Patents Assigned to Symed Labs Limited
  • Patent number: 9682946
    Abstract: Provided herein are novel, commercially viable and industrially advantageous processes for the preparation of benzofuran-2-carboxamide derivatives and their intermediates, or a pharmaceutically acceptable salt thereof, in high yield and purity. Provided particularly herein are novel, commercially viable and industrially advantageous processes for the preparation of vilazodone or a pharmaceutically acceptable salt thereof in high yield and purity. Provided also herein is an improved and commercially viable process for the preparation of 3-(4-hydroxybutyl)-1H-indole-5-carbonitrile, in high yield and purity, using novel intermediate compound 3-(4-hydroxybutyryl)-1H-indole-5-carbonitrile.
    Type: Grant
    Filed: October 5, 2015
    Date of Patent: June 20, 2017
    Assignee: Symed Labs Limited
    Inventors: Mohan Rao Dodda, Jithender Aadepu
  • Patent number: 9586913
    Abstract: Provided herein are improved, commercially viable and industrially advantageous processes for the preparation of Linezolid, in high yield and purity, using novel intermediates. In one aspect, provided herein are efficient, industrially advantageous and environmentally friendly processes for the preparation of linezolid, in high yield and with high purity, using novel intermediates. The processes disclosed herein avoid the tedious and cumbersome procedures of the prior processes, thereby resolving the problems associated with the processes described in the prior art, which is more convenient to operate at lab scale and in commercial scale operations.
    Type: Grant
    Filed: April 25, 2013
    Date of Patent: March 7, 2017
    Assignee: Symed Labs Limited
    Inventors: Mohan Rao Dodda, Venkat Reddy Buthukuri
  • Patent number: 9469628
    Abstract: Provided herein are improved, commercially viable and consistently reproducible processes for the preparation of highly pure crystal Modification I of Rivaroxaban, which is free from other polymorphs and undesired solvated forms. Provided also herein is a highly pure and stable crystal Modification I of Rivaroxaban essentially free of other solid state forms.
    Type: Grant
    Filed: January 21, 2015
    Date of Patent: October 18, 2016
    Assignee: Symed Labs Limited
    Inventors: Mohan Rao Dodda, Venugopal Bingi
  • Patent number: 9399630
    Abstract: Provided herein are novel, commercially viable and industrially advantageous processes for the preparation of benzofuran-2-carboxamide derivatives and their intermediates, or a pharmaceutically acceptable salt thereof, in high yield and purity. Provided particularly herein are novel, commercially viable and industrially advantageous processes for the preparation of vilazodone or a pharmaceutically acceptable salt thereof in high yield and purity. Provided also herein is an improved and commercially viable process for the preparation of 3-(4-hydroxybutyl)-1H-indole-5-carbonitrile, in high yield and purity, using novel intermediate compound 3-(4-hydroxybutyryl)-1H-indole-5-carbonitrile.
    Type: Grant
    Filed: July 1, 2013
    Date of Patent: July 26, 2016
    Assignee: Symed Labs Limited
    Inventors: Mohan Rao Dodda, Jithender Aadepu
  • Patent number: 9376427
    Abstract: The present inventors have surprisingly found that rivaroxaban of formula I can be prepared in a one-pot process, in high purity and with high yield, by reacting 5-chlorothiophene-2-carboxylic acid or a salt thereof with a sulfonylating agent to produce a sulfonyl ester intermediate, which is then condensed with 4-[4-[(SS)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one or an acid addition salt thereof to produce rivaroxaban.
    Type: Grant
    Filed: May 2, 2012
    Date of Patent: June 28, 2016
    Assignee: Symed Labs Limited
    Inventors: Mohan Rao Dodda, Venkat Reddy Buthukuri
  • Patent number: 9315456
    Abstract: Provided herein are novel, commercially viable and industrially advantageous processes for the preparation of benzofuran-2-carboxamide derivatives and their intermediates, or a pharmaceutically acceptable salt thereof, in high yield and purity. Provided particularly herein are novel, commercially viable and industrially advantageous processes for the preparation of vilazodone or a pharmaceutically acceptable salt thereof in high yield and purity. Provided also herein is an improved and commercially viable process for the preparation of 3-(4-hydroxybutyl)-1H-indole-5-carbonitrile, in high yield and purity, using novel intermediate compound 3-(4-hydroxybutyryl)-1H-indole-5-carbonitrile.
    Type: Grant
    Filed: October 5, 2015
    Date of Patent: April 19, 2016
    Assignee: Symed Labs Limited
    Inventors: Mohan Rao Dodda, Jithender Aadepu
  • Patent number: 9000221
    Abstract: The present invention relates to processes for the preparation of 4?-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidino]propoxy]-3?-methoxyacetophenone and intermediates thereof. The present invention also provides a process for purifying 4?-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidino]propoxy]-3?-methoxyacetophenone to obtain the purity greater than about 98.0 area % to about 99.0 area % as measured by HPLC, preferably greater than about 99.0 area % to about 99.5 area %, more preferably greater about 99.5 area % to about 99.9 area %. individual impurities lower than about 0.15 area %, preferably lower than about 0.1% and total impurities lower than about 0.5 area % by HPLC.
