The Spiro Includes The Lactone Ring Patents (Class 549/265)
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Patent number: 6103912Abstract: A novel class of bridged indicator dyes is disclosed which possess absorption in the infrared region of the electromagnetic spectrum. These bridged indicator dyes are useful as light-absorbing, pH-sensitive optical filter agents in diffusion transfer photographic processes adapted to be performed in the presence of ambient light and to diffusion transfer products useful in such processes. These indicator dyes will also find utility in titrations and other analytical techniques and products where pH-sensitive indicator dyes are employed and absorption of infrared is useful.Type: GrantFiled: March 31, 1993Date of Patent: August 15, 2000Assignee: Polaroid CorporationInventors: Charles E. Jandrue, Sr., Marcis M. Kampe, Myron S. Simon, David P. Waller, David C. Whritenour
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Patent number: 5981779Abstract: The present invention disclose to non-radioactive vitamin D compounds of formula (1) and methods to assay for the presence of vitamin D, vitamin D analogs and their metabolites which may be present in milk, blood or other biological fluids. The assay methods employed in this invention may be enzyme linked immununoassays (ELISAs) (with biotin containing compounds) and fluorimetric and chemiluminometric assays (with fluorescein or chemiluminiscence containing compounds).Type: GrantFiled: June 10, 1998Date of Patent: November 9, 1999Assignee: A and D Assay, IncorporatedInventors: Michael F. Holick, Rahul Ray
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Patent number: 5977169Abstract: This invention comprises novel substituted tetronic acid type compounds, 2, 4(3H, 5H)-furandiones, that are useful for the inhibition of the HIV protease enzyme. The compounds may be useful for the treatment of a person with AIDS or AIDS related diseases. The compounds may be used in the attempt to retard the further replication of any retrovirus containing the aspartyl protease enzyme. Compounds are represented by the formula below.Type: GrantFiled: July 28, 1997Date of Patent: November 2, 1999Inventors: Robert A. Chrusciel, Linda L. Maggiora, Suvit Thaisrivongs, James M. Tustin, Clark W. Smith, Ruben A. Tommasi, Paul A. Aristoff, Harvey I. Skulnick, W. Jeffrey Howe, Gordon L. Bundy
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Patent number: 5907047Abstract: This invention relates to a new biologically active compound as shown in formula (I) and its biologically active derivatives; whereas derivatives are produced by the reaction of formula (I) with nucleophiles.Type: GrantFiled: July 23, 1998Date of Patent: May 25, 1999Assignee: Boehringer Mannheim GmbHInventors: Fritz Hansske, Olov Sterner, Marc Satadler, Heidrun Anke, Liesel Dorge, Rudong Shan
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3-aryl-tetronic acid derivatives, the production thereof and the use thereof as antiparasitic agents
Patent number: 5830825Abstract: The present invention relates to new 3-aryl-4-hydroxy-.DELTA..sup.3 -dihydrofuranone derivatives of the formula (I) ##STR1## in which A and B together with the carbon atom to which they are bonded form an unsubstituted or substituted 5- to 7-membered ring which is interrupted by at least one hetero atom,X represents alkyl, halogen or alkoxy,Y represents hydrogen, alkyl, halogen, alkoxy or halogenoalkyl,Z represents alkyl, halogen or alkoxy,n represents a number 0, 1, 2 or 3,G represents hydrogen (a) or one of the groups ##STR2## E represents a metal Ion equivalent or an ammonium ion, L represents oxygen or sulphur,M represents oxygen or sulphur andR.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 have the meanings given in the description, to processes for their preparation, and to their use as pesticides.Type: GrantFiled: June 17, 1997Date of Patent: November 3, 1998Assignee: Bayer AktiengesellschaftInventors: Reiner Fischer, Thomas Bretschneider, Gunther Beck, Hermann Hagemann, Christoph Erdelen, Ulrike Wachendorff-Neumann, Wolfram Andersch, Norbert Mencke, Andreas Turberg -
Patent number: 5821374Abstract: A process for oxidizing primary and secondary alcohols to the corresponding aldehydes and ketones is disclosed. The oxidation is carried out by reacting the primary or secondary alcohol with an organic N-chloro compound oxidizing agent in the presence of a catalyst of the formula: ##STR1## wherein the substituent groups are as defined in the specification.Type: GrantFiled: November 12, 1996Date of Patent: October 13, 1998Assignee: Hoffmann-La Roche Inc.Inventors: Christian-Johannes Jenny, Bruno Lohri, Markus Schlageter
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Patent number: 5801254Abstract: Arteminolides obtained from Artemisia sylvatica MAXIMOWICZ and having a core structure of formula (I) or an isomeric structure thereof are effective farnesyl-protein transferase inhibitors as well as angiogenesis suppressors, and, accordingly, they are useful for the treatment of various cancers and angiogenesis-related diseases.Type: GrantFiled: August 5, 1997Date of Patent: September 1, 1998Assignee: Korea Institute of Science and TechnologyInventors: Byoung-Mog Kwon, Song-Hae Bok, Seung-Ho Lee, Young-Kook Kim, Mi-Jeong Kim, Jongheon Shin, Youngwan Seo, Soo-Ik Chang
