Nitrogen Containing Patents (Class 568/583)
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Patent number: 6008321Abstract: A substrate for solid phase synthesis of the formula: ##STR1## is disclosed. Also disclosed are processes for preparing the substrate and intermediates useful therein. Among the novel intermediates are compounds of the formula: ##STR2## wherein t is 0 or 1; n is 3-20; R is OH, an activated ester or the residue of a solid support having a plurality of amino functionalities; A is --O-- or --NH-- and Q is hydrogen or a protecting group for an amine or alcohol.Type: GrantFiled: March 16, 1998Date of Patent: December 28, 1999Assignee: Pharmacopeia, Inc.Inventors: Ge Li, Sian Louise Griffiths, Edward McDonald, Libo Xu
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Patent number: 5945393Abstract: Novel nonionic gemini surfactants are extremely effective emulsifiers for oil-in-water emulsions that provide improved detergency at even low concentration levels. The surfactants are characterized by the formula: ##STR1## wherein R.sub.1 is independently H or a C.sub.1 to C.sub.22 alkyl, R.sub.2 is C.sub.6 to C.sub.22 alkyl and R.sub.3 is D.sub.1 --R.sub.4 --D.sub.1 or R.sub.4 --D.sub.1 --R.sub.4 wherein R.sub.4 is independently a C.sub.1 -C.sub.10 alkyl group, --O--R.sub.5 --O--, or aryl, e.g. phenyl, and D.sub.1 is independently --O--, an amide group ?--C(O)N(R.sub.6)--!, an amino group ?--N(R.sub.6)--!, --O--R.sub.5 --O--, or aryl. (EO).sub.a (PO).sub.b is a polyether group and Z is a C.sub.1 -C.sub.4 alkyl, or an alkylaryl or hydrogen wherein EO represents ethyleneoxy radicals, PO represents propyleneoxy radicals, a and b are numbers of from 0 to 100, a is preferably from about 0 to about 30 and b is preferably from about 0 to 10, wherein a plus b is at least one, and the EO and PO alkyl or alkylaryl.Type: GrantFiled: November 7, 1997Date of Patent: August 31, 1999Assignee: Rhodia Inc.Inventors: David James Tracy, Ruoxin Li, Manilal S. Dahanayake, Jiang Yang
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Patent number: 5869715Abstract: For use in transporting biologically active species into and through membrane barriers, a cationic amine compound is utilized that has the general structure: ##STR1## wherein R.sub.4 and R.sub.5 are a pair of same or different lipoyl moieties selected from a group consisting of an alkyl, alkenyl, alkynyl, alkanoyl, alkenoyl, or alkynoyl groups and for R.sub.1 R.sub.2, and R.sub.3 at least two are hydroxylated, ether containing, or acyloxy containing alkyl, alkenyl, or alkynyl groups or at least one amine bonded halogen containing moiety selected from a group consisting of a halogenated alkyl, alkenyl, or alkynyl group or a mixture of at least one halogen containing moiety selected from a group consisting of a halogenated alkyl, alkenyl, or alkynyl group and at least one hydroxylated, ether containing, or acyloxy containing alkyl, alkenyl, or alkynyl group, and X.sup.- is an anion.Type: GrantFiled: September 27, 1995Date of Patent: February 9, 1999Assignee: The Reagents of the University of CaliforniaInventors: Michael H. Nantz, Michael J. Bennett, Rajiv P. Balasubramaniam
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Patent number: 5831114Abstract: Substituted N-phenyl- and N-heteroarylalkylcarbamates of formula (I), in which Q is a group (1), (2) or (3); R is halogen, trifluoromethyl, cyano, nitro or C.sub.1 -C.sub.3 haloalkoxy; Z is hydrogen or halogen; or Z and R together in the 2- and 3-position of the phenyl ring form a group --OCF.sub.2 O--; R.sub.1 is C.sub.1 -C.sub.5 alkyl; R.sub.2, R.sub.3, R.sub.4 and R.sub.5, independently of one another, are hydrogen, methyl or ethyl; X is oxygen, sulfur, --SO-- or --SO.sub.2 --, Y is hydrogen, halogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.3 alkoxy or cyano; n is 0, 1 or 2; n.sub.1 is 0 or 1; and m is 0 or 1, with the proviso that m is 1 if Q is group (1) or (2); and the diastereomers and enantiomers thereof, exhibit pre- and post-emergence herbicidal properties. The preparation of these compounds and their use as herbicidally active ingredients are described.Type: GrantFiled: May 28, 1997Date of Patent: November 3, 1998Assignee: Novartis Finance CorporationInventors: Hermann Rempfler, Fredrik Cederbaum, Felix Spindler, Willy Urs Lottenbach
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Patent number: 5831102Abstract: Enzymatically cleavable chemiluminescent 1,2-dioxetane compounds capable of producing light energy when decomposed, substantially stable at room temperature before a bond by which an enzymatically cleavable labile substituent thereof is intentionally cleaved, are disclosed. These compounds can be represented by the formula: ##STR1## wherein: X and X.sup.1 each represent, individually, hydrogen, a hydroxyl group, a halo substituent, an unsubstituted lower alkyl group, a hydroxy (lower) alkyl group, a halo (lower) alkyl group, a phenyl group, a halophenyl group, an alkoxyphenyl group, a hydroxyalkoxy group, a cyano group or an amide group, with at least one of X and X.sup.1 being other than hydrogen; andR.sub.1 and R.sub.2, individually or together, represent an organic substituent that does not interfere with the production of light when the dioxetane compound is enzymatically cleaved and that satisfies the valence of the dioxetane compound's 4-carbon atom, with the provisos that if R.sup.1 and R.sub.Type: GrantFiled: February 8, 1996Date of Patent: November 3, 1998
