Oxy Patents (Class 562/465)
  • Patent number: 5248814
    Abstract: Process for preparing regenerated humic acids from coal by means of the continuous oxidation on fluidized bed, characterized in that a coal of lignite, sub-bituminous or bituminous type is submitted to a preliminary oxidation under mild conditions in order to reduce the hydrogen content of said coal by an amount of 5 to 25% of hydrogen initially present in the starting coal, and that the resulting coal is subsequently submitted to an oxidation in order to produce the desired humic acids.
    Type: Grant
    Filed: September 11, 1992
    Date of Patent: September 28, 1993
    Assignee: Eniricerche S.p.A.
    Inventors: Vincenzo Calemma, Vincenzo Piccolo, Riccardo Rausa
  • 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: 5216024
    Abstract: The present invention discloses new and useful compounds including methyl p-hydroxyphenyllactate, its analogues, chemical derivatives and chemically related compounds and their use as antitumor agents, as inhibitors of proliferative cell growth and as prophylactic agents to inhibit and prevent cancer and non-malignant cell growth.
    Type: Grant
    Filed: July 15, 1988
    Date of Patent: June 1, 1993
    Assignee: Baylor College of Medicine
    Inventors: Barry M. Markaverich, James H. Clark, Rebecca Gregory, Mary Alejandro, Brian S. Middleditch, Gregory A. Johnson, Rajender S. Varma
  • Patent number: 5206392
    Abstract: A process for making acrylmaleic acid and arylmaleic anhydride derivative useful as intermediates for the preparation of arylmaleimides in the synthesis of compounds having activity in the central nervous system. The process involves reacting arylacetonitriles with glyoxylic acid to provide novel intermediate 3-aryl-3-cyanopropeneoates which may be converted to the arylmaleic acid and arylmaleic anhydride derivatives.
    Type: Grant
    Filed: April 27, 1992
    Date of Patent: April 27, 1993
    Assignee: American Cyanamid Company
    Inventor: William D. Dean
  • Patent number: 5202471
    Abstract: Retinoid like activity is exhibited by compounds of the formula ##STR1## where R.sub.1 -R.sub.4 independently are hydrogen, lower alkyl, cycloalkyl or lower alkenyl, A and B independently are hydrogen, lower alkyl cycloalkyl, lower alkenyl, SR* or OR* where R* is lower alkyl, cycloalkyl or lower alkenyl; Y is lower alkenyl, lower alkynyl, lower cycloalkyl, lower branched chain alkyl or (CH.sub.2).sub.n where n is 0-6; and Z is H, --COOH or a pharmaceutically acceptable salt, ester or amide thereof, --CH.sub.2 OH or an ether or ester derivative, or --CHO or an acetal derivative, or --COR' or a ketal derivative where R' is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons.
    Type: Grant
    Filed: February 6, 1990
    Date of Patent: April 13, 1993
    Assignee: Allergan, Inc.
    Inventor: Roshantha A. S. Chandraratna
  • Patent number: 5196570
    Abstract: The invention relates to new leukotriene-B.sub.4 analogs of formula I, ##STR1## in which R.sub.1 means radicals CH.sub.2 OH, CH.sub.3, CF.sub.3, COOR.sub.4, or radical CONHR.sub.5,A means a trans, trans--CH.dbd.CH--CH.dbd.CH-- group, trans--CH.sub.2 --CH.sub.2 --CH.dbd.CH-- group or tetramethylene group,B means a straight-chain or branched-chain, saturated or unsaturated alkylene group with up to 10 C atoms,D means a direct compound, oxygen, sulfur, a --C.tbd.C--group or a --CH.dbd.CR.sub.6 --group,B and D together mean a direct bond,R.sub.2 means a hydrogen atom or an acid radical of an organic acid with 1-15 C atoms andR.sub.3 means a hydrogen atom, an optionally substituted alkyl radical with 1-10 C atoms, a cycloalkyl radical with 3-10 C atoms, an optionally substituted aryl radical with 6-10 C atoms or a 5-6-member heterocyclic radical and, if R.sub.
    Type: Grant
    Filed: November 16, 1990
    Date of Patent: March 23, 1993
    Assignee: Schering Aktiengesellschaft
    Inventors: Bernd Buchmann, Werner Skuballa, Joseph Heindl, Wolfgang Frohlich, Roland Ekerdt
  • Patent number: 5191104
    Abstract: This invention relates to a process for the alkoxylation of a carboxylated compound comprising contacting the carboxylated compound with an alkylene oxide in the presence of a mixed metal oxide catalyst or a modified bimetallic or polymetallic catalyst under conditions effective to alkoxylate the carboxylated compound.
