Oxygen Bonded Directly To The Carbonyl Group (e.g., Carboxylic Acid Esters, Etc.) Patents (Class 558/441)
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Publication number: 20020187992Abstract: A prodrug composition containing a cinnamate moiety and a biologically active molecule moiety which can be released by hydrolysis or activated by light is disclosed. The cinnamate moiety can have substituents of various electronically donating or electronically withdrawing groups to modify the cinnamate moiety's electric properties as well as photo reactivities for the purpose of achieving a proper hydrolysis rate of the acyl bond between the biologically active molecule moiety and the cinnamic acid backbone. The biologically active molecule can be any biologically active agent or diagnostic, for example, a chemotherapeutic such as a paclitaxel, campotothecin, doxorubicin, amethopterin, etoposide, or fluconazole. The prodrug composition can be modified to add a carrier moiety on the prodrug composition for targeting or to facilitate uptake of the drug. The prodrug compositions can be activated with an energy source to release the drug at the desired site.Type: ApplicationFiled: January 31, 2002Publication date: December 12, 2002Inventors: Carl W. Gilbert, Eleanor B. McGowan, Kirby S. Black, T. Gregory P. Harper
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Patent number: 6492553Abstract: A method for preparing a N-[(aliphatic or aromatic)carbonyl)]-2-aminoacetamide compound, and for preparing a cyclized compound therefrom, as well as novel resin bound intermediate compounds that are useful for preparing such compounds.Type: GrantFiled: August 4, 1999Date of Patent: December 10, 2002Assignee: Aventis Pharamaceuticals Inc.Inventors: Christopher Hulme, George C. Morton, Joseph M. Salvino, Richard F. Labaudiniere, Helen J. Mason, Matthew M. Morrissette, Liang Ma, Marie-Pierre Cherrier
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Publication number: 20020183518Abstract: Y—X—C(R′)═C(R″)COOR″′ (A1)Type: ApplicationFiled: November 27, 2001Publication date: December 5, 2002Applicant: ONTOGEN CORPORATIONInventors: Adnan M. M. Mjalli, Xiaodong Cao, Edmund J. Moran
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Publication number: 20020147360Abstract: Compounds represented by the formula 1Type: ApplicationFiled: February 22, 2002Publication date: October 10, 2002Inventors: Phillip S. Athey, David A. Wilson
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Publication number: 20020115881Abstract: There are described 4-aminobut-2-ynecarboxylic acid derivatives of formula 1Type: ApplicationFiled: December 13, 2001Publication date: August 22, 2002Inventors: Werner Holzl, Wolfgang Haap, Jurgen Koppold, Dietmar Ochs, Karin Petzold, Marcel Schnyder
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Patent number: 6433213Abstract: An improved process for the preparation of cis-1,3-diols is described where a beta hydroxy ketone is treated with a trialkylborane or dialkylalkoxyborane or a mixture of a trialkylborane and a dialkylalkoxyborane followed by recovery and reuse of the alkylborane species to convert additional beta hydroxy ketone to the cis-1,3-diol.Type: GrantFiled: June 16, 2000Date of Patent: August 13, 2002Assignee: Warner-Lambert CompanyInventors: Robert Lee Bosch, Richard Joseph McCabe, Thomas Norman Nanninga, Robert Joseph Stahl
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Publication number: 20020107285Abstract: Compounds are provided that lower blood glucose concentrations, lower serum triglyceride concentrations, lower systolic blood pressure, and increase glucose uptake by adipose tissue, but do not affect the expression of PPAR-&ggr; by adipose tissue.Type: ApplicationFiled: February 15, 2002Publication date: August 8, 2002Applicant: Calyx Therapeutics, Inc.Inventors: Partha Neogi, Bishwajit Nag, Frederick J. Lakner, Debendranath Dev, Satyanarayana Medicherla
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Publication number: 20020086996Abstract: The present invention relates to novel N-cyanomethyl amides which are cysteine protease inhibitors, the pharmaceutically acceptable salts and N-oxides thereof, their uses as therapeutic agents and the methods of their making.Type: ApplicationFiled: December 14, 2001Publication date: July 4, 2002Applicant: AXYS PHARMACEUTICALS, INC.Inventors: Clifford M. Bryant, James T. Palmer, Robert M. Rydzewski, Eduardo L. Setti, Zong-Qiang Tian, Shankar Venkatraman, Dan-Xiong Wang
