Ether Oxygen Is Part Of The Chain Patents (Class 564/346)
- Hydroxy, bonded directly to carbon, or ether oxygen is attached directly or indirectly to the chain by acyclic nonionic bonding with no amino nitrogen between the hydroxy or attached ether oxygen and the aryl ring or ring system (H of -OH may be replaced by a substituted or unsubstituted ammonium ion or a Group IA or IIA light metal) (Class 564/348)
- The aryl ring or ring system is polycyclo (Class 564/352)
- Hydrogen or acyclic hydrocarbyl substituents only bonded directly to the part of the chain between the ether oxygen and amino nitrogen (Class 564/353)
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Patent number: 5210307Abstract: A process for reforming alkyleneamines to predominantly linearly-extended polyalkylenepolyamines comprising contacting an alkyleneamine or mixture thereof with a catalyst under conditions such that a mixture of polyalkylenepolyamines enriched in linearly-extended products is formed, said catalyst containing at least one compound selected from the group consisting of (a) Group VB metal oxides, (b) Group VB metal phosphates, (c) silicates of Groups IIA, IIIB, IVB, VB, and the lanthanide and actinide metals, and (d) tungsten oxides, with the proviso that the silicates and tungsten oxides are essentially free of aluminum. For example, ethylenediamine is contacted with a catalyst of niobium phosphate or niobic acid under reaction conditions to yield predominantly non-cyclic polyethylenepolyamines.Type: GrantFiled: January 31, 1992Date of Patent: May 11, 1993Assignee: The Dow Chemical CompanyInventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
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Patent number: 5196610Abstract: A compound of formula: ##STR1## wherein W represents one or two substituents selected from halo, alkyl, alkoxy, alkoxyalkyl, haloalkyl and haloalkoxy, or W represents a bidentate group linking adjacent carbon atoms selected from alkylene and alkylenedioxy; Z represents a fluoroalkyl group of up to two carbon atoms; Y represents a substituted aryl group where such substituent is selected from halo, alkyl, aryl, aralkyl, aryloxy and arylamino; and either X' is hydrogen and X is selected from hydrogen, halo, hydroxy, alkoxy and aryloxy, or X and X' together represent a second bond between the adjacent carbon atoms. The compounds have useful insecticidal properties.Type: GrantFiled: July 31, 1986Date of Patent: March 23, 1993Assignee: Imperial Chemical Industries PLCInventors: Michael J. Bushell, Alan J. Whittle, Robin A. E. Carr
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Patent number: 5171753Abstract: Derivatives of 2-amino-1-phenylethanol were prepared from substituted amines and benzoin, stilbene oxide or styrene oxide to give compounds of Formula: ##STR1## where R is H or (un)substituted phenyl and C is a linking group or terminal group. The compounds of this invention can inhibit ulceration in in-vivo studies in rats.Type: GrantFiled: May 15, 1991Date of Patent: December 15, 1992Assignee: A. H. Robins Company, IncorporatedInventors: Harry R. Munson, Jr., Robert F. Boswell
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Patent number: 5166437Abstract: An improved process for the preparation of fluoxetine. The invention is concerned with an improved process for the preparation of the antidepressant, fluoxetine hydrochloride, or N-methyl-3-(p-trifluoromethylphenoxy)-3-phenylpropylamine hydrochloride, by simultaneous debenzylation and catalytic hydrogenation of 2-benzoyl-1-(N-benzyl-N-methyl)ethylamine base with the aid of Pd/C, Pt/C or Pd-Pt/C at a hydrogen pressure of 5 bar at 50.degree. C. with ethyl acetate as a solvent to obtain 1-phenyl-3-(N-methylamino)-propan-1-ol. This compound is then selectively etherified with 1-chloro-4-trifluoromethylbenzene in N-methylpyrrolidone at 80.degree. C. in the presence of potassium t-butoxide to form N-methyl-3-(p-trifluoromethylphenoxy)-3-phenylpropylamine, or fluoxetine base, which is transformed in a known manner to fluoxetine hydrochloride, or N-methyl-3-(p-trifluoromethylphenoxy)-3-phenylpropylamine hydrochloride. The yield of fluoxetine hydrochloride is 85-87% of the theoretical.Type: GrantFiled: November 23, 1990Date of Patent: November 24, 1992Assignee: Orion-Yhtyma OyInventors: Pekka J. Kairisalo, Petri J. Hukka, Anitta H. Jarvinen
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Patent number: 5126375Abstract: Phenethanolamine derivatives are disclosed of formula ##STR1## wherein m is 2 to 8; n is 1 to 7 provided that m+n is 4 to 12;Ar is phenyl or phenyl substituted by one or two halogen atoms, alkyl or alkoxy groups or by an alkylenedioxy group;R.sup.1 and R.sup.2 are hydrogen or alkyl provided that the sum total of carbon atoms in R.sup.1 and R.sup.2 is not more than 4; and the physiologically acceptable salts and solvates thereof.The compounds have a selective stimulant action at .beta..sub.2 -adrenoreceptors and may be used inter alia in the treatment of diseases associated with reversible airways obstructions such as asthma and chronic bronchitis. The compounds may be formulated in conventional manner as pharmaceutical compositions with physiologically acceptable carriers or excipients.The compounds may be prepared, for example by alkylation of an amine: ##STR2## where R.sup.3, R.sup.5 and R.sup.6 is hydrogen or a protecting group, followed by removal of any protecting group.Type: GrantFiled: November 29, 1990Date of Patent: June 30, 1992Assignee: Glaxo Group Ltd.Inventors: Ian F. Skidmore, Lawrence H. C. Lunts, Harry Finch, Alan Naylor
