Phenolic Hydroxy Or Metallate Patents (Class 560/75)
  • Patent number: 4334079
    Abstract: 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: Grant
    Filed: November 3, 1980
    Date of Patent: June 8, 1982
    Assignee: Eli Lilly and Company
    Inventors: James M. Greene, Charles A. Bunnell
  • Patent number: 4332734
    Abstract: 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: Grant
    Filed: December 9, 1980
    Date of Patent: June 1, 1982
    Assignee: The Dow Chemical Company
    Inventors: Edmund P. Woo, Michael J. Mullins
  • Patent number: 4329507
    Abstract: 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: Grant
    Filed: January 14, 1980
    Date of Patent: May 11, 1982
    Assignee: Mitsubishi Petrochemical Co., Ltd.
    Inventors: Makoto Takeda, Masayuki Uchide, Hiroshi Iwane
  • Patent number: 4327036
    Abstract: 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: Grant
    Filed: May 8, 1980
    Date of Patent: April 27, 1982
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Frank D. Marsh
  • Patent number: 4313956
    Abstract: 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: Grant
    Filed: December 28, 1979
    Date of Patent: February 2, 1982
    Assignee: INTERx Research Corp.
    Inventors: Nicholas S. Bodor, Kenneth B. Sloan, Stefano A. Pogany
  • Patent number: 4311706
    Abstract: 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: Grant
    Filed: January 22, 1980
    Date of Patent: January 19, 1982
    Assignee: INTERx Research Corporation
    Inventors: Nicholas S. Bodor, Kenneth B. Sloan, Stefano A. Pogany
  • Patent number: 4305868
    Abstract: 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: Grant
    Filed: May 30, 1979
    Date of Patent: December 15, 1981
    Assignee: Uniroyal, Inc.
    Inventors: Edward L. Wheeler, Elmar H. Jancis, Richard A. Gencarelli, Franklin H. Barrows
  • Patent number: 4304714
    Abstract: Novel phenolic oxamide antioxidants for protecting organic materials such as synthetic and natural rubbers, petroleum products, and plastics from oxidative degradation.
    Type: Grant
    Filed: May 30, 1979
    Date of Patent: December 8, 1981
    Assignee: Uniroyal, Inc.
    Inventors: Edward L. Wheeler, Elmar H. Jancis, Richard A. Gencarelli, Franklin H. Barrows
  • Patent number: 4267358
    Abstract: 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: Grant
    Filed: March 13, 1980
    Date of Patent: May 12, 1981
    Assignee: Borg-Warner Corporation
    Inventors: Ingenuin Hechenbleikner, William P. Enlow, James H. Weis
  • Patent number: 4263446
    Abstract: 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: Grant
    Filed: May 30, 1979
    Date of Patent: April 21, 1981
    Assignee: Uniroyal, Inc.
    Inventors: Edward L. Wheeler, Elmar H. Jancis
  • Patent number: 4240970
    Abstract: 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: Grant
    Filed: December 18, 1979
    Date of Patent: December 23, 1980
    Assignee: Mobil Oil Corporation
    Inventor: Sheldon Chibnik
  • Patent number: 4232042
    Abstract: 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: Grant
    Filed: October 4, 1976
    Date of Patent: November 4, 1980
    Assignee: Akzona Incorporated
    Inventors: Alexander C. Campbell, Colin L. Hewett, Filippus J. Zeelen
  • Patent number: 4230484
    Abstract: 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: Grant
    Filed: April 25, 1978
    Date of Patent: October 28, 1980
    Assignee: Imperial Chemical Industries Limited
    Inventors: Jeremy J. Batch, Keith P. Parry, Colin F. Rowe, David K. Lawrence, Michael J. Brown
  • Patent number: 4229363
    Abstract: 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: Grant
    Filed: September 7, 1978
    Date of Patent: October 21, 1980
    Assignee: Yeda Research and Development Co., Ltd.
