The -c(=x)- Is Part Of A -c(=x)x- Group, Wherein The X's Are The Same Or Diverse Chalcogens Patents (Class 549/71)
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Patent number: 5463083Abstract: 2,5-Diaryl tetrahydrofurans, 2,5-diaryl tetrahydrothiophenes, 1,3-diaryl cyclopentanes are disclosed that reduce the chemotaxis and respiratory burst leading to the formation of damaging oxygen radicals of polymorphonuclear leukocytes during an inflammatory or immune response. The compounds exhibit this biological activity by acting as PAF receptor antagonists, by inhibiting the enzyme 5-lipoxygenase, or by exhibiting dual activity, i,e., by acting as both a PAF receptor antagonist and inhibitor of 5-lipoxygenase. Also disclosed is a method to treat disorders mediated by PAF and/or leukotrienes that includes administering an effective amount of one or more of the above-identified compounds or a pharmaceutically acceptable salt thereof, optionally in a pharmaceutically acceptable carrier, to a patient in need of such therapy.Type: GrantFiled: January 6, 1994Date of Patent: October 31, 1995Assignee: Cytomed, Inc.Inventors: Tesfaye Biftu, Xiong Cai, Sajjet Hussion, Gurmit Grewal, T. Y. Shen
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Patent number: 5439925Abstract: Di(aromatic) compounds corresponding to the following formula: ##STR1## in which: Ar represents either ##STR2## n=1 or 2 or: ##STR3## X represents a divalent radical, Z represents O, S or a divalent radical, and R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 represent a hydrogen atom or various organic radicals, and the salts of the compounds of formula (I) when R.sub.1 is a carboxylic acid function. Use is in human and veterinary medicine and in cosmetics.Type: GrantFiled: December 16, 1993Date of Patent: August 8, 1995Assignee: Centre International de Recherches Dermatologiques Galderma (Cird Galderma)Inventors: Jean-Michel Bernardon, Willliam R. Pilgrim
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Patent number: 5434151Abstract: 2,5-Diaryl tetrahydrofurans, 2,5-diaryl tetrahydrothiophenes, 2,4-diaryl tetrahydrofurans, 2,4-diaryl tetrahydrothiophenes, 1,3-diaryl cyclopentanes, 2,4-diaryl pyrrolidines, and 2,5-diaryl pyrrolidines are disclosed that reduce the chemotaxis and respiratory burst leading to the formation of damaging oxygen radicals of polymorphonuclear leukocytes during an inflammatory or immune response. The compounds exhibit this biological activity by acting as PAF receptor antagonists, by inhibiting the enzyme 5-lipoxygenase, or by exhibiting dual activity, i.e., by acting as both a PAF receptor antagonist and inhibitor of 5-lipoxygenase.A method to treat disorders mediated by PAF or leukotrienes is also disclosed, that includes administering an effective amount of one or more of the above-identified compounds or a pharmaceutically acceptable salt thereof, optionally in a pharmaceutically acceptable carrier.Type: GrantFiled: August 24, 1992Date of Patent: July 18, 1995Assignee: CytoMed, Inc.Inventors: Xiong Cai, Sajjat Hussoin, San-Bao Hwang, David Killian, T. Y. Shen
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Patent number: 5401868Abstract: The present invention relates to hitherto unknown intermediate of formula, in which R.sub.1 stands for hydrogen or a straight or branched aliphatic C.sub.1 -C.sub.20 carbon chain or an aryl or aralkyl group, aryl and "ar" meaning an aromatic or heterocyclic, 5- or 6-membered ring substituent containing 1 or 2 hetero atoms selected among O, S and N, R.sup.1 optionally being further substituted, and its chain being interrupted by hetero atoms like oxygen, or by carbonyl group(s); and R.sup.3 stands for hydrogen or C.sub.1 -C.sub.3 alkyl. The present intermediates can be used in a one step method for producing prodrugs of formula, where D-H =drug itself.Type: GrantFiled: February 26, 1992Date of Patent: March 28, 1995Assignee: Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Productionsaktieselskab)Inventor: Frantz J. Lund
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Patent number: 5399586Abstract: Retinoid-like compounds which act as agonists of the RXR retinoid receptor sites induce apoptosis of tumor cells in cell cultures, and are used as drugs to treat tumors in mammals including humans. Compounds which are specific agonists of RXR receptors and also compounds which are agonists of both RAR and RXR agonist (pan-agonists) induce apoptosis, although the RXR agonist compounds are preferred as drugs to avoid undesirable side effects associated with RAR agonist activity. The RXR agonists compounds are administered to mammals afflicted with tumors in pharmaceutical compositions adapted for systemic topical or for intralesional administration. The range of concentration of the active ingredient RXR agonist compound in the pharmaceutical compositions is approximately between 0.001 and 5 percent by weight, and such that the composition delivers approximately 0.1 mg to 100 mg of the active ingredient per kg body weight of the patient, per day of treatment.Type: GrantFiled: March 11, 1993Date of Patent: March 21, 1995Assignee: Allergan, Inc.Inventors: Peter A. J. Davies, Roshantha A. Chandraratna
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Patent number: 5391819Abstract: Disclosed herein is a process of making chiral 2-aryl-1,4-butanediamine derivatives useful as neurokinin-A antagonists of Formula 7 ##STR1##Type: GrantFiled: September 30, 1992Date of Patent: February 21, 1995Assignee: Merck & Co., Inc.Inventors: Paul E. Finke, Jeffrey J. Hale, Malcolm Maccoss, Sander G. Mills