    Type: Grant
    Filed: July 18, 2011
    Date of Patent: April 7, 2015
    Assignee: Symed Labs Limited
    Inventors: Dodda Mohan Rao, Pingili Krishna Reddy, Buthukuri Venkat Reddy
  • Patent number: 8835635
    Abstract: Disclosed herein is a stable amorphous form of vilazodone hydrochloride substantially free of crystalline forms, a process for the preparation, pharmaceutical compositions, and methods of treating thereof. Disclosed also herein are stable amorphous co-precipitates of vilazodone hydrochloride and a pharmaceutically acceptable excipient, methods for the preparation, pharmaceutical compositions, and method of treating thereof.
    Type: Grant
    Filed: October 22, 2012
    Date of Patent: September 16, 2014
    Assignee: Symed Labs Limited
    Inventors: Dodda Mohan Rao, Aadepu Jithender
  • Patent number: 8546615
    Abstract: The present invention relates to solid racemic dapoxetine, solid dapoxetine S(+)enantiomer, processes for their preparation and their use in the pharmaceutically active compound dapoxetine acid addition salt, and pharmaceutical compositions thereof.
    Type: Grant
    Filed: November 13, 2009
    Date of Patent: October 1, 2013
    Assignee: Symed Labs Limited
    Inventors: Dodda Mohan Rao, Pingili Krishnareddy, Aadepu Jithender
  • Patent number: 8084606
    Abstract: The present invention relates to a novel and commercially viable process for substantially optically pure levorotatory and dextrorotatory enantiomers of cetirizine intermediate, 1-[(4-chlorophenyl)phenylmethyl]piperazine, thereby producing substantially optically pure levorotatory and dextrorotatory enantiomers of cetirizine and their pharmaceutical acceptable acid addition salts thereof in high purity and in high yield using novel intermediates.
    Type: Grant
    Filed: June 15, 2007
    Date of Patent: December 27, 2011
    Assignee: Symed Labs Limited
    Inventors: Dodda Mohan Rao, Bitra Satyanarayana Rao
  • Patent number: 7741480
    Abstract: The present invention provides a novel process for preparation of 5-aminomethyl substituted oxazolidinones, key intermediates for oxazolidinone antibacterials including linezolid. Thus linezolid is prepared by a) reacting 3-fluoro-4-morpholinyl aniline with R-epichlorohydrin; b) subjecting N-[3-Chloro-2-(R)-hydroxypropyl]-3-fluoro-4-morpholinyl aniline produced above to carbonylation; c) reacting (5R)-5-(chloromethyl)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxazolidinone produced above with potassium phthalimide; d) reacting (S)-N-[[3-[3-Fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]phthalimide produced above with hydrazine hydrate; and e) reacting S-N-[[3-[3-Fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]amine produced above with acetic anhydride to produce linezolid.
    Type: Grant
    Filed: October 8, 2007
    Date of Patent: June 22, 2010
    Assignee: Symed Labs Limited
    Inventors: Dodda Mohan Rao, Pingili Krishna Reddy
  • Patent number: 7732597
    Abstract: The present invention relates to a novel crystalline form of linezolid, to processes for its preparation and to a pharmaceutical composition containing it.
    Type: Grant
    Filed: September 26, 2007
    Date of Patent: June 8, 2010
    Assignee: Symed Labs Limited
    Inventors: Dodda Mohan Rao, Pingili Krishna Reddy
  • Patent number: 7718799
    Abstract: The present invention relates to a novel crystalline form of linezolid, to processes for its preparation and to a pharmaceutical composition containing it.
    Type: Grant
    Filed: September 26, 2007
    Date of Patent: May 18, 2010
    Assignee: Symed Labs Limited
    Inventors: Dodda Mohan Rao, Pingili Krishna Reddy
  • Patent number: 7718800
    Abstract: The present invention relates to a novel crystalline form of linezolid, to processes for its preparation and to a pharmaceutical composition containing it.
    Type: Grant
    Filed: September 26, 2007
    Date of Patent: May 18, 2010
    Assignee: Symed Labs Limited
    Inventors: Dodda Mohan Rao, Pingili Krishna Reddy
  • Patent number: 7714128
    Abstract: The present invention relates to a novel crystalline form of linezolid, to processes for its preparation and to a pharmaceutical composition containing it.
