Chalcogen Bonded Directly At 2-position Of The Oxazole Ring Patents (Class 548/229)
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Patent number: 5461067Abstract: A retroviral protease inhibiting compound of the formula: ##STR1## is disclosed wherein R.sub.1, R.sub.2, R.sub.5, R.sub.6, Y.sub.m and Y'.sub.n are herein defined.Type: GrantFiled: February 1, 1994Date of Patent: October 24, 1995Assignee: Abbott LaboratoriesInventors: Daniel W. Norbeck, Hing L. Sham, Dale J. Kempf, Chen Zhao
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Patent number: 5455353Abstract: A process for the production of a .beta.-aminoalcohol 2-[3(S)-amino-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-decahydro-(4aS,8aS) -isoquinoline-3(S)-carboxamide of the formula ##STR1## via the oxazolidinone corresponding to the aminoalcohol 10, as well as intermediates occurring in this process.Type: GrantFiled: March 9, 1994Date of Patent: October 3, 1995Assignee: Hoffmann-La Roche Inc.Inventor: Hans Hilpert
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Patent number: 5453540Abstract: Fluorochemical compositions comprising fluorinated compounds, wherein the fluorinated compound comprises fluorochemical oligomeric portion, an organic moiety, and a group that can impart soft hand, stain release, water repellency, or a durable property when the compound is applied to a fibrous substrate, wherein the fluorochemical oligomeric portion is bonded to the organic moiety through an isocyanate-derived linking group. Also disclosed are fluorochemical compositions in the form of fluorochemical liquid dispersions and methods for preparing substrates treated with such compositions. Substrates so treated exhibit particularly durable and abrasion-resistant oil and water repellent properties. Intermediates in the preparation of the fluorochemical compositions are also disclosed. Some of the intermediates are useful as emulsifiers in fluorochemical liquid dispersions.Type: GrantFiled: November 29, 1993Date of Patent: September 26, 1995Assignee: Minnesota Mining and Manufacturing CompanyInventors: Rudolf J. Dams, Johan E. De Witte
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Patent number: 5446158Abstract: A process is described for the total synthesis of the macrolide immunosuppressant, FK-506, and important tricarbonyl process intermediates thereof. The tricarbonyl intermediates can be produced by the mild oxidation of 2,3-dihydroxy carboxylate compounds containing olefin moieties.Type: GrantFiled: October 12, 1990Date of Patent: August 29, 1995Assignee: Merck & Co., Inc.Inventors: Todd K. Jones, Sander G. Mills, David Askin, Robert A. Reamer, Richard Desmond, David M. Tschaen, Ralph P. Volante, Ichiro Shinkai
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Patent number: 5438148Abstract: The invention is the simultaneous addition of boron tribromide and a solution of [R-(R*,R*)]-5-(3-chlorophenyl-3-[2-(3,4-dimethoxyphenyl)-1-methylethyl]-2- oxazolidinone in methylene chloride to methylene chloride while maintaining a constant ratio of 2.10:1.00 of boron tribromide to the substrate [R-(R*,R*)]-5-(3-chlorophenyl-3-[2-(3,4-dimethoxyphenyl)-1-methylethyl]-2- oxazolidinone at a temperature of -5.degree. C. to 10.degree. C. gives [R-(R*,R*)]-5-(3-chlorophenyl-3-[2-(3,4-hydroxyoxyphenyl)-1-methylethyl]-2 -oxazolidinone in an isolated yield of 86.7% and a purity of 98.7%.Type: GrantFiled: September 20, 1994Date of Patent: August 1, 1995Assignee: American Cyanamid CompanyInventors: Arthur G. Mohan, David M. Blum
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Patent number: 5420291Abstract: The invention is a process improvement for producing [R-(R*, R*)]-5-(3-chlorophenyl)-3-[2-(3,4-dihydroxyphenyl)-1-methylethyl]-2-oxazol idinone which is an intermediate useful in making compounds that have antidiabetic and/or antihyperglycemic and/or antiobesity properties in mammals.Type: GrantFiled: September 20, 1994Date of Patent: May 30, 1995Assignee: American Cyanamid CompanyInventors: William T. Cain, Kelvin Cruz, Kevin M. McCoy