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Patent number: 5683965Abstract: The aryl-keto-enolic heterocycles according to the invention have the formula (I), in which Het stands for a heterocyclic group from the series (a), (b) or (c), and X, Y, Z, n, A, B, E, L and M have the meanings given in the description. The compounds having the formula (I) are pesticides, in particular acaricides, insecticides, fungicides and herbicides. Also disclosed is their preparation.Type: GrantFiled: May 13, 1996Date of Patent: November 4, 1997Assignee: Bayer AktiengesellschaftInventors: Jurgen Bachmann, Thomas Bretschneider, Reiner Fischer, Bernd-Wieland Kruger, Hans-Joachim Santel, Markus Dollinger, Christoph Erdelen, Ulrike Wachendorff-Neumann
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Patent number: 5559252Abstract: The present invention provides a process for the preparation of compounds of formula (V) below, and analogs thereof, which are useful as intermediates for the synthesis of HIV protease inhibitors, including cyclic ureas.Type: GrantFiled: June 30, 1994Date of Patent: September 24, 1996Assignee: The DuPont Merck Pharmaceutical CompanyInventor: Robert F. Kaltenbach III
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Patent number: 5547836Abstract: Chemiluminescent bioassays for the presence or concentration of an analyte in a sample use 1,2-dioxetanes as substrates for the enzyme of an enzyme complex that bind to the analyte. The chemiluminescence obtained from the decomposition of the dioxetane triggered by the enzyme through the formation of the corresponding 1,2-dioxetane oxyanion of the enzyme complex is enhanced by the addition of TBQ as an enhancement agent. Other polymeric quaternary onium salts can be used as enhancement agents in conjunction with enhancement additives which improve the ability of the enhancement agent to form hydrophobic regions in the aqueous sample, in which regions the 1,2-dioxetane oxyanion and its chemiluminescent decomposition products can be sequestered. A kit for performing such assays is also provided.Type: GrantFiled: March 15, 1993Date of Patent: August 20, 1996
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Patent number: 5498734Abstract: The magnesium complexes of cyclic hydrocarbons containing conjugated dienes, such as 1,2-dimethylenecycloalkanes, and 1,3-butadienes, are readily prepared in high yields using highly reactive magnesium. Reactions of these (2-butene-1,4 diyl)magnesium reagents with electrophiles such as dibromoalkanes, alkylditosylates, alkylditriflates, bromoalkylnitriles, esters, or amides serve as a convenient method for synthesizing carbocyclic systems. Significantly, carbocycles prepared by this method contain functional groups such as the exocyclic double bond or a keto group in one of the rings which could be used for further elaboration of these molecules. Furthermore, fused bicyclic systems containing a substituted five-membered ring can be conveniently prepared at high temperatures by the reactions of (2-butene-1,4-diyl)magnesium complexes with carboxylic esters or acid halides whereas low temperatures lead to regioselective synthesis of .beta.,.gamma.-unsaturated ketones. Additionally, .gamma.Type: GrantFiled: July 30, 1993Date of Patent: March 12, 1996Assignee: University of NebraskaInventor: Reuben D. Rieke
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Patent number: 5486622Abstract: 5-Oxaspiro[2.4]heptan-6-one: ##STR1## is obtained from [3-(hydroxymethyl)oxetan-3-yl]acetonitrile by reaction with hydrogen bromide and then cyclizing the intermediate product 4,4-bis(bromomethyl)dihydro-2-furanone with zinc. 5-Oxaspiro[2.4]heptan-6-one is an intermediate product for the production of leukotriene antagonists.Type: GrantFiled: April 5, 1995Date of Patent: January 23, 1996Assignee: Lonza Ltd.Inventor: Paul Hanselmann
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Patent number: 5468855Abstract: The invention relates to bislactone color formers having improved fastness to sublimation and migration stability, to their preparation, to pressure-sensitive and heat-sensitive recording materials containing said compounds and to their preparation. The novel bislactones have the formula (1) as defined in claim 1.Type: GrantFiled: August 31, 1994Date of Patent: November 21, 1995Assignee: Ciba-Geigy CorporationInventor: Rudolf Zink
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Patent number: 5461168Abstract: An intermediate useful in the synthesis of milbemycin derivatives having an ether bond at the 13-position and which is represented by the general formula (IIId): ##STR1## wherein R represents a methyl group, an ethyl group, an isopropyl group or a sec-butyl group, and R.sup.5 and R.sup.6' each individually represents a hydrogen atom or a protecting group,and related precursors as well as to a process for producing these intermediates.Type: GrantFiled: August 31, 1993Date of Patent: October 24, 1995Assignee: Sankyo Company, LimitedInventors: Mitsugi Shibano, Mutsauo Suzuki, Shunshi Kojima
