Having -c(=x)-, Wherein X Is Chalcogen, Bonded Directly To Ring Carbon Of The Oxazole Ring By Nonionic Bonding Patents (Class 548/248)
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Patent number: 5532259Abstract: Isoxazole-4-carboxamides and hydroxyalkylidenecyanoacetamides, pharmaceuticals containing these compounds and their useIsoxazole-4-carboxamide derivatives and hydroxyalkylidene-cyanoacetamide derivatives are suitable for the treatment of carcinoses. These compounds can be prepared by known processes. Some of the compounds are novel and are additionally suitable for the treatment of rheumatic disorders.Type: GrantFiled: June 7, 1995Date of Patent: July 2, 1996Assignee: Hoechst AktiengesellschaftInventors: Robert R. Bartlett, Friedrich-Johannes Kammerer
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Patent number: 5530117Abstract: The disclosure is drawn to novel 7-substituted-9-(substituted amino)-6-demethyl-6-deoxytetracycline compounds. These compounds are useful to treat infections caused by a wide spectrum of bacterial organisms, including those which are resistant to tetracycline.Type: GrantFiled: May 31, 1995Date of Patent: June 25, 1996Assignee: American Cyanamid CompanyInventors: Joseph J. Hlavka, Phaik-Eng Sum, Yakov Gluzman, Ving J. Lee, Adma A. Ross
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Patent number: 5516750Abstract: Substituted isoxazolines, process for their preparation, compositions containing them, and their use as safeners.Compounds of the formula (I) and salts thereof, ##STR1## in which R.sup.1 is carboxyl, formyl or another acyl radical or a derivative of the last-mentioned 3 groups,R.sup.2 is hydrogen, halogen, C.sub.1 -C.sub.18 -alkyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.2 -C.sub.8 -alkenyl, C.sub.2 -C.sub.8 -alkynyl, C.sub.1 -C.sub.18 -alkoxy, C.sub.2 -C.sub.8 -alkenyloxy, C.sub.2 -C.sub.8 -alkynyloxy, C.sub.1 -C.sub.18 -alkylthio, C.sub.2 -C.sub.8 -alkenylthio, each of the last-mentioned 9 radicals in each case being unsubstituted or substituted, or (C.sub.1 -C.sub.8 -alkoxy)carbonyl, andR.sup.3 and R.sup.Type: GrantFiled: September 14, 1994Date of Patent: May 14, 1996Assignee: Hoechst Schering AgrEvo GmbHInventors: Lothar Willms, Klaus Bauer, Hermann Bieringer
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Patent number: 5508450Abstract: Benzopyran derivatives which have an inhibitory effect on the Maillard reaction as well as an antioxidizing effect are described herein. These derivatives may be utilized in the treatment and/or prevention of diabetic complications such as, for example, coronary heart disease, peripheral circulatory insufficiency or failure, cerebrovascular hindrance, neurogenous diabetes, nephropathy, arteriosclerosis, arthrosclerosis, cataracts and retinopathy. Further, the derivatives may also be used in the treatment and/or prevention of diseases induced by aging and in the treatment and/or prevention of diseases caused by the formation of peroxidized fat.Type: GrantFiled: September 30, 1994Date of Patent: April 16, 1996Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Shuichi Ohuchida, Masaaki Toda, Tsumoru Miyamoto
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Patent number: 5506237Abstract: The invention relates to the compounds of formula (I): ##STR1## in which: A represents, with the carbon and nitrogen atoms to which it is attached, a heterocycle,B represents, with the nitrogen atom to which it is attached, a heterocycle,n is equal to 1, 2, 3 or 4,R represents phenyl substituted by at least one halogen or alkyl, hydroxyl, alkoxy, trifluoromethyl, nitro, amino, cyano, carboxyl or alkoxycarbonyl, benzyl, thienyl or pyridyl. The compounds may be used as medicaments.Type: GrantFiled: March 23, 1994Date of Patent: April 9, 1996Assignee: Adir et CompagnieInventors: Guillaume De Nanteuil, Bernard Protevin, Georges Remond, Jean Lepagnol, Veronique Heidet
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Patent number: 5506249Abstract: A compound selected from the group consisting of a compound of the formula ##STR1## wherein R.sub.1 is hydrogen or alkyl of 1 to 3 carbon atoms; R.sub.2 is cycloalkyl of 3 to 6 carbon atoms; R.sub.4 is selected from the group consisting of halogen, nitrile, nitro, --SCH.sub.3, -alkylcarbonyl of 1 to 6 carbon atoms, cycloalkylcarbonyl of 3 to 6 carbon atoms, --CX.sub.3, 'WCX.sub.3, --(CH.sub.2).sub.n CX.sub.3, --(CX.sub.2).sub.n CX.sub.3, --W(CX.sub.2).sub.n CX.sub.3 and a --W(CH.sub.2).sub.n CX.sub.3, in which X is halogen, W is oxygen or sulfur, and n is 1, 2 or 3; and R.sub.5 is selected from the group consisting of hydrogen, alkyl of 1 to 3 carbon atoms and cycloalkyl of 3 to 6 carbon atoms; with the proviso that if R.sub.5 is hydrogen, R.sub.4 is not --SCH.sub.3 or --CF.sub.3 and their non-toxic pharmaceutically acceptable salts having anti-prolifera-tive, anti-inflammatory and anti-tumor activity.Type: GrantFiled: December 5, 1994Date of Patent: April 9, 1996Assignee: Roussel UCLAFInventors: Elizabeth A. Kuo, Robert Westwood