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Patent number: 5412100Abstract: Fungicidal substituted acrylic esters of the formula ##STR1## in which R.sup.1 represents hydrogen, alkyl or alkenyl, or represents in each case optionally substituted aralkyl, aralkenyl, aryl or heteroaryl,R.sup.2 represents halogen, cyano, nitro, formyl, halogenoalkyl, alkoxyalkyl or alkylthioalkyl, or represents hydroximinoalkyl, alkoximinoalkyl, N-alkyliminoalkyl, N-aryliminoalkyl or N,N-dialkylhydrazonoalkyl, or represents alkoxy, alkylthio, halogenoalkoxy or halogenoalkylthio, or represents aryloxy or arylthio, or represents alkanoyl, alkoxycarbonyl, N,N-dialkylcarbamoyl or heterocyclylcarbonyl,R.sup.3 represents alkyl, or represents optionally substituted aralkyl,R.sup.4 represents dialkylamino or represents a radical --Z--R.sup.5,X represents oxygen or sulphur andY represents oxygen or sulphur or represents a radical ##STR2## where R.sup.5 represents alkyl or represents optionally substituted aralkyl,R.sup.Type: GrantFiled: July 1, 1993Date of Patent: May 2, 1995Assignee: Bayer AktiengesellschaftInventors: Alexander Klausener, Gerd Kleefeld, Wilhelm Brandes, Stefan Dutzmann, Gerd Hanssler
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Patent number: 5399574Type: GrantFiled: March 3, 1992Date of Patent: March 21, 1995Assignee: Burroughs Wellcome Co.Inventors: Alan D. Robertson, Alan P. Hill, Robert C. Glen, Graeme R. Martin
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Patent number: 5385930Abstract: The invention relates to compounds of the formula I: ##STR1## in which R.sub.1 is as defined in the description, their optical isomers and their addition salts with a pharmaceutically-acceptable acid or base, and medicinal products which are useful for treating Central Nervous System disorders.Type: GrantFiled: January 14, 1994Date of Patent: January 31, 1995Assignee: Adir et CompagnieInventors: Gerald Guillaumet, Gerard Coudert, Tchao Podona, Beatrice Guardiola-Lemaitre, Pierre Renard, Gerard Adam, Daniel Henri-Caignard
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Patent number: 5378839Abstract: There are provided 1-(substituted)thioalkylpyrrole compounds of formula I ##STR1## the use thereof for the control of insect, acarid and mollusk pests and methods and compositions for the protection of crops from the ravages of said pests.Type: GrantFiled: January 26, 1994Date of Patent: January 3, 1995Assignee: American Cyanamid CompanyInventors: David G. Kuhn, Venkataraman Kameswaran
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Patent number: 5362880Abstract: Disclosed is a method of preparing a photographic coupler comprised of 1-aryl-3-substituted-4-heterocyclic-5-pyrazolone development inhibitor releasing coupler for use in a photographic element, said coupler capable of reacting with oxidized color developer to release a heterocyclic coupling-off group containing an inhibitor.Type: GrantFiled: June 30, 1992Date of Patent: November 8, 1994Assignee: Eastman Kodak CompanyInventor: William J. Begley
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Patent number: 5344936Abstract: Selenium reagents when coupled to a compound containing an asymmetric carbon atom can be used in a highly sensitive method for determination of enantiomeric purity and for stereochemical assignment. Preferred reagents include a selenocarbonyl moiety (Se=C) and a reactive center for coupling to the compound of interest. Particularly preferred selenocarbonyls for use in the invention are chiral selenooxazolidinones of the formula ##STR1## wherein R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are selected from among hydrogen, alkyl of up to 10 carbons and aryl having up to 12 carbon atoms in the ring system. The substituent R.sup.1 is selected to facilitate the formation of a bond between the nitrogen atom of the selenooxazolidinone reagent and the compound of interest. Since the ability of the reagent to resolve enantiomers decreases as the number of bonds between the selenium and the asymmetric carbon increases, the reactive center is preferably located no more than three bonds from the selenium atom.Type: GrantFiled: March 5, 1993Date of Patent: September 6, 1994Assignee: University of South CarolinaInventors: Louis A. Silks, III, R. Bruce Dunlap, Jerome D. Odom
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Patent number: 5342959Abstract: Chiral compounds useful as radiosensitizers or chemosensitizers having the formula ##STR1## wherein X is halogen or ##STR2## intermediates used to prepare these compounds, and a novel process to prepare these compounds are described.Type: GrantFiled: August 5, 1993Date of Patent: August 30, 1994Assignees: Warner-Lambert Company, British Tech. GroupInventors: Vladimir Genukh Beylin, Anthony D. Sercel, Howard D. H. Showalter, Gerald E. Adams, Edward M. Fielden, Matthew A. Naylor, Ian J. Stratford
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Patent number: 5324723Abstract: 1,3-Oxazole and 1,3-thiazole compounds of formula I, and their pharmaceutically acceptable salts and prodrugs: ##STR1## wherein X represents oxygen or sulphur;R.sup.1 represents a non-aromatic azacyclic or azabicyclic ring system.Type: GrantFiled: July 1, 1993Date of Patent: June 28, 1994Assignee: Merck Sharpe & Dohme Ltd.Inventors: Raymond Baker, John Saunders, Roger J. Snow, Graham A. Showell
