Oxygen Bonded Directly To The Carbonyl Group (e.g., Carboxylic Acid Esters, Etc.) Patents (Class 558/441)
-
Patent number: 11081729Abstract: The present invention relates to a non-aqueous electrolyte solution additive, and a non-aqueous electrolyte solution for a lithium-ion battery and a lithium-ion battery which include the same, and particularly, to a non-aqueous electrolyte solution, which may remove an acid generated by the decomposition of a lithium salt while being able to suppress the dissolution of metal impurities causing failure in the battery by using and including a Lewis base compound containing a propargyl group as a non-aqueous electrolyte solution additive for a lithium-ion battery, and a lithium secondary battery in which transition metal dissolution in a positive electrode and a low-voltage phenomenon are improved.Type: GrantFiled: July 6, 2018Date of Patent: August 3, 2021Inventors: Hyun Seung Kim, Sung Hoon Yu, Jeong Woo Oh, Chul Haeng Lee
-
Patent number: 9682019Abstract: An aqueous dental glass ionomer composition comprising (a) a reactive particulate glass, (b) a linear or branched polymer comprising acidic groups, which is reactive with the particulate glass in a cement reaction, whereby the linear or branched polymer comprising acidic groups has a polymer backbone and optionally pendant groups, (c) optionally dispersed nanoparticles comprising grafted linear or branched polymer chains comprising acidic groups, and having a polymer backbone characterized in that a polymer backbone of the linear or branched polymer of component (b) and/or, if present, the grafted Sinear or branched polymer chains of component (c) are obtainable a process comprising (i) cyclopolymerizing or cyclocopolymerizing one or more compounds of the following formula (I).Type: GrantFiled: November 2, 2010Date of Patent: June 20, 2017Assignee: Dentsply DeTry GmbHInventors: Joachim E. Klee, Oliver Elsner, Sven Pohle, Helmut Ritter, Dominika Bernert
-
Publication number: 20130310577Abstract: Described is a method for the preparation of renin inhibitors such as aliskiren, and intermediates useful therein. The method introduces a nitrogen-containing intermediate such as a lactone of formula (8). with R4 being a branched C3-6 alkyl. In the preparation of the lactone, or related intermediates, a desired stereochemical configuration can be controlled by starting from a chiral aldehyde satisfying formula (10).Type: ApplicationFiled: July 11, 2013Publication date: November 21, 2013Applicant: DSM IP ASSETS B.V.Inventors: Ben DE LANGE, Anna Maria Cornelia Francisca CASTELIJNS, Johannes Gerardus DE VRIES, Andreas Hendrikus Maria DE VRIES, Jeroen Antonius Franciscus BOOGERS
-
Patent number: 8563279Abstract: Described is a method for the preparation of renin inhibitors such as aliskiren, and intermediates useful therein. The method introduces a nitrogen-containing intermediate such as a lactone of formula (8). with R4 being a branched C3—6 alkyl. In the preparation of the lactone, or related intermediates, a desired stereochemical configuration can be controlled by starting from a chiral aldehyde satisfying formula (10).Type: GrantFiled: December 19, 2008Date of Patent: October 22, 2013Assignee: DSM IP Assets B.V.Inventors: Ben De Lange, Anna Maria Cornelia Francisca Castelijns, Johannes Gerardus De Vries, Andreas Hendrikus Maria De Vries, Jeroen Antonius Franciscus Boogers, Quirinus Bernardus Broxterman
-
Publication number: 20130171092Abstract: The high temperatures required for cracking the cyanoacrylate oligomers, produced by the Knovenagel condensation of formaldehyde and a cyanoacetate, limit the synthetic diversity and the number of different side chains that can be incorporated into a cyanoacrylate prepared using this method. Accordingly, the diversity of cyanoacrylate monomers prepared industrially is quite limited. Disclosed herein is a method for the preparation of alpha-Cyanoacrylate ester monomers from a variety of phosphonium and ammonium alpha-cyanoacrylate salts.Type: ApplicationFiled: February 26, 2013Publication date: July 4, 2013Applicant: Henkel Ireland LimitedInventor: Henkel Ireland Limited
-
Publication number: 20130131370Abstract: The present invention relates to a process for producing 2-cyanoacetic acid anhydride, comprising the steps of a) preparing a reaction mixture, containing as reactants 2-cyanoacetic acid, and at least one C4-20 carboxylic acid anhydride in at least one organic solvent, wherein the molar ratio of 2-cyanoacetic acid to C4-20 carboxylic acid anhydride in said reaction mixture is greater than 1.5:1, and b) subjecting the reaction mixture to a temperature of 0° C. to 100° C. to form 2-cyanoacetic acid anhydride. The present invention also relates to process for producing 2-cyanoacetic acid esters, 2-cyanoacetic acid amides and/or 2-cyanoacetic acid thioesters from 2-cyanoacetic acid anhydride.Type: ApplicationFiled: January 18, 2013Publication date: May 23, 2013Applicant: Loctite (R&D) Limited Ltd.Inventor: Loctite (R&D) Limited Ltd.
