Carboxyl, Not Bonded Directly To A Ring, In Acid Moiety Patents (Class 560/105)
  • Patent number: 4271310
    Abstract: Cholinesterase activity is determined by means of the choline and/or acid obtained by the action of cholinesterase on a compound of the formula: ##STR1## [wherein A represents a hydrogen atom or a C.sub.1-5 alkyl or alkoxy group and B represents a group of the formula --R-COO-- (in which --R-- represents an alkenyl group with 2 to 6 carbon atoms); or A represents a hydroxy group in either or both o-positions of the benzene ring or a C.sub.1-5 alkyl group and B represents a group of the formula --COO--; X represents a stabilizing anion and n represents the charge on the anion]. The method of the invention ensures a high resistance to saturation, good stability of the compounds used as substrates, a conveniently low reaction rate and a high degree of accuracy.Certain of the compounds of formula I as defined above are novel compounds which are claimed per se.Examples of the method of the present invention are given and the preparation of the novel compounds is described and exemplified.
    Type: Grant
    Filed: April 12, 1979
    Date of Patent: June 2, 1981
    Assignee: Kyowa Hakko Kogyo Kabushiki Kaisha
    Inventors: Katsuyuki Watanabe, Tadatoshi Hayashi, Hiroaki Hayashi, deceased, by Atsuko Hayashi, heir, by Yuko Hayashi, heir, Toshio Tatano, Yoshiaki Shmizu
  • Patent number: 4268687
    Abstract: The present invention provides a novel process for the production of methyl or ethyl ester of (3-trifluoromethylphenyl)-acetic acid. The process comprises the steps of:(a) converting (3-trifluoromethyl)-benzotrichloride to the corresponding benzoyl chloride,(b) cyanation of the benzoyl chloride to produce the corresponding benzoyl cyanide,(c) hydrolyzing the benzoyl cyanide to produce the corresponding keto-acid,(d) hydrogenating the keto-acid to produce (3-trifluoromethylphenyl)-alpha-hydroxyacetic acid,(e) hydrogenating (3-trifluoromethylphenyl)-alpha-hydroxyacetic acid in the presence of glacial acetic acid to produce the corresponding substituted acetic acid, and(f) esterifying the substituted acetic acid using an alcohol selected from the group consisting of methyl and ethyl to obtain the corresponding methyl or ethyl ester of (3-trifluoromethylphenyl)-acetic acid.
    Type: Grant
    Filed: November 7, 1979
    Date of Patent: May 19, 1981
    Assignee: Hooker Chemicals & Plastics Corp.
    Inventors: David Y. Tang, Arthur M. Foster
  • Patent number: 4268685
    Abstract: Esters of salicylamide with anti-inflammatory and analgesic action are disclosed.These esters have the following general formula: ##STR1## wherein R is a radical of an acid selected among d-2-(6'-methoxy-2'-naphtyl)-propionic acid, 2[[3-(trifluoromethyl)phenyl]-amino]-3-pyridine carboxylic acid, 2- {[3-(trifluoromethyl)-phenyl]-amino}-3-pyridincarboxylic acid, 2-(4-isobutyl-phenyl)-propionic acid, 4-allyloxy-3-chloro-phenylacetic acid, 2-(3-benzoylphenyl)-propionic acid, 2-[(2,3-dimethylphenyl)amino]-benzoic acid and 2[[3-trifluoromethyl)phenyl]-amino]benzoic acid.The process for preparing the subject esters comprises reacting a halide, preferably a chloride of the desired acid, with a solution of salicylamide.
    Type: Grant
    Filed: March 12, 1980
    Date of Patent: May 19, 1981
    Assignee: Neopharmed S.p.A.
    Inventor: Alberto Reiner
  • Patent number: 4266082
    Abstract: A process for the preparation of 4-fluoro-3-phenoxy-toluene of the formula ##STR1## comprising reacting 3-bromo-4-fluoro-toluene, of the formula ##STR2## with potassium phenolate, or with sodium phenolate in the presence of a potassium salt, in a diluent in the presence of copper as catalyst at a temperature between about 120.degree. and 180.degree. C.
    Type: Grant
    Filed: August 17, 1979
    Date of Patent: May 5, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Reimer Collin, Hans-Joachim Diehr, Uwe Friesnitz
  • Patent number: 4266074
    Abstract: Substituted acetate compounds represented by the formula ##STR1## which are useful as pesticides and pesticidal composition containing the substituted acetate compounds as active ingredients, as well as processes for preparing the compounds and the compositions are disclosed.
