The Ring Is Bonded Directly To The Carbonyl Patents (Class 564/183)
-
Patent number: 5609848Abstract: Haloaryl compounds are lithiated and thereafter metalated with one of the following organometallic groups: Sn(n--Bu).sub.3 or SnMe.sub.3. The resulting aryltin compound can be transmetalated in site-specific reaction with one of the following organometallic groups: HgX, Hg(OAc).sub.2, BX.sub.3, or BZ.sub.2, wherein X is Cl, Br, or I, and Z is alkyl or alkoxy. The metalated compounds are subsequently radiohalogenated via a demetalation reaction. A functional group suitable for conjugation to protein can be added subsequent or preferably prior to the radiohalogenation.Also compounds of the formula: R.sub.1 --Ar--R.sub.2, wherein R.sub.1 is either a radiohalogen or any one of the organometallic groups stated above, Ar is aromatic or heteroaromatic ring, and R.sub.2 is a short-chain substituent that does not activate the aromatic ring and that bears a functional group, or a precursor thereof, suitable for conjugation to protein under conditions that preserve the biological activity of the protein.Type: GrantFiled: September 23, 1991Date of Patent: March 11, 1997Assignee: NeoRx CorporationInventors: D. Scott Wilbur, Alan R. Fritzberg
-
Patent number: 5587513Abstract: The present invention relates to novel polyether-substituted compounds of imides and their use as surface-active agents.Type: GrantFiled: January 20, 1995Date of Patent: December 24, 1996Inventors: Klaus Pohmer, Rainer Weber, Cornelia D orzbach-Lange, Reinhard Haida, Hans-Heinrich Moretto
-
Patent number: 5580893Abstract: Nitroxyalkylamide compounds having the formula: R.sup.1 --(A).sub.n --CONH--B'--ONO.sub.2 wherein R.sup.1 is an optionally substituted furyl, furyloxy, thienyl, thienyloxy, isoxazolyl, phenoxy, phenylthio or 1,4-dibenzodioxanyl, A is a C.sub.1 -C.sub.4 alkylene group; B' is a C.sub.1 -C.sub.4 alkylene group; and n is 0 or 1. The compounds of the present invention have a desirable vasodilator action for collateral vessels and an anti-anginal action, and are useful as therapeutic agents for treating angina pectoris.Type: GrantFiled: July 25, 1994Date of Patent: December 3, 1996Assignee: Sankyo Company, LimitedInventors: Sadao Ishihara, Fujio Saito, Mitsuru Kataoka, Hiroyuki Koike, Shigeki Miyake, Hiroshi Mizuno
-
Patent number: 5541347Abstract: The present invention provides a novel synthesis of the compounds of Formula (I): ##STR1## The compounds are produced in high yield and without utilizing expensive chromatographic separations. The synthesis is particularly advantageous because it is stereoselective.Type: GrantFiled: October 3, 1994Date of Patent: July 30, 1996Assignee: Eli Lilly and CompanyInventors: Margaret M. Faul, Michael R. Jirousek, Leonard L. Winneroski II
-
Patent number: 5532363Abstract: Process for the preparation of a taxol intermediate comprising contacting an alcohol with an oxazinone having the formula: ##STR1## wherein R.sub.1 is aryl, heteroaryl, alkyl, alkenyl, alkynyl or OR.sub.7 wherein R.sub.7 is alkyl, alkenyl, alkynyl, aryl or heteroaryl; R.sub.2 and R.sub.5 are independently selected from hydrogen, alkyl alkenyl, alkynyl, aryl, heteroaryl, and OR.sub.8 wherein R.sub.8 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, or hydroxyl protecting group; and R.sub.3 and R.sub.6 are independently selected from hydrogen, alkyl, alkenyl, alkynyl, aryl and heteroaryl.Type: GrantFiled: November 7, 1994Date of Patent: July 2, 1996Assignee: Florida State UniversityInventor: Robert A. Holton
-
Patent number: 5516931Abstract: A release tag reagent suitable for use in the chemical analysis of a substance to be detected comprises signal, release, and reactivity groups. A class of release tag compounds that are cleaved to release as signal groups very stable electrophoric ketones which are sufficiently volatile for determination in the gas phase of an analytical reaction mixture is disclosed.Type: GrantFiled: April 22, 1993Date of Patent: May 14, 1996Assignee: Northeastern UniversityInventors: Roger W. Giese, Samy Abdel-Baky, Linxiao Xu
-
Patent number: 5473095Abstract: The present invention relates to a process for the preparation of compounds of the formula ##STR1## in which R.sup.1 is --CN, --COOH, --COOR', R' being an organic radical having 1 to 6 carbon atoms, --CONH.sub.2, --COCl or --CHO and R.sup.2 is H or Cl, which comprises reacting a compound of the formula ##STR2## in which R.sup.1 is as defined above and R.sup.3 is H or Cl, with a chlorinating agent in the presence of a chlorination catalyst at -10.degree. to 200.degree. C.Type: GrantFiled: January 27, 1994Date of Patent: December 5, 1995Assignee: Hoechst AktiengesellschaftInventors: Ralf Pfirmann, Theodor Papenfuhs, Georg Weichselbaumer
