Acyclic Nitrogen Bonded Directly To A -c(=x)- Group, Wherein X Is Chalcogen Patents (Class 544/393)
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Patent number: 5340810Abstract: The invention provides compounds of formula (I): ##STR1## or a physiologically acceptable salt or solvate thereof wherein R.sup.1 represents a hydrogen atom or a halogen atom or a group selected from C.sub.1-6 alkyl and C.sub.1-6 alkoxy;R.sup.2 represents a phenyl group substituted by a group selected from ##STR2## and optionally further substituted by one or two substituents selected from halogen atoms, C.sub.1-6 alkoxy, hydroxy, and C.sub.1-6 alkyl;R.sup.3 represents the group ##STR3## 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 and C.sub.1-6 alkyl;R.sup.6 represents a hydrogen atom or a group selected from --NR.sup.9 R.sup.10 and a C.sub.1-6 alkyl group optionally substituted by one or two substituents selected from C.sub.1-6 alkoxy, hydroxy, C.sub.1-6 acyloxy and --SO.sub.2 R.sup.11 ;R.sup.7, R.sup.8 and R.sup.Type: GrantFiled: September 17, 1992Date of Patent: August 23, 1994Assignee: Glaxo Group LimitedInventors: John W. Clitherow, Malcolm Carter
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Patent number: 5340812Abstract: Piperazine derivatives of formula ##STR1## and their pharmaceutically acceptable acid addition salts are disclosed. In the formula n is 1 or 2, R is hydrogen or lower alkyl, R.sup.1 is an aryl or nitrogen containing heteroaryl radical, R.sup.2 is hydrogen or lower alkyl, R.sup.3 is aryl, C.sub.4-8 alkyl or aryl(lower)alkyl, and X is a functionalised group of specified meaning. The compounds exhibit activity as 5-HT.sub.1A antagonists and can be used, inter alia, for the treatment of CNS disorders, such as anxiety.Type: GrantFiled: January 7, 1993Date of Patent: August 23, 1994Assignee: John Wyeth & Brother, LimitedInventor: Ian A. Cliffe
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Patent number: 5324728Abstract: A naphthoic acid derivative represented by the following general formula or a salt thereof: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a lower alkyl group, a lower alkoxy group, a lower alkanoyloxy group, a hydroxy-lower alkyl group, a lower alkoxy-lower alkyl group, a lower alkanoyloxy-lower alkyl group or an aralkyloxy group;R.sub.4 is a hydrogen atom or a lower alkyl group;R.sub.5 is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaromatic group;X is a group ##STR2## a cycloalkylene group, a bivalent nitrogen-containing heterocyclic group, or a group ##STR3## --R.sub.8 --NH-- or --NH--R.sub.8, where R.sub.6 and R.sub.7 are each a hydrogen atom or a lower alkyl group and R.sub.8 is a cycloalkylene group, or R.sub.6 and R.sub.7, together with R.sub.4, may form an alkylene group of 1-3 carbon atoms;Y is --S(O).sub.p --, --(CH.sub.2).sub.Type: GrantFiled: December 2, 1991Date of Patent: June 28, 1994Assignee: Fujirebio Inc.Inventors: Yasuo Sekine, Tetsuaki Yamaura, Masato Nishimura, Eri Kojima, Yasuko Emoto, Yasushi Higashide
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Patent number: 5292755Abstract: Benzoylguanidines of the formula I ##STR1## where R(1) or R(2) is equal to R(6)--S(O).sub.n -- or R(7)R(8)N--O.sub.2 S--and the other substituent R(1) or R(2) is in each case equal to H, F, Cl, Br, I, alkyl, alkoxy or phenoxy, R(6)--S(O).sub.n or R(7)R(8)N--and R(6) is equal to alkyl, cycloalkyl, cyclopentylmethyl, cyclohexylmethyl or phenyl,R(7) and R(8) are equal to alkyl or phenylalkyl or phenyl,and in which R(7) and R(8) may also together be a C.sub.4 --C.sub.7 chain, and in which R(7) and R(8), together with the nitrogen atom to which they are bonded, may be a dihydroindole, tetrahydroquinoline or tetrahydroisoquinoline system,and where R(3), R(4) and R(5) are equal to hydrogen or alkyl, or R(3) and R(4) are together an alkylene chain or R(4) and R(4) are together an alkylene chain,and where n is equal to zero, 1 or 2and their pharmaceutically tolerable salts are outstanding antiarrhythmics.Type: GrantFiled: January 31, 1992Date of Patent: March 8, 1994Assignee: Hoechst AktiengesellschaftInventors: Heinrich C. Englert, Hans-Jochen Lang, Wolfgang Linz, Bernward Scholkens, Wolfgang Scholz
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Patent number: 5283248Abstract: The present invention relates to novel substituted pyrimidobenzimidazole derivatives of the formula ##STR1## wherein the substituents are as described in the specification, and pharmaceutically acceptable salts thereof.The products have an inhibitory action on the DNA-gyrase activity in bacteria. They can accordingly be used for the prevention or control of bacterial infections.Type: GrantFiled: June 25, 1992Date of Patent: February 1, 1994Assignee: Hoffmann-La Roche Inc.Inventors: Christian Hubschwerlen, Ivan Kompis, Jean-Luc Specklin
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Patent number: 5246935Abstract: Piperazinyl derivatives of the general formula I ##STR1## wherein R.sup.1 represents substituted phenyl, 1- or 2-diazanaphthyl, azadiazanaphtyl or diazanaphtyl groups; n is 1, 2, 3 or 4; X is --O-- or ##STR2## wherein R.sup.2 is hydrogen, C.sub.1-6 -alkyl or C.sub.3-8 -cycloalkyl; Y is .dbd.O or .dbd.S or .dbd.NZ wherein Z is hydrogen, C.sub.1-6 -alkyl or --CN and R.sup.3 is selected from a group consisting of various structures have been found to exhibit high affinity for various receptor subtypes including the 5-HT.sub.2 receptor, the 5-HT.sub.1A receptor, the alpha.sub.1 receptor the dopamine receptor or a combination of these and may therefore be useful for treating CNS system, cardiovascular system and gastrointestinal disorders.Type: GrantFiled: August 13, 1991Date of Patent: September 21, 1993Assignee: Novo Nordisk A/SInventors: Lone Jeppesen, Marit Kristiansen, John B. Hansen