-
Publication number: 20130075364Abstract: Methods for forming a pattern in a lithography process for semiconductor wafer manufacturing are provided. In an example, a method includes forming a photoresist layer over a material layer; performing a first exposure process on the photoresist layer, thereby forming an exposed photoresist layer having soluble portions and unsoluble portions; treating the exposed photoresist layer, wherein the treating includes one of performing a second exposure process on the exposed photoresist layer and forming an adsorbing chemical layer over the exposed photoresist layer; and developing the exposed and treated photoresist layer to remove the soluble portions of the photoresist layer, wherein the unsoluble portions of the photoresist layer form a photoresist pattern that exposes portions of the material layer.Type: ApplicationFiled: September 22, 2011Publication date: March 28, 2013Applicant: TAIWAN SEMICONDUCTOR MANUFACTURING COMPANY, LTD.Inventors: Chien-Wei Wang, Ko-Bin Kao, Wei-Liang Lin, Jui-Ching Wu, Chia-Hsiang Lin, Ai-Jen Jung
-
Publication number: 20120264967Abstract: The present invention relates generally to processes of making (R)-3-(2,3-Dihydroxypropyl)-6-fluoro-5-(2-fluoro-4-iodophenylamino)-8-methylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione, intermediates thereof, and a process for making a particular polymorph of (R)-3-(2,3-Dihydroxypropyl)-6-fluoro-5-(2-fluoro-4-iodophenylamino)-8-methylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione.Type: ApplicationFiled: March 15, 2012Publication date: October 18, 2012Applicant: TAKEDA PHARMACEUTICAL COMPANY LIMITEDInventors: David Paul Provencal, Todd Miller, Yuxin Zhao, Jonathon S. Salsbury
-
Publication number: 20120184769Abstract: A method for isolating methylglycinenitrile-N,N-diacetonitrile (MGDN) from an aqueous mixture comprising MGDN is provided The method comprises cooling the aqueous mixture in one or more steps In one of these steps the mixture is cooled at a cooling rate of at least 20 K/h from a temperature above the solidification point of MGDN to a temperature below the solidification point of MGDN The method is implemented continuouslyType: ApplicationFiled: September 29, 2010Publication date: July 19, 2012Applicant: BASF SEInventors: Bernd Judat, Alfred Oftring, Armin Stamm, Friedhelm Teich
-
Publication number: 20120171581Abstract: Disclosed are a nonaqueous electrolytic solution of an electrolyte dissolved in a nonaqueous solvent, which contains a carboxylate represented by the following general formula (I) in an amount of from 0.01 to 10% by mass of the nonaqueous electrolytic solution; and an electrochemical element using it.Type: ApplicationFiled: September 14, 2010Publication date: July 5, 2012Applicant: UBE INDUSTRIES, LTD.Inventors: Koji Abe, Shoji Shikita, Kazuyuki Kawabe, Masahide Kondo, Tatsuo Fujino
-
Patent number: 8138368Abstract: There is provided a process for stereoselectively producing E-form of 3-acyloxyacrylonitrile compound (3) or Z-form which comprises reacting 3-oxopropionitrile compound (1) with an acid chloride (2), characterized in that the reaction is conducted with removal of hydrogen chloride, or by using an organic base or an inorganic base, to thereby regulate the stereostructure of the product; a process for producing the compound (1) characterized by reacting acetonitrile compound (5) with an aromatic ester compound (6) by use of an alkali metal alkoxide in a hydrocarbon solvent while removing alcohol formed as a by-product by azeotropic distillation in a separating tank; and a process for isomerizing E-form of 3-acyloxyacrylonitrile compound to Z-form thereof by use of an organic base.Type: GrantFiled: October 8, 2009Date of Patent: March 20, 2012Assignee: Nissan Chemical Industries, Ltd.Inventors: Kenzo Fukuda, Yasuo Kondo, Norio Tanaka, Hideaki Suzuki, Masatoshi Ohnari, Koichi Nishio
-
Patent number: 8134023Abstract: Materials and methods for preparing (S)-(+)-3-aminomethyl-5-methyl-hexanoic acid and structurally related compounds via enzymatic kinetic resolution are disclosed.Type: GrantFiled: September 28, 2011Date of Patent: March 13, 2012Assignee: Pfizer IncInventors: Shanghui Hu, Carlos Alberto Martinez, Junhua Tao, William Eugene Tully, Patrick Kelleher, Yves Dumond
