Amidine, Azomethine, Ketimine Or Oxime In Acid Moiety Patents (Class 560/168)
  • Patent number: 4927964
    Abstract: An advantageous method of producing in large amounts on a commercial scale 2-substituted oxyimino-3-oxobutyric acids, which are useful as intermediates in the synthesis of e.g. aminothiazole cephalosporins, is characterized by reacting a tert-butyl 2-substituted oxyimino-3-oxobutyrate with a hydrogen halide in an anhydrous organic solvent.
    Type: Grant
    Filed: January 11, 1989
    Date of Patent: May 22, 1990
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Kenzo Naito, Yukio Ishibashi, Haruo Shinbo
  • 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: 4879314
    Abstract: Dihaloformaldoximes of the formula: ##STR1## wherein R, X, X.sup.1 and Y are as defined herein having biocidal, fungicidal and pesticidal activity are disclosed.
    Type: Grant
    Filed: January 8, 1986
    Date of Patent: November 7, 1989
    Inventor: Adam C. Hsu
  • Patent number: 4859788
    Abstract: Amino group containing curing component (A) for compounds (B) which contain epoxy or 1,3-dioxolan-2-one groups, comprising a reaction product of (a.sub.1) active CH alkyl esters of isocyanate adducts thereof with (a.sub.2) polyamines.Mixtures of (A) and (B) with or without diluents and additives give rapid curing even at low temperatures and high atmospheric humidity and are suitable in particular for paint formulations.
    Type: Grant
    Filed: April 7, 1988
    Date of Patent: August 22, 1989
    Assignee: Hoechst AG
    Inventors: Gerhard Brindopke, Claus Godau, Walter Weber
  • Patent number: 4845257
    Abstract: A method of producing a 4-halo-2-(substituted or unsubstituted)hydroxyimino-3-oxobutyric acid ester or amide, which is a synthetic intermediate of value for the production of cephalosporins containing an aminothiazole group, characterized by reacting a 2-(substituted or unsubstituted)-hydroxyimino-3-oxobutyric acid or an ester or amide thereof with a silylating agent and reacting the resulting novel 2-(substituted)hydroxyimino-3-silyloxy-3-butenoic acid ester or amide with a halogenating agent.
    Type: Grant
    Filed: May 18, 1987
    Date of Patent: July 4, 1989
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Kenzo Naito, Yukio Ishibashi
  • Patent number: 4812478
    Abstract: L-aminoacyl derivatives of L-carnitine of general formula (I) ##STR1## wherein R is an alkyl radical selected from 1-methyl-propyl, isobutyl, isopropyl, mercaptomethyl and 3-guanidino propyl, and their pharmacologically acceptable salts, are prepared e.g. by reacting a solution in an organic solvent of L-carnitine whose carboxyl group is protected with an N-protected aminoacid in the presence of a condensing agent and then removing the aminoacid and carnitine protecting groups, thus obtaining the desired compound.
    Type: Grant
    Filed: June 29, 1987
    Date of Patent: March 14, 1989
    Assignee: Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.
    Inventors: Maria O. Tinti, Carlo A. Bagolini, Domenico Misiti, Carlo Scolastico
  • Patent number: 4789681
    Abstract: Compounds of the general formula I ##STR1## wherein R.sub.1 is hydrogen or methyl;R.sub.2 and R.sub.3, which are the same or different, represent hydrogen or methyl, or taken together, form the amidine system to which an imidazole or imidazoline ring is bound;R.sub.4 is a linear or branched C.sub.1 -C.sub.10 alkyl group; cycloalkyl, aryl, aralkyl or hetaryl group;R.sub.5 is hydrogen or methyl;A is a propylene chain optionally substituted by one or two methyl groups in one or more of the positions thereof; a chain of formula --HN--CH.sub.2 --CH.sub.2 -- or of formula --N.dbd.CH--CH.sub.2 --; a 1,4-cyclohexylene group optionally substituted by one or more methyl groups; a 1,4- phenylene group optionally substituted by one or more halogen atoms, alkyl groups or C.sub.1 -C.sub.4 alkoxy group with the proviso that, when R.sub.4 is methyl or ethyl and R.sub.1 =R.sub.2 =R.sub.3 =R.sub.
    Type: Grant
    Filed: December 22, 1986
    Date of Patent: December 6, 1988
    Assignee: Italfarmaco S.p.A.
    Inventors: Giancarlo Sportoletti, Pietro Cremonesi, Moniquet Sarret
  • Patent number: 4776875
    Abstract: Compounds of the formula ##STR1## in which R.sub.1 and R.sub.2 denote alkyl, OH, CF.sub.3 or cyanoethyl, A preferably denotes --COOH, R.sub.3 denotes inter alia alkoxycarbonylalkoxy, fairly high-molecular (>C.sub.12) alkoxy, alkylcarbonylalkoxy or nitrobenzyloxy, are valuable herbicides and growth regulators.
