Carboxyl, Or Salt Thereof, Bonded Directly To A Ring Patents (Class 562/473)
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Patent number: 5608104Abstract: Described is a detection method of a pyrethroid compound which comprises providing a first antibody against the pyrethroid compound, said first antibody having been obtained by immunizing a responder with an immunogen which is a first conjugate between a first carrier and a first haptenic compound represented by the following formula (1) or (2): ##STR1## mixing the first antibody with the sample solution, causing any unreacted portion of the first antibody to be bound on a second conjugate as a coated antigen, said second conjugate being formed of a second carrier and a second haptenic compound and having been coated on a surface of a solid phase carrier, whereby an antigen-antibody conjugate is obtained; andreacting the antigen-antibody conjugate with a second antibody against the first antibody, said second antibody having a labelled enzyme linked therewith.Type: GrantFiled: September 27, 1994Date of Patent: March 4, 1997Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Hideo Ohkawa, Koji Kitajima, Kenji Kodaka, Yasunori Fumoto, Takako Kumeta
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Leukotriene-B.sub.4 antagonists, process for their production and their use as pharmaceutical agents
Patent number: 5559134Abstract: The invention relates to leukotriene-B.sub.4 antagonists of formula I ##STR1## in which n represents a whole number from 2 to 5,X represents a direct bond, 1 to 6 methylene units, an ortho-, meta- or para-substituted phenyl ring or a meta- or para-substituted pyridine ring,Y represents a bond to a hydrogen atom and simultaneously to a hydroxy group, a double-bound oxygen atom or --O--CH.sub.2 --CH.sub.2 --O--,R.sub.1 and R.sub.2 represent the radical OH, --O--(C.sub.1 -C.sub.4)--alkyl, O--(C.sub.3 -C.sub.6)--cycloalkyl, --O--(C.sub.6 -C.sub.10)--aryl, --O--(C.sub.7 -C.sub.12)--aralkyl, O--(CH.sub.2)--CO-- (C.sub.6 -C.sub.10)--aryl or the radical NHR.sub.3 with R.sub.3 meaning hydrogen, (C.sub.1 -C.sub.4)--alkyl, (C.sub.3 -C.sub.6)--cycloalkyl or (C.sub.7 -C.sub.12)--aralkyl as well as their salts with physiologically compatible bases and their cyclodextrin clathrates.Type: GrantFiled: March 23, 1995Date of Patent: September 24, 1996Assignee: Schering AktiengesellschaftInventors: Bernd Buchmann, Werner Skuballa, Josef Heindl, Wolfgang Fr ohlich, Roland Ekerdt, Claudia Giesen -
Patent number: 5530157Abstract: 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: GrantFiled: February 16, 1995Date of Patent: June 25, 1996Assignee: Scios Nova Inc.Inventors: Richard Mewshaw, Gregory S. Hamilton
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Patent number: 5527945Abstract: Diphenylheteroalkyl derivatives of the formula I ##STR1## where A and R.sup.1 -R.sup.6 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: GrantFiled: August 31, 1994Date of Patent: June 18, 1996Assignee: BASF AktiengesellschaftInventors: Bernd Janssen, Hans-Heiner Wuest
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Patent number: 5493051Abstract: A new modification of Lifibrol is described with a melting point of 132.degree. C.-138.degree. C. particularly from 134.degree. C.-136.degree. C. and a primary peak in an IR spectrum at a wave number of 3,200-3,400, preferably 3,250-3,350. The new modification of Lifibrol (modification II) is distinguished in that it allows for good crystallization and, therefore, can be formulated without problems on a large industrial scale for tablets of acceptable size and high stability.Type: GrantFiled: April 29, 1994Date of Patent: February 20, 1996Assignee: Klinge Pharma GmbHInventors: Artur Burger, Anita Lettenbichler, Fritz Stanislaus, Arnim Laicher, Karl Schwitzer, Axel Woschina
