Patents Assigned to Apotex Pharmachem Inc.
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Publication number: 20100324298Abstract: A novel process for the preparation of omeprazole and its enantiomers, such as esomeprazole, as well as the preparation of related 2-(2-pyridinylmethyl-sulphinyl)-1H-benzimidazoles, including pantoprazole, lansoprazole and rabeprazole, as recemates or single enantiomers, and their alkali or alkaline salts has been developed. The novel process involves the surprising discovery that protection of the free-base benzimidazole sulfoxide (e.g. omeprazole or esomeprazole), by reaction with an alkyl, aryl or aralkyl chloroformate following oxidation of the corresponding sulfide, eliminates the need for its direct isolation. Subsequent removal of the protecting group with a solution of alkali or alkaline earth alkoxide in a C1-C4 alcohol directly provides the corresponding salt. By eliminating the need to handle the free-base benzimidazole sulfoxide, this advantageous procedure provides increased chemical yields over processes described in the art.Type: ApplicationFiled: August 12, 2010Publication date: December 23, 2010Applicant: APOTEX PHARMACHEM INC.Inventors: Fan Wang, Laura Kaye Montemayor, Daqing Che, Stephen E. Horne
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Patent number: 7851619Abstract: A process for the preparation and purification of Eplerenone is described wherein hydroxylated impurities are removed using a novel derivatization procedure.Type: GrantFiled: March 26, 2007Date of Patent: December 14, 2010Assignee: Apotex Pharmachem Inc.Inventors: Elena Bejan, Bhaskar Reddy Guntoori, Svetoslav S. Bratovanov, Mohamed Ibrahim Zaki, Stephen E. Horne
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Patent number: 7834195Abstract: Atorvastatin calcium propylene glycol solvates and processes to prepare these novel solvates which are particularly useful and suitable for pharmaceutical applications.Type: GrantFiled: June 14, 2007Date of Patent: November 16, 2010Assignee: Apotex Pharmachem Inc.Inventors: K. S. Keshava Murthy, Yajun Zhao, Allan W. Rey, Daqing Che, David A. Stradiotto, Uma Kotipalli
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Publication number: 20100273798Abstract: This invention provides a process for the preparation of S-Rivaroxaban and/or R-Rivaroxaban comprising reacting, in the presence of a first base, a compound of Formula 9: with a compound of Formula 8:Type: ApplicationFiled: April 28, 2009Publication date: October 28, 2010Applicant: APOTEX PHARMACHEM INC.Inventors: Prabhudas BODHURI, Gamini Weeratunga
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Publication number: 20100273790Abstract: This invention provides a process for the preparation of S-Rivaroxaban and/or R-Rivaroxaban comprising reacting, in the presence of a first base, a compound of Formula 9: with a compound of Formula 8: .Type: ApplicationFiled: April 26, 2010Publication date: October 28, 2010Applicant: Apotex Pharmachem Inc.Inventors: Prabhudas BODHURI, Gamini Weeratunga
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Patent number: 7816355Abstract: This invention provides a process for the preparation of S-Rivaroxaban and/or R-Rivaroxaban comprising reacting, in the presence of a first base, a compound of Formula 9: with a compound of Formula 8:Type: GrantFiled: April 28, 2009Date of Patent: October 19, 2010Assignee: Apotex Pharmachem IncInventors: Prabhudas Bodhuri, Gamini Weeratunga
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Patent number: 7812179Abstract: A process is provided for preparing (R)-5-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]-5-hydroxy-3-oxo-1-heptanoic acid, R-substituted ester 9 comprising: (a) reacting the aldehyde 1 with the enolate form of (S)-2-hydroxy-1,2,2-triphenylethyl acetate substituent in a chelating co-solvent; (b) hydrolysis of (R,S)-5-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]-3-hydroxy-1-pentanoic acid, (S)-2-hydroxy-1,2,2-triphenylethyl ester (2a and 2b) using a base, preferably an alkali metal base, preferably in a solvent to form the carboxylic acid 7; (c) treating the acid 7 with a chiral base to form a salt and purifying the salt to obtain enantiomerically enriched (R)-7 chiral base salt; (d) alkylation of the (R)-7 chiral base salt or the free base derived from (R)-7, forming (R)-5-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]-5-hydroxy-3-oxo-1-heptanoic acid,Type: GrantFiled: August 14, 2008Date of Patent: October 12, 2010Assignee: Apotex PharmaChem Inc.Inventors: Fan Wang, Daqing Che, Bhaskar Reddy Guntoori, Yajun Zhao, Aaron C. Kinsman, Jody Faught, Alan Chow
