Processes Patents (Class 554/114)
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Patent number: 6696606Abstract: A solid phase synthetic method for preparing arylretinamides is provided. The method comprises reacting hexachloroacetone with a solvent-suspended resin-bound triphenylphosphine to provide a suspension comprising an activated chlorinating reagent; reacting retinoic acid with the activated chlorinating reagent to provide retinoyl chloride; adding pyridine and a select arylamine to the resulting mixture; and stirring the resulting mixture for a time and at a temperature sufficient for the select arylamine to react with the retinoyl chloride and provide the arylretinamide. Also provided, are select arylretinamides that can be prepared by the present method, and methods of using such arylretinamides to induce apoptosis in cancer cells.Type: GrantFiled: July 8, 2002Date of Patent: February 24, 2004Assignee: The Ohio State University Research FoundationInventors: Robert W. Curley, Jr., Serena M. Mershon
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Patent number: 6541649Abstract: The present invention provides processes for the synthesis of novel cationic amphiphiles capable of facilitating transport of biologically active molecules into cells wherein the said amphiphiles contain N-hydroxyalkyl group and have at least one hydroxyalkyl group containing 1-3 carbon atoms directly linked to the positively charged nitrogen atom.Type: GrantFiled: December 4, 2001Date of Patent: April 1, 2003Assignee: Council of Scientific & Industrial ResearchInventors: Rajkumar Banerjee, Prasanta Kumar Das, Gollapudi Venkata Srilakshmi, Nalam Madhusudhana Rao, Arabinda Chaudhuri
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Patent number: 6451761Abstract: A method of treating a CNS disorder in a subject in need of such treatment, the method comprising administering to the subject an effective amount of an N′N′-dichlorinated amino acid, peptide, peptidomimetic, amine, or a pharmacologically acceptable analogue or derivative thereof, such that a CNS disorder is treated. An N′N′-dichlorinated amino acid, peptide, peptidomimetic, or amine capable of crossing the blood-brain barrier of a subject when administered thereto.Type: GrantFiled: September 26, 2000Date of Patent: September 17, 2002Assignee: Queen's University at KingstonInventors: Nico M. van Gelder, Raymond J. Bowers
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Publication number: 20020007080Abstract: Novel compounds derived from traditional semi-drying and non-drying oils featuring internally plasticizing and crosslinkable properties are disclosed and claimed. Preferred embodiments include acrylate or methacrylate esters of hydroxy long-chain olefinic compounds derived from castor oil or lesquerella oil. A process for the preparation of the novel compounds is also disclosed, which involves esterification reaction of ethylenically unsaturated carboxylic acids or its derivatives with substituted hydroxy long-chain olefinic compounds. These compounds are suitable for forming latices, which form films at low minimum film forming temperatures (MFT) ranging from −5 to 10° C. and cure to above ambient glass transition (Tg) polymers without the use of traditional organic cosolvents which contribute to environmental pollution via volatile organic compounds (VOCs) emissions. These latices are therefore useful in waterborne coatings, contact and pressure sensitive adhesives, and inks.Type: ApplicationFiled: April 10, 2001Publication date: January 17, 2002Applicant: University of Southern MississippiInventors: Shelby Freland Thames, Kamlesh Gopichand Panjnani, Rajan Hariharan, Zhiyu Wang
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Publication number: 20020002298Abstract: The invention relates to a process for the production of esterquats in which triglycerides are transesterified with alkanolamines and the resulting fatty acid alkanolamine esters are subsequently quaternized with alkyl halides or dialkyl sulfates in the presence of solvents, characterized in that glycerol released during the transesterification is continuously removed from the reaction equilibrium.Type: ApplicationFiled: May 11, 2001Publication date: January 3, 2002Inventors: Joaquim Bigorra Llosas, Rafael Pi Subirana, Nuria Bonastre Gilabert