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Patent number: 5484935Abstract: Pharmaceutical compounds of the formula ##STR1## in which R.sup.1 and R.sup.3 are each C.sub.1-4 alkyl or C.sub.1-4 alkyl-carbonyl, and R.sup.2 is carboxy, tetrazolyl, C.sub.1-4 alkyl-sulphonamido or --CR.sup.4 R.sup.5 CO.sub.2 H where R.sup.4 and R.sup.5 are each hydrogen or C.sub.1-4 alkyl; provided that when R.sup.1 and R.sup.3 are both methyl and when R.sup.1 and R.sup.3 are both methylcarbonyl, R.sup.2 is not carboxy; and salts and esters thereof.Type: GrantFiled: August 11, 1994Date of Patent: January 16, 1996Assignee: Lilly Industries LimitedInventors: Peter T. Gallagher, Terence A. Hicks, William M. Owton
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Patent number: 5403952Abstract: Novel substituted cyclic compounds of Formula I are found to be useful inhibitors of matrix metalloendoproteinase-mediated diseases including osteoarthritis, rheumatoid arthritis, septic arthritis, tumor invasion in certain cancers, periodontal disease, corneal ulceration, proteinuria, dystrophic epidermolysis bullosa, and coronary thrombosis associated with atherosclerotic plaque rupture. The matrix metalloendoproteinases are a family of zinc-containing proteinases including but not limited to stromelysin, collagenase, and gelatinase, that are capable of degrading the major components of articular cartilage and basement membranes. The inhibitors claimed herein may also be useful in preventing the pathological sequelae following a traumatic injury that could lead to a permanent disability. These compounds may also be useful as novel birth control agents by preventing ovulation or implantation.Type: GrantFiled: October 8, 1993Date of Patent: April 4, 1995Assignee: Merck & Co., Inc.Inventors: William Hagmann, Charles G. Caldwell, Paul R. Gooley
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Patent number: 5391817Abstract: Certain novel biaryl compounds are effective phospholipase A.sub.2 (PLA.sub.2) inhibitors.Type: GrantFiled: December 21, 1993Date of Patent: February 21, 1995Assignee: Bristol-Myers SquibbInventors: Dane Springer, Bing-Yu Luh, Katharine M. Greene, Joanne J. Bronson, Muzammil M. Mansuri
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Patent number: 5385693Abstract: 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: GrantFiled: May 17, 1993Date of Patent: January 31, 1995Assignee: Sumitomo Chemical Company, LimitedInventors: Takayuki Higashii, Isao Kurimoto, Shoji Toda, Masayoshi Minai, Takeshi Tani, Chizu Kawakami, Koichi Fujisawa, Kiyoshi Imamura
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Patent number: 5374772Abstract: 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: GrantFiled: October 22, 1993Date of Patent: December 20, 1994Assignee: Hoffmann-LaRoche Inc.Inventors: Mathew Carson, Ru-Jen L. Han, Ronald LeMahieu, Vincent S. Madison
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Patent number: 5346690Abstract: There is provided a magnetic resonance contrast medium comprising magnetically responsive particles and a physiologically tolerable osmoactive agent.Type: GrantFiled: January 21, 1992Date of Patent: September 13, 1994Assignee: Nycomed Imaging ASInventors: Helge G. Gundersen, Jo Klaveness
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Patent number: 5344968Abstract: 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: GrantFiled: June 23, 1992Date of Patent: September 6, 1994Assignee: Nippon Chemical Industrial Co., Ltd.Inventors: Suchart Lilitkarntakul, Shukichi Nabekawa, Masao Takada, Katsuyuki Ogura
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Patent number: 5344958Abstract: 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: GrantFiled: November 23, 1992Date of Patent: September 6, 1994Assignee: Rohm and Haas CompanyInventors: Zev Lidert, Dat P. Le