-
Patent number: 5470878Abstract: Therapeutic compounds have the formula:(X)j-(non-cyclic core moiety),j being an integer from one to three, the core moiety is non-cyclic and X is a racemic mixture, R or S enantiomer, solvate, hydrate, or salt of: ##STR1## *C is a chiral carbon atom, n is an integer from one to four (preferably from one to three), one or more carbon atoms of (CH.sub.2).sub.n may be substituted by a keto or hydroxy group, and m is an integer from one to fourteen. Independently, R.sub.1 and R.sub.2 may be a hydrogen, a straight or branched chain alkane or alkene of up to twelve carbon atoms in length, or --(CH.sub.2).sub.w R.sub.5, w being an integer from two to fourteen and R.sub.5 being a mono-, di- or tri-substituted or unsubstituted aryl group, substituents on R.sub.5 being hydroxy, chloro, fluoro, bromo, or C.sub.1-6 alkoxy. Or jointly, R.sub.1 and R.sub.2 form a substituted or unsubstituted, saturated or unsaturated heterocyclic group having from four to eight carbon atoms, N being a hetero atom. R.sub.Type: GrantFiled: December 8, 1993Date of Patent: November 28, 1995Assignee: Cell Therapeutics, Inc.Inventors: John Michnick, Gail E. Underiner, J. Peter Klein, Glenn C. Rice
-
Patent number: 5430060Abstract: The invention concerns novel N-phenylacetyl and related acyl derivatives of (4-amino-2,6-dimethylphenylsulphonyl)nitromethane and pharmaceutically acceptable salts thereof which are inhibitors of the enzyme aldose reductase and are of value, for example, in the treatment of certain peripheral effects of diabetes and galactosemia. Also disclosed are pharmaceutical compositions containing one of the derivatives and processes for the manufacture and use of the derivatives.Type: GrantFiled: September 15, 1993Date of Patent: July 4, 1995Assignee: Zeneca LimitedInventors: David R. Brittain, Steven P. Brown, Anthony L. Cooper, Jethro L. Longridge, Jeffrey J. Morris, John Preston, Linda Slater
-
Patent number: 5393776Abstract: This invention relates to structurally novel acyclic tocotrienol analogs, which are useful for cholesterol/lipid lowering in cases of hypercholesterolemia and hyperlipidemia, and for atherosclerosis. Also provided are pharmaceutical compositions and a method of use employing those compositions.Type: GrantFiled: May 13, 1994Date of Patent: February 28, 1995Assignee: Bristol-Myers Squibb CompanyInventor: Bradley C. Pearce
-
Patent number: 5384399Abstract: Process for the preparation of a taxol intermediate comprising contacting an alcohol with an oxazinone having the formula: ##STR1## wherein R.sub.1 is aryl, heteroaryl, alkyl, alkenyl, alkynyl or OR.sub.7 wherein R.sub.7 is alkyl, alkenyl, alkynyl, aryl or heteroaryl; R.sub.2 and R.sub.5 are independently selected from hydrogen, alkyl alkenyl, alkynyl, aryl, heteroaryl, and OR.sub.8 wherein R.sub.8 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, or hydroxyl protecting group; and R.sub.3 and R.sub.6 are independently selected from hydrogen, alkyl, alkenyl, alkynyl, aryl and heteroaryl.Type: GrantFiled: June 15, 1992Date of Patent: January 24, 1995Assignee: Florida State UniversityInventor: Robert A. Holton
-
Patent number: 5356893Abstract: The invention provides compounds of formula (I): ##STR1## or a physiologically acceptable salt or solvate thereof wherein R.sup.1 represents a halogen or hydrogen atom or a C.sub.1-6 alkyl or C.sub.1-6 alkoxy group;R.sup.2 represents a phenyl group optionally substituted by one or two substituents;R.sup.3 represents the group ##STR2## R.sup.4 and R.sup.5, which may be the same or different, each independently represent a hydrogen atom or a halogen atom, or a group selected from hydroxy, C.sub.1-6 alkoxy or C.sub.1-6 alkyl.The compounds may be used in the treatment or prophylaxis of depression and other CNS disorders.Type: GrantFiled: September 17, 1992Date of Patent: October 18, 1994Assignee: Glaxo Group LimitedInventors: John Bradshaw, John W. Clitherow, Ian B. Campbell
-
Patent number: 5352703Abstract: 2-benzoylamino-3,5-dibromo-N-(4-hydroxycyclohexyl)benzylamine of formula (I), and pharmaceutically acceptable acid addition salts have antitussive and mucus regulating activities.Type: GrantFiled: November 23, 1992Date of Patent: October 4, 1994Assignee: Mediolanum Farmaceutici S.p.A.Inventor: Giuseppe Quadro
-
Patent number: 5318770Abstract: Methods and compositions are disclosed for enhancing .sup.19 F magnetic resonance imaging which utilize trifluorometyl derivatives of iodinated X-ray contrast media. Typical magnetic resonance contrast media within the scope of the present invention include bis(trifluoromethyl)benzene derivatives, tris(trifluoromethyl)benzene derivatives, tetrakis(trifluoromethyl)benzene derivatives, and other related trifluoromethylated benzene derivatives.Type: GrantFiled: October 25, 1991Date of Patent: June 7, 1994Assignee: Mallinckrodt Medical, Inc.Inventors: David H. White, Steven R. Woulfe, Youlin Lin, Mills T. Kneller
