Oxygen Bonded Directly To The Carbonyl Group (e.g., Carboxylic Acid Esters, Etc.) Patents (Class 558/441)
  • Publication number: 20020187992
    Abstract: 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: Application
    Filed: January 31, 2002
    Publication date: December 12, 2002
    Inventors: Carl W. Gilbert, Eleanor B. McGowan, Kirby S. Black, T. Gregory P. Harper
  • Patent number: 6492553
    Abstract: 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: Grant
    Filed: August 4, 1999
    Date of Patent: December 10, 2002
    Assignee: 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
  • Publication number: 20020183518
    Abstract: Y—X—C(R′)═C(R″)COOR″′  (A1)
    Type: Application
    Filed: November 27, 2001
    Publication date: December 5, 2002
    Applicant: ONTOGEN CORPORATION
    Inventors: Adnan M. M. Mjalli, Xiaodong Cao, Edmund J. Moran
  • Publication number: 20020147360
    Abstract: Compounds represented by the formula 1
    Type: Application
    Filed: February 22, 2002
    Publication date: October 10, 2002
    Inventors: Phillip S. Athey, David A. Wilson
  • Publication number: 20020115881
    Abstract: There are described 4-aminobut-2-ynecarboxylic acid derivatives of formula 1
    Type: Application
    Filed: December 13, 2001
    Publication date: August 22, 2002
    Inventors: Werner Holzl, Wolfgang Haap, Jurgen Koppold, Dietmar Ochs, Karin Petzold, Marcel Schnyder
  • Patent number: 6433213
    Abstract: 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: Grant
    Filed: June 16, 2000
    Date of Patent: August 13, 2002
    Assignee: Warner-Lambert Company
    Inventors: Robert Lee Bosch, Richard Joseph McCabe, Thomas Norman Nanninga, Robert Joseph Stahl
  • Publication number: 20020107285
    Abstract: 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: Application
    Filed: February 15, 2002
    Publication date: August 8, 2002
    Applicant: Calyx Therapeutics, Inc.
    Inventors: Partha Neogi, Bishwajit Nag, Frederick J. Lakner, Debendranath Dev, Satyanarayana Medicherla
  • Publication number: 20020086996
    Abstract: 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: Application
    Filed: December 14, 2001
    Publication date: July 4, 2002
    Applicant: AXYS PHARMACEUTICALS, INC.
    Inventors: Clifford M. Bryant, James T. Palmer, Robert M. Rydzewski, Eduardo L. Setti, Zong-Qiang Tian, Shankar Venkatraman, Dan-Xiong Wang
  • Publication number: 20020045748
    Abstract: 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 containing
    Type: Application
    Filed: March 13, 2001
    Publication date: April 18, 2002
    Inventors: Eit Drent, Willem Wabe Jager
  • Patent number: 6355490
    Abstract: 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: Grant
    Filed: September 4, 1997
    Date of Patent: March 12, 2002
    Inventors: Jill Edie Hochlowski, Thomas J. Sowin, Daniel W. Norbeck, Anne-Laure Marie Grillot, Rolf E. Swenson
  • Patent number: 6346640
    Abstract: 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: Grant
    Filed: February 26, 2001
    Date of Patent: February 12, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Slany, Martin Schäfer, Michael Schulz
  • Patent number: 6326508
    Abstract: 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: Grant
    Filed: September 5, 2000
    Date of Patent: December 4, 2001
    Assignee: The Standard Oil Company
    Inventors: Sanjay Purushottam Godbole, Richard Lee Wappelhorst, Paul Alan Jacobson
  • Publication number: 20010041709
    Abstract: The present invention relates to compounds of formula (I) 1
    Type: Application
    Filed: January 26, 2001
    Publication date: November 15, 2001
    Inventors: John Patrick Mogensen, Per Sauerberg, Paul Stanley Bury, Lone Jeppesen, Ingrid Pettersson
  • Patent number: 6288263
    Abstract: 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: Grant
    Filed: May 25, 2000
    Date of Patent: September 11, 2001
    Assignee: The Dow Chemical Company
    Inventors: Phillip S. Athey, David A. Wilson
  • Publication number: 20010016665
    Abstract: A method of making (±)-3-(aminomethyl)-5-methylhexanoic acid that comprises condensing isovaleraldehyde with 1
    Type: Application
    Filed: October 5, 1999
    Publication date: August 23, 2001
    Inventors: TODD MICHEL GROTE, BRIAN KEITH HUCKABEE, THOMAS MULHERN, DENIS MARTIN SOBIERAY, ROBERT DANIEL TITUS
  • Patent number: 5973200
    Abstract: 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: Grant
    Filed: January 20, 1998
    Date of Patent: October 26, 1999
    Assignee: Novus International, Inc.
