Ether Oxygen Is Part Of The Chain Patents (Class 564/346)
  • Patent number: 5210307
    Abstract: 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: Grant
    Filed: January 31, 1992
    Date of Patent: May 11, 1993
    Assignee: The Dow Chemical Company
    Inventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
  • Patent number: 5196610
    Abstract: 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: Grant
    Filed: July 31, 1986
    Date of Patent: March 23, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: Michael J. Bushell, Alan J. Whittle, Robin A. E. Carr
  • Patent number: 5171753
    Abstract: 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: Grant
    Filed: May 15, 1991
    Date of Patent: December 15, 1992
    Assignee: A. H. Robins Company, Incorporated
    Inventors: Harry R. Munson, Jr., Robert F. Boswell
  • Patent number: 5166437
    Abstract: 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: Grant
    Filed: November 23, 1990
    Date of Patent: November 24, 1992
    Assignee: Orion-Yhtyma Oy
    Inventors: Pekka J. Kairisalo, Petri J. Hukka, Anitta H. Jarvinen
  • Patent number: 5126375
    Abstract: 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: Grant
    Filed: November 29, 1990
    Date of Patent: June 30, 1992
    Assignee: Glaxo Group Ltd.
    Inventors: Ian F. Skidmore, Lawrence H. C. Lunts, Harry Finch, Alan Naylor
  • Patent number: 5118851
    Abstract: 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: Grant
    Filed: December 5, 1990
    Date of Patent: June 2, 1992
    Inventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
  • Patent number: 5118850
    Abstract: 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: Grant
    Filed: November 9, 1990
    Date of Patent: June 2, 1992
    Assignee: The Dow Chemical Company
    Inventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
  • Patent number: 5101060
    Abstract: 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: Grant
    Filed: November 19, 1990
    Date of Patent: March 31, 1992
    Assignee: Texaco Chemical Company
    Inventors: George P. Speranza, Jiang-Jen Lin
  • Patent number: 5085666
    Abstract: 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: Grant
    Filed: August 20, 1990
    Date of Patent: February 4, 1992
    Assignee: L'Oreal
    Inventors: Andree Bugaut, Alex Junino
  • Patent number: 5068439
    Abstract: 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: Grant
    Filed: October 12, 1990
    Date of Patent: November 26, 1991
    Assignee: The Goodyear Tire & Rubber Company
    Inventor: Kirkwood S. Cottman
  • Patent number: 5066824
    Abstract: 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: Grant
    Filed: August 3, 1990
    Date of Patent: November 19, 1991
    Assignee: Mobay Corporation
    Inventors: Robson Mafoti, Josef Sanders
  • Patent number: 5026401
    Abstract: 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: Grant
    Filed: September 13, 1989
    Date of Patent: June 25, 1991
    Assignee: L'Oreal
    Inventors: Andree Bugaut, Herve Borowiak
  • Patent number: 5026872
    Abstract: 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: Grant
    Filed: February 1, 1984
    Date of Patent: June 25, 1991
    Assignee: American Cyanamid
    Inventor: Dalip K. Kohli
  • Patent number: 5021429
    Abstract: 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: Grant
    Filed: December 22, 1986
    Date of Patent: June 4, 1991
    Assignee: Allen & Hansburys Limited
    Inventor: Michael Martin-Smith
  • Patent number: 5011999
    Abstract: 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: Grant
    Filed: February 23, 1989
    Date of Patent: April 30, 1991
    Assignee: The Dow Chemical Company
    Inventors: Robert G. Bowman, George E. Hartwell, David C. Molzahn, Enrique G. Ramirez, John E. Lastovica, Jr.
  • Patent number: 4994616
    Abstract: 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: Grant
    Filed: April 12, 1988
    Date of Patent: February 19, 1991
    Assignee: Ube Industries, Ltd.
