Abstract: The present invention relates to a process for the production of (S)-1,2,3,4-tetrahydro-6,7-dialkoxy-3-isoquinolinecarboxylic acid compounds (1) and their derivatives from Levodopa (L-Dopa). The ultimately prepared compounds are used as intermediates for, but not limited to, the preparation of substituted derivatives of 1,2,3,4-tetrahydro-6,7-dialkoxy-3-isoquinolinecarboxylic acid
wherein
R1 is hydrogen, lower alkyl, C2-C12 acyl, or R1O together are methylenedioxy;
R2 is hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, aryl, substituted aryl, aralkyl or substituted aralkyl group; and
R3 is hydrogen, C2-C12 acyl group, benzyl, alkoxylcarbonyl group, or aralkoxyl carbonyl group.
Abstract: There are disclosed novel Stavudine solvates as follows: Stavudine NN-dimethyllacetamide solvates; Stavudine NN-dimethylacrylamide solvates and Stavudine NN-dimethylpropionamide solvates and processes for producing Stavudine NN-dimethylacetamide solvates, Stavudine NN dimethylacrylamide solvates and Stavudine NN dimethylpropionamide solvates which results in pure Stavudine.
Abstract: A process for the preparation of 1,3-oxathiolane nucleoside analogues in predominantly the cis-form, from mixture of cis-/trans-1,3-oxathiolane nucleosides or their protected derivatives thereof, comprising:
(i) treatment of the cis-/trans-1,3-oxathiolane nucleosides (or protected derivatives thereof) with a pyrimidine base (or it derivatives thereof) and an acid,
(ii) adding a suitable acid to the obtained cis-/trans-mixture of isomers,
(iii) selective crystallization of the desired cis-isomer salt from a solvent or combination of solvents, and
(iv) treatment of the predominantly cis-isomer salt with a suitable base to offer the free 1,3-oxathiolane nucleosides, and thereafter optionally repeating steps (i) to (iv) inclusive.
Type:
Grant
Filed:
June 18, 2001
Date of Patent:
July 29, 2003
Assignee:
Brantford Chemicals Inc.
Inventors:
K. S. Keshava Murthy, Gurijala V. Reddy, Zhi-xian Wang, Chandrawansha B. W. Senanayake
Abstract: A process for the preparation of Nefazodone hydrochloride comprising direct conversion of semicarbazide dihydrochloride 3 into Nefazodone hydrochloride which process involves a reaction of triethyl orthopropionate in the presence of trimethylsilylchloride and hydrochloric acid.
Type:
Grant
Filed:
September 17, 2001
Date of Patent:
July 22, 2003
Assignee:
Brantford Chemicals Inc.
Inventors:
K. S. Keshava Murthy, Bhaskar Reddy Guntoori, Daqing Che
Abstract: This invention relates to the preparation of 3-sulfonamido-4-arylaminopyridines by heating a 3-sulfonamido-4-aminopyridine with an aryl halide in the presence of an alkaline compound, a copper-containing agent and in the presence of a polar protic solvent.
Type:
Grant
Filed:
November 14, 2002
Date of Patent:
July 15, 2003
Assignee:
Brantford Chemicals Inc.
Inventors:
Carlos B. Zetina-Rocha, Bhaskar Reddy Guntoori, Stephen E. Horne
Abstract: A process for the manufacture of 3,5-diamino-6-substituted-1,2,4-triazines is disclosed which comprises the steps of:
(a) reacting a compound of formula (II):
with aminoguanidine salts,
(b) dehydrating the compound obtained to form a compound of formula IV,
and
(c) cyclization of the compound of formula IV into a 3,5-diamino-6-substituted-1,2,4-triazine compound of formula I or into a hydrated form thereof.
Type:
Grant
Filed:
January 16, 2002
Date of Patent:
July 1, 2003
Assignee:
Brantford Chemicals Inc.
Inventors:
Bhaskar Reddy Guntoori, Daqing Che, K. S. Keshava Murthy
Abstract: A process for the preparation of Nefazodone hydrochloride comprising direct conversion of semicarbazide dihydrochloride 3 into Nefazodone hydrochloride which process involves a reaction of triethyl orthopropionate in the presence of trimethylsilylchloride and hydrochloric acid.
Type:
Application
Filed:
September 17, 2001
Publication date:
April 24, 2003
Applicant:
Brantford Chemicals Inc.
Inventors:
K. S. Keshava Murthy, Bhaskar Reddy Guntoori, Daqing Che
Abstract: A process for the preparation of tetrahydrothieno[3,2-c]pyridine derivatives of general formula I:
or their pharmaceutically acceptable salts, wherein the meaning of X is hydrogen, carboxyl, alkoxycarbonyl, aryloxycarbonyl, nitrile, or carbamoyl of formula
wherein R1 and R2 can be individually or simultaneously hydrogen, alkyl or part of a heterocyclic structure; Z can be hydrogen, halogen, alkyl, aryl, aryloxy or alkoxy group.
Type:
Grant
Filed:
July 11, 2001
Date of Patent:
December 17, 2002
Assignee:
Brantford Chemicals Inc.
Inventors:
Stephen E. Horne, Gamini Weeratunga, Bogdan M. Comanita, Jaipal Reddy Nagireddy, Laura Kaye McConachie
Abstract: Paroxetine hydrochloride anhydrous designated as Form IV having at least one, some or all of the following characteristics:
a) Infrared spectra as shown in FIG. 1 and 2,
b) A X-ray powder diffraction pattern as shown in Schedule “C”,
c) A melting point of between about 80°0 C. to about 95° C.
