Patents Examined by Vera C. Clarke
  • Patent number: 5245076
    Abstract: The invention relates to a process for the preparation of known .beta.-halogeno-tert.-alkyl isocyanates of the formula ##STR1## in which X represents chlorine,Y represents hydrogen or chlorine,R.sub.1 represents in each case straight-chain or branched alkyl or halogenoalkyl andR.sub.2 represents in each case straight-chain or branched alkyl, halogenoalkyl or optionally halogen- and/or trifluoromethyl-substituted phenyl,where tert.-alkyl isocyanates of the formula (II) ##STR2## in which R.sub.1 and R.sub.2 have the meaning given above,are converted to the corresponding tert.-alkylcarbamoyl chlorides by means of hydrogen chloride gas, these are reacted with elemental chlorine under irradiation or in the presence of catalysts, and finally the .beta.-halogeno-tert.-alkyl isocyanates are liberated by dehydrohalogenation at elevated temperature.
    Type: Grant
    Filed: April 2, 1992
    Date of Patent: September 14, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventor: Rudiger Schubart
  • Patent number: 5243067
    Abstract: A 3,4,3',4'-substituted biphenyl compound represented by the general formula (II): ##STR1## wherein, one of R.sup.1 and R.sup.2 is a -CH.sub.3 group and the one other is a --COOR.sup.5 group, --COOH group, or --COCl group, and one of R.sup.3 and R.sup.4 is a -CH.sub.3 group and the other one is a --COOR.sup.5 group, --COOH group, or --COCl group, is produced by the steps of oxidatively coupling an o-toluic acid alkyl ester in the presence of a catalyst containing a mixture of palladium salts with 1,10-phenanthroline or .alpha.,.alpha.'-bipyridine, a chelating product of a palladium salt with 1,10-phenanthroline, or a chelating products of a palladium salt with .alpha.,.alpha.
    Type: Grant
    Filed: February 20, 1991
    Date of Patent: September 7, 1993
    Assignee: Ube Industries, Ltd.
    Inventors: Akinori Shiotani, Michinori Suzuki, Fumio Matsuo
  • Patent number: 5243070
    Abstract: The enantiomers of 2,2-dimethylcyclopropanecarboxylic acid are separated by esterification with the hydroxy group of optically active mandelic acid methyl ester, crystallization of the diastereomeric esters and subsequent hydrolysis of the diastereomeric esters.
    Type: Grant
    Filed: June 6, 1991
    Date of Patent: September 7, 1993
    Assignee: Lonza Ltd.
    Inventor: Thomas Meul
  • Patent number: 5241105
    Abstract: In one embodiment this invention provides smoking compositions which contain a novel oxalate ester flavorantrelease additive.Under cigarette smoking conditions, a combustible filler additive such as methyl 4-oxo-.beta.-ionyl oxalate pyrolyzes and releases megastigma-5,7,9-trien-4-one as a natural flavorant component of the cigarette smoke.
    Type: Grant
    Filed: September 10, 1992
    Date of Patent: August 31, 1993
    Assignees: Philip Morris Incorporated, Philip Morris Products Inc.
    Inventor: W. Geoffrey Chan
  • Patent number: 5238832
    Abstract: Novel aryl aliphatic acids or derivatives thereof of the general formulaR--(C.sub.x --C.sub.y)--(C.sub.m H.sub.2m)--G--C(R.sup.1).sub.2 --Ar--(C.sub.n H.sub.2n)--COOR.sup.2are described which exhibit inhibiting activity against 12-lipoxygenase. The compounds are characterized by having a low level of toxicity. Also included are salts and esters of the aliphatic acids.
    Type: Grant
    Filed: June 8, 1992
    Date of Patent: August 24, 1993
    Assignees: Board of Governors of Wayne State University, Vanderbilt University
    Inventors: Carl R. Johnson, Gilles Gorins, Kenneth V. Honn, Lawrence J. Marnett
  • Patent number: 5237092
    Abstract: A process for efficiently producing aryl formate and aromatic carboxylic acid from aldehyde, which comprises oxidizing an aromatic aldehyde with an oxygen-containing gas in the presence of a volatile solvent up to a reaction ratio of 40 to 70 mol % to convert the aromatic aldehyde to a peracid, adding a stabilizer, and allowing the remaining aromatic aldehyde and the aromatic peracid to react while the volatile solvent is distilled off.