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Patent number: 5391753Abstract: Compounds of the formula ##STR1## where R.sub.1, R.sub.2, R.sub.3 and R.sub.4 independently are hydrogen, lower alkyl of 1-6 carbons, halogen or lower alkoxy of 1-6 carbons; R.sub.5 and R.sub.5 ' independently are hydrogen or lower alkyl of 1-6 carbons; Y is oxygen or sulfur; Z is n-alkyl having 1-10 carbons, cyclo or branch-chained alkyl of 3-10 carbons, and straight chain alkenyl having 2-10 carbons, or cyclo or branched chained alkenyl of 3-10 carbons; X is thienyl, pyridyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl and oxazolyl; A is (CH.sub.2).sub.n where n is 0-5, lower branched chain alkyl having 3-6 carbons, cycloalkyl having 3-6 carbons, alkenyl having 2-6 carbons and 1 or 2 double bonds, alkynyl having 2-6 carbons and 1 or 2 triple bonds; B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR.sub.8, CONR.sub.9 R.sub.10, --CH.sub.2 OH, CH.sub.2 OR.sub.11, CH.sub.2 OCOR.sub.11, CHO, CH(OR.sub.12).sub.2, CHOR.sub.13 O, --COR.sub.7, CR.sub.7 (OR.sub.12).sub.2, or CR.sub.Type: GrantFiled: September 27, 1993Date of Patent: February 21, 1995Assignee: Allergan, Inc.Inventor: Roshantha A. S. Chandraratna
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Patent number: 5371240Abstract: 3-substituted thiophene compounds contaminating the analogous 2-substituted thiophene compounds, e.g. 3-acetylthiophene contaminating 2-acetyl thiophene, are removed by a selective electrophilic substitution process, e.g. bromination, followed by fractional distillation. It has been found that electrophilic substitution as exemplified by bromination is highly selective towards the 3-substituted thiophenes, yielding compounds of significantly higher molecular weights for separation purposes, to give high purity 2-substituted thiophene compounds.Type: GrantFiled: November 30, 1992Date of Patent: December 6, 1994Assignee: Torcan Chemical Ltd.Inventor: Clarke Slemon
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Patent number: 5358938Abstract: 2,5-Diaryl tetrahydrofurans, 2,5-diaryl terahydrothiophenes, 2,4-diaryl tetrahydrofurans, 2,4-diaryl tetrahydrothiphenes, 1,3-diaryl cyclopentanes, 2,4-diaryl pyrrolidines, and 2,5-diaryl pyrrolidines are disclosed that reduce the chemotaxis and respiratory burst leading to the formation of damaging oxygen radicals of polymorphonuclear leukocytes during an inflammatory or immune response. The compounds exhibit this biological activity by acting as PAF receptor antagonists, by inhibiting the enzyme 5-lipoxygenase, or by exhibiting dual activity, i.e., by acting as both a PAF receptor antagonist and inhibitor of 5-lipoxygenase.A method to treat disorders mediated by PAF or leukotrienes is also disclosed, that includes administering an effective amount of one or more of the above-identified compounds or a pharmaceutically acceptable salt thereof, optionally in a pharmaceutically acceptable carrier.Type: GrantFiled: July 13, 1992Date of Patent: October 25, 1994Assignee: CytoMed, Inc.Inventors: Xiong Cai, Saijat Hussoin, San-Bao Hwang, David Killian, T. Y. Shen
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Patent number: 5334730Abstract: The present invention provides a process for the preparation of optically active carboxylic acids of the formula I* or II* ##STR1## in which X is an oxygen or sulfur atom and n is 1 or 2. The process comprises reacting a racemic carboxylic acid I or II or its derivatives with an optically active 2-amino-carboxylic acid ester to give the diastereomeric carboxylic acid amides, separating the diastereomers and, after cleavage of the amide bond, isolating the optically active carboxylic acids of the general formula I* or II*. The invention also provides certain novel optically active carboxylic acid amides and a tetrahydrothiopyran-2-carboxylic acid.Type: GrantFiled: July 1, 1992Date of Patent: August 2, 1994Assignee: Consortium fur Elektrochemische Industrie GmbHInventor: Elke Fritz-Langhals
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Patent number: 5330965Abstract: Cyclohexenone oxime ethers of the formula I ##STR1## (R.sup.1 =C.sub.1 -C.sub.6 -alkyl; A=substituted or unsubstituted alkylene or alkenylene;Z=a 5-membered or 6-membered heteroaromatic structure;X=substituted or unsubstituted amino, nitro, cyano, halogen, alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, substituted or unsubstituted benzyloxycarbonyl and phenyl;n=0 to 3, or 1 to 4 where Z is halogen-substituted pyridyl; andR.sup.Type: GrantFiled: January 15, 1993Date of Patent: July 19, 1994Assignee: BASF AktiengesellschaftInventors: Ulf Misslitz, Norbert Meyer, Juergen Kast, Norbert Goetz, Albrecht Harreus, Thomas Kuekenhoehner, Bruno Wuerzer, Helmut Walter, Karl-Otto Westphalen, Matthias Gerber
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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: 5310940Abstract: A method of producing a dibenzoxazolyl thiophene represented by the formula ##STR1## wherein R"' represents a hydrogen, an alkyl of 1-8 carbons, a cycloalkyl, a phenyl, a substituted phenyl or a benzyl, which includes: reacting a thiophene-2,5-dicarboxylic acid diester represented by the formula ##STR2## wherein R' represents a branched alkyl of 3-5 carbons, phenyl, or tolyl, with an aminophenol represented by the formula ##STR3## wherein R"' is the same as before, in the presence of an acid catalyst, wherein the acid catalyst is boric acid, phosphoric acid, polyphosphoric acid, zinc chloride, ferric chloride, or sulfuric acid.Type: GrantFiled: January 19, 1993Date of Patent: May 10, 1994Assignee: Sumitomo Seika Chemicals Co., Ltd.Inventors: Hiroshi Goda, Nario Kimura, Satoshi Kimura, Naohiro Yoshikawa, Masaki Teramoto, Yoshihide Masuda, Yuuji Matuzaki