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Patent number: 5324837Abstract: 3,4-Diaryl-4,5-dihydro-1H-pyrazole compounds having a selected 5- or 6-membered aromatic heterocyclic moiety in the 4-position and an optionally substituted phenyl moiety in the 3-position, such as 4,5-dihydro-3-(4-fluorophenyl)-4-(5-trifluoromethyl-2-pyridinyl)-1H-pyrazo le were prepared as intermediates in the preparation of insecticidal 3,4,N-triaryl-4,5-dihydro-1H-pyrazole-1-carboxamide compounds. The 3,4-diaryl-4,5-dihydro-1H-pyrazole compounds can be prepared from appropriate 1,2-diarylethanone compounds by successive treatments with N,N,N',N'-tetramethyldiaminomethane in dichloromethane in the presence of acetic anhydride (to form a Mannich adduct) and hydrazine in the presence of a catalytic amount of trifluoroacetic acid.Type: GrantFiled: August 17, 1992Date of Patent: June 28, 1994Assignee: DowElancoInventors: James M. Renga, Kevin L. McLaren, James T. Pechacek, Michael J. Ricks, Yulan C. Tong
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Patent number: 5321002Abstract: Herbicidal compounds, compositions containing them, and a method for controlling weeds by application of the compositions are disclosed. The herbicidal compounds are 2-(1-aryl-4-cyano-5-pyrazolylmethyleneiminooxy)alkanoic acid derivatives of the structure: ##STR1## in which R is lower alkyl, lower alkenyl, or lower alkynyl, each optionally substituted with halogen, or CH(R.sup.1)--C(O)--Y--R.sup.2 ; R.sup.1 is hydrogen or lower alkyl; R.sup.2 is one of a variety of substituents; Y is O or NH; Z is lower alkyl or lower alkoxy; and Ar is 3-chloro-5-trifluoromethyl-2-pyridyl, 2,6-dichloro-4-trifluoromethylphenyl, or 2,4,6-trichlorophenyl.Type: GrantFiled: August 11, 1993Date of Patent: June 14, 1994Assignee: FMC CorporationInventor: Lester L. Maravetz
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Patent number: 5310499Abstract: Chiral oxazolidinones of the formula (I) or (II) ##STR1## in which R.sup.1 is, for example, a straight-chain or branched alkyl radical having 1 to 16 carbon atoms orR.sup.2 and R.sup.3 are, for example, --H, --CH.sub.3 or phenyl,j, 1 and n are zero, 1 or 2,k and m are zero or 1,A.sup.1, A.sup.2 and A.sup.3 are, for example, phenyl or cyclohexyl,M.sup.1 and M.sup.2 are, for example, COO or CH.sub.2 O, andX is, for example, CH.sub.2 or COO,are suitable as dopes in liquid-crystal mixtures. They result in liquid-crystalline ferroelectric phases having short response times. A further advantage is that the oxazolidinones induce a helix of very low pitch, so that they are also suitable for helix compensation in LC mixtures.Type: GrantFiled: July 19, 1991Date of Patent: May 10, 1994Assignee: Hoechst AktiengesellschaftInventors: Gunter Scherowsky, Michael Sefkow, Gerd Illian, Rainer Wingen
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Patent number: 5298659Abstract: Azomethines can be prepared by the condensation of cycloalkanones and anilines in the presence of acid homogeneous catalysts while the water of reaction is removed azeotropically, the condensation being carried out in a continuous reaction in a column-like reactor to which a temperature profile is applied, the starting materials being fed in in the low-temperature region, and, of the reaction products, the water of reaction to be removed azeotropically being discharged also in the low-temperature region and the azomethine produced being discharged in the high-temperature region.Type: GrantFiled: January 14, 1993Date of Patent: March 29, 1994Assignee: Bayer AktiengesellschaftInventors: Reinhard Langer, Hans-Josef Buysch, Paul Wagner
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Patent number: 5288833Abstract: The present invention relates to quaternary .beta.-hydroxy-alkyl-ammonium halides and quaternary .beta.-hydroxy-cycloalkylammonium halides, which are liquid at temperatures lower than 60.degree. C., are easily and rapidly miscible in liquid epoxides, as well as in liquid poly-isocianates, generating liquid compositions which spontaneously polymerize, with fast polymerization rate, already at temperatures comprised within the range of from 0.degree. C. to 60.degree. C., yielding a solid, insoluble polymeric material endowed with very high values of softening temperature.Type: GrantFiled: May 20, 1992Date of Patent: February 22, 1994Assignee: Istituto Guido Donegani S.p.A.Inventors: Fabrizio Parodi, Carlo Belgiovine, Carla Zannoni
