Patents Assigned to Apotex, Inc.
  • Patent number: 6476229
    Abstract: 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: Grant
    Filed: March 19, 2002
    Date of Patent: November 5, 2002
    Assignee: Apotex, Inc.
    Inventors: Tim F. Tam, Wanren Li
  • Patent number: 6472532
    Abstract: 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: Grant
    Filed: March 19, 2002
    Date of Patent: October 29, 2002
    Assignee: Apotex, Inc.
    Inventors: Tim F. Tam, Wanren Li
  • Patent number: 6426418
    Abstract: 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: Grant
    Filed: November 2, 2001
    Date of Patent: July 30, 2002
    Assignee: Apotex, Inc.
    Inventors: Tim F. Tam, Wanren Li
  • Patent number: 6245903
    Abstract: 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: Grant
    Filed: August 13, 1999
    Date of Patent: June 12, 2001
    Assignee: Apotex, Inc.
    Inventors: Khashayar Karimian, Mehrnoush Motamedi
  • Patent number: 5914401
    Abstract: Novel process for the preparation of quinolone carboxylic acid derivatives of general formula I, and intermediates thereof as illustrated in Scheme 1 wherein the key intermediate is a compound of formula IX.
    Type: Grant
    Filed: March 11, 1998
    Date of Patent: June 22, 1999
    Assignee: Apotex, Inc.
    Inventors: Ian Egle, Regis C.S.H. Leung-Toung, Bo Lei, Tim Fat Tam, Tao Xin, Khashayar Karimian
  • Patent number: 5900485
    Abstract: Process for the manufacture of triazolone compounds and in particular nefazodone and intermediates useful in the manufacture thereof.
    Type: Grant
    Filed: October 15, 1997
    Date of Patent: May 4, 1999
    Assignee: Apotex, Inc.
    Inventors: Bo Lei, Tim Fat Tam, Khashayar Karimian, Rudolf Kubela
  • Patent number: 5847118
    Abstract: A process for preparing pure amorphous cefuroxime axetil comprising the steps of dissolving crystalline cefuroxime axetil in a highly polar organic solvent and adding the resulting solution to water, or alternatively, dissolving crystalline cefuroxime axetil in a highly polar solvent and adding small quantities of water to the organic solution and adding the resulting organic-aqueous solution to water.
    Type: Grant
    Filed: July 25, 1997
    Date of Patent: December 8, 1998
    Assignee: Apotex, Inc.
    Inventors: Khashayar Karimian, Mehrnoush Motamedi, Salvatore Zinghini
  • Patent number: 5723618
    Abstract: The invention relates to a novel process to prepare 1,4-dihydropyridines and in particular amlopidine and in novel intermediates obtained during the synthesis of the 1,4-dihydropyridines which have potential activity as antihypertensive agents.
    Type: Grant
    Filed: October 10, 1996
    Date of Patent: March 3, 1998
    Assignee: Apotex, Inc.
    Inventors: Regis Chung Soon Hin Leung-Toung, Khashayar Karimian, Tim Fat Tam
  • Patent number: 5691173
    Abstract: A novel microorganism, Penicillium adametzioides and a process of using the microorganism to produce compactin, the process consisting of fermentation in a nutrient medium.
    Type: Grant
    Filed: September 19, 1996
    Date of Patent: November 25, 1997
    Assignee: Apotex, Inc.
    Inventors: Scott Primrose, David King, Ed Yaworski, Jayaramaiyer Radhakrishnan, David He, Xinfa Xiao
  • Patent number: 5433256
    Abstract: A pill guide for use in combination with pill, capsule and caplet dispensing trays has a tapered guide channel for removable attachment to the pill return outlet of the tray. The guide combines with adjacent wall portions of the tray return outlet to form a convergent funnel, through which unwanted pills may be discarded back to the bulk supply from where they came. The pill guide may incorporate a guidance lip to facilitate alignment of the tray with the bulk receptacle.
    Type: Grant
    Filed: January 14, 1994
    Date of Patent: July 18, 1995
    Assignee: Apotex, Inc.
    Inventor: Val Vasers
  • Patent number: 5409820
    Abstract: A novel microorganism, Coniothyrium fuckelii ATCC 74227, and a process of using the microorganism for the production of lovastatin comprising fermenting Coniothyrium fuckelii ATCC 74227 or a lovastatin-producing mutant thereof in a nutrient medium containing assimilable sources of carbon, nitrogen, and inorganic salts under aerobic fermentation conditions.
    Type: Grant
    Filed: August 6, 1993
    Date of Patent: April 25, 1995
    Assignee: Apotex, Inc.
    Inventors: Donald F. Gerson, Xinfa Xiao
  • Patent number: 5393893
    Abstract: A process is disclosed for the preparation of simvastatin and its analogs through a novel intermediate (III), which enables a selective .alpha. carbon alkylation of the C-8 acyl side chain.
    Type: Grant
    Filed: November 8, 1993
    Date of Patent: February 28, 1995
    Assignee: Apotex, Inc.
    Inventors: Rudolf Kubela, Jayaramaiyer Radhakrishnan
  • Patent number: RE39087
    Abstract: 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: Grant
    Filed: June 5, 2003
    Date of Patent: May 2, 2006
    Assignee: Apotex, Inc.
    Inventors: Khashayar Karimian, Mehrnoush Motamedi