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Patent number: 5215989Abstract: Compounds of structural formula: ##STR1## wherein Ar is an aromatic ring, B is a cyclic moiety fused to Ar of 5-7 members, X and Y are bridging groups, Q is a nitrogen containing heterocycle, R.sup.2 and R.sup.3 are H, substituted or unsubtituted C.sub.1-3 alkyl, C.sub.1-3 alkoxy, N(R).sub.2, halogen, CF.sub.3 or R.sup.5 and R.sup.1 is H or an aryl group.Type: GrantFiled: July 15, 1991Date of Patent: June 1, 1993Assignee: Merck & Co., Inc.Inventors: John J. Baldwin, David A. Claremon, Jason M. Elliott, Gerald S. Ponticello, David C. Remy, Harold G. Selnick
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Patent number: 5166156Abstract: Compounds of formula I: ##STR1## in which: n=1-4,R represents hydrogen, halogen, alkyl, hydroxyl or alkoxy, R.sub.1 represents a radical --NHCOR2 (A.sub.1); (in which R.sub.2 represents alkyl, cycloalkyl, phenyl optionally substituted, -O-alkyl, 3-pyridyl, 2-pyrrolyl, quinolyl, 1-isoquinolyl, 2-thienyl or 3-indolyl); a radical of -NHSO2R3 (A.sub.2) (in which R.sub.3 represents alkyl, cycloalkyl or phenyl optionally substituted); a radical --NHCONHR4 (A.sub.3) (in which R.sub.4 represents alkyl or phenyl-optionally substituted); a phthalimido radical (A.sub.4); an o-sulfobenzoic imido radical (A.sub.5); a di(benzoyl)amino radical (A.sub.6) optionally substituted; a radical of formula A.sub.7 : ##STR2## (in which R.sub.5 represents carbamoyl, cyano, carboxy or alkoxycarbonyl); or a radical of formula A.sub.8 : ##STR3## their stereoisomers and their addition salts with a pharmaceutically-acceptable inorganic or organic acid, are disolosed to be useful as 5-HT.sub.Type: GrantFiled: August 29, 1991Date of Patent: November 24, 1992Assignee: Adir et CompagnieInventors: Gilbert Lavielle, Michel Laubie, Francis Colpaert
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Patent number: 5166157Abstract: Compounds of formula I: ##STR1## in which: N=1-4,R represents hydrogen, halogen, alkyl, hydroxyl or alkoxy, R.sub.1 represents a radical -NHCOR2 (A.sub.1); (in which R.sub.2 represents alkyl, cycloalkyl, phenyl, optionally substituted-, -O-alkyl, 3-pyridyl, 2-pyrrolyl, quinolyl, 1-isoquinolyl, 2-thienyl or 3-indolyl); a radical of --NHSO2R3 (A.sub.2) (in which R.sub.3 represents alkyl, cycloalkyl or phenyl optionally substituted); a radical --NHCONHR4 (A.sub.3) (in which R.sub.4 represents alkyl or phenyl-optionally substituted); a phthalimido radical (A.sub.4); an o-sulfobenzoic imido radical (A.sub.5); a di(benzoyl)amino radical (A.sub.6) optionally substituted; a radical of formula A.sub.7 : ##STR2## (in which R.sub.5 represents carbamoyl, cyano, carboxy or alkoxycarbonyl); or a radical of formula A.sub.8 : ##STR3## their stereoisomers and their addition salts with a pharmaceutically-acceptable inorganic or organic acid, are disclosed to be useful as 5-HT.sub.Type: GrantFiled: August 27, 1991Date of Patent: November 24, 1992Assignee: Adir et CompagnieInventors: Gilbert Lavielle, Michel Laubie, Francis Colpaert
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Patent number: 5162321Abstract: Compounds of formula I: ##STR1## in which: n=1-4;R represents hydrogen, halogen, alkyl, hydroxyl or alkoxy, R.sub.1 represents a radical --NHCOR2 (A.sub.1); (in which R.sub.2 represents alkyl, cycloalkyl, phenyl optionally substituted-, --O-alkyl, 3-pyridyl, 2-pyrrolyl, quinolyl, 1-isoquinolyl, 2-thienyl or 3-indolyl); a radical of --NHSO2R3 (A.sub.2) (in which R.sub.3 represents alkyl, cycloalkyl or phenyl optionally substituted); a radical --NHCONHR4 (A.sub.3) (in which R.sub.4 represents alkyl or phenyl-optionally substituted); a phthalimido radical (A.sub.4); an o-sulfobenzoic imido radical (A.sub.5); a di(benzoyl)amino radical (A.sub.6) optionally substituted; a radical of formula A.sub.7 : ##STR2## (in which R.sub.5 represents carbamoyl, cyano, carboxy or alkoxycarbonyl); or a radical of formula A.sub.8 : ##STR3## their stereoisomers and their addition salts with a pharamaceutically-acceptable inorganic or organic acid, are disclosed to be useful as 5-HT.sub.Type: GrantFiled: August 29, 1991Date of Patent: November 10, 1992Assignee: Adir et CompagnieInventors: Gilbert Lavielle, Michel Laubie, Francis Colpaert
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Patent number: 5162324Abstract: Compounds of formula I: ##STR1## in which: n=1-4,R represents hydrogen, halogen, alkyl, hydroxyl or alkoxy, R.sub.1 represents a radical --NHCOR2 (A.sub.1); (in which R.sub.2 represents alkyl, cycloalkyl, phenyl optionally substituted-, -O-alkyl, 3-pyridyl, 2-pyrrolyl, quinolyl, 1-isoquinolyl, 2-thienyl or 3-indolyl); a radical of --NHSO2R3 (A.sub.2) (in which R.sub.3 represents alkyl, cycloalkyl or phenyl optionally substituted); a radical --NHCONHR4 (A.sub.3) (in which R.sub.4 represents alkyl or phenyl-optionally substituted); a phthalimido radical (A.sub.4); an o-sulfobenzoic imido radical (A.sub.5); a di(benzoyl)amino radical (A.sub.6) optionally substituted; a radical of formula A.sub.7 : ##STR2## (in which R.sub.5 represents carbamoyl, cyano, carboxy or alkoxycarbonyl); or a radical of formula A.sub.8 : ##STR3## their stereoisomers and their addition salts with a pharmaceutically-acceptable inorganic or organic acid, are disclosed to be useful as 5-HT.sub.Type: GrantFiled: August 29, 1991Date of Patent: November 10, 1992Assignee: Adir et CompagnieInventors: Gilbert Lavielle, Michel Laubie, Francis Colpaert
