Nitrogen In Acid Moiety Patents (Class 560/16)
  • 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: 4387104
    Abstract: A pyruvic acid hydrazone derivative of the formula: ##STR1## wherein R is an aryl radical optionally substituted by lower alkyl or is an aliphatic hydrocarbon radical which can be substituted by a lower alkoxy, a cycloalkyl or an optionally substituted aryl radical,A is an alkylene radical containing 2 to 8 carbon atoms, with at least 2 carbon atoms between B and the nitrogen atom, andB is an oxygen or sulphur atom;or a physiologically acceptable salt, ester or amide thereof which possesses hypoglycaemic activity.
    Type: Grant
    Filed: August 14, 1981
    Date of Patent: June 7, 1983
    Assignee: Boehringer Mannheim GmbH
    Inventors: Ruth Heerdt, Hans P. Wolff, Fritz Kaiser, Wolfgang Schaumann, Hans Kuhnle
  • Patent number: 4372972
    Abstract: This invention relates to N-substituted alkynyl anilines, methods for their preparation and their use as systemic eradicant phytopathogenic fungicides which are useful in controlling Oomycetes.
    Type: Grant
    Filed: September 14, 1979
    Date of Patent: February 8, 1983
    Assignee: Rohm and Haas Company
    Inventor: Hak-Foon Chan
  • Patent number: 4369189
    Abstract: Novel unsymmetrical formamidine-sulfenylated carbamate compounds exhibit broad-spectrum insecticidal, miticidal and nematocidal activity.
    Type: Grant
    Filed: December 10, 1980
    Date of Patent: January 18, 1983
    Assignee: Union Carbide Corporation
    Inventor: Themistocles D. J. D'Silva
  • Patent number: 4363766
    Abstract: A process for the preparation of sulfur-containing N-benzyl-amino acids of the formula ##STR1## wherein X and Y, which may be identical to or different from each other, are each hydrogen or halogen;R.sub.1 is hydrogen or alkyl of 1 to 4 carbon atoms;R.sub.2 is hydrogen, alkyl of 1 to 3 carbon atoms, carboxy-lower alkyl or acyl;R.sub.3 is hydrogen or acyl; andn is 1 or 2;which comprises the steps of converting anthranilic acid or a halogenated anthranilic acid into the corresponding aldehyde, reacting the aldehyde with a compound of the formula ##STR2## wherein R.sub.1, R.sub.2 and n have the meanings previously defined, to form the corresponding Schiff's base, reducing the said Schiff's base, and recovering the reaction product.
    Type: Grant
    Filed: April 17, 1979
    Date of Patent: December 14, 1982
    Assignee: Boehringer Ingelheim GmbH
    Inventor: Bernard Bellegarde
  • Patent number: 4360531
    Abstract: [2-Amino(substituted cycloaliphatic)]benzeneacetamide and benzamide compounds, e.g., trans-3,4-dichloro-N-methyl-N-[7-(1-pyrrolidinyl)-1,4-dioxaspiro[4.5]dec-8 -yl]benzeneacetamide, have useful analgesic activity and low abuse or physical dependence liability, or are useful as chemical intermediates for producing such analgesic compounds. Processes for their preparation are disclosed. Pharmaceutical compositions and methods of use are also disclosed.
    Type: Grant
    Filed: April 9, 1981
    Date of Patent: November 23, 1982
    Assignee: The Upjohn Company
    Inventors: Moses W. McMillan, Jacob Szmuszkovicz
  • Patent number: 4359476
    Abstract: N-[2-Amino(oxy or thio group) substituted-cycloaliphatic]phenylacetamide and -benzamide compounds, having the oxy- or thio group substituents on a cycloaliphatic ring carbon adjacent to either of the nitrogen bearing carbons of the cycloaliphatic ring, e.g., cis- and trans-4-bromo-N-[3-methoxy-2-(1-pyrrolidinyl)cyclohexyl]-N-methylbenzamide , and trans-3,4-dichloro-N-methyl-N-[7-(1-pyrridolinyl)-1,4-dioxaspiro[4.5]dec-6 -yl]benzeneacetamide, and salts thereof, have useful analgesic activity and low abuse liability in humans and valuable warm blooded animals. Processes for their production and pharmaceutical compositions and method of use are also disclosed.
    Type: Grant
    Filed: April 9, 1981
    Date of Patent: November 16, 1982
    Assignee: The Upjohn Company
    Inventors: Lester J. Kaplan, Moses W. McMillan, Jacob Szmuszkovicz
  • Patent number: 4354975
    Abstract: This invention pertains to novel processes for preparing phosphorus derivatives of aminothiomethylcarbamates using as intermediates corresponding phosphorus derivatives of aminothiocarbamic halides. The carbamates are useful as pesticides against insects, mites, and nematodes. Two processes for preparing the corresponding intermediates are described. One preparation generally reacts an appropriate N-chlorothiophosphoramide with N-methylcarbamoyl halide. The other preparation generally reacts an N-chlorothiomethylcarbamoyl halide with an appropriate phosphoramide. The intermediate will react with various alcohols to produce the desired carbamates in the process of the invention.