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Patent number: 5830244Abstract: A fuel additive having the formula: ##STR1## wherein R.sub.1 and R.sub.2 are independently hydrogen or lower alkyl; R.sub.3 and R.sub.4 are independently hydrogen or lower alkyl and each R.sub.3 and R.sub.4 is independently selected in each --O--CHR.sub.3 --CHR.sub.4 -- unit; R.sub.5 is hydrogen, alkyl having 1 to 100 carbon atoms, phenyl, aralkyl having 7 to 100 carbon atoms or alkaryl having 7 to 100 carbon atoms, or an acyl group of the formula: ##STR2## where R.sub.6 is alkyl having 1 to 30 carbon atoms, phenyl, aralkyl having 7 to 36 carbon atoms or alkaryl having 7 to 36 carbon atoms; n is an integer from 5 to 100; and x is an integer from 0 to 10.Type: GrantFiled: December 30, 1996Date of Patent: November 3, 1998Assignee: Chevron Chemical CompanyInventor: Richard E. Cherpeck
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Patent number: 5801260Abstract: Novel substrates of phospholipases, lysophospholipases and lipases are disclosed.Type: GrantFiled: June 7, 1995Date of Patent: September 1, 1998Assignee: LaJolla Pharmaceuticals Co.Inventors: Lin Yu, Robert John Termansky
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Patent number: 5708092Abstract: A process for the preparation of hydrocarbon solutions of monofunctional ether initiators of the following general structure:M--Q.sub.n --Z--OA(R.sup.1 R.sup.2 R.sup.3)wherein M is defined as an alkali metal, selected from the group consisting of lithium, sodium and potassium, Q is a saturated or unsaturated hydrocarbyl group derived by incorporation of a compound selected from the group consisting of conjugated diene hydrocarbons and alkenylsubstituted aromatic hydrocarbons; Z is a branched or straight chain hydrocarbon group which contains 3-25 carbon atoms, optionally containing aryl or substituted aryl groups; A is an element selected from carbon and silicon; R.sup.1, R.sup.2, and R.sup.Type: GrantFiled: April 12, 1996Date of Patent: January 13, 1998Assignee: FMC CorporationInventors: James A. Schwindeman, Conrad W. Kamienski, Robert C. Morrison
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Patent number: 5658951Abstract: Diphenylcyclopropyl analogs in which one or more of the phenyl rings includes alkoxy substituents including a dialkylaminoalkoxy group, an unsubstituted piperazine alkoxy group, a substituted piperazine alkoxy group, an unsubstituted piperidine alkoxy group, and a substituted piperidine alkoxy group, and which may have one or two alkyl groups bonded to the cyclopropane. The compounds are useful as antiestrogens and anti-tumor agents.Type: GrantFiled: June 7, 1995Date of Patent: August 19, 1997Assignee: Research Corporation TechnologiesInventors: Robert A. Magarian, Joseph T. Pento, Lynette Overacre
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Patent number: 5639904Abstract: The 1-aryloxy-3-alkylamino-2-propanol nitrate esters, having formula I: ##STR1## the enantiomers and diastereoisomers and the therapeutically acceptable salts thereof, wherein R.sub.1 is a chain of general formula II --(CH.sub.2).sub.m --Z--R.sub.2, where: m is 1 or 2; Z is an --O-- ether, --CONH amide or --COO-- ester function; and R.sub.2 is a C.sub.2-3 straight or branched chain alkyl having at least one nitroxy group as substituent; and Ar is a benzene ring when Z is the ether or ester function, and a naphthalene ring when Z is the amide function, are of use for the treatment of cardiovascular affections.Type: GrantFiled: August 11, 1995Date of Patent: June 17, 1997Assignee: Prodesfarma, S.A.Inventors: Maria Prat Quinones, Joan Pi Sallent, Dagmar Vedrilla Veit
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Patent number: 5616745Abstract: New lipopolyamines of general formula (I), their salts, their preparation and their use. ##STR1## n=1 to 5 and m=2 to 6 R represents a radical ##STR2## (R.sub.1 and R.sub.2 : aliphatic radical containing 12 to 22 carbon atoms; R: hydrogen atom or alkyl radical optionally substituted with phenyl), or a radical ##STR3## (X=CH.sub.2, CO; R.sub.3 and R.sub.4 aliphatic radical containing 11 to 21 carbon atoms), their preparation and their use.The lipopolyamines of general formula (I) are especially useful as vectors for the transfection of eukaryotic cells.Type: GrantFiled: June 7, 1995Date of Patent: April 1, 1997Assignee: Centre National de la Recherche ScientifiqueInventors: Jean-Paul Behr, Jean-Philippe Loeffler