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Patent number: 5143916Abstract: Compounds of the formula I: ##STR1## in which: n=1-4,R represents hydrogen, halogen, alkyl, hydroxyl or alkoxy, R.sub.1 represents a radical --NHCOR2 (A.sub.1); (in which R.sub.2 represents alkyl, cycloalkyl, phenyl optionally substituted-, --O-alkyl, 3-pyridyl, 2-pyrrolyl, quinolyl, 1-isoquinolyl, 2-thienyl or 3-indolyl); a radical of --NHS02R3 (A.sub.2) (in which R.sub.3 represents alkyl, cycloalkyl or phenyl optionally substituted); a radical --NHCONHR4 (A.sub.3) (in which R.sub.4 represents alkyl or phenyl-optionally substituted); a phthalimido radical (A.sub.4); an o-sulfobenzoic imido radical (A.sub.5); a di(benzoyl)amino radical (A.sub.6) optionally substituted; a radical of formula A.sub.7 : ##STR2## (in which R.sub.5 represents carbamoyl, cyano, carboxy or alkoxycarbonyl); or a radical of formula A.sub.8 : ##STR3## their stereoisomers and their addition salts with a pharmaceutically-acceptable inorganic or organic acid, are disclosed to be useful as 5-HT.sub.Type: GrantFiled: December 19, 1990Date of Patent: September 1, 1992Assignee: Adir et CompagnieInventors: Gilbert Lavielle, Michel Laubie, Francis Colpaert
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Patent number: 5130315Abstract: Novel 1-piperazinyl-2-butenes and -2-butynes, intermediates and processes for the preparation thereof, and methods of treating psychoses utilizing compounds or compositions thereof are disclosed.Type: GrantFiled: January 10, 1991Date of Patent: July 14, 1992Assignee: Raymond R. WittekindInventors: Helen H. Ong, Nicholas J. Hrib, Joseph Perez, John G. Jurcak
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Patent number: 5130329Abstract: Novel all possible enantiomeric and diastereoisomeric forms of compounds of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of hydrogen, halogen, alkyl and alkoxy of 1 to 5 carbon atoms, --No.sub.2, --NH.sub.2 and mono and dialkylamino of 1 to 5 alkyl carbon atoms, A and B have the trans configuration, one of A and B being ##STR2## R.sub.2 is hydrogen or alkyl of 1 to 5 carbon atoms, Z is --(CH.sub.2).sub.n2, n.sub.2 being an integer from 0 to 5 or branched alkylene of 2 to 8 carbon atoms or --CH.sub.2 --O--, Y is selected from the group consisting of phenyl, naphthyl, indenyl, heteromonocycle of 5 to 6 ring atoms and heterobicycle, all optionally having at least one substituent and the other of A and B is ##STR3## R.sub.4 and R.sub.Type: GrantFiled: October 1, 1990Date of Patent: July 14, 1992Assignee: Roussel UclafInventors: Anne-Marie Moura, Francois Clemence, Daniel Frechet, Michel Fortin
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Patent number: 5068244Abstract: Novel all possible enantiomeric and diastereoisomeric forms of compounds of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of hydrogen, halogen, alkyl and alkoxy of 1 to 5 carbon atoms, --NO.sub.2, --NH.sub.2 and mono and dialkylamino of 1 to 5 alkyl carbon atoms, n is 1 or 2, A and B have the trans configuration, one of A and B being ##STR2## R.sub.2 is hydrogen or alkyl of 1 to 5 carbon atoms, Z is --(CH.sub.2)--.sub.n2, n.sub.2 being an integer from 0 to 5 or branched alkylene of 2 to 8 carbon atoms or --CH.sub.2 --O--, Y is selected from the group consisting of phenyl, naphthyl, indenyl, heteromonocycle of 5 to 6 ring atoms and heterobicycle, all optionally having at least one substituent and the other of A and B is ##STR3## R.sub.4 and R.sub.Type: GrantFiled: February 17, 1989Date of Patent: November 26, 1991Assignee: Roussel UclafInventors: Anne-Marie Moura, Francois Clemence, Daniel Frechet, Michel Fortin
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Patent number: 5051422Abstract: This invention relates to novel 2-substituted-1(4)-aryl piperazines and to a process for their preparation. The compounds of this invention have been found to have cardiovascular, primarily antiarrhythmic effects and are of the following general formula I ##STR1## wherein R is hydrogen, lower alkyl or benzyl; and R.sub.1 and R.sub.2 are the same or independently hydrogen, lower alkyl, lower alkoxy or halogen;Z is ##STR2## --NR.sub.3 --CH.sub.2 --, --OCH.sub.2 --, --NR.sub.3 --, --O-- or --NR.sub.3 SO.sub.2 -- andQ is (C.sub.1 -C.sub.4) alkyl--SO.sub.2 --NR.sub.4 -- or ##STR3## R.sub.3 is hydrogen, lower alkyl, allyl or loweralkoxyloweralkyl; and included in the descriptors of the compounds of Formula I is the proviso that when R.sub.4 is methyl then ##STR4## must be in the 2 position of Formula I.Type: GrantFiled: September 15, 1989Date of Patent: September 24, 1991Assignee: Schering AGInventors: William C. Lumma, Jr., Thomas K. Morgan, Jr., Gary B. Phillips
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Patent number: 5051423Abstract: Novel derivatized alkanolamines of the following structural formula ##STR1## are described as useful cardiovascular agents. Most especially described is their usefulness as cardiovascular agents exhibiting an antiarrhythmic effect. Said antiarrhythmic effect is of a combination Class II/Class III variety. Pharmaceutical formulations containing such compounds are also described.Type: GrantFiled: July 13, 1988Date of Patent: September 24, 1991Assignee: Schering AGInventors: Randall E. Lis, William C. Lumma, Jr., Thomas K. Morgan, Jr., Klaus Nickisch, Ronald A. Wohl
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Patent number: 5047417Abstract: A butenoic or propenoic acid derivative having the following formula in which G is an aryl or a heterocyclic ring, R11 and R12 are hydrogen or an alkyl, X is sulfur or oxygen, R2 and R3 are hydrogen, an substituent such as an alkyl and J is pyridyl or phenyl having substituents and a heterocyclic ring may be formed between R2, R3 and J is provided here and is useful in the pharmacological field.Type: GrantFiled: May 19, 1989Date of Patent: September 10, 1991Assignee: Eisai Co. Ltd.Inventors: Norio Minami, Fumihiro Ozaki, Keiji Ishibashi, Yasuhiro Kabasawa, Megumi Ikemori, Toshiaki Ogawa, Takanori Kawamura