-
Patent number: 8044227Abstract: Materials and methods for preparing (S)-(+)-3-aminomethyl-5-methyl-hexanoic acid and structurally related compounds via enzymatic kinetic resolution are disclosed.Type: GrantFiled: November 22, 2010Date of Patent: October 25, 2011Assignee: Pfizer Inc.Inventors: Shanghui Hu, Carlos Alberto Martinez, Junhua Tao, William Eugene Tully, Patrick Kelleher, Yves Dumond
-
Publication number: 20110008852Abstract: Described is a method for the preparation of renin inhibitors such as aliskiren, and intermediates useful therein. The method introduces a nitrogen-containing intermediate such as a lactone of formula (8). with R4 being a branched C3—6 alkyl. In the preparation of the lactone, or related intermediates, a desired stereochemical configuration can be controlled by starting from a chiral aldehyde satisfying formula (10).Type: ApplicationFiled: December 19, 2008Publication date: January 13, 2011Inventors: Ben De Lange, Anna Maria Cornelia Francisca Castelijns, Johannes Gerardus De Vries, Andreas Hendrikus Maria De Vries, Jeroen Antonius Boogers, Quirinus Bernardus Broxterman
-
Publication number: 20100256230Abstract: The invention relates to new butane acid derivatives comprising a cyanide group, pharmaceutical compositions containing said butane acid derivatives and the use of said butane acid derivatives in the production of pharmaceutical compositions for treating various illnesses.Type: ApplicationFiled: October 5, 2009Publication date: October 7, 2010Applicant: SCHEBO BIOTECH AGInventors: Erich Eigenbrodt, Stefan Mullner, Sybille Mazurek, Hugo Fasold
-
Publication number: 20100204503Abstract: The present invention is directed to a regio- and stereoselective bioconversion of selected aliphatic dinitriles into corresponding cyanocarboxylic acids. More particularly, the present invention provides methods for the conversion of 2-isobutyl-succinonitrile into (S)-3 cyano-5-methylhexanoic acid, which is a useful intermediate in the synthesis of (S)-3(aminomethyl)-5-methylhexanoic acid (pregabalin). Pregabalin can be used for treating certain cerebral diseases, for example, in the treatment and prevention of seizure disorders, pain, and psychotic disorders.Type: ApplicationFiled: April 20, 2010Publication date: August 12, 2010Inventors: Michael P. Burns, Justin K. Weaver, John Wing Wong
-
Publication number: 20100193727Abstract: A method of functionalizing nano-carbon materials with a diameter less than 1 ?m, comprising: contacting the nano-carbon materials with a free radical generating compound such as azo-compound in an organic solvent under an inert gas atmosphere, thereby obtaining nano-carbon materials with functional groups thereon. The physical and chemical properties of the nano-carbon materials can be modified through the aforementioned method.Type: ApplicationFiled: December 27, 2006Publication date: August 5, 2010Inventors: Chrong-Ching Lee, Kuo-Chen Shih, Mei Hua Wang, Sui-Wen Ho, Shu-Jiuan Huang
-
Patent number: 7737294Abstract: The present invention is directed to compositions of specific carboxylic acid, fatty acid or oil derivatives containing nitrile groups and methods of their preparation. The preparation involves a hydrocyanation reaction. A method of hydrgenating the nitrile containing carboxylic acid acids obtained by above hydrocyanation to produce amine containing carbixylic acids is also disclosed in this invention.Type: GrantFiled: September 8, 2004Date of Patent: June 15, 2010Assignee: Invista North America S.A R.L.Inventors: Alan Martin Allgeier, Christian Peter Lenges
-
Publication number: 20100029951Abstract: There is provided a process for stereoselectively producing E-form of 3-acyloxyacrylonitrile compound (3) or Z-form which comprises reacting 3-oxopropionitrile compound (1) with an acid chloride (2), characterized in that the reaction is conducted with removal of hydrogen chloride, or by using an organic base or an inorganic base, to thereby regulate the stereostructure of the product; a process for producing the compound (1) characterized by reacting acetonitrile compound (5) with an aromatic ester compound (6) by use of an alkali metal alkoxide in a hydrocarbon solvent while removing alcohol formed as a by-product by azeotropic distillation in a separating tank; and a process for isomerizing E-form of 3-acyloxyacrylonitrile compound to Z-form thereof by use of an organic base.Type: ApplicationFiled: October 8, 2009Publication date: February 4, 2010Applicant: Nissan Chemical Industries, Ltd.Inventors: Kenzo Fukuda, Yasuo Kondo, Norio Tanaka, Hideaki Suzuki, Masatoshi Ohnari, Koichi Nishio