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Publication number: 20020045748Abstract: Processes to prepare 5-cyanovaleric acid or its ester is 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 containingType: ApplicationFiled: March 13, 2001Publication date: April 18, 2002Inventors: Eit Drent, Willem Wabe Jager
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Patent number: 6355490Abstract: The present invention relates to a process of coding and identifying individual members of a chemical combinatorial library synthesized on a plurality of solid supports which undergo mix and split synthesis. The process provides for tagging the solid supports with a coding identifier that is attached to the solid support and which can be decoded by infrared or raman spectroscopy when directly attached to the support.Type: GrantFiled: September 4, 1997Date of Patent: March 12, 2002Inventors: Jill Edie Hochlowski, Thomas J. Sowin, Daniel W. Norbeck, Anne-Laure Marie Grillot, Rolf E. Swenson
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Patent number: 6346640Abstract: The process comprises reacting 2-, 3- or 4-pentenenitrile or mixtures thereof with carbon monoxide and a hydroxyl compound in the presence of a catalyst system comprising (i) a palladium(II) compound, (ii) a bidentate diphosphine ligand and (iii) an anion source. Novel catalyst systems containing diphosphine ligands of the bis(phosphinomethyl)amine type are also described.Type: GrantFiled: February 26, 2001Date of Patent: February 12, 2002Assignee: BASF AktiengesellschaftInventors: Michael Slany, Martin Schäfer, Michael Schulz
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Patent number: 6326508Abstract: The method of the present invention comprises feeding crude acetonitrile containing acrylonitrile as an impurity and water into the upper portion of a distillation column, distilling the crude acetonitrile in the presence of the water for a time sufficient to allow substantially all of the acrylonitrile impurity to be vaporized in the presence of the water, removing substantially all of the acrylonitrile in an overhead stream exiting from the distillation column and recovering the crude acetonitrile substantially free of acrylonitrile impurity from the lower portion of the distillation column. In particular, the method can be utilized to produce HPLC grade acetonitrile (UV cutoff <190).Type: GrantFiled: September 5, 2000Date of Patent: December 4, 2001Assignee: The Standard Oil CompanyInventors: Sanjay Purushottam Godbole, Richard Lee Wappelhorst, Paul Alan Jacobson
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Publication number: 20010041709Abstract: The present invention relates to compounds of formula (I) 1Type: ApplicationFiled: January 26, 2001Publication date: November 15, 2001Inventors: John Patrick Mogensen, Per Sauerberg, Paul Stanley Bury, Lone Jeppesen, Ingrid Pettersson
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Patent number: 6288263Abstract: 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: May 25, 2000Date of Patent: September 11, 2001Assignee: The Dow Chemical CompanyInventors: Phillip S. Athey, David A. Wilson
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Publication number: 20010016665Abstract: A method of making (±)-3-(aminomethyl)-5-methylhexanoic acid that comprises condensing isovaleraldehyde with 1Type: ApplicationFiled: October 5, 1999Publication date: August 23, 2001Inventors: TODD MICHEL GROTE, BRIAN KEITH HUCKABEE, THOMAS MULHERN, DENIS MARTIN SOBIERAY, ROBERT DANIEL TITUS
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Patent number: 5973200Abstract: A process for the free-radical addition of a mercaptan to a nonconjugated olefinic substrate having a terminal carbon-carbon double bond is disclosed. 2-Hydroxy-4-(ethylthio)butanoic acid (HMBA) or methionine can be prepared using this method. The nonconjugated olefinic substrate has the general formula: ##STR1## wherein R is selected from the group consisting of --COOH, --COOR.sup.2, --CONR.sup.3 R.sup.4, --CN and --CCl.sub.3, R.sup.1 is selected from the group consisting of --OH, --OCOR.sup.2, --NHCOR.sup.2 and --NH.sub.2, R.sup.2 is selected from the group consisting of alkyl, cycloalkyl and aryl and R.sup.3 and R.sup.4 are independently selected from the group consisting of --H and R.sup.2.Type: GrantFiled: January 20, 1998Date of Patent: October 26, 1999Assignee: Novus International, Inc.Inventor: Karl E. Koenig
