Patents Represented by Attorney Robert H. Uloth
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Patent number: 5413995Abstract: A lyophilized pharmaceutical solid composition containing cyclophosphamide for reconstitution with water to provide a solution for oral or parenteral administration. This lyophilized cyclophosphamide solid composition demonstrates improved stability, solubility characteristics and enhanced appearance compared with currently available dry powder pre-mix compositions of cyclophosphamide. The lyophilized solid composition contains about 20 parts by weight of cyclophosphamide, about 11/4-2 parts by weight of water and from about 10-85 parts by weight of excipient which is comprised mainly of mannitol. Processes for making the composition are disclosed.Type: GrantFiled: March 8, 1985Date of Patent: May 9, 1995Assignee: Mead Johnson & CompanyInventors: Robert L. Alexander, Robert J. Bequette, Terry T. Kensler, Joseph A. Scott
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Patent number: 5372823Abstract: A directly compressed cholestyramine tablet with a solvent-free coating is disclosed. The inner core of the tablet is made up of cholestyramine agglomerates consisting of numerous small, irregularly-shaped, jagged-edged fragments having relatively few smooth or flat surfaces with a moisture content ranging from about 8 to 14 percent by weight. A process is also disclosed for preparing cholestyramine agglomerates of the invention. The solvent-free coating comprises from about 60 percent to about 95 percent by weight of stearic acid and from about 5 percent to about 40 percent of polyethylene glycol.Type: GrantFiled: October 22, 1992Date of Patent: December 13, 1994Assignee: Bristol-Myers Squibb CompanyInventors: Robert J. Bequette, Bruce A. Bonenberger, Claude E. Gallian, John R. Reckelhoff
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Patent number: 5262540Abstract: Oxazole derivatives having Formula I or II are disclosed which are useful as inhibitors of mammalian blood platelet aggregation. ##STR1## Formula I and Formula XIX compounds are those wherein n is 7-9 and R is hydrogen or lower alkyl. Formula II compounds are those wherein R is hydrogen, lower alkyl or together with CO.sub.2 is tetrazol-1-yl; R.sub.1 is phenyl or thienyl; X is a divalent connecting group selected from the group consisting of CH.sub.2 CH.sub.2, CH.dbd.CH, and CH.sub.2 O; Y is a divalent connecting group attached to the 3 or 4 phenyl position selected from the group consisting of OCH.sub.2, CH.sub.2 CH.sub.2 and CH.dbd.CH. Formula XX compounds are those wherein the OCH.sub.2 CO.sub.2 R moiety is attached to the 3 or 4 phenyl position and R is hydrogen or lower alkyl.Type: GrantFiled: May 10, 1993Date of Patent: November 16, 1993Assignee: Bristol-Myers Squibb CompanyInventor: Nicholas A. Meanwell
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Patent number: 5096894Abstract: An improved oral rehydration solution comprising a mixture of rice dextrin and required electrolytes is provided. The functionality of the rice dextrin in oral rehydration solutions is superior to glucose in infants with chronic diarrhea resulting in lower stool output and enhanced water retention. Rice dextrin also has a polymer profile which provides more readily available glucose than corn dextrin or rice fluor. There is also provided a process for clarifying solutions of rice dextrin which involves a first filtration at 35.degree. C. and 50.degree. C. and a second filtration at temperatures above 80.degree. C. using filter aid and activated carbon.Type: GrantFiled: April 3, 1990Date of Patent: March 17, 1992Assignee: Bristol-Myers Squibb CompanyInventors: Michael C. Tao, Richard E. Litov, John R. Euber, Salim S. Akrabawi, J. Roberto Moran
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Patent number: 5077305Abstract: Heterocyclic acids and esters useful as inhibitors of mammalian blood platelet aggregation characterized by Formula I or II are disclosed.HET.sub.1 -(CH.sub.2).sub.n CO.sub.2 R (I) ##STR1## Formula I compounds are those wherein n is 6-9, R is hydrogen, lower alkyl or an alkali metal ion, and HET.sub.1 is the heterocyclic radical 4,5-diphenyl-2-thiazoyl.Formula II compounds are those wherein R.sub.1 is hydrogen, lower alkyl or an alkali metal ion, and the radical --OCH.sub.2 CO.sub.2 R is attached in the 3 or 4 ring position; and HET.sub.2 is the heterocyclic radical 4,5-diphenyl-2-thiazoyl.Type: GrantFiled: February 13, 1990Date of Patent: December 31, 1991Assignee: Bristol-Myers Squibb Co.Inventor: Nicholas A. Meanwell
