Halogen In Acid Moiety Patents (Class 560/184)
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Publication number: 20040186313Abstract: The invention relates to synthesis methods for the preparation of statin derivatives, which methods proceed by way of a key intermediate of formula I wherein X is halogen, acyloxy, activated hydrocarbyloxy, activated hydrocarbylthio or N(CH3)OCH3, Ra is a hydroxy-protecting group, and Rb is a carboxy-protecting group, and, as well as to the compound of formula I, to further intermediates and methods for their preparation by Friedel-Crafts acylation.Type: ApplicationFiled: December 31, 2003Publication date: September 23, 2004Inventors: Reinhold Ohrlein, Gabriele Baisch, Nicole End, Stephan Burkhardt, Martin Studer
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Patent number: 6790982Abstract: The present invention provides a process whereby fluorine atom-containing sulfonyl fluoride compound(s) useful as e.g. materials for ion-exchange membranes, can be produced efficiently and at low cost without structural limitations while solving the difficulties in production. The present invention is also directed to a compound of the following formula (I) or a compound of the following formula (II): FSO2CH2CH2OCH2OCOCF(CF3)OCF2CF2CF3 (I) FSO2CF2CF2OCF2CF2OCOCF(CF3)OCF2CF2CF3 (II).Type: GrantFiled: May 21, 2003Date of Patent: September 14, 2004Assignee: Asahi Glass Company, LimitedInventors: Masahiro Ito, Kunio Watanabe, Takashi Okazoe, Isamu Kaneko, Daisuke Shirakawa
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Publication number: 20040176636Abstract: There is provided a process for producing a fluorinated vinyl ether from a fluorinated acid fluoride compound having an ester group as a precursor of a carboxylic acid group, or a SO2F group as a precursor of a sulfonic acid group, in high yield by simple operations.Type: ApplicationFiled: December 29, 2003Publication date: September 9, 2004Inventors: Nobuto Hoshi, Nobuyuki Uematsu, Masanori Ikeda
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Patent number: 6743943Abstract: Vinyl ether compounds having the formula: R—O—X—O—CH═CH2 wherein R is a radical selected from R1—CnHm—, R1—CnHm—C(═O)—, R1—CnHm—CH[—O—X—O—CH═CH2—], R1—CnHm—CH[—O—X—O—CH═CH2—]C(═O)—, R1—CnHm—CH[—C(═O)—O—X—O—CH═CH2—], R1—CnHm—CH[—C(═O)—O—X—O—CH═CH2—]C(═O)—, R1—[CFCl—CF2—]pCH2— and HCFCl—CF2—, wherein R1 is hydrogen, an unsubstituted or substituted fluorinated aliphatic radical, an unsubstituted or substituted fluorinated cyclic aliphatic radical, an unsubstituted or substituted fluorinated aromatic radical, an unsubstituted or substituted fluorinated araliphatic radical, or an unsubstituted or substituted fluorinated heterocyclic radType: GrantFiled: May 11, 2001Date of Patent: June 1, 2004Assignee: Honeywell International Inc.Inventors: Russell F. Anderson, David E. Bradley, David Nalewajek, Haridasan K. Nair, Mariola J. Proszowski, Eugene V. Sitzman, Ellen L. Swan
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Patent number: 6723871Abstract: A novel production process capable of obtaining an optically active alcohol in a high optical purity by subjecting a &bgr;-keto ester such as a 3-perfluoroalkyl-3-oxopropionate ester or a 3-trichloroalkyl-3-oxopropionate ester to asymmetric reduction in simple and convenient operations.Type: GrantFiled: May 13, 2002Date of Patent: April 20, 2004Assignee: Takasago International CorporationInventors: Kenichi Tada, Takashi Miura
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Publication number: 20030204099Abstract: The invention provides a process for producing a fluorine-containing compound from an inexpensive material.Type: ApplicationFiled: April 24, 2003Publication date: October 30, 2003Applicant: ASAHI GLASS COMPANY, LIMITEDInventors: Takashi Okazoe, Kunio Watanabe, Shin Tatematsu, Hidenobu Murofushi
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Publication number: 20030187291Abstract: Iodohydroxylated olefins can be prepared by treating an olefin with an aqueous solution of an iodine monohalide selected from iodine monochloride and iodine monobromide.Type: ApplicationFiled: January 31, 2003Publication date: October 2, 2003Inventors: Yongkui Sun, Thorsten Rosner
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Patent number: 6548459Abstract: A process for the preparation of CNSL phenoxy carboxylic acid derivatives for use as an additive in a lubricant composition so as to impart improved rust inhibiting properties, including the steps of (a) partially hydrogenating distilled technical cashew nut shell liquid with palladium or nickel or platinum catalyst; to hydrogenate the olefinic chain; (b) reacting cashew nut shell liquid or partially hydrogenated technical cashew nut shell liquid with halogeno carboxylic acid derivatives to obtain unpolymerized cashew nut shell liquid phenoxy carboxylic acid derivatives, the reaction being carried out at a temperature ranging from 20 to 140° C. A lubricant containing a major proportion of a material selected from the group consisting of an oil of lubricating viscosity and a grease; and remainder an additive including CNSL phenoxy carboxylic acid derivative prepared by the foregoing process.Type: GrantFiled: April 2, 2002Date of Patent: April 15, 2003Assignee: Indian Oil Corporation LimitedInventors: Pankaj Kumar Mondal, Khem Chand Dohhen, Rakesh Sarin, Deepak Kumar Tuli, Niranjan Raghunath Raje, Akhilesh Kumar Bhatnagar
