Ester Function Attached Directly To A Ring Patents (Class 560/64)
  • Patent number: 5468897
    Abstract: Bi-aromatic esters have the formula ##STR1## wherein R.sub.1 represents H, OH, --CH.sub.3, --CH.sub.2 OH, --CH(OH)CH.sub.3, --COOR.sub.9, ##STR2## or SO.sub.2 R.sub.10 ; R.sub.9 represents H, C.sub.1 -C.sub.6 alkyl or mono or polyhydroxyalkyl; R.sub.10 represents OH, C.sub.1 -C.sub.6 alkyl or ##STR3## r' and r" represent H, C.sub.1 -C.sub.6 alkyl, aryl, aralkyl, mono or polyhydroxyalkyl, or r' and r" taken together form a heterocycle; R.sub.2 represents H, C.sub.1 -C.sub.6 alkyl, OR.sub.9, F or --CF.sub.3 ; R.sub.3, R.sub.4 and R.sub.5 represent H, F, OH, --CH.sub.3, --OCH.sub.3, --CF.sub.3, --COOH or --CH.sub.2 OH; R.sub.6 and R.sub.8 represent H, .alpha.-substituted C.sub.3 -C.sub.15 alkyl, .alpha., .alpha.'-disubstituted C.sub.4 -C.sub.12 alkyl, C.sub.3 -C.sub.12 cycloalkyl, C.sub.5 -C.sub.12 mono or polycyclic cycloalkyl whose linking carbon is trisubstituted, --SR.sub.11, --SO.sub.2 R.sub.11 or --SOR.sub.11 ; R.sub.11 represents C.sub.1 -C.sub.6 alkyl or cycloalkyl; R.sub.6 and R.sub.
    Type: Grant
    Filed: May 4, 1994
    Date of Patent: November 21, 1995
    Assignee: Centre International de Recherches Dermatologiques Galderma (Cird Galderma)
    Inventors: Braham Shroot, Jean-Michel Bernardon, William R. Pilgrim
  • Patent number: 5454974
    Abstract: Compounds of the formula ##STR1## wherein X.sup.1 denotes fluorine or chlorine and X.sup.2 denotes hydrogen, fluorine or chlorine; R.sup.1 is 3E-alkenyl, 4-alkenyl, 2E-alkenyloxy or 3-alkenyloxy; n stands for the number 0 or 1; one of the groups Y.sup.1 and Y.sup.2 is a single covalent bond, --COO--, --OOC--, --CH.sub.2 CH.sub.2 --, --CH.sub.2 O-- or --OCH.sub.2 -- and the other of the groups Y.sup.1 and Y.sup.2 is a single covalent bond; and rings A.sup.1 and A.sup.2 each individually are substituted or unsubstituted trans-1,4-cyclohexylene, in which optionally 2 non-adjacent CH.sub.2 groups are replaced by oxygen, or substituted or unsubstituted 1,4-phenylene, in which optionally 1 CH group or 2 CH groups is/are replaced by nitrogen; with the proviso that X.sup.2 denotes fluorine or chlorine and/or Y.sup.1 or Y.sup.2 denotes --CH.sub.2 O-- or --OCH.sub.2 -- when simultaneously X.sup.1 is fluorine and R.sup.1 is 3E-alkenyl,and their use for liquid crystalline mixtures and electro-optical purposes.
    Type: Grant
    Filed: January 6, 1994
    Date of Patent: October 3, 1995
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Arthur Boller, Richard Buchecker, Martin Schadt, Alois Villiger
  • Patent number: 5424479
    Abstract: The invention relates to a preparation process for aromatic methyl methoxycarboxylates by reaction of aromatic hydroxycarboxylic acids in the form of a mixture with the methoxycarboxylic acids with dimethyl sulphate in water.
    Type: Grant
    Filed: August 23, 1994
    Date of Patent: June 13, 1995
    Assignee: Cassella AG
    Inventors: Rolf Muller, Thomas Wessel
  • Patent number: 5399291
    Abstract: Fluorine-containing, chiral and achiral liquid crystal compounds comprise (a) an aliphatic fluorocarbon terminal portion comprising a perfluorinated or partially-fluorinated alkylene group and a terminal hydrocarbon alkyl group, the groups optionally containing at least one catenary ether oxygen atom; (b) an aliphatic hydrocarbon terminal portion; and (c) a central core connecting the terminal portions. The compounds have smectic mesophases or latent smectic mesophases and are useful, for example, in liquid crystal display devices.
    Type: Grant
    Filed: September 30, 1993
    Date of Patent: March 21, 1995
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Eugene P. Janulis, Gilbert C. Johnson, Marc D. Radcliffe, Patricia M. Savu, Daniel C. Snustad, Terence D. Spawn
  • Patent number: 5387718
    Abstract: Alkylphenyl alkyl ethers or alkylphenyl alkyl thioethers, of the formula ##STR1## where U represents O or S; and R.sub.1 -R.sub.6 each independently represent an alkyl or aryl group with 1-6 C atoms, but R.sub.1 -R.sub.5 may each independently represent a functional group other than these, particularly --COOR (R=C.sub.1-4 alkyl), --NO.sub.2, --NH.sub.2, --O--CH.sub.2 --CH.sub.2 --OH, --OH, --CHO, --H, or -halogen;R.sub.1 -R.sub.5 may be bridged by suitable bifunctional substituents, such as, e.g., --(CH.sub.2).sub.x --, or --(CH.sub.2).sub.x --Z--(CH.sub.2).sub.y -- (where Z represents a hetero atom; x=0-7 and y=0-7), or by unsaturated substituents or anellated ring systems; may be produced in high space-time yield by reacting the corresponding phenol or thiophenol with a arylalkyl carbonate at a temperature of 70.degree.-300.degree. C. under elevated or normal pressure, in the presence of a monocyclic, bicyclic, polycyclic, or acyclic amidine as a catalyst.
