Patents Represented by Attorney Alan M. Krubiner
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Patent number: 5470582Abstract: A controlled release pharmaceutical composition comprising a physiologically active agent dispersed in preformed porous polymeric microparticles is provided. The active agent concentration may be up to about 10% by weight to achieve controlled release. Each of the porous microparticles has a plurality of preformed pores into which active agent is loaded and from which the active agent is subsequently released to the environment of use. The compositions are capable of delivering physiologically effective amounts of active agent for at least about thirty days, which delivery may be reversibly controlled by exposure to ultrasound.Type: GrantFiled: February 5, 1993Date of Patent: November 28, 1995Assignee: Syntex (U.S.A.) Inc.Inventors: Andreas Supersaxo, Jim H. Kou
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Patent number: 5455045Abstract: Mycophenolate mofetil and mycophenolic acid can be conveniently manufactured into high dose oral formulations by the hot melt filling of a supercooled mycophenolate mofetil or mycophenolic acid liquid into a pharmaceutical dosage form. High dose oral pharmaceutical formulations and manufacturing methods therefor are disclosed.Type: GrantFiled: May 13, 1993Date of Patent: October 3, 1995Assignee: Syntex (U.S.A.) Inc.Inventors: Glenn J. Samuels, Jung-Chung Lee, Charles Lee, Stephen Berry, Paul J. Jarosz
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Patent number: 5449664Abstract: Nucleoside compounds of the formula ##STR1## wherein: B is a purine or a pyrimidine;X and X' are H, OH or F, provided that at least one is H;Y and Y' are H, OH, OCH.sub.3 or F, provided that at least one is H;Y' and Z together form a cyclic phosphate ester, provided that Y is H; orZ is ##STR2## where n is zero, one, two or three; and Z' is N.sub.3 or OCH.sub.3 ; provided that when X' and Y' are OH and Z' is N.sub.3, B is not cytosine, andwhen X' and Y' are OH and Z' is OCH.sub.3, B is not uracil, adenine or cytosine;and the pharmaceutically acceptable esters, ethers and salts thereof, have been found to have potent antiviral activity with a high therapeutic ratio.Type: GrantFiled: December 16, 1991Date of Patent: September 12, 1995Assignee: Syntex (U.S.A.) Inc.Inventors: Julien P. H. Verheyden, Hans Maag, Ernest J. Prisbe
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Patent number: 5405864Abstract: Maleimide derivatives, i.e., the compounds of Formula I: ##STR1## wherein: R.sup.1 is H, halo, alkyl, OH, alkoxy, haloalkyl, NO.sub.2, or NR.sup.5 R.sup.6 ;R.sup.2 is H or CN;R.sup.3 is aryl or heteroaryl, provided that R.sup.3 is heteroaryl when R.sup.2 is H and R.sup.4 is NR.sup.5 R.sup.6 ; andR.sup.4 is NR.sup.5 R.sup.6 or isothiourea,where R.sup.5 and R.sup.6 are independently H or lower alkyl;and the pharmaceutically acceptable salts thereof, and their use as chemotherapeutic agents.Type: GrantFiled: October 15, 1993Date of Patent: April 11, 1995Assignee: Syntex (U.S.A.) Inc.Inventor: Chris A. Broka
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Patent number: 5380739Abstract: Compounds of the Formula (I), (II), or (III): ##STR1## wherein the variables are as defined in the specification and the pharmaceutically acceptable salts thereof, exhibit useful pharmacological properties, and are particularly useful as angiotensin II antagonists.Type: GrantFiled: February 4, 1993Date of Patent: January 10, 1995Assignee: Syntex (U.S.A.) Inc.Inventors: Robin D. Clark, David E. Clarke, Lawrence E. Fisher, Alam Jahangir
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Patent number: 5380879Abstract: The disclosed derivatives of mycophenolic acid are therapeutic agents advantageous in the treatment of disease states indicated for mycophenolic acid and/or mycophenolate mofetil and other immunosuppressant agents.Type: GrantFiled: February 18, 1994Date of Patent: January 10, 1995Assignee: Syntex (U.S.A.) Inc.Inventor: Eric B. Sjogren