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Patent number: 5565585Abstract: A new and practical method for synthesizing heterocyclic polyhydroxylated alkaloids using enzymatic aldol condensation and catalytic intramolecular reductive amination is disclosed.Type: GrantFiled: April 8, 1994Date of Patent: October 15, 1996Assignee: G. D. Searle & Co.Inventors: Chi-Huey Wong, Richard L. Pederson, Yi-Fong Wang
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Patent number: 5502237Abstract: The 1-aryloxy-3-alkylamino-2-propanol nitrate esters of general formula I ##STR1## the enantiomers and diastereoisomers and the therapeutically acceptable salts thereof wherein R.sub.1 is a chain of general formula II-- (CH).sub.m,--Z--R.sub.2, where: m is 1 or 2; Z is an --O-- ether, --CONH-amide or --COO-- ester function; and R.sub.2 is a C.sub.2-3 straight or branched chain alkyl having at least one --ONO.sub.2 group as a substituent; and Ar is a benzene ring when Z is the ether or ester function, and a naphthalene ring when Z is the amide function, are of use for the treatment of cardiovascular affections.Type: GrantFiled: June 27, 1994Date of Patent: March 26, 1996Assignee: Prodesfarma, S. A.Inventors: Mari/ a Prat Quin, Joan Pi Sallent, Dagmar V. Veit
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Patent number: 5466872Abstract: Fuel compositions containing a major amount of hydrocarbons boiling in the gasoline or diesel range and an effective deposit-controlling amount of a poly(oxyalkylene) aromatic ether having the formula: ##STR1## where A.sub.1 is nitro, amino, N-alkylamino wherein the alkyl group contains 1 to 6 carbon atoms, or N,N-dialkylamino wherein each alkyl group independently contains 1 to 6 carbon atoms; R.sub.1 and R.sub.2 are independently hydrogen, hydroxy, lower alkyl, or lower alkoxy; R.sub.3 and R.sub.4 are independently hydrogen or lower alkyl and each R.sub.3 and R.sub.4 is independently selected in each --O--CHR.sub.3 --CHR.sub.4 -- unit; R.sub.5 is hydrogen, alkyl having 1 to 100 carbon atoms, phenyl, aralkyl having 7 to 100 carbon atoms or alkaryl having 7 to 100 carbon atoms, or an acyl group of the formula: ##STR2## where R.sub.Type: GrantFiled: February 21, 1995Date of Patent: November 14, 1995Assignee: Chevron Chemical CompanyInventor: Richard E. Cherpeck
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Patent number: 5440060Abstract: The demands on the properties of pigments, in particular in the areas of emulsion paints and printing inks, which are continuously becoming more specific made it necessary to develop selective and environmentally safe dispersing and emulsifying agents and coupling auxiliaries.The compounds according to the invention are alkoxylation products prepared from fatty amine dialkylenediamines which, if desired, are linked to give recurring structural units by means of esterification with dicarboxylic acids and in which, preferably, the hydroxyl end groups of these fatty amine alkylenediamine alkoxylates have been esterified with fatty acids, aromatic carboxylic acids and/or resin acids and any hydroxyl groups still present have been converted to the corresponding mono-ester-containing anionic radicals by means of dicarboxylic acids and sulfites.Type: GrantFiled: August 30, 1993Date of Patent: August 8, 1995Assignee: Hoechst AGInventors: Heinz Uhrig, Albert Munkel
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Patent number: 5434304Abstract: The present invention is directed to a process for preparing formoterol and related compounds and derivatives thereof and their pharmacologically and pharmaceutically acceptable fumarate salts and/or solvates. The present invention is also directed to certain formoterol related compounds per se.Type: GrantFiled: September 20, 1994Date of Patent: July 18, 1995Assignee: Aktiebolaget AstraInventors: Jan W. Trofast, Edib Jakupovic, Katarina L. Mansson
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Patent number: 5382702Abstract: Process for producing 5-alkoxy-2,4-dinitroalkylbenzenes of the general formula (I) ##STR1## R.sup.1 =C.sub.1 to C.sub.4 alkyl; R=C.sub.1 to C.sub.6 alkyl group, C.sub.2 to C.sub.4 hydroxyalkyl, C.sub.3 to C.sub.4 dihydroxyalkyl,in which a 3-fluoroalkylbenzene is nitrated and the obtained 2,4-dinitro-5-fluoroalkylbenzene is then reacted with a suitable alcohol at -5.degree. C. to +25.degree. C. with the addition of sodium hydroxide or potassium hydroxide.Type: GrantFiled: November 19, 1993Date of Patent: January 17, 1995Assignee: Wella AktiengesellschaftInventors: Wolfgang R. Balzer, Thomas Clausen, Alexa Weinges
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Patent number: 5360575Abstract: An optically active lactic acid derivative having the formula (1a): ##STR1## wherein A is O or S; B is --(CH.sub.2).sub.m -- or --(CH.sub.2).sub.n --O; R1 is an alkoxy group having 1-22 carbon atoms, a phenolate, a substituted phenolate, a hydroxy group, or a halogen atom; R2 is an alkyl group having 2-8 carbon atoms; m is 0, 1, 2, 3 or 4; n is 2, 3, 4 or 5; C* is an asymmetric carbon atom. Liquid crystal compositions and liquid crystal devices containing the above mentioned derivatives are also disclosed.Type: GrantFiled: November 8, 1991Date of Patent: November 1, 1994Assignee: Industrial Technology Research InstituteInventors: Wen-Liang Tsai, Hwei-Long Kuo
