Additional Nitrogen In Acid Moiety Patents (Class 560/22)
  • Patent number: 4734120
    Abstract: Dipeptides containing C-terminal phosphinothricin of the formula ##STR1## in which phosphinothricin is attached to a--preferably natural--amino acids at the amino group are effective herbicides in the pre-emergence and post-emergence techniques. The compounds are obtained, for example, by reacting phosphinothricin with the hydroxysuccinimide ester of an amino acids which is protected at the amino group in the presence of a base and subsequently splitting off the protective groups.
    Type: Grant
    Filed: December 12, 1986
    Date of Patent: March 29, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Heinz Kehne, Klaus Bauer, Hermann Bieringer
  • Patent number: 4727181
    Abstract: Prepare esters of .alpha.-halocinnamic acid and related compounds in high yield under relatively mild conditions.
    Type: Grant
    Filed: April 21, 1986
    Date of Patent: February 23, 1988
    Assignee: The Dow Chemical Company
    Inventor: William J. Kruper, Jr.
  • Patent number: 4723031
    Abstract: Process for preparing certain substituted and unsubstituted aminoacetate esters. The esters can be used as intermediates for preparing herbicidal products.
    Type: Grant
    Filed: August 27, 1984
    Date of Patent: February 2, 1988
    Assignee: Chevron Research Company
    Inventor: William C. Lo
  • Patent number: 4699992
    Abstract: Novel 3-amino-2-benzoyl-acrylic acid derivatives of the formula ##STR1## in which R.sup.1 represents the nitrile group, an ester group --COOR.sup.4 or carboxamide group ##STR2## R.sup.4 denoting C.sub.1 -C.sub.6 -alkyl, and R.sup.5 and R.sup.6 representing hydrogen or C.sub.1 -C.sub.3 -alkyl or phenyl,R.sup.2 and R.sup.3, which can be identical or different, represent a C.sub.1 -C.sub.6 -alkyl radical and, furthermore, can form, together with the nitrogen atom to which they are bonded, a 5- or 6-membered heterocyclic ring which can additionally contain as ring member the atoms or groups --O--, --S--, --SO-- or --SO.sub.2 --,X represents halogen,X.sup.1 denotes hydrogen, methyl, nitro or halogen,X.sup.2 denotes halogen or methyl, andX.sup.3 denotes hydrogen or halogen,are prepared by reacting ##STR3## The products can be converted into known antibacterials.
    Type: Grant
    Filed: September 12, 1985
    Date of Patent: October 13, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventor: Klaus Grohe
  • Patent number: 4694097
    Abstract: Carbamate esters are produced by reacting at ambient or elevated temperature an amine with carbon monoxide and an alcohol in the presence of a protonic acid, a dehydrating agent, for example a molecular sieve, and a catalyst comprising (a) at least one metal selected from the group palladium, rhodium, ruthenium, iridium and cobalt, and (b) at least one of the metals copper, molybdenum and iron, the components (a) and (b) being in the form of elemental metals or compounds thereof. The presence of the dehydrating agent reduces the formation of by-product carbon dioxide.
    Type: Grant
    Filed: April 25, 1986
    Date of Patent: September 15, 1987
    Assignee: The British Petroleum Company p.l.c.
    Inventors: Howard Alper, David J. H. Smith
  • Patent number: 4681971
    Abstract: The invention relates to pyrrolinones of formula (1) ##STR1## wherein R.sub.1 is an alkyl group containing at least 2 carbon atoms, an aralkyl group, an isocyclic or heterocyclic aromatic radical and R is an alkyl or aryl group.The invention also relates to aminodicarboxylates of formula (2) ##STR2## wherein R.sub.1 is as defined in claim 1 and R and R' are the same or different and are alkyl or aryl.The aminodicarboxylates of formula (2) are prepared by condensing a disuccinate of the formulaR'OOCCH.sub.2 CH.sub.2 COORwith a nitrile of the formula R.sub.1 CN, in the presence of a strong base and zinc chloride.The pyrrolinones of formula (1) are obtained by reacting the aminodicarboxylates of formula (2) in the presence of a strong base in an organic solvent.The compounds of formulae (1) and (2) are valuable intermediates for pigments.
    Type: Grant
    Filed: November 1, 1985
    Date of Patent: July 21, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Johannes Pfenninger, Abul Iqbal, Alain C. Rochat
  • Patent number: 4661515
    Abstract: Novel compounds possessing both angiotensin enzyme inhibitory activity and diuretic activity are disclosed. The compounds are represented by the general formula ##STR1## in which X is ##STR2## in which R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are hydrogen, alkyl, alkenyl, alkynyl, phenyl-alkyl, and cycloalkyl, and may be the same or different; n is an integer from 0 to 4 inclusive; M is alkenyl, alkynyl, cycloalkyl, cycloalkyl-alkyl, polycycloalkyl, polycycloalkyl-alkyl, aryl, aralkyl, heteroaryl, heteroaryl-alkyl, hetero-cyloalkyl, hetero-cycloalkyl-alkyl, fused aryl-cycloalkyl, fused aryl-cycloalkyl-alkyl, fused heteroaryl-cycloalkyl, fused heteroaryl-cycloalkyl-alkyl, alkoxyalkyl, alkylthioalkyl, alkylamino-alkyl, or dialkylaminoalkyl, or M and R.sub.6 taken together with the nitrogen to which M is bonded and the carbon to which R.sub.