    Type: Grant
    Filed: July 21, 1980
    Date of Patent: October 19, 1982
    Assignee: The Upjohn Company
    Inventor: Stephen J. Nelson
  • Patent number: 4348406
    Abstract: Compounds of the formula: ##STR1## and their pharmaceutically acceptable acid addition salts, useful as anthelmintics are disclosed.
    Type: Grant
    Filed: October 20, 1980
    Date of Patent: September 7, 1982
    Assignee: Schering Corporation
    Inventor: M. Mehdi Nafissi-Varchei
  • Patent number: 4346104
    Abstract: Phenylacetic acid amide compounds of the formula ##STR1## in which R.sub.1 is hydrogen, lower alkyl, lower alkoxy, halogen having an atomic number of not more than 35 or trifluoromethyl, R.sub.2 is hydrogen, lower alkyl, lower alkoxy, halogen having an atomic number of not more than 35 or trifluoromethyl, R.sub.3 is hydrogen, lower alkyl, lower alkoxy or halogen having an atomic number of not more than 35 and R.sub.4 is hydrogen, lower alkyl, lower alkoxy or halogen having an atomic number of not more than 35, and in which R.sub.5 is a radical of aliphatic character containing the group R.sub.6, R.sub.6 and R.sub.7 are each hydrogen or together are a divalent aliphatic radical and the group of the formula --C(.dbd.O)--R.sub.8 (Ia) is a carboxyl group, which can be functionally modified, and their salts are useful as anti-inflammatory agents.
    Type: Grant
    Filed: December 17, 1980
    Date of Patent: August 24, 1982
    Assignee: Ciba-Geigy Corporation
    Inventors: Alfred Sallmann, Gerhard Baschang
  • Patent number: 4330674
    Abstract: Carbamoyl sulfides such as dimethyl N,N'-[2,3-butanediylidenebis[nitrilooxycarbonyl(N-methylimino)thio(N-methy limino)carbonyloxy]]bis[ethanimidothioate] useful for control of insects and nematodes.This application is a divisional of application Ser. No. 139,836, filed Apr. 24, 1980, now U.S Pat. No. 4,254,141, which is a continuation-in-part of application Ser. No. 18,293, filed Mar. 6, 1979, and now abandoned.
    Type: Grant
    Filed: October 8, 1980
    Date of Patent: May 18, 1982
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Jiin-Duey Cheng
  • Patent number: 4329293
    Abstract: An improved process is disclosed for sulfenylating carbamates in the presence of a solvent and acid acceptor, in which the reaction between a carbamate and a sulfenyl halide is conducted in the presence of a catalytic amount of a complex of a lower alkylamine and sulfur dioxide. Several methods for preparing and utilizing the complex in the reaction are disclosed and exemplified.
    Type: Grant
    Filed: October 31, 1980
    Date of Patent: May 11, 1982
    Assignee: FMC Corporation
    Inventors: John W. Ager, Maurice J. C. Harding, Charles E. Hatch, III
  • Patent number: 4320142
    Abstract: Compounds of formula (I) are pesticides active against arthropods. ##STR1## wherein R.sup.1, R.sup.2, and R.sup.3 are H, alkyl, alkoxy, halo, CN or CF.sub.3 or two are linked to form a 3 or 4 carbon atom group;X is O or NA where A is H or alkyl;R is H or alkyl;R.sup.4 is H or optionally substituted alkyl, aryl, aralkyl, alkenyl or alkynyl; andR.sup.5 is --CB. R.sup.6 where B is O, S or NR.sup.7 where R.sup.7 is H, alkyl, alkoxy, or optionally substituted aryl or aralkyl;R.sup.6 is H, R.sup.8, OR.sup.8, SR.sup.8 or NR.sup.9 R.sup.10 where R.sup.8 is alkyl, alkenyl or optionally substituted aryl, aralkyl or aryloxyalkyl; and R.sup.9 and R.sup.10 are H, alkyl or optionally substituted aryl or aralkyl;The invention also comprises processes for the preparation of compounds (I), formulations containing them, and their use as pesticides.
    Type: Grant
    Filed: May 15, 1980
    Date of Patent: March 16, 1982
    Inventors: Malcolm H. Black, Alexander D. Frenkel, Peter T. Roberts
  • Patent number: 4315026
    Abstract: A novel class of chemical compounds useful as pesticides consists of alkylpolyoxysulfinyl and alkylpolythiosulfinyl derivatives of carbamate esters. The preparation of these compounds and their formulation to control insects are exemplified.
