Patents by Inventor Benoit Pugin

Benoit Pugin 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: 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: 20090082581
    Abstract: The invention relates to the compounds of formula (I) in the form of enantiomer-pure diastereomers or a mixture of diastereomers, wherein R?1 represents C1-C4 alkyl, C6-C10 aryl, C7-C10 alkyl or C7-C12 alkaralkyl and n is 0 or an integer of from 1 to 5; R1 represents a hydrogen atom, halogen, a hydrocarbon group with 1 to 20 C atoms that is either unsubstituted or substituted with —SC1-C4 alkyl, —OC1-C4 alkyl, —OC6-C10 aryl or —Si(C1C4 alkyl)3, or a silyl group with 3 C1-C12 hydrocarbon groups; Y represents vinyl, methyl, ethyl, —CH2—OR, —CH2—N(C1-C4 alkyl)2, a C-bound chiral group that directs metals of metallation reagents to the ortho position X1, or Y is a group —CHR2—OR?2; R2 represents C1-C8 alkyl, C5-C8 cycloalkyl, C6-C10 aryl, C7-C12 aralkyl or C7-C12 alkaralkyl; R?2 represents hydrogen or C1-C18 acyl; X1 and X2 independently represent a P-bound P(III) substituent, —SH or an S-bound group of mercaptan; and R represents hydrogen, a silyl group or an aliphatic, cycloaliphatic, aromatic or aromatic-aliph
    Type: Application
    Filed: May 2, 2006
    Publication date: March 26, 2009
    Inventors: Benoit Pugin, Xiangdong Feng
  • Publication number: 20080306263
    Abstract: Process for the preparation of tetrahydropterin and tetrahydropterin derivatives by hydrogenating pterin and pterin derivatives with hydrogen in the presence of a hydrogenating catalyst, in which the hydrogenation is carried out in a polar reaction medium and metal complexes that are soluble in the reaction medium are employed as the hydrogenation catalysts. The process is suited to the hydrogenation, particularly asymmetric hydrogenation, of folic acid, folio acid salts, folio acid esters, folio acid ester salts or dihydroforms thereof, with the proviso that in the event of using folic acid, carboxylic acid salts thereof or dihydroforms thereof the reaction medium is aqueous, and in the event of using folic acid esters, folic acid ester salts or dihydroforms thereof the reaction medium is an alcohol. The process opens up straightforward access to achiral and chiral pterin derivatives.
    Type: Application
    Filed: August 13, 2008
    Publication date: December 11, 2008
    Inventors: Hans Rudolf MULLER, Rudolf MOSER, Viola GROEHN, Benoit PUGIN
  • Patent number: 7435840
    Abstract: The invention relates to compounds having a structural element of formula (I) in an aromatic hydrocarbon ring, wherein: M represents —Li, —MgX3, (C1-C18-Alkyl)3Sn—, —ZnX3 or —B(O—C1-C4-Alkyl)2; X1 and X2, independent of one another, represent O or N, and C-bound hydrocarbon radicals or heterohydrocarbon radicals are bound to the free bonds of the O and N atoms; group —C?C—, together with C atoms, forms a hydrocarbon aromatic compound and represents X3 Cl, Br or I. The inventive compounds are easily obtained by directly substituting the hydrogen in the ortho position to the P atom with metalation reagents. The metal atoms can then be substituted by a reactive electrophilic compound. The group —P(X1—)(X2—) - - - -(BH3)0,1 can then be converted into a secondary phosphine group. The inventive method enables the production of monophosphines and diphosphines even on a large scale, which are valuable ligands for metal complexes serving as catalysts for, e.g. enantioselective hydrogenations.
    Type: Grant
    Filed: December 10, 2004
    Date of Patent: October 14, 2008
    Assignee: Solvias AG
    Inventors: Andreas Pfaltz, Matthias Lotz, Marc Schönleber, Benoît Pugin, Martin Kesselgruber, Marc Thommen
  • Patent number: 7375241
    Abstract: The invention relates to compounds of formula (I) provided in the form of racemic compounds, mixtures of diastereomers or essentially pure diastereomers, wherein R1 represents a hydrogen atom or C1-C4-alkyl, and at least one secondary phosphine depicts an unsubstituted or substituted cyclic phosphine group, or phosphonium salts thereof having one or two monovalent anions or a divalent anion.
    Type: Grant
    Filed: December 10, 2004
    Date of Patent: May 20, 2008
    Assignee: Solvias A.G.
