Patents by Inventor Felix Spindler

Felix Spindler 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).

  • Patent number: 7589196
    Abstract: 1,1?-Biphenyl-2,2?-diphosphines having at least one amine substituent in the para position relative to the phosphine group and having the formulae are ligands for metal complexes which serve as catalysts for asymmetric addition reactions of prochiral organic compounds and whose catalytic properties can be tailored specifically to particular substrates by substitution of the amine group.
    Type: Grant
    Filed: April 5, 2004
    Date of Patent: September 15, 2009
    Assignee: Solvias AG
    Inventors: Benoît Pugin, Pierre Martin, Markus Müller, Frédéric Maurice Naud, Felix Spindler, Marc Thommen, Gianpietro Melone, Martin Kesselgruber
  • Publication number: 20090227813
    Abstract: A process for producing 6-dimethylaminomethyl-1-(3-hydroxy- or 3-C1-C4 alkoxyphenyl)-cyclohexane-1,3-diols from 6-dimethylaminomethyl-1-hydroxy-1-(3-hydroxy- or 3-C1-C4 alkoxyphenyl)-cyclohexane-3-ones by catalytic hydrogenation in the presence of heterogeneous or homogeneous catalysts, or by using metal hydrides.
    Type: Application
    Filed: February 27, 2009
    Publication date: September 10, 2009
    Applicant: Gruenenthal GmbH
    Inventors: Wolfgang Hell, Oswald Zimmer, Markus Kegel, Olaf Schaefer, Felix Spindler, Anita Schnyder, Urs Siegrist, Detlef Heller, Hans-Joachim Drexler
  • Publication number: 20090221824
    Abstract: A process for the production of compounds comprising the enantioselective hydrogenation of 2-substituted acrylic acid derivatives.
    Type: Application
    Filed: August 12, 2005
    Publication date: September 3, 2009
    Inventors: Paul Howard Briner, Matthew Colin Thor Fyfe, John Paul Madeley, Peter John Murray, Martin James Procter, Felix Spindler
  • Publication number: 20090171114
    Abstract: Ligands of the formula (I) secondary phosphine-Q-P(?O)HR1 (I) in the form of mixtures of diastereomers or pure diastereomers, in which secondary phosphine is a secondary phosphine group with hydrocarbon radicals or heterohydrocarbon radicals as substituents; Q is a bivalent bisaryl or bisheteroaryl radical with an axial chiral centre to which the two phosphorus atoms are bonded in the ortho positions to the bisaryl or bisheteroaryl bridge bond, or Q is a bivalent ferrocenyl radical with a planar chiral centre or without a planar chiral centre, to which the phosphorus atom of the secondary phosphine is bonded directly or via a C1-C4-carbon chain to a cyclopentadienyl ring, the —P*(?O)HR1 group is bonded either on the same cyclopentadienyl ring in ortho position to the bonded secondary phosphine or on the other cyclopentadienyl ring; P* is a chiral phosphorus atom, and R1 is a hydrocarbon radical, a heterohydrocarbon radical or a ferrocenyl radical, where R1 is a ferrocenyl radical with a planar chiral centre w
    Type: Application
    Filed: May 23, 2007
    Publication date: July 2, 2009
    Inventors: Andreas Pfaltz, Yann Ribourdouille, Xiangdong Feng, Balamurugan Ramalingam, Benoit Pugin, Felix Spindler
  • Publication number: 20090156851
    Abstract: Compounds of the formula (I) in the form of racemates, mixtures of stereoisomers or optically pure stereoisomers, formula (I), where X1 and X2 are each, independently of one another, a secondary phosphino group; R1 is a halogen atom or a—substituent bound via a C atom, N atom, S atom, Si atom, a P(O) group or a P(S) group to the cyclopentadienyl ring; R2 is C1-C4-alkyl or phenyl; m is from 1 to 3 and n is 0 or from 1 to 5, are ligands for complexes of transition metals as enantioselective and homogeneous catalysts. As a result of the substitution, the conversion, the stereoselectivity and/or the configuration of the adduct formed can be influenced and optimization of catalysts can be made possible in this way.