    Type: Grant
    Filed: March 26, 1986
    Date of Patent: October 11, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Heinz J. Loher, Klaus Bauer, Hermann Bieringer
  • Patent number: 4772695
    Abstract: A process for the preparation of vinyl carbamates of formula I ##STR1## is described which comprises heating an .alpha.-halogeno-carbamate of formula II ##STR2## in which X is a halogen atom at a temperature between 70.degree. and 250.degree. C. for a period of time between several minutes up to several hours. R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are the same or different. The process is applicable to a great variety of products in which R.sub.1, R.sub.2, R.sub.3, and R.sub.4 have different meanings. The process permits to prepare in a simple and economical fashion, vinyl carbamates, which have industrial value and novel vinyl carbamates.
    Type: Grant
    Filed: September 19, 1983
    Date of Patent: September 20, 1988
    Assignee: Societe Nationale des Poudres et Explosifs
    Inventors: Roy A. Olofson, Gary P. Wooden, Jonathan T. Martz
  • Patent number: 4772714
    Abstract: Disclosed is a process for the preparation of alpha-aryl and alpha-heteroaryl ketones useful as intermediates in the synthesis of various pharmaceutical and agricultural chemicals, which process operates according to the following reaction scheme: ##STR1##
    Type: Grant
    Filed: July 7, 1986
    Date of Patent: September 20, 1988
    Assignee: Agency of Industrial Science & Technology
    Inventors: Masato Tanaka, Toshiyasu Sakakura
  • Patent number: 4744811
    Abstract: Substituted oxime-ethers of the formulae ##STR1## where R.sup.1 and R.sup.2 independently of one another are C.sub.1 -C.sub.6 -alkyl, n is 2 or 3 and R.sup.3 is hydrogen or C.sub.1 -C.sub.6 -alkyl.
    Type: Grant
    Filed: April 8, 1987
    Date of Patent: May 17, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Guenter Schulz, Wolfgang Will, Johann Jung, Hansjoerg Fritsch
  • Patent number: 4743691
    Abstract: 2-(Fluoromethyl or chloromethyl)-2,5-diaminopentanoic acid, 2-(fluoromethyl or chloromethyl)-2,6-diaminohexanoic acid, and 2-fluoromethyl-2-amino-5-guanidinopentanoic acid, and certain derivatives thereof, are inhibitors of ornithine decarboxylase. Methods of preparing the compounds and derivatives are also described.
    Type: Grant
    Filed: June 25, 1982
    Date of Patent: May 10, 1988
    Assignee: Merrell Dow France et Cie
    Inventors: Philippe Bey, Michel Jung
  • Patent number: 4742067
    Abstract: Compounds of the formula ##STR1## are disclosed. These compounds are useful as hypotensive agents due to their angiotensin converting enzyme inhibition activity and depending upon the definition of X may also be useful as analgesics due to their enkephalinase inhibition activity.
    Type: Grant
    Filed: July 30, 1986
    Date of Patent: May 3, 1988
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Sesha I. Natarajan, Eric M. Gordon
  • Patent number: 4695588
    Abstract: Novel substituted .alpha.-fluoromethyl-.alpha.-amino alkanoic acids and esters thereof are disclosed. The novel compounds have biological activity including decarboxylase inhibition.
    Type: Grant
    Filed: March 16, 1978
    Date of Patent: September 22, 1987
    Assignee: Merck & Co., Inc.
    Inventors: Janos Kollonitsch, Arthur A. Patchett
  • Patent number: 4684722
    Abstract: Antibacterial activity is exhibited by monocyclic .beta.-lactam antibiotics having in the 1-position an --O--SO.sub.3 H activating group and in the 3-position an acylamino group of the formula ##STR1## wherein R.sub.3 and R.sub.4 are each independently hydrogen or alkyl.
    Type: Grant
    Filed: January 6, 1986
    Date of Patent: August 4, 1987
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Joseph E. Sundeen
  • Patent number: 4652671
    Abstract: It is suggested to produce 5-chloro-1H-tetrazolecarboxylic acid esters by reaction of dichloroisonitriloacetic acid esters with alkali or metal azides or ammonium azide.The dichloroisonitriloacetic acid esters required for this purpose are formed by reacting N-formylaminocarboxylic acid esters with chlorine or with compounds which split off chlorine.
    Type: Grant
    Filed: September 12, 1985
    Date of Patent: March 24, 1987
    Assignee: Dynamit Nobel Aktiengesellschaft
    Inventors: Gunter Bison, Norbert Linkat, Klaus Thewalt
  • Patent number: 4624695
    Abstract: The invention relates to novel urease inhibited fertilizer compositions containing urea and a urease inhibiting amount of one or more o-diaminophosphinyl derivatives of oximes, and methods and composition for inhibiting the activity of urease through use of such compounds.