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Patent number: 5286881Abstract: A benzodifuranone compounds of the formula, ##STR1## wherein R.sup.1 and R.sup.2 are each independently a naphthyl group or an unsubstituted or substituted phenyl group, which is useful for dyeing or printing hydrophobic fiber materials, is prepared in high purity and high yield by allowing benzofuran compounds of the formula, ##STR2## wherein R.sup.1 is as defined above, to react with acetonitrile compounds of the formula, ##STR3## wherein R.sup.2 is as defined above, and then carrying out an oxidation reaction to give the benzodifuranone compound.Type: GrantFiled: September 30, 1992Date of Patent: February 15, 1994Assignee: Sumitomo Chemical Company LimitedInventors: Junichi Sekihachi, Jun Yamamoto, Yutaka Kayane
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Patent number: 5276037Abstract: The invention concerns an aryl derivative of the formula I, ##STR1## wherein Ar.sup.1 is optionally substituted phenyl, naphthyl or a heterocyclic moiety, and X.sup.1 is oxy, thio, sulphinyl, sulphonyl, difluoromethylene, imino, (1-4C)alkylimino or optionally substituted (1-4C)alkylene, or X.sup.1 is a group of the formula--X.sup.4 --CR.sub.2 -- or --CR.sub.2 --X.sup.4 --whereinX.sup.4 is oxy, thio, sulphinyl, sulphonyl or carbonyl and each R is hydrogen, methyl or ethyl;each of Ar.sup.2 and Ar.sup.3 is optionally substituted phenylene;X.sup.2 is oxy, thio, sulphinyl or sulphonyl;R.sup.1 is (1-4C)alkyl; andR.sup.2 and R.sup.3 together form a group of the formula --A.sup.1 --X.sup.3 --A.sup.2 -- which together with the carbon atom to which A.sup.1 and A.sup.2 are attached define a ring having 5 to 7 ring atoms, wherein each of A.sup.1 and A.sup.2 is (1-3C)alkylene and X.sup.Type: GrantFiled: April 14, 1993Date of Patent: January 4, 1994Assignees: Imperial Chemical Industries PLC, ICI PharmaInventors: Robert I. Dowell, Philip N. Edwards, Keith Oldham
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Patent number: 5272163Abstract: Amides having formula I: ##STR1## wherein E, X, R.sup.2 and R.sup.3 have the meanings given in the specification, and pharmaceutically acceptable salts and pharmaceutically acceptable in vivo hydrolysable esters thereof, which are useful in the treatment of urinary incontinence. Further provided are processes for preparing the amides and pharmaceutical compositions containing them.Type: GrantFiled: July 23, 1992Date of Patent: December 21, 1993Assignees: Imperial Chemical Industries PLC, Imperial Chemical HouseInventors: Keith Russell, Cyrus J. Ohnmacht, Keith H. Gibson
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Patent number: 5254693Abstract: Fungicidal substituted acrylic esters of the formula ##STR1## in which R.sup.1 represents hydrogen, alkyl or alkenyl, or represents in each case optionally substituted aralkyl, aralkenyl, aryl or heteroaryl,R.sup.2 represents halogen, cyano, nitro, formyl, halogenoalkyl, alkoxyalkyl or alkylthioalkyl, or represents hydroximinoalkyl, alkoximinoalkyl, N-alkyliminoalkyl, N-aryliminoalkyl or N,N-dialkylhydrazonoalkyl, or represents alkoxy, alkylthio, halogenoalkoxy or halogenoalkylthio, or represents aryloxy or arylthio, or represents alkanoyl, alkoxycarbonyl, N,N-dialkylcarbamoyl or heterocyclylcarbonyl,R.sup.3 represents alkyl, or represents optionally substituted aralkyl,R.sup.4 represents dialkylamino or represents a radical --Z--R.sup.5,X represents oxygen or sulphur andY represents oxygen or sulphur or represents a radical ##STR2## where R.sup.5 represents alkyl or represents optionally substituted aralkyl,R.sup.Type: GrantFiled: November 5, 1991Date of Patent: October 19, 1993Assignee: Bayer AktiengesellschaftInventors: Alexander Klausener, Gerd Kleefeld, Wilhelm Brandes, Stefan Dutzmann, Gerd Hanssler
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Patent number: 5254577Abstract: Novel aminomethyloxooxazolidinyl arylbenzene derivatives, wherein the aryl includes the phenyl, substituted phenyl, pyridyl, and substituted pyridyl groups, such as (l)-N-{3-[4-(4'-pyridyl)phenyl]-2-oxooxazolidin-5-ylmethyl}acetamide, possess useful antibacterial activity.Type: GrantFiled: August 14, 1992Date of Patent: October 19, 1993Assignee: The Du Pont Merck Pharmaceutical CompanyInventors: Randall K. Carlson, Chung-Ho Park, Walter A. Gregory