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Patent number: 5118851Abstract: A process of preparing a mixture of polyalkylenepolyamines and alkanolpolyamines comprising contacting a difunctional aliphatic alcohol with a primary or secondary aliphatic amine in the presence of a metal silicate catalyst wherein the metal is selected from the group consisting of Groups IIA, IIIB, and the lanthanide and actinide metals. For example, monoethanolamine reacts with diethylenetriamine in the presence of magnesium silicate to yield a mixture of higher molecular weight linear and branched polyethylenepolyamines and their corresponding alkanolpolyamines. These product mixtures are useful in the formation of specialty polyurethanes.Type: GrantFiled: December 5, 1990Date of Patent: June 2, 1992Inventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
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Patent number: 5118850Abstract: A process for reforming alkyleneamines to predominantly linearly-extended polyalkylenepolyamines comprising contacting an alkyleneamine or mixture thereof with a catalyst under conditions such that a mixture of polyalkylenepolyamines enriched in linearly-extended products is formed, said catalyst containing at least one compound selected from the group consisting of (a) Group VB metal oxides, (b) Group VB metal phosphates, (c) silicates of Groups IIA, IIIB, IVB, VB, and the lanthanide and actinide metals, and (d) tungsten oxdies, with the proviso that the silicates and tungsten oxides are essentially free of aluminum. For example, ethylenediamine is contacted with a catalyst of niobium phosphate or niobic acid under reaction conditions to yield predominantly non-cyclic polyethylenepolyamines.Type: GrantFiled: November 9, 1990Date of Patent: June 2, 1992Assignee: The Dow Chemical CompanyInventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
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Patent number: 5101060Abstract: Normally liquid final Mannich condensates prepared by reacting a para C.sub.1 -C.sub.15 alkyl phenol with formaldehyde and a first polyoxyalkylene diamine to form an intermediate Mannich condensate that is reacted with formaldehyde and a second polyoxyalkylene diamine to form a final Mannich condensate, the first and second polyoxyalkylene diamines having the formula: ##STR1## wherein R represents hydrogen or methyl and R' represents an alkyl group containing 1 to 4 carbon atoms or cyanoethyl group, and n represents positive numbers having a value of 1 to about 6, the final Mannich condensate having the formula: ##STR2## wherein X and Y are polyoxyalkylene amine groups derived from the first and second polyoxyalkylene diamines and formaldehyde.Type: GrantFiled: November 19, 1990Date of Patent: March 31, 1992Assignee: Texaco Chemical CompanyInventors: George P. Speranza, Jiang-Jen Lin
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Patent number: 5085666Abstract: The invention relates to a process for the preparation of nitroanilines, which consists in reacting an amine RNH.sub.2, or ammonia, with 3,4-methylenedioxynitrobenzene to give the products of the formula: ##STR1## in which R denotes hydrogen, alkyl, monohydroxyalkyl or polyhydroxyalkyl, alkoxyalkyl or aminoalkyl of the formula: ##STR2## in which R.sub.1 and R.sub.2, which are identical or different, denote hydrogen, alkyl or monohydroxyalkyl or polyhydroxyalkyl and n denotes an integer from 2 to 4, or of the formula: ##STR3## in which A denotes OCH.sub.2 or ##STR4## and R.sub.1 denotes --CH.sub.2 CH.sub.2 OH or ##STR5## or their salts.Type: GrantFiled: August 20, 1990Date of Patent: February 4, 1992Assignee: L'OrealInventors: Andree Bugaut, Alex Junino
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Patent number: 5068439Abstract: The present invention relates to a process for the preparation of a N-substituted phenylenediamine of the formula: ##STR1## comprising reacting N-phenylquinoneimine of the formula: ##STR2## with a primary amine of the formula:R--NH.sub.2 (III),wherein the molar ratio of II to III in the reaction mixture ranges from about 1:1 to 1:10; and wherein R is selected from the group of radicals consisting of alkyls having 1 to 20 carbon atoms, cycloalkyls having 6 to 8 carbon atoms and radicals of the structural formula: ##STR3## wherein R.sup.2 may be the same or different and is independently selected from the group of radicals consisting of hydrogen and an alkyl having 1 carbon atom, R.sup.3 is selected from the group of radicals consisting of an alkyl having 1 to 12 carbon atoms and n is an integer of from 0 to 6. The present process is characterized by its excellent yields of high purity N-substituted phenylenediamines.Type: GrantFiled: October 12, 1990Date of Patent: November 26, 1991Assignee: The Goodyear Tire & Rubber CompanyInventor: Kirkwood S. Cottman
