Halogen Patents (Class 562/474)
  • Patent number: 6066761
    Abstract: A process for the isolation of 3-[2-chloro-4-(trifluoromethyl)phenoxy]benzoic acid of the formula I ##STR1## from an aqueous solution of its metal salt comprises a) reacting the metal salt of 3-[2-chloro-4-(trifluoromethyl)phenoxy]benzoic acid with an organic or inorganic acid;b) heating the reaction mixture until a liquid two-phase system of organic and aqueous phase has formed; andc) separating the organic phase from the aqueous phase.
    Type: Grant
    Filed: July 28, 1999
    Date of Patent: May 23, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans Rupert Merkle, Ronald R. Eva, Dirk Franke, Simon A. Jones, Wolfgang Mattmann, Manfred Munzinger
  • Patent number: 6015911
    Abstract: Herbicidal 1-alkyl-4-(2-chloro-3-alkoxy-4-alkylsulfonylbenzoyl)-5-hydroxypyrazole compounds, as well as 1-halo-2-chloro-3-alkoxy-4-alkylsulfonylbenzene compounds and 2-chloro-3-alkoxy-4-alkylsulfonylbenzoic acid compounds, were prepared in good yield by the reaction of the corresponding 3-chloro compound with an alkali metal alkoxide compound. 1-Halo-2-chloro-3-alkoxy-4-alkylsulfonylbenzene and 1-halo-2,3-dichloro-4-alkylsulfonylbenzene compounds were converted to compounds having hydroxycarbonyl, alkoxycarbonyl, or 1-alkyl-5-hydroxypyrazole-4-carbonyl substituents in place of the 1-halo substituent by reaction with carbon monoxide and water, an alcohol, or a 1-alkyl-5-hydroxypyrazole compound, respectively, in the presence of a palladium II salt:trihydrocarbylphosphine complex type catalyst.
    Type: Grant
    Filed: March 24, 1998
    Date of Patent: January 18, 2000
    Assignee: Dow AgroSciences LLC
    Inventors: Thomas L. Siddall, Mark V. M. Emonds, Karl L. Krumel, Jennifer M. Schomaker, Mark W. Zettler
  • Patent number: 5977117
    Abstract: Methods, compositions, and compounds for modulating the activity of an endothelin peptide are provided. The methods use compositions that contain compounds of formula (I): ##STR1## where X and Y are selected from groups that include O, S, and NH; and Ar.sup.1, Ar.sup.2 and Ar.sup.3 are independently selected from substituted or unsubstituted groups that include 5 to 6 membered aryl groups and heteraryl groups that contain one or two heteroatom(s). The methods are effected by contacting endothelin receptors with one or more of the compounds or with compositions containing one or more of the compounds prior to, simultaneously with, or subsequent to contacting the receptors with an endothelin peptide.
    Type: Grant
    Filed: January 23, 1996
    Date of Patent: November 2, 1999
    Assignee: Texas Biotechnology Corporation
    Inventors: Ming Fai Chan, Vitukudi Narayanaiyengar Balaji, Rosario Silvestre Castillo, Adam Kois, Bore Gowda Raju, Chengde Wu
  • Patent number: 5965741
    Abstract: The invention provides compounds of formula I: ##STR1## wherein A, B, D, X, R.sup.1, and R.sup.3 have any of the values defined in the specification, as well as N-oxides thereof, S-oxides thereof, pharmaceutically acceptable salts thereof, and in vivo hydrolizable esters and amides thereof, that are useful to relieve pain. The invention also provides pharmaceutical compositions as well as synthetic and therapeutic methods relating to such compounds.
    Type: Grant
    Filed: February 21, 1997
    Date of Patent: October 12, 1999
    Assignee: Zeneca Limited
    Inventors: Gloria Anne Breault, Howard Tucker, John Oldfield, Peter Warner
  • Patent number: 5922905
    Abstract: Substituted benzoic acid compounds are disclosed, having the formula: ##STR1## The compounds find use as intermediates for the production of agricultural fungicides.
    Type: Grant
    Filed: October 17, 1997
    Date of Patent: July 13, 1999
    Assignee: American Cyanamid Company
    Inventors: Juergen Curtze, Werner Simon, Gerd Morschhaeuser, Andreas Waldeck, Karl-Otto Stumm, Henry Van Tuyl Cotter, Guido Albert, Annerose Rehnig, Gunther Reichert
  • Patent number: 5866723
    Abstract: The present invention relates to novel 4-halo-2-fluoro-5-alkylbenzoyl compounds and their methods of manufacture. These compounds are useful for the preparation of agricultural chemicals and medicines, particularly as intermediates for an active class of aryl-haloalkylpyrazole and aryl alkylsulfonylpyrazole herbicides.
    Type: Grant
    Filed: June 27, 1996
    Date of Patent: February 2, 1999
    Assignee: Monsanto Company
    Inventors: Bruce C. Hamper, Kindrick L. Leschinsky
  • Patent number: 5849934
    Abstract: A perfluorinated polyimide comprising a repeating unit represented by general formula (1): ##STR1## and a perfluorinated poly(amic acid) comprising a repeating unit represented by general formula (6): ##STR2## wherein R.sub.1 is a tetravalent organic group; and R.sub.2 is a divalent organic group, provided that chemical bonds between carbon atoms and monovalent elements contained in R.sub.1 and R.sub.2 are exclusively carbon-to-fluorine bonds; methods for preparing them; and optical material including the perfluorinated polyimide. 1,4-Bis(3,4-dicarboxytrifluorophenoxy)-tetrafluorobenzene dianhydride, 1,4-difluoropyromellitic anhydride, 1,4-bis(3,4-dicarboxytrifluorophenoxy)-tetrafluorobenzene, 1,4-difluoropyromellitic acid, and 1,4-bis(3,4-dicyanotrifluorophenoxy)-tetrafluorobenzene as well as methods preparing them. The perfluorinated polyimide has a thermal stability and has a low optical loss in an optical communication wavelength region (0.8 to 1.7 .mu.m).