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Patent number: 5231179Abstract: A compound of the formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are each a hydrogen atom, a lower alkyl group, an ar(lower)alkyl group or an aryl group, or R.sub.1 and R.sub.2 may be combined together to form a lower alkylene group and/or R.sub.3 and R.sub.4 are combined together to form a lower alkylene group, or R.sub.1, R.sub.2, R.sub.3 and R.sub.4 may be combined together to form an o-phenylene group, X is a halogen atom and Y is an oxygen atom or a nitrogen atom substituted with lower alkyl or aryl, which is useful as an intermediate in the synthesis of 1.beta.-methylcarbapenem compounds valuable as antibiotics.Type: GrantFiled: April 12, 1991Date of Patent: July 27, 1993Assignee: Sumitomo Pharmaceuticals Company, LimitedInventors: Shiro Terashima, Yoshio Ito, Takeo Kawabata, Kunikazu Sakai, Tamejiro Hiyama, Yoshikazu Kimura, Makoto Sunagawa, Katsumi Tamoto, Akira Sasaki
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Patent number: 5225565Abstract: The present invention relates to 3-(fused-ring substituted)phenyl-5.beta.-amidomethyloxazolidin-2-one (XXI) ##STR1## where either R.sub.2 and R.sub.4 is --H and the other of R.sub.2 and R.sub.4 taken together with R.sub.3 is --(CH.sub.2).sub.n5 --CH.dbd.CH--(CH.sub.2).sub.n6 --. Also claimed are various alkyl substituted fused ring substituted alkanones, preferred is 3-(1'-oxo-2'.alpha./.beta.-methyl-5'-indanyl)-5.beta.-(acetamidomethyl)oxa zolidin-2-one. These compounds are useful as antibacterial agents.Type: GrantFiled: April 23, 1992Date of Patent: July 6, 1993Assignee: The Upjohn CompanyInventor: Steven J. Brickner
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Patent number: 5223616Abstract: A heterocyclic compound which is useful for dyeing or printing hydrophobic fiber materials and which has the following formula (I), ##STR1##wherein A.sub.1, A.sub.2, A.sub.3 and A.sub.4 are each hydrogen, halogen, alkyl, alkoxy or alkenyl, X.sub.1 is --O-- or the like, R.sub.1 is a methylene or the like, X.sub.2 is a direct linkage or a divalent group of --O--, --S--, --SO--, --SO.sub.2 --, ##STR2## in which R.sub.3 is a hydrogen atom or a C.sub.1-4 alkyl group, ##STR3## in which R.sub.3 is as defined above, T and u are each independently hydrogen or a C.sub.1-4 alkyl, l is O or an integer of 1 to 3, Q is an unsubstituted or substituted 5-, 6- or 7-membered saturated or unsaturated heterocyclic residue, Y is hydrogen, C.sub.1-4 alkyl, a C.sub.1-4 alkoxy group or the like.Type: GrantFiled: November 4, 1991Date of Patent: June 29, 1993Assignee: Sumitomo Chemical Company, Ltd.Inventors: Jun Yamamoto, Junichi Sekihachi, Yosuke Yamamoto, Kazuhiro Machiguchi, Yutaka Kayane
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Patent number: 5221684Abstract: Hydroquinone diethers of the formula I ##STR1## where A.sup.1 and A.sup.2 are substituted or unsubstituted alkylene;R.sup.1 is hydrogen, halogen or alkyl;R.sup.2 is substituted or unsubstituted pyrazolyl or pyridyl;X is a substituted or unsubstituted 5-membered heteroaromatic radical, are prepared as described using the described intermediates, and are used as pesticides.Type: GrantFiled: October 8, 1991Date of Patent: June 22, 1993Assignee: BASF AktiengesellschaftInventors: Christoph Nuebling, Hans Theobald, Wolfgang Krieg, Uwe Kardorff, Christoph Kuenast
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Patent number: 5208333Abstract: (2R)-1-(Aryloxy)-3-(butyryloxy)-2-propanols of the general formula (I), ##STR1## where Ar is a monocyclic or polycyclic aromatic or heteroaromatic radical, and a process for their preparation by the reaction of (2R)-glycidyl butyrate with an aromatic hydroxy compound Ar--OH in the presence of a quaternary ammonium halide.Type: GrantFiled: December 9, 1988Date of Patent: May 4, 1993Assignee: BASF AktiengesellschaftInventors: Axel Paul, Wolfgang Ladner, Hardo Siegel
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Patent number: 5182403Abstract: The present invention relates to 3 indazol substituted 5 Beta amidomethyloxazolidin-2ones, useful as antibacterial agents and to intermediates for their production.Type: GrantFiled: April 23, 1992Date of Patent: January 26, 1993Assignee: The Upjohn CompanyInventor: Steven J. Brickner
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Patent number: 5177207Abstract: Novel forskolin derivatives, intermediates and processes for the preparation thereof, and methods for treating cardiac failure and memory deficit utilizing compounds or compositions thereof are disclosed.Type: GrantFiled: November 21, 1990Date of Patent: January 5, 1993Assignee: Hoechst-Roussel Pharmaceuticals, Inc.Inventors: Raymond W. Kosley, Jr., Gerard O'Malley, Bettina Spahl
