Nitrogen In Acid Moiety Patents (Class 560/16)
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Patent number: 4400529Abstract: 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: GrantFiled: March 22, 1982Date of Patent: August 23, 1983Assignee: Stauffer Chemical CompanyInventor: Hsiao-Ling M. Chin
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Patent number: 4387104Abstract: 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: GrantFiled: August 14, 1981Date of Patent: June 7, 1983Assignee: Boehringer Mannheim GmbHInventors: Ruth Heerdt, Hans P. Wolff, Fritz Kaiser, Wolfgang Schaumann, Hans Kuhnle
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Patent number: 4372972Abstract: 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: GrantFiled: September 14, 1979Date of Patent: February 8, 1983Assignee: Rohm and Haas CompanyInventor: Hak-Foon Chan
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Patent number: 4369189Abstract: Novel unsymmetrical formamidine-sulfenylated carbamate compounds exhibit broad-spectrum insecticidal, miticidal and nematocidal activity.Type: GrantFiled: December 10, 1980Date of Patent: January 18, 1983Assignee: Union Carbide CorporationInventor: Themistocles D. J. D'Silva
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Patent number: 4363766Abstract: 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: GrantFiled: April 17, 1979Date of Patent: December 14, 1982Assignee: Boehringer Ingelheim GmbHInventor: Bernard Bellegarde
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Patent number: 4360531Abstract: [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: GrantFiled: April 9, 1981Date of Patent: November 23, 1982Assignee: The Upjohn CompanyInventors: Moses W. McMillan, Jacob Szmuszkovicz
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Patent number: 4359476Abstract: 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: GrantFiled: April 9, 1981Date of Patent: November 16, 1982Assignee: The Upjohn CompanyInventors: Lester J. Kaplan, Moses W. McMillan, Jacob Szmuszkovicz
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Patent number: 4354975Abstract: 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: GrantFiled: July 21, 1980Date of Patent: October 19, 1982Assignee: The Upjohn CompanyInventor: Stephen J. Nelson
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Patent number: 4348406Abstract: Compounds of the formula: ##STR1## and their pharmaceutically acceptable acid addition salts, useful as anthelmintics are disclosed.Type: GrantFiled: October 20, 1980Date of Patent: September 7, 1982Assignee: Schering CorporationInventor: M. Mehdi Nafissi-Varchei
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Patent number: 4346104Abstract: 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: GrantFiled: December 17, 1980Date of Patent: August 24, 1982Assignee: Ciba-Geigy CorporationInventors: Alfred Sallmann, Gerhard Baschang
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Patent number: 4330674Abstract: 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: GrantFiled: October 8, 1980Date of Patent: May 18, 1982Assignee: E. I. Du Pont de Nemours and CompanyInventor: Jiin-Duey Cheng
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Patent number: 4329293Abstract: 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: GrantFiled: October 31, 1980Date of Patent: May 11, 1982Assignee: FMC CorporationInventors: John W. Ager, Maurice J. C. Harding, Charles E. Hatch, III
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Patent number: 4320142Abstract: 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: GrantFiled: May 15, 1980Date of Patent: March 16, 1982Inventors: Malcolm H. Black, Alexander D. Frenkel, Peter T. Roberts
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Patent number: 4315026Abstract: 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: GrantFiled: April 11, 1980Date of Patent: February 9, 1982Assignee: The Regents of the University of CaliforniaInventors: Mohamed A. H. Fahmy, Tetsuo R. Fukuto, Teruomi Jojima
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Patent number: 4309425Abstract: 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: GrantFiled: April 11, 1980Date of Patent: January 5, 1982Assignee: E. I. Du Pont de Nemours and CompanyInventor: Jiin-Duey Cheng
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Patent number: 4303673Abstract: 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: GrantFiled: September 5, 1980Date of Patent: December 1, 1981Assignee: A. Nattermann & Cie. GmbHInventors: Jurgen Biedermann, Armin Wendel, Hans Betzing, Volker Neuser
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Patent number: 4302460Abstract: 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: GrantFiled: March 24, 1980Date of Patent: November 24, 1981Assignee: The Boots Company LimitedInventors: Roy V. Davies, James Fraser, Kenneth J. Nichol, Raymond Parkinson, Malcolm F. Sim, David B. Yates
