Halogen, Bonded Directly To Carbon, Containing Patents (Class 564/510)
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Patent number: 5461117Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.Type: GrantFiled: June 13, 1994Date of Patent: October 24, 1995Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy J. Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5352785Abstract: 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: GrantFiled: March 30, 1993Date of Patent: October 4, 1994Assignee: Minnesota Mining and Manufacturing CompanyInventors: Thomas C. Herzberg, Robert B. Fletcher, Randall F. Henderson
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Patent number: 5334765Abstract: 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: GrantFiled: October 14, 1993Date of Patent: August 2, 1994Assignee: Imperial Chemical Industries PLCInventor: Robert T. Jacobs
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Patent number: 5332790Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.Type: GrantFiled: March 8, 1993Date of Patent: July 26, 1994Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5322904Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.Type: GrantFiled: March 8, 1993Date of Patent: June 21, 1994Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy J. Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5322903Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.Type: GrantFiled: January 17, 1992Date of Patent: June 21, 1994Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5274118Abstract: 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: GrantFiled: December 4, 1991Date of Patent: December 28, 1993Assignee: Imperial Chemical Industries PLCInventors: Robert T. Jacobs, Andrew G. Brewster, George J. Sependa
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Patent number: 5256825Abstract: 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: GrantFiled: December 28, 1992Date of Patent: October 26, 1993Assignees: Agency of Industrial Science & Technology, Ministry of International Trade & IndustryInventors: Haruhiko Fukaya, Takashi Abe, Eiji Hayashi, Yoshio Hayakawa
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Diluent for perfluorocarbons employed for retinal unfolding (unfolding PFCL) and method of treatment
Patent number: 5244924Abstract: 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: GrantFiled: January 24, 1992Date of Patent: September 14, 1993Assignee: Adatomed Pharmazeutische und Medizintechnische Gesellschaft mbHInventor: Hasso Meinert -
Patent number: 5225561Abstract: 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: GrantFiled: September 12, 1990Date of Patent: July 6, 1993Assignee: Advanced Technology Materials, Inc.Inventors: Peter S. Kirlin, Duncan W. Brown, Robin A. Gardiner
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Patent number: 5214214Abstract: 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: GrantFiled: March 30, 1992Date of Patent: May 25, 1993Assignee: The Green Cross CorporationInventors: Kirby V. Scherer, Jr., Kouichi Yamanouchi, Kazumasa Yokoyama, Kimie Naito
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Patent number: 5196595Abstract: 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: GrantFiled: April 28, 1992Date of Patent: March 23, 1993Assignee: Ausimont S.R.L.Inventors: Walter Navarrini, Darryl D. Desmarteau
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Patent number: 5169868Abstract: 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: GrantFiled: March 1, 1991Date of Patent: December 8, 1992Assignee: University of SaskatchewanInventors: Peter H. Yu, Bruce A. Davis, Alan A. Boulton
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Patent number: 5169548Abstract: 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: GrantFiled: April 26, 1991Date of Patent: December 8, 1992Assignee: Ausimont S.r.l.Inventors: Ezio Strepparola, Piero Gavezotti, Costante Corti
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Patent number: 5117055Abstract: A perfluoroalkyl halogenide represented by the formula: ##STR1## wherein X stands for one element selected from the group consisting of iodine and bromine, R.sub.f for a perfluorohydrocarbon group, n for an integer in the range of 1 to 3, and m for an integer in the range of 1 to 3, provided that n and m satisfy the relationship, n.gtoreq.m, is produced by a method which consists essentially in subjecting a perfluorocarboxylic acid fluoride represented by the formula, ##STR2## wherein R.sub.f and n have the same meanings as defined above, to a thermal reaction with a lithium halogenide represented by XI, wherein X has the same meaning as defined above.Type: GrantFiled: February 22, 1990Date of Patent: May 26, 1992Assignees: Agency of Industrial Science and Technology, Ministry of International Trade & IndustryInventors: Takashi Abe, Eiji Hayashi, Haruhiko Fukaya
