Patents by Inventor Arne Grumann

Arne Grumann has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).

  • Publication number: 20230174517
    Abstract: The present invention relates to an improved process for the preparation of 2-chloro-4-(1-tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)benzonitrile (III) which is useful as an intermediate in preparation of carboxamide structured androgen receptor antagonists. The process comprises preparation of compound (III) using heterogeneous palladium catalyst.
    Type: Application
    Filed: May 10, 2021
    Publication date: June 8, 2023
    Inventors: Arne GRUMANN, Oskari KARJALAINEN
  • Patent number: 9321712
    Abstract: The present invention is related to the process for the preparation ospemifene or (Z)-2-[4-(4-chloro-1,2-diphenyl-but-1-enyl)phenoxy]ethanol (I) and to intermediate compounds used in the process.
    Type: Grant
    Filed: October 17, 2013
    Date of Patent: April 26, 2016
    Assignee: FERMION OY
    Inventors: Jan Tois, Ainoliisa Pihko, Arne Grumann
  • Publication number: 20150274624
    Abstract: The present invention is related to the process for the preparation ospemifene or (Z)-2-[4-(4-chloro-1,2-diphenyl-but-1-enyl)phenoxy]ethanol (I) and to intermediate compounds used in the process.
    Type: Application
    Filed: October 17, 2013
    Publication date: October 1, 2015
    Applicant: Fermion Oy
    Inventors: Jan Tois, Ainoliisa Pihko, Arne Grumann
  • Patent number: 8420807
    Abstract: The invention relates to a method for the preparation of 11-(4-[2-(2-hydroxyethoxy)ethyl]-1-piperazinyl]dibenzo [b,f]-1,4-thiazepine and pharmaceutically acceptable salts thereof comprising the reaction of 1-[2-(hydroxyethoxy)-ethyl]piperazine with dibenzo[b,f][1,4]thiazepin-11-ylamine.
    Type: Grant
    Filed: January 30, 2009
    Date of Patent: April 16, 2013
    Assignee: Fermion Oy
    Inventors: Arne Grumann, Dzintra Muceniece, Otto Soidinsalo
  • Patent number: 8044038
    Abstract: The present invention relates to a process for preparing crystalline quetiapine hemifumarate, which comprises crystallizing or re-crystallizing quetiapine hemifumarate from a mixture of water and a water soluble alcohol.
    Type: Grant
    Filed: September 28, 2006
    Date of Patent: October 25, 2011
    Assignee: Fermion Oy
    Inventors: Petteri Rummakko, Arne Grumann, Soini Huhta, Tuomas Koiranen
  • Patent number: 8044039
    Abstract: The present invention relates to a process for preparing and purifying crystalline quetiapine hemifumarate, which comprises preparing crystalline quetiapine hemifumarate via a crystalline salt, which is not a salt of fumaric acid.
    Type: Grant
    Filed: October 26, 2006
    Date of Patent: October 25, 2011
    Assignee: Fermion Oy
    Inventors: Arne Grumann, Soini Huhta, Petteri Rummakko, Viesturs Lusis
  • Publication number: 20110112290
    Abstract: The invention relates to a method for the preparation of 11-(4-[2-(2-hydroxyethoxy)ethyl]-1-piperazinyl]dibenzo[b,f]-1,4-thiazepine and pharmaceutically acceptable salts thereof comprising the reaction of 1-[2-(hydroxyethoxy)-ethyl]piperazine with dibenzo[b,f][1,4]thiazepin-11-ylamine.
    Type: Application
    Filed: January 30, 2009
    Publication date: May 12, 2011
    Applicant: FERMION OY
    Inventors: Arne Grumann, Dzintra Muceniece, Otto Soidinsalo
  • Patent number: 7863441
    Abstract: The present invention discloses a process for the preparation of quetiapine, which comprises the ring closure of a compound of the formula shown below, as well as novel intermediates in the process.
    Type: Grant
    Filed: September 23, 2004
    Date of Patent: January 4, 2011
    Assignee: Fermion Oy
    Inventors: Petteri Rummakko, Soini Huhta, Arne Grumann
  • Patent number: 7858777
    Abstract: The present invention discloses a process for the preparation of quetiapine, which comprises the ring closure and deprotection of a compound of the formula (I), as well as novel intermediates in the process.
    Type: Grant
    Filed: September 23, 2004
    Date of Patent: December 28, 2010
    Assignee: Fermion Oy
    Inventors: Leif Hilden, Arne Grumann, Soini Huhta, Petteri Rummakko
  • Publication number: 20090137844
    Abstract: The invention relates to a process for the production of tamsulosin hydrochloride crystals where the crystal size distribution is controlled by controlling the temperature where hydrochloric acid is added to the reaction mixture.
    Type: Application
    Filed: June 14, 2006
    Publication date: May 28, 2009
    Applicant: Fermion Oy
    Inventors: Arne Grumann, Soini Huhta, Eila Luukkonen, Tuomas Koiranen
  • Publication number: 20090118497
    Abstract: The present invention relates to a process for preparing crystalline quetiapine hemifumarate, which comprises crystallizing or re-crystallizing quetiapine hemifumarate from a mixture of water and a water soluble alcohol.
