Oxygen Bonded Directly To Sulfur (e.g., Sulfoxides, Etc.) Patents (Class 568/27)
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Patent number: 5308512Abstract: The process of producing alkoxylated thiodiglycol sulfoxide derivatives and thiodiglycol sulfone derivatives corresponding to formula I ##STR1## wherein X.sub.1 and X.sub.2 may be the same or different and represent a hydroxyl-substituted aklyl radical containing 8 to 30 carbon atoms, an acyl radical of an alkyl monocarboxylic acid containing 8 to 30 carbon atoms, and X.sub.1 or X.sub.2 may be hydrogen, R represents hydrogen or methyl, z is 1 or 2, n is 0 to 25 and m is 1 to 25, by reacting an alkoxylated thiodiglycol with a C.sub.8 14 C.sub.30 .alpha.-olefin expoide or a C.sub.8 -C.sub.30 monocarboxylic acid in a molar ratio of about 1:1 to about 1:2, and oxidizing the mono- and bis- ethers or mono- and bis- esters formed to the sulfoxide or sulfone derivatives.Type: GrantFiled: March 5, 1993Date of Patent: May 3, 1994Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Gerhard Stoll, Peter Daute, Ingo Wegener, Faize Berger
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Patent number: 5304682Abstract: Disclosed is a method of making 1,1'-sulfonylbis[3-nitro-5-(trifluoromethyl) benzene] by reacting dibenzotrifluoride sulfide with at least four equivalents of fuming nitric acid and at least four equivalents of fuming sulfuric acid at a temperature below 20.degree. C., until the sulfide link is oxidized to a sulfone link, then raising the temperature to above 20.degree. C. until the reaction is complete. Also disclosed is the preparation of 1,1'-sulfonylbis[3-nitro-(5-trifluoromethyl) benzenamine] by reducing the benzene compound.Type: GrantFiled: August 17, 1989Date of Patent: April 19, 1994Assignee: Occidental Chemical CorporationInventors: Jeffrey S. Stults, Henry C. Lin
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Patent number: 5274139Abstract: A method of effecting a reaction between oxygen and an organic substance comprising the stages of:a. forming a reaction mixture comprising an N-alkylpyrrolidinone, at least one organic substance capable of reaction with oxygen and a hydroperoxide decomposition catalytically effective amount of a transition metal oxidation catalyst under a partial pressure of oxygen of at least about 16 psig, the molar ratio of organic substance to N-alkylpyrrolidinone being at least about 1:100;b. subjecting the reaction mixture to conditions such that an oxidation reaction occurs, whereby:(1) at least a portion of the N-alkylpyrrolidinone is oxidized, in situ, to the corresponding hydroperoxide;(2) the hydroperoxide is subsequently decomposed by the catalytic action of the transition metal oxidation catalyst to the corresponding N-alkylsuccinimide, the decomposition resulting in the production of active oxygen which reacts with the organic substance;c.Type: GrantFiled: February 26, 1993Date of Patent: December 28, 1993Assignee: University of FloridaInventors: Russell S. Drago, Douglas E. Patton
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Patent number: 5258433Abstract: Sulfoxides of alkylthiomethylphenols of the formula I ##STR1## in which R.sub.1 is hydrogen, C.sub.1 -C.sub.20 alkyl, C.sub.2 -C.sub.18 alkenyl, C.sub.5 -C.sub.7 cycloalkyl, C.sub.5 -C.sub.7 cycloalkenyl, phenyl or C.sub.7 -C.sub.9 phenylalkyl, R.sub.2 is hydrogen, C.sub.1 -C.sub.20 alkyl, C.sub.2 -C.sub.18 alkenyl, C.sub.5 -C.sub.7 cycloalkyl, C.sub.5 -C.sub.7 cycloalkenyl, phenyl, C.sub.7 -C.sub.9 phenylalkyl or a radical --CH.sub.2 --SO--R.sub.5, in which R.sub.5 is C.sub.8 -C.sub.20 alkyl which may be interrupted by --O--, --S-- or --SO-- groups, mono- or dihydroxy-substituted C.sub.2 -C.sub.12 alkyl, phenyl, benzyl, --(CH.sub.2).sub.n COOR.sub.6 or --CH(CH.sub.3)COOR.sub.6, in which R.sub.6 is C.sub.1 -C.sub.20 alkyl and n is 1 or 2, R.sub.3 is hydrogen or a group --CH.sub.2 --SO--R.sub.5, in which R.sub.5 is as defined above, and R.sub.4 has the same meanings as R.sub.2 , with the proviso that only one of the radicals R.sub.2, R.sub.3 or R.sub.4 is the group --CH.sub.2 --SO--R.sub.5 and that, if R.sub.Type: GrantFiled: August 20, 1991Date of Patent: November 2, 1993Assignee: Ciba-Geigy CorporationInventors: Hans-Rudolf Meier, Paul Dubs