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Patent number: 5093432Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.Type: GrantFiled: September 28, 1989Date of Patent: March 3, 1992Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5075508Abstract: 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: GrantFiled: July 19, 1989Date of Patent: December 24, 1991Assignee: Daikin Industries Ltd.Inventors: Kenji Mikami, Yoshio Iwai, Nobuyoshi Iwashita, Yasuhisa Furutaka
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Patent number: 5057623Abstract: 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: GrantFiled: October 13, 1989Date of Patent: October 15, 1991Assignee: Matsushita Electric Industrial Co., Ltd.Inventors: Yoshiaki Kai, Takashi Suzuki
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Patent number: 5019654Abstract: 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: GrantFiled: March 19, 1987Date of Patent: May 28, 1991Assignee: Bayer AktiengesellschaftInventors: Bernd Baasner, Hermann Hagemann, Michael Schwamborn
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Patent number: 5017718Abstract: 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: GrantFiled: January 26, 1984Date of Patent: May 21, 1991Assignee: Sagami Chemical Research CenterInventors: Iwao Ojima, Takamasa Fuchikami
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Patent number: 4990633Abstract: New fluorinated bisaryloxy-substituted alkenes are prepared by reaction of substituted phenols with perhaloalkenes and can be used as electrical insulating agents.Type: GrantFiled: May 4, 1989Date of Patent: February 5, 1991Assignee: Bayer AktiengesellschaftInventors: Michael Negele, Dietmar Beilefeldt, Thomas Himmler, Albrecht Marhold
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Patent number: 4985556Abstract: 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: GrantFiled: September 9, 1988Date of Patent: January 15, 1991Assignees: Agency of Industrial Science & Technology, Ministry of International Trade & IndustryInventors: Takashi Abe, Eiji Hayashi
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Patent number: 4943595Abstract: 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: GrantFiled: February 22, 1984Date of Patent: July 24, 1990Assignee: The Green Cross CorporationInventors: Kirby V. Scherer, Jr., Kouichi Yamanouchi, Kazumasa Yokoyama, Ryoichi Naito, deceased
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Patent number: 4921957Abstract: 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: GrantFiled: July 6, 1989Date of Patent: May 1, 1990Assignee: Ausimont S.r.l.Inventors: Alessandro Malacrida, Darryl D. Desmarteau
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Patent number: 4914240Abstract: Gem-dihalo-1,8-diamino-4-aza-octane derivatives useful as antiproliferative or antitumor agents.Type: GrantFiled: March 30, 1989Date of Patent: April 3, 1990Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Fritz Gerhart, Pierre Mamont
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Patent number: 4912216Abstract: 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: GrantFiled: July 10, 1987Date of Patent: March 27, 1990Assignees: Agency of Industrial Science & Technology, Ministry of International Trade & IndustryInventor: Takashi Abe
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Patent number: 4886915Abstract: 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: GrantFiled: June 24, 1988Date of Patent: December 12, 1989Assignee: Great Lakes Chemical CorporationInventor: Nicolai A. Favstritsky
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Patent number: 4886610Abstract: 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: GrantFiled: December 15, 1988Date of Patent: December 12, 1989Assignee: Ciba-Geigy CorporationInventors: Hermann O. Wirth, Hans-Helmut Friedrich
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Patent number: 4879327Abstract: 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: GrantFiled: March 31, 1988Date of Patent: November 7, 1989Assignee: AtochemInventors: Pierre Poisson, Nadine Rivas, Pierre Deloy
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Patent number: 4859357Abstract: 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: GrantFiled: June 9, 1988Date of Patent: August 22, 1989Assignee: Societe AtochemInventors: Laurent Germanaud, Marc Hermant
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Patent number: 4853141Abstract: 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: GrantFiled: June 10, 1988Date of Patent: August 1, 1989Assignee: Societe ATOCHEMInventors: Pierre Durual, Marc Hermant, Charles Laviron
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Patent number: 4851448Abstract: Gem-dihalo-1,8-diamino-4-aza-octane derivatives useful as antiproliferative or antitumor agents.Type: GrantFiled: June 15, 1987Date of Patent: July 25, 1989Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Fritz Gerhart, Pierre Mamont
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Patent number: 4782148Abstract: 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: GrantFiled: July 18, 1986Date of Patent: November 1, 1988Assignees: Agency of Industrial Science & Technology, Ministry of International Trade & IndustryInventor: Takashi Abe
