Patents Assigned to Apotex, Inc.
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Publication number: 20160024165Abstract: A method for purifying rHuEPO through the use of a multi-step filtration process which provides for a rHuEPO product having superior stability and shelf-life.Type: ApplicationFiled: March 14, 2014Publication date: January 28, 2016Applicant: Apotex Inc.Inventors: Jason Everett Dowd, Robert Weik, Thomas Hemetsberger
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Publication number: 20150353490Abstract: The invention relates to organic salts of Saxagliptin and processes for their preparation.Type: ApplicationFiled: May 24, 2013Publication date: December 10, 2015Applicant: APOTEX INC.Inventors: Padiyath Mohammed AKBARALI, Venkata Ramana KINTALI, Shreenivasa Murthy H N, Prakash Bhaskar SHETTY, Narendra Manjeshwar MALLYA, Venkataramana Lachhi REDDY
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Patent number: 8097624Abstract: The present invention provides an cycloalkyl derivative of 3-hydroxy-4-pyridinone which is useful for the chelation of metal ions such as iron. Its preparation and use is described. In particular, the invention concerns the removal of iron in chemical and biological systems including chelating agents having the formula I wherein R1 is X with the proviso that R2 is Y; or R1 is T with the proviso that R2 is W; or R1 is X with the proviso that R2R5N when taken together form a heterocyclic ring selected from piperidinyl, morpholinyl, pyrrolidinyl or piperazinyl, wherein the group piperidinyl, morpholinyl, pyrrolidinyl or piperazinyl is either unsubstituted or substituted with one to three C1 to C6 alkyl groups.Type: GrantFiled: May 9, 2008Date of Patent: January 17, 2012Assignee: Apotex Inc.Inventors: Tim Fat Tam, Michael Spino, Wanren Li, Yingsheng Wang, Yanqing Zhao, Birenkumar Hasmukhbhai Shah
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Patent number: 7893269Abstract: The present invention relates to a novel process for the preparation of 1-alkyl or 1-cycloalkyl derivatives of 3-hydroxy-4-oxo-1,4-dihydropyridine-2-carboxamide of formula (I). The process includes reacting an amine R2NH2 with a compound of formula (II) in a solution of metal hydroxide in water to give a compound of formula (III). Subsequent reaction of the compound of formula (III) with an acid chloride formation reagent in an inert solvent gives compounds of formula (I). The acid chloride formation reagent is selected from oxalyl chloride and dimethylformamide, dimethylchloromethylene-ammonium chloride and thionyl chloride and dimethylformamide. If desired, a compound of formula (I) where R5 is hydrogen may be formed when an intermediate substituent is used wherein R5 is an alcohol protective group removable by catalytic hydrogenation.Type: GrantFiled: November 17, 2005Date of Patent: February 22, 2011Assignee: Apotex IncInventors: Tim Fat Tam, Regis Leung-Toung, Yanqing Zhao, Wanren Li, Yingsheng Wang, Sandra Vittoria Agostino, Birenkumar Hasmukhbhai Shah
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Patent number: 7410985Abstract: The present invention provides an cycloalkyl derivative of 3-hydroxy-4-pyridinone which is useful for the chelation of metal ions such as iron. Its preparation and use is described. In particular, the invention concerns the removal of iron in chemical and biological systems including chelating agents having the formula (I); wherein R1 is X with the proviso that R2 is Y; or R1 is T with the proviso that R2 is W; or R1 is X with the proviso that R2 R5 N when taken together form a heterocyclic ring selected from piperidinyl, morpholinyl, pyrrolidinyl or piperazinyl, wherein the group piperidinyl, morpholinyl, pyrrolidinyl or piperazinyl is either unsubstituted or substituted with one to three C1 to C6 alkyl groups.Type: GrantFiled: November 18, 2004Date of Patent: August 12, 2008Assignee: Apotex Inc.Inventors: Tim Fat Tam, Michael Spino, Wanren Li, Yingsheng Wang, Yanqing Zhao, Birenkumar Hasmukhbhai Shah