    Type: Grant
    Filed: December 20, 1983
    Date of Patent: November 25, 1986
    Assignee: Allied Corporation
    Inventors: Michael D. Swerdloff, Milorad M. Rogic, Larry L. Hendrickson
  • Patent number: 4622413
    Abstract: Amino acid ester hydrohalide is produced by reacting amino acid, alcohol, and halocarbonyl compound represented by the formula: ##STR1## in the presence of an excess of the alcohol and under substantially anhydrous conditions, wherein X.sub.1 and X.sub.2 are each independently fluoro, chloro, bromo, trichloromethoxy or tribromomethoxy.
    Type: Grant
    Filed: August 31, 1984
    Date of Patent: November 11, 1986
    Assignee: PPG Industries, Inc.
    Inventor: James A. Krogh
  • Patent number: 4594188
    Abstract: An enkephalin-degrading aminopentidase enzyme is inhibited by compounds having the formula ##STR1## and pharmaceutically acceptable salt thereof, wherein R.sub.1 and R.sub.2 are each independently hydrogen, alkyl, carboxyalkyl, halo substituted alkyl, hydroxyalkyl, aminoalkyl, mercaptoalkyl, alkylthioalkyl, (cycloalkyl)alkyl, (heteroaryl)alkyl, arylalkyl, carbamoylalkyl, guanidinylalkyl, or heteroaryl;R.sub.3 is hydroxy, alkoxy, (substituted alkyl)oxy, arylalkoxy, (heteroaryl)alkoxy or --NY.sub.1 Y.sub.2, wherein Y.sub.1 and Y.sub.2 are each independently hydrogen, alkyl, aryl, or arylalkyl or Y.sub.1 is hydrogen and Y.sub.2 is substituted alkyl or (heteroaryl)alkyl;A.sub.1 is glycyl, alanyl, leucyl, phenylalanyl, arginyl, sarcosyl, seryl, asparagyl, lysyl, glutamyl, histidyl, tryptophyl, cysteinyl, methionyl, threonyl, tyrosyl, leucyl, valyl, aspartyl, prolyl, norleucyl, norvalyl, or ##STR2## wherein n.sub.6 is an integer of 2 to 15; A.sub.2, A.sub.3, A.sub.4 and A.sub.
    Type: Grant
    Filed: May 20, 1985
    Date of Patent: June 10, 1986
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Norma G. Delaney, Eric M. Gordon
  • Patent number: 4594446
    Abstract: The invention relates to new antimicrobially active 3-cephem compounds, processes for preparing such compounds, new intermediate compounds comprising alkoxyimino dioxy butyric acid derivatives useful in said processes, and processes for preparation of said intermediates.
    Type: Grant
    Filed: January 14, 1985
    Date of Patent: June 10, 1986
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Ikuo Ueda, Takao Takaya, Masakazu Kobayashi, Takashi Masugi, Hisashi Takasugi, Hiromu Kochi, Tadashi Kitaguchi
  • Patent number: 4593118
    Abstract: 2,3-Diaminocarboxylic acid compounds are prepared by (A) nitrosating a .beta.-keto ester to form a 3-keto-2-oximino ester, (B) converting the resultant oxime to a protected 2-amine, (C) reductively aminating the 3-position of the protected 2-amine to form a 2,3-diaminocarboxylic acid ester wherein the 2-amino group is protected, and (D) when desired, treating the 2,3-diaminocarboxylic acid ester to deprotect one or more of the amino and carboxyl groups.
    Type: Grant
    Filed: March 6, 1985
    Date of Patent: June 3, 1986
    Assignee: Ethyl Corporation
    Inventor: Beverly A. Bauer
  • Patent number: 4585887
    Abstract: Process for the production of an optically active 3-aminocarboxylic acid ester from a .beta.-keto acid ester. The .beta.-keto acid ester is converted with a chiral amine into the corresponding enamine. The enamine is converted by hydrogenation in the presence of a platinum catalyst into the corresponding N-substituted amino acid esters. Such ester mix is converted by means of HCl gas into the hydrochlorides. The latter are neutralized. Then by liberation and isolation from the neutralized products by hydrogenolysis in the presence of a palladium catalyst, the desired optically-active 3-aminocarboxylic acid ester is obtained.
    Type: Grant
    Filed: December 4, 1984
    Date of Patent: April 29, 1986
    Assignee: Lonza Ltd.