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Patent number: 5300655Abstract: This invention relates to novel 3-substituted-2-oxindole derivatives which are inhibitors of prostaglandin H.sub.2 synthase, 5-lipoxygenase and interleukin-1 biosynthesis. The compounds of the invention are useful as inhibitors of prostaglandin H.sub.2 synthase and interleukin-1 biosynthesis, per se, and as analgesic, antiinflammatory and antiarthritic agents in the treatment of chronic inflammatory diseases. This invention also relates to pharmaceutical compositions comprising said 3-substituted-2-oxindole derivatives; to methods of inhibiting prostaglandin H.sub.2 synthase and biosynthesis of interleukin-1; and to treating chronic inflammatory diseases in a mammal with said compounds. Further, this invention relates to certain novel carboxylic acids useful as intermediates in the preparation of the 3-substituted-2-oxindole derivatives of this invention and to a process for the preparation of the 3-substituted-2-oxindole derivatives.Type: GrantFiled: December 16, 1992Date of Patent: April 5, 1994Assignee: Pfizer Inc.Inventors: Frederick J. Ehrgott, Carl J. Goddard, Gary R. Schulte
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Patent number: 5296601Abstract: A process for producing a carboxylic acid ester, which comprises reacting an organic chloride having at least one chlorine atom on its ring of a substituted or unsubstituted, aromatic or heterocyclic hydrocarbon with carbon monoxide and an amine or an alcohol in the presence of a base by using as catalysts a palladium compound and a phosphine compound represented by the general formula (V):(R).sub.2 P--X--P(R).sub.2 (V)wherein R is an alkyl group or a substituted or unsubstituted phenyl group, and X is an alkylene group having 1 to 6 carbon atoms, ##STR1## or a binaphthyl group.Type: GrantFiled: May 27, 1992Date of Patent: March 22, 1994Assignee: Nihon Nohyaku Co., Ltd.Inventors: Keiji Suto, Masaaki Kudo, Moriharu Yamamoto
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Patent number: 5292767Abstract: A compound of the formula [I] and pharmaceutically acceptable salts thereof; and a synthetic intermediate represented by the formula [II] and pharmaceutically acceptable salts thereof, ##STR1## wherein R 1 is hydrogen or lower alkyl;R 2 is hydrogen or a protective group of thiol;R 3 is hydroxy, a remainder of ester group or a remainder of amido group;A is straight or branched lower alkylene, andthe sulfur atom in the side chain may be directly join with --CO-- to conform a thiolactone ring.The compounds of this invention have excellent thymulin-like activities and are expected to be useful for treatment of various immune disorders such as immunodeficiency and autoimmune diseases.Type: GrantFiled: February 18, 1993Date of Patent: March 8, 1994Assignee: Santen Pharmaceutical Co., Ltd.Inventors: Shiro Mita, Yoichi Kawashima, Nobuharu Kato, Hiroshi Suhara, Koji Yoneda, Masataka Morishita
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Patent number: 5278333Abstract: A process for the .alpha.-monoalkylation of arylacetonitriles, arylacetoesters and arylacetic acids with dialkyl carbonates in liquid phase, in the presence of bases at temperatures ranging from about 100.degree. C. to about 270.degree. C.Type: GrantFiled: July 30, 1992Date of Patent: January 11, 1994Assignee: Tessenderlo Chemie N.V.Inventors: Pierre C. Loosen, Pietro Tundo, Maurizio Selva
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Patent number: 5246962Abstract: Retinoid-like activity is exhibited by compounds of the formula ##STR1## where R is hydrogen or lower alkyl; A is pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl or pyrazinyl; n is 0-5; and B is H, --COOH or an ester or amide thereof, --CH.sub.2 OH or an ether or ester derivative thereof, or --CHO or an acetal derivative thereof, or --COR.sub.1 or a ketal derivative thereof where R.sub.1 is --(CH.sub.2).sub.m CH.sub.3 where m is 0-4; or a pharmaceutically acceptable salt thereof.Type: GrantFiled: September 21, 1992Date of Patent: September 21, 1993Assignee: Allergan, Inc.Inventor: Roshantha A. S. Chandraratna
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Patent number: 5235101Abstract: An improved process for the separation of enantiomers of a mixture of certain aliphatic carboxylic acids or esters thereof is disclosed. The process involves adding an inert liquid to the reaction solution formed by: (i) forming a salt solution comprising said racemic mixture of a C.sub.1 to C.sub.6 linear or branched aliphatic carboxylic acid and an organic or inorganic base; (ii) treating said salt solution with less that equimolar equivalents of a chiral organic nitrogenous base; (iii) precipitating from the reaction solution formed in step (ii) the less soluble diastereomeric salt; (iv) addition of a countersolvent to the slurry formed in step (iii); (v) extracting the more soluble diastereomeric salt or the salt of carboxylic acid and the base added in step (i) into the countersolvent. The inert liquid and the countersolvent must be of sufficiently different density.Type: GrantFiled: January 24, 1992Date of Patent: August 10, 1993Assignee: Ethyl CorporationInventors: Deepak R. Patil, Azfar A. Choudhury, Abbas Kadkhodayan
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Patent number: 5235095Abstract: An improved process for the separation of enantiomers of a racemic mixture of certain aliphatic carboxylic acids or esters thereof is disclosed. The process involves: (i) forming a salt solution comprising said racemic mixture of a C.sub.1 to C.sub.6 linear or branched aliphatic carboxylic acid and an organic or inorganic base; (ii) treating said salt solution with one-half molar equivalent of a chiral organic nitrogenous base having a base strength no stronger than said organic or inorganic base; and (iii) precipitating from the reaction solution formed in step (ii) the less soluble diastereomeric salt, the improvement being adding to the salt solution of step (ii) an inert organic or inorganic base that is soluble in the salt solution.Type: GrantFiled: January 24, 1992Date of Patent: August 10, 1993Assignee: Ethyl CorporationInventors: Abbas Kadkhodayan, Deepak R. Patil, Azfar A. Choudhury