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Patent number: 5066824Abstract: The present invention is directed to a process for preparing amine terminated compounds by reacting a polyfunctional acetoacetic acid ester with either ammonia or an organic compound which contains one or more primary amino groups in the presence of a solvent and an acidic catalyst selected from the group consisting of (i) boron trifuloride etherate and (ii) organic acids having pKa values of from 0.1 to 0.8 with the proviso that if the primary amino group containing compound contains no aromatically bound amino groups, the pKa of said organic acid is from 0.1 to less than 0.7.Type: GrantFiled: August 3, 1990Date of Patent: November 19, 1991Assignee: Mobay CorporationInventors: Robson Mafoti, Josef Sanders
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Patent number: 5026401Abstract: There are described dyeing compositions for keratin fibres, and in particular for human hair, containing a dyestuff of the formula: ##STR1## in which A denotes an alkylene group, an alkylene group substituted by one or more OH groups, or an alkylene group interrupted by a hetero-atom such as oxygen or by an --NH-- group, R.sub.1 and R.sub.2, which are identical or different, denote hydrogen, alkyl, monohydroxyalkyl or polyhydroxyalkyl, or R.sub.1 and R.sub.2 can together form a heterocyclic ring chosen from among piperidino or morpholino groups, Y denotes alkoxy or NO.sub.2, R denotes hydrogen or lower alkyl, and if Y denotes alkoxy, Z denotes NO.sub.2 and is located in the para-position to the amine group, and if Y denotes NO.sub.2, (a) Z denotes alkoxy or OH and is located in the para-position to the NO.sub.2 group, or alternatively (b) Z denotes OH and is located in the para-position to the amine group, and also their cosmetically acceptable salts. Many of these dyestuff are novel.Type: GrantFiled: September 13, 1989Date of Patent: June 25, 1991Assignee: L'OrealInventors: Andree Bugaut, Herve Borowiak
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Patent number: 5026872Abstract: Novel aromatic ether ketone diamine compounds and methods for their preparation are disclosed which comprise from about 3 to 8 aromatic rings interspersed with ether and ketone linkages. The novel ether ketone diamine compounds are useful as monomeric starting materials for the preparation of useful intermediates and useful thermoplastic and high temperature resistant polymers. In preferred embodiments, the novel ether ketone diamines are useful as curing agents for epoxy resin compositions and composite materials.Type: GrantFiled: February 1, 1984Date of Patent: June 25, 1991Assignee: American CyanamidInventor: Dalip K. Kohli
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Patent number: 5021429Abstract: Compounds of the general formula: ##STR1## and physiologically acceptable salts, and hydrates, N-oxides and bioprecursors of such compounds and such salts in whichR.sub.1 and R.sub.2, which may be the same or different, represent hydrogen or lower alkyl, cycloalkyl, aralkyl or lower alkenyl groups, or lower alkyl groups interrupted by an oxygen atom or a group ##STR2## in which R.sub.4 represents hydrogen or lower alkyl; or R.sub.1 and R.sub.2 may, together with the nitrogen atom to which they are attached form a heterocyclic ring which may contain the hetero functions --O-- and ##STR3## R.sub.3 represents hydrogen, lower alkyl, alkenyl or alkoxyalkyl; X represents --O--, --S-- or --CH.sub.2 -- or ##STR4## where R.sub.5 is hydrogen or lower alkyl; Y represents .dbd.S, .dbd.O, .dbd.NR.sub.6 or .dbd.CHR.sub.7 ;in which R.sub.6 represents hydrogen, nitro, cyano, lower alkyl, aryl, arylsulphonyl or lower alkylsulphonyl; R.sub.Type: GrantFiled: December 22, 1986Date of Patent: June 4, 1991Assignee: Allen & Hansburys LimitedInventor: Michael Martin-Smith
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Patent number: 5011999Abstract: A process for the preparation of predominantly non-cyclic polyalkylenepolyamines comprising contacting a difunctional aliphatic alcohol with ammonia or a primary or secondary aliphatic amine in the presence of a catalyst selected from the group consisting of Group VB metal oxides, niobium phosphates, tantalum phosphates, and mixtures thereof. For example, monoethanolamine is aminated by ethylenediamine to predominantly linear and branched polyethylenepolyamines in the presence of a catalyst containing niobium oxide supported on boehmite alumina.Type: GrantFiled: February 23, 1989Date of Patent: April 30, 1991Assignee: The Dow Chemical CompanyInventors: Robert G. Bowman, George E. Hartwell, David C. Molzahn, Enrique G. Ramirez, John E. Lastovica, Jr.