    Inventors: Synese Jolidon, Thomas Meul
  • Patent number: 4584014
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is hydrogen, alkyl, cycloalkyl, phenylalkyl, alkoxyalkyl, alkoxyaryl, aryl or an agronomically acceptable cation; R.sup.2 and R.sup.3 are each independently hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted phenylalkyl, carboxy, alkoxycarbonyl or phenyl group; X is hydrogen, fluoro, bromo, chloro or iodo atom; Y is a hydrogen, fluoro, bromo, chloro, iodo, alkyl, cycloalkyl, carboxy, alkoxycarbonyl, phenylalkyl, alkenyl and alkynyl group, wherein the alkyl, cycloalkyl, phenylalkyl and phenyl group may have up to three optional substituents; and B is hydrogen, carboxy, alkoxycarbonyl, methylene (--CH.sub.2 R.sup.4) or CZZ.sup.1 Z.sup.2 group wherein R.sup.4 is an alkyl or alkenyl group and Z, Z.sup.1 and Z.sup.2 are each independently a hydrogen, fluoro, bromo, chloro or iodo atom, provided that Z, Z.sup.1, Z.sup.2, X and Y are not all hydrogens.
    Type: Grant
    Filed: July 2, 1984
    Date of Patent: April 22, 1986
    Assignee: Rohm and Haas Company
    Inventor: Dennis R. Patterson
  • Patent number: 4560795
    Abstract: Novel halomethyl derivatives of .alpha.-amino acids of the following general structure: ##STR1## wherein Y is F.sub.2 CH--, F.sub.3 C--, Cl.sub.2 CH--; Z is .beta.-methylthioethyl, .beta.-thioethyl, .beta.-benzylthioethyl; S-(5'-desoxyadenosin-5'-yl)-S-methylthioethyl, .gamma.-guanidinopropyl, R.sub.a HN(CH.sub.2).sub.n -- wherein n is the integer 3 or 4 or ##STR2## wherein Y.sub.2 is F.sub.2 CH--, or F.sub.3 C--; each of R.sub.a and R.sub.b can be the same or different and is hydrogen, alkylcarbonyl wherein the alkyl moiety has from 1 to 4 carbon atoms and is straight or branched, alkoxycarbonyl wherein the alkoxy moiety has from 1 to 4 carbon atoms and is straight or branched, or ##STR3## wherein R.sub.2 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl; R.sub.1 is hydroxy, a straight or branched alkoxy group of from 1 to 8 carbon atoms, --NR.sub.4 R.sub.5 wherein each of R.sub.4 and R.sub.
    Type: Grant
    Filed: February 6, 1984
    Date of Patent: December 24, 1985
    Assignee: Merrell Dow France et Cie.
    Inventors: Philippe Bey, Michel Jung
  • Patent number: 4539148
    Abstract: Useful intermediates, 7.alpha.-acylamino-3-(oxo or exomethylene)-1-dethia-1-oxacepham-4.alpha.-carboxylates, are produced by the intramolecular carbenoid insertion of a 2-diazo-3-(oxo or exomethylene)-4-(3.alpha.-acylamino-2-oxoazetidin-4.beta.-yl)oxybutyrate prepared in several steps from the corresponding oxazolinoazetidinone and diketone.
    Type: Grant
    Filed: August 16, 1983
    Date of Patent: September 3, 1985
    Assignee: Shionogi & Co., Ltd.
    Inventors: Sadao Yamamoto, Hikaru Itani, Hiromi Takahashi, Teruji Tsuji, Wataru Nagata
  • Patent number: 4526987
    Abstract: Lactones of the formula ##STR1## wherein R is hydrogen or a CX.sub.3 group, and each X is a chlorine or bromine atom, are converted to the known cis-3-(2,2-dihalovinyl)-2,2-dimethylcyclopropanecarboxylic acids or lower alkyl esters, from which pyrethroid insecticides are obtained.
    Type: Grant
    Filed: January 3, 1979
    Date of Patent: July 2, 1985
    Assignee: FMC Corporation
    Inventors: Kiyoshi Kondo, Toshiyuki Takashima, Daiei Tunemoto
  • Patent number: 4487957
    Abstract: A novel alkyl 4-methyl-3-formyl-penten-1-oate of the formula ##STR1## wherein R is alkyl of 1 to 5 carbon atoms and the dotted lines represent a double bond in the 3,4 or 4,5-position and their preparation and novel intermediates therefore and a novel process for the preparation of 4-methyl-3-formyl-pent-3-en-1-oic acid which is an intermediate for the preparation of compounds of the formula ##STR2## wherein R.sub.3 is selected from the group consisting of hydrogen and the residue of an alcohol R.sub.3 OH by the process of European Patent Application Ser. No. 0023849 published Feb. 11, 1981, which are used to prepare very active insecticidal esters.
    Type: Grant
    Filed: April 21, 1983
    Date of Patent: December 11, 1984
    Assignee: Roussel Uclaf
    Inventors: Jacques Martel, Jean Tessier, Jean-Pierre Demoute
  • Patent number: 4480120
    Abstract: Alkyl-2-alkoxyimino-3-oxo-4-chlorobutyrates are prepared in good yield by treating an alkyl-2-alkoxyimino-3-oxobutyrate with sulfuryl chloride in the presence of a catalytic amount of a N,N-dialkyl-substituted carboxamide wherein the mole ratio of sulfuryl chloride to oxobutyrate compound is at least about 1:1, the reaction being conducted in the presence of a chlorinated aliphatic or aromatic hydrocarbon solvent at a temperature of about 10.degree. to 50.degree. C.
