Halogen, Bonded Directly To Carbon, Containing Patents (Class 564/510)
  • Patent number: 5461117
    Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.
    Type: Grant
    Filed: June 13, 1994
    Date of Patent: October 24, 1995
    Assignee: Exfluor Research Corporation
    Inventors: Thomas R. Bierschenk, Timothy J. Juhlke, Hajimu Kawa, Richard J. Lagow
  • Patent number: 5352785
    Abstract: A process for the purification of a perfluorochemical composition comprises continuously mixing the perfluorochemical composition, comprising a liquid mixture of inert perfluorochemicals (e.g., perfluoroalkanes, perfluoroethers, perfluoroaminoethers, or perfluoroalkyl tertiary amines) and isomeric fluorohydrochemicals, with a stabilization composition comprising water-miscible alkanol and an aqueous solution of base (such as potassium hydroxide) made by dissolving the base in an amount of water sufficient to dissolve or disperse the fluoride salt by-products of the subsequent reaction of the base with the fluorohydrochemicals to form fluoroolefins, the amount of the alkanol in the stabilization composition being in stoichiometric excess of the amount needed to completely convert the fluoroolefins to alkoxyvinyl ethers. The process can be utilized to purify the product mixtures resulting from fluorination methods such as direct fluorination or ECF.
    Type: Grant
    Filed: March 30, 1993
    Date of Patent: October 4, 1994
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Thomas C. Herzberg, Robert B. Fletcher, Randall F. Henderson
  • Patent number: 5334765
    Abstract: The present invention concerns novel carbamoyl derivatives of formula I, set out herein, which antagonize the pharmacological actions of one or more of the arachidonic acid metabolites known as leukotrienes, making them useful whenever such antagonism is desired, such as in the treatment of those diseases in which leukotrienes are implicated, for example, in the treatment of allergic or inflammatory diseases, or of endotoxic or traumatic shock conditions. The invention also provides pharmaceutical compositions containing the novel derivatives for use in such treatments, methods for their use and processes and intermediates for the manufacture of the novel derivatives.
    Type: Grant
    Filed: October 14, 1993
    Date of Patent: August 2, 1994
    Assignee: Imperial Chemical Industries PLC
    Inventor: Robert T. Jacobs
  • Patent number: 5332790
    Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.
    Type: Grant
    Filed: March 8, 1993
    Date of Patent: July 26, 1994
    Assignee: Exfluor Research Corporation
    Inventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
  • Patent number: 5322904
    Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.
    Type: Grant
    Filed: March 8, 1993
    Date of Patent: June 21, 1994
    Assignee: Exfluor Research Corporation
    Inventors: Thomas R. Bierschenk, Timothy J. Juhlke, Hajimu Kawa, Richard J. Lagow
  • Patent number: 5322903
    Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.
    Type: Grant
    Filed: January 17, 1992
    Date of Patent: June 21, 1994
    Assignee: Exfluor Research Corporation
    Inventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
  • Patent number: 5274118
    Abstract: A process for the preparation of (2R)-methyl-4,4,4-trifluorobutylamine, or an acid addition salt thereof which comprisesa) acylating an optically active amine with 2-methyl-4,4,4-trifluorobutanoic acid or a reactive derivative thereof to afford a butyramide;b) separating (R)-diastereomeric butyramide from (S)-diastereomeric butyramide; andc) converting the (R)-diastereomeric butyramide into the desired (2R)-methyl-4,4,4-trifluorobutylamine, or an acid addition salt thereof. The product may be acylated with a carboxylic acid of formula III ##STR1## wherein U is carboxy, or a reactive derivative thereof to afford (R)-4-[5-(N-[4,4,4-trifluoro-2-methylbutyl]carbamoyl)-1-methylindol-3-yl-m ethyl]-3-methoxy-N-o-tolylsulphonylbenzamide. The indole is useful as a leukotriene antagonist, for example in the treatment of asthma or allergic rhinitis.
    Type: Grant
    Filed: December 4, 1991
    Date of Patent: December 28, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: Robert T. Jacobs, Andrew G. Brewster, George J. Sependa
  • Patent number: 5256825
    Abstract: A nitrogen-containing perfluoroalkanoyl peroxide is provided which is represented by the formula: ##STR1## wherein Rf.sub.1 and Rf.sub.2 independently stand for an alkyl group of 1 to 5 carbon atoms, provided that Rf.sub.1 and Rf.sub.2 are joined to each other in one of the three patterns of union, 1) direct union, 2) union through the medium of an oxygen atom or 3) union through the medium of a nitrogen atom to form one of the three rings, i.e. five membered ring, six-membered ring or seven-membered ring.