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Publication number: 20080096886Abstract: The present invention relates to a novel process for the preparation of 1-alkyl or 1-cycloalkyl derivatives of 3-hydroxy-4-oxo-1,4-dihydropyridine-2-carboxamide of formula I. The process includes reacting an amine R2NH2 with a compound of formula II in a solution of metal hydroxide in water to give a compound of formula III. Subsequent reaction of the compound of formula III with an acid chloride formation reagent in an inert solvent gives compounds of formula I. The acid chloride formation reagent is selected from oxalyl chloride and dimethylformamide, dimethylchloromethylene-ammonium chloride and thionyl chloride and dimethylformamide. If desired, a compound of formula I where R5 is hydrogen may be formed when an intermediate substituent is used wherein R5 is an alcohol protective group removable by catalytic hydrogenation.Type: ApplicationFiled: November 17, 2005Publication date: April 24, 2008Applicant: APOTEX INC.Inventors: Tim Tam, Regis Leung-Toung, Yanqing Zhao, Wanren Li, Yingsheng Wang, Sandra Agostino, Birenkumar Shah
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Patent number: 7049328Abstract: A method of treating iron induced cardiac disease in a patient with iron overload, such as in thalassemia or the like comprising administering to the patient a therapeutically effective amount of deferiprone or a physiologically acceptable salt thereof sufficient to treat iron induced cardiac disease normally associated with iron overload.Type: GrantFiled: June 28, 2001Date of Patent: May 23, 2006Assignee: Apotex Inc.Inventors: Michael Spino, Antonio Piga
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Publication number: 20030225007Abstract: A method of inhibiting the activity of transglutaminases containing a cysteine residue comprising administering to a mammal an effective amount of a sulfonamide derivative of imidazo[1,2-d]-1,2,4-thiadiazoles sufficient to inhibit the activity.Type: ApplicationFiled: March 27, 2003Publication date: December 4, 2003Applicant: Apotex Inc.Inventors: Tim Fat Tam, Khashayar Karimian, Regis C.S.H. Leung-Toung, Yanqing Zhao, Jolanta Maria Wodzinska, Wanren Li, Jayme Nicole Lowrie
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Patent number: 6531486Abstract: Solid pharmaceutical compositions comprising quinapril magnesium can be made by reacting a quinapril or an acid addition salt thereof with an alkaline magnesium compound in the presence of a solvent so as to convert the quinapril or quinapril acid addition salt to quinapril magnesium.Type: GrantFiled: June 7, 2001Date of Patent: March 11, 2003Assignee: Apotex Inc.Inventor: Bernard Charles Sherman
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Patent number: 6506929Abstract: A process is disclosed for the preparation of simvastatin which enables highly regio selective C-methylation of the 2′-position group of lovastatin without requiring protection/deprotection of 13-OH of lovastatin and lactone ring opening/closure.Type: GrantFiled: April 24, 2001Date of Patent: January 14, 2003Assignee: Apotex Inc.Inventors: Khashayar Karimian, Tim Fat Tam, Yong Tao, Yiwei Li, Gary Doucette
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Patent number: 6476229Abstract: The present invention relates to a novel process for the preparation of 3-hydroxy-N,1,6-trialkyl-4-oxo-1,4-dihydropyridine-2-carboxamide of formula I: The method comprises of the TEMPO oxidation of a primary alcohol of 3-O-protected-2-hydroxymethyl-6-alkyl-4H-pyran-4-one of formula III to 3-O-protected-6-alkyl-4-oxo-4H-pyran-2-carboxylic acid of formula II. Reaction of compound of formula II with methylamine and 1,1-carbonyldiimidazole in an inert solvent affords 3-O-protected-N, 1,6-trialkyl-4-oxo-1,4-dihydropyridine-2-carboxamide, which is deprotected to give of 3-hydroxy-N,1,6-trialkyl-4-oxo-1,4-dihydropyridine-2-carboxamide of formula I.Type: GrantFiled: March 19, 2002Date of Patent: November 5, 2002Assignee: Apotex, Inc.Inventors: Tim F. Tam, Wanren Li