    Type: Grant
    Filed: March 24, 1983
    Date of Patent: October 30, 1984
    Assignee: Eastman Kodak Company
    Inventor: Linda M. Jewell
  • Patent number: 4438270
    Abstract: Novel halomethyl derivatives of .alpha.-amino acids of the following general structure: wherein Y is ClCH.sub.2, F.sub.2 CH--, F.sub.3 C--, ClCH.sub.2 --, Cl.sub.2 CH--; Z is .beta.-methylthioethyl, .beta.-thioethyl, .beta.-benzylthioethyl; S-(5'-desoxyadenosin-5'-yl)-S-methylthioethyl, .gamma.-guanidinopropyl, R.sub.a HN(CH.sub.2).sub.n -- wherein n is the integer 3 or 4 or ##STR1## wherein Y.sub.2 is F.sub.2 CH--, or F.sub.3 C--; each of R.sub.a and R.sub.b can be the same or different and is hydrogen, alkylcarbonyl wherein the alkyl moiety has from 1 to 4 carbon atoms and is straight or branched, alkoxycarbonyl wherein the alkoxy moiety has from 1 to 4 carbon atoms and is straight or branched, or ##STR2## wherein R.sub.2 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or .rho.-hydroxybenzyl; R.sub.1 is hydroxy, a straight or branched alkoxy group of from 1 to 8 carbon atoms, --NR.sub.4 R.sub.5 wherein each of R.sub.4 and R.sub.
    Type: Grant
    Filed: June 25, 1982
    Date of Patent: March 20, 1984
    Assignee: Merrell Toraude et Compagnie
    Inventors: Philippe Bey, Michel Jung
  • Patent number: 4425360
    Abstract: The present invention provides pyruvic acid oximes of the general formula: ##STR1## wherein R is a hydrogen atom, a C.sub.3 -C.sub.8 cycloalkyl, C.sub.1 -C.sub.6 alkoxy, cinnamyloxy, phenylamino, phenyl-N-alkylamino or phenylthio radical or an aryl or aryloxy radical, the aryl moiety of which can be substituted one or more times by C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, halogen, hydroxyl, trifluoromethyl, amino, acetylamino, nitrile, nitro or methylenedioxy, A is a straight-chained or branched, saturated or unsaturated aliphatic hydrocarbon chain containing up to 10 carbon atoms, which can be substituted one or more times by halogen or hydroxyl, and R.sub.1 is a C.sub.1 -C.sub.8 alkyl radical, which can be substituted one or more times by halogen, hydroxyl, nitrile, phenyl or carboxyl, or is a nitrile or formyl group, with the proviso that when R--A-- is a methyl or ethyl radical, R.sub.1 is not a methyl radical or a nitrile group and when R--A-- is a benzyl radical, R.sub.
    Type: Grant
    Filed: September 8, 1981
    Date of Patent: January 10, 1984
    Assignee: Boehringer Mannheim GmbH
    Inventors: Hans P. Wolff, Ruth Heerdt, Manfred Hubner, deceased, Hans Kuhnle, Felix H. Schmidt
  • Patent number: 4400529
    Abstract: Herbicide antidote compounds, compositions, and methods of use are disclosed in which compounds of the formula ##STR1## wherein R can be selected from the group consisting of alkyl groups having from about 1 to about 7 carbon atoms, aryl, and substituted aryl groups in which the substituent group can be lower alkyl having from about 1 to about 3 carbon atoms, substituted lower alkyls of from about 1 to about 3 carbon atoms in which the substituent group is halogen or nitro, lower alkoxy having from about 1 to about 3 carbon atoms; R.sub.1 can be selected from the group consisting of hydrogen or lower alkyl having from about 1 to about 6 carbon atoms; R.sub.2 can be selected from the group consisting of lower alkoxy having from about 1 to about 3 carbon atoms, and X is oxygen or sulfur; are disclosed as suitable for use as suitable for use as herbicide antidotes, when used in conjunction with thiolcarbamate herbicides.
    Type: Grant
    Filed: March 22, 1982
    Date of Patent: August 23, 1983
    Assignee: Stauffer Chemical Company
    Inventor: Hsiao-Ling M. Chin
  • Patent number: 4393215
    Abstract: Dialkoxyketoximes such as dimethoxycyclohexanone cleave with halogen and water under basic conditions to yield a series of products having an ester functionality and another functionality which is oximohalide, nitrile oxide or furoxan, depending upon the base strength and/or work-up conditions. Each of those products can be further reacted with sulfur dioxide to produce an adduct, from which an isocyanate is derived. Both the adduct and the isocyanate retain the ester functionality.