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Patent number: 5354901Abstract: Perfluoro(cycloaliphatic methyleneoxyalkylene) compositions are provided. These compositions comprise perfluoro(cycloaliphatic methyleneoxyalkylene) carbonyl fluoride compounds having (a) a perfluorocycloaliphatic moiety which can have up to two perfluoroalkyl substituents and a perfluoroalkylene substituent, and (b) a perfluoromethyleneoxyalkylene carbonyl fluoride radical, the methylene group of the radical being bonded to a ring carbon atom or the perfluoroalkylene substituent of the moiety and the alkylene group of the perfluoromethyleneoxyalkylene carbonyl fluoride being a perfluoro(methyl)methylene group, a perfluoroisopropyleneoxy(methyl)methylene group, or a poly(perfluoroisopropyleneoxy)perfluoro(methyl)methylene group having up to about 10 perfluoroisopropyleneoxy units.Type: GrantFiled: February 1, 1993Date of Patent: October 11, 1994Assignee: Minnesota Mining and Manufacturing CompanyInventors: Richard M. Flynn, Patricia M. Savu
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Patent number: 5347050Abstract: The compounds of formula I, ##STR1## wherein the substituents have various significances, and physiologically acceptable hydrolyzable derivatives thereof having the hydroxy group in the 2 position of the 3-aminopropoxy side chain in esterified form, are useful as cardioselective .beta.-adrenoceptor blocking agents.Type: GrantFiled: April 13, 1993Date of Patent: September 13, 1994Inventors: Richard Berthold, William J. Louis
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Patent number: 5334756Abstract: A process for preparing carboxylates of polyoxyalkylene siloxanes and -amines, alkylpolyoxyalkylenes, polyoxyalkylene block polymers, alkylamidepolyoxyalkylenes and alkylpolyglucosides comprising subjecting a primary hydroxyl group-containing polyoxyalkylene compound or alkylpolyglucoside to mild oxidiation. The invention also relates to the novel polyoxyalkylene amine and alkylamidepolyoxyalkylene carboxylates prepared by the process.Type: GrantFiled: March 26, 1991Date of Patent: August 2, 1994Assignee: Sandoz Ltd.Inventors: Parfait J. M. Likibi, Robert V. Casciani, Gregory L. McCraw
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Patent number: 5310770Abstract: Water-reducible curing agents for epoxy resins are made from the diglycidyl ether of cyclohexane dimethanol and a diamine selected from the group consisting of meta-xylylene diamine, isophorone diamine, diaminocyclohexane and 1,3-bisaminomethyl cyclohexane.Type: GrantFiled: December 30, 1992Date of Patent: May 10, 1994Assignee: Hi-Tek Polymers, Inc.Inventors: William J. DeGooyer, George A. Roy, II
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Patent number: 5290912Abstract: The present invention has an object of producing a polyoxyalkylene compound by ring-opening polymerization of an alkylene oxide to a certain specific highly hydrophobic initiator. The present invention provides a process for producing a polyoxyalkylene compound, characterized in that the polyoxyalkylene compound is produced by ring-opening polymerization of an alkylene oxide, in the presence of a plural metal cyanide complex catalyst, with an initiator selected from an organopolysiloxane compound having an active hydrogen-containing functional group to which an alkylene oxide is reactive, and a fluorine-containing compound having such an active hydrogen-containing functional group and a fluorinated hydrocarbon group.Type: GrantFiled: January 10, 1992Date of Patent: March 1, 1994Assignee: Asahi Glass Company Ltd.Inventors: Takashi Watabe, Hiromitsu Takeyasu, Shigeyuki Kozawa
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Patent number: 5273686Abstract: Organic-solvent soluble magnesium hydrides or formulas ##STR1## are prepared by catalytically hydrogenating finely powdered magnesium, optionally in the presence of a magnesium halide, in an organic solvent in the presence of their MgH.sub.2 -free counterparts in whichQ is an alkyl, alkenyl, alkoxy, dialkylamino, aralkyl, aryl or diarylamino group, each with up to 18 carbon atoms,R is an alkenyl, aralkyl or aryl group, each with up to 18 carbon atoms,X is chlorine, bromine, or iodine, ##STR2## is a chelating ligand, E is --CH.sub.2, --N(R)-- or --O--,is an alkylene radical of the formula --(CH.sub.2).sub.p,D is a dialkylamino, diarylamino or alkoxy group, each with up to 18 carbon atoms,M is aluminum or boron,m is 1, 2, or 3, and1<n.ltoreq.50.Type: GrantFiled: August 28, 1991Date of Patent: December 28, 1993Assignee: Studiengesellschaft Kohle mbHInventors: Borislav Bogdanovic, Manfred Schwickardi