    Type: Grant
    Filed: September 20, 1990
    Date of Patent: March 2, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventor: Stephen W. King
  • Patent number: 5183660
    Abstract: Polyethylene glycol derivatives of the formula ##STR1## wherein R.sub.1 and R.sub.2 are the same or different and each represents a lower alkyl, m and n are the same or different and each represents a positive integer and p is 0 or a positive integer, peptides modified by the polyethylene glycol derivatives, methods for producing them and use of the modified peptides. The peptides modified by the polyethylene glycol derivatives (I) of the invention, as compared with the corresponding non-modified peptides, show decreased antigenicity, are considerably delayed in biological clearance, and exhibit their physiological activities effectively over a long period, rendering them very effective as pharmaceuticals as well as drugs for animals.
    Type: Grant
    Filed: August 15, 1991
    Date of Patent: February 2, 1993
    Assignee: Sumitomo Pharmaceuticals Company, Limited
    Inventors: Yoshiharu Ikeda, Yoshiyuki Kai, Keiichi Ono
  • Patent number: 5179124
    Abstract: An anti-inflammatory drug which is phenylacetic acid derivative and methods of using the same in topically controlling eye inflammations. The preferred drug is 2-[4(2-hydroxypropoxy)phenyl]propionic acid.
    Type: Grant
    Filed: October 1, 1990
    Date of Patent: January 12, 1993
    Assignee: University of Iowa Research Foundation
    Inventors: Ronald D. Schoenwald, Charles F. Barfknecht
  • Patent number: 5151545
    Abstract: Variously substituted 3,5-dihydroxy-6,8-nonadienoic acids and esters, are blood cholesterol lowering agents and so are useful in the prevention and treatment of cardiovascular diseases such as atherosclerosis.
    Type: Grant
    Filed: March 27, 1990
    Date of Patent: September 29, 1992
    Assignee: Pfizer Inc.
    Inventors: Peter A. McCarthy, Frederick J. Walker
  • Patent number: 5145992
    Abstract: A process for producing an .alpha.-alkoxy acetic acids and salts thereof which comprises reacting an alcohol of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 can be hydrogen, alkyl, alkoxy, halo, phenyl, substituted phenyl, or hydroxy; A can be S, O or --CH.sub.2 --; and Alk is straight or branched chain alkylene, with a base in an aprotic solvent, then reacting the resulting alkoxide with a monohaloacetic acid ester to give an alkoxyacetate followed by reaction of the alkoxyacetate with a hydrogen halide, organic acid or Lewis acid in nitromethane to give the corresponding .alpha.-alkoxyacetic acid which then may be recovered or may optionally be converted to the corresponding salt by contracting the .alpha.-alkoxyacetic acid with a base.
    Type: Grant
    Filed: May 6, 1991
    Date of Patent: September 8, 1992
    Assignee: G. D. Searle & Co.
    Inventors: Richard A. Mueller, Richard A. Partis
  • Patent number: 5140046
    Abstract: Novel phenylene derivatives shown by the general formula ##STR1## where A represents a hydrogen atom, a phenyl group or a phenoxy group, n represents an integer of 3 to 10, R.sub.1 represents a hydrogen atom or a lower alkoxy group, X.sub.1 represents --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --CONH--, B represents ##STR2## wherein R.sub.2 represents a hydrogen atom, a halogen atom, a nitro group, etc.), ##STR3## (wherein R.sub.3 represents a hydrogen atom, a hydroxyl group or a lower alkoxy group), X.sub.2 represents --CH.dbd.CH--, --CH.sub.2 CH.sub.2 --, etc. and D represents a carboxy group, a lower alkoxycarbonyl group or ##STR4## which are useful as drugs, particularly SRS-A(slow reacting substance of anaphylaxis) antagonist, i.e. they are useful as prophylaxis and treatment for various allergic diseases (e.g. bronchial asthma, allergic rhinitis, urticaria) or, ischemic heart diseases, inflammation, etc. induced by SRS-A.
    Type: Grant
    Filed: August 13, 1990
    Date of Patent: August 18, 1992
    Assignee: Yamanouchi Pharmaceutical Co., Ltd.
    Inventors: Toshiyasu Mase, Kiyoshi Murase, Hiromu Hara, Kenichi Tomioka
  • Patent number: 5117038
    Abstract: Herbicidal substituted phenoxyphenylpropionic acid derivatives of the formula ##STR1## in which Q represents S, SO or SO.sub.2,m represents the numbers 0 or 1,R.sup.1 represents hydrogen, halogen, cyano or trifluoromethyl,R.sup.2 represents hydrogen or halogen,R.sup.3 represents halogen, cyano, trifluoromethyl, trifluoromethoxy or trifluoromethylsulphonyl,R.sup.4 represents hydrogen or halogen,R.sup.5 represents hydrogen or halogen,R.sup.6 represents hydrogen, cyano, carboxyl, alkyl optionally substituted by halogen or alkoxycarbonyl,R.sup.7 represents halogen, hydroxyl, amino, alkylamino, alkenylamino, alkynylamino, arylamino, aralkylamino, alkoxycarbonyl-alkylamino, cyanoamino, dialkylamino, dialkenylamino, alkylsulphonylamino, arylsulphonylamino, hydroxyamino, alkoxyamino, hydrazino, alkylsulphonylhydrazino, arylsulphonylhydrazino, alkylthio, arylthio, aralkylthio, alkoxycarbonylalkylthio or the grouping O--R.sup.8.