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Patent number: 7786309Abstract: A novel process for the preparation of omeprazole and its enantiomers, such as esomeprazole, as well as the preparation of related 2-(2-pyridinylmethyl-sulphinyl)-1H-benzimidazoles, including pantoprazole, lansoprazole and rabeprazole, as recemates or single enantiomers, and their alkali or alkaline salts has been developed. The novel process involves the surprising discovery that protection of the free-base benzimidazole sulfoxide (e.g. omeprazole or esomeprazole), by reaction with an alkyl, aryl or aralkyl chloroformate following oxidation of the corresponding sulfide, eliminates the need for its direct isolation. Subsequent removal of the protecting group with a solution of alkali or alkaline earth alkoxide in a C1-C4 alcohol directly provides the corresponding salt. By eliminating the need to handle the free-base benzimidazole sulfoxide, this advantageous procedure provides increased chemical yields over processes described in the art.Type: GrantFiled: May 9, 2007Date of Patent: August 31, 2010Assignee: Apotex Pharmachem Inc.Inventors: Fan Wang, Laura Kaye Montemayor, Daqing Che, Stephen E. Horne
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Patent number: 7767843Abstract: A process for the preparation of aminoalkyl phenyl carbamate compounds of Formula I, wherein R1 and R2 independently are hydrogen or a C1-6 alkyl; R3 and R4 are the same or different and each is a C1-6 alkyl; or R3 and R4 together with the nitrogen to which they are attached form a cyclic three to eight membered ring, with or without a heteroatom like nitrogen or oxygen; R5 and R6 independently are hydrogen, linear, branched or cyclic C1-6 alkyl; or R5 and R6 together with the nitrogen to which they are attached form a cyclic three to eight membered ring, with or without a heteroatom like nitrogen or oxygen; the carbon centre designated “*” can be racemic or enantiomerically enriched in the (R)- or (S)- configuration; and pharmaceutically acceptable acid addition salts thereof.Type: GrantFiled: March 2, 2006Date of Patent: August 3, 2010Assignee: Apotex Pharmachem Inc.Inventors: Zhi-Xian Wang, Stephen E. Horne, K. S. Keshava Murthy
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Publication number: 20100168111Abstract: A polymorphic form of rivaroxaban, 5-chloro-N-{[(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]oxa-zolidin-5-yl]-methyl}thiophene-2-carboxamide (termed form APO-A), processes for the preparation thereof, and compositions and formulations comprising form APO-A are provided. Also provided are compositions comprising a crystalline form of rivaroxaban and solvents selected from C3 to C6 ketones, C3 to C4 amides and mixtures thereof.Type: ApplicationFiled: December 31, 2008Publication date: July 1, 2010Applicant: Apotex Pharmachem Inc.Inventors: Prabhudas Bodhuri, Gamini Weeratunga
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Patent number: 7709634Abstract: A stable amorphous form of rifaximin is disclosed. This form is chemically and polymorphically stable on storage and can be prepared by dissolving rifaximin in a solvent to form a solution, which is precipitated by adding an anti-solvent and isolating of the precipitated amorphous rifaximin as an end product.Type: GrantFiled: September 20, 2007Date of Patent: May 4, 2010Assignee: Apotex PharmAchem Inc.Inventors: Kiran Kumar Kothakonda, Daqing Che
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Patent number: 7696183Abstract: A novel form of Ibandronate sodium which is particularly suitable for pharmaceutical applications, and a process for preparing said novel form.Type: GrantFiled: December 15, 2006Date of Patent: April 13, 2010Assignee: Apotex Pharmachem Inc.Inventors: David A. Stradiotto, Allan W. Rey, Probal Kanti Datta, Krista Lyn Traynor, Cameron L. McPhail
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Publication number: 20100056802Abstract: In illustrative embodiments, there is provided an amorphous form of L-arginine salt of perindopril which may be particularly suitable for pharmaceutical applications, and processes for preparing said form.Type: ApplicationFiled: September 3, 2009Publication date: March 4, 2010Applicant: Apotex Pharmachem Inc.Inventors: Gamini WEERATUNGA, Carlos B. Zetina-Rocha
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Patent number: 7615647Abstract: A process is provided for preparing pharmaceutical grade atorvastatin hemicalcium salt comprising: (a) deesterifying, wherein R is an ester protecting group to (b) extracting R(R*,R*)-3 into an organic solvent or mixture of solvents, (c) adding a base of formula NR1R2R3 wherein R1, R2 and R3 are independently selected from H, substituted or non-substituted C1 to C7 alkyl, C6 to C9 aryl, C8 to C10 aralkyl or aminoalkyl to form atorvastatin base salt, (d) isolating by precipitation of the above atorvastatin base salt and purifying when necessary, (e) converting atorvastatin base salt to atorvastatin hemicalcium salt by treatment with a calcium salt solution, and (f) isolating the atorvastatin hemicalcium salt.Type: GrantFiled: August 5, 2005Date of Patent: November 10, 2009Assignee: Apotex Pharmachem Inc.Inventors: K.S. Keshava Murthy, Yajun Zhao, Daqing Che, Bhaskar Reddy Guntoori, Sammy Chris Duncan, Stephen E. Horne