-
Patent number: 5298647Abstract: Aromatic compounds absorbing UVB and/or UVA, substituted with an amide function, selected from the group consisting of ##STR1## whose variable substituents are as defined in the specification, e.g. ##STR2## are useful as photoprotective agents or tanning accelerators.Type: GrantFiled: December 14, 1987Date of Patent: March 29, 1994Inventors: Dominique Robert, Louis Jung
-
Patent number: 5278338Abstract: A method for racemizing an optically active carboxylic acid, or ester thereof, of the formula: ##STR1## where R.sub.1 is hydrogen, hydroxy, halo, cyano, C.sub.1 to C.sub.6 linear or branched alkoxy, amino or substituted amino or the group ##STR2## is nitrile; R.sub.2, R.sub.3 and R.sub.4 are different and are hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl, C.sub.1 to C.sub.6 linear or branched haloalkyl, aralkyl, cycloalkyl, alkyl substituted cycloalkyl, C.sub.6 to C.sub.10 aryl, C.sub.1 to C.sub.6 linear or branched alkoxy, C.sub.6 to C.sub.10 aryloxy, C.sub.1 to C.sub.6 alkylthio, C.sub.3 to C.sub.8 cycloalkylthio, C.sub.6 to C.sub.10 arylthio, C.sub.6 to C.sub.10 arylcarbonyl, C.sub.4 to C.sub.8 cycloalkenyl, trifluoromethyl, halo, C.sub.4 to C.sub.5 heteroaryl, C.sub.10 to C.sub.14 aryl, or biphenyl unsubstituted or substituted with methyl or halo, comprising heating said optically active carboxylic acid or ester thereof in the presence of water at a temperature of from about 40.degree. C.Type: GrantFiled: November 4, 1992Date of Patent: January 11, 1994Assignee: Ethyl CorporationInventor: Rhonda L. Trace
-
Patent number: 5270342Abstract: The invention concerns novel N-phenylacetyl and related acyl derivatives of (4-amino-2,6-dimethylphenylsulphonyl)nitromethane and pharmaceutically acceptable salts thereof which are inhibitors of the enzyme aldose reductase and are of value, for example, in the treatment of certain peripheral effects of diabetes and galactosemia. Also disclosed are pharmaceutical compositions containing one of the derivatives and processes for the manufacture and use of the derivatives.Type: GrantFiled: July 31, 1991Date of Patent: December 14, 1993Assignee: Imperial Chemical Industries PLCInventors: David R. Brittain, Steven P. Brown, Anthony L. Cooper, Jethro L. Longridge, Jeffrey J. Morris, John Preston, Linda Salter
-
Patent number: 5260483Abstract: Methods of producing N-aryl amides comprise reacting an aromatic isocyanate compound with substantially anhydrous carboxylic acid and recovering the resulting N-aryl amide. Additionally, or alternatively, methods of forming N-aryl amides comprise reacting an aromatic isocyanate compound with substantially anhydrous carboxylic acid in the presence of an anhydrous hydrogen halide or hydrolytically unstable halide compound and recovering the resulting N-aryl amide. These reactions may occur in the presence of an aprotic solvent.Type: GrantFiled: September 9, 1991Date of Patent: November 9, 1993Assignee: Drexel UniversityInventors: Franklin A. Davis, William E. Starner
-
Patent number: 5238962Abstract: Benzamides of the formula ##STR1## wherein R.sup.1 and R.sup.2 each independently is hydrogen, halogen, lower alkyl, lower alkoxy, cyano, trifluoromethyl, sulfamoyl, mono(lower alkyl)sulfamoyl or di(lower alkyl)sulfamoyl or R.sup.1 and R.sup.2 on adjacent carbon atoms together are a methylenedioxy group, with the proviso that R.sup.2 is different from hydrogen when R.sup.1 are bromine in the 3-position,and their pharmaceutically acceptable acid addition salts have monoamine oxidase inhibiting properties with low toxicity and can accordingly be used for the treatment of depressive states and Parkinsonism.Type: GrantFiled: June 9, 1992Date of Patent: August 24, 1993Assignee: Hoffmann-La Roche Inc.Inventors: Mose Da Prada, Renato Joos, Emilio Kyburz, Pierre C. Wyss
-
Patent number: 5233074Abstract: The invention describes a process for selectively preparing ortho-fluorinated substituted aromatic compounds wherein an aromatic compound containing a substituent capable of directing ortho metalation is contacted with a metalating reagent under reaction conditions sufficient to form an ortho-metalated substituted aromatic compound. The ortho-metalated substituted aromatic compound is reacted with an electrophilic fluorinating reagent under reaction conditions sufficient to form the desired ortho-fluorinated substituted aromatic compound which is then recovered from the reaction mixture. The process which utilizes a metalation intermediate prior to effecting the electrophilic fluorination step overcomes problems associated with prior art electrophilic fluorination processes which do not proceed through a regiospecifically controlled intermediate.Type: GrantFiled: June 1, 1992Date of Patent: August 3, 1993Assignee: Air Products and Chemicals, Inc.Inventor: Gauri S. Lal
