Oxygen Bonded Directly To The Carbonyl (e.g., Benzoic Acid Esters, Etc.) Patents (Class 558/416)
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Patent number: 4864053Abstract: This invention concerns certain substituted diphenyl ethers, their method of preparation, and herbicidal uses thereof.Type: GrantFiled: August 12, 1980Date of Patent: September 5, 1989Inventor: William S. Grove
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Patent number: 4861799Abstract: A benzoylurea compound having the formula: ##STR1## wherein each of X.sub.1 and X.sub.2 is a hydrogen atom, a halogen atom or a methyl group, provided that X.sub.1 and X.sub.2 are not simultaneously hydrogen atoms, Y is independently a hydrogen atom, a halogen atom, an alkyl group which may be substituted by halogen, a --CO.sub.2 R.sub.1 group wherein R.sub.1 is a hydrogen atom, a cation or an alkyl group, or a --OR.sub.1 group wherein R.sub.1 is as defined above, A.sub.1 is .dbd.N--or ##STR2## wherein Y is as defined above, W is an oxygen atom, a sulfur atom or ##STR3## wherein R.sub.1 is as defined above, k is an integer of from 1 to 3, l is 0 or 1, and Ar is ##STR4## wherein Z is independently a hydrogen atom, a halogen atom, an alkyl group which may be substituted by halogen, an alkoxy group which may be substituted by halogen, a nitro group, a cyano group or a --S(O).sub.n R.sub.2 group wherein R.sub.2 is an alkyl group which may be substituted by halogen and n is 0, 1 or 2, A.sub.Type: GrantFiled: September 30, 1987Date of Patent: August 29, 1989Assignee: Ishihara Sangyo Kaisha Ltd.Inventors: Takahiro Haga, Tadaaki Toki, Toru Koyanagi, Yasuhiro Fujii, Kiyomitsu Yoshida, Osamu Imai
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Patent number: 4859789Abstract: Diarylnitrones are provided which are useful for near UV photolithography.Type: GrantFiled: March 5, 1986Date of Patent: August 22, 1989Assignee: General Electric CompanyInventors: Bruce F. Griffing, Paul R. West
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Patent number: 4855076Abstract: A novel fluorophenylcyclohexane derivative useful as a component of liquid crystal compositions used for liquid crystal display elements, and a liquid crystal composition containing the same are provided, which fluorophenylcyclohexane derivative is expressed by the formula ##STR1## wherein R.sup.1 represents an alkyl group of 1 to 10 carbon atoms; R.sup.2 represents an alkyl group or an alkoxy group each of 1 to 10 carbon atoms; a.sup.1 represents a hydrogen atom and a.sup.2 represents a fluorine atom; A represents a 1,4-phenylene group; l and m each represent an integer of 0, 1 or 2 or 3; and a value of (l+m) is 2 or 3.Type: GrantFiled: September 15, 1986Date of Patent: August 8, 1989Assignee: Chisso CorporationInventors: Yasuyuki Goto, Tetsuya Ogawa, Shigeru Sugimori
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Patent number: 4846998Abstract: Cyclohexane derivatives of the formula IR.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --R.sup.2 Iin whichR.sup.1 and R.sup.2 are each an alkyl group having 1-10 C atoms, in which one or two non-adjacent CH.sub.2 groups can also be replaced by O atoms and/or --CO-- groups and/or --CO--O-- groups and/or --CH.dbd.CH-- groups, one of the radicals R.sup.1 and R.sup.2 also being H, F, Cl, Br, CN or R.sup.3 --A.sup.3 --Z.sup.2 --,A.sup.1 is --A--, A.sup.4 --A-- or --A--A.sup.4 --,A is a trans-1,4-cyclohexylene group which can be substituted in the 2-, 3-, 5- and/or 6-position one or more times by F and/or Cl and/or Br and/or CN and/or an alkyl group or a fluorinated alkyl group which each have 1-10 C atoms and in which one or two non-adjacent CH.sub.2 groups can also be replaced by 0 atoms and/or --CO-- groups and/or --CO--O-- groups, and which may also be substituted in the 1- and/or 4-position,A.sup.2, A.sup.3 and A.sup.Type: GrantFiled: November 21, 1986Date of Patent: July 11, 1989Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Ludwig Pohl, Bernhard Scheuble, Reinhard Hittich, Rudolf Eidenschink, Hans A. Kurmeier, Andreas Wachtler
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Patent number: 4845119Abstract: 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 of 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 substitutent;wherein R.sup.5 and R.sup.6, each is hydrogen, halogeno or alkyl;wherein 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 --; andwherein R.sup.9 is alkyl or up to 6 carbon atoms which contains one or more defined substituents, processes for their manufacture and pharmaceutical compositions containing them.Type: GrantFiled: February 18, 1986Date of Patent: July 4, 1989Assignee: Imperial Chemical Industries PLCInventors: Leslie R. Hughes, Howard Tucker