    Type: Grant
    Filed: January 17, 1986
    Date of Patent: April 28, 1987
    Assignee: USV Pharmaceutical Corporation
    Inventors: Edward S. Neiss, John T. Suh, John J. Piwinski
  • Patent number: 4657929
    Abstract: There are provided pharmaceutical compounds useful in treating hypertension, heart diseases and renal failure. These compounds are 4-hydroxy phenethylamines wherein the 3 position on the phenyl nucleus is occupied by either an amino, amide, carbamyl, urea sulfonamide, substituted alkyl or fluorine atom, and the amine group is further linked to another phenyl radical through an alkylene radical which may contain nitrogen, oxygen, sulfur or cyclic hydrocarbon radicals as intervening groups.
    Type: Grant
    Filed: October 18, 1984
    Date of Patent: April 14, 1987
    Assignee: Fisons plc
    Inventors: Francis Ince, Alan C. Tinker
  • Patent number: 4652303
    Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein: W are selected from the group consisting of:the groups R.sup.5 --CO-- and R.sup.5 --CS-- wherein: R.sup.5 is selected from alkenyl, alkynyl, benzyl, phenyl, substituted alkyl, substituted alkenyl, substituted alkynyl, substituted benzyl, substituted phenyl and the acetal, hemiacetal, oxime, imine and Schiff base derivatives of the group R.sup.5 --CO--;the groups Y--CO-- and Y--CS-- wherein Y is selected from hydroxy, mercapto, alkylthio and the groups MO-- and MS-- wherein M is an organic or an inorganic cation;the groups R.sup.6 R.sup.7 NCO-- and R.sup.6 R.sup.7 NCS-- wherein R.sup.6 and R.sup.7 are independently selected from hydrogen, alkyl, substituted alkyl, alkanoyl, carboxy, alkoxycarbonyl, alkylsulfonyl, benzoyl, benzenesulfonyl, substituted benzoyl, substituted benzenesulfonyl, or R.sup.6 and R.sup.
    Type: Grant
    Filed: July 2, 1984
    Date of Patent: March 24, 1987
    Assignee: ICI Australia Limited
    Inventors: Keith G. Watson, Graham J. Bird, Graeme J. Farquharson
  • Patent number: 4643763
    Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein: m is an integer selected from 1 to 4;n is zero or an integer selected from 1 to 4;x are selected from halogen, nitro, cyano, alkyl, substituted alkyl, hydroxy, alkoxy, alkylthio, sulfamoyl, substituted sulfamoyl, amino, substituted amino, the group --(CH.sub.2).sub.p C(.dbd.A)Z in which p is zero or one A is oxygen or sulfur, and Z is hydrogen, hydroxy, alkoxy, alkylthio, alkyl, substituted alkyl, amino or substituted amino; the group --NHC(.dbd.B(NR.sup.7 R.sup.8 in which B is oxygen or sulfur and R.sup.7 and R.sup.8 are hydrogen or alkyl;R.sup.1 is selected from hydrogen, acyl and an inorganic or organic cation;R.sup.2 is selected from alkyl, substituted alkyl, alkenyl, haloalkenyl, alkynyl and haloalkynyl;R.sup.3 is selected from alkyl, fluoroalkyl, alkenyl, alkynyl, and phenyl; andR.sup.4 is selected from hydrogen, halogen, alkyl, cyano and alkoxycarbonyl.
    Type: Grant
    Filed: September 10, 1985
    Date of Patent: February 17, 1987
    Assignee: ICI Australia Limited
    Inventors: Graeme J. Farquharson, Keith G. Watson, Graham J. Bird
  • Patent number: 4640708
    Abstract: Compounds of the formula ##STR1## wherein: R.sup.5 is a bicyclic aryl or nitrogen-containing heteroaryl ring system such as naphthyl, quinolyl, isoquinolyl or tetrahydroisoquinolyl, optionally substituted by a wide variety of groups;R.sup.4 and R.sup.1 are preferably hydrogen but may be other groups andR.sup.2 and R.sup.3 are selected from alkyl, haloalkyl, alkenyl, haloalkenyl and alkynyl, show high general grass-killing activity with good selectivity to many broad-leaf crops and in some instances selectivity to small-grain cereals. Processes for the preparation of compounds of formula I, intermediates in the preparation of compounds I and the herbicidal properties of compounds I are described.
    Type: Grant
    Filed: March 20, 1984
    Date of Patent: February 3, 1987
    Assignee: ICI Australia Limited
    Inventors: Graham J. Bird, Graeme J. Farquharson, Keith G. Watson
  • Patent number: 4639267
    Abstract: The invention concerns novel compounds of the formula I and isomers thereof ##STR1## wherein: n is an integer selected from 2 to 4;m is zero or an integer selected from 1 to 3;X, which may be the same or different, are independently selected from halogen, alkyl, alkoxy and alkylthio;R.sup.1 is selected from hydrogen, acyl and an inorganic or organic cation;R.sup.2 is selected from alkyl, substituted alkyl, alkenyl, haloalkenyl, alkynyl and haloalkynyl;R.sup.3 is selected from alkyl, fluoroalkyl, alkenyl, alkynyl, and phenyl; andR.sup.4 is selected from hydrogen, halogen, alkyl, cyano and alkoxycarbonyl.