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Patent number: 5340931Abstract: Allene compounds have the formula:(CH.sub.2 .dbd.C.dbd.CH--O).sub.n --R--(A).sub.m (I)in which R is a substituted or unsubstituted mono- or polyvalent benzene, naphthalene, anthracene, azobenzene, bisphenol or polyphenyl (containing 2 to 10 benzene rings connected in line) nucleus, or a group--Ph--R.sup.1 --Ph-- (II)(in which each group Ph is a phenylene, halophenylene, alkylphenylene, cyanophenylene or alkoxyphenylene group, and the chain R.sup.1 linking the two group Ph is a C.sub.1 -C.sub.6 aliphatic hydrocarbon or an alicyclic hydrocarbon group, the chain optionally being interrupted by one or more oxygen atoms); A is a carboxyl or sulphonyl group or a group --CH.dbd.C.dbd.CH.sub.2 ; n is an integer of from 1 to 10; m is 0, 1, 2 or 3; and the sum of m and n is equal to the valence of the group R.They may be prepared by isomerization of corresponding propargyloxy compounds.Type: GrantFiled: March 15, 1989Date of Patent: August 23, 1994Assignee: Nippon Paint Co., Ltd.Inventors: Mitsuo Yamada, Hiromichi Kayano, Kei Aoki, Keizou Ishii
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Patent number: 5338881Abstract: This invention concerns a process for preparing diketones and keto-acids by reacting a dicarboxylic acid and an aromatic compound in the presence of an alkylsulfonic acid such as methanesulfonic acid and a phosphorus pentoxide. The diketones and keto-acids can be used to prepare polyketones which are useful as molding plastics, coatings, films, fibers, and the like.Type: GrantFiled: July 23, 1990Date of Patent: August 16, 1994Assignee: Eastman Chemical CompanyInventors: Theodore R. Walker, Jr., Winston J. Jackson, Jr., Jean C. Fleischer
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Patent number: 5338773Abstract: 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: GrantFiled: April 19, 1993Date of Patent: August 16, 1994Assignee: Dentsply Research & Development Corp.Inventors: Kewang Lu, Chin-Teh Huang, Paul Hammesfahr
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Patent number: 5266721Abstract: 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: GrantFiled: June 4, 1992Date of Patent: November 30, 1993Assignee: Klinge Pharma GmbHInventors: Friedemann Reiter, Hans-Helmut Henschel
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Patent number: 5261953Abstract: Inks, in particular for ink-jet printing, containing, as stabilizer, a water-soluble compound of the formula ##STR1## in which R.sub.1 to R.sub.7 are as defined in claim 1, and recording materials containing these compounds.Type: GrantFiled: November 20, 1991Date of Patent: November 16, 1993Assignee: Ciba-Geigy CorporationInventors: Eric Vieira, David G. Leppard, Hugh S. Laver, Vien V. Toan
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Patent number: 5237092Abstract: 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: GrantFiled: June 16, 1992Date of Patent: August 17, 1993Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Toru Tanaka, Kazuo Tanaka, Teruo Aratake
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Patent number: 5202471Abstract: 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: GrantFiled: February 6, 1990Date of Patent: April 13, 1993Assignee: Allergan, Inc.Inventor: Roshantha A. S. Chandraratna
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Patent number: 5191108Abstract: 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: GrantFiled: April 3, 1991Date of Patent: March 2, 1993Assignee: Hoffmann-La Roche Inc.Inventors: Matthew Carson, Ru-Jen L. Han, Ronald A. Lemahieu
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Patent number: 5183660Abstract: 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: GrantFiled: August 15, 1991Date of Patent: February 2, 1993Assignee: Sumitomo Pharmaceuticals Company, LimitedInventors: Yoshiharu Ikeda, Yoshiyuki Kai, Keiichi Ono
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Patent number: 5164527Abstract: 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: GrantFiled: April 3, 1991Date of Patent: November 17, 1992Assignee: Imperial Chemical Industries PLCInventor: Alan B. Newton