    Type: Grant
    Filed: February 16, 1990
    Date of Patent: May 26, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Michael Haug, Albrecht Marhold, Hans-Joachim Santel, Klaus Lurssen, Robert R. Schmidt
  • Patent number: 5107053
    Abstract: A ruthenium phosphine complex having catalytic, hydrogenation activity is disclosed. The catalyst as the formula ##STR1## wherein R and R' are the same or different and are C.sub.1 to C.sub.6 linear or branched alkyl; R" is hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl; R.sub.1 is C.sub.1 to C.sub.6 linear or branched alkyl; and n is an integer from 1 to 6.The phosphine complex is particularly useful in the asymmetric hydrogenation of unsaturated carboxylic acids or alkyl esters thereof.
    Type: Grant
    Filed: October 25, 1991
    Date of Patent: April 21, 1992
    Assignee: Ethyl Corporation
    Inventor: Tse-Chong Wu
  • Patent number: 5091565
    Abstract: New poly-dicarboxylic acid anhydrides, which are suitable as bio-degradable matrix materials for the controlled release of medicinal agents in humans.
    Type: Grant
    Filed: August 21, 1990
    Date of Patent: February 25, 1992
    Assignee: Sandoz Ltd.
    Inventor: Gerd Ziegast
  • Patent number: 5041638
    Abstract: An alkenoic acid derivative of the formula ##STR1## in which X and Y are identical or different and represent sulfur, sulfoxide, sulfone, an alkylene chain, --SCH.sub.2 --, or oxygen or a direct bond,W represents --CH.dbd.CH-- or --CH.sub.2 --CH.sub.2 --,o represents a number 1 to 5,A and B are identical or different and represent carboxyl, carboxymethylene, tetrazolyl or tetrazolylmethylene, or --CO.sub.2 R.sup.9 or --CH.sub.2 CO.sub.2 R.sup.9 or --CONR.sup.10 R.sup.11 or nitrilen represents a number 1 to 10,m represents a number 0 to 7,T and Z are identical or different and represent oxygen or a direct bond andR.sup.2, R.sup.3, R.sup.8 are identical or different and represent hydrogen, alkyl, alkoxy, halogen, trifluoromethyl, trifluoromethoxy, cyano or nitro andR.sup.9 is lower alkyl and R.sup.10 and R.sup.11 are hydrogen, lower alkyl, alkylsulfonyl or arylsulfonyl or together are an alkylene chain to form a ringand pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: May 9, 1989
    Date of Patent: August 20, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Ulrich Rosentreter, Harold C. Kluender, Trevor S. Abram, Peter Norman, Steven R. Tudhope
  • Patent number: 5019298
    Abstract: Disclosed are optically active aromatic carboxylic acid derivatives represented by the formula (I): ##STR1## (wherein R.sub.2 represents an alkoxyalkyl group having 1 to 20 carbon atoms or an alkyl group having 1 to 20 carbon atoms, which alkyl group may be substituted with a halogen atom; represents a number of 1 or 2; m represents a number of 0 or 1; and * indicates asymmetric carbon atom) and a process for producing such derivatives through the following reaction steps: ##STR2## The optically active aromatic carboxylic acid derivatives represented by the above-described formula (I) are useful as a liquid crystal material and can be also utilized as an intermeidate for the preparation of pharmaceuticals, agricultural chemicals and the like.
    Type: Grant
    Filed: April 25, 1988
    Date of Patent: May 28, 1991
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masayoshi Minai, Takayuki Higashii
  • Patent number: 5017723
    Abstract: Substituted ethylamines of the formula ##STR1## wherein R.sub.1 is phenyl optionally mono-, di- or trisubstituted by halogen, lower alkyl, lower haloalkyl or lower alkoxy, or is an aromatic heterocycle having 5 to 7 chains wherein the heteroatom is nitrogen, oxygen or sulfur,R.sub.2 is lower alkyl,R.sub.3 and R.sub.4, each independently, represent hydrogen, lower alkyl or lower alkenyl,R.sub.5 is phenyl optionally mono-, di- or trisubstituted by halogen or lower alkoxy or is an aromatic heterocycle having 5 to 7 chains wherein the heteroatom is nitrogen, oxygen or sulfur andQ represents a --CH.dbd.CH-- ethylene group or a 1,2-diyl ##STR2## propane group, their acid addition salts and their optically active forms. These substituted ethylamines have psycotropic properties and are useful as medicines.