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Publication number: 20030050198Abstract: A process for the preparation of CNSL phenoxy carboxylic acid derivatives for use as an additive in a lubricant composition so as to impart improved rust inhibiting properties, including the steps of (a) partially hydrogenating distilled technical cashew nut shell liquid with palladium or nickel or platinum catalyst; to hydrogenate the olefinic chain; (b) reacting cashew nut shell liquid or partially hydrogenated technical cashew nut shell liquid with halogeno carboxylic acid derivatives to obtain unpolymerized cashew nut shell liquid phenoxy carboxylic acid derivatives, the reaction being carried out at a temperature ranging from 20 to 140° C. A lubricant containing a major proportion of a material selected from the group consisting of an oil of lubricating viscosity and a grease; and remainder an additive including CNSL phenoxy carboxylic acid derivative prepared by the foregoing process.Type: ApplicationFiled: April 2, 2002Publication date: March 13, 2003Applicant: Indian Oil Corporation LimitedInventors: Pankaj Kumar Mondal, Khem Chand Dohhen, Rakesh Sarin, Deepak Kumar Tuli, Niranjan Raghunath Raje, Akhilesh Kumar Bhatnagar
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Publication number: 20030004362Abstract: A novel production process capable of obtaining an optically active alcohol in a high optical purity by subjecting a &bgr;-keto ester such as a 3-perfluoroalkyl-3-oxopropionate ester or a 3-trichloroalkyl-3-oxopropionate ester to asymmetric reduction in simple and convenient operations.Type: ApplicationFiled: May 13, 2002Publication date: January 2, 2003Applicant: TAKASAGO INTERNATIONAL CORPORATIONInventors: Kenichi Tada, Takashi Miura
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Patent number: 6492545Abstract: A novel process in which an optically active alcohol compound having a desired absolute configuration and a high optical purity can be obtained by asymmetrically hydrogenating a &bgr;-keto acid compound through a simple operation. An optically active alcohol represented by general formula (III) as defined is obtained by asymmetrically hydrogenating a &bgr;-keto ester compound represented by general formula (I) as defined in the presence of at least one ruthenium complex having as a ligand an optically active tertiary diphosphine compound represented by general formula (II) as defined.Type: GrantFiled: July 23, 2001Date of Patent: December 10, 2002Assignee: Takasago International CorporationInventors: Takao Saito, Tohru Yokozawa, Kazuhiko Matsumura, Noboru Sayo
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Patent number: 6482979Abstract: A method for the preparation of a perfluorinated acid fluoride (especially 3-alkoxy propionic acid fluoride) is provided. The method results in high yields of the acid fluoride.Type: GrantFiled: December 22, 1999Date of Patent: November 19, 2002Assignees: Dyneon LLC, 3M Innovative Properties CompanyInventors: Klaus Hintzer, Zai-Ming Qiu, George G. I. Moore, Werner Schwertfeger, Jay F. Schulz, Allan T. Worm, Christopher L. Gross
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Patent number: 6417390Abstract: Use of surfactants in the suspension polymerization of fluorinated monomers for preparing fluoropolymers containing hydrogen, said surfacants having the general formula: Rf—[L—(OCHR1—CHR2)m—OZ)]i wherein: i is equal to 1 or 2; m is an integer comprised between 4 and 60; L can be chosen between: —(CFY—CO—O)pR′— and —(CFY—CO—NH)pR′— wherein is an integer equal to 0 or to 1; Y═F, CF3; R′=alkylic radical C1-C5, linear or branched when possible; R1, R2 can be both H or the former H and the latter CH3; Z can be H, alkyl radical C1-C3, linear or branched when possible; or (CH2)nOH with n an integer from 1 to 6; Rf is a perfluoroalkylic radical or a perfluoropolyether radical, having a number average molecular weight comprised between 250 and 1500.Type: GrantFiled: November 8, 1999Date of Patent: July 9, 2002Assignee: Ausimont S.p.A.Inventors: Julio A. Abusleme, Paolo Lazzari
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Patent number: 6407282Abstract: Monoester monoacid fluoride of dicarboxylic acid is produced by allowing dicaroxylic acid fluoride represented by the following general formula: FOCCF(CF3)OCF2(A)p(CF2)qCOF where A is a bifunctional perfluorinated group having 1 to 10 carbon atoms; p is 0 or 1; and q is 0 or an integer of 1-10, to react with an alcohol having at least 3 carbon atoms, thereby esterifying the terminal CF2COF group. Such selective monoesterification reaction is effective for separation and purification of a dicarboxylic acid difluoride isomer mixture comprising symmetrical dicarboxylic acid difluoride and asymmetrical dicarboxylic acid difluoride.Type: GrantFiled: October 30, 2000Date of Patent: June 18, 2002Assignee: Nippon Mektron, LimitedInventors: Hiroaki Murata, Sunao Ikeda, Satoru Saito