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Patent number: 5153353Abstract: 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: GrantFiled: August 8, 1991Date of Patent: October 6, 1992Assignee: Klinge Pharma GmbHInventors: Friedemann Reiter, Peter Jank, Michael Schliack, Kaisli Kaipainen-Reiter, Gerhard Lang, Anke Schink
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Patent number: 5149865Abstract: 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: GrantFiled: December 20, 1991Date of Patent: September 22, 1992Assignee: Klinge Pharma GmbHInventors: Friedemann Reiter, Helmut Grill, Hans-Helmut Henschel, Michael Schliack, Klaus Seibel, Roland Loser, Gerhard Lang
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Patent number: 5147892Abstract: Benzyl ketones of the formula ##STR1## where X is CH or N,Y is O or NR.sup.4,R.sup.1, R.sup.2 are H or alkyl,R.sup.3 is halogen, cyano, nitro, alkyl, cycloalkyl, alkoxy, haloalkyl, arylalkyl, arylalkoxy, aryloxy or aryl, and the aryl groups in turn may be substituted,R.sup.4 is OH, alkoxy or arylalkoxy andR.sup.5 is H, methyl, halogen or methoxy,and fungicides containing these compounds.Type: GrantFiled: June 27, 1991Date of Patent: September 15, 1992Assignee: BASF AktiengesellschaftInventors: Horst Wingert, Hubert Sauter, Franz Roehl, Reinhard Doetzer, Gisela Lorenz, Eberhard Ammermann
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Patent number: 5128479Abstract: 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: GrantFiled: January 29, 1990Date of Patent: July 7, 1992Assignee: BASF AktiengesellschaftInventors: Bernd Janssen, Hans-Heiner Wuest
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Patent number: 5117002Abstract: 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: GrantFiled: January 14, 1991Date of Patent: May 26, 1992Assignee: Occidental Chemical CorporationInventors: Robert A. Buchanan, Jeffrey S. Stults
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Patent number: 5091565Abstract: New poly-dicarboxylic acid anhydrides, which are suitable as bio-degradable matrix materials for the controlled release of medicinal agents in humans.Type: GrantFiled: August 21, 1990Date of Patent: February 25, 1992Assignee: Sandoz Ltd.Inventor: Gerd Ziegast
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Patent number: 5086067Abstract: 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: GrantFiled: December 18, 1989Date of Patent: February 4, 1992Assignee: G. D. Searle & Co.Inventors: Stevan W. Djuric, Richard A. Haack, Julie M. Miyashiro
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Patent number: 5043450Abstract: Quinolonecarboxylic acid derivatives of the following formula, ##STR1## wherein R indicates a hydrogen atom or lower alkyl group, R.sup.1 indicates a lower alkyl group, R.sup.2 indicates a hydrogen atom, amino group or nitro group, X indicates a halogen atom, and Z indicates a halogen atom, piperazino group, N-methylpiperazino group, 3-methylpiperazino group, 3-hydroxypyrrolidino group, or pyrrolidino group of the following formula, ##STR2## (here, n is 0 or 1, R.sup.3 indicates a hydrogen atom or lower alkyl group, R.sup.4 indicates a hydrogen atom, lower alkyl group or substituted lower alkyl group and R.sup.5 indicates a hydrogen atom, lower alkyl group, acyl group or alkoxycarbonyl group), the hydrates and pharmaceutically acceptable salts thereof are useful as antibacterial agents.Type: GrantFiled: October 22, 1990Date of Patent: August 27, 1991Assignee: Kyorin Pharmaceutical Co., Ltd.Inventors: Kuniyoshi Masuzawa, Seigo Suzue, Keiji Hirai, Takayoshi Ishizaki
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Patent number: 5041604Abstract: 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: GrantFiled: June 20, 1990Date of Patent: August 20, 1991Assignee: Sanko Kaihatsu Kagaku KenkyushoInventors: Toranosuke Saito, Masakatu Kitani, Takashi Ishibashi
