Oxygen Attached Indirectly To The Cyano Group By Nonionic Bonding Patents (Class 558/423)
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Patent number: 4760160Abstract: The invention provides a process for the preparation of 4-fluorophenols of formula ##STR1## wherein n is 0 to 3, each R independently represents a halogen atom or an alkyl, alkoxy, cyano or optionally substituted amino group and Z represents a hydrogen or halogen atom or a cyano group characterized by reacting a fluorohalocyclohexadienone of formula ##STR2## wherein X represents a halogen atom, with a compound of formula A-Z, wherein Z is as defined above and A represents a hydrogen or alkali metal atom, provided that when both A and Z are hydrogen, the reaction is carried out in the additional presence of a Group VIII metal hydrogenation catalyst, and 4-fluorophenols of formula I per se wherein Z is a CN group.Type: GrantFiled: January 14, 1986Date of Patent: July 26, 1988Assignee: Shell Oil CompanyInventors: Jan H. H. Meurs, David W. Sopher
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Patent number: 4760174Abstract: Tetralin derivatives of the formula I ##STR1## where X, R.sup.1, R.sup.2 and R.sup.3 have the meanings stated in the description, and their preparation are described. The novel compounds are useful for the treatment of disorders.Type: GrantFiled: September 20, 1985Date of Patent: July 26, 1988Assignee: BASF AktiengesellschaftInventors: Fritz-Frieder Frickel, Hans-Heiner Wuest, Axel Nuerrenbach
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Patent number: 4755511Abstract: This invention relates to tricyclic pyridazinone compounds, pharmaceutical compositions containing the compounds, and a method of stimulating cardiac activity in a mammal by administering an effective amount of the compound. A compound of the invention is 7-carboxamido-4,4a-dihydro-4a-methyl-[5H]-indeno[1,2-c]-pyridazin-3[2H]-on e.Type: GrantFiled: September 22, 1987Date of Patent: July 5, 1988Assignee: Smith Kline & French Laboratories LimitedInventor: Brian H. Warrington
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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: 4739099Abstract: The invention provides a compound of formula (II): ##STR1## and the corresponding isomers and salts; in this formula, a equals 0 or 1; R.sub.1 and R.sub.2 represent, independently, H or a C.sub.1 -C.sub.4 alkyl group; R.sub.3 denotes --C.tbd.N; oxazolinyl; --CH.sub.2 OR.sub.4 (R.sub.4 =H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.6 mono- or poly-hydroxyalkyl, cyclopentyl or cyclohexyl, or --OR.sub.4 =tetrahydropyranyl); --COR.sub.5 (R.sub.5 =H, C.sub.1 -C.sub.4 alkyl, --NR'R" where R' and R" have various meanings); --OR.sub.6 (R.sub.6 =H, C.sub.1 -C.sub.18 alkyl, C.sub.2 -C.sub.3 monohydroxyalkyl or C.sub.3 -C.sub.6 polyhydroxyalkyl with 2-5 OH groups), which has useful medicinal and cosmetic applications.Type: GrantFiled: September 30, 1985Date of Patent: April 19, 1988Assignee: L'OrealInventors: Gerard Lang, Serge Forestier, Alain Lagrange, Braham Shroot
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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: 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: 4710315Abstract: Anisotropic compounds of the formula (1) specified in claim 1 are suitable, owing to their low .DELTA..epsilon./.epsilon..perp. values for liquid crystal displays which have high information densities of for examples up to 10.sup.6 image dots and accordingly need to be highly multiplexible; compared with known compounds they offer improved application properties and are relatively simple to synthesize.Type: GrantFiled: December 16, 1985Date of Patent: December 1, 1987Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Hans P. Schad, Stephen M. Kelly