    Type: Grant
    Filed: April 11, 1980
    Date of Patent: February 9, 1982
    Assignee: The Regents of the University of California
    Inventors: Mohamed A. H. Fahmy, Tetsuo R. Fukuto, Teruomi Jojima
  • Patent number: 4309425
    Abstract: Sulfonamides, such as N-[N-(2-chloro-5-(trifluoromethyl)phenyl]-N-[2,4-dinitro-6-(trifluoromethy l)phenyl]aminothio]-N,4-dimethylbenzenesulfonamide, are useful for control of arthropod pests of plants and animals and fungus disease of plants.
    Type: Grant
    Filed: April 11, 1980
    Date of Patent: January 5, 1982
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Jiin-Duey Cheng
  • Patent number: 4303673
    Abstract: The invention provides N-propionylsarcosineanilides of the formula: ##STR1## wherein n is an integer of 1 to about 3 and the substituent A which can be the same or different when n is greater than 1 is selected from the group consisting of trifluoromethyl; halogen; nitro; acetyl; a straight-chain or branched alkyl group having 1 to 4 carbon atoms; a straight-chain or branched alkoxy group having 1 to 4 carbon atoms; a straight-chain or branched alkylmercapto group having 1 to 7 carbon atoms; a substituted alkylmercapto group of the formula: ##STR2## wherein n is an integer of 1 or 2, R.sub.1 can represent hydrogen and methyl, and R.sub.2 can represent hydroxyl, and an amino group of the formula:--NR.sub.6 R.sub.7 Vwherein R.sub.6 can represent hydrogen, and methyl, and R.sub.7 can represent methyl, substituted benzyl, and R.sub.6 and R.sub.7, together with the nitrogen, can constitute a substituted pyrrolidine ring; a sulphonyl group of the formula:--SO.sub.2 R.sub.3 IIIwherein R.sub.
    Type: Grant
    Filed: September 5, 1980
    Date of Patent: December 1, 1981
    Assignee: A. Nattermann & Cie. GmbH
    Inventors: Jurgen Biedermann, Armin Wendel, Hans Betzing, Volker Neuser
  • Patent number: 4302460
    Abstract: Compositions which contain a quinolone compound of the general formula ##STR1## wherein n is 0, 1 or 2; R.sub.1 is lower alkyl optionally substituted by hydroxy or C.sub.1-4 alkoxycarbonyl; allyl; propynyl or phenyl- lower alkyl in which the phenyl ring is optionally substituted by 1 or 2 C.sub.1-4 alkoxy groups; R.sub.2 is C.sub.1-4 alkyl with the proviso that when n is 0, R.sub.2 is methyl; and R.sub.3, R.sub.4 and R.sub.5, which may be the same or different, are hydrogen, lower alkyl, lower alkoxy, lower alkanoyl, halo, trifluoromethyl or lower alkylthio show antihypertensive activity.Compounds of general formula ##STR2## in which n, R.sub.1 R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are as described above are novel subject to the following provisos (a) when R.sub.3, R.sub.4 and R.sub.4 and R.sub.5 are hydrogen R.sub.2 is methyl and R.sub.1 is lower alkyl, R.sub.1 contains more than one carbon atom, and(b) when R.sub.3 and R.sub.4 are hydrogen, R.sub.5 is hydrogen or 7-methyl, and R.sub.1 is ethyl, R.sub.
    Type: Grant
    Filed: March 24, 1980
    Date of Patent: November 24, 1981
    Assignee: The Boots Company Limited
    Inventors: Roy V. Davies, James Fraser, Kenneth J. Nichol, Raymond Parkinson, Malcolm F. Sim, David B. Yates
  • Patent number: 4294850
    Abstract: New acylanilides of the formula ##STR1## wherein R.sub.1 represents alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or halogen, R.sub.2 represents hydrogen, alkyl of 1 to 3 carbon atoms, alkoxy of 1 to 4 carbon atoms or halogen, R.sub.7 represents hydrogen, alkyl of 1 to 3 carbon atoms, alkoxy of 1 to 4 carbon atoms or halogen, R.sub.8 represents hydrogen or methyl, the total number of carbon atoms of the substituents R.sub.1, R.sub.2, R.sub.7 and R.sub.8 in the phenyl ring not exceeding 8, X represents ##STR2## wherein each of R', R" and R'" independently represents hydrogen, methyl, or ethyl, and Y represents one of the following groups: ##STR3## wherein Hal is a halogen anion, (b) --O--R.sub.4,(c) --S--R.sub.4, wherein R.sub.4 represents alkyl of 1 to 6 carbon atoms, alkenyl of 3 to 6 carbon atoms, alkynyl of 3 to 6 carbon atoms, each of them unsubstituted or substituted by a halogen atom, or R.sub.
