Carbonyl Containing (e.g., Ketone Containing, Etc.) Patents (Class 568/31)
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Patent number: 4853028Abstract: Compounds of the formula ##STR1## wherein R is halogen, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, cyano, nitro, (S(O).sub.n R wherein R is C.sub.1 -C.sub.4 alkyl and n is the integer 0, 1 or 2; and R.sup.2 through R.sup.8 are hydrogen or certain substituents, their salts, herbicidal compositions containing the compound or salts and the herbicidal use thereof.Type: GrantFiled: December 4, 1987Date of Patent: August 1, 1989Assignee: Stauffer Chemical CompanyInventors: Charles G. Carter, David L. Lee, William J. Michaely
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Patent number: 4845129Abstract: The invention discloses certain diaryl substituted cyclopentane and cyclopentene derivatives useful as PAF inhibitors, pharmaceutical compositions containing said compounds as an active ingredient thereof and a method of using such compositions for inhibiting PAF-induced blood platelet aggregation, PAF-mediated broncho-constriction and extravasation, PAF-induced hypotension, PAF-induced ischemic bowel disease and PAF-mediated, endotoxin induced lug injury.Type: GrantFiled: March 14, 1988Date of Patent: July 4, 1989Assignee: Sandoz Pharm. Corp.Inventors: Robert C. Anderson, William J. Houlihan, Howard C. Smith, Edwin B. Villhauer
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Patent number: 4837352Abstract: An intermediate compound having the structural formula ##STR1## wherein 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; or R.sup.1 and R.sup.2 together are alkylene having 2 to 5 carbon atoms; 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; or R.sup.3 and R.sup.4 together can be oxo; R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.6 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.5 and R.sup.6 together are alkylene having 2 to 5 carbon atoms; R.sup.7 and R.sup.8 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub. 1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (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.Type: GrantFiled: March 21, 1988Date of Patent: June 6, 1989Assignee: Stauffer Chemical CompanyInventor: Christopher G. Knudsen
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Patent number: 4833164Abstract: 2-Substituted-1-naphthols are 5-lipoxygenase inhibitors which make them useful in the treatment of inflammation, obstructive lung diseases and/or psoriasis. Useful 2-substituent groups are alkyls, alkenyls, alkynyls, cycloalkyls, cycloalkenyls, the groups CH.sub.2 --C.tbd.C--(CH.sub.2).sub.m R.sup.5 and CH.dbd.CH--(CH.sub.2).sub.n R.sup.5 (where m is 1-4, n is 0-3 and R.sup.5 includes phenyl, COOR.sup.9, where R.sup.9 is H or alkyl of 1-4 carbons, AR.sup.6 (where A is a methylene chain and R.sup.6 is a variety of groups including Cl, Br, I, CHO, CN, COOR.sup.9, NH.sub.2, SC(NH)NH.sub.2, phenyl, P(O)(OR.sup.9).sub.2, etc.), and CHR.sup.7 R.sup.21 (where R.sup.7 is a variety of aromatic and heterocyclic groups and R.sup.21 is H, optionally substituted phenyl and a variety of heterocyclic groups).Type: GrantFiled: March 19, 1986Date of Patent: May 23, 1989Assignee: E. I. Du Pont de Nemours and CompanyInventor: Douglas G. Batt
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Patent number: 4827004Abstract: Novel Isoprene Derivatives which have mucosa-protective and gastric acid secretion-inhibiting properties and are useful for combatting ulcers both by treating and as a prophylaxis against gastric and/or duodenal ulcers.Type: GrantFiled: August 24, 1987Date of Patent: May 2, 1989Assignee: Hoffmann-La Roche Inc.Inventors: Albert Fischli, Max Schmid, Rudolf Schmid
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Patent number: 4822905Abstract: Compounds having the structural formula ##STR1## wherein R.sub.1, R.sub.2 R.sub.3, R.sub.4 and R.sup.5 are the same or different and are selected from the group consisting of hydrogen, chlorine, bromine, iodine, nitro, alkyl having from 1 to 4 carbon atoms, alkoxy having from 1 to 4 carbon atoms, trifluoromethyl, trifluoromethoxy, cyano, alkylsulfonyl, and alkylthio having from 1 to 4 carbon atoms, and wherein R.sub.2 and R.sub.3 or R.sub.3 and R.sub.4 together can be methylene or ethylenedioxy.Type: GrantFiled: June 9, 1986Date of Patent: April 18, 1989Assignee: Stauffer Chemical CompanyInventors: David L. Lee, Donald R. James, William J. Michaely
