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).
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Patent number: 5600015Abstract: 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: GrantFiled: May 19, 1995Date of Patent: February 4, 1997Assignee: Hoffmann-La Roche Inc.Inventors: Emil A. Broger, Robert K. M uller
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Patent number: 5543559Abstract: 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: GrantFiled: June 8, 1995Date of Patent: August 6, 1996Assignee: Hoffman-La Roche Inc.Inventors: Emil A. Broger, Yvo Crameri, Rudolf Schmid, Theodor Siegfried
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Patent number: 5516944Abstract: 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: GrantFiled: September 30, 1994Date of Patent: May 14, 1996Assignee: Hoffmann-La Roche Inc.Inventors: Emil A. Broger, Marco Cereghetti, Alain Rageot
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Patent number: 5514805Abstract: 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: GrantFiled: April 8, 1994Date of Patent: May 7, 1996Assignee: Hoffmann-La Roche Inc.Inventors: Emil A. Broger, Werner Hofheinz, Arthur Meili
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Patent number: 5508438Abstract: 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: GrantFiled: September 24, 1993Date of Patent: April 16, 1996Assignee: Hoffmann-La Roche Inc.Inventors: Emil A. Broger, Marco Cereghetti
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Patent number: 5481008Abstract: 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: GrantFiled: August 31, 1994Date of Patent: January 2, 1996Assignee: Hoffmann-La Roche Inc.Inventors: Emil A. Broger, Martin Karpf, Ulrich Zutter
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Patent number: 5374727Abstract: 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: GrantFiled: May 27, 1993Date of Patent: December 20, 1994Assignee: Hoffmann-La Roche Inc.Inventor: Emil A. Broger
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Patent number: 5360908Abstract: 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: GrantFiled: September 26, 1991Date of Patent: November 1, 1994Assignee: Hoffman-LaRoche Inc.Inventors: Emil A. Broger, Bernd Heiser
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Patent number: 5288928Abstract: 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: GrantFiled: July 20, 1992Date of Patent: February 22, 1994Assignee: Ciba-Geigy CorporationInventors: Emil A. Broger, Yvo Crameri, Hans P. Isenring, Albert Pfiffner
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Patent number: 5274125Abstract: 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: GrantFiled: November 13, 1992Date of Patent: December 28, 1993Assignee: Hoffmann-La Roche Inc.Inventors: Emil A. Broger, Joseph Foricher, Bernd Heiser, Rudolf Schmid
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Patent number: 5142063Abstract: 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: GrantFiled: November 20, 1990Date of Patent: August 25, 1992Assignee: Hoffmann-La Roche, Inc.Inventors: Emil A. Broger, Yvo Crameri
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Patent number: 4857648Abstract: 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: GrantFiled: November 8, 1988Date of Patent: August 15, 1989Assignee: Hoffmann-La Roche Inc.Inventors: Emil A. Broger, Yvo Crameri, Bernd Heiser
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Patent number: 4652657Abstract: 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: GrantFiled: April 10, 1985Date of Patent: March 24, 1987Assignee: Hoffmann-La Roche Inc.Inventors: Emil A. Broger, Yvo Crameri
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Patent number: 4620013Abstract: Novel chiral phosphines are disclosed which when complexed with rhodium provide catalyst compositions for asymmetric hydrogenations.Type: GrantFiled: June 14, 1985Date of Patent: October 28, 1986Assignee: Hoffmann-La Roche Inc.Inventors: Emil A. Broger, Yvo Crameri
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Patent number: 4544770Abstract: 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: GrantFiled: July 11, 1983Date of Patent: October 1, 1985Assignee: Hoffmann-La Roche Inc.Inventor: Emil A. Broger
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Patent number: 4539411Abstract: Novel chiral phosphines are disclosed which when complexed with rhodium provide catalyst compositions for asymmetric hydrogenations.Type: GrantFiled: January 17, 1983Date of Patent: September 3, 1985Assignee: Hoffmann-La Roche Inc.Inventors: Emil A. Broger, Yvo Crameri
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Patent number: 4283559Abstract: 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: GrantFiled: May 21, 1979Date of Patent: August 11, 1981Assignee: Hoffmann-La Roche Inc.Inventors: Emil A. Broger, Yvo Crameri, Hans G. W. Leuenberger, Erich Widmer, Reinhard Zell
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Patent number: 4258210Abstract: A process for producing sodium pantothenate from .beta.-aminopropionitrile is disclosed.Type: GrantFiled: May 8, 1979Date of Patent: March 24, 1981Assignee: Hoffmann-La Roche Inc.Inventors: Dieter Bartoldus, Emil Broger
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Patent number: 4249023Abstract: 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: GrantFiled: May 21, 1979Date of Patent: February 3, 1981Assignee: Hoffmann-La Roche Inc.Inventor: Emil A. Broger
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Patent number: 4246204Abstract: 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: GrantFiled: May 21, 1979Date of Patent: January 20, 1981Assignee: Hoffmann-La Roche Inc.Inventor: Emil A. Broger