Sulfur Or Halogen Attached Directly Or Indirectly To The Hetero Ring By Nonionic Bonding Patents (Class 549/511)
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Patent number: 5059699Abstract: Sulfonated 2'-acryloyltaxol and sulfonated 2'-O-acyl acid taxol derivatives are synthesized which have improved water solubility and stability while maintaining bio-activity. In particular, 2'-[(3-sulfo-1-oxopropyl)oxy]taxol sodium salt is synthesized by reacting taxol with acrylic acid, and subsequently reacting the 2'-acryloyltaxol with bisulfite in a Michael reaction. 2'-{[4-((2-sulfoethyl)amino)-1,4-dioxobutyl]oxy}taxol sodium salt and 2'-{[4-((3-sulfopropyl)amino-1,4-dioxobutyl]oxy}taxol sodium salt are synthesized by reacting 2'-succinyltaxol with the tetrabutylammonium salts of taurine and 3-aminopropyl sulfonic acid, respectively, and subsequently exchanging the ammonium with sodium. Glycol derivatives of 2'-O-acyl acid taxols with improved water solubility are synthesized by reaction of a glycol with 2'-O-acyl acid taxol.Type: GrantFiled: August 28, 1990Date of Patent: October 22, 1991Assignee: Virginia Tech Intellectual Properties, Inc.Inventors: David G. I. Kingston, Zhi-Yang Zhao
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Patent number: 5015744Abstract: Process for the preparation of a taxol intermediate comprising contacting an alcohol with an oxazinone having the formula: ##STR1## wherein R.sub.1 is aryl, substituted aryl, alkyl, alkenyl, or alkynyl; R.sub.2 is hydrogen, ethoxyethyl, 2,2,2-trichloroethoxymethyl or other hydroxyl protecting group; and R.sub.3 is aryl, substituted aryl, alkyl, alkenyl, or alkynyl; the contacting of said alcohol and oxazinone being carried out in the presence of a sufficient amount of an activating agent under effective conditions to cause the oxazinone to react with the alcohol to form a .beta.-amido ester which is suitable for use as an intermediate in the synthesis of taxol.Type: GrantFiled: November 14, 1989Date of Patent: May 14, 1991Assignee: Florida State UniversityInventor: Robert A. Holton
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Patent number: 4987130Abstract: Substituted amino derivatives represented by the formula: ##STR1## wherein R.sup.1 and R.sup.2 each stand for an acyclic hydrocarbon residue or an alicyclic hydrocarbon residue; R.sup.3 and R.sup.4 each stand for hydrogen or a hydrocarbon residue optionally containing hetero-atom(s); A stands for a carbon chain having two or more carbon atoms optionally containing ether linkage or sulfide linkage, which may be substituted and which may per se form a ring; X.sup.1 and X.sup.2 each stand for oxygen atom or sulfur atom; and Y stands for amino group or an organic residue bonded through nitrogen atom, which may form a ring by combining with a carbon atom constituting A; and their salts have anti-arrhythmic activity and are useful for prevention and treatment of a variety of arrhythmias.Type: GrantFiled: December 22, 1989Date of Patent: January 22, 1991Assignee: Takeda Chemical Industries, Ltd.Inventors: Susumu Tsushima, Muneo Takatani, Minoru Hirata
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Patent number: 4983779Abstract: An improved process for the preparation of vinyl ethers by the coupling reaction of an ester of the formula ##STR1## with a carbonyl containing compound of the formula ##STR2## wherein A and R are passive organic groups and OY is a hydroxyl group or OP where P is a protecting group is described. The ester and the carbonyl containing compound are reacted in an organic solvent with a titanium salt, a metallic reducing agent and an amine base to provide the vinyl ether. The reaction is safe and produces high yields. The vinyl ethers are useful for producing dioxetanes which produce light upon triggering.Type: GrantFiled: December 14, 1989Date of Patent: January 8, 1991Assignee: The Board of Governors of Wayne State UniversityInventor: Arthur P. Schaap
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Patent number: 4973716Abstract: A process for fluorinating hydrogenated ethereal compounds by direct reaction with elemental F.sub.2 diluted with an inert gas, wherein the starting compound is in the liquid phase, said fluorination being carried out in the presence of a per fluoropolyetheral compound and of an alkaline metal fluoride.Type: GrantFiled: December 11, 1989Date of Patent: November 27, 1990Assignee: Ausimont S.p.A.Inventors: Pierangelo Calini, Silvana Modena