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Patent number: 5164510Abstract: The present invention relates to 5'-indolinyloxazolidin-2-ones (XI) ##STR1## 3-(fused-ring) substituted)phenyl-5.beta.-amidomethyloxazolidin-2-ones (XXI) ##STR2## and 3-(nitrogen substituted)phenyl-5.beta.-amidomethyloxazolidin-2-ones (LV) which are useful as antibacterial agents and the intermediates (VI), (VII) and (VIII) useful for their production.Type: GrantFiled: February 20, 1991Date of Patent: November 17, 1992Assignee: The Upjohn CompanyInventor: Steven J. Brickner
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Patent number: 5162354Abstract: A 3-halo-5-halomethyl-2-oxazolidinone, a method of making the same and a method of using the compound as a microbicide and for controlling the growth of at least one microorganism in an aqueous system or on a surface. A process for making 5-halomethyl-2-oxazolidinone utilizing an alkali cyanate and an epihalohydrin.Type: GrantFiled: December 20, 1991Date of Patent: November 10, 1992Assignee: Buckman Laboratories International, Inc.Inventors: Luis Fernando Del Corral, S. Rao Rayudu, Marilyn Whittemore
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Patent number: 5151439Abstract: The present invention discloses substituted 1,3-benzodioxoles which possess anti-diabetic and/or anti-hyperglycemic and/or anti-obesity properties in humans and other animals.Type: GrantFiled: August 1, 1991Date of Patent: September 29, 1992Assignee: American Cyanamid CompanyInventors: Jonathan D. Bloom, Thomas H. Claus, Vern G. DeVries, Jo A. Dolan, Minu D. Dutia
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Patent number: 5122472Abstract: Selenium reagents when coupled to a compound containing an asymmetric carbon atom can be used in a highly sensitive method for determination of enantiomeric purity and for stereochemical assignment. Preferred reagents include a selenocarbonyl moiety (Se.dbd.C) and a reactive center for coupling to the compound of interest. Particularly preferred selenocarbonyls for use in the invention are selenooxazolidinones of the formula ##STR1## wherein R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are selected from among hydrogen, alkyl of up to 10 carbons and aryl having up to 12 carbon atoms in the ring system. The substituent R.sup.1 is selected to facilitate the formation of a bond between the nitrogen atom of the selenooxazolidinone reagent and the compound of interest. Since the ability of the reagent to resolve enantiomers decreases as the number of bonds between the selenium and the asymmetric carbon increases, the reactive center is preferably located no more than three bonds from the selenium atom.Type: GrantFiled: October 6, 1989Date of Patent: June 16, 1992Assignee: University of South CarolinaInventors: Louis A. Silks, III, R. Bruce Dunlap, Jerome D. Odom
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Patent number: 5120755Abstract: Fungicidal substituted acrylic acid esters of the formula ##STR1## in which R.sup.1 and R.sup.2 independently of one another each stand for hydrogen, alkyl, alkenyl or for in each case optionally substituted aralkyl, aralkenyl, aryl or heteroaryl,R.sup.3 stands for alkyl or for optionally substituted aralkyl,R.sup.4 stands for dialkylamino or for a radical --Z--R.sup.5,X stands for oxygen or sulphur andY stands for oxygen, sulphur or for a radical ##STR2## wherein R.sup.5 stands for alkyl or for optionally substituted aralkyl,R.sup.6 stands for hydrogen, alkyl, alkanoyl or for in each case optionally substituted aralkyl or aryl andZ stands for oxygen or sulphur.Some intermediates are also new.Type: GrantFiled: August 6, 1990Date of Patent: June 9, 1992Assignee: Bayer AktiengesellschaftInventors: Gerd Kleefeld, Alexander Klausener, Wolfgang Kramer, Wilhelm Brandes, Stefan Dutzmann, Gerd Hanssler
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Patent number: 5110986Abstract: This application relates to a process for preparing a N-t-alkyl-1,2-diacylhydrazine by reacting a 1,3,4-oxadiazole with a tertiary alkyl cation precursor in the presence of a strong acid catalyst. Preferably, the 1,3,4-oxadiazole is a 2,5-disubstituted-1,3,4-oxadiazole and more preferably a 2,5-diaryl-1,3,4-oxadiazole. The strong acid catalyst is preferably a sulfur containing acid and more preferably sulfuric acid.Type: GrantFiled: April 26, 1988Date of Patent: May 5, 1992Assignee: Rohm and Haas CompanyInventor: Martha J. Kelly
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Patent number: 5106867Abstract: The present invention discloses substituted 1,3-benzodioxoles which possess anti-diabetic and/or anti-hyperglycemic and/or anti-obesity properties in humans and other animals.Type: GrantFiled: April 5, 1991Date of Patent: April 21, 1992Assignee: American Cyanamid CompanyInventors: Jonathan D. Bloom, Thomas H. Claus, Vern G. DeVries, Jo A. Dolan, Minu D. Dutia