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Patent number: 5498619Abstract: Aminoketone derivative compounds containing a heterocyclic ring bonded to an aminoketone moiety and useful as effective ingredients of centrally acting muscle relaxants and pollakiurea curing agents.(+)3-phenyl-5-[2-(1-pyrrolidinylmethyl)butyryl]isoxazole, which has a more remarkable central muscle relaxant action as compared with its racemic modification, can be effectively separated from the racemic modification using optically active 10-camphorsulfonic acid as the agent for the optical resolution.Type: GrantFiled: May 16, 1994Date of Patent: March 12, 1996Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Hideki Tanada, Kazuya Sakai, Seitaro Kajiya, Norio Ohto, Kazutoshi Horikomi, Akira Matsubara, Hideshi Shimizu, Akira Mizuchi
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Patent number: 5494911Abstract: Isoxazole-4-carboxamide derivatives and hydroxyalkylidene-cyanoacetamide derivatives are suitable for the treatment of carcinoses. These compounds can be prepared by known processes. Some of the compounds are novel and are additionally suitable for the treatment of rheumatic disorders.Type: GrantFiled: November 16, 1992Date of Patent: February 27, 1996Assignee: Hoechst AktiengesellschaftInventors: Robert R. Bartlett, Friedrich-Johannes Kammerer
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Patent number: 5495023Abstract: A new nitro compound of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are each lower alkyl or lower alkoxy(lower)alkyl, or ##STR2## is cyclized to form ##STR3## X is --O--, --S-- or --NH--, m is an integer 0 or 1, andR.sup.3 is carbamoyl, lower alkylcarbamoyl, lower alkanoyl, di-lower alkylaminosulfonyl, lower alkylsulfonyl, oxamoyl or a group of the formula: --(Y).sub.n --R.sup.4whereinY is --CO--, --SO.sub.2 --, --COCH.sub.2 -- or ##STR4## n is an integer of 0 or 1, and R.sup.4 is heterocyclic group which is optionally substituted with one or more substituents selected from lower alkyl, lower alkoxy, phenyl, carbamoyl, halogen, amino, lower alkylthio, hydroxy, lower alkylsulfonylamino and carbamoylmethyl, and pharmaceutically acceptable salt thereof, which are useful as vasodilators.Type: GrantFiled: May 3, 1994Date of Patent: February 27, 1996Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Masayuki Kato, Shigetaka Nishino, Mitsuko Hamano, Hisashi Takasugi
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Patent number: 5489570Abstract: The invention relates to isoxazole derivatives of formula (I): ##STR1## wherein: Ar represents phenyl optionally substituted by from one to three groups and wherein two substituents on adjacent positions of the phenyl ring, together with the two atoms to which they are attached, form a 5- to 7-membered ring which is optionally substituted;R represents the hydrogen atom or a group --CO.sub.2 R.sup.3 ;R.sup.1 represents alkyl, haloalkyl or optionally substituted cycloalkyl;R.sup.3 represents alkyl, alkenyl or alkynyl containing up to six carbon atoms which is optionally substituted by one or more halogen atoms;and their use as herbicides.Type: GrantFiled: July 29, 1994Date of Patent: February 6, 1996Assignee: Rhone-Poulenc Agriculture LimitedInventors: Neil Geach, David W. Hawkins, Christopher J. Pearson, Philip H. G. Smith, Nicolas White
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Patent number: 5488061Abstract: Novel 1-alkyl-, 1-alkenyl-, and 1-alkynylaryl-2-amino-1,3-propanediols, intermediates and processes for the preparation thereof, and methods of reducing inflammation and cell proliferation, and relieving memory dysfunction, and inhibiting bacterial and fungal growth are disclosed.Type: GrantFiled: May 23, 1994Date of Patent: January 30, 1996Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventors: John J. Tegeler, Barbara S. Rauckman, Russell R. L. Harmer, Brian S. Freed, Gregory H. Merriman
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Patent number: 5484780Abstract: This invention provides novel phenyl and heterocyclic derivatives, their pharmaceutical formulations and their methods of use for antagonizing angiotensin II receptors in mammals.Type: GrantFiled: December 14, 1994Date of Patent: January 16, 1996Assignee: Eli Lilly and CompanyInventors: Donald B. Boyd, Kenneth L. Hauser, Sherryl L. Lifer, Winston S. Marshall, Alan D. Palkowitz, William Pfeifer, Jon K. Reel, Richard L. Simon, Mitchell I. Steinberg, Kumiko Takeuchi, K. Jeff Thrasher, Celia A. Whitesitt