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Patent number: 5908954Abstract: A process for the preparation of five-membered or six-membered ring lactams from aliphatic .alpha.,.omega.-dinitriles has been developed. In the process an aliphatic .alpha.,.omega.-dinitrile is first converted to an ammonium salt of an .omega.-nitrile-carboxylic acid in aqueous solution using a catalyst having an aliphatic nitrilase (EC 3.5.5.7) activity, or a combination of nitrile hydratase (EC 4.2.1.84) and arnidase (EC 3.5.1.4) activities. The ammonium salt of the .omega.-nitrilecarboxylic acid is then converted directly to the corresponding lactam by hydrogenation in aqueous solution, without isolation of the intermediate .omega.-nitrilecarboxylic acid or .omega.-aminocarboxylic acid. When the aliphatic .alpha.,.omega.-dinitrile is also unsymmetrically substituted at the .alpha.-carbon atom, the nitrilase produces the .omega.-nitrilecarboxylic acid ammonium salt resulting from hydrolysis of the .omega.Type: GrantFiled: July 1, 1998Date of Patent: June 1, 1999Assignee: E. I. du Pont de Nemours and CompanyInventors: Robert Di Cosimo, Robert Donald Fallon, John Edward Gavagan, Frank Edward Herkes
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Patent number: 5908953Abstract: Crude (R)-4-cyano-3-hydroxybutyric acid lower alkyl ester, obtained by subjecting an (S)-4-halogeno-3-hydroxybutyric acid lower alkyl ester to a cyano-introducing reaction, is purified by distillation carried out in the presence of a solvent having a boiling point within the range of 50.degree. C. to 160.degree. C. at 10 Torr.Type: GrantFiled: December 10, 1997Date of Patent: June 1, 1999Assignee: Mitsubishi Chemical CorporationInventors: Hitoshi Matsuda, Toshiharu Shibata, Hidekichi Hashimoto, Mitsumasa Kitai
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Patent number: 5902895Abstract: A method for the continuous production of esters of thermally unstable acids by the esterification, with or without a catalyst, of the acids with alcohols is provided. The method involves esterification at temperatures of approximately 80.degree. C. to approximately 130.degree. C., essentially in a single reaction zone, to which the acid and an excess of alcohol are continuously supplied and from which a vapor stream containing alcohol and water produced by the esterification reaction are removed, while at the same time removing an ester-rich liquid reaction mixture from the single reaction zone, from which the ester is obtained.Type: GrantFiled: May 5, 1997Date of Patent: May 11, 1999Assignee: Huels AktiengesellschaftInventor: Manfred Kaufhold
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Patent number: 5847193Abstract: The present invention provides a labelled .beta.-cyano-L-alanine and a .gamma.-cyano-.alpha.-aminobutyric acid, of which cyano group carbon is labelled with radionuclide .sup.11 C or .sup.14 C, or stable isotope .sup.13 C. The present invention also provides a labelled amino acids such as asparagine, asparatic acid, DABA, GABA, glutamine and glutamic acid synthesized by using the labelled .beta.-cyano-L-alanine and the .gamma.-cyano-.alpha.-aminobutyric acid as an intermediate. The labelled amino acids are useful for in vivo imaging of tumors and brain functions.Type: GrantFiled: March 22, 1996Date of Patent: December 8, 1998Inventors: Yasuyoshi Watanabe, Hironori Omura, Yuji Furuya, Bengt Langstrom, Gunnar Antoni
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Patent number: 5840956Abstract: A method of making (.+-.)-3-(aminomethyl)-5-methylhexanoic acid that comprises condensing isovaleraldehyde with ##STR1## to form primarily ##STR2## reacting the ##STR3## with a cyanide source to form ##STR4## decarboxylating the ##STR5## to form ##STR6## hydrolyzing the ##STR7## with an alkali or alkaline earth metal hydroxide to form an alkali or alkaline earth metal carboxylate salt; and hydrogenating the alkali or alkaline earth metal carboxylate salt to form (.+-.)-3-(aminomethyl)-5-methylhexanoic acid, wherein R.sub.1 and R.sub.2 are the same or different and are hydrogen, C.sub.1 -C.sub.6 alkyl, aryl, benzyl, or C.sub.3 -C.sub.6 cycloalkyl. The present invention also provides a method of making (.+-.Type: GrantFiled: February 6, 1997Date of Patent: November 24, 1998Assignee: Warner-Lambert CompanyInventors: Todd Michel Grote, Brian Keith Huckabee, Thomas Mulhern, Denis Martin Sobieray, Robert Daniel Titus