    Type: Grant
    Filed: January 28, 1998
    Date of Patent: December 15, 1998
    Assignee: Nippon Telegraph and Telephone Corporation
    Inventors: Shinji Ando, Toru Matsuura, Shigekuni Sasaki, Fumio Yamamoto
  • Patent number: 5792876
    Abstract: A process is described for producing acetals comprising reacting an aldehyde or a ketone with an alcohol in the presence of a titanium compound having an acetylacetone as a ligand, or in the presence of a compound selected from the group consisting of stannous chloride dihydrate, cerium chloride hexahydrate and bismuth chloride. The process can be used in the synthesis of unstable acetals or when water exists in the reaction mixture, and therefore the process can be used for a wide variety of applications.
    Type: Grant
    Filed: November 6, 1996
    Date of Patent: August 11, 1998
    Assignee: Kuraray Co., Ltd.
    Inventors: Hideharu Iwasaki, Masahiko Kitayama, Takashi Onishi
  • Patent number: 5766610
    Abstract: Novel pharmaceutically/cosmetically-active polycyclic aromatic compounds have the structural formula (I): ##STR1## wherein Ar is a radical having one of the formulae (a)-(e): ##STR2## and are useful for the treatment of a wide variety of disease states, whether human or veterinary, for example dermatological, rheumatic, respiratory, cardiovascular and ophthalmological disorders, as well as for the treatment of mammalian skin and hair conditions/disorders.
    Type: Grant
    Filed: April 26, 1995
    Date of Patent: June 16, 1998
    Assignee: Centre International De Recherches Dermatologiques Galderma
    Inventor: Jean-Michel Bernardon
  • Patent number: 5756814
    Abstract: (1) CF.sub.2 .dbd.CFO(CF.sub.2).sub.n COOR is allowed to react with chlorine or bromine to obtain CF.sub.2 XCFXO(CF.sub.2).sub.n COOR', (2) which is allowed to react with a Grignard reagent MgBrC.sub.6 H.sub.3 (CH.sub.3).sub.2 to convert the terminal group to --COC.sub.6 H.sub.3 (CH.sub.3).sub.2, (3) followed by reaction with diethylaminosulfur trifluoride to convert --COC.sub.6 H.sub.3 (CH.sub.3).sub.2 to --CF.sub.2 C.sub.6 H.sub.3 (CH.sub.3).sub.2, (4) followed further by oxidation of the resulting methyl group and by esterification to convert the methyl group to --CF.sub.2 C.sub.6 H.sub.3 (COOR).sub.2 and (5) followed by dechlorination or debromination to obtain CF.sub.2 .dbd.CFO(CF.sub.2).sub.n CF.sub.2 C.sub.6 H.sub.3 (COOR).sub.2. The resulting bifunctional vinyl ether compound having an aromatic ring is a novel compound and can be used as a copolymer component for fluorine-containing elastomers.
    Type: Grant
    Filed: June 23, 1997
    Date of Patent: May 26, 1998
    Assignee: Nippon Mektron, Limited
    Inventors: Leng-Tain Lin, Kenji Iimura, Takehiro Sonoi
  • Patent number: 5750731
    Abstract: A perfluorinated aromatic compound represented by general formula (7): ##STR1## wherein R.sub.3 is a tetravalent perfluorinated aromatic group represented by formula (8): ##STR2## wherein (R.sub.4)s are the same, each being a carboxyl group or a cyano group, or two adjacent (R.sub.4)s combine to form a divalent group represented by formula (10): ##STR3## provided that when R.sub.4 is a cyano group, R.sub.3 denotes said tetravalent perfluorinated aromatic group represented by formula (9).
    Type: Grant
    Filed: September 20, 1996
    Date of Patent: May 12, 1998
    Assignee: Nippon Telegraph & Telephone Corporation
    Inventors: Shinji Ando, Toru Matsuura, Shigekuni Sasaki, Fumio Yamamoto
  • Patent number: 5746998
    Abstract: A radiographic imaging agent including a plurality of block copolymers forming a micelle, the block copolymers including a hydrophilic polymer linked to a hydrophobic polymer, and the hydrophobic polymer including a backbone incorporating radiopaque molecules via covalent bonds.
    Type: Grant
    Filed: August 8, 1996
    Date of Patent: May 5, 1998
    Assignee: The General Hospital Corporation
    Inventors: Vladimir P. Torchilin, Vladimir S. Trubetskoy, Gerald L. Wolf, G. Scott Gazelle
  • Patent number: 5739388
    Abstract: The present invention relates to a process for the preparation of compounds of the formula ##STR1## in which the radicals R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are identical or different and are COOH, H, F, Cl, Br, CF.sub.3, OH, an alkoxy or alkyl radical having in each case 1 to 4 carbon atoms or a radical --NR.sup.6 R.sup.7, in which R.sup.6 and R.sup.7 are identical or different and are H, an alkyl radical having 1 to 4 carbon atoms or a phenyl radical, by dissolving in water a compound of the formula ##STR2## in which the radicals R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are identical or different and have the abovementioned meaning or, in departure therefrom, instead of H can be COOH, admixing the aqueous solution with a water-insoluble amine which is inert under the reaction conditions and carrying out the decarboxylation at a pH of 3 to 9 and a temperature of 70.degree. to 210.degree. C.