    Type: Grant
    Filed: July 16, 1975
    Date of Patent: May 5, 1981
    Assignee: Sumitomo Chemical Company Limited
    Inventors: Keimei Fujimoto, Nobuo Ohno, Yoshitoshi Okuno, Toshio Mizutani, Isao Ohno, Masachika Hirano, Nobushige Itaya, Takashi Matsuo
  • Patent number: 4264775
    Abstract: A simple process for the preparation of .beta.-aminostyrenes proceeds from anilines by successively diazotizing, reacting with a vinyl ester, and reacting with a secondary amine without purification of the intermediate products. The compounds are reactive enamines useful in organic synthesis.
    Type: Grant
    Filed: October 27, 1976
    Date of Patent: April 28, 1981
    Assignee: Eli Lilly and Company
    Inventor: William A. White
  • Patent number: 4263447
    Abstract: Allylic cycloalkenols and/or allylic cycloalkenol esters are prepared by autoxidation of the corresponding cycloolefins using elemental oxygen contacted with solutions of cycloolefins containing catalytic amounts of soluble cobalt and copper compounds with a carboxylic acid activator.
    Type: Grant
    Filed: July 16, 1979
    Date of Patent: April 21, 1981
    Assignee: Union Carbide Corporation
    Inventors: Benjamin Phillips, Walter J. Skraba, Daniel W. McNeil
  • Patent number: 4263443
    Abstract: Hydrocarbons and esters and/or acids are produced by heating aldehydes in the presence of an alcohol or an alcohol equivalent and in the presence of an iodine or bromine moiety and a rhodium or iridium catalyst.
    Type: Grant
    Filed: November 22, 1978
    Date of Patent: April 21, 1981
    Assignee: Halcon Research and Development Corp.
    Inventor: John F. White
  • Patent number: 4263319
    Abstract: Novel compounds of the formula ##STR1## are disclosed in which R.sup.1 is a phenyl, phenoxy, phenylthio, benzyl or heterocyclic radical which may be substituted, and R.sup.2 is hydrogen, a substituted-vinylcyclopropanecarbonyl group, a tetramethylcyclopropanecarbonyl group, or a 1-(substituted-phenyl)-2-methylpropylcarbonyl group. The compounds wherein R.sup.2 is other than hydrogen are insecticides.
    Type: Grant
    Filed: May 24, 1979
    Date of Patent: April 21, 1981
    Assignee: FMC Corporation
    Inventor: John F. Engel
  • Patent number: 4260551
    Abstract: Polyprenyl derivatives having the formula ##STR1## in which R.sup.1 and R.sup.2 may be the same or different and each represents hydrogen atom, hydroxyl group, an alkoxy group having 1-8 carbon atoms, an aliphatic acyloxy group having 2-18 carbon atoms, an aromatic acyloxy group or an araliphatic acyloxy group having 2-3 carbon atoms in the aliphatic acyl moiety, R.sup.3 represents hydrogen atom, an alkyl group having 1-8 carbon atoms, an aliphatic acyl group having 2-18 carbon atoms, an aromatic acyl group or an araliphatic acyl group having 2-3 carbon atoms in the aliphatic acyl moiety, n is an integer of 1-4 and, when n is an integer of 2-4, R.sup.2 's may be the same or different; provided that, when n is 1 or 2, at least one of R.sup.1 and R.sup.2 's is hydroxyl group, an alkoxy group, an aliphatic acyloxy group, an aromatic acyloxy group or an araliphatic acyloxy group. These derivatives are useful as medicines for treating peptic ulcer.
    Type: Grant
    Filed: February 12, 1979
    Date of Patent: April 7, 1981
    Assignee: Sankyo Company Limited
    Inventors: Hiroshi Mishima, Akira Ogiso, Shinsaku Kobayashi
  • Patent number: 4260811
    Abstract: The level of 2-oxazoline or an oxazine impurity in an isocyanatoalkyl ester of an organic carboxylic acid is reduced by (i) reacting the impurity with an organic acid chloride, a chloroformate, a thiochloroformate, a sulfonyl chloride, phosphoryl chloride, sulfuryl chloride or thionyl chloride and (ii) fractionally distilling the reaction mixture to recover the isocyanatoalkyl ester. As an example, crude 2-isocyanatoethyl methacrylate (IEM) containing 0.19 weight percent 2-isopropenyl-2-oxazoline (IPO) is contacted with terephthaloyl chloride for 0.5 hour at 90.degree. C. The reaction mixture is fractionally distilled to recover 97 weight percent of the IEM containing only 0.02 weight percent IPO.