-
Patent number: 5223645Abstract: Unsaturated phenone derivatives of the general formula I ##STR1##whereR.sup.1 is C.sub.1 -C.sub.4 -alkyl, cyclopropyl, cyclopentyl, cyclohexyl, indanonyl, tetralonyl, phenyl or phenyl in which some or all of the hydrogen atoms have been replaced by a C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -thioalkyl group, or together with R.sup.2 or R.sup.6 forms an ethylene or propylene bridge,R.sup.2 to R.sup.6 are each hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -thioalkyl, and R.sup.3, R.sup.4 and R.sup.5 may each additionally be hydroxyl, R.sup.2 or R.sup.6 may additionally together with R.sup.1 form an ethylene or propylene bridge and one or more, but not more than three, of the radicals R.sup.2 to R.sup.6 are a group of the general formula II ##STR2##whereK is C.sub.1 -C.sub.10 -alkylene which may contain 1 or 2 oxygen or sulfur atoms,Y is straight-chain or branched C.sub.1 -C.sub.10 -alkylene or is C.sub.1 -C.sub.Type: GrantFiled: September 23, 1991Date of Patent: June 29, 1993Assignee: BASF AktiengesellschaftInventors: Juergen Barwich, Gerd Rehmer, Kaspar Bott
-
Patent number: 5213787Abstract: Haloaryl compounds are lithiated and thereafter metalated with one of the following organometallic groups: Sn(n-Bu).sub.3 or SnMe.sub.3. The resulting aryltin compound can be transmetalated in site-specific reaction with one of the following organometallic groups: HgX, Hg(OAc).sub.2, BX.sub.3, or BZ.sub.2, wherein X is Cl, Br, or I, and Z is alkyl or alkoxy. The metalated compounds are subsequently radiohalogenated via a demetalation reaction. A functional group suitable for conjugation to protein can be added subsequent or preferably prior to the radiohalogenation.Also compounds of the formula: R.sub.1 -Ar-R.sub.2, wherein R.sub.1 is either a radiohalogen or any one of the organometallic groups stated above, Ar is aromatic or heteroaromatic ring, and R.sub.2 is a short-chain substituent that does not activate the aromatic ring and that bears a functional group, or a precursor thereof, suitable for conjugation to protein under conditions that preserve the biological activity of the protein.Type: GrantFiled: December 12, 1990Date of Patent: May 25, 1993Assignee: NeoRx CorporationInventors: Daniel S. Wilbur, Alan R. Fritzberg
-
Patent number: 5214202Abstract: This invention relates to a synthesis method favorable for the industrial production of a benzoic acid derivative having a retinoid activity of the general formula: ##STR1## wherein the derivative can be obtained by a simple procedure in safety with high yield.Specifically, this invention relates to a synthesis method characterized in that only one vessel is needed for several reactions in the different steps of subjecting acetanilide as a starting material, which is readily available and safe to handle, to Friedel-Crafts reaction with 2,5-dimethyl-2,5-dichlorohexane; subjecting the thus obtained compound to acyl exchange reaction with monomethyl ester terephthalic chloride, followed by hydrolysis; and recrystallizing from a mixture of methanol and water.Moreover, the crystals in novel form obtained by the synthesis method of this invention are suitable for formulation, because the amount of solvents remaining therein after recrystallization is small and the grain size thereof is uniform.Type: GrantFiled: November 6, 1991Date of Patent: May 25, 1993Assignee: Shionogi & Co., Ltd.Inventors: Yoshinori Hamada, Isamu Yamada, Masaaki Uenaka, Teruo Sakata
-
Patent number: 5179231Abstract: Hexene-1,6-dioic acids, e.g., hex-3-ene-1,6-dioic acid, are prepared by reacting carbon monoxide with at least one butenediol, in a polar, aprotic, basic solvent, in the presence of a catalytically effective amount of palladium values and at least one inorganic halide, the cation of which halide being an alkali or alkaline earth metal and the anion thereof being a chloride or bromide.Type: GrantFiled: December 13, 1990Date of Patent: January 12, 1993Assignee: Rhone-Poulenc ChimieInventor: Philippe Denis
-
Patent number: 5136060Abstract: Process for the preparation of a taxol intermediate comprising contacting an alcohol with an oxazinone having the formula: ##STR1## wherein R.sub.1 is aryl, heteroaryl, alkyl, alkenyl, alkynyl or OR.sub.7 wherein R.sub.7 is alkyl, alkenyl, alkynyl, aryl or heteroaryl; R.sub.2 and R.sub.5 are independently selected from hydrogen, alkyl alkenyl, alkynyl, aryl, heteroaryl, and OR.sub.8 wherein R.sub.8 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, or hydroxyl protecting group; and R.sub.3 and R.sub.6 are independently selected from hydrogen, alkyl, alkenyl, alkynyl, aryl and heteroaryl.Type: GrantFiled: October 30, 1990Date of Patent: August 4, 1992Assignee: Florida State UniversityInventor: Robert A. Holton