    Inventor: Karl E. Koenig
  • Patent number: 5908953
    Abstract: 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: Grant
    Filed: December 10, 1997
    Date of Patent: June 1, 1999
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Hitoshi Matsuda, Toshiharu Shibata, Hidekichi Hashimoto, Mitsumasa Kitai
  • Patent number: 5908954
    Abstract: 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: Grant
    Filed: July 1, 1998
    Date of Patent: June 1, 1999
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Robert Di Cosimo, Robert Donald Fallon, John Edward Gavagan, Frank Edward Herkes
  • Patent number: 5902895
    Abstract: 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: Grant
    Filed: May 5, 1997
    Date of Patent: May 11, 1999
    Assignee: Huels Aktiengesellschaft
    Inventor: Manfred Kaufhold
  • Patent number: 5847193
    Abstract: 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: Grant
    Filed: March 22, 1996
    Date of Patent: December 8, 1998
    Inventors: Yasuyoshi Watanabe, Hironori Omura, Yuji Furuya, Bengt Langstrom, Gunnar Antoni
  • Patent number: 5840956
    Abstract: 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: Grant
    Filed: February 6, 1997
    Date of Patent: November 24, 1998
    Assignee: Warner-Lambert Company
    Inventors: Todd Michel Grote, Brian Keith Huckabee, Thomas Mulhern, Denis Martin Sobieray, Robert Daniel Titus
  • Patent number: 5817603
    Abstract: 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: Grant
    Filed: February 11, 1997
    Date of Patent: October 6, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Ralf Klintz, Elisabeth Heistracher, Peter Schaefer, Gerhard Hamprecht, Peter Plath, Uwe Kardorff, Matthias Gerber, Karl-Otto Westphalen, Helmut Walter
  • Patent number: 5817613
    Abstract: 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: Grant
    Filed: October 21, 1997
    Date of Patent: October 6, 1998
    Assignee: The Dow Chemical Company
    Inventors: Phillip S. Athey, David A. Wilson, Druce K. Crump
  • Patent number: 5726341
    Abstract: 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: Grant
    Filed: October 31, 1996
    Date of Patent: March 10, 1998
    Assignee: The Dow Chemical Company
    Inventors: Phillip S. Athey, Druce K. Crump, David A. Wilson
  • Patent number: 5488130
    Abstract: 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: Grant
    Filed: March 31, 1995
    Date of Patent: January 30, 1996
    Assignee: The Dow Chemical Company
    Inventors: Phillip S. Athey, Druce K. Crump, David A. Wilson
  • Patent number: 5468870
    Abstract: 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: Grant
    Filed: October 20, 1994
    Date of Patent: November 21, 1995
    Assignee: AGFA-GAVAERT, N.V.
    Inventor: Luc J. Vanmaele
  • Patent number: 5434290
    Abstract: 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: Grant
    Filed: February 28, 1994
    Date of Patent: July 18, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Stefan Stahl, Wolfgang Harder, Arthur Hoehn
  • Patent number: 5430171
    Abstract: 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: Grant
    Filed: July 11, 1994
    Date of Patent: July 4, 1995
    Assignee: Takasago International Corporation
    Inventors: Shigeru Mitsuhashi, Kazutoshi Sakurai, Hidenori Kumobayashi
  • Patent number: 5412146
    Abstract: 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: Grant
    Filed: June 3, 1994
    Date of Patent: May 2, 1995
    Assignee: Huels Aktiengesellschaft
    Inventors: Manfred Kaufhold, Marcel Feld
  • Patent number: 5393917
    Abstract: 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: Grant
    Filed: December 16, 1993
    Date of Patent: February 28, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Siegmund Besecke, Andreas Deckers, Harald Lauke
  • Patent number: 5324852
    Abstract: 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: Grant
    Filed: November 16, 1992
    Date of Patent: June 28, 1994
    Assignee: Chisso Corporation
    Inventors: Naoyuki Yoshida, Kazutoshi Miyazawa
  • Patent number: 5292918
    Abstract: 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: Grant
    Filed: October 6, 1992
    Date of Patent: March 8, 1994
    Assignee: Schering Corporation
    Inventors: Jacques Gosteli, Ingrid Mergelsberg, Markus Tanner
  • Patent number: 5210280
    Abstract: 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: Grant
    Filed: February 19, 1992
    Date of Patent: May 11, 1993
    Assignee: Shell Oil Company
    Inventor: Eit Drent
  • Patent number: 5204322
    Abstract: 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: Grant
    Filed: December 31, 1991
    Date of Patent: April 20, 1993
    Assignee: Union Camp Corporation
    Inventor: Walter C. Frank
  • Patent number: 5169979
    Abstract: 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: Grant
    Filed: November 30, 1990
    Date of Patent: December 8, 1992
    Assignee: Hoechst AG
    Inventors: Uwe Kubillus, Gerhard Brindopke, Helmut Plum
  • Patent number: 5110985
    Abstract: 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: Grant
    Filed: November 9, 1990
    Date of Patent: May 5, 1992
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Hiroshi Hayakawa, Kiyoshi Morimoto
  • Patent number: 5017705
    Abstract: 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: Grant
    Filed: May 8, 1989
    Date of Patent: May 21, 1991
    Assignee: Luxembourg Industries (Pamol) Ltd.