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Patent number: 5235100Abstract: A process for the separation of a racemic mixture of certain aliphatic carboxylic acids or esters thereof is disclosed. The process comprises:i) separating a racemic mixture of an aliphatic carboxylic acid or ester thereof having the formula: ##STR1## where R.sub.1 is hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl; 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; cycloalkyl; alkyl-substituted cycloalkyl; C.sub.6 to C.sub.14 aryl; C.sub.1 to C.sub.6 alkylthio; C.sub.2 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; or C.sub.4 to C.sub.Type: GrantFiled: January 24, 1992Date of Patent: August 10, 1993Assignee: Ethyl CorporationInventors: Azfar A. Choudhury, Abbas Kadkhodayan, Deepak R. Patil
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Patent number: 5219886Abstract: Novel mercapto-acylamino acids of the formula ##STR1## wherein Q is hydrogen or R.sup.7 CO--;R.sup.1 is lower alkyl, cyclolower alkyl, aryl or heteroaryl;R.sup.2 is hydrogen; lower alkyl; cyclolower alkyl; lower alkyl substituted with hydroxy, lower alkoxy, mercapto, lower alkylthio, aryl or heteroaryl; aryl; or heteroaryl;R.sup.3 is --OR.sup.5 or --NR.sup.5 R.sup.6 ;R.sup.4 and R.sup.9 are independently --(CH.sub.2).sub.q R.sup.8, provided that when R.sup.4 and R.sup.9 are both hydrogen, R.sup.2 is biphenylyl, phenoxyphenyl, phenylthiophenyl, naphthyl, heteroaryl, or lower alkyl substituted with hydroxy, lower alkoxy, mercapto or lower alkylthio;R.sup.5 and R.sup.6 are independently selected from the group consisting of hydrogen, lower alkyl, hydroxy lower alkyl, lower alkoxy lower alkyl and aryl lower alkyl, or R.sup.5 and R.sup.6 together with the nitrogen to which they are attached form a 5-7 membered ring;R.sup.7 is hydrogen, lower alkyl or aryl;R.sup.Type: GrantFiled: October 1, 1991Date of Patent: June 15, 1993Assignee: Schering CorporationInventors: Elizabeth M. Smith, Philip M. DeCapite, Bernard R. Neustadt
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Patent number: 5216139Abstract: Thiopheneazo dyes of the formula ##STR1## where R.sup.1 is cyano, C.sub.1 -C.sub.4 -alkoxycarbonyl, phenylazo, phenylsulfonyl, formyl or the radical ##STR2## where R.sup.7 and R.sup.8 are independently of the other cyano or C.sub.1 -C.sub.4 -alkoxycarbonyl,R.sup.2 is C.sub.1 -C.sub.4 -alkyl, phenyl, halogen, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkoxycarbonyl, or R.sup.1 and R.sup.2 together are the radical (CH.sub.2).sub.3 --CO, which may be substituted by 1 or 2 methyl groups and whose carbonyl group is bonded to the thiophene ring in the ortho position relative to the sulfur atom,R.sup.3 is cyano or C.sub.1 -C.sub.4 -alkoxycarbonyl,R.sup.4 is C.sub.1 -C.sub.8 -alkyl, cyclohexyl, phenoxy-C.sub.1 -C.sub.4 -alkyl, substituted or unsubstituted phenyl, or substituted or unsubstituted thienyl,R.sup.5 is C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.7 -alkyl whose alkyl chain is interrupted by 1 or 2 oxygen atoms, or C.sub.1 -C.sub.4 -alkoxy andR.sup.6 is cyanoethyl, phenylethyl or C.sub.3 -C.sub.Type: GrantFiled: December 4, 1990Date of Patent: June 1, 1993Assignee: BASF AktiengesellschaftInventors: Karl-Heinz Etzbach, Guenter Hansen, Gunther Lamm, Helmut Reichelt
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Patent number: 5201934Abstract: Carboxamides of the formulae Ia to Ic ##STR1## where X is oxygen or sulfur;R.sup.1 is hydrogen or substituted or unsubstituted cycloalkyl or alkyl;R.sup.2 is hydroxy, alkoxy, cyanoalkyl, substituted or unsubstituted alkenyl, alkynyl, phenyl or naphthyl, or one of the groups stated for R.sup.1 ;R.sup.3 and R.sup.4 are nitro, cyano, halogen, substituted or unsubstituted amino, alkoxy, alkylthio, substituted or unsubstituted alkenyl, alkynyl, phenyl, phenoxy or phenylthio, or one of the groups stated for R.sup.1 ;R.sup.5 is formyl, 4,5-dihydrooxazol-2-yl or COYR.sup.6 (Y.dbd.O,S);R.sup.6 is hydrogen, cycloalkyl, substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkenyl or phenyl,phthalimido, tetrahydrophthalimido, succinimido, maleimido, benzotriazolyl ora group --N.dbd.CR.sup.7 R.sup.8, whereR.sup.7 and R.sup.8 are hydrogen or alkyl, and R.sup.8 may also be cycloalkyl, phenyl, or R.sup.7 and R.sup.8 together form a 4- to 7-membered alkylene chain;and if R.sup.Type: GrantFiled: October 3, 1990Date of Patent: April 13, 1993Assignee: BASF AktiengesellschaftInventors: Peter Muenster, Gerd Steiner, Wolfgang Freund, Bruno Wuerzer, Karl-Otto Westphalen
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Patent number: 5200553Abstract: Biologically active carboxylic acid esters which promote antitumor or immune response are selected from the group consisting of compounds having formulas (I), (II) and (III):XCH.sub.2 --CHX--CHX--C(.dbd.O)--O--Z (I)CH.sub.3 --CO--CH.sub.2 --C(.dbd.O)--O--Z (II)CH.sub.3 --CH.sub.2 --CO--C(.dbd.O)--O--Z (III)wherein X is H, or one X only may be OH; Z is --CHR--O--(O.dbd.Type: GrantFiled: July 25, 1988Date of Patent: April 6, 1993Assignee: Kupat Holim Health Insurance Institution of the General Federation of LaborInventors: Abraham Nudelman, Matitiahu Shaklai, Ada Rephaeli