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Patent number: 5266500Abstract: A method for attaching a reactive amine- or sulfhydryl-containing compound to polymeric particles using dication ether salts is disclosed.Type: GrantFiled: August 3, 1989Date of Patent: November 30, 1993Assignee: Eastman Kodak CompanyInventors: Patricia M. Scensny, Chung-yuan Chen
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Patent number: 5264511Abstract: Monomers, B-stage polymers, C-stage polymers, cured polymers and electricy conducting polymers of acetylene-terminated aromatic monomers containing three benzene rings separated by ethylene groups are disclosed. These new polymers can withstand aggressive environments and are particularly adapted for use in high temperature composites in addition to the utilization of their electrical conducting properties. Preparation of these materials is accomplished by melt polymerization and heat treatment at high temperatures.Type: GrantFiled: June 30, 1992Date of Patent: November 23, 1993Assignee: The United States of America as represented by the Secretary of the NavyInventor: Theordore R. Walton
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Patent number: 5225607Abstract: This invention relates to novel fluorinated ethers, useful as insecticides and acaricides, to processes and intermediates for their preparation, to insecticidal and acaricidal compositions thereof and to methods of combating and controlling insect and acarine pests therewith.Type: GrantFiled: December 30, 1987Date of Patent: July 6, 1993Assignee: Imperial Chemical Industries PLCInventors: Michael J. Bushell, Robin A. E. Carr, Alan J. Whittle
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Patent number: 5220048Abstract: Benzocyclobutene-1,2-dichlorides, -bromides and -iodides which are substituted in the benzene ring are accessible in good yields and short reaction times by reacting substituted 1,2-(dichloromethyl or dibromomethyl)-benzenes with NaI in acetonitrile as the solvent. They can be used together with dienophils, for example 1,4-quinones, in Diels-Alder reactions.Type: GrantFiled: May 24, 1989Date of Patent: June 15, 1993Assignee: Ciba-Geigy CorporationInventors: Marcus Baumann, Walter Fischer, Vratislav Kvita, Carl W. Mayer
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Patent number: 5141676Abstract: Organic-solvent soluble magnesium hydrides of the formulas(MgH.sub.2).sub.n. MgQ.sub.2 (II)(MgH.sub.2).sub.n. RMgX (III) ##STR1## are prepared by catalytically hydrogenating finely powdered magnesium, optionally in the presence of a magnesium halide, in an organic solvent in the presence of their MgH.sub.2 -free counterparts in whichQ is an alkyl, alkenyl, alkoxy, dialkylamino, aralkyl, aryl or diarylamino group, each with up to 18 carbon atoms,R is an alkenyl, aralkyl or aryl group, each with up to 18 carbon atoms,X is chlorine, bromine, or iodine,--E D.fwdarw. is a chelating ligand,E is --CH.sub.2, --N(R)-- or --O--,is an alkylene radical of the formula --(CH.sub.2).sub.p,D is a dialkylamino, diarylamino or alkoxy group, each with up to 19 carbon atoms,M is aluminum or boron,m is 1, 2, or 3, and1<n.ltoreq.50.Type: GrantFiled: April 17, 1991Date of Patent: August 25, 1992Assignee: Studiengesellschaft Kohle mbHInventors: Borislav Bogdanovic, Manfred Schwickardi
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Patent number: 5124334Abstract: The invention relates to benylalcohol phospholipase A.sub.2 inhibitors, pharmaceutical compositions containing them, and methods of treating phospholipase A.sub.2 -mediated conditions in mammals by administration of a therapeutically effective amount of such a benzylalcohol phospholipase A.sub.2 inhibitor.Type: GrantFiled: July 28, 1989Date of Patent: June 23, 1992Assignee: Du Pont Merck Pharmaceutical CompanyInventor: Wendell W. Wilkerson
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Patent number: 5117055Abstract: A perfluoroalkyl halogenide represented by the formula: ##STR1## wherein X stands for one element selected from the group consisting of iodine and bromine, R.sub.f for a perfluorohydrocarbon group, n for an integer in the range of 1 to 3, and m for an integer in the range of 1 to 3, provided that n and m satisfy the relationship, n.gtoreq.m, is produced by a method which consists essentially in subjecting a perfluorocarboxylic acid fluoride represented by the formula, ##STR2## wherein R.sub.f and n have the same meanings as defined above, to a thermal reaction with a lithium halogenide represented by XI, wherein X has the same meaning as defined above.Type: GrantFiled: February 22, 1990Date of Patent: May 26, 1992Assignees: Agency of Industrial Science and Technology, Ministry of International Trade & IndustryInventors: Takashi Abe, Eiji Hayashi, Haruhiko Fukaya