    Type: Grant
    Filed: July 14, 1992
    Date of Patent: February 7, 1995
    Assignee: Huels Aktiengesellschaft
    Inventors: Gunther Kohler, Peter Bickert
  • Patent number: 5382380
    Abstract: New p-terphenyl derivatives useful as components for preparing practical ferroelectric liquid crystalline compositions and excellent in chemical stability, as well as liquid crystalline compositions containing at least one of the p-terphenyl derivatives.
    Type: Grant
    Filed: June 1, 1992
    Date of Patent: January 17, 1995
    Assignee: Kanto Kagaku Kabushiki Kaisha
    Inventors: Makoto Kurihara, Hiromi Inoue, Atsushi Sugiura, Kenji Suzuki, Tsunenori Fujii
  • Patent number: 5380915
    Abstract: A liquid-crystalline copolymer comprising the repeating units represented by the following general formulas ##STR1## wherein each of r and p is an integer of 2 to 5, q is an integer of 0 to 3, m is an integer of 1 to 20, and R.sup.1 is ##STR2## R.sup.2 being --COOR.sup.3, --OR.sup.3 or --OCOR.sup.3 R.sup.3, ##STR3## each of R.sup.4 and R.sup.5 being --CH.sub.3 or a halogen atom, each of a and d being an integer of 0 to 10, b being an integer of 0 or 1, with the proviso that d is not 0 when R.sup.5 is --CH.sub.3, the repeating units [I] and [II] being present in the liquid-crystalline copolymer in a substantial molar ratio [I]:[II] of 1:1, exhibits ferroelectricity even at a temperature neighboring room temperature and having a high response speed to changes of external electric fields.
    Type: Grant
    Filed: May 26, 1993
    Date of Patent: January 10, 1995
    Assignee: Idemitsu Kosan Co., Ltd.
    Inventors: Kazuharu Morita, Satoshi Hachiya, Fumio Moriwaki, Hiroyuki Endo
  • Patent number: 5374376
    Abstract: Disclosed are herein optically active aromatic compounds represented by the formula (I): ##STR1## wherein X represents --COO-- or --OCO--; Y represents --COO--, --OCO-- or --O--; R.sub.2 represents an alkyl or alkoxyalkyl group having 1 to 20 carbon atoms unsubstituted or substituted by a halogen atom; R.sub.1 represents an alkyl group having 3 to 20 carbon atoms;Z represents ##STR2## wherein p represents a number of 1 to 5 and * indicates an asymmetric carbon atom; l and k each represents a number of 1 or 2; m and s each represents a number of 0 or 1, which are useful as a liquid crystal.
    Type: Grant
    Filed: September 21, 1993
    Date of Patent: December 20, 1994
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takayuki Higashii, Isao Kurimoto, Shoji Toda, Masayoshi Minai, Shigeaki Chika, Koichi Fujisawa, Kiyoshi Imamura
  • Patent number: 5374772
    Abstract: The invention relates to compounds of the formula ##STR1## R is hydrogen, lower alkyl, --(CH.sub.2).sub.2 N(R.sub.3).sub.2 or --CH.sub.2 OOCR.sub.3 wherein R.sub.3 is lower alkyl;R.sub.1 is CH.sub.3 (CH.sub.2).sub.n --, wherein n is 0-17, or R.sub.4 (CH.sub.2).sub.p --, wherein p is 2-18 and R.sub.4 is 1- or 2-naphthyloxy, 2,3- or 3,4-dihydroxyphenyl, phenyl, phenoxy, or substituted phenyl or phenoxy wherein the substituent is selected from the group consisting of hydroxy, benzyloxy, methylsulfinyl, methylsulfonyl or phenyl;R.sub.2 is R.sub.4 (CH.sub.2).sub.p --, 1-adamantyl--CO-- or diphenylmethyl--CO--, and, when R is hydrogen, pharmaceutically acceptable salts with bases.The compounds of formula I are potent inhibitors of phospholipases A.sub.2 (PLA.sub.2 's) and are therefore useful in the treatment of diseases, such as psoriasis, inflammatory bowel disease, asthma, allergy, arthritis, dermatitis, gout, pulmonary disease, myocardial ischemia, and trauma induced inflammation, such as spinal cord injury.
    Type: Grant
    Filed: October 22, 1993
    Date of Patent: December 20, 1994
    Assignee: Hoffmann-LaRoche Inc.