    Type: Grant
    Filed: December 7, 1979
    Date of Patent: October 13, 1981
    Assignee: Ciba-Geigy Corporation
    Inventor: Adolf Hubele
  • Patent number: 4294835
    Abstract: A compound represented by the formula: ##STR1## wherein R.sub.1 is hydrogen, acetyl or alkoxycarbonyl having 1-3 carbon atoms of the alkoxy, R.sub.2 is alkyl having 1-12 carbon atoms, alkoxycarbonylmethyl having 1-12 carbon atoms of the alkoxy, benzyl, 2-pyridyl, cyclohexyl phenyl or phenyl substituted by one or two members selected from the group consisting of alkyl having 1-3 carbon atoms, halogen and nitro, and n is 0 or 1, with the proviso that when n is one, R.sub.1 represents acetyl exclusively, and use thereof as a fungicide.
    Type: Grant
    Filed: February 20, 1980
    Date of Patent: October 13, 1981
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Taizo Nakagawa, Hiroshi Matsumoto, Kaoru Ohmori, Shizuo Shimano, Kengo Koike
  • Patent number: 4291049
    Abstract: Acyl anilines are disclosed having the formula ##STR1## wherein R and R.sup.1 (like or unlike each other)=H; CH.sub.3 ; C.sub.2 H.sub.5 ; n.C.sub.3 H.sub.7 ; --CH.sub.2 --CH.dbd.CH.sub.2 ; --CH.dbd.CH--CH.sub.3 ;R.sup.3 and R.sup.4 (like or unlike each other)=H; alkyl C.sub.1 -C.sub.3 ; halomethyl; Cl; F; CN; O-alkyl; S-alkyl; alkoxymethyl;or R.sup.3 and R.sup.4 together are (CH.sub.2 .dbd.) ##STR2## (R.sup.9 =alkyl C.sub.1 -C.sub.3); CN; --CH(OR.sup.5).sub.2 (R.sup.5 =alkyl or alkylidene ); ##STR3## (R.sup.6 and R.sup.7 =H, alkyl) `n=0,1 Z=phenyl optionally substituted; ##STR4## And R.sup.2 =H, CH.sub.3 ; m=1,2; Y=alkynyl C.sub.2 -C.sub.8 ; phenyl optionally substituted; phenyl-acetyl; furyl, thienyl; pyridyl; heterocyclic groups containing 2 or 3 heteroatoms, one of them different from nitrogen;R.sup.8 =CH.sub.3 ; alkoxymethyl; halomethy; O-alkyl.The compounds of formula I are endowed with a high fungicidal activity and with a low phytotoxicity.
    Type: Grant
    Filed: February 1, 1979
    Date of Patent: September 22, 1981
    Assignee: Montedison S.p.A.
    Inventors: Enrico Bosone, Giovanni Camaggi, Lambertus de Vries, Carlo Garavaglia, Luigi Garlaschelli, Franco Gozzo, Jan C. Overeem, Simone Lorusso
  • Patent number: 4289903
    Abstract: There are provided certain p-phenylalkoxy phenylurea and thiourea compounds useful for the control of undesirable plants in the presence of agronomic crops and to methods for the preparation of said phenylalkoxy phenylurea and thiourea compounds.
    Type: Grant
    Filed: June 25, 1979
    Date of Patent: September 15, 1981
    Assignee: American Cyanamid Company
    Inventors: David M. Spatz, Barrington Cross
  • Patent number: 4287210
    Abstract: There are described acylaniline derivatives which in the phenyl ring are substituted in the meta-position with respect to the amino group by an aliphatic oxymethyl group or aryloxymethyl group, or by an aliphatic thiomethyl group or arylthiomethyl group. Compounds of this type have a very favorable microbicidal spectrum. They are used principally for combating phytopathogenic fungi and bacteria.
    Type: Grant
    Filed: November 21, 1979
    Date of Patent: September 1, 1981
    Assignee: Ciba-Geigy Corporation
    Inventors: Wolfgang Eckhardt, Walter Kunz, Adolf Hubele
  • Patent number: 4284790
    Abstract: 3-Hydroxylbenzyl compounds of formula, ##STR1## in which each of R.sub.1, R.sub.2 and R.sub.3 is a hydrocarbon group, e.g. alkyl, R.sub.4 is hydrogen or alkyl, or forms with R.sub.1 --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --, and Z is either an oxygen- or sulphur-containing group featuring at least one ester or amide moiety, or a disubstituted amino group, Z being bound to the rest of the molecule via the oxygen or sulphur atom, or nitrogen atom, respectively, are useful as antioxidants. Organic materials which are susceptible to the degradative effects of oxygen are treated with one or more of such compounds, e.g. by incorporation into the body of the organic material, in order to be stabilized against such effects.
    Type: Grant
    Filed: January 23, 1979
    Date of Patent: August 18, 1981
    Assignee: Sandoz Ltd.