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Patent number: 5817613Abstract: A novel intermediate useful in the synthesis of 2-hydroxyethyl iminodiacetic acid is disclosed. The intermediate can be formed by contacting 2-hydroxyethyl amine with glycolonitrile to form an aminonitrile which can be hydrolyzed and contacted with additional glycolonitrile to form the nitrile intermediate which can be converted to 2-hydroxylethyl iminodiacetic acid via hydrolysis.Type: GrantFiled: October 21, 1997Date of Patent: October 6, 1998Assignee: The Dow Chemical CompanyInventors: Phillip S. Athey, David A. Wilson, Druce K. Crump
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Patent number: 5817603Abstract: Substituted cyclohexene-1,2-dicarboxylic acid derivatives I ##STR1## where R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are herein defined, or the agriculturally useful salts of Ia and Ib and intermediates for their preparation, which compounds are useful as herbicides and for the desiccation/defoliation of plants.Type: GrantFiled: February 11, 1997Date of Patent: October 6, 1998Assignee: BASF AktiengesellschaftInventors: Ralf Klintz, Elisabeth Heistracher, Peter Schaefer, Gerhard Hamprecht, Peter Plath, Uwe Kardorff, Matthias Gerber, Karl-Otto Westphalen, Helmut Walter
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Patent number: 5726341Abstract: A novel intermediate useful in the synthesis of 2-hydroxyethyl iminodiacetic acid is disclosed. The intermediate can be formed by contacting 2-hydroxyethyl amine with glycolonitrile to form an aminonitrile which can be hydrolyzed and contacted with additional glycolonitrile to form the nitrile intermediate which can be converted to 2-hydroxylethyl iminodiacetic acid via hydrolysis.Type: GrantFiled: October 31, 1996Date of Patent: March 10, 1998Assignee: The Dow Chemical CompanyInventors: Phillip S. Athey, Druce K. Crump, David A. Wilson
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Patent number: 5488130Abstract: A novel intermediate useful in the synthesis of 2-hydroxypropyl iminodiacetic acid is disclosed. The intermediate can be formed by contacting 2-hydroxypropyl amine with glycolonitrile to form an aminonitrile which can be hydrolyzed and contacted with additional glycolonitrile to form the nitrile intermediate which can be converted to 2-hydroxylpropyl iminodiacetic acid via hydrolysis.Type: GrantFiled: March 31, 1995Date of Patent: January 30, 1996Assignee: The Dow Chemical CompanyInventors: Phillip S. Athey, Druce K. Crump, David A. Wilson
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Patent number: 5468870Abstract: Dye-donor element for use according to thermal dye sublimation transfer comprising a support having thereon a dye layer containing a dye corresponding to the following formula ##STR1## wherein Z represents CN, COOR.sup.1 or CONR.sup.2 R.sup.3 ;R.sup.1, R.sup.2 and R.sup.3 each independently represent hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or R.sup.2 and R.sup.3 together represent the necessary atoms to close a heterocyclic nucleus or substituted heterocyclic nucleus;Y represents OR.sup.4 or NR.sup.5 R.sup.6 or CN;R.sup.4 represents hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, SO.sub.2 R.sup.7, COR.sup.7, CSR.sup.7, POR.sup.7 R.sup.8 ;R.sup.5 and R.sup.6 each independently has one of the significances given to R.sup.4 or represent substituted or unsubstituted amino, or R.sup.5 and R.sup.Type: GrantFiled: October 20, 1994Date of Patent: November 21, 1995Assignee: AGFA-GAVAERT, N.V.Inventor: Luc J. Vanmaele
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Patent number: 5434290Abstract: Preparation of 5-cyanovalerates (I) by the carbonylation of a 1-cyanobutene with carbon monoxide and an alkanol (II) corresponding to the ester radical at an elevated temperature and under superatmospheric pressure in the presence of a cobalt catalyst as well as in the presence of an activating solvent, in which the activating solvent used is an effective amount of a carbonic diester, a carbamate, or a urea of the general formula IIIa, IIIb, or IIIcR--O--CO--O--R (IIIa)R.sub.2 N--CO--O--R (IIIb)R.sub.2 N--CO--NR.sub.2 (IIIc)or a mixture of these compounds (R's same or different, C.sub.1 -C.sub.6 alkyl, C.sub.5 -C.sub.7 cycloalkyl groups or together form 5-membered to 7-membered rings).The end products I serve as intermediates, chiefly for the preparation of .epsilon.-caprolactam.Type: GrantFiled: February 28, 1994Date of Patent: July 18, 1995Assignee: BASF AktiengesellschaftInventors: Stefan Stahl, Wolfgang Harder, Arthur Hoehn
