Phenolic Hydroxy Or Metallate Patents (Class 560/75)
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Patent number: 4334079Abstract: A process for preparing certain substituted benzyl esters of phenylacetic acids by esterification in a solvent in which the salt of the acid is insoluble, and in the presence of a phase transfer catalyst.Type: GrantFiled: November 3, 1980Date of Patent: June 8, 1982Assignee: Eli Lilly and CompanyInventors: James M. Greene, Charles A. Bunnell
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Patent number: 4332734Abstract: New homopolymerizable or copolymerizable 3,3-disubstituted furan dione compounds are described of the formula ##STR1## wherein X is a reactive moiety and Y and R are unreactive moieties.Type: GrantFiled: December 9, 1980Date of Patent: June 1, 1982Assignee: The Dow Chemical CompanyInventors: Edmund P. Woo, Michael J. Mullins
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Patent number: 4329507Abstract: New substituted aryl ethylenes are disclosed which are produced by dehydration of the corresponding .alpha.- or .beta.-(substituted aryl)ethyl alcohols or by dehydrohalogenation of the corresponding .alpha.- or .beta.-(substituted aryl)ethyl halides.Type: GrantFiled: January 14, 1980Date of Patent: May 11, 1982Assignee: Mitsubishi Petrochemical Co., Ltd.Inventors: Makoto Takeda, Masayuki Uchide, Hiroshi Iwane
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Patent number: 4327036Abstract: Process for nuclear chlorination of non-phenolic aromatic compounds, said process comprising contacting and reacting a non-phenolic aromatic compound having a net Hammett .sigma. value of about -0.1 to about 2.0 with chlorine monoxide in the presence of at least one-half an equivalent amount, based on the chlorine monoxide, of an acid having a pK.sub.a no greater than that of trichloroacetic acid, provided, however, when the net Hammett .sigma. value is about 0.7 to about 2.0, the acid has a pK.sub.a no greater than that of trifluoroacetic acid.Type: GrantFiled: May 8, 1980Date of Patent: April 27, 1982Assignee: E. I. Du Pont de Nemours and CompanyInventor: Frank D. Marsh
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Patent number: 4313956Abstract: Novel, transient prodrug forms of the phenolic dihydroxy sympathomimetic amines have (i) the structural formula (I): ##STR1## wherein X is O, S or NR.sup.5 ; n is 1 or 2; R.sup.1 is the monodehydroxylated residue of a phenolic, nuclear dihydroxy natural sympathetic or sympathomimetic amine when n is 1, and the didehydroxylated residue of a phenolic, nuclear dihydroxy natural sympathetic or sympathomimetic amine when n is 2; R.sup.Type: GrantFiled: December 28, 1979Date of Patent: February 2, 1982Assignee: INTERx Research Corp.Inventors: Nicholas S. Bodor, Kenneth B. Sloan, Stefano A. Pogany
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Patent number: 4311706Abstract: Novel, transient prodrug forms of dopa and dopamine have (i) the structural formula (I): ##STR1## wherein each R is independently selected from the group consisting of hydrogen, R.sup.3 -CO- and ##STR2## wherein X is O, S or NR.sup.6 ; R.sup.1 is hydrogen or --COOR.sup.8 ; R.sup.2 is hydrogen or OR; R.sup.Type: GrantFiled: January 22, 1980Date of Patent: January 19, 1982Assignee: INTERx Research CorporationInventors: Nicholas S. Bodor, Kenneth B. Sloan, Stefano A. Pogany
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Patent number: 4305868Abstract: Novel phenolically substituted esterbisamides as antioxidants useful for the protection of organic materials such as synthetic and natural rubbers, plastics and petroleum products against oxidative degradation.Type: GrantFiled: May 30, 1979Date of Patent: December 15, 1981Assignee: Uniroyal, Inc.Inventors: Edward L. Wheeler, Elmar H. Jancis, Richard A. Gencarelli, Franklin H. Barrows
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Patent number: 4304714Abstract: Novel phenolic oxamide antioxidants for protecting organic materials such as synthetic and natural rubbers, petroleum products, and plastics from oxidative degradation.Type: GrantFiled: May 30, 1979Date of Patent: December 8, 1981Assignee: Uniroyal, Inc.Inventors: Edward L. Wheeler, Elmar H. Jancis, Richard A. Gencarelli, Franklin H. Barrows