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Patent number: 5384078Abstract: A soluble highly reactive form of calcium, prepared from Ca(II) salts and a reducing agent in ethereal, polyethereal, or hydrocarbon solvents, is presented. This form of calcium can be used in the preparation of organocalcium reagents. The organocalcium reagents resulting from the reaction of the soluble highly reactive calcium with organic compounds containing either halide, cyanide, a 1,3-diene, or a polyunsaturated functionality, are stable, useful reagents for organic synthesis. The organocalcium halide reagents undergo Grignard-type reactions. They also undergo reactions with Cu(I) salts to form organocalcium cuprate reagents. The organocalcium cuprate reagents undergo a variety of cross-coupling reactions. The soluble highly reactive calcium reacts with 1,3-dienes to yield the corresponding 2-butene-1,4-diylcalcium complexes. These bis-organocalcium reagents can undergo dialkylation reactions with .alpha.,.omega.Type: GrantFiled: December 15, 1993Date of Patent: January 24, 1995Assignee: Board of Regents of the University of NebraskaInventor: Reuben D. Rieke
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Patent number: 5294375Abstract: Disclosed is a class of bridged phthalides and sulfinate esters which exhibit reversible thermochromism. At room temperature and in the presence of base, these compounds are substantially colorless but upon the application of heat they become colored, reverting to their original colorless or weakly colored state upon cooling. This colorless to colored, temperature-dependent cycle can be repeated many times. These compounds have utility as temperature sensors and as thermal pH indicators.Type: GrantFiled: August 20, 1991Date of Patent: March 15, 1994Assignee: Polaroid CorporationInventors: Marcis M. Kampe, David P. Waller, David C. Whritenour
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Patent number: 5268386Abstract: A novel heterocyclic compound capable of lowering the uric acid levels in plasma and urine having the formula (I): ##STR1## wherein R.sup.1 and R.sup.2 are independently hydrogen, lower alkyl, phenyl or substituted phenyl, or R.sup.1 and R.sup.2 may form a four- to eight-membered carbon ring together with the carbon atom to which they are attached; R.sup.3 is hydrogen or lower alkyl; R.sup.4 is one or two radicals selected from a group consisting of hydrogen, halogen, nitro, lower alkyl, phenyl, substituted phenyl, --OR.sup.5 and --SO.sub.2 NR.sup.6 R.sup.6' ; R.sup.5 is hydrogen, lower alkyl, phenyl-substituted lower alkyl, carboxymethyl or ester thereof, hydroxyethyl or ether thereof, or allyl; R.sup.6 and R.sup.6' are independently hydrogen or lower alkyl; R.sup.Type: GrantFiled: July 26, 1990Date of Patent: December 7, 1993Assignee: Shionogi & Co., Ltd.Inventors: Hiroshi Harada, Eiichi Ohsugi, Yukio Yonetani, Toshihiro Shinosaki
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Patent number: 5229415Abstract: Avermectin compounds are substituted at the 4", 4' or 13-postion hydroxy group with an alkylthioalkyl group and are optionally substituted at the other reactive positions of the avermectin molecule. The compounds are prepared by reacting protected avermectins, avermectin monosaccharides or avermectin aglycones with dialkylsulfoxides. The compounds are potent antiparasitic agents and compositions for such uses are also disclosed.Type: GrantFiled: March 24, 1992Date of Patent: July 20, 1993Assignee: Merck & Co., Inc.Inventors: Bruce O. Linn, Helmut Mrozik
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Patent number: 5212322Abstract: Compounds with acaricidal, insecticidal and anthelmintic activities have the formula: ##STR1## wherein: --X--Y-- is selected from the group consisting of --CH.sub.2 --CH.sub.2 --, --CH.sub.2 --CHOH--, --CH.dbd.CH--, and --CH.sub.2 --C(.dbd.O)--;R.sup.1 is selected from the group consisting of a methyl group, an ethyl group, an isopropyl group, a sec-butyl group and groups of formula --C(CH.sub.3).dbd.CHR.sup.5 in which R.sup.5 is selected from the group consisting of a methyl group, an ethyl group and an isopropyl group;R.sup.2 represents a group of formula --(CH.sub.2).sub.n --C(R.sup.6).dbd.C(R.sup.7)(R.sup.8) in which n is 0, 1 or 2, R.sup.6 and R.sup.7 each is selected from the group consisting of a hydrogen atom and a methyl group and R.sup.8 is selected from the group consisting of a hydrogen atom, a C.sub.1-4 alkyl group, a phenyl group and a phenyl group substituted with at least one substituent selected from the group consisting of halogen, methyl and nitro substituents;R.sup.Type: GrantFiled: January 22, 1991Date of Patent: May 18, 1993Assignee: Sankyo Company, LimitedInventors: Takao Okazaki, Shuji Takahashi, Seigo Iwado, Keiji Tanaka, Toshiaki Yanai, Hisaki Kajino