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Patent number: 4841088Abstract: A compound having a fungicidal activity represented by the general formula, ##STR1## wherein X, which may be the same or different, represents a cyano, nitro, halogenated lower alkyl, C.sub.1 -C.sub.12 alkoxy, lower alkoxy-substituted lower alkyl, lower alkenyloxy, lower alkynyloxy, halogenated lower alkoxy, lower alkoxycarbonyl or lower alkylthio group, R.sup.1 and R.sup.2, which may be the same or different, represent a hydrogen atom or a methyl group, Y represents a hydrogen or chlorine atom, m represents an integer of from 1 to 5, and n represents an integer of from 0 to 4, the sum of m and n being less than 6.Type: GrantFiled: August 13, 1987Date of Patent: June 20, 1989Assignee: Sumitomo Chemical Company, LimitedInventors: Tomoyuki Kusaba, Junya Takahashi, Masayo Sugano, Tamon Uematsu, Yukio Oguri, Tomohiro Teramae
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Patent number: 4833264Abstract: A 5- or 6-alkoxycarbonyl-2,3-dicyanonaphthalene is a useful intermediate for synthesizing a tetrakis(alkoxycarbonyl) metal naphthalocyanine.Type: GrantFiled: March 23, 1988Date of Patent: May 23, 1989Assignee: Hitachi Chemical Co., Ltd.Inventors: Seiji Tai, Shigeru Hayashida, Nobuyuki Hayashi
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Patent number: 4830470Abstract: Compounds of the formula ##STR1## wherein m represents is the number 0 or 1; A is a single covalent bond, --CH.sub.2 --CH.sub.2 --, --OCH.sub.2 --, --COO-- or --OOC--; rings B, C and D are 1,4-phenylene optionally substituted with cyano, halogen or lower alkyl; Y.sup.1 and Y.sup.2 are hydrogen or one of them also is cyano; and R.sup.1 and R.sup.2 each represents C.sub.1 -C.sub.18 -alkyl or C.sub.2 -C.sub.18 alkenyl, either of which is optionally halogen-substituted, in which one CH.sub.2 group or two non-adjacent CH.sub.2 groups is/are optionally replaced by oxygen; with the provisos that at least one of R.sup.1 and R.sup.2 has a chiral carbon atom or a C--C double bond or both when A is --COO-- and at least one of R.sup.1 and R.sup.2 has a C--C double bond when A is a single covalent bond, their preparation, liquid crystalline mixtures containing these compounds and their use for electro-optical purposes are described.Type: GrantFiled: May 20, 1987Date of Patent: May 16, 1989Assignee: Hoffmann-La Roche Inc.Inventors: Richard Buchecker, Hans-Jurgen Fromm, Stephen Kelly, Martin Schadt
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Patent number: 4822906Abstract: Intermediate compounds of the structural formula ##STR1## wherein R.sup.60 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.n -- wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl, trifluoromethyl or difluoromethyl; or trifluoromethoxy or difluoromethoxy; R.sup.61 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.62 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.61 and R.sup.62 together are C.sub.2 -C.sub.5 alkylene; R.sup.63 C.sub.1 -C.sub.4 alkyl; R.sup.64 is C.sub.1 -C.sub.4 alkyl; or R.sup.63 R.sup.64 together are C.sub.2 -C.sub.5 alkylene; R.sup.65 and R.sup.66 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: December 4, 1987Date of Patent: April 18, 1989Assignee: Stauffer Chemical CompanyInventor: Charles G. Carter
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Patent number: 4822902Abstract: Certain N-acetonylbenzamides exhibit low toxicity to plants are particularly useful for control of fungi, especially Phycomycetes.Type: GrantFiled: July 26, 1984Date of Patent: April 18, 1989Assignee: Rohm and Haas CompanyInventors: H. Edwin Carley, Ashok K. Sharma
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Patent number: 4816597Abstract: Novel blocked diisocyanate monomers are provided. These monomers are useful for filling dental cavities, for cementing teeth and for general dental restorative procedures.Methods for preparing the monomers as well as methods for using them are described.Type: GrantFiled: January 5, 1987Date of Patent: March 28, 1989Assignee: New Jersey Institute of TechnologyInventors: William H. Snyder, II, deceased, David Kristol
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Patent number: 4816604Abstract: The compounds of formula I, ##STR1## where the substituents have various significances, and physiologically acceptable hydrolyzable derivatives thereof having the hydroxy group in the 2 position of the 3-aminopropoxy side chain in esterifield form, are useful as cardioselective .beta.-adrenoceptor blocking agents.Type: GrantFiled: March 9, 1987Date of Patent: March 28, 1989Assignee: William J. LouisInventors: William J. Louis, Richard Berthold, Andre Stoll
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Patent number: 4814349Abstract: The present invention relates to methods for controlling insect populations and for protecting living plants from insect attack by applying to said plants or to the soil in which they are growin an insecticidally-effective amount of a substituted benzoic acid 1 or 2-alkyl or 2-cycloalkylhydrazide.Novel substituted benzoic acid 1 and 2-alkyl and 2-cycloalkylhydrazides effective as insecticides or intermediates for the preparation of insecticidal diacylhydrazides also are presented.Type: GrantFiled: November 12, 1986Date of Patent: March 21, 1989Assignee: American Cyanamid CompanyInventors: Roger W. Addor, David G. Kuhn, Donald P. Wright, Jr.