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Patent number: 5097075Abstract: 1,1,1-Trifluoro-2-hydroxy-5-benzyloxy compounds represented by the following formula (I) and optical isomers thereof: ##STR1##The compounds of the present invention are R-form and S-form when X is --C.tbd.C-- and are trans-form and cis-form both of which have respectively R-form and S-form when X is --CH.dbd.CH-- or ##STR2## ##STR3## the compound of the present invention is ##STR4## The compounds of the present invention are useful for asymmetric introduction of trifluoromethyl group and molecular designing of biologically active substances, ferroelectric liquid crystal compounds and so on.Type: GrantFiled: October 10, 1990Date of Patent: March 17, 1992Assignee: Showa Shell Sekiyu Kabushiki KaishaInventor: Tomoya Kitazume
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Patent number: 5091536Abstract: Organic-solvent soluble magnesium hydrides of the formulas ##STR1## are prepared by catalytically hydrogenating finely powdered magnesium, optionally in the presence of a magnesium halide, in an organic solvent in the presence of their MgH.sub.2 -free counterparts in whichQ is an alkyl, alkenyl, alkoxy, dialkylamide, aralkyl, aryl or diarylamide group, each with up to 18 carbon atoms,R is an alkenyl, aralkyl or aryl group, each with up to 18 carbon atoms,X is chlorine, bromine, or iodine,--E D.fwdarw. is a chelating ligand,E is --CH.sub.2, --N(R)-- or --O--,is an alkylene radical of the formula --(CH.sub.2).sub.p,D is a dialkylamide, diarylamide or alkoxy group, each with up to 18 carbon atoms,M is aluminum or boron,m is 1, 2, or 3, and1<n.ltoreq.50.Type: GrantFiled: February 9, 1988Date of Patent: February 25, 1992Assignee: Studiengesellschaft Kohle mbhInventors: Borislav Bogdanovic, Manfred Schwickardi
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Patent number: 5066681Abstract: 1-Trifluoromethyl-1-nitro-2-alkoxy-2-aryl-ethanes of the formula ##STR1## in which R.sup.1 represents a straight-chain or branched alkyl radical andR.sup.2 represents an optionally substituted aryl or hetaryl radical,their preparation from an aldehyde of the formula R.sup.2 -CHO, an alcohol of the formula R.sup.1 -OH and trifluoromethylnitromethane in the presence of a compound containing basic groups and antimycotic agents containing these compounds.Type: GrantFiled: September 20, 1989Date of Patent: November 19, 1991Assignee: Bayer AktiengesellschaftInventors: Bernd Baasner, Gunther Beck, Helmut Heitzer, Klaus Scaller
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Patent number: 5001275Abstract: Disclosed herein are a benzyl ether compound represented by the general formula (I): ##STR1## wherein R represents a branched alkyl group of 4 to 8 carbon atoms, a cycloalkyl group of 4 to 8 carbon atoms, an alkyl group of 1 to 3 carbon atoms having an alicyclic group of 3 to 7 carbon atoms, an aralkyl group of 7 to 9 carbon atoms, an alkyl group of 2 to 4 carbon atoms having an alkoxy group of 1 to 4 carbon atoms, an unsaturated alkyl group of 3 to 6 carbon atoms, a straight-chain alkyl group of 2 to 8 carbon atoms which has been substituted by 1 to 15 fluorine atoms, or a branched alkyl group of 3 to 8 carbon atoms which has been substituted by 1 to 15 fluorine atoms, and X represents a nitro group or an amino group, provided that when X is a nitro group, R is neither an aralkyl group nor an ethyl group substituted by fluorine atom(s), a process for producing the same.Type: GrantFiled: November 7, 1989Date of Patent: March 19, 1991Assignee: Kureha Kagaku Kogyo Kabushiki KaishaInventors: Takafumi Shida, Yoshikazu Kubota, Isao Ichinose
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Patent number: 4968836Abstract: The invention relates to a process for the preparation of cyclopropanecarbaldehydes of formula ##STR1## in which R.sub.1 is C.sub.1 -C.sub.4 alkyl or benzyl, which comprises (a) reacting a tetrahydrofuran of formula ##STR2## in which X is halogen and R.sub.2 is unsubstituted or halo-substituted C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.6 -cycloalkyl that is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl or by C.sub.1 -C.sub.4 alkoxy, or phenyl or benzyl each of which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro or cyano, with a halogenating agent to form a 1,2,4-trihalobutyl ether of formula ##STR3## in which X is halogen and R.sub.2 is unsubstituted or halo-substituted C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.6 cycloalkyl that is unsubstituted or substituted by halogen C.sub.1 -C.sub.4 alkyl or by C.sub.1 -C.sub.4 alkoxy, or phenyl or benzyl each of which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.Type: GrantFiled: January 30, 1990Date of Patent: November 6, 1990Assignee: Ciba-Geigy CorporationInventors: Hans-Ruedi Kanel, John G. Dingwall
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Patent number: 4908388Abstract: Derivatives of carbonyl-group containing behavior modifying compounds, in which said carbonyl group has been converted to a photolabile group which regenerates the carbonyl group on exposure to radiation, are of value in various methods for the control of animal, and in particular insect, species.Type: GrantFiled: January 20, 1988Date of Patent: March 13, 1990Assignee: National Research Development CorporationInventors: John A. Pickett, Ewen D. M. Macaulay