    Type: Grant
    Filed: September 10, 1985
    Date of Patent: January 27, 1987
    Assignee: ICI Australia Limited
    Inventors: Graeme J. Farquharson, Keith G. Watson, Graham J. Bird
  • Patent number: 4623652
    Abstract: Novel compounds of the general formula ##STR1## wherein R.sub.1 is lower alkyl, lower cycloalkyl, lower alkenyl, lower alkynyl, lower alkyl carboxymethyl, aryl carboxymethyl, aryl, or aralkyl; A is a direct bond, lower alkylene, or lower alkenylene; x is 1 or 2, provided that when x is greater than 1, different occurrences of the ##STR2## group may be the same or different; Ar is heterocyclic, unsubstituted aromatic or aromatic substituted with lower alkyl, lower alkenyl, lower alkynyl, lower alkoxy, halogen, acetamido, amino, nitro, lower alkylamino, hydroxy, lower hydroxyalkyl or cyano; W is alkylene containing from 1 to about 10 carbon atoms; and B is --NR.sub.2 COR.sub.3, --NR.sub.2 CONR.sub.3 R.sub.4, --NR.sub.2 SO.sub.2 R.sub.3, --NR.sub.2 SO.sub.2 NR.sub.3 R.sub.4, or --NR.sub.2 COOR.sub.5, wherein R.sub.2, R.sub.3, R.sub.4 and R.sub.5 may be the same or different and may be hydrogen, alkyl, alkoxyalkyl, alkoxyaryl, cycloalkyl, alkenyl, alkynyl, aryl, heteroaryl, or aralkyl, except that R.sub.3 and R.
    Type: Grant
    Filed: January 16, 1985
    Date of Patent: November 18, 1986
    Assignee: American Hospital Supply Corporation
    Inventors: Paul W. Erhardt, William L. Matier
  • Patent number: 4621149
    Abstract: A process for producing a urethane compound which comprises reacting at least one compound selected from the group consisting of a primary amine, a secondary amine and a urea compound with carbon monoxide and an organic hydroxyl compound in the presence of a catalyst system comprising:(a) at least one member selected from the group consisting of platinum group metals and compounds containing at least one platinum group element; and(b) at least one halogen-containing compound selected from the group consisting of alkali or alkaline earth metal halides, onium halides, compounds capable of forming onium halides in the reaction, oxo acids of halogen atoms and their salts, complex compounds containing halogen ions, organic halides and halogen molecules,in the presence of molecular oxygen and/or an organic nitro compound as an oxidizing agent at a temperature of from about 80.degree. C. to about 300.degree. C. under a pressure of from about 1 Kg/cm.sup.2 to about 500 Kg/cm.sup.2.
    Type: Grant
    Filed: December 10, 1984
    Date of Patent: November 4, 1986
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Shinsuke Fukuoka, Masazumi Chono
  • Patent number: 4611079
    Abstract: A method for the production of N-aryl substituted di- and polyurethanes in high yield, by the reaction of an aromatic di- or polyamine with urea and alcohol at high temperatures. The di- and polyurethanes thus produced have utility as isocyanate precursors.
    Type: Grant
    Filed: June 11, 1984
    Date of Patent: September 9, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Friedrich Towae
  • Patent number: 4610985
    Abstract: Allophanate derivatives of the formula ##STR1## in which R.sup.1 and R.sup.2 can be identical or different and represent an aliphatic, cycloaliphatic, araliphatic or aromatic radical each of which is optionally monosubstituted or polysubstituted by identical or different substituents andR.sup.3 represents the radical --XR.sup.4 or --NR.sup.5 R.sup.6,whereinR.sup.4 represents alkyl, alkoxyalkyl, or aryl which is optionally monosubstituted or polysubstituted by identical or different substituents, X represents oxygen or sulphur andR.sup.5 and R.sup.6 are identical or different and represent hydrogen, alkyl, or aryl which is optionally monosubstituted or polysubstituted by identical or different substituents, orR.sup.5 and R.sup.6, together with the nitrogen atom on which they stand, form a saturated heterocyclic radical which is optionally monosubstituted or polysubstituted by identical or different substituents and can be interrupted by further hetero-atoms,which possess fungicidal activity.
    Type: Grant
    Filed: April 10, 1985
    Date of Patent: September 9, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolfgang Fuhrer, Engelbert Kuhle, Gerd Hanssler
  • Patent number: 4608200
    Abstract: Chloramphenicol derivatives are provided for use in the preparing of antigen conjugates for the production of antibodies specifically for chloramphenicol. Specifically, the aryl amino group is derivatized to introduce a non-oxo-carbonyl group which is used for amide formation with an antigen. The conjugate is then injected into a vertebrate for production of antisera which is isolated in conventional ways and find particular use in competitive protein binding assays.
    Type: Grant
    Filed: November 30, 1984
    Date of Patent: August 26, 1986
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Pyare L. Khanna, Evan S. Snyder, Prithipal Singh
  • Patent number: 4600797
    Abstract: Process for the preparation of a nitroaminobenzene by nitrating an aminobenzene which is protected at the nitrogen wherein the nitration is carried out by the simultaneous combination of nitric acid and the aminobenzene to be nitrated, in the presence of inert solvents such as methylene chloride.
    Type: Grant
    Filed: February 18, 1983
    Date of Patent: July 15, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventor: Willi Schossler
  • Patent number: 4593119
    Abstract: A method for the treatment or prophylaxis of cardiac disorders in a mammal, comprising administering to such mammal a short-acting .beta.-blocking compound of the formula: ##STR1## wherein R may be lower alkyl, aryl, or aralkyl; n may be an integer from 0 to about 10; x may be an integer from 1 to 3; Ar may be substituted or unsubstituted aromatic; R.sub.1 may be lower alkyl, or aralkyl; and pharmaceutically accepted salts thereof. Novel compounds possessing short-acting .beta.-adrenergic blocking activity are also disclosed.