    Type: Grant
    Filed: December 28, 1992
    Date of Patent: October 26, 1993
    Assignees: Agency of Industrial Science & Technology, Ministry of International Trade & Industry
    Inventors: Haruhiko Fukaya, Takashi Abe, Eiji Hayashi, Yoshio Hayakawa
  • Patent number: 5244924
    Abstract: A diluent for perfluorocarbons used for retinal unfolding (unfolding PFCL), consisting of a perfluorocarbon (diluent PFCL), which has a low viscosity and is volatile at room temperature, with a boiling point between body temperature (about 38.degree. C.) and 100.degree. C., for removing residual quantities of unfolding PFCL from the eye after performance of a retinal unfolding treatment. A method of treatment consisting of introducing into an eye the above diluent for the above purpose.
    Type: Grant
    Filed: January 24, 1992
    Date of Patent: September 14, 1993
    Assignee: Adatomed Pharmazeutische und Medizintechnische Gesellschaft mbH
    Inventor: Hasso Meinert
  • Patent number: 5225561
    Abstract: Metal organic chemical vapor deposition (MOCVD) formation of copper oxide superconductor materials. Various source reagents of Group II elements suitable for high temperature superconductor (HTSC) material formation are described, including beta-diketonates, cyclopentadienyls, alkyls, perfluoroalkyls, alkoxides, perfluoroalkoxides, and Schiff bases, as well as complexes of such Group II compounds, utilizing monodentate or multidentate ligands to provide additional coordination to the Group IIA atom, so that the resulting complex is of enhanced volatility characteristics, and enhanced suitability for MOCVD applications. Also disclosed are methods of synthesizing such compounds and complexes, including a method of making Group II metal beta-diketonate compounds having enhanced thermal stability characteristics. Further disclosed are a vertical inverted reactor for chemical vapor deposition, and various methods of processing applied metal oxide films for enhanced HTSC character.
    Type: Grant
    Filed: September 12, 1990
    Date of Patent: July 6, 1993
    Assignee: Advanced Technology Materials, Inc.
    Inventors: Peter S. Kirlin, Duncan W. Brown, Robin A. Gardiner
  • Patent number: 5214214
    Abstract: There is provided a novel perfluorochemical represented by the formula, ##STR1## wherein R.sub.F is a perfluoroalkyl group, a perfluoro alkoxyalkyl group or a perfluoroalkyloxy group, X and X' are same as or different from each other and are a fluorine atom or a perfluoroalkyl group, and Y is a perfluoroalkyloxy group or a perfluoro dialkylamino group, the total number of the carbon atoms contained being an integer of 8 to 11 inclusive. The perfluorochemical is prepared by perfluorinating the corresponding partially fluorinated compound which may have unsaturated hydrocarbon moiety, only with molecular fluorine in a stoichiometric excess amount in an inert solvent.The perfluorochemical is used for preparing a stable emulsion as blood substitutes or perfusion media.
    Type: Grant
    Filed: March 30, 1992
    Date of Patent: May 25, 1993
    Assignee: The Green Cross Corporation
    Inventors: Kirby V. Scherer, Jr., Kouichi Yamanouchi, Kazumasa Yokoyama, Kimie Naito
  • Patent number: 5196595
    Abstract: New perfluoroaminoether polymers and a process for preparing them which comprises copolymerizing fluorinated olefins with oxaziridines in the presence of ultra-violet radiations or of chemical initiators.
    Type: Grant
    Filed: April 28, 1992
    Date of Patent: March 23, 1993
    Assignee: Ausimont S.R.L.
    Inventors: Walter Navarrini, Darryl D. Desmarteau
  • Patent number: 5169868
    Abstract: A component having the following formula I: ##STR1## wherein X represents an integer ranging from 1 to 2 or 7 to 13;Y represents an integer ranging from 0 to 5;Z represents an integer ranging from 0 to 5;R.sub.1, R.sub.2 and R.sub.3 are the same or different and represent H or a straight chain or branched lower alkyl; andR' and R" are the same or different and represent H or halogen,and pharmaceutically acceptable salts thereof. Preferably, the lower alkyl has between 1 and 4 carbon atoms and the halogen is selected from the group consisting of fluorine, chlorine, bromine and iodine. The compound is useful as a MAO-B inhibitor. Also within the scope of the present invention is a composition for the inhibition of MAO-B activity and a method for alleviating Parkinsonism, Alzheimer's disease, depression, attention deficit hyperactive disorders, aging and other neuropsychiatric disorders and for improving the quality of life.