    Inventors: Mathew Carson, Ru-Jen L. Han, Ronald LeMahieu, Vincent S. Madison
  • Patent number: 5366656
    Abstract: Optically active compounds of general formulae ##STR1## wherein A is O or S, R.sub.1 is a hydrogen atom, an alkyl group having 1-22 carbon atoms, a hydroxy containing alkyl group, para-alkyl substituted phenyl, para-alkyl substituted biphenyl, hydroxyphenyl, hydroxybiphenyl or tosyl; R.sub.2 is an alkyl group having 2-8 carbon atoms; m is an integer of 0-5, n is 0 or 1, where when m=0, n is not 1; p is 0 or 1; q is 0 or 1; D and E are independently H or a halogen atom; R.sub.3 is a linear alkyl group having 1 to 22 carbon atoms; and * and ** are asymmetric centers.
    Type: Grant
    Filed: February 24, 1994
    Date of Patent: November 22, 1994
    Assignee: Industrial Technology Research Institute
    Inventors: Wen-Liang Tsai, Shu-Hui Yang
  • Patent number: 5360575
    Abstract: An optically active lactic acid derivative having the formula (1a): ##STR1## wherein A is O or S; B is --(CH.sub.2).sub.m -- or --(CH.sub.2).sub.n --O; R1 is an alkoxy group having 1-22 carbon atoms, a phenolate, a substituted phenolate, a hydroxy group, or a halogen atom; R2 is an alkyl group having 2-8 carbon atoms; m is 0, 1, 2, 3 or 4; n is 2, 3, 4 or 5; C* is an asymmetric carbon atom. Liquid crystal compositions and liquid crystal devices containing the above mentioned derivatives are also disclosed.
    Type: Grant
    Filed: November 8, 1991
    Date of Patent: November 1, 1994
    Assignee: Industrial Technology Research Institute
    Inventors: Wen-Liang Tsai, Hwei-Long Kuo
  • 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: 5344959
    Abstract: Compounds of the formula ##STR1## wherein m is 1-4; R.sub.1 -R.sub.4 independently are hydrogen, lower alkyl of 1 to 6 carbons, Cl, Br, or I; R.sub.5 is hydrogen, lower alkyl of 1 to 6 carbons, Cl, Br, I, lower alkoxy or lower thioalkoxy of 1-6 carbons; R.sub.6 is hydrogen, lower alkyl, Cl, Br, I, OR.sub.11, SR.sub.11, OCOR.sub.11, SCOR.sub.11, NH2, NHR.sub.11, N(R.sub.11).sub.2, NHCOR.sub.11 OR NR.sub.11 --COR.sub.11 ; R.sub.20 is independently hydrogen or lower alkyl; 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.11, CHO, CH(OR.sub.12).sub.2, CHOR.sub.13 O, --COR.sub.7, CR.sub.7 (OR.sub.12).sub.2, or CR.sub.7 OR.sub.13 O, where R.sub.
    Type: Grant
    Filed: May 18, 1993
    Date of Patent: September 6, 1994
    Assignee: Allergan, Inc.
    Inventor: Roshantha A. Chandraratna
  • Patent number: 5338773
    Abstract: The invention provides dental cement compositions and methods of using them for binding hard tooth material, metal and ceramic. The cement compositions include polymerizable acid reactive ethylenically unsaturated monomers, and a source of cations reactive therewith, to further crosslink the resulting polymer. The cements have superior adhesion to tooth without separately acid etching dentin or enamel. Compositions of are useful as dental luting cements, liners, bases and restoratives.
    Type: Grant
    Filed: April 19, 1993
    Date of Patent: August 16, 1994
    Assignee: Dentsply Research & Development Corp.
    Inventors: Kewang Lu, Chin-Teh Huang, Paul Hammesfahr
  • Patent number: 5332856
    Abstract: Bi-aromatic esters have the formula ##STR1## wherein R.sub.1 represents H, OH, --CH.sub.3, --CH.sub.2 OH, --CH(OH)CH.sub.3, --COOR.sub.9, ##STR2## or SO.sub.2 R.sub.10 ; R.sub.9 represents H, C.sub.1 -C.sub.6 alkyl or mono or polyhydroxyalkyl; R.sub.10 represents OH, C.sub.1 -C.sub.6 alkyl or ##STR3## r' and r'' represent H, C.sub.1 -C.sub.6 alkyl, aryl, aralkyl, mono or polyhydroxyalkyl, or r' and r'' taken together form a heterocycle; R.sub.2 represents H, C.sub.1 -C.sub.6 alkyl, OR.sub.9, F or --CF.sub.3 ; R.sub.3, R.sub.4 and R.sub.5 represent H, F, OH, --CH.sub.3, --OCH.sub.3, --CF.sub.3, --COOH or --CH.sub.2 OH; R.sub.6 and R.sub.8 represent H, .alpha.-substituted C.sub.3 -C.sub.15 alkyl, .alpha.,.alpha.'-disubstituted C.sub.4 -C.sub.12 alkyl, C.sub.3 -C.sub.12 cycloalkyl, C.sub.5 -C.sub.12 mono or polycyclic cycloalkyl whose linking carbon is trisubstituted, --SR.sub.11, --SO.sub.2 R.sub.11 or --SOR.sub.11 ; R.sub.11 represents C.sub.1 -C.sub.6 alkyl or cycloalkyl; R.sub.6 and R.sub.