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Patent number: 4971979Abstract: Substituted alkadienes of formula: ##STR1## in which R.sub.1 is hydroxy or acetoxy, R.sub.2 is hydrogen, carboxy, alkoxycarbonyl, phenyl or benzoyl, andR.sub.3 is alkylthio or alkoxy and R.sub.4 is naphthoyl or optionally substituted benzoyl,or R.sub.3 is alkoxycarbonyl, cycloalkyloxycarbonyl or cyano and R.sub.4 is alkyl, naphthyl, optionally substituted phenyl, alkylthio, naphthylmethanethio, optionally substituted benzylthio, optionally substituted phenylthio, naphthylthio, phenethylthio or allylthio,or R.sub.3 and R.sub.4 form, with the carbon atom to which they are attached, a ring-system of formula: ##STR2## in which R.sub.5 is hydrogen or alkoxy and X is methylene or S inhibit 5-lipoxygenase and are useful, for example, as anti-inflammatories.Type: GrantFiled: July 19, 1989Date of Patent: November 20, 1990Assignee: Rhone-Poulenc SanteInventors: Jean-Luc Malleron, Gerard Ponsinet, Gerard Roussel
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Patent number: 4952707Abstract: Chemiluminescent 1,2-dioxetane compounds are disclosed in which the molecule is stabilized at the 3-position on the dioxetane ring against decomposition prior to the molecule's coming in contact with a labile group-removing substance (e.g., an enzyme that will cleave the labile group to cause the molecule to decompose to form at least one light-emitting fluorophore) and substituted at the 4-position on the dioxetane ring with a fused polycyclic ring-containing fluorophore moiety bearing a labile ring substituent whose point of attachment to the fused polycyclic ring, in relation to this ring's point(s) of attachment to the dioxetane ring, is such that the total number of ring atoms separating these points of attachment, including the ring atoms at the points of attachment, is an odd whole number. These odd pattern substituted compounds decompose to emit light of greater intensity and of a different wavelength than that emitted by the corresponding even pattern substituted isomers.Type: GrantFiled: June 30, 1988Date of Patent: August 28, 1990
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Patent number: 4946972Abstract: A novel process for distillation of a mixture comprising 2,2,3,3-tetrafluorooxetane, which method comprises distilling the mixture comprising 2,2,3,3-tetrafluorooxetane in a metallic distillation column in the presence of at least one additive compound selected from the group consisting of an organic nitro compound and an aromatic compound.Type: GrantFiled: January 23, 1989Date of Patent: August 7, 1990Assignee: Daikin Industries, Ltd.Inventors: Yohnosuke Ohsaka, Shoji Takaki
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Patent number: 4942184Abstract: Antineoplastic, water soluble, taxol derivatives and methods for preparing the same are described.Type: GrantFiled: March 7, 1988Date of Patent: July 17, 1990Assignee: The United States of America as represented by the Department of Health and Human ServicesInventors: Rudiger D. Haugwitz, Leon Zalkow, Jan Glinski, Mathew Suffness, Howard M. Deutsch, Venkatachala Narayanan
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Patent number: 4931569Abstract: Methods are disclosed for purifying chemiluminescent water-soluble 1,2-dioxetane derivatives suitable for use as reporter molecules in a variety of biological analytical systems, including enzyme-linked immunoassays, nucleic acid probe techniques, and structural determinations. The methods are based upon high pressure, medium pressure or low pressure liquid chromatography using as the stationary phase alkaline pH-stable compositions with the chromatographic characteristics of reversed-phase adsorbents, at alkaline pH values, and in the absence of acid-forming compounds or compounds with an unshared pair of electrons. Desalting of substantially pure water soluble 1,2-dioxetane derivatives may be accomplished by the same chromatographic systems or by molecular sieve chromatography systems, but in the absence of salt buffers. Under some circumstances, purification and desalting may be combined in a single chromatographic step.Type: GrantFiled: September 14, 1988Date of Patent: June 5, 1990
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Patent number: 4924011Abstract: Process for preparing taxol by the condensation of a (2R, 3S) acid of general formula (I) with a taxan derivative of general formula (II), followed by the removal of the groups R.sub.2 and R.sub.3 protecting the hydroxy groups.Type: GrantFiled: April 3, 1989Date of Patent: May 8, 1990Assignee: Centre National De La Recherche ScientifiqueInventors: Jean-Noel Denis, Andrew E. Greene, Daniel Guenard, Francoise Gueritte-Voegelein
