Abstract: A process for preparing pyridinecarboxylic esters of the general formula: ##STR1## wherein R.sup.1 is hydrogen, a C.sub.1 -C.sub.6 -alkyl group, a C.sub.1 -C.sub.4 -alkoxycarbonyl group or a C.sub.1 -C.sub.4 -alkoxymethyl group, R.sup.2 is a C.sub.1 -C.sub.4 -alkyl group and X is chlorine or bromine. The pyridinecarboxylic esters are obtained by reacting the corresponding 2,3-dihalopyridines with carbon monoxide and a C.sub.1 -C.sub.4 -alkanol in the presence of a weak base and a complex of palladium with a bis(diphenylphosphine). Pyridinecarboxylic esters are intermediates for preparing herbicides and drugs against fibrotic diseases.
Type:
Grant
Filed:
March 30, 1999
Date of Patent:
February 8, 2000
Assignee:
Lonza Ltd.
Inventors:
Yves Bessard, Gerhard Stucky, Jean-Paul Roduit
Abstract: A process for the production of 2-chloro-5-chloromethylpyridine of the formula: ##STR1## starting from 6-hydroxynicotinic acid of the formula: ##STR2## In this way 6-hydroxynicotinic acid is reacted with an acid chloride to 6-hydroxynicotinoyl chloride of the formula: ##STR3## The latter is then catalytically hydrogenated with hydrogen to 6-hydroxy-5-hydroxymethylpyridine of the formula: ##STR4## The latter is then catalytically hydrogenated with hydrogen to 2-hydroxy-5-hydroxymethylpyridine of the formula: ##STR5## which is then chlorinated to the end product according to formula I.
Abstract: A novel process for the preparation of malononitrile which involves subjecting a (2-cyano-N-alkoxy)acetimidoyl halide to a high-temperature treatment.
Type:
Grant
Filed:
March 19, 1999
Date of Patent:
February 1, 2000
Assignee:
Lonza, Ltd.
Inventors:
Peter Chen, Johannes Hoffner, Andre Mueller, Rudolf Fuchs
Abstract: 2-Amino-4,5,3',4'-tetramethoxybenzophenone of the formula: ##STR1## is prepared by mononitration of 3,3',4,4'-tetramethyoxybenzophenone using nitric acid in the presence of acetic acid, and subsequent reduction of the nitro group. The compound is an intermediate in the synthesis of active ingredients against rheumatoid arthritis.
Type:
Grant
Filed:
March 12, 1999
Date of Patent:
January 4, 2000
Assignee:
Lonza, Ltd.
Inventors:
Oleg Werbitzky, Walter Brieden, Etienne Heinzmann
Abstract: Substituted pyridines of the general formula: ##STR1## wherein R.sup.1 is hydroxyl or chlorine, and a) X is hydrogen or chlorine, R.sup.2 and R.sup.3 together are .dbd.O, R.sup.4 is a group of the formula --OR.sup.5 and R.sup.5 is hydrogen, C.sub.1 -C.sub.4 -alkyl or benzyl orb) X is hydrogen and R.sup.2, R.sup.3 and R.sup.4 together are .dbd.N--NH--, orc) X and R.sup.2 each is hydrogen and R.sup.3 and R.sup.4 together are --O--, ord) X and R.sup.2 each is hydrogen, R.sup.3 is hydroxyl and R.sup.4 is amino or hydroxy.The compounds are obtained by subjecting nicotine to microbiological oxidation to give 5-succinoyl-2-pyridone, followed by chemical reactions. The compounds are suitable as intermediates for the preparation of pharmaceutically active compounds.
Type:
Grant
Filed:
April 30, 1998
Date of Patent:
November 30, 1999
Assignee:
Lonza, Ltd.
Inventors:
Andreas Kiener, Jean-Paul Roduit, Alain Wellig
Abstract: A novel process for the preparation of malononitrile, which involves subjecting an isonitrile, optionally in the presence of a nitrile, to a high-temperature treatment.
Type:
Grant
Filed:
March 19, 1999
Date of Patent:
September 28, 1999
Assignee:
Lonza, Ltd.
Inventors:
Peter Chen, Johannes Hoffner, Andre Mueller, Rudolf Fuchs
Abstract: A process for the production of aryl cyanates of the general formula I: ##STR1## A phenol of the general formula II: ##STR2## a tertiary amine and cyanogen chloride, of which at least one of the three components is present as a solution in an organic solvent, are fed essentially simultaneously and continuously at a temperature of -20.degree. C. to 0.degree. C. and in a molar ratio of cyanogen chloride to the reactive hydroxy groups of the phenol of 1.0:1.0 to 1.2:1.0 in a cooled loop reactor, so that the reaction components, before they come in contact with one another, are prediluted by the reaction mixture circulating in the loop reactor. Simultaneously, a stream of the reaction mixture corresponding to the fed volume of the reaction components is drawn off from the circulation.