-
Patent number: 7649104Abstract: There is provided a process for stereoselectively producing E-form of 3-acyloxyacrylonitrile compound (3) or Z-form which comprises reacting 3-oxopropionitrile compound (1) with an acid chloride (2), characterized in that the reaction is conducted with removal of hydrogen chloride, or by using an organic base or an inorganic base, to thereby regulate the stereostructure of the product; a process for producing the compound (1) characterized by reacting acetonitrile compound (5) with an aromatic ester compound (6) by use of an alkali metal alkoxide in a hydrocarbon solvent while removing alcohol formed as a by-product by azeotropic distillation in a separating tank; and a process for isomerizing E-form of 3-acyloxyacrylonitrile compound to Z-form thereof by use of an organic base.Type: GrantFiled: March 26, 2004Date of Patent: January 19, 2010Assignee: Nissan Chemical Industries, Ltd.Inventors: Kenzo Fukuda, Yasuo Kondo, Norio Tanaka, Hideaki Suzuki, Masatoshi Ohnari, Koichi Nishio
-
Patent number: 7595418Abstract: This invention describes protected 5,7-dihydroxy-4,4-dimethyl-3-oxoheptanoic acid ester and 5,7-dihydroxy-2-alkyl-4,4-dimethyl-3-oxoheptanoic acid ester for the synthesis of epothilones and epothilone derivatives and process for the production of these esters.Type: GrantFiled: June 5, 2004Date of Patent: September 29, 2009Assignee: Bayer Schering Pharma AktiengesellschaftInventors: Juergen Westermann, Johannes Platzek, Orlin Petrov
-
Patent number: 7560585Abstract: The present invention relates to an environmentally benign process for the preparation of (S)-?-cyano-3-phenoxybenzyl-(S)-2-(4-chlorophenyl)isovalerate from its diastereomeric mixture (RS)-?-cyano-3-phenoxybenzyl-(S)-2-(4-chlorophenyl) isovalerate.Type: GrantFiled: December 10, 2004Date of Patent: July 14, 2009Assignee: Council of Scientific & Industrial ResearchInventors: Vaddu Venkata Narayana Reddy, Khwaja Ishratullah, Penumatcha Venkata Krishnam Raju, Tella Ramesh Babu, Masna Mahesh, Chappeta Venkateswara Reddy
-
Patent number: 7534907Abstract: A monomer composition comprising at least one polymerizable alkyl ester ?-cyanoacrylate monomer. Specifically, the ?-cyanoacrylate monomer is an alkyl ester ?-cyanoacrylate monomer of the general formula having a spacer R1: n is from 2 to 12; R3 and R4 are each an alkyl group or a hydrogen, and at least one of R3 or R4 is an alkyl group (e.g. linear or branched, or cyclic) having from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 and 13 carbon atoms; R2 is an alkyl group (e.g. linear or branched, or cyclic) having from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 and 13 carbon atoms; and the combined number of carbon atoms (N) in the spacer R1 is at least n+1.Type: GrantFiled: May 30, 2007Date of Patent: May 19, 2009Assignee: Ethichon, Inc.Inventor: Hongbo Liu
-
Publication number: 20090018360Abstract: This invention is related to the preparation of alkyl or alkoxyalkyl-?-cyanoacrylates in monomeric form by depolymerisation of the corresponding poly(alkyl-?-cyanoacrylates) or poly(alkoxyalkyl-?-cyanoacrylates) (PCA). The PCA's are obtained preferably by base-catalyzed condensation of a cyanoacetate with formaldehyde (or a polymer of the latter). According to the invention, the poly(alkyl-?-cyanoacrylate) or poly(alkoxyalkyl-?-cyanoacrylate), the condensation product, is mixed with a depolymerisation system comprising phosphorus pentoxide P2O5, hydroquinone, ortho-phosphoric acid and para-toluenesulfonic acid. This process is realized in a batch reactor fitted with a condenser, heated at a temperature in the range of 100-300° C., under a vacuum of 0.5-50 Torr (7.10?5-7.10?3 MPa) and gives rise to monomeric alkyl-?-cyanoacrylates or monomeric alkoxyalkyl-?-cyanoacrylates, being stable in both gaseous and liquid phase.Type: ApplicationFiled: May 5, 2006Publication date: January 15, 2009Inventors: Zlatan Zlatev Denchev, Milena Ivanova Tomanova, Antonio Magalhaes Da Cunha