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Patent number: 5194631Abstract: A process for producing a carboxylic acid which comprises reacting an organic chloride having at least one chloride atom on its ring of a substituted or unsubstituted, aromatic or heterocyclic hydrocarbon with carbon monoxide in the presence of an inorganic base or an organic base and water at a reaction temperature of 150.degree. to 300.degree. C., and preferably 160.degree. to 300.degree. C., by using as catalysts a palladium compound and a phosphine compound represented by the general formula (III):(R).sub.2 P--X--P(R).sub.2 (III)wherein R is an alkyl group or a substituted or unsubstituted phenyl group, and X is an alkylene group having 1 to 6 carbon atoms, ##STR1## or a binaphthyl group.Type: GrantFiled: July 11, 1989Date of Patent: March 16, 1993Assignee: Nihon Nohyaku Co., Ltd.Inventors: Keiji Suto, Koji Nakasa, Masaaki Kudo, Moriharu Yamamoto
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Patent number: 5190573Abstract: Cyclohexenone oxime ethers ##STR1## where R.sup.1 is alkyl;A is substituted or unsubstituted alkylene or alkenylene, where methylene is replaced by an oxygen atom, a sulfur atom, a sulfoxyl group, a sulfonyl group or --NR.sup.a --,Z is phenyl or a 5- or 6-membered heteroaromatic structure;X is substituted or unsubstituted amino, nitro, cyano, halogen, alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, substituted or unsubstituted benzyloxycarbony or phenyl;n is 0 to 3, or 1 to 5 where X is halogen;R.sup.Type: GrantFiled: May 8, 1991Date of Patent: March 2, 1993Assignee: BASF AktiengesellschaftInventors: Ulf Misslitz, Norbert Meyer, Juergen Kast, Norbert Goetz, Albrecht Harreus, Bruno Wuerzer, Helmut Walter, Karl-Otto Westphalen, Matthias Gerber
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Patent number: 5183818Abstract: The present invention provides compounds having the structureY-Het-[Q.sub.1 ]-X-[Q.sub.2 ]-Zwhich inhibit the catalytic action of lipoxygenase enzymes, particularly 5-lipoxygenase, and thereby reduce the biosynthesis of leukotrienes B.sub.4, C.sub.4, D.sub.4, and E.sub.4.In the generic formula given above, X is oxygen or sulfur and Het is a heteroaryl group selected from the group consisting of furyl, thienyl, 2-, 3-, and 4-pyridyl, 2- and 3-benzo[b]furyl, 2- and 3-benzo[b]thienyl and thienothienyl.Y is one or two substituents independently selected from hydrogen, hydroxy, halogen, cyano, alkyl, haloalkyl, alkoxy, alkylthio, alkoxyaryl), alkylthioaryl, arylalkoxy, arylalkylthio, aryloxy, arylthio, alkylamido, cycloalkyl, alkanoyl, alkoxycarbonyl, amino, alkylamino, dialkylamino, and the following groups wherein R, at each occurrence, is independently selected from hydrogen and alkyl of from one to six carbon atoms: --CRROR, --NRC(O)R, --NRC(O)OR, and --C(O)NRR.The group Q.sub.Type: GrantFiled: August 27, 1991Date of Patent: February 2, 1993Assignee: Abbott LaboratoriesInventors: Dee W. Brooks, Andrew O. Stewart, Jonathan G. Martin
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Patent number: 5182348Abstract: Compounds of the formula (1) ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7 and R.sup.8 have the meanings given in the description, and the other radicals have the following meanings:X, Y and Z denote identical or different divalent radicals --O--, --S--, --N(R.sup.9)-- or --C(R.sup.10).dbd.C(R.sup.11)--, with the proviso that at least one of the radicals, X, Y and Z is not a radical of the formula --C(R.sup.10).dbd.C(R.sup.11)--, and whereinR.sup.9 is a hydrogen atom, a branched or unbranched C.sub.1 - to C.sub.8 -alkyl radical or an optionally substituted phenyl radical, andR.sup.10 and R.sup.11 are, in each case, identical or different radicals which have one of the meanings of R.sup.1,R.sup.7 and R.sup.8 denote identical or different radicals, that is to say hydrogen atoms or C.sub.1 - to C.sub.6 -alkyl or phenyl radicals, andn, m and o denote identical or different integers with a value of from 1 to 10.Type: GrantFiled: August 19, 1991Date of Patent: January 26, 1993Assignee: Wacker-Chemie GmbHInventors: Hermann Braeunling, Richard Becker, Georg Bloechl
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Patent number: 5175185Abstract: Retinoid like activity is exhibited by compounds of the formula ##STR1## R.sub.1 -R.sub.3 independently are hydrogen, lower alkyl, cycloalkyl or lower alkenyl, A and A.sub.1 independently are hydrogen, lower alkyl, cycloalkyl, lower alkenyl, SR.sub.4 or OR.sub.4 where R.sub.4 is lower alkyl, cycloalkyl or lower alkenyl; Y is selected from a group consisting of thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl or oxazolyl; E is lower alkenyl, lower alkynyl, lower cycloalkyl, lower branched chain alkyl, or is characterized by the formula (CH.sub.2).sub.n where n is 0-5, and Z is H, OH, OR.sub.5, OCOR.sub.5, --COOH or a pharmaceutically acceptable salt, ester or amide thereof, --CH.sub.2 OH, CH.sub.2 OR.sub.6, CH.sub.2 OCOR.sub.6, or --CHO, CH(OR.sub.7).sub.2, CHOR.sub.8 O, or COR.sub.9, CR.sub.9 (OR.sub.7).sub.2, CR.sub.9 OR.sub.8 O where R.sub.5 is lower alkyl, phenyl or lower alkylphenyl, R.sub.6 is lower alkyl, phenyl or lower alkylphenyl, R.sub.7 is lower alkyl, R.sub.Type: GrantFiled: March 14, 1991Date of Patent: December 29, 1992Assignee: Allergan, Inc.Inventor: Roshantha A. S. Chandraratna
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Patent number: 5166218Abstract: Tertiary and secondary amines of the formulas ##STR1## and ##STR2## wherein n is the integer 1 or 2,R is hydrogen, lower-alkanoyl or phenyl-lower-alkanoyl,X.sup.1 is phenoxymethyl optionally mono-fluorinated or mono-chlorinated in the ortho-position,X.sup.2 is lower-alkyl, phenoxymethyl optionally mono-fluorinated or mono-chlorinated in the ortho-position or phenyl optionally monosubstituted by fluorine, chlorine, trifluoromethyl or lower-alkoxy,Y is hydrogen or methyl, andZ is a phenyl or thienyl residue substituted as hereinafter described,and the physiologically and pharmaceutically compatible salts are described. The compounds of formulas I and V-1 have catabolic activity and can be used for the treatment of obesity and diabetes mellitus or for the treatment of conditions which are associated with an increased protein breakdown, or as feed additives for fattening animals. The compounds of formulas I and V-1 can be prepared starting from corresponding primary amines.Type: GrantFiled: August 12, 1991Date of Patent: November 24, 1992Assignee: Hoffmann-La Roche Inc.Inventors: Leo Alig, Marcel Muller