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Patent number: 4988814Abstract: Compounds of the formula: ##STR1## in which R.sup.1 is alkyl; R.sup.2 and R.sup.3 are alkyl or taken together they are polymethylene, R.sup.2 and R.sup.3 complete a 5-norbornen-2-yl moiety; X is --CO.sub.2 --, --OCO--, --OCO.sub.2 --, --N(R.sup.7)CO--, --NHNHCO--, --ON(R.sup.7)CO--, --CON(R.sup.7)--, --N(R.sup.7)CO.sub.2 --, --OCON(R.sup.7)-- or --N(R.sup.7)CON(R.sup.8)--, wherein R.sup.7 and R.sup.8 are, independently, hydrogen, alkyl, phenyl, benzyl, substituted phenyl or substituted benzyl in which the substituents are halo, alkyl alkoxy, cyano, nitro or perhalomethyl; R.sup.4 is hydrogen or alkyl; R.sup.5 is hydrogen, alkyl, hydroxyalkyl, phenyl, benzyl, substituted phenyl or substituted benzyl in which the substituents are hydroxy, halo, alkyl alkoxy, trifluoromethyl, nitro, cyano, carbalkoxy, carboxamido, amino, alkylamino or dialkylamino; R.sup.Type: GrantFiled: October 27, 1989Date of Patent: January 29, 1991Assignees: American Home Products Corp., John Wyeth & Bro.Inventors: Magid A. Abou-Gharbia, John P. Yardley, Ian A. Cliffe
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Patent number: 4977166Abstract: New benzopyran derivatives of formula: ##STR1## in which R.sub.1 is hydrogen, halogen, hydroxy, alkoxy, nitro, amino, alkylsulphonamido, bis(alkylsulphonyl) amino or acylamino,X is nitrogen or a >CH-radicalR is a radical of formula: ##STR2## in which A denotes a single bond or methylene or, when X is nitrogen, A may denote carbonyl, and R.sub.2 and R.sub.3, which are identical or different, are hydrogen, halogen, hydroxy, alkyl, alkoxy, nitro, amino, alkylsulphonamido, bis(alkylsulphonyl)amino, acylamino, sulphamoyl or cyano, or, when they are adjacent, together form a methylenedioxy or ethylenedioxy radical, or elseR is pyridyl or 2(2H)-benzimidazolonyl if X denotes >CH--, andR' and R" are identical and are hydrogen or alkyl, their isomeric forms and mixtures thereof, and their acid addition salts, can be used as antiarrhythmic and antifibrillation agents.Type: GrantFiled: March 22, 1989Date of Patent: December 11, 1990Assignee: Rhone-Poulenc SanteInventors: Jean-Claude Hardy, Christian Renault
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Patent number: 4940711Abstract: N-piperazinylalkanoylanilides of the formula ##STR1## wherein n is 0, 1 or 2, each of R and R.sub.1 is H or alkyl, and each of R.sub.2, R.sub.3 and R.sub.4 is H, halogen, alkyl, hydroxyalkyl, alkoxy, aralkoxy, alkylthio, aralkylthio, alkylsulphonyl, alkylsulphenyl, NO.sub.2, NH.sub.2, alkylamino, acylamino, ureido, alkylureido, alkylsulphonylamino, CF.sub.3, acyl, CN, COOH, alkoxycarbonyl, NH.sub.2 CO, SO.sub.3 H, guanidinosulphonyl, carbamoyloxy, OH, acyloxy, alkylsulphonyloxy, alkylenedioxy or SO.sub.2 NR.sub.5 R.sub.6 wherein each of R.sub.5 and R.sub.6 is H, alkyl, aryl or acyl and their pharmaceutically acceptable acid addition salts, are antihypertensive agents.Type: GrantFiled: June 30, 1989Date of Patent: July 10, 1990Assignee: Recordati, S.A., Chemical and Pharmaceutical CompanyInventors: Dante Nardi, Amedeo Leonardi, Alberto Catto, Gabriele Graziani
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Patent number: 4931444Abstract: 4-(4-phenyl-1-piperazinyl)phenols for use as 5-lipoxygenase inhibitors and a method of treating warm-blooded animals suffering from leukotriene mediated diseases and disorders using the same. Pharmaceutical compositions containing the same as active ingredient. Novel compounds used in said method and processes for preparing said novel compounds.Type: GrantFiled: January 12, 1989Date of Patent: June 5, 1990Assignee: Janssen Pharmaceutica N.V.Inventors: Jean P. F. Van Wauwe, Jan Heeres, Leo J. J. Backx
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Patent number: 4895847Abstract: Novel 2,3-dihydro-1H-indene derivatives and salts thereof represented by the general formula (1), ##STR1## [wherein R.sup.1 and R.sup.2 are each a hydrogen atom, a lower alkyl group, a phenyl group which may have halogen atoms and/or alkyl groups as the substituents on the phenyl ring; R.sup.3 is a halogen atom or a lower alkyl group; R.sup.4 is a hydrogen atom, a halogen atom, a phenyl-lower alkyl group, a cycloalkyl-lower alkyl group or the like; R.sup.5 is a hydroxyimino group, an alkylamino group or a group of the formula --NHR.sup.8 (wherein R.sup.8 is a hydrogen atom, a halogen-substituted lower alkanoyl group or the like); R.sup.6 is a hydrogen atom or a phenyl group; and R.sup.7 is a hydrogen atom or a lower alkyl group].Type: GrantFiled: September 21, 1988Date of Patent: January 23, 1990Assignee: Otsuka Pharmaceutical Co., Ltd.Inventors: Yasuo Oshiro, Hiraki Ueda, Kazuyuki Nakagawa
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Patent number: 4894472Abstract: The invention relates to new dicyanoethylaryl derivatives and to processes for their preparation. The compounds according to the invention can be used as redox indicators, such as, for example, for the detection of hydrogen peroxide with the aid of peroxidases or peroxidatively active substances.These redox indicators are futhermore suitable for the detection of peroxidases or peroxidatively active compounds, it also being possible to use other peroxides as oxidizing agents.Type: GrantFiled: March 21, 1988Date of Patent: January 16, 1990Assignee: Miles Inc.Inventors: Florin Seng, Klaus Wehling
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Patent number: 4882432Abstract: The compounds of the formula: ##STR1## wherein Ad is 1-adamantyl, 2-adamantyl or 3-noradamantyl; X is --O-- or ##STR2## n is 1,2,3 or 4; R.sup.1 and R.sup.2 are, independently, hydrogen, alkyl, phenyl, benzyl, or substituted phenyl or benzyl in which the substituent is alkyl, alkoxy, halo, cyano, nitro or trifluoromethyl; and R.sup.3 is phenyl, benzyl or substituted phenyl or benzyl in which the substituent is alkyl, alkoxy, halo, nitro, cyano or perhalomethyl, 2-, 3-, or 4-pyridinyl, 2-, 4-or 5-pyrimidiny; or 2- or 3-pyrazinyl; R.sup.4 and R.sup.5 are independently, hydrogen, methyl, phenyl or benzyl; or a pharmaceutically acceptable salt thereof, are useful anxiolytic/antidepressant agents, with elements of antipsychotic activity.Type: GrantFiled: January 9, 1989Date of Patent: November 21, 1989Assignee: American Home Products CorporationInventors: Magid A. Abou-Gharbia, John P. Yardley, Wayne E. Childers, Jr.
