Patents by Inventor Emil A. Broger

Emil A. Broger 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: 5600015
    Abstract: There is described a process for the manufacture of isoprene derivatives of the general formula ##STR1## wherein the asymmetric centres can each individually have the (R)- or (S)-configuration, R represents a residue of the formulae ##STR2## R.sup.1 signifies lower alkyl or both R.sup.1 's together signify ethylene or propylene and n stands for the number 0, 1 or 2,in which a compound, which is present in the (E)- or (Z)-form, of the general formula ##STR3## wherein R, n and an optionally present asymmetric centre have the above significance,is asymmetrically hydrogenated with a ruthenium complex of an optically active atropisomeric diphosphine.
    Type: Grant
    Filed: May 19, 1995
    Date of Patent: February 4, 1997
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Emil A. Broger, Robert K. M uller
  • Patent number: 5543559
    Abstract: The present invention is concerned with a process for the manufacture of optically active compounds of the formula ##STR1## wherein R signifies lower alkyl, lower alkoxy, phenyl, benzyl or --NR.sub.2.sup.1, R.sup.1 signifies lower alkyl, phenyl, benzyl or hydrogen and * signifies an optically active center, by asymmetrically hydrogenating an enol derivative of ketoisophorone of the formula ##STR2## wherein R has the significance given above, in the presence of a rhodium complex of an optically active diphosphine ligand.
    Type: Grant
    Filed: June 8, 1995
    Date of Patent: August 6, 1996
    Assignee: Hoffman-La Roche Inc.
    Inventors: Emil A. Broger, Yvo Crameri, Rudolf Schmid, Theodor Siegfried
  • Patent number: 5516944
    Abstract: The present invention is concerned with novel optically active phosphorus compounds of the general formula ##STR1## wherein R and R.sup.1 each independently signify hydroxy, a protected hydroxy group, lower alkyl or lower alkoxy andR.sup.2 to R.sup.5 each independently signify alkyl with 3 to 7 carbon atoms, cycloalkyl or aryl or R.sup.2 and R.sup.3 or R.sup.4 and R.sup.5 together with the phosphorus form a group of the formula ##STR2## wherein R2 and R3 are different when R4 and R5 are the same, and R4 and R5 are different when R2 and R3 are the same,the manufacture of such compounds, their use for enantioselective reactions, such as, e.g., asymmetric hydrogenations, enantioselective hydrogen displacements in prochiral allylic systems and the like, as well as complexes of the compounds of formula I with Group VIII metals.
    Type: Grant
    Filed: September 30, 1994
    Date of Patent: May 14, 1996
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Emil A. Broger, Marco Cereghetti, Alain Rageot
  • Patent number: 5514805
    Abstract: A novel process for the asymmetric hydrogenation of compounds of the formula: ##STR1## wherein R represent aryl or heteroaryl, to compounds of the formula: ##STR2## wherein R has the above significance, is carried out using rhodium-diphosphine complexes.
    Type: Grant
    Filed: April 8, 1994
    Date of Patent: May 7, 1996
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Emil A. Broger, Werner Hofheinz, Arthur Meili
  • Patent number: 5508438
    Abstract: Novel, racemic and optically active phosphorus compounds of the formula ##STR1## wherein R signifies lower alkyl, lower alkoxy, hydroxy or a protected hydroxy group, R.sup.1 and R.sup.2 are different from each other and represent lower alkyl, cycloalkyl, aryl, a five-membered heteroaromatic or a group of the formula ##STR2## are described. The compounds of formula I are useful in the form of complexes with a metal of Group VIII as catalysts for asymmetric hydrogenations and for enantioselective hydrogen displacements in prochiral allylic systems.
    Type: Grant
    Filed: September 24, 1993
    Date of Patent: April 16, 1996
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Emil A. Broger, Marco Cereghetti
  • Patent number: 5481008
    Abstract: A catalytic process for the manufacture of optically active compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2 are alkyl, which is optionally interrupted by an O atom in a position other than the .alpha.-or .beta.-position, or optionally substituted benzyl,R.sup.3 is hydrogen, lower alkyl, optionally substituted benzyl, --CO--R.sup.4, --COOR.sup.4 or --CONR.sub.2.sup.4, andR.sup.4 is lower alkyl or aryl,comprising asymmetrically hydrogenating a compound of the formula ##STR2## wherein R.sup.1, R.sup.2 and R.sup.3 have the above significance, in the presence of a complex of an optically active, preferably atropisomeric, diphospine ligand with a metal of Group VIII.