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Patent number: 4795488Abstract: Compounds of the formula ##STR1## wherein R is halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; trifluoromethoxy or difluoromethoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; R.sup.a SO.sub.n --wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl, trifluoromethyl or difluoromethyl;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; orR.sup.1 and R.sup.2 together are C.sub.2 -C.sub.5 alkylene;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; orR.sup.3 and R.sup.4 together are C.sub.2 -C.sub.5 alkylene;R.sup.5, R.sup.6, R.sup.7 and R.sup.8 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (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.Type: GrantFiled: September 12, 1986Date of Patent: January 3, 1989Assignee: Stauffer Chemical CompanyInventor: David L. Lee
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Patent number: 4783278Abstract: In general, inorganic or organic peroxyacids are unstable in the presence of a nonionic surfactant, so that it was not feasible to contemplate storing liquid compositions containing both components. It has now been discovered that storable compositions containing both components can be obtained by the use of particulate potassium-4-sulphoperoxybenzoic acid dispersed in the liquid nonionic surfactant containing phase. Additionally, the compositions can also include a dispersed particulate water-insoluble builder such as zeolite or water-soluble builder such as STPP. It is preferable to include a small amount of a chelating peroxidic stabilizer such as dipicolinic acid or 1,1,1-hydroxyethylidene diphosphonic acid.Type: GrantFiled: February 4, 1987Date of Patent: November 8, 1988Assignee: Interox Chemicals LimitedInventors: William R. Sanderson, John D. Wharne
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Patent number: 4783213Abstract: Compounds of the formula ##STR1## wherein X is oxy, thio, sulfinyl or sulfonyl;R is halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; trifluoromethoxy; difluoromethoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; R.sup.a SO.sub.n -- wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl, trifluoromethyl or difluoromethyl;R.sup.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, phenyl or substituted phenyl;R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.1 and R.sup.2 together are C.sub.2 -C.sub.5 alkylene;R.sup.3 is hydrogen, C.sub.1 -C.sub.4 alkyl, phenyl or substituted phenyl with the proviso that R.sup.1 and R.sup.3 are not both phenyl or substituted phenyl;R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.6 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, or phenyl;R.sup.7 and R.sup.8 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.Type: GrantFiled: August 20, 1987Date of Patent: November 8, 1988Assignee: Stauffer Chemical CompanyInventor: David L. Lee
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Patent number: 4781751Abstract: Compounds of the formula ##STR1## wherein R is halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; trifluoromethoxy; difluoromethoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; R.sup.a SO.sub.n -- wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl; trifluoromethyl or difluoromethyl;R.sup.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, halogen, phenyl or substituted phenyl;R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.1 and R.sup.2 together are C.sub.2 -C.sub.5 alkylene;R.sup.3 is hydrogen, C.sub.1 -C.sub.4 alkyl, phenyl or substituted phenyl, with the proviso that R.sup.1 and R.sup.3 are not both phenyl or substituted phenyl;R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.5 is hydrogen, halogen or C.sub.1 -C.sub.4 alkyl;R.sup.6 is halogen, cyano, nitro, trifluoromethyl, --C(O)--OR.sup.f wherein R.sup.f is C.sub.1 -C.sub.4 alkyl, or --C(O)NR.sub.2.sup.b wherein R.sup.b is hydrogen or C.sub.1 -C.sub.2 alkyl;R.sup.7 and R.sup.8 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.Type: GrantFiled: October 2, 1987Date of Patent: November 1, 1988Assignee: Stauffer Chemical CompanyInventor: Hsiao-Ling M. Chin
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Patent number: 4772727Abstract: A multistage method for producing R-(+)-.alpha.-lipoic acid and S-(-)-.alpha.-lipoic acid (thioctic acid) by reacting a compound of formula II ##STR1## by means of enantioselective epoxidation to the epoxy alcohol of formula III, ##STR2## reduction to 1,3-diol-dihydroxynone-8-ene of formula IV, ##STR3## reaction with a substituted sulfonic acid chloride to 1,3-disulfoxynone-8-ene of formula V, ##STR4## oxidation with ruthenium tetroxide to 6,8-disulfoxyoctanoic acid of formula VI ##STR5## and subsequent reaction with sodium sulfide/sulfur.Type: GrantFiled: August 7, 1987Date of Patent: September 20, 1988Assignee: DegussaInventors: Ian O. Sutherland, Philip C. B. Page, Christopher M. Rayner
