Plural Chalcogens Bonded Directly To The Hetero Ring Patents (Class 549/476)
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Patent number: 5256797Abstract: A process for separating an anomeric mixture of alpha and beta 2-deoxy-2,2-difluoro-D-ribofuranosyl-1-alkylsulfonates by contacting the anomeric mixture with a solvent; heating; adding a countersolvent; and lowering the temperature.Type: GrantFiled: June 22, 1992Date of Patent: October 26, 1993Assignee: Eli Lilly and CompanyInventors: Ta-Sen Chou, Timothy J. McCarthy
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Patent number: 5256798Abstract: A process for providing an alpha-anomer enriched ribofuranosyl sulfonate from a beta-anomer ribofuranosyl sulfonate; comprising treating a beta-anomer ribofuranosyl sulfonate or anomeric mixture thereof with a conjugate anion of a sulfonic acid source at elevated temperatures in an inert solvent.Type: GrantFiled: June 22, 1992Date of Patent: October 26, 1993Assignee: Eli Lilly and CompanyInventors: Ta-Sen Chou, Charles D. Jones
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Patent number: 5252756Abstract: A stereoselective process for preparing 2-deoxy-2,2-difluoro-D-ribofuranosyl beta-anomer enriched aryl sulfonates or substituted arylsulfonates involving reacting a lactol with an acid scavenger and a sulfonating reagent in an inert solvent.Type: GrantFiled: June 22, 1992Date of Patent: October 12, 1993Assignee: Eli Lilly and CompanyInventors: Ta-Sen Chou, Charles D. Jones
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Patent number: 5250567Abstract: The compounds of the present invention comprise substituted phenolic thioethers represented by the formula (I): ##STR1## wherein: R.sup.1 and R.sup.2 are the same or different and independently represent tert-alkyl or phenyl; R.sup.3 represents hydrogen or alkyl; X represents --(CH.sub.2).sub.w --B--(CH.sub.2).sub.y -- wherein B represents O, S, or CH.sub.2 and w and y can each independently be an integer from 0 to 3 with the proviso that the sum of w+y is equal to or less than 3; A represents O or S(O).sub.n wherein n is 0, 1 or 2; p is an integer from 1 to 4; and R represents alkyl; OH; OR.sup.4 wherein R.sup.4 is alkyl of 1 to 4 carbon atoms; NR.sup.5 R.sup.6 wherein R.sup.5 is hydrogen or alkyl and R.sup.6 is hydrogen, alkyl, heterocyclealkyl in which the hetercyclic ring may optionally be substituted; cycloalkyl; substituted cycloalkyl; phenyl; substituted phenyl; phenylalkyl; or substituted phenylalkyl; or NR.sup.5 R.sup.Type: GrantFiled: June 24, 1992Date of Patent: October 5, 1993Assignee: G. D. Searle & Co.Inventors: Richard A. Mueller, Richard A. Partis
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Patent number: 5234950Abstract: The invention concerns a heterocyclic derivative of the formula I, ##STR1## wherein Ar.sup.1 is optionally substituted phenyl or naphthyl;A.sup.1 is (1-6C)alkylene, (3-6C)alkenylene, (3-6C)alkynylene or cyclo-(3-6C)alkylene;Ar.sup.2 is optionally substituted phenylene, or a 6 membered heterocyclene moiety containing up to three nitrogen atoms;R.sup.1 is hydrogen, (1-6C)alkyl, (3-6C)alkenyl, (3-6C)alkynyl, cyano-(1-4C)alkyl or (2-4C)alkanoyl, or optionally substituted benzoyl; andR.sup.2 and R.sup.3 together form a group of the formula --A.sup.2 --X--A.sup.3 -- wherein each of A.sup.2 and A.sup.3 is (1-4C)alkylene and X is oxy, thio, sulphinyl, sulphonyl or imino;or a pharmaceutically-acceptable salt thereof.The compounds of the invention are inhibitors of the enzyme 5-lipoxygenase.Type: GrantFiled: January 3, 1992Date of Patent: August 10, 1993Assignees: Imperial Chemical Industries PLC, ICI PharmaInventors: Philip N. Edwards, Jean-Marc M. M. Girodeau
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Patent number: 5229393Abstract: Compounds of formula (I): ##STR1## and stereoisomers thereof, wherein V is an oxygen or a sulphur atom; X and Y, which may be the same or different, are hydrogen or halogen atoms, or optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkynyl, haloalkyl, alkoxy, haloalkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted acyloxy, optionally substituted amino, acylamino, nitro, nitrile, --CO.sub.2 R.sup.3, --CONR.sup.4 R.sup.5, or --COR.sup.6 groups; or the groups X and Y, when they are in adjacent positions on the phenyl ring, may join to form a fused ring, either aromatic or aliphatic, optionally containing one or more heteroatoms; and Z is optionally substituted methylene, optionally substituted amino, oxygen or sulphur and when Z is a substituted methylene group, the substituent may join the 2-position of the phenyl ring to form a non-aromatic fused ring; R.sup.1 and R.Type: GrantFiled: April 6, 1992Date of Patent: July 20, 1993Assignee: Imperial Chemical Industries PLCInventors: John M. Clough, Christopher R. A. Godfrey