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Patent number: 6372923Abstract: The present invention provides a process for preparing an alcohol derivative, where the alcohol derivative is an ester, acetal, ketal, ether glycoside, or alkyl glycoside, by reacting an alcohol with a carbonyl compound, alcohol, olefin, epoxy compound or saccharide, where C2-4 vicinal alkylene oxides are excluded, in the presence of (A) an aluminum alkoxide and (B) sulfuric acid or phosphoric acid.Type: GrantFiled: May 31, 2000Date of Patent: April 16, 2002Assignee: Kao CorporationInventors: Mitsuru Uno, Munehisa Okutsu, Tomohito Kitsuki
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Publication number: 20020035283Abstract: A novel process in which an optically active alcohol compound having a desired absolute configuration and a high optical purity can be obtained by asymmetrically hydrogenating a &bgr;-keto acid compound through a simple operation. An optically active alcohol represented by general formula (III) as defined is obtained by asymmetrically hydrogenating a &bgr;-keto ester compound represented by general formula (I) as defined in the presence of at least one ruthenium complex having as a ligand an optically active tertiary diphosphine compound represented by general formula (II) as defined.Type: ApplicationFiled: July 23, 2001Publication date: March 21, 2002Applicant: TAKASAGO INTERNATIONAL CORPORATIONInventors: Takao Saito, Tohru Yokozawa, Kazuhiko Matsumura, Noboru Sayo
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Patent number: 6353012Abstract: HETE derivatives and methods of their use for treating dry eye are disclosed.Type: GrantFiled: October 23, 2000Date of Patent: March 5, 2002Assignee: Alcon Universal Ltd.Inventors: Mark R. Hellberg, John M. Yanni, Gustav Graff, Daniel A. Gamache, Peter G. Klimko
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Patent number: 6316505Abstract: Block copolymers containing a fluorinated hydrocarbon unit, a hydrocarbon unit, and a poly(oxyethylene) unit are useful in fluid formulations of pharmaceutical agents. A typical embodiment is: C11H23—CONHC2H4NHCO—C8F16—CONHC2H4NHCOO—(C2H4O)34—H.Type: GrantFiled: August 5, 1999Date of Patent: November 13, 2001Assignee: Supratek Pharma, Inc.Inventors: Alexander V. Kabanov, Serguei V. Vinogradov
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Publication number: 20010034458Abstract: Vinyl ether compounds having the formula:Type: ApplicationFiled: May 11, 2001Publication date: October 25, 2001Applicant: AlliedSignal Inc.Inventors: Russell F. Anderson, David E. Bradley, David Nalewajek, Haridasan K. Nair, Mariola J. Proszowski, Eugene V. Sitzmann, Ellen L. Swan
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Patent number: 6307094Abstract: The present invention provides a solventless process for the catalytic hydrogenation of esters of 4,4,4-trihaloacetoacetic acid using a platinum catalyst in the presence of an acid or base co-catalyst to provide the analagous 3-hydroxybutyrate ester. Such 3-hydroxybutyrate esters are useful as solvents, cleaners or fine chemical intermediates.Type: GrantFiled: May 2, 2000Date of Patent: October 23, 2001Inventors: Joshua Anthony Chong, Fereydon Abdesaken, Lori Ann Spangler, Renee Caroline Roemmele, Randall Wayne Stephens, Peter David Nightingale, David John Hartley
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Patent number: 6300511Abstract: The present invention provides a method of substituting a carbonyl compound with fluorine at the &agr;-position, comprising reaching the carbonyl compound with a fluorinating present of a metal-containing catalyst. The reaction results in replacement of a hydrogen atom by fluorine. The catalyst, which is used in a catalytically effective amount, is preferably a transition metal. In one class of methods the catalyst is a transition metal compound. In another class of methods, the catalyst is an elemental metal, in which case the carbonyl compound has an activating group attached to the carbon atom which is substituted by fluorine.Type: GrantFiled: March 27, 2000Date of Patent: October 9, 2001Assignee: F2 Chemicals LimitedInventors: Richard Dickinson Chambers, John Hutchinson, John Stewart Moilliet
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Patent number: 6291704Abstract: Vinyl ether compounds having the formula: R—O—X—O—CH═CH2 wherein R is a radical selected from R1—CnHm—, R1—CnHm—C(═O)—, R1—CnHm—CH[—O—X—O—CH═CH2—], R1—CnHm—CH[—O—X—O—CH═CH2—]C(═O)—, R1—CnHm—CH[—C(═O)—O—X—O—CH═CH2—], R1—CnHm—CH[—C(═O)—O—X—0—CH═CH2—]C(═O)—, R1—[CFCl—CF2—]pCH2— and HCFCl—CF2—, wherein R1 is hydrogen, an unsubstituted or substituted fluorinated aliphatic radical, an unsubstituted or substituted fluorinated cyclic aliphatic radical, an unsubstituted or substituted fluorinated aromatic radical, an unsubstituted or substituted fluorinated araliphatic radical, or an unsubstituted or substituted fluorinated heterocyclic radiType: GrantFiled: March 18, 1999Date of Patent: September 18, 2001Assignee: AlliedSignal Inc.Inventors: Russell F. Anderson, David E. Bradley, David Nalewajek, Haridasan K. Nair, Mariola J. Proszowski, Eugene V. Sitzman, Ellen L. Swan