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Patent number: 5025036Abstract: 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: GrantFiled: May 3, 1989Date of Patent: June 18, 1991Assignee: Hoffmann-La Roche Inc.Inventors: Matthew Carson, Ru-Jen L. Han, Ronald A. LeMahieu
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Patent number: 5019298Abstract: 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: GrantFiled: April 25, 1988Date of Patent: May 28, 1991Assignee: Sumitomo Chemical Company, LimitedInventors: Masayoshi Minai, Takayuki Higashii
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Patent number: 5004817Abstract: 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: GrantFiled: February 27, 1989Date of Patent: April 2, 1991Assignee: Montefibre, S.p.A.Inventors: Catia Bastioli, Salvatore Garlisi, Dario Fornara, Vittorio Bellotti
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Patent number: 4992574Abstract: A compound of the formula ##STR1## wherein R.sup.1 is hydroxy, lower-alkoxy, amino, mono- or di-lower-alkylamino;R.sup.2 is hydrogen, alkyl, akoxy or halogen;R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.11 and R.sup.12 independently are hydrogen or lower-alkyl;R.sup.3 and R.sup.5 taken together are methylene or hydroxymethylene;R.sup.7, R.sup.8, R.sup.9 and R.sup.10 independently are hydrogen or lower-alkyl;R.sup.11 and R.sup.12 taken together are oxo or spiro-cyclo-lower alkyl; or R.sup.11 is hydrogen and R.sup.12 is hydroxy or acetoxy; and one of the residues R.sup.13 and R.sup.14 is hydrogen and the other is lower-alkyl or trifluoromethyl, as well as physiologically compatible salts of carboxylic acids of formula I, which can be used as medicaments, especially for the treatment of neoplasms, acne and psoriasis, are described. The compounds of the invention can be prepared by the synthesis of the C(R.sup.13).dbd.C(R.sup.Type: GrantFiled: October 27, 1988Date of Patent: February 12, 1991Assignee: Hoffmann-La Roche Inc.Inventors: Michael Klaus, Peter Mohr
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Patent number: 4992577Abstract: A process for preparing a compound of the formula ##STR1## in which Y is halogen, alkyl or cycloalkyl optionally substituted by halogen or C.sub.1-4 -alkoxy, alkenyl optionally substituted by halogen, aryl, heteroaryl or alkoxycarbonyl,X is hydrogen, halogen or optionally halogen-substituted alkyl, orX and Y, together with the adjacent C atom, form a saturated cycloalkphatic ring having up to 6 C atoms, andR is hydrogen or C.sub.1 -C.sub.4 -alkyl, comprising reacting an aldehyde of the formula ##STR2## with 2-methylbutan-3-one of the formula ##STR3## in the presence of a hydrohalic acid thereby to form a 4,4-dimethyl-3-halogeno-1-hexen-5-one of the formula ##STR4## in which Hal is halogen, halogenating said compound to produce a compound of the formula ##STR5## and reacting said compound with a base of the formulaR--OM (VI)in whichM is one equivalent of an alkali or alkaline earth metal ion.Compounds IV and V are new. By suitable conditions the trans isomer is selectively produced.Type: GrantFiled: May 22, 1989Date of Patent: February 12, 1991Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Dieter Arlt, Manfred Jautelat