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Patent number: 5430171Abstract: T-butyl (R)-(-)-4-cyano-3-hydroxybutyrate having an optical purity of 99%ee or higher and a process for producing the same are disclosed, the process comprising cyanogenation of a t-butyl (S)-(-)-4-halogeno-3-hydroxybutyrate obtained by enantioselective hydrogenation of a t-butyl 4-halogenoacetoacetate. Recrystallization of the resulting crude product gives the optically active compound with high optical purity.Type: GrantFiled: July 11, 1994Date of Patent: July 4, 1995Assignee: Takasago International CorporationInventors: Shigeru Mitsuhashi, Kazutoshi Sakurai, Hidenori Kumobayashi
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Patent number: 5412146Abstract: For the preparation of 2-cyanoacetoxypropionic esters, a mixture of lactic ester and cyanoacetic ester is introduced, an alkali metal alcoholate is added as catalyst and the mixture is heated while the alcohol eliminated during the course of the reaction is distilled off. The course of the reaction is followed by means of gas chromatographic analysis and the reaction is terminated prior to eliminating the theoretical amount of alcohol by destroying the catalyst by acidification. The reaction mixture is worked up by distillation and the product easily separated from the reaction mass due to the substantial absence of high boiling components.Type: GrantFiled: June 3, 1994Date of Patent: May 2, 1995Assignee: Huels AktiengesellschaftInventors: Manfred Kaufhold, Marcel Feld
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Patent number: 5393917Abstract: A process for isolating and purifying oxadimethacrylics of the general formula ICH.sub.2 .dbd.C(A)CH.sub.2 --O--CH.sub.2 C(B).dbd.CH.sub.2 Iwhere A and B are selected from the group consisting of --COOR.sup.1, --COR.sup.1, --CONR.sup.2 R.sup.3 and --CN and R.sup.1, R.sup.2 and R.sup.3 are each defined as follows:R.sup.1 is hydrogen, alkyl, substituted or unsubstituted cycloalkyl or cycloalkylalkyl, hydroxyalkyl, aminoalkyl, N-alkylaminoalkyl, N,N-dialkylaminoalkyl, substituted or unsubstituted aryl or arylalkyl,R.sup.2 and R.sup.3 are each hydrogen, alkyl, substituted or substituted cycloalkyl or cycloalkylalkyl, substituted or unsubstituted aryl or arylalkyl,comprises precipitating or crystallizing them from their solutions that contain at least one liquid hydrocarbon compound.Type: GrantFiled: December 16, 1993Date of Patent: February 28, 1995Assignee: BASF AktiengesellschaftInventors: Siegmund Besecke, Andreas Deckers, Harald Lauke
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Patent number: 5324852Abstract: The present invention provides an optically active 4-substituted-2-hydroxybutanoate represented by the general formula: ##STR1## wherein X is Cl, Br, I or Cn, R is alkyl, and * shows an asymmetric carbon.The compounds which are useful as starting materials for medical agents, are obtained by a process comprising ring-opening optically active .alpha.-hydroxy-.gamma.-butyrolactone and esterifying the compound obtained.Type: GrantFiled: November 16, 1992Date of Patent: June 28, 1994Assignee: Chisso CorporationInventors: Naoyuki Yoshida, Kazutoshi Miyazawa
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Patent number: 5292918Abstract: A process for preparing an (S,S) or (R,R) diastereoisomer of the formula: ##STR1## or salts, esters or amides thereof, wherein R.sup.3 and R.sup.4 independently represent hydrogen, alkyl, aryl or aryl substituted with halogen, alkyl, nitro or alkoxy, and n and m independently represent integers from one to six, comprising combining a cyanide compound of the formula:M.sup.1 C.tbd.N (III)wherein M.sup.1 is hydrogen, trimethylsilyl or a metal, with an optional proton source, a solvent and a Lewis acid of the formula:M.sup.2 X.sub.4, AlCl.sub.3 or BF.sub.3 (IV)wherein M.sup.2 is Sn or Ti and X represents chloro, bromo, fluoro or iodo, with an .alpha.-amino acid compound or salts or esters thereof, followed by addition of an acyl or acetal compound to give the diastereoisomer of formula (X).Type: GrantFiled: October 6, 1992Date of Patent: March 8, 1994Assignee: Schering CorporationInventors: Jacques Gosteli, Ingrid Mergelsberg, Markus Tanner
