Patents Assigned to Solvias AG
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Patent number: 11220484Abstract: An economic, one-step method for the production of N-substituted aromatic hydroxylamines of formula (I) R—N(OH)—C(?O)—(O)R1??(I), with hydrogen, by catalytic hydration with possibly modified hydration catalysts in an aprotic solvent and in the presence of a halogen formic acid ester and in some cases in the presence of a base.Type: GrantFiled: January 30, 2018Date of Patent: January 11, 2022Assignee: SOLVIAS AGInventor: Heinz Steiner
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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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Patent number: 8450501Abstract: Compounds of the formula (I), in the form of mixtures comprising predominantly one diastereomer or in the form of pure diastereomers, Z1-Q-P*R0R1 (I) in which Z1 is a C-bonded, secondary phosphine group —P(R)2; in which R is in each case independently hydrocarbon radicals or heterohydrocarbon radicals, or Z1 is the —P*R0R1 group; Q is a bivalent, achiral, aromatic base skeleton, a bivalent, achiral ferrocene base skeleton, an optionally substituted bivalent cycloalkane or heterocycloalkane skeleton, or a C1-C4-alkylene skeleton.Type: GrantFiled: November 14, 2008Date of Patent: May 28, 2013Assignee: Solvias AGInventors: Benoît Pugin, Matthias Lotz, Heidi Landert, Adrian Wyss, Raphael Aardoom, Björn Gschwend, Andreas Pfaltz, Felix Spindler
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Patent number: 8415488Abstract: Compounds of the formula I, in the form of mixtures comprising predominantly one enantiomer or in the form of pure enantiomers, secondary phosphine-Q-P*(?O)HR1 (I) in which secondary phosphine is a C-bonded, secondary phosphine group —P(R)2; in which R is in each case independently hydrocarbon radicals or heterohydrocarbon radicals; Q is a bivalent, achiral, aromatic base skeleton, a bivalent, achiral ferrocene base skeleton, an optionally substituted bivalent cycloalkane or heterocycloalkane skeleton, or a C1-C4-alkylene skeleton, and in which base skeletons a secondary phosphine group is bonded directly to a carbon atom, or, in the case of cyclic base skeletons, directly to a carbon atom or via a C1-C4-alkylene group, and in which base skeletons a P-chiral group —P*(O)HR1 is bonded to a carbon atom such that the phosphorus atoms are linked via 1 to 7 atoms of a carbon chain optionally interrupted by heteroatoms from the group of O, S, N, Fe or Si; P* is a chiral phosphorus atom; and R1 is a hydrocarbon radiType: GrantFiled: November 14, 2008Date of Patent: April 9, 2013Assignee: Solvias AGInventors: Benoît Pugin, Heidi Landert, Björn Gschwend, Andreas Pfaltz, Felix Spindler
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Patent number: 8008529Abstract: 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: GrantFiled: May 23, 2007Date of Patent: August 30, 2011Assignee: Solvias AGInventors: Andreas Pfaltz, Yann Ribourdouille, Xiangdong Feng, Balamurugan Ramalingam, Benoît Pugin, Felix Spindler
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Patent number: 7994355Abstract: The present invention relates to metallocene-based phosphine ligands having chirality at phosphorus and at least one other element of chirality (planar chirality and/or chirality at carbon); and to the use of such ligands in asymmetric transformation reactions to generate high enantiomeric excesses of formed compounds. A method for the preparation of ligands according to the invention involving the conversion of the ortho-lithiated substituted metallocene to a phosphine chiral at phosphorus is also disclosed.Type: GrantFiled: January 14, 2005Date of Patent: August 9, 2011Assignee: Solvias AGInventors: Wei-Ping Chen, John Whittall
