Processes Patents (Class 554/114)
  • Patent number: 6696606
    Abstract: 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: Grant
    Filed: July 8, 2002
    Date of Patent: February 24, 2004
    Assignee: The Ohio State University Research Foundation
    Inventors: Robert W. Curley, Jr., Serena M. Mershon
  • Patent number: 6541649
    Abstract: 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: Grant
    Filed: December 4, 2001
    Date of Patent: April 1, 2003
    Assignee: Council of Scientific & Industrial Research
    Inventors: Rajkumar Banerjee, Prasanta Kumar Das, Gollapudi Venkata Srilakshmi, Nalam Madhusudhana Rao, Arabinda Chaudhuri
  • Patent number: 6451761
    Abstract: 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: Grant
    Filed: September 26, 2000
    Date of Patent: September 17, 2002
    Assignee: Queen's University at Kingston
    Inventors: Nico M. van Gelder, Raymond J. Bowers
  • Publication number: 20020007080
    Abstract: 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: Application
    Filed: April 10, 2001
    Publication date: January 17, 2002
    Applicant: University of Southern Mississippi
    Inventors: Shelby Freland Thames, Kamlesh Gopichand Panjnani, Rajan Hariharan, Zhiyu Wang
  • Publication number: 20020002298
    Abstract: 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: Application
    Filed: May 11, 2001
    Publication date: January 3, 2002
    Inventors: Joaquim Bigorra Llosas, Rafael Pi Subirana, Nuria Bonastre Gilabert
  • Publication number: 20010031883
    Abstract: 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: Application
    Filed: April 10, 2001
    Publication date: October 18, 2001
    Applicant: The University of Southern Mississippi
    Inventors: Shelby Freland Thames, Kamlesh Gopichand Panjnani, Rajan Hariharan, Zhiyu Wang
  • Patent number: 6271185
    Abstract: Industrial oils containing partial esters of triacylglycerol and triethanolamine or ethoxylated triethanolamine are described, as well as methods for making such oils.
    Type: Grant
    Filed: October 29, 1999
    Date of Patent: August 7, 2001
    Assignee: Cargill, Incorporated
    Inventors: Dharma Kodali, Scott C. Nivens
  • Patent number: 6235914
    Abstract: 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: Grant
    Filed: August 18, 2000
    Date of Patent: May 22, 2001
    Assignee: Goldschmidt Chemical Company
    Inventors: Philip Howard Steiger, Christopher Joseph Toney
  • Patent number: 6235916
    Abstract: 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: Grant
    Filed: December 24, 1996
    Date of Patent: May 22, 2001
    Assignee: University of Southern Mississippi
    Inventors: Shelby Freland Thames, Kamlesh Gopichand Panjnani, Rajan Hariharan, Zhiyu Wang
  • Patent number: 6200624
    Abstract: 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: Grant
    Filed: January 26, 1996
    Date of Patent: March 13, 2001
    Assignee: Abbott Laboratories
    Inventors: Terrence Bruce Mazer, Robert Alan Miller, Charles Allan McCombs, Scott Donald Barnicki, James Cecil Phillips, Charles Edwan Sumner, Jr.
  • Patent number: 6187938
    Abstract: 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: Grant
    Filed: December 21, 1999
    Date of Patent: February 13, 2001
    Assignee: 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
  • Patent number: 6090958
    Abstract: 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: Grant
    Filed: February 7, 1997
    Date of Patent: July 18, 2000
    Assignee: Emisphere Technologies, Inc.
    Inventors: Andrea Leone-Bay, Koc-Kan Ho, Donald J. Sarubbi, Harry R. Leipold
  • Patent number: 6084112
    Abstract: 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: Grant
    Filed: December 15, 1997
    Date of Patent: July 4, 2000
    Assignee: Emisphere Technologies, Inc.