-
Patent number: 5136085Abstract: Process for synthesizing 2-aminobenzophenones such as the following formula (I): ##STR1## wherein X.sup.1 and X.sup.2 are substituents and r and s are 1 or 2, by reacting an anthranilic acid amide e.g. an N-alkoxy-N-alkyl anthranilic acid amide, with a halobenzene in the presence of an alkyllithium reagent.Type: GrantFiled: July 3, 1991Date of Patent: August 4, 1992Assignee: Glaxo Inc.Inventors: Marty C. Johnson, Stephen V. Frye
-
Patent number: 5118846Abstract: Disclosed is a method which comprises introducing into a reaction zone a feed which comprises a hydroxyl compound reactant, R"OH at least one amide reactant selected from R--CONH.sub.2 and R--CONHR', and a Lewis base as catalyst, thereby reacting R"OH with said amide reactant to produce a reaction mixture containing at least one disubstituted amide selected from R--CONR".sub.2 and R--CONR'R", whereineach of R, R' and R" contains no acetylenic unsaturation and 1 to 30 carbon atoms;each of R, R' and R" is selected from a hydrocarbyl groups and a hydrocarbyl group that is substituted with a group selected from carbamoyl, hydrocarbylcarbamoyl, dihydrocarbylcarbamoyl, and hydroxyl.Type: GrantFiled: April 27, 1990Date of Patent: June 2, 1992Assignee: The Standard Oil CompanyInventor: Mark C. Cesa
-
Patent number: 5106407Abstract: The present invention discloses the antimicrobial utility of certain iodonium ylide compounds. The particular iodonium ylide compounds are phenyl iodonium ylides having an ortho substituent that stabilizes the positive charge on the polyvalent iodine by a nonbonded electrostatic interaction. The polyvalent iodine is further stabilized by a cyclic 1,3-dicarbonyl anion.Type: GrantFiled: December 4, 1989Date of Patent: April 21, 1992Assignee: The Dow Chemical CompanyInventors: Attila G. Relenyi, Gerald F. Koser, Richard W. Walter, Jr., William J. Kruper, Jr., Ravi B. Shankar, Anthony P. Zelinko
-
Patent number: 5089638Abstract: Analogs of glutamic acid and related amino acids and pharmaceutically-acceptable salts thereof which antagonize the function of cholecystokinins and gastrin disease states in animals and compositions for and methods of preventing or treating disorders of the gastrointestinal, central nervous and appetite regulatory systems of mammals, especially of humans.Type: GrantFiled: August 30, 1989Date of Patent: February 18, 1992Assignee: Merck & Co., Inc.Inventor: Roger M. Freidinger
-
Patent number: 5082654Abstract: A clathrate compound which comprises diethyltoluamide and a polymolecular host compound capable of taking up diethyltoluamide.The host compound is bisphenol compounds. Diethyltoluamide is stabilized by forming the clathrate compound.Type: GrantFiled: October 19, 1989Date of Patent: January 21, 1992Assignee: Kurita Water Industries Ltd.Inventors: Hideo Sugi, Ryoichi Takahashi, Kenji Tahara
-
Patent number: 5082862Abstract: An N-substituted benzamide of the formula ##STR1## in which R.sup.1 represents hydrogen or alkyl,R.sup.2 represents halogenoalkyl with more than one carbon atom, or represents cycloalkyl which is substituted by halogen or halogenoalkyl and R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are identical or different and represent hydrogen, halogen, nitro, alkyl, halogenoalkyl, halogenoalkoxy or halogenoalkylthio, or represent the radical --CONR.sup.1 R.sup.2.The N-substituted benzamides are active as insecticides and nematicides and can be prepared by reacting a benzoyl halide of the formula (II) ##STR2## in which R.sup.8, R.sup.9, R.sup.10, R.sup.11 and R.sup.12 are identical or different and represent hydrogen, halogen, nitro, alkyl, halogenoalkyl, halogenoalkoxy or halogenoalkylthio, or represent the radical --CO--Hal and Hal represents halogen,with an amine of the formula (III)HNR.sup.1 R.sup.2 (III)in whichR.sup.1 and R.sup.2 have the abovementioned meanings, or with the corresponding hydrohalides.Type: GrantFiled: January 4, 1989Date of Patent: January 21, 1992Assignee: Bayer AktiengesellschaftInventors: Horst Tarnow, Bernhard Homeyer
-
Patent number: 5072038Abstract: 2,3,4,5-trihalogenobenzene derivatives of the formula ##STR1## in which R is --COOH, --COCl, --COF, --CN, --CONH.sub.2, --CH.sub.2 OH, --CH.sub.2 Cl, --CHCl.sub.2, --CCl.sub.3 or --CHO,R.sup.1 is H, Cl or F, andR.sup.2 is Cl or F,it only being possible for R.sup.1 or R.sup.2 to be F, and processes for their preparation starting from benzonitriles reacted with potassium fluoride. The novel compounds are intermediates for antibacterials such as quinolone carboxylic acids.Type: GrantFiled: January 2, 1990Date of Patent: December 10, 1991Assignee: Bayer AktiengesellschaftInventors: Erich Klauke, Uwe Petersen, Klaus Grohe
