Patents by Inventor Leander Tenud
Leander Tenud 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: 5162540Abstract: (3aS,6aR)-[(R)-(1-phenylethyl)-3,4-methoxybenzyl dihydro-1H-furo-[3,4-d]-imidazol-2,4(3H,3aH)-dione and 1H-furo-[3,4-d]-imidazol-2,4-(3H,3aH)-dione derivatives which are useful as intermediates for preparing (+) biotin, also known as vitamin H.Type: GrantFiled: October 17, 1991Date of Patent: November 10, 1992Assignee: Lonza Ltd.Inventors: John McGarrity, Leander Tenud
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Patent number: 5117003Abstract: Process for the production of (+) biotin.Type: GrantFiled: January 10, 1989Date of Patent: May 26, 1992Assignee: Lonza Ltd.Inventors: John McGarrity, Leander Tenud
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Patent number: 5093503Abstract: Process for the production of thiotetronic acid wherein 4-chloroacetoacetic acid chloride is reacted with hydrogen sulfide in the presence of an amine.Type: GrantFiled: September 11, 1990Date of Patent: March 3, 1992Assignee: Lonza Ltd.Inventors: Thomas Meul, Leander Tenud
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Patent number: 4997957Abstract: Process for the production of thiotetronic acid wherein 4-chloroacetoacetic acid chloride is reacted with hydrogen sulfide in the presence of an amine.Type: GrantFiled: July 23, 1987Date of Patent: March 5, 1991Assignee: Lonza, Ltd.Inventors: Thomas Meul, Leander Tenud
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Patent number: 4880940Abstract: 4-Alkoxy-3-pyrrolin-2-on-1-yl acetic acid alkyl esters are intermediate products for the production of cerebrally-active pharmaceutical products. The advantageous process for production of the new intermediate products is described.Type: GrantFiled: July 22, 1988Date of Patent: November 14, 1989Assignee: Lonza Ltd.Inventors: Thomas Muel, Leander Tenud, Laurent Duc, John McGarrity
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Patent number: 4876350Abstract: Process for the production of (+) biotin. A compound of the formula: ##STR1## wherein R.sub.1 is e.g., an (R)-1-phenylalkyl group, and R.sub.2 is, e.g., hydrogen. The desired diastereomer of the formula: ##STR2## is separated out. If R.sub.2 is H, a protective group is introduced by reaction with, e.g., an aliphatic acid chloride. The diastereomer is converted by reaction with a thiocarboxylic acid salt derivative into the corresponding thiolacetone, which is reacted with a Grignard reactant and subsequently water is split off. Alternatively, the corresponding thiolacetone is reacted with a compound of the formula:(C.sub.6 H.sub.5).sub.3 P.sup..sym. (CH.sub.2).sub.4 COOR.sub.3.X.sup..crclbar.wherein R.sub.3 is, e.g., H, and X is a halogen atom, in the presence of a base to provide a compound of the formula: ##STR3## Such compound is catalytically hydrogenated and then converted into (+) biotin by cleavage of the protective groups.Type: GrantFiled: December 16, 1987Date of Patent: October 24, 1989Assignee: Lonza Ltd.Inventors: John McGarrity, Leander Tenud
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Patent number: 4873339Abstract: Imidazole derivatives of the formula: ##STR1## wherein R.sub.1 is an (R)- or (S)-1-phenylalkyl group, an (R)- or (S)-1-alkoxycarbonyl-1-phenylmethyl group or an (R)- or (S)-1-aryloxycarbonyl-1-phenylmethyl group, R.sub.2 is hydrogen, a substituted or unsubstituted alkanoyl group, a substituted or unsubstituted benzoyl group, a substituted or unsubstituted benzyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an alkoxyalkyl group, a pyranyl group, a substituted or unsubstituted benzenesulfonyl group, an alkylsufonyl group, a diarylphosphinyl group, a dialkoxyphosphinyl group or a trialkylsilyl group, and A is a sulfur or oxygen atom. The imidazole derivatives are intermediate products for the production of (+) biotin.Type: GrantFiled: November 30, 1988Date of Patent: October 10, 1989Assignee: Lonza Ltd.Inventors: John McGarrity, Leander Tenud, Thomas Meul