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Patent number: 4766248Abstract: .beta.-Substituted polyfluoroethyl compounds, process for the preparation thereof, copolymers thereof, compound intermediates, and process therefor. The copolymers are useful as ion exchange resins or structural foams.Type: GrantFiled: January 16, 1986Date of Patent: August 23, 1988Assignee: E. I. Du Pont de Nemours and CompanyInventor: Carl G. Krespan
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Patent number: 4762551Abstract: A compound of the formula ##STR1## wherein 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; or R.sup.1 and R.sup.2 together are alkylene having 2 to 5 carbon atoms; 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; or R.sup.3 and R.sup.4 can be oxo; R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.6 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.5 and R.sup.6 together are alkylene having 2 to 5 carbon atoms; and R.sup.7 and R.sup.8 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (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.Type: GrantFiled: June 9, 1986Date of Patent: August 9, 1988Assignee: Stauffer Chemical CompanyInventor: Christopher G. Knudsen
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Patent number: 4751240Abstract: A phenol derivative of the formulaNU--A--X--R.sup.1wherein NU is a defined phenolic nucleus including a phenyl-hydroxynaphthyl; hydroxyphenyl-naphthyl; phenyl-hydroxyindanyl, phenyl-hydroxybenzothienyl or mono-hydroxyphenyl-ethylene or vinylene nucleus; wherein A is alkylene, alkenylene or alkynylene which may be interrupted by phenylene or other linkages, wherein R.sup.1 is hydrogen, or alkyl, alkenyl, alkynyl, cycloalkyl, halogenoalkyl, alkoxyalkyl, halogenoalkoxyalkyl, aryl or arylalkyl, or R.sup.1 is joined to R.sup.2, and wherein X is --CONR.sup.2 --, --CSNR.sup.2 --, --NR.sup.12 CO--, --NR.sup.12 CS--, --NR.sup.12 CONR.sup.2 --, ##STR1## --SO.sub.2 NR.sup.2 --or --CO--, or, when R.sup.1 is not hydrogen, is --NR.sup.12 COO--, --(PO)R.sup.2 13 , --S--, --SO--or --SO.sub.2 --, wherein R.sup.2 is hydrogen or alkyl, or R.sup.1 and R.sup.2 together form alkylene; wherein R.sup.12 is hydrogen or alkyl, and wherein R.sup.22 is hydrogen, cyano or nitro; or a salt thereof when appropriate.Type: GrantFiled: April 24, 1985Date of Patent: June 14, 1988Assignee: Imperial Chemical Industries PLCInventors: Jean Bowler, Graham C. Crawley, Philip N. Edwards, Alasdair T. Glen, Michael S. Large, Brian S. Tait
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Patent number: 4724263Abstract: Compounds of the formula ##STR1## wherein R is hydrogen; 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.m --wherein m is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl;R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are methyl or ethyl;R.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) trifluoromethoxy; (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.sup.c and R.sup.d independently are hydrogen or C.sub.1 -C.sub.4 alkyl; (11) R.sup.e C(O)--wherein R.sup.e is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy; or (12) --SO.sub.2 NR.sup.c R.sup.d wherein R.sup.c and R.sup.d are as defined; and (13) --N(R.sup.c)C(O)R.sup.d wherein R.sup.c and R.sup.Type: GrantFiled: June 9, 1986Date of Patent: February 9, 1988Assignee: Stauffer Chemical CompanyInventor: Charles G. Carter
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Patent number: 4724267Abstract: Bis(haloacylaromatic) compounds have been made by a new process in which monohaloacylated aromatic compounds have been reacted by a coupling reaction. These bis(haloacylaromatic) compounds can be employed as monomers in the preparation of polyesters and polyamides which have easy processability. The monohaloacylated compound is coupled by reacting two moles of the monomer with a carbon or sulfur compound containing at least two halogen atoms in the presence of a Friedel-Crafts catalyst.Type: GrantFiled: May 23, 1986Date of Patent: February 9, 1988Assignee: The Dow Chemical CompanyInventors: George M. St. George, Marlin E. Walters
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Patent number: 4686235Abstract: Substituted cinnamyl-2,3-dihydrobenzofurans and analogs were prepared from the nucleophlic substitution of a cinnamylhalide with a 2,3-dihydrobenzofuran anion or an analog thereof. These compounds were found to be potent topical anti-inflammatory agents.Type: GrantFiled: August 12, 1985Date of Patent: August 11, 1987Assignee: Merck & Co., Inc.Inventors: Michael N. Chang, Norman P. Jensen, Milton L. Hammond, Robert A. Zambias, John McDonald, Kathleen M. Rupprecht