    Inventors: Matthias Lotz, Martin Kesselgruber, Marc Thommen, Benoît Pugin
  • Publication number: 20080076937
    Abstract: Compounds of the formula (I) in the form of racemates, mixtures of diastereomers or pure diastereomers, where RO and Roo are each, independently of one another, hydrogen, C1-C20-alkyl, C3-C8-cycloalkyl, C6-C14-aryl or C3-C12-heteroaryl having heteroatoms selected from the group consisting of O, S and N, which are unsubstituted or substituted by C1-C6-alkyl, C1-C6-alkoxy, C5-C8-cycloalkyl, C5-C8-cycloalkoxy, phenyl, C1-C6-alkylphenyl, C1-C6-alkoxyphenyl, C3-C8-heteroaryl, F or trifluoromethyl; the radicals R1 are each, independently of one another, a hydrogen atom, a halogen atom or a substituent bound to the cyclopentadienyl rings via a C atom, S atom, Si atom, a P(O) or P(S) group; R2 and R02 are each, independently of one another, a hydrogen atom, C1-C20-alkyl, C3-C8-cycloalkyl, C6-C14-aryl or C3-C12-heteroaryl having heteroatoms selected from the group consisting of O, S and N, which are unsubstituted or substituted by C1-C6-alkyl, C1-C6-alkoxy, C5-C8-cycloalkyl, C5-C8-cycloalkoxy, phenyl, C1-C6-alkylpheny
    Type: Application
    Filed: July 4, 2005
    Publication date: March 27, 2008
    Inventors: Benoit Pugin, Xaing Dong Feng, Marc Thommen
  • 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
  • Publication number: 20070281915
    Abstract: A compound of formula I: wherein X1, X2, X3, X4, Y1, Y2, Y3, Y4 and Z have meanings given in the description, and metallated forms of such compounds, which are useful in the treatment of medical conditions for which a photodynamic compound is indicated. Pharmaceutical formulations and methods of treatment of a medical condition for which a photodynamic agent is indicated are also disclosed. Sterilising solutions comprising a compound of the invention, and the use thereof, are also disclosed.
    Type: Application
    Filed: November 21, 2006
    Publication date: December 6, 2007
    Inventors: William Love, Derek Brundish, William Rhys-Williams, Xiang Feng, Benoit Pugin
  • Patent number: 7244841
    Abstract: A compound of formula I: wherein X1, X2, X3, X4, Y1, Y2, Y3, Y4 and Z have meanings given in the description, and metallated forms of such compounds, which are useful in the treatment of medical conditions for which a photodynamic compound is indicated. Pharmaceutical formulations and methods of treatment of a medical condition for which a photodynamic agent is indicated are also disclosed. Sterilizing solutions comprising a compound of the invention, and the use thereof, are also disclosed.
    Type: Grant
    Filed: December 23, 2003
    Date of Patent: July 17, 2007
    Assignees: Destiny Pharma Limited, Solvias AG
    Inventors: William Love, Derek Brundish, William Rhys-Williams, Xiang Dong Feng, Benoit Pugin
  • Publication number: 20070149796
    Abstract: The invention relates to compounds having a structural element of formula (I) in an aromatic hydrocarbon ring, wherein: M represents —Li, —MgX3, (C1-C18-Alkyl)3Sn—, —ZnX3 or —B(O—C1C4-Alkyl)2; X1 and X2, independent of one another, represent O or N, and C-bound hydrocarbon radicals or heterohydrocarbon radicals are bound to the free bonds of the O and N atoms; group —C?C—, together with C atoms, forms a hydrocarbon aromatic compound and represents X3 Cl, Br or I. The inventive compounds are easily obtained by directly substituting the hydrogen in the ortho position to the P atom with metalation reagents. The metal atoms can then be substituted by a reactive electrophilic compound. The group —P(X1—)(X2—) - - - (BH3)0,1 can then be converted into a secondary phosphine group. The inventive method enables the production of monophosphines and diphosphines even on a large scale, which are valuable ligands for metal complexes serving as catalysts for, e.g. enantioselective hydrogenations.
    Type: Application
    Filed: December 10, 2004
    Publication date: June 28, 2007
    Applicant: SOLVIAS AG
    Inventors: Andreas Pfaltz, Matthias Lotz, Marc Schonleber, Benoit Pugin, Martin Kesselgruber, Marc Thommen
  • Publication number: 20070142655
    Abstract: The invention relates to compounds of formula (I) provided in the form of racemic compounds, mixtures of diastereomers or essentially pure diastereomers, wherein R1 represents a hydrogen atom or C1-C4-alkyl, and at least one secondary phosphine depicts an unsubstituted or substituted cyclic phosphine group, or phosphonium salts thereof having one or two monovalent anions or a divalent anion. The compounds of formula (I) can be obtained by means of a novel method and are valuable ligands for catalytically active metal complexes in asymmetrical synthesis.
