Patents by Inventor Donald F. Page
Donald F. Page has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 4599423Abstract: Disclosed and claimed is the cardiotonic use of 1-R.sub.1 -5-(3-R'-4-R"-phenyl)-6-R-2(1H)-pyridinones (II), where R.sub.1 is hydrogen, lower-alkyl or lower-hydroxyalkyl, R is lower-alkyl or hydrogen, and, R' and R" are each hydrogen, amino or hydroxy, at least one of R' or R" being other than hydrogen, or where R' is nitro when R" is hydroxy, or pharmaceutically acceptable acid-addition salts thereof where at least one of R' and R" is amino. Also disclosed and claimed are 1-R.sub.1 -5-(3-R'-4-R"-phenyl)-6-R-2(1H)-pyridinones (I), where R.sub.1, R' and R" are defined as above and R is lower-alkyl and acid-addition salts thereof where at least one of R' and R" is amino. Also shown and claimed is the process which comprises reacting 1-R.sub.1 -1,2-dihydro-2-oxo-5-(3-R'-4-R"-phenyl)-6-R-nicotinonitrile, where R.sub.Type: GrantFiled: April 2, 1984Date of Patent: July 8, 1986Assignee: Sterling Drug Inc.Inventors: George Y. Lesher, Chester J. Opalka, Jr., Donald F. Page, Ruthann M. McGarry
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Patent number: 4559352Abstract: 1-R.sub.1 -3-amino-5-(3-R'-4-R"-phenyl)-6-R-2(1H)-pyridinones or salts thereof, which are useful as cardiotonics, where R.sub.1 is hydrogen, lower-alkyl, or lower-hydroxyalkyl, R is hydrogen or lower-alkyl, and, R' and R" are each hydrogen, hydroxy or amino at least one of R' or R" being other than hydrogen, are prepared by reacting the corresponding 3-carbamyl compound with a reagent capable of converting carbamyl to amino or by first reacting the corresponding 3-carbamyl compound where R' and R" are each hydrogen, nitro or lower-alkoxy at least one of R' and R" being other than hydrogen with a reagent capable of converting carbamyl to amino and then reacting the resulting 3-amino compound where R' and/or R" are/is lower-alkoxy and/or nitro with a reagent capable of converting lower-alkoxy to hydroxy and/or with a reagent capable of converting nitro to amino. Preparation of the corresponding 3-carbamyl and 3-cyano compounds is shown, the latter including cardiotonically active novel 1-R.sub.Type: GrantFiled: July 30, 1984Date of Patent: December 17, 1985Assignee: Sterling Drug Inc.Inventors: George Y. Lesher, Chester J. Opalka, Jr., Donald F. Page
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Patent number: 4515797Abstract: 1-R.sub.1 -3-amino-5-(3-R'-4-R"-phenyl)-6-R-2(1H)-pyridinones or salts thereof, which are useful as cardiotonics, where R.sub.1 is hydrogen, lower-alkyl, or lower-hydroxyalkyl, R is hydrogen or lower-alkyl, and, R' and R" are each hydrogen, hydroxy or amino at least one of R' or R" being other than hydrogen, are prepared by reacting the corresponding 3-carbamyl compound with a reagent capable of converting carbamyl to amino or by first reacting the corresponding 3-carbamyl compound where R' and R" are each hydrogen, nitro or lower-alkoxy at least one of R' and R" being other than hydrogen with a reagent capable of converting carbamyl to amino and then reacting the resulting 3-amino compound where R' and/or R" are/is lower-alkoxy and/or nitro with a reagent capable of converting lower-alkoxy to hydroxy and/or with a reagent capable of converting nitro to amino. Preparation of the corresponding 3-carbamyl and 3-cyano compounds is shown, the latter including cardiotonically active novel 1-R.sub.Type: GrantFiled: March 5, 1982Date of Patent: May 7, 1985Assignee: Sterling Drug Inc.Inventors: George Y. Lesher, Chester J. Opalka, Jr., Donald F. Page