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Patent number: 5149705Abstract: Retinoid-like activity is exhibited by compounds of the formula ##STR1## where R is hydrogen or lower alkyl; A is pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl or pyrazinyl; n is 0-5; and B is H, --COOH or an ester or amide thereof, --CH.sub.2 OH or an ether or ester derivative thereof, or --CHO or an acetal derivative thereof, or --COR.sub.1 or a ketal derivative thereof where R.sub.1 is --(CH.sub.2).sub.m CH.sub.3 where m is 0-4; or a pharmaceutically acceptable salt thereof.Type: GrantFiled: March 13, 1987Date of Patent: September 22, 1992Assignee: Allergan, Inc.Inventor: Roshantha A. S. Chandraratna
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Patent number: 5131945Abstract: Compounds of formula I ##STR1## are useful as herbicides, effective against dicotyledonous weeds.Type: GrantFiled: July 13, 1990Date of Patent: July 21, 1992Assignee: Shell Research LimitedInventors: Hans-Joachim Bissinger, Ludwig Schoeder, Helmut Baltruschat, Manfred Garrecht, Erich Raddatz, Wolfgang Fruhstorfer
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Patent number: 5118683Abstract: Compounds of the formula I ##STR1## wherein R.sup.5 represents C.sub.1 to C.sub.6 -alkyl or the group --(CH.sub.2).sub.n --Z--(CH.sub.2).sub.m --Ar;Z represents O, S or --CH.sub.2 --;n represents an integer of 1 to 8;m represents zero or an integer of 1 to 8;one of R.sup.1 and R.sup.2 represents the group ##STR2## and the other represents hydrogen or R.sup.7 CO--; R.sup.7 is C.sub.1 to C.sub.10 alkyl, C.sub.3 to C.sub.8 cycloalkyl, aryl, heteroaryl, --N(R.sup.9 R.sup.10), or R.sup.11 O--; R.sup.3, R.sup.4, R.sup.9, and R.sup.10 are each independently selected from hydrogen, C.sub.1 to C.sub.6 alkyl and Ar.sup.1 ; R.sup.6 and R.sup.11 are each independently C.sub.1 -C.sub.8 alkyl; Ar and Ar.sup.1 are each independently selected from the group consisting of phenyl or phenyl substituted by one or two substituents selected from the group consisting of R.sup.12, R.sup.13 O--; R.sup.14 S(O).sub.x --, R.sup.15 CO--, (R.sup.16 R.sup.17)NCO--, F, Cl, Br, I, NO.sub.2, CF.sub.3, CN, or phenyl; R.sup.12, R.sup.13, R.sup.Type: GrantFiled: June 13, 1990Date of Patent: June 2, 1992Assignee: Schering CorporationInventors: David J. Blythin, Ho-Jane Shue
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Patent number: 5112864Abstract: This invention relates to novel compounds for treating inflammatory conditions by inhibition of phospholipase A.sub.2 activity of the formula ##STR1## wherein X is oxygen, sulfur or --CH.dbd.CH--; wherein R.sup.1 is hydrogen, alkyl of 1 to 6 carbons or a pharmaceutically acceptable cation;wherein R.sup.2 is phenoxy, alkoxy, methyl, trifluoromethyl or phenyl;wherein n is an integer from 1 to 20;compositions comprised of the novel compounds; and methods of treating inflammatory conditions with these compositions.Type: GrantFiled: May 30, 1991Date of Patent: May 12, 1992Assignee: G. D. Searle & Co.Inventors: Stevan W. Djuric, Stephen H. Docter, Richard A. Haack
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Patent number: 5101049Abstract: Novel compounds, 2-(.alpha.-alkoxyimino)ethylthiophenes are susceptible to electrophilic substitution reactions, and the acetylation, nitration, sulfonation and halogenation of the compounds provide 5-acetyl-2-(.alpha.-alkoxyimino)ethylthiophenes, 5-nitro-2-(.alpha.-alkoxyimino)ethylthiophenes, 5-(.alpha.-alkoxyimino)ethyl-2-thiophenesulfonic acid and 5-halo-2-(.alpha.-alkoxyimino)ethylthiophenes, respectively.The hydrolysis of 5-acetyl-2-(.alpha.-alkoxyimino)ethylthiophenes readily provides a known compound, 2,5-diacetylthiophene which is an important intermediate for the production of medicines, whereas the haloform reaction provides novel compounds, 5-(.alpha.-alkoxyimino)ethyl-2-thiophenecarboxylic acids, the hydrolysis of which compounds readily provides a known compound, 5-acetyl-2-thiophenecarboxylic acids, an important intermediate for the production of medicines.The hydrolysis of 5-(.alpha.Type: GrantFiled: August 20, 1990Date of Patent: March 31, 1992Assignee: Seitetsu Kagaku Co., Ltd.Inventors: Hiroshi Goda, Masao Kawamura, Kunioki Kato, Makoto Sato
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Patent number: 5098466Abstract: Substituted semicarbazones, thiosemicarbazones and isothiosemicarbazones and salts thereof, intermediates therefor, synthesis thereof, and the use of said compounds for the control of weeds.Type: GrantFiled: August 21, 1990Date of Patent: March 24, 1992Assignee: Sandoz Ltd.Inventors: Richard J. Anderson, Michael M. Leippe, Joe T. Bamberg
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Patent number: 5093504Abstract: There is disclosed a method of producing a thiophene-2,5-dicarboxylic acid diester represented by the formula ##STR1## wherein R' represents an alkyl of 1-8 carbons, a phenyl, a substituted phenyl or benzyl, which comprises:halogenating a tetrahydrothiophene-2,5-dicarboxylic acid diester represented by the formula ##STR2## wherein R' is the same as before, with a halogenating agent selected from the group consisting of halogens and sulfuryl halides in an amount of 2-4 moles per mole of the tetrahydrothiophene-2,5-dicarboxylic acid diester; and thendehydrohalogenating the resultant halogenated tetrahydrothiphpene-2,5-dicarboxylic acid diester in the presence of an alcohol, a base, a metal or a metal ion.There is also disclosed a method of producing tetrahydrothiophene-2,5-dicarboxylic acid diester and dibenzoxazolyl thiophenes. Some of the thiophene-2,5-dicarboxylic acid diesters and tetrahydrothiophene-2,5-dicarboxylic acid diesters are novel.Type: GrantFiled: March 12, 1990Date of Patent: March 3, 1992Assignee: Sumitomo Seika Chemicals, Co., Ltd.Inventors: Hiroshi Goda, Nario Kimura, Satoshi Kimura, Naohiro Yoshikawa, Masaki Teramoto, Yoshihide Masuda, Yuuji Matuzaki