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Patent number: 4845221Abstract: The compounds ##STR1## in which R.sub.1 is hydroxy, alkoxy of 1 to 6 carbon atoms, amino, alkylamino of 1 to 6 carbon atoms, dialkylamino where each alkyl substituent contains 1 to 6 carbon atoms, or alkanoylamino of 2 to 6 carbon atoms;R.sub.2 is 3-trifluoromethylphenyl, 3-halophenyl, 2-pyrimidinyl, halopyrimidin-2-yl, 2-pyrazinyl or halopyrazin-2-yl; andn is one of the integers 1 or 2;or a pharmaceutically acceptable salt thereof, are selective serotonergic agents useful in the treatment of depression and/or anxiety, as well as related sexual dysfunctions and appetite disorders.Type: GrantFiled: April 15, 1988Date of Patent: July 4, 1989Assignee: American Home Products CorporationInventors: Gary P. Stack, Edward J. Podlesny
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Patent number: 4780495Abstract: N-(substituted)-1-(piperazinealkyl)-.alpha.-(3,5-dialkyl-4-hydroxyphenyl)-. alpha.,.alpha.-disubstited acetamides, are novel compounds prepared by a novel modification of the ketoform process. The compounds are useful as stabilizers for organic materials subject to degradation in an environment in which the materials are exposed to heat, oxidation and light, particularly ultraviolet light. The compounds are especially useful in combination with known secondary stabilizers.Type: GrantFiled: January 25, 1988Date of Patent: October 25, 1988Assignee: The B. F. Goodrich CompanyInventors: John T. Lai, Pyong N. Son
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Patent number: 4749703Abstract: Compounds of the formula: ##STR1## wherein A means an alkylene; Y--Z means ##STR2## --CH.dbd.CH--, --CH.sub.2 CH.sub.2 --, or ##STR3## R.sub.1 and R.sub.2 are each a substituent; R.sub.3 is hydrogen atom, alkyl, or alkoxy; R.sub.4 is phenyl, phenylalkyl, phenylalkenyl, diphenylmethyl, naphthyl, thiazolyl, optionally substituted pyridyl, optionally substituted pyrimidinyl, quinolyl, benzoylalkyl, benzoyl, furoyl, thenoyl, phenyloxycarbonyl, phenyloxysulfonyl, or phenylsulfonyl; a is 2 or 3, b and c are each 1 or 2, and d is an integer of 0 to 2, provided that the phenyl, phenyl moiety and naphthyl may optionally be substituted, and a pharmaceutically acceptable salt thereof, process for the preparation thereof, and pharmaceutical composition containing the same. The compounds and salt thereof show potent calcium antagonistic activity and are useful for prophylaxis and treatment of hypertension and/or ischemic heart disease.Type: GrantFiled: April 10, 1986Date of Patent: June 7, 1988Assignee: Dainippon Pharmaceutical Co., Ltd.Inventors: Hitoshi Uno, Mikio Kurokawa, Fuminori Sato, Naonobu Hatano
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Patent number: 4735959Abstract: There are described novel carboxylic acid derivatives of the formula ##STR1## and derivatives of the formula ##STR2## and the addition salts thereof, which exhibit an effect on the intermediary metabolism. Furthermore, the compounds of Formula Ia as well as the compounds of Formula I possess blood-sugar lowering properties.Type: GrantFiled: May 14, 1985Date of Patent: April 5, 1988Assignee: Dr. Karl Thomae GmbHInventors: Wolfgang Grell, Gerhart Griss, Robert Sauter, Rudolf Hurnaus, Eckhard Rupprecht, Nikolaus Kaubisch, Joachim Kahling, Bernhard Eisele
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Patent number: 4713382Abstract: Compounds having the formula ##STR1## wherein R, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 have the definitions given herein, are useful as antiarrhythmic agents.Type: GrantFiled: May 30, 1985Date of Patent: December 15, 1987Assignee: Syntex (U.S.A.) Inc.Inventor: Jean-Claude Pascal
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Patent number: 4686220Abstract: This disclosure describes certain substituted piperazine-1,4-naphthalenediones useful as anti-asthmatic agents.Type: GrantFiled: December 19, 1985Date of Patent: August 11, 1987Assignee: American Cyanamid CompanyInventors: Jeffrey B. Medwid, Lawrence W. Torley, Andrew S. Tomcufcik
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Patent number: 4666911Abstract: An analgesic compositon containing as active ingredient an allophanoylpiperazine compound represented by the general formula ##STR1## wherein R.sup.1 represents a lower alkyl group or phenyl group; R.sup.2 and R.sup.3 each represents a hydrogen atom or a lower alkyl group; and R.sup.4 represents a phenyl group or a substituted phenyl group having as substituent a halogen atom or methyl, trifluoromethyl, hydroxyl, methoxy, methylenedioxy, nitro, or carboxyl group; pyridyl group, pyrimidyl group, thiazolyl group, benzyl group, cinnamyl group, cyclohexyl group, a lower alkyl group, a substituted lower alkyl group having chlorine atom or hydroxyl group as substituent; or a lower alkenyl group.Type: GrantFiled: July 8, 1981Date of Patent: May 19, 1987Assignee: Taiho Pharmaceutical Company LimitedInventors: Hajime Fujimura, Yasuzo Hiramatu, Takahiro Yabuuchi, Masakatu Hisaki, Katsuo Takikawa, Takaji Honna, Hidekazu Miyake, Makoto Kajitani
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Patent number: 4616086Abstract: The present invention is concerned with new carboxylic acid derivatives, with processes for the preparation thereof and with pharmaceutical compositions for lipid depression and thrombocyte aggregation, containing them, and to methods for treating infirmaties caused by excess lipids or thrombocyte aggregation.Type: GrantFiled: October 1, 1984Date of Patent: October 7, 1986Assignee: Boehringer Mannheim GmbHInventors: Ernst-Christian Witte, Hans P. Wolff, Bernd Hagenbruch, Karlheinz Stegmeir, Johannes Pill