    Type: Application
    Filed: August 10, 2006
    Publication date: June 18, 2009
    Inventors: Walter Weissensteiner, Yaping Wang, Felix Spindler, Benoit Pugin, Xiangdong Feng
  • Publication number: 20090124812
    Abstract: Compounds of the formula I in the form of enantiomerically pure diastereomers or a mixture of diastereomers, (I), where the radicals R1 are identical or different and are each C1-C4-alkyl; m is 0 or an integer from 1 to 3; n is 0 or an integer from 1 to 4; R2 is a hydrocarbon radical or a C-bonded heterohydrocarbon radical; Cp is unsubstituted or C1-C4-alkyl-substituted cyclopentadienyl; Y is a C-bonded chiral group which directs metals of metallation reagents into the ortho position; and Phos is a P-bonded P(III) substituent. The compounds are chiral ligands for complexes of transition metals which are used as homogeneous catalysts in asymmetric syntheses.
    Type: Application
    Filed: April 11, 2007
    Publication date: May 14, 2009
    Inventors: Weiping Chen, Felix Spindler, Benoit Pugin
  • Publication number: 20090105481
    Abstract: Process for stereoselective hydrogenation by reacting racemic aldehydes or ketones having a stereogenic carbon atom in the position relative to the C(O) group and containing the structural element —(O)C—C—CH— by means of hydrogen in the presence of a base and a ruthenium complex containing a bidentate ligand having coordinating P and N atoms, a monophosphine ligand and anionic and/or uncharged ligands as homogeneous catalyst, with the charge being balanced by one or two monovalent acid anions or a divalent acid anion when uncharged ligands are present.
    Type: Application
    Filed: March 8, 2007
    Publication date: April 23, 2009
    Inventors: Felix Spindler, Ulrike Nettekoven, Mauro Perseghini
  • Publication number: 20090088576
    Abstract: A process for the synthesis of an alcohol of formula (I), using as intermediate a compound of formula (V).
    Type: Application
    Filed: January 29, 2007
    Publication date: April 2, 2009
    Inventors: Peter Herold, Stefan Stutz, Robert Mah, Aleksandar Stojanovic, Isabelle Lyothier, Dirk Behnke, Felix Spindler, Erhard Bappert
  • Patent number: 7495123
    Abstract: The present invention relates to a process for the efficient preparation of enantiomerically enriched beta amino acid derivatives wherein the amino group is unprotected. The product chiral beta amino acid derivatives are useful in the asymmetric synthesis of biologically active molecules. The process comprises an enantioselective hydrogenation of an amine-unprotected prochiral beta-amino acrylic acid or derivative thereof in the presence of a rhodium metal precursor complexed with a chiral mono- or bisphosphine ligand.
    Type: Grant
    Filed: April 5, 2005
    Date of Patent: February 24, 2009
    Assignees: Solvias AG, Merck & Co., Inc.
    Inventors: Yi Xiao, Yongkui Sun, Thorsten Rosner, Nelo R. Rivera, Shane W. Krska, Andrew M. Clausen, Joseph D. Armstrong, III, Felix Spindler, Christophe Malan
  • Publication number: 20090043132
    Abstract: Compounds of the formula II can be hydrogenated to the corresponding butane derivatives in the presence of homogeneous cataslysts composed of metal salts or complexes containing metals selected from the group consisting of Rh, Ir, and Ru and preferably containing diphosphine ligands, with, in addition, excellent optical yields being achieved when one of R2 and R3 is not a hydrogen atom and the diphosphine ligand is chiral.