-
Patent number: 7470812Abstract: The invention encompasses the synthesis of (S)-(+)-3-(aminomethyl)-5-methylhexanoic acid, (S)-Pregabalin, via the intermediate, (3R)-5-methyl-3-(2-oxo-2{[(1R)-1-phenylethyl]amino}ethyl)hexanoic acid.Type: GrantFiled: August 21, 2007Date of Patent: December 30, 2008Assignee: Teva Pharmaceutical Industries Ltd.Inventors: Vinod Kumar Kansal, Brijnath P. Chaurasia, Anand Prakash Tiwari
-
Patent number: 7465826Abstract: The invention encompasses the synthesis of (S)-(+)-3-(aminomethyl)-5-methylhexanoic acid, (S)-Pregabalin, via the intermediate, (3R)-5-methyl-3-(2-oxo-2{[(1R)-1-phenylethyl]amino}ethyl)hexanoic acid.Type: GrantFiled: August 21, 2007Date of Patent: December 16, 2008Assignee: Teva Pharmaceutical Industries Ltd.Inventors: Vinod Kumar Kansal, Brijnath P. Chaurasia, Anand Prakash Tiwari
-
Patent number: 7439266Abstract: The present invention relates to a novel malononitrile compound represented by the formula (A): wherein, R1 represents C1 to C6 alkyl that may be substituted with halogen, C2 to C6 alkenyl that may be substituted with halogen, etc; R2 represents hydrogen atom or C1 to C6 alkyl that may be substituted with halogen; R3 represents hydrogen atom or C1 to C6 alkyl; R4 represents hydrogen atom or C1 to C6 alkyl; R5 represents C1 to C6 alkyl that may be substituted with halogen, C3 to C6 alkenyl that may be substituted with halogen, etc, or R4 and R5 may be combined at their terminal and represent ethylene that may be substituted with C1 to C3 alkyl or trimethylene that may be substituted with C1 to C3 alkyl; and Z1 and Z2, which are the same or different, represent oxygen atom or sulfur atom. The malononitrile compound has an efficient pesticidal activity and can control effectively pests such as insect pests, acarine pests, nematode pests and the like.Type: GrantFiled: August 26, 2003Date of Patent: October 21, 2008Assignee: Sumitomo Chemical Company, LimitedInventors: Satoshi Okada, Daisuke Oohira, Ken Otaka
-
Publication number: 20080108844Abstract: A process for producing a monomer comprising thermally cracking a pre-polymer in the presence of a stabiliser to form a monomer as a distillate , the stabiliser preventing the re-polymerisation of the monomer during cracking while not being carried over in the distillate in normally detectable amounts.Type: ApplicationFiled: September 13, 2007Publication date: May 8, 2008Inventor: John Baggaley
-
Patent number: 7358382Abstract: The invention relates to 3,5-dihydroxy-2,2-dimethyl-valeronitriles for the synthesis of epothilones and epothilone derivatives and process for the production of these new intermediate products in the synthesis and the use for the production of epothilones or epothilone derivatives.Type: GrantFiled: July 26, 2005Date of Patent: April 15, 2008Assignee: Bayer Schering Pharma AGInventors: Jurgen Westermann, Johannes Platzek, Orlin Petrov
-
Patent number: 7238828Abstract: A monomer composition comprising at least one polymerizable alkyl ester ?-cyanoacrylate monomer. Specifically, the ?-cyanoacrylate monomer is an alkyl ester ?-cyanoacrylate monomer of the general formula having a spacer R1: wherein n is from 2 to 12; R3 and R4 are each an alkyl group or a hydrogen, and at least one of R3 or R4 is an alkyl group (e.g. linear or branched, or cyclic) having from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 and 13 carbon atoms; R2 is an alkyl group (e.g. linear or branched, or cyclic) having from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 and 13 carbon atoms; and the combined number of carbon atoms (N) in the spacer R1 is at least n+1.Type: GrantFiled: March 24, 2005Date of Patent: July 3, 2007Assignee: Ethicon, Inc.Inventor: Hongbo Liu
-