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Patent number: 4699993Abstract: Novel compounds having greatest interest as biologically-active materials for the treatment of diabetic complications in mammals, or intermediates for such materials, are perfluoroalkyl compounds corresponding to the formula: ##STR1## wherein R and R' are independently selected from chloro, fluoro, nitro, hydroxy, and alkyl and alkoxy substituents containing 1-6 carbons; Q is --CN, --COOL, --COX, or --CTN(R")CH.sub.2 COOL; L is hydrogen, alkali metal, or saturated hydrocarbyl; X is halo; T is oxygen or sulfur; R" is an alkyl group containing 1-6 carbons; m is 0 or 1; and n is an integer of at least one.Type: GrantFiled: December 12, 1985Date of Patent: October 13, 1987Assignee: Ethyl CorporationInventor: Vernon O. Brandt
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Patent number: 4695648Abstract: A compound having a potentially inhibitory effect on 15-hydroxy-prostaglandin dehydrognase (PGDH) and having the formula ##STR1## in which R.sub.1 and R.sub.2 are hydrogen or lower alkyl;R.sub.3 is hydrogen, lower alkyl or substituted or unsubstituted phenyl;R.sub.4, R.sub.5, and R.sub.6 are hydrogen, halogen, lower alkyl, lower alkoxy, cyano, carboxy or nitro; at least one of the groups R.sub.4 to R.sub.6 being hydrogen;R.sub.7 to R.sub.11 are hydrogen, halogen, cyano, lower alkyl, trifluoromethyl, lower alkoxy, hydroxy, lower acyl, lower alkoxycarbonyl, N,N,-diloweralkyl-aminocarbonyl or N,N-loweralkylene-aminocarbonyl; and R.sub.8 and R.sub.10 may in addition be carboxy; at least two of R.sub.7 to R.sub.11 always being hydrogen; and--A-- is --CO--, --CH.sub.2 --CO--, --CH.dbd.CH--, --CH.dbd.CH--CO-- or corresponding groups in which a hydrogen atom is replaced by a lower alkyl group.The invention comprises also lactones of those compounds in which R.sub.Type: GrantFiled: August 29, 1985Date of Patent: September 22, 1987Assignee: Pharmacia ABInventors: Karl H. Agback, Tamara Agback, Alf S. Nygren
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Patent number: 4695573Abstract: There are disclosed compounds having the formula ##STR1## wherein n is 1, 2 or 3; X is hydrogen, loweralkyl, loweralkoxy, halogen, hydroxy, nitro, trifluoromethyl, NHCOR.sub.2 where R.sub.2 is loweralkyl, or NR.sub.3 R.sub.4 where R.sub.3 and R.sub.4 are independently hydrogen or loweralkyl; R is hydrogen or loweralkyl; R.sub.1 is hydrogen, loweralkyl, diloweralkylaminoloweralkyl, arylloweralkyl, diarylloweralkyl, furylloweralkyl, thienylloweralkyl, oxygen-bridged arylloweralkyl, oxygen-bridged diarylloweralkyl, oxygen-bridged furylloweralkyl or oxygen-bridged thienylloweralkyl; Y is C.dbd.O or CR.sub.5 OH where R.sub.5 is hydrogen or loweralkyl; Z is CH.sub.2 or C.dbd.CR.sub.6 R.sub.7 where R.sub.6 and R.sub.7 are independently hydrogen or loweralkyl; or Y and Z taken together is CR.sub.5 .dbd.CH where CR.sub.Type: GrantFiled: October 1, 1985Date of Patent: September 22, 1987Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventors: Gregory M. Shutske, Frank A. Pierrat
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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: 4684734Abstract: Organic fluorine compounds such as pentafluorobenzonitrile, tetrafluorophthalonitriles, and pentafluoropyridine are produced by a method which comprises causing a chloro- or bromo-organic compound to react with a fluorinating agent such as an alkali metal fluoride in benzonitrile as a solvent at temperatures in the range of 190.degree. to 400.degree. C. under at least spontaneously generated pressure.Type: GrantFiled: September 13, 1985Date of Patent: August 4, 1987Assignee: Nippon Shokubai KK Co., Ltd.Inventors: Osamu Kaieda, Masaru Awashima, Isao Okitaka, Toshiaki Nakamura
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Patent number: 4677219Abstract: An improved process for the preparation of 6-substituted-5-alkyl-2,4-quinazolinediamines, useful in the production of trimetrexate and similar antifolate agents, together with several novel intermediates are disclosed.Type: GrantFiled: July 17, 1986Date of Patent: June 30, 1987Assignee: Warner-Lambert CompanyInventors: Ellen M. Berman, Mark J. Suto