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Patent number: 4681621Abstract: Compounds of the formula ##STR1## wherein R is halogen, preferably chlorine or bromine; C.sub.1 -C.sub.4 alkoxy, preferably methoxy; nitro; cyano; --S(O).sub.n R' wherein n is the integer 0, 1 or 2, preferably 2 and R' is C.sub.1 -C.sub.4 alkyl, preferably methyl; or R is C.sub.1 -C.sub.4 alkyl or methyl and most preferably R is chlorine, bromine, methoxy, nitro, methyl or CF.sub.3 ; R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.2 is hydrogen, C.sub.1 -C.sub.4 alkyl or ##STR2## wherein R.sup.a is C.sub.1 -C.sub.4 alkyl; R.sup.1 and R.sup.2 together are alkylene having 3 to 6 carbon atoms; 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; and R.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) OCF.sub.3 ; (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.Type: GrantFiled: December 3, 1985Date of Patent: July 21, 1987Assignee: Stauffer Chemical CompanyInventors: David L. Lee, William J. Michaely
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Patent number: 4670577Abstract: A novel process for the preparation of pent-4-enoic acids of the formula ##STR1## wherein X is selected from the group consisting of hydrogen, cyano and alkoxycarbonyl of 2 to 5 carbon atoms and Y is selected from the group consisting of hydrogen, cyano, alkoxycarbonyl 2 to 5 carbon atoms, acyl of an organic carboxylic acid of 2 to 7 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms and arylsulfonyl of 6 to 7 carbon atoms with the proviso that X and Y are not both hydrogen comprising reacting a compound of the formula ##STR2## wherein R is selected from the group consisting of acyloxy of an organic carboxylic acid of 1 to 7 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms and arylsulfonyl of 6 to 7 carbon atoms with an anion derivative of a compound of the formula ##STR3## wherein X.sub.1 and Y.sub.Type: GrantFiled: February 24, 1984Date of Patent: June 2, 1987Assignee: Roussel UclafInventors: Marc Julia, Therese Cuvigny
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Patent number: 4661636Abstract: Compounds of the formula I ##STR1## where R.sup.1 is hydrogen, lower alkyl, lower alkoxy, amino or dialkylamino; R.sup.2 and R.sup.3 are O-alkyl, N-dialkyl or S-alkyl, or R.sup.2 and R.sup.3 together represent --X--(CH.sub.2).sub.m --X, a carbonyl group or an imino group NR, and m is 2-6; where R.sup.4 is lower alkyl, cycloalkyl, alkenyl or dialkylamino, and where R.sup.5 is lower alkyl or cycloalkyl, and where n is 1 or 2, have excellent cytoprotective effects.They are prepared by reacting compounds II ##STR2## with formaldehyde or a reagent producing formaldehyde.Type: GrantFiled: September 7, 1984Date of Patent: April 28, 1987Assignee: Hoechst AktiengesellschaftInventors: Heinrich C. Englert, Hans-Jochen Lang, Dieter Mania, Martin Bickel
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Patent number: 4657956Abstract: Additives for rubber compositions, giving vulcanizates having improved retention of optimum physical properties, are compounds having the formula R--S--B--S--R where B is an organic bridging group and R is an electron-withdrawing group, for example CN, CCl.sub.3, a radical containing an activated methylene group linked to the sulphur atom or the enolic tautomer of a keto-activated methylene group. Also useful as stabilizing agents are oligomeric analogues of such compounds.Type: GrantFiled: September 13, 1985Date of Patent: April 14, 1987Assignee: Monsanto Europe, S. A.Inventors: Albert F. L. G. Devaux, Philippe G. Moniotte
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Patent number: 4625066Abstract: Novel substituted acetylene-ketones of the formulaR.sup.2 --C.tbd.C--CO--R.sup.1 (I)in whichR.sup.1 represents optionally substituted cycloalkyl with 4 to 7 carbon atoms or the groupings ##STR1## or represents optionally substituted aryl, if R.sup.2 represents optionally substituted cycloalkenyl or optionally substituted cycloalkylalkyl;R.sup.2 represents alkyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted cycloalkylalkyl, optionally substituted aryl or optionally substituted aralkyl;R.sup.3 represents halogen;R.sup.4 represents hydrogen or halogen;R.sup.5 represents alkyl with more than 1 carbon atom, alkenyl, alkinyl or the CHO group or a derivative thereof, or represents methyl, if R.sup.2 represents optionally substituted cycloalkenyl or optionally substituted cycloalkylalkyl;R.sup.6 represents cyano, optionally substituted aryl or the groupings --XR.sup.7 or --CONR.sup.8 R.sup.9 ;R.sup.Type: GrantFiled: November 29, 1984Date of Patent: November 25, 1986Assignee: Bayer AktiengesellschaftInventor: Hans-Ludwig Elbe