    Inventors: Hans Hinsken, Horst Mayerhoefer, Wolfgang Mueller
  • Patent number: 4273708
    Abstract: Cyan azo dye-providing compounds have the formula: ##STR1## wherein: R.sup.1 is selected from the group consisting of aryl, alkyl or NR.sup.11 R.sup.12 wherein R.sup.11 is alkyl or aryl and R.sup.12 is alkyl, or R.sup.11 and R.sup.12, taken together with the nitrogen atom to which they are attached, is a heterocyclic group;X is --CO-- or --SO.sub.2 --;R.sup.3 is --COOH or --CAR and is attached in the meta or para position to X in the benzene ring;R is alkyl; ##STR2## can be taken together with R and the nitrogen atom to which it is attached to form a heterocyclic ring unsubstituted or substituted with a carboxy group; andCAR is a carrier moiety which, as a function of oxidation under alkaline conditions, releases a diffusible dye, with the proviso that the compound contains at least one CAR group and, excepting when R and R.sup.2 form a heterocyclic group and X is --SO.sub.2 --, must contain at least one carboxy group.
    Type: Grant
    Filed: June 6, 1979
    Date of Patent: June 16, 1981
    Assignee: Eastman Kodak Company
    Inventors: Kenneth N. Kilminster, Colin Holstead
  • Patent number: 4261897
    Abstract: N-chlorosulfinylcarbamate esters are produced by the reaction of thionyl chloride with carbamate esters having one unsubstituted hydrogen on the carbamate nitrogen atom, preferably in the presence of a hydrogen chloride acceptor. The resulting N-chlorosulfinylcarbamate esters are useful intermediates in the preparation of pesticides having relatively low mammalian toxicity.
    Type: Grant
    Filed: March 7, 1979
    Date of Patent: April 14, 1981
    Assignee: The Regents of the University of California
    Inventors: Mohamed A. H. Fahmy, Tetsuo R. Fukuto
  • Patent number: 4262015
    Abstract: A novel class of chemical compounds useful as pesticides consists of N-alkylthio- and N-arylthiosulfinylcarbamate esters. The preparation of these compounds and their formulation to control insects are exemplified.
    Type: Grant
    Filed: March 7, 1979
    Date of Patent: April 14, 1981
    Assignee: The Regents of the University of California
    Inventors: Mohamed A. H. Fahmy, Tetsuo R. Fukuto
  • Patent number: 4256761
    Abstract: Compounds of the structure: ##STR1## wherein 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, or cycloalkyl,n is an integer from 0 to 4 inclusive,M is alkenyl, alkynyl, cycloalkyl, cycloalkyl-alkyl, polycycloalkyl, polycyclo-alkyl-alkyl, aryl, aralkyl, heteroaryl, heteroaryl-alkyl, hetero-cycloalkyl, hetero-cycloalkyl-alkyl, alkoxyalkyl, alkylthioalkyl, alkylamino-alkyl, dialkylamino-alkyl, fused aryl-cycloalkyl, fused aryl-cycloalkyl-alkyl, fused heteroaryl-cycloalkyl, or fused heteroaryl-cycloalkyl-alkyl,Y is hydroxy, alkoxy, amino, or substituted amino, aminoalkanoyl, aryloxy, aminoalkoxy, or hydroxyalkoxy, andR.sub.7 is hydrogen, alkanoyl, carboxylalkanoyl, hydroxyalkanoyl, amino-alkanoyl, cyano, amidino, carbalkoxy, ZS, or ##STR2## wherein Z is hydrogen, alkyl, hyroxyalkyl, aminoalkyl or the radical ##STR3## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.
    Type: Grant
    Filed: July 13, 1979
    Date of Patent: March 17, 1981
    Assignee: USV Pharmaceutical Corporation
    Inventors: John T. Suh, Jerry W. Skiles, Bruce E. Williams, Alfred Schwab
  • Patent number: 4250192
    Abstract: Phenylacetic acid amide compounds of the formula ##STR1## in which R.sub.1 is hydrogen, lower alkyl, lower alkoxy, halogen having an atomic number of not more than 35 or trifluoromethyl, R.sub.2 is hydrogen, lower alkyl, lower alkoxy, halogen having an atomic number of not more than 35 or trifluoromethyl, R.sub.3 is hydrogen, lower alkyl, lower alkoxy or halogen having an atomic number of not more than 35 and R.sub.4 is hydrogen, lower alkyl, lower alkoxy or halogen having an atomic number of not more than 35, and in which R.sub.5 is a radical of aliphatic character containing the group R.sub.6, R.sub.6 and R.sub.7 are each hydrogen or together are a divalent alipahtic radical and the group of the formula --C(.dbd.O)--R.sub.8 (Ia) is a carboxyl group, which can be functionally modified, and their salts are useful as anti-inflammatory agents.