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Patent number: 5210280Abstract: A process for the preparation of alkanedioic acid derivatives comprising reacting an alkenoic acid derivative with carbon monoxide and a nucleophilic compound having a mobile hydrogen atom in the presence of a catalyst system comprising a source of a Group VIII metal, a source of a bidentate diphosphine liquid, a source of an anion and a source of a quinone promoter.Type: GrantFiled: February 19, 1992Date of Patent: May 11, 1993Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 5204322Abstract: The present invention relates to novel nitrile and aldoxime indane compounds, such as 1,1,2,3,3,4,6-heptamethylindane-5-nitrile and 1,1,2,3,3,4,6-heptamethylindane-5-aldoxime, and to compositions containing the same. Compounds and compositions of the invention possess a fragrant musk-like aroma, and thus are useful in the perfumery and/or other industries.Type: GrantFiled: December 31, 1991Date of Patent: April 20, 1993Assignee: Union Camp CorporationInventor: Walter C. Frank
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Patent number: 5169979Abstract: The invention relates to a curing component (A) containing active CH groups, which contains at least two groups of the formula (I) ##STR1## or structural units of the formula (I') or (I") ##STR2## in which: A denotes ##STR3## X and Y are identical or different and denote ##STR4## CO.sub.2 R.sup.1, CN, NO.sub.2, CONH.sub.2, CONR.sup.1 H or CONR.sup.1 R.sup.1, where the R.sup.1 radicals may be identical or different and represent a hydrocarbon radical, preferably an alkyl radical having 1 to 12 carbon atoms, which may also be interrupted by oxygen or an N-alkyl radical, with the proviso that only one of the two radicals X and Y may represent the NO.sub.2 group;A' denotes ##STR5## X' and Y' are identical or different and denote ##STR6## Curable mixtures of (A) and a Michael acceptor (B) and, if appropriate diluents and customary additivies cure rapidly even at low temperatures and are suitable, in particular for surface-coating preparations.Type: GrantFiled: November 30, 1990Date of Patent: December 8, 1992Assignee: Hoechst AGInventors: Uwe Kubillus, Gerhard Brindopke, Helmut Plum
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Patent number: 5110985Abstract: A process for preparing a carboxyalkyl-substituted hydroxylamine represented by formula (I) ##STR1## where L represents an alkylene group; A represents a hydrogen atom, a sulfo group, a carboxy group, a phosphono group, a trialkylammonio group, a hydroxy group, an amino group, an acyl group, a carbamoyl group, a sulfamoyl group, an alkoxycarbonyl group, or a cyano group; and R.sub.1, R.sub.2, and R.sub.3, which may be the same or different, each represent a hydrogen atom, an alkyl group, or an aryl group; which comprises: reacting an .alpha.,.beta.-unsaturated carboxylic acid represented by formula (II) as an alkylating agent ##STR2## where R'.sub.1, R'.sub.2, and R'.sub.3, which may be the same or different, each represent the same group as defined for R.sub.1, R.sub.2, and R.sub.Type: GrantFiled: November 9, 1990Date of Patent: May 5, 1992Assignee: Fuji Photo Film Co., Ltd.Inventors: Hiroshi Hayakawa, Kiyoshi Morimoto
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Patent number: 5017705Abstract: Novel aryl and heteroaryl 4-cyano-2,2,4-trichlorobutyrates are prepared by reacting a corresponding aryl or heteroaryl trichloroacetate with acrylonitrile in the presence of a catalyst. Also provided is a novel process for producing 3,5,6-trichloropyridin-2-ol comprising cyclization of an aryl or heteroaryl 4-cyano-2,2,4-trichlorobutyrate in an inert organic solvent at elevated temperatures, in the presence of anhydrous hydrogen chloride.Type: GrantFiled: May 8, 1989Date of Patent: May 21, 1991Assignee: Luxembourg Industries (Pamol) Ltd.Inventor: Yigal Becker
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Patent number: 5010189Abstract: The invention relates to novel processes and intermediates for the preparation of 5-amino-4-hydroxyvaleric acid derivatives of the formula ##STR1## in which R.sup.1 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl or the radical of a natural amino acid, R.sup.2 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl, amino, hydroxy, mercapto, sulphinyl, sulphonyl or the radical of a natural amino acid, and R.sup.3 represents optionally substituted hydroxy or amino, by sigmatropic rearrangement of a suitable allyl ester, halolactonization of the resulting .gamma.,.delta.-unsaturated acid or of a suitable derivative thereof, exchange of halogen for a nitrogen-containing nucleophile, opening of the lactone ring and freeing of the amino group. Compounds of the formula I are starting materials for the preparation of renin-inhibitors which have an anti-hypertensive action.Type: GrantFiled: October 24, 1989Date of Patent: April 23, 1991Assignee: Ciba-Geigy CorporationInventors: Peter Herold, Christof Angst