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Patent number: 4994616Abstract: A novel herbicide of formula I ##STR1## wherein R.sub.1 represents a halogen atom or an alkyl, haloalkoxy, haloalkyl or alkoxycarbonyl group;R.sub.2 represents a hydrogen or halogen atom;each of R.sub.3 to R.sub.6 independently represents a hydrogen or halogen atom or a cyano, alkyl, haloalkyl, alkoxy or haloalkoxy group;R.sub.7 represents a hydrogen or halogen atom, or an alkyl, haloalkoxy, haloalkyl or alkoxycarbonyl group;and A represents a nitrogen atom or a --CH-- group, together with its formulation and use as a herbicide, and its preparation.Type: GrantFiled: April 12, 1988Date of Patent: February 19, 1991Assignee: Ube Industries, Ltd.Inventor: David Munro
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Patent number: 4973757Abstract: The invention relates to a process for the preparation of nitroanilines, which consists in reacting an amine RNH.sub.2, or ammonia, with 3,4-methylenedioxynitriobenzene to give the products of the formula: ##STR1## in which R denotes hydrogen, alkyl, monohydroxyalkyl or polyhydroxyalkyl, alkoxyalkyl or aminoalkyl of the formula: ##STR2## in which R.sub.1 and R.sub.2, which are identical or different, denote hydrogen, alkyl or monohydroxyalkyl or polyhydroxyalkyl and n denotes an integer from 2 to 4, or of the formula: ##STR3## in which A denotes OCH.sub.2 or ##STR4## and R.sub.1 denotes --CH.sub.2 CH.sub.2 OH or ##STR5## or their salts.Type: GrantFiled: January 17, 1986Date of Patent: November 27, 1990Assignee: L'OrealInventors: Andree Bugaut, Alex Junino
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Patent number: 4937268Abstract: This invention relates to compounds of the general formula (I) and physiologically acceptable salts and solvates thereof whereinAr represents ##STR1## where R.sup.3 is a bond or a straight or branched C.sub.1-2 alkylene group,R.sup.4 is a hydroxy group or a group R.sup.5 NH-- whereR.sup.5 represents a group CH.sub.3 SO.sub.2 --, HCO-- or NH.sub.2 CO--, ##STR2## where R.sup.6 is a chlorine atom or the group F.sub.3 C--, ##STR3## k represents an integer from 1 to 8, m represents zero or an integer from 2 to 7 andn represents an integer from 2 to 7 with the proviso that the sum total of k, m and n is 4 to 12;R.sup.1 and R.sup.2 each represents a hydrogen atom or a methyl or ethyl group with the proviso that the sum total of carbon atoms in R.sup.1 and R.sup.2 is not more than 2;R.sup.30 represents hydrogen or C.sub.Type: GrantFiled: March 11, 1988Date of Patent: June 26, 1990Assignee: Glaxo Group LimitedInventors: Ian F. Skidmore, Harry Finch, Alan Naylor, Lawrence H. C. Lunts, David Hartley, William L. Mitchell
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Patent number: 4935409Abstract: Animal growth promoters of the formula ##STR1## The intermediates of the formula ##STR2## are also new.Type: GrantFiled: April 27, 1988Date of Patent: June 19, 1990Assignee: Bayer AktiengesellschaftInventors: Hartmund Wollweber, Jurgen Stoltefuss, Friedrich Berschauer
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Patent number: 4922024Abstract: A process for preparing amines comprising contacting an alcohol with a reactant amine in the presence of hydrogen and a catalyst comprising at least one compound containing an element of Group VIB and at least one non-metallic element of Groups IIIA, IVA, and VA of the Periodic Table, the contacting occurring under conditions such that the hydroxyl moiety of the alcohol is replaced by the reactant amine to form an amine product.Type: GrantFiled: April 14, 1988Date of Patent: May 1, 1990Assignee: The Dow Chemical CompanyInventors: Robert G. Bowman, Marvin H. Tegen, George E. Hartwell
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Patent number: 4916252Abstract: A process for preparing an optically active alcohol is disclosed, which comprises asymmetrically hydrogenating a 1,3-diketone in the presence of a ruthenium-optically active phosphine complex as a catalyst. The resulting alcohol has high optical purity.Type: GrantFiled: June 16, 1988Date of Patent: April 10, 1990Assignee: Takasago International CorporationInventors: Noboru Sayo, Takao Saito, Hidenori Kumobayashi, Susumu Akutagawa, Ryoji Noyori, Hidemasa Takaya
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Patent number: 4888447Abstract: A process is described for selectively preparing alkoxylated tertiary amine compounds, such as aminated ethoxylated amines, at ambient pressure by reacting an oxyalkylated alcohol with a secondary amine in the presence of a reductive amination catalyst at above ambient temperature using, as a reductive amination catalyst, a combination of Raney nickel and molybdenum.Type: GrantFiled: June 30, 1988Date of Patent: December 19, 1989Assignee: Ethyl CorporationInventor: Kim R. Smith
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Patent number: 4885392Abstract: Polyamines based on derivatives of 1,3-bissubstituted 2-propanol containing a multiplicity of amino groups, the latter containing at least one primary amino group and additionally further N-basic groupings, prepared by reacting 1,2,3-trisubstituted propane compounds with bis(primary amines or with monoamines and bis(primary amines).The polyamines according to the invention are clear to yellowish or yellow products which, at room temperature, form viscous to highly viscous liquids or may be paste-like or wax-like. They may be used, inter alia, advantageously as starting products for the preparation of thermosetting, in particular water-dispersible and cataphoretically depositable binders based on aminourethanes for coating solid substrates, in particular metals.Type: GrantFiled: December 22, 1987Date of Patent: December 5, 1989Assignee: Hoechst AGInventors: Rudiger Lenz, Gerd Walz, Michael Honel, Peter Ziegler