Abstract: The process for the preparation of bicyclic amidines of the general formula: ##STR1## wherein A is selected from the group consisting of --CR.sup.1 R.sup.2 --CR.sup.3 R.sup.4 --CR.sup.5 R.sup.6 --, --CR.sup.1 R.sup.2 --CR.sup.3 R.sup.4 --CR.sup.5 R.sup.6 --CR.sup.7 R.sup.8 -- and --CR.sup.1 R.sup.2 --CR.sup.3 R.sup.4 --CR.sup.5 R.sup.6 --CR.sup.7 R.sup.8 --CR.sup.9 R.sup.10 --, wherein the substituents in A are in each case numbered starting from the nitrogen atom, and B is selected from the group consisting of --CR.sup.11 R.sup.12 --CR.sup.13 R.sup.14 --, --CR.sup.11 R.sup.12 --CR.sup.15 R.sup.16 --CR.sup.13 R.sup.14 -- and --CR.sup.11 R.sup.12 --CR.sup.15 R.sup.16 --CR.sup.17 R.sup.18 --CR.sup.13 R.sup.14 --, and R.sup.1, R.sup.2 and R.sup.11 to R.sup.14 are, in each case independently of one another, hydrogen, C.sub.1 -C.sub.4 -alkyl, aryl, or are C.sub.1 -C.sub.4 -alkyl which is substituted with hydroxyl, amino, C.sub.1 -C.sub.4 -alkylamino or mercapto, and R.sup.3 to R.sup.10 and R.sup.15 to R.sup.
Abstract: New microorganisms with plasmids stable relative to betaine utilization. These new microorganisms contain (a) a hybrid plasmid with a DNA fragment that contains a genetic sequence that codes for betaine utilization and (b) a mutation in the chromosomal gene coding for the betaine utilization.
Type:
Grant
Filed:
July 21, 1997
Date of Patent:
April 6, 1999
Assignee:
Lonza Ltd.
Inventors:
Thomas Zimmermann, Cristiana Boraschi, Knut Burgdorf, Catherine Caubere
Abstract: Optically active 1-(p-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline having the formula (I) is prepared by asymmetric hydrogenation of the corresponding 3,4,5,6,7,8-hexahydro-compound or of the new 1-(p-methoxybenzyl)-3,4,5,6,7,8-hexahydroisoquinoline dihydrogenated phosphate in the present of chiral iridium-phosphine complexes. This product is an intermediate product in the synthesis of cough-relieving dextromethorphanne and analgesic levorphanol.
Abstract: Optically active piperazine-2-carboxylic acid derivatives of the general formula: ##STR1## wherein R.sup.1 and R.sup.2 are inter alia hydrogen, alkyl or acyl and X is alkoxy or a (substituted) amino group, are prepared by asymmetric hydrogenation of the corresponding 1,4,5,6-tetrahydropyrazines, catalyzed by optically active rhodium, ruthenium or iridium complexes. The compounds of the Formula 1 are intermediates for the preparation of pharmaceutical active ingredients, for example, HIV protease inhibitors.
Abstract: Substituted pyridines of the general formula: ##STR1## wherein R.sup.1 is hydroxyl or chlorine, and a) X is hydrogen or chlorine, R.sup.2 and R.sup.3 together are .dbd.O, R.sup.4 is a group of the formula --OR.sup.5 and R.sup.5 is hydrogen, C.sub.1 -C.sub.4 -alkyl or benzyl, orb) X is hydrogen and R.sup.2, R.sup.3 and R.sup.4 together are .dbd.N--NH--, orc) X and R.sup.2 each is hydrogen and R.sup.3 and R.sup.4 together are --O--, ord) X and R.sup.2 each is hydrogen, R.sup.3 is hydroxyl and R.sup.4 is amino or hydroxyl.The compounds are obtained by subjecting nicotine to microbiological oxidation to give 5-succinoyl-2-pyridone, followed by chemical reactions. The compounds are suitable as intermediates for the preparation of pharmaceutically active compounds.
Type:
Grant
Filed:
November 21, 1995
Date of Patent:
June 2, 1998
Assignee:
Lonza, Ltd.
Inventors:
Andreas Kiener, Jean-Paul Roduit, Alain Wellig
Abstract: A process for preparing acetoacetates of the general formula: ##STR1## They are prepared by the addition of diketene onto an alcohol of the general formula:HO--R.sup.
Abstract: A process for the asymmetric hydrogenation of the furoimidazole derivatives of the general formula: ##STR1## wherein R.sub.1 is a protective group, which is cleavable in a known way, and R.sub.2 is hydrogen or a protective group, which is cleavable in a known way, with hydrogen in the presence of a homogeneous catalyst to the corresponding diastereomeric tetrahydrofuroimidazole derivatives of the general formula: ##STR2## The tetrahydrofuroimidazole derivatives of the general formula II are intermediate products for the production of vitamin (+) biotin.
