Abstract: A new process for the production of tetronic acid alkyl esters of the general formula: ##STR1## starting from 4-haloacetoacetic acid alkyl esters of the general formula: ##STR2## The 4-haloacetoacetic acid alkyl esters of general formula II are converted in a first step with a dialkylsulfite of the general formula:(RO).sub.2 S.dbd.O IIIin the presence of a strong acid into a 4-halo-3-alkoxy-but-2E-enoic acid alkyl ester of the general formula: ##STR3## The latter is cyclized in a second step with a formate and a strong acid to the end product according to formula I.
Abstract: Polyol impurities in a sorbitan ester mixture is removed by treating a polyol-containing sorbitan ester dissolved in a solution containing a hydrocarbon and a polar organic solvent with an aqueous metal halide salt solution.
Abstract: 2,5-bis(1,1-dialkoxy-2-propyl)-2,5-dihydrofurans of the formula I ##STR1## where R.sup.1 and R.sup.2 can be identical or different and can be alkyl of 1 to 4 carbons, the preparation thereof by reaction of 2,5-dialkoxy-2,5-dihydrofurans of the formula II ##STR2## In the presence of protic acids or Lewis acids with an alkyl propenyl ether of the formula III ##STR3## and the use thereof for preparing 2,7-dimethyl-2,4,6-octatrienedial and symmetric C.sub.40 -carotenoids such as .beta.-carotene, canthaxanthin and astaxanthin, are described.
Type:
Grant
Filed:
April 10, 1992
Date of Patent:
April 5, 1994
Assignee:
BASF Aktiengesellschaft
Inventors:
Juergen Frank, Udo Rheude, Bernhard Schulz, Joachim Paust, Eckhard Hickmann
Abstract: A process for producing coumarin or a derivative thereof, which process comprises dehydrogenation of 3,4-dihydrocoumarin or a derivative thereof in the presence of a palladium catalyst by heating under reduced pressure.
Abstract: Chiral epoxybutyrates are prepared in high yield from novel dihydro-3R-substituted sulfonyloxy-4R-hydroxy-2-(3H)furanones via based catalyzed alcoholysis. The product chiral epoxy butyrates are useful intermediates for the synthesis of 1-carba-1-dethia cephem antibiotics.
Abstract: There are provided cycloalkyl piperidine compounds which are useful in the treatment of physiological or drug-induced psychosis or dyskinesia in a mammal. These novel compounds are selective sigma receptor antagonists and have a low potential for movement disorder side effects associated with typical antipsychotic agents.
Type:
Grant
Filed:
February 6, 1992
Date of Patent:
March 22, 1994
Assignee:
The Du Pont Merck Pharmaceutical Company
Inventors:
Gary A. Cain, Paul J. Gilligan, Sang W. Tam
Abstract: Compounds of formula I: ##STR1## wherein: R1 is hydrogen or alkyl;R2 is alkyl optionally substituted by one or more alkoxy groups or halogen atoms;X is a group of formula --OR3 wherein R3 is alkyl, cycloalkyl, or arylalkyl; or X is a group of formula --NHCVR4 wherein V is oxygen or sulphur, R4 is hydrogen, alkyl, cycloalkyl (which alkyl and cycloalkyl groups may be substituted), alkenyl, aryl, arylalkyl, amino, mono- or di-alkylamino or a group of the formula --OR5 wherein R5 is optionally substituted alkyl, aryl or arylalkyl; or X is a group of formula --NHSO.sub.2 R4a wherein R4a is alkyl, aryl or a group of formula --CH.sub.2 COR4b wherein R4b is alkyl or aryl;Y is optionally substituted alkoxy, cycloalkoxy, arylalkoxy or a group of formula --NR6R7 wherein R6 is hydrogen or alkyl and R7 is alkyl, cycloalkyl (which alkyl and cycloalkyl groups may be substituted), aryl or arylalkyl or R7 is a group of formula --COOR8 wherein R8 is alkyl are useful intermediates in the synthesis of beta-lactam antibiotics.
Type:
Grant
Filed:
July 23, 1992
Date of Patent:
March 22, 1994
Assignee:
Imperial Chemical Industries plc
Inventors:
Richard W. Bayles, Anthony P. Flynn, Ralph W. Turner
Abstract: A process for the stereoselective preparation of 5-substituted .delta.-lactones of the formulae Ia, Ib, Ic and Id ##STR1## in which R.sup.1 is a straight-chain or branched alkyl or alkenyl group or methylhydroxy, novel 5-substituted .delta.-lactones and novel intermediates, and use thereof as pharmaceuticals having cholesterol synthesis-inhibiting action, fragrances and flavorings is described.