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Publication number: 20010031883Abstract: Novel compounds derived from traditional semi- drying and non-drying oils featuring internally plasticizing and crosslinkable properties are disclosed and claimed. Preferred embodiments include acrylate or methacrylate esters of hydroxy long-chain olefinic compounds derived from castor oil or lesquerella oil. A process for the preparation of the novel compounds is also disclosed, which involves esterification reaction of ethylenically unsaturated carboxylic acids or its derivatives with substituted hydroxy long-chain olefinic compounds. These compounds are suitable for forming latices, which form films at low minimum film forming temperatures (MFT) ranging from −5 to 10° C. and cure to above ambient glass transition (Tg) polymers without the use of traditional organic cosolvents which contribute to environmental pollution via volatile organic compounds (VOCs) emissions. These latices are therefore useful in waterborne coatings, contact and pressure sensitive adhesives, and inks.Type: ApplicationFiled: April 10, 2001Publication date: October 18, 2001Applicant: The University of Southern MississippiInventors: Shelby Freland Thames, Kamlesh Gopichand Panjnani, Rajan Hariharan, Zhiyu Wang
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Patent number: 6271185Abstract: Industrial oils containing partial esters of triacylglycerol and triethanolamine or ethoxylated triethanolamine are described, as well as methods for making such oils.Type: GrantFiled: October 29, 1999Date of Patent: August 7, 2001Assignee: Cargill, IncorporatedInventors: Dharma Kodali, Scott C. Nivens
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Patent number: 6235914Abstract: A process for making a tertiary amine ester of the following formula (I): the process comprising: (a) reacting a ketone or an aldehyde having the formula with a glycol to form a ketal or an acetal; (b) reacting the ketal or the acetal with acrylonitrile to form an ether nitrile; (c) reducing the ether nitrile to a tertiary amine ketal or a tertiary amine acetal; (d) hydrolyzing the tertiary amine ketal or the tertiary amine acetal to a tertiary amine diol; and (e) esterifying the tertiary amine diol to the tertiary amine ester of formula (I), wherein R1 and R2 are each independently a hydrogen atom or a linear, branched, or cyclic alkyl, alkylene, alkaryl, or aryl-containing group containing 1 to 18 carbon atoms; and each R3 are each independently of one another fatty acid radicals having 6-22 carbon atoms.Type: GrantFiled: August 18, 2000Date of Patent: May 22, 2001Assignee: Goldschmidt Chemical CompanyInventors: Philip Howard Steiger, Christopher Joseph Toney
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Patent number: 6235916Abstract: Novel compounds derived from traditional semi-drying and non-drying oils featuring internally plasticizing and crosslinkable properties are disclosed and claimed. Preferred embodiments include acrylate or methacrylate esters of hydroxy long-chain olefinic compounds derived from castor oil or lesquerella oil. A process for the preparation of the novel compounds is also disclosed, which involves esterification reaction of ethylenically unsaturated carboxylic acids or its derivatives with substituted hydroxy long-chain olefinic compounds. These compounds are suitable for forming latices, which form films at low minimum film forming temperatures (MFT) ranging from −5 to 10° C. and cure to above ambient glass transition (Tg) polymers without the use of traditional organic cosolvents which contribute to environmental pollution via volatile organic compounds (VOCs) emissions. These latices are therefore useful in waterborne coatings, contact and pressure sensitive adhesives, and inks.Type: GrantFiled: December 24, 1996Date of Patent: May 22, 2001Assignee: University of Southern MississippiInventors: Shelby Freland Thames, Kamlesh Gopichand Panjnani, Rajan Hariharan, Zhiyu Wang
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Patent number: 6200624Abstract: This invention is directed to the use of triglycerides containing fatty ester moieties that include arachidonic acid (AA) and docosahexaenoic acid (DHA) in enteral nutritionals or nutritional supplements. These triglycerides are derived from lipid mixtures which have high levels of sterols and phosphorous. A preferred embodiment of the invention comprises an infant or enteral nutritional, or nutritional supplement, that comprises a lipid source derived from egg yolk. The lipid source derived from egg yolk is prepared by transesterification or hydrolysis, subjecting the mixture to distillation, and esterification with glycerin to result in a triglyceride containing the desired fatty acids of AA and DHA and little or no sterols and phosphorus.Type: GrantFiled: January 26, 1996Date of Patent: March 13, 2001Assignee: Abbott LaboratoriesInventors: Terrence Bruce Mazer, Robert Alan Miller, Charles Allan McCombs, Scott Donald Barnicki, James Cecil Phillips, Charles Edwan Sumner, Jr.