Type:
Grant
Filed:
November 24, 1997
Date of Patent:
August 20, 2002
Assignee:
Brantford Chemicals Inc.
Inventors:
K. S. Keshava Murthy, Allan Rey, Gamini Weeratunga
Abstract: A process for separating diastereomeric mixtures of compounds of formula 1 and formula 2
wherein R1=H or R1 denotes a carboxyl-esterifying group selected from C1-C6 alkyl and C7-C8 aralkyl, by treating the mixture of 1 and 2 with a solvent or mixture of solvents to obtain a substantially pure compound of formula 1.
Abstract: A compound of the formula A,
wherein R* is a chiral auxiliary, and where the configuration at the asymmetric carbon atom between oxygen and sulfur is (R), (S), or combinations of (R) and (S), useful in the preparation of enantiomerically enriched 1,3-oxathiolane nucleoside analogues, for example (−)-FTC and 3TC.
Type:
Grant
Filed:
May 18, 2000
Date of Patent:
April 30, 2002
Assignee:
Brantford Chemicals Inc.
Inventors:
K. S. Keshava Murthy, Stephen E. Horne, Gurijala V. Reddy, Chandrawansha B. W. Senanayake, Bruno K. Radatus
Abstract: A process for manufacturing Simvastatin is provided comprising reacting lovastatin with an organic boronic acid to produce a derivative of lovastatin (lovastatin phenylboronate) methylating the 2-methylbutyryloxy group on the lovastatin derivative to form a 2,2-dimethylbutyryloxy group on the lovastatin derivative and thereafter removing the boronate group to produce simvastatin.
Type:
Grant
Filed:
November 21, 1996
Date of Patent:
October 23, 2001
Assignee:
Brantford Chemicals Inc.
Inventors:
K. S. Keshava Murthy, Stephen E. Horne, Gamini Weeratunga, Shawn Young
Abstract: A process is provided for the preparation of 1,2,5,6-tetrahydro-3-carboalkoxypyridines of formula (III) ##STR1## wherein R is a straight or cyclic substituted or unsubstituted alkyl chain having 1 to 6 carbon atoms, phenyl C.sub.1-6 alkyl, menthol or a derivative of menthol, or a derivative of camphor, and R' is an alkyl chain having 1 to 4 carbon atoms or phenyl C.sub.1-6 alkyl comprising reacting an alkyl pyridinium salt of formula ##STR2## wherein R and R' are as defined above and X is a suitable leaving group with sodium triacetoxyborohydride in the presence of an acid.
Type:
Grant
Filed:
August 19, 1997
Date of Patent:
October 17, 2000
Assignee:
Brantford Chemicals Inc.
Inventors:
K. S. Keshave Murthy, Allan W. Rey, Dan S. Matu
Abstract: A process is provided for the manufacture of 4-lower-alkyl-5-hydroxymethyl-imidazole comprising reacting (4)-lower-alkyl imidazole with formaldehyde in an alkanol solvent having from 2 to 5 carbon atoms in the presence of a solid mild base suspended in the solvent.
Type:
Grant
Filed:
December 13, 1995
Date of Patent:
August 22, 2000
Assignee:
Brantford Chemicals Inc.
Inventors:
K. S. Keshava Murthy, Gamini Weeratunga, Derek John Norris
Abstract: This invention relates to new stereoselective processes for preparing 3-substituted-4-aryl piperidines and methods for controlling the absolute stereochemistry at the C-3 and C-4 positions of the piperidine ring. Compounds of this type are key intermediates in the preparation of paroxetine, femoxetine, and other medicaments.
Abstract: A process is provided for the manufacture of: where R is: ##STR1## comprising reacting: ##STR2## wherein R.sub.1 may be selected from H, Methyl, Ethyl and suitable lower alkyl groups, C.sub.n H.sub.2n+1 (where n is from 3 to 5) or any other suitable group and thereafter if desired converting the resultant product to a salt thereof.
Type:
Grant
Filed:
April 4, 1996
Date of Patent:
July 6, 1999
Assignee:
Brantford Chemicals Inc.
Inventors:
K. S. Keshava Murthy, Gamini Weeratunga, Tianhao Zhou, Bhaskar Reddy Guntoori
Abstract: A process of manufacture of:R--CH.sub.2 --S--CH.sub.2 --CH.sub.2 --NH.sub.2 2HC1wherein R is selected from the group consisting of ##STR1## is provided, the said process comprising reacting R--CH.sub.2 OH.HCL with HSCH.sub.2 CH.sub.2 NH.sub.2 .HC1 in a suitable solvent in the presence of an effective amount of Hydrochloric acid.
Type:
Grant
Filed:
December 13, 1995
Date of Patent:
May 12, 1998
Assignee:
Brantford Chemicals Inc.
Inventors:
K.S. Keshava Murthy, Gamini Weeratunga, Bruno Konrad Radatus, Kanwar Pal Singh Sidhu
Abstract: Novel methods for the synthesis of substituted ureas and guanidines including Terazosin, Prazosin, Doxazosin, Tiodazosin, Trimazosin, Quinasin and Bunazosin (exemplary of 2-amino substituted Quinazolines), Meobentine and Bethanidine and novel intermediates suitable for use in such methods of synthesis are taught.
Type:
Grant
Filed:
May 30, 1995
Date of Patent:
November 11, 1997
Assignee:
Brantford Chemicals Inc.
Inventors:
Khashayar Karimian, Keshava Murthy, Darren Hall