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Patent number: 5378847Abstract: The invention provides a new and efficient process for preparing 2,4(5)-substituted or 1,2,4-substituted imidazole derivatives.The invention also provides a process for preparing substituted aminoalkylimidazole derivatives, useful for the treatment of mammals having a variety of disease states, including stroke, epilepsy, hypertension, angina, migraine, arrhythmia, thrombosis, embolism, and the like.Type: GrantFiled: December 21, 1993Date of Patent: January 3, 1995Assignee: Syntex Pharmaceuticals, Ltd.Inventors: Gary McCort, Jean-Claude Pascal
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Patent number: 5366737Abstract: This invention relates to compounds of the formulaor an optical isomer thereof wherein R.sup.1 and R.sup.2 are the same or different and are an alkyl or alkenyl group of 6 to 24 carbon atoms; R.sup.3, R.sup.4 and R.sup.5 are the same or different and are alkyl of 1 to 8 carbon atoms, aryl, aralkyl of 7 to 11 carbon atoms, or when two or three of R.sup.3, R.sup.4, and R.sup.5 are taken together to form quinuclidino, piperidino, pyrrolidino, or morpholino; n is 1 to 8; and X is a pharmaceutically acceptable anion.Type: GrantFiled: February 10, 1993Date of Patent: November 22, 1994Assignee: Syntex (U.S.A.) Inc.Inventors: Deborah A. Eppstein, Philip L. Felgner, Thomas R. Gadek, Gordon H. Jones, Richard B. Roman
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Patent number: 5342953Abstract: Compounds of the formula: ##STR1## wherein: A is oxo or dioxo;R.sup.1, R.sup.2 and R.sup.3 are independently hydrogen or lower alkyl of one to six carbon atoms;R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are independently hydrogen, lower alkyl of one to six carbon atoms, alkoxy, acyl or halo;are advantageously converted to thieno[3,2-c]pyridine derivatives and the pharmaceutically acceptable salts thereof, particularly ticlopidine hydrochloride.Type: GrantFiled: January 31, 1991Date of Patent: August 30, 1994Assignee: Syntex (U.S.A.) Inc.Inventors: Gary F. Cooper, Keith E. McCarthy
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Patent number: 5296609Abstract: The invention provides a new and efficient process for preparing 2,4(5)-substituted or 1,2,4-substituted imidazole derivatives.The invention also provides a process for preparing substituted aminoalkylimidazole derivatives, useful for the treatment of mammals having a variety of disease states, including stroke, epilepsy, hypertension, angina, migraine, arrhythmia, thrombosis, embolism, and the like.The invention also relates to novel aminoalkylimidazole compounds.Type: GrantFiled: April 9, 1993Date of Patent: March 22, 1994Assignee: Syntex Pharmaceuticals, Ltd.Inventors: Gary McCort, Jean-Claude Pascal
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Patent number: 5284971Abstract: Compounds of general formula (I) ##STR1## wherein R.sup.1 is (CH.sub.2).sub.n ((CHNR.sup.7 R.sup.8).sub.m C(O)R.sup.9 ; n=1-3; and m=0 or 1;R.sup.3 and R.sup.5 are independently Cl, Br, I, or CH.sub.3 ;R.sup.7 and R.sup.8 are independently H or (C.sub.1 -C.sub.4)alkyl;R.sup.9 is OH, (C.sub.1 -C.sub.4)alkoxy, or NR.sup.7 R.sup.8 ;R.sup.31 is H, Cl, Br, I, (C.sub.1 -C.sub.4)alkyl, (C.sub.4 -C.sub.6)cycloalkyl, (C.sub.1 -C.sub.4)haloalkyl, (C.sub.4 -C.sub.6)halocycloalkyl, or --CH(R.sup.10)Ar where Ar is selected from 5-hydroxypyrid-2-yl, 6-hydroxypyrid-3-yl, 6-hydroxypyridazin-3-yl, 6-methoxypyridazin-3-yl, 6-hydroxypyridazin-3-yl N-oxide, and 6-methoxypyridazin-3-yl N-oxide and R.sup.10 is H or (C.sub.1 -C.sub.4)alkyl;R.sup.41 is OH or a bioprecursor thereof; and the pharmaceutically acceptable salts thereof; are structural analogs of the thyroid hormones T.sub.3 and T.sub.4 and exhibit selective thyromimetic activity.Type: GrantFiled: July 16, 1992Date of Patent: February 8, 1994Assignee: Syntex (U.S.A.) Inc.Inventors: Keith A. Walker, Sharada S. Labadie, Denis J. Kertesz, Craig W. Laughton