    Inventor: David Munro
  • Patent number: 4973757
    Abstract: 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: Grant
    Filed: January 17, 1986
    Date of Patent: November 27, 1990
    Assignee: L'Oreal
    Inventors: Andree Bugaut, Alex Junino
  • Patent number: 4937268
    Abstract: 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: Grant
    Filed: March 11, 1988
    Date of Patent: June 26, 1990
    Assignee: Glaxo Group Limited
    Inventors: Ian F. Skidmore, Harry Finch, Alan Naylor, Lawrence H. C. Lunts, David Hartley, William L. Mitchell
  • Patent number: 4935409
    Abstract: Animal growth promoters of the formula ##STR1## The intermediates of the formula ##STR2## are also new.
    Type: Grant
    Filed: April 27, 1988
    Date of Patent: June 19, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hartmund Wollweber, Jurgen Stoltefuss, Friedrich Berschauer
  • Patent number: 4922024
    Abstract: 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: Grant
    Filed: April 14, 1988
    Date of Patent: May 1, 1990
    Assignee: The Dow Chemical Company
    Inventors: Robert G. Bowman, Marvin H. Tegen, George E. Hartwell
  • Patent number: 4916252
    Abstract: 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: Grant
    Filed: June 16, 1988
    Date of Patent: April 10, 1990
    Assignee: Takasago International Corporation
    Inventors: Noboru Sayo, Takao Saito, Hidenori Kumobayashi, Susumu Akutagawa, Ryoji Noyori, Hidemasa Takaya
  • Patent number: 4888447
    Abstract: 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: Grant
    Filed: June 30, 1988
    Date of Patent: December 19, 1989
    Assignee: Ethyl Corporation
    Inventor: Kim R. Smith
  • Patent number: 4885392
    Abstract: 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: Grant
    Filed: December 22, 1987
    Date of Patent: December 5, 1989
    Assignee: Hoechst AG
    Inventors: Rudiger Lenz, Gerd Walz, Michael Honel, Peter Ziegler
  • Patent number: 4853381
    Abstract: 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: Grant
    Filed: October 15, 1986
    Date of Patent: August 1, 1989
    Assignee: Glaxo Group Limited
    Inventors: Harry Finch, Lawrence H. C. Lunts, Alan Naylor, Ian F. Skidmore, Ian B. Campbell
  • Patent number: 4835316
    Abstract: 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: Grant
    Filed: October 2, 1987
    Date of Patent: May 30, 1989
    Assignee: Rhone-Poulenc Chimie
    Inventors: Robert Corriu, Genevieve Cerveau, Claude Chuit, Catherine Reye, Alain Boudin
  • Patent number: 4825000
    Abstract: 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: Grant
    Filed: July 31, 1986
    Date of Patent: April 25, 1989
    Assignee: Texaco Inc.
    Inventors: John M. Larkin, Robert L. Zimmerman, Michael Cuscurida, Harold G. Waddill
  • Patent number: 4803225
    Abstract: 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: Grant
    Filed: December 2, 1987
    Date of Patent: February 7, 1989
    Assignee: Fisons, plc
    Inventors: John Dixon, Francis Ince
  • Patent number: 4751278
    Abstract: 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: Grant
    Filed: April 29, 1987
    Date of Patent: June 14, 1988
    Assignee: Ciba-Geigy Corporation
    Inventor: Vincent Brytus
  • Patent number: 4748276
    Abstract: 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: Grant
    Filed: March 6, 1985
    Date of Patent: May 31, 1988
    Assignee: Sterling Drug Inc.
    Inventors: John R. Handley, Allen F. Dow
  • Patent number: 4720586
    Abstract: 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: Grant
    Filed: October 18, 1984
    Date of Patent: January 19, 1988
    Assignee: Fisons, plc
    Inventors: John Dixon, Francis Ince
  • Patent number: 4661635
    Abstract: 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: Grant
    Filed: October 29, 1984
    Date of Patent: April 28, 1987
    Assignee: McNeilab, Inc.
    Inventor: John R. Carson
  • Patent number: 4659721
    Abstract: 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: Grant
    Filed: January 22, 1985
    Date of Patent: April 21, 1987
    Assignee: Ludwig Heumann & Co. GmbH
    Inventors: Helmut Schickaneder, Stefan Postius, Istvan Szelenyi, Peter Morsdorf, Rolf Herter, Kurt H. Ahrens
  • Patent number: 4636568
    Abstract: 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: Grant
    Filed: August 27, 1984
    Date of Patent: January 13, 1987
    Assignee: Polaroid Corporation
    Inventors: Myron S. Simon, David P. Waller
  • Patent number: 4588719
    Abstract: 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: Grant
    Filed: October 24, 1984
    Date of Patent: May 13, 1986
    Assignee: William H. Rorer, Inc.