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Patent number: 5217991Abstract: Non-peptidyl compounds characterized generally as cycloalkyl/cycloalkylalkyl-N-terminal cycloalkoxy-C-terminal amino hydroxy .beta.-amino acid derivatives are useful as renin inhibitors for treatment of hypertension. Compounds of particular interest are of the formula ##STR1## wherein R.sub.1 is selected from cycloalkyl and cycloalkylalkyl groups, wherein said cycloalkyl group contains three to about eight carbon atoms and the acyclic alkyl portion of said cycloalkylalkyl group contains one to about eight carbon atoms; wherein each of R.sub.2 and R.sub.4 is independently selected from hydrido and methyl; wherein R.sub.3 is methyl or ethyl: wherein R.sub.5 is cyclohexylmethyl; wherein R.sub.6 and R.sub.Type: GrantFiled: May 28, 1992Date of Patent: June 8, 1993Assignee: G. D. Searle & Co.Inventors: Gunnar J. Hanson, John S. Baran, Dave Weissing, Mark Russell
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Patent number: 5216013Abstract: Non-peptidyl compounds characterized generally as heterocyclic acyl aminodiol .beta.-amino acid derivatives are useful as renin inhibitors for treatment of hypertension. Compounds of particular interest are compounds of the formula ##STR1## wherein R.sub.1 is selected from aryl and aralkyl groups represented by ##STR2## and wherein R.sub.1 may be further selected from heteroaryl and heteroaralkyl represented by ##STR3## wherein each of T and A is independently selected from N and CH; wherein n is a number selected from zero through five, inclusive; wherein X is selected from oxygen atom, methylamino and NH; wherein each of Y and Z is independently selected from chloro, fluoro, methoxy and dimethylamino; wherein Q is oxygen atom; and wherein each of T and A is independently selected from N and CH; wherein each of R.sub.2 and R.sub.4 is independently selected from hydrido and methyl; wherein R.sub.3 is selected from methyl and ethyl; wherein R.sub.5 is cyclohexylmethyl; wherein R.sub.6 is hydroxy; wherein R.Type: GrantFiled: July 16, 1992Date of Patent: June 1, 1993Assignee: G. D. Searle & Co.Inventor: Gunnar J. Hanson
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Patent number: 5210238Abstract: Perfluorinated cyclic hemiketals of formula: ##STR1## where n=1-6, m=2-3, and their corresponding perfluoridiketones. The latter are prepared by means of perfluoroalkylation reaction of diacyl fluorides with perfluoroalkyl-trialkyl silanes. The perfluorodiketones can be then reacted with H.sub.2 O in order to obtain said cyclic hemiketals.Type: GrantFiled: January 23, 1992Date of Patent: May 11, 1993Assignee: Ausimont S.p.A.Inventors: John D. Anderson, Darryl D. Desmarteau, Walter Navarrini
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Patent number: 5128348Abstract: Certain hexane and heptane amines including geometric and stereoisomers, agricultural compositions containing them and their use as fungicides.Type: GrantFiled: September 12, 1990Date of Patent: July 7, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventor: Gregory S. Basarab
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Patent number: 5102905Abstract: The invention concerns heterocyclic nitromethane derivatives of the formula 1 as defined hereinafter (and their non-toxic salts) wherein the heterocyclic moiety Q is thienyl, benzothienyl or dibenzothienyl and may bear a wide variety of optional substituents, together with pharmaceutical compositions containing them. The nitromethane derivatives are inhibitors of the enzyme aldose reductase and are of value in the treatment of certain complications of diabetes and galactosemia.Type: GrantFiled: April 28, 1989Date of Patent: April 7, 1992Assignee: Imperial Chemical Industries PLCInventors: Steven P. Brown, Anthony L. Cooper, Jethro L. Longridge, Jeffrey Morris, John Preston
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Patent number: 5102909Abstract: The compounds 2-(5-methylthiomethyl-2-furyl)-2-hydroxy-3-keto-4- dihydroxyethylbutyrolactone and 2-(5-methoxymethyl-2- furyl)-2-furyl(-2-hydroxy-3-keto-4-dihydroxyethylbutyrolactone and pharmaceutical compositions containing them are useful to regulate the immune response in mammals.Type: GrantFiled: June 11, 1990Date of Patent: April 7, 1992Assignee: Theracel CorporationInventors: Robert W. Veltri, Gabor B. Fodor, Kawporn Sussangkarn