-
Patent number: 5064861Abstract: A compound selected from the group consisting of a compound of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of Ar-O- and aryl, polyaryl and condensed polyaryl unsubstituted or substituted and heterocycle unsubstituted or substituted, Ar is aryl of 6 to 14 carbon atoms unsubstituted or substituted, heteroaryl unsubstituted or substituted and heterocyclic unsubstituted or substituted, W is selected from the group comsisting of --(CH.sub.2).sub.n.sbsb.1 --or --(CH.sub.2).sub.n.sbsb.2 --NY--(CH.sub.2).sub.n.sbsb.3, n.sub.1, n.sub.2 and n.sub.3 are individually integers from 2 to 6, Y is selected from the group consisting of hydrogen, alkyl of 1 to 12 carbon atoms, aryl of 6 to 12 carbon atoms and aralkyl of 7 to 14 carbon atoms unsubstituted or substituted, --COOAlk and --COR.sub.2, Alk is alkyl of 1 to 12 carbon atoms, R.sub.Type: GrantFiled: December 21, 1989Date of Patent: November 12, 1991Assignee: Roussel UclafInventors: Jean-Louis Brayer, Laurent Taliani, Jean Tessier
-
Patent number: 5057623Abstract: An organic fluorine compound represented by the general formulaR.sub.f -(X).sub.h -R-Mwherein R.sub.f is a group selected from the following (a) and (b); ##STR1## X denotes a linking group selected from --O--, --S--, and --COO--, h denotes 0 or 1, R is a hydrocarbon chain comprising a phenylene group having an alkylene group with a total carbon number of 10 or more, or the derivative thereof, or an aliphatic alkylene group of a carbon number of 10 or more, and M is a group selected from --OH, --COOH, --SH, and --CONH.sub.2.The organic fluorine compound of the present invention greatly improves the dispersibility of magnetic powders in magnetic coating materials, has also an excellent rust prevention effect on metallic magnetic powders, and exhibits a marked dispersing effect even on fluorocarbon resin fine powders, which can be difficultly dispersed with conventional dispersing agents.Type: GrantFiled: October 13, 1989Date of Patent: October 15, 1991Assignee: Matsushita Electric Industrial Co., Ltd.Inventors: Yoshiaki Kai, Takashi Suzuki
-
Patent number: 5053543Abstract: Process for synthesizing 2-aminobenzophenones such as the following formula (I): ##STR1## wherein X.sup.1 and X.sup.2 are substituents and r and s are 1 or 2, by reacting an anthranilic acid amide e.g. an N-alkoxy-N-alkyl anthranilic acid amide, with a halobenzene in the presence of an alkyllithium reagent.Type: GrantFiled: November 28, 1990Date of Patent: October 1, 1991Assignee: Glaxo Inc.Inventors: Marty C. Johnson, Stephen V. Frye
-
Patent number: 5047410Abstract: New pharmacologically active amidino and guanidino derivatives which are 5-HT.sub.3 receptor antagonists useful as antiemetic, gastric prokinetic and antimigrainic agents of the following general formula (I) ##STR1## , wherein the substituents are defined hereinbelow, which compounds are 5-HT.sub.3 receptor antagonists useful as antiemetic gastric prokinetic and antimigraine agents, inter alia.Type: GrantFiled: July 12, 1989Date of Patent: September 10, 1991Assignee: Istituto de Angeli S.p.A.Inventors: Arturo Donetti, Marco Turconi, Massimo Nicola, Rosamaria Micheletti
-
Patent number: 5045303Abstract: Haloaryl compounds are lithiated and thereafter metalated with one of the following organometallic groups: Sn(n-Bu).sub.3 or SnMe.sub.3. The resulting aryltin compound can be transmetalated in site-specific reaction with one of the following organometallic groups: HgX, Hg(OAc).sub.2, BX.sub.3, or BZ.sub.2, wherein X is Cl, Br, or I, and Z is alkyl or alkoxy. The metalated compounds are subsequently radiohalogenated via a demetalation reaction. A functional group suitable for conjugation to protein can be added subsequent of preferably prior to the radiohalogenation.Also compounds of the formula: R.sub.1 -Ar-R.sub.2, wherein R.sub.1 is either a radiohalogen or any one of the organometallic groups stated above, Ar is aromatic or heteroaromatic ring, and R.sub.2 is a short-chain substituent that does not activate the aromatic ring and that bears a functional group, or a precursor thereof, suitable for conjugation to protein under conditions that preserve the biological activity of the protein.Type: GrantFiled: November 23, 1987Date of Patent: September 3, 1991Assignee: NeoRx CorporationInventors: Daniel S. Wilbur, Alan R. Fritzberg
-