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Patent number: 4621098Abstract: The present invention provides thioethers of the general formula: ##STR1## wherein Ar is a phenyl radical which is optionally substituted one, two or three times by alkyl, alkenyl, alkoxy, alkylthio, alkanoyl, hydroxyl, hydroxyalkyl, carboxyl, alkoxycarbonyl, carbamoyl, nitro, amino or halogen, Q is an oxygen or sulphur atom or an NH group, A is a straight-chained or branched C.sub.2 -C.sub.8 alkylene radical which is optionally substituted by a hydroxyl group or can be interrupted by an ethenylene or ethynylene group, n is 0, 1 or 2, and R is a hydrogen atom or a straight-chained or branched alkyl radical which is optionally substituted one or more times by the same or different radicals selected from alkoxycarbonyl, alkoxy, hydroxyl, carboxyl or optionally substituted carbamoyl or amino; as well as the pharmacologically acceptable salts thereof, with the proviso that A cannot be ethylene when Ar is a phenyl radical, Q is an oxygen atom and R is the group --CH.sub.2 COOH.Type: GrantFiled: July 2, 1984Date of Patent: November 4, 1986Assignee: Boehringer Mannheim GmbHInventors: Robert Umminger, Walter-Gunar Friebe, Wolfgang Kampe, Androniki Roesch, Otto-Henning Wilhelms
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Patent number: 4612394Abstract: A process for producing aminophenyl-.beta.-hydroxyethylsulfone of the formula (I), ##STR1## which comprises the following steps: (1) condensing nitrohalobenzene with mercaptoethanol in the presence of an alkali hydroxide and at least one reaction medium selected from N-alkyl-substituted amides and sulfoxides to produce mononitrophenyl-.beta.-hydroxyethylsulfide of the formula (II): ##STR2## (2) oxidizing the mononitrophenyl-.beta.-hydroxyethylsulfide (II) to produce mononitrophenyl-.beta.-hydroxyethylsulfone of the formula (III): ##STR3## and (3) reducing the mononitrophenyl-.beta.-hydroxyethylsulfone to produce the aminophenyl-.beta.-hydroxyethylsulfone of the formula (I). This compound is useful as an intermediate for aminophenyl-.beta.-sulfatoethylsulfone represented by the following formula: ##STR4## which is an important intermediate for vinyl sulfone type reactive dyes largely used for dyeing cellulose fiber materials.Type: GrantFiled: March 21, 1983Date of Patent: September 16, 1986Assignee: Sumitomo Chemical Company, LimitedInventors: Norio Kotera, Kazuhiro Tada, Shinzaburo Masaki, Kunihisa Goto, Tatsuo Kaneoya
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Patent number: 4605745Abstract: A method is provided for making aromatic ethers by effecting the displacement of reactive radicals on an activated aromatic nucleus such as a phthalimide with a mono or bisalkali metal phenoxide in the presence of an organic solvent and a dialkylamino branched alkyl substituted pyridinium salt as a phase transfer catalyst. Improved yields of bis(aromatic ethers) are achieved without the production of undesirable by-products, such as akylated phenols.Type: GrantFiled: December 24, 1984Date of Patent: August 12, 1986Assignee: General Electric CompanyInventors: Daniel J. Brunelle, Daniel A. Singleton
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Patent number: 4597913Abstract: A novel fluorinated cation exchange membrane containing carboxylic acid groups and sulfonic acid groups, both in the form of a specific pendant structure, the carboxylic acid groups being at least 20% on one surface of the membrane and gradually decreasing toward the innerside of the membrane, which membrane is useful in electrolysis of an aqueous alkali metal halide solution with advantageously stable performance for a long term under more severe operational conditions than those conventionally used. The membrane can be prepared from a novel copolymer of a fluorinated olefin with a novel sulfur containing fluorinated vinylether of the formula: ##STR1## wherein k is 0 or 1, l is an integer of 3 to 5, Z is --S-- or --SO.sub.2 -- and R is C.sub.1 -C.sub.10 alkyl, an aryl, C.sub.1 -C.sub.10 perfluoroalkyl.Type: GrantFiled: August 29, 1983Date of Patent: July 1, 1986Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Kyoji Kimoto, Hirotsugu Miyauchi, Jukichi Ohmura, Mikio Ebisawa, Toshioki Hane
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Patent number: 4582843Abstract: Triazolyl-alkanones or triazolyl-alkanols of the formula ##STR1## in which R.sup.1 is alkyl, cycloalkyl, aryl or substituted aryl, andR.sup.2 is hydrogen, alkyl, cycloalkyl, aryl or substituted aryl, orR.sup.1 and R.sup.2 are joined to form an aliphatic ring, andA is a keto group or a CH(OH) group,or a salt thereof which possess fungicidal, microbicidal and plant-growth regulating properties.Type: GrantFiled: August 10, 1981Date of Patent: April 15, 1986Assignee: Bayer AktiengesellschaftInventors: Helmut Timmler, Wolfgang Kramer, Karl H. Buchel, Helmut Kaspers, Wilhelm Brandes