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Patent number: 5232915Abstract: 9.alpha.-Hydroxy-19,11.beta.-bridged steroids of general formula I ##STR1## are described. The more detailed meaning of A, B, R.sup.1, R.sup.2, G, Z, R.sup.4 --Y and R.sup.4' --Y' follows from the description. The steroids of general formula I have antigestagen and/or antiglucocorticoidal action and can be used for the production of pharmaceutical agents.Type: GrantFiled: January 14, 1992Date of Patent: August 3, 1993Assignee: Schering AktiengesellschaftInventors: Eckhard Ottow, Gunter Neef, Rudolf Wiechert, Walter Elger, Sybille Beier, Karl-Heinrich Fritzemeier
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Patent number: 5225601Abstract: Abstract of the Disclosure: Diphenylheteroalkyl derivatives of the formula I ##STR1## where A and R.sup.1 -R.sup.6 have the meanings specified in the description, and the preparation thereof are described.The substances are suitable for controlling diseases and as cosmetic agents.Type: GrantFiled: October 31, 1991Date of Patent: July 6, 1993Assignee: BASF AktiengesellschaftInventors: Bernd Janssen, Hans-Heiner Wuest
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Patent number: 5167846Abstract: Sulfoxides of bisthiomethylated and tristhiomethylated phenols of formulae I and II ##STR1## wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.18 alkyl, cyclohexyl or C.sub.7 -C.sub.9 phenylalkyl,R.sub.2 and R.sub.3 are each independently of the other hydrogen or methyl,R.sub.4 is C.sub.4 -C.sub.18 alkyl, phenyl, C.sub.7 -C.sub.9 phenylalkyl, C.sub.1 -C.sub.4 alkyl-substituted phenyl,hydroxyethyl or a radical --(CH.sub.2).sub.r COOR.sub.5, wherein r is 1 or 2 and R.sub.5 is C.sub.1 -C.sub.18 alkyl,Z is sulfur ##STR2## wherein R.sub.2 and R.sub.3 are as defined above, or are a direct bond, and n, m and p are each independently of one another 0 or 1, and mixtures thereof with the corresponding non-oxidized compounds, are suitable stabilizers for materials which are sensitive to oxidative, thermal and/or light-induced degradation.Type: GrantFiled: January 25, 1991Date of Patent: December 1, 1992Assignee: Ciba-Geigy CorporationInventors: Hans-Rudolf Meier, Rita Pitteloud
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Patent number: 5123953Abstract: Compounds of formula: ##STR1## in which: n=0, 1, 2f=0, 1Ar is an optionally substituted phenyl or pyridyl groupU a chlorine or bromine atomV a bromine or chlorine or iodine atomB is C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.10 cycloalkyl, which are optionally substituted by 1 to 6 halogen atoms, phenyl or pyridyl or oxidized pyridyl, which are optionally substituted.Use of these compounds as herbicides which are selective but especially antigraminaceous at preemergence.Type: GrantFiled: April 10, 1990Date of Patent: June 23, 1992Assignee: Rhone-Poulenc AgrochimieInventors: Philipe Desbordes, Michel Euvrard, Francois De Reinach Hirtzbach, Christopher Pearson
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Patent number: 5100460Abstract: Herbicides of formula: ##STR1## in which: n=0,1, 2f=0,1A is chosen from the groups ##STR2## in which: Ar is chosen from the groups ##STR3## B is chosen from optionally substituted C.sub.1 -C.sub.10 alkyl and C.sub.3 -C.sub.Type: GrantFiled: July 13, 1989Date of Patent: March 31, 1992Assignee: Rhone-Poulenc AgrochimieInventors: Philippe Desbordes, Michel Euvrard
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Patent number: 5084478Abstract: A compound of the formula ##STR1## wherein X has the formula --CR.sup.5 .dbd.CR.sup.6 --, --C.tbd.C-- or ##STR2## wherein ring A is phenyl, naphthyl or heterocyclic; wherein R.sup.1 is hydrogen, alkyl, alkanoyl or aroyl;wherein R.sup.2, R.sup.3 and R.sup.4, which may be the same or different, each is an electron withdrawing substituent or each is hydrogen or alkyl, alkoxy or dialkylamino, provided that when ring A is phenyl or naphthyl at least one of R.sup.2, R.sup.3 and R.sup.4 is an electron-withdrawing substituent;wherein R.sup.5 and R.sup.6, each is hydrogen, halogeno or alkylwherein R.sup.7 is alkyl or halogenoalkyl; and wherein R.sup.8 has the formula --Y--Q--R.sup.9 wherein Y is straight- or branched-chain alkylene or alkenylene; wherein Q is --O--, --S--, --SO-- or --SO.sub.2 --;and wherein R.sup.9 is alkyl of up to 6 carbon atoms which contains one or more defined substituents, processes for their manufacture and pharmaceutical compositions containing them.Type: GrantFiled: April 14, 1989Date of Patent: January 28, 1992Assignee: Imperial Chemical Industries PLCInventors: Leslie R. Hughes, Howard Tucker