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Patent number: 5162550Abstract: Bisphthalide lactones of formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are each independently of one another hydrogen, alkyl of at most 12 carbon atoms which is unsubstituted or substituted by halogen, hydroxy, cyano, tetrahydrofuryl or lower alkoxy; or are acyl of 1 to 12 carbon atoms, cycloalkyl of 5 to 10 carbon atoms or unsubstituted aralkyl or aryl, or aralkyl or aryl each substituted by halogen, cyano, nitro, trifluormethyl, lower alkyl, lower alkoxy, lower alkoxycarbonyl, --NX'X"-- or 4--NX'X--"phenylamino, wherein X' and X" are each independently of the other hydrogen, lower alkyl, cyclohexyl, benzyl or phenyl, or the pairs of substituents --NR.sub.1 R.sub.2 and --NR.sub.3 R.sub.4 are each a 5- or 6-membered, preferably saturated, heterocyclic radical, V.sub.1 and V.sub.2 are hydrogen, halogen, lower alkyl, C.sub.1 -C.sub.12 alkoxy, C.sub.1 -C.sub.Type: GrantFiled: August 24, 1990Date of Patent: November 10, 1992Assignee: Ciba-Geigy CorporationInventors: Rudolf Zink, Ian J. Fletcher
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Patent number: 5142054Abstract: Disclosed are new 1,3-dioxenones having the formulae ##STR1## in an optically pure state, a process for preparing same and the use thereof.Type: GrantFiled: February 12, 1991Date of Patent: August 25, 1992Assignee: Studiengesellschaft Kohle mbHInventors: Kurt Schaffner, Martin Demuth
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Patent number: 5137035Abstract: This invention provides a process for the production of novel smoking compositions which contain a benzofuranone flavorant additive, and further provides novel benzofuranone compounds as illustrated by the cis 6-phenyl-3a, 4,5,7a-tetrahydro-2(3H)-benzofuranone: ##STR1## Under normal cigarette smoking conditions, the benzofuranone additive in an invention smoking composition enhances the flavor and aroma of the mainstream and sidestream smoke.Type: GrantFiled: March 21, 1990Date of Patent: August 11, 1992Assignees: Philip Morris Incorporated, Philip Morris Products Inc.Inventor: Kenneth F. Podraza
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Patent number: 5114461Abstract: A 2-benzoylcyclic-1,3-dione derivative of the formula: ##STR1## wherein X represents methylene, oxygen, sulphur or --NR.sup.4 --, Y represents --C(R.sup.5) (R.sup.6)-- or oxygen, R.sup.1 represents hydrogen or alkyl optionally substituted by halogen or represents cycloalkyl, R.sup.2 represents hydrogen or R.sup.7 or R.sup.1 and R.sup.2 together represent alkylene, R.sup.3 represents halogen, hydroxy, carboxy, nitro, cyano or amino or carbamoyl (which may be substituted by one or two alkyl groups), alkoxycarbonyl, alkanoyl, or alkanoylamino, R, RO, RS, RSO or RSO.sub.2 in which R represents alkyl optionally substituted by halogen, R.sup.4 represents hydrogen or alkyl or alkoxycarbonyl, R.sup.5 represents hydrogen or alkyl or alkoxycarbonyl, R.sup.6 represents hydrogen or alkyl, R.sup.7 represents alkyl which may be substituted by halogen or alkylthio or by a group (R.sup.8).sub.n -phenyl-S-, or represents cycloalkyl or tetrahydrothiapyran-3-yl or represents a group (R.sup.8).sub.n -phenyl- in which R.sup.Type: GrantFiled: November 22, 1989Date of Patent: May 19, 1992Assignee: May & Baker LimitedInventors: Neil J. Geach, James Gilmour, Leslie R. Hatton, Philip H. G. Smith
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Patent number: 5109136Abstract: A novel series of tetracyclic amines, methods of preparation, compositions containing the amines, and methods for using them in the treatment and/or prevention of cerebrovascular disorders are disclosed.Type: GrantFiled: August 9, 1990Date of Patent: April 28, 1992Assignee: Warner-Lambert CompanyInventor: Thomas C. Malone
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Patent number: 5106994Abstract: This invention relates to new agents designated LL-F28249.alpha., LL-F28249.beta., LL-F28249.gamma., LL-F28249.delta., LLF28249.epsilon., LL-F28249.zeta., LL-F28249.eta., LL-F28249.theta., LL-F28249.iota., LL-F28249.kappa., LL-F28249.lambda., LL-F28249.mu., LL-F28249.nu., and LL-F28249.omega., to their production by fermentation, to methods for their recovery and concentration from crude solutions, to processes for their purification and to pharmaceutically and pharmacologically-acceptable salts thereof. The present invention includes within its scope the biologically pure culture which produces there agents, derived from a newly-discovered and previously uncultured microorganism, Streptomyces cyaneogriseus subsp. noncyanogenus, NRRL 15773.Type: GrantFiled: May 10, 1985Date of Patent: April 21, 1992Assignee: American Cyanamid CompanyInventors: Guy T. Carter, Margaret J. Torrey, Michael Greenstein
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Patent number: 5099034Abstract: A compound of the formula (I): ##STR1## wherein R.sup.1, R.sup.2, and R.sup.3 are --COOR.sup.4, --COOR.sup.5, and --COOR.sup.6, respectively; R.sup.4, R.sup.5, and R.sup.6 each is hydrogen, lower alkyl, or alkali metal; W is hydroxyl; X, Y, and Z each is hydrogen or hydroxyl; a dotted line indicates the presence or absence of a single bond; or where W/R.sup.3, X/R.sup.1, and/or Z/R.sup.3 may be combined together, a lactone is formed, which compound is useful as a phospholipase A.sub.2 inhibitor. Process for the production of the compound (I) and a cell culture of a microorganism Circinotrichum falcatisporum RF-641 producing the same are also provided.Type: GrantFiled: June 27, 1990Date of Patent: March 24, 1992Assignee: Shionogi & Co., Ltd.Inventors: Tadashi Yoshida, Hiroshi Itazaki, Hitoshi Arita, Yoshimi Kawamura, Koichi Matsumoto