Patent number: 4997984Abstract: A process for the preparation of an N-(.alpha.-alkoxyethyl)carboxylic acid amide represented by the following formula [I]: ##STR1## wherein R stands for a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a benzyl group or an aryl group, and R.sup.1 stands for an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group,which comprises reacting an ethylidene-bisamide represented by the following formula [II]:CH.sub.3 CH(NHCOR).sub.2 [II]wherein R stands for a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a benzyl group or an aryl group,with an alkanol in the presence of an acid catalyst. According to this process, a high-purity N-(.alpha.-alkoxyethyl)carboxylic acid amide, which is valuable as an intermediate for the production of an N-vinylcarboxylic acid amide and the like, can be easily prepared from cheap and easily available starting materials.Type: GrantFiled: December 19, 1989Date of Patent: March 5, 1991Assignee: Shawa Denko K.K.Inventors: Shuichi Sugita, Tetsuo Kudo, Kuniomi Marumo
-
Patent number: 4987257Abstract: Disclosed is a diacetylene compound comprising, as structural units, (a) at least one member selected from diacetylene group-containing organic groups of the formulae (I) and (II):R.sup.I --C.tbd.C--C.tbd.C--R.sup.II -- (I)and--R.sup.III --C.tbd.C--C.tbd.C--R.sup.IV -- (II)wherein R.sup.I is hydrogen or a (C1-16) monovalent organic group, and R.sup.II, R.sup.III and R.sup.IV are a (C1-13) divalent organic group, (b) at least one organic group having at least one carbon-to-carbon double bond, and (c) at least one connecting group connecting the units (a) and (b), which connecting group is selected from amide, imide, ester, ether, amino, imino, urethane, sulfonyl and carbonyl bonds. A cured shaped article made of this compound exhibits isotropically a high elastic modulus and has excellent mechanical properties.Type: GrantFiled: February 23, 1990Date of Patent: January 22, 1991Assignee: Director-General of Agency of Industrial Science and TechnologyInventors: Katsuyuki Nakamura, Satoru Yamazaki, Jinichiro Kato, Kensaku Tokushige
-
Patent number: 4983630Abstract: There are provided new 2,2-difluorocyclopropylethane derivatives of general formula I ##STR1## in which A, B and R.sup.1-5 have the meanings given in the description and processes for their preparation. The compounds of the invention can be used as pesticides, especially against insects and mites.Type: GrantFiled: November 28, 1988Date of Patent: January 8, 1991Assignee: Schering AktiengesellschaftInventors: Peter Wegner, Hartmut Joppien, Gunter Homberger, Arnim Kohn
-
Patent number: 4983747Abstract: Disclosed is a process for the preparation of a perfluoroorganic compound, which comprises fluorinating a partially fluorinated or unfluorinated organic compound having carbon-to-fluorine bonds under mild conditions and then, contacting the resulting reaction mixture with a fluorine gas at a temperature of 110.degree. to 180.degree. C.Type: GrantFiled: March 15, 1990Date of Patent: January 8, 1991Assignee: Tokuyama Soda Kabushiki KaishaInventors: Masakatsu Nishimura, Naoya Okada, Yasuo Murata, Yasuhiko Hirai
-
Patent number: 4939291Abstract: For the preparation of saline derivatives of mercaptoethansulfonic acid belonging to the class of the salts of alkali metals and of the salts with basic aminoacids, the sodium salt of the acid is obtained with a process comprising the reaction between sodium bromoethansulfonate with thiobenzoic acid and sodium bicarbonate and subsequent reaction of the resulting sodium benzoylethansulfonate with ammonia in water solution.Type: GrantFiled: May 1, 1989Date of Patent: July 3, 1990Assignee: Schering SpAInventor: Alberto Reiner
-
Patent number: 4908388Abstract: Derivatives of carbonyl-group containing behavior modifying compounds, in which said carbonyl group has been converted to a photolabile group which regenerates the carbonyl group on exposure to radiation, are of value in various methods for the control of animal, and in particular insect, species.Type: GrantFiled: January 20, 1988Date of Patent: March 13, 1990Assignee: National Research Development CorporationInventors: John A. Pickett, Ewen D. M. Macaulay
-
Patent number: 4883916Abstract: A polyprenyl compound terminated with a group of ##STR1## is novel and useful as an antihypercholesterolemic agent and an antiarteriosclerotic agent, in which X is a group of the formula ##STR2## wherein K and L are independently a hydrogen atom or form a single valence bond between the carbon atoms to which they are attached, a group represented by the formula --CH.sub.2 -- or a group represented by the formula --(CH.sub.2).sub.2 --, m is an integer of 0 or 1, and R stands for a hydroxy group, a group represented by the Formula ##STR3## wherein R.sup.1 and R.sup.2 may be the same or different and each stands for a hydrogen atom or a lower alkyl group and p stands for an integer of 1 or 2, a group represented by the formula --NH--(CH.sub.2).sub.Type: GrantFiled: April 1, 1988Date of Patent: November 28, 1989Assignee: Eisai Co., Ltd.Inventors: Kouji Nakamoto, Takeshi Suzuki, Shinya Abe, Kenji Hayashi, Akiharu Kajiwara, Isao Yamatsu, Issei Otsuka, Hiroyuki Shiojiri