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Patent number: 5480857Abstract: 4-heteroaroylisoxazole derivatives of formula I: ##STR1## wherein: Ar represents an optionally substituted group Het, wherein Het represents a first heterocyclic ring containing from one to four heteroatoms in the ring selected from oxygen, nitrogen and sulphur, which is optionally fused with a benzene, or carbocyclic or second heterocyclic ring (which is optionally saturated or partially saturated) to form a bicyclic system, wherein the first heterocyclic ring of the group Het is attached to the carbonyl group in the 4-position of the isoxazole ring;R represents hydrogen or --CO.sub.2 R.sup.3 ;R.sup.1 represents alkyl or haloalkyl or a cycloalkyl group optionally substituted by one or more groups R.sup.4 ;R.sup.3 and R.sup.4 independently represent alkyl or haloalkyl;agriculturally acceptable salts thereof and their use in weed control is described.Type: GrantFiled: September 17, 1993Date of Patent: January 2, 1996Assignee: Rhone-Poulenc Agriculture LimitedInventors: Susan M. Cramp, Philip H. G. Smith
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Patent number: 5478856Abstract: A styrene derivative represented by the formula (1) or a salt thereof: ##STR1##Type: GrantFiled: June 27, 1994Date of Patent: December 26, 1995Assignee: Taiho Pharmaceutical Co., Ltd.Inventors: Masahiro Suzuki, Kenzi Nozaki, Toshiyuki Hosoya, Takashi Suzuki, Yuzi Basaki, Mitiyo Kozima, Naosuke Matsuura
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Patent number: 5476866Abstract: A compound selected from the group consisting of a compound of the formula ##STR1## wherein R.sub.1 is hydrogen or alkyl of 1 to 3 carbon atoms; R.sub.2 is cycloalkyl of 3 to 6 carbon atoms; R.sub.4 is selected from the group consisting of halogen, nitrile, nitro, --SCH.sub.3, -alkylcarbonyl of 1 to 6 carbon atoms, cycloalkylcarbonyl of 3 to 6 carbon atoms, --CX.sub.3, --WCX.sub.3, --(CH.sub.2).sub.n CX.sub.3, --(CX.sub.2).sub.n CX.sub.3, --W(CX.sub.2).sub.n CX.sub.3 and a --W(CH.sub.2).sub.n CX.sub.3, in which X is halogen, W is oxygen or sulfur, and n is 1, 2 or 3; and R.sub.5 is selected from the group consisting of hydrogen, alkyl of 1 to 3 carbon atoms and cycloalkyl of 3 to 6 carbon atoms; with the proviso that if R.sub.5 is hydrogen, R.sub.4 is not --SCH.sub.3 or --CF.sub.3 and their non-toxic pharmaceutically acceptable salts having anti-prolifera-tive, anti-inflammatory and anti-tumor activity.Type: GrantFiled: August 22, 1994Date of Patent: December 19, 1995Assignee: Roussel UclafInventors: Elizabeth A. Kuo, Robert Westwood
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Patent number: 5473069Abstract: The preparation of isoxazole-4,5-dicarboxylic diester of the formula I ##STR1## where R.sup.1 is any organic radical which is inert under the reaction conditions, and R.sup.2 and R.sup.3 are each alkyl, cycloalkyl or benzyl, entails reacting an aldoxime of the formula II ##STR2## with a diester of maleic or fumaric acid, of the formula IIIR.sup.2 OOC--C.dbd.C--COOR.sup.3 (III)where R.sup.2 and R.sup.3 are identical or different and have the abovementioned meanings, in the presence of an aqueous solution of a hypohalite which is present in excess relative to II.Type: GrantFiled: March 11, 1991Date of Patent: December 5, 1995Assignee: BASF AktiengesellschaftInventors: Thomas Kuekenhoehner, Volker Maywald
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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: 5459163Abstract: A pharmaceutical composition for use in the treatment of chronic Graft-versus-host diseases as well as autoimmune diseases, in particular for the treatment of systemic lupus erythematosus containing as an active ingredient at least one compound of the formulae 1 or 2 ##STR1## the latter being present per se or in the form of a physiologically tolerable salt.The invention also relates to a dosage unit form of said pharmaceutical composition and a method of treating chronic Graft-versus host diseases as well as autoimmune diseases, in particular systemic lupus erythematosus.Type: GrantFiled: September 13, 1993Date of Patent: October 17, 1995Assignee: Hoechst AktiengesellschaftInventors: Robert R. Bartlett, Rudolph Schleyerbach, Friedrich-Johannes Kammerer
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Patent number: 5399544Abstract: Isoxazole- and isothiazole-5-carboxamides of the formula ##STR1## where X is oxygen or sulfur, R.sup.1 is hydrogen, substituted or unsubstituted alkyl, cycloalkyl, cycloalkenyl, alkenyl (may be epoxidized at the double bond), alkynyl, alkoxy, a heterocyclic radical or phenyl, R.sup.2 is a derivative carboxylic acid function and R.sup.3 and R.sup.4 have the meanings given in the disclosure, and herbicidal agents containing compounds I.Type: GrantFiled: September 14, 1993Date of Patent: March 21, 1995Assignee: BASF AktiengesellschaftInventors: Volker Maywald, Peter Muenster, Hartmann Koenig, Gerhard Hamprecht, Thomas Kuekenhoehner, Wolfgang Rohr, Helmut Walter, Karl-Otto Westphalen, Matthias Gerber