    Type: Grant
    Filed: January 14, 1980
    Date of Patent: April 7, 1981
    Assignee: The Dow Chemical Company
    Inventor: Abel Mendoza
  • Patent number: 4259350
    Abstract: Iodopropargyl derivatives of formula:IC.tbd.CCH.sub.2 OR[wherein R represents an alkanoyl group (which may be unsubstituted or have one or more halogen, cyano, substituted or unsubstituted .alpha.
    Type: Grant
    Filed: March 13, 1979
    Date of Patent: March 31, 1981
    Assignee: Sankyo Company Limited
    Inventors: Yasuhiro Morisawa, Kiyoshi Konishi, Mitsuru Kataoka
  • Patent number: 4255591
    Abstract: There is provided an improved continuous homogeneous catalytic carbonylation process wherein a mixed gas stream is removed from the carbonylation reactor, condensable liquids separated from said gas stream and said gas stream vented, the improvement comprising contacting said gas stream with a plurality of hollow fiber membranes selectively permeable to hydrogen under conditions substantially non-degrading of the membranes to generate a non-permeated gas stream of higher carbon monoxide content and recycling said non-permeated gas stream to the carbonylation process reactor. There is also provided for the recovery and recycle to the process of carbonylation products such as acetic or propionic acids by adsorption and removal from a solid adsorbent or absorption in a liquid absorbent.
    Type: Grant
    Filed: November 20, 1978
    Date of Patent: March 10, 1981
    Assignee: Monsanto Company
    Inventors: Earle C. Makin, Jerry L. Price, Yu W. Wei
  • Patent number: 4249019
    Abstract: A carboxylic ester is produced in one step in a high yield and with a high selectivity by reacting an aldehyde with an alcohol in the presence of oxygen by using a catalyst comprising (I) palladium, (II) at least one compound selected from the group consisting of lead compounds, thallium compounds and mercury compounds and (III) at least one compound selected from the group consisting of alkali metal compounds and alkaline earth metal compounds.
    Type: Grant
    Filed: November 13, 1978
    Date of Patent: February 3, 1981
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Nobuhiro Tamura, Yohei Fukuoka, Setsuo Yamamatsu, Yoshio Suzuki, Ryoichi Mitsui, Tadayuki Ibuki
  • Patent number: 4242357
    Abstract: 3-Phenoxybenzyl alcohols and carboxylic acid esters thereof for combating pests of the formula ##STR1## in which R and R.sup.1 are different and each represent hydrogen, fluorine or bromine,R.sup.2 represents cyano or ethynyl andR.sup.3 represents the ##STR2## or the ##STR3## wherein the phenyl ring can optionally carry one or more substituents selected independently from halogen, alkyl, alkylthio and alkoxy with in each case 1 to 4 carbon atoms, nitro and methylenedioxy, andR.sup.4 and R.sup.5 are identical and each represent chlorine, bromine or methyl, andR.sup.2 represents hydrogen in case thatR.sup.3 represents the ##STR4## wherein R.sup.4 and R.sup.5 are identical and each represent chlorine or bromine andR.sup.3 represents the ##STR5## wherein the phenyl ring can carry the above mentioned substituents which possess insecticidal and acaricidal properties. The benzyl alcohols from which the esters are made are also new.
    Type: Grant
    Filed: March 31, 1977
    Date of Patent: December 30, 1980
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rainer A. Fuchs, Ingeborg Hammann, Wolfgang Behrenz, Bernhard Homeyer, Wilhelm Stendel
  • Patent number: 4238413
    Abstract: The present invention relates to a novel organic compound, (3-trifluoromethyl)-benzoyl cyanide, and a process for the preparation thereof comprising(a) converting (3-trifluoromethyl)-benzotrichloride to the corresponding benzoyl chloride,b) cyanation of the benzoyl chloride to produce the corresponding benzoyl cyanide, (3-trifluoromethyl)-benzoyl cyanide.
    Type: Grant
    Filed: November 7, 1979
    Date of Patent: December 9, 1980
    Assignee: Hooker Chemicals & Plastics Corp.
    Inventors: David Y. Tang, Arthur M. Foster
  • Patent number: 4237306
    Abstract: Improved supported thallium(III) reagents are provided which significantly improve reaction rates and product selectivity of oxythallation reactions. The present reagents have a thallium(III) salt of an acid on the surface and within montmorillonite clay minerals.
    Type: Grant
    Filed: May 10, 1979
    Date of Patent: December 2, 1980
    Assignee: Emery Industries, Inc.