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Patent number: 4267358Abstract: Phenolic esters wherein the phenolic groups are hindered by at least one ortho substituent. The esters are effective to impart thermal stability to olefin polymers. Their structure is as follows: ##STR1## where R is alkyl or cycloalkyl of 3-8 carbon atoms, R.sup.1 is alkyl of 1-6 carbon atoms and n is 1-2.Type: GrantFiled: March 13, 1980Date of Patent: May 12, 1981Assignee: Borg-Warner CorporationInventors: Ingenuin Hechenbleikner, William P. Enlow, James H. Weis
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Patent number: 4263446Abstract: An improved method for making 3-(3,5-dialkyl-4-hydroxyphenyl)propionates of hydroxyalkyloxamides involved heating the hydroxyalkyloxamide with a lower alkyl ester of 3-(3,5-dialkyl-4-hydroxyphenyl)propionic acid in the presence of an alkanestannoic acid at a temperature of 150.degree. to 230.degree. C., the lower boiling alcohol being removed by distillation.Type: GrantFiled: May 30, 1979Date of Patent: April 21, 1981Assignee: Uniroyal, Inc.Inventors: Edward L. Wheeler, Elmar H. Jancis
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Patent number: 4240970Abstract: Novel products suitable for use as detergents in lubricant compositions are provided. Such products include the reaction products of (1) the product of reaction between an alkenylsuccinic acid, ester or anhydride and a hydroxyaromatic compound, (2) the product of reaction between (1) and an amine selected from the group consisting of an alkanepolyol such as an amino alkanediol and a polyalkylenepolyamine; (3) the reaction product of (2) and an aldehyde; (4) the reaction product of (3) with a metal salt capable of forming a stable complex with amines; (5) the reaction product of (2) with a metal salt; and (6) the product of reaction between an alkenylsuccinic acid or anhydride and an alkyl phenyl ether.Type: GrantFiled: December 18, 1979Date of Patent: December 23, 1980Assignee: Mobil Oil CorporationInventor: Sheldon Chibnik
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Patent number: 4232042Abstract: The invention relates to novel compounds of general formula I: ##STR1## and salts, esters and amides thereof, in which R.sub.1 and R.sub.2 represent hydrogen, alkyl or alkenyl (1-4 C),R.sub.3 represents hydrogen, halogen, hydroxy, alkyl (1-4 C) or alkoxy (1-4 C),n has the value 0, 1 or 2 andALK is a saturated or unsaturated hydrocarbon radical with 3-12 carbon atoms, in which a straight carbon chain in between the benzene rings is present, containing 3-8 carbon atoms, andthe dotted line indicates an optional extra bond between the first and second carbon counted from the phenyl ring, in case of an extra bond the group R.sub.2 and one hydrogen attached to said second carbon being absent, having valuable hypocholesterolaemic and hypotriglyceriolaemic properties.Type: GrantFiled: October 4, 1976Date of Patent: November 4, 1980Assignee: Akzona IncorporatedInventors: Alexander C. Campbell, Colin L. Hewett, Filippus J. Zeelen
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Patent number: 4230484Abstract: A method of controlling pollen formation in a hermaphrodite plant, the method comprising applying to the plant, to seed of the plant or to the locus surrounding the plant or seed, a compound of formula: ##STR1## wherein R.sup.1 is hydrogen or alkyl, R.sup.2 is hydrogen, alkyl, alkyl substituted with up to three halogens (e.g. trichloro- or trifluoro-methyl), cycloalkyl, alkoxyalkyl (e.g. 2-methoxy-ethyl), substituted or unsubstituted aryl or aralkyl or an alkali metal (e.g. sodium or potassium), alkaline earth metal or quaternary ammonium cation, R.sup.3 is halogen, nitro, alkyl, alkyl substituted with up to three halogens (e.g. trichloro- or trifluoro-methyl), cycloalkyl, alkoxy, alkylthio, amino, acylamino (e.g. acetylamino), mono- or di-alkylamino, acyl (e.g. acetyl), haloacyl (e.g. bromoacetyl), cyano, amido, hydroxy, carboxy, alkoxycarbonyl (e.g.Type: GrantFiled: April 25, 1978Date of Patent: October 28, 1980Assignee: Imperial Chemical Industries LimitedInventors: Jeremy J. Batch, Keith P. Parry, Colin F. Rowe, David K. Lawrence, Michael J. Brown
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Patent number: 4229363Abstract: New 4-hydroxy-3-(substitutedmethyl)benzeneacetic acids have been prepared which are useful as starting materials in the preparation of cephalosporin and penicillin derivatives.Type: GrantFiled: September 7, 1978Date of Patent: October 21, 1980Assignee: Yeda Research and Development Co., Ltd.Inventors: Abraham Nudelman, Abraham Patchornik