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Patent number: 6187724Abstract: A lubricant composition comprising (A) a compound of the formula: R1—COO—R2 wherein R1 is a higher aliphatic hydrocarbon residue and R2 is an aliphatic hydrocarbon residue which may contain fluorine atom(s) and/or oxygen atom(s), and (B) a compound of the formula: wherein R3 is a higher aliphatic hydrocarbon residue; R4 and R5 are independently a hydrogen atom or an aliphatic hydrocarbon residue which may contain fluorine atom(s) and/or oxygen atom(s), gives a lubricant layer in a magnetic recording medium having good running durability, still life and weather resistance.Type: GrantFiled: September 28, 1998Date of Patent: February 13, 2001Assignees: Wako Pure Chemical Industries, Ltd., TDK CorporationInventors: Tsunehiko Ikarashi, Koji Kobayashi, Hiromichi Kanazawa, Takahiro Hayashi, Takehiko Iritani
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Patent number: 6184376Abstract: Methods and novel intermediates of the formula: wherein R6 and R7 are lower alkyl or benzyl or R6 and R7 taken together are —CH2CH2—, —CH2CH2CH2— or —CH2CH2CH2CH2CH2—, R8 is C1-C21 alkyl or a C2-C21 monounsaturated alkenyl, which may optionally be substituted with substitution substituents independently selected from the group consisting of hydroxy, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkanoyl, amino, halo, cyano, azido, oxo, mercapto and nitro, and R9 is an alcohol protecting group. The intermediates are useful for the preparation of acyclic nucleoside derivatives of the formula: where one of R1 and R2 is an amino acid acyl group and the other of R1 and R2 is a —C(O)C3-C21 saturated or monounsaturated, optionally substituted alkyl and R3 is OH or H; or a pharmaceutically acceptable salt thereof.Type: GrantFiled: August 6, 1998Date of Patent: February 6, 2001Assignee: Mediver ABInventors: M. Robert Leanna, Steven M. Hannick, Michael Rasmussen, Jien-Heh J. Tien, Lakshmi Bhagavatula, Pulla Reddy Singam, Bradley D. Gates, Lawrence Kolaczkowski, Ramesh R. Patel, Greg Wayne, Greg Lannoye, Weijiang Zhang, Zhenping Tian, Kirill A. Lukin, Bikshandarkoil A. Narayanan, David A. Riley, Howard Morton, Sou-Jen Chang, Cynthia B. Curty, Daniel Plata, John Bellettini, Bhadra Shelat, Tiffany Spitz, Cheng-Xi Yang
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Patent number: 6166260Abstract: The present invention relates to a tandem process of reduction and host-guest complexation using metal-hydride complexes to reduce chemical entities bearing carbonyl groups or their equivalents, and host-guest complexation to achieve improved optical resolution of the reduction product. In the complexation step, the reduction product is optically resolved via inclusion into the crystalline complex where it resides as guest and another complex component acts as host. Additional crystallization stages are performed if further improvements in the enantiomeric excess is desired.Type: GrantFiled: August 6, 1999Date of Patent: December 26, 2000Assignee: Zeeland Chemicals, Inc.Inventor: Glenn L. Heise
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Patent number: 6160161Abstract: Per(poly)fluorinated polyoxyethylated carbamates of general formula (I) in which R.sub.F represents a perfluorinated group containing between 1 and 18 carbon atoms, W represents an oxo group or nothing, n is an integer from 1 to 10, m is from values 2 to 6, 80 or not defined, R is an alkyl group, R.sub.F W(CH.sub.2).sub.n+1 NHC(O)-- in which R.sub.F and W are as defined above, --(CHCH.sub.3 CH.sub.2 O).sub.30 (CH.sub.2 CH.sub.2).sub.80 C(O)NH(CH.sub.2).sub.n+1 R.sub.F in which R.sub.F is a perfluorinated group containing from 1 to 18 carbon atoms, R' is a hydrogen atom, an alkyl group containing between 1 and 18 carbon atoms which is optionally substituted, an optionally substituted aryl or aralkyl group, an allyl, methallyl or propargyl group or a perfluorinated chain having between 1 and 18 carbon atoms.Type: GrantFiled: December 23, 1998Date of Patent: December 12, 2000Assignee: F2 Chemicals LimitedInventors: Hedi Trabelsi, Wolfgang Roehlke, Peter Reuter, Massimo Napoli, Philippe Lucas, Kenneth Charles Lowe, Giampaolo Gambaretto, Ralf-Peter Franke, Carl Martin Edwards, Lino Conte, Aime Cambon