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Patent number: 5097044Abstract: Pyran-containing phthalides of the formula ##STR1## in which R is hydrogen, alkyl which has not more than 12 carbon atoms and is unsubstituted or substituted by halogen, cyano, hydroxyl or lower alkoxy, or is cycloalkyl, phenalkyl or phenyl each of which is unsubstituted or substituted, or an unsubstituted or substituted heterocyclic radical, R' is hydrogen, or R together with R' is C.sub.2 -C.sub.3 alkylene which is unsubstituted or substituted by methyl,X is hydrogen, alkyl having 1 to 12 carbon atoms or a monocyclic or polycyclic aromatic or heteroaromatic radical and the ring A is a benzene or naphthalene ring which is unsubstituted or monosubstituted or polysubstituted by halogen, lower alkyl, lower alkoxy or lower alkoxycarbonyl, and the ring B is an aromatic or heteroaromatic radical which has 6 ring atoms and which can contain an aromatic fused ring, it being possible for both the ring B and the fused ring to be substituted.Type: GrantFiled: September 20, 1990Date of Patent: March 17, 1992Assignee: Ciba-Geigy CorporationInventor: Rox Phaff
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Patent number: 5093499Abstract: Novel monomeric compounds containing aliphatic and/or aromatic substituents on the 1,6-diazaspiro[4.4]nonane-2,7-dione ring system are produced by contacting an amine or an amine hydrohalide and a 1,6-dioxaspiro[4.4]nonane-2,7-dione or a 4-oxoheptanedioic acid. The resulting spirodilactam compounds are characterized by improved hydrolytic and thermal oxidative stability and some of the compounds are useful as intermediates to polymers containing the 1,6-diazaspiro[4.4]nonane-2,7-dione ring system.Type: GrantFiled: April 9, 1990Date of Patent: March 3, 1992Assignee: Shell Oil CompanyInventor: Pen-Chung Wang
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Patent number: 5087706Abstract: Novel fluoran compounds represented by the formula (I): ##STR1## wherein R.sup.1 is an alkyl group having from 1 to 4 carbon atoms, preparation process of the fluoran compounds, and a heat-sensitive and a pressure-sensitive recording material comprising the fluoran compound, are disclosed.Type: GrantFiled: September 18, 1990Date of Patent: February 11, 1992Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Atsuo Otsuji, Masakatsu Nakatsuka, Kiyoharu Hasegawa, Masatoshi Takagi, Akihiro Yamaguchi
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Patent number: 5086187Abstract: Compounds of the general formula, including isomers and tautomers thereof: ##STR1## wherein: R.sup.1 to R.sup.5 are as defined in the text; the compounds have herbicidal and plant growth regulating properties; including compositions containing them, methods for using them and intermediates for making them.Type: GrantFiled: May 31, 1990Date of Patent: February 4, 1992Assignee: Dunlena Pty. LimitedInventors: Janet E. Anderson-McKay, Andris J. Liepa
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Patent number: 5077308Abstract: There are disclosed avermectin aglycone derivatives which incorporate a ketal at position 13. The synthetic ketal analogs are derived from the corresponding ketones which in turn are prepared by chemical modification of naturally occurring avermectins. The compounds are active antiparasitic agents and compositions for that use are disclosed.Type: GrantFiled: July 23, 1990Date of Patent: December 31, 1991Assignee: Merck & Co., Inc.Inventor: Timothy A. Blizzard
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Patent number: 5064856Abstract: Compound of formulae (I) and (II) are HMG-CoA synthase inhibitors and exhibit antifungal activity.Type: GrantFiled: July 31, 1989Date of Patent: November 12, 1991Assignee: Merck & Co., Inc.Inventors: George M. Garrity, Robert Giacobbe, Michael D. Greenspan, Otto D. Hensens, Henry Joshua, Maria T. D. Matas, Isabel Martin, James A. Milligan, Sagrario M. del Val, Walter Rozdilsky, Janet C. Onishi, Jerrold M. Liesch
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Patent number: 5057499Abstract: There are disclosed novel avermectin derivatives wherein the outer oleandrose ring of avermectin or avermectin monosaccharide is homologated by addition of diazomethane to 4"- or 4'-oxo-avermectin to afford the perhydrooxepine derivatives. The homologated avermectins can then be further derivatized to afford additional novel avermectins. The new compounds are potent antiparasitic agents, in particular, the compounds are anthelmintic, insecticidal and acaricidal agents.Type: GrantFiled: June 2, 1989Date of Patent: October 15, 1991Assignee: Merck & Co. Inc.Inventors: Helmut Mrozik, Peter J. Sinclair