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Patent number: 5105009Abstract: Intermediates of Formula ##STR1## where R is a methylthio, methylsulfoxy, methylsulfonyl or a nitro group; andX1 is hydrogen, 1-6 C alkyl, 1-6 C haloalkyl, 3-6 C cycloalkyl, phenyl or phenylalkyl(1-6C), where the phenyl ring may be substituted by one or two halogen, 1-3 C alkyl, 1-3 C alkoxy or nitro; orX1 together with X2 is an oxygen atom or an alkylene having from two to five Carbon atoms; orX1 together with X2 and R4 is a chain of formula ##STR2## where p is 3 or 4 and q is 1 or 2; and X2 is hydrogen, 1-6 C alkyl, 1-6 C haloalkyl, 3-6 C cycloalkyl or phenyl which may be substituted by one or two halogen, 1-3 C alkyl, 1-3 C alkoxy or nitro; orX2 together with R4 is ##STR3## where n is 1 or 2; m is 0 or 1; X is hydrogen, halogen, 1-3 C alkyl, 1-3 C alkoxy or nitro; andX3 is hydrogen or --CO--R4 where R4 is hydrogen, 1-6 alkyl, 1-6 C haloalkyl, 3-6 C cycloalkyl, phenylalkyl(1-6C) or phenyl where the phenyl ring may be substituted by one or two halogen, 1-3 alkyl, 1-3 alkoxy or nitro; andX4 is --OH, fluorine,Type: GrantFiled: February 29, 1988Date of Patent: April 14, 1992Assignee: Zambon S.p.A.Inventors: Giancarlo Jommi, Dario Chiarino
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Patent number: 5103007Abstract: Lipid derivatives represented by the formula: ##STR1## wherein R.sup.1 stands for an optionally substituted higher alkyl group, R.sup.2 stands for an optionally substituted lower alkyl group or an optionally substituted nitrogen-containing heterocyclic group, R.sup.3 stands for a tertiary amino group or a quaternary ammonium group, J stands for oxygen atom or S(O)t (where t deontes 0, 1 or 2), m and n respectively denotes 1 or 2, p denotes 0, 1 or 2, q and r respectively denote an integer of 2 to 5.and salts thereof have antitumor activities including differentiation-inducing activity and are useful as antitumor agents.Type: GrantFiled: October 27, 1989Date of Patent: April 7, 1992Assignee: Takeda Chemical Industries, Ltd.Inventors: Hiroaki Nomura, Hiroshi Akimoto, Keizo Inoue
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Patent number: 5101034Abstract: A process for the preparation of a heteroaryloxyacetamide of the formula ##STR1## in which R is a 5 membered heterocycle which may be benzo-fused, andR.sup.1 and R.sup.2 each independently is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl, halogenoalkyl, alkoxyalkyl, alkoxy, aralkyl or aryl, orR.sup.1 and R.sup.2, together with the nitrogen atom to which they are bonded, form a heterocycle,which comprises reacting a sulphonylated heteroaromatic of the formulaR--SO.sub.2 --R'in whichR' is lower alkyl or benzyl,with an .alpha.-oxyacetamide of the formula ##STR2## in which R" is hydrogen or acyl,in the presence of an inorganic base as an acid acceptor and of solvent as a diluent at a temperature of about -50.degree. C. to +150.degree. C. The products are known herbicides.Type: GrantFiled: March 7, 1991Date of Patent: March 31, 1992Assignee: Bayer AktiengesellschaftInventors: Thomas Schmidt, Hans-Joachim Diehr
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Patent number: 5099026Abstract: Fluorochemical oxazolidinone compositions are provided. They are normally solid, water-insoluble, fluoroaliphatic radical-containing 2-oxazolidinone compounds which have one or more 2-oxazolidinone moieties, at least one of which has a monovalent fluoroaliphatic radical bonded to the 5-position carbon atom thereof by an organic linking group.Type: GrantFiled: February 7, 1991Date of Patent: March 24, 1992Inventors: Davis H. Crater, Richard D. Howells, Richard M. Stern, John A. Temperante
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Patent number: 5081245Abstract: A compound represented by the formula: ##STR1## wherein R represents a hydrogen atom or a lower alkyl group;R.sup.1 represents a higher alkyl group which may be substituted;R.sup.2 represents a hydrogen atom or a lower alkyl group, a lower alkanoyl group or a nitrogen-containing 5- to 7-membered heterocyclic group each of which may be substituted; X represents a divalent group represented by the formula:--(OCH.sub.2 CH.sub.2).sub.p --wherein p represents an integer of 1 to 5, a divalent group represented by the formula:--O(CH.sub.2).sub.q --wherein q represents an integer of 3 to 8, or a divalent group represented by the formula:--(OCH.sub.2 CH.sub.2).sub.p --J--(CH.sub.2).sub.q --wherein J represents an oxygen atom or a group represented by the formula: --S(O).sub.Type: GrantFiled: August 18, 1989Date of Patent: January 14, 1992Assignee: Takeda Chemical Industries, Ltd.Inventors: Hiroaki Nomura, Hiroshi Akimoto, Eiko Imamiya, Keizo Inoue