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Patent number: 6127517Abstract: Before hexafluoropropene oxide (HFPO) is polymerized in a polymerization initiator solution of a polymerization initiator of the formula: CSOCF.sub.2 --Rf--CF.sub.2 OCs wherein Rf is a perfluoroalkylene group which may have an ether bond in an aprotic polar solvent, the initiator solution is treated by adding a perfluoroolefin thereto at a sufficient temperature for the removal of protonic substances, cesium fluoride and hydrogen fluoride. This simple treatment restrains chain transfer reaction, and the process is successful in producing a difunctional HFPO polymer having a high degree of polymerization while suppressing formation of a monofunctional HFPO polymer.Type: GrantFiled: April 1, 1999Date of Patent: October 3, 2000Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Noriyuki Koike, Shinichi Sato, Nobuyuki Kobayashi
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Patent number: 5985859Abstract: A method of inhibiting bacterial sialidase comprising administering to a subject an inhibiting effective amount of a compound of formula I: ##STR1## wherein A is CO.sub.2 H, PO.sub.2 H, or SO.sub.2 H; B is N; R.sub.1 and R.sub.2 are H; R.sub.3 and R.sub.4 are, independently, H, OH, NO.sub.2, guanidino, or alkyl or alkenyl of from 1 to 3 carbons where the alkyl or alkenyl is unsubstituted or is substituted, independently, with one or more of OH, NH2, or halide; R.sub.5 is H; and R.sub.6 is COCH.sub.3, or COCI.sub.3 ; or an analog, pharmaceutically acceptable salt, derivative, or mixture thereof. A method of preventing a bacterial or trypanosomal infection using the compounds of formula I. A method of treating a bacterial or trypanosomal infection using the compounds of formula I. A pharmaceutical composition comprising a pharmaceutically acceptable carrier admixed with an inhibiting effective amount of a compound of formula I.Type: GrantFiled: June 7, 1995Date of Patent: November 16, 1999Assignee: The University of AlabamaInventor: Ming Luo
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Patent number: 5919973Abstract: The invention provides a process for polymerizing hexafluoropropene oxide in a polymerization initiator solution to produce a fluorinated polyether. The initiator solution contains a polymerization initiator of the formula: CSOCF.sub.2 -Rf-CF.sub.2 OCs wherein Rf is a C1-C4 perfluoroalkylene group or a C2-C1O perfluoroalkylene group having an ether bond in a linear or cyclic hydrocarbon compound having at least 5 ether bonds in a molecule. An aprotic polar solvent having a melting point of lower than -40.degree. C. under atmospheric pressure is added to the initiator solution.Type: GrantFiled: December 2, 1997Date of Patent: July 6, 1999Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Takashi Matsuda, Noriyuki Koike, Shinichi Sato
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Patent number: 5831131Abstract: A process for the faster manufacturing of hydrocarbon, fluorocarbon and chlorocarbon acyl peroxides is disclosed wherein a hydroxide, a peroxide and an acyl halide are reacted under continuous vigorous agitation conditions so as to bring the reaction to substantial completion is less than one minute.Type: GrantFiled: August 26, 1996Date of Patent: November 3, 1998Assignee: E. I. du Pont de Nemours and CompanyInventors: Carl George Krespan, Robert Clayton Wheland
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Patent number: 5827883Abstract: A method of using vitamin D derivatives of the formula ##STR1## wherein X is .dbd.CH.sub.2 or H,H;Y is a moiety--CH(CH.sub.3)--(A).sub.n --C(O)--OR.sup.1 (a)--CH(CH.sub.3)--CH.sub.2 --O--C(O)--R.sup.2 (b)or--C(O)--OR.sup.1 (c);A is --CH.dbd.CH-- or CH.sub.2 --CH.sub.2 --R.sup.1 is lower alkyl, cycloalkyl, cycloalkylmethyl, --CH.sub.2 R.sup.3 or --CH.sub.2 --CH.sub.2 R.sup.3 ;R.sup.2 is lower alkyl, cycloalkyl or R.sup.3 ;R.sup.3 is hydroxy-lower alkyl, hydroxy-cycloalkyl or trifluoromethyl-hydroxy-lower-alkyl;n is 0 or 1;and the dotted bond in the five membered ring is optional;in the treatment of dermatological conditions, in particular keratinization disorders such as psoriasis, as well as acne and photodamaged skin, is described.Vitamin D derivatives of the formula I above, wherein X, Y, A, R.sup.1, R.sup.2, R.sup.3 and n are as set forth above; with the proviso that X is H,H when Y is --CH(CH.sub.3)--CH.sub.2 --OC(O)--C(OH)(CH.sub.3).sub.Type: GrantFiled: July 21, 1997Date of Patent: October 27, 1998Assignee: Hoffmann-La Roche Inc.Inventors: Pierre Barbier, Marc Muller, Josef Stadlwieser
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Patent number: 5792876Abstract: A process is described for producing acetals comprising reacting an aldehyde or a ketone with an alcohol in the presence of a titanium compound having an acetylacetone as a ligand, or in the presence of a compound selected from the group consisting of stannous chloride dihydrate, cerium chloride hexahydrate and bismuth chloride. The process can be used in the synthesis of unstable acetals or when water exists in the reaction mixture, and therefore the process can be used for a wide variety of applications.Type: GrantFiled: November 6, 1996Date of Patent: August 11, 1998Assignee: Kuraray Co., Ltd.Inventors: Hideharu Iwasaki, Masahiko Kitayama, Takashi Onishi