    Type: Grant
    Filed: August 31, 1994
    Date of Patent: January 2, 1996
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Emil A. Broger, Martin Karpf, Ulrich Zutter
  • Patent number: 5374727
    Abstract: A process for the asymmetric hydrogenation of 6,7-dihydropyrido[1,2-a]indole-8-methanol or its aromatically-substituted derivatives of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 each, independently, is hydrogen, halogen, C.sub.1-7 -alkyl, C.sub.1-7 -haloalkyl, hydroxy, C.sub.1-7 -alkoxy, C.sub.1-7 -alkylthio, C.sub.1-7 -alkylsulfinyl, C.sub.1-7 -alkylsulfonyl, nitro, amino or acylamino, to (S)- or (R)-compounds of the formula ##STR2## wherein R.sup.1, R.sup.2 and R.sup.3 have the significances given above and the asterisk (*) denotes the chiral center, carried out using optically active rhodium-diphosphine complexes as catalysts, is described. The production of the compounds II, which also form an object of the invention, is also described. The compounds I and II are valuable intermediates, for example, for the preparation of pharmaceutically active substances.
    Type: Grant
    Filed: May 27, 1993
    Date of Patent: December 20, 1994
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Emil A. Broger
  • Patent number: 5360908
    Abstract: A process for the preparation of isoquinoline derivatives of the formulas ##STR1## wherein R.sup.1 and R.sup.2 have the significances herein after set forth in the description, is described.The compounds of formula IV are obtained by asymmetrically hydrogenating the compounds of formula I.
    Type: Grant
    Filed: September 26, 1991
    Date of Patent: November 1, 1994
    Assignee: Hoffman-LaRoche Inc.
    Inventors: Emil A. Broger, Bernd Heiser
  • Patent number: 5288928
    Abstract: There is disclosed a process for the asymmetrical hydrogenation of (E)-2-methyl-3-phenyl-2-propen-1-ol of formula ##STR1## wherein R.sub.1 is as defined herein, to give compounds of formula ##STR2## The catalyst is a neutral or cationic rhodium complex of a chiral atropisomeric phosphine.
    Type: Grant
    Filed: July 20, 1992
    Date of Patent: February 22, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Emil A. Broger, Yvo Crameri, Hans P. Isenring, Albert Pfiffner
  • Patent number: 5274125
    Abstract: Novel, racemic and optically active phosphorus compounds of the formula ##STR1## wherein R signifies lower alkyl, lower alkoxy or a protected hydroxy group, R.sup.1 signifies a five membered heteroaromatic ring, R.sup.2 stands for lower alkyl or lower alkoxy and n represents the number 0, 1 or 2, are described. The compounds of formula I serve in the form of complexes with a metal of Group VIII as catalyst for asymmetric hydrogenations and for enantioselective hydrogen displacements in prochiral allylic systems.
    Type: Grant
    Filed: November 13, 1992
    Date of Patent: December 28, 1993
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Emil A. Broger, Joseph Foricher, Bernd Heiser, Rudolf Schmid
  • Patent number: 5142063
    Abstract: The present invention describes novel chiral rhodium-diphosphine complexes having the formula[Rh(X) (Y) (Lp)]owherein X represents a residue of the formula X--COO.sup.- in which Z signifies a group ##STR1## aryl or substituted aryl, wherein R.sup.1, R.sup.2, R.sup.3 =hydrogen, halogen, lower alkyl, aryl-lower alkyl, perfluoro-C.sub.1-20 -alkyl, aryl, substituted aryl, the group --OR.sup.7, --(CH.sub.2).sub.m --COA or AOC--(CF.sub.2).sub.n, with the proviso that at least one of R.sup.1, R.sup.2, and R.sup.3 represents --OR.sup.7, aryl or substituted aryl,R.sup.4, R.sup.5, R.sup.6 =hydrogen, halogen, lower alkyl, aryl-lower alkyl, perfluoro--C.sub.1-20 -alkyl, aryl, substituted aryl, --(CH.sub.2).sub.m --COA or AOC--(CF.sub.2).sub.n,R.sup.7 =hydrogen, lower alkyl, partially or completely halogenated lower alkyl, aryl, substituted aryl or aryl-lower alkyl,A=The residue --OR or NR'.sub.
    Type: Grant
    Filed: November 20, 1990
    Date of Patent: August 25, 1992
    Assignee: Hoffmann-La Roche, Inc.
    Inventors: Emil A. Broger, Yvo Crameri
  • Patent number: 4857648
    Abstract: The invention is concerned with novel isoquinoline derivatives of the formula ##STR1## wherein R.sup.1 is hydrogen, lower alkyl, lower alkoxy, aryl, aryloxy, aryl-lower alkyl or aryl-lower alkoxy andR.sup.2 is phenyl or substituted phenyl.These novel isoquinoline derivatives are valuable intermediates in the manufacture of morphinan derivatives.