    Type: Application
    Filed: September 28, 2006
    Publication date: May 7, 2009
    Inventors: Petteri Rummakko, Arne Grumann, Soini Huhta, Tuomas Koiranen
  • Publication number: 20090082597
    Abstract: The invention relates to the use of copper-catalyzed nucleophilic aromatic substitution reaction for preparing 3-aryloxy-3-arylpropylamines and more specifically to a method of preparing certain 3-aryloxy-3-arylpropylamines and the pharmaceutically acceptable addition salts thereof, comprising reacting an amino alcohol with a haloaromatic compound in the presence of a base and a catalytic copper source, and in the absence of a separate ligand.
    Type: Application
    Filed: July 14, 2006
    Publication date: March 26, 2009
    Applicant: FERMION OY
    Inventors: Arne Grumann, Kari Lappalainen, Peter Maiwald, Pekka Pietikainen, Petteri Rummakko
  • Publication number: 20070111987
    Abstract: The present invention discloses a process for the preparation of quetiapine, which comprises the ring closure of a compound of the formula shown below, as well as novel intermediates in the process.
    Type: Application
    Filed: September 23, 2004
    Publication date: May 17, 2007
    Applicant: Fermion Oy
    Inventors: Petteri Rummakko, Soini Huhta, Arne Grumann
  • Publication number: 20050209467
    Abstract: The present invention is directed to novel processes for the preparation of citalopram comprising halogenation of a phthalide compound of formula II, wherein R is a suitable group to be changed to CN, to afford an acid halogenide compound of formula III wherein R is as defined as above and X is halogen, and thereafter obtaining citalopram through two successive reactions with suitable organometallic halides or organoboranes or by a reaction with organometallic 4-fluorophenylhalide or 4-fluorophenylborane followed by reduction and alkylation, and an exchange of R to cyano to afford citalopram. The order of the reactions can be varied depending for example on the starting compound used.
    Type: Application
    Filed: January 31, 2005
    Publication date: September 22, 2005
    Applicant: Fermion Oy
    Inventors: Leif Hilden, Petteri Rummakko, Arne Grumann, Pekka Pietikaeinen
  • Patent number: 6753433
    Abstract: Method for the preparation of 1-(3-dimethylaminopropyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile (citalopram) comprising the reaction of a compound of formula wherein X is a halogen, with organometallic dimethylaminopropyl halide. Other aspects of the invention are new compounds of formula II and formula III and their preparation.
    Type: Grant
    Filed: February 24, 2003
    Date of Patent: June 22, 2004
    Assignee: Orion Corporation, FERMION
    Inventors: Leif Hilden, Tuomas Huuhtanen, Petteri Rummakko, Arne Grumann, Pekka Pietikaeinen
  • Publication number: 20030130527
    Abstract: Method for the preparation of 1-(3-dimethylaminopropyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile (citalopram) comprising the reaction of a compound of formula 1
    Type: Application
    Filed: February 24, 2003
    Publication date: July 10, 2003
    Applicant: ORION CORPORATION FERMION
    Inventors: Leif Hilden, Tuomas Huuhtanen, Petteri Rummakko, Arne Grumann, Pekka Pietikaeinen
  • Patent number: 6579993
    Abstract: Method for the preparation of 1-(3-dimethylaminopropyl)-1-(4-fluoro-phenyl)-1,3-dihydroisobenzofuran-5-carbonitrile (citalopram) comprising the reaction of a compound of formula wherein X is a halogen, with organometallic dimethylaminopropyl halide. Other aspects of the invention are new compounds of formula II and formula III and their preparation.
    Type: Grant
    Filed: January 30, 2002
    Date of Patent: June 17, 2003
    Assignee: Orion Corporation, Fermion
    Inventors: Leif Hilden, Tuomas Huuhtanen, Petteri Rummakko, Arne Grumann, Pekka Pietikaeinen
  • Publication number: 20020115872
    Abstract: Method for the preparation of 1-(3-dimethylaminopropyl)-1-(4-fluoro-phenyl)-1,3-dihydroisobenzofuran-5-carbonitrile (citalopram) comprising the reaction of a compound of formula 1
    Type: Application
    Filed: January 30, 2002
    Publication date: August 22, 2002
    Applicant: ORION CORPORATION FERMION
    Inventors: Leif Hilden, Tuomas Huuhtanen, Petteri Rummakko, Arne Grumann, Pekka Pietikaeinen
  • Patent number: 6103929
    Abstract: Disclosed is a process for the preparation of cyclopropylglycine by a 5-step process wherein cyclopropanecarboxaldehyde is reacted with an .alpha.-aminoalkylaromatic compound to obtain an imine which is reacted with a cyanide to produce an aminonitrile compound; the aminonitrile compound is hydrolyzed to the corresponding aminocarboxylic acid and finally the arylalkyl residue is removed from the amino group by hydrogenolysis.
    Type: Grant
    Filed: November 16, 1999
    Date of Patent: August 15, 2000
    Assignee: Eastman Chemical Company
    Inventors: Daniel John Bayston, Jonathan Luke William Griffin, Arne Grumann, Mario Eugenio Cosimino Polywka, Ronald Michael Scott