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Patent number: 5026877Abstract: Disclosed are new 1,3-dioxenones having the formulae ##STR1## in an optically pure state, a process for preparing same and the use thereof.Type: GrantFiled: May 10, 1989Date of Patent: June 25, 1991Assignee: Studiengesellschaft Kohle mbHInventors: Kurt Schaffner, Martin Demuth
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Patent number: 5008250Abstract: There are disclosed novel avermectin compounds having a cleaved furan ring and a hydroxy group in the 8a position. Processes for preparing these novel compounds are also disclosed. These compounds have utility as anti-parasitic agents and as insecticides against agricultural pests.Type: GrantFiled: May 25, 1988Date of Patent: April 16, 1991Assignee: Merck & Co., Inc.Inventors: Michael H. Fisher, Matthew J. Wyvratt, Helmut Mrozik
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Patent number: 4996229Abstract: Scytophycins A, B, C, D and E, an aldehyde and alcohol derivative of scytophycin B and the specified alkanoyl and benzoyl esters of scytophycins A, B, C, D and E and the B derivatives (scytophycin compounds) are novel antineoplastic and antifungal agents. Antifungal compositions containing a scytophycin compound and methods of inhibiting fungi, especially plant pathogenic fungi, using these compositions are included. A method for producing the scytophycin complex, comprising scytophycins A, B, C, D and E, using a new strain of the blue-green alga Scytonema pseudohofmanni, and a biologically purified culture of the alga are also provided.Type: GrantFiled: August 31, 1989Date of Patent: February 26, 1991Assignees: University of Hawaii, Eli Lilly and CompanyInventors: Richard E. Moore, Eiichi Furusawa, Ted R. Norton, Gregory M. L. Patterson, Jon S. Mynderse
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Patent number: 4973712Abstract: Novel 2-aralkylaminofluorans of formula ##STR1## wherein Q is --CH.sub.2 --, --CH.sub.2 --O-- or --CO--,R.sub.1, R.sub.2 and R.sub.3 are each independently of one another hydrogen, halogen, lower alkyl or lower alkoxy,X.sub.1 and X.sub.2 are each independently of the other hydrogen, alkyl which is unsubstituted or substituted by halogen, hydroxy, cyano, tetrahydrofuryl or lower alkoxy, or ar cycloalkyl or benzyl or phenyl, each unsubstituted or substituted by halogen, cyano, nitro, lower alkyl, lower alkoxy or lower alkoxycarbonyl; or--NX.sub.1 X.sub.2 is a 5- 6-membered heterocyclic radical, and wherein the benzene rings A and B are independently of the other unsubstituted or substituted by halogen, cyano, lower alkyl, lower alkoxy, lower alkylthio, lower alkoxycarbonyl or trifluoromethyl, and the ring D is unsubstituted or substituted by halogen, nitro, lower alkyl, lower alkoxy, lower alkylthio, amino, mono-lower alkylamino or di-lower alkylamino.Type: GrantFiled: February 21, 1989Date of Patent: November 27, 1990Assignee: Ciba-Geigy CorporationInventor: Rudolf Zink
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Patent number: 4939278Abstract: Compounds of the general formula (2) and isomeric and/or tautomeric forms thereof ##STR1## characterized in that R.sup.1 is selected from the group consisting of: hydrogen; alkyl; alkenyl; alkynyl; cycloalkyl; cycloalkenyl; substituted alkyl or substituted cycloalkyl wherein the alkyl or cycloalkyl group is substituted with a substituent selected from the group consisting of alkoxy, alkylthio, optionally substituted phenyl, optionally substituted heterocycle; optionally substituted phenyl; optionally substituted heterocycle, alkyl sulfonyl; optionally substituted benzene sulfonyl; an acyl group; and an inorganic or organic cation;R.sup.Type: GrantFiled: April 13, 1988Date of Patent: July 3, 1990Assignee: Dunlena Pty. LimitedInventors: Janet E. Anderson-McKay, Andris J. Liepa
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Patent number: 4931584Abstract: The invention relates to novel monoesters and diesters of 9,10-endoethano-9,10-dihydroanthracene-11,11-dicarboxylic acid.These novel monoesters and diesters correspond to the following structural chemical formula (II): ##STR1## in which R.sup.1 and R.sup.2 are identical or different and can represent H, an alkali metal or alkaline earth metal atom, a linear or branched alkyl group having from 1 to 6 carbon atoms, an alicyclic group having from 3 to 6 carbon atoms, an alkenyl group having from 2 to 6 carbon atoms, defined in their cis or trans variety, or an alkynyl group having from 2 to 6 carbon atoms, the said groups optionally being substituted by one or more functional groups such as ether, epoxide, halogeno, cyano, ester, aldehyde, ketone, aryl etc., where R.sup.1 and R.sup.2 cannot be H or ethyl simultaneously. These addition products constitute valuable intermediates for the preparation of methylidenemalonates in high yields and with a high purity.Type: GrantFiled: March 1, 1988Date of Patent: June 5, 1990Assignee: Laboratoires UPSAInventors: Nicole Bru-Magniez, Christian De Cock, Jacques Poupaert, Jean-Luc De Keyser, Pierre Dumont