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Patent number: 4924012Abstract: Process for preparing derivatives of baccatine III and of 10-deacetylbaccatine III, of general formula (I), in which R is hydrogen or acetyl, by condensation of an acid of general formula (II) with a derivative of baccatine III or of 10-deacetylbaccatine III of general formula (III), R.sub.1, R.sub.2 and R.sub.3 denoting hydroxy-protecting groups, followed by the replacement of the protecting groups by hydrogen.Type: GrantFiled: April 3, 1989Date of Patent: May 8, 1990Assignee: Rhone-Poulenc SanteInventors: Michel Colin, Daniel Guenard, Francoise Gueritte-Voegelein, Pierre Potier
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Patent number: 4908460Abstract: A process for purifying 2,2,3,3-tetrafluorooxetane which contains at least one impurity compound selected from the group consisting of hydrogen fluoride and trifluoropropionylfluoride, which process comprises contacting 2,2,3,3-tetrafluorooxetane with at least one adsorbent selected from the group consisting of silica gel and alumina and causing said impurity to be adsorbed on said particles to remove it from the 2,2,3,3-tetrafluorooxetane.Type: GrantFiled: January 23, 1989Date of Patent: March 13, 1990Assignee: Daikin Industries Ltd.Inventors: Yohnosuke Ohsaka, Shoji Takaki
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Patent number: 4886581Abstract: By extracting hydrogen fluoride from 2,2,3,3-tetrafluorooxetane with a halogenated hydrocarbon, a mixture of 2,2,3,2-tetrafluorooxetane and the halogenated hydrocarbon containing a small amount of hydrogen fluoride is obtained. The mixture may be distilled at least twice to obtain a mixture of 2,2,3,2-tetrafluorooxetane and the halogenated hydrocarbon containing substantially no hydrogen fluoride.Type: GrantFiled: July 1, 1987Date of Patent: December 12, 1989Assignee: Daikin Industries Ltd.Inventors: Yohnosuke Ohsaka, Shoji Takaki, Hiroo Sakai
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Patent number: 4864040Abstract: A novel monohalogenotrifluorooxetane of the formula: ##STR1## (wherein X is chlorine, bromine or iodine) which is prepared by reacting monohalogenotrifluoroethylene of the formula:CF.sub.2 .dbd.CFX (III)(wherein X is the same as defined above)with a compound having a --(CH.sub.2 O)-- unit.Type: GrantFiled: July 14, 1987Date of Patent: September 5, 1989Inventors: Yohnosuke Ohsaka, Satoru Kohno
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Patent number: 4857653Abstract: Taxol and 10-deacetyltaxol are prepared from a compound of formula: ##STR1## in which R' represents acetyl or 2,2,2-trichloroethoxycarbonyl radical, by removal of the t-butoxycarbonyl radical, benzoylation of the amine product obtained, and removal of the 2,2,2-trichloroethoxycarbonyl group(s).Type: GrantFiled: July 14, 1987Date of Patent: August 15, 1989Assignee: Rhone-Poulenc SanteInventors: Michel Colin, Daniel Guenard, Francoise Gueritte-Voegelein, Pierre Potier
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Patent number: 4857652Abstract: Novel light producing 1,2-dioxetanes are described of the formula ##STR1## wherein ArOX is an aryl ring substituted with an X oxy group and A are passive organic groups which allow the 1,2-dioxetane to produce light when triggered by removing X. X is a chemically labile group which is removed by an activating agent. The 1,2-dioxetane compounds can be triggered to produce light at room temperatures.Type: GrantFiled: August 23, 1988Date of Patent: August 15, 1989Assignee: Board of Governors of Wayne State UniversityInventor: Arthur P. Schaap
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Patent number: 4857651Abstract: This invention provides novel .alpha.-[2,2-di(C.sub.1 -C.sub.4 alkoxy)ethylamino]-.beta.-cyanostyrene and .alpha.-[2,2-di(C.sub.1 -C.sub.4 alkoxy)ethylamino]-.beta.-nitrostyrene compounds that are useful for the preparation of pesticidal arylpyrroles. The invention also provides a method for the preparation of the above-said .beta.-cyanostyrene and .beta.-nitrostyrene compounds.Type: GrantFiled: July 29, 1987Date of Patent: August 15, 1989Assignee: American Cyanamid CompanyInventors: Dale G. Brown, Jack K. Siddens, Robert E. Diehl, Donald P. Wright, Jr.
