Abstract: This invention provides processes for preparation of 3-alkyl indoles of Formula 1: wherein A1, A2 and A3 are independently selected from the group consisting of: H, X, OR1, CN, CONR22 and C02R3; R1 is C1-C6 alkyl; R2 is H or C1-C6 alkyl; R3 is C1-C6 alkyl; LG is a leaving group; X is a halogen; and n is 1, 2 or 3.
Type:
Grant
Filed:
September 12, 2013
Date of Patent:
January 3, 2017
Assignee:
Apotex Pharmachem Inc.
Inventors:
Craig Stewart, Peter Garth Blazecka, Gamini Weeratunga, Uma Kotipalli, Sammy Chris Duncan, Yajun Zhao
Abstract: There is provided processes for preparing Lubiprostone and intermediates thereof. Also provided are compounds, including intermediates for preparing Lubiprostone as well compositions comprising Lubiprostone and other compounds, including intermediates for preparing Lubiprostone and other compounds.
Type:
Grant
Filed:
January 22, 2010
Date of Patent:
July 5, 2016
Assignee:
Apotex Pharmachem Inc.
Inventors:
Kiran Kumar Kothakonda, Fan Wang, Bhaskar Reddy Guntoori, Minh T. N. Nguyen, Alfredo Paul Ceccarelli, Yajun Zhao, Uma Kotipalli, Sammy Chris Duncan, Kaarina K. Milnes, Kevin Wade Kells, Laura Kaye Montemayor
Abstract: Provided for in the instant application are two additional forms of rifaximin, namely rifaximin polymorphic forms APO-III and APO-IV. Also provided are allegedly novel processes for preparing the previously disclosed rifaximin polymorphic forms APO-I and APO-II. Rifaximin is a non-aminoglycoside antibiotic that has previously been found to be useful for the treatment of traveller's diarrhea caused by Escherichia coli bacteria, as well as in the treatment of irritable bowel syndrome, diverticular disease, hepatic encephalopathy, pyogenic skin infections and as an antibacterial prophylactic prior to colon surgery.
Type:
Grant
Filed:
June 13, 2013
Date of Patent:
June 7, 2016
Assignee:
Apotex Pharmachem Inc.
Inventors:
Peter Garth Blazecka, Nageib Mohamed, Cameron L. McPhail, Sammy Chris Duncan, Randa E. El-Haj, Yajun Zhao
Abstract: Provided is dexlansoprazole propylene glycolate hydrate. Polymorphic forms thereof are also provided. The dexlansoprazole propylene glycolate hydrate maybe such that the propylene glycol component is present in approximately equal proportions of (R) absolute configuration and (S) absolute configuration, or present in predominantly (R) absolute configuration, or predominantly (S) absolute configuration. Salts of dexlansoprazole are also provided. In particular, crystalline dexlansoprazole isopropylammonium salt and crystalline MTBE solvate of dexlansoprazole t-butylammonium salt are provided. Pharmaceutical formulations comprising dexlansoprazole propylene glycolate hydrate are also provided. Furthermore, processes for preparation of dexlansoprazole propylene glycolate hydrate are provided.
Type:
Grant
Filed:
August 19, 2010
Date of Patent:
May 19, 2015
Assignee:
APOTEX PHARMACHEM INC.
Inventors:
Fan Wang, Kevin W. Kells, Kaarina Milnes, Cameron L. McPhail
Abstract: There is provided a crystalline form of Lapatinib, termed APO-I, and methods for making APO-I. There is also provided a crystalline solvate form of Lapatinib, termed APO-II, and methods for making APO-II.
Type:
Grant
Filed:
April 21, 2011
Date of Patent:
March 31, 2015
Assignee:
Apotex Pharmachem Inc
Inventors:
Carlos Zetina-Rocha, Eduardo Gustavo Cammisa, Gamini Weeratunga
Abstract: There is provided processes for preparing Lapatinib and pharmaceutically acceptable salts thereof by the reductive amination of the aldehyde of Formula II by treatment with 2-methanesulphonylethylamine followed by catalytic hydrogenation in the presence of a suitable hydrogenation catalyst.
Type:
Grant
Filed:
December 23, 2011
Date of Patent:
February 10, 2015
Assignee:
Apotex Pharmachem Inc.
Inventors:
Mohammed Abdul Raheem, Gamini Weeratunga, Carlos Zetina-Rocha, Eduardo Gustavo Cammisa
Abstract: Provided for in the instant application are two additional polymorphic forms of rifaximin; namely substantially pure APO-I and APO-II. Also provided are processes for preparing substantially pure APO-I and APO-II. Rifaximin is a non-aminoglycoside antibiotic that has previously been found to be useful for the treatment of traveller's diarrhea caused by Escherichia coli bacteria, as well as in the treatment of irritable bowel syndrome, diverticular disease, hepatic encephalopathy, pyogenic skin infections and as an antibacterial prophylactic prior to colon surgery.
Abstract: This invention relates to 1,3-oxathiolane derivatives (I), processes for the preparation of 1,3-oxathiolane derivatives and intermediate compounds thereof.
Type:
Grant
Filed:
April 12, 2013
Date of Patent:
September 16, 2014
Assignee:
Apotex Pharmachem Inc.