    Inventors: John F. White, Edward C. Taylor, Chih-Shu Chiang
  • Patent number: 4233206
    Abstract: A process for the production of a colored polyolefin molded articles comprising adding to a polyolefin either a compound of the formula D--CH.sub.2 O.OC--R]).sub.n as a colorant wherein D is the residue of a common organic pigment, R is an alkyl, alkenyl or aryl group having up to 20 carbon atoms and n is an integer of 1-4, or a mixture of the compound of the above formula with at least one usual pigment, to form a mixture, and then molding the mixture thereby producing the desired colored articles. This invention also relates to the compound of said formula and to a mixture thereof with at least one common pigment.
    Type: Grant
    Filed: November 6, 1975
    Date of Patent: November 11, 1980
    Assignee: Toyo Ink Manufacturing Co., Ltd.
    Inventors: Hiromitsu Katsura, Morihiko Endo, Takashi Kanno
  • Patent number: 4233230
    Abstract: A process for preparing esters and halides is disclosed comprising the step of reacting a cyclic olefin having the formula I ##STR1## wherein R.sub.1 and R.sub.4 are the same or different from each other and each represents hydrogen, methyl, or ethyl;R.sub.2 and R.sub.3 are the same or different from each other and each represents hydrogen or alkyl containing 1 to 5 carbon atoms; andn represents a whole number from 2 to 12, with an acyclic olefin having the formula II ##STR2## wherein R.sub.5 represents hydrogen, methyl, ethyl or the group ##STR3## wherein R.sub.12 and R.sub.13 are the same or different from each other and each represents hydrogen or alkyl containing 1 to 5 carbon atoms;Y represents halogen; an acyloxy group R.sub.14 --CO--O wherein R.sub.14 represents alkyl containing 1-12 carbon atoms, phenyl or phenyl alkyl containing 7-12 carbon atoms, or an oxycarbonyl group R.sub.15 --O--CO wherein R.sub.
    Type: Grant
    Filed: May 4, 1978
    Date of Patent: November 11, 1980
    Assignee: Rhone-Poulenc Industries
    Inventor: Jean Otton
  • Patent number: 4233457
    Abstract: This invention relates to an improved process for preparing 5-fluoro-2-methyl-1-(p-methylsulfinylbenzylidene)-3-indenyl acetic acid.
    Type: Grant
    Filed: May 17, 1979
    Date of Patent: November 11, 1980
    Assignee: Merck & Co., Inc.
    Inventors: Robert F. Czaja, Edward J. J. Grabowski
  • 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: 4228109
    Abstract: This invention relates to aliphatic phosphorous containing compounds which are useful as herbicides. Additionally, they demonstrate tolerance towards desired, crops, e.g. wheat and rice.
    Type: Grant
    Filed: August 1, 1978
    Date of Patent: October 14, 1980
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Richard F. Sauers
  • Patent number: 4227015
    Abstract: Aryl substituted diketones and keto-esters, useful as antiviral agents and insecticides, are prepared by reacting an arylalkyl or arylalkenyl iodide with a metal salt of the appropriate diketone or keto-ester. The intermediate iodides are prepared by condensing a methyl cyclopropyl ketone with an aromatic aldehyde to give an arylvinyl cyclopropyl ketone, reducing the latter to an arylethyl cyclopropyl carbinol or arylvinyl cyclopropyl carbinol, treating the carbinol with phosphorus tribromide and then with zinc bromide to give an arylalkyl or arylalkenyl bromide, and then replacing the bromine atom by iodine.
    Type: Grant
    Filed: February 14, 1979
    Date of Patent: October 7, 1980
    Assignee: Sterling Drug Inc.
    Inventor: Joseph C. Collins
  • Patent number: 4225726
    Abstract: This invention relates to an improved method for the catalyzed condensation of aldehydes in the liquid phase to form 1,3-glycol monoesters utilizing tin metal or a tin oxide catalyst. Condensation can be visualized as an aldol condensation followed by a Tischenko reaction between the aldol and a third molecule of aldehyde. In its simplest form the condensation can be illustrated by the following general formula ##STR1## R or R.sup.1 =Hydrogen or alkyl group of 1 to 20 carbon atoms or aromatic groups. R and R.sup.1 can also be part of a cyclic system.
    Type: Grant
    Filed: May 23, 1979
    Date of Patent: September 30, 1980
    Assignee: Eastman Kodak Company
    Inventors: Don L. Morris, Anthony W. McCollum
  • Patent number: 4225521
    Abstract: This invention relates to phosphorus containing compounds which are useful as herbicides.Additionally, they demonstrate tolerance towards desired crops, e.g., cotton, soybeans and sugarbeets.