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Patent number: 6472532Abstract: The present invention relates to a novel process for the preparation of 3-hydroxy-N,1,6-trialkyl-4-oxo-1,4-dihydropyridine-2-carboxamide of formula I: The method comprises of the TEMPO oxidation of a primary alcohol of 3-O-protected-2-hydroxymethyl-6-alkyl-4H-pyran-4-one of formula III to 3-O-protected-4-alkyl-4-oxo-4H-pyran-2-carboxylic acid of formula II. Reaction of compound of formula II with methylamine and 1,1-carbonyidiimidazole in an inert solvent affords 3-O-protected-N,1,6-trialkyl-4-oxo-1,4-dihydropyridine-2-carboxamide, which is deprotected to give of 3-hydroxy-N,1,6-trialkyl-4-oxo-1,4-dihydropyridine-2-carboxamide of formula I.Type: GrantFiled: March 19, 2002Date of Patent: October 29, 2002Assignee: Apotex, Inc.Inventors: Tim F. Tam, Wanren Li
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Patent number: 6468977Abstract: Novel 1,2,4-thiadiazole compounds are provided, which are effective as inhibitors of cysteine activity-dependent enzymes and in particular of cysteine proteases. The compounds are useful in treating acne by inhibition of transglutaminase, common cold by inhibition of human rhinovirus 3C protease and inflammatory joint disease by inhibition of cathepsins. The compounds of the present invention are 3,5-disubstituted 1,2,4-thiadazole of the general formula (I): where Z is a nitrogen containing group with recognition sequence for the enzyme and Y is a substituent that tunes the reactivity of the inhibitor towards the thiol group of the cysteine activity-dependent enzyme. The Y group may also serve in recognition.Type: GrantFiled: May 23, 2000Date of Patent: October 22, 2002Assignee: Apotex Inc.Inventors: Khashayar Karimian, Tim Fat Tam, Regis C. S. H. Leung-Toung, Wanren Li, Steve Patrick Bryson, Jolanta Maria Wodzinska
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Patent number: 6426418Abstract: The present invention relates to a novel process for the preparation of 3-hydroxy-N,1,6-trialkyl-4-oxo-1,4-dihydropyridine-2-carboxamide of formula I: The method comprises of the TEMPO oxidation of a primary alcohol of 3-O-protected-2-hydroxymethyl-6-alkyl-4H-pyran-4-one of formula III to 3-O-protected-6-alkyl-4-oxo-4H-pyran-2-carboxylic acid of formula II. Reaction of compound of formula II with methylamine and 1,1-carbonyldiimidazole in an inert solvent affords 3-O-protected-N,1,6-trialkyl-4-oxo-1,4-dihydropyridine-2-carboxamide, which is deprotected to give of 3-hydroxy-N,1,6-trialkyl-4-oxo-1,4-dihydropyridine-2-carboxamide of formula I.Type: GrantFiled: November 2, 2001Date of Patent: July 30, 2002Assignee: Apotex, Inc.Inventors: Tim F. Tam, Wanren Li
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Patent number: 6245903Abstract: A novel form of azithromycin and processes for preparation of pure azithromycin monohydrate isopropanol clathrate (3 molecules of isopropanol for every 10 molecules of azithromycin monohydrate) has been obtained. Preparation of the novel form of azithromycin comprises the steps of dissolving azithromycin in isopropanol, followed by the slow addition of water to the organic solution.Type: GrantFiled: August 13, 1999Date of Patent: June 12, 2001Assignee: Apotex, Inc.Inventors: Khashayar Karimian, Mehrnoush Motamedi