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Patent number: 5077426Abstract: A process for preparing .alpha.-formylamino nitriles of the formula Ia ##STR1## and Ib ##STR2## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are identical or different and each is hydrogen or unsubstituted or substituted, with substituents which are inert under the reaction conditions, aliphatic or heteroaliphatic radicals with 1 to 10, cycloaliphatic or heterocycloaliphatic radicals with 3 to 6, araliphatic radicals with 7 to 12, heteroaraliphatic radicals with 4 to 12, aromatic radicals with 6 to 10 or heteroarometic radicals with 3 to 10 carbon atoms, with the priviso that at least one of R.sup.1 and R.sup.2 or R.sup.3 and R.sup.4 is hydrogen, comprises reacting an iminodiacetonitrile of the formula II ##STR3## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the abovementioned meanings, with formamide of the formula III ##STR4## in the presence of formic acid or with a compound which provides formic acid, in the presence of acids.Type: GrantFiled: December 13, 1990Date of Patent: December 31, 1991Assignee: BASF AktiengesellschaftInventors: Rolf Fikentscher, Michael Kroener
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Patent number: 5059690Abstract: Antiviral activity is exhibited by compounds having the formula ##STR1## and pharmaceutically acceptable salts thereof wherein R.sub.1 is a purine or pyrimidine base or an analog thereof and R.sub.2 and R.sub.3 are independently hydrogen, --PO.sub.3 H.sub.2 or ##STR2## wherein X.sub.7 is hydrogen, alkyl, substituted alkyl or aryl.Type: GrantFiled: May 1, 1990Date of Patent: October 22, 1991Assignee: E. R. Squibb & Sons, Inc.Inventors: Robert Zahler, Joseph A. Tino
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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: 5053430Abstract: Novel compounds having the general formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are as defined herein. These compounds are useful in the treatment of schizophrenia.Type: GrantFiled: September 22, 1989Date of Patent: October 1, 1991Assignee: Boehringer Ingelheim KGInventors: Matthias Grauert, Herbert Merz, Joachim Mierau, Gunter Schingnitz, Claus Schneider
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Patent number: 5049673Abstract: The present invention discloses a new class of calcium specific fluorescent indicator dyes having visible excitation and emission wavelengths. The new fluorescent indicator dyes combine at least one tricyclic chromophore with a tetracarboxylate parent CA.sup.2+ chelating compound having the octacoordinate pattern of liganding groups characteristic of BAPTA to give a rhodamine-like or fluorescein-like fluorophore. Binding of calcium.sup.2+ increases the fluorescence of the new compounds by up to 40-fold. The calcium.sup.2+ dissociation constants are in the range 0.37-2.3 microM, so that the new indicators give better resolution of high [CA.sup.2+ ] levels than were previously obtainable with predecessor compounds such as quin-2 or fluo-2. The visible excitation wavelengths of the new compounds are more convenient for fluorescent microscopy and flow cytometry than the UV required by previous indicators.Type: GrantFiled: October 30, 1987Date of Patent: September 17, 1991Assignee: The Regents of the University of CaliforniaInventors: Roger Y. Tsien, Akwasi Minta
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Patent number: 5039685Abstract: Novel O-alkylated oximes of the general formula I ##STR1## wherein R.sup.1 and R.sup.2 are optionally substituted aromatic or heteroaromatic rings, R.sup.3 is hydrogen or lower alkyl, R.sup.4 is a nitrogen containing, substituted ring or an amino group carrying a substituted ring, and n and m independently are 0, 1 or 2, are potent inhibitors of GABA reuptake from the synaptic cleft.Type: GrantFiled: May 10, 1989Date of Patent: August 13, 1991Assignee: Novo Nordisk A/SInventors: Lars J. S. Knutsen, Knud E. Andersen, Anker S. Jorgensen, Ursula Sonnewald
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Patent number: 5023355Abstract: A process for the preparation of stabilized B-carotene wherein polysorbate is heated under an inert atmosphere to about 100.degree. to about 120.degree. C. in the presence of butylated hydroxytoluene for a period of time sufficient to allow substantially all of the water present in the polysorbate to be driven off. The temperature is then increased to about 160.degree. to about 180.degree. C. and the resultant polysorbate product further heated at this temperature while maintaining the inert atmosphere and under strong stirring for 1 to 11/2 hours. The thus heated polysorbate is then cooled rapidly to about 100.degree. to about 120.degree. C. and 2.0 to 4.0% by weight of B-carotene, based on the weight of the polysorbate, introduced under strong stirring in the presence of para-aminobenzoic acid and a conventional antioxidant such as butylhydroxyquinone under containued maintenance of the inert atmosphere. The resulting liquid composition is cooled to room temperature.Type: GrantFiled: June 20, 1990Date of Patent: June 11, 1991Inventors: Alfred R. Globus, Joseph Vernice