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Patent number: 4613598Abstract: A piperazine derivative according to the present invention has the following general formula [I]: ##STR1## wherein R.sup.1 is --OH, --OR.sup.3, --SR.sup.3, --SOR.sup.3 or --SO.sub.2 R.sup.3 wherein R.sup.3 is alkyl group having 1 to 3 carbon atoms;R.sup.2 is --SO.sub.2 NH.sub.2, --SO.sub.2 NHR.sup.4, --SO.sub.2 NR.sup.4 R.sup.5, --COOH, --COOR.sup.4, --CONH.sub.2, --CONHR.sup.4, --CONR.sup.4 R.sup.5, --NHCONH.sub.2, --NHCSNH.sub.2, --NHCONHR.sup.4, --NHCOR.sup.4 or --NHSO.sub.2 R.sup.4 wherein R.sup.4 and R.sup.5 are independently alkyl group having 1 to 3 carbon atoms; orR.sup.1 and R.sup.2 together with carbon atoms to which they are attached form ##STR2## Z is --CO-- or --CH(OH)--; Ar is pyridyl or substituted or unsubstituted phenyl; andn is an integer of 3 to 5.An acid addition salt of the piperazine derivative having the above formula [I] is included in the present invention.Type: GrantFiled: March 6, 1985Date of Patent: September 23, 1986Assignee: Mitsubishi Chemical Industries LimitedInventors: Harukazu Fukami, Shinya Inoue, Issei Nitta, Kenichiro Nakao, Ryoji Kikumoto
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Patent number: 4597912Abstract: A compound of the formula: ##STR1## wherein R.sup.1 and R.sup.2 independently of one another are unsubstituted or hydroxy substituted, C.sub.1 -C.sub.4 alkoxy substituted, cyano substituted, C.sub.1 -C.sub.4 alkoxycarbonyl substituted, di-C.sub.1 -C.sub.4 alkylamino substituted, (CH.sub.3)(C.sub.6 H.sub.5 CH.sub.2)NC.sub.2 H.sub.4 substituted, chlorine substituted or bromine substituted C.sub.1 -C.sub.4 -alkyl, cyclohexyl, benzyl, phenylethyl or phenyl, R.sup.1 and R.sup.2 together with the nitrogen are morpholino, pyrrolidino, piperidino or N-methylpiperazino;R.sup.3 is hydrogen, chlorine, bromine, methyl, ethyl, methoxy, ethoxy or nitro;R.sup.4 and R.sup.5 independently of one another are hydrogen, C.sub.1 -C.sub.4 -alkyl or benzyl; X is oxygen or imino; A.sup.Type: GrantFiled: May 17, 1985Date of Patent: July 1, 1986Assignee: BASF AktiengesellschaftInventors: Manfred Eisert, Klaus Grychtol
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Patent number: 4560686Abstract: Compounds of the formula ##STR1## (wherein R.sub.1 is a lower alkyl group, R.sub.2, R.sub.3 and R.sub.4, which may be the same or different, represent a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a hydroxyl group, a trifluoromethyl group or a lower alkoxycarbonyl group; two adjacent groups of R.sub.2, R.sub.3 and R.sub.4 may combine to form a methylenedioxy group; n is an integer of 2 to 6) or salts thereof, are disclosed.These compounds are useful as agents for treating circulatory diseases because they have hypotensive action and are capable of increasing the cerebral blood flow, decreasing the heart rate and suppressing ventricular arrhythmia due to myocardial ischemia.Type: GrantFiled: September 14, 1983Date of Patent: December 24, 1985Assignee: Chugai Seiyaku Kabushiki KaishaInventors: Hiroyuki Nagano, Mitiro Takagi, Noboru Kubodera, Isao Matsunaga, Hiroyuki Nabata, Yasuhiro Ohba, Kazushige Sakai, Shun-ichi Hata, Yasumi Uchida
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Patent number: 4446133Abstract: The present invention relates to a novel piperazine compound represented by the following general formula (I): ##STR1## wherein X stands for a hydrogen or halogen atom, an alkoxy, carboxy or alkoxycarbonyl group or a group R.sup.3 CO-- in which R.sup.3 stands for an alkyl group having 1 to 4 carbon atoms, R.sup.1 stands for a hydrogen atom or an alkyl group, and R.sup.2 stands for a hydrogen atom or an alkyl group.These compounds are valuable as immunopotentiators, such as for the treatment of chronic rheumatoid arthritis and other diseases accompanied by reduction or abnormal change of the immune function.Type: GrantFiled: February 13, 1981Date of Patent: May 1, 1984Assignee: Misuitoatsu Chemicals, Inc.Inventors: Yutaka Okazaki, Hiroshi Tokuda, Shiyoichiro Miyahara, Yoshitsugu Yamada
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Patent number: 4435399Abstract: A series of novel 2-aryl-1-(imidazol-1-yl)-8-(4-piperazin-1-ylphenoxy)octan-2-ol derivatives has been prepared, including their pharmaceutically acceptable acid addition salts. These particular compounds are useful in therapy as antifungal agents for the treatment of various topical, mucosal and systemic fungal infections in animals, including humans. Preferred member compounds include 2-(2,4-dichlorophenyl)-1-(imidazol-1-yl)-8-[4-ethylpiperazin-1-yl)phenoxy] octan-2-ol, 2-(2,4-dichlorophenyl)-1-(imidazol-1-yl)-8-[4-(4-n-propylpiperazin-1-yl)ph enoxy]octan-2-ol and 2-(2,4-dichlorophenyl)-1-(imidazol-1-yl)-8-[4-(4-isopropylpiperazin-1-yl)p henoxy]octan-2-ol, respectively. Methods for preparing these compounds from known starting materials are provided.Type: GrantFiled: June 25, 1982Date of Patent: March 6, 1984Assignee: Pfizer Inc.Inventors: Kenneth Richardson, Geoffrey E. Gymer