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Patent number: 4965399Abstract: Disclosed are novel 1,5-bis(substituted-aryl)-3-pentanols which are useful in the preparation of polymeric materials and have the formula: ##STR1## wherein: R.sup.1 and R.sup.2 each is hydrogen, alkyl containing up to about 6 carbon atoms or phenyl or collectively R.sup.1 and R.sup.2 are 1,2- or 1,3-alkylene or 1,2-phenylene; andeach X is carboxyl, alkoxycarbonyl of up to about 7 carbon atoms, hydroxyalkoxycarbonyl of up to about 9 carbon atoms, formamido, alkanoylamido having up to about 6 carbon atoms or hydroxyalkoxy having up to about 10 carbon atoms. The novel compounds may be prepared by first condensing certain 4-substituted-benzaldehydes with ketones to obtain intermediate 1,5-bis(4-substituted-aryl)penta-1,4-dien-3-ones and hydrogenating the intermediates with certain catalysts. Mixed copper-chromium oxides are especially effective in converting the pentadienone compounds to the pentanol compounds.Type: GrantFiled: August 19, 1988Date of Patent: October 23, 1990Assignee: Eastman Kodak CompanyInventors: Joseph R. Zoeller, William W. Blount
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Patent number: 4946865Abstract: A compound of the formula: ##STR1## wherein X is a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.3 alkyl group or a C.sub.1 -C.sub.3 alkoxy group and Y is a hydrogen atom, a halogen atom, a cyano group, a formyl group, an ethylene-dioxymethyl group, a hydroxyl group, a hydroxymethyl group or a group of either one of the formulas: --CH.dbd.N--OR.sup.1, --COOR.sup.2, --CONH--R.sup.2 and --CH(OR.sup.3).sub.2 in which R.sup.1 is a hydrogen atom, a C.sub.1 -C.sub.3 alkyl group, a C.sub.3 -C.sub.5 alkenyl group, a C.sub.3 -C.sub.5 alkynyl group, a halo(C.sub.3 -C.sub.5)alkynyl group or a C.sub.1 -C.sub.3 alkyl group substituted with a phenyl group or a cyano group, R.sup.2 is a hydrogen atom, a C.sub.1 -C.sub.3 alkyl group, a C.sub.3 -C.sub.5 alkenyl group or a C.sub.3 -C.sub.5 alkynyl group and R.sup.3 is a C.sub.1 -C.sub.Type: GrantFiled: December 24, 1986Date of Patent: August 7, 1990Assignee: Sumitomo Chemical Company, LimitedInventors: Junya Takahashi, Shigeko Nakamura
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Patent number: 4898883Abstract: The present invention relates to 1-substituted derivatives of 4-methoxy-2,3,6-trimethylbenzene which are useful in cosmetic or pharmaceutical preparations for use in the treamtnet of dermatological complaints connected with a keratinisation disorder, dermatological complaints having an inflammatory and/or immuno-alleric component or ophthalmological complaints.Type: GrantFiled: July 21, 1987Date of Patent: February 6, 1990Assignee: L'OrealInventors: Gerard Lang, Serge Forestier, Alain Lagrange, Braham Shroot
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Patent number: 4885384Abstract: A process for the production of aromatic carboxylic acids which comprises carbonylating substituted iodoaromatic compounds in the presence of carbon monoxide, a catalytic amount of a transition metal catalyst, and a Bronsted base in a mixture of a carboxylic acid and water under aromatic carboxylic acid forming conditions of temperature and pressure.Type: GrantFiled: March 14, 1988Date of Patent: December 5, 1989Inventors: Guy R. Steinmetz, Kevin J. Edgar, Stephen N. Falling
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Patent number: 4880560Abstract: An optically active lactic acid derivative represented by the following formula (Ia) or (Ib): ##STR1## wherein R is a linear, branched or cyclic saturated or unsaturated hydrocarbon group having 1-16 carbon atoms,R.sup.1 is an alkyl group having 4-16 carbon atoms,m and n are respectively 1 or 2,k is 0 or 1, andC* is an asymmetric carbon atom.A liquid crystal composition containing the lactic acid derivative and a liquid crystal device using the liquid crystal composition are also disclosed.Type: GrantFiled: January 3, 1989Date of Patent: November 14, 1989Assignee: Canon Kabushiki KaishaInventors: Kazuo Yoshinaga, Kazuharu Katagiri, Kenji Shinjo
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Patent number: 4871712Abstract: Provided are dialkyloxy-substituted terephthalic acids of the formula ##STR1## wherein R is an alkyl group having about 8 to 12 carbon atoms. Also provided is a method for preparing these dialkyloxy-substituted terephthalic acids.Type: GrantFiled: September 8, 1988Date of Patent: October 3, 1989Assignee: The United States of America as represented by the Secretary of the Air ForceInventors: Bruce A. Reinhardt, Marilyn R. Unroe