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Patent number: 4465686Abstract: Disclosed and claimed is the cardiotonic use of 1-R.sub.1 -5-(3-R'-4-R"-phenyl)-6-R-2(1H)-pyridinones (II), where R.sub.1 is hydrogen, lower-alkyl or lower-hydroxyalkyl, R is lower-alkyl or hydrogen, and, R' and R" are each hydrogen, amino or hydroxy, at least one of R' or R" being other than hydrogen, or where R' is nitro when R" is hydroxy, or pharmaceutically acceptable acid-addition salts thereof where at least one of R' and R" is amino. Also disclosed and claimed are 1-R.sub.1 -5-(3-R'-4-R"-phenyl)-6-R-2(1H)-pyridinones (I), where R.sub.1, R' and R" are defined as above and R is lower-alkyl and acid-addition salts thereof where at least one of R' and R" is amino. Also shown and claimed is the process which comprises reacting 1-R.sub.1 -1,2-dihydro-2-oxo-5-(3-R'-4-R"-phenyl)-6-R-nicotinonitrile, where R.sub.Type: GrantFiled: April 26, 1982Date of Patent: August 14, 1984Assignee: Sterling Drug Inc.Inventors: George Y. Lesher, Chester J. Opalka, Jr., Donald F. Page, Ruthann M. McGarry
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Patent number: 4420617Abstract: 5-PY-6-Q-pyridin-2-amines (I) or pharmaceutically acceptable acid-addition salts thereof are useful cardiotonics, where Q is hydrogen or lower-alkyl, and PY is 4-pyridinyl or 4-pyridinyl having one or two lower-alkyl substituents. Their preparation from the corresponding 5-PY-6-Q-2(1H-pyridinones via the corresponding 2-halo-5-PY-6-Q-pyridines is shown.Type: GrantFiled: July 6, 1982Date of Patent: December 13, 1983Assignee: Sterling Drug Inc.Inventors: George Y. Lesher, Chester J. Opalka, Jr., Donald F. Page
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Patent number: 4391811Abstract: 2-(NB)-3-R-6-PY-5-Q-3H-imidazo[4,5-b]pyridines (I) and salts, useful as cardiotonics, where NB is amino or dimethylamino, R is lower-alkyl, Q is hydrogen or lower-alkyl, and PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, are prepared by reacting a 2-RNH-3-amino-5-PY-6-Q-pyridine with a di-(lower-alkyl) 2-methylthiopseudourea-1,3-dicarboxylate to produce 2-carbo(lower-alkoxy)amino-3-R-6-PY-5-Q-3H-imidazo[4,5-b] pyridine and hydrolyzing the latter to produce I where NB is amino and by reacting a 2-RNH-3-amino-5-PY-6-Q-pyridine with dichloromethylene-N,N-dimethylammonium chloride to produce I where NB is dimethylamino. Cardiotonic use of I is disclosed and claimed.Type: GrantFiled: October 2, 1981Date of Patent: July 5, 1983Assignee: Sterling Drug Inc.Inventors: George Y. Lesher, Chester J. Opalka, Jr., Donald F. Page
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Patent number: 4377585Abstract: Disclosed and claimed are a cardiac composition and a method for increasing cardiac contractility using an effective amount of a cardiotonic 4-[4-(or 3)-AcNH-phenyl]-2-R.sub.2 -3-R.sub.3 -5-R.sub.5 -6-R.sub.6 -pyridine (I) or pharmaceutically-acceptable salt thereof, where R.sub.2 is hydrogen, methyl, ethyl or hydroxyl, R.sub.6 is hydrogen, methyl or ethyl, R.sub.3 and R.sub.5 are each hydrogen or methyl, and Ac is hydrogen, hydroxyacetyl, acetoxyacetyl, .alpha.-hydroxypropionyl, .alpha.-acetoxypropionyl, methyoxyacetyl, 2-butenoyl or carbamyl or when NHAc is attached to the 4-position of the phenyl ring Ac also is formyl, n-propanoyl, 2,2-dimethyl-n-propanoyl or 3-carboxypropanoyl or when NHAc is attached to the 3-position of the phenyl ring Ac also is acetyl. Novel compounds shown and claimed are 4-[4-(or 3)-Ac'NH-phenyl]-2-R.sub.2 -3-R.sub.3 -5-R.sub.5 -6-R.sub.6 -pyridines (II) or pharmaceutically-acceptable acid-addition salts thereof, where R.sub.2, R.sub.3, R.sub.5 and R.sub.Type: GrantFiled: July 20, 1981Date of Patent: March 22, 1983Assignee: Sterling Drug Inc.Inventors: George Y. Lesher, Donald F. Page
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Patent number: 4376775Abstract: Disclosed and claimed are N-R-N-40 [4-(4-2-R.sub.2 -3-R.sub.3 -5-R.sub.5 -6-R.sub.6 -4-pyridinyl)phenyl]ureas (I) or pharmaceutically-acceptable acid-addition salts thereof, where R is hydrogen, methyl or ethyl, R.sub.2 is hydrogen, methyl, ethyl or hydroxyl, R.sub.6 hydrogen, methyl or ethyl, and R.sub.3 and R.sub.5 are each hydrogen or methyl, their cardiotonic use and their preparation.Type: GrantFiled: July 20, 1981Date of Patent: March 15, 1983Assignee: Sterling Drug Inc.Inventors: George Y. Lesher, Donald F. Page