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Patent number: 4814476Abstract: A liquid crystalline compound represented by the following general formula: ##STR1## where m and l represent individually integers within a range: 6.ltoreq.m.ltoreq.14 and 1.ltoreq.l.ltoreq.5, the symbol * represents an asymmetric carbon atom and the compound is required to be optically active. The compound can induce the twisting arrangement when added to the TN system or phase transition type liquid crystal mixture, as well as can improve the spontaneous polarization as the index of the ferroelectric property when added to the SmC* liquid crystal mixture.Type: GrantFiled: September 28, 1987Date of Patent: March 21, 1989Assignee: Alps Electric Co., Ltd.Inventors: Mitsuru Kano, Jun Nakanowatari
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Patent number: 4806682Abstract: Sulfonium and sulfoxonium salts of the formula ##STR1## wherein X and Y are independently a hydrogen atom, a halogen atom, a trihalomethyl group, a nitro group, an alkyl group or a cyano group; Z is a halogen atom, a trihalomethyl group, an alkyl group, cyano group or --S(O).sub.m R, wherein m is 0, 1 or 2 and R is an alkyl group; A is a halogen atom, a nitro group or a cyano group; B is a negatively charged organic substituent; n is 0 or 1, each R.sup.1 is independently an alkyl group, an aryl group or --N(R.sup.2).sub.2 wherein R.sup.2 is an alkyl group or an aryl group; S is sulfur; and N is nitrogen, and compositions containing these salts exhibit herbicidal activity.Type: GrantFiled: December 22, 1986Date of Patent: February 21, 1989Assignee: Rohm and Haas CompanyInventor: Roy Y. Yih
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Patent number: 4797150Abstract: Compounds of the formula ##STR1## wherein R.sup.60 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.61 through R.sup.66 are hydrogen or certain substituents, their salts, herbicidal compositions containing the compound or salts and the herbicidal use thereof.Type: GrantFiled: November 30, 1987Date of Patent: January 10, 1989Assignee: Stauffer Chemical CompanyInventor: Charles G. Carter
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Patent number: 4785128Abstract: A fluorescent brightener is proposed which consists of 51-99% of an unsymmetrically substituted compound of the formula ##STR1## in which R and R.sub.1 are identical or different and, if R and R.sub.1 are identical, R.sub.1 must occupy a position in the phenyl ring to which it is bonded which differs from the position occupied by R in its phenyl ring, and in which R and R.sub.1 independently of one another are CN or a carboxylic acid ester group, and 49-1% of a symmetrically substituted compound of the formula ##STR2## in which R is as defined above and the two R's are bonded to identical positions in their phenyl rings, as are also agents which contain these fluorescent brighteners and the use of these fluorescent brighteners for the fluorescent brightening of, in particular, textile materials, preferably made of polymer.Type: GrantFiled: March 18, 1983Date of Patent: November 15, 1988Assignee: Ciba-Geigy CorporationInventor: Leonardo Guglielmetti
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Patent number: 4770810Abstract: The invention relates to a family of organic compounds of the 1(4 hydroxyphenyl)2(4' cyanophenyl) ethane ester type which have a smectic A type mesomorphic phase, to the mixture obtained from these compounds as well as the method for manufacturing the molecules of this family. The compound of the invention corresponds to the general chemical formula: ##STR1## n being between 1 and 15.Type: GrantFiled: November 6, 1985Date of Patent: September 13, 1988Assignee: Thomson-CSFInventors: Jean C. Dubois, Gilles Ravaux, Pierre Le Barny
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Patent number: 4767879Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein: X is selected from halogen, nitro, cyano, alkyl, substituted alkyl, hydroxy, alkoxy, substituted alkoxy, alkenyl, alkynyl, alkenyloxy, alkynyloxy, acyloxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, sulfamoyl, substituted sulfamoyl, amino, substituted amino, and the groups formyl and alkanoyl and the oxime, imine and Schiff base derivatives thereof;R.sup.1 is selected from hydrogen, alkyl, alkenyl, alkynyl, substituted alkyl, alkylsulfonyl, arylsulfonyl, acyl and an inorganic or organic cation;R.sup.2 is selected from alkyl, substituted alkyl, alkenyl, haloalkenyl, alkynyl and haloalkynyl;R.sup.3 is selected from alkyl, fluoroalkyl, alkenyl, alkynyl, and phenyl;m is an integer chosen from 3 to 5.Type: GrantFiled: December 17, 1986Date of Patent: August 30, 1988Assignee: ICI Australia LimitedInventors: Keith G. Watson, Lynette A. Garson, Graham J. Bird, Lindsay E. Cross, Graeme J. Farquharson