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Patent number: 5047246Abstract: A directly compressible pharmaceutical composition comprising cyclophosphamide and a partially or fully pregelatinized starch is disclosed. The pharmaceutical composition, when directly compressed into a tablet, exhibits unexpected stability when compared to cyclophosphamide in combination with other direct compression vehicles.Type: GrantFiled: September 9, 1988Date of Patent: September 10, 1991Assignee: Bristol-Myers CompanyInventors: Claude E. Gallian, Charles Williams
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Patent number: 5034409Abstract: Heterocyclic acids and esters useful as inhibitors of mammalian blood platelet aggregation characterized by Formula I are disclosed.HET.sub.1 --(CH.sub.2).sub.n CO.sub.2 R (I)Formula I compounds are those wherein n is 6-9, R is hydrogen, lower alkyl or an alkali metal ion, and HET.sub.1 is the heterocyclic radical 3,4-diphenyl-1H-pyrrol-1-yl.Type: GrantFiled: February 13, 1990Date of Patent: July 23, 1991Assignee: Bristol-Myers Squibb CompanyInventor: Nicholas A. Meanwell
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Patent number: 5021415Abstract: Heterocyclic acids and esters useful as inhibitors of mammalian blood platelet aggregation characterized by Formula I or II are disclosed. ##STR1## Formula I compounds are those wherein n is 6-9, R is hydrogen, lower alkyl or an alkali metal ion, and HET.sub.1 is the heterocyclic radical 2,3-dihydro-3-oxo-5,6-diphenyl-1,2,4-triazin-2-yl.Formula II compounds are those wherein R.sub.1 is hydrogen, lower alkyl or an alkali metal ion, and the radical --OCH.sub.2 CO.sub.2 R is attached in the 3 or 4 ring position; and HET.sub.2 is the heterocyclic radical 2,3-dihydro-3-oxo-5,6-diphenylmethyl-1,2,3-triazin-2-yl.Type: GrantFiled: February 13, 1990Date of Patent: June 4, 1991Assignee: Bristol-Myers Squibb Co.Inventor: Nicholas A. Meanwell
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Patent number: 5011283Abstract: A support device for a workpiece, such as a spectrophotometric flow cell is provided. The device includes a base plate, a mounting bar attached to the base plate, a support arm slidably mounted on the base plate/mounting bar assembly, an adjustment plug contained in an elongate cavity formed in the support arm, and a workpiece rotatably friction mounted on the adjustment plug. With the base plate mounted horizontally, the orientation and position of the work piece may be adjusted horizontally by sliding the support arm along the mounting bar, vertically by moving the adjustment plug within the elongate cavity and rotationally by rotating the workpiece, which is retained in its new position by the friction mount.Type: GrantFiled: January 8, 1990Date of Patent: April 30, 1991Assignee: Bristol-Myers Squibb Co.Inventors: Tony R. Carrie, Robert A. Newton
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Patent number: 5011851Abstract: Heterocyclic acids and esters useful as inhibitors of mammalian blood platelet aggregation characterized by Formula I or II are disclosed.HET.sub.1 --(CH.sub.2).sub.n CO.sub.2 R (I) ##STR1## Formula I compounds are those wherein n is 6-9, R is hydrogen, lower alkyl or an alkali metal ion, and HET.sub.1 is the heterocyclic radical 4,5-diphenyl-1H-imidazol-2-yl.Formula II compounds are those wherein R.sub.1 is hydrogen, lower alkyl or an alkali metal ion, and the radical --OCH.sub.2 CO.sub.2 R is attached in the 3 or 4 ring position; and HET.sub.2 is the heterocyclic radical 4,5-diphenyl-1H-imidazol-2-yl.Formula VIII compounds are those wherein R.sub.1 is hydrogen, lower alkyl or an alkali metal ion, and the radical --OCH.sub.2 CO.sub.2 R is attached in the 3 or 4 ring position.Type: GrantFiled: June 20, 1990Date of Patent: April 30, 1991Assignee: Bristol-Myers Squibb Co.Inventor: Nicholas A. Meanwell