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Patent number: 5082976Abstract: Benzaldehydes of the formula ##STR1## can be obtained by reaction of substituted .beta.-amino-styrenes of the formula ##STR2## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.8, R.sup.9, R.sup.10, m, n and o have the scope of meaning indicated in the description, with oxygen in the presence of a Cu compound in the solution of an aprotic polar solvent at 0.degree.-120.degree. C.Type: GrantFiled: October 25, 1990Date of Patent: January 21, 1992Assignee: Bayer AktiengesellschaftInventors: Heinz U. Blank, Helmut Kraus
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Patent number: 5082974Abstract: 3-Haolgeno-2,3-diphenylacrylaldehyde derivatives represented by the formula ##STR1## wherein R is an alkyl group having 1 to 6 carbon atoms, X and Y each represent a halogen atom, and n is 0, 1, or 2, a process for preparing the derivatives, a medicament for preventing and treating hyperlipidemia containing a pharmacologically effective amount of the derivative, and a method for preventing or treating hyperlipidemia using the medicament.Type: GrantFiled: December 10, 1990Date of Patent: January 21, 1992Assignee: Otsuka Pharaceutical Factory, Inc.Inventors: Kinji Hashimoto, Makoto Inoue, Junichi Minamikawa
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Patent number: 5075339Abstract: The invention relates to benzylketone phospholipase A.sub.2 inhibitors, pharmaceutical compositions containing them, and methods of treating phospholipase A.sub.2 -mediated conditions in mammals by administration of a therapeutically effective amount of such a benzylketone phospholipase A.sub.2 inhibitor. These compounds are also intermediates in the synthesis of other PLA.sub.2 inhibitors.Type: GrantFiled: June 1, 1990Date of Patent: December 24, 1991Assignee: Du Pont Merck Pharmaceutical CompanyInventor: Wendell W. Wilkerson
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Patent number: 5068408Abstract: A process for oxidizing an organic compound selected from an aliphatic, aromatic, aliphatic/aromatic, cycloaliphatic and heterocyclic alcohol, thiol, sulfide, aldehyde, amine, amide, ketone, acid, ether, ester, and organic compounds containing an activated carbon-carbon double bond, which process comprises contacting said organic compound dissolved in an organic solvent with a hypochlorous acid solution.Type: GrantFiled: January 31, 1990Date of Patent: November 26, 1991Assignee: Olin CorporationInventors: Robert J. Raynor, Budd L. Duncan
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Patent number: 5047420Abstract: Novel 1,3-diaryl cyclopentanes of the following general formula were prepared. ##STR1## These compounds were found to have potent and specific PAF (Platelet Activating Factor) antagonistic activities and as such useful in the treatment or amelioration of various diseases or disorders mediate by the PAF, for example, hypotension, inflammation, nephritis, stroke and other cardiovascular disorders, asthma, allergic and skin diseases, peptic or stomach ulcer, shock, lung edema, psoriasis, adult respiratory distress syndrome, pain including dental pain, and aggregation of platelets.Type: GrantFiled: August 21, 1989Date of Patent: September 10, 1991Assignee: Merck & Co., Inc.Inventors: Donald W. Graham, Tesfaye Biftu, John C. Chabala, Michael N. Chang, Yuan-Ching P. Chiang, Kathryn L. Thompson, Shu S. Yang
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Patent number: 5032592Abstract: A compound of the formula ##STR1## wherein X has the formula ##STR2## wherein ring a is phenyl, naphthyl or heterocyclic; wherein R.sup.1 is hydrogen, alkyl, alkanoyl or aroyl; wherein R.sup.2, R.sup.3 and R.sup.4, which may be the same or different, each is an electron withdrawing substituent selected from halogeno, nitro, cyano, trifluoromethyl, alkylthio, alkylsulphinyl, and alkylsulphonyl or each is hydrogen, alkyl, alkoxy or dialkylamino provided that when ring A is phenyl or naphthyl at least one of R.sup.2, R.sup.3 and R.sup.4 is an electron-withdrawing substituent; wherein R.sup.5 and R.sup.6, which may be the same or different, each is hydrogen, halogeno or alkyl; wherein R.sup.7 is alkyl or halogenoalkyl; and wherein R.sup.8 is carbamoyl, alkyl, cycloalkyl, alkenyl, alkynyl, halogenoalkyl, halogenoalkenyl, halogenoalkynyl, alkanoyl, alkylcarbamoyl, dialkylcarbamoyl or aroyl; or wherein R.sup.Type: GrantFiled: May 30, 1989Date of Patent: July 16, 1991Assignee: Imperial Chemical Industries PLCInventors: Leslie R. Hughes, John Oldfield, Howard Tucker