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Patent number: 4764619Abstract: An optically active compound having the formula: ##STR1## wherein each of Z and Z' is a single bond, --COO--, --OCO--, --CH.sub.2 CH.sub.2 --, --OCH.sub.2 -- or --CH.sub.2 O--, R is an alkyl group having from 1 to 12 carbon atoms, an alkoxyl group having from 1 to 12 carbon atoms, a cyano group or a halogen atom, each of rings A and B is a 1,4-di-substituted phenylene group or a trans-1,4-di-substituted cyclohexylene group, n is 0 or 1, X is ##STR2## wherein * indicates an optical center, and R' is an alkyl group having from 2 to 12 carbon atoms or ##STR3## where R" is a hydrogen atom, an alkyl or alkoxy group having from 1 to 12 carbon atoms, provided that when X is ##STR4## R is the alkyl group or the alkoxy group.Type: GrantFiled: March 21, 1986Date of Patent: August 16, 1988Assignee: Asahi Glass Company Ltd.Inventors: Tomoki Gunjima, Ryutaro Takei, Eriko Aoyama
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Patent number: 4754052Abstract: A process of recycling nitrated by-products formed during the manufacture of the compound of the formula ##STR1## and salts thereof wherein J is ##STR2## and further wherein: R.sup.1 is fluorine, chlorine, bromine, or iodine or a trifluoromethyl group;R.sup.2 is a hydrogen atom, a fluorine, chlorine, bromine or iodine atom or a trifluoromethyl group;R.sup.3 is a hydrogen atom, a C.sub.1 -C.sub.4 alkyl group, a trifluoromethyl group, a cyano group or a fluorine, chlorine, bromine or iodine group; X is ##STR3## R.sup.4 is R.sup.5 or an acyl radical of the formula ##STR4## wherein Alk is a C.sub.1-6 alkyl group; R.sup.5 is a hydrogen atom or a C.sub.1-6 alkyl group optionally substituted with either one or more halogen atoms or a phenyl group;B is a C.sub.1-10 alkyl, OR.sup.7 or SR.sup.7 ;y is 1 to 4;R.sup.6 is a hydrogen atom or a C.sub.1-2 alkyl group;R.sup.7 is hydrogen, or a C.sub.1-8 alkyl group, a C.sub.Type: GrantFiled: November 7, 1986Date of Patent: June 28, 1988Assignee: ICI Americas Inc.Inventors: William W. Brand, John F. Stephen
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Patent number: 4746678Abstract: The invention relates to new phenanthrene derivatives wherein R stand for C.sub.1-10 alkylamino; C.sub.1-10 alkylthio; C.sub.1-5 alkoxy; or phenyl or phenylamino, the two latter groups being optionally substituted on the phenyl ring by one or more identical or different C.sub.1-4 alkyl, C.sub.1-4 alkoxy, nitro, amino, cyano and/or halogen substituent(s) .The compounds of the present invention possess valuable fungicidal properties and may be used in agriculture, horticulture and therapy as active ingredient of fungicidal or antifungal compositions.The compounds of the general Formula I ##STR1## may be prepared by acylating 9,10-phenanthrene-dione-9-oxime or an alkali or alkali earth metal salt thereof.Type: GrantFiled: June 4, 1986Date of Patent: May 24, 1988Assignee: EGIS GyoryszergyarInventors: Pal Benko, Tibor Zsolnai, Marta Kininczky, Laszlo Pallos, Iren Zsolnai nee Csillag, Peter Tetenyi, Jeno Bernath
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Patent number: 4743703Abstract: The 4-fluoroalkyl-4'-nitrodiphenyl ethers comprise a class of compounds that are highly effective herbicides.Type: GrantFiled: September 19, 1983Date of Patent: May 10, 1988Assignee: Rohm and Haas CompanyInventor: Colin Swithenbank
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Patent number: 4740620Abstract: This invention relates to a process for producing ring alkylated aromatic amines. In the process an aromatic amine is reacted with an olefin using an acidic crystalline molecular sieve as a catalyst. Under the conditions of the process the catalyst is extremely active and with amines that are capable of alkylation at the ortho and para positions, high selectivity to the ortho alkylated isomer can be achieved.Type: GrantFiled: November 8, 1985Date of Patent: April 26, 1988Assignee: Air Products and Chemicals, Inc.Inventors: Dale D. Dixon, William F. Burgoyne, Jr.