    Type: Grant
    Filed: March 1, 1991
    Date of Patent: December 8, 1992
    Assignee: University of Saskatchewan
    Inventors: Peter H. Yu, Bruce A. Davis, Alan A. Boulton
  • Patent number: 5169548
    Abstract: An antirust additive for lubricants based on perfluoropolyethers, comprising one of the fluoropolyether compounds having functionalized end groups selected from --CN, --CH.sub.2 NR.sub.1 R.sub.2 and ##STR1## and in particular a combination of these with small amounts of a fluoropolyether with acid end groups.
    Type: Grant
    Filed: April 26, 1991
    Date of Patent: December 8, 1992
    Assignee: Ausimont S.r.l.
    Inventors: Ezio Strepparola, Piero Gavezotti, Costante Corti
  • Patent number: 5117055
    Abstract: 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: Grant
    Filed: February 22, 1990
    Date of Patent: May 26, 1992
    Assignees: Agency of Industrial Science and Technology, Ministry of International Trade & Industry
    Inventors: Takashi Abe, Eiji Hayashi, Haruhiko Fukaya
  • Patent number: 5093432
    Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.
    Type: Grant
    Filed: September 28, 1989
    Date of Patent: March 3, 1992
    Assignee: Exfluor Research Corporation
    Inventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
  • Patent number: 5075508
    Abstract: Triperfluoroalkylamines of the formula: ##STR1## wherein, Rf.sup.1 and Rf.sup.2 are each a perfluoroalkyl group having 1 to 4 carbon atoms, and Rf.sup.3 is a perfluoroalkyl group having 3 to 11 carbon atoms, have good thermal stability, good voltage resistance, good fluidity at low temperature and low surface energy and which produce no toxic perfluoroisobutene.
    Type: Grant
    Filed: July 19, 1989
    Date of Patent: December 24, 1991
    Assignee: Daikin Industries Ltd.
    Inventors: Kenji Mikami, Yoshio Iwai, Nobuyoshi Iwashita, Yasuhisa Furutaka
  • Patent number: 5057623
    Abstract: An organic fluorine compound represented by the general formulaR.sub.f -(X).sub.h -R-Mwherein R.sub.f is a group selected from the following (a) and (b); ##STR1## X denotes a linking group selected from --O--, --S--, and --COO--, h denotes 0 or 1, R is a hydrocarbon chain comprising a phenylene group having an alkylene group with a total carbon number of 10 or more, or the derivative thereof, or an aliphatic alkylene group of a carbon number of 10 or more, and M is a group selected from --OH, --COOH, --SH, and --CONH.sub.2.The organic fluorine compound of the present invention greatly improves the dispersibility of magnetic powders in magnetic coating materials, has also an excellent rust prevention effect on metallic magnetic powders, and exhibits a marked dispersing effect even on fluorocarbon resin fine powders, which can be difficultly dispersed with conventional dispersing agents.
    Type: Grant
    Filed: October 13, 1989
    Date of Patent: October 15, 1991
    Assignee: Matsushita Electric Industrial Co., Ltd.
    Inventors: Yoshiaki Kai, Takashi Suzuki
  • Patent number: 5019654
    Abstract: New fluorinated tertiary butylamines of the formula ##STR1## are prepared from halogenated pivalic acid halides by a reaction sequence which comprises preparing the fluorinated pivalic acid and decomposition of the azide to the corresponding isocyanate. The isocyanate can be converted to the fluorinated tertiary butylamine acid addition salt by acid hydrolysis or directly to the amine by treatment with base. In addition, the present amines can be prepared by reaction of a pivalic acid amide with hypochlorite. The new butylamines can be used in the preparation of benzoic acid amides having insecticidal action.