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Patent number: 4853381Abstract: The invention provides compounds of the general formula (I) ##STR1## whereinAr represents a phenyl group optionally substituted by one or more substituents selected from halogen atoms, or the groups C.sub.1-6 alkyl, C.sub.1-6 alkoxy, nitro, --(CH.sub.2).sub.q R [where R is hydroxy, --NR.sup.3 R.sup.4 (where R.sup.3 and R.sup.4 each represent a hydrogen atom or a C.sub.1-4 alkyl group, or --NR.sup.3 R.sup.4 forms a saturated heterocyclic amino group which has 5-7 ring members and optionally contains in the ring one or more atoms selected from --O--, or --S-- or a group --NH-- or --N(CH.sub.3)--), --NR.sup.5 COR.sup.6 (where R.sup.5 represents a hydrogen atom or a C.sub.1-4 alkyl group, and R.sup.6 represents a hydrogen atom or a C.sub.1-4 alkyl, C.sub.1-4 alkoxy, phenyl or --NR.sup.3 R.sup.4 group), --NR.sup.5 SO.sub.2 R.sup.7 (where R.sup.7 represents a C.sub.1-4 alkyl, phenyl or --NR.sup.3 R.sup.4 group), --COR.sup.8 (where R.sup.8 represents hydroxy, C.sub.1-4 alkoxy or --NR.sup.3 R.sup.4), --SR.sup.Type: GrantFiled: October 15, 1986Date of Patent: August 1, 1989Assignee: Glaxo Group LimitedInventors: Harry Finch, Lawrence H. C. Lunts, Alan Naylor, Ian F. Skidmore, Ian B. Campbell
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Patent number: 4835316Abstract: Organgomagnesium complexes which correspond to the formula (I): ps(RMgX).sub.m /N[--CHR.sub.1 --CHR.sub.2 --O--(CHR.sub.3 --CHR.sub.4 --O).sub.n --R.sub.5 ].sub.3 (I)wherein:m is 1, 2, or 3;R denotes a substituted or unsubstituted group which is:linear or branched alkyl containing from 1 to 18 carbon atoms,alkenyl or alkynyl containing from 2 to 18 carbon atoms,cycloalkyl or cycloalkenyl containing from 3 to 12 carbon atoms,alkoxyalkyl, dialkoxyalkyl or alkylthiocarbonyl, aryl (which aryl may particularly be position-substituted by at least a halogen or an alkoxy, trifluoroemethyl, trifluoromethoxy or trifluromethoylthio group), oralkoxyaryl or alkylthioaryl;X denotes a chlorine, iodine or bromine atom;n is an integer ranging from 0 to about 10;R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which are identical or di fferent, denote a hydrogen atom or an alkyl or cycloalkyl radical containing from 1 to 4 carbon atoms; andR.sub.5, which is identical or different in each of the three [--CHR.sub.1 --CHR.sub.2 --O--(CHR.Type: GrantFiled: October 2, 1987Date of Patent: May 30, 1989Assignee: Rhone-Poulenc ChimieInventors: Robert Corriu, Genevieve Cerveau, Claude Chuit, Catherine Reye, Alain Boudin
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Patent number: 4825000Abstract: A series of polyoxyalkylene diamines modified with phenoxy groups is disclosed. This series of diamines is of the general formula: ##STR1## wherein R.sub.1 and R.sub.2 are independently hydrogen or an alkyl of 1 to 4 carbon atoms, R.sub.3 is a alkyl of 1 to 4 carbon atoms, Ph is phenyl, x ranges from 2 to 40, y ranges from 1 to 20 and z ranges from 1 to 40.These diamines are cured with liquid epoxy resins. The cured resins demonstrated improved tensile strength and modulus, elongation and flexural strength and modulus over a commercially used curative.The diamines are also useful in RIM elastomers, in polyamides and as chain extenders in polyurethane foams.Type: GrantFiled: July 31, 1986Date of Patent: April 25, 1989Assignee: Texaco Inc.Inventors: John M. Larkin, Robert L. Zimmerman, Michael Cuscurida, Harold G. Waddill
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Patent number: 4803225Abstract: There are provided compounds of formula I, ##STR1## and pharmaceutically acceptable derivatives thereof. There are also described the use of the compounds of formula I as pharmaceuticals, methods for making the compounds and pharmaceutical, e.g. cardiac, compositions containing the compounds.Type: GrantFiled: December 2, 1987Date of Patent: February 7, 1989Assignee: Fisons, plcInventors: John Dixon, Francis Ince
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Patent number: 4751278Abstract: The adducts of monoepoxides with selected diamines, preferably m-xylylenediamine, are useful as curing agents for the curing of epoxy resin compositions at very low temperatures (25.degree.-50.degree. F., -4.degree. to 10.degree. C.).Type: GrantFiled: April 29, 1987Date of Patent: June 14, 1988Assignee: Ciba-Geigy CorporationInventor: Vincent Brytus
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Patent number: 4748276Abstract: Improvements are shown in the successive preparations of N,N-bis(2-hydroxyethyl)benzylamine starting with benzyl chloride, its conversion to the corresponding N,N-bis(2-chloroethyl)benzylamine in substantially quantitative yield in toluene solution and using the latter by reaction with phenylacetonitrile in the presence of aqueous sodium hydroxide solution and a tetra-n-butylammonium salt, preferably the hydrogen sulfate, to produce improved over-all yields of up to over 75% (based on benzyl chloride) of 1-benzyl-4-cyano-4-phenylpiperidine hydrochloride, an intermediate for preparing meperidine.Type: GrantFiled: March 6, 1985Date of Patent: May 31, 1988Assignee: Sterling Drug Inc.Inventors: John R. Handley, Allen F. Dow