    Type: Application
    Filed: May 1, 2008
    Publication date: February 12, 2009
    Applicant: Gruenenthal GmbH
    Inventors: Wolfgang Hell, Markus Kegel, Helmut Buschmann, Felix Spindler, Detlef Heller, Hans-Joachin Drexler
  • Publication number: 20080287698
    Abstract: Compounds of the formula (I) or (I?), where R1 is a hydrogen atom or C1-C4-alkyl and R?1 is C1-C4-alkyl; X1 and X2 are each, independently of one another, a secondary phosphine group; R2 is hydrogen, R01R02R03Si—, C1-C18acyl substituted by halogen, hydroxy, C1-C8-alkoxy or R04R05N—, -or R06—X01—C(O)—; R01, R02 and R03 are each, independently of one another, C1-C12-alkyl, unsubstituted or C1-C4-alkyl or C1-C4-alkoxy-substituted C6-C10-aryl or C7-C12-aralkyl; R04 and R05 are each, independently of one another, hydrogen, C1-C12-alkyl, C3-C8-cycloalkyl, C6-C10-aryl or C7-C12-aralkyl, or R04 and R05 together are trimethylene, tetramethylene, pentamethylene or 3-oxapcntylene; R06 is C1-C18-alkyl, unsubstituted or C1-C4-alkyl- or C1-C4-alkoxy-substituted C3-C8-cycloalkyl, C6-C10-aryl or C7-C12-aralkyl; X01 is —O— or —NH—; T is C6-C20-arylene; v is 0 or an integer from 1 to 4; and * denotes a mixture of racemic or enantiomerically pure diastereomers or pure racemic or enantiomerically diastereomers, are excellent chi
    Type: Application
    Filed: May 3, 2005
    Publication date: November 20, 2008
    Inventors: Matthias Lotz, Felix Spindler
  • Publication number: 20080058522
    Abstract: The present invention relates to a process for the efficient preparation of enantiomerically enriched beta amino acid derivatives wherein the amino group is unprotected. The product chiral beta amino acid derivatives are useful in the asymmetric synthesis of biologically active molecules. The process comprises an enantioselective hydrogenation of an amine-unprotected prochiral beta-amino acrylic acid or derivative thereof in the presence of a rhodium metal precursor complexed with a chiral mono- or bisphosphine ligand.
    Type: Application
    Filed: April 5, 2005
    Publication date: March 6, 2008
    Inventors: Yi Xiao, Yongkui Sun, Thorsten Rosner, Nelo Rivera, Shane Krska, Andrew Clausen, Joseph Armstrong, Felix Spindler, Christophe Malan
  • Publication number: 20080026933
    Abstract: In ferrocene diphosphines of formula (I), in which R represents, for example, methyl or phenyl, the catalytic properties of corresponding metal complexes can, in many instances, be distinctly influenced by structural changes on one or both of the CP rings, and the catalytic reaction with regard to selected substrates can be optimized and significantly improved. Diphosphine ligands of this type are accessible by using novel production methods.
    Type: Application
    Filed: July 4, 2005
    Publication date: January 31, 2008
    Inventors: Benoit Pugin, Xiang Dong Feng, Felix Spindler
  • Patent number: 7244860
    Abstract: Compounds of the formula (I), in which R1 is C1-C4alkyl, C6-C10aryi or C7-C11, aralkyl, R2 is an open-chain or cyclic secondary amino group, and R is a radical of the formula in which R3 is C1-C4alkyl or C1-C4alkoxy, and R4 is H, C1-C4alkyl or C1-C4alkoxy, are ligands for metal complexes as homogeneous hydrogenation catalysts for prochiral organic compounds containing double bonds, by means of which a very high activity and productivity and also enantioselectivity can be achieved
    Type: Grant
    Filed: May 7, 2004
    Date of Patent: July 17, 2007
    Assignee: Umicore AG & Co. KG
    Inventors: Felix Spindler, Matthias Lotz, Marc Thommen
  • Publication number: 20060241315
    Abstract: Compounds of the formula (1), in which R1 is C1-C4alkyl, C6-C10aryi or C7-C11,aralkyl, R2 is an open-chain or cyclic secondary amino group, and R is a radical of the formula in which R3 is C1-C4alkyl or C1-C4alkoxy, and R4 is H, Cl-C4alkyl or C1-C4alkyloxy, are ligands for metal complexes as homogeneous hydrogenation catalysts for prochiral organic compounds containing double bonds, by means of which a very high activity and productivity and also enantioselectivity can be achieved.