    Type: Grant
    Filed: May 2, 1996
    Date of Patent: April 14, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ralf Pfirmann, Hans Schubert
  • Patent number: 5567410
    Abstract: A radiographic imaging agent including a plurality of block copolymers forming a micelle, the block copolymers including a hydrophilic polymer linked to a hydrophobic polymer, and the hydrophobic polymer including a backbone incorporating radiopaque molecules via covalent bonds.
    Type: Grant
    Filed: June 24, 1994
    Date of Patent: October 22, 1996
    Assignee: The General Hospital Corporation
    Inventors: Vladimir P. Torchilin, Vladimir S. Trubetskoy, Gerald L. Wolf, G. Scott Gazelle
  • Patent number: 5530157
    Abstract: Novel benzoic acid derivatives have the formula: ##STR1## wherein --X-- represents C.sub.1 to C.sub.6 alkylene, C.sub.2 to C.sub.6 alkenylene or a divalent moiety having the structure --(CH.sub.2).sub.m --Z-- in which m is an integer from 0 to 3 and Z represents --O--, --S-- or --NH--;--Y-- represents a direct bond, C1 to C.sub.6 alkylene, C.sub.2 to C.sub.6 alkenylene or a divalent moiety having the structure --(CH.sub.2).sub.m --Z--(CH.sub.2).sub.n in which m and n are each, independently, an integer from 0 to 3 and --Z-- represents --O--, --S-- or --NH--;R represents a 5- or 6-membered carbocyclic or heterocyclic ring or a carbocyclic or heterocyclic fused ring system containing up to 10 members in the ring, which carbocyclic, heterocyclic or fused ring system may be saturated or unsaturated and may contain up to two substituents selected from lower alkyl, methoxy, halo and trifluoromethyl; andR.sup.1 and R.sup.
    Type: Grant
    Filed: February 16, 1995
    Date of Patent: June 25, 1996
    Assignee: Scios Nova Inc.
    Inventors: Richard Mewshaw, Gregory S. Hamilton
  • Patent number: 5523476
    Abstract: A process for producing tetrafluorophthalic anhydride, which comprises chlorinating tetrachlorophthalic anhydride to obtain 3,3,4,5,6,7-hexachloro-1-[3H]-isobenzofuranone, then fluorinating it to obtain 3,4,5,6-tetrafluorophthaloyldifluoride and/or 3,3,4,5,6,7-hexafluoro-1-[3H]-isobenzofuranone, and further reacting the tetrafluorophthalolyldifluoride and/or the hexafluoro-1-[3H]-isobenzofuranone with an inorganic base or an organic acid to obtain tetrafluorophthalic anhydride.
    Type: Grant
    Filed: February 21, 1995
    Date of Patent: June 4, 1996
    Assignee: Asahi Glass Company Ltd.
    Inventors: Ryuji Seki, Koji Sugimoto, Seisaku Kumai
  • Patent number: 5498795
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1 -R.sub.3 and R.sub.5 independently are hydrogen, lower alkyl of 1 to 6 carbons, branched chain alkyl or cycloalkyl of 3 to 15 carbons, lower alkyl substituted cycloalkyl of 3 to 15 carbons; R.sub.4 is lower alkyl of 1 to 6 carbons, branched chain alkyl or cycloalkyl of 3 to 15 carbons or lower alkyl substituted cycloalkyl of 3 to 15 carbons; X is S or O; Y is a phenyl group, or heteroaryl selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, imidazolyl and oxazolyl, said groups being substituted with the R.sub.5 group defined above; A is (CH.sub.2).sub.n where n is 0-5, lower branched chain alkyl having 3-6 carbons, cycloalkyl having 3-6 carbons, alkenyl having 2-6 carbons and 1 or 2 double bonds, alkynyl having 2-6 carbons and 1 or 2 triple bonds; B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR.sub.8, CONR.sub.9 R.sub.10, --CH.sub.2 OH, CH.sub.2 OR.sub.11, CH.sub.2 OCOR.sub.
    Type: Grant
    Filed: December 29, 1994
    Date of Patent: March 12, 1996
    Assignee: Allergan, Inc.
    Inventors: Tae K. Song, Roshantha A. Chandraratna
  • Patent number: 5488152
    Abstract: The present invention relates to a process for the preparation of 4-alkoxy-3,5,6-trifluorophthalic acids of the formula ##STR1## in which R is an alkyl radical having 1 to 5 carbon atoms which may be monofluorinated or polyfluorinated, a cycloalkyl radical having 3 to 5 carbon atoms in the ring which may be monofluorinated or polyfluorinated, or an araliphatic radical which may be monofluorinated or polyfluorinated, or, if desired, of 3-alkoxy-2,4,5-trifluorobenzoic acids of the formula ##STR2## in which R is as defined above, which involves reacting tetrafluorophthalic acid or tetrafluorophthalic anhydride with an alcohol of the formula ROH in which R is as defined above and with a water-soluble base in water at elevated temperature, isolating the 4-alkoxy-3,5,6-trifluorophthalic acid formed and, if desired, decarboxylating the 4-alkoxy-3,5,6-trifluorophthalic acid in the presence of a basic solvent and, if desired, of an inert solvent at from 70.degree. to 180.degree. C.
