The Metal Is Bonded Directly To Chalcogen Of A -c(=x)x- Group, Wherein The X's Are The Same Or Diverse Chalcogens, Which Group Is Attached Directly Or Indirectly To The Six-membered Hetero Ring By Nonionic Bonding Patents (Class 546/5)
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Patent number: 4473395Abstract: This invention relates to a method of inducing tillering in cereal plants using certain 5-phenyl-3-pyridinecarboxylate compounds, to certain of the compounds themselves, to a process for preparing these compounds, and to agricultural compositions containing them. The compounds are also useful as intermediates for preparing other of the compounds.Type: GrantFiled: May 17, 1982Date of Patent: September 25, 1984Assignee: Imperial Chemical Industries PLCInventors: Alan F. Hawkins, David P. J. Pearson, Gilbert J. Stacey
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Patent number: 4472405Abstract: The compound 6,7-dihydro-5,8-dimethyl-9-fluoro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carbo xylic acid is disclosed as a potent antimicrobial agent with a broad spectrum of activity. Esters, acyl chlorides, alkylaminoalkyl ester salts and pharmaceutically acceptable carboxylate salts of the acid are also disclosed. Methods of using these compounds, pharmaceutical compositions comprising these compounds and synthetic intermediates for preparing these compounds are described.Type: GrantFiled: November 12, 1982Date of Patent: September 18, 1984Assignee: Riker Laboratories, Inc.Inventor: Richard M. Stern
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Patent number: 4472406Abstract: Certain 6,7-dihydro-8-(imidazol-1-yl)-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxyli c acids are disclosed as potent antimicrobial agents with an unusual spectrum of activity. Esters, acyl chlorides, alkylaminoalkyl ester salts, salts of a nitrogen atom of the imidazole ring, and pharmaceutically acceptable carboxylate salts are also disclosed. Novel synthetic intermediates are also described.Type: GrantFiled: November 12, 1982Date of Patent: September 18, 1984Assignee: Riker Laboratories, Inc.Inventor: John F. Gerster
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Patent number: 4434178Abstract: Aluminum compounds containing organic groups of the formula ##STR1## when R.sup.1 and R.sup.2 are as hereinafter set forth are disclosed as having activity as antiperspirants. Antiperspirant compositions containing one or more of these compounds as transpiration-inhibiting active ingredients and methods for preparing the compounds are also disclosed.Type: GrantFiled: September 29, 1981Date of Patent: February 28, 1984Assignee: Hoffmann-La Roche, Inc.Inventors: Hans U. Hostettler, Horst Pauling
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Patent number: 4420616Abstract: A process for the preparation of copper quinolinate in which quinoline is oxidized by hydrogen peroxide in sulfuric acid in the presence of copper sulfate wherein the reaction is carried out at a pressure of less than 400 mm Hg. The reduced pressure enables the reaction to be performed at higher temperatures and with greater control; also the reaction time is shortened and the yield improved.Copper quinolinate is used to prepare quinolinic acid which is the starting material for some chromogenic materials used in the pressure-sensitive record material field.Type: GrantFiled: February 20, 1981Date of Patent: December 13, 1983Assignee: Yamamoto Kagaku Gosei Co., Ltd.Inventors: Seishi Ikegami, Yoshihiro Hatano