    Type: Grant
    Filed: December 16, 1992
    Date of Patent: July 26, 1994
    Assignee: Centre International de Recherches Dermatologiques Galderma (CIRD Galderma)
    Inventors: Braham Shroot, Jean-Michel Bernardon, William R. Pilgrim
  • Patent number: 5296638
    Abstract: An improved process for preparing carboxylated 2-allyl-phenols of general formula (I): ##STR1## is disclosed, which consists of a first step of simultaneous esterification and etherification of a carboxylated phenol, subsequent rearrangement of the resulting product to yield allyl-carboxylated allyl-phenol and end saponification of the latter into carboxylated 2-allyl-phenol.
    Type: Grant
    Filed: August 20, 1992
    Date of Patent: March 22, 1994
    Assignee: Eniricerche S.p.A.
    Inventors: Alessandro Lezzi, Arnaldo Roggero, Ugo Pedretti, Cesarina Bonfanti
  • Patent number: 5296601
    Abstract: A process for producing a carboxylic acid ester, which comprises reacting an organic chloride having at least one chlorine atom on its ring of a substituted or unsubstituted, aromatic or heterocyclic hydrocarbon with carbon monoxide and an amine or an alcohol in the presence of a base by using as catalysts a palladium compound and a phosphine compound represented by the general formula (V):(R).sub.2 P--X--P(R).sub.2 (V)wherein R is an alkyl group or a substituted or unsubstituted phenyl group, and X is an alkylene group having 1 to 6 carbon atoms, ##STR1## or a binaphthyl group.
    Type: Grant
    Filed: May 27, 1992
    Date of Patent: March 22, 1994
    Assignee: Nihon Nohyaku Co., Ltd.
    Inventors: Keiji Suto, Masaaki Kudo, Moriharu Yamamoto
  • Patent number: 5276205
    Abstract: Novel insecticides have the formula ##STR1## in which R.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.2 -C.sub.5 carboalkoxy, C.sub.2 -C.sub.5 alkylcarbonyl, nitro or cyano;R.sub.2 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkylthio, C.sub.3 haloalkenoxy, nitro, cyano, C.sub.2 -C.sub.5 alkylcarbonyl, C.sub.1 -C.sub.4 alkylsulfonyl or C.sub.2 -C.sub.5 carboalkoxy;R.sub.3 is hydrogen, halogen, C.sub.1 -C.sub.4 haloalkyl or C.sub.1 -C.sub.4 alkoxy;provided that:R.sub.1, R.sub.2 and R.sub.3 are not all hydrogen; orR.sub.1 and R.sub.2 taken together are C.sub.2 -C.sub.4 alkylene, C.sub.2 -C.sub.4 alkyleneoxy, C.sub.1 -C.sub.2 perhaloalkyleneoxy, C.sub.1 -C.sub.4 alkylenedioxy or halo-C.sub.1 -C.sub.3 alkylenedioxy;R.sub.
    Type: Grant
    Filed: May 11, 1989
    Date of Patent: January 4, 1994
    Assignee: ICI Americas Inc.
    Inventor: Karl J. Fisher
  • Patent number: 5266721
    Abstract: The preparation of the pure enantiomers of LIFIBROL and its alkyl esters is achieved with surprisingly good yield by reacting the pure enantiomeric forms of S(-) R(+)-4-(4-tert.butylphenyl)-1,2-epoxy butane with 4-hydroxybenzoic acid alkyl ester at elevated temperature in DMF and in the presence of 4-hydroxybenzoic acid alkyl ester sodium salt. Thereafter, the raw reaction product is separated. Either the stereochemically pure LIFIBROL ester is then recovered by recrystallization or the precipitated LIFIBROL enantiomer is made in pure crystalline form by mild alkaline saponification and subsequent acidification.
    Type: Grant
    Filed: June 4, 1992
    Date of Patent: November 30, 1993
    Assignee: Klinge Pharma GmbH
    Inventors: Friedemann Reiter, Hans-Helmut Henschel
  • Patent number: 5264152
    Abstract: An optically active compound represented by the formula (I): ##STR1## wherein R is a straight or branched chain alkyl or alkoxy group having 1 to 15 carbon atoms, ##STR2## is a 1,4-cyclohexylene or 1,4-phenylene group, ##STR3## is a 1,4-phenylene or 3-fluoro-1,4-phenylene group, X is a mono-, di- or tri-fluoromethyl group, W is a straight or branched chain or cyclic alkylene group having 1 to 16 carbon atoms or a straight or branched chain alkenylene group having 2 to 16 carbon atoms, Y is a bond or --COO--, and Z is a straight or branched chain alkyl group having 1 to 8 carbon atoms, a phenyl group or a hydrogen atom, which is useful as a component of ferroelectric liquid crystal compositions or as a device utilizing said composition.
    Type: Grant
    Filed: April 7, 1992
    Date of Patent: November 23, 1993
    Assignee: Sharp Kabushiki Kaisha
    Inventors: Makoto Shiomi, Mitsuhiro Koden, Tomoaki Kuratate, Fumiaki Funada
  • Patent number: 5262082
    Abstract: Fluorine-containing liquid crystal compounds are provided. The compounds comprise a fluorocarbon terminal portion having at least one catenary ether oxygen and a hydrocarbon terminal portion, the terminal portion being connected by a central core, the compounds having smectic mesophases or having latent smectic mesophases.