    Type: Grant
    Filed: December 16, 1982
    Date of Patent: June 3, 1986
    Assignee: American Hospital Supply Corporation
    Inventors: Paul W. Erhardt, Robert J. Borgman, John P. O'Donnell
  • Patent number: 4582923
    Abstract: Urethanes are made by reacting a primary amine with carbon monoxide and a compound containing at least one hydroxyl group in the presence of an oxidizing agent and a catalyst system. The catalyst system is made up of (i) a noble metal and/or a noble metal compound of a metal of the Eighth Secondary Group of the Periodic System of Elements and (ii) an oxidizing quinoid and/or a compound capable of being converted to an oxidizing quinoid compound under the reaction conditions. The catalyst system may optionally include (iii) metal compounds of elements of the Third to Fifth Main Groups and/or First to Eighth Secondary Groups of the Periodic System of Elements and/or (iv) a tertiary amine. This reaction is generally carried out at a temperature of from 100.degree. to 300.degree. C. and at a pressure of from 5 to 500 bars. The product urethanes are useful in the production of isocyanates and pesticides.
    Type: Grant
    Filed: May 17, 1985
    Date of Patent: April 15, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gunter Stammann, Robert Becker, Johann Grolig, Helmut Waldmann
  • Patent number: 4570002
    Abstract: The invention relates to new carbazic acid derivatives, a process for the preparation thereof and compositions--particularly feed additives and animal feeds--containing the same.The new compounds according to the invention correspond to the formula (I)R.sup.1 .dbd.N--NH--COOR.sup.3 (I)whereinR.sup.1 stands for a C.sub.7-12 cycloalkylidene group, an indanylidene group or a group of the formula (IX) ##STR1## wherein A represents a phenyl group optionally carrying one or more identical or different substituents selected from the group consisting of halo nitro, hydroxy, C.sub.1-14 alkoxy, C.sub.1-4 alkyl, amino or C.sub.1-4 alkoxycarbonylhydrazino; phenyl-(C.sub.1-4 alkyl), C.sub.1-16 alkyl, C.sub.3-7 cycloalkyl or indolyl or a C.sub.3 -C.sub.6 cycloalkyl group substituted by a C.sub.3 -C.sub.6 cycloalkyl group;R.sup.2 denotes a hydrogen atom, a C.sub.1-16 alkyl or a C.sub.3-7 cycloalkyl group; andR.sup.3 represents a C.sub.1-4 alkyl group.
    Type: Grant
    Filed: January 24, 1984
    Date of Patent: February 11, 1986
    Assignee: Egyt Gyogyszervegyeszeti Gyar
    Inventors: Zoltan Budai, Pal Benko, Ildiko Ratz nee Simonek, Eva Rakoczy nee Pinter, Karoly Magyar, Jozsef Kelemen, Attila Mandi
  • Patent number: 4564695
    Abstract: An N.sup..alpha. -protected-N.sup.G -protected-arginyl-p-nitro-anilide with high purity can be produced in high yield by reacting an N.sup..alpha. -protected-N.sup.G -protected-arginine with p-nitroaniline in pyridine in the presence of a condensing agent.
    Type: Grant
    Filed: September 13, 1984
    Date of Patent: January 14, 1986
    Assignee: Nitto Boseki Co., Ltd.
    Inventors: Katsumasa Kuroiwa, Shuichi Nakatsuyama, Takeshi Nagasawa
  • Patent number: 4559172
    Abstract: This invention relates to a novel acylation process which comprises using as the acylating agent an o-hydroxy-substituted aromatic oxime ester represented by the general formula (I) ##STR1## and mixing said acylating agent with an amine substance represented by the general formula (III) ##STR2## to form a compound represented by the general formula (IV) ##STR3##
    Type: Grant
    Filed: May 1, 1984
    Date of Patent: December 17, 1985
    Assignee: Nitto Boseki
    Inventors: Ikuo Hayashi, Keizo Ogihara, Tadao Itikawa, Kiyoshi Shimizu
  • Patent number: 4532342
    Abstract: N-substituted amino acids are described which when coupled with 1,2,3,4-tetrahydroisoquinolines result in substituted acyl derivatives of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acids as anti-hypertensive agents. The novel intermediates are in turn prepared by reacting an amino acid such as alanine with 2-bromo-4-phenyl butanoic acid or an ester thereof.
    Type: Grant
    Filed: June 8, 1982
    Date of Patent: July 30, 1985
    Assignee: Warner-Lambert Company
    Inventors: Milton L. Hoefle, Sylvestor Klutchko
  • Patent number: 4519834
    Abstract: The ethynyl-phenylureas of the formula I ##STR1## wherein X is hydrogen, halogen, lower alkyl, lower alkoxy, haloalkyl or nitro, Y is oxygen or sulfur, R.sub.1 is hydrogen, alkyl, alkoxy, alkenyl, phenyl or benzyl, R.sub.2 is hydrogen, alkyl, cycloalkyl, alkenyl, alkynyl or benzyl, R.sub.1 and R.sub.2 together with the nitrogen atom to which they are bound are also a pyrrolidine, piperidine, morpholino or piperazine ring, R.sub.3 is hydrogen or lower alkyl, and R.sub.4 is hydrogen, alkyl, phenyl, pyridyl, alkenyl, cycloalkyl or cycloalkenyl, are novel substances. They are characterized by strong herbicidal activity.
    Type: Grant
    Filed: July 11, 1983
    Date of Patent: May 28, 1985
    Assignee: Ciba-Geigy Corporation
    Inventor: Henry Szczepanski
  • Patent number: 4507318
    Abstract: The present invention concerns new derivatives of 1-aryl 2-aminomethyl cyclopropane carboxylates (Z), their preparation and their use as useful drugs for the treatment of various pains.The new derivatives of the present invention have the general formula I ##STR1## in which: R represents a hydrogen or halogen atom, a C.sub.1 to C.sub.4 lower alkyl group, a C.sub.1 to C.sub.4 lower alkoxy group, or a nitro, amino, sulfamoyl or hydroxy group;n represents the values 1, 2 or 3;(R).sub.n may together with the benzene ring also form the naphthyl group;R.sub.1 represents a linear or branched C.sub.1 to C.sub.5 alkyl or alkenyl group or an aryl or benzyl group;R.sub.2 and R.sub.3 represent a hydrogen atom, a linear or branched C.sub.1 to C.sub.5 alkyl, alkenyl, alkynyl, hydroxyalkyl, alkoxyalkyl, carboxyalkyl or dialkylaminoalkyl group or an aryl, arylalkyl or cycloalkyl group;R.sub.2 and R.sub.3 possibly also forming a heterocycle of 5 or 6 members with the adjacent nitrogen atom,provided however that when R.sub.