    Type: Grant
    Filed: April 25, 1979
    Date of Patent: February 10, 1981
    Assignee: Ciba-Geigy Corporation
    Inventors: Alfred Sallmann, Gerhard Baschang
  • Patent number: 4240823
    Abstract: Compounds of the formula: ##STR1## in which R.sub.1 is hydrogen, optionally halogenated alkyl, optionally halogenated cycloalkyl, optionally halogenated alkenyl, optionally halogenated aralkenyl or aryloxyalkenyl mono or bicyclic aryl (optionally substituted by halogen, alkyl, trifluoromethyl, nitro, cyano, amino, hydroxyl, alkoxy, aminosulphonyl or alkylcarbonyloxy), or monocyclic or bicyclic heterocyclic of 5-11 chain members and having one or two hetero-atoms (optionally substituted), and R.sub.2 is a carboxylic acid group or a salt or ester thereof, is found to have plant growth regulating activity.
    Type: Grant
    Filed: March 1, 1977
    Date of Patent: December 23, 1980
    Assignee: Philagro S.A.
    Inventors: Claude Clapot, Jean Vial, Jacqueline Mourier, Jean C. Boch
  • Patent number: 4233054
    Abstract: New phenoxy-alkanecarboxylic acid derivatives which have a herbicidal action and which are effective in regulating plant growth are described. They correspond to the formula ##STR1## in which A is the cyano group, a carboxylic acid, a salt, ester, thioester or amide thereof,Q is a mono- to trisubstituted phenyl or pyrid-2-yl radical,R.sub.3 is hydrogen, halogen, cyano, nitro, alkyl or carbamoyl,R.sub.4 is alkyl, alkoxyalkyl, cycloalkyl, alkenyl, alkynyl, phenyl or benzyl, andX, Y and Z are each oxygen or sulfur.They can be used as selective herbicides in cereal and rice crops, or for reducing the vegetative growth, for example in soya-bean crops, and also for defoliation and desiccation in cotton or potato crops shortly before the harvesting thereof.
    Type: Grant
    Filed: March 12, 1979
    Date of Patent: November 11, 1980
    Assignee: Ciba-Geigy Corporation
    Inventors: Henry Szczepanski, Otto Rohr, Georg Pissiotas, Beat Bohner, Hermann Rempfler
  • 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: 4219497
    Abstract: The present invention comprises compounds of the formula ##STR1## and the biologically acceptable acid addition salts thereof wherein R.sub.1 represents hydrogen, or lower alkyl having 1-4 carbon atoms; R.sub.2 represents p-hydroxybenzyl or benzyl; R.sub.3 represents an alkyl having 1-6 carbon atoms; R.sub.4 represents amino or guanidino; R.sub.5 represents p-nitrophenyl, methylnitrophenyl, dinitrophenyl, naphthyl, or nitronaphthyl; and n is 3 or 4.
    Type: Grant
    Filed: April 6, 1979
    Date of Patent: August 26, 1980
    Assignee: Abbott Laboratories
    Inventors: Jacob J. Plattner, Stephen D. Stroupe, Houston F. Voss
  • Patent number: 4218462
    Abstract: Disclosed are 1-substituted-6-(1-hydroxyethyl)-2-(2-aminoethylthio)-1-carbadethiapen-2-e m-3-carboxylic acids (I) and their pharmaceutically acceptable salts and esters which are useful as antibiotics; such compounds are prepared by total synthesis. ##STR1## wherein R.sup.1 is, inter alia, substituted and unsubstituted alkyl, aryl and aralkyl.
    Type: Grant
    Filed: October 24, 1978
    Date of Patent: August 19, 1980
    Assignee: Merck & Co., Inc.
    Inventors: Burton G. Christensen, David H. Shih
  • Patent number: 4216225
    Abstract: Methylmethioninesulfonium compounds of the formula ##STR1## wherein X.crclbar. represents an anion;R.sup.1 represents a hydrogen atom or an acyl group of the formula -COR.sup.3 in which R.sup.3 represents an alkyl group with 1 to 20 carbon atoms, the group --CH.sub.2).sub.2 COOH or the group ##STR2## in which Z represents a direct bond or a methylene or vinylene linkage, Y represents C or N, R.sup.4 represents a member selected from the class consisting of a hydrogen atom, lower alkyl groups, lower alkoxy groups, di-lower-alkylamino groups and a sulfamoyl group, n is a number of 1 to 3, and two or more R.sup.4 groups may be identical or different; andR.sup.2 represents the group --COOR.sup.5 in which R.sup.5 represents a hydrogen atom, an alkyl group with 1 to 5 carbon atoms or a metal- or metal complex-forming moiety, or the group ##STR3## in which R.sup.6 groups may be identical or different, and each represent a hydrogen atom or an alkyl group with 1 to 5 carbon atoms, with the proviso that when R.sup.
    Type: Grant
    Filed: May 16, 1978
    Date of Patent: August 5, 1980
    Assignee: Kowa Company, Ltd.