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Patent number: 4994476Abstract: A series of compounds useful in treating cardiovascular disorders due to the combined expression of both .beta.-block and calcium-block activity by these agents. This useful combination of actions is effected by a novel combination of structural subunits forming these compounds. Essentially, .beta.-blocking aryloxypropanolamine moieties are attached via their aryl ring or amino nitrogen at one of the carboxylate groups of calcium-blocking 4-aryl-1,4-dihydropyridine-3,5-dicarboxylates. These compounds are prepared from new 4-aryl-1,4-dihydropyridine intermediate compounds.Type: GrantFiled: September 23, 1985Date of Patent: February 19, 1991Assignee: Bristol-Myers CompanyInventor: Graham S. Poindexter
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Patent number: 4992439Abstract: Heterocyclic acids andesters useful as inhibitors of mammalian blood platelet aggregation characterized by Formula I or II are disclosed. ##STR1## Formula I compounds are those wherein n is 6-9, R is hydrogen, lower alkyl or an alkali metal ion, and HET.sub.1 is the heterocyclic radical 1,6-dihydro-6-oxo-3,4-diphenyl-1-pyridazinyl.Formula II compounds are those wherein R.sub.1 is hydrogen, lower alkyl or an alkali metal ion, and the radical --OCH.sub.2 CO.sub.2 R is attached in the 3 or 4 ring position; and HET.sub.2 is the heterocyclic radical 1,6-dihydro-6-oxo-3,4-diphenyl-1-pyridazinyl.Type: GrantFiled: February 13, 1990Date of Patent: February 12, 1991Assignee: Bristol-Myers Squibb CompanyInventor: Nicholas A. Meanwell
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Patent number: 4990344Abstract: This invention concerns a process for preparing soluble rice protein concentrate with reduced levels of manganese, aluminum, selenium and phytic acid and improved digestibility from rice raw material comprising:digesting the raw material reduced in particle size to permit efficient enzyme action in an aqueous medium with an alpha-amylase enzyme at an operable pH and temperature for a period of time sufficient to solubilize a substantial portion of the rice starch and form a liquid slurry;heating the rice starch slurry at 105.degree. C. to 130.degree. C. for 30 to 60 seconds;separating the high protein rice flour from the rice syrup;treating a slurry of the high protein rice flour with a protease enzyme at an operable pH and temperature in an amount and for a period of time to solubilize the rice protein:clarifying the protease treated slurry to provide a soluble rice protein concentrate with reduced manganese, aluminum, selenium and phytic acid and improved digestibility.Type: GrantFiled: July 11, 1989Date of Patent: February 5, 1991Assignee: Bristol-Myers CompanyInventors: John R. Euber, Gabor Puski, Grant H. Hartman, Jr.
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Patent number: 4983610Abstract: Heterocyclic acids and esters useful as inhibitors of mammalian blood platelet aggregation characterized by Formula I are disclosed.HET.sub.1 --(CH.sub.2).sub.n CO.sub.2 R (I)Formula I compounds are those wherein n is 6-9, R is hydrogen, lower alkyl or an alkali metal ion, and HET.sub.1 is the heterocyclic radical 1-oxo-4,5-diphenyl-2H-pyrimidin-1-yl.Type: GrantFiled: February 13, 1990Date of Patent: January 8, 1991Assignee: Bristol-Myers Squibb CompanyInventor: Nicholas A. Meanwell
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Patent number: 4970225Abstract: Heterocyclic acids and esters useful as inhibitors of mammalian blood platelet aggregation characterized by Formula I are disclosed.HET.sub.1 -(CH.sub.2).sub.n CO.sub.2 R (I)Formula I compounds are those wherein n is 6-9, R is hydrogen, lower alkyl or an alkali metal ion, and HET.sub.1 is the heterocyclic radical 2,5-dioxo-3,4-diphenylimidazolidin-1-yl.Type: GrantFiled: February 13, 1990Date of Patent: November 13, 1990Assignee: Bristol-Myers Squibb CompanyInventor: Nicholas A. Meanwell