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Patent number: 4294850Abstract: 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: GrantFiled: December 7, 1979Date of Patent: October 13, 1981Assignee: Ciba-Geigy CorporationInventor: Adolf Hubele
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Patent number: 4294835Abstract: 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: GrantFiled: February 20, 1980Date of Patent: October 13, 1981Assignee: Nippon Kayaku Kabushiki KaishaInventors: Taizo Nakagawa, Hiroshi Matsumoto, Kaoru Ohmori, Shizuo Shimano, Kengo Koike
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Patent number: 4291049Abstract: 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: GrantFiled: February 1, 1979Date of Patent: September 22, 1981Assignee: Montedison S.p.A.Inventors: Enrico Bosone, Giovanni Camaggi, Lambertus de Vries, Carlo Garavaglia, Luigi Garlaschelli, Franco Gozzo, Jan C. Overeem, Simone Lorusso
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Patent number: 4289903Abstract: 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: GrantFiled: June 25, 1979Date of Patent: September 15, 1981Assignee: American Cyanamid CompanyInventors: David M. Spatz, Barrington Cross
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Patent number: 4287210Abstract: 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: GrantFiled: November 21, 1979Date of Patent: September 1, 1981Assignee: Ciba-Geigy CorporationInventors: Wolfgang Eckhardt, Walter Kunz, Adolf Hubele
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Patent number: 4284790Abstract: 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: GrantFiled: January 23, 1979Date of Patent: August 18, 1981Assignee: Sandoz Ltd.Inventors: Hans Hinsken, Horst Mayerhoefer, Wolfgang Mueller
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Patent number: 4273708Abstract: 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: GrantFiled: June 6, 1979Date of Patent: June 16, 1981Assignee: Eastman Kodak CompanyInventors: Kenneth N. Kilminster, Colin Holstead
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Patent number: 4261897Abstract: 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: GrantFiled: March 7, 1979Date of Patent: April 14, 1981Assignee: The Regents of the University of CaliforniaInventors: Mohamed A. H. Fahmy, Tetsuo R. Fukuto
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Patent number: 4262015Abstract: 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: GrantFiled: March 7, 1979Date of Patent: April 14, 1981Assignee: The Regents of the University of CaliforniaInventors: Mohamed A. H. Fahmy, Tetsuo R. Fukuto
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Patent number: 4256761Abstract: 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: GrantFiled: July 13, 1979Date of Patent: March 17, 1981Assignee: USV Pharmaceutical CorporationInventors: John T. Suh, Jerry W. Skiles, Bruce E. Williams, Alfred Schwab
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Patent number: 4250192Abstract: 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: GrantFiled: April 25, 1979Date of Patent: February 10, 1981Assignee: Ciba-Geigy CorporationInventors: Alfred Sallmann, Gerhard Baschang
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Patent number: 4240823Abstract: 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: GrantFiled: March 1, 1977Date of Patent: December 23, 1980Assignee: Philagro S.A.Inventors: Claude Clapot, Jean Vial, Jacqueline Mourier, Jean C. Boch
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Patent number: 4233054Abstract: 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: GrantFiled: March 12, 1979Date of Patent: November 11, 1980Assignee: Ciba-Geigy CorporationInventors: Henry Szczepanski, Otto Rohr, Georg Pissiotas, Beat Bohner, Hermann Rempfler
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Patent number: 4228184Abstract: New carboxyalkylacylamino acids which have the general formula ##STR1## are useful as angiotensin converting enzyme inhibitors.Type: GrantFiled: May 4, 1978Date of Patent: October 14, 1980Assignee: E. R. Squibb & Sons, Inc.Inventors: Miguel A. Ondetti, David W. Cushman
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Patent number: 4219497Abstract: 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: GrantFiled: April 6, 1979Date of Patent: August 26, 1980Assignee: Abbott LaboratoriesInventors: Jacob J. Plattner, Stephen D. Stroupe, Houston F. Voss
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Patent number: 4218462Abstract: 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: GrantFiled: October 24, 1978Date of Patent: August 19, 1980Assignee: Merck & Co., Inc.Inventors: Burton G. Christensen, David H. Shih
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Patent number: 4216225Abstract: 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: GrantFiled: May 16, 1978Date of Patent: August 5, 1980Assignee: Kowa Company, Ltd.Inventors: Masami Shiratsuchi, Kiyoshi Kawamura, Hisashi Kunieda, Naoki Machida, Toshihiro Akashi, Masahiko Nagakura