    Inventors: William L. Studt, Donald E. Kuhla, Henry F. Campbell
  • Patent number: 4578462
    Abstract: 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: Grant
    Filed: August 22, 1983
    Date of Patent: March 25, 1986
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Hans-Jurgen Hansen, Rudolf Schmid, Max Schmid
  • Patent number: 4543352
    Abstract: 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: Grant
    Filed: April 29, 1983
    Date of Patent: September 24, 1985
    Assignee: William H. Rorer, Inc.
    Inventors: Donald E. Kuhla, Henry F. Campbell, William L. Studt
  • Patent number: 4526973
    Abstract: 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: Grant
    Filed: June 9, 1982
    Date of Patent: July 2, 1985
    Assignee: Bristol-Myers Company
    Inventors: Aldo A. Algieri, Ronnie R. Crenshaw
  • Patent number: 4522943
    Abstract: 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: Grant
    Filed: April 21, 1982
    Date of Patent: June 11, 1985
    Assignee: Bristol-Myers Company
    Inventors: Aldo A. Algieri, Ronnie R. Crenshaw
  • Patent number: 4500541
    Abstract: 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: Grant
    Filed: June 17, 1983
    Date of Patent: February 19, 1985
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Hans-Heinrich Hausberg, Jurgen Uhl, Christoph Seyfried, Klaus-Otto Minck
  • Patent number: 4448992
    Abstract: 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: Grant
    Filed: September 9, 1982
    Date of Patent: May 15, 1984
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Helmut Diery, Bernhard Mees
  • Patent number: 4417896
    Abstract: 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: Grant
    Filed: April 6, 1982
    Date of Patent: November 29, 1983
    Assignee: Societe Anonyme dite: L'Oreal
    Inventors: Andree Bugaut, Patrick Andrillon
  • Patent number: 4388469
    Abstract: 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: Grant
    Filed: April 2, 1980
    Date of Patent: June 14, 1983
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Keiichi Ono, Hajime Kawakami, Junki Katsube
  • Patent number: 4337061
    Abstract: 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: Grant
    Filed: May 3, 1976
    Date of Patent: June 29, 1982
    Assignee: Societe Anonyme dite: L'OREAL
    Inventors: Andree Bugaut, Patrick Andrillon
  • Patent number: 4330677
    Abstract: 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: Grant
    Filed: October 31, 1979
    Date of Patent: May 18, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Siegfried Linke, Mithat Mardin, Hans P. Krause, Rudiger Sitt
  • Patent number: 4324739
    Abstract: (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: Grant
    Filed: March 31, 1980
    Date of Patent: April 13, 1982
    Assignee: Ciba-Geigy Corporation
    Inventors: Helmut Zondler, Roland Moser
  • Patent number: 4322530
    Abstract: 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: Grant
    Filed: February 22, 1980
    Date of Patent: March 30, 1982
    Assignee: W. R. Grace & Co.
    Inventor: Felek Jachimowicz
  • Patent number: 4317819
    Abstract: 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: Grant
    Filed: December 5, 1980
    Date of Patent: March 2, 1982
    Assignee: Glaxo Group Limited
    Inventors: John W. Clitherow, Barry J. Price, John Bradshaw, Michael Martin-Smith
  • Patent number: 4317932
    Abstract: 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: Grant
    Filed: February 22, 1980
    Date of Patent: March 2, 1982
    Assignee: W. R. Grace & Co.
    Inventor: Felek Jachimowicz
  • Patent number: 4312861
    Abstract: 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: Grant
    Filed: June 13, 1977
    Date of Patent: January 26, 1982
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Istvan Boksay, Alfons Soder, Volkher Bollmann, Rolf-Ortwin Weber
  • Patent number: 4313005
    Abstract: 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: Grant
    Filed: April 3, 1980
    Date of Patent: January 26, 1982
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Michael E. Ford, Randall J. Daughenbaugh