Patents Represented by Attorney Robert H. Uloth
  • Patent number: 5413995
    Abstract: 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: Grant
    Filed: March 8, 1985
    Date of Patent: May 9, 1995
    Assignee: Mead Johnson & Company
    Inventors: Robert L. Alexander, Robert J. Bequette, Terry T. Kensler, Joseph A. Scott
  • Patent number: 5372823
    Abstract: 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: Grant
    Filed: October 22, 1992
    Date of Patent: December 13, 1994
    Assignee: Bristol-Myers Squibb Company
    Inventors: Robert J. Bequette, Bruce A. Bonenberger, Claude E. Gallian, John R. Reckelhoff
  • Patent number: 5262540
    Abstract: 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: Grant
    Filed: May 10, 1993
    Date of Patent: November 16, 1993
    Assignee: Bristol-Myers Squibb Company
    Inventor: Nicholas A. Meanwell
  • Patent number: 5096894
    Abstract: 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: Grant
    Filed: April 3, 1990
    Date of Patent: March 17, 1992
    Assignee: Bristol-Myers Squibb Company
    Inventors: Michael C. Tao, Richard E. Litov, John R. Euber, Salim S. Akrabawi, J. Roberto Moran
  • Patent number: 5077305
    Abstract: 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: Grant
    Filed: February 13, 1990
    Date of Patent: December 31, 1991
    Assignee: Bristol-Myers Squibb Co.
    Inventor: Nicholas A. Meanwell
  • Patent number: 5047246
    Abstract: 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: Grant
    Filed: September 9, 1988
    Date of Patent: September 10, 1991
    Assignee: Bristol-Myers Company
    Inventors: Claude E. Gallian, Charles Williams
  • Patent number: 5034409
    Abstract: 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: Grant
    Filed: February 13, 1990
    Date of Patent: July 23, 1991
    Assignee: Bristol-Myers Squibb Company
    Inventor: Nicholas A. Meanwell
  • Patent number: 5021415
    Abstract: 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: Grant
    Filed: February 13, 1990
    Date of Patent: June 4, 1991
    Assignee: Bristol-Myers Squibb Co.
    Inventor: Nicholas A. Meanwell
  • Patent number: 5011851
    Abstract: 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: Grant
    Filed: June 20, 1990
    Date of Patent: April 30, 1991
    Assignee: Bristol-Myers Squibb Co.
    Inventor: Nicholas A. Meanwell
  • Patent number: 5011283
    Abstract: 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: Grant
    Filed: January 8, 1990
    Date of Patent: April 30, 1991
    Assignee: Bristol-Myers Squibb Co.
    Inventors: Tony R. Carrie, Robert A. Newton
  • Patent number: 4994476
    Abstract: 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: Grant
    Filed: September 23, 1985
    Date of Patent: February 19, 1991
    Assignee: Bristol-Myers Company
    Inventor: Graham S. Poindexter
  • Patent number: 4992439
    Abstract: 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: Grant
    Filed: February 13, 1990
    Date of Patent: February 12, 1991
    Assignee: Bristol-Myers Squibb Company
    Inventor: Nicholas A. Meanwell
  • Patent number: 4990344
    Abstract: 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: Grant
    Filed: July 11, 1989
    Date of Patent: February 5, 1991
    Assignee: Bristol-Myers Company
    Inventors: John R. Euber, Gabor Puski, Grant H. Hartman, Jr.
  • Patent number: 4983610
    Abstract: 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: Grant
    Filed: February 13, 1990
    Date of Patent: January 8, 1991
    Assignee: Bristol-Myers Squibb Company
    Inventor: Nicholas A. Meanwell
  • Patent number: 4970225
    Abstract: 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: Grant
    Filed: February 13, 1990
    Date of Patent: November 13, 1990
    Assignee: Bristol-Myers Squibb Company
    Inventor: Nicholas A. Meanwell
  • Patent number: 4956376
    Abstract: 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: Grant
    Filed: February 13, 1990
    Date of Patent: September 11, 1990
    Assignee: Bristol-Myers Squibb Company
    Inventor: Nicholas A. Meanwell
  • Patent number: 4956182
    Abstract: 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: Grant
    Filed: March 16, 1989
    Date of Patent: September 11, 1990
    Assignee: Bristol-Myers Company
    Inventors: Robert J. Bequette, Bruce A. Bonenberger, Claude E. Gallian, John R. Reckelhoff
  • Patent number: 4956379
    Abstract: 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: Grant
    Filed: February 13, 1990
    Date of Patent: September 11, 1990
    Assignee: Bristol-Myers Squibb Company
    Inventor: Nicholas A. Meanwell
  • Patent number: 4943573
    Abstract: 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: Grant
    Filed: November 1, 1989
    Date of Patent: July 24, 1990
    Assignee: Bristol-Myers Squibb Company
    Inventor: Nicholas A. Meanwell
  • Patent number: 4895846
    Abstract: 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: Grant
    Filed: December 18, 1987
    Date of Patent: January 23, 1990
    Assignee: Bristol-Myers Company
    Inventors: Graham S. Poindexter, Davis L. Temple, Jr.