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Patent number: 5264437Abstract: The present invention relates to optionally substituted pyrido[2,3-d]pyrimidine-2,4(1H,3H)-diones or optionally substituted pyrido[2,3-d]pyrimidine-2(1H,3H)-ones, i.e., compounds of Formula I: ##STR1## wherein: Y is --CH.sub.2 -- or --C(O)--;R.sup.1 is hydrogen or --(CH.sub.2).sub.n --R.sup.7, wherein:R.sup.7 is aryl or heteroaryl, andn is 1 or 2,provided that when Y is --C(O)--, R.sup.7 is heteroaryl; andR.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are hydrogen, or one is selected from lower alkyl, halo, carboxy, methoxycarbonyl, carbamoyl, methylcarbamoyl, di-methylcarbamoyl, methylcarbonyl, methylthio, methylsulfinyl, methylsulfonyl, hydroxymethyl, amino, trifluoromethyl, cyano or nitro; orR.sup.2, R.sup.3, R.sup.4 and R.sup.5 are independently selected from hydrogen, lower alkyl, nitro, chloro, fluoro, methoxycarbonyl or methylcarbonyl, provided at least one is hydrogen, and R.sup.6 is hydrogen;or a pharmaceutically acceptable ester, ether or salt thereof.Type: GrantFiled: March 20, 1992Date of Patent: November 23, 1993Assignee: Syntex (U.S.A.) Inc.Inventors: Robert S. Wilhelm, Ronnie L. Chin, Bruce H. Devens, Robert Alvarez
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Patent number: 4962091Abstract: An active agent delivery system for the controlled administration of macromolecular polypeptides which comprises a micro-suspension of water-soluble components in a polylactide matrix.Type: GrantFiled: May 23, 1986Date of Patent: October 9, 1990Assignee: Syntex (U.S.A.) Inc.Inventors: Deborah A. Eppstein, Brian B. Schryver
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Patent number: 4956365Abstract: Compounds of formulas (1) and (2): ##STR1## in which: X and Y are independently hydrogen, hydroxy, lower alkyl, lower alkoxy or halo, or X and Y taken together is methylenedioxy or ethylene-1,2-dioxy;W is oxygen or sulfur; andZ is --R.sup.1, --OR.sup.2 or --NR.sup.3 R.sup.4, whereinR.sup.1 is lower alkyl, lower haloalkyl, cycloalkyl, optionally substituted phenyl or phenyl lower alkyl, or heteroaryl;R.sup.2 is lower alkyl, optionally substituted phenyl or phenyl lower alkyl;R.sup.3 and R.sup.4 are independently hydrogen, alkyl, optionally substituted phenyl or phenyl lower alkyl; orR.sup.3 and R.sup.4 taken together with the nitrogen to which they are attached represent a heterocycle of the formula: ##STR2## wherein A is --(CH.sub.2).sub.m, --N(R.sup.5)-- or oxygen, in which m is an integer of 0-2 and R.sup.5 is hydrogen or lower alkyl;or a pharmaceutically acceptable salt thereof, are useful as .alpha..sub.2 -blockers.Type: GrantFiled: October 12, 1988Date of Patent: September 11, 1990Assignee: Syntex (U.S.A.) Inc.Inventors: Robin D. Clark, Andrew T. Kilpatrick, Michael Spedding
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Patent number: 4940556Abstract: A long acting sustained release pharmaceutical composition for dihydropyridine calcium channel blockers wherein the calcium channel blocker and a pH-dependent binde are intimately admixed in essentially spherically shaped non-rugose particles of up to 1.2 mm in diameter.Type: GrantFiled: July 26, 1987Date of Patent: July 10, 1990Assignee: Syntex (U.S.A.) Inc.Inventors: Calum B. MacFarlane, Alastair B. Selkirk, Michael J. Dey