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Patent number: 4996323Abstract: The preparation of 3,5,6-trichloropyridin-2-ol from trichloroacetyl chloride and acrylonitrile is improved by separately conducting the individual addition, cyclization and aromatization steps. By separating the steps, water and HCl, by-products of the latter steps, can be precluded from interfering with the earlier steps. The individual process steps have also been improved.Type: GrantFiled: May 12, 1989Date of Patent: February 26, 1991Assignee: The Dow Chemical CompanyInventor: R. Garth Pews
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Patent number: 4973730Abstract: Serine-N,N-diacetic acid and derivatives thereof are prepared in various ways and used in particular as complexing agents, bleaching agent stabilizers and builders in detergents.Type: GrantFiled: April 4, 1988Date of Patent: November 27, 1990Assignee: BASF AktiengesellschaftInventors: Richard Baur, Felix Richter, Stefan Birnbach, Rolf Fikentscher, Alfred Oftring, Ekhard Winkler
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Patent number: 4960881Abstract: The invention relates to carbonates of formula: ##STR1## in which X is a fluorine, chlorine or bromine atom and R.sup.1 is different from the ##STR2## group and represents: a substituted or non-substituted, saturated or unsaturated, aliphatic, araliphatic, primary, secondary, tertiary or cycloaliphatic radical. These .alpha.-chlorinated carbonates are prepared by the action of a compound of formula R.sup.1 OH on a chloroformate of formula: ##STR3## in a solvent medium in the presence of an acid scavenger which is added after the two preceding compounds. They are used to block the amine function of amino acids. The .alpha.-chlorinated carbonate and amino acid are reacted in a solvent medium at a temperature of -5.degree. to 100.degree. C. in the presence of an acid scavenger. Blocked amines are very useful in peptide synthesis.Type: GrantFiled: June 6, 1988Date of Patent: October 2, 1990Assignee: Societe Nationale des Poudres et ExplosifsInventors: Gerard Barcelo, Jean-Pierre Senet, Gerard Sennyey
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Patent number: 4950778Abstract: Manufacture of 5-cyanovaleric acid by carbonylation of pentenenitriles from a mixture consisting essentially of pentenenitrile, CO and at least one compound of the formula ROH, where R is hydrogen or alkyl of 1 to 6 carbon atoms, and a cyclic urea and/or a cyclic amide, where the combined weight of the cosolvents is between about 70% and 99% of the total weight of the reaction mixture.Type: GrantFiled: November 8, 1989Date of Patent: August 21, 1990Assignee: E. I. Du Pont de Nemours & CompanyInventors: Patrick M. Burke, James B. Sieja
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Patent number: 4945179Abstract: Process for the preparation of esters of carboxylic acids by contacting an olefinically unsaturated compound with CO and an alcohol, in the presence of (a) a ruthenium compound and (b) an iodide salt, LiBr and/or an onium bromide, with a molar ratio of CO to olefinically unsaturated compound.ltoreq.2.0 being applied when "b" is an iodide salt.Type: GrantFiled: August 15, 1988Date of Patent: July 31, 1990Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 4933483Abstract: Manufacture of 5-cyanovaleric acid and its esters by carbonylation of pentenenitriles from a mixture consisting essentially of pentenenitrile, CO and at least one compound of the formula R'OH, where R is hydrogen or alkyl of 1 to 6 carbon atoms.Type: GrantFiled: December 12, 1988Date of Patent: June 12, 1990Assignee: E. I. Du Pont de Nemours and CompanyInventors: Patrick M. Burke, James B. Sieja
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Patent number: 4927954Abstract: A continuous process for efficiently co-producing secondary alcohols of long-chain olefins and lower carboxylic acid esters, comprising (I) performing an acid/olefin reaction in the presence of a heterogeneous catalyst such as Amberlyst 15, and (II) performing an ester-exchange reaction in the presence of, e.g., titanium alcoholate. A desirable feature of the process is the ability to produce co-products of choice.Type: GrantFiled: April 19, 1989Date of Patent: May 22, 1990Assignee: Union Carbide Chemicals and Plastics Company, Inc.Inventors: Robert J. Knopf, Louis F. Theiling Jr., Leroy P. Berti