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Patent number: 5399577Abstract: An isoxazole derivative represented by the general formula (1) or a salt thereof: ##STR1## a method for preparing the same; compositions for inhibiting lipoxygenase and cyclooxygenase comprising an effective amount of the derivative and a pharmaceutically acceptable carrier therefor; and a method for inhibiting lipoxygenase and cyclooxygenase which comprises administering to a patient the derivative.Type: GrantFiled: November 1, 1993Date of Patent: March 21, 1995Assignee: Taiho Pharmaceutical Co., Ltd.Inventors: Takashi Shindo, Naosuke Matsuura, Naohiko Ono, Yushiro Akizawa, Kenji Nozaki, Masahiro Suzuki
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Patent number: 5374606Abstract: The invention relates to 4-benzoylisoxazole derivatives of formula (I): ##STR1## wherein: R represents the hydrogen atom or a group --CO.sub.2 R.sup.4 ;R.sup.1 represents alkyl, haloalkyl or optionally substituted cycloalkyl;R.sup.2 represents halogen, optionally halogenated alkyl, alkenyl or alkynyl, alkyl substituted by one or more groups --OR.sup.5 ; or a group selected from nitro, cyano, --CO.sub.2 R.sup.5, --S(O).sub.p R.sup.6, --O(CH.sub.2).sub.m OR.sup.5, --COR.sup.5, --NR.sup.61 R.sup.62, --N(R.sup.8)SO.sub.2 R.sup.7, --OR.sup.5, --OSO.sub.2 R.sup.7 and --(CR.sup.9 R.sup.10).sub.t --S(O).sub.q R.sup.7 ;R.sup.3 represents --S(O).sub.q R.sup.7 ;X represents --(CR.sup.9 R.sup.10).sub.t --;n represents zero or an integer from one to four;R.sup.4 represents alkyl or haloalkyl;R.sup.5 represents optionally halogenated alkyl, alkenyl or alkynyl;R.sup.6, R.sup.61 and R.sup.62, which may be the same or different, each represents alkyl, haloalkyl or optionally substituted phenyl;R.sup.Type: GrantFiled: February 3, 1994Date of Patent: December 20, 1994Assignee: Rhone-Poulenc Agriculture LimitedInventors: Susan M. Cramp, Claude Lambert, Gillian M. Little, John Morris
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Patent number: 5374605Abstract: The invention relates to isoxazolecarboxylic acid derivatives of the general formula (I) ##STR1## in which A represents alkanediyl,Q represents oxygen, sulphur, imino (NH) or alkylimino (N-alkyl),R.sup.1 represents an in each case optionally substituted radical from the series comprising alkyl, cycloalkyl or phenyl,R.sup.2 represents hydrogen, halogen or optionally substituted alkyl, andR.sup.3 represents in each case optionally substituted cyclohexyl or phenyl,with the exception of the compounds: N-benzyl-5-cyclopropyl-isoxazole-3-carboxamide N-(2-phenyl-ethyl)-5-methyl-isoxazole-3-carboxamide and N-benzyl-5-methyl-isoxazole-3-carboxamide, a process for their preparation, and their use as herbicides.Type: GrantFiled: January 8, 1993Date of Patent: December 20, 1994Assignee: Bayer AktiengesellschaftInventors: Werner Hallenbach, Hans-Joachim Santel, Klaus Lurssen, Robert R. Schmidt
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Patent number: 5371063Abstract: The invention relates to 4-benzoylisoxazole derivatives of formula (I): ##STR1## wherein R represents hydrogen or --CO.sub.2 R.sup.4 ; R.sup.1 represents alkyl, haloalkyl or optionally substituted cycloalkyl;R.sup.2 represents halogen, alkyl, haloalkyl, alkyl substituted by one or more groups --OR.sup.5 ; ora group selected from nitro, cyano, --CO.sub.2 R.sup.5, --S(O).sub.p R.sup.6, --O(CH.sub.2).sub.m OR.sup.5, --COR.sup.5, --OR.sup.5 and --N(R.sup.8)SO.sub.2 R.sup.7 ;R.sup.3 represents --SO.sub.2 R.sup.7 ;X represents the oxygen atom;n represents zero or an integer from one to four;R.sup.4 represents alkyl or haloalkyl;R.sup.5 and R.sup.6, independently represent alkyl, haloalkyl or optionally substituted phenyl;R.sup.7 represents alkyl, haloalkyl, optionally substituted phenyl or --NR.sup.5 R.sup.6 ;R.sup.8 represents hydrogen, optionally halogenated alkyl, alkenyl or alkynyl; cycloalkyl, optionally substituted phenyl, --SO.sub.2 R.sup.6 or --OR.sup.Type: GrantFiled: February 3, 1994Date of Patent: December 6, 1994Assignee: Rhone-Poulenc Agriculture LimitedInventors: Susan M. Cramp, Tibor Musil, Simon N. Pettit, Philip H. G. Smith
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Patent number: 5371064Abstract: 4-Benzoylisoxazole derivatives of formula (I): ##STR1## wherein: R represents hydrogen or --CO.sub.2 R.sup.4 ;R.sup.1 represents alkyl, haloalkyl or optionally substituted cycloalkyl;R.sup.2 represents halogen, alkyl, haloalkyl or alkyl substituted by --OR.sup.5, or a group selected from nitro, cyano, --CO.sub.2 R.sup.4, --S(O).sub.p R.sup.6, --O(CH.sub.2).sub.r OR.sup.5 and --OR.sup.5 ;R.sup.3 represents optionally substituted phenyl;X represents oxygen or --S(O)--.sub.q ;n represents zero or an integer from one to four;R.sup.4 and R.sup.5 independently represent alkyl or haloalkyl;R.sup.6 represents alkyl, haloalkyl or optionally substituted phenyl;R.sup.7 represents halogen, alkyl or haloalkyl or a group selected from nitro, cyano, --OR.sup.5 and --S(O).sub.p R.sup.6 ;p represents 0, 1 or 2; q represents 0, 1 or 2;r represents 1, 2 or 3;the herbicidal properties of these derivatives and their application to crop protection are described.Type: GrantFiled: July 22, 1993Date of Patent: December 6, 1994Assignee: Rhone-Poulenc Agriculture Ltd.Inventors: Susan M. Cramp, Claude Lambert, John Morris