    Type: Grant
    Filed: February 9, 1995
    Date of Patent: January 30, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ralf Pfirmann, Theodor Papenfuhs
  • Patent number: 5481032
    Abstract: A process for the preparation of halogenated benzoic acids of formula (1): ##STR1## in which R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are hydrogen, fluorine, chlorine or bromine atoms or C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, nitro, cyano, trifluoromethyl, aidehyde, C.sub.1 -C.sub.4 -alkoxycarbonyl, -SO.sub.2 -C.sub.1 -C.sub.4 -alkyl, -SO.sub.2 -phenyl, -CONH.sub.2, -CON(C.sub.1 -C.sub.4 -alkyl).sub.2, hydroxy, carboxy, -NH.sub.2 or -N(C.sub.1 -C.sub.4 - alkyl).sub.2 groups, at least one of the substituents R.sub.1 -R.sub.5 being one of said halogen atoms, which comprises reacting 1 mol of a benzophenone, asymmetrically substituted on the benzene rings A and B, of general formula (2): ##STR2## in which R.sup.1 -R.sup.10 are as defined above for R.sub.1 -R.sub.
    Type: Grant
    Filed: November 29, 1993
    Date of Patent: January 2, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Ralf Pfirmann
  • Patent number: 5436367
    Abstract: Compounds of formula (I): ##STR1## (in which: R.sup.1 represents fluorinated methoxy; R.sup.2 represents a nitrogen-containing heterocyclic group and R.sup.3 represents hydrogen or amino) and pharmaceutically acceptable salts, esters and amides thereof are valuable antibacterial agents, which may be prepared by reacting a compound similar to that of formula (I) but in which R.sup.2 is replaced by a halogen atom with a compound providing the required group R.sup.2.
    Type: Grant
    Filed: April 14, 1994
    Date of Patent: July 25, 1995
    Assignees: Sanko Company, Limited, UBE Industries Limited
    Inventors: Masayuki Iwata, Tomio Kimura, Teruhiko Inoue, Yoshimi Fujihara, Tetsushi Katsube
  • Patent number: 5385693
    Abstract: Disclosed herein are optically active carboxylic acid or acid halide compounds of formula III: ##STR1## Wherein R.sub.2 represents an optically active alkyl or alkoxyalkyl group having 3 to 15 carbon atoms optionally substituted by halogen atoms; R' represents a hydroxyl group or a halogen atom; k is 0 or 1; and n represents an integer of 1 to 6.
    Type: Grant
    Filed: May 17, 1993
    Date of Patent: January 31, 1995
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takayuki Higashii, Isao Kurimoto, Shoji Toda, Masayoshi Minai, Takeshi Tani, Chizu Kawakami, Koichi Fujisawa, Kiyoshi Imamura
  • Patent number: 5380926
    Abstract: Disclosed is a method of making 3-methoxy-2,4,5-trifluorobenzoic acid. A tetrafluorophthalimide is reacted with an alkali metal hydroxide to produce a mixture of alkali metal salts of 4-hydroxy-3,5,6-trifluoro-N-alkylphthalamic acid and 3-hydroxy-2,4,5-trifluoro-N-alkylbenzamide. Those products are reacted with a methylating agent to produce 4-methoxy-3,5,6-trifluoro-N-alkylphthalamic acid and 3-methoxy-2,4,5-trifluoro-N-alkylbenzamide. Those products are reacted with an acid to produce 4-methoxy-3,5,6-trifluorophthalic acid and 3-methoxy-2,4,5-trifluorobenzoic acid. Finally, the 4-methoxy-3,5,6-trifluorophthalic acid is reacted with a decarboxylating agent to produce additional 3-methoxy-2,4,5-trifluorobenzoic acid.
    Type: Grant
    Filed: March 28, 1994
    Date of Patent: January 10, 1995
    Assignee: Occidental Chemical Corporation
    Inventors: Lawrence B. Fertel, William S. Derwin
  • Patent number: 5344968
    Abstract: o-Methoxy benzoic acid is produced by reacting chlorobenzoic acids having at least one chlorine atom at least at the ortho position with lower alcohol in the presence of a copper salt and a lower alkyl as a catalyst under moderate reaction conditions. o-Methoxy benzoic acid is useful as an intermediate for pharmaceutical, agricultural chemicals, and the like.
    Type: Grant
    Filed: June 23, 1992
    Date of Patent: September 6, 1994
    Assignee: Nippon Chemical Industrial Co., Ltd.
    Inventors: Suchart Lilitkarntakul, Shukichi Nabekawa, Masao Takada, Katsuyuki Ogura
  • Patent number: 5344958
    Abstract: Insecticidal compounds having the formula N-(2-R.sup.a -3-R.sup.b -benzoyl)-N'-(2-R.sup.c -3-R.sup.d -4-R.sup.e -5-R.sup.f -benzoyl)-N'-R.sup.g -hydrazine, where R.sup.a is a halogen or a lower alkyl; R.sup.b is lower alkoxy; R.sup.c-f are selected from hydrogen, bromo, chloro, fluoro, lower alkyl and lower alkoxy; and Rg is a (C.sub.4 -C.sub.6)alkyl or (C.sub.4 -C.sub.6)alkenyl; as well as compositions comprising an agronomically acceptable carrier and an insecticidally effective amount of such compounds; and methods of using such compounds and compositions.Also, methods for the production of the compounds and their intermediates, which methods comprise admixing a 3-amino-2-(substituted)-benzoic acid, sodium nitrite and methanol under acidic conditions.