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Patent number: 4228297Abstract: An improved process for the production of hydroxyalkylphenyl derivatives, especially esters and amides containing hydroxyalkylphenyl groups is disclosed, which process comprises gradually adding methyl acrylate, in the presence of an alkaline catalyst, to the alkyl substituted phenolic compound, and adding to the resultant reaction mixture a suitable alcohol or amine, optionally in the presence of a second catalyst which is different from the first catalyst. The improved process results in good yields and in a reduction of undesirable by-products while avoiding isolation of the intermediates.Type: GrantFiled: March 21, 1979Date of Patent: October 14, 1980Assignee: Ciba-Geigy CorporationInventors: Joerg Haeberli, Kyong P. Park, Anthony F. Vellturo, George F. Nurnberger
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Patent number: 4204001Abstract: The disclosure relates to .omega.-aryl substituted .omega.-nor prostaglandin analogues bearing an oxygenated function at C-10, such as a hydroxy radical, or a 9,10- or 10,11-epoxide. A typical compound is 16-(3-chlorophenoxy)-9.alpha.,10.beta.,11.alpha.,15.alpha.-tetrahydroxy-17 ,18,19,20-tetranor-5-cis,13-trans-prostadienoic acid. Also disclosed are chemical processes for the manufacture of said compounds, pharmaceutical and veterinary compositions containing said compounds, and a method of achieving luteolysis in mammals by the use of such compounds.Type: GrantFiled: May 30, 1978Date of Patent: May 20, 1980Assignee: Imperial Chemical Industries LimitedInventors: Jean Bowler, Graham E. Robinson
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Patent number: 4196301Abstract: Ester and amides having the formula ##STR1## wherein R, R.sup.1 and R.sup.2 are independently lower alkyl or cycloalkyl groups, R.sup.3 is hydrogen, alkyl, cycloalkyl, alkylene, phenyl, phenyl substituted by alkyl groups, alkylthioethyl, thiobis-alkylene, alkyleneoxyalkylene, polyoxyalkylene or a polyvalent cyclic or acyclic hydrocarbon radical, R.sup.4 is hydrogen, lower alkyl, cycloalkyl, R.sup.5 is hydrogen, alkyl, phenyl, phenyl substituted by alkyl groups, alkylene, a polyvalent cyclic or acyclic hydrocarbon radical or alkyleneoxyalkylene, A is lower alkylene, m is 1 to 4 and n is 1 to 6.Type: GrantFiled: March 30, 1978Date of Patent: April 1, 1980Assignee: Ciba-Geigy CorporationInventors: John D. Spivack, Martin Dexter
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Patent number: 4192796Abstract: Tertiary phosphine oxide compounds are disclosed as well as their use as stabilizers for polymers.Type: GrantFiled: March 26, 1979Date of Patent: March 11, 1980Assignee: American Cyanamid CompanyInventors: William L. Mosby, William B. Hardy
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Patent number: 4186139Abstract: Condensation products made by reacting an alpha-hydroxyalkyl hydroxy-aromatic compound also having at least one non-fused hydrocarbyl substituent with at least one olefinic nitrile, carboxylic acid or carboxylic acid derivative are useful as additives for fuels and lubricants. The total number of carbon atoms in the non-fused hydrocarbyl substituents is at least about seven while the alpha-hydroxyalkyl group contains from one to about 36 carbons and the olefinic acid or nitrile reactant usually contains two to about forty carbon atoms. Products made from hydroxymethyl alkyl-substituted phenols and .alpha.,.beta.-olefinic acid derivatives such as maleic anhydride are particularly useful. Similarly useful post-treated products can be made from these condensation products by further reaction with alcohols, amines, metal salts or metals.Type: GrantFiled: August 11, 1978Date of Patent: January 29, 1980Assignee: The Lubrizol CorporationInventor: Charles P. Bryant
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Patent number: 4179449Abstract: Condensation products made by reacting an alpha-haloalkyl hydroxy-aromatic compound also having at least one non-fused hydrocarbyl substituent with at least one olefinic nitrile, carboxylic acid or carboxylic acid derivative are useful as additives for fuels and lubricants. The number of carbon atoms in the aromatic hydrocarbyl compound's substituents are each about 25 while the haloalkyl group contains from one to about 36 carbons. The acid or nitrile reactant usually contains three to about forty carbons. Products made from halomethyl alkyl-substituted phenols and .alpha.,.beta.-olefinic diacid derivatives such as maleic anhydride are particularly useful. Similarly useful products can be made from these condensation products by further reacting their acid, acid derivative or nitrile groups with alcohols, polyols, monoamines, polyamines, metal salts or metals.Type: GrantFiled: August 11, 1978Date of Patent: December 18, 1979Assignee: The Lubrizol CorporationInventor: David E. Ripple