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Patent number: 4419515Abstract: This invention relates to a two stage process for preparing 2,6-pyridinedicarboxylic acid or dipicolinic acid from 2,6-dimethyl-pyridine through oxidation of the latter in an acid environment with hexavalent chromium salts and formation of a molar addition compound between dicarboxylic acid, being formed by oxidation, and chromic anhydride in the first stage, and subsequent hot hydrolysis of the addition product so obtained, thus isolating 2,6-pyridinedicarboxylic acid therefrom in the second stage. The invention also comprises the above mentioned intermediate complex addition compound and the 2,6-pyridinedicarboxylic acid of high purity, obtained by the process according to said invention.Type: GrantFiled: July 13, 1981Date of Patent: December 6, 1983Assignee: Luigi Stoppani S.p.A.Inventors: Giovanni Ghelli, Enrico Bruschi, Gino Agnese
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Patent number: 4404206Abstract: Bicyclic imino acids, particularly 2-carboxylic acid derivatives of azabicycloalkanes and process for preparing them.These compounds have therapeutical activity and may be used as medicines, particularly as cardiovascular and antihypertensive drugs in human or veterinary medicine.Type: GrantFiled: December 3, 1980Date of Patent: September 13, 1983Assignee: Science Union et CieInventors: Michel Vincent, Georges Remond, Michel Laubie
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Patent number: 4400513Abstract: There are disclosed new 4-spiro-oxirane derivatives of substituted piperidine having the general formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, either like or unlike one another, are each an alkyl radical having 1 to 4 C, or R.sub.1 and R.sub.2, and/or R.sub.3 and R.sub.4 together form a cyclo-alkylene radical having 3 to 13 C; R.sub.5 may be hydrogen, an alkyl, oxyalkyl or alkoxy radical having 1 to 6 C, an aryl or aryl-alkyl radical having 6 to 18 C, an alkenyl radical having 2 to 6 or a --(CH.sub.2).sub.X CO.sub.2 R.sub.7 radical in which X is an integer from 0 to 12, R.sub.7 =H, metal, an alkyl, alkylene, alkenyl, alkenylene radical having 1 to 20 C and R.sub.6 is hydrogen or an alkyl radical containing 1 to 4 C.Type: GrantFiled: March 15, 1982Date of Patent: August 23, 1983Assignee: Montedison, S.p.A.Inventor: Piero Di Battista
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Patent number: 4387227Abstract: Novel zinc N,N'-alkenylsuccinoyl dipyridyl succinate is prepared by the novel reaction between an alkenylsuccinic anhydride, pyridine and zinc catalyzed by zinc chloride in pyridine reaction solvent. The novel zinc salt is useful to inhibit oxidation of hydrocarbon distillates and lubricant oils.Type: GrantFiled: October 16, 1981Date of Patent: June 7, 1983Assignee: Standard Oil Company (Indiana)Inventor: Richard J. Lee
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Patent number: 4316026Abstract: A process for the preparation of copper quinolinate in which quinoline is oxidized by hydrogen peroxide in 10 to 30% sulfuric acid in the presence of copper sulfate at a temperature of 55.degree. to 75.degree. C., the molar ratio of sulfuric acid to quinoline being greater than 1:1. The concentration and amount of sulfuric acid enable greater control of the reaction temperature and result in copper quinolate in improved yield and purity.Copper quinolinate is used to prepare quinolinic acid which is the starting material for some chromogenic materials used in the pressure-sensitive record material field.Type: GrantFiled: August 12, 1980Date of Patent: February 16, 1982Assignee: Yamamoto Kagaku Gosei Co., Ltd.Inventors: Yoshihiro Hatano, Seishi Ikegami, Kenji Itoh, Mansuke Matsumoto