    Type: Grant
    Filed: November 23, 1992
    Date of Patent: September 6, 1994
    Assignee: Rohm and Haas Company
    Inventors: Zev Lidert, Dat P. Le
  • Patent number: 5326898
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 independently are hydrogen, lower alkyl of 1 to 6 carbons, halogen or lower alkoxy of 1 to 6 carbons; R.sub.5 and R.sub.5 ' independently are hydrogen or lower alkyl of 1 to 6 carbons; Y is oxygen or sulfur; Z is n-alkyl having 2 to 10 carbons, cyclo or branch-chained alkyl of 3 to 10 carbons, and straight chain alkenyl having 2 to 10 carbons, or cyclo or branched chained alkenyl of 3 to 10 carbons, and the Z-Y substituent is in a 1,2 (ortho) or 1,3 (meta) position on the phenyl ring relative to the ethene moiety; A is (CH.sub.2).sub.n where n is 0-5, lower branched chain alkyl having 3 to 6 carbons, cycloalkyl having 3 to 6 carbons, alkenyl having 2 to 6 carbons and 1 or 2 double bonds, alkynyl having 2 to 6 carbons and 1 or 2 triple bonds; B is COOH or a pharmaceutically acceptable salt thereof, COOR.sub.8, CONR.sub.9 R.sub.10, --CH.sub.2 OH, CH.sub.2 OR.sub.11, CH.sub.2 OCOR.sub.11, CHO, CH(OR.sub.12).sub.2, CHOR.sub.
    Type: Grant
    Filed: February 11, 1992
    Date of Patent: July 5, 1994
    Assignee: Allergan, Inc.
    Inventor: Roshantha A. S. Chandraratna
  • Patent number: 5312975
    Abstract: A process for the preparation of 5-(2,4-difluorophenyl)-salicylic acid comprising the reaction of an organometallic derivative with a suitable substituted benzene in the presence of a transition-metal based catalyst is described.
    Type: Grant
    Filed: December 27, 1991
    Date of Patent: May 17, 1994
    Assignee: Zambon Group S.p.A.
    Inventors: Claudio Giordano, Laura Coppi, Francesco Minisci
  • Patent number: 5248817
    Abstract: A novel procedure for bromination of aromatic moieties utilizes N-bromosuccinimide or dibromodimethylhydantoin in an aqueous alkali medium. The bromination procedure is employed for the preparation of an intermediate used in the preparation of remoxipride, an antipsychotic compound.
    Type: Grant
    Filed: July 8, 1992
    Date of Patent: September 28, 1993
    Assignee: Merck & Co., Inc.
    Inventors: Joseph Auerbach, Steven A. Weissman
  • Patent number: 5239114
    Abstract: A process for the preparation of 4-(2,4-difluorophenyl)-phenyl 4-nitro-benzoate, an intermediate for the preparation of 5-(2,4-difluorophenyl)-salicylic acid, which is a drug known with the international non-proprietary name Diflunisal, is described.
    Type: Grant
    Filed: April 10, 1992
    Date of Patent: August 24, 1993
    Assignee: Zambon Group S.p.A.
    Inventors: Claudio Giordano, Laura Coppi, Maurizio Paiocchi
  • Patent number: 5233082
    Abstract: Disclosed is a method of making 3-hydroxy-2,4,5-trifluorobenzoic acid. A aqueous solution is prepared of an alkali metal base and a tetrafluorophthalimide. The solution is heated to produce a mixture of a salt of a 4-hydroxy-3,5,6-trifluorophthalamic acid and a salt of a 3-hydroxy-2,4,5-trifluorobenzamide. The solution is neutralized with acid to form a precipitate of the 4-hydroxy-3,5,6-trifluorophthalamic acid and the 3-hydroxy-2,4,5-trifluorobenzamide. The precipitate is reacted with a mineral acid to produce 3-hydroxy-2,4,5-trifluorobenzoic acid.
    Type: Grant
    Filed: November 16, 1982
    Date of Patent: August 3, 1993
    Assignee: Occidental Chemical Corporation
    Inventors: Lawrence B. Fertel, William S. Derwin
  • Patent number: 5208388
    Abstract: 2,2-Difluorocyclopropyl derivatives of the formula ##STR1## in which R represents alkyl, optionally substituted aryl or optionally substituted aralkyl andX represents hydroxymethyl, 2-hydroxyethyl, isocyanato, amino, amino hydrohalide or a radical of the formula --CO--R.sup.1, whereR.sup.1 represents hydrogen, hydroxyl, alkoxy, alkyl, halogen or amino,are intermediates for fungicides.