    Type: Grant
    Filed: February 26, 1990
    Date of Patent: May 21, 1991
    Assignee: Jouveinal S.A.
    Inventors: Gilbert G. Aubard, Alain P. Calvet, Claude J. Gouret, Agnes M. Grouhel, Henry L. Jacobelli, Jean-Louis Junien, Xavier B. Pascaud, Francois J. Roman, Claude D. Soulard, James P. Hudspeth, Yuan Lin
  • Patent number: 5013864
    Abstract: A process for producing an .alpha.-alkoxy acetic acids and salts thereof which comprises reacting an alcohol of the formula R--OH wherein R is alkyl, substituted alkyl, or cycloalkyl, or cycloalkyl alkyl with a base in an aprotic organic solvent to give an alkoxide followed by removal of the organic solvent and reaction of the alkoxide with a salt of a monohaloacetic acid in a polar aprotic solvent such as DMSO to give the corresponding alkoxyacetate salt which then may be recovered or may optionally be converted to the corresponding acid by contacting the alkoxy acetate salt with an acid.
    Type: Grant
    Filed: December 8, 1989
    Date of Patent: May 7, 1991
    Assignee: G. D. Searle & Co.
    Inventors: Arthur L. Campbell, Richard A. Mueller, John S. Ng, Richard A. Partis
  • Patent number: 5004832
    Abstract: Compounds are described of formula ##STR1## in which: Ar represents an aryl, possibly substituted;R represents a C.sub.1 -C.sub.4 alkyl;R' represents a hydroxyl, an alkoxy, an amino group possibly mono or di-alkyl substituted, or an O.sup.-- M.sup.+ group where M.sup.+ represents the cation of an alkaline metal;X represents a hydrogen, chlorine, bromine or iodine atom, a hydroxyl, or an acyloxy, alkylsulphonyloxy or arylsulphonyloxy group.The compounds of formula I can be easily transformed into alpha-arylalkanoic acids of formula ##STR2## in which Ar and R have the aforesaid meanings.
    Type: Grant
    Filed: February 6, 1989
    Date of Patent: April 2, 1991
    Assignee: Zambon S.p.A.
    Inventors: Graziano Castaldi, Claudio Giordano
  • Patent number: 4999429
    Abstract: Aryl difluoromethyl sulfone adds to aldehydes under phase transfer conditions to give novel substituted alcohols of the general formulaRCH(OH)CF.sub.2 SO.sub.2 Ar (I)wherein R is an aryl, cycloaliphatic, sec- or tert-aliphatic, or heterocyclic group and Ar is an aryl group. The substituted alcohols of formula I are of particular utility as intermediates in the synthesis of a variety of useful end products. For example, the products of formula I may be utilized in desulfonylation reactions, oxidation reactions and fluorination reactions.
    Type: Grant
    Filed: November 13, 1989
    Date of Patent: March 12, 1991
    Assignee: Ethyl Corporation
    Inventor: G. Patrick Stahly
  • Patent number: 4990633
    Abstract: New fluorinated bisaryloxy-substituted alkenes are prepared by reaction of substituted phenols with perhaloalkenes and can be used as electrical insulating agents.
    Type: Grant
    Filed: May 4, 1989
    Date of Patent: February 5, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Michael Negele, Dietmar Beilefeldt, Thomas Himmler, Albrecht Marhold
  • Patent number: 4962230
    Abstract: A process for producing an optically active carboxylic acid represented by formula (I): ##STR1## wherein R.sup.1, and R.sup.2, and R.sup.3 each represents a hydrogen atom, an alkyl group, an alkenyl group, or a phenyl or naphthyl group which may have a substituent, provided that all of R.sup.1, R.sup.2, and R.sup.3 are not simultaneously a hydrogen atom; when R.sup.1 and R.sup.2 are simultaneously a hydrogen atom, then R.sup.3 is not a methyl group; and that when R.sup.3 is a hydrogen atom, then R.sup.1 and R.sup.2 are each a group other then a hydrogen atom,is disclosed, comprising asymmetrically hydrogenating an .alpha.,.beta.-unsaturated carboxylic acid represented by formula (II): ##STR2## wherein R.sup.1, R.sup.2, and R.sup.3 are the same as defined above, in the presence of a ruthenium-optically active phosphine complex as a catalyst.
    Type: Grant
    Filed: November 16, 1987
    Date of Patent: October 9, 1990
    Assignee: Takasago International Corporation
    Inventors: Hidemasa Takaya, Tetsuo Ohta, Ryoji Noyori, Noboru Sayo, Hidenori Kumobayashi, Susumu Akutagawa
  • Patent number: 4942174
    Abstract: Novel alkyl aryl ether derivatives corresponding to the formula: ##STR1## in which R.sup.1 is a C.sub.8 -C.sub.20 alkyl group with one or more branches, E is a group --CH.sub.2 --CH.sub.2 -- or --CH.dbd.CH-- and R.sup.2 is a C.sub.1 -C.sub.4 alkyl group, a C.sub.2 -C.sub.4 hydroxyalkyl group, an alkoxyalkyl group containing 1 to 4 C atoms in the alkoxy group and 2 to 4 C atoms in the alkyl group, hydrogen or a salt-forming cation, are highly effective sebosuppressive agents in cosmetic or pharmaceutical preparations for topical application to the hair and to the skin.