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Patent number: 4171298Abstract: New ortho-alkylhydroxybenzylpropanediol compounds of carboxylic acids, aldehydes, ketones, phosphites, phosphates, and phosphonates are disclosed. The propanediol compounds have in the molecule from one to four preferably from one to three ortho-alkylhydroxybenzylpropanediol units, each of which carries one to two ortho-alkylhydroxybenzyl groups, and are highly effective stabilizers for a variety of synthetic resins.Stabilizer compositions comprising a orthoalkylhydroxybenzylpropanediol compound and a known polymer stabilizer, as well as synthetic resins stabilized with such stabilizer compositions, are also disclosed.Type: GrantFiled: October 31, 1977Date of Patent: October 16, 1979Assignee: Argus Chemical CorporationInventors: Motonobu Minagawa, Yutaka Nakahara, Masayuki Takahashi
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Patent number: 4153597Abstract: A stabilizer suitable for use to protect organic materials into which it is soluble or miscible against oxidative degradation having the general formula ##STR1## wherein R.sub.1 and R.sub.2 are lower alkyl or a radical of the structure ##STR2## wherein "x" represents a tertiary butyl radical.Type: GrantFiled: June 26, 1978Date of Patent: May 8, 1979Assignee: Uniroyal, Inc.Inventors: Edward L. Wheeler, Elmar H. Jancis
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Patent number: 4145556Abstract: Novel N,N'-bis?(alkylhydroxyphenyl)alkanoyloxyhydrocarbyl!oxamides which can be prepared by reacting an alkylhydroxyphenylalkanoic acid, an ester or anhydride thereof or a corresponding acid halide with an N,N'-bis(hydroxyhydrocarbyl)oxamide, are useful as stabilizers of organic materials normally subject to oxidative deterioration, e.g. polymers such as polyolefins.Type: GrantFiled: December 21, 1977Date of Patent: March 20, 1979Assignee: Monsanto CompanyInventors: Richard H. Hirsch, William H. Selcer
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Patent number: 4139545Abstract: Novel compounds of the formulae ##STR1## wherein R represents lower alkyl or lower alkoxy, A represents --CH.sub.2 --, --CO-- or ##STR2## n represents an integer of 1 to 8, X represents hydrogen or hydroxyl which may be protected and Y represents hydroxyl which may be protected, and their esters show an excellent action on the lysosomal membranes of cells, and exhibit excellent pharmacological activities such as physiologic host defense control activity, especially immuno-potentiating activity.Type: GrantFiled: April 30, 1975Date of Patent: February 13, 1979Assignee: Takeda Chemical Industries, Ltd.Inventors: Hiroshi Morimoto, Isuke Imada, Masazumi Watanabe, Mitsuru Kawada
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Patent number: 4134879Abstract: Compounds of the general formula I ##STR1## in which R.sub.1 and R.sub.5 independently of one another denote hydrogen or lower alkyl, one of R.sub.2 and R.sub.3 denotes hydroxyl and the other denotes alkyl, cycloalkyl or aralkyl, R.sub.4 denotes hydrogen or, if R.sub.3 denotes hydroxyl, additionally also denotes alkyl, cycloalkyl or aralkyl, X denotes a group ##STR2## wherein R.sub.8 is alkyl, aralkyl or phenyl and R.sub.9 is alkyl, aralkyl, phenyl or the group ##STR3## or R.sub.9 and R.sub.8 together are alkylene, Y.sub.1 and Y.sub.2 independently of one another denote oxygen or sulphur, p denotes 1 or 2, q denotes 0 or 1, with the proviso that p + q = 2, and R.sub.6, if q is 0, denotes alkyl, cycloalkyl, aralkyl or thiaalkyl, in which case Y.sub.1 is linked to a carbon atom in the thiaalkyl radical which does not carry a further hetero-atom, or denotes oxaalkyl, in which case Y.sub.Type: GrantFiled: November 5, 1976Date of Patent: January 16, 1979Assignee: Ciba-Geigy CorporationInventor: Andreas Schmidt