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Patent number: 4929638Abstract: Antiparasitic milbemycin derivatives having at the C.25 position a substituted 2-propenyl group --C(CH.sub.3).dbd.CH--R.sup.2 wherein R.sup.2 is a C.sub.3 -C.sub.8 alkyl, alkenyl or alkynyl group which may optionally contain an oxygen or sulphur atom as part of the chain, or a C.sub.3 -C.sub.8 cycloalkyl or cycloalkenyl group, or a 3 to 6 membered oxygen or sulphur containing heterocyclic ring which may optionally be substituted by one or more alkyl groups or halogen atoms; and process for their preparation.Type: GrantFiled: May 25, 1989Date of Patent: May 29, 1990Assignee: Pfizer Inc.Inventors: Christopher Dutton, David Perry
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Patent number: 4927847Abstract: Antiparasitic milbemycin derivatives having at the C.25 position a substituted 2-propenyl group --C(CH.sub.3).dbd.CH--R.sup.2 wherein R.sup.2 is a C.sub.3 -C.sub.8 alkyl, alkenyl or alkynyl group which may optionally contain an oxygen or sulphur atom as part of the chain, or a C.sub.3 -C.sub.8 cycloalkyl or cycloalkenyl group, or a 3 to 6 membered oxygen or sulphur containing heterocyclic ring which may optionally be substituted by one or more alkyl groups or halogen atoms; and process for their preparation.Type: GrantFiled: July 18, 1989Date of Patent: May 22, 1990Assignee: Pfizer Inc.Inventors: Christopher J. Dutton, David A. Perry
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Patent number: 4918097Abstract: The present invention relates to novel derivatives of formula I that can be derived from milbemycins, to their preparation and their use for controlling pests, and also to pesticides that contain at least one of these compounds as active ingredient.The novel compounds have the general formula I ##STR1## in which X is one of the groups --CH(OR.sub.1)--, --C(O)-- or --C(=N--OR)--;R.sub.1 is hydrogen or an OH-protecting group;R is hydrogen, an OH-protecting group, or an alkyl or cycloalkyl group;R.sub.2 is methyl, ethyl, isopropyl or sec.-butyl;andPh is a phenyl ring that is substituted by R.sub.a, R.sub.b, R.sub.c and R.sub.d, wherein each of R.sub.a, R.sub.b, R.sub.c and R.sub.d, independently of the others, is hydrogen, C.sub.1 -C.sub.10 alkyl, C.sub.2 -C.sub.10 alkoxyalkyl, C.sub.2 -C.sub.10 alkenyl, C.sub.1 -C.sub.10 alkoxy, C.sub.2 -C.sub.10 alkoxyalkoxy, or a phenyl or phenoxy radical that is unsubstituted or is substituted by at least one substituent from the group C.sub.1 -C.sub.3 alkyl and C.sub.1 -C.Type: GrantFiled: March 1, 1989Date of Patent: April 17, 1990Assignee: Ciba-Geigy CorporationInventor: Anthony C. O'Sullivan
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Patent number: 4876359Abstract: Novel .gamma.-butyrolactone derivatives having strong ACE inhibitory activity are provided. They are represented by the following general formula (I): ##STR1## wherein R.sup.1 and R.sup.2 may be the same or different and mean individually a hydrogen atom or a straight-chain or branched alkyl or cycloalkyl group, or R.sup.1 and R.sup.2 are bonded together to mean an alkylene group having 2-6 carbon atoms, R.sup.3 denotes a hydrogen atom or a lower alkyl, aralkyl, amino lower alkyl or lower alkoxycarbonylamino lower alkyl group, R.sup.4 means a lower alkyl, cycloalkyl or aralkyl group, R.sup.5 means a hydrogen atom or a lower alkyl group, or R.sub.4 and R.sub.5 are bonded together to denote an alkylene group having 2-4 carbon atoms, and R.sup.6 stands for a hydrogen atom or a lower alkyl or aralkyl group; or a pharmacologically acceptable salt thereof.Type: GrantFiled: October 1, 1987Date of Patent: October 24, 1989Assignee: SS Pharmaceutical Co., Ltd.Inventors: Hiroshi Hasegawa, Noriaki Shioiri, Tadashi Narita, Tatsuhiko Katori
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Patent number: 4871719Abstract: Novel 13-spiro-2'-[tetrahydrofuran]-milbemycins of the formula I ##STR1## in which X represents one of the groups --CH(OR.sub.1)--, --C(.dbd.O)-- or --C(.dbd.N--OH)--;R.sub.1 represents hydrogen or a OH-protecting group;R.sub.2 represents methyl, ethyl, isopropyl or sec.-butyl or the group --C(CH.sub.3).dbd.CH--A in which A represents methyl, ethyl or isopropyl; andR.sub.3 represents hydrogen; C.sub.1 -C.sub.10 -alkyl; C.sub.1 -C.sub.10 -alkyl substituted by at least one substituent selected from the group consisting of halogen, C.sub.1 -C.sub.6 -alkoxy, C.sub.2 -C.sub.6 -alkoxyalkoxy C.sub.3 -C.sub.9 -alkoxyalkoxyalkoxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.3 -C.sub.7 -cycloalkyl, C.sub.1 -C.sub.3 -alkyl-substituted C.sub.3 -C.sub.7 -cycloalkyl, hydroxy, benzyloxy, C.sub.1 -C.sub.6 -acyl and C.sub.1 -C.sub.6 -acyloxy, it being possible for each of the above-mentioned radicals representing or containing an alkoxy group to be terminally substituted at a terminal alkoxy group by hydroxy, halogen, C.sub.1 -C.sub.Type: GrantFiled: March 16, 1988Date of Patent: October 3, 1989Assignee: Ciba-Geigy CorporationInventor: Peter Maienfisch
