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).

  • Patent number: 6015919
    Abstract: The invention relates to a compound of formula I ##STR1## R.sub.1 is C.sub.1 -C.sub.8 alkyl, phenyl or phenyl substituted by from 1 to 3 C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy substituents;R.sub.2 and R.sub.3 are each independently of the other hydrogen or C.sub.1 -C.sub.12 alkyl; andHal is F, Cl, Br or I.Compounds of formula I are valuable intermediates for compounds of formula III which are also a subject of this invention: ##STR2## R.sub.1, R.sub.2, R.sub.3 and Hal are as defined above; R.sub.10 and R.sub.11 are identical or different and are C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.12 cycloalkyl, phenyl, C.sub.5 -C.sub.12 cycloalkyl substituted by C.sub.1 -C.sub.4 alkyl or by C.sub.1 -C.sub.4 alkoxy, or phenyl substituted by from one to three C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, --SiR.sub.4 R.sub.5 R.sub.6, halogen, --SO.sub.3 M, --CO.sub.2 M, --PO.sub.3 M, --NR.sub.7 R.sub.8, --[.sup.+ NR.sub.7 R.sub.8 R.sub.9 ]X.sup.- or C.sub.1 -C.sub.5 fluoroalkyl substituents; orthe group --PR.
    Type: Grant
    Filed: February 8, 1999
    Date of Patent: January 18, 2000
    Assignee: Novartis AG
    Inventor: Benoit Pugin
  • Patent number: 5925778
    Abstract: The invention relates to a compound of formula (I), wherein R.sub.1 is C.sub.1 -C.sub.8 alkyl, phenyl or phenyl substituted by from 1 to 3 C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy substituents; R.sub.2 and R.sub.3 are each independently of the other hydrogen or C.sub.1 -C.sub.12 alkyl; and Hal is F, Cl, Br or I. Compounds of formula (I) are valuable intermediates for compounds of formula (III) which are also a subject of this invention, wherein R.sub.1, R.sub.2, R.sub.3 and Hal are as defined above; R.sub.10 and R.sub.11 are identical or different and are C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.12 cycloalkyl, phenyl, C.sub.5 -C.sub.12 cycloalkyl substituted by C.sub.1 -C.sub.4 alkyl or by C.sub.1 -C.sub.4 alkoxy, or phenyl substituted by from one to three C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, --SiR.sub.4 R.sub.5 R.sub.6, halogen, --SO.sub.3 M, --CO.sub.2 M, --PO.sub.3 M, --NR.sub.7 R.sub.8, --?.sup.+ NR.sub.7 R.sub.8 R.sub.9 !X.sup.- or C.sub.1 -C.sub.
    Type: Grant
    Filed: October 9, 1997
    Date of Patent: July 20, 1999
    Assignee: Novartis AG
    Inventor: Benoit Pugin
  • Patent number: 5883283
    Abstract: The invention relates to a process for the preparation of substituted 3-amninobenzonitriles, which comprises reacting the appropriate substituted 3-aminochlorobenzene with a cyano-donating reagent, and to the compounds thereby produced. The compounds are intermediates, which after further reaction, produce 1,2,3-benzothiadiazole-derivatives having plant immunizing properties.
    Type: Grant
    Filed: August 1, 1997
    Date of Patent: March 16, 1999
    Assignee: Novartis Finance Corporation
    Inventors: Richard Breitschuh, Benoit Pugin, Adriano Indolese, Verena Gisin
  • Patent number: 5783715
    Abstract: The invention relates to ferrocenyldiphosphine ligands containing a silylene group, ferrocenyldiphosphines bound to inorganic or polymeric organic supports by this silylene group, their preparation and also their metal complexes with transition metals such as rhodium or iridium. The invention also relates to the use of these complexes for hydrogenating organic double or triple bonds, in particular olefinic double bonds and carbon-heteroatom double bonds. The complexes are particularly suitable for enantioselective hydrogenation using chiral diphosphines and prochiral unsaturated compounds.