    Type: Grant
    Filed: June 16, 1992
    Date of Patent: August 17, 1993
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Toru Tanaka, Kazuo Tanaka, Teruo Aratake
  • Patent number: 5235101
    Abstract: An improved process for the separation of enantiomers of a mixture of certain aliphatic carboxylic acids or esters thereof is disclosed. The process involves adding an inert liquid to the reaction solution formed by: (i) forming a salt solution comprising said racemic mixture of a C.sub.1 to C.sub.6 linear or branched aliphatic carboxylic acid and an organic or inorganic base; (ii) treating said salt solution with less that equimolar equivalents of a chiral organic nitrogenous base; (iii) precipitating from the reaction solution formed in step (ii) the less soluble diastereomeric salt; (iv) addition of a countersolvent to the slurry formed in step (iii); (v) extracting the more soluble diastereomeric salt or the salt of carboxylic acid and the base added in step (i) into the countersolvent. The inert liquid and the countersolvent must be of sufficiently different density.
    Type: Grant
    Filed: January 24, 1992
    Date of Patent: August 10, 1993
    Assignee: Ethyl Corporation
    Inventors: Deepak R. Patil, Azfar A. Choudhury, Abbas Kadkhodayan
  • Patent number: 5235100
    Abstract: A process for the separation of a racemic mixture of certain aliphatic carboxylic acids or esters thereof is disclosed. The process comprises:i) separating a racemic mixture of an aliphatic carboxylic acid or ester thereof having the formula: ##STR1## where R.sub.1 is hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl; R.sub.2, R.sub.3 and R.sub.4 are different and are hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl; cycloalkyl; alkyl-substituted cycloalkyl; C.sub.6 to C.sub.14 aryl; C.sub.1 to C.sub.6 alkylthio; C.sub.2 to C.sub.8 cycloalkylthio; C.sub.6 to C.sub.10 arylthio; C.sub.6 to C.sub.10 arylcarbonyl; C.sub.4 to C.sub.8 cycloalkenyl; trifluoromethyl; halo; or C.sub.4 to C.sub.
    Type: Grant
    Filed: January 24, 1992
    Date of Patent: August 10, 1993
    Assignee: Ethyl Corporation
    Inventors: Azfar A. Choudhury, Abbas Kadkhodayan, Deepak R. Patil
  • Patent number: 5235095
    Abstract: An improved process for the separation of enantiomers of a racemic mixture of certain aliphatic carboxylic acids or esters thereof is disclosed. The process involves: (i) forming a salt solution comprising said racemic mixture of a C.sub.1 to C.sub.6 linear or branched aliphatic carboxylic acid and an organic or inorganic base; (ii) treating said salt solution with one-half molar equivalent of a chiral organic nitrogenous base having a base strength no stronger than said organic or inorganic base; and (iii) precipitating from the reaction solution formed in step (ii) the less soluble diastereomeric salt, the improvement being adding to the salt solution of step (ii) an inert organic or inorganic base that is soluble in the salt solution.
    Type: Grant
    Filed: January 24, 1992
    Date of Patent: August 10, 1993
    Assignee: Ethyl Corporation
    Inventors: Abbas Kadkhodayan, Deepak R. Patil, Azfar A. Choudhury
  • Patent number: 5233075
    Abstract: A process comprising preparing an aromatic carboxylic ester and an alkyl iodide by carboxylating an aromatic iodide in the presence of an alkylating agent and a catalytic amount of a transition metal under aromatic carboxylic ester and alkyl iodide forming conditions of temperature, pressure and ultrasound.
    Type: Grant
    Filed: October 15, 1991
    Date of Patent: August 3, 1993
    Assignee: Eastman Kodak Company
    Inventors: Guy R. Steinmetz, Andrew J. Matosky
  • Patent number: 5233078
    Abstract: The invention relates to a process for preparing dialkyl malonates by ozonolysis of diketene, subsequent catalytic hydrogenation and esterification of the reaction products, the by-products being alkyl formates and dialkyl acetals.