    Inventors: Koc-Kan Ho, Andrea Leone-Bay
  • Patent number: 6046344
    Abstract: 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: Grant
    Filed: December 10, 1997
    Date of Patent: April 4, 2000
    Assignee: L'Oreal
    Inventors: Michel Philippe, Alain Campos
  • Patent number: 5886201
    Abstract: 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: Grant
    Filed: April 8, 1996
    Date of Patent: March 23, 1999
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Nuria Bonastre, Joaquim Bigorra Llosas, Rafael Pi Subirana
  • Patent number: 5880299
    Abstract: 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: Grant
    Filed: October 24, 1996
    Date of Patent: March 9, 1999
    Assignee: Henkel Corporation
    Inventors: Oriol Ponsati Obiols, Nuria Bonastre, Joaquim Bigorra Llosas
  • Patent number: 5869716
    Abstract: 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: Grant
    Filed: September 16, 1996
    Date of Patent: February 9, 1999
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Rafael Pi Subirana, Joaquim Bigorra Llosas, Antonio Trius Oliva
  • Patent number: 5851982
    Abstract: 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: Grant
    Filed: March 27, 1996
    Date of Patent: December 22, 1998
    Assignee: Kao Corporation
    Inventors: Yuushi Sakata, Junichi Inokoshi, Osamu Tachizawa, Tohru Katoh, Uichiro Nishimoto, Yasuki Ohtawa, Akira Sakaguchi, Kohshiroh Sotoya, deceased, Noriko Yamaguchi
  • Patent number: 5783534
    Abstract: 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: Grant
    Filed: July 15, 1996
    Date of Patent: July 21, 1998
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Bernd Wahle, Joaquim Bigorra Llosas, Rafael Pi, Antoni Soler Codina, Emili Brau Balague, Yvonne Reichert, Peter Waltenberger
  • Patent number: 5705663
    Abstract: 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: Grant
    Filed: December 7, 1995
    Date of Patent: January 6, 1998
    Assignee: Servo Delden B.V.
    Inventors: Michael Brock, Meinolf Enneking, Kurt Kosswig
  • Patent number: 5696070
    Abstract: 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: Grant
    Filed: February 23, 1996
    Date of Patent: December 9, 1997
    Assignee: Kao Corporation
    Inventors: Osamu Tachizawa, Akira Sakaguchi, Tohru Katoh, Kohshiro Sotoya, deceased, Noriko Yamaguchi, Junichi Inokoshi, Muneo Aoyagi
  • Patent number: 5670677
    Abstract: 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: Grant
    Filed: September 18, 1995
    Date of Patent: September 23, 1997
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Oriol Ponsati Obiols, Joaquim Bigorra Llosas
  • Patent number: 5625067
    Abstract: 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: Grant
    Filed: December 14, 1994
    Date of Patent: April 29, 1997
    Assignee: Schering Aktiengesellschaft
    Inventors: Hartmut Rehwinkel, Ulrich Klar, Helmut Vorbruggen, Karl-Heinz Thierauch, Peter Verhallen
  • Patent number: 5530148
    Abstract: 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: Grant
    Filed: March 15, 1995
    Date of Patent: June 25, 1996
    Assignee: Howard University
    Inventors: Chukwuma P. Nwaonicha, Folahan O. Ayorinde
  • Patent number: 5523433
    Abstract: 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: Grant
    Filed: September 29, 1994
    Date of Patent: June 4, 1996
    Assignee: Witco Corporation
    Inventors: Christopher J. Toney, Phillip S. Welte, Robert K. Lagerman
  • Patent number: 5245060
    Abstract: 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: Grant
    Filed: March 12, 1992
    Date of Patent: September 14, 1993
    Assignee: Eisai Co. Ltd.
    Inventors: Kimio Hamamura, Yoshio Urawa, Yukio Narabe, Yoshihiko Hisatake, Shizumasa Kijima
  • Patent number: 5223638
    Abstract: 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: Grant
    Filed: April 29, 1991
    Date of Patent: June 29, 1993
    Assignee: Monsanto Company
    Inventors: William D. McGhee, Barry L. Parnas, Dennis P. Riley, John J. Talley