    Type: Grant
    Filed: April 28, 1992
    Date of Patent: November 16, 1993
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Eugene P. Janulis, Gilbert C. Johnson, Patricia M. Savu, Terence D. Spawn
  • Patent number: 5256826
    Abstract: A process for the preparation of aromatic carbonyl or sulfonyl compounds with a diaryl ether structure by reacting phenols with halogenated carbonyl- or sulfonylaromatic compounds in a dipolar aprotic solvent is carried out in the presence of catalytic amounts of alkali metal nitrite or an aromatic nitro, nitroso, azo, azoxy or hydrazo compound.
    Type: Grant
    Filed: August 31, 1992
    Date of Patent: October 26, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Erwin Hahn, Heinrich J. Eilingsfeld, Helmut Reichelt, Alexander Aumueller, Bernd Hupfeld
  • Patent number: 5238603
    Abstract: A liquid crystal compound having specific features suitable to use for a display mode utilizing ferroelectric liquid crystals, particularly a large spontaneous polarization value and a liquid crystal composition using the compound are provided, which compound is an optically active liquid crystalline compound of the formula ##STR1## wherein l and m each are 0 or 1; at least one of R.sup.1 and R.sup.2 is an optically active alkoxy group of the formula ##STR2## wherein R.sup.3 is 2 or 3C alkyl and R.sup.4 is 3-18C alkyl, but R.sup.3 .noteq.R.sup.4 and the other thereof is 1-20C alkyl, alkoxy or alkanoyloxy, halogen or cyano; and A is a specified two or three rings compound.
    Type: Grant
    Filed: April 7, 1992
    Date of Patent: August 24, 1993
    Assignee: Chisso Corporation
    Inventors: Kazutoshi Miyazawa, Naoyuki Yoshida, Masakazu Kaneoya
  • 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: 5229375
    Abstract: Phosphine oxide-terminated allene-ene-yne compounds are disclosed that possess DNA-cleaving, antimicobial and tumor growth-inhibiting properties. Methods of making and using those compounds are also disclosed.
    Type: Grant
    Filed: August 1, 1990
    Date of Patent: July 20, 1993
    Assignee: Scripps Clinic and Research Foundation
    Inventors: Peter E. Maligres, Kyriacos C. Nicolaou
  • Patent number: 5227512
    Abstract: An optically active stilbene compound of formula (I): ##STR1## wherein R is an alkoxy group with 20 or less carbon atoms; n is an integer of 1 or 2; and R* is an optically active group, a substituted benzylphosphonate compound of formula (II) serving as an intermediate for preparing the above active stilbene compound, ##STR2## wherein X represents ##STR3## R' is an alkyl group having 1 to 5 carbon atoms, or an unsubstituted or substituted aryl group; and R* is the same as in formula (I), a method of producing the optically active stilbene compound of formula (I), and a liquid crystal composition containing the optically active stilbene compound of formula (I) are disclosed.
    Type: Grant
    Filed: December 20, 1990
    Date of Patent: July 13, 1993
    Assignee: Ricoh Company, Ltd.
    Inventor: Masayuki Shoshi
  • Patent number: 5209867
    Abstract: Novel derivatives of aromatic carboxylic acid esters which are useful as a dopant for liquid crystal compositions, and smectic liquid crystal compositions containing at least one of said derivatives.
    Type: Grant
    Filed: December 30, 1991
    Date of Patent: May 11, 1993
    Assignee: Sharp Kabushiki Kaisha
    Inventors: Mitsuhiro Koden, Tomoaki Kuratate, Fumiaki Funada
  • Patent number: 5204018
    Abstract: Compounds of the formula ##STR1## wherein n stands for the number 0 or 1; R.sup.1 denotes a group R.sup.3 or R.sup.3 --A.sup.3 --Z.sup.2 -- and R.sup.2 denotes a group R.sup.4 or R.sup.4 --A.sup.4 --Z.sup.3 --; ring A.sup.1 signifies unsubstituted or halogen-, cyano- and/or methyl-substituted 1,4-phenylene in which optionally 1 CH group or 2 CH groups is/are replaced by nitrogen; A.sup.3, A.sup.4 and ring A.sup.2 each independently represent unsubstituted or halogen-, cyano- and/or methyl-substituted 1,4-phenylene in which optionally 1 CH group or 2 CH groups is/are replaced by nitrogen or trans-1,4-cyclohexylene, trans-1,3-dioxane-2,5-diyl, 1-cyano-trans-1,4-cyclohexylene, bicyclo[2.2.2]octane-1,4-diyl, naphthalene-2,6-diyl, tetralin-2,6-diyl or trans-decalin-2,6-diyl; Z.sup.1, Z.sup.2 and Z.sup.3 each independently signify a single covalent bond, --COO--, --OOC--, --CH.sub.2 O--, --OCH.sub.2 --, --CH.tbd.C--, --(CH.sub.2).sub.3 O--, --O(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4 -- or the trans form of --CH.