    Type: Grant
    Filed: August 1, 1978
    Date of Patent: September 30, 1980
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Richard F. Sauers
  • Patent number: 4221918
    Abstract: Carboxylic acid anhydrides are contacted with hydrogen in the presence of an insoluble metal hydrogenation catalyst and strong protonic acid to produce 1,1-diesters.
    Type: Grant
    Filed: October 30, 1978
    Date of Patent: September 9, 1980
    Assignee: Chevron Research Company
    Inventor: Shigeto Suzuki
  • Patent number: 4218469
    Abstract: 3-Phenoxy-fluoro-benzyl carboxylic acid esters of the formula ##STR1## in which R.sup.2 is hydrogen, cyano or ethynyl,R.sup.3 is ##STR2## R.sup.4 and R.sup.5 represent chlorine, bromine or methyl, and R.sup.6 is phenyl or phenyl substituted with halogen, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, nitro or methylenedioxy,which possess arthropodicidal properties. The alcohols are also new.
    Type: Grant
    Filed: February 13, 1978
    Date of Patent: August 19, 1980
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rainer Fuchs, Ingeborg Hammann, Wolfgang Behrenz, Wilhelm Stendel
  • Patent number: 4217312
    Abstract: This invention relates to phosphorus containing compounds which are useful as herbicides.Additionally, they demonstrate tolerance towards desired crops, e.g., cotton, soybeans and sugarbeets.
    Type: Grant
    Filed: August 1, 1978
    Date of Patent: August 12, 1980
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Richard F. Sauers
  • Patent number: 4215044
    Abstract: Process for preparing an organic compound of the formula R.sup.2 R.sup.2 CFC(O)R.sup.3, which process comprises contacting and reacting in a reaction mixture which includes an inert solvent, at a temperature of -40.degree. C. to -100.degree. C., ROF and ##STR1## R is polyfluoroperhaloalkyl of 1-6 carbon atoms or FOCF.sub.2 ; R.sup.1 is hydrocarbyl of 1-6 carbon atoms;each R.sup.2 is selected from H, alkyl of 1-17 carbon atoms, cycloalkyl of 3-6 carbon atoms, aryl, heteroaryl and such alkyl, cycloalkyl, aryl and heteroaryl substituted by halogen or alkoxy of 1-6 carbon atoms;R.sup.3 is selected from H, alkyl and haloalkyl of 1-16 carbon atoms, cycloalkyl of 3-10 carbon atoms, aryl and haloaryl, OSi(R.sup.1).sub.3, OH, NH.sub.2, alkoxy of 1-6 carbon atoms, aryloxy, NHR.sup.1 and NR.sup.1.sub.2 wherein R.sup.1 is alkyl of 1-6 carbon atoms, N-arylamino and nitrogen or sulfur heterocyclic of 4-5 carbon atoms;R.sup.3 and one R.sup.2 taken together is a diradical which with the C.dbd.
    Type: Grant
    Filed: April 23, 1979
    Date of Patent: July 29, 1980
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: William J. Middleton
  • Patent number: 4206310
    Abstract: An improved process for producing an ester from a carboxylic acid and an alcohol which comprises reacting said carboxylic acid with said alcohol by the use of a 1-substituted-2-halopyridinium salt or a 1-substituted-2-haloquinolinium salt as a condensing agent in the presence of a hydrogen halide captor. According to this process, various esters, even if they have some steric hindrances, may be obtained in good yields.
    Type: Grant
    Filed: September 8, 1978
    Date of Patent: June 3, 1980
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Teruaki Mukaiyama, Masahiro Usui, Kazuhiko Saigo, Eiichiro Shimada
  • Patent number: 4199596
    Abstract: Fluorine substituted phenoxybenzylcarbonyl derivatives of the formula ##STR1## in which R.sup.1 represents hydrogen, cyano or ethynyl andR.sup.2 represents the radical ##STR2## wherein R.sup.3 and R.sup.4, which are identical, each represent chlorine, bromine or methyl, orR.sup.2 represents the radical ##STR3## wherein R.sup.5 represents a phenyl ring which optionally carries one or more substituents each selected independently from halogen, alkyl, alkylthio and alkoxy each with 1-4 carbon atoms, nitro and methylenedioxy,which possess arthropodicidal properties. The benzyl alcohol components of these esters are also new.