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Patent number: 5017693Abstract: The present invention provides cleavable conjugates whose linkers contain a labile bond that is cleavable under a variety of mild conditions, including weakly acidic. Since the agent may be bonded directly to the linker, cleavage can result in release of native agent. The invention also provides methods for producing cleavable conjugates. Preferred agents include drugs, toxins, biological response modifiers, radiodiagnostic compounds, radiotherapeutic compounds, and derivatives thereof. The targeting molecule employed in the invention may be an intact molecule, a fragment thereof, or a functional equivalent thereof. In a particularly preferred embodiment, the targeting molecule is a monoclonal antibody directed towards a tumor-associated antigen in man. The invention further provides methods for delivering to the cytoplasm of target cell an agent free of its targeting molecular carrier.Type: GrantFiled: December 19, 1989Date of Patent: May 21, 1991Assignee: NeoRx CorporationInventors: Mark D. Hylarides, Ananthachari Srinivasan, Jeffrey N. Fitzner, Vivekananda M. Vrudhula
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Patent number: 4992568Abstract: o-Iodoaryl allyl ethers undergo facile palladium-promoted cyclization to benzofurans.Type: GrantFiled: August 25, 1989Date of Patent: February 12, 1991Assignee: Iowa State University Research Foundation, Inc.Inventor: Richard C. Larock
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Patent number: 4990631Abstract: This invention is directed to a process for the synthesis of 2,2-dialkoxy cyclic ortho esters derived from lactones which comprises reacting trialkyl orthoformate with boron trifluoride to give dialkoxymethylium tetrafluoroborate; reacting dialkoxymethylium tetrafluoroborate with a lactone to give the corresponding O-alkyllactonium tetrafluoroborate; and reacting the O-alkyllactonium tetrafluoroborate with an alkoxide, or alternatively with an alkanol in the presence of a base; wherein the first two steps of the process of the invention are conducted in the absence of solvents, other than the reactants themselves. The third step may also optionally be run without solvents.The invention is also directed to the preparation of the O-alkyllactonium tetrafluoroborate in one reaction vessel; that is, the boron trifluoride is added to the trialkyl orthoformate and the lactone in a single reaction vessel.Type: GrantFiled: May 30, 1990Date of Patent: February 5, 1991Assignee: Alza CorporationInventor: Karol Alster
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Patent number: 4968820Abstract: The new compounds produced from a molecular structural element with two chirality centers and at least one mesogenic structural element are defined by the general formula (I) ##STR1## in which the symbols have the following meaning: Y.sup.1, Y.sup.2, Y.sup.3, Y.sup.4 = in any two cases (a) hydroxy and MC--CO--O or, independently of each other, MC--CO--O and (b), independently of each other (C.sub.1 -C.sub.10)alkoxy, MC denoting the molecular radical of a mesogenic carboxylic acid after splitting off a COOH group, and it being possible for Y.sup.2 and Y.sup.3, in the case of (C.sub.1 -C.sub.10)alkoxy, also to be jointly part of a dioxolane ring, or Y.sup.1 and Y.sup.4 jointly = 0 as part of a tetrahydrofuran ring, and Y.sup.2 and Y.sup.3 = hydroxy and MC--CO--O or, independently of each other, MC--CO--O. Said esters preferably find application as dopants in twistable liquid crystal phases in which they produce temperature compensation and twisting.Type: GrantFiled: July 11, 1988Date of Patent: November 6, 1990Assignee: Hoechst AktiengesellschaftInventors: Gunter Scherowsky, Manel Gunaratne
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Patent number: 4958037Abstract: Novel precursors for the synthesis of methyl-9-oxo-11.alpha.,16-dihydroxy-16-vinyl-5-cis-13-trans prostadienoates having the formulae ##STR1## wherein R.sub.1 is H or C.sub.1 -C.sub.4 alkyl; R.sub.2 is C.sub.1 -C.sub.4 alkyl, R.sub.3 is H, C.sub.1 -C.sub.4 trialkylsilyl or C.sub.1 -C.sub.6 alkyl; X.sub.1 is halogen, cyano, C.sub.1 -C.sub.4 alkoxycarbonyl, carboxy or tri (C.sub.1 -C.sub.4 alkoxy)methyl; n is 2-4 inclusive; and P.sub.1 is H or a blocking or protective group; congeners and racemic mixture of these compounds and processes of synthesizing them.Type: GrantFiled: April 25, 1988Date of Patent: September 18, 1990Assignee: American Cyanamid CompanyInventor: Middleton B. Floyd, Jr.