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Patent number: 6187938Abstract: The invention relates to amino acid derivatives of general formula (I), wherein R1 is H or CH3, X is H or NR2R3, wherein R2 is H, CH3, COH or COCH3 and R3 is H, CH3 or COO—Z wherein Z is R2R3 NH+CHR1(CH2)nCOO(CH2)mCH2Y; Y is H, CH3 or NHR4, wherein R4 a COO—NH3+CH2(CH2)mOOC(CH2)nCH3, the meaning of group (CH2)m being selected from alkyls, secondary alkyls, monocycloalkyls, bicycloalkyls and tricycloalkyls having from 4 to 15 carbon atoms and n having a value of from 3 to 14.Type: GrantFiled: December 21, 1999Date of Patent: February 13, 2001Assignee: Bochemie, s.r.o.Inventors: Alexandr Hrabálek, Pavel Dole{haeck over (z)}al, Old{haeck over (r)}ich Farsa, Ale{haeck over (s)} Krebs, Ale{haeck over (s)} Kroutil, Martin Roman, Zde{haeck over (n)}ka {haeck over (S)}klubalová
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Patent number: 6090958Abstract: Carrier compounds and compositions therewith which are useful in the delivery of active agents are provided. Methods of administration and preparation are provided as well.Type: GrantFiled: February 7, 1997Date of Patent: July 18, 2000Assignee: Emisphere Technologies, Inc.Inventors: Andrea Leone-Bay, Koc-Kan Ho, Donald J. Sarubbi, Harry R. Leipold
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Patent number: 6084112Abstract: A convenient synthetic route to .omega.-aminoalkanoic acids, N-Boc protected .omega.-aminoalkanoic acids and Boc-amino acid coupled .omega.-aminoalkanoic acids is disclosed. The method provides high purity compounds that generally do not require further purification.Type: GrantFiled: December 15, 1997Date of Patent: July 4, 2000Assignee: Emisphere Technologies, Inc.Inventors: Koc-Kan Ho, Andrea Leone-Bay
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Patent number: 6046344Abstract: A process for the preparation of hydroxypropylated quaternary ammonium compounds containing an ester functional group, preferably a fatty acid ester functional group, of formula (I): ##STR1## in which: R denotes a saturated or unsaturated, linear or branched C.sub.7 -C.sub.35 alkyl chain;R.sub.1, R.sub.2 and R.sub.3 independently denote a saturated or unsaturated, linear or branched C.sub.1 -C.sub.18 alkyl chain;X.sup.- denotes a halide or another anion chosen from: ##STR2## in which: R.sub.4 and R.sub.5 independently denote a saturated or unsaturated, linear or branched C.sub.1 -C.sub.8 alkyl chain, wherein the process comprises reacting, in a single step and in an alcoholic solvent at reflux, an aliphatic carboxylic acid (RCOOH) salt or an aliphatic carboxylic acid under basic catalysis conditions with a compound of formula (II): ##STR3## in which R.sub.1, R.sub.2, R.sub.3 and X.sup.- are defined as above.Type: GrantFiled: December 10, 1997Date of Patent: April 4, 2000Assignee: L'OrealInventors: Michel Philippe, Alain Campos
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Patent number: 5886201Abstract: A process for producing quaternized fatty acid triethanolamine ester salts having improved solubility in water, by esterifiying a fatty acid mixture containinga) 40% to 60% by weight of linear fatty acids containing 6 to 22 carbon atoms, andb) 60% to 40% by weight of branched fatty acids containing 6 to 22 carbon atoms,wherein the esterifying step is conducted with triethanolamine or ethylene oxide adducts of triethanolamine, and the resultant esters are then quaternized.Type: GrantFiled: April 8, 1996Date of Patent: March 23, 1999Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Nuria Bonastre, Joaquim Bigorra Llosas, Rafael Pi Subirana
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Patent number: 5880299Abstract: The invention relates to new esterquats which are obtained by reacting trialkanolamines with a mixture of fatty acids and dicarboxylic acids and quaternizing the resulting esters in known manner, optionally after alkoxylation. Cationic surfactants are obtained which show particularly high ecotoxicological compatibility, provide synthetic and natural fibers with a pleasant feel and, at the same time, reduce electrostatic charging between the filaments.Type: GrantFiled: October 24, 1996Date of Patent: March 9, 1999Assignee: Henkel CorporationInventors: Oriol Ponsati Obiols, Nuria Bonastre, Joaquim Bigorra Llosas