    Type: Grant
    Filed: January 22, 1991
    Date of Patent: April 20, 1993
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Stephen Kelly
  • 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: 5200550
    Abstract: Bi-aromatic esters have the formula ##STR1## wherein R.sub.1 represents H, OH, --CH.sub.3, --CH.sub.2 OH, --CH(OH)CH.sub.3, --COOR.sub.9, ##STR2## or SO.sub.2 R.sub.10 ; R.sub.9 represents H, C.sub.1 -C.sub.6 alkyl or monoor polyhydroxyalkyl; R.sub.10 represents OH, C.sub.1 -C.sub.6 alkyl or ##STR3## r' and r" represent H, C.sub.1 -C.sub.6 alkyl, aryl, aralkyl, mono or polyhydroxyalkyl, or r' and r" taken together form a heterocycle; R.sub.2 represents H, C.sub.1 -C.sub.6 alkyl, OR.sub.9, F or --CF.sub.3 ; R.sub.3, R.sub.4 and R.sub.5 represent H, F, OH, --CH.sub.3, --OCH.sub.3, --CF.sub.3, --COOH or --CH.sub.2 OH; R.sub.6 and R.sub.8 represent H, .alpha.-substituted C.sub.3 -C.sub.15 alkyl, .alpha.,.alpha.'-disubstituted C.sub.4 -C.sub.12 alkyl, C.sub.3 -C.sub.12 cycloalkyl, C.sub.5 -C.sub.12 mono or polycyclic cycloalkyl whose linking carbon is trisubstituted, --SR.sub.11, --SO.sub.2 R.sub.11 or --SOR.sub.11 ; R.sub.11 represents C.sub.1 -C.sub.6 alkyl or cycloalkyl; R.sub.6 and R.sub.
    Type: Grant
    Filed: July 17, 1990
    Date of Patent: April 6, 1993
    Assignee: Centre International de Recherces Dermatologiques Galderma (Cird Galderma)
    Inventors: Braham Shroot, Jean-Michel Bernardon
  • Patent number: 5198571
    Abstract: A region-specific monofunctionalization of a phenolic hydroxy onto a polyphenol for the preparation of a compound of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms, alkenyl and alkynyl of 2 to 8 carbon atoms, --CN, formyl, carboxy, alkoxy carbonyl of up to 9 carbon atoms, aralkoxy carbonyl or up to 12 carbon atoms and halogen and R' is a hydroxy protective group comprising reacting a polyphenol of the formula ##STR2## wherein R has the above definition with a base to form the corresponding dianion, reacting the latter with a trialkyl borate of the formulaB(OAlk).sub.3wherein Alk is alkyl of 1 to 6 carbon atoms to form a compound of the formula ##STR3## reacting the latter with a reagent capable of introducing a hydroxy protective group and reacting the latter with a hydrolysis agent for the oxygen-boron bond to obtain the corresponding compound of Formula I.
    Type: Grant
    Filed: December 16, 1991
    Date of Patent: March 30, 1993
    Assignee: Roussel Uclaf
    Inventors: Jean-Louis Brayer, Daniel Calvo, Francois Ottello
  • Patent number: 5191108
    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 cycloalky, 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: April 3, 1991
    Date of Patent: March 2, 1993
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Matthew Carson, Ru-Jen L. Han, Ronald A. Lemahieu
  • Patent number: 5188762
    Abstract: A mesomorphic compound represented by the following formula (I): ##STR1## wherein R.sub.1 denotes a linear or branched alkyl group having 2-16 carbon atoms capable of including one or two non-neighboring methylene groups which can be replaced with ##STR2## and capable of including fluorine substituted for hydrogen; A denotes --A.sub.1 -- or --A.sub.1 --A.sub.2 -- and B denotes --B.sub.1 -- or --B.sub.1 --B.sub.2 -- wherein A.sub.1, A.sub.2, B.sub.1 and B.sub.2 respectively denote ##STR3## wherein Y.sub.1 and Y.sub.2 respectively denote H, F, Cl, Br, --CH.sub.3, --CN or --CF.sub.3 ; Z.sub.1 and Z.sub.2 respectively denote ##STR4## Z.sub.3 denotes ##STR5## R.sub.2, R.sub.3 and R.sub.4 respectively denote a linear or branched alkyl group having 1-16 carbon atoms including a methylene group which can be replaced with ##STR6## with proviso that it is not adjacent to the silicon atom; p and q are respectively 0 or 1 with proviso that p+q is 0 or 1; and n is an integer of 1-12.
    Type: Grant
    Filed: May 20, 1991
    Date of Patent: February 23, 1993
    Assignee: Canon Kabushiki Kaisha
    Inventors: Takashi Iwaki, Takao Takiguchi, Takeshi Togano, Yoko Yamada, Shinichi Nakamura
  • Patent number: 5185454
    Abstract: Symmetrical diaryl-acetylenes can be prepared by reacting an aryl halide with acetylene in the presence of a palladium catalyst and a base. If the acetylene is introduced into the liquid reaction mixture using a high intensity gas dispersion means, the aryl halide used can be an aryl bromide.
    Type: Grant
    Filed: October 2, 1990
    Date of Patent: February 9, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Axel Bader, Dieter Arlt
  • Patent number: 5184847
    Abstract: Ferrelectric chiral smetic liquid crystal compound are provided which have the formula, for example ##STR1## wherein R is a C.sub.1-20 alkyl group.