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Patent number: 4853151Abstract: Dispirotetradecanes of the formula I ##STR1## wherein R.sup.1 and R.sup.2 are each independently of each other alkyl containing 1 to 12 carbon atoms wherein one or more non-adjacent CH.sub.2 groups may also be replaced by --O--, --CO--, --CO--O--, --O--CO--, --O--COO-- and/or --CH.dbd.CH-- (trans), one of the radicals R.sup.1 and R.sup.2 also being H, F, Cl, Br, I, CN, NO.sub.2, NCS,A.sup.1 and A.sup.2 are each independently of each other trans-1,4-cyclohexylene wherein one or two non-adjacent CH.sub.2 groups may be replaced by --O-- and/or --S--, or 1,4-phenylene wherein one or more CH groups may also be replaced by N, with it also being possible optionally for A.sup.1 and A.sup.2 to be substituted laterally or axially by F, Cl, CN, CH.sub.3,Z.sup.1 and Z.sup.2 are each independently of each other --C--O--, --O--CO--, --CH.sub.2 CH.sub.2 --, --CH.sub.2 O--, --OCH.sub.2 -- or a single bond,m and n are each 0, 1 or 2,(m+n) 0, 1 or 2,X.sup.1, X.sup.2, X.sup.3 and X.sup.Type: GrantFiled: August 11, 1987Date of Patent: August 1, 1989Assignee: Merck Patent Gesellschaft Mit Beschrankfter HaftungInventors: Fritz Vogtle, Wolfgang Calaminus
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Patent number: 4849546Abstract: A multi-step process for the preparation of ethynylbenzaldehydes from bromo- or iodobenzaldehydes is disclosed. The arylhalogen is replaced with a protected ethynyl compound which is subsequently cleaved by base to form the arylacetylene. The aldehydic functionlity is preserved by formation of a corresponding Schiff's base or acetal, and its subsequent regeneration by treatment with aqueous acid.Type: GrantFiled: May 9, 1988Date of Patent: July 18, 1989Assignee: National Starch and Chemical CorporationInventors: Robert D. Rossi, Steven P. Fenelli
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Patent number: 4833258Abstract: Novel intermediates and a novel process for their preparation, where said intermediates are useful in the preparation of 6-hydroxymethyl and related oxidation derivatives of mevinolin and analogs thereof, are disclosed.Type: GrantFiled: February 17, 1987Date of Patent: May 23, 1989Assignee: Merck & Co., Inc.Inventors: Robert L. Smith, Ta Jyh Lee
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Patent number: 4678811Abstract: New substituted benzyl-type ethers of formula I ##STR1## in which R.sub.1 is aryl or aryl substituted by C.sub.1-4 -alkyl, halo-C.sub.1-4 -alkyl, phenyl-C.sub.1-4 -alkyl, C.sub.2-4 -alkenyl, halo-C.sub.2-4 -alkenyl, phenyl-C.sub.2-4 -alkenyl, C.sub.2-4 -alkynyl, halo-C.sub.2-4 -alkynyl, phenyl-C.sub.2-4 -alkynyl, C.sub.1-4 -alkoxy, halo-C.sub.1-4 -alkoxy, phenyl-C.sub.1-4 -alkoxy, C.sub.2-4 -alkenyloxy, halo-C.sub.2-4 -alkenyloxy, phenyl-C.sub.2-4 -alkenyloxy, C.sub.2-4 -alkynyloxy, halo-C.sub.2-4 -alkynyloxy, phenyl-C.sub.2-4 -alkynyloxy, alkylsulfonyloxy, haloalkylsulfonyloxy, arylsulfonyloxy, halo, cyano, nitro, aryloxy, haloaryloxy, C.sub.1-4 -alkyl-aryloxy, or nitroaryloxy,R.sub.2 is hydrogen or C.sub.1-4 alkyl,R.sub.3 is hydrogen, cyano or ethynyl,R.sub.4 is phenyl or pyridyl or one of these groups substituted by one or more of C.sub.1-6 -alkyl, halo-C.sub.1-6 -alkyl, phenyl-C.sub.1-6 -alkyl, C.sub.1-6 -alkyl interrupted by an O--, N-- or S-- atom, C.sub.2-4 -alkenyl, halo-C.sub.2-4 -alkenyl, phenyl-C.Type: GrantFiled: October 17, 1985Date of Patent: July 7, 1987Assignee: Schering AktiengesellschaftInventors: Helga Franke, Heinrich Franke, Hans-Rudolf Kruger, Hartmut Joppien
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Patent number: 4528406Abstract: Production of bis(alpha-alkylbenzyl)ethers or substituted derivatives thereof by reaction at elevated temperature of the corresponding alpha alkylbenzyl alcohols in the presence of a particular acidic clay catalyst, quenching of the catalyst and recovery of the desired ether by distillation directly from the reaction mixture containing the quenched catalyst, is disclosed. The alkyl methylbenzyl alcohol may be present as a component of an aromatic rich distilland product mixture derived from the ethyl benzene hydroperoxide epoxidation of an olefinically unsaturated compound.Type: GrantFiled: November 30, 1983Date of Patent: July 9, 1985Assignee: Atlantic Richfield CompanyInventors: Mary T. Arnold, George R. Siciliano
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Patent number: 4521637Abstract: Production of bis-(alpha-alkylbenzyl)ethers or substituted derivatives thereof by reaction at elevated temperature of the corresponding alpha alkylbenzyl alcohols in the presence of an aryl sulfonic acid treated calcined alumina catalyst, quenching the catalyst with a basic compound and recovery of the desired ether by distillation following separation of the quenched catalyst, is disclosed. The alkyl methylbenzyl alcohol may be present as a component of an aromatic rich distilled product mixture derived from the ethyl benzene hydroperoxide epoxidation of an olefinically unsaturated compound.Type: GrantFiled: December 16, 1983Date of Patent: June 4, 1985Assignee: Atlantic Richfield CompanyInventor: Frank Stevens