    Type: Grant
    Filed: December 13, 1996
    Date of Patent: July 21, 1998
    Assignee: Novartis Corporation
    Inventor: Benoit Pugin
  • Patent number: 5777062
    Abstract: The invention relates to polymers having structural repeating units of at least one monomer MM which contains a hydroxyl group or a primary or secondary amine group as a functional group bonded directly or in a side chain, wherein the functional group is bonded via a bridge group Q formed by a diisocyanate to the hydroxyl group or primary or secondary amino group of an aliphatic, cycloaliphatic, heterocycloaliphatic, aromatic or heteroaromatic ditertiary diphosphine, the phosphine groups of which are bonded to a carbon chain in the 1,2-, 1,3-, 1,4- or 1,5-position relative to one another. The invention also relates to a process for their preparation and to rhodium and iridium complexes with these diphosphine ligands.
    Type: Grant
    Filed: February 23, 1996
    Date of Patent: July 7, 1998
    Assignee: Novartis Corporation
    Inventor: Benoit Pugin
  • Patent number: 5627293
    Abstract: The invention relates to ferrocenyldiphosphine ligands containing a silylene group, ferrocenyldiphosphines bound to inorganic or polymeric organic supports by this silylene group, their preparation and also their metal complexes with transition metals such as rhodium or iridium. The invention also relates to the use of these complexes for hydrogenating organic double or triple bonds, in particular olefinic double bonds and carbon-heteroatom double bonds. The complexes are particularly suitable for enantioselective hydrogenation using chiral diphosphines and prochiral unsaturated compounds.The preparation of these immobilized ferrocenyldiphosphines has only been made possible by the provision of correspondingly functionalized ferrocenyldiphosphines. These compounds and their preparation are likewise novel.Accordingly, the invention also provides compounds of the formula I ##STR1## in which R.sub.1 is C.sub.1 -C.sub.8 alkyl, phenyl or phenyl substituted by from 1 to 3 C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.
    Type: Grant
    Filed: February 23, 1996
    Date of Patent: May 6, 1997
    Assignee: Ciba-Geigy Corporation
    Inventor: Benoit Pugin
  • Patent number: 5432289
    Abstract: Compounds of formula I ##STR1## wherein R.sub.1 denotes identical or different radicals and is linear or branched C.sub.1 -C.sub.12 alkyl, unsubstituted C.sub.5 -C.sub.6 cycloalkyl or C.sub.5 -C.sub.6 cycloalkyl which is substituted by C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, or is phenyl or benzyl, or both substituents R.sub.1 of a group (R.sub.1).sub.2 P are o,o'-diphenylene, R.sub.2 is hydrogen, linear or branched C.sub.1 -C.sub.12 alkyl, phenyl or benzyl, R.sub.3 is C.sub.1 -C.sub.12 alkylene, R.sub.4 is C.sub.2 -C.sub.18 alkylene, phenylene or benzylene, and R.sub.5 is C.sub.1 -C.sub.6 alkyl or phenyl, can be applied to solid carriers, such as silica gel or aerosils, and complexed with rhodium or iridium compounds. These materials are heterogeneous and separable catalysts for the asymmetrical hydrogenation of prochiral compounds containing carbon double bonds or carbon/hetero atom double bonds, for example ketones and imines.
    Type: Grant
    Filed: September 9, 1994
    Date of Patent: July 11, 1995
    Assignee: Ciba-Geigy Corporation
    Inventors: Benoit Pugin, Felix Spindler, Manfred Muller
  • Patent number: 5382729
    Abstract: Compounds of formula I ##STR1## wherein R.sub.1 denotes identical or different radicals and is linear or branched C.sub.1 -C.sub.12 alkyl, unsubstituted C.sub.5 -C.sub.6 cycloalkyl or C.sub.5 -C.sub.6 cycloalkyl which is substituted by C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, or is phenyl or benzyl, or both substituents R.sub.1 of a group (R.sub.1).sub.2 P are o,o-diphenylene, R.sub.2 is hydrogen, linear or branched C.sub.1 -C.sub.12 alkyl, phenyl or benzyl, R.sub.3 is C.sub.1 -C.sub.12 alkylene, R.sub.4 is C.sub.2 -C.sub.18 alkylene, phenylene or benzylene, and R.sub.5 is C.sub.1 -C.sub.6 alkyl or phenyl, can be applied to solid carriers, such as silica gel or aerosils, and complexed with rhodium or iridium compounds. These materials are heterogeneous and separable catalysts for the assymetrical hydrogenation of prochiral compounds containing carbon double bonds or carbon/hetero atom double bonds, for example ketones and imines.