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Patent number: 4824975Abstract: A process for the preparation of an oxetane-3-carboxylic acid of the formula ##STR1## in which R represents hydrogen, alkyl, cycloalkyl or optionally substitute phenyl, comprising reacting a 3-hydroxymethyl-oxetane of the formula ##STR2## with oxygen in an aqueous alkaline medium at a temperature between about 0.degree. C. and the boiling point of the reaction mixture on a palladium and/or platinum catalyst. The product is an intermediate for known fungicides and herbicides.Type: GrantFiled: May 13, 1987Date of Patent: April 25, 1989Assignee: Bayer AktiengesellschaftInventors: Helmut Fiege, Manfred Jautelat, Dieter Arlt
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Patent number: 4806662Abstract: Oxetane-structure fluids of well-defined composition and free from not completely fluorinated compounds, characterized in that they have at least a perfluoroether chain bound to an oxetane ring, having improved characteristics for special applications, being liquid up to temperatures of at least -70.degree. C., having boiling temperatures in the range of from 50.degree. to 270.degree. C. or higher, and a very high range between the boiling temperature and the pour point.Type: GrantFiled: February 12, 1986Date of Patent: February 21, 1989Assignee: Ausimont S.p.A.Inventors: Gianangelo Bargigia, Gerardo Caporiccio, Claudio Tonelli, Luciano Flabbi
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Patent number: 4739068Abstract: N-Phenylsulfonyl-N'-pyrimidinylureas and --N'-triazinylureas of the general formula ##STR1## and the salts of these compounds with amines, alkali metal bases and alkaline earth metal bases or with quaternary ammonium bases, have good selective herbicidal and plant growth regulating properties when applied pre- and postemergence.In the formulaR.sub.1 is hydrogen, halogen, nitro, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.5 alkenyl or C.sub.1 -C.sub.4 alkoxycarbonyl,R.sub.2 is C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy, each unsubstituted or substituted by 1 to 3 halogen atoms,R.sub.3 is halogen, hydrogen, --NR.sub.4 R.sub.5, C.sub.1 -C.sub.3 alkyl, unsubstituted or substituted by 1 to 3 halogen atoms or C.sub.1 -C.sub.4 alkoxy, or is C.sub.1 -C.sub.3 alkoxy, unsubstituted or substituted by methoxy, ethoxy, or 1 to 3 halogen atoms,R.sub.4 is hydrogen or methyl,R.sub.5 is hydrogen, C.sub.1 -C.sub.2 alkyl or methoxy,A is C.sub.1 -C.sub.4 alkylene or C.sub.Type: GrantFiled: July 21, 1986Date of Patent: April 19, 1988Assignee: Ciba-Geigy CorporationInventors: Karl Gass, Werner Fory, Willy Meyer, Werner Topfl
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Patent number: 4736045Abstract: Fluorinated ether, process for their preparation, and use of the fluorinated ethers as inert fluids.Type: GrantFiled: September 11, 1984Date of Patent: April 5, 1988Inventors: Frederick G. Drakesmith, Richard L. Powell, Richard D. Chambers, Brian Grievson
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Patent number: 4714710Abstract: There are described new compounds of general formula I ##STR1## in which R.sub.1 is aryl or aryl substituted by C.sub.1-4 -alkyl, halo-C.sub.1-4 -alkyl, phenyl-C.sub.1-4 -alkyl, C.sub.2-4 -alkenyl, halo-C.sub.2-4 -alkenyl, phenyl-C.sub.2-4 -alkenyl, C.sub.2-4 -alkynyl, halo-C.sub.2-4 -alkynyl, phenyl-C.sub.2-4 -alkynyl, C.sub.1-4 -alkoxy, halo-C.sub.1-4 -alkoxy, phenyl-C.sub.1-4 -alkoxy, C.sub.2-4 -alkenyloxy, alkylsulphonyloxy, haloalkylsulphonyloxy, arylsulphonyloxy, halo-C.sub.2-4 -alkenyloxy, phenyl-C.sub.2-4 -alkenyloxy, halo, cyano, nitro, aryloxy, haloaryloxy, C.sub.1-4 -alkylaryloxy, or nitro-C.sub.1-4 -alkylaryloxy,R.sub.2 and R.sub.3 are the same or different and are hydrogen, fluorine, cyano or ethynyl,R.sub.4 is phenyl or pyridyl or these groups substituted by one or more of C.sub.1-6 -alkyl, halo-C.sub.1-6 -alkyl, phenyl-C.sub.1-6 -alkyl, C.sub.1-6 -alkyl interrupted by an O--, N-- or S-- atom, C.sub.2-4 -alkenyl, halo-C.sub.2-4 -alkenyl, phenyl-C.sub.2-4 -alkenyl, C.sub.1-4 -alkoxy, halo-C.sub.Type: GrantFiled: September 9, 1986Date of Patent: December 22, 1987Assignee: Schering AktiengesellschaftInventors: Heinrich Franke, Hartmut Joppien, Helga Franke
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Patent number: 4709060Abstract: A substituted trifluorooxetane of the formula: ##STR1## wherein R.sub.f is a C.sub.1 -C.sub.10 perfluoroalkyl group and n is 0, 1 or 2, which is useful as a solvent or a monomer.Type: GrantFiled: July 11, 1986Date of Patent: November 24, 1987Assignee: Daikin Industries, Ltd.Inventors: Yohnosuke Ohsaka, Shoji Takaki
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Patent number: 4687864Abstract: The present invention describes 5-fluoro-3-oxaprostacyclin (PGI.sub.2) derivatives of Formula I. These compounds are useful for the treatment of platelet dysfunction, atherosclerosis, hypertension and tumor cell metastasis. Also disclosed is the process for preparing them and the appropriate intermediates. ##STR1## wherein R.sup.1 is: (a) Na, K, or 1/2 Ca, or other pharmaceutically acceptable cation(b) NR.sup.3 .sub.2 with the adjacent connecting oxygen omitted, where R.sup.3 =H, methyl, ethyl, isopropyl or a combination of these groups;(c) Alkyl of 1 to 6 carbon atoms, either branched or straight chain(d) Hydrogenwherein OH on carbon 15 is optionally on carbon 16;wherein X=OCH.sub.3 or OC.sub.2 H.sub.5 when neither C.sub.5 -C.sub.6 or C.sub.6 -C.sub.7 is a double bond and nothing if C.sub.5 -C.sub.6 or C.sub.6 -C.sub.7 is a double bond;wherein R.sup.Type: GrantFiled: September 18, 1985Date of Patent: August 18, 1987Assignee: G. D. Searle & Co.Inventors: Stevan W. Djuric, Leland J. Chinn, Kurt J. Rorig
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Patent number: 4638060Abstract: Antibacterial activity is exhibited by compounds having the formula ##STR1## and pharmaceutically acceptable salts thereof.Type: GrantFiled: April 29, 1985Date of Patent: January 20, 1987Assignee: E. R. Squibb & Sons, Inc.Inventors: Joseph E. Sundeen, William H. Koster, Robert Zahler
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Patent number: 4608385Abstract: Use of an N-phenylcarbamate of the formula: ##STR1## as a fungicidal agent against phytopathogenic fungi, particularly their strains resistant to benzimidazole thiophanate fungicides and/or cyclic imide fungicides.Type: GrantFiled: October 22, 1982Date of Patent: August 26, 1986Assignee: Sumitomo Chemical Company, LimitedInventors: Hiroshi Noguchi, Toshiro Kato, Junya Takahashi, Yukio Ishiguri, Shigeo Yamamoto, Katsuzo Kamoshita
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Patent number: 4594446Abstract: The invention relates to new antimicrobially active 3-cephem compounds, processes for preparing such compounds, new intermediate compounds comprising alkoxyimino dioxy butyric acid derivatives useful in said processes, and processes for preparation of said intermediates.Type: GrantFiled: January 14, 1985Date of Patent: June 10, 1986Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Ikuo Ueda, Takao Takaya, Masakazu Kobayashi, Takashi Masugi, Hisashi Takasugi, Hiromu Kochi, Tadashi Kitaguchi