    Type: Grant
    Filed: June 22, 1982
    Date of Patent: March 26, 1985
    Assignee: Pierre Fabre S.A.
    Inventors: Henri Cousse, Gilbert Mouzin, Bernard Bonnaud, Marie Charveron, Francois Fauran
  • Patent number: 4504671
    Abstract: Aldoxime or ketoxime-O-alkanoic acid is prepared by transoximation of an aldehyde or ketone, the reaction being conducted in a liquid phase at a pressure below one atmosphere. Conversion of the aldoxime or ketoxime-O-alkanoic acid to the ester or salt form is also described.
    Type: Grant
    Filed: October 15, 1982
    Date of Patent: March 12, 1985
    Assignee: PPG Industries, Inc.
    Inventors: Dennis K. Krass, John C. Crano, Melvin S. Newman
  • Patent number: 4504492
    Abstract: Compounds of the general formula ##STR1## wherein Ph is a phenyl group which is optionally substituted by one or more substituents selected from halo (i.e. fluoro, chloro, bromo or iodo), C.sub.1-4 alkyl, amino, C.sub.1-4 alkylamino, di-C.sub.1-4 alkylamino, nitro, sulphonyl, aminosulphonyl, trihalomethyl, carboxy, C.sub.1-4 alkoxycarbonyl, amido, C.sub.1-4 alkylamido, C.sub.1-4 alkoxy, C.sub.2-4 alkenyl, cyano, aminomethyl, or methylsulphonyl; Y is a group of formula ##STR2## where R.sup.1 is hydrogen or methyl; R.sup.2 is alkyl of 1 to 3 carbon atoms or is methylthiomethyl; and Z is --OR.sup.3 or --NR.sup.4 R.sup.5 where R.sup.3, R.sup.4 and R.sup.5 are each hydrogen or alkyl of 1 to 4 carbon atoms and R.sup.3 can further be phenylalkyl having 1 to 3 carbon atoms in the alkylene moiety thereof, or phenyl; and basic salts thereof. These compounds have an advantageous enkephalinase inhibitory activity which renders the compounds useful in medical therapy, e.g.
    Type: Grant
    Filed: September 24, 1982
    Date of Patent: March 12, 1985
    Assignee: Burroughs Wellcome Co.
    Inventors: Samuel Wilkinson, George W. Hardy
  • Patent number: 4495362
    Abstract: A process for preparing alkyl nitroacetates by reacting an alkyl phenyl carbonate with a nitroparaffin in a polar aprotic solvent in the presence of a cyanide ion. The process permits a higher reaction rate, and thus the reaction can be completed even at room temperature.
    Type: Grant
    Filed: November 4, 1982
    Date of Patent: January 22, 1985
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Tadatoshi Honda, Yoichi Hosono
  • Patent number: 4492683
    Abstract: New compounds and a method for inhibiting the growth of fungus is disclosed which comprises contacting said fungus with a fungicidal amount of a phenyl glycine compound of the formula: ##STR1## wherein R.sub.1 and R.sub.2 are independently hydrogen, lower alkyl, substituted lower alkyl, cycloalkyl, substituted cycloalkyl, alkenyl, phenyl, substituted phenyl, halogen, amino or hydroxy groups; R.sub.3 is a hydrogen, lower alkyl, substituted lower alkyl, cycloalkyl, benzoyl, halo or nitro substituted benzoyl, substituted cycloalkyl, methylcarbamoyl, cyclohexylcarbamoyl, phenylcarbamoyl, halophenylcarbamoyl, methylphenylcarbamoyl, methylthiocarbamoyl, phenyl, substituted phenyl, napthyl group or --SO.sub.2 R.sub.7 where R.sub.7 is a hydrogen, alkyl, substituted alkyl, phenyl, substituted phenyl or amino group; R.sub.4 and R.sub.5 are independently hydrogen, lower alkyl or substituted lower alkyl groups and R.sub.6 is a hydrogen, lower alkyl or substituted lower alkyl, alkenyl or substituted alkenyl group.
    Type: Grant
    Filed: August 6, 1982
    Date of Patent: January 8, 1985
    Assignee: Buffalo Color Corporation
    Inventor: Krishen L. Nagpal
  • Patent number: 4491671
    Abstract: The present invention relates to a process for the preparation of N-substituted imido-dicarboxylic acid diaryl ester compound of the formulaR.sup.1 --N(CO--OR.sup.2).sub.2 (I)whereinR.sup.1 is an optionally substituted aliphatic, cycloaliphatic, araliphatic, aromatic or heterocyclic radical; andR.sup.2 is an optionally substituted aryl radical, which are useful as intermediates for the production of known herbicides, which process comprises reacting a primary amine of the formulaR.sup.1 --NH.sub.2 (II)with a carbonic acid aryl ester halide of the formulaX--CO--OR.sup.2 (III)wherein X is a halogen atom, at a temperature between 100.degree. and 300.degree. C.