    Type: Application
    Filed: May 7, 2004
    Publication date: October 26, 2006
    Inventors: Felix Spindler, Matthias Lotz, Marc Thommen
  • Patent number: 6881868
    Abstract: Compounds of formula (I), wherein R1 and R2 are, independently of one another, H,C1-C6alkyl, C1-C6halogenalkyl, C1-C6alkoxyl, C1-C6alkoxy-C1-C6alkyl, or C1-C6alkoxy-C1-C6alkyloxy, and R3 is C1-C6alkyl, are obtainable in high yiedls by stereoselective addition of R3-substituted propionic acid esters to R1- and R2-substituted benzaldehydes of formula R—CHO to form corresponding 3-R-3-hydroxy-2-R3-propionic acid esters, conversion of the OH group to a leaving group, subsequent regioselective elimination to form 3-R-2-R3-propenic acid esters, and reduction to corresponding 3-R-2-R3-allyl alcohols and their enantioselective hydrogenation, wherein R is (a).
    Type: Grant
    Filed: June 26, 2001
    Date of Patent: April 19, 2005
    Assignee: Speedel Pharma AG
    Inventors: Stefan Stutz, Peter Herold, Felix Spindler, Walter Weissensteiner, Thomas Sturm
  • Patent number: 6822118
    Abstract: A process for the hydrogenation of imines with hydrogen under elevated pressure in the presence of iridium catalysts and with or without an inert solvent, wherein the reaction mixture contains an ammonium or metal chloride, bromide or iodide and additionally an acid.
    Type: Grant
    Filed: September 10, 1997
    Date of Patent: November 23, 2004
    Assignee: Syngenta Crop Protection, Inc.
    Inventors: Hans-Peter Jalett, Felix Spindler, Hans-Ulrich Blaser, Reinhard Georg Hanreich
  • Patent number: 6777567
    Abstract: Compounds of the formula (I) and (Ia) in the form of racemates, mixtures of diastereomers or in essentially enantiomerically pure form, (I), (Ia), where R is hydrogen, C1-C8alkyl, C5-C12cycloakyl, phenyl or phenyl substituted by from 1 to 3 C1-C4alky or C1-C4alkoxy groups; n is 0 or an integer from 1 to 4 and R1 are identical or different substituents selected from the group consisting of C1-C4alkyl, C1-C4fluoroalkyl and C1-C4alkoxy; X1 and X2 are each, independently of one another, secondary phosphino; T is C6-C20arylene or C3-C16heteroarylene; and X2 is bound in the ortho position relative to the T-cyclopentadienyl bond.
    Type: Grant
    Filed: December 31, 2002
    Date of Patent: August 17, 2004
    Assignee: Solvias AG
    Inventors: Walter Weissensteiner, Thomas Sturm, Felix Spindler
  • Publication number: 20040092766
    Abstract: Compounds of formula (I), wherein R1 and R2 are, independently of one another, H,C1-C6alkyl, C1-C6halogenalkyl, C1-C6alkoxyl, C1-C6alkoxy-C1-C6alkyl, or C1-C6alkoxy-C1-C6alkyloxy, and R3 is C1-C6alkyl, are obtainable in high yiedls by stereoselective addition of R3-substituted propionic acid esters to R1- and R2-substituted benzaldehydes of formula R—CHO to form corresponding 3-R-3-hydroxy-2-R3-propionic acid esters, conversion of the OH group to a leaving group, subsequent regioselective elimination to form 3-R-2-R3-propenic acid esters, and reduction to corresponding 3-R-2-R3-allyl alcohols and their enantioselective hydrogenation, wherein R is (a).
    Type: Application
    Filed: January 3, 2003
    Publication date: May 13, 2004
    Inventors: Stefan Stutz, Peter Herold, Felix Spindler, Walter Weissensteiner, Thomas Sturm
  • Patent number: 6730798
    Abstract: Compounds of formula (II) are simultaneously halogenated in the 5 position and hydroxylated in the 4 position under lactonization, the halolactone is converted into a hydroxylactone and then the hydroxy group into a leaving group, the leaving group is replaced with azide, the lactone amidated and then the azide converted to the amine group, in order to obtain compounds of formula (I).
    Type: Grant
    Filed: January 3, 2003
    Date of Patent: May 4, 2004
    Assignee: Speedel Pharma AG
    Inventors: Stefan Stutz, Peter Herold, Felix Spindler