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Patent number: 5763552Abstract: A partially-fluorinated surfactant having internal methylene groups and having the formula R.sub.f --(CH.sub.2).sub.m --R'.sub.f --COOM wherein m is 1-3, R.sub.f is perfluoroalkyl or perfluoroalkoxy, containing 3-8 carbon atoms, R'.sub.f is linear or branched perfluoroalkylene containing 1-4 carbon atoms, and M is NH.sub.4, Li, Na, K, or H is useful in polymerization of fluorinated monomers. High molecular weight can be achieved in homopolymerization of tetrafluoroethylene.Type: GrantFiled: July 1, 1997Date of Patent: June 9, 1998Assignee: E. I. du Pont de Nemours and CompanyInventors: Andrew E. Feiring, Ming-Hong Hung, Jose M. Rodriguez-Parada, Roger J. Zipfel
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Patent number: 5750769Abstract: The invention provides novel compounds of formula:CF.sub.3 --CXCl--CH(OH)CH.sub.2 --C(CH.sub.3).sub.2 --CH.sub.2 --CO.sub.2 R(I)where X represents chloro or bromo and R represents hydrogen or alkyl of up to 4 carbon atoms, processes for preparing them and their use as intermediates in the preparation of insecticidal cyclopropane derivatives. Also provided are novel compounds of formula:BrCH.sub.2 --CH.sub.2 --C(CH.sub.3).sub.2 --CH.sub.2 --CO.sub.2 R(IV)wherein R represents alkyl of up to 4 carbon atoms, useful as intermediates in the preparation of the compounds of formula I.Type: GrantFiled: November 8, 1995Date of Patent: May 12, 1998Assignee: Zeneca LimitedInventor: Martin Charles Bowden
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Patent number: 5739394Abstract: The invention relates to novel 3,3-dioxy-4,4,4-trifluorobutyric acid derivatives of the formula (I) ##STR1## in which R.sup.1 and R.sup.2 independently of one another represent C.sub.1 -C.sub.10 -alkyl, or represent cyclohexyl, or represent optionally substituted C.sub.6 -C.sub.10 -aryl or C.sub.7 -C.sub.14 -arylalkyl, orR.sup.1 and R.sup.2 together represent C.sub.2 -C.sub.4 -alkylene which is optionally mono- or disubstituted by methyl, or optionally substituted ortho-arylene,R.sup.3 represents hydrogen or C.sub.1 -C.sub.10 -alkyl, or represents cycloalkyl, or represents optionally substituted C.sub.6 -C.sub.10 -aryl or C.sub.7 -C.sub.Type: GrantFiled: December 16, 1996Date of Patent: April 14, 1998Assignee: Bayer AktiengesellschaftInventor: Norbert Lui
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Patent number: 5693251Abstract: An optically active phenol useful in the preparation of liquid crystalline compounds which is represented by the formula (V): ##STR1## wherein R.sub.2 represents an alkyl or alkoxyalkyl group having 1 to 20 carbon atoms optionally substituted by halogen atoms; Z' represents ##STR2## wherein q represents a number of 1 to 5 and * indicates asymmetric carbon atom; l represents a number of 2; t represents a number of 1 to 5; s represents a number of 0 or 1.Type: GrantFiled: November 23, 1994Date of Patent: December 2, 1997Assignee: Sumitomo Chemical Company, LimitedInventors: Takayuki Higashii, Isao Kurimoto, Shoji Toda, Masayoshi Minai, Takeshi Tani, Chizu Kawakami, Koichi Fujisawa
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Patent number: 5621144Abstract: New compounds are described typically having the formula CH.sub.3 C(CH.sub.2 R).sub.3 or ZCH.sub.2 C(CH.sub.2 R).sub.3 where R is a fluorohydrocarbon or perfluorocarbon group, preferably containing 4-16 carbon atoms and more F atoms that H atoms. Z is a hydrophilic group which may make the compound self-emulsifiable. The compounds are useful as oxygen transport agents in vivo, for which purpose aqueous emulsions are used, as a blood substitute.Type: GrantFiled: January 9, 1995Date of Patent: April 15, 1997Assignee: Isis Innovation LimitedInventor: Stephen R. Cooper
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Patent number: 5606098Abstract: Amides and esters of perfluoropolyoxaalkylene-sulfo- or perfluoropolyoxaalkylene-carboxylic acids of the general following formula:R.sub.F R.sub.F.sup.I ZQ, whereR.sub.F =CF.sub.3 O--, C.sub.2 F.sub.5 O--, C.sub.3 F.sub.7 O--, C.sub.8 F.sub.17 O--,R.sub.F.sup.I= ##STR1## --(CF.sub.2 CF.sub.2 O--).sub.n CF.sub.2 --, --(CF.sub.2 CF.sub.2 CF.sub.2 O).sub.n CF.sub.2 CF.sub.2 --,where n=8-55;Z=--CO--, --SO.sub.2 --,Q=--N(C.sub.m H.sub.2m OH).sub.2, where m=2, 3, 4, 6, 8, 10--N[(C.sub.2 H.sub.4 O).sub.4 C.sub.3 H.sub.6 OH].sub.2,--NH--C.sub.2 H.sub.4 OR.sub..eta., where R.eta.=CH.sub.3 --, C.sub.2 H.sub.5 --, C.sub.3 H.sub.7 --,--NH(C.sub.2 H.sub.4 O).sub.5 H,--OC.sub.1 H.sub.21 N(C.sub.1 H.sub.21 OH).sub.2, where .eta.=1, 2, 4C.sub.k H.sub.2k+1 O--, where k=6, 8, 10.Type: GrantFiled: October 3, 1995Date of Patent: February 25, 1997Assignee: AO "Avtokoninvest"Inventors: Nikolai A. Ryabinin, Aleksandr N. Ryabinin