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Patent number: 4576752Abstract: .beta.-Substituted polyfluoroethyl compounds, process for the preparation thereof, copolymers thereof, compound intermediates, and process therefor. The copolymers are useful as ion exchange resins or structural foams.Type: GrantFiled: July 19, 1982Date of Patent: March 18, 1986Assignee: E. I. Du Pont de Nemours and CompanyInventor: Carl G. Krespan
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Patent number: 4567004Abstract: Monomethyl-substituted methylene compounds are obtained by reacting methylene compounds of the formula ##STR1## in which R.sup.1 and R.sup.2 independently of one another represent --CN, --CO--R.sup.3, --SO.sub.2 --R.sup.3 or --NO.sub.2 andR.sup.1 can additionally denote -aryl(R.sup.1).sub.n,whereinR.sup.3 denotes --OH, alkyl, aralkyl, aryl, alkoxy, aralkoxy or aryloxy, or amino which is substituted by alkyl and/or aralkyl and/or aryl, and furthermoretwo radicals R.sup.3 together can be an alkylene group, the radical of an aliphatic diol or of an aliphatic diamine or the group --NH--CO--NH-- and n represents 1, 2 or 3,with formaldehyde and with hydrogen in the presence of a condensation catalyst and a hydrogenation catalyst at elevated temperature, the methylene compound being introduced into the liquid phase of the mixture of reactants in the course of the reaction.Type: GrantFiled: July 18, 1984Date of Patent: January 28, 1986Assignee: Bayer AktiengesellschaftInventors: Heinz U. Blank, Erich Wolters
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Patent number: 4554381Abstract: A process for sulfonylation of halobenzenes, in which a halobenzene is reacted with a sulfonic acid, a precursor or a derivative thereof in the presence of boron trifluoride in an amount such that the absolute pressure of boron trifluoride within the reaction vessel exceeds 1 bar, and in the presence of hydrofluoric acid as a solvent. The resultant products are useful as intermediates in the synthesis of compounds having a phytosanitary (e.g., herbicidal) or pharmaceutical activity.Type: GrantFiled: June 28, 1982Date of Patent: November 19, 1985Assignee: Rhone-Poulenc Specialites ChimiquesInventor: Michel Desbois
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Patent number: 4552984Abstract: A process for the preparation of .alpha.,.alpha.-difluoroalkoxy or .alpha.,.alpha.-difluoroalkylthiophenyl sulfones, in which a polyhaloalkoxybenzene or a polyhaloalkylthiobenzene is reacted with a sulfonic acid, a derivative or a precursor of this acid, in the presence of boron trifluoride in an amount such that the absolute pressure of the boron trifluoride within the reaction vessel exceeds 1 bar, and in the presence of hydrofluoric acid as a solvent. The resultant products are useful as intermediates in the synthesis of compounds having a phytosanitary (e.g., herbicidal) or pharmaceutical activity.Type: GrantFiled: June 28, 1982Date of Patent: November 12, 1985Assignee: Rhone-Poulenc Specialites ChimiquesInventor: Michel Desbois
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Patent number: 4548640Abstract: Novel allylthiodiphenyl ether compounds exhibit excellent herbicidal activity against broadleaf weeds while leaving crops such as corn, wheat, rice and soybeans unaffected. Preparation and herbicidal activity of the compounds is disclosed and exemplified.Type: GrantFiled: October 21, 1983Date of Patent: October 22, 1985Assignee: FMC CorporationInventor: Elsayed A. Aly
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Patent number: 4547592Abstract: Arylether compounds containing terminal phenylethynyl groups are provided. Also provided is a process for producing these compounds. The following compounds are claimed; 4,4'-bis(3-phenylethynyl-phenoxy) diphenylsulfone; 2,2-bis[([([3-phenoxy]-3-phenoxy)-3-phenylethynyl]-3-phenoxy)-4-phenyl]-pr opane and 2,2-bis[([([3-phenoxy]-3-phenoxy)-3-phenyl ethynyl]-3-phenoxy)-4-phenyl]-hexafluoropropane.Type: GrantFiled: July 25, 1984Date of Patent: October 15, 1985Assignee: The United States of America as represented by the Secretary of the Air ForceInventors: Bruce A. Reinhardt, Fred E. Arnold, Marilyn R. Unroe
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Patent number: 4522950Abstract: 2,4,5-Trisubstituted-2,3-dihydrofurans useful for fungicidal applications are provided herein. The 2,3-dihydrofuran compounds correspond to the general formula ##STR1## where R is an ethyl or vinyl group, R.sub.1 is a C.sub.1-10 hydrocarbon radical and X is a nitrile, amide or sulfonyl group. The compounds of this invention are effective fungicides for the treatment of seeds and also find use in other agricultural fungicidal applications.Type: GrantFiled: June 13, 1983Date of Patent: June 11, 1985Assignee: National Distillers and Chemical CorporationInventors: Allen L. Hall, Richard G. Fayter, Jr.