    Type: Grant
    Filed: June 4, 1992
    Date of Patent: August 3, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Ludwig Schuster, Klaus Halbritter
  • Patent number: 5233079
    Abstract: Disclosed herein is a free-flowing solid of 4,4'-diisocyanato dicyclohexylmethane consisting essentially of at least 90 percent of the trans,trans isomer.
    Type: Grant
    Filed: October 8, 1991
    Date of Patent: August 3, 1993
    Assignee: Miles Inc.
    Inventors: Stephen D. Seneker, Peter H. Markusch
  • Patent number: 5232920
    Abstract: Novel N-(mercaptoalkyl)amides of the formula ##STR1## wherein R.sub.1 is lower alkyl, cyclolower alkyl, aryl or heteroaryl;R.sub.2 is (COR.sub.3)-aryl, heteroaryl, substituted (COR.sub.3)-aryl or substituted heteroaryl, wherein the substituents are 1-3 substituents selected from the group consisting of carboxy, alkoxycarbonyl, lower alkyl, hydroxy, halo, lower alkoxy, cyclolower alkyl, cyano, trifluoromethyl, phenyl, phenoxy and phenylthio;R.sub.3 is --OR.sub.4 or --NR.sub.4 R.sub.5 ;R.sub.4 and R.sub.5 are independently selected from the group consisting of hydrogen, lower alkyl, hydroxy lower alkyl, lower alkoxy lower alkyl and aryl lower alkyl, or R.sub.4 and R.sub.5 together with the nitrogen to which they are attached form a 5-, 6- or 7-membered ring;Q is hydrogen or R.sub.6 CO--;R.sub.
    Type: Grant
    Filed: December 21, 1990
    Date of Patent: August 3, 1993
    Assignee: Schering Corporation
    Inventor: Bernard R. Neustadt
  • Patent number: 5231113
    Abstract: Retinoid-like activity is exhibited by compounds of the formula ##STR1## where the R groups are independently hydrogen, or lower alkyl; A is --C(O)O--, --OC(O)--, --C(O)S--, or --SC(O)--; n is 0-5; and Z is H, --COB where B is --OH or a pharmaceutically acceptable salt, or B is --OR.sub.1 where R.sub.1 is an ester-forming group, or B is --N(R).sub.2 where R is hydrogen or lower alkyl, or Z is --OE where E is hydrogen or an ether-forming group or --COR.sub.2 where R.sub.2 is hydrogen, lower alkyl, phenyl or lower alkyl phenyl, or Z is --CHO or an acetal derivative thereof, or Z is --COR.sub.3 where R.sub.3 is --(CH.sub.2).sub.m CH.sub.3 where m is 0-4 and the sum of n and m does not exceed 4.
    Type: Grant
    Filed: June 4, 1992
    Date of Patent: July 27, 1993
    Assignee: Allergan, Inc.
    Inventors: Roshantha A. S. Chandraratna, Robert J. Weinkam
  • Patent number: 5221765
    Abstract: A method for racemizing an optically active carboxylic acid, or ester thereof, of the formula: ##STR1## where R.sub.1 is hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl; R.sub.2, R.sub.3 and R.sub.4 are different and are hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl, C.sub.1 to C.sub.6 linear or branched haloalkyl, aralkyl, cycloalkyl, alkyl substituted cycloalkyl, C.sub.6 to C.sub.10 aryl, C.sub.1 to C.sub.6 linear or branched alkoxy, C.sub.6 to C.sub.10 aryloxy, C.sub.1 to C.sub.6 alkylthio, C.sub.2 to C.sub.8 cycloalkylthio, C.sub.6 to C.sub.10 arylthio, C.sub.6 to C.sub.10 arylcarbonyl, C.sub.4 to C.sub.8 cycloalkenyl, trifluoromethyl, halo, C.sub.4 to C.sub.5 heteroaryl, C.sub.10 to C.sub.14 aryl, or biphenyl unsubstituted or substituted with methyl or halo, comprising heating said optically active carboxylic acid or ester thereof in the presence of water at a temperature of from about 75.degree. C. to about 200.degree. C.