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Patent number: 4720586Abstract: There are provided compounds of formula I, ##STR1## in which R.sub.1 represents OH,R.sub.2 and R.sub.3, which may be the same or different, each independently represent hydrogen, fluorine, chlorine, bromine, alkyl C1 to 6, nitro, nitrile, (CH.sub.2).sub.p R.sub.9 or SR.sub.9,W represents a single bond, a 1,2; 1,3; or 1,4-disubstituted benzene ring; a --CH.dbd.CH--group or a 1,4-cyclohexanediyl group;X respresents NH, O, S, SO.sub.2, CO, CH.sub.2, CONH or --COO;Y represents (CH.sub.2)q, CO, CS, SO.sub.2 and R.sub.20 represents hydrogen,or Y represents CR.sub.15 R.sub.16 CR.sub.17 R.sub.18,wherein the carbon atom bearing R.sub.15 and R.sub.16 is adjacent to X and in whichR.sub.15 and R.sub.18, together with the carbon atom to which they are attached form a carbonyl group, and R.sub.15, R.sub.16 and R.sub.20 each represent hydrogen, orR.sub.15 and R.sub.20 together form a chain --CH.sub.2 --, and R.sub.16, R.sub.17 and R.sub.18 each represent hydrogen, orR.sub.15, R.sub.16, R.sub.17 and R.sub.Type: GrantFiled: October 18, 1984Date of Patent: January 19, 1988Assignee: Fisons, plcInventors: John Dixon, Francis Ince
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Patent number: 4661635Abstract: Acetylenes of the formula (I): ##STR1## wherein Y, m, R.sup.1, R.sup.2 q, Alk, R.sup.3, n and R.sup.4 are as defined herein and Ar.sup.1 and Ar.sup.2 are aromatic, including the salts and ammonium derivatives of formula (I), in treating angina, hypertension and cardiac arrhythmias. Pharmaceutical compositions, methods of use and synthesis and novel intermediates are also part of the invention.Type: GrantFiled: October 29, 1984Date of Patent: April 28, 1987Assignee: McNeilab, Inc.Inventor: John R. Carson
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Patent number: 4659721Abstract: Alkanol derivatives corresponding to the general formula IR.sup.1 R.sup.2 N--(CH.sub.2).sub.m --Q--CH.sub.2 X--CH.sub.2 --Y--(CH.sub.2).sub.n --NHR.sup.3 (I)which have a highly selective action on histamine-H.sub.2 receptors are described. Due to this action, these compounds may advantageously be used for treatment of diseases caused by raised gastric secretion.Type: GrantFiled: January 22, 1985Date of Patent: April 21, 1987Assignee: Ludwig Heumann & Co. GmbHInventors: Helmut Schickaneder, Stefan Postius, Istvan Szelenyi, Peter Morsdorf, Rolf Herter, Kurt H. Ahrens
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Patent number: 4636568Abstract: There are disclosed certain aminoether compounds which are useful as intermediates in the preparation of photographic image dye providing materials. The aminoethers are represented either by the formula ##STR1## wherein R is hydrogen or an alcohol protecting group and R.sub.1 is hydrogen, alkyl or aralkyl such as benzyl or phenethyl; or the formula ##STR2## wherein R.sub.2 and R.sub.3 are alkyl having from 1 to 6 carbon atoms or R.sub.2 and R.sub.3 together represent the carbon atoms necessary to form, together with the oxygen atoms to which they are bonded and >CH, a five or six member saturated heterocyclic moiety which may include substituted rings and fused rings.Type: GrantFiled: August 27, 1984Date of Patent: January 13, 1987Assignee: Polaroid CorporationInventors: Myron S. Simon, David P. Waller
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Patent number: 4588719Abstract: A class of bicyclic benzenoid aminoalkylene ether and thioether compounds exhibiting pharmacological activity, including anti-secretory and anti-ulcerogenic activity, pharmaceutical compositions comprising these compounds, and methods for the treatment of gastrointestinal hyperacidity and ulcerogenic disorders in mammals using said compositions.Type: GrantFiled: October 24, 1984Date of Patent: May 13, 1986Assignee: William H. Rorer, Inc.Inventors: William L. Studt, Donald E. Kuhla, Henry F. Campbell
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Patent number: 4578462Abstract: The manufacture of optically active bifunctional compounds of the general formula ##STR1## wherein R represents protected hydroxymethyl, protected formyl or alkoxycarbonyl and R.sup.1 represents a group of the formula ##STR2## or --CH.sub.2 --CH.dbd.NR.sup.2 in which R.sup.2 and R.sup.3 represent lower alkyl or cycloalkyl or R.sup.2 and R.sup.3 together with the nitrogen atom represent a heterocyclic ring,by isomerizing compounds of the general formula ##STR3## wherein R, R.sup.2 and R.sup.3 have the above significance and R.sup.3 can additionally signify hydrogen,is described.The compounds of formula I are potential intermediates in the manufacture of, inter alia, natural vitamin E and natural vitamin K.sub.1.Type: GrantFiled: August 22, 1983Date of Patent: March 25, 1986Assignee: Hoffmann-La Roche Inc.Inventors: Hans-Jurgen Hansen, Rudolf Schmid, Max Schmid
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Patent number: 4543352Abstract: A class of naphthalene aminoalkylene ether and thioether compounds exhibiting pharmacological activity including anti-secretory and anti-ulcerogenic activity, pharmaceutical compositions comprising these compounds, and methods for the treatment of gastrointestinal hyperacidity and ulcerogenic disorders in mammals using said compositions are disclosed.Type: GrantFiled: April 29, 1983Date of Patent: September 24, 1985Assignee: William H. Rorer, Inc.Inventors: Donald E. Kuhla, Henry F. Campbell, William L. Studt