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Patent number: 4943584Abstract: Novel (p-phenoxyphenoxy)-methyl-five-membered heeroaromatic radicals of the formula ##STR1## where the substituents have the following meanings: R.sup.1, R.sup.2, R.sup.3 hydrogen, halogen, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.3 -C.sub.10 -cycloalkyl, nitro or cyano,R.sup.4 hydrogen or C.sub.1 -C.sub.4 -alkyl, and a five-membered heteroaromatic ring, and their use for combating pests.Type: GrantFiled: April 20, 1988Date of Patent: July 24, 1990Assignee: BASF AktiengesellschaftInventors: Hans Theobald, Christoph Kuenast, Peter Hofmeister, Hans-Juergen Neubauer, Thomas Kuekenhoehner, Wolfgang Krieg, Joachim Leyendecker, Uwe Kardorff
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Patent number: 4939277Abstract: A tetrahydrofuran derivative of the formula: ##STR1## wherein each of R.sub.1 and R.sub.2 is an alkyl group having from 1 to 20 carbon atoms, and the two alkoxy groups OR.sub.1 and OR.sub.2 take a cis form to the plane of the tetrahydrofuran ring.Type: GrantFiled: February 7, 1989Date of Patent: July 3, 1990Assignee: Mitsubishi Kasei CorporationInventors: Naoshi Imaki, Isao Kawakami, Sinichiro Nakamura
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Patent number: 4913721Abstract: Compounds of formula (I): ##STR1## and stereoisomers thereof, wherein V is an oxygen or a sulphur atom; X and Y, which may be the same or different, are hydrogen or halogen atoms, or optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkynyl, haloalkyl, alkoxy, haloalkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted acyloxy, optionally substituted amino, acylamino, nitro, nitrile, --CO.sub.2 R.sup.3, --CONR.sup.4 R.sup.5, or --COR.sup.6 groups; or the groups X and Y, when they are in adjacent positions on the phenyl ring, may join to form a fused ring, either aromatic or aliphatic, optionally containing one or more heteroatoms; and Z is optionally substituted methylene, optionally substituted amino, oxygen or sulphur and when Z is a substituted methylene group, the substituent may join the 2-position of the phenyl ring to form a non-aromatic fused ring; R.sup.1 and R.Type: GrantFiled: October 31, 1988Date of Patent: April 3, 1990Assignee: Imperial Chemical Industries PLCInventors: John M. Clough, Christopher R. A. Godfrey
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Patent number: 4900324Abstract: The acetals, 2,3-dihydroxy-1,1,4,4-tetramethoxybutane, 3,4-dihydroxy-2,5-dimethoxytetrahydrofuran, and glyceraldehyde dimethylacetal, when applied to cotton fabric by conventional pad-dry-cure procedures using special combined acid catalysts, were found to crosslink cellulose hydroxy groups at a very rapid rate (e.g., 20 seconds at 160.degree. C.), thereby imparting improved wrinkle recovery in the range of that required for durable press finishing. Cotton fabrics treated with these acetals have the advantage of no formaldehyde release.Type: GrantFiled: August 8, 1988Date of Patent: February 13, 1990Assignee: The United States of America, as represented by the Secretary of AgricultureInventors: Leon H. Chance, Gary F. Danna, Bethlehem K. Andrews
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Patent number: 4871761Abstract: Novel pesticides of the formula ##STR1## in which R.sup.1 represents in each case optionally substituted cycloalkyl, cycloalkenyl, tetrahydronaphthyl, decahydronaphthyl, phenyl, naphthyl or thienyl,R.sup.2 represents alkyl,R.sup.3 represents hydrogen alkyl, alkenyl, alkinyl, hydroxyalkyl, alkoxyalkyl, dialkoxyalkyl, hydroxyalkoxyalkyl, cyano or formyl, or in each case optionally substituted cycloaklyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl, aralkyl, aryl, furanylmethyl or tetrahydrofuranylmethyl,R.sup.4 represents hydrogen or alkyl, andHet represents an optionally substituted heterocyclic ring of the formula ##STR2## and acid-addition salts thereof.Type: GrantFiled: March 18, 1988Date of Patent: October 3, 1989Assignee: Bayer AktiengesellschaftInventors: Detlef Wollweber, Stefan Dutzmann