    Type: Grant
    Filed: August 10, 1978
    Date of Patent: April 22, 1980
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rainer Fuchs, Ingeborg Hammann, Wolfgang Behrenz, Bernhard Homeyer, Wilhelm Stendel
  • Patent number: 4189596
    Abstract: 2-Aryl-C.sub.2 to C.sub.5 -alkanoic acids and esters thereof are prepared by heating a 2-(2-oxo-3-cyclohexenyl)-alkanoic acid or ester derivative in the presence of a sulfonic acid or a phosphonic acid at 75.degree. C. to 130.degree. C. while providing a means for removing water from the reaction mixture. In the process new butenolide derivative intermediates have been discovered. Alternatively, the 2-aryl-C.sub.2 to C.sub.6 -alkanoic acids can be prepared from the butenolides by forming a mixture of the 2-(2-oxo-3-cyclohexenyl)-alkanoic acid with acetic anhydride in the presence of an acid scavenging base, allowing the mixture to stand for a time sufficient to form an acetate intermediate, heating the resulting mixture to about 75.degree. C. to about 130.degree. C. to form the betenolide intermediates. Thereafter these intermediates can be heated with sulfonic or phosphonic acid as above while removing water to form the 2-aryl-C.sub.2 to C.sub.
    Type: Grant
    Filed: May 2, 1977
    Date of Patent: February 19, 1980
    Assignee: The Upjohn Company
    Inventor: Verlan H. VanRheenen
  • Patent number: 4182761
    Abstract: Acyloxy-substituted aryloxyalkyl diketones, useful as anti-viral agents, are prepared either by esterification of the corresponding hydroxy-substituted compounds or by reacting a haloalkyl diketone with an alkali metal salt of an acyloxy-substituted phenol.
    Type: Grant
    Filed: June 7, 1978
    Date of Patent: January 8, 1980
    Assignee: Sterling Drug Inc.
    Inventors: Joseph C. Collins, Guy D. Diana
  • Patent number: 4181674
    Abstract: The stereospecific alkylation of a novel 3-endo-protected hydroxyl-tricyclo[3,2,0,0.sup.2,7 ]heptan-6-one is described using a range of lithium-, copper or magnesium-containing organometallic reagents. This reaction provides a 5-endo-protected hydroxyl-bicyclo[2,2,1]-heptan-2-one system from which prostaglandin compounds of the F series having a protecting group at the 9-position hydroxyl group may readily be obtained by a sequence of reactions.
    Type: Grant
    Filed: December 2, 1976
    Date of Patent: January 1, 1980
    Assignee: Allen & Hanburys Limited
    Inventors: Roger F. Newton, Stanley M. Roberts, David K. Rainey, Michael J. Dimsdale
  • Patent number: 4173574
    Abstract: Phenolic age resistors such as 4-(3,5-ditertiary butyl-4-hydroxyphenyl)-2-butyl 2-methyl-4-thia-6-octanoyloxyhexanoate are used as antioxidants in diene rubbers, such as butadiene-styrene types and in polyolefins, such as polypropylene.
    Type: Grant
    Filed: October 11, 1977
    Date of Patent: November 6, 1979
    Assignee: The Goodyear Tire & Rubber Company
    Inventor: Richard H. Kline
  • Patent number: 4171318
    Abstract: 9-Substituted, 4- or 6-fluorine substituted retinoic acid derivatives useful as antitumor agents and in the treatment of acne as well as a method for their manufacture are disclosed. Substituents at the 9-position include substituted phenyl, thienyl and furyl groups.
    Type: Grant
    Filed: August 24, 1978
    Date of Patent: October 16, 1979
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Ka-Kong Chan, Beverly A. Pawson
  • Patent number: 4166820
    Abstract: Selenium compounds, and a method of their preparation, are disclosed which have a structure that renders the compounds useful in immunoassays or in competitive protein binding assays wherein either radio-labeled selenium compounds or nonradioactive selenium compounds are used respectively, with radiologic or fluorometric analysis. One class of these compounds have the generalized structural formula of: ##STR1## wherein: X is hydrogen or oxo;R.sub.1 and R.sub.2, together, are ethylene, trimethylene, or 5,6-phenylene;R.sub.3 is alkylene of 1 to 6 carbons;R.sub.4 is alkyl or isoalkyl of 1 to 6 carbons, phenyl or benzyl; orR.sub.3 and R.sub.4 together are 1,2,3-propanetriyl;And n is 1 or 2. The compounds in the aforementioned structure are N-pyrrolidine derivatives wherein R.sub.1 and R.sub.2 together are ethylene; N-succinimdyl derivatives when R.sub.1 and R.sub.2 together are ethylene and the X groups are oxo groups; N-phthalimidyl derivatives when R.sub.1 and R.sub.