Type:
Grant
Filed:
September 1, 1992
Date of Patent:
March 8, 1994
Assignee:
Hoechst Aktiengesellschaft
Inventors:
Peter Hammann, Susanne Grabley, Ernold Granzer, Yvonne Romeyke
Abstract: The present invention relates to a compound of the formula: ##STR1## wherein R.sup.1 is 2-methyl-1-propenyl group or isobutyl group; R.sup.2 and R.sup.3 are each hydrogen atom, an optionally substituted hydrocarbon residue or an optionally substituted acyl group or R.sup.2 and R.sup.3 may form a ring together with the adjacent nitrogen atom; and the bonding mark .about. represents an .alpha.-linkage or .beta.-linkage, or a salt thereof. The compound (I) of the present invention has, among others, angiogenesis inhibiting activity, cell-growth inhibiting activity and immune reaction inhibiting activity, thus being useful as medicines, etc.
Abstract: Taxane derivatives of the formula ##STR1## wherein R.sub.1 is butenyl,R.sub.3 is phenyl,T.sub.1 is hydrogen, hydroxyl protecting group, or --COT.sub.2,T.sub.2 is H, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl or monocylic aryl,Ac is acetyl, andE.sub.1 and E.sub.2 are independently selected from hydrogen and functional groups which increase the water solubility of the taxane derivative are useful as antitumor agents.
Abstract: Taxane derivatives of the formula ##STR1## wherein R.sub.1 is phenyl or p-nitrophenyl,R.sub.3 is furyl or thienyl,T.sub.1 is hydrogen, hydroxyl protecting group, or --COT.sub.2,T.sub.2 is H, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl or monocylic aryl,Ac is acetyl, andE.sub.1 and E.sub.2 are independently selected from hydrogen and functional groups which increase the water solubility of the taxane derivative are useful as antitumor agents.
Type:
Grant
Filed:
November 13, 1992
Date of Patent:
February 1, 1994
Assignee:
Florida State University
Inventors:
Robert A. Holton, Kasthuri Rengan, Hossain Nadizadeh
Abstract: A polycylic dye of the Formula (1): ##STR1## wherein: R.sup.1 is --OSO.sub.2 R in which R is optionally substituted alkyl, alkoxy, aryl, alkoxyaryl, cycloalkyl or heteroaryl;Ring A is unsubstituted or is substituted by from one to three groups; andRing B is unsubstituted or is substituted by one or two groups in addition to the group R.sup.1.Dyes of the present invention are useful for the coloration of textile materials particularly synthetic textile materials such as polyester, dye mixtures comprising a polycyclic dye of Formula (1) and a different polycyclic dye or an azo dye show improved build-up on polyester material.
Abstract: The present invention is a method that uses an absorption column for the cleavage and recovery of taxanes, which are not normally detected as free taxanes. The method processes a first solution that contains standard detectable taxanes and other undetectable taxane compounds to generate a second solution that contains a higher percentage of detectable standard taxane then the first solution. The first step of this method is loading a column having a first opening and a second opening with an ion exchange media. The next step is placing the first solution in the first opening of the column so that the first solution passes through the ion exchange media in the column and flows to the second opening. Thus, the taxane compounds are converted to standard taxanes by an ion exchange reaction and the second solution is formed.
Type:
Grant
Filed:
November 27, 1992
Date of Patent:
January 25, 1994
Assignee:
NaPro BioTherapeutics, Inc.
Inventors:
David R. Carver, Timothy R. Prout, Christopher T. Workman, Donia L. Henderson, Charles L. Hughes
Abstract: Sulfonated 2'-acryloyltaxol and sulfonated 2'-O-acyl acid taxol derivatives are synthesized which have improved water solubility and stability while maintaining bioactivity. In particular, 2'-[(3-sulfo-1-oxopropyl)oxy]taxol sodium salt is synthesized by reacting taxol with acrylic acid, and subsequently reacting the 2'-acryloyltaxol with bisulfite in a Michael reaction. 2'-{[4-((2-sulfoethyl)amino)-1,4-dioxobutyl]oxy}taxol sodium salt and 2'-{[4-((3-sulfopropyl)amino)-1,4-dioxobutyl]oxy}taxol sodium salt are synthesized by reacting 2'-succinyltaxol with the tetrabutylammonium salts of taurine and 3-aminopropyl sulfonic acid, respectively, and subsequently exchanging the ammonium with sodium. Glycol derivatives of 2'-O-acyl acid taxols with improved water solubility are synthesized by reaction of a glycol with 2'-O-acyl acid taxol.