    Type: Grant
    Filed: March 19, 1987
    Date of Patent: May 28, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bernd Baasner, Hermann Hagemann, Michael Schwamborn
  • Patent number: 5017718
    Abstract: A process for preparing a perfluoroalkyl-substituted compound is disclosed. The process comprises reacting a halopolyfluoroalkane having 1 to 20 carbon atoms with a compound selected from the group consisting of (1) a substituted or unsubstituted ethylene, (2) a substituted or unsubstituted acetylene and (3) a substituted or unsubstituted allylsilane, in the presence of a metal-carbonyl complex of the metal of the Group VIII of the Periodic Table. Alternatively, the reaction between the halopolyfluoroalkane and the substituted or unsubstituted allylsilane is effected under radical generating condition.
    Type: Grant
    Filed: January 26, 1984
    Date of Patent: May 21, 1991
    Assignee: Sagami Chemical Research Center
    Inventors: Iwao Ojima, Takamasa Fuchikami
  • Patent number: 4990633
    Abstract: New fluorinated bisaryloxy-substituted alkenes are prepared by reaction of substituted phenols with perhaloalkenes and can be used as electrical insulating agents.
    Type: Grant
    Filed: May 4, 1989
    Date of Patent: February 5, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Michael Negele, Dietmar Beilefeldt, Thomas Himmler, Albrecht Marhold
  • Patent number: 4985556
    Abstract: Perfluorocarboxylic acid fluorides represented by the formula A-B, wherein A is either ##STR1## and B stands for a perfluoro-di-substituted amino group, and perfluoro(dialkylaminopropenes) represented by the formula A"-B", wherein A" stands for ##STR2## and B" has the same meaning as B defined above, are novel compounds. Methods for the production of these novel compounds are also disclosed.
    Type: Grant
    Filed: September 9, 1988
    Date of Patent: January 15, 1991
    Assignees: Agency of Industrial Science & Technology, Ministry of International Trade & Industry
    Inventors: Takashi Abe, Eiji Hayashi
  • Patent number: 4943595
    Abstract: There is provided a novel perfluorochemical represented by the formula, ##STR1## wherein R.sub.F is a perfluoroalkyl group, a perfluoro alkoxyalkyl group or a perfluoroalkyloxy group, X and X' are same as or different from each other and are a fluorine atom or a perfluoroalkyl group, and Y is a perfluoroalkyloxy group or a perfluoro dialkylamino group, the total number of the carbon atoms contained being an integer of 8 to 11 inclusive. The perfluorochemical is prepared by perfluorinating the corresponding partially fluorinated compound which may have unsaturated hydrocarbon moiety, only with molecular fluorine in a stoichiometric excess amount in an inert solvent.The perfluorochemical is used for preparing a stable emulsion as blood substitutes or perfusion media.
    Type: Grant
    Filed: February 22, 1984
    Date of Patent: July 24, 1990
    Assignee: The Green Cross Corporation
    Inventors: Kirby V. Scherer, Jr., Kouichi Yamanouchi, Kazumasa Yokoyama, Ryoichi Naito, deceased
  • Patent number: 4921957
    Abstract: By reacting 3,3,4,4-tetrafluoro-2-(trifluoromethyl)-1,2-oxazetidine (I) with a Lewis acid, in particular SbF.sub.5, three novel fluorinated compounds (II), (III) and (IV) are obtained: ##STR1## The compounds are useful as lubricants.
    Type: Grant
    Filed: July 6, 1989
    Date of Patent: May 1, 1990
    Assignee: Ausimont S.r.l.
    Inventors: Alessandro Malacrida, Darryl D. Desmarteau
  • Patent number: 4914240
    Abstract: Gem-dihalo-1,8-diamino-4-aza-octane derivatives useful as antiproliferative or antitumor agents.
    Type: Grant
    Filed: March 30, 1989
    Date of Patent: April 3, 1990
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Fritz Gerhart, Pierre Mamont
  • Patent number: 4912216
    Abstract: A perfluoro-(N-vinylamine) compound containing a >NCF.dbd.CF.sub.2 group is produced from a perfluoro-compound containing a group of the general formula: ##STR1## (wherein X stands for a fluorine atom or a --OM group having an alkali or alkaline earth metal ion for M) and having connected to the group of the general formula a perfluoro-alkyl group having a total of 2 to 6 carbon atoms contained in the main carbon chain thereof by heating the perfluoro-compound at a temperature in the range of 100.degree. C. to 500.degree. C. thereby effecting conversion of the group of the foregoing general formula into the aforementioned >NCF.dbd.CF.sub.2 group.