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Patent number: 4829078Abstract: This invention relates to compounds presented by the general formula: ##STR1## [wherein R.sup.1 and R.sup.2 are: (i) R.sup.1, R.sup.2 and carbon atoms to which R.sup.1 and R.sup.2 are linked, together represent the group of the general formula: ##STR2## (wherein R.sup.5 and R.sup.6 represent hydrogen, alkyl, cycloalkyl, cycloalkyl-alkyl or phenyl, independently, with the proviso that R.sup.5 and R.sup.6 is not hydrogen atoms at the same time), or(ii) R.sup.1 represents hydrogen and R.sup.2 represents the group of the formula: --COR.sup.7 (wherein R.sup.7 represents the group of the formula: ##STR3## (wherein Y represents a single-bond, alkylene, alkenylene, W represents oxygen or sulfur, m represents 1 to 3, R.sup.8 represents hydrogen, halogen, nitro, hydroxy, alkyl or alkoxy, with the proviso that when m represents two or more, plural R.sup.8 s may be different each, and R.sup.9 represents hydrogen, alkyl or phenyl group, with the proviso that two of R.sup.9 may be different each)), R.sup.Type: GrantFiled: February 22, 1988Date of Patent: May 9, 1989Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Katsuhiro Imaki, Tadao Okegawa, Yoshinobu Arai
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Patent number: 4792606Abstract: A process for the preparation of a dimeric aromatic acyl cyanide of the formula ##STR1## in which Ar is optionally substituted phenyl, naphthyl or hetaryl,comprising reaction an acyl halide of the formulaAr--CO--Halin whichHal is fluorine, chlorine or bromine, with an alkali metal cyanide in a two-phase system comprising water and a water-immiscible or only sparingly water-miscible aliphatic ketone, and in the presence of a phase-transfer catalyst. The products are known intermediates for pesticides.Type: GrantFiled: July 16, 1987Date of Patent: December 20, 1988Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Hermann-Dieter Krall
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Patent number: 4785794Abstract: A method for processing aqueous sugar juice containing a mixture of aldehyde-function saccharides and ketonic-function saccharides for separating and selecting ketonic-function saccharides, comprising (a) producing a hydro-organic medium by mixing the juice with an active methylene ketonic compound, a calcium-based catalyst and preferably ethanol, (b) mixing the medium until furanic polyalcohol is formed by condensation of the ketonic compound and the aldehyde-function saccharides and (c) allowing the furanic polyalcohol to precipitate and separating it by physical means from the liquid medium.Type: GrantFiled: January 20, 1987Date of Patent: November 22, 1988Assignee: Institut National Polytechnique de ToulouseInventors: Louis F. Jo, Marie E. Borredon, Michel Delmas, Antoine Gaset
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Patent number: 4785109Abstract: These is described a process for producing sulfonylureas of the formula ##STR1## wherein G is an unsubstituted or substituted furanyl, thienyl, pyrrolyl, pyridinyl or phenyl radical,X is alkyl, haloalkyl, alkoxy, alkylthio, halogen, haloalkoxy, alkylamino or dialkylamino,Y is alkyl, alkoxy or haloalkoxy,Z is a nitrogen atom or the methyne group --CH.dbd..This novel process comprises reacting a sulfonamide of the formulaG--SO.sub.2 --NH.sub.2,in the presence of a base, with a chloroformic acid ester of the formulaCl--CO--Q--T,or a sulfonyl chloride of the formulaG--SO.sub.2 Cl,in the presence of a base, with a urethane of the formulaH.sub.2 N--CO--Q--T;and converting the formed carbamate of the formulaG--SO.sub.2 --NH--CO--Q--Tby reaction with an amine of the formula ##STR2## into the sulfonylurea of the above formula. There are also described novel sulfonylcarbamates of the above formula as intermediates.Type: GrantFiled: January 30, 1987Date of Patent: November 15, 1988Assignee: Ciba-Geigy CorporationInventors: Willy Meyer, Werner Fory, Werner Topfl
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Patent number: 4762848Abstract: Heterocyclic sulfides of the general formula heterocycle-S-R, a process for their preparation and, in particular, their use for immunostimulation, immunorestoration and cytostatic treatment, and pharmaceutical agents, which contain a sulfide of this type, for these indications.Type: GrantFiled: March 10, 1986Date of Patent: August 9, 1988Assignee: Hoechst AktiengesellschaftInventors: Karl-Heinz Scheunemann, Walter Durckheimer, Jurgen Blumbach, Michael Limbert, Hans-Ulrich Schorlemmer, Gerhard Dickneite, Hans-Harald Sedlacek
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Patent number: 4743617Abstract: This invention relates to novel heterocyclyl-2-propyn-1-amines which are useful as dopamine beta hydroxylase inhibitors in the treatment of hypertension.Type: GrantFiled: August 31, 1987Date of Patent: May 10, 1988Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Thomas M. Bargar, Lawrence C. Creemer, James R. McCarthy