Patent number: 7232920Abstract: In one aspect, the invention provides a process for the preparation of compounds of Formula I wherein R1 is —CN, —OP, alkyl, aryl or heteroaryl; wherein P represents any suitable protecting group; and R2 is alkyl or aryl; by reacting a compound of Formula II wherein R1 is —CN, —OP, alkyl, aryl or heteroaryl; wherein P represents any suitable protecting group; and R2 is alkyl or aryl; with a reducing agent (e.g. sodium borohydride) in the presence of a metal halid (e.g. CeCl3) or a metal alkoxid (e.g. Ti(OiPr)4).Type: GrantFiled: April 22, 2003Date of Patent: June 19, 2007Assignee: BioconInventors: Tom Thomas Puthiaparampil, Acharya Poornaprajna, Chandrashekar Aswathanarayanappa, Madhavan Sridharan, Sambasivam Ganesh
-
Patent number: 7193101Abstract: A bromine/nitro moiety linked into the backbone of an ester or other compound over a wide range of occurrence rates provides antimicrobial, bio-resistant and fungal resistant properties for metal working fluids (MWF)s, coatings, plastics, and medical devices. The moiety can be have the bromo and nitro groups linked to the same or different carbon atoms. The present invention also relates to urethanes, urea, amides, imides, carbonates, ethers, siloxanes, and many other types of linkages essential to MWF bases.Type: GrantFiled: August 23, 2005Date of Patent: March 20, 2007Assignee: TPAT IPInventor: Thomas Daly
-
Patent number: 7078555Abstract: Disclosed in a process for making (1) a compound of the formula NC—CH2—CH2—CH2—CH2—CO2R?, wherein R? is H or C1 to C12 alkyl, or (2) adipic acid or (3) dimethyl adipate, using as the substrate, 3-pentenenitrile, (2) 3-pentenoic acid or methyl 3-pentenoate, respectively, by contacting the substrate with carbon monoxide and a nucleophile in the presence of a Group VIII metal, a selected ligand, and an acid promoter. The nucleophile, which (a) an alcohol or water, or (b) water or (c) methanol, respectively, in the presence of a Group VIII metal, preferably palladium, a selected phosphine ligand, and an acid promoter.Type: GrantFiled: October 2, 2003Date of Patent: July 18, 2006Assignee: Invista North America S.A.R.L.Inventors: Emilio E. Bunel, David A. Clark
-
Patent number: 7026473Abstract: Processes to prepare 5-cyanovaleric acid or its ester are provided, by carbonylation of a pentenenitrile, wherein pentenenitrile is reacted with carbon monoxide and water and/or an alcohol in the presence of a catalyst system. The catalyst system contains: (a) a metal of Group VIII or a compound thereof and (b) a bidentate phosphine, arsine and/or stibine ligand, wherein the bidentate ligand has the general formula (I): R1R2-M1-R-M2-R3R4??(I) ?wherein M1 and M2 are independently P, As or Sb, R is a divalent organic bridging group, which bridging group comprises a chain of 3 to 5 atoms directly connecting the 2 phosphorus atoms, which chain consists of carbon atoms and optionally a nitrogen, oxygen or sulphur atom or a silano or dialkylsilicon group, which alkyl groups independently comprise from 1 to 4 carbon atoms, and R1–R4 represent the same or different optionally substituted tertiary alkyl groups, (c) an acid having a pKa less than 3, as measured at 18° C. in an aqueous solution.Type: GrantFiled: April 30, 2004Date of Patent: April 11, 2006Assignee: Shell Oil CompanyInventors: Eit Drent, Willem Wabe Jager
-
Patent number: 7012158Abstract: Provided are processes and synthetic intermediates useful for the preparation of ?-difluoromethylornithine (DFMO) having the formulaType: GrantFiled: February 26, 2004Date of Patent: March 14, 2006Assignee: Skinmedica, Inc.Inventors: Jingyang Zhu, Scott T. Chadwick, Benjamin A. Price, Shannon X. Zhao, Carrie A. Costello, Purushotham Vemishetti
-
Patent number: 6891059Abstract: This invention provides a method of making (S)-(+)-3-(aminomethyl)-5-methylhexanoic acid (pregabalin) or a salt thereof via an asymmetric hydrogenation synthesis. Pregabalin is useful for the treatment and prevention of seizure disorders, pain, and psychotic disorders. The invention also provides intermediates useful in the production of pregabalin.Type: GrantFiled: January 11, 2001Date of Patent: May 10, 2005Assignee: Warner-Lambert CompanyInventors: Mark Joseph Burk, Om Prakash Goel, Marvin Simon Hoekstra, Thomas Frederick Mich, Thomas Mulhern, James A. Ramsden
-