    Type: Grant
    Filed: September 20, 1991
    Date of Patent: May 4, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Rudolf Gassen, Bernd Baasner
  • Patent number: 5194666
    Abstract: An improved process for the synthesis of esters of 3,5,6-trichlorosalicylic acid in quantitative yield comprises reacting the acid with an alcohol under distillation conditions in the presence of a titanium ester or chelate catalyst, whereby byproduct ether formation from the alcohol is suppressed. The process is especially applicable to a process by which salicylic acid is chlorinated first in concentrated sulfuric acid and then with iodine catalyst to make the trichlorosalicylic acid which is extracted and then reacted with an alcohol and a titanium catalyst to make the ester.
    Type: Grant
    Filed: July 30, 1992
    Date of Patent: March 16, 1993
    Assignee: American Cyanamid Company
    Inventors: John A. Sedlak, Mark A. Higgins, Amy P. Essenfeld
  • Patent number: 5175353
    Abstract: The 2-(2'-aminoethoxy)ethanol salt of dicamba is useful as a herbicidal and has the advantages of a lower volatility and excellent solubility in water and organic solvents.
    Type: Grant
    Filed: September 21, 1987
    Date of Patent: December 29, 1992
    Assignee: Sandoz Ltd.
    Inventors: Rita S. Jones, Michael T. Chirchirillo, Johnny L. Burns
  • Patent number: 5175299
    Abstract: A pyrazole derivative having the formula ##STR1## is disclosed; the groups A, B, Q, V, W, X, Y, and Z are defined in the description.
    Type: Grant
    Filed: November 1, 1991
    Date of Patent: December 29, 1992
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Masatoshi Baba, Takuya Kakuta, Norio Tanaka, Eiichi Oya, Takashi Ikai, Tsutomu Nawamaki, Shigeomi Watanabe
  • Patent number: 5166365
    Abstract: A novel fluorine-containing aromatic compound of the formula: ##STR1## wherein X is ##STR2## in which R.sub.f is a perfluoroalkyl group having 1 to 10 carbon atoms,R.sub.f ' is a perfluoroalkyl group having 1 to 12 carbon atoms,p is an integer of 1 to 3,q is an integer of 0 to 3,r is 0 or 1,s is an integer of 0 to 5and t is an integer of 0 to 5,Y is X, a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or a fluoroalkyl group having 1 to 8 carbon atoms, andeach A is independently ##STR3## in which D is an amino, carboxyl, hydroxyl, methyl or haloformyl group, and n is an integer of 1 or 2, or ##STR4## can be used to derive various compounds, some of which are useful for preparing a fluorine-containing epoxy compound of polyimide with good properties.
    Type: Grant
    Filed: May 10, 1990
    Date of Patent: November 24, 1992
    Assignee: Daikin Industries Ltd.
    Inventors: Yohnosuke Ohsaka, Tsutomu Kobayashhi, Motonobu Kubo
  • Patent number: 5166404
    Abstract: Oxydiphthalic acid esters of the formula ##STR1## where Z is H or alkyl, and X is halo, X' is H or halo, or X and X' together represent an oxygen atom; are prepared by the esterification reaction of the corresponding halo-oxydiphthalic anhydride or dioxydiphthalic anhydride with an alkanol.
    Type: Grant
    Filed: October 4, 1991
    Date of Patent: November 24, 1992
    Assignee: Occidental Chemical Corporation
    Inventors: Jeffrey S. Stults, Willis T. Schwartz, Frank J. Dinan
  • Patent number: 5130475
    Abstract: Disclosed herein is a derivative of 1,5-diphenyl-1H-1,2,4-triazole-3-carboxamide represented by the following formula (I): ##STR1## wherein R represents an alkyl group of 2 to 10 carbon atoms, which is substituted by fluorine atom(s), and X represents a hydrogen atom or a fluorine atom, a process for producing the derivative and a herbicidal compositions containing the derivative of 1,5-diphenyl-1H-1,2,4-triazole-3-carboxamide as an active ingredient.
    Type: Grant
    Filed: November 26, 1991
    Date of Patent: July 14, 1992
    Assignee: Kureha Kagaku Kogyo Kabushiki Kaisha
    Inventors: Takafumi Shida, Hideo Arabori, Takeo Watanabe, Shiro Yamazaki, Hiroyasu Shinkawa
  • Patent number: 5095147
    Abstract: 2,2-Difluorocyclopropyl derivatives of the formula ##STR1## in which R represents alkyl, optionally substituted aryl or optionally substituted aralkyl andX represents hydroxymethyl, 2-hydroxyethyl, isocyanato, amino, amino hydrohalide or a radical of the formula --CO--R.sup.1, whereR.sup.1 represents hydrogen, hydroxyl, alkoxy, alkyl, halogen or amino,are intermediates for fungicides.
    Type: Grant
    Filed: April 26, 1991
    Date of Patent: March 10, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Rudolf Gassen, Bernd Baasner
  • Patent number: 5087764
    Abstract: 1,4-disubstituted 2,3-difluorobenzenes according to formula I are suitable as intermediates for the synthesis of liquid crystalline compounds.
    Type: Grant
    Filed: May 12, 1989
    Date of Patent: February 11, 1992
    Assignee: Merck Patent Gesellschaft mit beschrankter Hafung
    Inventors: Volker Reiffenrath, Joachim Krause
  • Patent number: 5086067
    Abstract: This invention relates to a compound of the formula: ##STR1## or a pharmaceutically acceptable salt thereof wherein X is oxygen, sulfur, --CH.dbd.CH-- or --CH.dbd.N--; wherein R.sub.1 is alkyl, alkenyl or alkynyl of about 1 to 20 carbon atoms; wherein R is --CO.sub.2 R.sup.2, tetrazole, methylsulfonamide or benzenesulfonamide, wherein R.sup.2 is hydrogen, alkyl of 1 to 6 carbon atoms or a pharmaceutically acceptable cation and R.sup.3 is hydroxyl or halogen, having utility as LTB.sub.4 synthesis inhibitors.