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Patent number: 4864034Abstract: Spiro(bis)indane bis-oxyphthalic acid bisimides are prepared by the reaction of a nitro- or halo-substituted phthalimide with a salt of a 6,6'-dihydroxy-3,3,3'3'-tetramethylspiro(bis)indane. The bisimides may be converted to the corresponding dianhydrides, which react with diamines to form polyetherimides, or to the free tetracarboxylic acids or their salts, esters or amides.Type: GrantFiled: January 20, 1988Date of Patent: September 5, 1989Assignee: General Electric CompanyInventors: James A. Cella, Gary R. Faler
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Patent number: 4845276Abstract: 2,6-dialkoxybenzoic acid is made by metalation of 1,3-dialkoxybenzene by reaction with potassium dialkylamide. The metalated dialkoxybenzene is carbonated and acidified to form the dialkoxybenzoic acid.Type: GrantFiled: August 22, 1988Date of Patent: July 4, 1989Assignee: Mine Safety Appliances CompanyInventor: Lin-Chen Yu
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Patent number: 4845277Abstract: 2,6-dialkoxybenzoic acid is made by direct metalation of 1,3-dialkoxybenzene by potassium. The metalated dialkoxybenzene is carbonated and acidified to form the dialkoxybenzoic acid.Type: GrantFiled: August 22, 1988Date of Patent: July 4, 1989Assignee: Mine Safety Appliances CompanyInventor: Lin-Chen Yu
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Patent number: 4826876Abstract: 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: GrantFiled: December 21, 1987Date of Patent: May 2, 1989Assignee: Smith Kline & French Laboratories LimitedInventors: David Ellis, John C. Emmett, Anthony H. Underwood, Paul D. Leeson
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Patent number: 4812259Abstract: An optically active lactic acid derivative represented by the following formula (Ia) or (Ib): ##STR1## wherein R is a linear, branched or cyclic saturated or unsaturated hydrocarbon group having 1-16 carbon atoms, R.sup.1 is an alkyl group having 4-16 carbon atoms, m and n are respectively 1 or 2, k is 0 or 1, and C* is an asymmetric carbon atom. A liquid crystal composition containing the lactic acid derivative and a liquid crystal device using the liquid crystal composition are also disclosed.Type: GrantFiled: October 23, 1986Date of Patent: March 14, 1989Assignee: Canon Kabushiki KaishaInventors: Kazuo Yoshinaga, Kazuharu Katagiri, Kenji Shinjo
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Patent number: 4812594Abstract: Aqueous solutions of crude p-hydroxymethylbenzoic acid are purified to relatively low levels of 4-carboxybenzaldehyde by hydrogenation in the presence of a nickel on kieselguhr catalyst. 4-carboxybenzaldehyde is hydrogenated to p-hydroxymethylbenzoic acid. Toluic acid production is minimal.Type: GrantFiled: September 8, 1987Date of Patent: March 14, 1989Assignee: Amoco CorporationInventor: Bruce Petty-Weeks
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Patent number: 4778925Abstract: Para substituted benzoic acid derivatives of general formula (1) ##STR1## and their physiologically compatible salts, where R.sup.1 may be H, isopropyl, t-butyl p0 X may be ##STR2## and R.sup.2 may be --OH, --OR', where R' is a linear or branched, saturated or unsaturated C.sub.1 to C.sub.3 alkylmoiety, or a --NHCH.sub.2 COOH-- group, have hypolipedemic activity. They may be obtained by known methods either from the corresponding unsaturated ketones or from saturated hydroxycompounds, where the esterified benzoic acid moiety may be saponified or converted to a carboxymethylamide.Type: GrantFiled: May 22, 1987Date of Patent: October 18, 1988Assignee: Klinge Pharma GmbHInventors: Helmut Grill, Friedemann Reiter, Michael Schliack, Roland Loser, Klaus Seibel