Patent number: 6864385Abstract: 4-Haloalkylnicotinonitriles having the formula (I) which are suitable as intermediates in the preparation of pesticides, are obtained by: (a) reacting a 3-amino-1-haloalkyl-2-propen-1-one RF—C(O)—CH?CH—NH2??(II) in a condensation reaction with a compound of the formula (III) to (VII), (R1Z)CH?CH—CN??(III) (R1Z)2CH—CH2—CN??(IV) Hal-CH?CH—CN??(V) Hal2CH—CH2CN??(VI) HC?C—CN??(VII), to give a compound of the formula (VIII), (IX) and/or (X), RF—C(O)—CH?CH—NH—CH?CH—CN??(VIII) RF—C(O)—CH?CH—NH—CH(ZR1)—CH2—CN??(IX) RF—C(O)—CH?CH—NH—CH(Hal)—CH2—CN??(X), wherein RF is (C1-C4)-haloalkyl, R1 is alkyl, Hal is Cl or Br and each Z, independently, is O, S, NR1 or OCO; and (b) subjecting the reaction product to a ring closure reaction.Type: GrantFiled: December 30, 2002Date of Patent: March 8, 2005Assignee: Aventis CropScience GmbHInventors: Sergiy Pazenok, Henricus Maria Martinus Bastiaans
-
Patent number: 6843890Abstract: A process of treating waste solvent acetonitrile streams which contain at least one water extractable impurity such as isopropyl acetate to remove substantially all of the impurity by distilling the waste solvent acetonitrile in the presence of water for a time sufficient to allow the water extractable impurity to be extractively distilled from the acetonitrile. In preferred embodiments of the present invention the feed may contain either a mixture of waste solvent acetonitrile and crude acetonitrile or crude acetonitrile free of hydrogen cyanide by itself.Type: GrantFiled: July 23, 1999Date of Patent: January 18, 2005Assignee: The Standard Oil CompanyInventor: Sanjay Purushottam Godbole
-
Publication number: 20040214890Abstract: The present invention relates to compounds of formula (AA) (I) and (X): 1Type: ApplicationFiled: September 8, 2003Publication date: October 28, 2004Inventors: Yvette M. Fobian, John N. Freskos, Barbara Jagodzinska
-
Publication number: 20040204594Abstract: This invention relates to preparation of enantio-enriched compounds, and more particularly to enantio-enriched kavalactone compounds and derivatives thereof. The methods provide compounds that are useful as reagents, or building blocks, in the construction of other enantio-enriched compounds.Type: ApplicationFiled: January 12, 2004Publication date: October 14, 2004Inventors: Shoujun Chen, Lijun Sun, Joel McCleary
-
Publication number: 20040162440Abstract: Disclosed in a process for making (1) a compound of the formula NC—CH2—CH2—CH2—CH2—CO2R′, wherein R′ is H or C1 to C12 alkyl, or (2) adipic acid or (3) dimethyl adipate, using as the substrate, 3-pentenenitrile, (2) 3-pentenoic acid or methyl 3-pentenoate, respectively, by contacting the substrate with carbon monoxide and a nucleophile in the presence of a Group VIII metal, a selected ligand, and an acid promoter. The nucleophile, which (a) an alcohol or water, or (b) water or (c) methanol, respectively, in the presence of a Group VIII metal, preferably palladium, a selected phosphine ligand, and an acid promoter.Type: ApplicationFiled: October 2, 2003Publication date: August 19, 2004Inventors: Emilio E. Bunel, David A. Clark
-
Patent number: 6743911Abstract: Processes to prepare 5-cyanovaleric acid or its ester are provided, by carbonylation of a pentenenitrile, wherein pentenenitrile is reacted with carbon monoxide and water and/or an alcohol in the presence of a catalyst system. The catalyst system contains: (a) a metal of Group VIII or a compound thereof, (b) a certain bidentate phosphine, arsine and/or stibine ligand, and (c) an acid having a pKa less than 3, as measured at 18° C. in an aqueous solution. &egr;-caprolactam is also prepared by reduction of 5-cyanovaleric acid or ester obtained above to 6-aminocaproic acid or ester, and then cyclisation of the 6-aminocaproic acid or ester to &egr;-caprolactam.Type: GrantFiled: March 13, 2001Date of Patent: June 1, 2004Assignee: Shell Oil CompanyInventors: Eit Drent, Willem Wabe Jager
-
Patent number: 6730809Abstract: Provided are processes and synthetic intermediates useful for the preparation of &agr;-difluoromethylornithine (DFMO) having the formulaType: GrantFiled: August 19, 2002Date of Patent: May 4, 2004Assignee: Women First Healthcare, Inc.Inventors: Jingyang Zhu, Scott T. Chadwick, Benjamin A. Price, Shannon X. Zhao, Carrie A. Costello, Purushotham Vemishetti