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Patent number: 5574182Abstract: An ester is caused to act on a 2-substituted-3-hydroxycarboxylic acid ester as a racemate in the presence of hydrolase under substantially anhydrous conditions to effect a transesterification resulting in the resolution.The compound thus resolved is converted to an optically active 2,6-cis-2,5,6-substituted-1,3-dioxan-4-one and the resulting compound is recrystallized to give optically active 5,6-anti-2,5,6-substituted-1,3-dioxan-4-one and 5,6-syn-2,5,6-substituted-1,3-dioxan-4-one. Thus an optically active compound having plural chiral centers.Further, an optically active 2,5,6-substituted-1,3-dioxan-4-one obtained by transesterification and recrystallization is reacted with an alcohol to produce an optically active 2-substituted-3-hydroxycarboxylic acid ester.Type: GrantFiled: January 30, 1995Date of Patent: November 12, 1996Assignee: Chisso CorporationInventors: Kazutoshi Miyazawa, Naoyuki Yoshida
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Patent number: 5510512Abstract: Process for the preparation of 2-(dialkoxymethyl)carboxylic acid esters of the formula I ##STR1## by oxidizing .beta.-acetalization of acrylic acid esters with alcohols R.sup.1 OH, wherein R.sup.1 has the meaning mentioned, in the presence of oxygen as the oxidant and of a catalyst system based on one or more metals of the platinum group and/or compounds thereof and of a copper compound, comprises carrying out the reaction at a temperature of up to 80.degree. C. and in which the catalyst system contains 1 to 4 equivalents of anions, based on the sum of the metal atoms and metal cations, of which at most 3 equivalents are halide ions, the halogen having a molecular weight of at least 35.Type: GrantFiled: November 14, 1994Date of Patent: April 23, 1996Assignee: Hoechst AktiengesellschaftInventor: Heinz Strutz
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Patent number: 5504248Abstract: Halogenated compounds are prepared by ring opening reactions of highly fluorinated cyclopropanes with chlorine, bromine, iodine, or mixtures thereof at temperatures over 100.degree. C. A novel compound, which is one type of compound produced, is a highly fluorinated and halogenated ether and other novel compounds are starting materials or products. The products of the process are useful as chain transfer agents for certain free radical polymerizations, and as chemical intermediates in the preparation of various products such as surfactants and textile surface treatments.Type: GrantFiled: July 28, 1994Date of Patent: April 2, 1996Assignee: E. I. Du Pont de Nemours and CompanyInventors: Paul J. Krusic, Zhen-Yu Yang
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Patent number: 5491261Abstract: Di-, tri- and poly-perfluoroalkyl-substituted alcohols and acids and derivatives thereof are described which are prepared from perfluoroalkyl iodides and di-, tri- or polyallyl alcohols or acids. These compounds contain two or more perfluoroalkyl-iodoalkyl or perfluoroalkyl-alkenyl groups and one or two alcohol or acid groups or derivatized alcohol or acid functions. They can be reacted with isocyanates, epoxy compounds, anhydrides, acids or acid derivatives to prepare a great variety of oil- and water-repellent compositions which are useful for oil- and water-repellent treatment of textiles, glass, paper, leather and other substrates.Type: GrantFiled: July 1, 1994Date of Patent: February 13, 1996Assignee: Ciba-Geigy CorporationInventors: Marlon Haniff, Robert Falk, Ted Deisenroth, Karl F. Mueller
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Patent number: 5481028Abstract: A process for the preparation of perfluoroalkyl iodides, especially perfluoroethyl iodide, by reaction of perfluorinated compounds which contain a carbon carbon double bond with ICl in HF solvent in the presence of Lewis acid catalysts. The compounds are used as telogens for the telomerization of tetrafluoroethylene to long-chain perfluoroalkyl iodides.Type: GrantFiled: August 12, 1994Date of Patent: January 2, 1996Assignee: E. I. Du Pont de Nemours and CompanyInventors: Viacheslav A. Petrov, Carl G. Krespan
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Patent number: 5468904Abstract: A fluorine-containing benzophenone derivative of the formula (1), (2) or (3):.PHI..sup.1 (--X.sup.1 --Q.sup.1 --R.sub.f.sup.1).sub.n (1).PHI..sup.2 --X.sup.2 --Q.sup.2 --R.sub.f.sup.2 --Q.sup.3 --X.sup.3 --.PHI..sup.3 (2).PHI..sup.4 --X.sup.4 --Q.sub.f --X.sup.5 --.PHI..sup.5 (3)wherein .PHI..sup.1 is a 2-hydroxybenzophenone structure of the formula ka-1: ##STR1## (wherein Y is a hydrogen atom or a hydroxyl group, each of k and m indicates the number of bond sites, k is an integer of from 0 to 3, and m is an integer of from 0 to 3, provided that 1.ltoreq.(k+m).ltoreq.4), n corresponds to (k+m) and is an integer of from 1 to 4, each of .PHI..sup.2, .PHI..sup.3, .PHI..sup.4 and .PHI..sup.5 is a 2-hydroxybenzophenone structure of the formula ka-1 wherein (k+m) is 1, each of X.sup.1, X.sup.2, X.sup.3, X.sup.4 and X.sup.5 is a single bond or an oxygen atom, Q.sup.1 is a single bond or a bivalent linking group having a carbon atom directly bonded to X.sup.1, each of Q.sup.2 and Q.sup.Type: GrantFiled: February 4, 1994Date of Patent: November 21, 1995Assignee: Asahi Glass Company Ltd.Inventors: Ryoko Osawa, Takashige Maekawa, Tatsuo Momii, Satoshi Kamata