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Patent number: 7531658Abstract: The present invention relates to a process for producing 17-N-substituted-carbamoyl-4-aza-androst-1-en-3-ones of formula 1, including Finasteride and Dutasteride.Type: GrantFiled: January 20, 2006Date of Patent: May 12, 2009Assignee: Apotex Pharmachem Inc.Inventors: Zhi-Xian Wang, Alfredo Paul Ceccarelli, Mohammed Abdul Raheem, Bhaskar Reddy Guntoori
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Patent number: 7485754Abstract: Provided is an efficient method for the preparation of 3-aryloxy-3-arylpropylamines, their optical stereoisomers, and pharmaceutically acceptable salts thereof. The process allows for the isolation of 3-aryloxy-3-arylpropylamines in high yield and purity. The present invention further relates to a process for producing fluoxetine, tomoxetine, norfluoxetine, duloxetine, nisoxetine, and their optically enriched (R)- and (S)-enantiomers.Type: GrantFiled: July 8, 2005Date of Patent: February 3, 2009Assignee: Apotex Pharmachem Inc.Inventors: Zhi-Xian Wang, Mohammed Abdul Raheem, Gamini Weeratunga, Bhaskar Reddy Guntoori
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Patent number: 7429613Abstract: A process is provided for preparing (R)-5-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]-5-hydroxy-3-oxo-1-heptanoic acid, R-substituted ester 9 comprising: (a) reacting the aldehyde 1 with the enolate form of (S)-2-hydroxy-1,2,2-triphenylethyl acetate substituent in a chelating co-solvent; (b) hydrolysis of (R,S)-5-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]-3-hydroxy-1-pentanoic acid, (S)-2-hydroxy-1,2,2-triphenylethyl ester (2a and 2b) using a base, preferably an alkali metal base, preferably in a solvent to form the carboxylic acid 7; (c) treating the acid 7 with a chiral base to form a salt and purifying the salt to obtain enantiomerically enriched (R)-7 chiral base salt; (d) alkylation of the (R)-7 chiral base salt or the free base derived from (R)-7, forming (R)-5-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]-5-hydroxy-3-oxo-1-heptanoic acid,Type: GrantFiled: July 17, 2006Date of Patent: September 30, 2008Assignee: Apotex Pharmachem Inc.Inventors: Fan Wang, Daqing Che, Bhaskar Reddy Guntoori, Yajun Zhao, Aaron C. Kinsman, Jody Faught, Alan Chow
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Patent number: 7375233Abstract: The present invention provides a novel and improved process for the preparation of Zonisamide and the intermediates thereof.Type: GrantFiled: December 16, 2005Date of Patent: May 20, 2008Assignee: Apotex Pharmachem Inc.Inventors: Gamini Weeratunga, Eckardt C. G. Wolf, Nageib Mohamed, Allan W. Rey, Bhaskar Reddy Guntoori
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Patent number: 7365201Abstract: A process for the preparation of the boron difluoride chelate of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolone carboxylic acid via: (a) the reaction of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolone carboxylic acid ethyl ester with, (b) fluoroboric acid in the presence of poly(methylhydrosiloxane) or hexamethyldisiloxane.Type: GrantFiled: March 2, 2006Date of Patent: April 29, 2008Assignee: Apotex Pharmachem Inc.Inventors: Zhi-Xian Wang, Murali Kondamreddy, Joseph DiMartino, Bhaskar Reddy Guntoori
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Patent number: 7271253Abstract: A process for the preparation of Balsalazide and its pharmaceutically acceptable salts wherein the reaction comprises: a. the intermediate N-(4-aminobenzoyl)-?-alanine is converted to N-(4-ammoniumbenzoyl)-?-alanine sulfonate salt using a sulfonic acid in water, b. the N-(4-ammoniumbenzoyl)-?-alanine sulfonate salt is treated with aqueous sodium nitrite solution at low temperature to generate N-(4-diazoniumbenzoyl)-?-alanine sulfonate salt, c. the aqueous solution obtained is quenched with aqueous disodium salicylate to furnish Balsalazide disodium solution, d. the solution is acidified to allow isolation of Balsalazide, and e. optionally converting the Balsalazide to a pharmaceutically acceptable salt (such as disodium salt).Type: GrantFiled: August 10, 2006Date of Patent: September 18, 2007Assignee: Apotex Pharmachem Inc.Inventors: Eckardt C. G. Wolf, Nageib Mohamed, Bhaskar Reddy Guntoori