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Patent number: 4517354Abstract: The compositions disclosed herein comprise compounds of the formula:DOOCArO-ArSO.sub.2 Ar'QAr'SO.sub.2 Ar-OArCOOD (I)and also derivatives and polymers therefrom or from the compound:X-ArSO.sub.2 Ar'QAr'SO.sub.2 Ar-Xin which compounds D is hydrogen, halogen or a monovalent hydrocarbon radical, preferably of 1-20 carbon atoms; Q is either --O-- or --SO.sub.2 --; Ar and Ar' are divalent aromatic groups including a multiplicity of aromatic groups linked by O, SO.sub.2, hydrocarbon groups, etc.; and X is preferably Cl but may be other halogen atoms. In these compounds, the central core or residue --ArSO.sub.2 Ar'QAr'SO.sub.2 Ar-- may be represented by A. Various derivatives and polymers having the core A are prepared, such as diamides of the formula R.sub.2 NOCArO-A-OArCONR.sub.2 ; polyester polymers of the formula [--OROOCArO-A-OArCO--]; polyarylate polymers of the formula [--ArCOOArO-A-OArOOCArCOO--]; polycarbonate polymers of the formula [--OCOOArO-A-OArOOCO--]; phenolic resins, and many other derivatives.Type: GrantFiled: October 31, 1983Date of Patent: May 14, 1985Assignee: Plastics Engineering CompanyInventor: Gaetano F. D'Alelio, deceased
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Patent number: 4513141Abstract: A method is provided for making aromatic ethers by effecting the displacement of reactive radicals on an activated aromatic nucleus such as a phthalimide with a mono or bisalkali metal phenoxide in the presence of an organic solvent and a dialkylamino branched alkyl substituted pyridinium salt as a phase transfer catalyst. Improved yields of bis(aromatic ethers) are achieved without the production of undesirable by-products, such as alkylated phenols.Type: GrantFiled: April 28, 1983Date of Patent: April 23, 1985Assignee: General Electric CompanyInventors: Daniel J. Brunelle, Daniel A. Singleton
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Patent number: 4469891Abstract: Novel 2-vinyl- and 2-ethyl-cyclopropyl sulfones are provided. In addition to the ethyl or vinyl group at the 2-position of the ring, the compounds of this invention are disubstituted at the 1-position with a sulfonyl group and an acyl, nitrile or nitrile-derived radical. The sulfones of this invention are useful chemical intermediates from which a wide variety of pesticidal, herbicidal or biologically active compounds can be prepared and are useful monomers for anionic or radical polymerizations.Type: GrantFiled: January 13, 1984Date of Patent: September 4, 1984Assignee: National Distillers and Chemical CorporationInventors: Richard G. Fayter, Jr., Allen L. Hall
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Patent number: 4460786Abstract: The selective addition of a compound having an activated carbon atom onto the carbon atom in the 4-position of a buta-1,3-diene carrying a hydrocarbon substituent on the carbon atom in the 2-position is achieved by reacting the compound having the activated carbon atom with the buta-1,3-diene carrying the hydrocarbon substituent in water or in an aqueous-alcoholic mixture in the presence of a catalyst which consists of at least one water-soluble phosphine and at least one rhodium compound, the catalyst being in solution in the water or aqueous alcoholic mixture. The products obtained are useful as precursors of intermediates for the synthesis of vitamins and perfumes.Type: GrantFiled: June 7, 1983Date of Patent: July 17, 1984Assignee: Rhone-Poulenc IndustriesInventor: Didier Morel
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Patent number: 4449001Abstract: Oxy- and thio-aryl-phenylated aromatic biscyclopentadienones are prepared from aromatic bis-benzils and benzylketones.Type: GrantFiled: March 8, 1983Date of Patent: May 15, 1984Assignee: The United States of America as represented by the Secretary of the Air ForceInventors: Bruce A. Reinhardt, Fred E. Arnold
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Patent number: 4433171Abstract: Sulphones useful for preparing polyenes have the formula: ##STR1## where the sulphonyl group replaces a hydrogen atom on carbon atom (a) or (b), R represents alkyl, aralkyl or aryl, optionally substituted, A and Q represent an optionally substituted hydrocarbon of 5n+1 carbon atoms (n is 1-5), methyl, optionally substituted by halogen, sulphide or sulphone, CH.sub.2 OH (or an ether or ester thereof), CHO (optionally protected), COOH (or an acid chloride, ester or nitrile thereof), with the proviso that when A represents a 2-(2,6,6-trimethylcyclohex-1-enyl) ethenyl radical, Q cannot represent --COOH or an ester thereof.Type: GrantFiled: February 4, 1982Date of Patent: February 21, 1984Assignee: Rhone-Poulenc S.A.Inventors: Pierre Chabardes, Marc Julia, Albert Menet
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Patent number: 4408076Abstract: 3-Alkoxy-4-substituted-phenoxy-2,3-unsaturated acid esters and derivatives thereof and the use thereof for the control of weeds.Type: GrantFiled: September 4, 1981Date of Patent: October 4, 1983Assignee: Zoecon CorporationInventor: Shy-Fuh Lee
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Patent number: 4400540Abstract: Oxy- and thio-aryl-phenylated aromatic biscyclopentadienones are prepared from aromatic bis-benzils and benzylketones.Type: GrantFiled: April 8, 1982Date of Patent: August 23, 1983Assignee: The United States of America as represented by the Secretary of the Air ForceInventors: Bruce A. Reinhardt, Fred E. Arnold