    Inventors: Abraham Nudelman, Abraham Patchornik
  • Patent number: 4228297
    Abstract: 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: Grant
    Filed: March 21, 1979
    Date of Patent: October 14, 1980
    Assignee: Ciba-Geigy Corporation
    Inventors: Joerg Haeberli, Kyong P. Park, Anthony F. Vellturo, George F. Nurnberger
  • Patent number: 4204001
    Abstract: 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: Grant
    Filed: May 30, 1978
    Date of Patent: May 20, 1980
    Assignee: Imperial Chemical Industries Limited
    Inventors: Jean Bowler, Graham E. Robinson
  • Patent number: 4196301
    Abstract: 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: Grant
    Filed: March 30, 1978
    Date of Patent: April 1, 1980
    Assignee: Ciba-Geigy Corporation
    Inventors: John D. Spivack, Martin Dexter
  • Patent number: 4192796
    Abstract: Tertiary phosphine oxide compounds are disclosed as well as their use as stabilizers for polymers.
    Type: Grant
    Filed: March 26, 1979
    Date of Patent: March 11, 1980
    Assignee: American Cyanamid Company
    Inventors: William L. Mosby, William B. Hardy
  • Patent number: 4186139
    Abstract: 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: Grant
    Filed: August 11, 1978
    Date of Patent: January 29, 1980
    Assignee: The Lubrizol Corporation
    Inventor: Charles P. Bryant
  • Patent number: 4179449
    Abstract: 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: Grant
    Filed: August 11, 1978
    Date of Patent: December 18, 1979
    Assignee: The Lubrizol Corporation
    Inventor: David E. Ripple
  • Patent number: 4171298
    Abstract: 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: Grant
    Filed: October 31, 1977
    Date of Patent: October 16, 1979
    Assignee: Argus Chemical Corporation
    Inventors: Motonobu Minagawa, Yutaka Nakahara, Masayuki Takahashi
  • Patent number: 4153597
    Abstract: 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: Grant
    Filed: June 26, 1978
    Date of Patent: May 8, 1979
    Assignee: Uniroyal, Inc.
    Inventors: Edward L. Wheeler, Elmar H. Jancis
  • Patent number: 4145556
    Abstract: 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: Grant
    Filed: December 21, 1977
    Date of Patent: March 20, 1979
    Assignee: Monsanto Company
    Inventors: Richard H. Hirsch, William H. Selcer
  • Patent number: 4139545
    Abstract: 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: Grant
    Filed: April 30, 1975
    Date of Patent: February 13, 1979
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hiroshi Morimoto, Isuke Imada, Masazumi Watanabe, Mitsuru Kawada
  • Patent number: 4134879
    Abstract: 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: Grant
    Filed: November 5, 1976
    Date of Patent: January 16, 1979
    Assignee: Ciba-Geigy Corporation
    Inventor: Andreas Schmidt
  • Patent number: 4124724
    Abstract: 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: Grant
    Filed: November 29, 1976
    Date of Patent: November 7, 1978
    Inventor: John W. Agoro
  • Patent number: 4120867
    Abstract: 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: Grant
    Filed: September 29, 1976
    Date of Patent: October 17, 1978
    Assignee: Becton, Dickinson & Company
    Inventors: Anandrao S. Akerkar, Herman Rutner
  • Patent number: 4107137
    Abstract: 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: Grant
    Filed: December 23, 1976
    Date of Patent: August 15, 1978
    Assignee: Societe Francaise d'Organo Synthese
    Inventors: Yves Proux, Christian Julien
  • Patent number: 4103025
    Abstract: 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: Grant
    Filed: March 17, 1977
    Date of Patent: July 25, 1978
    Assignee: Inverni Della Beffa S.p.A.
    Inventor: Giuseppe Mustich
  • Patent number: 4085132
    Abstract: 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: Grant
    Filed: June 24, 1975
    Date of Patent: April 18, 1978
    Assignee: Ciba-Geigy Corporation
    Inventors: Kyong P. Park, Anthony F. Vellturo
  • Patent number: 4049713
    Abstract: 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: Grant
    Filed: May 3, 1976
    Date of Patent: September 20, 1977
    Assignee: Ciba-Geigy Corporation
    Inventor: John D. Spivack