    Type: Grant
    Filed: November 10, 1988
    Date of Patent: July 17, 1990
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Hinrich Moeller, Siegfried Wallat
  • Patent number: 4937379
    Abstract: A process is described for preparing alpha-arylalkanoic acids, which comprises preparing and subsequently rearranging ketals of formula ##STR1## (in which Ar, R, R.sub.1, R.sub.2 and R.sub.4 have the meanings given in the description).The ketals of formula II are prepared from the corresponding alpha-hydroxyketals.The rearrangement reaction is conducted under mild conditions.
    Type: Grant
    Filed: July 30, 1987
    Date of Patent: June 26, 1990
    Assignee: Zambon S.p.A.
    Inventors: Claudio Giordano, Marco Villa
  • Patent number: 4912256
    Abstract: This invention relates to the production of a solid oxidized coal containing humic acids. Coal with a mean particle size of less than 3 mm is slurried with water and then oxidized with oxygen or mixtures of oxygen and air at temperatures ranging from 100.degree. to 300.degree. C., at partial oxygen pressures ranging from 0,1 to 10 MPa and reaction periods ranging from 5 to 600 minutes. In the absence of catalysts, e.g. alkaline bases, the main product of oxidation is humic acids. These humic acids are not dissolved because the pH of this slurry is in the range 4 to 9. Small amount of fulvic acids are formed and these are soluble in the water of the slurry.The coal-derived humic acids may for example find application as soil conditioners, organic fertilisers, briquette and pellet binders, drilling fluid dispersants and viscosity control agents, while the coal-derived fulvic acids may be utilized for the production of fuel extenders, plasticizers and petrochemicals.
    Type: Grant
    Filed: July 7, 1988
    Date of Patent: March 27, 1990
    Assignee: National Energy Council
    Inventor: Izak J. Cronje
  • Patent number: 4897397
    Abstract: Certain aryl-alkynoic, alkenoic and alkanoic acids and derivatives and their use in treating inflammation, allergy and hyperproliferative skin disease are disclosed.
    Type: Grant
    Filed: December 16, 1988
    Date of Patent: January 30, 1990
    Assignee: Schering Corporation
    Inventors: Neng Y. Shih, David J. Blythin
  • Patent number: 4883613
    Abstract: The compounds 9-phenyl-3,7-dimethyl-2,4,6,8 nonatetraenoic acids wherein the phenyl group is substituted with an alkyl, aminoalkyl, hydroxyalkyl, alkoxy, hydroxyalkylamino, and a hydroxy alkoxy group, and derivatives thereof which are used as disease modifying anti-rheumatic agents and as immunosuppressants.
    Type: Grant
    Filed: July 31, 1987
    Date of Patent: November 28, 1989
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Edward R. Aig, John W. Coffey, Allen J. Lovey, Michael Rosenberger
  • Patent number: 4855324
    Abstract: This invention relates to a compound of the formula: ##STR1## or a pharmaceutically acceptable salt thereof wherein X is oxygen, sulfur, or --CH.dbd.CH--;wherein Z is OR.sup.1 or --NR.sup.4 R.sup.5 ;wherein R.sup.1 is hydrogen, lower alkyl, or a pharmaceutically acceptable cation;wherein R.sup.2 is H, --CH.sub.3 or --C.sub.2 H.sub.5 ;wherein R.sup.3 is OH, H or .dbd.O;wherein R.sup.4 and R.sup.5 may independently be hydrogen, or lower alkyl having 1-6 carbon atoms, or R.sup.4 and R.sup.5 may act together with N to form a cyclic amide of the formula: ##STR2## wherein n is an integer from 4-5; and m is an integer from 0-4. More particularly, this invention relates to compounds of the above formula which have utility as LTB.sub.4 antagonists.
    Type: Grant
    Filed: February 18, 1988
    Date of Patent: August 8, 1989
    Assignee: G. D. Searle & Co.
    Inventors: Stevan W. Djuric, Richard A. Haack, Stella S. Yu
  • Patent number: 4826876
    Abstract: This invention relates to chemical compounds which have selective thyromimetic activity. A compound of this invention is 3,5-dibromo-3'-[6-oxo-3(1H)-pyridazinyl-methyl]-thyronine.