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Patent number: 4526973Abstract: Certain 1-(substituted amino)-2-(amino or substituted amino)cyclobutene-3,4-diones of the general formula ##STR1## are potent histamine H.sub.2 -antagonists useful in the treatment of peptic ulcers. A preferred compound, 1-amino-2-[3-(3-piperidinomethylphenoxy)propylamino]cyclobutene-3,4-dione, is prepared by treating an intermediate, 1-methoxy-2-[3-(3-piperidinomethylphenoxy)propylamino]cyclobutene-3,4-dion e, with ammonia.Type: GrantFiled: June 9, 1982Date of Patent: July 2, 1985Assignee: Bristol-Myers CompanyInventors: Aldo A. Algieri, Ronnie R. Crenshaw
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Patent number: 4522943Abstract: Compounds of the formula ##STR1## wherein R.sup.12 is a leaving group, Z is S, O or CH.sub.2 and A is a phenyl, furyl, thienyl or pyridyl ring substituted by a ##STR2## moiety, in which R.sup.8 and R.sup.9 are various substituents or, when taken together with the nitrogen, may be a specified heterocyclic ring, are intermediates in the preparation of histamine H.sub.2 -antagonist anti-ulcer agents of the formula ##STR3## in which R.sup.1 and R.sup.2 are any of several specified substituents.Type: GrantFiled: April 21, 1982Date of Patent: June 11, 1985Assignee: Bristol-Myers CompanyInventors: Aldo A. Algieri, Ronnie R. Crenshaw
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Patent number: 4500541Abstract: Cyclopropane derivatives of the formula ##STR1## wherein Ar is phenyl or phenyl monosubstituted or polysubstituted by F, Cl, Br, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.2-4 alkenyloxy, C.sub.1-4 alkylthio, OH, SH, CN, methylenedioxy or CF.sub.3 ; and R is H, C.sub.1-4 alkyl or benzyl, or a physiologically acceptable acid addition salt thereof, have valuable pharmacological properties, e.g., as antidepressants.Type: GrantFiled: June 17, 1983Date of Patent: February 19, 1985Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Hans-Heinrich Hausberg, Jurgen Uhl, Christoph Seyfried, Klaus-Otto Minck
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Patent number: 4448992Abstract: Addition products obtained by reaction of triethanolamine condensation products of the formula 1, ##STR1## wherein n is intended to denote a number from 1 to 3, with bisglycidyl ethers of the formula 2, ##STR2## wherein R.sup.1 can be identical or different and denote hydrogen, C.sub.1 -C.sub.4 -alkyl or halogen, in particular chlorine, A denotes a direct bond, a sulfonyl or cyclohexyl group or a group of the formula ##STR3## wherein R.sup.2 denotes hydrogen, methyl or phenyl and a denotes a whole number from 0 to 10, and their use as demulsifiers for oil-water emulsions, as lubricants and as paper auxiliaries.Type: GrantFiled: September 9, 1982Date of Patent: May 15, 1984Assignee: Hoechst AktiengesellschaftInventors: Helmut Diery, Bernhard Mees
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Patent number: 4417896Abstract: Novel compounds of the general formula ##STR1## wherein Z represents a substituted lower alkyl radical; each of R.sub.1 and R.sub.2 is hydrogen atom, a lower alkyl or a substituted lower alkyl identical with or different from Z and the functional groups NO.sub.2 and NR.sub.1 R.sub.2 can occupy all ring positions in relation to OZ, with the exception that if Z is .beta.-hydroxyethyl, --NO.sub.2 is in the 4 position and --N(R.sub.1)(R.sub.2) is in the 2 position then either R.sub.1 or R.sub.2 is other than hydrogen.The novel compounds are for dyeing human hair in a variety of yellow shades. The compounds of formula (I) may be used as aqueous or water-alcohol solutions to form dye compositions for dyeing human hair.Type: GrantFiled: April 6, 1982Date of Patent: November 29, 1983Assignee: Societe Anonyme dite: L'OrealInventors: Andree Bugaut, Patrick Andrillon
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Patent number: 4388469Abstract: Diphenylalkanoether and diphenylalkanone oxime-ether derivatives of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are each independently an aryl group optionally substituted with 1 to 3 substituents selected from the group consisting of halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro, cyano, di(C.sub.1 -C.sub.4)alkylamino, amino, benzyloxy, hydroxyl, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 alkanoylamino, C.sub.1 -C.sub.4 alkylamino and N-(C.sub.1 -C.sub.4)alkyl-N-(C.sub.1 -C.sub.4)alkanoylamino, Z.sup.1 is a group of the formula: ##STR2## (wherein R.sup.3 and R.sup.4 are each independently a hydrogen atom, a C.sub.1 -C.sub.4 alkyl group or an ar(C.sub.1 -C.sub.Type: GrantFiled: April 2, 1980Date of Patent: June 14, 1983Assignee: Sumitomo Chemical Company, LimitedInventors: Keiichi Ono, Hajime Kawakami, Junki Katsube
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Patent number: 4337061Abstract: Novel compounds of the general formula ##STR1## wherein Z represents a substituted lower alkyl radical; each of R.sub.1 and R.sub.2 is hydrogen atom, a lower alkyl or a substituted lower alkyl identical with or different from Z and the functional groups NO.sub.2 and NR.sub.1 R.sub.2 can occupy all ring positions in relation to OZ, with the exception that if Z is .beta.-hydroxyethyl, --NO.sub.2 is in the 4 position and --N(R.sub.1)(R.sub.2) is in the 2 position then either R.sub.1 or R.sub.2 is other than hydrogen.The novel compounds are for dyeing human hair in a variety of yellow shades. The compounds of formula (I) may be used as aqueous or water-alcohol solutions to form dye compositions for dyeing human hair.Type: GrantFiled: May 3, 1976Date of Patent: June 29, 1982Assignee: Societe Anonyme dite: L'OREALInventors: Andree Bugaut, Patrick Andrillon