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Patent number: 4851540Abstract: Process for the production of imidazole derivatives of the formula: ##STR1## wherein R.sub.1 is an (R)- or (S)-1-phenylalkyl group, an (R)- or (S)-1-alkoxycarbonyl-1-phenylmethyl group or an (R)- or (S)-1-aryloxycarbonyl-1-phenylmethyl group, R.sub.2 is hydrogen, a substituted or unsubstituted alkanoyl group, an unsubstituted or a substituted benzoyl group, a substituted or an unsubstituted benzyl group, an alkoxycarbonyl group, and aryloxycarbonyl group, an alkoxyalkyl group, a pyranyl group, a substituted or unsubstituted benzenesulfonyl group, an alkylsulfonyl group, a diarylphosphinyl group, a dialkoxyphosphinyl group or a trialkylsilyl group, and A is a sulfur or oxygen atom.Type: GrantFiled: December 1, 1987Date of Patent: July 25, 1989Assignee: Lonza Ltd.Inventors: John McGarrity, Leander Tenud, Thomas Meul
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Patent number: 4801750Abstract: Process for the production of 2-chloroacetoacetic acid amides. Diketene is converted at a temperature of +30.degree. to -40.degree. C. with the help of hydrogen chloride into acetoacetic acid chloride. Chlorine is introduced into the mixture at a temperature of +30.degree. to -40.degree. C., whereby 2-chloroacetoacetic acid chloride is formed. The latter is converted into the corresponding amide at a temperature of +50.degree. to -40.degree. C. by reaction with a N-compound having the formula: ##STR1## wherein (i) R=R'=H, or(ii) R=R'=alkyl, substituted alkyl, aryl, substituted aryl, alkyl aryl, substituted alkyl aryl, alkoxy aryl, substituted alkoxy aryl, alkoxy alkyl or substituted alkoxy alky, or(iii) R=H, and R'=alkyl, substituted alkyl, aryl, substituted aryl, alkyl aryl, substituted alkyl aryl, alkoxy aryl, substituted alkoxy aryl, alkoxy alkyl or substituted alkoxy alkyl.Type: GrantFiled: March 24, 1982Date of Patent: January 31, 1989Assignee: Lonza Ltd.Inventors: Leander Tenud, Raimund Miller, Barry Jackson
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Patent number: 4780545Abstract: 4-Alkoxy-3-pyrrolin-2-on-1-yl acetic acid alkyl esters are intermediate products for the production of cerebrally-active pharmaceutical products. The advantageous process for production of the new intermediate products is described.Type: GrantFiled: November 18, 1986Date of Patent: October 25, 1988Assignee: Lonza Ltd.Inventors: Thomas Meul, Leander Tenud, Laurent Duc, John McGarrity
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Patent number: 4732999Abstract: Process for the production of optically-active di-[3-chloro-2-oxy-propyltrimethylammonium]-tartrate. Racemic 3-chloro-2-oxy-propyltrimethylammonium-chloride is converted by racemate resolution with optically-active tartaric acid into the optically-active di-[3-chloro-2-oxy-propyltrimethylammonium]-tartrate. Such optically-active tartrate compound is dissociated in tartaric acid to optically-active 3-chloro-2-oxy-propyltrimethylammonium-chloride and the latter is converted with inorganic cyanides. From the product, the production of optically-active carnitine nitrile chloride can be achieved.Type: GrantFiled: June 24, 1986Date of Patent: March 22, 1988Assignee: Lonza Ltd.Inventors: Leander Tenud, Jacques Gosteli