    Type: Grant
    Filed: July 10, 1987
    Date of Patent: March 27, 1990
    Assignees: Agency of Industrial Science & Technology, Ministry of International Trade & Industry
    Inventor: Takashi Abe
  • Patent number: 4886915
    Abstract: Water soluble biocidal water treatment perhalides of the formula: ##STR1## where R.sub.1 and R.sub.2 are independently hydrogen, hydroxyethyl, alkyl, cyclic alkyl, (alpha, omega)-alkyl, alkyl ether, polyether, heterocyclic ring-substituted alkyl, and halogenated alkyl; X is chlorine, bromine or iodine; and only one of R.sub.1 and R.sub.2 may be hydrogen.
    Type: Grant
    Filed: June 24, 1988
    Date of Patent: December 12, 1989
    Assignee: Great Lakes Chemical Corporation
    Inventor: Nicolai A. Favstritsky
  • Patent number: 4886610
    Abstract: The invention relates to compositions comprising a lubricant or a hydraulic fluid and at least one compound of the general formula ##STR1## wherein n is 2, 3 or 4, X is --S--, --O--, --O--CO--or --CH.sub.2 --, R.sup.1 is C.sub.1 -C.sub.22 alkyl, C.sub.5 -C.sub.6 cycloalkyl or phenyl, and R.sup.2 is hydrogen, C.sub.1 -C.sub.8 -alkyl, C.sub.2 -C.sub.4 alkyl which is substituted by an --OH group, or a group of the formula --CH.sub.2 --CH(OH)--CH.sub.2 --X--R.sup.1, wherein X and R.sup.1 have the given meanings, and to novel compounds of the formula indicated above. The glucamine derivatives of formula I are especially suitable for use as antiwear agents and as extreme pressure additives for mineral and synthetic lubricant oils and hydraulic fluids, and also as amphipolar ligands for imparting lipophilic properties to intrinsically hydrophilic metal salts, metal oxides, metal hydroxides and to protic acids. The complex compounds so obtained of the formulaM.sub.n.sup.m .multidot.X.sub.m.sup.n .multidot.pY.
    Type: Grant
    Filed: December 15, 1988
    Date of Patent: December 12, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Hermann O. Wirth, Hans-Helmut Friedrich
  • Patent number: 4879327
    Abstract: The invention relates to amine salts of phosphorous acid having a structure of the s-triazine, 1,2,4-triazole, benzimidazole, heptazine, pyrimidine, or piperazine type which may be combined with a polyhydroxylated compound as fireproofing agents for plastics, particularly polyamides and polyolefins, the process of fireproofing said plastics, and the resultant fireproofed plastics.
    Type: Grant
    Filed: March 31, 1988
    Date of Patent: November 7, 1989
    Assignee: Atochem
    Inventors: Pierre Poisson, Nadine Rivas, Pierre Deloy
  • Patent number: 4859357
    Abstract: The invention relates to new polyfluorinated compounds which are usable as anti-wear additives for lubricants.These compounds are of general formula: ##STR1## in which R.sub.F is a perfluorinated radical, X denotes a divalent linkage--(CH.sub.2 CF.sub.2).sub.a (CH.sub.2).sub.b --, --CF.dbd.CH--CH.sub.2 -- or --CFH--CH.sub.2 CH.sub.2 --, a is an integer ranging from 0 to 10, b is an integer ranging from 1 to 4 but equal to 2 if a is other than zero, R.sub.1 denotes a hydrogen atom or an alkyl radical, R.sub.2 denotes a hydrogen atom or a methyl radical and R.sub.3 denotes an alkyl radical. They are prepared by condensing an amino alcohol, R.sub.F --X--NH--CH.sub.2 CH(R.sub.1)OH, with an alkyl ester of an unsaturated carboxylic acid, CH.sub.2 .dbd.C(R.sub.2)--COOR.sub.3.
    Type: Grant
    Filed: June 9, 1988
    Date of Patent: August 22, 1989
    Assignee: Societe Atochem
    Inventors: Laurent Germanaud, Marc Hermant
  • Patent number: 4853141
    Abstract: The invention relates to new polyfluorinated compounds which are usable as anti-wear additives for lubricants.These compounds are of general formula: ##STR1## in which R.sub.F is a perfluoroalkyl radical, R.sub.1 and R.sub.3 each denote a hydrogen atom or an alkyl, cycloalkyl or aryl radical, R.sub.2 and R.sub.4 each denote a hydrogen atom or an acyl residue, m equals 0 or 1 and X denotes a hydrogen atom or a 2-hydroxy-1-phenylethyl group. They are prepared by hydrogenation of amino alcohols of formula:R.sub.F --CF.dbd.CH--CH.sub.2 --NH--CH.sub.2 CH(R.sub.1)--OHfollowed, where appropriate, by a reaction with an epoxide and/or an esterification.