    Type: Application
    Filed: December 10, 2004
    Publication date: June 21, 2007
    Applicant: SOLVIAS AG
    Inventors: Matthias Lotz, Martin Kesselgruber, Marc Thommen, Benoit Pugin
  • Publication number: 20060276643
    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: Application
    Filed: April 5, 2004
    Publication date: December 7, 2006
    Inventor: Benoit Pugin
  • Publication number: 20040143001
    Abstract: A compound of formula I: 1
    Type: Application
    Filed: December 23, 2003
    Publication date: July 22, 2004
    Applicants: Destiny Pharma Limited, Solvias AG
    Inventors: William Love, Derek Brundish, William Rhys-Williams, Xiang Dong Feng, Benoit Pugin
  • Publication number: 20030120122
    Abstract: Compounds of formula III, 1
    Type: Application
    Filed: December 9, 2002
    Publication date: June 26, 2003
    Inventors: Benoit Pugin, Ivo Steiner, Rhony Niklaus Aufdenblatten, Antonio Togni
  • Patent number: 6515183
    Abstract: Compounds of formula III, wherein R6 und R7 signify identical or different secondary phosphino; R8 is —CH2—OH, —CH2—NH2, —CH2—O—B—FU, —CH2—NH2—B—FU, or —O—B—FU; R9 has the same significance as R8 or is C1-C4-alkyl or C1-C4-alkoxy; or R8 and R9 together signify HOCH(CH2—O—)2, H2NCH—(CH2—O—)2, FU—B—OCH(CH2—O—)2 or FU-B-HNCH(CH2—O—)2; B is a bridging group; and FU is a functional group. The compounds may be bonded to inorganic or organic carriers. Their d-8 metal complexes are valuable catalysts for the enantioselective hydrogenation of prochiral organic compounds with carbon multiple bonds or carbon/hetero atom multiple bonds.
    Type: Grant
    Filed: July 6, 2001
    Date of Patent: February 4, 2003
    Assignee: Solvias AG
    Inventors: Benoît Pugin, Ivo Steiner, Rhony Niklaus Aufdenblatten, Antonio Togni
  • Publication number: 20020022731
    Abstract: A description is given of a process for the transesterification of carboxylic esters, characterized in that the catalyst used is a tin(IV) compound comprising a radical of the formula 1
    Type: Application
    Filed: March 29, 2001
    Publication date: February 21, 2002
    Inventors: Benoit Pugin, Benoit Dubuis, Adrian Muller
  • Publication number: 20010056210
    Abstract: Compounds of formula III, 1
    Type: Application
    Filed: July 6, 2001
    Publication date: December 27, 2001
    Inventors: Benoit Pugin, Ivo Steiner, Rhony Niklaus Aufdenblatten, Antonio Togni
  • Patent number: 6281390
    Abstract: Compounds of formula III, wherein R6 und R7 signify identical or different secondary phosphino; R8 is —CH2—OH, —CH2—NH2—, —CH2O——B—FU, —CH2—NH2—B—FU, or —O—B—FU; R9 has the same significance as R8 or is C1-C4-alkyl or C1-C4-alkoxy; or R8 and R9 together signify HOCH(CH2—O—)2, H2NCH—(CH2—O—)2, FU—B—OCH(CH2—O—)2 or FU—B—HNCH(CH2—O—)2; B is a bridging group; and FU is a functional group. The compounds may be bonded to inorganic or organic carriers. Their d-8 metal complexes are valuable catalysts for the enantioselective hydrogenation of prochiral organic compounds with carbon multiple bonds or carbon/hetero atom multiple bonds.
    Type: Grant
    Filed: November 17, 1999
    Date of Patent: August 28, 2001
    Assignee: Solvias AG
    Inventors: Benoît Pugin, Ivo Steiner, Rhony Niklaus Aufdenblatten, Antonio Togni
  • Patent number: 6248899
    Abstract: A description is given of a process for the transesterification of carboxylic esters, characterized in that the catalyst used is a tin(IV) compound comprising a radical of the formula bound to an inorganic support, where L is an at least divalent radical and at least one of the free valences of the Si in formula (I) is bound to the inorganic support, novel tin(IV) compounds and their preparation.
    Type: Grant
    Filed: August 9, 1999
    Date of Patent: June 19, 2001
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Benoît Pugin, Benoît Dubuis, Adrian Müller
  • Patent number: 6133464
    Abstract: The invention relates to chiral ferrocenyls of formula (I) ##STR1## wherein R.sub.a is --P(R.sub.10 R.sub.11) or --SR.sub.12 ;R.sub.b is --P(R'.sub.10 R'.sub.11), --SR'.sub.12, --CH.dbd.NR.sub.12, --CH.sub.2 --NH--R.sub.12 or --CH.sub.2 --O--P(R.sub.10 R.sub.11); and the other substituents are as defined in claim 1,which may be used as ligands for transition metal catalysts in enantioselective reactions.
    Type: Grant
    Filed: March 8, 1999
    Date of Patent: October 17, 2000
    Assignee: Novartis AG
    Inventors: Benoit Pugin, Heidi Landert, Giorgio Pioda