    Type: Grant
    Filed: November 8, 1988
    Date of Patent: August 15, 1989
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Emil A. Broger, Yvo Crameri, Bernd Heiser
  • Patent number: 4652657
    Abstract: There are described novel chiral rhodium-diphosphine complexes of the formula[Rh (X) (Y) (L.sub.0,1,2)].sub.1,2 Iwherein X, which may be fixed to a carrier, is Z--COO.sup.-, wherein Z is ##STR1## perfluorophenyl, perfluorobiphenyl or a residue of the formula ##STR2## and R.sup.1, R.sup.2 and R.sup.3 is halogen, lower alkyl, perfluorophenyl, perfluoro-C.sub.1-20 -alkyl, hydrogen or the group --COA or AOC--(CF.sub.2).sub.n -- in which A is --OR or --NR'.sub.2, except that at least one of the substituents R.sup.1, R.sup.2 and R.sup.3 is fluorine, R is hydrogen, lower alkyl or a cation, R' is hydrogen or lower alkyl and n is 1 to 20 and wherein Y is a chiral diphosphine ligand and L is a neutral ligand.
    Type: Grant
    Filed: April 10, 1985
    Date of Patent: March 24, 1987
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Emil A. Broger, Yvo Crameri
  • Patent number: 4620013
    Abstract: Novel chiral phosphines are disclosed which when complexed with rhodium provide catalyst compositions for asymmetric hydrogenations.
    Type: Grant
    Filed: June 14, 1985
    Date of Patent: October 28, 1986
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Emil A. Broger, Yvo Crameri
  • Patent number: 4544770
    Abstract: Compounds of the formula: ##STR1## wherein R.sup.1 is a 2,6,6-trimethyl-1-cyclohexen-1-yl or 2,3,6-trimethylphenyl group, either of which may be unsubstituted or substituted by a hydroxy group or a protected hydroxy group, R.sup.2 is aryl, and X.sup.- is an anionare manufactured by hydrogenating a compound of the formula: ##STR2## wherein R.sup.1, R.sup.2 and X.crclbar. are as above, in an organic solvent or aqueous-organic solvent in the presence of a nickel-, palladium-, platinum-, cobalt-, rhodium-, iridium-, or ruthenium-containing catalyst.The process is suitable as an intermediate step in carotenoid and retinoid syntheses.
    Type: Grant
    Filed: July 11, 1983
    Date of Patent: October 1, 1985
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Emil A. Broger
  • Patent number: 4539411
    Abstract: Novel chiral phosphines are disclosed which when complexed with rhodium provide catalyst compositions for asymmetric hydrogenations.
    Type: Grant
    Filed: January 17, 1983
    Date of Patent: September 3, 1985
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Emil A. Broger, Yvo Crameri
  • Patent number: 4283559
    Abstract: The compound 6-hydroxy-3-(5-hydroxy-3-methyl-1,3-pentadienyl)-2,4,4-trimethyl-2-cyclohe xen-1-one useful as intermediate for producing the natural coloring agent astaxanthin as well as a method for synthesizing astaxanthin from this compound and synthesizing the compound from 2-hydroxyketo isophorone.
    Type: Grant
    Filed: May 21, 1979
    Date of Patent: August 11, 1981
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Emil A. Broger, Yvo Crameri, Hans G. W. Leuenberger, Erich Widmer, Reinhard Zell
  • Patent number: 4258210
    Abstract: A process for producing sodium pantothenate from .beta.-aminopropionitrile is disclosed.
    Type: Grant
    Filed: May 8, 1979
    Date of Patent: March 24, 1981
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Dieter Bartoldus, Emil Broger
  • Patent number: 4249023
    Abstract: A process is disclosed for producing triphenylphosphine in which a triphenylphosphine dichloride-chloroform adduct, obtained by reacting triphenylphosphine oxide with phosgene in chloroform, is reduced with hydrogen. The reduction proceeds in a chloroform solvent or in the absence of a solvent.
    Type: Grant
    Filed: May 21, 1979
    Date of Patent: February 3, 1981
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Emil A. Broger
  • Patent number: 4246204
    Abstract: A process is disclosed for producing triphenylphosphine by hydrogenating triphenylphosphine dichloride in an inert solvent in the presence of a platinum, palladium, rhodium, ruthenium and/or iridium catalyst.
    Type: Grant
    Filed: May 21, 1979
    Date of Patent: January 20, 1981
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Emil A. Broger