    Type: Grant
    Filed: August 4, 1977
    Date of Patent: September 4, 1979
    Inventor: Julian E. Spallholz
  • Patent number: 4166131
    Abstract: This invention provides new compounds of formula I, ##STR1## wherein R.sub.1 is lower alkyl,R.sub.2 is hydrogen or lower alkyl,R.sub.3 is hydrogen or lower alkyl,R.sub.4 is hydrogen or lower alkyl,R.sub.5 is hydrogen, chlorine or lower alkyl, and each ofR.sub.6 and R.sub.7 is hydrogen, or, when R.sub.5 is hydrogen, R.sub.6 may also be chlorine or lower alkyl, and R.sub.7 chlorine or lower alkyl,Useful as anti-phlogistic and anti-arthritic agents.
    Type: Grant
    Filed: October 24, 1974
    Date of Patent: August 28, 1979
    Assignee: Hexachimie Societe Anonyme
    Inventor: Trevor G. Payne
  • Patent number: 4164615
    Abstract: A catalyst comprising a titanium compound, an alkali metal ion, and a halide, is effective for the conversion of conjugated diolefins to diacyloxy olefins.
    Type: Grant
    Filed: August 25, 1977
    Date of Patent: August 14, 1979
    Assignee: Phillips Petroleum Company
    Inventor: Paul R. Stapp
  • Patent number: 4164510
    Abstract: Isopropylphenyl esters are converted to di- or trihydric phenols via a novel autoxidation of the esters at high conversion rates to the corresponding hydroperoxyisopropylphenyl esters in the presence of a catalyst combination comprising at least two members selected from the group consisting of (i) a metal phthalocyanine; (ii) a di-tertiary alkyl peroxide; and (iii) a tertiary alkyl hydroperoxide.Rearrangement of the hydroperoxyisopropylphenyl esters to the corresponding hydroxyphenyl esters and the hydrolysis of the latter compounds provides the phenols in overall yields (from the starting esters) heretofore not obtainable. Novel bis(hydroperoxyisopropylphenyl)carbonates are described which are attractive intermediates for the intermediate bisphenol carbonate or the final hydroquinone hydrolysis product.
    Type: Grant
    Filed: February 21, 1978
    Date of Patent: August 14, 1979
    Assignee: The Upjohn Company
    Inventor: Sheng-Hong A. Dai
  • Patent number: 4162363
    Abstract: Conjugated dienes or monoolefins are converted to diesters in a process utilizing a catalyst system comprising an alkali metal compound and a sulfur source comprising elemental sulfur or a sulfur halide, optionally with a halide source, in carboxylic acid media.
    Type: Grant
    Filed: August 25, 1977
    Date of Patent: July 24, 1979
    Assignee: Phillips Petroleum Company
    Inventor: Paul R. Stapp
  • Patent number: 4162366
    Abstract: New insecticides, organic esters wherein the alcohol moiety is .alpha.-trifluoromethyl-3-phenoxybenzyl alcohol and the acid moiety is a pyrethroid carboxylic acid, are described and shown to control a broad spectrum of insects, including acarids.
    Type: Grant
    Filed: April 7, 1978
    Date of Patent: July 24, 1979
    Assignee: FMC Corporation
    Inventor: John F. Engel
  • Patent number: 4161610
    Abstract: This invention involves a method of producing vinyl esters by the reaction of olefins with carboxylic acids in the presence of alkali and alkaline earth metal salts of carboxylic acids, a noble metal compound, and a regenerative oxidant capable of maintaining the noble metal in oxidized form.
    Type: Grant
    Filed: September 29, 1961
    Date of Patent: July 17, 1979
    Assignee: Union Oil Company of California
    Inventor: Donald L. Klass
  • Patent number: 4159991
    Abstract: .alpha.-Acyloxy-N,N'-diacylmalonamides of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are the same or different and are hydrogen, straight chain or branched alkyl radicals having from one to eleven carbon atoms, or hydrocarbon radicals with six to twelve carbon atoms and comprising at least one aromatic ring, are novel compounds prepared by the action of a mixture of carboxylic acids R.sub.3 COOH and R.sub.4 COOH upon an .alpha.-acyloxymalononitrile, R.sub.1 COO--C(CN).sub.2 --R.sub.2, in the presence of an acid catalyst and are useful as intermediates in organic synthesis and low temperature activators in bleaching or scouring compositions.