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Patent number: 4377522Abstract: There are presented novel benzodiazepine derivatives of the formula ##STR1## wherein R.sup.1 is lower alkyl, lower hydroxyalkyl or lower dialkylaminoalkyl, R.sup.2 and R.sup.3 each are lower alkyl, R.sup.4 is halogen, R.sup.5, R.sup.7 and R.sup.8 each are hydrogen or halogen and R.sup.6 is nitro, amino, lower alkylamino, lower dialkylamino or a group of the formula H.sub.2 N--C(CH.sub.3).sub.2 --CO--NH--, R.sup.9 R.sup.10 N--CO--NH-- or ##STR2## and either R.sup.9 is hydrogen or lower alkyl and R.sup.10 is lower alkyl or lower hydroxyalkyl or R.sup.9 and R.sup.10 together with the nitrogen atom are a 3- to 7-membered heterocycle which, provided it is at least 5-membered, can contain as a ring member an oxygen or sulfur atom or a group of the formula >N--R in which R is hydrogen or lower alkyl,and their pharmaceutically acceptable acid addition salts.Type: GrantFiled: July 6, 1981Date of Patent: March 22, 1983Assignee: Hoffmann-La Roche Inc.Inventors: Quirico Branca, Albert E. Fischli, Andre Szente
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Patent number: 4342756Abstract: Compounds are described of the formula ##STR1## (and their salts and solvates) in which: X is cis or trans --CH.dbd.CH--;R.sup.1 is C.sub.1-7 alkyl terminated by --COOR.sup.3 where R.sup.3 is H, C.sub.1-6 alkyl or C.sub.7-10 aralkyl;Y is a saturated heterocyclic amino group having 5-8 ring members; andR.sup.2 is C.sub.2-4 alkanoyl, C.sub.3-6 alkenyl (optionally substituted), C.sub.1-12 alkyl, or substituted or unsubstituted phenylalkyl, biphenylalkyl or naphthylalkyl.These compounds inhibit blood platelet aggregation and bronchoconstriction and may be formulated for use as antithrombotic and anti-asthmatic agents.Type: GrantFiled: April 29, 1981Date of Patent: August 3, 1982Assignee: Glaxo Group LimitedInventors: Eric W. Collington, Peter Hallett, Christopher J. Wallis, John Bradshaw, Norman F. Hayes
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Patent number: 4336382Abstract: There are disclosed compounds of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of lower alkyl; R.sub.8 is selected from the group consisting of --O--(CH.sub.2).sub.n --wherein n is 2 to 20, ##STR2## and R.sub.6 is selected from the group consisting of hydrogen or lower alkoxy, and ##STR3## wherein R.sub.1 is selected from the group consisting of lower alkyl; R.sub.8 is selected from the group consisting of --O--(CH.sub.2).sub.n --wherein n is 2 to 20, ##STR4## and R.sub.6 is selected from the group consisting of hydrogen or lower alkoxy and racemates thereof.There are also disclosed processes and intermediates utilized to produce the end products.The end products have utility as agents exhibiting both .alpha. and selective .beta. adrenergic blocking action.Type: GrantFiled: August 25, 1980Date of Patent: June 22, 1982Assignee: Hoffmann-La Roche Inc.Inventors: Kenneth E. Fahrenholtz, Robert W. Guthrie, Richard W. Kierstead, Jefferson W. Tilley
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Patent number: 4283538Abstract: In one embodiment, the present invention is concerned with novel triarylmethane compounds possessing in their triaryl structure a 4'-oxo-1'-naphthylidene (or a 4'-oxo-1'-phenylidene) moiety and a phenyl moiety substituted in the ortho-position to the central carbon atom with the group ##STR1## wherein R is an alkyl group or a phenyl group, unsubstituted or substituted with a solubilizing group; R' is selected from ##STR2## wherein R" is methyl, unsubstituted or substituted with one or two halo groups or substituted with a phenyl, alkoxy or phenoxy group and ##STR3## wherein Y is an electron-withdrawing group; and R and R' taken with said ##STR4## represents ##STR5## In another embodiment the present invention is concerned with a method of synthesizing the aforementioned compounds by reacting, e.g., a 2-R'-3-(4'-hydroxy-1'-phenyl/naphthyl)-3-(phenyl/naphthyl)-2,3-dihydrobenz [d]isothiazole-1,1-dioxide with an alkylation reagent in the presence of base.Type: GrantFiled: December 26, 1979Date of Patent: August 11, 1981Assignee: Polaroid CorporationInventor: James W. Foley
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Patent number: 4252804Abstract: Compounds of the formula I ##STR1## wherein m and n are 0, 1 or 2, X represents oxygen, imino, benzylimino, or morpholinoethylimino, Y represents CO, CONH, COO or SO.sub.2, and NR.sub.1 R.sub.2 represents a dimethylamino, diethylamino, dipropylamino, dibutylamino, allylamino, isobutenylamino, cyclopentylamino, cyclohexylamino, cycloheptylamino, cyclooctylamino, N-methyl N-cyclopentylamino, N-methyl N-cyclohexylamino, N-allyl N-cyclohexylamino, adamantylamino, diethoxyethylamino, dimethylaminoethylamino, dimethylaminopropylamino, N-methyl N-dimethylaminopropyl-amino, benzylamino, 3,4,5-trimethoxybenzylamino, phenethylamino, p-chlorophenethylamino, tetrahydrofurfurylamino, tetrahydropyranylmethylamino, pyrrolidino, isoxazolidinyl, piperidino, 4-hydroxypiperidino, 4-m-chlorophenyl-4-hydroxypiperidino, homopiperidino, 1,2,3,6-tetrahydropyridyl, morpholino, 2-methylmorpholino, 2,6-dimethylmorpholino, 2-morpholinoethylamino, thiamorpholino, piperazino, 4-methylpiperazino, 4-(.alpha.Type: GrantFiled: January 13, 1978Date of Patent: February 24, 1981Assignee: Metabio-JoullieInventors: Maurice Joullie, Gabriel Maillard, Lucien Lakah, Christian J. M. Warolin