    Type: Grant
    Filed: June 10, 1982
    Date of Patent: January 1, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karlfried Dickore, Engelbert Kuhle
  • Patent number: 4490552
    Abstract: A novel process for the preparation of aryl esters of organic carboxylic acids in high isomer purity by decomposing a compound of the formula ##STR1## wherein Ar is an aryl radical, X is an acyloxy of an organic carboxylic acid and Y is selected from the group consisting of an acyloxy of an organic carboxylic acid and an anion of a strong organic and mineral acid in an aqueous media in the presence of a palladium salt or in the form of a two-phase reaction, wherein the aryl thallium salt is dissolved in water and the catalytic palladium salt is dissolved in a water-immiscible organic solvent and the reaction takes place with mixing.
    Type: Grant
    Filed: December 20, 1982
    Date of Patent: December 25, 1984
    Assignee: Rutgerswerke AG
    Inventor: Ulrich Knips
  • Patent number: 4482737
    Abstract: N-substituted N-isocyanatocarbonyl-carbamates, some of which are new, of the general formula ##STR1## are prepared by reacting an N-substituted carbamic acid ester of the general formulaR--NH--COOR.sup.1 (II)with chlorocarbonyl isocyanate of the formulaCl--CO--NCO (III)in a diluent, at a temperature between 50.degree. and 200.degree. C. The compounds (I) can be used as intermediate products for the preparation of new pest-combating agents.
    Type: Grant
    Filed: November 3, 1982
    Date of Patent: November 13, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Engelbert Kuhle, Hermann Hagemann
  • Patent number: 4474806
    Abstract: Sulfonyl or carbonyl derivatives of inositols are found to be effective phospholipase C inhibitors and thereby potent anti-inflammatory and analgesic agents. These inositol derivatives are prepared by condensation of a protected inositol with a substituted sulfonic or carboxylic acid derivative followed by removal of protecting groups.
    Type: Grant
    Filed: May 10, 1982
    Date of Patent: October 2, 1984
    Assignee: Merck & Co., Inc.
    Inventors: Thomas R. Beattie, Shu S. Yang
  • Patent number: 4457872
    Abstract: A novel 2-hydroxyoxanilic acid derivative shown by the following formula ##STR1## or a salt thereof. This compound possesses an immunoregulatory action and is useful as an antiallergic agent, an antiasthmatic, an antirheumatic, a carcinostatic agent, a therapeutic agent for autoimmune disease, and a suppressant of rejection at the tissue transplantation and skin graft.
    Type: Grant
    Filed: September 9, 1982
    Date of Patent: July 3, 1984
    Assignee: Yamanouchi Pharmaceutical Co.
    Inventors: Kiyoshi Murase, Toshiyasu Mase, Hideki Arima, Kenichi Tomioka, Yoso Numasaki
  • Patent number: 4454337
    Abstract: A new chemical sequence for preparing certain indoles is disclosed which employes certain 2-substituted-6-nitrophenylacetaldehyde semicarbazones claimed here. Said semicarbazones are cyclized to the indoles by low pressure hydrogenation.
    Type: Grant
    Filed: March 2, 1983
    Date of Patent: June 12, 1984
    Assignee: SmithKline Beckman Corporation
    Inventor: Lawrence I. Kruse
  • Patent number: 4451406
    Abstract: Novel N-substituted imido-dicarboxylic acid diaryl ester compounds of the general formula ##STR1## in which R.sup.1 represents an optionally substituted aliphatic, cycloaliphatic, araliphatic, aromatic, heterocyclic radical andR.sup.2 and R.sup.3 can be identical or different and represent an optionally substituted aryl radical,and a process for their preparation characterized in that a carbamic acid aryl ester of the general formula:R.sup.1 --NH--CO--OR.sup.2 (II)in which R.sup.1 and R.sup.2 have the abovementioned meanings, is reacted with a carbonic acid aryl ester halide of the general formulaX--CO--OR.sup.3 (III)in whichR.sup.3 has the abovementioned meaning andX represents a halogen atom, optionally in the presence of a diluent, optionally at a temperature between 100.degree. and 300.degree. C.The new compounds (I) can be used as intermediate products for the preparation of known herbicidal active compounds from the 1,3,5-triazine,2,4-(1H,3H)-dione series.
    Type: Grant
    Filed: August 5, 1983
    Date of Patent: May 29, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karlfried Dickore, Engelbert Kuhle
  • Patent number: 4450173
    Abstract: A short-acting .beta.-blocking compound of the formula ##STR1## wherein Ar may be substituted or unsubstituted aromatic, Y may be a straight or branched carbon chain or aralkyl, R may be lower alkyl, lower alkenyl, lower alkynyl, aryl or aralkyl, and x is an integer from 1 to about 3; or a pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: June 21, 1982
    Date of Patent: May 22, 1984
    Assignee: American Hospital Supply Corporation
    Inventors: Paul W. Erhardt, Robert J. Borgman
  • Patent number: 4448773
    Abstract: Compounds of the formula ##STR1## in which Ar is 2-alkyl-, -alkoxy- or -halo-methyl-phenyl or .alpha.-naphthyl, each of which is further substituted,R.sub.1 is 2-furyl, 2-tetrahydrofuryl, alkenyl, cyclopropyl, .beta.-alkoxyethyl, hydroxymethyl, triazolylmethyl, imidazolylmethyl, pyrazolylmethyl, alkylsulfinyl, alkylsulfonyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynylthio, alkylsulfinyloxy, dialkylaminosulfinyloxy, phosphoric or thiophosphoric esters or amides, or alkylcarbonyloxy,R.sub.7 is hydrogen or optionally-substituted methyl or ethyl, andR.sub.8 is alkyl optionally substituted by alkoxy,are microbicidally, in particular fungicidally, active. Preferred compounds are those in which Ar is 2-methylphenyl, 2-methoxyphenyl, 2-chlorophenyl or .alpha.-naphthyl, each of which is further substituted by azido, and each of R.sub.7 and R.sub.8 is methyl.