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Patent number: 4374141Abstract: Shown is a process for preparing cardiotonically active 1,3-dihydro-3-R-6-PY-5-Q-2H-imidazo[4,5-b]pyridin-2-ones, where Q is hydrogen or lower-alkyl, R is lower-alkyl, lower-hydroxyalkyl, lower-alkoxyalkyl or Y-NB where Y is lower-alkylene and NB is di-(lower-alkyl)amino or 4-morpholinyl, and PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two substituents, by reacting a 2-RNH-5-PY-6-Q-nicotinamide with an alkali metal hypohalite. Also shown are cardiotonic compositions and a method for increasing cardiac contractility using 2-RR'N-5-PY-6-Q-nicotinamides or pharmaceutically acceptable acid-addition salts thereof, where R' is hydrogen or methyl. Also shown is the process for preparing said 2-RR'N-5-PY-6-Q-nicotinamides by reacting a 2-halo-5-PY-6-Q-nicotinamide with an amine of the formula RR'NH.Type: GrantFiled: August 17, 1981Date of Patent: February 15, 1983Assignee: Sterling Drug Inc.Inventors: George Y. Lesher, Chester J. Opalka, Jr., Donald F. Page
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Patent number: 4362734Abstract: Shown are cardiotonically active 2-RR'N-5-PY-6-Q-nicotinonitriles where R is methyl or ethyl, R' is hydrogen or methyl, PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two substituents, and Q is hydrogen or methyl, the latter only when R' is hydrogen, or pharmaceutically acceptable acid-addition salts thereof. Also shown are cardiotonic compositions and a method for increasing cardiac contractility using as active components 2-RR'N-5-PY-6-Q-nicotinonitriles or pharmaceutically acceptable acid-addition salts thereof, where R, R', PY and Q are defined as above. Also shown is the process for preparing said 2-RR'N-5-PY-6-Q-nicotinonitriles by reacting a 2-halo-5-PY-6-Q-nicotinonitrile with an amine of the formula RR'NH.Type: GrantFiled: August 26, 1981Date of Patent: December 7, 1982Assignee: Sterling Drug Inc.Inventors: George Y. Lesher, Chester J. Opalka, Jr., Donald F. Page
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Patent number: 4351941Abstract: 2-[R.sub.1 NHN(R)]-3-Q'-5-PY-6-Q-pyridines or pharmaceutically-acceptable acid-addition salts thereof are useful as cardiotonic agents, where Q is hydrogen or lower-alkyl, PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, Q' is hydrogen or halo, R is hydrogen, lower-alkyl or lower-hydroxyalkyl, and R.sub.1 is hydrogen or when R is other than hydrogen R.sub.1 is the same as R. These compounds are prepared by reacting a 2-halo-3-Q'-5-PY-6-Q-pyridine with R.sub.1 NHNHR where 2-halo is bromo or chloro. Also shown are: the use of said 2-[R.sub.1 NN(R)]-3-Q'-5-PY-6-Q-pyridines as cardiotonic agents; and, the intermediates, 2,3-dihalo-5-PY-6-Q-pyridines, and their preparation from 3-nitro-5-PY-6-Q-2(1H)-pyridinones.Type: GrantFiled: November 2, 1981Date of Patent: September 28, 1982Assignee: Sterling Drug Inc.Inventors: George Y. Lesher, Chester J. Opalka, Jr., Donald F. Page
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Patent number: 4331672Abstract: 2-[R.sub.1 NHN(R)]-3-Q'-5-Py-6-Q-pyridines or pharmaceutically-acceptable acid-addition salts thereof are useful as cardiotonic agents, where Q is hydrogen or lower-alkyl, PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, Q' is hydrogen or halo, R is hydrogen, lower-alkyl or lower-hydroxyalkyl, and R.sub.1 is hydrogen or when R is other than hydrogen R.sub.1 is the same as R. These compounds are prepared by reacting a 2-halo-3-Q'-5-PY-6-Q-pyridine with R.sub.1 NHNHR where 2-halo is bromo or chloro. Also shown are: the use of said 2-[R.sub.1 NN(R)]-3-Q'-5-PY-6-Q-pyridines as cardiotonic agents; and, the intermediates, 2,3-dihalo-5-PY-6-Q-pyridines, and their preparation from 3-nitro-5-PY-6-Q-2(1H)-pyridinones.Type: GrantFiled: February 4, 1981Date of Patent: May 25, 1982Assignee: Sterling Drug Inc.Inventors: George Y. Lesher, Chester J. Opalka, Jr., Donald F. Page