Inventors:
Craig Stewart, Michael B. Johansen, Probal Kanti Datta, Yajun Zhao
Abstract: There is provided crystalline solvate forms of Warfarin potassium, termed APO-I and APO-II, and processes for making APO-I and APO-II. APO-I and APO-II are polymorphic solvate forms of Warfarin potassium.
Type:
Grant
Filed:
May 20, 2011
Date of Patent:
July 1, 2014
Assignee:
Apotex Pharmachem Inc.
Inventors:
Prabhudas Bodhuri, Gamini Weeratunga, Keshava K. S. Murthy
Abstract: There is provided processes for preparing Lapatinib and pharmaceutically acceptable salts thereof by the reductive amination of the aldehyde of Formula II by treatment with 2-methanesulphonylethylamine followed by catalytic hydrogenation in the presence of a suitable hydrogenation catalyst.
Type:
Application
Filed:
December 23, 2011
Publication date:
January 16, 2014
Applicant:
APOTEX PHARMACHEM INC.
Inventors:
Mohammed Abdul Raheem, Gamini Weeratunga, Carlos Zetina-Rocha, Eduardo Gustavo Cammisa
Abstract: 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:
Grant
Filed:
August 12, 2010
Date of Patent:
October 22, 2013
Assignee:
Apotex Pharmachem Inc
Inventors:
Fan Wang, Laura Kaye Montemayor, Daqing Che, Stephen E. Horne
Abstract: This invention relates to 1,3-oxathiolane derivatives (I), processes for the preparation of 1,3-oxathiolane derivatives and intermediate compounds thereof.
Type:
Application
Filed:
April 12, 2013
Publication date:
October 17, 2013
Applicant:
APOTEX PHARMACHEM INC.
Inventors:
Craig Stewart, Michael B. Johansen, Probal Kanti Datta, Yajun Zhao
Abstract: A process for the preparation of an acid addition salt of an organic base comprising exposing the organic base in solid form to a gaseous acid, with the proviso that ziprasidone, its acid addition salts and intermediates thereof are excluded.
Type:
Grant
Filed:
June 29, 2005
Date of Patent:
June 25, 2013
Assignee:
Apotex PharmaChem Inc.
Inventors:
Allan W. Rey, Lotfi Derdour, K. S. Keshava Murthy, Probal Kanti Datta, Martin Ehlert, Stephen E. Horne
Abstract: There is provided crystalline solvate forms of Warfarin potassium, termed APO-I and APO-II, and processes for making APO-I and APO-II. APO-I and APO-II are polymorphic solvate forms of Warfarin potassium.
Abstract: There is provided a crystalline form of Lapatinib, termed APO-I, and methods for making APO-I. There is also provided a crystalline solvate form of Lapatinib, termed APO-II, and methods for making APO-II.
Type:
Application
Filed:
April 21, 2011
Publication date:
May 16, 2013
Applicant:
APOTEX PHARMACHEM INC.
Inventors:
Carlos Zetina-Rocha, Eduardo Gustavo Cammisa, Gamini Weeratunga
Abstract: There is provided a crystalline form of Lubiprostone, termed APO-II and methods for making APO-II. APO-II is a polymorphic form of Lubiprostone.
Type:
Application
Filed:
January 28, 2011
Publication date:
April 18, 2013
Applicant:
APOTEX PHARMACHEM INC.
Inventors:
Alfredo Paul Ceccarelli, Kiran Kumar Kothakonda
Abstract: Provided for in the instant application are two additional polymorphic forms of rifaximin; namely substantially pure APO-I and APO-II. Also provided are processes for preparing substantially pure APO-I and APO-II. Rifaximin is a non-aminoglycoside antibiotic that has previously been found to be useful for the treatment of traveller's diarrhea caused by Escherichia coli bacteria, as well as in the treatment of irritable bowel syndrome, diverticular disease, hepatic encephalopathy, pyogenic skin infections and as an antibacterial prophylactic prior to colon surgery.
Abstract: Provided are process for the preparation of (R)- and/or (S)-Rivaroxaban, and compounds which are intermediate compounds used in the processes for the preparation of (R)- and/or (S)-Rivaroxaban.
Abstract: Provided is dexlansoprazole propylene glycolate hydrate. Polymorphic forms thereof are also provided. The dexlansoprazole propylene glycolate hydrate maybe such that the propylene glycol component is present in approximately equal proportions of (R) absolute configuration and (S) absolute configuration, or present in predominantly (R) absolute configuration, or predominantly (S) absolute configuration. Salts of dexlansoprazole are also provided. In particular, crystalline dexlansoprazole isopropylammonium salt and crystalline MTBE solvate of dexlansoprazole t-butylammonium salt are provided. Pharmaceutical formulations comprising dexlansoprazole propylene glycolate hydrate are also provided. Furthermore, processes for preparation of dexlansoprazole propylene glycolate hydrate are provided.
Type:
Application
Filed:
August 19, 2010
Publication date:
March 14, 2013
Applicant:
APOTEX PHARMACHEM INC.
Inventors:
Fan Wang, Kevin W. Kells, Kaarina Milnes, Cameron L. McPhail
Abstract: The present invention provides a process for the preparation of Efavirenz. A compound of Formula 1: may be prepared by a process comprising cyclizing, in the presence of a first base, a compound of Formula 5 with a haloformate of Formula 6. Other processes are also provided as well as novel compounds prepared by and used in such processes.