    Inventor: Yigal Becker
  • Patent number: 5010189
    Abstract: 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: Grant
    Filed: October 24, 1989
    Date of Patent: April 23, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Herold, Christof Angst
  • Patent number: 4996323
    Abstract: 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: Grant
    Filed: May 12, 1989
    Date of Patent: February 26, 1991
    Assignee: The Dow Chemical Company
    Inventor: R. Garth Pews
  • Patent number: 4973730
    Abstract: 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: Grant
    Filed: April 4, 1988
    Date of Patent: November 27, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Richard Baur, Felix Richter, Stefan Birnbach, Rolf Fikentscher, Alfred Oftring, Ekhard Winkler
  • Patent number: 4960881
    Abstract: 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: Grant
    Filed: June 6, 1988
    Date of Patent: October 2, 1990
    Assignee: Societe Nationale des Poudres et Explosifs
    Inventors: Gerard Barcelo, Jean-Pierre Senet, Gerard Sennyey
  • Patent number: 4950778
    Abstract: 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: Grant
    Filed: November 8, 1989
    Date of Patent: August 21, 1990
    Assignee: E. I. Du Pont de Nemours & Company
    Inventors: Patrick M. Burke, James B. Sieja
  • Patent number: 4945179
    Abstract: 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: Grant
    Filed: August 15, 1988
    Date of Patent: July 31, 1990
    Assignee: Shell Oil Company
    Inventor: Eit Drent
  • Patent number: 4933483
    Abstract: 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: Grant
    Filed: December 12, 1988
    Date of Patent: June 12, 1990
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Patrick M. Burke, James B. Sieja
  • Patent number: 4927954
    Abstract: 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: Grant
    Filed: April 19, 1989
    Date of Patent: May 22, 1990
    Assignee: Union Carbide Chemicals and Plastics Company, Inc.
    Inventors: Robert J. Knopf, Louis F. Theiling Jr., Leroy P. Berti
  • Patent number: 4921995
    Abstract: 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: Grant
    Filed: February 9, 1988
    Date of Patent: May 1, 1990
    Assignee: Teijin Limited
    Inventors: Toshio Tanaka, Atsuo Hazato, Seizi Kurozumi, Masahiro Koga
  • Patent number: 4914232
    Abstract: 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: Grant
    Filed: September 28, 1987
    Date of Patent: April 3, 1990
    Assignee: The B. F. Goodrich Company
    Inventor: John Ta-Yuan Lai
  • Patent number: 4902334
    Abstract: 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: Grant
    Filed: October 31, 1984
    Date of Patent: February 20, 1990
    Assignee: Teijin Limited
    Inventors: Shizuo Azuma, Toshiyuki Hiramatsu, Teizo Yamaji, Yataro Ichikawa
  • Patent number: 4898977
    Abstract: 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: Grant
    Filed: August 13, 1987
    Date of Patent: February 6, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Herold, Christof Angst
  • Patent number: 4889948
    Abstract: 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: Grant
    Filed: August 18, 1987
    Date of Patent: December 26, 1989
    Assignee: University of Southern Mississippi
    Inventors: Lon J. Mathias, Selim H. Kusefoglu