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Patent number: 4680420Abstract: A process is described for producing 2,5-dimethoxytetrahydrofuran and 2,5-diethoxytetrahydrofuran by treating 4,4-dimethoxy-1-butanal and 4,4-diethoxy-1-butanal with a strongly acidic ion exchange resin at a temperature of between 0.degree. and 70.degree. C.Type: GrantFiled: December 1, 1986Date of Patent: July 14, 1987Assignee: Degussa AktiengesellschaftInventors: Juan Andrade, Gunter Prescher
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Patent number: 4659844Abstract: The invention relates to new cyclic ethers which are substituted in the .alpha.-position by an isocyanide-dichloride group, of the formula ##STR1## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and n have the meaning indicated in the description, and to a process for their preparation.Type: GrantFiled: July 25, 1985Date of Patent: April 21, 1987Assignee: Bayer AktiengesellschaftInventors: Tillmann Hassel, Hanns P. Muller, Horst Boshagen
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Patent number: 4643849Abstract: This invention relates to amine derivatives and salts thereof. These compounds have an anti-ulcer activity which is effective to human beings and animals. This disclosure relates to such compounds, a process for the preparation thereof and an anti-ulcer agent containing the same.Type: GrantFiled: November 14, 1983Date of Patent: February 17, 1987Assignee: Toyama Chemical Co., Ltd.Inventors: Shiro Hirai, Hiroshi Hirano, Hirotoshi Arai, Yasuo Kiba, Hisanari Shibata, Yoshikazu Kusayanagi, Minako Yotsuji, Kazuhiko Hashiba, Kikuko Tanada
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Patent number: 4634783Abstract: Amidine compounds of the formula ##STR1## and pharmaceutically acceptable acid addition salts thereof are novel compounds and are useful as powerful anti-trypsin, anti-plasmin, anti-kallikrein and anti-thrombin agents. They are also useful as a powerful anti-complement agent.Type: GrantFiled: January 23, 1984Date of Patent: January 6, 1987Assignee: Torii & Co. Ltd.Inventors: Setsuro Fujii, Toyoo Nakayama, Shigeki Nunomura, Ryoji Matsui, Shin-ichi Watanabe, Kimio Sudo, Toshiyuki Okutome, Masateru Kurumi, Yojiro Sakurai, Takuo Aoyama
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Patent number: 4600761Abstract: Acrylic emulsion copolymers are prepared by emulsion polymerization of (A) a surfactant monomer, (B) an .alpha., .beta.-ethylenically unsaturated carboxylic acid monomer, (C) a nonionic .alpha., .beta.-ethylenically unsaturated monomer and (D) optionally a polyethylenically unsaturated cross-linking monomer. The surfactant monomer is prepared by condensing a polyhydric alcohol or primary amine-containing nonionic surfactant with a monoethylenically unsaturated monoisocyanate. At a low pH the copolymer may be in the form of an aqueous dispersion or latex, but thickens upon neutralization of at least some of the carboxyl groups.Type: GrantFiled: October 1, 1985Date of Patent: July 15, 1986Assignee: Alco Chemical CorporationInventors: Charles G. Ruffner, John M. Wilkerson, III
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Patent number: 4593057Abstract: Novel phenolic compounds derived from hexitans are disclosed which are useful stabilizers of synthetic polymer resins. A process for manufacture of these stabilizers is also provided.Type: GrantFiled: August 15, 1985Date of Patent: June 3, 1986Assignee: ICI Americas Inc.Inventors: John F. Stephen, Jerry H. Smith
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Patent number: 4564692Abstract: A simplified economical process is provided for preparing pure anhydro sugar alcohols by a controlled crystallization from concentrated aqueous solutions or melts containing these alcohols. These pure anhydro sugar alcohols are useful as polyol components in making polyester and polyurethane polymers.Type: GrantFiled: July 18, 1983Date of Patent: January 14, 1986Assignee: CPC International Inc.Inventors: John Feldmann, Hubert Koebernick, Klaus Richter, Hans-Ulrich Woelk