    Type: Grant
    Filed: December 21, 1987
    Date of Patent: May 2, 1989
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: David Ellis, John C. Emmett, Anthony H. Underwood, Paul D. Leeson
  • Patent number: 4814494
    Abstract: An effective method for producing highly pure (aryl substituted)carboxylic acid or its salt which comprises the steps of:(I) oxidizing (aryl substituted)aldehyde in an acidic phase in the presence of hypohalogenite; and(II) bringing the oxidized product obtained in the preceding step into contact in a liquid phase with hydrogen in the presence of a catalyst of transistion metal of the group VIII in the periodic table.
    Type: Grant
    Filed: February 6, 1987
    Date of Patent: March 21, 1989
    Assignee: Nippon Petrochemicals Company, Ltd.
    Inventors: Isoo Shimizu, Yasuo Matsumura, Yoshihisa Inomata
  • Patent number: 4788360
    Abstract: A process is disclosed for the production of humic acids, which comprises an oxidation of coal in dry phase with oxygen or mixtures of oxygen and nitrogen in a fluidized-bed reactor, by using coal with a granulometry comprised within the range of from 100 .mu.m to 3 mm and operating at a temperature comprised within the range of from 150.degree. to 300.degree. C., under a partial pressure of oxygen comprised within the range of from 1.1 abs.atm. to 10 abs.atm., for a contact time comprised within the range of from 30 minutes to 600 minutes.
    Type: Grant
    Filed: December 8, 1987
    Date of Patent: November 29, 1988
    Assignee: Eniricerche S.p.A.
    Inventors: Vincenzo Calemma, Riccardo Rausa
  • Patent number: 4720505
    Abstract: Compounds having the formula: ##STR1## are antagonists of leukotrienes of C.sub.4, D.sub.4 and E.sub.4, the slow reacting substance of anaphylaxis. These compounds are useful as anti-asthmatic, anti-allergic and anti-inflammatory agents.
    Type: Grant
    Filed: November 13, 1984
    Date of Patent: January 19, 1988
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Patrice C. Belanger, John W. Gillard, Joshua Rokach
  • Patent number: 4709089
    Abstract: An effective method for refining 2-(aryl substituted)propionic acid or its salt which is characterized in that 2-(aryl substituted)propionic acid or its salt containing halogenated by-products is brought into contact with hydrogen in a liquid phase containing water under a basic condition at temperatures in the range of 20.degree. C. to 170.degree. C. in the presence of a catalyst of transition metal of the group VIII in the periodic table, thereby dehalogenating said halogenated by-product and producing highly pure 2-(aryl substituted)propionic acid or its salt.
    Type: Grant
    Filed: February 6, 1987
    Date of Patent: November 24, 1987
    Assignee: Nippon Petrochemicals Company, Limited
    Inventors: Isoo Shimizu, Yasuo Matsumura, Yoshihisa Inomata
  • Patent number: 4690948
    Abstract: Ring opened halogenated Resorcyclic Acid Lactone (RAL) derivatives having the structure: ##STR1## are used to increase rumen fermentation efficiency.
    Type: Grant
    Filed: December 1, 1986
    Date of Patent: September 1, 1987
    Assignee: International Minerals & Chemical Corp.
    Inventor: Jing-Jong Lu
  • Patent number: 4670586
    Abstract: A method for the production of an .alpha.-aryl-alkanoic acid represented by the general formula II: ##STR1## wherein R.sup.3 stands for a hydrogen atom or an alkyl group and Ar for an aromatic residue, characterized by subjecting an .alpha.-haloalkyl-aryl ketal represented by the general formula I: ##STR2## wherein Ar has the same meaning as defined above, R.sup.1 and R.sup.2 independently stand for an alkyl group and embrace the case wherein they jointly form a cyclic acetal, R.sup.3 has the same meaning as defined above, and X stands for a halogen atom to a rearrangement reaction in the presence of at least one zinc compound selected from the group consisting of oxide, hydroxide, sulfide, carbonate, and basic carbonate of zinc and subsequently hydrolyzing the product of said rearrangement reaction.
    Type: Grant
    Filed: September 10, 1985
    Date of Patent: June 2, 1987
    Assignee: Nippon Chemicals Co., Ltd.
    Inventors: Yuta Yabe, Takamichi Watanabe, Hisayuki Suzuki
  • Patent number: 4667056
    Abstract: A process for preparing hydratropic acids and the esters thereof, of formula Ar--CH(CH.sub.3)--COOR where R=H or lower alkyl and Ar=phenyl possibly substituted. This process consists in reacting on the propiophenones of formula ArCOCH.sub.2 CH.sub.3, a chlorinating or brominating agent, an alcohol R'OH where R'=lower alkyl, an orthoester R.sub.1 --C(OR').sub.3 wherein R.sub.1 =H or lower alkyl, and metal zinc; then possibly hydrolyzing the esters obtained.With this process can be prepared hydratropic acids known for their anti-inflammatory activity.