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Patent number: 4737313Abstract: Novel ferroelectric liquid crystals exhibiting a chiral smectic C phase and liquid crystal compositions containing the same are provided, which liquid crystals are substituted biphenyl esters expressed by the general formula ##STR1## wherein R.sub.1 * represents an optically active alkyl group of 4 to 18 carbon atoms; ##STR2## represents ##STR3## or ##STR4## Z represents R.sub.2, R.sub.2 CO or R.sub.2 COO wherein R.sub.2 represents an alkyl group or an alkoxy group each of 1 to 18 carbon atoms; and X and Y each represent hydrogen atom (H), bromine atom (Br), chlorine atom (Cl), fluorine atom (F) or cyano group (CN), and either one of X or Y is always hydrogen atom.Type: GrantFiled: August 8, 1986Date of Patent: April 12, 1988Assignee: Chisso CorporationInventors: Shinichi Saito, Hiromichi Inoue, Kanetsugu Terashima, Takashi Inukai, Kenji Furukawa
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Patent number: 4735959Abstract: There are described novel carboxylic acid derivatives of the formula ##STR1## and derivatives of the formula ##STR2## and the addition salts thereof, which exhibit an effect on the intermediary metabolism. Furthermore, the compounds of Formula Ia as well as the compounds of Formula I possess blood-sugar lowering properties.Type: GrantFiled: May 14, 1985Date of Patent: April 5, 1988Assignee: Dr. Karl Thomae GmbHInventors: Wolfgang Grell, Gerhart Griss, Robert Sauter, Rudolf Hurnaus, Eckhard Rupprecht, Nikolaus Kaubisch, Joachim Kahling, Bernhard Eisele
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Patent number: 4732912Abstract: A phenol derivative of the formulaNU--A--X--R.sup.1wherein NU is a defined bis-phenolic nucleus including a hydroxyphenyl-hydroxynaphthyl; hydroxyphenyl-hydroxyindanyl, hydroxyphenyl-hydroxybenzothienyl or di-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, cycloalkyl, halogenoalkyl, 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--, --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 27, 1984Date of Patent: March 22, 1988Assignee: Imperial Chemical Industries PLCInventors: William R. Pilgrim, Derek W. Young, Brian S. Tait, Graham C. Crawley, Philip N. Edwards, George B. Hill
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Patent number: 4728740Abstract: There is provided a novel and efficient stereoselective total synthesis of epipodophyllotoxin and related epipodophyllotoxin compounds of the general formula ##STR1## wherein R.sup.1 and R.sup.2 each are independently hydrogen or (lower)alkoxy, or R.sup.1 and R.sup.2, taken together, is methylenedioxy; R.sup.4 and R.sup.6 each are independently hydrogen or (lower)alkoxy; and R.sup.5 is hydrogen or a phenol-protecting group; or an acid addition salt thereof. The present invention also provides novel intermediates and processes for the preparation of said intermediates, which are then converted into known antineoplastic agents.Type: GrantFiled: September 15, 1986Date of Patent: March 1, 1988Assignee: Bristol-Myers CompanyInventors: Dolatrai M. Vyas, Paul M. Skonezny
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Patent number: 4727180Abstract: Polyhalohydroxyisopropyl phenylalkanoic and phenylalkenoic acids, amides, and esters, such as methyl 2-methoxy-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzenepro panoate, are useful as antihypertensive agents.Type: GrantFiled: January 4, 1985Date of Patent: February 23, 1988Assignee: E. I. Du Pont de Nemours and CompanyInventors: Paul E. Aldrich, Gilbert H. Berezin
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Patent number: 4723005Abstract: New anisotropic compounds of the formula (1) are useful in liquid crystal mixtures for electrooptical displays; at least one of the end groups of the compounds (1) is an alkyl group which carries cyano or halogen in a terminal or non-terminal position. This offers advantages for longitudinal polarization and/or cross-polarization of the anisotropic compounds with the aid of the comparatively highly polarizing cyano or halogen substituents, in particular high clear points, low .DELTA..epsilon./.epsilon..perp. values and/or negative .DELTA..epsilon. values.Type: GrantFiled: September 10, 1984Date of Patent: February 2, 1988Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Tuong Huynh-Ba, Maged A. Osman
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Patent number: 4717736Abstract: Compounds having the formula: ##STR1##are antagonists of leukotrienes of C.sub.4, D.sub.4 and E.sub.4, the slow reacting substance of anaphylaxis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory agents and cytoprotective agents.Type: GrantFiled: November 21, 1984Date of Patent: January 5, 1988Assignee: Merck Frosst Canada, Inc.Inventors: Joshua Rokach, Robert N. Young