    Type: Grant
    Filed: April 22, 1982
    Date of Patent: May 15, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Riebli, Hanspeter Fischer, Rudolph C. Thummel, Adolf Hubele
  • Patent number: 4447635
    Abstract: Novel N-substituted imido-dicarboxylic acid diaryl ester compounds of the general formula ##STR1## in which R.sup.1 represents an optionally substituted aliphatic, cycloaliphatic, araliphatic, aromatic, heterocyclic radical andR.sup.2 and R.sup.3 can be identical or different and represent an optionally substituted aryl radical, and a process for their preparation characterized in that a carbamic acid aryl ester of the general formulaR.sup.1 --NH--CO--OR.sup.2 (II)in which R.sup.1 and R.sup.2 have the abovementioned meanings, is reacted with a carbonic acid aryl ester halide of the general formulaX--CO--OR.sup.3 (III)in whichR.sup.3 has the abovementioned meaning andX represents a halogen atom, optionally in the presence of a diluent, optionally at a temperature between 100.degree. and 300.degree. C.The new compounds (I) can be used as intermediate products for the preparation of known herbicidal active compounds from the 1,3,5-triazine,2,4-(1H,3H)-dione series.
    Type: Grant
    Filed: June 30, 1982
    Date of Patent: May 8, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karlfried Dickore, Engelbert Kuhle
  • Patent number: 4441913
    Abstract: Novel substituted phenoxypropionates of the formula ##STR1## in which R.sup.1 and R.sup.2 each independently are a hydrogen atom or a C.sub.1 to C.sub.6 alkyl group,X is a hydrogen or halogen atom, nitro, C.sub.1 to C.sub.6 alkyl or C.sub.1 to C.sub.6 alkoxy,a and n each independently are 1 or 2, andAr is a group of the formula ##STR2## wherein Y is a trifluoromethyl group, a halogen atom ora nitro, cyano or C.sub.1 to C.sub.6 alkyl group, andb is 1, 2 or 3,and their use as herbicides.Novel intermediates of the formulae ##STR3## in which formulae R.sup.1, R.sup.2, X, a and n have the meanings given above andZ.sup.1 represents halogen.
    Type: Grant
    Filed: June 17, 1982
    Date of Patent: April 10, 1984
    Assignee: Nihon Tokushu Noyaku Seizo K.K.
    Inventors: Masahiro Aya, Junichi Saito, Kazuomi Yasui, Kozo Shiokawa, Koichi Moriya
  • Patent number: 4442117
    Abstract: There are described novel homoserine derivatives of the formula (I) ##STR1## which possess valuable microbicidal properties. In the formula: Ar is substituted phenyl or naphthyl; R.sub.1 is C.sub.2 -C.sub.6 alkyl optionally interrupted by oxygen or sulfur, 2-furyl, 2-tetrahydrofuryl, 1H-1,2,4-triazolylmethyl, 1-imidazolylmethyl, 1-pyrazolylmethyl, C.sub.2 -C.sub.4 alkenyl or cyclopropyl, each of which is optionally substituted by halogen; R.sub.2 is hydrogen or methyl; R.sub.3 is hydrogen or C.sub.1 -C.sub.4 alkyl; and B is halogen or an ester, thioester, sulfonic acid ester or sulfonic acid amide group. Additionally, where B is halogen, R.sub.1 may be halomethyl. The novel derivatives can be used for combating microorganisms harmful to plants, particularly for combating phytopathogenic fungi, and they have for practical requirements a very favorable curative and protective action for protecting cultivating plants, without the plants being impaired as a result of undesirable secondary effects.
    Type: Grant
    Filed: October 23, 1980
    Date of Patent: April 10, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: Walter Kunz, Wolfgang Eckhardt, Adolf Hubele, Peter Riebli
  • Patent number: 4440941
    Abstract: Compounds of the structure ##STR1## wherein: Q is oxygen, sulfur or imino.X and Y are hydrogen, halogen, hydroxy, alkoxy, trifluoromethyl, nitro, carboxy, cyano, sulfonamido, sulfhydryl, alkyl, alkenyl, alkynyl, alkanoyl, alkylmercapto, amino, alkylamino, dialkylamino, alkysulfinyl, and alkylsulfonyl and may be the same or different;R.sub.1 is hydrogen, alkanoyl, substituted alkanoyl wherein the substituent is hydroxy, amino or cycloalkyl, aroyl, arylalkanoyl, or cycloalkylcarbonyl,n is an integer from 1 to 4 inclusive,R.sub.2 and R.sub.
    Type: Grant
    Filed: December 22, 1980
    Date of Patent: April 3, 1984
    Assignee: USV Pharmaceutical Corporation
    Inventors: John T. Suh, Paul R. Menard, Howard Jones
  • Patent number: 4438136
    Abstract: Novel bicyclo [2,2,1] heptanes and hept-2-enes are substituted at the 5-position by a 6-carboxyhex-2-enyl group or a modification thereof, and at the 6-position by a grouping --C(R).dbd.N--NHCO--(NH).sub.a --R' in which R is hydrogen, an aliphatic hydrocarbon residue, an aromatic residue or an aliphatic hydrocarbon residue substituted by an aromatic residue, a is 0 or 1 and R' is an aliphatic hydrocarbon residue, an aromatic residue, or an aliphatic hydrocarbon residue substituted directly or through an oxygen or sulphur atom by an aromatic residue. The compounds are of value for use in pharmaceutical compositions particularly in the context of the inhibition of thromboxane activity.