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Patent number: 4563476Abstract: Substituted 5-hydroxy-2,3-dihydrobenzofuran and analogs such as the substituted 6-hydroxy-2,3-dihydrobenzopyrans were prepared from an appropriately substituted (5-hydroxy-2,3-dihydrobenzofuran-6-yl) formaldehyde or analog thereof with an aryl amine followed by reduction. These compounds were found to be potent topical anti-inflammatory agents.Type: GrantFiled: November 21, 1983Date of Patent: January 7, 1986Assignee: Merck & Co., Inc.Inventors: Michael N. Chang, Milton L. Hammond, Norman P. Jensen, Robert A. Zambias
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Patent number: 4470984Abstract: An N-sulphenylated oxime-carbamate of the formula ##STR1## in which R.sup.1 is optionally substituted alkyl, cycloalkyl, aryl or aralkyl,R.sup.2 is alkyl, alkenyl or alkynyl, orR.sup.1 and R.sup.2 together are an alkylene bridge having 1-6 C atoms, one of R.sup.3 and R.sup.4 is the radical ##STR2## and the other is alkyl, alkenyl, alkynyl, halogenoalkyl, halogenoalkenyl or alkoxyalkyl,R.sup.5 is alkyl,R.sup.6 is alkyl, halogenoalkyl, optionally substituted phenyl, alkoxycarbonyl or dialkylamino, NR.sup.8 --SO.sub.2 R.sup.7, or a radical identical to the radical to which the grouping --S--R.sup.6 is bonded,R.sup.7 is alkyl, dialkylamino or optionally substituted phenyl,R.sup.8 is alkyl, andX is O or S,which possesses pesticidal activity.Type: GrantFiled: January 27, 1982Date of Patent: September 11, 1984Assignee: Bayer AktiengesellschaftInventors: Johannes Schmetzer, J/o/ rg Stetter, Ingeborg Hammann, Bernhard Homeyer
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Patent number: 4468397Abstract: Hydroxamic acid esters of the formula ##STR1## in which R.sup.1 is an optionally substituted alkyl, cycloalkyl, aryl or aralkyl radical andR.sup.2 is an alkyl, alkenyl or alkinyl radical, orR.sup.1 and R.sup.2 together are an alkylene bridge with 2 to 4 carbon atoms,one of the radicals R.sup.3 and R.sup.4 is ##STR2## while the other is an alkyl, alkenyl, alkinyl, halogenoalkenyl or alkoxyalkyl radical, andX is O or S,which possess pesticidal properties. Intermediates therefor wherein one of N--OR.sup.3 and N--OR.sup.4 is N--OH or a carbonyl group are also new.Type: GrantFiled: September 30, 1981Date of Patent: August 28, 1984Assignee: Bayer AktiengesellschaftInventors: Johannes Schmetzer, Jorg Stetter, Ingeborg Hammann, Bernhard Homeyer
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Patent number: 4411911Abstract: Novel sulfonate derivatives represented by the formulaR.sub.1 SO.sub.3 CH.sub.2 CO(CH.sub.2).sub.n R.sub.2act to inhibit esterases and chymotripsin and are useful as antilipemic agents, anti-inflammatory agents, immunity controlling agents, etc.Type: GrantFiled: January 19, 1981Date of Patent: October 25, 1983Assignee: Taiho Pharmaceutical Company, LimitedInventors: Setsuro Fujii, Toshihiro Hamakawa, Kazuo Ogawa, Yoshiyuki Muranaka, Sadao Hashimoto
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Patent number: 4371717Abstract: The present invention is directed to a process for the preparation of certain N-substituted-2-haloacetanilides via the reaction of a secondary 2-haloacetanilide with a haloalkyl ether, particularly, halomethyl ethers, which comprises forming the ether in situ by the in-solvent reaction of an alcohol, formaldehyde or other aldehyde and an acid halide to produce high purity haloalkyl ethers, while decreasing the concentration of undesirable bis by products, as for example bis(chloromethyl) ether. The ether formed in situ thereafter reacts with the secondary 2-haloacetanilide in the presence of a phase transfer catalyst and base to form the N-substituted-2-haloacetanilide.Type: GrantFiled: February 3, 1981Date of Patent: February 1, 1983Assignee: Monsanto CompanyInventors: Gerhard H. Alt, John P. Chupp