    Type: Grant
    Filed: February 16, 1994
    Date of Patent: January 17, 1995
    Assignee: Ciba-Geigy Corporation
    Inventors: Benoit Pugin, Felix Spindler, Manfred Muller
  • Patent number: 5308819
    Abstract: Compounds where a solid carrier material which contains diphosphine rhodium or iridium complexes fixed on the surface thereof, of which the carrier material has the formula IV or IVa: ##STR1## wherein Y denotes two monoolefin ligands or a diene ligand, M is Ir(I) or Rh(i), Z is --Cl, --Br or -I, A.crclbar. is the anion of an oxyacid or complex acid, T is a solid carrier material, r is 0, 1 or 2, and R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are as defined in claim 1. These materials are heterogeneous and separable catalysts for the asymmetrical hydrogenation of prochiral compounds containing carbon double bonds or carbon/hetero atom double bonds, for example ketones and imines.
    Type: Grant
    Filed: July 14, 1993
    Date of Patent: May 3, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Benoit Pugin, Felix Spindler, Manfred Muller
  • Patent number: 5306853
    Abstract: Compounds of formula II ##STR1## wherein the groups (R.sub.1).sub.2 P(CH.sub.2).sub.m bzw.n are in o- or m-position to each other and the substituents R.sub.1 are identical or different radicals, m and n are each independently of the other 0 or 1, R.sub.1 is linear or branched C.sub.1 -C.sub.12 alkyl, unsubstituted C.sub.5 -C.sub.6 cycloalkyl or C.sub.5 -C.sub.6 cycloalkyl which is substituted by C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, or is phenyl or benzyl, or both substituents R.sub.1 in a group (R.sub.1).sub.2 P together are o,o'-diphenylene, --R.sub.2 --X-- is a bond or --(C.sub.x H.sub.2x --O).sub.y --, or X-- is O-- and R.sub.2 is C.sub.1 -C.sub.6 alkylene, x is an integer from 2 to 6 and y is an integer from 2 to 6, R.sub.3 is C.sub.2 -C.sub.18 alkylene, phenylene or benzylene, and R.sub.4 is C.sub.1 -C.sub.6 alkyl or phenyl, can be applied to solid carriers, such as silica gel or aerosils, and complexed with rhodium or iridium compounds.
    Type: Grant
    Filed: June 17, 1993
    Date of Patent: April 26, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Benoit Pugin, Manfred Muller, Felix Spindler
  • Patent number: 5252751
    Abstract: Compounds of formula I ##STR1## wherein R.sub.1 denotes identical or different radicals and is linear or branched C.sub.1 -C.sub.12 alkyl, unsubstituted C.sub.5 -C.sub.6 cycloalkyl or C.sub.5 -C.sub.6 cycloalkyl which is substituted by C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, or is phenyl or benzyl, or both substituents R.sub.1 of a group (R.sub.1).sub.2 P are o,o'-diphenylene, R.sub.2 is hydrogen, linear or branched C.sub.1 -C.sub.12 alkyl, phenyl or benzyl, R.sub.3 is C.sub.1 -C.sub.12 alkylene, R.sub.4 is C.sub.2 -C.sub.18 alkylene, phenylene or benzylene, and R.sub.5 is C.sub.1 -C.sub.6 alkyl or phenyl, can be applied to solid carriers, such as silica gel or aerosils, and complexed with rhodium or iridium compounds. These materials are heterogeneous and separable catalysts for the asymmetrical hydrogenation of prochiral compounds containing carbon double bonds or carbon/hetero atom double bonds, for example ketones and imines.