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Patent number: 4778926Abstract: Gem-dihalo and gem-tetrahalo-1,12-diamino-4,9-diazadodecane derivatives useful as antiproliferative or antitumor agents.Type: GrantFiled: June 15, 1987Date of Patent: October 18, 1988Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Fritz Gerhart, Pierre Mamont
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Patent number: 4760377Abstract: 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: GrantFiled: March 29, 1985Date of Patent: July 26, 1988Assignee: Giordano Associates, Inc.Inventor: Philip C. Jackson
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Patent number: 4719312Abstract: 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: GrantFiled: September 2, 1986Date of Patent: January 12, 1988Assignee: Merck & Co., Inc.Inventor: Raymond A. Firestone
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Patent number: 4719313Abstract: Gem-dihalo and gem-tetrahalo-1,12-diamino-4,9-diaza-dodecane derivatives useful as antiproliferative or antitumor agents.Type: GrantFiled: February 12, 1986Date of Patent: January 12, 1988Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Fritz Gerhart, Pierre Mamont
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Patent number: 4707498Abstract: 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: GrantFiled: January 14, 1986Date of Patent: November 17, 1987Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Michael Kolb, David A. Kendrick
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Patent number: 4695654Abstract: Gem-dihalo-1,8-diamino-4-aza-octane derivatives useful as antiproliferative or antitumor agents.Type: GrantFiled: August 21, 1985Date of Patent: September 22, 1987Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Fritz Gerhart, Pierre Mamont
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Patent number: 4670470Abstract: Organic sulfoxides having a latent allyl group bound to the sulfur are enzyme inhibitors of the suicide or K.sub.cat type.Type: GrantFiled: August 29, 1985Date of Patent: June 2, 1987Assignee: Merck & Co., Inc.Inventor: Raymond A. Firestone
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Patent number: 4585569Abstract: 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: GrantFiled: December 24, 1984Date of Patent: April 29, 1986Assignee: Imperial Chemical Industries PLCInventor: Richard L. Powell
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Patent number: 4558071Abstract: Organic sulfoxides having a latent allyl group bound to the sulfur are enzyme inhibitors of the suicide or K.sub.cat type.Type: GrantFiled: February 25, 1983Date of Patent: December 10, 1985Assignee: Merck & Co., Inc.Inventor: Raymond A. Firestone
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Patent number: 4541943Abstract: 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: GrantFiled: May 16, 1984Date of Patent: September 17, 1985Assignee: Imperial Chemical Industries PLCInventor: Richard L. Powell
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Patent number: 4435425Abstract: 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: GrantFiled: April 9, 1982Date of Patent: March 6, 1984Assignee: Merrell Toraude et CompagnieInventors: Albert Sjoerdsma, Philippe Bey, Michel Jung, Fritz Gerhart, Daniel Schirlin
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Patent number: 4418077Abstract: 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: GrantFiled: August 21, 1981Date of Patent: November 29, 1983Assignee: Merrell Toraude et CompagnieInventors: Philippe Bey, Fritz Gerhart, Michel Jung, Daniel Schirlin
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Patent number: 4388475Abstract: Organic sulfoxides having a latent allyl group bound to the sulfur are enzyme inhibitors of the suicide or K.sub.cat type.Type: GrantFiled: May 7, 1980Date of Patent: June 14, 1983Assignee: Merck & Co., Inc.Inventor: Raymond A. Firestone
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Patent number: 4335045Abstract: 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: GrantFiled: March 24, 1976Date of Patent: June 15, 1982Assignee: Sachim S.A.Inventor: Eric-Alain Denzler
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Patent number: 4294828Abstract: 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: GrantFiled: January 18, 1979Date of Patent: October 13, 1981Assignee: Societe d'Etudes Scientifiques et Industrielles de l'Ile de-FranceInventors: Michel Thominet, Jacques Acher, Jean-Claude Monier
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Patent number: 4269788Abstract: 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: GrantFiled: October 4, 1979Date of Patent: May 26, 1981Assignee: Hoffmann-La Roche Inc.Inventors: Peter M. Muller, Rudolf Pfister, Rene Urban
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Patent number: 4246200Abstract: 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: GrantFiled: May 29, 1979Date of Patent: January 20, 1981Assignee: Agence Nationale de Valorisation de la Recherche (ANVAR)Inventors: Claude Wakselman, Marc Tordeux