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Patent number: 5869716Abstract: Esterquats based on natural fats and oils can be directly produced by subjecting fatty acid glyerine ester to ester interchange, in the presence of alkaline and/or alkaline earth boron hydrides and hypophosphoric acid or their alkaline and/or alkaline earth salts and possibly free fatty acid, with hydroxy-functionalised tertiary amines and quaternising the resultant products in the manner known per se.Type: GrantFiled: September 16, 1996Date of Patent: February 9, 1999Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Rafael Pi Subirana, Joaquim Bigorra Llosas, Antonio Trius Oliva
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Patent number: 5851982Abstract: To provide a liquid softener composition which is satisfactory in respects of softening effect, storage stability and water absorption properties, is excellent in biodegradability and is gentle with the environment. A liquid softener composition comprising 3 to 40% by weight of a quaternary ammonium salt (7-I) and water ##STR1## wherein R.sup.1 represents C.sub.20 -C.sub.44 alkyl or alkenyl group; R.sup.2, R.sup.3, and R.sup.4 are the same of different from each other and are C.sub.1 -C.sub.5 alkyl or hydroxyalkyl group; Y represents C.sub.2 -C.sub.4 alkylene group; m is a number of 0 to 20; n is an integer of 1 to 6; and X.sup.- represents an anion group.Type: GrantFiled: March 27, 1996Date of Patent: December 22, 1998Assignee: Kao CorporationInventors: Yuushi Sakata, Junichi Inokoshi, Osamu Tachizawa, Tohru Katoh, Uichiro Nishimoto, Yasuki Ohtawa, Akira Sakaguchi, Kohshiroh Sotoya, deceased, Noriko Yamaguchi
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Patent number: 5783534Abstract: A process for the production of a solid esterquat free from solvents comprising the steps ofA) forming a mixture comprising(i) at least one fatty acid triethanolamine ester corresponding to formula (I) ##STR1## in which R.sup.1 CO is a saturated and/or unsaturated acyl radical containing 6 to 22 carbon atoms, R.sup.2 and R.sup.3 independently of one another represent hydrogen or have the same meaning as R.sup.1 CO, and n, m and p together stand for O or for a number of from 1 to 10;(ii) at least one fatty alcohol polyglycol ether, and(iii) at least one fatty acid partial glyceride; andB) adding an alkylating agent to the above mixture to form said solid esterquat.Type: GrantFiled: July 15, 1996Date of Patent: July 21, 1998Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Bernd Wahle, Joaquim Bigorra Llosas, Rafael Pi, Antoni Soler Codina, Emili Brau Balague, Yvonne Reichert, Peter Waltenberger
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Patent number: 5705663Abstract: The invention relates to quaternized triethanolamine difatty acid esters prepared from triethanolamine, fatty acid, fatty acid ester and a quaternizing agent and to a process for their preparation and to their use. The quaternized triethanolamine difatty acid esters thus prepared can be used to produce particularly storage-, temperature- and viscosity-stable rinse cycle laundry softeners having a high active content.Type: GrantFiled: December 7, 1995Date of Patent: January 6, 1998Assignee: Servo Delden B.V.Inventors: Michael Brock, Meinolf Enneking, Kurt Kosswig
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Patent number: 5696070Abstract: A liquid softener composition comprising a quaternary ammonium salt represented by the general formula (1) and a method for its preparation: ##STR1## wherein R.sup.1, R.sup.2, and R.sup.3 are an alkyl group or hydroxyalkyl group of 1 to 4 carbon atoms, R.sup.4 and R.sup.5 are an unsubstituted or hydroxyl group-substituted linear or branched alkyl group or alkenyl group of 8 to 36 carbon atoms, A is a linear or branched alkylene group of 2 or 3 carbon atoms, X is an anion group, n is an integer in the range of 1 to 6, and m is a numeral in the range of 0 to 20.Type: GrantFiled: February 23, 1996Date of Patent: December 9, 1997Assignee: Kao CorporationInventors: Osamu Tachizawa, Akira Sakaguchi, Tohru Katoh, Kohshiro Sotoya, deceased, Noriko Yamaguchi, Junichi Inokoshi, Muneo Aoyagi