    Type: Grant
    Filed: July 6, 1981
    Date of Patent: July 12, 1983
    Assignee: Allied Corporation
    Inventors: Milorad M. Rogic, Bryce C. Oxenrider
  • Patent number: 4325961
    Abstract: Novel substituted .alpha.-fluoromethyl-.alpha.-amino alkanoic acids and esters thereof are disclosed. The novel compounds have biological activity including decarboxylase inhibition.
    Type: Grant
    Filed: June 1, 1977
    Date of Patent: April 20, 1982
    Assignee: Merck & Co., Inc.
    Inventors: Janos Kollonitsch, Arthur A. Patchett
  • Patent number: 4323704
    Abstract: Novel compounds of the formula ##STR1## wherein A is methylene, ethylene or ethylidene; R.sub.1 is --C.tbd.CH or --CH.dbd.CH.sub.2 ; R.sub.2 is hydrogen or COR wherein R is hydroxy, a straight or branched alkoxy group of from 1 to 8 carbon atoms, --NR.sub.4 R.sub.5 wherein each of R.sub.4 and R.sub.5 is hydrogen or a straight or branched lower alkyl group of from 1 to 4 carbon atoms or ##STR2## wherein R.sub.6 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl; R.sub.a is hydrogen, ##STR3## alkylcarbonyl wherein the alkyl moiety has from 1 to 4 carbon atoms and is straight or branched, alkoxycarbonyl wherein the alkoxy moiety has from 1 to 4 carbon atoms and is straight or branched or ##STR4## wherein R.sub.7 is selected from hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl and p-hydroxybenzyl; and R.sub.b has the same meaning as defined for R.sub.a except R.sub.b is not ##STR5## and R.sub.a and R.sub.
    Type: Grant
    Filed: January 16, 1981
    Date of Patent: April 6, 1982
    Assignee: Merrell Toraude et Compagnie
    Inventors: Brian W. Metcalf, Michel Jung, Charles Danzin
  • Patent number: 4322364
    Abstract: A process for the production of a modified isocyanate by reacting a composition containing carbodiimide groups and free isocyanate groups with a diester of an aliphatic dicarboxylic acid in the presence of oxalic or formic acid.The process permits the production of liquid forms of diphenylmethane diisocyanate useful in the manufacture of polyurethanes.
    Type: Grant
    Filed: January 2, 1981
    Date of Patent: March 30, 1982
    Assignee: Imperial Chemical Industries Limited
    Inventors: Jeffrey Hughes, Gerard J. Murray
  • Patent number: 4315022
    Abstract: Compounds of the formula (I): ##STR1## having pharmacological activities similar to those of natural prostaglandins wherein:n is 0 to 5;X is CO, CS or CH.sub.2 ;Y is --CH.sub.2 --CH.sub.2 --; or, when n is 1 to 5, --CH.dbd.CH-- or --C.tbd.C--;R.sub.1 is either CH.sub.2 NR.sub.5 R.sub.6, wherein R.sub.5 and R.sub.6 are separately hydrogen or C.sub.1-6 alkyl, or R.sub.5 is hydrogen and R.sub.6 is (CH.sub.2).sub.m CO.sub.2 R.sup.1.sub.9 wherein m is 0 to 4 and R.sup.1.sub.9 is optionally substituted C.sub.1-6 alkyl or benzyl, optionally substituted in the phenyl ring by chlorine or bromine atoms or by nitro or CF.sub.3 groups; or R.sub.5 and R.sub.6 are both the same (CH.sub.2).sub.m CO.sub.2 R.sup.1.sub.9 as hereinbefore defined; or C(NH.sub.2).dbd.NOH; or C(OR.sub.7).dbd.NH.sub.2.sup.+ B.sup.- wherein R.sub.7 is C.sub.1-6 alkyl and B.sup.- is a salting ion; or CH.sub.2 NHR.sub.8, wherein R.sub.8 is SO.sub.2 R.sup.1.sub.9, COR.sup.1.sub.9 or CZNHR.sub.9 and R.sup.1.sub.9 is as hereinbefore defined, R.sub.
    Type: Grant
    Filed: May 23, 1980
    Date of Patent: February 9, 1982
    Assignee: Beecham Group Limited
    Inventors: Gordon Wootton, Stephen A. Smith
  • Patent number: 4289897
    Abstract: A process is provided for production of acylhydrazones of formyl-acetic acid ester of the general formula ##STR1## wherein R.sub.1 is an alkyl group with from 1 to 6 carbon atoms and R.sub.2 is an alkoxy group or an amino group. A propiolic acid ester of the general formulaH--C.tbd.C--COOR.sub.1is contacted with hydrazine derivatives of the general formulaH.sub.2 N--NH--CO--R.sub.2in the presence of a solvent such as water or a lower alcohol. The resulting products are technically valuable starting materials for the production of biocides, for example of 1,2,3-thiadiazole derivatives.
