregnancy is disclosed which comprises administration to a mammal an interceptive agent selected from a group of sulfonamidoaminopropiophenones. Illustrative of sulfonamidoaminopropiophenone interceptive agents useful in the process of the present invention for interrupting pregnancy are 4'-[3-(benzylmethylamino)propionyl]methanesulfonanilide and 4'-(3-hexamethyleniminopropionyl)methanesulfonanilide.Type: GrantFiled: August 26, 1974Date of Patent: July 6, 1976Assignee: Mead Johnson & CompanyInventors: Duane G. Gallo, William T. Comer
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Patent number: 3966082Abstract: A rotatable annular collar adapted for use with a conventional overcap of the snap-fit type and a container having a cylindrical mouth, an inwardly directed annular groove extending completely around the wall of the container and an outwardly projecting annular bead positioned at or between the mouth of the container and the annular groove formed for releasable holding engagement with the snap-fit cap is provided. The snap-fit cap has a top panel, an annular skirt depending therefrom and a lift tab extending outwardly from the lower margin of the depending skirt which also has an inwardly projecting annular bead adapted to snap over the outwardly projecting annular bead of the container. The rotatable annular collar has an upstanding exterior wall member with an access gate therein, an inwardly extending flange connecting the exterior wall member and an interior annular rib member frictionally fitted to the annular groove of the container.Type: GrantFiled: February 24, 1975Date of Patent: June 29, 1976Assignee: Mead Johnson & CompanyInventor: Brian D. Hopkins