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Patent number: 4322533Abstract: 1-R.sub.1 -4- or 5-[4-pyridinyl-(CH.sub.2).sub.n ]-1H-indole-2,3-dione 3-Q derivatives, useful as cardiotonics, bronchodilators, anti-asthmatics, anti-allergics and anti-cholinergics, are prepared by cyclization of N-{3- or 4-[4-pyridinyl-(CH.sub.2).sub.n ]phenyl}glyoxalamide oxime with acid; reaction of the product thus obtained with a carbonyl reactive reagent to prepare a compound where Q is other than O; and reaction of a compound where Q is either O or other than O with a lower-alkyl, hydroxy-lower-alkyl or di-lower-alkylamino-lower-alkyl ester of a strong mineral acid or with a carbo-lower-alkoxy-lower-alkyl halide to prepare compounds where R.sub.1 is other than hydrogen.Type: GrantFiled: January 16, 1981Date of Patent: March 30, 1982Inventors: George Y. Lesher, Donald F. Page, Monte D. Gruett
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Patent number: 4317827Abstract: Disclosed and claimed are a cardiac composition and a method for increasing cardiac contractility using an effective amount of a cardiotonic 4-[4-(or 3)-AcNH-phenyl]-2-R.sub.2 -3-R.sub.3 -5-R.sub.5 -6-R.sub.6 -pyridine (I) or pharmaceutically-acceptable salt thereof, where R.sub.2 is hydrogen, methyl, ethyl or hydroxyl, R.sub.6 is hydrogen, methyl or ethyl, R.sub.3 and R.sub.5 are each hydrogen or methyl, and Ac is hydrogen, hydroxyacetyl, acetoxyacetyl, .alpha.-hydroxypropionyl, .alpha.-acetoxypropionyl, methyoxyacetyl, 2-butenoyl or carbamyl or when NHAc is attached to the 4-position of the phenyl ring Ac also is formyl, n-propanoyl, 2,2-dimethyl-n-propanoyl or 3-carboxypropanoyl or when NHAc is attached to the 3-position of the phenyl ring Ac also is acetyl. Novel compounds shown and claimed are 4-[4-(or 3)-Ac'NH-phenyl]-2-R.sub.2 -3-R.sub.3 -5-R.sub.5 -6-R.sub.6 -pyridines (II) or pharmaceutically-acceptable acid-addition salts thereof, where R.sub.2, R.sub.3, R.sub.5 and R.sub.Type: GrantFiled: May 27, 1980Date of Patent: March 2, 1982Assignee: Sterling Drug Inc.Inventors: George Y. Lesher, Donald F. Page
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Patent number: 4312875Abstract: 1-R.sub.1 -6-(lower-alkyl)-5-(pyridinyl)-2(1H)-pyridinones or 1-R.sub.1 -1,2-dihydro-2-oxo-6-(lower-alkyl)-5-(pyridinyl)nicotinic acids or lower-alkyl esters thereof or pharmaceutically-acceptable acid-addition or cationic salts thereof are useful as cardiotonic agents, where R.sub.1 is hydrogen, lower-alkyl or lower-hydroxyalkyl. These compounds are prepared by hydrolyzing the corresponding 3-cyano compounds to produce the corresponding 3-carboxylic acids and then either by decarboxylating or esterifying the acids.Type: GrantFiled: November 6, 1980Date of Patent: January 26, 1982Assignee: Sterling Drug Inc.Inventors: George Y. Lesher, Chester J. Opalka, Jr., Donald F. Page
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Patent number: 4309537Abstract: 1,3-Dihydro-1-R.sub.1 -3-R.sub.3 -6-PY-5-Q-2H-imidazo[4,5-b]pyridin-2-ones or -2-thiones or pharmaceutically-acceptable acid-addition salts thereof, which are useful as cardiotonic agents, where Q is hydrogen or lower-alkyl, R.sub.1 and R.sub.3 are each hydrogen, lower-alkyl, lower-hydroxyalkyl, 2,3-dihydroxypropyl, lower-alkoxyalkyl or Y-NB where Y is lower-alkylene and NB is di-(lower-alkyl)amino or 4-morpholinyl, at least one of R.sub.1 and R.sub.3 being hydrogen, and PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two substituents, are prepared by reacting a 2-R.sub.3 NH-3-R.sub.1 NH-5-PY-6-Q-pyridine with urea or carbonyldiimidazole to produce said -2-one or with an alkali metal xanthate, thiourea or thiocarbonyldiimidazole to produce said -2-thione. Also shown and claimed are cardiotonic compositions and a method for increasing cardiac contractility using said cardiotonic agents. Also shown are processes for preparing said intermediate 2-R.sub.3 NH-3-R.sub.Type: GrantFiled: February 20, 1981Date of Patent: January 5, 1982Assignee: Sterling Drug Inc.Inventors: George Y. Lesher, Chester J. Opalka, Jr., Donald F. Page
