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).
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Patent number: 8598371Abstract: Compounds of the formula (I) in the form of a mixture of predominantly one diastereomer or in the form of pure diastereomers, Z1-Q-P*R0R1??(I), wherein: Z1 is a C-bonded, secondary phosphine group of the formula —P(R)2, wherein R is a hydrocarbon radical or O-atom(s)-containing heterohydrocarbon radical having 1 to 18 carbon atoms and optionally substituted by C1-C6-alkyl, trifluoromethyl, C1-C6-alkoxy, trifluoromethoxy, (C1-C4-alkyl)2amino, (C6H5)3Si, (C1-C12-alkyl)3Si or halogen; Q is selected from the group consisting of: (i) an optionally substituted achiral aromatic group, wherein the achiral aromatic group is bonded directly to Z1 through a carbon atom of the achiral aromatic group and bonded directly to P*R0R1 through a carbon atom of the achiral aromatic group, and (ii) an optionally substituted C1-C4-alkylene group; P* is a chiral phosphorus atom; R0 is methyl; and R1 is a C-bonded optically enriched or optically pure chiral, mono- or polycyclic, nonaromatic hydrocarbon ring; and preparatType: GrantFiled: April 26, 2013Date of Patent: December 3, 2013Assignee: Solvias AGInventors: Benoit Pugin, Matthias Lotz, Heidi Landert, Adrian Wyss, Raphael Aardoom, Bjorn Gschwend, Andreas Pfaltz, Felix Spindler
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Publication number: 20130267714Abstract: Compounds of the formula (I) in the form of a mixture of predominantly one diastereomer or in the form of pure diastereomers, Z1-Q-P*R0R1??(I), wherein: Z1 is a C-bonded, secondary phosphine group of the formula —P(R)2, wherein R is a hydrocarbon radical or O-atom(s)-containing heterohydrocarbon radical having 1 to 18 carbon atoms and optionally substituted by C1-C6-alkyl, trifluoromethyl, C1-C6-alkoxy, trifluoromethoxy, (C1-C4-alkyl)2-amino, (C6H5)3Si, (C1-C12-alkyl)3Si or halogen; Q is selected from the group consisting of: (i) an optionally substituted achiral aromatic group, wherein the achiral aromatic group is bonded directly to Z1 through a carbon atom of the achiral aromatic group and bonded directly to P*R0R1 through a carbon atom of the achiral aromatic group, and (ii) an optionally substituted C1-C4-alkylene group; P* is a chiral phosphorus atom; R0 is methyl; and R1 is a C-bonded optically enriched or optically pure chiral, mono- or polycyclic, nonaromatic hydrocarbon ring; and preparType: ApplicationFiled: April 26, 2013Publication date: October 10, 2013Inventors: Benoit PUGIN, Matthias LOTZ, Heidi LANDERT, Adrian WYSS, Raphael AARDOOM, Bjorn GSCHWEND, Andreas PFALTZ, Felix SPINDLER
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Patent number: 8084602Abstract: 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: GrantFiled: November 21, 2006Date of Patent: December 27, 2011Assignee: Destiny Pharma LimitedInventors: William Love, Derek Brundish, William Rhys-Williams, Xiang Dong Feng, Benoit Pugin
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Publication number: 20110251416Abstract: Process for preparing ligands of the formula (1), in which R1 is C1-C8-alkyl, unsubstituted cyclopentyl, cyclohexyl, norbornyl or adamantyl, or cyclopentyl or cyclohexyl, substituted by 1 to 3 C1-C4-alkyl or C1-C4-alkoxy, or benzyl, phenyl, naphthyl and anthryl which are unsubstituted or substituted by 1 to 3 C1-C4-alkyl, C1-C4-alkoxy, C1-C4-fluoroalkyl or C1-C4-fluoroalkoxy, F and Cl, each of R2 and R3 is independently a C-bonded hydrocarbon radical or a heterohydrocarbon radical, and R4 is C1-C4-alkyl, cyclopentyl, cyclohexyl, phenyl, methylphenyl, methylbenzyl or benzyl, which comprises (a) stereoselective metallation in ortho position to the amine side-chain of a compound of formula (A) in which R4 is as defined above, reaction with a dihalide of formula R1—PX2 in which R1 is as defined above and X is Cl or Br, stereoselective hydrolysis to give a compound containing an SPO group, and reaction with a secondary phosphine of formula H—PR2R3 in which R2 and R3 are as defined above, to give the compounds of fType: ApplicationFiled: November 13, 2009Publication date: October 13, 2011Inventors: Benoit Pugin, Adrian Wyss
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Patent number: 7816525Abstract: 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, folic acid salts, folic acid esters, folic 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: GrantFiled: July 12, 2000Date of Patent: October 19, 2010Assignee: Merck & CieInventors: Hans Rudolf Muller, Rudolf Moser, Viola Groehn, Benoit Pugin