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Patent number: 4708441Abstract: Compounds of the formula ##STR1## wherein X.sup.2 is a single covalent bond or --COO--; X.sup.1 is a single covalent bond, --COO--, --CH.sub.2 CH.sub.2 -- or when X.sup.2 is --COO--, X.sup.1 also can be p--C.sub.6 H.sub.4 --, p--C.sub.6 H.sub.4 --CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 --p--C.sub.6 H.sub.4, p--C.sub.6 H.sub.4 --COO-- or --COO--p--C.sub.6 H.sub.4 ; ring A is a benzene ring or trans-1,4-cyclohexylene; ring B is a benzene ring or when X.sup.2 is --COO-- and X.sup.1 is a single covalent bond, --COO-- or --CH.sub.2 CH.sub.2 --, ring B also can be trans-1,4-cyclohexylene; Z.sup.1, Z.sup.2 and Z.sup.3 individually are hydrogen or when positioned on a benzene ring which is not linked directly with a further ring via a single covalent bond, Z.sup.1, Z.sup.2 and Z.sup.3 also can be halogen, cyano or methyl; Y.sup.2 is cyano, nitro, 2,2-dicyanovinyl or when Y.sup.1 is hydrogen Y.sup.2 also can be 2,2-dicyano-1-methylvinyl; Y.sup.1 is halogen, cyano, C.sub.1 -C.sub.3 -alkyl or, when X.sup.Type: GrantFiled: August 16, 1985Date of Patent: November 24, 1987Assignee: Hoffman-La Roche Inc.Inventors: Martin Petrzilka, Martin Schadt, Alois Villiger
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Patent number: 4708966Abstract: The present invention relates to novel specifically-substituted phenyl compounds, especially substituted di-tert-butyl phenol derivatives, which are effective as anti-inflammatory, analgesic and/or antipyretic agents. These phenyl compounds are substituted with a low molecular weight alkyl chain which terminates in a specific unsaturated functional group. These unsaturated functionalities are --C.tbd.CH, C.dbd.CH.sub.2, C.dbd.C.dbd.CH.sub.2, and aldehydes in the form of their acetals.The present invention further relates to pharmaceutical compositions which contain an anti-inflammatory agent of the present invention and a pharmaceutically-acceptable carrier.Finally, the present invention relates to methods for treating diseases characterized by inflammation, such as rheumatoid arthritis and osteoarthritis, in humans or lower animals.Type: GrantFiled: June 27, 1986Date of Patent: November 24, 1987Assignee: The Procter & Gamble CompanyInventors: Maurice E. Loomans, Randall S. Matthews, Joseph A. Miller
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Patent number: 4709030Abstract: Liquid crystalline mixtures containing compounds of the formula ##STR1## wherein n stands for the number 0 or 1; X.sup.1 and X.sup.2 denote single covalent bonds or one of the symbols X.sup.1 and X.sup.2 also denotes --COO--, --OOC-- or --CH.sub.2 CH.sub.2 --; the rings A.sup.1, A.sup.2 and A.sup.3 represent 1,4-phenylene, 2-fluoro-1,4-phenylene or trans-1,4-cyclohexylene or one of these rings also represents a 2,5-disubstituted pyrimidine ring or a trans-2,5-disubstituted m-dioxane ring; R.sup.1 signifies 4-alkenyl or on a cyclohexyl ring also 2Z-alkenyl; and R.sup.2 denotes alkyl, alkoxy, --CN or --NCS,as well as the manufacture of these compounds and the use for electro-optical purposes are described.Type: GrantFiled: July 11, 1986Date of Patent: November 24, 1987Assignee: Hoffmann-La Roche Inc.Inventors: Martin Petrzilka, Martin Schadt
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Patent number: 4707296Abstract: A novel liquid crystal compound having a large positive dielectric anisotropy value and when added to a liquid crystal composition, forming no deposit in the resulting composition at low temperatures, and a liquid crystal composition containing the same are provided, which compound is an alkoxyethoxybenzoic acid ester derivative expressed by the formula ##STR1## wherein R represents an alkyl group of 1 to 10 carbon atoms.Type: GrantFiled: November 21, 1986Date of Patent: November 17, 1987Assignee: Chisso CorporationInventors: Shigeru Sugimori, Yasuyuki Goto
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Patent number: 4701547Abstract: New liquid-crystalline ester compounds which exhibit a liquid-crystalline phase within a broad temperature range and have a positive, dielectric anisotropy, and a liquid-crystalline composition comprising the same are provided which ester compounds are expressed by the general formula ##STR1## wherein R represents hydrogen atom or an alkyl group of 1 to 10 carbon atoms; ##STR2## each represent ##STR3## X represents ##STR4## Y represents hydrogen atom, F, Cl or CN; and Z represents F, Cl or CN.Type: GrantFiled: December 19, 1984Date of Patent: October 20, 1987Assignee: Chisso CorporationInventors: Shigeru Sugimori, Tetsuhiko Kojima