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Patent number: 5670677Abstract: A process for the production of color- and odor-stable quaternized fatty acid triethanolamine ester salts comprising the steps ofA) partially or fully esterifying triethanolamine with at least one fatty acid in the presence of hypophosphorous acid;B) adding a peroxide compound and an alkali metal boranate to the esterification product from step A); andC) quaternizing the esterification product with an alkyl halide, a (di)alkyl sulfate or an alkylene oxide in the presence of a phenol derivative and a hydroxycarboxylic acid.Type: GrantFiled: September 18, 1995Date of Patent: September 23, 1997Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Oriol Ponsati Obiols, Joaquim Bigorra Llosas
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Patent number: 5625067Abstract: The invention relates to cyclopentane ether derivatives of Formula I ##STR1## their salts with physiologically compatible bases, as well as the .alpha.-, .beta.- or .gamma.-cyclodextrin clathrates, and also the liposome-encapsulated compounds of Formula I, processes for their production, and their pharmaceutical usage.Type: GrantFiled: December 14, 1994Date of Patent: April 29, 1997Assignee: Schering AktiengesellschaftInventors: Hartmut Rehwinkel, Ulrich Klar, Helmut Vorbruggen, Karl-Heinz Thierauch, Peter Verhallen
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Patent number: 5530148Abstract: A process for producing 12-oxododecanoic acid oxime, a novel compound which can be used as a raw material in several industrial processes, is disclosed. The disclosed process relies on a renewable raw material, vernolic (cis-12,13-epoxy-cis-9-octadecenoic) acid. The process utilizes readily available chemical technology which does not involve the use of gaseous hydrocarbon or petrochemical-base feedstock. Hydrogenation of vernolic acid produces 12,13-epoxystearic acid, which can be oxidized with periodic acid to give 12-oxododecanoic acid, which can be reacted with hydroxylamine to yield 12-oxododecanoic acid oxime. A process for reducing the 12-oxododecanoic acid oxime to yield 12-aminododecanoic acid, the monomer for nylon-12, is also disclosed.Type: GrantFiled: March 15, 1995Date of Patent: June 25, 1996Assignee: Howard UniversityInventors: Chukwuma P. Nwaonicha, Folahan O. Ayorinde
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Patent number: 5523433Abstract: Disclosed is a process for making di(acyloxyalkyl) di(alkyl) ammonium compounds useful as fabric softeners. The corresponding di(hydroxyalkyl) tertiary amine is diesterified under conditions determined to minimize the formation of monoester side product and then the diester is quaternized under conditions effective to minimize degradation of the quaternized diester.Type: GrantFiled: September 29, 1994Date of Patent: June 4, 1996Assignee: Witco CorporationInventors: Christopher J. Toney, Phillip S. Welte, Robert K. Lagerman
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Patent number: 5245060Abstract: A terpene derivative represented by the general formula (I): ##STR1## wherein R.sup.1 represents a lower alkyl group; R.sup.2 represents an alkyl group, a cycloalkyl group, a cycloalkylalkyl group, an aryl group, an arylalkyl group or a heteroaryl group; n is 0 or 1 or 2; and the symbol " " represents a single or double bond with the proviso that both of the linkages adjacent to each other are not simultaneously single bonds or double bonds which are useful for the preparation of drug, food, perfume and so on, and a process for preparing thereof.Type: GrantFiled: March 12, 1992Date of Patent: September 14, 1993Assignee: Eisai Co. Ltd.Inventors: Kimio Hamamura, Yoshio Urawa, Yukio Narabe, Yoshihiko Hisatake, Shizumasa Kijima
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Patent number: 5223638Abstract: The present invention provides a process for preparing urethanes and carbonates from an amine or an alcohol, carbon dioxide and a hydrocarbyl halide. The amine or alcohol is reacted with carbon dioxide in a suitable solvent system and in the presence of an amidine or guanidine base, to form the ammonium carbamate or carbonate salt which is then reacted in a polar aprotic solvent with a hydrocarbyl halide. Polymer products can also be prepared utilizing this process or utilizing the resulting urethanes and carbonates under standard polymerization conditions.Type: GrantFiled: April 29, 1991Date of Patent: June 29, 1993Assignee: Monsanto CompanyInventors: William D. McGhee, Barry L. Parnas, Dennis P. Riley, John J. Talley