    Type: Grant
    Filed: January 24, 1992
    Date of Patent: June 22, 1993
    Assignee: Ethyl Corporation
    Inventors: Deepak R. Patil, Azfar A. Choudhury, Abbas Kadkhodayan
  • Patent number: 5220069
    Abstract: A process for preparing nitrogen-containing compounds which comprises contacting a carboxylated N-monosubstituted nitrogen-containing compound or a carboxylated N,N-disubstituted nitrogen-containing compound with a mixed metal oxide catalyst under conditions effective to produce the nitrogen-containing compound.
    Type: Grant
    Filed: September 20, 1990
    Date of Patent: June 15, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Stephen W. King, Bernard C. Ream
  • Patent number: 5220053
    Abstract: An improved process for the separation of enantiomers of a racemic mixture of certain aliphatic carboxylic acids or esters thereof is disclosed. The process involves adding a mixture of the aliphatic carboxylic acid to the material formed by: (i) forming a solution comprising said racemic mixture of a C.sub.1 to C.sub.6 linear or branched aliphatic carboxylic acid and an organic or inorganic solvent; (ii) treating said solution with a chiral organic nitrogenous base; (iii) precipitating from the reaction solution formed in step (ii) a crystalline material comprised of the less soluble diastereomeric salt. The solution is admixed with the crystalline material for a time sufficient to cause an increase in the amount of the less soluble diastereomeric salt in the crystalline material.
    Type: Grant
    Filed: January 24, 1992
    Date of Patent: June 15, 1993
    Assignee: Ethyl Corporation
    Inventors: Azfar A. Choudhury, Abbas Kadkhodayan, Deepak R. Patil
  • Patent number: 5214199
    Abstract: A malonic monoester is prepared in a good yield by a single step reaction by reacting malonic acid with an alcohol in the presence of a base and an activator of malonic acid selected from the group consisting of an acyl halide or halocarbonate and an acid anhydride or dicarbonate.
    Type: Grant
    Filed: August 30, 1991
    Date of Patent: May 25, 1993
    Assignee: Kanegafuchi Chemical Industries Co., Ltd.
    Inventors: Teruyoshi Koga, Noboru Ueyama, Kenji Inoue, Satomi Takahashi
  • Patent number: 5214198
    Abstract: There is provided a method of manufacture of dialkyl monohalomaleate and dialkyl monohalofumarate and mixtures thereof via a dehydrohalogenation of the appropriate dialkyl dihalosuccinate precursor in the presence of an aqueous base and a phase transfer catalyst.
    Type: Grant
    Filed: December 20, 1991
    Date of Patent: May 25, 1993
    Assignee: American Cyanamid Company
    Inventor: Albert A. Cevasco
  • Patent number: 5214193
    Abstract: A bisphenol monoester represented by the formula (I): ##STR1## wherein R.sup.1 is hydrogen or alkyl, R.sup.2 and R.sup.3 are each alkyl, and R.sup.4 is alkyl, alkenyl or phenyl, is produced by continuous two step reactions in which an aldehyde R.sup.1 -CHO and 2,4-dialkylphenol are subjected to a condensation reaction in a C.sub.6 -C.sub.10 aliphatic or C.sub.6 -C.sub.12 aromatic hydrocarbon solvent, and then a resulting bisphenol compound dissolved in the solvent is subjected to an esterification with a carboxylic acid R.sup.4 --COOH or its derivative. Prior to the esterification, the organic layer containing the bisphenol compound is subjected to a dehydration treatment, thereby enabling the two steps to proceed continuously without isolating the intermediate bisphenol compound. A purification process for the bisphenol monoester of the formula (I) is also disclosed in which the monoester is purified from a mixed solvent comprising a C.sub.6 -C.sub.12 aromatic hydrocarbon solvent and a C.sub.1 -C.sub.
    Type: Grant
    Filed: February 12, 1992
    Date of Patent: May 25, 1993
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kikumitsu Inoue, Manji Sasaki, Kazuaki Yamamoto, Shinichi Yachigo