Type:
Grant
Filed:
October 15, 1991
Date of Patent:
January 11, 1994
Assignee:
Virginia Tech Intellectual Properties, Inc.
Abstract: A process for simultaneously producing a lactone and an aromatic carboxylic acid, which comprises oxidizing a cyclic ketone and an aromatic aldehyde wherein: the cyclic ketone/aromatic aldehyde molar ratio is set at 1.1:1 to 20:1 and the throughput of the aromatic aldehyde per a unit reaction solution volume and a unit time is set at 0.05 to 1.5 mol/1.hour.
Abstract: A process for the treatment of a quaternary onium salt is described. The process comprises the steps of (i) contacting an organic phase soaringly miscible in water containing a quaternary onium fluorine-containing carboxylate of RfCO.sub.2.sup.-+ AR.sup.1 R.sup.2 R.sup.3 R.sup.4 as defined in the present Specification with an aqueous phase containing a thiocyanate ion to form a quaternary onium thiocyanate in the organic phase and (ii) contacting the organic phase containing the quaternary onium thiocyanate with an aqueous solution containing a water-soluble oxidizing agent to decompose the thiocyanate ion and to form an easily ion exchangeable quaternary onium salt. Also, applications of this treatment to a process for preparing hexafluoropropylene oxide from hexafluoropropylene in a two-phase system of an aqueous phase and an organic phase by using a hypochlorite as an oxidizing agent in the presence of a quaternary onium salt as a catalyst are described.
Abstract: There is disclosed a new process for the epoxidization of olefins by reaction with hydrogen peroxide according to the double phase technique with "onium" salts, characterized in that the reaction is conducted in a liquid aqueous-organic biphasic system consisting of:(a) an organic phase substantially containing the olefin, and(b) an aqueous acid phase substantially containing hydrogen peroxide,in the presence of a catalytic system consisting of a first component which is at least one element selected from W. Mo, V or at least one derivative of said elements, and of a second component which is at least one derivative selected from the derivatives of P and As.
Type:
Grant
Filed:
September 14, 1990
Date of Patent:
December 28, 1993
Assignee:
Instituto Guido Donegani, S.p.A.
Inventors:
Carlo Venturello, Enzo Alneri, Giulio Lana
Abstract: A metal alkoxide having the following formula: ##STR1## wherein T.sub.1 is hydrogen or a hydroxy protecting group, Z is --OT.sub.2, or --OCOCH.sub.3, T.sub.2 is hydrogen or a hydroxy protecting group, and M is selected from the group comprising Group IA, IIA and transition metals are useful in the preparation of biologically active derivatives of baccatin III and 10-deacetyl baccatin III.
Abstract: A taxol intermediate selected from the group consisting of: ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and each selected from hydrogen, hydroxyl, or a protected hydroxyl; or R.sup.1 and R.sup.2 together form an oxo or a protected oxo; R.sup.3 is formyl, a protected formyl, or --CH(X)--OY wherein X is hydrogen or a monovalent metal and Y is hydrogen or a hydroxyl protecting group; and R.sup.4 and R.sup.5 are different and each selected from chloro or cyano; or R.sup.4 and R.sup.5 together form an oxo or a protected oxo, with the proviso that R.sup.1 and R.sup.2 are not both hydroxyl; R.sup.6 is hydroxyl or a protected hydroxyl; R.sup.7 is hydrogen, hydroxyl, or a protected hydroxyl; R.sup.8 is carboxyl, hydroxylmethyl, or a protected hydroxylmethyl; or R.sup.7 and R.sup.8 when taken together with carbon atoms 3 and 4, form an oxetane ring; or R.sup.6 and R.sup.8 when taken together with carbon atoms 1 and 4, form a bridged lactone; R.sup.9 is hydrogen or a hydroxyl protecting group; R.sup.
Type:
Grant
Filed:
June 23, 1992
Date of Patent:
December 28, 1993
Inventors:
K. C. Nicolaou, Chan-Kou Hwang, Erik J. Sorensen, Jin-Jun Liu