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Patent number: 7977499Abstract: Abstract Compounds of the formula (I) in the form of racemates, enantiomerically pure diastereomers or a mixture of diastereomers, where the radicals R1 are identical or different and are each C1-C4-alkyl; m is 0 or an integer from 1 to 4; n is 0 or an integer from 1 to 3; p is 0 or an integer from 1 to 5; R2 is an aromatic hydrocarbon radical or a C-bonded heterohydrocarbon radical and R3 is an aliphatic or C-bonded heteroaliphatic hydrocarbon radical; R2 and R3 are identical or different and are each an aliphatic or C-bonded heteroaliphatic hydrocarbon radical; R4 is an unsubstituted or C1-C6-alkyl-, C1-C6-alkoxy- or halogen-substituted hydrocarbon radical; and A is a secondary amino group, are ligands for metal complexes which are suitable as catalysts for homogeneous enantioselective hydrogenation.Type: GrantFiled: February 15, 2008Date of Patent: July 12, 2011Assignee: Solvias AGInventors: Weiping Chen, Felix Spiindler, Ulrike Nettekoven, Benoît Pugin
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Patent number: 7906669Abstract: The present invention concerns a metallocene-based phosphine ligand for use in enantioselective catalysis, the ligand having the Formula (I): Wherein M is a metal; Z is P or As; L is a suitable linker; R1 is selected from alkyl, alkoxy, alkylamino, cycloalkyl, cycloalkoxy, cycloalkylamino carbocyclic aryl, substituted and unsubstituted carbocyclic aryloxy, heteroaryl, heteroaryloxy, carbocyclic arylamino and heteroarylamino; X* is selected from (II): Wherein R, R2 and R3 are independently selected from optionally substituted branched- and straight-chain alkyl, cycloalkyl, heterocycloalkyl, carbocyclic aryl, and heteroaryl.Type: GrantFiled: January 13, 2006Date of Patent: March 15, 2011Assignee: Solvias AGInventors: Peter McCormack, Chen Weiping, John Whittall
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Patent number: 7892354Abstract: A process for the detection of polymorphic or pseudopolymorphic forms of solid, molecular and crystallizing compounds, or of molecular, cocrystalline compounds or of solid solutions which consist of at least two solid, molecular and crystallizing compounds, in a series investigation using an apparatus for parallel investigations in vessels of an array under different conditions in each vessel, in which substantially only the amorphous form of the crystallizing compound, a solvate of the crystallizing compound or substantially only the amorphous form or a solvate of a compound in a mixture of at least two compounds is used as a suspension or solution, the solutions of amorphous compound having, at the same temperature, a higher content of crystallizable compounds than is achievable with a corresponding crystalline compound.Type: GrantFiled: October 4, 2004Date of Patent: February 22, 2011Assignee: Solvias AGInventors: Fritz Blatter, Martin Szelagiewicz, Markus von Raumer
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Patent number: 7589196Abstract: 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: GrantFiled: April 5, 2004Date of Patent: September 15, 2009Assignee: Solvias AGInventors: Benoît Pugin, Pierre Martin, Markus Müller, Frédéric Maurice Naud, Felix Spindler, Marc Thommen, Gianpietro Melone, Martin Kesselgruber
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Patent number: 7504071Abstract: A device includes a support (1) and at least two seals (2), which are arranged in a row and are hermetically fitted into cavities, and protrude from the support laterally with respect to inlet and outlet openings, one end of the support being provided with an inlet opening (3) and one end being provided with an outlet opening (4), and the seals being provided with a least one inlet opening and one outlet opening, and the support containing at least one first channel (5) which starts at the inlet opening (3) and is continuous, and is arranged in such a way that it opens into the inlet openings in the side walls of the seals arranged in a row, and one second channel (6) which starts at the outlet opening and is continuous, and is arranged in such a way that it opens into the outlet openings in the side walls of the seals arranged in a row.Type: GrantFiled: September 13, 2002Date of Patent: March 17, 2009Assignee: Solvias AGInventors: Fritz Blatter, Brigitte Cron-Eckhardt, Urs Christoph Hofmeier, Peter Koller, Claudia Marcolli, Martin Szelagiewicz
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Patent number: 7495123Abstract: 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: GrantFiled: April 5, 2005Date of Patent: February 24, 2009Assignees: 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