Type:
Grant
Filed:
July 22, 1997
Date of Patent:
May 26, 1998
Assignee:
Lonza, Ltd.
Inventors:
Martin Eyer, Rudolf Fuchs, John McGarrity
Abstract: The process for the preparation of bicyclic amidines of the general formula: ##STR1## wherein A is selected from the group consisting of --CR.sup.1 R.sup.2 --CR.sup.3 R.sup.4 --CR.sup.5 R.sup.6 --, --CR.sup.1 R.sup.2 --CR.sup.3 R.sup.4 --CR.sup.5 R.sup.6 --CR.sup.7 R.sup.8 -- and --CR.sup.1 R.sup.2 --CR.sup.3 R.sup.4 --CR.sup.5 R.sup.6 --CR.sup.7 R.sup.8 --CR.sup.9 R.sup.10 --, wherein the substituents in A are in each case numbered starting from the nitrogen atom, and B is selected from the group consisting of --CR.sup.11 R.sup.12 --CR.sup.13 R.sup.14 --, --CR.sup.11 R.sup.12 --CR.sup.15 R.sup.16 --CR.sup.13 R.sup.14 -- and --CR.sup.11 R.sup.12 --CR.sup.15 R.sup.16 --CR.sup.17 R.sup.18 --CR.sup.13 R.sup.14 --, and R.sup.1, R.sup.2 and R.sup.11 to R.sup.14 are, in each case independently of one another, hydrogen, C.sub.1 -C.sub.4 -alkyl, aryl, or are C.sub.1 -C.sub.4 -alkyl which is substituted with hydroxyl, amino, C.sub.1 -C.sub.4 -alkylamino or mercapto, and R.sup.3 to R.sup.10 and R.sup.15 to R.sup.
Abstract: In a process for preparing 3-methylpiperidine or 3-methylpyridine from 2-methyl-1,5-diaminopentane in the gaseous phase, the initial product is made to flow over catalysts. In the first step, 3-methylpiperidine is produced, and if required 3-methylpyridine is produced in a second step.
Type:
Grant
Filed:
November 2, 1995
Date of Patent:
February 3, 1998
Assignee:
Lonza Ltd.
Inventors:
Josef Heveling, Erich Armbruster, Walter Siegrist
Abstract: A microbiological process for the preparation of a heteroaromatic carboxylic acid or one of its physiologically tolerated salts of the formulae I or II: ##STR1## wherein R.sub.1 and R.sub.2 are identical or different and each denotes a hydrogen or halogen atom, and X denotes a nitrogen atom or CH--, from a heteroaromatic nitrile of the formulae III or IV, respectively: ##STR2## First, a microorganism, Alcaligenes faecalis (DSM 6335), is cultured in the presence of an inducer, 2-cyanopyridine, and a carbon source such as a dicarboxylic acid, a tricarboxylic acid or a carbohydrate. Substrate III or IV is then reacted with the cultured microorganism. The biotransformation is carried out under anaerobic conditions for compounds of the formula I, and under aerobic conditions for compounds of the formula II.
Type:
Grant
Filed:
June 6, 1996
Date of Patent:
December 30, 1997
Assignee:
Lonza, Ltd.
Inventors:
Andreas Kiener, Jean-Paul Roduit, Rainer Glockler
Abstract: A process for the preparation of 2-substituted 5-chloroimidazole-4-carbaldehydes of the general formula: ##STR1## wherein R is hydrogen, an alkyl group, an alkenyl group, a cycloalkyl group, a benzyl group or a phenyl group. The imidazole compounds are important starting products for the preparation of hypotensive pharmaceuticals or herbicides.
Abstract: A new catalytic composition, comprising the oxides of vanadium, titanium, zirconium and molybdenum is disclosed. The new catalytic composition is applied in the oxidative ammonolysis of alkylpyridines.
Type:
Grant
Filed:
January 7, 1997
Date of Patent:
December 16, 1997
Assignees:
Lonza Ltd., Institute of Chemical Science of the National Academy of Science of the Republic of Kazakstan
Inventors:
Dauren C. Sembaev, Faina A. Ivanovskaya, Ernest M. Guseinov, Roderick J. Chuck
Abstract: A process for the preparation of 2-substituted 5-chloroimidazole-4-carbaldehydes of the general formula: ##STR1## in which glycine is reacted with an imido ester of the general formula: ##STR2## and the resultant intermediate is converted into the product by a Vilsmeier reagent. The 2-substituted 5-chloroimidazole-4-carbaldehydes are valuable intermediates for the preparation of pharmaceuticals or herbicidally active compounds.