    Type: Grant
    Filed: October 16, 2003
    Date of Patent: May 11, 2010
    Assignee: Symed Labs Limited
    Inventors: Dodda Mohan Rao, Pingili Krishna Reddy
  • Patent number: 7524954
    Abstract: The present invention provides a novel process for preparation of 5-aminomethyl substituted oxazolidinones, key intermediates for oxazolidinone antibacterials including linezolid. Thus linezolid is prepared by a) reacting 3-fluoro-4-morpholinyl aniline with R-epichlorohydrin; b) subjecting N-[3-Chloro-2-(R)-hydroxypropyl]-3-fluoro-4-morpholinyl aniline produced above to carbonylation; c) reacting (5R)-5-(chloromethyl)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxazolidinone produced above with potassium phthalimide; d) reacting (S)—N-[[3-[3-Fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]phthalimide produced above with hydrazine hydrate; and e) reacting S—N—[[3-[3-Fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]amine produced above with acetic anhydride to produce linezolid.
    Type: Grant
    Filed: October 8, 2007
    Date of Patent: April 28, 2009
    Assignee: Symed Labs Limited
    Inventors: Dodda Mohan Rao, Pingili Krishna Reddy
  • Patent number: 7429661
    Abstract: The present invention provides a novel process for preparation of 5 aminomethyl substituted oxazolidinones, key intermediates for oxazolidinone antibacterials including linezolid. Thus, the key intermediate of linezolid is prepared by a) reacting N-[3-Chloro-2-(R)-hydroxypropyl]-3-fluoro-4-morpholinyl aniline with potassium phthalimide; b) subjecting N-[3-pthalimido-2-(R)-hydroxypropyl]-3-fluoro-4-(morpholinyl) aniline produced in the above step to carbonylation; and c) reacting (S)-N-[[3-[3-Fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidiriyl]methyl]phthalimide produced in the above step with hydrazine hydrate to produce (S)-N-[[3-[3-Fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]amine.
    Type: Grant
    Filed: July 20, 2004
    Date of Patent: September 30, 2008
    Assignee: Symed Labs Limited
    Inventors: Dodda Mohan Rao, Pingili Krishna Reddy
  • Patent number: 7351824
    Abstract: The present invention provides a novel process for preparation of 5-aminomethyl substituted oxazolidinones, key intermediates for oxazolidinone antibacterials including linezolid. Thus linezolid is prepared by a) reacting 3-fluoro-4-morpholinyl aniline with R-epichlorohydrin; b) subjecting N-[3-Chloro-2-(R)-hydroxypropyl]-3-fluoro-4-morpholinyl aniline produced above to carbonylation; c) reacting (5R)-5-(chloromethyl)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxazolidinone produced above with potassium phthalimide; d) reacting (S)—N-[[3-[3-Fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]phthalimide produced above with hydrazine hydrate; and e) reacting S—N-[[3-[3-Fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]amine produced above with acetic anhydride to produce linezolid.
    Type: Grant
    Filed: October 8, 2007
    Date of Patent: April 1, 2008
    Assignee: Symed Labs Limited
    Inventors: Dodda Mohan Rao, Pingili Krishna Reddy
  • Publication number: 20080021213
    Abstract: The present invention provides a novel process for preparation of 5-aminomethyl substituted oxazolidinones, key intermediates for oxazolidinone antibacterials including linezolid. Thus linezolid is prepared by a) reacting 3-fluoro-4-morpholinyl aniline with R-epichlorohydrin; b) subjecting N-[3-Chloro-2-(R)-hydroxypropyl]-3-fluoro-4-morpholinyl aniline produced above to carbonylation; c) reacting (5R)-5-(chloromethyl)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxazolidinone produced above with potassium phthalimide; d) reacting (S)—N-[[3-[3-Fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]phthalimide produced above with hydrazine hydrate; and e) reacting S—N-[[3-[3-Fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]amine produced above with acetic anhydride to produce linezolid.
    Type: Application
    Filed: October 8, 2007
    Publication date: January 24, 2008
    Applicant: Symed Labs Limited
    Inventors: Dodda Rao, Pingili Reddy
  • Patent number: 7307163
    Abstract: The present invention provides a novel process for preparation of 5-aminomethyl substituted oxazolidinones, key intermediates for oxazolidinone antibacterials including linezolid. Thus linezolid is prepared by a) reacting 3-fluoro-4-morpholinyl aniline with R-epichlorohydrin; b) subjecting N-[3-Chloro-2-(R)-hydroxypropyl]-3-fluoro-4-morpholinyl aniline produced above to carbonylation; c) reacting (5R)-5-(chloromethyl)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxazolidinone produced above with potassium phthalinide; d) reacting (S)-N-[[3-[3-Fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]phthalimide produced above with hydrazine hydrate; and e) reacting S-N-[[3-[3-Fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazo-lidinyl]methyl]amine produced above with acetic anhydride to produce linezolid.
    Type: Grant
    Filed: April 19, 2004
    Date of Patent: December 11, 2007
    Assignee: Symed Labs Limited
    Inventors: Dodda Mohan Rao, Pingili Krishna Reddy