-
Publication number: 20030212290Abstract: This invention provides a method of making (S)-(+)-3-(aminomethyl)-5-methylhexanoic acid (pregabalin) or a salt thereof via an asymmetric hydrogenation synthesis. Pregabalin is useful for the treatment and prevention of seizure disorders, pain, and psychotic disorders. The invention also provides intermediates useful in the production of pregabalin.Type: ApplicationFiled: March 7, 2003Publication date: November 13, 2003Inventors: Mark Joseph Burk, Omprakash Goel, Marvin Simon Hoekstra, Thomas Frederick Mich, Thomas Mulhern, James A. Ramsden
-
Patent number: 6627772Abstract: Compounds represented by the formula wherein R and R1 independently represent H, —CH2CN or —CH2CO2X, with the proviso that R and R1 can not be both H or —CH2CO2X; and X represents hydrogen, an alkali metal or alkaline earth metal are disclosed. These compounds are useful as intermediate compounds in the preparation of N-[2-(carboxymethoxy)ethyl]-N-(carboxy-methyl)glycine. These intermediates can be formed by contacting 3-morpholinone with glycolonitrile under alkaline conditions to form an aminonitrile which can be hydrolyzed and contacted with additional glycolonitrile to form the nitrile intermediate which can be converted to N-[2-(carboxymethoxy)ethyl]-N-(carboxymethyl)glycine via hydrolysis.Type: GrantFiled: February 22, 2002Date of Patent: September 30, 2003Assignee: The Dow Chemical CompanyInventors: Phillip S. Athey, David A. Wilson
-
Publication number: 20030144533Abstract: The &bgr;-keto ester compound, &bgr;-hydroxy acid compound and acetonide form of a 1,3-diol derivative of the formulas (I), (V) and (VIII) 1Type: ApplicationFiled: September 30, 2002Publication date: July 31, 2003Applicant: Sumika Fine Chemicals Co., Ltd.Inventors: Mitsuhiro Iwasaki, Kiyoshi Sugi, Hideto Miyamoto, Nobushige Itaya
-
Patent number: 6590106Abstract: Disclosed are novel compounds represented by Structural Formula II, IX or XXVIII: R1, R2, and R22 are independently an aliphatic group, a substituted aliphatic group, an aromatic group or a substituted aromatic group. R2 is —NR4R5 or —N+≡C−. Alternatively, R1, and R2, taken together with the methine group to which they are bonded, are a moiety represented by the following structural formula: R3 is —NH2, —OH, —OC(O)H or —OR9. R5, R6 and R7 are independently —H or an amine protecting group. R8 is —H, —OH or —OR8. R9 is an alcohol protecting group. Also disclosed are methods of preparing these compounds.Type: GrantFiled: June 21, 2002Date of Patent: July 8, 2003Assignee: Pharm-Eco Laboratories, Inc.Inventors: Richard L. Gabriel, Jurjus Jurayj
-
Publication number: 20030105347Abstract: There are provided a method for producing a 4-cyano-3-oxobutanoate by reacting a 4-halo-3-oxobutanoate with an alkaline metal cyanide in methanol, a process for producing 4-cyano-3-hydroxybutanoate therefrom.Type: ApplicationFiled: October 29, 2001Publication date: June 5, 2003Inventors: Ryuhei Wakita, Nobuya Ito
-
Patent number: 6555706Abstract: This invention is directed to a process for making an iminodiacetic acid compound from a monoethanolamine substrate having the formula: wherein R1 is hydrogen, hydrocarbyl, or substituted hydrocarbyl. The process includes a series of reactions comprising a cyanomethylation, a hydrolysis and a dehydrogenation with the hydrolysis and dehydrogenation steps being carried out either sequentially or concurrently. In a particular embodiment, the iminodiacetic acid produced is disodium iminodiacetic acid and the monoethanolamine substrate used is 2-aminoethanol.Type: GrantFiled: May 15, 2001Date of Patent: April 29, 2003Assignee: Monsanto CompanyInventors: Howard C. Berk, Thaddeus S. Franczyk, II, Robert B. Weisenfeld, David A. Morgenstern, Juan P. Arhancet, William L. Moench, James C. Peterson
-
Publication number: 20030009053Abstract: An unsaturated monocarboxylic ester compound has at least two structures represented by the following general formula (1): 1Type: ApplicationFiled: July 25, 2002Publication date: January 9, 2003Inventors: Tadatomi Nishikubo, Atsushi Kameyama, Masaki Sasaki, Masatoshi Kusama