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Patent number: 5004841Abstract: Aromatic compounds, such as benzene or biphenyl, are alkylated with an alkylating agent having from one to eight carbons atoms, such as propylene, in the presence of an acidic mordenite zeolite catalyst under conditions sufficient to produce a mixture of substituted aromatic compounds enriched in the linear alkylated isomers, such as p-diisopropylbenzene or p,p'-di(isopropyl)biphenyl, respectively. The novel acidic mordenite catalyst is characterized by its silica/alumina molar ratio, its porosity, and a Symmetry Index. The p,p'-disubstituted isomers of aromatic compounds are useful as monomers in the preparation of thermotropic, liquid crystal polymers.Type: GrantFiled: March 14, 1989Date of Patent: April 2, 1991Assignee: The Dow Chemical CompanyInventors: Guo-shuh J. Lee, Juan M. Garces, Joseph J. Maj, Stephen C. Rocke
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Patent number: 4990676Abstract: A process for preparing single enantiomers of chiral sulphoxides is provided. The process involves (a) reacting an achiral sulphur-containing, e.g. a disulphide, with a single enantiomer of a chiral template having the formula T--(CO)--CH.sub.2 R.sup.1, wherein T is suitably (eta.sup.5 --C.sub.5 H.sub.5)Fe(CO)(PPh.sub.3)-- (Ph=phenyl) and (b) thereafter sterospecifically oxidizing the sulphur atom with an oxidizing agent. A single enantiomer of the chiral sulphoxide can then be generated by reacting the oxidized product with a carbanion. In a preferred embodiment the reaction mixture is thereafter treated with further achiral sulphide to provide a process which is catalytic on the chiral template.Type: GrantFiled: February 17, 1989Date of Patent: February 5, 1991Assignee: British Petroleum Company p.l.c.Inventor: Stephen G. Davies
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Patent number: 4980509Abstract: An aromatic polycyclic compound has the formula ##STR1## wherein R represents --SO.sub.3 H, SO.sub.2 NHR.sub.3, ##STR2## --SO.sub.2 R.sub.3, --SOR.sub.3 or --SR.sub.3, R.sub.3 represents lower alkyl, monohydroxyalkyl, polyhydroxyalkyl, aminoalkyl, carboxyalkyl, aminocarboxyalkyl or alkoxyalkyl,R' represents hydrogen, lower alkyl, lower alkoxy, hydroxy, C.sub.1 -C.sub.4 acyloxy or amino,R" represents hydrogen, lower alkyl or lower alkoxy, orR' and R", taken together, form an oxo, methano or hydroxyimino radical,R.sub.1 represents hydrogen or lower alkyl,n is 0 or 1,when n=1, R.sub.2 represents hydrogen or lower alkyl, or R.sub.1 and R.sub.2, taken together form a vinylene radical, andAr represents an aromatic radical selected from ##STR3## wherein R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.sub.10 and R.sub.11 represent hydrogen or lower alkyl, at least one of R.sub.4 and/or R.sub.5 being other than hydrogen, and at least two of R.sub.8 -R.sub.Type: GrantFiled: July 1, 1988Date of Patent: December 25, 1990Assignee: Societe Anonyme dite: L'OrealInventors: Jean Maignan, Gerard Lang, Gerard Malle, Serge Restle
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Patent number: 4963535Abstract: Cosmetic compositions for cleaning hair, the skin or for removing make-up from the face or from the eyes, containing (a) a foaming surface-active agent, (b) an aqueous, hydroalcoholic or oily carrier and (c) a nonfoaming, nonionic product, poorly soluble in water, of general formula (I):R--O--[C.sub.2 H.sub.3 --CH.sub.2 R.sub.1 --O].sub.p [C.sub.2 H.sub.3 O--CH.sub.2 OH].sub.n H (I)in which R denotes a C.sub.8 -C.sub.20 alkyl radical, R.sub.1 denotes a C.sub.7 -C.sub.17 alkyl radical or an alkoxy radical containing from 8 to 20 carbon atoms, R+R.sub.1 containing from 21 to 31 carbon atoms and preferably from 23 to 27, p denotes the exact value of 1 or a statistical mean value of between 1 and 2, and n denotes a statistical mean value of between 2 and 10 and preferably between 2.5 and 7.The presence of the component (c) improves the compatibility of the foaming surface-active agents (a) with the skin and the mucosa.Type: GrantFiled: February 2, 1988Date of Patent: October 16, 1990Assignee: L'OrealInventors: Henri Sebag, Guy Vanlerberghe
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Patent number: 4959494Abstract: A method for oxidizing organic compounds by contacting organic compounds with molecular oxygen in the presence of a noble metal pyrochlore having the formula:A.sub.2+x B.sub.2-x O.sub.7-ywherein A is a pyrochlore structure metal cation, and B is one or more of Ru, Rh, Ir, Os, and Pt; x and y are greater than or equal to 0 and less than or equal to 1.0, at a temperature up to about 200.degree. C.Type: GrantFiled: July 6, 1987Date of Patent: September 25, 1990Assignee: Monsanto CompanyInventor: Timothy R. Felthouse