    Type: Grant
    Filed: June 10, 1988
    Date of Patent: August 1, 1989
    Assignee: Societe ATOCHEM
    Inventors: Pierre Durual, Marc Hermant, Charles Laviron
  • Patent number: 4851448
    Abstract: Gem-dihalo-1,8-diamino-4-aza-octane derivatives useful as antiproliferative or antitumor agents.
    Type: Grant
    Filed: June 15, 1987
    Date of Patent: July 25, 1989
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Fritz Gerhart, Pierre Mamont
  • Patent number: 4782148
    Abstract: A perfluoro compound containing a group of the general formula: ##STR1## wherein X stands for a fluorine atom, perfluoro-alkoxy groups, or --OM where M stands for an alkali metal ion or an alkaline earth earth ion and having connected to the aforementioned group a perfluoro-alkyl group possessing a total of 2 to 6 carbon atoms in the trunk carbon chain thereof is subjected to a temperature in the range of 100.degree. to 500.degree. C. to produce a perfluoro-(N-vinylamine) compound now containing the aforementioned group as converted into the formula:>NCF.dbd.CF.sub.
    Type: Grant
    Filed: July 18, 1986
    Date of Patent: November 1, 1988
    Assignees: Agency of Industrial Science & Technology, Ministry of International Trade & Industry
    Inventor: Takashi Abe
  • Patent number: 4778926
    Abstract: Gem-dihalo and gem-tetrahalo-1,12-diamino-4,9-diazadodecane derivatives useful as antiproliferative or antitumor agents.
    Type: Grant
    Filed: June 15, 1987
    Date of Patent: October 18, 1988
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Fritz Gerhart, Pierre Mamont
  • Patent number: 4760377
    Abstract: Disclosed is a decompaction system for reading compacted paralled data from a memory and providing in real time uncompacted serial data therefrom. The decompaction system is especially suited to be utilized in pin electronics automatic test equipment for real time testing of units such as integrated circuits, circuit boards, etc. The decompaction system includes a separate channel for each pin of the unit under test (UUT) and is capable of decoding a number of types of compacted parallel data and providing serail data to each pin of the UUT in the most prevalently used test patterns. The data is compacted by software algorithms according to these patterns, stored in a memory and retrieved and decoded by the decompaction system during real-time testing of the UUT. In a specific embodiment, compacted parallel data is stored in 16-bit words in a separate memory for each channel, and is decompacted into serial data sequences of from 8 to 4096 bits per channel for each access of the respective memory.
    Type: Grant
    Filed: March 29, 1985
    Date of Patent: July 26, 1988
    Assignee: Giordano Associates, Inc.
    Inventor: Philip C. Jackson
  • Patent number: 4719312
    Abstract: The present invention is concerned with the preparation of lysosomotropic detergent agents and pharmaceutical composition useful in the treatment of cancer. These compounds are amine derivatives having a pK of 3.5 of the general structure ##STR1## in which R.sub.1 is C.sub.8-30 alkyl, C.sub.8-30 -alkenyl, substituted C.sub.4-30 alkyl or substituted C.sub.4-30 -alkenyl; R.sub.2 is hydrogen or C.sub.1-4 alkyl and Y is an electron withdrawing group, to control the pK, selected from trifluoroethyl, and difluoroethyl.
    Type: Grant
    Filed: September 2, 1986
    Date of Patent: January 12, 1988
    Assignee: Merck & Co., Inc.
    Inventor: Raymond A. Firestone
  • Patent number: 4719313
    Abstract: Gem-dihalo and gem-tetrahalo-1,12-diamino-4,9-diaza-dodecane derivatives useful as antiproliferative or antitumor agents.
    Type: Grant
    Filed: February 12, 1986
    Date of Patent: January 12, 1988
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Fritz Gerhart, Pierre Mamont
  • Patent number: 4707498
    Abstract: Novel fluorinated diaminoalkyne derivatives are inhibitors of ornithine decarboxylase enzyme and have the following general Formula I: ##STR1## wherein R represents C.sub.1 -C.sub.4 alkyl, or preferably, hydrogen.