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Patent number: 5081224Abstract: This invention relates to processes for producing an olefin-terminated polyester. In one of the processes which comprises reacting an olefin-terminated diester compound with a lactone in the presence of a polymerization catalyst with transesterification ability, the lactone is in a limited amount added to the reaction system. In another process which comprises reacting an olefin-terminated diester compound, a lactone compound, a cyclic acid anhydride and an epoxy compound in the presence of a polymerization catalyst with transesterification ability, the lactone, cyclic acid anhydride and epoxy compound are each in a limited amount added to the reaction system. In accordance with this invention, olefin-terminated polyesters having high terminal modification rates can be synthesized.Type: GrantFiled: October 12, 1990Date of Patent: January 14, 1992Assignee: Kanegafuchi Chemical Industry Co., Ltd.Inventors: Hiroshi Ando, Kazumasa Hashimoto, Jun Hattori, Kazuya Yonezawa
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Patent number: 5073184Abstract: Compounds of formula (I): ##STR1## and stereoisomers thereof, wherein W is R.sup.1 O.sub.2 C--C.dbd.CH--ZR.sup.2, wherein R.sup.1 and R.sup.2, which are the same or different, are alkyl or fluoroalkyl groups, and Z is either an oxygen or sulphur atom; A is an oxygen or sulphur atom, --NR.sup.3 --, or --CR.sup.4 R.sup.5 --; X, Y and Z.sup.Type: GrantFiled: April 9, 1990Date of Patent: December 17, 1991Assignee: Imperial Chemical Industries PLCInventors: Vivienne M. Anthony, John M. Clough, Paul deFraine, Christopher R. A. Godfrey, Kevin Beautement
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Patent number: 5064863Abstract: Tertiary and secondary amines of the formulas ##STR1## wherein n is the integer 1 or 2, p0 R is hydrogen, lower-alkanoyl or phenyl-lower-alkanoyl,X.sup.1 is phenoxymethyl optionally mono-fluorinated or mono-chlorinated in the ortho-position,X.sup.2 is lower-alkyl, phenoxymethyl optionally mono-fluorinated or mono-chlorinated in the ortho-position or phenyl optionally monosubstituted by fluorine, chlorine, trifluoromethyl or lower-alkoxy,Y is hydrogen or methyl, andZ is a phenyl or thienyl residue substituted as hereinafter described,and the physiologically and pharmaceutically compatible salts are described. The compounds of formulas I and V-1 have catabolic activity and can be used for the treatment of obesity and diabetes mellitus or for the treatment of conditions which are associated with an increased protein breakdown, or as feed additives for fattening animals. The compounds of formulas I and V-1 can be prepared starting from corresponding primary amines.Type: GrantFiled: December 10, 1987Date of Patent: November 12, 1991Assignee: Hoffmann-La Roche Inc.Inventors: Leo Alig, Marcel Muller
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Patent number: 5055471Abstract: This invention relates to derivatives of propanoic acid of the formula ##STR1## Useful as fungicides, insecticides and miticides, to processes for preparing them, to compositions containing them, and to methods of using them to combat fungi, especially fungal infections of plants, and to kill or control insects and mites.Type: GrantFiled: November 15, 1989Date of Patent: October 8, 1991Assignee: Imperial Chemical Industries PLCInventors: Paul J. de Fraine, Anne Martin
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Patent number: 5034049Abstract: Thiophene-2-carboxylic acid derivatives of the general formula I ##STR1## where R.sup.1 to R.sup.3 are each hydrogen, halogen, branched or straight-chain C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.8 -alkoxy, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -haloalkoxy, nitro, cyano, unsubstituted phenyl or phenyl which is mono- to trisubstituted by C.sub.1 -C.sub.4 -alkyl, halogen, C.sub.1 -C.sub.5 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.5 -haloalkoxy;X is --OR.sup.4 or --NH--OR.sup.5,R.sup.4 being branched or straight-chain C.sub.3 -C.sub.10 -alkynylalkyl which is unsubstituted or substituted by halogen; andR.sup.5 being branched or straight-chain C.sub.1 -C.sub.5 -alkyl which is unsubstituted or substituted by halogen, or branched or straight-chain C.sub.3 -C.sub.10 -alkynylalkyl which is unsubstituted or substituted by halogen;with the proviso that R.sup.4 is not propargyl when R.sup.2 and R.sup.3 are both hydrogen or when R.sup.2 is halogen or R.sup.3 is chlorine, methyl or methoxy.Type: GrantFiled: January 9, 1990Date of Patent: July 23, 1991Assignee: BASF AktiengesellschaftInventors: Reiner Kober, Rainer Seele, Hans-Juergen Neubauer, Thomas Saupe, Bruno Wuerzer, Norbert Meyer, Karl-Otto Westphalen