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Patent number: 5371099Abstract: A compound selected from the group consisting of a compound of the formula ##STR1## wherein R.sub.1 is hydrogen or alkyl of 1 to 3 carbon atoms, R.sub.2 is alkyl of 1 to 3 carbon atoms or cycloalkyl of 3 to 6 carbon atoms, R.sub.3 is --COOR.sub.6, R.sub.6 is hydrogen or alkyl of 1 to 3 carbon atoms, R.sub.4 is selected from the group consisting of halogen, --CN, --NO.sub.2, --SCH.sub.3, alkylcarbonyl of 1 to 6 alkyl carbon atoms, --CX.sub.3, --WCX.sub.3, --(CH.sub.2).sub.n --CX.sub.3, --(CX.sub.2).sub.n --CX.sub.3, --W--(CX.sub.2).sub.n --CX.sub.3, and --W--(CH.sub.2).sub.n --CX.sub.3, X is halogen, W is --O-- or --S--, n is 1, 2 or 3, R.sub.5 is selected from the group consisting of hydrogen, alkyl of 1 to 3 carbon atoms and cycloalkyl of 3 to 6 carbon atoms and their salts with non-toxic pharmaceutically acceptable bases with the proviso that if R.sub.2 is alkyl of 1 to 3 carbon atoms, R.sub.1 is hydrogen and R.sub.4 is selected from the group consisting of halogen, --CX.sub.3, --(CH.sub.2).sub.n --CX.sub.Type: GrantFiled: April 28, 1993Date of Patent: December 6, 1994Assignee: Roussel-UclafInventors: Robert R. Bartlett, Matharu S. Singh, Elizabeth A. Kuo, Rudolf Schleyerbach, Robert Westwood
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Patent number: 5366957Abstract: 5-Aryl isoxazole derivatives of formula (I): ##STR1## wherein: Ar represents phenyl optionally substituted substituted by one or more groups R.sup.2 ;R represents hydrogen, --CO.sub.2 R.sup.3, --COR.sup.4, cyano, halogen, alkyl or haloalkyl;R.sup.1 represents alkyl, haloalkyl or cycloalkyl;R.sup.2 represents a halogen atom, R.sup.4, nitro, --CO.sub.2 R.sup.3, --OR.sup.4, --S(O).sub.m R.sup.4, --S(O).sub.m R.sup.5, --O--(CH.sub.2).sub.p --OR.sup.4 or an alkyl group substituted by --OR.sup.4 ;R.sup.3 and R.sup.4, which may be the same or different, each represent alkyl or haloalkyl;R.sup.5 represents optionally substituted phenyl;p represents an integer from 1 to 3; andm represents zero, 1 or 2;the herbicidal properties of these derivatives and their application to crop protection is described.Type: GrantFiled: July 17, 1992Date of Patent: November 22, 1994Assignee: Rhone-Poulenc Argriculture LtdInventors: Paul A. Cain, Susan M. Cramp, Claude Lambert
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Patent number: 5338857Abstract: Aminoketone derivative compounds containing a heterocyclic ring bonded to an aminoketone moiety and useful as effective ingredients of centrally acting muscle relaxants and pollakiurea curing agents.(+)3-phenyl-5-[2-(1-pyrrolidinylmethyl)butyryl]isoxazole, which has a more remarkable central muscle relaxant action as compared with its racemic modification, can be effectively separated from the racemic modification using optically active 10-camphorsulfonic acid as the agent for the optical resolution.Type: GrantFiled: February 24, 1992Date of Patent: August 16, 1994Assignee: Mitsui Toatsu Chemicals IncorporatedInventors: Norio Ohto, Kazutoshi Horikomi, Akira Matsubara, Hideki Tanada, Kazuya Sakai, Seitaro Kajiya, Akira Mizuchi, Hideshi Shimizu
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Patent number: 5331011Abstract: Disclosed is an N-benzyl-N-phenoxyethylamine selected from the group consisting of the N-benzyl-N-phenoxyethylamine represented by the following formula (I): ##STR1## and an agriculturally acceptable acid addition salt represented by the following formula (II): ##STR2## wherein m represents a number of 1 or 2 with a proviso that when m is 1 and a chlorine atom in the ring A is present at para(4)-position of the ring A, two chlorine atoms in the ring B are present at 2,3-, 2,5-, 2,6-, 3,4- or 3,5-positions of the ring B, and HX represents an acid.Type: GrantFiled: April 7, 1993Date of Patent: July 19, 1994Assignee: Mitsubishi Gas Chemical Co., Inc.Inventors: Mitsunori Oda, Kazutoshi Kikkawa, Akinori Tanaka, Satoko Imaruoka, Shigeo Yoshinaka
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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: 5312831Abstract: The invention relates to novel ureas and urethanes of Formula I: ##STR1## which stimulate cytokine production and may be used to accelerate recovery from neutropenia accompanying radio- or chemotherapy, bone marrow transplantation, or infections. Compounds in the invention or pharmaceutical compositions employing these compounds may be useful in the treatment of cancer, AIDS, aplastic anemia, myelodysplastic syndrome, and infectious diseases, and in the enhancement of immune response.Type: GrantFiled: May 12, 1993Date of Patent: May 17, 1994Assignee: American Cyanamid CompanyInventors: Semiramis Ayral-Kaloustian, Steven R. Schow, Mila T. Du, James J. Gibbons, Jr.