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Patent number: 4954165Abstract: An herbicidally effective benzoyl derivative having the formula: ##STR1## wherein X.sub.1 is C.sub.1 -C.sub.4 alkoxy or halogen;X.sub.4 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen;X.sub.5 is hydrogen or fluorine;Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4 and Y.sub.5 are independently hydrogen or C.sub.1 -C.sub.4 alkyl;R.sub.1 is C.sub.1 -C.sub.4 alkyl;R.sub.4 is C.sub.1 -C.sub.3 alkyl;n is an integer of 0, 1 or 2 is discosed.In addition, the herbicidally effective benzoyl derivative having the formula: ##STR2## wherein: X.sub.1 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy halogen;X.sub.4 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen;X.sub.5 is hydrogen or fluorine;Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4 and Y.sub.5 are independently hydrogen or C.sub.1 -C.sub.4 alkyl;R.sub.1 is C.sub.1 -C.sub.4 alkyl;R.sub.4 is C.sub.1 -C.sub.3 alkyl;n is an integer of 0, 1 or 2;L is C.sub.1 -C.sub.4 alkylene is disclosed.Type: GrantFiled: October 18, 1988Date of Patent: September 4, 1990Assignee: Nissan Chemical Industries Ltd.Inventors: Masatoshi Baba, Takuya Kakuta, Norio Tanaka, Eiichi Oya, Takashi Ikai, Tsutomu Nawamaki, Shigeomi Watanabe, Koichi Suzuki
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Patent number: 4952235Abstract: (Hetero) aryloxynaphthalenes having substituents bonded via sulphur having herbicidal activity and of the formula ##STR1## in which m represents the number 0, 1 or 2,n represents the numbers 0 or 1,R.sup.1 represents hydrogen, halogen, cyano or trifluoromethyl,R.sup.2 represents hydrogen or halogen,R.sup.3 represents halogen, trifluoromethyl, trifluoromethoxy, trifluoromethylthio or trifluoromethylsulphonyl,R.sup.4 represents hydrogen or halogen,X represents nitrogen or the group C--R.sup.5, whereinR.sup.5 represents hydrogen or halogen,Y represents oxygen or one of the groupings ##STR2## wherein R.sup.6 represents hydrogen, alkyl, --CO--Z or --SO.sub.2 --Z andZ represents hydrogen, halogen or an optionally substituted alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, alkinyl, aryl or heteroaryl radical.Type: GrantFiled: June 22, 1989Date of Patent: August 28, 1990Assignee: Bayer AktiengesellschaftInventors: Roland Andree, Michael Haug, Hans-Joachim Santel, Robert R. Schmidt, Harry Strang
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Patent number: 4937388Abstract: The invention provides insecticidally active compounds of formula I: ##STR1## wherein A is selected from oxygen and a group of formula S(O).sub.n, where n represents 0, 1 or 2; W represents one or two substituents selected from halo, alkyl, alkoxy, alkoxyalkyl, haloalkyl and haloalkoxy, or W represents a bidentate group linking adjacent carbon atoms, selected from alkylene and alkylenedioxy; Y represents a substituted aryl group where each substituent is selected from halo, alkyl, aryl, aralkyl, aryloxy and arylamino; Z represents a fluoroalkyl group of up to two carbon atoms; and either X' represents hydrogen and X is selected from hydrogen, halo, hydroxy, alkoxy and acyloxy, or X and X' together represent a second bond between the adjacent carbon atoms.The invention also provides processes and intermediates useful for the preparation of the compounds of formula I, insecticidal compositions comprising the compounds of formula I, and methods of combating and controlling pests therewith.Type: GrantFiled: October 29, 1987Date of Patent: June 26, 1990Assignee: Imperial Chemical Industries PLCInventors: Michael J. Bushell, Robin A. E. Carr
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Patent number: 4911754Abstract: This invention relates to aryloxy dihydrobenzofuran, oxoindole or benzofuranone derivatives having herbicidal activity and to the use of such compounds to control the growth of noxious plants, i.e., weeds.Type: GrantFiled: July 16, 1987Date of Patent: March 27, 1990Assignee: American Cyanamid CompanyInventors: David A. Hunt, James A. Schwindeman
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Patent number: 4891448Abstract: Polycyclic aromatic compounds, such as biphenyl, are alkylated with an alkylating agent, such as propylene, in the presence of an acidic mordenite zeolite catalyst under conditions sufficient to produce a mixture of substituted polycyclic aromatic compounds enriched in the para alkylated isomers, such as p,p'-di(isopropyl)biphenyl. The novel acidic mordenite catalyst is characterized by its silica/alumina molar ratio, its porosity, and a Symmetry Index. The p,p'-disubstituted isomers of polycyclic aromatic compounds are useful as monomers in the preparation of thermotropic, liquid crystal polymers.Type: GrantFiled: November 23, 1987Date of Patent: January 2, 1990Assignee: The Dow Chemical CompanyInventors: Juan Garces, Joseph J. Maj, G. John Lee, Stephen C. Rocke