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Patent number: 4396553Abstract: This invention is directed to tetrahydronaphthalene and indane compounds and processes thereto. These compounds are useful as tumor inhibiting agents, in the treatment of neoplasms and dermatological conditions.Type: GrantFiled: February 4, 1982Date of Patent: August 2, 1983Assignee: Hoffmann-La Roche Inc.Inventor: Michael Klaus
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Patent number: 4393079Abstract: Anti-inflammatory compositions are prepared which comprise a therapeutically effective amount of a compound of the formula ##STR1## wherein X is CO or CHOH; Y is CO; the dotted line represents a double bond which is present or absent; R.sub.1 is hydrogen or methyl; R.sub.2 is hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxyl, hydroxyl, acetoxyl, nitro or amino; R.sub.3 is alkyl of 3 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, alkenyl of 3 to 8 carbon atoms, cycloalkenyl of 5 to 8 carbon atoms or phenyl unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, methoxyl, ethoxyl, benzyloyl, hydroxyl, acetoxyl, trifluoromethyl, nitro, amino, acetyl, methylthiol, methylsulphonyl, methylamino and dimethylamino. Compounds of formula I above are also novel.Type: GrantFiled: December 15, 1976Date of Patent: July 12, 1983Assignee: Beecham Group LimitedInventors: William G. Cole, Alexander C. Goudie, Carl J. Rose
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Patent number: 4386220Abstract: New polyunsaturated compounds, their preparation and their use as starting materials for preparing monounsaturated bicyclic compounds useful as intermediates in the preparation of macrocyclic ketones.Type: GrantFiled: April 8, 1982Date of Patent: May 31, 1983Assignee: Firmenich, SAInventor: Charles Fehr
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Patent number: 4371708Abstract: 4-substituted 3,3-dimethyl-butan-2-ones of the formula ##STR1## in which R represents cyano or the grouping --X--R.sup.1,whereinR.sup.1 represents n-alkyl with 1 to 4 carbon atoms, isopropyl, isobutyl, sec.-butyl, alkenyl with 3 to 4 carbon atoms, alkynyl with 3 to 4 carbon atoms, optionally substituted aryl or substituted aralkyl, or represents cyano provided that X represents --O-- or --S--, andX represents --O--, --S--, --SO--, or --SO.sub.2 --,which are intermediates for the synthesis of fungicides.Type: GrantFiled: May 20, 1981Date of Patent: February 1, 1983Assignee: Bayer AktiengesellschaftInventors: Wolfgang Kramer, Hans-Ludwig Elbe
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Patent number: 4355184Abstract: .alpha., .beta.-unsaturated-ketones are synthesized by reacting with an aldehyde and an alkali metal salt of acetoacetic acid in the presence of an aliphatic secondary amine in the mixture of heterogeneous solvents producing an oil layer and a water layer.Type: GrantFiled: April 27, 1981Date of Patent: October 19, 1982Assignee: Nippon Soda Company LimitedInventors: Tsutomu Kaku, Kiyoshi Katsuura, Mikio Sawaki
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Patent number: 4349568Abstract: Novel compounds exhibiting antiviral activity are disclosed, such compounds are represented by the formula: ##STR1## wherein m represents the integer 0, 1 or 2; R represents trihalomethyl, alkyl or phenyl; R.sub.1 represents hydrogen, bromo, chloro, fluoro, cyano, nitro, amino, alkyl, alkoxy or trifluoromethyl; R.sub.2 represents hydroxyl, bromo, chloro, fluoro, cyano, acetyl, benzoyl, substituted benzoyl, alkyl, alkoxy, substituted alkoxy, benzyl, substituted benzyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, or the radical --O(CH.sub.2).sub.n R.sub.4 wherein n represents the integer 1, 2 or 3 and R.sub.4 represents cyano or dialkylamino; R.sub.3 represents hydrogen, hydroxyl, bromo, chloro, fluoro, cyano, acetyl, benzoyl, substituted benzoyl, alkyl, alkoxy, substituted alkoxy, benzyl, substituted benzyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, or the radical --O(CH.sub.2).sub.n R.sub.Type: GrantFiled: June 12, 1980Date of Patent: September 14, 1982Assignee: The Dow Chemical CompanyInventors: Lowell D. Markley, Yulan C. Tong, Steven G. Wood
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Patent number: 4338316Abstract: The disclosure relates to 9.beta.-aryloxy prostane derivatives, for example 16-(3-chlorophenoxy)-11.alpha.,15.alpha.-dihydroxy-16-methyl-9.beta.-pheno xy-18,19,20-trinor-5-cis,13-trans-prostadienoic acid, which possess high activity as abortifacients, cervical softeners, inducers of parturition or inhibitors of gastric acid production in mammals. These properties are typical of prostaglandin analogues of the E series, but chemically the new 9.beta.-aryloxy prostane derivatives are prostaglandin F series analogues and are therefore more stable than the E series analogues previously used for the above purposes. The new derivatives are manufactured by known analogy processes, and are formulated in conventional manner.Type: GrantFiled: September 26, 1979Date of Patent: July 6, 1982Assignee: Imperial Chemical Industries LimitedInventor: Peter R. Marsham
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Patent number: 4338122Abstract: 2-Aryl-1,3-cyclopentanedione compounds and their alkali metal and ammonium salts exhibit outstanding herbicidal and acaricidal activity.Type: GrantFiled: October 16, 1980Date of Patent: July 6, 1982Assignee: Union Carbide CorporationInventor: Thomas N. Wheeler