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Patent number: 4921995Abstract: A novel process for manufacturing 16-substituted .DELTA..sup.7 -prostaglandin Es, which include compounds expressed by the following formula (I), their enanantiomers, or their mixtures of arbitrary mixing ratio, ##STR1## wherein R.sup.1 indicates COOR.sup.2, CH.sub.2 OR.sup.3, or COCH.sub.2 OR.sup.3, in which R.sup.2 indicates a hydrogen atom, a substituted or unsubstituted C.sub.1 -C.sub.10 alkyl group, a substituted or unsubstituted C.sub.3 -C.sub.10 cycloalkyl group, or a substituted or unsubstituted phenyl group, and R.sup.3 indicates a hydrogen atom, a tri(C.sub.1 -C.sub.7) hydrocarbon silyl group, a group which forms an acetal bond together with the oxygen atom of a hydroxyl group, or a C.sub.2 -C.sub.7 acyl group; R.sup.4 and R.sup.5 are identical or different, each representing a hydrogen atom, a tri(C.sub.1 -C.sub.7) hydrocarbon silyl group, or a group which forms an acetal bond together with the oxygen atom of a hydroxyl group; R.sup.6 indicates a hydrogen atom, a C.sub.1 -C.sub.Type: GrantFiled: February 9, 1988Date of Patent: May 1, 1990Assignee: Teijin LimitedInventors: Toshio Tanaka, Atsuo Hazato, Seizi Kurozumi, Masahiro Koga
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Patent number: 4914232Abstract: An essentially single stage reaction has been discovered in which a disubstituted ethanolamine, that is, a 2,2'-substituted-2-aminoethanol, may be reacted with a haloform and a carbonyl containing compound selected from the group consisting of monoketones and benzaldehyde, in the presence of an alkali metal hydroxide, and optionally in the presence of a phase transfer catalyst, to produce an alkali metal hydroxyethylaminoacetate ("HEAA") which has N-adjacent C atoms on which there are a total of at least three substituents (hence "polysubstituted"), and one or both pairs of substituents on each N-adjacent C atom may be cyclized. The HEAA may be cyclized by the action of a mineral acid to produce a 2-morpholone hydrochloride which is characterized by having a total of at least three substituents on the N-adjacent C atoms of the ring. The 2-morpholone so produced may be reduced to a polysubstituted aminodiol.Type: GrantFiled: September 28, 1987Date of Patent: April 3, 1990Assignee: The B. F. Goodrich CompanyInventor: John Ta-Yuan Lai
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Patent number: 4902334Abstract: A plant metabolism regulating agent comprising as an active ingredient an alpha,beta or beta,gamma-un-saturated carboxylic acid or its derivative. It is useful for controlling the metabolism of a plant, facilitating the growth of a beneficial plant such as cereals by inhibiting the growth of undesirable plants or eradicating them, regulating the growth of a plant and dwarfing a plant.Type: GrantFiled: October 31, 1984Date of Patent: February 20, 1990Assignee: Teijin LimitedInventors: Shizuo Azuma, Toshiyuki Hiramatsu, Teizo Yamaji, Yataro Ichikawa
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Patent number: 4898977Abstract: The invention relates to novel processes and intermediates for the preparation of 5-amino-4-hydroxyvaleric acid derivatives of the formula ##STR1## in which R.sup.1 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl or the radical of a natural amino acid, R.sup.2 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl, amino, hydroxy, mercapto, sulphinyl, sulphonyl or the radical of a natural amino acid, and R.sup.3 represents optionally substituted hydroxy or amino, by sigmatropic rearrangement of a suitable allyl ester, halolactonisation of the resulting .gamma.,.delta.-unsaturated acid or of a suitable derivative thereof, exchange of halogen for a nitrogen-containing nucleophile, opening of the lactone ring and freeing of the amino group. Compounds of the formula I are starting materials for the preparation of renin-inhibitors which have an anti-hypertensive action.Type: GrantFiled: August 13, 1987Date of Patent: February 6, 1990Assignee: Ciba-Geigy CorporationInventors: Peter Herold, Christof Angst
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Patent number: 4889948Abstract: A process for synthesizing ethers of alkyl alpha(hydroxymethyl)-acrylate by reacting alkyl acrylate and formaldehyde in the presence of a DABCO catalyst. The ethers may be used as cross-linking agents for thermoplastic polymers. Further, these ethers in turn enable synthesis of cyclopolymers that may show promising biological activity.Type: GrantFiled: August 18, 1987Date of Patent: December 26, 1989Assignee: University of Southern MississippiInventors: Lon J. Mathias, Selim H. Kusefoglu