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Patent number: 5453533Abstract: An influenza virus neuraminidase inhibitor, its analogs, its pharmaceutically acceptable salts, derivatives, and mixtures thereof having the following formula: ##STR1## where A is CO.sub.2 H, CO.sub.2 H.sub.3, NO.sub.2, SO.sub.3 H or PO.sub.3 H.sub.2, B is CH, N, O or S, R.sub.1 and R.sub.2 are H, NO.sub.2 or (CH.sub.m).sub.n X.sub.1 where m=1 or 2, n is an integer from 0 to 4 and X.sub.1 is guanidino, OH, NH.sub.2, SH, NO.sub.2, F, Cl, Br, I, CN, CF.sub.3, CO.sub.2 H, SO.sub.3 H or PO.sub.3 H.sub.2, R.sub.3 and R.sub.4 are H, (CH.sub.o).sub.p X.sub.2, (CH.sub.o).sub.p CHX.sub.2 CH.sub.2 X.sub.2, NH(CH.sub.o).sub.p CHX.sub.2 CH.sub.2 X.sub.2, NHCO(CH.sub.o).sub.p CH.sub.2 X.sub.2 or NHCO(CH.sub.o).sub.p CHX.sub.2 CH.sub.2 X.sub.2 where o=1 or 2, p is an integer from 0 to 4 and X.sub.2 is H, guanidino, OH, NH.sub.2, SH, NO.sub.2, CF.sub.3, CO.sub.2 H, SO.sub.3 H or PO.sub.3 H.sub.2 , R.sub.5 =H, OH, NH.sub.2, (CH.sub.k).sub.1 X.sub.3, CO(CH.sub.k).sub.1 X.sub.3, SO(CH.sub.k).sub.1 X.sub.3 or SO.sub.2 (CH.sub.Type: GrantFiled: April 14, 1994Date of Patent: September 26, 1995Assignee: The University of Alabama at BirminghamInventors: Ming Luo, Wayne J. Brouillette, Gillian Air
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Patent number: 5434289Abstract: A process for producing an optically active .beta.-hydroxyketone represented by formula (I): ##STR1## by catalytic asymmetrical aldol reaction is disclosed, comprising reacting a silyl-enol ether represented by formula (II): ##STR2## with a substituted aldehyde represented by formula (III):R.sup.5 CHO (III)in the presence of a binaphthol-titanium complex represented by formula (IV): ##STR3## An optically active .beta.-hydroxyketone is efficiently produced with diastereo-specificity and enantio-specificity.Type: GrantFiled: March 10, 1994Date of Patent: July 18, 1995Assignee: Takasago International CorporationInventors: Koichi Mikami, Satoru Matsukawa, Masaki Shimizu, Masahiro Terada, Noboru Sayo
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Patent number: 5399718Abstract: A liquid phase process for making perfluorinated organic substances which comprises directly contacting in a temperature-controlled reactor a diluted solution or dispersion of a perfluorinateable, organic substance in a liquid, inert medium with a stoichiometric excess of fluorine gas, optionally diluted with an inert gas, to perfluorinate said organic substance at a temperature and a flow rate of inert gas (if used) sufficient to volatilize the resulting by-product hydrogen fluoride, removing said hydrogen fluoride from the reactor as it is produced, and separately removing from the reactor the resultant solution or dispersion of perfluorinated organic substance.Type: GrantFiled: February 1, 1994Date of Patent: March 21, 1995Assignee: Minnesota Mining and Manufacturing CompanyInventors: Michael G. Costello, George G. I. Moore
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Patent number: 5385693Abstract: Disclosed herein are optically active carboxylic acid or acid halide compounds of formula III: ##STR1## Wherein R.sub.2 represents an optically active alkyl or alkoxyalkyl group having 3 to 15 carbon atoms optionally substituted by halogen atoms; R' represents a hydroxyl group or a halogen atom; k is 0 or 1; and n represents an integer of 1 to 6.Type: GrantFiled: May 17, 1993Date of Patent: January 31, 1995Assignee: Sumitomo Chemical Company, LimitedInventors: Takayuki Higashii, Isao Kurimoto, Shoji Toda, Masayoshi Minai, Takeshi Tani, Chizu Kawakami, Koichi Fujisawa, Kiyoshi Imamura
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Patent number: 5336484Abstract: Disclosed are x-ray contrast compositions for oral or retrograde examination of the gastrointestinal tract comprising a polymeric material capable of forming a coating on the gastrointestinal tract and an x-ray producing agent of the formula ##STR1## and methods for their use in diagnostic radiology of the gastrointestinal tract wherein ##STR2## Z=H, halo, C.sub.1 -C.sub.20 alkyl, cycloalkyl, lower alkoxy, cyano, where the alkyl and cycloalkyl groups can be substituted with halogen or halo-lower-alkyl groups;R=C.sub.1 -C.sub.25 alkyl, cycloalkyl, aryl or halo-lower-alkyl, optionally substituted with halo, fluoro-lower-alkyl, lower-alkoxy, hydroxy, carboxy or lower-alkoxy carbonyl, lower-alkenyl, lower-alkynyl, lower-alkylene or lower-alkoxy-carbonyloxy,n is 1-5;y is 0-4; andw is 1-4.Type: GrantFiled: March 31, 1993Date of Patent: August 9, 1994Assignee: Sterling Winthrop Inc.Inventors: Edward R. Bacon, Sol J. Daum, Kimberly G. Estep, Kurt A. Josef, Brent D. Douty, Carl R. Illig
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Patent number: RE35060Abstract: Photoinitiators having at least one terminal fluoroalkyl moiety are useful for photopolymerizing and photocuring fluorinated as well as non-fluorinated monomers, especially fluorinated acrylic monomers.Type: GrantFiled: June 2, 1994Date of Patent: October 10, 1995Assignee: AlliedSignal Inc.Inventor: Chengjiu Wu