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Patent number: 4505862Abstract: An analgesic and sleep-aid composition containing an analgesic (e.g. aspirin, APAP or combinations thereof) and diphenhydramine dihydrogencitrate. Discloses several dosage forms including a two layer tablet in which aspirin is contained in one layer and APAP contained in the other layer; the preferred form being such that the diphenhydramine dihydrogencitrate is contained in the APAP layer.Type: GrantFiled: September 13, 1982Date of Patent: March 19, 1985Assignee: Bristol-Myers CompanyInventors: Harold Sheinaus, Arnold D. Marcus
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Patent number: 4450297Abstract: A process for the preparation of o-nitrobenzaldehyde, comprising converting to the corresponding acetals a mixture of nitrated benzaldehyde which contains about 10 to 30% of o-nitrobenzaldehyde and about 70 to 90% of m-nitrobenzaldehyde, removing the o-nitrobenzaldehyde acetal by distillation, and then converting the o-nitrobenzaldehyde acetal to o-nitrobenzaldehyde.Type: GrantFiled: March 17, 1983Date of Patent: May 22, 1984Assignee: Bayer AktiengesellschaftInventors: Michael Preiss, Wolfgang Gau, Horst Behre
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Patent number: 4424398Abstract: A process for synthesizing energetic ethers, esters and acetals is disclosed that comprises reacting certain alcohols with certain alkenes or alkynes in the presence of mercuric or mercurous sulfate. The products obtained are particularly useful as plasticizers, monomers or prepolymers for propellant binder systems.Type: GrantFiled: September 25, 1974Date of Patent: January 3, 1984Assignee: The United States of America as represented by the Secretary of the Air ForceInventors: Raymond R. McGuire, Robert E. Cochoy, Scott A. Shackelford
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Patent number: 4361494Abstract: New anisotropic compounds suitable for use in LC-display devices are disclosed and claimed. The new compounds are cyclohexyl cyclohexylmethyl ethers of formula (1): ##STR1## in which X and Y are respectively hydrogen, alkyl group with 1 to 12 C-atoms, alkoxy group with 1 to 12 C-atoms, monoalkylamino group with 1 to 12 C-atoms, nitrile group, nitro group, halogen, or cyclic radical of formula (1a) or (1b): ##STR2## in which R.sup.1 and R.sup.2 represent hydrogen alkyl group with 1 to 12 C-atoms, alkoxy group with 1 to 12 C-atoms, monoalkylamino group with 1 to 12 C-atoms, nitrile group, nitro group or halogen, and Z.sup.1 and Z.sup.2 represent simple covalent bonds or grounds of the formulas --COO--, --OOC--, --CH.sub.2 O-- or --OCH.sub.2, with the requirement that only one of the groups X, Y can be a cyclicradical or formula (1a) or (1b). Also disclosed and claimed are LC-mixtures containing these compounds and methods for their synthesis.Type: GrantFiled: December 17, 1980Date of Patent: November 30, 1982Assignee: BBC Brown, Boveri, & Company, LimitedInventors: Maged A. Osman, Laszlo Revesz
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Patent number: 4182911Abstract: Novel optically-active (S)- 1-aryloxy-2,3-epoxy-propane derivatives, a process for their manufacture, various intermediates used in the preparation thereof, and a process for using them for the manufacture of optically-active (S)-1-aryloxy-3-amino-2-propanol derivatives useful as .beta.-adrenergic blocking agents.Type: GrantFiled: December 20, 1977Date of Patent: January 8, 1980Assignee: Imperial Chemical Industries LimitedInventor: Howard Tucker
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Patent number: 4180679Abstract: There are provided substituted dinitrotoluenes and methods of preparation thereof, said dinitrotoluenes being useful as intermediates for the preparation of certain herbicidal 2,6-dinitroanilines.Type: GrantFiled: August 22, 1978Date of Patent: December 25, 1979Assignee: American Cyanamid CompanyInventor: Inder P. Kapoor
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Patent number: 4163758Abstract: 2-Nitroethylcyclopentane compounds represented by the formula (I) ##STR1## wherein X represents a ##STR2## R and R.sup.1 each represents a hydrogen atom or a protective group for a hydroxy group, R.sup.2 represents an unsubstituted or substituted alkyl group having 1 to 8 carbon atoms and R.sup.5 represents a hydrogen atom or an alkyl group havng 1 to 4 carbon atoms, which are useful as intermediates for the synthesis of prostaglandin compounds, and a process for preparing the 2-nitroethylcyclopentane compounds of the formula (I).Type: GrantFiled: September 6, 1978Date of Patent: August 7, 1979Assignee: Sagami Chemical Research CenterInventors: Kiyosi Kondo, Daiei Tunemoto, Teruo Umemoto