    Type: Grant
    Filed: January 14, 1986
    Date of Patent: November 17, 1987
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Michael Kolb, David A. Kendrick
  • Patent number: 4695654
    Abstract: Gem-dihalo-1,8-diamino-4-aza-octane derivatives useful as antiproliferative or antitumor agents.
    Type: Grant
    Filed: August 21, 1985
    Date of Patent: September 22, 1987
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Fritz Gerhart, Pierre Mamont
  • Patent number: 4670470
    Abstract: Organic sulfoxides having a latent allyl group bound to the sulfur are enzyme inhibitors of the suicide or K.sub.cat type.
    Type: Grant
    Filed: August 29, 1985
    Date of Patent: June 2, 1987
    Assignee: Merck & Co., Inc.
    Inventor: Raymond A. Firestone
  • Patent number: 4585569
    Abstract: An absorption heat pump wherein the working fluid is a fluoroalkylamine of the formula: ##STR1## wherein each of X and X.sup.1, independently, represents hydrogen or fluorine,R represents hydrogen or a lower alkyl radical,n represents an integer from 1 to 4, each of m and q represents an integer from 0 to 2,p represents an integer from 0 to 4 provided that p is not zero when X.sup.1 is fluorine, and r represents an integer from 1 to 3, the fluoroalkylamine having a maximum of 6 carbon atomsand the solvent is a phenol.
    Type: Grant
    Filed: December 24, 1984
    Date of Patent: April 29, 1986
    Assignee: Imperial Chemical Industries PLC
    Inventor: Richard L. Powell
  • Patent number: 4558071
    Abstract: Organic sulfoxides having a latent allyl group bound to the sulfur are enzyme inhibitors of the suicide or K.sub.cat type.
    Type: Grant
    Filed: February 25, 1983
    Date of Patent: December 10, 1985
    Assignee: Merck & Co., Inc.
    Inventor: Raymond A. Firestone
  • Patent number: 4541943
    Abstract: A mechanical vapor recompression heat pump system wherein the working fluid is a saturated fluorohydrocarbon or fluorohydrocarbon ether having from 3 to 5 carbon atoms or a fluorinated amine containing up to 6 carbon atoms and having the formula: ##STR1## wherein each of X and X.sup.1, independently, represents hydrogen or fluorine,R represents hydrogen or a lower alkyl radical,n represents an integer from 1 to 4,each of m and q represents an integer from 0 to 2,p represents an integer from 0 to 4 provided thatp is not zero when X.sup.1 is fluorine, andr represents an integer from 1 to 3;or the formula: ##STR2## wherein W represents hydrogen or fluorine, a represents an integer from 3 to 5, b represents an integer from 1 to 3 and c represents an integer from 0 to 2 provided that c is not zero when W is fluorine.
    Type: Grant
    Filed: May 16, 1984
    Date of Patent: September 17, 1985
    Assignee: Imperial Chemical Industries PLC
    Inventor: Richard L. Powell
  • Patent number: 4435425
    Abstract: Fluorinated diaminobutane compounds in vivo are inhibitors of gamma-aminobutyric acid transaminase and have the following formula: ##STR1## wherein: R.sub.1 represents hydrogen, C.sub.1 -C.sub.6 alkyl, or phenyl-(C.sub.1 -C.sub.4 alkyl);R.sub.2 represents hydrogen, C.sub.1 -C.sub.6 alkyl, phenyl-(C.sub.1 -C.sub.4 alkyl), or R.sub.4, where R.sub.4 is as defined below;R.sub.3 represents hydrogen, or, except when R.sub.2 represents R.sub.4, R.sub.4, where R.sub.4 is as defined below;each R.sub.4, independently, represents C.sub.2 -C.sub.5 alkylcarbonyl, phenylcarbonyl, phenyl-(C.sub.1 -C.sub.4 alkyl) carbonyl, or an aminocarboxylic acid residue derived by removal of an hydroxy group from the carboxy moiety of an L-aminocarboxylic acid; andp represents 1 or 2,and pharmaceutically acceptable acid addition salts thereof.