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Patent number: 5278316Abstract: Novel unnatural dipeptoids of .alpha.-substituted Trp-Phe derivatives useful as agents in the treatment of obesity, hypersecretion of gastric acid in the gut, gastrin-dependent tumors, or as antipsychotics are disclosed. Further the compounds are antianxiety agents, antiulcer agents, antidepressant agents, and are agents useful for preventing the withdrawal response produced by chronic treatment or use followed by chronic treatment followed by withdrawal from nicotine, diazepam, alcohol, cocaine, caffeine, or opiods. Also disclosed are pharmaceutical compositions and methods of treatment using the dipeptoids as well as processes for preparing them and novel intermediates useful in their preparation. An additional feature of the invention is the use of the subject compounds to prepare pharmaceutical and diagnostic compositions.Type: GrantFiled: December 19, 1990Date of Patent: January 11, 1994Assignee: Warner-Lambert CompanyInventors: David C. Horwell, Martyn C. Pritchard, Reginald S. Richardson, Edward Roberts, Julian Aranda
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Patent number: 5276160Abstract: Abstract of the Disclosure: 3-Carbamoylisoxazole-4-carboxylic esters of the formula I ##STR1## where R.sup.1 is hydrogen, alkyl, cycloalkyl, phenyl or a 5- to 6-membered heterocyclic radical, it being possible for the organic radicals to carry substituents which are inert under the reaction conditions;R.sup.2 is alkyl, cycloalkyl, benzyl or C.sub.1 -C.sub.3 -alkenyl;R.sup.3 is hydrogen, alkyl or cycloalkyl andR.sup.4 is an aliphatic or cycloaliphatic radical or unsubstituted or substituted phenyl, or R.sup.4 together with R.sup.3 is a 4- to 7-membered alkylene chain which can be interrupted by oxygen, sulfur or N-methyl, are prepared by selective amidation of an isoxazole-3,4-dicarboxylic diester of the formula II ##STR2## where R.sup.2 has the meanings of R.sup.2 and is identical to or different from R.sup.2.Type: GrantFiled: March 23, 1993Date of Patent: January 4, 1994Assignee: BASF AktiengesellschaftInventors: Volker Maywald, Thomas Kuekenhoehner, Gerhard Hamprecht
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Patent number: 5273989Abstract: Novel 3,5-disubstituted 2-isoxazolines and isoxazoles and novel pharmaceuticals are described which are suitable, in particular, for the prophylaxis and/or treatment of pathological, neurodegenerative disorders in humans and animals. Processes for the preparation of these 3,5-disubstituted 2-isoxazolines and isoxazolines and isoxazoles are additionally indicated.Type: GrantFiled: April 10, 1991Date of Patent: December 28, 1993Assignee: Hoechst AktiengesellschaftInventors: Wilfried Schwab, Hiristo Anagnostopulos, Elena Porsche-Wiebking, John Grome
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Patent number: 5264580Abstract: A process for preparing isoxazole-3,4-dicarboxylic acid derivatives of the formula I ##STR1## where R.sup.1 is hydrogen, alkyl, cycloalkyl or phenyl, or a 5- to 6-membered heterocyclic radical, and the organic radicals can have substituents which are inert under the reaction conditions;R.sup.2 is hydrogen, alkyl, cycloalkyl, benzyl or C.sub.3 -C.sub.6 -alkenyl;A is NR.sup.3 R.sup.4 where R.sup.3 is hydrogen or an aliphatic or cycloaliphatic radical and R.sup.4 is an aliphatic or cycloaliphatic radical or unsubstituted or substituted phenyl, or R.sup.3 forms together with R.sup.4 a 4- to 7-membered alkylene chain which can be interrupted by oxygen, sulfur or N-methyl, or is OR.sup.5 where R.sup.5 is alkyl, cycloalkyl, benzyl or alkenyl;by deprotonation of a CH-acid compound of the formula II ##STR2## using a base and reacting with hydroximyl chlorides of the formula III ##STR3## wherein a magnesium alcoholate of the formula IVMg(OR.sup.6 ).sub.2 IVwhere R.sup.Type: GrantFiled: March 23, 1993Date of Patent: November 23, 1993Assignee: BASF AktiengesellschaftInventors: Volker Maywald, Thomas Kuekenhoehner, Peter Muenster, Stefan Stahl
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Patent number: 5258397Abstract: The object of the invention is heterocyclic compounds of general formula (I) endowed with anticonvulsant activity: ##STR1## in which Y is selected from --O--, --S-- and ##STR2## R.sub.4 being H or optionally substituted alkyl, acyl or benzyl, Z is selected from the groups --CO--N(R.sub.6)--,--NH--CO--CH.dbd.CH-- and --N(R.sub.6)--CO, R.sub.6 being H or alkyl;R.sub.1 is C.sub.1 -C.sub.4 alkyl; R.sub.2 is C.sub.1 -C.sub.4 alkyl or halogen; R.sub.3 represents optionally substituted C.sub.1 -C.sub.4 alkyl, alkoxy or hydroxyalkyl, or C.sub.2 -C.sub.7 alkanoyl.Type: GrantFiled: May 9, 1991Date of Patent: November 2, 1993Assignee: NovapharmeInventors: Francis Lepage, Bernard Hublot
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Patent number: 5256632Abstract: Herbicidal sulphonylated carboxamides of the formulaR.sup.1 --CO--NH--SO.sub.2 --(A).sub.n --R.sup.2 (I)in whichn represents the numbers 0 or 1,A represents oxygen, iminio (NH) or methylene (CH.sub.2),R.sup.1 represents a five-membered heteroaryl radical which contains 1 or 2 nitrogen atoms and additionally one oxygen or sulphur atom in the ring and which is optionally substituted by halogen or by alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino or phenyl which are in each case optionally substituted, andR.sup.2 represents aryl or heteroaryl which are in each case optionally substituted,or salts thereof, with the exclusion of the compound 2-dimethylamino-N-(4-methyl-phenylsulphonyl)-5-thiazole carboxamide.Type: GrantFiled: June 18, 1992Date of Patent: October 26, 1993Assignee: Bayer AktiengesellschaftInventors: Hilmar Wolf, Rolf Kirsten, Hans-Joachim Santel, Klaus Lurssen, Robert R. Schmidt