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Patent number: 4876381Abstract: The invention relates to a compound of the formula (II) ##STR1## and the corresponding isomers and salts, in which formula: a and b are integers which independently of one another can assume the values 0 or 1,R.sub.1, R.sub.2, R.sub.3 and R.sub.4 represent, independently, a hydrogen atom, a linear or branched C.sub.1 -C.sub.6 -alkyl radical or a C.sub.1 -C.sub.4 -alkoxy radical,R.sub.6 represents a C.sub.1 -C.sub.6 -alkyl radical,R.sub.5 and R.sub.12 represent a hydrogen atom or a C.sub.1 -C.sub.4 -alkyl radical, with the proviso that R.sub.5 cannot represent hydrogen if a=b=0 andR.sub.11 has various meanings.These compounds have useful dermatological properties.Type: GrantFiled: August 18, 1987Date of Patent: October 24, 1989Assignee: L'OrealInventors: Gerard Lang, Jean Maignan, Serge Forestier, Serge Restle, Alain Lagrange, Braham Shroot
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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: 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: 4822869Abstract: A method for introducing gases into liquids, wherein a stirred kettle is used which has the form of a cylindrical vessel in which the length/diameter ratio should be at least 1; and wherein the stirred kettle is filled to a level of more than 70% with the liquid into which gas is to be introduced, the gas feed rate is adapted to the absorption capacity of the liquid, and the stirrer speed is adjusted such that the largest coherent amount of gas is 10% of the volume of the stirred kettle.Type: GrantFiled: September 16, 1986Date of Patent: April 18, 1989Assignee: Chemische Werke Huls AktiengesellschaftInventors: Franz-Michael Bollenrath, Martin Bartmann, Bernhard Hentschel
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Patent number: 4802912Abstract: This invention relates to haloalkyl-sulfenoxyl-2, 3-dibromopropane compounds and their use as antidotes for thiocarbamate herbicides.Type: GrantFiled: December 27, 1983Date of Patent: February 7, 1989Assignee: Stauffer Chemical Co.Inventor: Don R. Baker
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Patent number: 4795831Abstract: Novel cyclopentane derivatives which are useful as an intermediate for the preparation of N-(L-aspartyl)-N'-(2,2,5,5-tetramethylcyclopetanecarbonyl)-R-1,1-diaminoet hane are represented by the formula (I) ##STR1## wherein R.sub.1 is hydrogen and R.sub.2 is cyano, formyl, carbamoyl, alkanesulfonyloxy, or ##STR2## wherein R.sub.3 and R.sub.4 are the same or different and represent alkyl, substituted alkyl or R.sub.1 and R.sub.2 are combined to be methylsulfinylmethylene, acetoxymethylthiomethylene, halomethylthiomethylene, methylthiomethylene, alkoxymethylene, or --CH.sub.2 --O--.Type: GrantFiled: October 1, 1987Date of Patent: January 3, 1989Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Takayoshi Yamauchi, Kaneaki Hattori, Shunichi Ikeda, Kentaro Tamaki
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Patent number: 4734522Abstract: Six-membered ring compounds of the formula I ##STR1## wherein A is a benzene or cyclohexane ring,X.sup.1 to X.sup.6 independently of one another in each case are H, --OR, --COOR, --SR, --SOR, --SO.sub.2 R or, if A is a cyclohexane ring, also --O--COR, andR is in each case an alkyl group which has up to 15 C atoms and in which one or two CH.sub.2 groups can be replaced by O atoms, at least three of the substituents X.sup.1 to X.sup.6 being other than H,can be used as constituents of discotic liquid-crystal phases for liquid-crystal display elements.Type: GrantFiled: January 7, 1986Date of Patent: March 29, 1988Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Klaus Praefcke, Bernd Kohne, Wadi Poules, Rudolf Eidenschink, Bernhard Scheuble