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Patent number: 4697037Abstract: The preparation of dibenzo[b,f]thiepin compounds by a process comprising the direct carboxylation of an ortho-toluyl-aryl sulfide to introduce a phenylacetic acid side chain is disclosed.Type: GrantFiled: October 11, 1985Date of Patent: September 29, 1987Assignee: Merck & Co., Inc.Inventor: Thomas R. Verhoeven
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Patent number: 4689176Abstract: A novel optically active compound suitable for use in a display mode utilizing a ferroelectric liquid crystal, and a chiral smectic liquid crystal composition containing the same are provided, which novel optically active compound is expressed by the formula ##STR1## wherein R represents an alkyl group of 2 to 15 carbon atoms; X represents CN group or a halogen atom; Y and Z each represent a halogen atom or hydrogen atom, but either one of Y and Z is hydrogen atom; l is 1 or 2; m is 0 or 1; and a symbol * shows that the carbon atom having this symbol attached thereto constitutes an optically active center.Type: GrantFiled: December 20, 1985Date of Patent: August 25, 1987Assignee: Chisso CorporationInventors: Hiromichi Inoue, Shinichi Saito, Kazutoshi Miyazawa, Takashi Inukai, Kanetsugu Terashima
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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: 4684737Abstract: A process for producing a substituted phthalic acid which comprises heating a substituted tetrahydrophthalic acid compound having a substituent in at least one of the 3-, 4-, 5- and 6-positions in the presence of sulfur to dehydrogenate it, and heat-treating the product in the presence of water optionally together with an organic solvent. As required, the heat-treated product is dehydrocyclized to form a substituted phthalic acid anhydride.Type: GrantFiled: August 17, 1984Date of Patent: August 4, 1987Assignee: Nippon Zeon Co., Ltd.Inventors: Hiroshi Horino, Michiro Ohnaka, Atsushi Hayashi, Yoshiko Ikeno
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Patent number: 4673529Abstract: A novel liquid crystal compound useful as a component of liquid crystal compositions and a liquid crystal composition containing the same are provided, which compound is a phenoxypropanol ester derivative expressed by the formula ##STR1## wherein R.sup.1 and R.sup.2 each represent an alkyl group or an alkoxy group each of 1 to 15 carbon atoms, F atom, Cl atom or CN group, but either one of R.sup.1 and R.sup.Type: GrantFiled: November 27, 1985Date of Patent: June 16, 1987Assignee: Chisso CorporationInventors: Shigeru Sugimori, Tetsuya Ogawa, Yasuyuki Goto, Toyoshiro Isoyama, Kazunori Nigorikawa, Kisei Kitano, Naoyuki Yoshida, Yoshito Furukawa
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Patent number: 4673756Abstract: A compound of the general formula ##STR1## wherein A denotes a substituted ring structure represented by the formula ##STR2## the substituent R denotes a linear alkyl group having 1 to 9 carbon atoms, and the cyclohexane rings are both arranged in a trans(equatorial-equatorial)-form.Type: GrantFiled: June 17, 1985Date of Patent: June 16, 1987Assignee: Dainippon Ink and Chemicals, Inc.Inventors: Makoto Sasaki, Haruyoshi Sasaki, Hisato Sato
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Patent number: 4670465Abstract: Long chain unsaturated hydrocarbon derivatives, having from 13 to 21 carbon atoms, which are substituted at the 1-position by a phenoxy, phenylthio or a phenyl that bear a carboxylic acid group at the ortho, meta or para positions, and up to 4 carbon-carbon triple bonds, methods of preparing them, and pharmaceutical preparations containing them. These compounds are useful as lipoxygenase inhibitors, and therefore as antiinflammatory agents.Type: GrantFiled: May 21, 1986Date of Patent: June 2, 1987Assignee: Syntex (U.S.A.) Inc.Inventors: Angel Guzman, Joseph M. Muchowski
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Patent number: 4664840Abstract: Anisotropic compounds of the following formula: ##STR1## wherein ##STR2## is selected from the group consisting of ##STR3## Z represents a covalent bond or a carboxyl group --C(O)O--, R is selected from the group consisting of hydrogen, C.sub.1 -C.sub.12 alkyl, and C.sub.1 -C.sub.12 alkoxy and X.sup.2 and X.sup.3 may be the same or different and are selected from the group consisting of hydrogen, halogen, and nitrile, with the proviso that at least one of the groups X.sup.2 and X.sup.3 is not hydrogen, are useful as components of liquid crystal mixtures for elektrooptical twist cells.Type: GrantFiled: November 20, 1984Date of Patent: May 12, 1987Assignee: E. MerckInventor: Maged A. Osman