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Patent number: 4732709Abstract: Process for the production of optically-active di-[3-chloro-2-oxy-propyltrimethylammonium]-tartrate. Racemic 3-chloro-2-oxy-propyltrimethylammonium-chloride is converted by racemate resolution with optically-active tartaric acid into the optically-active di-[3-chloro-2-oxy-propyltrimethylammonium]-tartrate. Such optically-active tartrate compound is dissociated in tartaric acid and optically-active 3-chloro-2-oxy-propyltrimethylammonium-chloride and the latter is converted with inorganic cyanides. From the product, the production of optically-active carnitine nitrile chloride can be achieved.Type: GrantFiled: June 24, 1986Date of Patent: March 22, 1988Assignee: Lonza Ltd.Inventors: Leander Tenud, Jacques Gosteli
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Patent number: 4692543Abstract: Process for the production of optically-active di-[3-chloro-2-oxy-propyltrimethylammonium]-tartrate. Racemic 3-chloro-2-oxy-propyltrimethylammonium-chloride is converted by racemate resolution with CaCl.sub.2, for example, into the optically-active di-[3-chloro-2-oxy-propyltrimethylammonium]-tartrate. Such optically-active tartrate compound is dissociated into calcium tartrate and optically-active 3-chloro-2-oxy-propyltrimethylammonium-chloride, and the latter is converted with inorganic cyanides. From the product, the production of optically-active carnitine nitrile chloride can be achieved.Type: GrantFiled: February 25, 1986Date of Patent: September 8, 1987Assignee: Lonza Ltd.Inventors: Leander Tenud, Jacques Gosteli
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Patent number: 4670192Abstract: Process for the production of optically-active di-[3-chloro-2-hydroxy-propyltrimethylammonium]-tartrate. Racemic 3-chloro-2-hydroxy-propyltrimethylammonium-chloride is converted by racemate resolution with optically-active tartaric acid into the optically-active di-[3-chloro-2-hydroxy-propyltrimethylammonium]-tartrate. Such optically-active tartrate compound is dissociated in tartaric acid and optically-active 3-chloro-2-hydroxy-propyltrimethylammonium-chloride and the latter is converted with inorganic cyanides. From the product, the production of optically-active carnitine nitrile chloride can be achieved.Type: GrantFiled: June 24, 1986Date of Patent: June 2, 1987Assignee: Lonza Ltd.Inventors: Leander Tenud, Jacques Gosteli
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Patent number: 4558158Abstract: Process for the production of 4-(trialkylammonium)-acetoacetarylides having the formula: ##STR1## wherein R is H, a lower alkyl, --OCH.sub.3, --OC.sub.2 H.sub.5, --Cl, --Br, --NO.sub.2, --NHCOCH.sub.3 or an anilated heterocyclic ring; n is 1 to 3; R.sup.1, R.sup.2 and R.sup.3 each is an alkyl having 1 to 18 C atoms; and X is Cl or Br. Such arylide is prepared by reacting a corresponding trialkylamine with a corresponding 4-haloacetoacetarylide at a low temperature in the presence of an organic solvent.Type: GrantFiled: June 7, 1983Date of Patent: December 10, 1985Assignee: Lonza Ltd.Inventors: Leander Tenud, Synese Jolidon
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Patent number: 4552983Abstract: Process for the production of 4-(trialkylammonium)-acetoacetarylides having the formula: ##STR1## wherein: R is H, a lower alkyl, --OCH.sub.3, --OC.sub.2 H.sub.5, --Cl, --Br, --NO.sub.2, --NHCOCH.sub.3 or an anilated heterocyclic ring; n is 1 to 3; R.sup.1, R.sup.2 and R.sup.3 each is an alkyl having 1 to 18 C atoms; and X is Cl or Br. Such arylide is prepared by reacting a corresponding trialkylamine with a corresponding 4-haloacetoacetarylide at a low temperature in the presence of an organic solvent.Type: GrantFiled: September 20, 1984Date of Patent: November 12, 1985Assignee: Lonza Ltd.Inventors: Leander Tenud, Synese Jolidon