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Patent number: 4309546Abstract: Pyrrolidiones of the formula I ##STR1## wherein n is 1, 2, 3 or 4, R.sub.1 is free or esterified hydroxyl or hydroxyl which has been converted to a salt or is substituted or unsubstituted amino, X is a direct bond or a linking member and Pip is a substituted or unsubstituted 2,2,6,6-tetraalkylpiperidin-4-yl or a 2,2,6,6-tetraalkylpiperidin-4-ylidene, which pyrrolidones can be oligomerized or polymerized by linking R.sub.1 with X or by linking R.sub.1 with Pip. These compounds are used as light stabilizers for polymers.Type: GrantFiled: April 24, 1980Date of Patent: January 5, 1982Assignee: Ciba-Geigy CorporationInventor: Friedrich Karrer
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Patent number: 4299769Abstract: This disclosure describes novel substituted .omega.-heteroaroyl(propionyl or butyryl)-L-prolines and the esters and cationic salts thereof which are useful as hypotensive agents in mammals.Type: GrantFiled: April 28, 1980Date of Patent: November 10, 1981Assignee: American Cyanamid CompanyInventors: Francis J. McEvoy, William B. Wright, Jr., Gary H. Birnberg, Jay D. Albright
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Patent number: 4278798Abstract: 1-Ethyl-1,4-dihydro-6-(2-naphthyl)-4-oxonicotinic acid and C.sub.1-6 -alkyl esters thereof as well as their alkali metal, alkaline earth metal or ammonium salts are described. The foregoing compounds are useful as central nervous system stimulants. Also described are 1-ethyl-6-(2-naphthyl)-4-oxo-1,4,5,6-tetrahydronicotinic acid and C.sub.1-6 -alkyl esters thereof, which are useful as intermediates.Type: GrantFiled: July 7, 1980Date of Patent: July 14, 1981Assignee: Hoffmann-La Roche Inc.Inventor: Alexander E. Wick
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Patent number: 4264494Abstract: Metal complex compounds which in the form of the free acids correspond to the formula I ##STR1## where A is an aliphatic, carbocyclic or heterocyclic radical,E is an aliphatic or carbocyclic radical,B is a cyano, acyl, substituted sulfonyl, carboxylic acid ester or carboxamide radical, orB and E together with the carbon atoms by which they are linked may be an alicyclic or heterocyclic radical,F is an aliphatic, carbocylic or heterocyclic radical,L is --O--, --COO--, ##STR2## n is 1, 2, 3 or 4, Y is .dbd.CH-- or .dbd.N-- andZ is ##STR3## or the radical of a coupling component, alkyl being of 1 to 4 carbon atoms, andR is hydrogen or unsubstituted or substituted alkyl, cycloalkyl, aryl or acyl and R.sup.1 and R.sup.2 are substituents conventionally present in dyes.The compounds of the formula I give fast dyeings on natural polyamides and synthetic nylons.Type: GrantFiled: August 2, 1978Date of Patent: April 28, 1981Assignee: BASF AktiengesellschaftInventors: Klaus Grychtol, Hans Baumann
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Patent number: 4229448Abstract: 5-Substituted picolinic acid derivatives represented by the formula (I): ##STR1## wherein R.sub.1 represents a straight or branched chain halogen-substituted alkyl group having 2 to 6 carbon atoms or a substituted phenyl group having the formula ##STR2## wherein R.sub.3 and R.sub.4, which may be the same or different, each represents a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a nitro group, an amino group, an N-alkyl-substituted amino group, an acylamino group, an acetyl group, an acyloxy group, a hydroxy group or a halogen-substituted alkyl group or R.sub.3 and R.sub.4, when taken together, represent a polymethylene chain; and R.sub.Type: GrantFiled: March 23, 1979Date of Patent: October 21, 1980Assignee: Meuji Seika Kaisha Ltd.Inventors: Yasuharu Sekizawa, Takashi Tsuruoka, Mitsugu Hachisu, Masaji Sezaki, Masashi Miyamoto, Uichi Shibata, Kazuko Mizutani, Shigeharu Inouye, Takemi Koeda, Keizo Shimomura, Taro Niida