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Publication number: 20100029967Abstract: Compounds of the formulae I and Ia in the form of mixtures of diastereomers or pure diastereomers, (I), (Ia), 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 sec-phosphino group; T is C6-C20-arylene or C4-C18-heteroarylene having heteroatoms selected from the group consisting of O, S, —N? and N(C1-C4-alkyl); v is 0 or an integer from 1 to 4; X1 is bound in the ortho position relative to the T-C* bond; Q is vinyl, methyl, ethyl, —CH2—OR, —CH2—N(C1-C4-alkyl)2 or a C- or S-bonded chiral group which directs metals of metallation reagents into the ortho position; R is hydrogen, a silyl radical or an aliphatic, cycloaliphatic, aromatic or aromatic-aliphatic hydrocarbon radical which has from 1 to 18 carbon atoms and is unsubstituted or substituted by C1-C4-alkyl, C1-C4-alkoxy, F or CF3; are ligands for metal complexes as homogeneous catalyst in asymmetric syntheses.Type: ApplicationFiled: June 29, 2007Publication date: February 4, 2010Inventors: Benoit Pugin, Xiangdong Feng, Felix Spindler
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Publication number: 20100003212Abstract: The present invention relates to novel articles and the like, typically exhibiting antimicrobial efficacy which articles contain for example a carrier, a spacer attached to the carrier and one or more quaternary ammonium groups attached directly or indirectly to said spacer.Type: ApplicationFiled: June 25, 2007Publication date: January 7, 2010Inventors: Georg L. Kis, Benoit Pugin, Barbel Fobel
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Publication number: 20090171114Abstract: 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 wType: ApplicationFiled: May 23, 2007Publication date: July 2, 2009Inventors: Andreas Pfaltz, Yann Ribourdouille, Xiangdong Feng, Balamurugan Ramalingam, Benoit Pugin, Felix Spindler
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Publication number: 20090156851Abstract: 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: ApplicationFiled: August 10, 2006Publication date: June 18, 2009Inventors: Walter Weissensteiner, Yaping Wang, Felix Spindler, Benoit Pugin, Xiangdong Feng
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Publication number: 20090124812Abstract: 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: ApplicationFiled: April 11, 2007Publication date: May 14, 2009Inventors: Weiping Chen, Felix Spindler, Benoit Pugin
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Publication number: 20090082581Abstract: 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-aliphType: ApplicationFiled: May 2, 2006Publication date: March 26, 2009Inventors: Benoit Pugin, Xiangdong Feng
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Publication number: 20080306263Abstract: 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: ApplicationFiled: August 13, 2008Publication date: December 11, 2008Inventors: Hans Rudolf MULLER, Rudolf MOSER, Viola GROEHN, Benoit PUGIN
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Publication number: 20080076937Abstract: 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-alkylphenyType: ApplicationFiled: July 4, 2005Publication date: March 27, 2008Inventors: Benoit Pugin, Xaing Dong Feng, Marc Thommen
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Publication number: 20080026933Abstract: 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: ApplicationFiled: July 4, 2005Publication date: January 31, 2008Inventors: Benoit Pugin, Xiang Dong Feng, Felix Spindler
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Publication number: 20070281915Abstract: 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: ApplicationFiled: November 21, 2006Publication date: December 6, 2007Inventors: William Love, Derek Brundish, William Rhys-Williams, Xiang Feng, Benoit Pugin
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Patent number: 7244841Abstract: 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: GrantFiled: December 23, 2003Date of Patent: July 17, 2007Assignees: Destiny Pharma Limited, Solvias AGInventors: William Love, Derek Brundish, William Rhys-Williams, Xiang Dong Feng, Benoit Pugin
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Publication number: 20070149796Abstract: 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: ApplicationFiled: December 10, 2004Publication date: June 28, 2007Applicant: SOLVIAS AGInventors: Andreas Pfaltz, Matthias Lotz, Marc Schonleber, Benoit Pugin, Martin Kesselgruber, Marc Thommen
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Publication number: 20070142655Abstract: 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: ApplicationFiled: December 10, 2004Publication date: June 21, 2007Applicant: SOLVIAS AGInventors: Matthias Lotz, Martin Kesselgruber, Marc Thommen, Benoit Pugin
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Publication number: 20060276643Abstract: 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: ApplicationFiled: April 5, 2004Publication date: December 7, 2006Inventor: Benoit Pugin
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Publication number: 20040143001Abstract: A compound of formula I: 1Type: ApplicationFiled: December 23, 2003Publication date: July 22, 2004Applicants: Destiny Pharma Limited, Solvias AGInventors: William Love, Derek Brundish, William Rhys-Williams, Xiang Dong Feng, Benoit Pugin