    Type: Grant
    Filed: October 10, 1980
    Date of Patent: September 15, 1981
    Assignee: Schering Aktiengesellschaft
    Inventor: Hans-Rudolf Kruger
  • Patent number: 4282371
    Abstract: Disclosed are selected aminoester derivatives of the formula: ##STR1## wherein R is hydrogen, lower alkyl having 1 to 4 carbon atoms, phenyl, benzyl, and substituted phenyl and benzyl in which said phenyl ring substituents are selected from lower alkyl having 1 to 4 carbon atoms, lower alkoxy having 1 to 4 carbon atoms, halo, hydroxy, nitro, amino and mixtures thereof; wherein R' is lower alkyl having 1 to 4 carbon atoms; and n is 1 or 2. Examples of these compounds have shown bactericidal and herbicidal activity.
    Type: Grant
    Filed: April 28, 1980
    Date of Patent: August 4, 1981
    Assignee: Olin Corporation
    Inventor: Eugene F. Rothgery
  • Patent number: 4275217
    Abstract: A chiral .alpha.-amino acid having a hydrogen substituent in a position alpha to the carboxylic function thereof is prepared by subjecting a corresponding optical antipode with a chiral amino acid to a strong base whereby the proton in a position alpha to the carboxylic function is removed and thereafter reacting the resulting product with a chiral protonation agent.
    Type: Grant
    Filed: July 9, 1979
    Date of Patent: June 23, 1981
    Assignee: Agence Nationale de Valorisation de la Recherche (ANVAR)
    Inventors: Lucette Duhamel, Jean-Christophe Plaquevent
  • Patent number: 4275220
    Abstract: A process for preparing .alpha.-amino acids or ester thereof having an .alpha.-vinyl substituent and certain intermediates are disclosed.
    Type: Grant
    Filed: August 6, 1979
    Date of Patent: June 23, 1981
    Assignee: Merck & Co., Inc.
    Inventors: Arthur A. Patchett, William J. Greenlee
  • Patent number: 4228184
    Abstract: New carboxyalkylacylamino acids which have the general formula ##STR1## are useful as angiotensin converting enzyme inhibitors.
    Type: Grant
    Filed: May 4, 1978
    Date of Patent: October 14, 1980
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Miguel A. Ondetti, David W. Cushman
  • Patent number: 4206231
    Abstract: A 2-hydrazonopropionic acid derivative of the formula ##STR1## wherein R is an aliphatic hydrocarbon radical, andX is a valency bond or a divalent aliphatic hydrocarbon radical containing up to 4 carbon atoms, with the proviso that when X is a valency bond, R cannot be saturated cycloalkyl, ora physiologically compatible salt, lower alkyl ester or amide thereof, which exhibit hypoglycaemic activity.
    Type: Grant
    Filed: August 17, 1978
    Date of Patent: June 3, 1980
    Assignee: Boehringer Mannheim GmbH
    Inventors: Rainer Haeckel, Michael Oellerich, Ruth Heerdt, Manfred Hubner, Felix H. Schmidt
  • Patent number: 4205180
    Abstract: Novel cephem compounds of the formula; ##STR1## wherein R.sup.1 represents amino or hydroxyl group which may be protected, R.sup.2 represents amino or hydroxyl group or a group convertible into these groups, R.sup.3 represents hydrogen or methoxy group or a group convertible into methoxy group, R.sup.4 represents hydrogen or a residue of a nucleophilic compound and R.sup.8 represents hydrogen or a halogen, or a pharmaceutically acceptable salt or ester thereof, have strong antibiotic properties against a wide variety of microorganisms including gram-positive bacteria as well as gram-negative ones, especially by oral administration and can be used as therapeutic agent for various bacterial infections of animals including human beings.
    Type: Grant
    Filed: January 18, 1978
    Date of Patent: May 27, 1980
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Michihiko Ochiai, Taiiti Okada, Osami Aki, Akira Morimoto, Kenji Kawakita, Yoshihiro Matsushita
  • Patent number: 4190728
    Abstract: Lower alkyl 2-chloro-2-hydroxyiminoacetates are produced by (A) reacting chloral with a lower alkanol and a hydroxylamine salt in the presence of a Lewis acid or a metal oxide which is convertible into said Lewis acid during the course of the reaction to give a lower alkyl 2-hydroxyiminoacetate and then chlorinating the resulting product or (B) reacting chloral oxime with a lower alkanol in the presence of a base to give a lower alkyl 2-hydroxyiminoacetate and finally chlorinating the thus formed product.
    Type: Grant
    Filed: April 11, 1978
    Date of Patent: February 26, 1980
    Assignee: Shionogi & Co., Ltd.