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Patent number: 4297360Abstract: 2-R.sub.3 RN-3-R.sub.1 R'N-5-PY-6-Q-pyridines (I) or pharmaceutically-acceptable acid-addition salts thereof are useful as intermediates in the preparation of 1- or 3-substituted-1,3-dihydro-5-Q-6-PY-2H-imidazo[4,5-b]pyridin-2-ones or -2-thiones and also as intermediates for preparing 1- or 3-substituted-5-Q-6-PY-3H(or 1H)-imidazo[4,5-b]pyridines, where R.sub.1, R.sub.3, R, R', PY and Q are defined hereinbelow. Also shown are processes for preparing I and the following intermediates used therein: 2-halo-3-nitro-5-PY-6-Q-pyridines (III), 2-R.sub.3 RN-3-nitro-5-PY-6-Q-pyridines (V), 2-halo-5-PY-6-Q-pyridines (VII), 2-R.sub.3 RN-5-PY-6-Q-pyridines (VIII) and 2-R.sub.3 RN-3-halo-5-PY-6-Q-pyridines (IX) or salts thereof. Certain embodiments of II and VIII also are useful as cardiotonics and are shown as active components of cardiac compositions and methods for increasing cardiac contractility.Type: GrantFiled: March 28, 1980Date of Patent: October 27, 1981Assignee: Sterling Drug Inc.Inventors: George Y. Lesher, Chester J. Opalka, Jr., Donald F. Page
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Patent number: 4294837Abstract: 1,3-Dihydro-1-R.sub.1 -3-R.sub.3 -6-PY-5-Q-2H-imidazo[4,5-b]pyridin-2-ones or -2-thiones or pharmaceutically-acceptable acid-addition salts thereof, which are useful as cardiotonic agents, where Q is hydrogen or lower-alkyl, R.sub.1 and R.sub.3 are each hydrogen, lower-alkyl, lower-hydroxyalkyl, 2,3-dihydroxypropyl, lower-alkoxyalkyl or Y-NB where Y is lower-alkylene and NB is di-(lower-alkyl)amino or 4-morpholinyl, at least one of R.sub.1 and R.sub.3 being hydrogen, and PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two substituents, are prepared by reacting a 2-R.sub.3 NH-3-R.sub.1 NH-5-PY-6-Q-pyridine with urea or carbonyldiimidazole to produce said -2-one or with an alkali metal xanthate, thiourea or thiocarbonyldiimidazole to produce said -2-thione. Also shown and claimed are cardiotonic compositions and a method for increasing cardiac contractility using said cardiotonic agents. Also shown are processes for preparing said intermediate 2-R.sub.3 NH-3-R.sub.Type: GrantFiled: March 28, 1980Date of Patent: October 13, 1981Assignee: Sterling Drug Inc.Inventors: George Y. Lesher, Chester J. Opalka, Jr., Donald F. Page
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Patent number: 4276293Abstract: 2-R.sub.2 -3-R.sub.3 -6-PY-5-Q-3H-imidazo[4,5-b]pyridines (I) or 1-R.sub.1 -2-R.sub.2 -6-PY-5-Q-1H-imidazo[4,5-b]pyridines (IA) or pharmaceutically-acceptable acid-addition salts thereof, where Q and R.sub.2 are each hydrogen or lower-alkyl, R.sub.1 and R.sub.3 are each hydrogen, lower-alkyl, lower-hydroxyalkyl, 2,3-dihydroxypropyl, lower-alkoxyalkyl or Y-NB where Y is lower-alkylene having at least two carbon atoms between its connecting linkages and NB is di-(lower-alkyl)amino or 4-morpholinyl, at least one of R.sub.1 or R.sub.3 being hydrogen, and PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, which are useful as cardiotonics, are prepared by reacting 2-R.sub.3 NH-3-R.sub.1 NH-5-PY-6-Q-pyridine (II) with a tri-(lower-alkyl) ortho-(lower-alkanoate). Also shown are: the use of I or IA or salts in cardiotonic compositions and a method for increasing cardiac contractility; and, the preparation of the intermediates II, as well as intermediates used to prepare II.Type: GrantFiled: March 28, 1980Date of Patent: June 30, 1981Assignee: Sterling Drug Inc.Inventors: George Y. Lesher, Chester J. Opalka, Jr., Donald F. Page