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Patent number: 4545934Abstract: Process for the production of 4-substituted acetoacetic acid derivatives. An acetoacetic acid derivative having the formula: ##STR1## wherein R is alkoxy having 1 to 6 C atoms, phenoxy, --NR'.sub.2, wherein R' is alkyl having 1 to 6 C atoms or aryl, or NR'.sub.2, which is azetidine, pyrrolidine or piperidine, is treated with a secondary amine at an elevated temperature and in the presence of an organic solvent. The water formed is separated. The intermediate is converted into the corresponding 3-enamine carboxylic acid derivative. The derivative is converted by treatment with sodium amide in liquid ammonia into the corresponding sodium salt. The sodium salt is converted by treatment with a halogen compound having the formula R.sub.1 CH.sub.2 X or R.sub.1 R.sub.2 CHX, wherein R.sub.1 and R.sub.2 each are alkyl, alkenyl, alkinyl or aryl and X is chlorine, bromine or iodide, into the corresponding 4-substituted enamino derivative. The derivative is hydrolyzed into the 4-substituted acetoacetic acid derivative.Type: GrantFiled: March 21, 1984Date of Patent: October 8, 1985Assignee: Lonza Ltd.Inventors: Felix Previdoli, Leander Tenud
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Patent number: 4503234Abstract: Process for the production of 2-(2-aminothiazole-4-yl)-2-(syn)-methoxyimino acetic ester. First 4-chloroacetoacetic ester is oximized and then the resultant chlorohydroxyimino ester, in solution form, reacted with thiourea to produce 2-(2-aminothiazole-4-yl)-2-(syn)-hydroxyimino acetic ester. The latter is methylated with dimethyl sulfate using phase transfer catalysis.Type: GrantFiled: July 24, 1981Date of Patent: March 5, 1985Assignee: Lonza Ltd.Inventors: Alfred Huwiler, Leander Tenud
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Patent number: 4443627Abstract: Process for the production of carnitine amide in the form of a chloride. The carnitine ethyl ester is obtained by reaction of 4-chloroacetoacetic acid ethyl ester with trimethyl amine and the subsequent hydrogenation is carried out with the help of a Pt/C catalyst. Such carnitine ethyl ester, without isolating it, is reacted with ammonia in an autoclave at -30.degree. to +10.degree. C. Everything is heated to 40.degree. to 80.degree. C. The mixture is stirred at such temperature at an ammoniac pressure of 8 to 24 atu. The product is filtered after cooling it to ambient temperature and counterbalancing the excess pressure. The product is then washed with alcohol and subsequently dried at 30.degree. to 50.degree. C. and at a pressure of 15 to 25 torr.Type: GrantFiled: January 20, 1982Date of Patent: April 17, 1984Assignee: Lonza Ltd.Inventors: Leander Tenud, Rene Blum
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Patent number: 4421922Abstract: Process for the production of tetronic acid from 4-haloacetoacetic ester which begins by converting a 4-haloacetoacetic ester into the corresponding 4-benzyloxyacetoacetic ester. The 4-benzyl ester is then hydrogenolyzed into an intermediate product. The 4-hydroxyacetoacetic ester is converted by treatment with acid into tetronic acid. The 4-hydroxyacetoacetic ester can be isolated before conversion. The 4-benzyloxyacetoacetic ester can be produced by conversion of the 4-haloacetoacetic ester with a metal salt of benzyl alcohol. The hydrogenolysis can be carried out in the presence of an acid, whereby the 4-hydroxyacetoacetic ester forming in situ is rearranged directly into tetronic acid. The hydrogenolysis can be carried out under pressure in the presence of a hydrogenation catalyst.Type: GrantFiled: June 14, 1982Date of Patent: December 20, 1983Assignee: Lonza Ltd.Inventors: Raimund Miller, Leander Tenud