    Type: Grant
    Filed: April 9, 1982
    Date of Patent: March 6, 1984
    Assignee: Merrell Toraude et Compagnie
    Inventors: Albert Sjoerdsma, Philippe Bey, Michel Jung, Fritz Gerhart, Daniel Schirlin
  • Patent number: 4418077
    Abstract: Fluorinated aminobutyric acid and diaminobutane compounds in vivo are inhibitors of gamma-aminobutyric acid transaminase and have the following formula: ##STR1## wherein: Y represents hydrogen or fluorine;Z represents --CH.sub.2 NR.sub.1 R.sub.2, where R.sub.1 and R.sub.2 are as defined below, or --COR.sub.3 where R.sub.3 is as defined below;R.sub.a represents hydrogen or R.sub.4, where R.sub.4 is as defined below;R.sub.1 represents hydrogen, C.sub.1 -C.sub.6 alkyl or phenyl-(C.sub.1 -C.sub.4 alkyl);R.sub.2 represents hydrogen, C.sub.1 -C.sub.6 alkyl, phenyl-(C.sub.1 -C.sub.4 alkyl) or, when R.sub.a is hydrogen, R.sub.4, where R.sub.4 is as defined below;R.sub.3 represents hydroxy, or when R.sub.a is hydrogen, C.sub.1 -C.sub.8 alkoxy, --NR.sub.5 R.sub.6, where R.sub.5 and R.sub.6 are as defined below, or an aminocarboxylic acid residue derived by removal of an hydrogen atom from the amino moiety of an L-aminocarboxylic acid;each R.sub.4, independently, represents C.sub.2 -C.sub.
    Type: Grant
    Filed: August 21, 1981
    Date of Patent: November 29, 1983
    Assignee: Merrell Toraude et Compagnie
    Inventors: Philippe Bey, Fritz Gerhart, Michel Jung, Daniel Schirlin
  • Patent number: 4388475
    Abstract: Organic sulfoxides having a latent allyl group bound to the sulfur are enzyme inhibitors of the suicide or K.sub.cat type.
    Type: Grant
    Filed: May 7, 1980
    Date of Patent: June 14, 1983
    Assignee: Merck & Co., Inc.
    Inventor: Raymond A. Firestone
  • Patent number: 4335045
    Abstract: An N-alkenyl-2-aminomethyl-pyrrolidine is prepared by firstly reacting tetrahydrofurfurylamine with gaseous hydrochloric acid and thionyl chloride to produce 2,5 dichloropentylamine hydrochloride. This is acetylized, possibly by acetyl chloride in dichloroethane in the presence of triethylamine, into N-acetyl-2,5-dichloropentylamine which is condensed with an alkenylamine into an N-alkenyl-2-acetylaminomethyl pyrrolidine from which the acetyl group is separated, for example by boiling with concentrated hydrochloric acid.
    Type: Grant
    Filed: March 24, 1976
    Date of Patent: June 15, 1982
    Assignee: Sachim S.A.
    Inventor: Eric-Alain Denzler
  • Patent number: 4294828
    Abstract: There are provided certain N-(1-lower alkyl-2-pyrrolidylmethyl)2-lower aly-4-amino-5-lower alkyl sulphonyl benzamides and derivatives thereof which provide surprising antiapomorphine and antiserotonin activity.
    Type: Grant
    Filed: January 18, 1979
    Date of Patent: October 13, 1981
    Assignee: Societe d'Etudes Scientifiques et Industrielles de l'Ile de-France
    Inventors: Michel Thominet, Jacques Acher, Jean-Claude Monier
  • Patent number: 4269788
    Abstract: Cyclohexadiene derivatives of the formula ##STR1## wherein R.sup.1,R.sup.2,R.sup.3 and R.sup.4 are as hereinafter set forth, are described. The compounds of formula I are useful as analgesic agents.
    Type: Grant
    Filed: October 4, 1979
    Date of Patent: May 26, 1981
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Peter M. Muller, Rudolf Pfister, Rene Urban
  • Patent number: 4246200
    Abstract: This invention relates to compounds having the formula ##STR1## in which R.sub.F is a perfluoro radical C.sub.n F.sub.2n+1 with n=1-20, and R is a C.sub.1-20 alkyl radical, a C.sub.4-15 cycloalkyl radical, a C.sub.5-20 cycloalkyl-alkyl radical, or a C.sub.6-20 aromatic radical.Said compounds constitute valuable intermediates for the synthesis of surface-active agents.
    Type: Grant
    Filed: May 29, 1979
    Date of Patent: January 20, 1981
    Assignee: Agence Nationale de Valorisation de la Recherche (ANVAR)
    Inventors: Claude Wakselman, Marc Tordeux