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Patent number: 4247710Abstract: There are disclosed compounds of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of lower alkyl; R.sub.8 is selected from the group consisting of --O--(CH.sub.2).sub.n --wherein n is 2 to 20, ##STR2## R.sub.6 is selected from the group consisting of hydrogen or lower alkoxy, and ##STR3## wherein R.sub.1 is selected from the group consisting of lower alkyl; R.sub.8 is selected from the group consisting of --O--(CH.sub.2).sub.n --wherein n is 2 to 20, ##STR4## and R.sub.6 is selected from the group consisting of hydrogen or lower alkoxy and racemates thereof.There are also disclosed processes and intermediate utilized to produce the end products.The end products have utility as agents exhibiting both .alpha. and selective .beta. adrenergic blocking action.Type: GrantFiled: September 6, 1979Date of Patent: January 27, 1981Assignee: Hoffmann-La Roche Inc.Inventors: Kenneth E. Fahrenholtz, Robert W. Guthrie, Richard W. Kierstead, Jefferson W. Tilley
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Patent number: 4223144Abstract: Compounds of the general formula I ##STR1## where B is a bridge member,the radicals R independently of one another are hydrogen or substituted or unsubstituted alkyl, or two radicals R together with the nitrogen are a heterocyclic saturated 5-membered or 6-membered ring,the radicals R.sup.1 independently of one another are hydrogen or C.sub.1 -C.sub.4 -alkyl,the radicals R.sup.2 independently of one another are hydrogen, C.sub.1 -C.sub.4 -alkyl or halogen,the radicals R.sup.3 independently of one another are hydrogen or substituted or unsubstituted alkyl or together are an alkylene group, and X.crclbar. is an anion. The compounds of the formula I are particularly suitable for dyeing paper.Type: GrantFiled: September 5, 1978Date of Patent: September 16, 1980Assignee: BASF AktiengesellschaftInventors: Hellmut Kast, Klaus Grychtol, Franz Feichtmayr
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Patent number: 4216216Abstract: Compounds of general formula ##STR1## are disclosed wherein appropriate substituents for R.sup.1, R.sup.2 to R.sup.5, R.sup.6, A, Q, X, and Z are defined for these novel hexahydropyrimidines. Procedures for the preparation of these compounds are also given. Because of the highly effective serotonin antagonistic activity in combination with a strong inhibiting effect on thrombocyte aggregation and good compatibility these compounds are effective in treating migraine. Additionally, the compounds also exhibit an anti-histamine activity, cause an increase in erythrocyte fluidity, a psychotropic activity, a weak bradykinin antagonism and hypotensive effects.Type: GrantFiled: June 15, 1978Date of Patent: August 5, 1980Assignee: Hoechst AktiengesellschaftInventors: Rolf-Ortwin Weber, Hiristo Anagnostopulos, Ulrich Gebert
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Patent number: 4202978Abstract: There are disclosed compounds of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of lower alkyl; R.sub.8 is selected from the group consisting of --O--(CH.sub.2).sub.n --wherein n is 2 to 20, ##STR2## and R.sub.6 is selected from the group consisting of hydrogen or lower alkoxy, and ##STR3## wherein R.sub.1 is selected from the group consisting of lower alkyl; R.sub.8 is selected from the group consisting of --O--(CH.sub.2).sub.n --wherein n is 2 to 20, ##STR4## and R.sub.6 is selected from the group consisting of hydrogen or lower alkoxy and racemates thereof.There are also disclosed processes and intermediates utilized to produce the end products.The end products have utility as agents exhibiting both .alpha. and selective .beta. adrenergic blocking action.Type: GrantFiled: February 8, 1978Date of Patent: May 13, 1980Assignee: Hoffmann-La Roche Inc.Inventors: Kenneth E. Fahrenholtz, Robert W. Guthrie, Richard W. Kierstead, Jefferson W. Tilley
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Patent number: 4177290Abstract: Novel acetamide derivatives have been discovered to have useful pharmaceutical activity on the central nervous system. They may be prepared by reacting the corresponding ester or acid halide with the appropriately substituted amine.Type: GrantFiled: March 9, 1978Date of Patent: December 4, 1979Assignee: Laboratoire L. LafonInventor: Louis Lafon
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Patent number: 4177270Abstract: 1,3-Benzodithiole-2-one and 1,3-benzodithiole-2-thione compounds are disclosed including the novel method of preparing said compounds and their biocidal activity.Type: GrantFiled: December 14, 1977Date of Patent: December 4, 1979Assignee: The Ansul CompanyInventors: Khalid Rasheed, James D. Warkentin
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Patent number: 4153609Abstract: A 3-indolyl-3-bis-aminophenyl-phthalide compound of the formula ##STR1## wherein R.sub.1 represents alkyl which has at most 12 carbon atoms and is unsubstituted or substituted by halogen, hydroxyl, cyano or lower alkoxy, cycloalkyl, or unsubstituted or substituted phenyl or benzyl wherein the substituents are halogen, nitro, lower alkyl or lower alkoxy,R.sub.2 represents hydrogen, alkyl which has at most 12 carbon atoms and is unsubstituted or substituted by halogen, hydroxyl, cyano or lower alkoxy, cycloalkyl, or benzyl which is unsubstituted or substituted by halogen, nitro, lower alkyl or lower alkoxy, orR.sub.1 and R.sub.2 together with the nitrogen atom linking them represent a 5- or 6-membered heterocyclic radical,X.sub.1 and X.sub.2 independently of one another represent hydrogen, lower alkyl, cycloalkyl, benzyl which is unsubstituted or substituted by halogen, nitro, lower alkyl or lower alkoxy, or acyl having 1 to 8 carbon atoms, and X.sub.Type: GrantFiled: January 10, 1977Date of Patent: May 8, 1979Assignee: Ciba-Geigy CorporationInventors: Jean C. Petitpierre, Robert Garner