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Patent number: 4124724Abstract: Novel crystalline products of manufacture are represented by the formula: ##STR1## wherein R.sub.1 and R.sub.2 are selected from the group consisting of hydroxyl and the caffeoyl group, with the limitation that only one of R.sub.1 and R.sub.2 can be hydroxyl, and the pharmaceutically acceptable salts of the indicated compounds. The compounds are useful as anti-venom agents for hemolytic snake venoms. Pharmaceutical preparations containing the above compounds, or the compound commonly known as caffeic acid wherein both R.sub.1 and R.sub.2 are hydroxyl, are provided for treatment of snakebite victims, as well as the method of using those preparations in such treatment.Type: GrantFiled: November 29, 1976Date of Patent: November 7, 1978Inventor: John W. Agoro
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Patent number: 4120867Abstract: Monoradioiodinated derivatives of compounds employed in a radioassay prepared from precursors which are either active esters, amino acids, or amines, including a phenolic or imidazole substituent group in which one of the possible two sites on the group for radioiodination is substituted to permit production of a monoradioiodinated derivative. A preferred precursor is an active ester of 3-fluoro-5-radioidotyrosine which can be coupled to a compound including an amino group to produce a monoradioiodinated derivative of the compound.Type: GrantFiled: September 29, 1976Date of Patent: October 17, 1978Assignee: Becton, Dickinson & CompanyInventors: Anandrao S. Akerkar, Herman Rutner
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Patent number: 4107137Abstract: This invention relates to compounds of formula Q--O--R--O--Q wherein Q represents a substituted or unsubstituted 2-(2-hydroxybenzyl) phenyl group, and R is a residue of a di- or tri-basic, organic or inorganic acid. Compounds in accordance with the invention can be used as stabilizers for plastics materials, in particular to provide them with thermal stability and stability against ultra violet light. The low volatilities of these compounds compared with the analogous di-phenols Q--O--H render them of particular value.Type: GrantFiled: December 23, 1976Date of Patent: August 15, 1978Assignee: Societe Francaise d'Organo SyntheseInventors: Yves Proux, Christian Julien
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Patent number: 4103025Abstract: Pharmaceutically active compounds of the formula ##STR1## wherein --OR.sub.1, --OR.sub.2, --OR.sub.3 and --OR.sub.4, which may be the same or different, each represents a free or esterified hydroxyl group and --COOR.sub.5 represents a free or esterified carboxyl group, are provided together with processes for their production and pharmaceutical compositions containing them. Compounds of formula II and III possess valuable cicatrizing and anti-inflammatory properties.Type: GrantFiled: March 17, 1977Date of Patent: July 25, 1978Assignee: Inverni Della Beffa S.p.A.Inventor: Giuseppe Mustich
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Patent number: 4085132Abstract: An improved process for the production of hydroxyalkylphenyl derivatives, especially esters containing hydroxyalkylphenyl groups is disclosed, which process comprises gradually adding methyl acrylate, in the presence of an alkaline catalyst, to the alkyl substituted phenolic compound and a suitable alcohol. The improved process results in good yields and in a reduction of undesirable by-products while avoiding isolation of the intermediates.Type: GrantFiled: June 24, 1975Date of Patent: April 18, 1978Assignee: Ciba-Geigy CorporationInventors: Kyong P. Park, Anthony F. Vellturo
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Patent number: 4049713Abstract: The compounds are esters and amides of trialkylhydroxyphenylalkanoic acid having the formula ##STR1## wherein R, R.sup.1 and R.sup.2 are independently lower alkyl or cycloalkyl groups, R.sup.3 is hydrogen, alkyl, cycloalkyl, alkylene, phenyl, phenyl substituted by alkyl groups, alkylthioethyl, thiobis-alkylene, alkyleneoxyalkylene, polyoxyalkylene or a polyvalent cyclic or acyclic hydrocarbon radical, R.sup.4 is hydrogen, lower alkyl, cycloalkyl, R.sup.5 is hydrogen, alkyl, phenyl, phenyl substituted with alkyl groups, alkylene, polyoxyalkylene or polyvalent cyclic or acyclic hydrocarbon radical, A is lower alkylene, m is 1 to 4 and n is 1 to 6.The compounds are useful as stabilizers for organic materials, especially polyolefins, which deteriorate upon exposure to light and heat.Type: GrantFiled: May 3, 1976Date of Patent: September 20, 1977Assignee: Ciba-Geigy CorporationInventor: John D. Spivack