-
Patent number: 4880938Abstract: Analogs of glutamic acid and related amino acids and pharmaceutically-acceptable salts thereof which antagonize the function of cholecystokinins and gastrin disease states in animals and compositions for and methods of preventing or treating disorders of the gastrointestinal, central nervous and appetite regulatory systems of mammals, especially of humans.Type: GrantFiled: June 16, 1986Date of Patent: November 14, 1989Assignee: Merck & Co., Inc.Inventor: Roger M. Freidinger
-
Patent number: 4880894Abstract: Novel quaternary ammonium salts of general formula (I) ##STR1## wherein: R is a saturated or unsaturated, linear or branched alkyl radical of C.sub.1 to C.sub.8.R' is a saturated or unsaturated, linear or branched alkyl radical of C.sub.1 to C.sub.12, or a benzyl radical.n is a number equal to 2 or 3.X.sup..theta. is a halogenide anion, such as Cl.sup..theta., Br.sup..theta., I.sup..theta., are used as phase transfer catalysts, in heterogeneous ionic reactions wherein the reagents are in different phase and have different polarity.Type: GrantFiled: September 26, 1988Date of Patent: November 14, 1989Assignee: Alter, S.A.Inventors: Carlos Sunkel, Miguel Fay de Casa Juana, Fernando Dorrego, Basilio Pando, Julio Alvarez-Builla, Juan J. Vaquero, Carlos Galera, Maria L. Vazquez
-
Patent number: 4876269Abstract: Benzo-fused cycloalkane and oxa- and thia-cycloalkane trans-1,2-diamine compounds of the formula: ##STR1## wherein A, B, C, D, n, X, Y, R, R.sup.1, R.sup.2 and R.sup.3 are as defined in the specification, e.g., trans-3,4-dichloro-N-methyl-N-[2-(pyrrolidin-1-yl)-5-methoxy-1,2,3,4-tetra hydronaphth-1-yl]benzeneacetamide, and the pharmaceutically acceptable salts of N-oxides thereof, are useful as analgesics and/or diuretics.Type: GrantFiled: July 16, 1987Date of Patent: October 24, 1989Assignee: E. I. Du Pont de Nemours and CompanyInventors: Penio Pennev, Parthasarathi Rajagopalan, Richard M. Scribner
-
Patent number: 4840969Abstract: An N-substituted benzamide of the formula ##STR1## in which R.sup.1 represents hydrogen or alkyl,R.sup.2 represents halogenoalkyl with more than one carbon atom, or represents cycloalkyl which is substituted by halogen or halogenoalkyl andR.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are identical or different and represent hydrogen, halogen, nitro, alkyl, halogenoalkyl, halogenoalkoxy or halogenoalkylthio, or represent the radical--CONR.sup.1 R.sup.2.The N-substituted benzamides are active as insecticides and nematicides and can be prepared by reacting a benzoyl halide of the formula (II) ##STR2## in which R.sup.8, R.sup.9, R.sup.10, R.sup.11 and R.sup.12 are identical or different and represent hydrogen, halogen, nitro, alkyl, halogenoalkyl, halogenoalkoxy or halogenoalkylthio, or represent the radical --CO--Hal and Hal represents halogen,with an amine of the formula (III)HNR.sup.1 R.sup.2 (III)in whichR.sup.1 and R.sup.2 have the abovementioned meanings, or with corresponding hydrohalides.Type: GrantFiled: March 19, 1987Date of Patent: June 20, 1989Assignee: Bayer AktiengesellschaftInventors: Horst Tarnow, Bernhard Homeyer
-
Patent number: 4826982Abstract: Quinolonecarboxylic acid derivatives of the following formula, ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each independently hydrogen atom or lower alkyl group; the hydrates or the pharmaceutically acceptable acid addition or alkali salts thereof are useful as an antibacterial agent.Type: GrantFiled: September 2, 1986Date of Patent: May 2, 1989Assignee: Kyorin Pharmaceutical Co., Ltd.Inventors: Kuniyoshi Masuzawa, Seigo Suzue, Keiji Hirai, Takayoshi Ishizaki
-
Patent number: 4804765Abstract: The invention concerns a novel process for the synthesis of N-[(1'-allyl-2'-pyrrolidinyl) methyl]-2-methoxy-4,5-azimidobenzamide, which successively comprises the preparation of 2-methoxy-4,5-diaminobenzoic acid, 2-methoxy-4,5-diacetylaminobenzoic acid, N-(2',5'-dihalopentyl)-2-methoxy-4,5-diacetylaminobenzamide, N-[(1'-allyl-2'-pyrrolidinyl) methyl]-2-methoxy-4,5-diacetylaminobenzamide and then N-[(1'-allyl-2'-pyrrolidinyl) methyl]-2-methoxy-4,5-azimido benzamide.Type: GrantFiled: December 18, 1985Date of Patent: February 14, 1989Assignee: Societe D'Etudes Scientifiques et Industrielles de L'Ile-d-FranceInventors: Jacques Acher, Jean-Claude Monier