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Patent number: 4716241Abstract: Novel cyclopentane derivatives which are useful as an intermediate for the preparation of N-(L-aspartyl)-N'-(2,2,5,5-tetramethylcyclopentanecarbonyl)-R-1,1-diaminoe thane are represented by the formula (I) ##STR1## wherein R.sub.1 is hydrogen and R.sub.2 is cyano, formyl, carbamoyl, alkanesulfonyloxy, or ##STR2## wherein R.sub.3 and R.sub.4 are the same or different and represent alkyl, substituted alkyl or R.sub.1 and R.sub.2 are combined to be methylsulfinylmethylene, acetoxymethylthiomethylene, halomethylthiomethylene, methylthiomethylene, alkoxy-methylene, or --CH.sub.2 --O--.Type: GrantFiled: February 28, 1986Date of Patent: December 29, 1987Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Takayoshi Yamauchi, Kaneaki Hattori, Shunichi Ikeda, Kentaro Tamaki
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Patent number: 4687871Abstract: A racemate may be resolved into its enantiomers by stereoselective adsorption on a crystalline molecular sieve having an assymetric crystal structure for example zeolite ZSM11. The resolution may be assisted by the presence of an enantiomer of a compound separable from that of the racemate either preadsorbed on the molecular sieve or included in a polar solvent solution of the racemate to be treated. Resolution of an alkyl aryl sulphoxide racemate is exemplified.Type: GrantFiled: November 7, 1985Date of Patent: August 18, 1987Assignee: Laporte Industries LimitedInventors: Alan E. Comyns, Gareth W. Morris, John P. Sankey
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Patent number: 4670495Abstract: Novel o-bridged polynuclear polyphenols of the formula I ##STR1## which contain at least one organic radical, such as alkyl, cycloalkyl or aryl, per phenyl nucleus and are formed by condensation of the monomeric phenolic components with customary bridging reagents, such as formaldehyde, acetone or sulfur dichloride, or by oxidative coupling of the monomeric phenolic components, and which, depending on the reaction procedure, can contain between 2 and 50 monomer units, are described.The substances according to the invention can be used for stabilizing plastics from oxidative degradation and have a good resistance to extraction.Type: GrantFiled: June 20, 1986Date of Patent: June 2, 1987Assignee: Ciba-Geigy CorporationInventor: Samuel Evans
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Patent number: 4666711Abstract: The invention relates to non-ionic surface-active agents which correspond to the formula ##STR1## in which R denotes a linear or branched, saturated or unsaturated aliphatic radical containing 4 to 20 carbon atoms, R.sub.1 denotes (1) a, preferably linear, alkyl radical, (2) a linear or branched alkoxymethyl radical or (3) an alkenyloxymethyl radical, the alkyl or alkenyl parts of these radicals containing from 4 to 20 carbon atoms,and Z denotes a polyether linkage corresponding to the formula ##STR2## in which n denotes an average statistical value of 2 to 20 and A denotes (a) the group OH,(b) the group ##STR3## in which u denotes 0 or 1, or (c) the group ##STR4## in which u dentoes 0 or 1, the radicals R and R.sub.1 containing a total of 12 to 38 carbon atoms, as well as to the derivatives of the above compounds which result from the reaction of ethylene oxide or glycidol with the OH groups.Type: GrantFiled: September 18, 1985Date of Patent: May 19, 1987Assignee: L'OrealInventors: Guy Vanlerberghe, Henri Sebag
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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: 4628087Abstract: Process for the preparation of pharmacologically active compounds containing a sulfoxide group by oxidation of a thioether with hypochlorite in an alkaline medium at a pH higher than 10 and at a temperature comprised between 0.degree. and 40.degree. C.Type: GrantFiled: May 7, 1984Date of Patent: December 9, 1986Assignee: Zambon S.p.A.Inventor: Mariano Meneghin
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Patent number: 4625065Abstract: A method for the production of trimethylsulfoxonium salts is described in which trimethylsulfonium salts are oxidized with ruthenium tetroxide in the presence of an inert solvent to form the corresponding trimethylsulfoxonium salts.Type: GrantFiled: March 11, 1985Date of Patent: November 25, 1986Assignee: Stauffer Chemical CompanyInventor: James B. Heather
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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: 4613703Abstract: An isomeric mixture of C- and O-allylated aromatic compounds is prepared by contacting an allyl halide, a hydroxyaromatic reactant, an alkaline agent, water and a quaternary salt catalyst. This mixture may be thermally isomerized to obtain the C-allylated compounds in high yield.Type: GrantFiled: April 5, 1982Date of Patent: September 23, 1986Assignee: The Dow Chemical CompanyInventor: Robert E. Hefner, Jr.