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Patent number: 4207333Abstract: The compound, N-carbomethoxy-N'-[2'-nitro-4'-propyloxyphenyl]-S-methyl-isothiourea, is useful in the treatment of helminth infestation in ruminants.Type: GrantFiled: November 15, 1978Date of Patent: June 10, 1980Assignee: Schering CorporationInventor: Mohammed M. Nafissi-Varchei
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Patent number: 4204064Abstract: 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: GrantFiled: January 24, 1978Date of Patent: May 20, 1980Assignee: L'OrealInventor: Gregoire Kalopissis
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Patent number: 4203902Abstract: 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: GrantFiled: April 21, 1978Date of Patent: May 20, 1980Assignee: Merck & Co., Inc.Inventor: David H. Shih
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Patent number: 4200760Abstract: 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: GrantFiled: September 26, 1978Date of Patent: April 29, 1980Assignee: Bristol-Myers CompanyInventors: Aldo A. Algieri, Ronnie R. Crenshaw
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Patent number: 4194052Abstract: 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: GrantFiled: May 1, 1969Date of Patent: March 18, 1980Assignee: Rohm and Haas CompanyInventors: Sheldon N. Lewis, Jerome F. Levy
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Patent number: 4185114Abstract: 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: GrantFiled: June 27, 1977Date of Patent: January 22, 1980Assignee: Boehringer Ingelheim GmbHInventors: Henri Baille-Barrelle, Maurice Vigneron, Charles Lespagnol
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Patent number: 4182891Abstract: 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: GrantFiled: July 1, 1977Date of Patent: January 8, 1980Assignee: Merrell Toraude et CompagnieInventors: Brian W. Metcalf, Michel Jung
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Patent number: 4177277Abstract: 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: GrantFiled: September 15, 1978Date of Patent: December 4, 1979Assignee: E. R. Squibb & Sons, Inc.Inventors: Miguel A. Ondetti, Michael E. Condon
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Patent number: 4169899Abstract: 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: GrantFiled: January 6, 1978Date of Patent: October 2, 1979Assignee: Yoshitomi Pharmaceutical Industries, Ltd.Inventors: Masami Shiroki, Yutaka Maruyama, Kazuhiro Goto
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Patent number: 4165310Abstract: A novel class of N-sulfenyl derivatives of di(carbamic acid esters) are described. The new compounds inhibit premature vulcanization of rubber.Type: GrantFiled: September 27, 1978Date of Patent: August 21, 1979Assignee: Monsanto CompanyInventor: Eiichi Morita
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Patent number: 4162331Abstract: 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: GrantFiled: January 24, 1977Date of Patent: July 24, 1979Assignee: Nippon Shinyaku Co., Ltd.Inventors: Hiromu Murai, Katsuya Ohata, Hiroshi Enomoto, Shoichi Chokai, Mitsuhiro Machara, Katsuhide Saito, Takayuki Ozaki
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Patent number: 4156786Abstract: New substituted acyl derivatives of amino acids which have the general formula ##STR1## are useful as angiotensin converting enzyme inhibitors.Type: GrantFiled: June 26, 1978Date of Patent: May 29, 1979Assignee: E. R. Squibb & Sons, Inc.Inventors: Miguel A. Ondetti, Michael E. Condon
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Patent number: 4154756Abstract: This disclosure describes 2-substituted 4'-(monoalkylamino)-acetophenones useful as hypolipidemic and anti-atherosclerotic agents.Type: GrantFiled: December 15, 1977Date of Patent: May 15, 1979Assignee: American Cyanamid CompanyInventor: Robert G. Shepherd
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Patent number: 4154960Abstract: New substituted acyl derivatives of amino acids which have the general formula ##STR1## are useful as angiotensin converting enzyme inhibitors.Type: GrantFiled: June 29, 1978Date of Patent: May 15, 1979Assignee: E. R. Squibb & Sons, Inc.Inventors: Miguel A. Ondetti, Michael E. Condon
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Patent number: 4154946Abstract: New substituted acyl derivatives of amino acids which have the general formula ##STR1## are useful as angiotensin converting enzyme inhibitors.Type: GrantFiled: June 28, 1978Date of Patent: May 15, 1979Assignee: E. R. Squibb & Sons, Inc.Inventors: Miguel A. Ondetti, Michael E. Condon
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Patent number: RE30578Abstract: 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: GrantFiled: November 22, 1977Date of Patent: April 14, 1981Assignee: Bayer AktiengesellschaftInventors: Carl Metzger, Gerhard Jager, Klaus Lurssen