    Type: Grant
    Filed: September 17, 1982
    Date of Patent: March 20, 1984
    Assignee: National Research Development Corporation
    Inventors: Robert L. Jones, Norman H. Wilson
  • Patent number: 4430505
    Abstract: A process for the preparation of N,O-disubstituted urethanes. Urea or polyurets, primary amines and alcohols are reacted at 120.degree.-350.degree. C. in the presence of N-substituted urethanes and/or N-mono- or N,N'-disubstituted ureas or polyureas. In a preferred embodiment, the reactants further include catalysts known to be useful in esterification of carboxylic acids. The urethanes produced in accordance with this process are particularly useful as starting materials for preparation of isocyanates.
    Type: Grant
    Filed: October 15, 1980
    Date of Patent: February 7, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Peter Heitkamper, Klaus Konig, Kurt Findeisen, Rudolf Fauss, Rudolf Sundermann
  • Patent number: 4424394
    Abstract: Arylacetic acids and their esters, of the formula Ar(CH.sub.2 -COOR).sub.n (where Ar=aryl, R is H or a hydrocarbon radical, and n is 1 or 2) are manufactured by carbonylation of halomethylaryl compounds Ar(CH.sub.2 C).sub.n (where X is Cl, Br or I) with carbon monoxide and a catalyst m.sup.+ ?Fe(O).sub.3 NO!.sup.- (where M is an alkali metal, ammonium or one equivalent of an alkaline earth metal) in the presence of stoichiometric amounts of an inorganic base or of an alcoholate of an alcohol ROH.
    Type: Grant
    Filed: November 8, 1979
    Date of Patent: January 3, 1984
    Assignee: BASF Aktiengesellschaft
    Inventors: Kurt Schneider, Rudolf Kummer, Kurt Schwirten, Hans-Dieter Schindler, deceased, Maria E. Schindler, heir-at-law, Ute Lang, heir-at-law, Rainer Schindler, heir-at-law
  • Patent number: 4423242
    Abstract: Compounds of the general formula ##STR1## wherein Ph is a phenyl group which is optionally substituted by one or more substituents selected from halo (i.e. fluoro, chloro, bromo or iodo), C.sub.1-4 alkyl, amino, C.sub.1-4 alkylamino, di-C.sub.1-4 alkylamino, nitro, sulphonyl, aminosulphonyl, trihalomethyl, carboxy, C.sub.1-4 alkoxycarbonyl, amido, C.sub.1-4 alkylamido C.sub.1-4 alkoxy, C.sub.2-4 alkenyl, cyano, aminomethyl or methylsulphonyl; R.sup.a and R.sup.b, which may be the same or different, each represents a hydrogen or alkali metal (e.g. sodium or lithium) atom or a C.sub.1-4 (e.g. ethyl) group; m is 0 or 1; Y is a group of formula:--NH--CH.sub.2 --CO--or a group of formula: ##STR2## where R.sup.1 is hydrogen or methyl;R.sup.2 is alkyl of 1 to 3 carbon atoms or is methylthiomethyl; andZ is --OR.sup.3 or --NR.sup.4 R.sup.5 where R.sup.3, R.sup.4 and R.sup.5 are each hydrogen or alkyl of 1 to 4 carbon atoms (i.e. methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, or t-butyl) and R.sup.
    Type: Grant
    Filed: September 24, 1982
    Date of Patent: December 27, 1983
    Assignee: The Wellcome Foundation Ltd.
    Inventors: Samuel Wilkinson, George W. Hardy, Roger Wrigglesworth
  • Patent number: 4417896
    Abstract: Novel compounds of the general formula ##STR1## wherein Z represents a substituted lower alkyl radical; each of R.sub.1 and R.sub.2 is hydrogen atom, a lower alkyl or a substituted lower alkyl identical with or different from Z and the functional groups NO.sub.2 and NR.sub.1 R.sub.2 can occupy all ring positions in relation to OZ, with the exception that if Z is .beta.-hydroxyethyl, --NO.sub.2 is in the 4 position and --N(R.sub.1)(R.sub.2) is in the 2 position then either R.sub.1 or R.sub.2 is other than hydrogen.The novel compounds are for dyeing human hair in a variety of yellow shades. The compounds of formula (I) may be used as aqueous or water-alcohol solutions to form dye compositions for dyeing human hair.
    Type: Grant
    Filed: April 6, 1982
    Date of Patent: November 29, 1983
    Assignee: Societe Anonyme dite: L'Oreal
    Inventors: Andree Bugaut, Patrick Andrillon
  • Patent number: 4415743
    Abstract: Novel oxime ethers and oxime esters of the formula I given herein have various advantageous effects with regard to stimulation of plant growth, particularly in the early stage of development of the plant. Furthermore, such compounds have the property of rendering, in the sense of an antidote action, agricultural chemicals which would otherwise damage the plants (phytotoxic chemicals) more compatible with the cultivated plants. Herbicides that are insufficiently selective can be used for example in the presence of such oxime derivatives in specific cultivated crops for combating weeds, without disadvantageous consequences for the cultivated plants.
    Type: Grant
    Filed: September 30, 1982
    Date of Patent: November 15, 1983
    Assignee: Ciba-Geigy Corporation
    Inventor: Henry Martin
  • Patent number: 4411912
    Abstract: Esters and thiolesters of amino acids, intermediates therefor, synthesis thereof, and the use of said esters and thiolesters and compositions for the control of pests.
    Type: Grant
    Filed: November 13, 1979
    Date of Patent: October 25, 1983
    Assignee: Zoecon Corporation
    Inventors: Clive A. Henrick, Barbara A. Garcia