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Patent number: 5073639Abstract: The present invention is a novel process for preparing both known and novel nitroimidazoles having novel intermediates. The process advantageously reduces the number of process steps, provides increased yield with both greater safety and greater control of stereoisomerism in the products.Type: GrantFiled: June 4, 1990Date of Patent: December 17, 1991Assignee: Warner-Lambert CompanyInventor: Mark J. Suto
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Patent number: 5066662Abstract: Oxazolidin-2-ones and 1,2,4-oxadiazolin-5-ones substituted in the 4-position of the oxazolidin-2-one ring and the 3-position of the 1,2,4-oxadiazolin-5-one ring with a 5- or 6-member heteroaromatic, a bicyclic heteroaromatic group or a 5- or 6-member heterocyclic group either directly or via a one or two carbon bridge and derivatives thereof are described, as well as methods for the preparation and pharmaceutical compositions of same, which are useful as centrally acting muscarinic agents and are useful as analgesic agents for the treatment of pain, as sleep aids and as agents for treating the symptoms of senile dementia, Alzheimer's disease, Huntington's chorea, tardive dyskinesia, hyperkinesia, mania, or similar conditions of cerebral insufficiency characterized by decreased cerebral acetycholine production or release.Type: GrantFiled: May 21, 1990Date of Patent: November 19, 1991Assignee: Warner-Lambert CompanyInventors: Sheila H. Hobbs, Stephen J. Johnson
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Patent number: 5061727Abstract: The present invention discloses substituted 1,3-benzodioxoles which possess anti-diabetic and/or anti-hyperglycemic and/or anti-obesity properties in humans and other animals.Type: GrantFiled: May 4, 1990Date of Patent: October 29, 1991Assignee: American Cyanamid CompanyInventors: Jonathan D. Bloom, Thomas H. Claus, Vern G. DeVries, Jo A. Dolan, Minu D. Dutia
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Patent number: 5043454Abstract: 1-Aryl- and 1-hetarylimidazolecarboxylic esters of the general formulae Ia and Ib ##STR1## where R.sup.1 is halogen or substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl;R.sup.2 is substituted or unsubstituted C.sub.1 -C.sub.6 -alkyl; C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl or C.sub.3 -C.sub.6 -cycloalkyl;R.sup.3 is hydrogen or C.sub.1 -C.sub.4 -alkyl;R.sup.4 is substituted or unsubstituted phenyl or 5- or 6-membered heteroaromatic,processes for their manufacture, and agents containing them.Type: GrantFiled: January 9, 1990Date of Patent: August 27, 1991Assignee: BASF AktiengesellschaftInventors: Ulrich Wriede, Gerhard Hamprecht, Hermann Koehler, Bruno Wuerzer
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Patent number: 5043443Abstract: Novel aminomethyloxooxazolidinyl arylbenzene derivatives, wherein the aryl includes the phenyl, substituted phenyl, pyridyl, and substituted pyridyl groups, such as (l)-N-{3-[4- (4'-pyridyl)phenyl]-2-oxooxazolidin-5-ylmethyl}acetamide, possess useful antibacterial activity.Type: GrantFiled: July 24, 1990Date of Patent: August 27, 1991Assignee: Du Pont Merck Pharmaceutical CompanyInventors: Randall K. Carlson, Chung-Ho Park, Walter A. Gregory
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Aminomethyl oxooxazolidinyl oxa or thia cycloalkylbenzene derivatives useful as antibacterial agents
Patent number: 5039690Abstract: Aminomethyl oxooxazolidinyl cycloalkylbenzene derivatives, such as l-N-[3-(2,3-dihydro-oxa or thio-lH-inden-5-yl)-2-oxooxazolidin-5-ylmethyl]acetamide, possess useful antibacterial activity.Type: GrantFiled: March 15, 1990Date of Patent: August 13, 1991Assignee: Du Pont Merck Pharmaceutical CompanyInventors: Chia-Lin J. Wang, Mark A. Wuonola -
Patent number: RE33778Abstract: Substituted 1,3-dithietane-2-carboxylic acid derivatives useful as intermediates for the preparation of highly effective penicillin and cephalosporin derivatives and the preparation thereof.Type: GrantFiled: December 8, 1989Date of Patent: December 24, 1991Assignee: Yamanouchi Pharmaceutical Co., Ltd.Inventors: Masaru Iwanami, Tetsuya Maeda, Yoshinobu Nagano, Masaharu Fujimoto, Noriaki Nagano, Atsuki Yamazaki, Kasaharu Tamazawa, Kiyoshi Murase, Tadao Shibanuma