    Type: Grant
    Filed: May 3, 1985
    Date of Patent: May 19, 1987
    Assignee: Delalande S.A.
    Inventor: Guy P. Adrian
  • Patent number: 4644085
    Abstract: The invention relates to a new anti-cancer chemical compound which has been called rooperol and certain derivatives thereof of the general formula ##STR1## in which A is chosen from the group including a phenyl group, a substituted phenyl group and --CH.sub.2 --O--R.sup.5 where R.sup.5 =H, an alkyl (C.sub.1 -C.sub.5), aralkyl or acyl substituent; R.sup.1 and R.sup.2 are chosen from substituents including H for both or singly if one of them is --OH, --NH.sub.2, --SH, ##STR2## or taken together R.sup.1 and R.sup.2 are =0; R.sup.3 is H or ##STR3## where R.sup.6 is an alkyl group (C.sub.1 -C.sub.7); either of R.sup.4 or B are chosen from substituents including H, ##STR4## a phenyl group, substituted phenyl group or a furyl group.
    Type: Grant
    Filed: June 4, 1985
    Date of Patent: February 17, 1987
    Assignee: Rooperol (NA) NV
    Inventors: Siegfried Drewes, Roelof W. Liebenberg
  • Patent number: 4626597
    Abstract: 16-Fluoro-16,17-didehydro prostanoids, processes for their preparation, compositions containing them and methods of using them are disclosed. The compounds and compositions have pharmaceutical utility including, for example, luteolytic activity.
    Type: Grant
    Filed: August 22, 1984
    Date of Patent: December 2, 1986
    Assignee: Farmitalia Carlo Erba, S.p.A.
    Inventors: Franco Faustini, Roberto d'Alessio, Achille Panzeri, Enrico di Salle
  • Patent number: 4620031
    Abstract: Alpha-alkyl-alkanoic acids are prepared by heating at boiling temperature a mixture of an alpha-halogen-alkyl-arylketone in a saturated aliphatic diol or in a mixture of saturated aliphatic diols in the presence of a Broensted's acid and by successively alkalifying the reaction mixture.
    Type: Grant
    Filed: February 1, 1985
    Date of Patent: October 28, 1986
    Assignee: Zambon S.p.A.
    Inventors: Fulvio Uggeri, Graziano Castaldi, Claudio Giordano
  • Patent number: 4618697
    Abstract: This invention relates to a process for preparing an alpha-arylalkanoic acid or salt thereof which comprises the rearrangement of an alpha-halo-alkylarylketal in neutral or slightly alkaline conditions, in the presence of a dipolar aprotic diluent and of a protic substance having a high dielectric constant, and the subsequent hydrolysis of the thus obtained ester.
    Type: Grant
    Filed: February 3, 1984
    Date of Patent: October 21, 1986
    Assignee: Zambon SpA
    Inventors: Graziano Castaldi, Claudio Giordano
  • Patent number: 4616082
    Abstract: New hydroquinone ether compounds of formula I are described: ##STR1## wherein p is 1 or 2 and Q is 0 or 1, provided that p+q is 1 or 2, R is a residue of formula II ##STR2## and R.sub.o, R.sub.oo, R.sub.1, R.sub.2, R.sub.3, Q, n and k are as defined in the specification,The new compounds are useful e.g. as stabilizers in photographic material.
    Type: Grant
    Filed: June 7, 1985
    Date of Patent: October 7, 1986
    Assignee: Ciba-Geigy AG
    Inventor: Frederick H. Howell
  • Patent number: 4610819
    Abstract: A process for the preparation of 1,4-oxazepinones and thiones having the formula: ##STR1## wherein A is an aromatic ring selected from benzene, naphthalene, quinoline or pyridine; n is 1 to 3; Z is an amino radical; R is hydrogen, loweralkyl, cycloalkyl or phenylloweralkyl; and R.sup.4 and R.sup.5 are hydrogen and loweralkyl starting from chloroaromatic carboxylates and alkanolamines is disclosed.
    Type: Grant
    Filed: September 19, 1984
    Date of Patent: September 9, 1986
    Assignee: A. H. Robins Company, Inc.
    Inventors: Young S. Lo, Albert D. Cale, Jr.
  • Patent number: 4608441
    Abstract: Process for preparing an arylalkanoic acid by adding iodine to a mixture of an arylalkanone and an excess of an orthoester, heating of the mixture thus obtained, adding an inorganic base and finally an acid.
    Type: Grant
    Filed: July 12, 1985
    Date of Patent: August 26, 1986
    Assignee: BLASCHIM S.p.A.