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Patent number: 4863955Abstract: Scytophycins A, B, C, D and E, an aldehyde and alcohol derivative of scytophycin B and the specified alkanoyl and benzoyl esters of scytophycins A, B, C, D and E and the B derivatives (scytophycin compounds) are novel antineoplastic and antifungal agents. Antifungal compositions containing a scytophycin compound and methods of inhibiting fungi, especially plant pathogenic fungi, using these compositions are included. A method for producing the scytophycin complex, comprising scytophycins A, B, C, D and E, using a new strain of the blue-green alga Scytonema pseudohofmanni, and a biologically purified culture of the alga are also provided.Type: GrantFiled: May 21, 1986Date of Patent: September 5, 1989Assignees: Eli Lilly and Company, University of HawaiiInventors: Richard E. Moore, Eiichi Furusawa, Ted R. Norton, Gregory M. L. Patterson, Jon S. Mynderse
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Patent number: 4857509Abstract: The invention relates to parasiticidally and insecticidally highly active compounds of formula I ##STR1## wherein R is C.sub.1 -C.sub.10 alkyl;R.sub.1 is hydrogen, a silyl group or a sugar residue; andR.sub.2 is methyl, ethyl, isopropyl or sec-butyl, and to the preparation thereof starting from suitably substituted 15-ester or 13.beta.-ester milbemycins.Type: GrantFiled: January 17, 1986Date of Patent: August 15, 1989Assignee: CIBA-GEIGY CorporationInventors: Bruno Frei, Anthony C. O'Sullivan, Jean-Claude Gehret
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Patent number: 4820840Abstract: An improved process for producing fluorene compounds of the following formula (II) is disclosed: ##STR1## (wherein R.sub.1, R.sub.2 and R.sub.3 are independently a hydrogen atom, an alkylamino group, a dialkylamino group, a pyrrolidino group or a piperdino group; X and Y are independently a carbon atom or a nitrogen atom; and with the proviso that R.sub.1 and R.sub.2 are not hydrogen atoms simultaneously). The process comprises reacting a lactone compound of the formula (I) (variables being defined as in formula (II) ) ##STR2## with a mixture of an aluminum halide, a carbonyl compound, and a hydroxy bearing compound.Type: GrantFiled: January 22, 1988Date of Patent: April 11, 1989Assignee: Appleton Papers Inc.Inventors: Seishi Ikegami, Satoshi Nakao
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Patent number: 4808733Abstract: An intermediate compound having the structural formula ##STR1## wherein X is oxygen or sulfur;R is halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; or R.sup.a SO.sub.n --wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl;R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.1 and R.sup.3 together are alkylene having 2-5 cation atoms; orR.sup.2 and R.sup.4 together are alkylene having 2-5 carbon atoms; andR.sup.5 and R.sup.6 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifuoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n --wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR.sup.C R.sup.d wherein R.Type: GrantFiled: December 21, 1987Date of Patent: February 28, 1989Assignee: Stauffer Chemical CompanyInventors: Christopher G. Knudsen, William J. Michaely, Donald R. James, Hsiao-Ling M. Chin
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Patent number: 4797219Abstract: According to the present invention, novel oil soluble compositions useful as dispersants are provided by reaction of a mono- or polycarboxylic acid acylating reactant with at least one heterocyclic polyol of the formula: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are the same or different and are selected from the group consisting of H, alkyl and --CH(OH)R.sup.5, wherein R.sup.5 is C.sub.1 to C.sub.10 alkyl, and wherein X and Y are the same or different and are H or C.sub.1 to C.sub.10 alkyl, with the proviso that at least one of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 is the --CH(OH)R.sup.5 moiety.Type: GrantFiled: April 24, 1987Date of Patent: January 10, 1989Assignee: Exxon Chemical Patents Inc.Inventors: Antonio Guttierrez, Jack Ryer
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Patent number: 4794069Abstract: Spirobenzanthracene phthalide compounds are disclosed of the formula (I) ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 independently represent C.sub.1 -C.sub.8 alkyl optionally substituted by C.sub.1 -C.sub.5 alkoxy; C.sub.5 or C.sub.6 cycloalkyl; or aralkyl or aryl optionally substituted by C.sub.1 -C.sub.5 alkyl or C.sub.1 -C.sub.5 alkoxy, and R.sup.1 and R.sup.2, R.sup.3 and R.sup.4, and R.sup.5 and R.sup.6 taken together with the nitrogen atom to which they are attached, may form pyrrolidino, piperidino or morpholino ring, and R.sup.7, R.sup.8, R.sup.9 and R.sup.10 independently represent hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkoxy or trifluoromethyl. The compounds are used, together with a developer, in color for materials such as pressure-sensitive copying papers, heat-sensitive recording papers and the like.Type: GrantFiled: July 14, 1987Date of Patent: December 27, 1988Assignee: Shin Nisso Kako Co., Ltd.Inventors: Yutaka Ohnishi, Shinji Yoshinaka, Toshiyuki Tanaka, Minoru Koguchi, Takeo Obitsu