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Patent number: 4661283Abstract: A novel organic compound usable as a component of liquid crystal compositions having a positive value of dielectric anisotropy and a liquid crystal composition usable as a material for liquid-crystalline display devices operated under a low driving voltage are provided which compound is a benzoic acid ester derivative expressed by the formula ##STR1## wherein R represents an alkyl group of 1 to 10 carbons and X represents ##STR2##Type: GrantFiled: February 28, 1985Date of Patent: April 28, 1987Assignee: Chisso CorporationInventors: Shigeru Sugimori, Yasuyuki Goto, Toyoshiro Isoyama, Kazunori Nigorikawa
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Patent number: 4659502Abstract: Ethane derivatives of the formula IR.sup.1 --A.sup.1 --CH.sub.2 CH.sub.2 --A.sup.2 --(A.sup.3).sub.n --R.sup.2 IwhereinR.sup.1 is H, an alkyl group with 1-12 C atoms, in which one or two non adjacent CH.sub.2 groups can also be replaced by O atoms and/or CO groups and/or --O--CO-- groups and/or --CO--O groups, F, Cl, Br or R.sup.3 --A.sup.4 --Z.sup.1 --,R.sup.2 is --CN or --Z.sup.2 --A.sup.4 --CN,A.sup.1 is --A--, --A--A.sup.5 -- or --A.sup.5 --A--,A.sup.2 is an 1,4-phenylene group which is unsubstituted or substituted by one or two F and/or Cl atoms and/or CH.sub.3 groups and/or CN groups and in which one or two CH groups can also be replaced by N atoms,A is a 1,4-cyclohexylene group, in which one or two non adjacent CH.sub.2 groups can also be replaced by O atoms, or is a 1,3-dithiane-2,5-diyl group or 1,4-bicyclo(2,2,2)-octylene group,A.sup.3, A.sub.4 are each a 1,4-cyclohexylene group, in which one or two non adjacent CH.sub.Type: GrantFiled: January 17, 1985Date of Patent: April 21, 1987Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: Julie E. Fearon, Wendy E. Smith, George W. Gray, David Lacey, Kenneth J. Toyne, Georg Weber
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Patent number: 4659501Abstract: Novel liquid crystal compounds, 2-cyano-4-halogenophenyl substituted-benzoates suitable as a component constituting a liquid crystal composition which exhibits a negative dielectric anisotropy, and a liquid crystal composition containing the same are provided, which benzoates are expressed by the formula ##STR1## wherein R represents an alkyl group or an alkoxy group each of 1 to 10 carbon atoms; ##STR2## represents ##STR3## or ##STR4## X and Y each represents H or a halogen atom of F or Cl and at least one of X and Y is necessarily H; and Z represents a halogen atom of F, Cl or Br.Type: GrantFiled: January 17, 1985Date of Patent: April 21, 1987Assignee: Chisso CorporationInventors: Shigeru Sugimori, Toyoshiro Isoyama, Yasuyuki Goto
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Patent number: 4652672Abstract: For the analytical and preparative separation of the optical isomers of optically active alkanolamines into their optically pure antipodes a new resolution method is presented which involves an ester formation of the alkanolamines with optically pure and symmetrically O,O disubstituted (R,R)- or (S,S)-tartaric acids. The derivitization reactions are carried out in aprotic solvents and the primary and secondary functions are blocked via ion-pair formations with strong acids, e.g. dichloroacetic acid. The tartaric acid anhydrides are predominantly used as reagents but other ester formation methods are also practicable. The mixture of the diastereomeric alkanolamine tartaric acid monoesters are separable into their optically active and pure isomers by various chromotographic separation techniques, e.g. straight or reverse phase LC, but also by extraction methods e.g. Soxhlet extraction.Type: GrantFiled: October 17, 1983Date of Patent: March 24, 1987Inventor: Wolfgang F. Lindner
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Patent number: 4652089Abstract: This invention concerns compounds of the formula: ##STR1## wherein n is 1 and X is --COO--, --OOC-- or --CH.sub.2 CH.sub.2 --; or n is O and X is --CH.sub.2 CH.sub.2 --;ring A is p-phenylene or trans-1,4-cyclohexylene;R.sup.2 is cyano, p-cyanophenyl or, when X is --COO-- or --OOC--, R.sup.2 may also be p-R.sup.3 -phenyl or trans-4-R.sup.3 -cyclohexyl;and R.sup.1 and R.sup.3 each are straight-chain C.sub.1 -C.sub.10 -alkyl.their manufacture and their use for electro-optical purposes and in gas chromatography are described.Type: GrantFiled: October 22, 1984Date of Patent: March 24, 1987Assignee: Hoffmann-La Roche Inc.Inventors: Gottfried Oesterhelt, Martin Petrzilka