    Inventors: Attilio Citterio, Laura Tinucci, Aldo Belli, Lucio Filippini
  • Patent number: 4605758
    Abstract: Pharmaceutically useful optically active .alpha.-arylalkanoic acids or esters, ortho esters, or amides thereof are stereoselectively prepared by contacting an aryl magnesium Grignard reagent with an optically active .alpha.-substituted acyl halide to form the optically active aryl .alpha.-substituted alkyl ketone, which is ketalized and rearranged to the desired optically active .alpha.-arylalkanoic acid or the corresponding ester, ortho ester or amide. In an alternate embodiment, the aryl .alpha.-substituted alkyl ketone is reduced to the corresponding alkanol, which is rearranged to the .alpha.-arylalkanal. The alkanal so produced is converted to the desired optically active .alpha.-arylalkanoic acid by conventional methods.
    Type: Grant
    Filed: April 23, 1984
    Date of Patent: August 12, 1986
    Assignee: Syntex Pharmaceuticals International Ltd.
    Inventor: George C. Schloemer
  • Patent number: 4604243
    Abstract: An olefin, especially an activated olefin, is arylated by reaction with an arylamine, such as an aniline, in an inert polar organic solvent and in the presence of an alkyl nitrite, a hydrogen halide, and a catalytic amount of a copper catalyst having the copper in an oxidation state below +2.
    Type: Grant
    Filed: July 25, 1985
    Date of Patent: August 5, 1986
    Assignee: Ethyl Corporation
    Inventor: Robert I. Davidson
  • Patent number: 4590291
    Abstract: An ether derivative of a dihydroxybenzene of the formula ##STR1## in which R.sup.1 is 1 to 3 identical or different substituents selected from hydrogen, halogen, trifluoromethyl, carboxyl, alkyl, alkoxy, alkylmercapto and carbalkoxy, with in each case 1 to 4 carbon atoms in the alkyl and alkoxy groups, andR.sup.2 and R.sup.3 are different and each is an alkyl or alkenyl chain in which 1 or 2 CH.sub.2 chain members are optionally replaced by O, S, CO or a phenylene group, and/or in which the chain is optionally substituted by 1 to 3 identical or different substituents selected from hydroxyl, halogen, trifluoromethyl, phenyl, carboxyl, alkyl, alkoxy, alkylmercapto, carbalkoxy, and acyl, the phenyl radical in turn optionally being substituted by halogen, trifluoromethyl, carboxyl, alkyl, alkoxy, alkylmercapto or carbaloxy, and the abovementioned alkyl, alkoxy and acyl groups in each case containing 1 to 4 carbon atoms, and in which at least one of the radicals R.sup.2 or R.sup.
    Type: Grant
    Filed: June 7, 1982
    Date of Patent: May 20, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Horst Boshagen, Ulrich Horlein, Gerd Reinhardt, Friedel Seuter, Elisabeth Perzborn
  • Patent number: 4585594
    Abstract: 4-Substituted but-3-ene-1-carboxylic acids and their esters R.sup.1 R.sup.2 C.dbd.CH--CH.sub.2 --CO--O--R.sup.3 (I, where R.sup.1 is an organic radical, R.sup.2 is H or R.sup.1, or R.sup.1 and R.sup.2 together form a 5-membered to 20-membered ring, and R.sup.3 is H or lower alkyl) are prepared by carbonylation of R.sup.1 R.sup.2 C(OH)--CH.dbd.CH.sub.2 (II) in the presence of an alcohol R.sup.3' --OH (III, where R.sup.3' is lower alkyl) or, for the preparation of the acids I alone, in the absence of an alcohol III, at from 50.degree. to 150.degree. C. and under from 200 to 700 bar, using a complex of a palladium halide and a tertiary organic phosphine.
    Type: Grant
    Filed: December 11, 1984
    Date of Patent: April 29, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Walter Himmele, Werner Hoffmann, Lothar Janitschke
  • Patent number: 4582930
    Abstract: A process is disclosed for the preparation of optically active alpha-arylalkanoic acids, consisting in the rearrangement of optically active alpha-(haloalkyl)-aryl-ketals and in submitting to hydrolysis the so-obtained esters of alpha-arylalkanoic acids.The rearrangement reaction is carried out under neutral or slightly alkaline conditions in a polar protic medium.
    Type: Grant
    Filed: February 22, 1985
    Date of Patent: April 15, 1986
    Assignee: Zambon S.p.A.
    Inventors: Graziano Castaldi, Claudio Giordano, Fulvio Uggeri
  • Patent number: 4579968
    Abstract: A process is disclosed for the preparation of optically active alpha-arylalkanoic acids, consisting in the rearrangement of optically active (alpha-haloalkyl)-aryl-ketals and in submitting to hydrolysis the thus obtained esters of alpha-arylalkanoic acids. The rearrangement reaction is carried out under neutral or alightly alkaline conditions, in an aprotic dipolar diluent and in the presence of a protic substance having a high dielectric constant.
    Type: Grant
    Filed: February 22, 1985
    Date of Patent: April 1, 1986
    Assignee: Zambon S.p.A.
    Inventors: Graziano Castaldi, Claudio Giordano, Fulvio Uggeri