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Patent number: 4330677Abstract: The invention relates to polyethers having an an average molecule weight of 3000 to 5000 and having a propylene oxide proportion of 60 to 80% and an ethylene oxide proportion of 20 to 40%. Also included in the invention are compositions containing said polyethers and methods for the use of said polyethers and compositions, particularly for their anti-lipidaemic effect.Type: GrantFiled: October 31, 1979Date of Patent: May 18, 1982Assignee: Bayer AktiengesellschaftInventors: Siegfried Linke, Mithat Mardin, Hans P. Krause, Rudiger Sitt
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Patent number: 4324739Abstract: (Dimethylaminoalkyl)carboxylic and -carbamic acid esters and (dimethylaminoalkyl) ethers and ureas are compounds which are especially suitable for use as amine curing agents for polyepoxide compounds. They impart longer curing times to the curable mixtures and thus good processing properties, especially when the mixtures are used as adhesives. In addition, the mechanical properties are often improved. Further, these compounds afford advantages when used as curing agents on account of their low volatility.Type: GrantFiled: March 31, 1980Date of Patent: April 13, 1982Assignee: Ciba-Geigy CorporationInventors: Helmut Zondler, Roland Moser
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Patent number: 4322530Abstract: A process for alkylating a polyamine by contacting, in a liquid media, a polyamine, an olefinic compound, carbon monoxide, and a hydrogen source in the presence of a catalytic amount of a rhodium atom containing compound selected from metallic rhodium, rhodium salts, rhodium oxides, rhodium carbonyls and ligands thereof at a temperature of from about 50.degree. C. to 250.degree. C. and at a pressure of from about 30 to about 300 atmospheres.Type: GrantFiled: February 22, 1980Date of Patent: March 30, 1982Assignee: W. R. Grace & Co.Inventor: Felek Jachimowicz
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Patent number: 4317819Abstract: The invention provides compounds of general formula ##STR1## and physiologically acceptable salts, hydrates and bioprecursors thereof, in whichY and Z, which may be the same or different, each represent oxygen, sulphur, .dbd.CHNO.sub.2 or .dbd.NR.sub.3 where R.sub.3 is hydrogen, nitro, cyano, lower alkyl, aryl, alkylsulphonyl or arylsulphonyl;p has a value from 2 to 12;R.sub.1 represents ##STR2## in which R.sub.4 and R.sub.5 which may be the same or different, each represent hydrogen, lower alkyl, cycloalkyl, lower alkenyl, aralkyl or lower alkyl interrupted by an oxygen atom or a group >N-R.sub.6 in which R.sub.6 represents hydrogen or lower alkyl, or R.sub.4 and R.sub.5 together with the nitrogen atom to which they are attached form a 5 to 7-membered saturated heterocyclic ring which may contain an additional oxygen atom or the group >NR.sub.Type: GrantFiled: December 5, 1980Date of Patent: March 2, 1982Assignee: Glaxo Group LimitedInventors: John W. Clitherow, Barry J. Price, John Bradshaw, Michael Martin-Smith
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Patent number: 4317932Abstract: A process for forming amines by contacting, in a liquid media, an olefinic compound, carbon monoxide, water, and ammonia in the presence of a rhodium atom containing compound selected from metallic rhodium, rhodium salts, rhodium oxides, and rhodium carbonyls and ligands thereof at a temperature of from 50.degree. to 250.degree. C. and at a pressure of from about 10 to about 300 atmospheres.Type: GrantFiled: February 22, 1980Date of Patent: March 2, 1982Assignee: W. R. Grace & Co.Inventor: Felek Jachimowicz
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Patent number: 4312861Abstract: Aralkylamines of the formula:R.sup.1 --CH.sub.2 --N(R.sup.3)--R.sup.2whereinR.sup.1 is a phenyl substituted by one of:(I) alkyls,(II) halo and(III) nitro;R.sup.2 is(IV) alkyl having from 4 to 10 carbon atoms, four of which are in one chain,(V) alkyl interrupted by an oxygen atom, i.e. an alkoxyalkyl or ether radical, or(VI) hydroxyalkyl wherein the alkyl is either (IV) or (V) and the hydroxy is the sole substituent;R.sup.3 is a hydrogen atom, alkyl having from 1 to 4 carbon atoms or such alkyl substituted by a dialkylphosphinyl group;a physiologically-compatible acid-addition salt thereof and a pharmaceutical composition containing such compound(s) as active ingredient(s) are valuable in view of the physiological activity, e.g. vasotonic, capillary sealing and antiarrhythmic, of the aralkylamines and their physiologically-compatible acid-addition salts.Type: GrantFiled: June 13, 1977Date of Patent: January 26, 1982Assignee: Hoechst AktiengesellschaftInventors: Istvan Boksay, Alfons Soder, Volkher Bollmann, Rolf-Ortwin Weber
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Patent number: 4313005Abstract: This invention relates to a process for reducing amidine formation during reduction of organonitriles. The process comprises including a boron compound in the reaction medium in sufficient amount to complex the amidine compound as it is formed.Type: GrantFiled: April 3, 1980Date of Patent: January 26, 1982Assignee: Air Products and Chemicals, Inc.Inventors: Michael E. Ford, Randall J. Daughenbaugh