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Patent number: 4554363Abstract: Process for the preparation of bicyclic ketones containing blocked hydroxy groups, of general Formula I ##STR1## wherein R.sub.1 is the residues --CH.sub.2 OR.sub.2 wherein R.sub.2 means benzyl, dimethyl-tert-butylsilyl, diphenyl-tert-butylsilyl, dimethylphenylsilyl, tribenzylsilyl, or tetrahydropyranyl, ##STR2## with R.sub.2 having the meanings given above, R.sub.4 meaning hydrogen or methyl, and R.sub.5 meaning a straight-chain or branched-chain, saturated or unsaturated alkyl residue which can contain fluorine, chlorine, 1,2-methylene, 1,1-trimethylene, or methoxy substitutents, or a CH.sub.2 --X-Aryl residue with X meaning CH.sub.2 or O and Aryl meaning phenyl or a heterocyclic residue, which residues can be substituted by methyl, methoxy, fluorine, chlorine, bromine, or trifluoromethyl, or ##STR3## with the meanings for R.sub.2, R.sub.4, and R.sub.5 as indicated above, and R.sub.3 having the meanings set forth for R.sub.2, it being possible for R.sub.3 to be identical to R.sub.2 or different from R.sub.Type: GrantFiled: June 23, 1983Date of Patent: November 19, 1985Assignee: Schering AktiengesellschaftInventor: Helmut Vorbrueggen
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Patent number: 4539332Abstract: Analogs of 2,5-Diaryl tetrahydrofurans which were substituted or unsubstituted at 3,4-positions were prepared.These compounds are found to have potent and specific PAF (Platelet Activating Factor) antagonistic activities and thereby useful in the treatment of various diseases or disorders mediated by the PAF, for example, inflammation, cardiovascular disorder, asthma, lung edema, adult respiratory distress syndrome, pain, and aggregation of platelets.Type: GrantFiled: November 14, 1983Date of Patent: September 3, 1985Assignee: Merck & Co., Inc.Inventors: Tesfaye Biftu, San-Bao Hwang, Thomas W. Doebber, Thomas R. Beattie, Tsung-Ying Shen
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Patent number: 4522630Abstract: Cetane number of diesel fuel is increased by the addition of a tetrahydro-2,5-furandimethanol dinitrate.Type: GrantFiled: March 29, 1984Date of Patent: June 11, 1985Assignee: Ethyl CorporationInventor: Paul D. Seemuth
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Patent number: 4441910Abstract: Novel thiophenes or furans show herbicidal activity and may also have post- and pre-emergence crop tolerance, especially to corn.Type: GrantFiled: February 8, 1982Date of Patent: April 10, 1984Assignee: E. I. Du Pont de Nemours and CompanyInventor: Rafael Shapiro
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Patent number: 4435586Abstract: A high yield process for the polyalkylation of hexitols and hexitol inner ethers is presented wherein aqueous dispersions of monoalkali metal alkoxides thereof in organic solvent are reacted with alkyl monohalides to first form the monoalkylated hexitols or hexitol inner ether and thereafter further alkylated by addition of reactants to form the completely alkylated derivative.Type: GrantFiled: April 28, 1982Date of Patent: March 6, 1984Inventors: Walter M. Kruse, John F. Stephen
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Patent number: 4388469Abstract: Diphenylalkanoether and diphenylalkanone oxime-ether derivatives of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are each independently an aryl group optionally substituted with 1 to 3 substituents selected from the group consisting of halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro, cyano, di(C.sub.1 -C.sub.4)alkylamino, amino, benzyloxy, hydroxyl, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 alkanoylamino, C.sub.1 -C.sub.4 alkylamino and N-(C.sub.1 -C.sub.4)alkyl-N-(C.sub.1 -C.sub.4)alkanoylamino, Z.sup.1 is a group of the formula: ##STR2## (wherein R.sup.3 and R.sup.4 are each independently a hydrogen atom, a C.sub.1 -C.sub.4 alkyl group or an ar(C.sub.1 -C.sub.Type: GrantFiled: April 2, 1980Date of Patent: June 14, 1983Assignee: Sumitomo Chemical Company, LimitedInventors: Keiichi Ono, Hajime Kawakami, Junki Katsube
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Patent number: RE33008Abstract: Acrylic emulsion copolymers are prepared by emulsion polymerization of (A) a surfactant monomer, (B) an .alpha..beta.-ethylenically unsaturated carboxylic acid monomer, (C) a nonionic.alpha..beta.-ethylenically unsaturated monomer and (D) optionally a polyethylenically unsaturated cross-linking monomer. The surfactant monomer is prepared by condensing a polyhydric alcohol or primary amine-containing nonionic surfactant with a monoethylenically unsaturated monoisocyanate. At a low pH the copolymer may be in the form of an aqueous dispersion or latex, but thickens upon neutralization of at least some of the carboxyl groups.Type: GrantFiled: June 13, 1988Date of Patent: August 1, 1989Assignee: Alco Chemical CorporationInventors: Charles G. Ruffner, John M. Wilkerson, III