    Inventors: Masami Shiratsuchi, Kiyoshi Kawamura, Hisashi Kunieda, Naoki Machida, Toshihiro Akashi, Masahiko Nagakura
  • Patent number: 4207333
    Abstract: The compound, N-carbomethoxy-N'-[2'-nitro-4'-propyloxyphenyl]-S-methyl-isothiourea, is useful in the treatment of helminth infestation in ruminants.
    Type: Grant
    Filed: November 15, 1978
    Date of Patent: June 10, 1980
    Assignee: Schering Corporation
    Inventor: Mohammed M. Nafissi-Varchei
  • Patent number: 4204064
    Abstract: A method, composition and compounds useful in said compositions for treating the skin and scalp characterized by an excessive secretion of sebum to improve the condition thereof by reducing said excessive secretion of sebum includes topically applying to a human having skin and/or a scalp so characterized a cosmetic composition containing as an active ingredient a derivative of cysteine or cysteamine. The composition contains about 0.1-5 weight percent of said derivative and also contains as a carrier for the active ingredient, water, a mixture of water and a lower alkanol, a lower alkanol, a mixture of a lower alkanol and a cosmetic resin, a reducing agent, a neutralizing agent or a vegetable oil.
    Type: Grant
    Filed: January 24, 1978
    Date of Patent: May 20, 1980
    Assignee: L'Oreal
    Inventor: Gregoire Kalopissis
  • Patent number: 4203902
    Abstract: A process is disclosed for preparing antibiotic 6- and 2-substituted-1-carbadethiapen-2-em-3-carboxylic acids and their pharmaceutically acceptable salts and esters (I) ##STR1## wherein: R.sup.1 and R.sup.2 are selected from hydrogen, alkyl aryl, and aralkyl; and R.sup.3 is hydrogen, --R, --OR, or --SR, wherein R is hydrogen, alkyl, aryl or aralkyl. The process comprises complexing an appropriately substituted .delta.,.omega.-unsaturated amino acid with a transition metal carbonyl complex, followed by oxidatively induced ligand transfer and ring closure: ##STR2## wherein: F.sub.p =.eta..sup.5 --C.sub.5 H.sub.5 Fe(CO).sub.2 and F.sub.p (isobutene.sup..sym. represents a cationic complex between F.sub.p and an olefin such as isobutene, which complex cation is employed in the initial ligand exchange reaction; R.sup.4 is lower alkyl or phenyl; R.sup.5 is a readily removable blocking group or pharmaceutically acceptable ester radical; and R.sup.1, R.sup.2 and R.sup.3 are as defined above.
    Type: Grant
    Filed: April 21, 1978
    Date of Patent: May 20, 1980
    Assignee: Merck & Co., Inc.
    Inventor: David H. Shih
  • Patent number: 4200760
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is a straight or branched chain alkynyl group containing from 3 to 9 carbon atoms, inclusive; R.sup.2 is hydrogen, (lower)alkyl, halogen or hydroxymethyl; m is 1 or 2, and n is 2 or 3, provided that the sum of m and n is 3 or 4; X and Y each are independently hydrogen, nitro, cyano, --SO.sub.2 Ar or --COR.sup.3, provided that X and Y are not both hydrogen; R.sup.3 is (lower)alkyl, Ar, (lower)alkoxy, amino or (lower)-alkylamino; and Ar is an optionally substituted phenyl group; and nontoxic pharmaceutically acceptable acid addition salts thereof, are potent anti-ulcer agents. Processes for their preparation and novel intermediates are also disclosed.
    Type: Grant
    Filed: September 26, 1978
    Date of Patent: April 29, 1980
    Assignee: Bristol-Myers Company
    Inventors: Aldo A. Algieri, Ronnie R. Crenshaw
  • Patent number: 4194052
    Abstract: A sulfonic acid salt of an acyloxyalkylamine is prepared by reaction of an organic acid or amino-acid with a sulfonic acid salt of an alkanolamine. Isocyanates are prepared therefrom by reaction with phosgene.
    Type: Grant
    Filed: May 1, 1969
    Date of Patent: March 18, 1980
    Assignee: Rohm and Haas Company
    Inventors: Sheldon N. Lewis, Jerome F. Levy
  • Patent number: 4185114
    Abstract: Compounds of the formula ##STR1## wherein X and Y, which may be identical to or different from each other, are each hydrogen or halogen,R.sub.1 is hydrogen or straight or branched alkyl of 1 to 4 carbon atoms,R.sub.2 is hydrogen, straight or branched alkyl of 1 to 3 carbon atoms, carboxy-lower alkyl or acyl, preferably lower aliphatic carboxylic acyl,R.sub.3 is hydrogen or acyl, preferably lower aliphatic carboxylic acyl, andn is 1 or 2;non-toxic, pharmacologically acceptable acid addition salts thereof; sulfonium salts thereof; and, when R.sub.1 is hydrogen, salts thereof formed with inorganic or organic bases or basic aminoacids. The compounds as well as their various salts are useful as mucolytics.