    Type: Grant
    Filed: November 4, 1991
    Date of Patent: February 9, 1993
    Assignee: Showa Shell Sekiyu Kabushiki Kaisha
    Inventors: Yoshiichi Suzuki, Hiroyuki Mogamiya, Ichiro Kawamura
  • Patent number: 5175339
    Abstract: A process for producing a dialkyl ester (i.e. BTDE) from its corresponding dianhydride (i.e., BTDA) comprising mixing the dianhydride, an organic solvent, solid catalyst and an alcohol capable of reacting with the dianhydride stirring the solution until the dianhydride and alcohol have reacted to form the dialkyl ester, separating the dialkyl ester from the catalyst and drying the ester to form a solid paticulate product. The product has a purity of over 85%.
    Type: Grant
    Filed: May 14, 1990
    Date of Patent: December 29, 1992
    Assignee: The Standard Oil Company
    Inventors: Eduard P. Babayan, Douglas G. Soden, Anthony Bosch
  • Patent number: 5175348
    Abstract: The invention relates to a novel process for the preparation of halogenated carboxylic acid esters of formula I ##STR1## wherein R.sub.1 is alkyl, alkenyl, alkynyl, cycloalkyl, aralkyl or aryl, R.sub.2 hydrogen is alkyl or cycloalkyl, and R.sub.3 is halogen having an atomic number of from 9 up to and including 53, which process comprises reacting an acylal of formula II ##STR2## with a hydrogen halide of the formula H--R.sub.3 (III).
    Type: Grant
    Filed: March 10, 1992
    Date of Patent: December 29, 1992
    Assignee: Saurefabrik Schweizerhall
    Inventors: Pasquale Gallegra, Gerhard Degischer
  • Patent number: 5171879
    Abstract: The invention relates to a novel process for the preparation of chlorinated carboxylic acid esters of formula I ##STR1## wherein R.sub.1 is alkyl, alkenyl, alkynyl, cycloalkyl, aralkyl or aryl and R.sub.2 hydrogen is alkyl or cycloalkyl, which process comprises reacting an acylal of formula II ##STR2## with thionyl chloride.
    Type: Grant
    Filed: March 10, 1992
    Date of Patent: December 15, 1992
    Assignee: Saurefabrik Schweizerhall
    Inventors: Pasquale Gallegra, Gerhard Degischer
  • Patent number: 5171878
    Abstract: Process for the preparation of .beta.-resorcylic acid derivatives of the general formula ##STR1## in which R, R.sup.2 and R.sup.3 can be identical or different and denote a hydrogen atom or an alkyl radical and R.sup.1 and R.sup.4 can be identical or different and denote an alkyl radical, by reaction of a diketone with .beta.-ketocarboxylic acid derivatives in the presence of an alkaline earth metal compound. The derivatives are useful as fragrances, or in perfumes.
    Type: Grant
    Filed: February 4, 1991
    Date of Patent: December 15, 1992
    Assignee: Consortium for elektrochemische Industrie GmbH
    Inventor: Rolf Hirsenkorn
  • Patent number: 5164527
    Abstract: Acylation or sulphonylation of aromatic compounds, one of which is selected from aromatic carboxylic and sulphonic acids and esters and anhydrides thereof, using an aluminosilicate catalyst having acidic sites.
    Type: Grant
    Filed: April 3, 1991
    Date of Patent: November 17, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventor: Alan B. Newton
  • Patent number: 5164112
    Abstract: .alpha.-hydroxyketone derivatives represented by the general formula (I) which are novel optically active compounds; liquid crystal compositions, such as chiral smectic or chiral nematic compositions, containing the derivatives; and liquid crystal devices using the compositions. ##STR1## wherein A and B are independently a radical represented by the general formula (II): ##STR2## wherein R.sup.2 is an aliphatic hydrocarbon having 1 to 16 carbon atoms, which may contain --O-- and may be substituted by a cyano group and/or a halogen atom, ##STR3## are independently a single bond, ##STR4## etc., X and Y are independently a single bond, or --CH.sub.2 CH.sub.2 --, etc., or an aliphatic hydrocarbon having 1 to 16 carbon atoms; R.sup.1 is an alkyl group, a phenyl group, or a cyclohexyl group; n is 0 or 1; and the asterisk (*) indicates an asymmetric carbon atom.
    Type: Grant
    Filed: July 17, 1990
    Date of Patent: November 17, 1992
    Assignee: Chisso Corporation
    Inventors: Shinichi Saito, Hiromichi Inoue, Kouji Ohno
  • Patent number: 5153353
    Abstract: p-Oxybenzoic acid derivatives of the general formula (1) ##STR1## their physiologically compatible salts and their enantiomeric and diastereomeric forms have hypolipemic properties and are therefore suitable for the preparation of drugs with hypolipemic action.
    Type: Grant
    Filed: August 8, 1991
    Date of Patent: October 6, 1992
    Assignee: Klinge Pharma GmbH
    Inventors: Friedemann Reiter, Peter Jank, Michael Schliack, Kaisli Kaipainen-Reiter, Gerhard Lang, Anke Schink
  • Patent number: 5149865
    Abstract: The invention relates to p-oxibenzoic acid derivatives of the general formula (1) where: ##STR1## their diastereomers and enantiomers in pure form or as mixture of stereoisomeric forms and their physiologically compatible salts, a process for the preparation thereof and the use thereof for preparing drugs with hypolipemic effect.