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Patent number: 4929630Abstract: The present invention is directed to certain 3,5 substituted, 4,5-dihydroisoxazoles, and methods for their use. These compounds are transglutaminase inhibitors, and are particularly effective in the inhibition of epidermal transglutaminase and the treatment of acne.Type: GrantFiled: September 8, 1989Date of Patent: May 29, 1990Assignee: Syntex (U.S.A.) Inc.Inventors: Arlindo L. Castelhano, Lawrence M. DeYoung, Alexander Krantz, Diana H. Pliura, Michael C. Venuti
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Patent number: 4921862Abstract: The invention concerns a method of inhibiting both thromboxane synthetase and cyclic-AMP phosphodiesterase in a mammal having a disease characterized by elevated thromboxane levels or an imbalance of prostacyclin/thromboxane levels with a compound of the formula: ##STR1## or a pharmaceutically acceptable acid addition salt or ester thereof, wherein:X is chosen from the group consisting of: ##STR2## and a covalent bond in which R.sup.1 is H, alkyl having 1-6 carbon atoms, optionally substituted phenyl or optionally substituted phenyl lower alkyl, when R.sup.2 is H or OH, or R.sup.1 and R.sup.2 taken together represent oxo, alkylidene having 1-6 carbon atoms or optionally substituted benzylidene;R.sup.3 is H or alkyl having 1-6 carbon atoms, R.sup.4 is H and R.sup.3 and R.sup.4 are either cis or trans to each other, or R.sup.3 and R.sup.4 taken together represent a covalent bond;n is an integer from 0-3;Het is 1-imidazolyl or 3-pyridyl; and the dotted line represents an optional covalent bond.Type: GrantFiled: September 21, 1988Date of Patent: May 1, 1990Assignee: Syntex (U.S.A.) Inc.Inventors: Keith A. M. Walker, John J. Bruno, Gregory R. Martinez
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Patent number: 4920225Abstract: Optically active compounds of formula 1 ##STR1## wherein R.sub.1 is H or lower alkyl;R.sub.2 and R.sub.6 are each independently lower alkyl, aryl, or arylalkyl;R.sub.3 is CN, NO.sub.2, CO.sub.2 R.sub.5, CONHR.sub.5, SO.sub.2 R.sub.5, or P(O)(OR.sub.5).sub.2, where R.sub.5 is lower alkyl, lower alkoxyalkyl, aryl, or arylalkyl;R.sub.4 is aryl, heterocyclyl, or fused-ring heterocyclyl, optionally substituted with one, two, or three halo, NO.sub.2, CN, lower alkyl, lower alkoxy, lower alkylamino, CF.sub.3, OCH.sub.2 F, or OCF.sub.3 ;are prepared by fractional crystallization from hot organic solvent and water in the presence of a suitable optically active amine base.Type: GrantFiled: December 22, 1986Date of Patent: April 24, 1990Assignee: Laboratoires Syntex S.A.Inventor: Gilles Genain
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Patent number: 4916238Abstract: This invention relates to a novel process for making an allenic prostanoic acid derivative in the form of a single stereoisomer, or a mixture of stereosiomers, represented by the formula (I): ##STR1## wherein R is lower alkyl, R.sup.1 is a protecting group which can be selectively removed in the presence of R.sup.2, R.sup.2 is an acid-labile, base-stable protecting group, X is --(CH.sub.2).sub.2 --, trans --CH.dbd.CH-- or --C.tbd.C--, Y is --C(R.sup.3)(OR.sup.2)CH.sub.2 --, in which --OR.sup.2 is in the .alpha. or .beta. configuration and R.sup.3 is hydrogen or methyl, Z is alkyl, or phenyl, benzyl or phenoxy each optionally substituted on the phenyl ring, and the wavy lines represent the .alpha. or .beta. configuration with the proviso that when one wavy line is .alpha. the other is .beta..Type: GrantFiled: December 13, 1988Date of Patent: April 10, 1990Assignee: Syntex (U.S.A.) Inc.Inventors: Gary F. Cooper, Colin C. Beard, David Y. Jackson, Douglas L. Wren
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Patent number: 4873232Abstract: Novel alkoxycarbonylamino benzoates and related copounds (carbamoyl benzoates) are disclosed for treatment of auto-immune disease states, such as arthritis.Type: GrantFiled: October 29, 1986Date of Patent: October 10, 1989Assignee: SyntexInventors: Alexander Krantz, John M. Young