    Type: Grant
    Filed: August 22, 1977
    Date of Patent: July 3, 1979
    Assignee: Produits Chimiques Ugine Kuhlmann
    Inventors: Bernard Dubreux, Serve Y. Delavarenne, Jean-Pierre Schirmann
  • Patent number: 4160035
    Abstract: A plant protecting composition with pesticidal effects contains an effective amount of at least one compound of the formula ##STR1## wherein R is a C.sub.1-20 alkyl group or a phenyl or phenyl-C.sub.1-3 alkylene group having optionally one or more C.sub.1-3 alkyl or halogen substituents on the phenyl ring, and a diluent in an amount necessary to make up the final weight of the composition. To kill plant pests, the composition is applied to growing plants either prior to or after emergence.
    Type: Grant
    Filed: November 3, 1977
    Date of Patent: July 3, 1979
    Assignee: Egyt Gyogyszervegyeszeti Gyar
    Inventors: Laszlo Levai, Gyula Mikite, Attila Kis-Tamas
  • Patent number: 4156694
    Abstract: The present invention relates to novel benzo(b) bicyclo[3.3.1]nones of the general formula I: ##STR1## and a salt or nitrogen oxide thereof, in which R.sub.1 and R.sub.2 stand for hydrogen, alkyl of 1-6 carbon atoms, alkenyl of 1-6 carbon atoms, an optionally substituted aralkyl group or an acyl group orR.sub.1 and R.sub.2 together with the nitrogen atom represent a heterocyclic 5- or 6-membered ringR.sub.3 is a free, etherified or esterified hydroxy,X and Y stand for hydrogen, hydroxy, halogen, alkyl or alkoxy of 1-6 C-atoms, nitro, CF.sub.3 or an acyloxy group, having valuable biological activities, particularly anorectic activity.
    Type: Grant
    Filed: December 30, 1977
    Date of Patent: May 29, 1979
    Assignee: Akzona Incorporated
    Inventors: Colin L. Hewett, David S. Savage, James Redpath, Thomas Sleigh, Duncan R. Rae
  • Patent number: 4152455
    Abstract: New insecticides, organic esters wherein the alcohol moiety is .alpha.-trifluoromethyl-3-phenoxybenzyl alcohol and the acid moiety is a pyrethroid carboxylic acid, are described and shown to control a broad spectrum of insects, including acarids.
    Type: Grant
    Filed: February 2, 1977
    Date of Patent: May 1, 1979
    Assignee: FMC Corporation
    Inventor: John F. Engel
  • Patent number: 4150137
    Abstract: The present invention relates to phenylacetic acid ester derivatives of the following general formula: ##STR1## wherein, R is selected from the group consisting of lower alkyl (other than ethyl) and substituted lower alkyl, and R' may be a hydrogen or methyl.The compounds obtained by the present invention possess a high degree of analgetic ,antipyretic and anti-inflammatory activites and cause little side effects on the gastro-intestinal tracts, when administered orally and topically, and they may be useful as oral and topical analgetics, antipyretics and antiinflammatory agents.
    Type: Grant
    Filed: October 25, 1977
    Date of Patent: April 17, 1979
    Assignee: Hisamitsu Pharmaceutical Co. Inc.
    Inventors: Kanji Noda, Akira Nakagawa, Yuji Ishikura, Hiroyuki Ide
  • Patent number: 4146554
    Abstract: A process for the preparation of certain cyano substituted esters and optical isomers thereof useful as insecticides by dehydration of the precursor carboxamido esters.
    Type: Grant
    Filed: June 3, 1977
    Date of Patent: March 27, 1979
    Assignee: Imperial Chemical Industries Limited
    Inventor: Thomas Leigh
  • Patent number: 4142054
    Abstract: 2-Aryl-C.sub.3 to C.sub.6 -alkanoate esters are prepared economically by reacting an enol ether of an aryl alkyl ketone with a trivalent thallium salt in an organic solvent. The trivalent thallium ions can be regenerated by adding a peracid and a reactive form of manganese, ruthenium, cobalt, iridium, hafnium, osmium or neobium to oxidize monovalent thallium ions to the trivalent state, in a sequential, continuous or stoichiometric procedure. A continuous process using a Scheibel column is disclosed. The ester intermediate product is then converted to the corresponding 2-aryl-C.sub.3 - to C.sub.6 -alkanoic acid or salt thereof. The aryl group is selected so the resulting acid product will be a useful compound such as an anti-inflammatory, analgesic and anti-pyretic drug or agriculturally useful product. Examples of drug acids which can be made by this process include ibuprofen, flurbiprofen, fenoprofen and naproxen and the like.
    Type: Grant
    Filed: June 16, 1977
    Date of Patent: February 27, 1979
    Assignee: The Upjohn Company
    Inventors: Sanjay I. Amin, Jerry A. Walker