    Type: Grant
    Filed: December 18, 1989
    Date of Patent: February 4, 1992
    Assignee: G. D. Searle & Co.
    Inventors: Stevan W. Djuric, Richard A. Haack, Julie M. Miyashiro
  • Patent number: 5081283
    Abstract: Novel intermediates for fungicides, comprising fluorocyclopropyl derivatives of the formula ##STR1## in which R represents alkyl, optionally substituted aryl or optionally substituted aralkyl,X represents hydrogen, chlorine or bromine andR.sup.1 represents hydroxyl, alkoxy, alkyl or halogen.
    Type: Grant
    Filed: April 26, 1991
    Date of Patent: January 14, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Rudolf Gassen, Bernd Baasner
  • Patent number: 5081263
    Abstract: The invention relates to the dioxane adducts of armoatic meta-or para-hydroxycarboxylic acids, which consist, per mole, of 1 mole of 1,4-dioxane and about 2 moles of hydroxycarboxylic acid. The invention further relates to a process for the preparation of these adducts, which comprises dissolving the hydroxycarboxylic acids in dioxane or a mixture of the latter with water or with an organic solvent and then allowing the adducts to crystallize.
    Type: Grant
    Filed: December 14, 1989
    Date of Patent: January 14, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: von Helmold Plessen, Siegbert Rittner
  • Patent number: 5047584
    Abstract: A process for the preparation of pentahaloethoxy benzoyl halide compounds comprisingA) chlorinating p-cresyl trifluoroacetate to form p-.alpha., .alpha.-dichloro-.beta.-,.beta.-,.beta.-trifluoroethoxy benzotrichloride;B) converting the p-.alpha., .alpha.-dichloro-.beta.-,.beta.-,.beta.-trifluoroethoxy benzotrichloride to p-pentafluoroethoxy benzoyl fluoride.
    Type: Grant
    Filed: December 9, 1985
    Date of Patent: September 10, 1991
    Assignee: Occidental Chemical Corp.
    Inventors: James J. Maul, Byron R. Cotter
  • Patent number: 5041604
    Abstract: A process for producing a high quality di(aryloxy)alkane with a high yield by the use of readily commercially available materials, without using any particular solvent or agent and by means of a simple operation and a general apparatus is provided, which process comprises subjecting a halogenated alkane of the formula (II)X--A--Y (II)wherein X and Y each represent a halogen atom and A represents a lower alkylene group, and a phenol of the formula (III) ##STR1## wherein R.sub.1 to R.sub.5 each are same or different, represent hydrogen, halogen, lower alkyl, lower alkoxy, carboxylic acid salt, acyl or nitro group, and may form a ring in conjunction of two adjacent groups,to condensation reaction in the presence of an alkali in an aqueous medium to form a di(aryloxy)alkane of the formula (I) ##STR2## and is characterized (i) by carrying out the condensation reaction in a molar ratio of the compound of the formula (II): the phenol of the formula (III): the alkali in terms of monovalent base of 1:1.5 to 3.0:1.
    Type: Grant
    Filed: June 20, 1990
    Date of Patent: August 20, 1991
    Assignee: Sanko Kaihatsu Kagaku Kenkyusho
    Inventors: Toranosuke Saito, Masakatu Kitani, Takashi Ishibashi
  • Patent number: 5041610
    Abstract: Ring-opened resorcyclic acid lactone derivatives of the formla ##STR1## wherein X is ethylene or ethenylene; Y and Z, which may be the same or different, are methylene, hydroxymethylene or carbonyl; R.sub.1 is hydrogen or lower alkyl of from 1 to about 6 carbon atoms; R.sub.2, R.sub.3, R.sub.4 and R.sub.5, which may be the same or different, are hydrogen, hydroxyl, halogen, nitro, amino or a radical selected from the group consisting of --R', --OR', --COOR' and --OCOR' wherein R' is lower alkyl of from 1 to about 6 carbon atoms, lower cycloalkyl of from 3 to about 8 carbon atom, alkenyl of from 2 to about 6 carbon atoms, substituted or unsubstituted aryl of from 6 to about 8 carbon atoms, or substituted or unsubstituted aralkyl wherein the alkyl portion contains from 1 to about 6 carbon atoms and the aryl portion contains from 6 to about 8 carbon atoms. These compounds are useful as growth-promotants in food-producing animals.
    Type: Grant
    Filed: November 28, 1986
    Date of Patent: August 20, 1991
    Assignee: International Minerals & Chemical Corp.
    Inventor: Keith A. Drengler
  • Patent number: 5026895
    Abstract: The invention relates to novel fungicidally active compounds, a process for the preparation thereof, composition comprising the said composition as active ingredient and their use for agricultural purpose.The novel (trifluoromethyl)-phenoxy benzoic acid derivate can be described by formula (I), ##STR1## wherein X is hydrogen or halogen, preferably chlorine, nitro or trifluoromethyl,Y is hydrogen or halogen, preferably chlorine,Z is hydrogen, trifluoromethyl or nitro,V is hydrogen, halogen, preferably chlorine, or nitro,W is hydrogen, nitro or trifluoromethyl,R.sub.1 is alkyl having 1-4 carbon atoms, preferably ethyl, hydrogen, alkali metal, preferably sodium, potassium, or ammonium or ammonium-ion having a formula (II),NH.sub.3.sup.+ R.sub.2 (II)whereinR.sub.