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Patent number: 4214088Abstract: Stabilization of chlorine-containing thermoplasts with 1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylic acid esters alone or, in particular, together with a metal-containing stabilizer as synergist.Type: GrantFiled: November 8, 1978Date of Patent: July 22, 1980Assignee: Ciba-Geigy CorporationInventors: Gerd Abeler, Rudolf Maul
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Patent number: 4193979Abstract: Sodium 3-[[[2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl]-amino]carbonyl]-2-pyridin ecarboxylic acid and related compounds which are labeled with radioactive technetium-99m are described as well as their preparations. These novel complexes are useful by reason of their utility as radiopharmaceutical imaging agents. Particularly, these complexes are useful as gallbladder and liver imaging agents.Type: GrantFiled: May 22, 1978Date of Patent: March 18, 1980Assignee: G. D. Searle & Co.Inventors: Patricia Frank, Stephen Kraychy, Ernest F. LeVon
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Patent number: 4191682Abstract: Compounds having the formula ##STR1## wherein R.sub.1 and R.sub.2 are lower alkyl or together lower alkylene,R.sub.3 is hydrogen, alkyl, methoxyethyl, alkenyl, propargyl, benzyl, alkyl substituted benzyl, or acyl,R.sub.4 is alkylene, alkyl-thio-alkyl or alkyl-oxo-alkyl,M is hydrogen or a metal, and z has a value of from 1 to 4, and either(a) R.sub.5 is alkyl of 1 to 6 carbon atoms, R.sub.6 is alkyl of 1 to 6 carbon atoms, and R.sub.7 and R.sub.8 are independently hydrogen or alkyl of 1 to 5 carbon atoms, provided that R.sub.7 and R.sub.8 are not both hydrogen, or(b) R.sub.5 and R.sub.6 are together lower alkylene and R.sub.7 and R.sub.8 are independently hydrogen or alkyl of 1 to 5 carbon atoms,are good light stabilizers. The carboxylic acids are prepared for example, from 2,3,6-trimethyl-2,6-diethylpiperidin-4-ol and sebacic acid to give 2,3,6-trimethyl-2,6-diethyl-4-piperidyl hydrogen sebacate.Type: GrantFiled: June 22, 1978Date of Patent: March 4, 1980Assignee: Ciba-Geigy CorporationInventors: Chester E. Ramey, John J. Luzzi
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Patent number: 4191829Abstract: Compounds having the formula ##STR1## wherein R.sub.1 and R.sub.2 are lower alkyl or cycloalkyl,R.sub.3 is hydrogen, alkyl, methoxyethyl, alkenyl, propargyl, benzyl or alkyl substituted benzyl,R.sub.4 is alkylene of 1 to 4 carbon atoms substituted with alkyl or alkenyl of 1 to 18 carbon atoms, alkenylene of 1 to 4 carbon atoms, cycloalkylene, cycloalkenylene, bicycloalkylene, bicycloalkenylene, or phenyllene,M is hydrogen or a metal, andz has a value of from 1 to 4,are good light stabilizers. The carboxylic acids are prepared for example, from 2,2,6,6-tetramethylpiperidin-4-ol and cyclohexane-1,2-dicarboxylic anhydride to give (O-mono (2,2,6,6-tetramethylpiperidin-4-ol)cyclohexane(1,2-dicarboxylate. The metal salts of the acids are readily prepared by reacting the acids or their salts with a reactive form of the metal or metal complex.Type: GrantFiled: April 25, 1978Date of Patent: March 4, 1980Assignee: Ciba-Geigy CorporationInventors: Chester E. Ramey, John J. Luzzi