    Type: Grant
    Filed: June 27, 1977
    Date of Patent: January 22, 1980
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Henri Baille-Barrelle, Maurice Vigneron, Charles Lespagnol
  • 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: 4177277
    Abstract: A method for alleviating or reducing angiotensin related hypertension in hypertensive mammals comprises administering an effective amount of a compound having the general formula ##STR1## Intermediates for the preparation of such compounds are also included.
    Type: Grant
    Filed: September 15, 1978
    Date of Patent: December 4, 1979
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Miguel A. Ondetti, Michael E. Condon
  • Patent number: 4169899
    Abstract: Penicillamine compounds of the formula: ##STR1## and of the formula: ##STR2## wherein R.sup.1, R.sup.2, R.sup.3, A and B are as defined hereinafter, and pharmaceutically acceptable acid addition salts thereof are disclosed. II are the products of hydrolysis or alcoholysis of I, and I are in turn the products of dehydration of II or alcohol removal form II. I and II are useful for the treatment of rheumatoid arthritis.
    Type: Grant
    Filed: January 6, 1978
    Date of Patent: October 2, 1979
    Assignee: Yoshitomi Pharmaceutical Industries, Ltd.
    Inventors: Masami Shiroki, Yutaka Maruyama, Kazuhiro Goto
  • Patent number: 4165310
    Abstract: A novel class of N-sulfenyl derivatives of di(carbamic acid esters) are described. The new compounds inhibit premature vulcanization of rubber.
    Type: Grant
    Filed: September 27, 1978
    Date of Patent: August 21, 1979
    Assignee: Monsanto Company
    Inventor: Eiichi Morita
  • Patent number: 4162331
    Abstract: New carboxylic acid derivatives are proposed for use as agents in the treatment or prevention of arteriosclerosis. 1-(p-chlorophenoxy)-3-(N-phenyl-N-carbomethoxymethylamino)-2-propanol is a typical compound.
    Type: Grant
    Filed: January 24, 1977
    Date of Patent: July 24, 1979
    Assignee: Nippon Shinyaku Co., Ltd.
    Inventors: Hiromu Murai, Katsuya Ohata, Hiroshi Enomoto, Shoichi Chokai, Mitsuhiro Machara, Katsuhide Saito, Takayuki Ozaki
  • Patent number: 4156786
    Abstract: New substituted acyl derivatives of amino acids which have the general formula ##STR1## are useful as angiotensin converting enzyme inhibitors.
    Type: Grant
    Filed: June 26, 1978
    Date of Patent: May 29, 1979
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Miguel A. Ondetti, Michael E. Condon
  • Patent number: 4154756
    Abstract: This disclosure describes 2-substituted 4'-(monoalkylamino)-acetophenones useful as hypolipidemic and anti-atherosclerotic agents.
    Type: Grant
    Filed: December 15, 1977
    Date of Patent: May 15, 1979
    Assignee: American Cyanamid Company
    Inventor: Robert G. Shepherd
  • Patent number: 4154960
    Abstract: New substituted acyl derivatives of amino acids which have the general formula ##STR1## are useful as angiotensin converting enzyme inhibitors.
    Type: Grant
    Filed: June 29, 1978
    Date of Patent: May 15, 1979
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Miguel A. Ondetti, Michael E. Condon
  • Patent number: 4154946
    Abstract: New substituted acyl derivatives of amino acids which have the general formula ##STR1## are useful as angiotensin converting enzyme inhibitors.
    Type: Grant
    Filed: June 28, 1978
    Date of Patent: May 15, 1979
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Miguel A. Ondetti, Michael E. Condon
  • Patent number: RE30578
    Abstract: New N-arylcarbamic acid esters of the formula ##STR1## in which R is lower aliphatic hydrocarbyl, optionally substituted,R.sup.1, R.sup.2 and R.sup.3, which may be identical or different, are each hydrogen, alkyl, cycloalkyl, alkoxy, haloalkyl or halogen,R.sup.4 is alkyl, alkenyl, cycloalkenyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl or alkylthioalkyl, acylalkyl (i.e., alkanoyloxyalkyl), alkoxycarbonylalkyl, carbalkoxyalkyl, carbalkoxyalkenyl, or an optionally substituted cycloalkyl, aryl, aralkyl, aryloxyalkyl or arylthioalkyl radical, or the grouping ##STR2## wherein R.sup.4' is hydrogen or is defined as R.sup.4 is defined above, andY and Y' are oxygen or sulfur,are outstandingly effective in regulating the growth of plants, i.e., to inhibit, stimulate or alter the growth of plants.
    Type: Grant
    Filed: November 22, 1977
    Date of Patent: April 14, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Carl Metzger, Gerhard Jager, Klaus Lurssen