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Patent number: 6162791Abstract: Novel 1,2,4-thiadiazole compounds are provided, which are effective as inhibitors of cysteine activity-dependent enzymes and in particular of cysteine proteases. The compounds are useful in treating acne by inhibition of transglutaminase, common cold by inhibition of human rhinovirus 3C protease and inflammatory joint disease by inhibition of cathepsins. The compounds of the present invention are 3,5-disubstituted 1,2,4-thiadazole of the general formula (I): ##STR1## where Z is a nitrogen containing group with recognition sequence for the enzyme and Y is a substituent that tunes the reactivity of the inhibitor towards the thiol group of the cysteine activity-dependent enzyme. The Y group may also serve in recognition.Type: GrantFiled: March 2, 1998Date of Patent: December 19, 2000Assignee: Apotex Inc.Inventors: Khashayar Karimian, Tim Fat Tam, Regis C. S. H. Leung-Toung, Wanren Li
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Patent number: 6114537Abstract: Thiols are trapped, and converted to disulfide compounds, by a process of reacting them with compounds containing a 1,2,4-thiadiazole ring structure carrying a substituent at position 3 of the thiadiazole ring, and being unsubstituted at position N-2. The process is useful pharmacologically, in inhibiting certain thiol-containing enzymes such as H.sup.+ /K.sup.+ -ATPase (the proton pump), and industrially, in selective removal of thiol compounds from gas or liquid mixtures.Type: GrantFiled: February 21, 1997Date of Patent: September 5, 2000Assignee: Apotex Inc.Inventors: Khashayar Karimian, Tim F. Tam, Denis Desilets, Sue Lee, Tullio Cappelletto, Wanren Li
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Patent number: 6060472Abstract: Novel 3,5-disubstituted 1,2,4-thiadiazole compounds are provided, which are effective in treating peptic ulcers by the inhibition of H.sup.+ /K.sup.+ -ATPase. The compounds of the present invention are 3,5-disubstituted 1,2,4-thiadiazole corresponding to the general formula (I): ##STR1## where R.sup.1 is a group with cell penetration properties for the inhibition of the enzyme in-vitro and in-vivo, and Y is a substituent that tunes the reactivity of the inhibitor towards the cysteine residue of H.sup.+ /K.sup.+ -ATPase. The Y group may also serve in recognition.Type: GrantFiled: April 6, 1998Date of Patent: May 9, 2000Assignee: Apotex Inc.Inventors: Khashayar Karimian, Tim Fat Tam, Regis C. S. H. Leung-Toung, Wanren Li
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Patent number: 6024247Abstract: Solid dosage forms of pharmaceuticals, e.g. tablets, may be removed from blister packs with a deblistering machine. The machine has a roller and a stationary plate. The roller has a longitudinal axis of rotation and means for rotating the roller about the axis. The roller has an inner core and a cover thereon with a non-slip surface. The stationary plate has at least as many slots as there are columns of blisters, and each of the slots has a width parallel to the rotational axis of the roller, the width of each slot being at least as large as the width of a blister. Each of the slots has a length transverse to the slot's width and is at least as large as the length of a blister. The plate is situated to provide a throat, between the cover and the plate, into which the blister pack may be fed and through which the blister pack may pass as a result of rotation of the roller. The plate has a guide to ensure that each column of blisters is aligned with corresponding slots.Type: GrantFiled: December 29, 1997Date of Patent: February 15, 2000Assignee: Apotex Inc.Inventor: Geoffrey Charles Birr
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Patent number: RE39087Abstract: A novel form of azithromycin and processes for preparation of pure azithromycin monohydrate isopropanol clathrate (3 molecules of isopropanol for every 10 molecules of azithromycin monohydrate) has been obtained. Preparation of the novel form of azithromycin comprises the steps of dissolving azithromycin in isopropanol, followed by the slow addition of water to the organic solution.Type: GrantFiled: June 5, 2003Date of Patent: May 2, 2006Assignee: Apotex, Inc.Inventors: Khashayar Karimian, Mehrnoush Motamedi