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Patent number: 4189489Abstract: 5-Alkoxy-picolinic acids and the salts and the esters thereof represented by the formula (I): ##STR1## wherein R represents an alkyl group having 1 to 6 carbon atoms and M represents a hydrogen atom; a calcium atom; a sodium atom; a potassium atom; an aluminum atom; an unsubstituted phenyl group; a phenyl group substituted with one or more of an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms or a halogen atom (such as a chlorine, bromine, iodine, etc., atom); a phthalidyl group; an alkoxyalkyl group wherein the alkyl moiety and the alkoxy moiety each has 1 to 4 carbon atoms; or an acyloxyalkyl group having the formula ##STR2## wherein R.sub.2 represents a hydrogen atom or a methyl group and R.sub.3 represents an alkyl group having 1 to 5 carbon atoms (such as a methyl, n-propyl, isobutyl, t-butyl, etc.Type: GrantFiled: September 30, 1977Date of Patent: February 19, 1980Assignee: Meiji Seika Kaisha, Ltd.Inventors: Takemi Koeda, Takashi Tsuruoka, Uichi Shibata, Hiroyasu Asaoka, Mitsugu Hachisu, Osamu Itoh, Yasuharu Sekizawa, Shigeharu Inouye, Taro Niida
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Patent number: 4180395Abstract: Compounds are prepared which correspond to the formula ##STR1## wherein X represents chloro, bromo or iodo; R' represents hydrogen or methyl and R represents carboxy (--COOH), the alkyl esters thereof (--COOR.sup.6 wherein R.sup.6 represents alkyl of 1 to 8 carbon atoms, (2-alkoxyethoxy)carbonyl (--COOCH.sub.2 CH.sub.2 OR.sup.2) or (1-methyl-2-alkoxyethoxy)carbonyl ##STR2## wherein R.sup.2 represents alkyl of 1 to 4 carbon atoms) or the metal salts thereof (--COOMe wherein Me represents ammonium or substituted ammonium ion (N.sup.+ H(R.sup.6).sub.3 wherein each R.sup.6 independently represents hydrogen, alkyl of 1 to 4 carbon atoms or hydroxyalkyl of 2 to 3 carbon atoms), alkali metal, alkaline earth metal, aluminum or a transition group metal); alkanoyloxymethyl (--CH.sub.2 OCOR.sup.2); (2,2-dichloropropionyloxy)methyl (--CH.sub.2 OCOC(Cl).sub.2 CH.sub.3); alkoxymethyl (--CH.sub.2 OR.sup.2); phenoxymethyl (--CH.sub.2 O.phi.); (2-alkoxyethoxy)methyl (--CH.sub.2 OCH.sub.2 CH.sub.2 OR.sup.2); hydroxyalkyl (--R.Type: GrantFiled: April 11, 1977Date of Patent: December 25, 1979Assignee: The Dow Chemical CompanyInventors: Howard Johnston, Herman O. Senkbeil
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Patent number: 4171313Abstract: A catalytic system for oxidation of organic compounds including olefins, cyclic ketones and secondary alcohols. Soluble peroxo or solid supported oxo or peroxo complexes of molybdenum or tungsten are used in the presence of hydrogen peroxide to effect the oxidation. The resulting products include lactones, hydroxy acids, ketoacids, hydroxy esters and ketoesters from cyclic ketones; ketones from secondary alcohols and polyols or derivatives thereof from allylic alcohols.Type: GrantFiled: October 14, 1977Date of Patent: October 16, 1979Assignee: Allied Chemical CorporationInventors: Frank Mares, Stephen E. Jacobson, Reginald T. Tang
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Patent number: 4133675Abstract: The present invention concerns new pyridyloxy-phenoxy-alkanecarboxylic acid derivatives of the formula ##STR1## wherein A is hydrogen, halogen, alkyl, alkoxy, cyano, nitro or carbothiamideB is hydrogen, halogen, alkyl, cyano, mono- or dialkylamino, alkoxy-carbonyl or carbothiamideC is hydrogen, halogen, cyano, nitro or carbothiamideD is hydrogen, halogen, alkyl, mono- or dialkylaminoR.sub.1 is hydrogen, alkyl, alkoxyalkyl or benzyl R is the rest of the acid a salt or an ester,With the proviso that if the pyridine ring is substituted by halogen and/or alkyl and C is also halogen, then the radicals A, B and D must contain no less than two halogen atoms or alkyl radicals.These derivatives have herbicidal and plant-growth regulating activity.Type: GrantFiled: July 18, 1977Date of Patent: January 9, 1979Assignee: Ciba-Geigy CorporationInventors: Rolf Schurter, Hermann Rempfler