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Patent number: 5032609Abstract: The invention relates to compounds of general formula (I) and physiologically acceptable salts and solvates thereof, methods for their preparation and pharmaceutical formulations thereof. ##STR1## wherein Ar represents a substituted phenyl or nitrogen-containing heterocyclic ring;X and Y represent alkylene, alkenylene or alkynylene chains;R.sup.1, R.sup.2 and R.sup.18 each represent hydrogen or alkyl groups; andQ represents an optionally substituted furan or thiophene ring.The compounds of the invention have a stimulant action at .beta..sub.2 -adrenoreceptors and are useful in the treatment of diseases associated with reversible airways obstruction such as asthma and chronic bronchitis.Type: GrantFiled: December 16, 1988Date of Patent: July 16, 1991Assignee: Glaxo Group LimitedInventors: Ian F. Skidmore, Harry Finch, Alan Naylor, Lawrence H. C. Lunts, Charles Willbe, David Middlemiss
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Patent number: 5006548Abstract: Compounds of the general formula: ##STR1## wherein R.sup.1 is heterocyclic group other than pyridyl and which is unsubstituted or substituted with lower alkyl or lower alkoxycarbonyl, R.sup.2 is hydrogen, halogen, or nitro, and R.sup.3 is carboxy group or its functional derivative, with the proviso that when R.sup.1 is an unsubstituted furyl, or furyl mono- or polysubstituted with alkyl and R.sup.2 is hydrogen, then R.sup.3 is functional derivative of carboxy and, where applicable, pharmaceutically acceptable salts thereof are hyaluronidase inhibitors and useful as anti-allergic agent.Type: GrantFiled: August 7, 1989Date of Patent: April 9, 1991Assignee: Sawai Pharmaceutical Co., Ltd.Inventors: Toshio Satoh, Hitoshi Matsumoto, Hisao Kakegawa, Yoshiko Kato, Juichi Riku, Junji Yoshinaga, Yoshifumi Kanamoto
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Patent number: 4997848Abstract: Compounds of formula (I): ##STR1## in which: R represents hydrogen, methyl of hydroxy; X represents an alkyl, alkenyl, cycloalkyl, aryl, aralkyl, or heterocyclic group; A represents a single bond, or an alkylene, alkenylene, alkynylene or alkadienylene group; Y represents hydrogen, or an aryl, cycloalkyl or heterocyclic group] have valuable antihypercholesteremic activities and may be used in the treatment of disorders arising from a blood cholesterol imbalance in humans and other animals.Type: GrantFiled: October 21, 1988Date of Patent: March 5, 1991Assignee: Sankyo Company, LimitedInventors: Masaaki Kurabayashi, Hiroshi Kogen, Hiroshi Kadokawa, Hideshi Kurihara, Kazuo Hasegawa, Masao Kuroda
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Patent number: 4990522Abstract: Esterified ephedrine derivatives with prolonged antiulcer activity and low toxicity, having the following general formula: ##STR1## in which R is: ##STR2## The invention also describes a process for preparing derivatives of formula (I) and compositions containing them as active principle.Type: GrantFiled: March 2, 1990Date of Patent: February 5, 1991Assignee: Establissement TexcontorInventor: Federico Butelman
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Patent number: 4990287Abstract: An optical resonant assembly which comprises a plurality of partially light-transmitting mirrors, a layer of photochromic material disposed between the mirrors, a light source providing a light beam of variable intensity incident on the layer of photochromic material and detecting means for determining transmittance values of said incident beam at different intensity levels, said photochromic material having a low quantum yield for bleaching with light of a wavelength corresponding to said light beam and being selected from pyran compounds of the general formula (I) below: ##STR1## wherein X and Y together represent a spiro-adamantylidene group or a spiro-carbocyclic or heterocyclic group or X and Y independently represent hydrogen, alkyl (preferably lower alkyl having 1 to 5 carbon atoms) or phenyl and R.sub.3 and R.sub.4 each independently represent hydrogen, alkyl, aralkyl, aryl, halogen or a heterocyclic group and R.sup.Type: GrantFiled: February 19, 1988Date of Patent: February 5, 1991Assignee: The Plessey Company PLCInventors: Ian Bennion, Rosemary Cush, Christopher J. Groves-Kirby, Clive Trundle
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Patent number: 4980484Abstract: Retinoid-like activity is exhibited by compounds of the formula ##STR1## wherein A is pyridyl, furyl, thienyl, pyridazinyl, pyrimidinyl or pyrazinyl; n is 0-5; and B is H, --COOH and its esters, amides and pharmaceutically acceptable salts, --CHO and its acetal derivatives, --COR.sub.1 and its ketal derivatives where R.sub.1 is --(CH.sub.2).sub.n CH.sub.3 where n is defined above, or --CH.sub.2 OH and its ether and acyl ester derivatives; or a pharmaceutically acceptable salt.Type: GrantFiled: March 13, 1990Date of Patent: December 25, 1990Assignee: Allergan, Inc.Inventor: Roshantha A. S. Chandraratna
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Patent number: 4952580Abstract: Polyhaloalkene compounds of the formula: ##STR1## wherein X is sulfur, oxygen, or nitrogen, Y.sup.1 and Y.sup.2 are fluorine, Z is hydrogen or the same as Y.sup.1 and Y.sup.2, and n is 1-4; provided that:(A) when X is sulfur, Z is fluorine and R is thienyl or substituted thienyl, thianaphthyl or substituted thianaphthyl, thiazolinyl or substituted thiazolinyl, oxadiazolyl or substituted oxadiazolyl, 3,4,4-trifluoro-3-butenyloxycarbonylmethyl, thiadiazolyl substituted by halogen or R.sup.2 S, wherein R.sup.2 is 3,4,4-trifluoro-3-butenyl or R.sup.2 is phenylmethyl or phenylthiomethyl each optionally substituted by halogen or nitro; or R is thiadiazolyl substituted by R.sup.3, wherein R.sup.3 is substituted aryl, arylalkyl, aryloxyalkyl, alkylthio, haloalkylthio, haloarylthio, cyanoalkylthio, arylalkylthio, aryloxyalkylthio, arylthioalkylthio, heterocycloalkylthio, alkenylthio, haloalkenylthio, halocycloalkylalkenylthio, wherein said aryl or heterocyclic groups of R.sup.Type: GrantFiled: November 9, 1988Date of Patent: August 28, 1990Assignee: FMC CorporationInventors: Anthony J. Martinez, Thomas G. Cullen