    Type: Grant
    Filed: November 12, 1985
    Date of Patent: June 25, 1991
    Assignee: Budapesti Vegyimuvek
    Inventors: Jozsef Bakos, Balint Neil, Laszlo Kollar, Szilard Toros, Gvula Eifert, Ferenc Bihari, Peter Boros, Anna Durko nee Ponacz, Istvan Kuronya, Istvan Magyari, Judit Timar, Peter Bohus, Laszlo Wohl
  • Patent number: 5025036
    Abstract: The invention relates to catechol carboxylic acid derivatives of the formula ##STR1## wherein, R.sub.1 is ##STR2## acetyl, hydrogen, hydroxy or alkanoyloxy, R.sub.2 is ##STR3## hydroxy, hydrogen or alkanoyloxy, wherein R is hydrogen, lower alkyl or --(CH.sub.2).sub.n --N--(lower alkyl).sub.2,R.sub.3 is hydrogen, lower alkyl or amino,R.sub.4 is hydrogen, lower alkyl, halogen or aminoA is ##STR4## wherein, R.sub.5 is hydrogen or acyl, R.sub.6 is hydrogen, halogen, lower alkyl, aryl or cycloalkyl, and R.sub.7 and R.sub.8, independently, are hydrogen, lower alkyl or halogen, orA is ##STR5## wherein, R.sub.5 is hydrogen or acyl, R.sub.9 is hydrogen, lower alkyl, R.sub.10 is hydrogen, lower alkyl or halogen, R.sub.11 is hydrogen, lower alkyl, cycloalkyl or halogen, m is 0 or 1, n is an integer of 2-10, provided, that no more than one of R.sub.1 or R.sub.2 can be hydroxy, alkanoyloxy or ##STR6## and when R is hydrogen, salts thereof with pharmaceutically acceptable bases or when R is --(CH.sub.2).sub.
    Type: Grant
    Filed: May 3, 1989
    Date of Patent: June 18, 1991
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Matthew Carson, Ru-Jen L. Han, Ronald A. LeMahieu
  • Patent number: 5013866
    Abstract: An improved method of synthesizing 3,5-dibromosalicylic acid provides a highly purified pharmaceutical grade product free of toxic by-products and solvents. The purified product may be utilized as an intermediate in synthesizing pharmaceutical grade substances, as a bactericide when incorporated into topical ointments, and as an adjuvant in drug absorption systems.
    Type: Grant
    Filed: November 28, 1989
    Date of Patent: May 7, 1991
    Assignee: Baxter International Inc.
    Inventors: Ton T. Hai, Deanna J. Nelson
  • Patent number: 5004817
    Abstract: Compounds having the formula (I): ##STR1## wherein: M is an alkali or alkaline-earth metal or a C.sub.1 -C.sub.18 alkyl group;X is a group selected from --CH.sub.2 --, --CO--, --CH.sub.2 --CO--, --CH(CH.sub.3)--CO--,p is 0 or 1;Ar is a simple or condensed aromatic ring or Ar represents two or more aromatic nuclei bonded either by a simple bond or by an --O--, --S--, --SO.sub.2 --, --SO--, --CO--, --CS--, or --NH-- group;y is H or CH.sub.3 ;m is 1 when Y=--CH.sub.3, or an integer from 1 to 5 (including both values) when Y=H; n is a number ranging from 1 to 500 (including both values); andZ is H; a C.sub.1 -C.sub.18 alkyl; benzyl; glycidyl; acetyl; allyl; --CO--NH--R or --CO--NH--R.sub.1 --NCO group.
    Type: Grant
    Filed: February 27, 1989
    Date of Patent: April 2, 1991
    Assignee: Montefibre, S.p.A.
    Inventors: Catia Bastioli, Salvatore Garlisi, Dario Fornara, Vittorio Bellotti
  • Patent number: 5002960
    Abstract: Compounds of the formulas: ##STR1## wherein Het is an oxazole or oxazine moiety; X is O, S or SO, n is an integer from 3 to 9, Y is an aliphatic bridge; and the various R groups represent hydrogen or various substituents as described herein, are useful as antiviral agents, especially against picornaviruses. N-(Chloroalkyl)amide intermediates for the compounds of Formula I are also active as antiviral agents. Related compounds outside the scope of the above formulas are also disclosed. Also disclosed are novel intermediates, N-halo-alkyl-4-(isoxazol-5-yl)alkoxybenzamides, also useful as antiviral agents.
    Type: Grant
    Filed: June 12, 1989
    Date of Patent: March 26, 1991
    Assignee: Sterling Drug, Inc.
    Inventor: Guy D. Diana
  • Patent number: 5001256
    Abstract: Novel trisubstituted benzoic acid intermediates which are useful in the preparation of certain herbicidal 2-(2,3,4-trisubstituted benzoyl)-1,3-cyclohexanediones are described.
    Type: Grant
    Filed: July 31, 1989
    Date of Patent: March 19, 1991
    Assignee: ICI Americas Inc.
    Inventors: William J. Michaely, Jeff K. Curtis