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Patent number: 4609712Abstract: Bis(dicarboxyphenyl) sulfone compounds, including the free tetracarboxylic acids and their functional derivatives such as salts, esters, amides, anhydrides and imides, are prepared by oxidizing the corresponding sulfides with a relatively strong oxidizing agent, preferably a peroxy reagent such as acetyl peroxide or m-chloroperbenzoic acid. The reaction is especially useful for the preparation of sulfone polyimides, since films of the sulfide polyimides may be oxidized without dissolving or otherwise degrading their structural integrity.Type: GrantFiled: June 18, 1984Date of Patent: September 2, 1986Assignee: General Electric CompanyInventors: Thomas L. Evans, Marsha M. Grade
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Patent number: 4578210Abstract: Six-membered ring compounds of the formula I ##STR1## wherein A is a benzene or cyclohexane ring,X.sup.1 to X.sup.6 independently of one another in each case are H, --OR, --COOR, --SR, --SOR, --SO.sub.2 R or, if A is a cyclohexane ring, also --O--COR, andR is in each case an alkyl group which has up to 15 C atoms and in which one or two CH.sub.2 groups can be replaced by O atoms, at least three of the substituents X.sup.1 to X.sup.6 being other than H,can be used as constituents of discotic liquid-crystal phases for liquid-crystal display elements.Type: GrantFiled: September 13, 1984Date of Patent: March 25, 1986Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Klaus Praefcke, Bernd Kohne, Wadi Poules, Rudolf Eidenschink, Bernhard Scheuble
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Patent number: 4558129Abstract: Novel compounds of the general formula: ##STR1## and the pharmaceutically acceptable esters and acid addition salts thereof, wherein:R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8 and R.sup.9 are each independently hydrogen, lower alkyl, lower alkoxy, trifluoromethyl, halo, lower alkylthio, lower alkyl sulfinyl, lower alkyl sulfonyl; orR.sup.2 and R.sup.3 together form --OCH.sub.2 O--; andR.sup.10 and R.sup.11 are each independently hydrogen or lower alkyl.These compounds combine .beta.-blockade and calcium entry blockade properties in the same compound and therefore are useful in therapy in the treatment of cardiovascular diseases, including hypertension, arrhythmias and variant and exercise induced angina.Type: GrantFiled: May 18, 1983Date of Patent: December 10, 1985Assignee: Syntex (U.S.A.) Inc.Inventors: Arthur F. Kluge, Robin D. Clark, Arthur M. Strosberg
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Patent number: 4552565Abstract: Hair dyes containing oxidation dye precursors in a cosmetic carrier contain as coupler substances compounds corresponding to formula I ##STR1## in which Z is a sulfur atom, an >SO group or an >SO.sub.2 group or salts thereof. As developer substances, the hair dyes contain the developers normally used in oxidation hair dyes, preferably aromatic and/or heterocyclic diamines or a 2,4,5,6-tetraamino pyrimidine. The new couplers produce color tones in the brown range with good fastness properties and a negligible tendency towards skin staining.Type: GrantFiled: November 1, 1984Date of Patent: November 12, 1985Assignee: Henkel KGaAInventors: Norbert Maak, Edgar Lieske
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Patent number: 4517384Abstract: Perfluoroalkyl alkylene vinyl sulfoxides and sulfones of the formula ##STR1## wherein R.sub.f is perfluoroalkyl of 3 to 18 carbon atoms, R.sub.1 is hydrogen or lower alkyl, m is 1 to 3 and n is 1 or 2, intermediates thereof, methods for their preparation, and the uses of such compounds to render cellulosic, and natural and synthetic polyamide, materials hydrophobic and oleophobic are described.Type: GrantFiled: January 21, 1983Date of Patent: May 14, 1985Assignee: Ciba-Geigy CorporationInventor: Neal O. Brace
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Patent number: 4507492Abstract: Allyl derivatives of phenols, thiophenols and arylamines are prepared by contacting such aromatic reactant with an allyl lower alkyl carbonate in the presence of a molybdenum, tungsten or Group VIII metal.Type: GrantFiled: May 6, 1983Date of Patent: March 26, 1985Assignee: The Dow Chemical CompanyInventor: Edmund P. Woo
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Patent number: 4502973Abstract: Electroviscous (EV) fluids consisting of solid hydrophilic particles dispersed in hydrophobic liquids, where the liquid contains a diaryl derivative component of general formula I ##STR1## in which R is CY.sub.2,O,S,SO,SO.sub.2,SiF.sub.2, or O--SiY.sub.2 --O,X.sup.1 and X.sup.2 are halogens, (m+n) is between 1 and 3 on average, and (p+q) is between 0 and 1 on average. EV fluids containing these novel components possess generally improved properties in terms of lower viscosities, electrical conductivities, toxicities and freezing points. In a preferred embodiment, the component is a mixture of brominated diphenyl methanes in which R is CH.sub.2,n=O,X.sup.1 =Br,(m+n) is approximately one, and (p+q)=0.Type: GrantFiled: February 3, 1983Date of Patent: March 5, 1985Assignee: National Research Development CorporationInventor: James E. Stangroom
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Patent number: 4501902Abstract: A process for removing compounds from aprotic solvents in which aprotic solvent containing at least one acidic compound is contacted with a solid inorganic compound chosen from alkaline earth carbonates, alkaline earth hydroxides, alkaline earth oxides, and alumina in which the contact of the solvent with a solid inorganic compound is by the process of fluidized bed contact, stirred slurry contact or trickle bed contact. Contaminated NMP from poly(phenylene sulfide) production is substantially freed of acidic contaminants by a series of fractionations with a treatment of the kettle liquid of at least one fractionation by the method described above and/or a treatment of the overhead of the last fractionation in series by the method described above.Type: GrantFiled: December 21, 1982Date of Patent: February 26, 1985Assignee: Phillips Petroleum CompanyInventor: James W. Cleary