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Patent number: 4956182Abstract: A directly compressed cholestyramine tablet with a solvent-free coating is disclosed. The inner core of the tablet is made up of cholestyramine agglomerates consisting of numerous small, irregularly-shaped, jagged-edged fragments having relatively few smooth or flat surfaces with a moisture content ranging from about 8 to 14 percent by weight. A process is also disclosed for preparing cholestyramine agglomerates of the invention. The solvent-free coating comprises from about 60 percent to about 95 percent by weight of stearic acid and from about 5 percent to about 40 percent of polyethylene glycol.Type: GrantFiled: March 16, 1989Date of Patent: September 11, 1990Assignee: Bristol-Myers CompanyInventors: Robert J. Bequette, Bruce A. Bonenberger, Claude E. Gallian, John R. Reckelhoff
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Patent number: 4956379Abstract: Heterocyclic acids and esters useful as inhibitors of mammalian blood platelet aggregation characterized by Formula I or II are disclosed.HET.sub.1 --(CH.sub.2).sub.n CO.sub.2 R (I) ##STR1## Formula I compounds are those wherein n is 6-9, R is hydrogen, lower alkyl or an alkali metal ion, and HET.sub.1 is the heterocyclic radical 1,5-diphenyl-1H-pyrazol-3-yl.Formula II compounds are those wherein R.sub.1 is hydrogen, lower alkyl or an alkali metal ion, and the radical --OCH.sub.2 CO.sub.2 R is attached in the 3 or 4 ring position; and HET.sub.2 is a heterocyclic radical selected from the group consisting of 3,4-diphenyl-1H-pyrazol-1-yl, 4,5-diphenyl-1H-pyrazol-1-yl and 1,5-diphenyl-1H-pyrazol-3-yl.Type: GrantFiled: February 13, 1990Date of Patent: September 11, 1990Assignee: Bristol-Myers Squibb CompanyInventor: Nicholas A. Meanwell
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Patent number: 4956376Abstract: Heterocyclic acids and esters useful as inhibitors of mammalian blood platelet aggregation characterized by Formula I or II are disclosed. ##STR1## Formula I compounds are those wherein n is 6-9, R is hydrogen, lower alkyl or an alkali metal ion, and HET.sub.1 is the heterocyclic radical 5-(diphenylmethyl)-2H-tetrazol-2-yl.Formula II compounds are those wherein R.sub.1 is hydrogen, lower alkyl or an alkali metal ion, and the radical --OCH.sub.2 CO.sub.2 R is attached in the 3 or 4 ring position; and HET.sub.2 is the heterocyclic radical 5-(diphenylmethyl)-2H-tetrazol-2-yl.Type: GrantFiled: February 13, 1990Date of Patent: September 11, 1990Assignee: Bristol-Myers Squibb CompanyInventor: Nicholas A. Meanwell
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Patent number: 4943573Abstract: A novel series of 2,3-dihydro-2-oxo-1H-imidazo[4,5-b]quinolinyloxyalkanoic acid amides having enhanced water solubility is disclosed of the formula ##STR1## wherein n is 3 to 5; R.sub.1 is alkyl of 1 to 4 carbon atoms; R.sub.2 is hydrogen; R.sub.3 is 1-piperidinylethyl, 1-benzylpiperidin-4-yl, 4-(1-piperidinyl)piperidine, (1-alkyl-2-pyrrolidinyl)alkyl where alkyl is 1 to 4 carbon atoms, 3-quinuclidinyl; R.sub.2 and R.sub.3 together with the nitrogen atom to which they are attached form 4-R.sub.4 -piperazin-1-yl wherein R.sub.4 is alkyl of 1 to 7 carbon atoms, alkoxyethyl of 3 to 7 carbon atoms, pyridinyl, pyrimidinyl, tetrahydropyranylmethyl, thienylmethyl, cycloalkyl-(CH.sub.2).sub.m where m is zero or one and cycloalkyl is 5 to 7 carbon atoms except m is zero when cycloalkyl is 7 carbon atoms, benzyl, 4-fluorobenzyl, 3-trifluoromethylbenzyl, 4-alkoxybenzyl where alkoxy is 1 to 4 carbon atoms.Type: GrantFiled: November 1, 1989Date of Patent: July 24, 1990Assignee: Bristol-Myers Squibb CompanyInventor: Nicholas A. Meanwell
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Patent number: 4895846Abstract: A series of 1,4-dihydropyridin-3,5-yl dicarboxylic acid amides and esters incorporating an arylpiperazinylalkyl moiety have been prepared possessing the general formula ##STR1## wherein R.sup.4 is cycloalkyl, aryl or hetaryl, generally with electron-withdrawing substituents; R.sup.2 and R.sup.6 are lower alkyl, alkanol, alkoxyalkyl, or alkylaminoalkyl; R.sup.5 is R.sup.2 or arylpiperazinylalkyl; X is O or NH; Y is lower alkylene, alkoxyalkylene, alkylaminoalkylene; and Z is phenyl, substituted pheny, pyridinyl, substituted pyridinyl, or pyrimidinyl. Compounds of this series demonstrate activity as calcium and alpha-adrenergic blockers in in vitro testing and antihypertensive, anti-ischemic, and platelet function inhibiting actions in in vivo screens.Type: GrantFiled: December 18, 1987Date of Patent: January 23, 1990Assignee: Bristol-Myers CompanyInventors: Graham S. Poindexter, Davis L. Temple, Jr.