    Type: Grant
    Filed: December 20, 1991
    Date of Patent: September 22, 1992
    Assignee: Klinge Pharma GmbH
    Inventors: Friedemann Reiter, Helmut Grill, Hans-Helmut Henschel, Michael Schliack, Klaus Seibel, Roland Loser, Gerhard Lang
  • Patent number: 5137653
    Abstract: This invention provides a novel alkanoyl ester compound represented by general formula (I): ##STR1## (wherein A is of --, --O--, ##STR2## B is ##STR3## l and m are 1 or 2 provided that both are not simultaneously 2, k and n are an integer of 1 or more, respectively, provided that k>n, and R is an alkyl group), a liquid crystal composition containing this compound, a novel alkanoylphenyl compound or a novel alkanoylbiphenyl compound as an intermediate for the production of the above compound, and a method of producing the same. These novel alkanoyl ester compounds are excellent in the stability against light and the like and can take a liquid crystal state at a wide temperature range. Particularly, these compounds form liquid crystals of ferroelectricity having a large spontaneous polarization and a fast response rate by introducing an optically active group into the compound, so that they develop a very excellent effect as a starting material for optoelectronics and its related elements.
    Type: Grant
    Filed: October 18, 1991
    Date of Patent: August 11, 1992
    Assignee: Nippon Mining Co., Ltd.
    Inventors: Toshihiro Hirai, Atsushi Yoshizawa, Isa Nishiyama, Mitsuo Fukumasa, Nobuyuki Shiratori, Akihisa Yokoyama
  • Patent number: 5131945
    Abstract: Compounds of formula I ##STR1## are useful as herbicides, effective against dicotyledonous weeds.
    Type: Grant
    Filed: July 13, 1990
    Date of Patent: July 21, 1992
    Assignee: Shell Research Limited
    Inventors: Hans-Joachim Bissinger, Ludwig Schoeder, Helmut Baltruschat, Manfred Garrecht, Erich Raddatz, Wolfgang Fruhstorfer
  • Patent number: 5130454
    Abstract: Polytetrahydrofuran derivatives of the general formula ##STR1## where n is from 2 to 70, X is the bridge member --NH-- or --O-- and R.sup.1 and R.sup.4 are each hydrogen or various radicals.
    Type: Grant
    Filed: December 19, 1990
    Date of Patent: July 14, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Eckhard Hickmann, Ulrich Koehler, Hardo Siegel
  • Patent number: 5128479
    Abstract: Oxidized diphenylheteroalkanes of the formula I ##STR1## where R.sup.1 to R.sup.6 and A have the meanings specified in the description, and the preparation thereof are described. The substances are suitable for controlling diseases and as cosmetic agents.
    Type: Grant
    Filed: January 29, 1990
    Date of Patent: July 7, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Janssen, Hans-Heiner Wuest
  • Patent number: 5124070
    Abstract: Disclosed are herein optically active ester derivatives represented by the formula (I): ##STR1## (wherein R.sub.1 represents an alkyl group having 3 to 20 carbon atoms; R.sub.2 represents an optically active alkyl or alkoxyalkyl group having 3 to 15 carbon atoms optionally substituted by halogen atoms; Y represents --O--, --COO-- or --OCO--; X represents --COO-- or --OCO--; l represents a number of 1 or 2; k and m each represents a number of 0 or 1; n represents a number of 1 to 6), preparation processes therefor, liquid crystal materials containing such ester derivatives as active ingredient, and a light switching element using said liquid crystal materials as liquid crystal element.
    Type: Grant
    Filed: August 28, 1989
    Date of Patent: June 23, 1992
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takayuki Higashii, Isao Kurimoto, Shoji Toda, Masayoshi Minai, Takeshi Tani, Chizu Kawakami, Koichi Fujisawa, Kiyoshi Imamura
  • Patent number: 5117002
    Abstract: A process for the production of diaryl ethers which comprises heating, to a temperature of 80.degree. C. to 220.degree. C., a compound of the formula ##STR1## wherein X and Y are selected from the group consisting of H, CN, CO.sub.2 H, CHO, NO.sub.2, and CF.sub.3, provided that both X and Y may not simultaneously be H, in a solvent, in the presence of an inorganic base selected from the group consisting of the alkali metal carbonates, bicarbonates, and hydroxides, and in the presence of a catalyst selected from the group consisting of benzoic acid, substituted benzoic acids, C2-C4 aliphatic carboxylic acids, and alkali metal salts of said acids.
    Type: Grant
    Filed: January 14, 1991
    Date of Patent: May 26, 1992
    Assignee: Occidental Chemical Corporation
    Inventors: Robert A. Buchanan, Jeffrey S. Stults
  • Patent number: 5114615
    Abstract: A liquid crystal compound of the formula: ##STR1## wherein m and n are independently integers of 1 to 22; k and l are independently integers of 1 to 2; and C* is an asymmetric carbon atom, is chemically stable and can be applied to liquid crystal display devices operable at room temperature.
    Type: Grant
    Filed: September 25, 1991
    Date of Patent: May 19, 1992
    Assignees: Wako Pure Chemical Industries, Ltd., Nippon Telegraph and Telephone Corporation
    Inventors: Shigeki Ishibashi, Kouzaburou Nakamura, Tohru Maruno, Masaaki Nakahata, Takaaki Negishi, Fumiyoshi Urano