    Type: Grant
    Filed: January 21, 1992
    Date of Patent: October 12, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Benoit Pugin, Felix Spindler, Manfred Muller
  • Patent number: 5244857
    Abstract: Compounds of formula II ##STR1## wherein the groups (R.sub.1).sub.2 P(CH.sub.2).sub.m and n are in o- or m-position to each other and the substituents R.sub.1 are identical or different radicals, m and n are each independently of the other 0 or 1, R.sub.1 is linear or branched C.sub.1 -C.sub.12 alkyl, unsubstituted C.sub.5 -C.sub.6 cycloalkyl or C.sub.5 -C.sub.6 cycloalkyl which is substituted by C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, or is phenyl or benzyl, or both substituents R.sub.1 in a group (R.sub.1).sub.2 P together are o,o'-diphenylene, --R.sub.2 --X-- is a bond or --(C.sub.x H.sub.2x --O).sub.y --, or X-- is O-- and R.sub.2 is C.sub.1 -C.sub.6 alkylene, x is an integer from 2 to 6 and y is an integer from 2 to 6, R.sub.3 is C.sub.2 -C.sub.18 alkylene, phenylene or benzylene, and R.sub.4 is C.sub.1 -C.sub.6 alkyl or phenyl, can be applied to solid carriers, such as silica gel or aerosils, and complexed with rhodium or iridium compounds.
    Type: Grant
    Filed: January 21, 1992
    Date of Patent: September 14, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Benoit Pugin, Manfred Muller, Felix Spindler
  • Patent number: 5011995
    Abstract: Asymmetric hydrogenation of prochiral N-aliphatic ketimines to give optically active secondary amines at a temperature from -20.degree. to 80.degree. C., a hydrogen pressure of 10.sup.5 to 10.sup.7 Pa, with the addition of catalytic amounts of an iridium compound of the formula III or IIIa[XIrYZ] (III)or[XIrY].sup..sym. A.sup..crclbar. (IIIa)in which X is two olefin ligands or a diene ligand, Y is a chiral diphosphine the secondary phosphine group of which are attached through 2-4 C atoms and which, together with the Ir atom, forms a 5-membered, 6-membered or 7-membered ring, or Y is a chiral diphosphinite the phosphinite groups of which are attached via 2 C atoms and which, together with the Ir atom, forms a 7-membered ring, Z is Cl, Br or I and A.sup.- is the anion of an oxygen acid or complex acid, and, if appropriate, with the addition of an ammonium chloride, bromide or iodide or an alkali metal chloride, bromide or iodide.
    Type: Grant
    Filed: July 19, 1988
    Date of Patent: April 30, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Benoit Pugin, Gerardo Ramos, Felix Spindler
  • Patent number: 4994615
    Abstract: Asymmetric hydrogenation of prochiral N-arylketimines to give optically active secondary amines at a temperature of -20.degree. to 80.degree. C., a hydrogen pressure of 10.sup.5 to 6.10.sup.6 Pa with the addition of catalytic amounts of an iridium compound of the formula III or IIIa[XIrYZ] (III)or[XIrY.sup..sym. A.sup..crclbar. (IIIa)in which X is two olefin ligands or one diene ligand, Y is a chiral diphosphine, the secondary phosphine groups of which are linked by 2-4 C atoms and which, together with the Ir atom, forms a 5-, or 6- or 7-ring, or Y is a chiral diphosphinite, the phosphinite groups of which are linked via 2 C atoms and which together with the Ir atom forms a 7-ring, Z is Cl, Br or I and A.sup.63 is the anion of an oxygen acid or complex acid, and if appropriate with the addition of an ammonium or alkali metal chloride, bromide or iodide.
    Type: Grant
    Filed: July 29, 1987
    Date of Patent: February 19, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Felix Spindler, Benoit Pugin