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Isoxazolylimidazole derivatives, process for their production and their use in pharmaceutical agents
Patent number: 5256682Abstract: 4-Isoxazolyl-imidazole derivatives of formula I ##STR1## in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the meanings indicated, as well as their production and use in pharmaceutical agents, are described.Type: GrantFiled: April 13, 1992Date of Patent: October 26, 1993Assignee: Schering AktiengesellschaftInventors: Martin Kruger, Rolf Russe, Herbert Schneider, Ralph Schmiechen, Lechoslaw Turski -
Patent number: 5250553Abstract: Methyl .alpha.-arylacrylates substituted by a heterocyclic radical and having the general formula ##STR1## where R is alkyl, alkenyl, haloalkyl, cycloalkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, halogen or aryl, the aromatic ring being unsubstituted or substituted, Het is a five-membered heteroaromatic ring which is unsubstituted or substituted and has from one to three heteroatoms, and A is ethenylene, ethylene, methyleneoxy or methylenethio, and fungicides and pesticides containing these compounds.Type: GrantFiled: July 30, 1992Date of Patent: October 5, 1993Assignee: BASF AktiengesellschaftInventors: Franz Schuetz, Hans-Juergen Neubauer, Thomas Kuekenhoehner, Ulrich Schirmer, Peter Hofmeister, Christoph Kuenast, Eberhard Ammermann, Gisela Lorenz, Uwe Kardorff
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Patent number: 5250501Abstract: A compound of formula (I): ##STR1## or a salt, enamine or the like, acylate, sulphonate, carbamate or ether derivative thereof; wherein X, X.sup.1 and X.sup.2 are independently oxygen or sulphur, R.sup.1 is an optionally substituted heterocyclic or cycloalkyl group, and Y is an optionally substituted C.sub.2 -C.sub.4 alkylene group which is optionally interposed by an oxygen atom, a group ##STR2## or an optionally mono-substituted nitrogen atom, wherein p is 0, 1 or 2, s is 0 or 1 and R.sup.b is alkyl or alkoxy; provided that when X, X.sup.1 and X.sup.2 are oxygen R.sup.1 is not pyridyl or pyrimidinyl. Processes for the preparation of these compounds and herbicidal compositions containing them are also described and claimed.Type: GrantFiled: January 10, 1992Date of Patent: October 5, 1993Assignees: Imperial Chemical Industries PLC, ICI Americas, Inc.Inventors: John E. D. Barton, David Cartwright, John M. Cox, Glynn Mitchell, Charles G. Carter, David L. Lee, Francis H. Walker, Frank X. Woolard
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Patent number: 5234937Abstract: The novel 3,5-di-tertiary-butyl-4-hydroxyphenyloxazolyl methanones and methanone oximes of the present invention are antiinflammatory agents having activity as inhibitors of 5-lipoxygenase, cyclooxygenase or both.Type: GrantFiled: October 17, 1991Date of Patent: August 10, 1993Assignee: Warner-Lambert CompanyInventors: Thomas Capiris, David T. Connor, Jagadish C. Sircar
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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: 5208251Abstract: The present invention is 3,5-substituted, isoxazoles, pyrazoles, isothiazoles, and analogs thereof having 5-lipoxygenase or cyclooxygenase inhibiting activity or as a sunscreen.Type: GrantFiled: August 16, 1989Date of Patent: May 4, 1993Assignee: Warner-Lambert CompanyInventors: Thomas R. Belliotti, David T. Connor, Daniel L. Flynn, Catherine R. Kostlan, Donald E. Nies
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Patent number: 5203907Abstract: Isoxazole- and isothiazole-5-carboxamides of the formula I ##STR1## where X is oxygen or sulfur, R.sup.1 is halogen, alkylthio, haloalkoxy, haloalkylthio, cyano, formyl, alkanoyl, alkoxycarbonyl, alkylaminocarbonyl, di-(C.sub.1 -C.sub.3)-alkylaminocarbonyl, cyclopropylaminocarbonyl, methylsulfonyl, trifluoromethylsulfonyl, unsubstituted or substituted phenoxy or phenylthio; R.sup.2 is formyl, haloformyl, 4,5-dihydro-2-oxazolyl, COOR.sup.5, COSR.sup.5 or CONR.sup.6 R.sup.7, and R.sup.3 to R.sup.7 have the meanings specified in the description, are suitable as herbicides.Type: GrantFiled: March 11, 1992Date of Patent: April 20, 1993Assignee: BASF AktiengesellschaftInventors: Volker Maywald, Peter Muenster, Hartmann Koenig, Gerhard Hamprecht, Thomas Kuekenhoehner, Helmut Walter, Karl-Otto Westphalen, Matthias Gerber
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Patent number: 5204482Abstract: Ethylenediamine monoamides of the formulaR--CO--NH--CH.sub.2 --CH.sub.2 --NH.sub.2 Iwherein R is one of groups ##STR1## in which R.sup.1 is phenyl, monohalophenyl, monolower-alkylphenyl, monolower-alkoxyphenyl, monotrifluoromethylphenyl, monocyanophenyl or monaryl-lower-alkoxyphenyl, dihalophenyl, furyl, thienyl or monohalothienyl, R.sup.2 is hydrogen, halogen or amino, R.sup.3, R.sup.5 and R.sup.7 each are phenyl, monohalophenyl, dihalophenyl, thienyl, furyl or monohalofuryl, R.sup.4 and R.sup.6 each are hydrogen or amino and R.sup.8 is hydrogen or lower-alkyl,as well as their pharmaceutically usable acid addition salts are disclosed. The compounds have monoamine oxidase inhibiting properties with low toxicity and are useful for the treatment of depressive states and cognitive disorders.Type: GrantFiled: February 4, 1991Date of Patent: April 20, 1993Assignee: Hoffman-LaRoche Inc.Inventors: Walter Gassner, Rene Imhof