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Patent number: 7491671Abstract: Process for preparing a catalyst solution by reacting metal complexes and diphosphines in the presence of an inert organic solvent, which is characterized in that a) an uncharged or cationic metal complex having a TM8 metal as central atom, and b) a salt of a chiral ditertiary diphosphine which has one or two phospholane groups which are bound to a carbon chain having from 2 to 4 carbon atoms and contain anions selected from the group consisting of RCCOO?, RCSO3?, BF4?, PF6?, AsF6?, SbF6?, B(C6F5)4? and B(3,5-bistrifluoromethylphenyl)4?, are reacted with one another, where the ratio of the components a) and b) is from 1:1 to 1:2 and RC is C1-C6-haloalkyl, C5-C10-halocycloalkyl or C6-C10-haloaryl.Type: GrantFiled: May 7, 2004Date of Patent: February 17, 2009Assignee: Solvias AGInventors: Martin Kesselgruber, Marc Thommen
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Patent number: 7446236Abstract: Process for catalytically hydrogenating carbon-heteroatom double bonds, in particular for asymmetrically catalytically hydrogenating simple ketones, which includes the step of reacting the substrate with hydrogen in the presence of a hydrogenation catalyst and of a base, characterized in that the hydrogenation catalyst is a 5-coordinate ruthenium complex which in each case has a monophosphine ligand and a bidentate P-N ligand.Type: GrantFiled: November 27, 2003Date of Patent: November 4, 2008Assignee: Solvias AGInventors: Frédéric Maurice Naud, Ulrich Pittelkow
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Patent number: 7435840Abstract: 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: GrantFiled: December 10, 2004Date of Patent: October 14, 2008Assignee: Solvias AGInventors: Andreas Pfaltz, Matthias Lotz, Marc Schönleber, Benoît Pugin, Martin Kesselgruber, Marc Thommen
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Patent number: 7407910Abstract: The invention relates to a process for the manufacture of bidentate ligands of the formula IA and IIA, characterized in that N,N-(optionally substituted) dialkylamino phosphines bound to an aromatic carbon are lithiated in ortho-position and the lithiated compounds are further converted to said bidentate ligands: wherein X1 is NR, O or S; X2 is CHR1 or CR1; X3 is CHR2 or NR2 or, if X2 is CR1, X3 is CR2 or N; and R, R1 and R2 are radicals such as alkyl groups or R1 and R2 together form an annealed ring; Y1*, Y2* and Y1?* are, independently of each other, an element of the fifth group of the periodic table of elements as such or in thioxo or oxo form; Z1*, Z2*, Z3*, Z4*, Z1?*, Z2?* are, independently of each other, for example halogen, hydrogen, or an unsubstituted or substituted moiety selected from radicals such as alkyl groups; the substituents have otherwise the meanings given in the specification; and the ligands are capable of forming metal complexes, which can be used as catalysts in stereoselectiveType: GrantFiled: June 23, 2006Date of Patent: August 5, 2008Assignee: Solvias AGInventor: Ulrich Berens
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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: 20070134803Abstract: A process for the detection of polymorphic or pseudopolymorphic forms of solid, molecular and crystallizing compounds, or of molecular, cocrystalline compounds or of solid solutions which consist of at least two solid, molecular and crystallizing compounds, in a series investigation using an apparatus for parallel investigations in vessels of an array under different conditions in each vessel, in which substantially only the amorphous form of the crystallizing compound, a solvate of the crystallizing compound or substantially only the amorphous form or a solvate of a compound in a mixture of at least two compounds is used as a suspension or solution, the solutions of amorphous compound having, at the same temperature, a higher content of crystallizable compounds than is achievable with a corresponding crystalline compound.Type: ApplicationFiled: October 4, 2004Publication date: June 14, 2007Applicant: SOLVIAS AGInventors: Fritz Blatter, Martin Szelagiewicz, Markus von Raumer