    Inventors: Ikuo Adachi, Teruo Yamamori, Yoshiharu Hiramatsu
  • Patent number: 4182891
    Abstract: Novel acetylenic derivatives of .alpha.-amino acids of the following general structure: ##STR1## wherein Z is .beta.-methylthioethyl, .beta.-benzylthioethyl, S-(5'-desoxyadenosin-5' -yl)-S-methylthioethyl, .gamma.-guanidinopropyl, or RHN(CH.sub.2).sub.n --; n is the integer 3 or 4; each R is hydrogen, alkylcarbonyl wherein the alkyl moiety has from 1 to 4 carbon atoms and is straight or branched, alkoxycarbonyl wherein the alkoxy moiety has from 1 to 4 carbon atoms and is straight or branched, or ##STR2## wherein R.sub.2 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl; R.sub.1 is hydroxy, a straight or branched alkoxy group of from 1 to 8 carbon atoms, --NR.sub.4 R.sub.5 wherein each of R.sub.4 and R.sub.5 is hydrogen or a lower alkyl group of from 1 to 4 carbon atoms, or ##STR3## wherein R.sub.3 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl; and the lactams thereof when Z is RHN(CH.sub.
    Type: Grant
    Filed: July 1, 1977
    Date of Patent: January 8, 1980
    Assignee: Merrell Toraude et Compagnie
    Inventors: Brian W. Metcalf, Michel Jung
  • Patent number: 4152432
    Abstract: Compounds of the formula ##STR1## wherein R is selected from the group consisting of hydrogen and groups easily removable by acid hydrolysis or hydrogenolysis, R' is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms, alkenyl and alkynyl of 2 to 4 carbon atoms and groups easily removable by acid hydrolysis or hydrogenolysis, A is selected from the group consisting of hydrogen, alkali metal and equivalents of an alkaline earth metal or magnesium and an organic amine base with the proviso that when R' is a group easily removable by acid hydrolysis or hydrogenolysis, R is also and when R' is hydrogen, R also is hydrogen and the wavy line means the OR' group may be in either one of the two possible syn or anti positions having antibiotic activity and process for their preparation.
    Type: Grant
    Filed: July 19, 1977
    Date of Patent: May 1, 1979
    Assignee: Roussel Uclaf
    Inventors: Rene Heymes, Andre Lutz
  • Patent number: 4140681
    Abstract: N.sup.2 -arylsulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof have been found to be effective as pharmaceutical agents for the inhibition and suppression of thrombosis in mammals.
    Type: Grant
    Filed: June 7, 1977
    Date of Patent: February 20, 1979
    Assignee: Mitsubishi Chemical Industries, Limited
    Inventors: Shosuke Okamoto, Akiko Hijikata, Ryoji Kikumoto, Yoshikuni Tamao, Kazuo Ohkubo, Tohru Tezuka, Shinji Tonomura
  • Patent number: 4125604
    Abstract: N.sup.2 -Arylsulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof have been found to be effective as pharmaceutical agents for the inhibition and suppression of thrombosis in mammals.
    Type: Grant
    Filed: June 7, 1977
    Date of Patent: November 14, 1978
    Assignees: Mitsubishi Chemical Industries Limited, Shosuke Okamoto
    Inventors: Shosuke Okamoto, Akiko Hijikata, Ryoji Kikumoto, Yoshikuni Tamao, Kazuo Ohkubo, Tohru Tezuka, Shinji Tonomura
  • Patent number: 4117154
    Abstract: Oxime-carbamates of fluorinated ketones of the formula ##STR1## in which X represents hydrogen or fluorine,R represents alkyl, cycloalkyl, phenyl or phenylalkyl, any of which can optionally be substituted,R.sup.1 and R.sup.2, which may be identical or different, each represent hydrogen, alkyl, alkenyl, alkynyl, halogenoalkyl, halogenoalkenyl, alkoxyalkyl, alkylthioalkyl or optionally substituted phenyl, andR.sup.2 can also represent the --SR.sup.3 grouping,R.sup.3 represents alkyl, halogenoalkyl, optionally substituted phenyl or alkoxycarbonyl, or represents a radical identical to that to which the --SR.sup.3 grouping is bonded, or represents the ##STR2## grouping, WHEREINR.sup.4 represents alkyl andR.sup.5 represents alkyl, dialkylamino or optionally substituted phenyl,And acid addition salts thereof, which possess insecticidal, acaricidal, nematicidal and fungicidal properties.
    Type: Grant
    Filed: July 12, 1977
    Date of Patent: September 26, 1978
    Assignee: Bayer Aktiengesellschaft
    Inventors: Jorg Stetter, Ingeborg Hammann, Bernhard Homeyer, Wolfgang Behrenz
  • Patent number: 4105789
    Abstract: New carboxyalkylacylamino acids which have the general formula ##STR1## are useful as angiotensin converting enzyme inhibitors.
    Type: Grant
    Filed: May 10, 1976
    Date of Patent: August 8, 1978
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Miguel Angel Ondetti, David W. Cushman