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Patent number: 5204359Abstract: Insecticidally active nitro compounds of the formula ##STR1## wherein R.sup.1 is hydrogen, cyano or alkyl,R.sup.2 is hydrogen or an organic radical,R.sup.3 is ##STR2## R.sup.4 is an organic radical, R.sup.5 and R.sup.6 are hydrogen or organic radicals,Y is CH or N, andZ is an optionally substituted 5- or 6-membered heterocyclic group,with certain conditions and exceptions.Type: GrantFiled: September 11, 1991Date of Patent: April 20, 1993Assignee: Nihon Bayer Agrochem K.K.Inventors: Kozo Shiokawa, Shinichi Tsuboi, Koichi Moriya, Yumi Hattori, Ikuro Honda, Katsuhiko Shibuya
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Patent number: 5201932Abstract: Carboxamides Ia, Ib, Ic and Id ##STR1## (X=O, S; R.sup.1 =H, halogen, substituted or unsubstituted alkyl, substituted or unsubstituted benzyl, alkoxy, alkylthio, haloalkoxy, haloalkylthio, substituted or unsubstituted phenyl, substituted or unsubstituted phenoxy or phenylthio, a substituted or unsubstituted 5- or 6-membered heterocyclic radical containing one or two heteroatoms, cycloalkyl-substituted alkyl, substituted or unsubstituted alkenyl which may be epoxidized, substituted or unsubstituted alkynyl, substituted or unsubstituted cycloalkyl or cycloalkenyl; R.sup.1 '=cycloalkyl-substituted alkyl, substituted or unsubstituted alkenyl which may be epoxidized, substituted or unsubstituted cycloalkenyl; R.sup.2 =CHO, 4,5-dihydrooxazol-2-yl, COYR.sup.5, CONR.sup.6 R.sup.7 ; Y=O, S; R.sup.Type: GrantFiled: May 4, 1992Date of Patent: April 13, 1993Assignee: BASF AktiengesellschaftInventors: Volker Maywald, Wolfgang Freund, Gerhard Hamprecht, Thomas Kuekenhoehner, Peter Plath, Bruno Wuerzer, Karl-Otto Westphalen
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Patent number: 5194622Abstract: A process for the preparation of a compound of the formula ##STR1## wherein R.sub.1 and R.sub.2 are individually selected from the group consisting of hydrogen, halogen, --CF.sub.3, alkyl, alkoxy and alkylthio of 1 to 8 carbon atoms, alkenyl and alkynyl of 2 to 8 carbon atoms, --SO.sub.2 alk and alk is alkyl of 1 to 8 carbon atoms, optionally substituted aryl, aryloxy and arylthio of 6 to 18 carbon atoms and optionally substituted heteroaryl, heteroaryloxy and heterocyclic of 5 to 6 ring members, R.sub.3 is selected from the group consisting of alkyl of 1 to 8 carbon atoms, alkenyl and alkynyl of 2 to 8 carbon atoms, aryl of 6 to 18 carbon atoms and alkoxyalkoxyalkyl of 3 to 14 carbon atoms, X is selected from the group consisting of --O--, --S-- and --NR.sub.4 --, R.sub.4 is selected from the group consisting of hydrogen, alkyl, alkenyl and alkynyl of up to 8 carbon atoms, --SO.sub.2 alkyl, --SO.sub.2 alkenyl and --SO.sub.2 alkynyl of up to 8 carbon atoms and optionally substituted aryl and --SO.sub.Type: GrantFiled: November 18, 1991Date of Patent: March 16, 1993Assignee: Roussel UclafInventors: Jean-Louis Brayer, Jean-Pierre Demoute
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Patent number: 5194606Abstract: Novel aminoketones useful as central muscle relaxants and their preparation processes are disclosed. The disclosed processes are novel processes which do not use any heavy metal in view of the facts that their products are will be used as drugs and which require no complex purification step such as liberation of the aminoketones from their hydrochlorides or the like.Type: GrantFiled: July 23, 1991Date of Patent: March 16, 1993Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Akira Matsubara, Kazuya Sakai, Hideki Tanada, Hironori Komatsu
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Patent number: 5166153Abstract: Novel N-acylated 2-[4-(halophenoxy)-phenoxy]-ethylcarbamic acid esters of formula I ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.8 alkyl or C.sub.3 -C.sub.5 alkenyl,R.sub.2 is C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 alkoxy, --CO--R.sub.7 or --NR.sub.8 R.sub.9,R.sub.3 and R.sub.4 independently of one another are hydrogen or methyl,R.sub.5 is chlorine or fluorine,R.sub.6 is either the same substituent as R.sub.5 or is hydrogen,R.sub.7 is C.sub.1 -C.sub.8 alkoxy or --NR.sub.10 R.sub.11,R.sub.8 is C.sub.1 -C.sub.4 alkyl,R.sub.9 is C.sub.1 -C.sub.4 alkyl orR.sub.8 and R.sub.9 together form a C.sub.4 -C.sub.6 alkylene chain which may be interrupted by oxygen, sulfur or --NCH.sub.3 --,R.sub.10 is hydrogen or C.sub.1 -C.sub.4 alkyl andR.sub.11 is hydrogen or C.sub.1 -C.sub.4 alkyl, benzyl, phenyl, or phenyl substituted by halogen or by methyl, orR.sub.10 and R.sub.11 together form a C.sub.4 -C.sub.6 alkylene chain which may be interrupted by oxygen, sulfur or --NCH.sub.Type: GrantFiled: April 24, 1990Date of Patent: November 24, 1992Assignee: Ciba-Geigy CorporationInventor: Friedrich Karrer
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Patent number: 5151441Abstract: 3-Isoxazolylbenzyl esters of the general formulae Ia and Ib ##STR1## where R is halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.2 --C.sub.4 -alkenyl, C.sub.2 -C.sub.4 -haloalkenyl, C.sub.2 -C.sub.4 -alkynyl, C.sub.2 -C.sub.4 -haloalkynyl, unsubstituted or substituted phenylethenyl, C.sub.3 -C.sub.8 -cycloalkyl, aryl, hetaryl, CO.sub.2 R.sup.3 or CONR.sup.4 R.sup.5,R.sup.3, R.sup.4 and R.sup.5 are each hydrogen or C.sub.1 -C.sub.6 -alkyl,n is 0, 1 or 2, and the radicals R may be different when n is 2,R.sup.1 is halogen or C.sub.1 -C.sub.4 -alkyl,R.sup.2 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl, C.sub.2 -C.sub.4 -alkynyl or cyano andA is the carbonyl radical of an acid component usually found in pyrethroids, are contained in pesticides.Type: GrantFiled: May 14, 1991Date of Patent: September 29, 1992Assignee: BASF AktiengesellschaftInventors: Stefan Mueller, Hans Theobald, Bernd Wolf, Peter Hofmeister, Uwe Kardorff, Christoph Kuenast