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Patent number: 4654162Abstract: A novel compound usable as a component constituting liquid crystal materials having a positive dielectric anisotropy value and a liquid crystal composition containing the same are provided, which compound is an alcohol derivative expressed by the general formula ##STR1## wherein R.sup.1 represents a hydroxyalkyl group of 1 to 10 carbon atoms having hydroxyl group at the end or an intermediate position thereof; R.sup.2 represents an alkyl group or an alkoxy group each of 1 to 10 carbon atoms or --C.tbd.N; and ##STR2## represents ##STR3## and when R.sup.2 represents --C.tbd.Type: GrantFiled: August 12, 1985Date of Patent: March 31, 1987Assignee: Chisso CorporationInventors: Shigeru Sugimori, Yasuyuki Goto, Toyoshiro Isoyama, Kazunori Nigorikawa
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Patent number: 4637897Abstract: Nematic compounds with a negative DC antisotropy, characterized by the formula I ##STR1## in which m=1 or 2, r is zero or 1 and m+r=1 or 2, and R.sup.1 and R.sup.2 are identical or different and are selected from alkyl and alkoxy groups each having 1-12 carbon atoms in a straight or branched chain, which may be chiral, Z is a bridge member selected from a single bond and the groups of the formulae --CH.sub.2 CH.sub.2 --, --OCH.sub.2 --, --O--CO-- or --CO--O--, one of the groups X and Y is selected from fluorine, chlorine, bromine and cyano and the other of the groups X and Y is selected from hydrogen, fluorine, chlorine, bromine and cyano, with the proviso that m=r=1 if X and Y are both cyano, are suitable as components for liquid crystal mixtures having an overall negative DC anisotropy, such as are required in particular for electro-optical displays of the type of guest/host displays or homotropic-nematic displays.Type: GrantFiled: August 6, 1984Date of Patent: January 20, 1987Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventor: Stephen M. Kelly
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Patent number: 4631286Abstract: There are disclosed compounds having the formula ##STR1## wherein X is hydrogen, loweralkyl, loweralkoxy, halogen, hydroxy, nitro, NHCOR.sub.2 wherein R.sub.2 is loweralkyl, or a group of the formula NR.sub.3 R.sub.4 wherein R.sub.3 and R.sub.4 are independently hydrogen or loweralkyl; R and R.sub.1 are independently hydrogen, loweralkyl, phenylloweralkyl, phenylloweralkyl in which the phenyl group is substituted by one or more loweralkyl, loweralkoxy, halogen, hydroxy or trifluoromethyl, diphenylloweralkyl or diphenylloweralkyl in which one or both phenyl groups are substituted by one or more loweralkyl, loweralkoxy, halogen, hydroxy or trifluoromethyl; Y is C.dbd.O or CR.sub.5 OH wherein R.sub.5 is hydrogen or loweralkyl; Z is CH.sub.2 or C.dbd.CR.sub.6 R.sub.7 wherein R.sub.6 and R.sub.7 are independently hydrogen or loweralkyl; or Y and Z taken together is CR.sub.5 .dbd.CH wherein CR.sub.Type: GrantFiled: October 25, 1984Date of Patent: December 23, 1986Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventors: Gregory M. Shutske, Frank A. Pierrat
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Patent number: 4630896Abstract: Compounds of the formula: ##STR1## wherein one of X.sup.1 and X.sup.2 is --CH.sub.2 CH.sub.2 -- and the other is --CH.sub.2 CH.sub.2 -- or a single covalent bond,ring A is 1,4-phenylene or trans-1,4-cyclohexylene, andR.sup.1 is straight-chain C.sub.1 -C.sub.12 -alkyl or when positioned on a 1,4-phenylene ring R.sup.1 may also be straight chain C.sub.1 -C.sub.12 -alkoxy.Type: GrantFiled: May 29, 1984Date of Patent: December 23, 1986Assignee: Hoffmann-La Roche Inc.Inventors: Martin Petrzilka, Alois Villiger
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Patent number: 4623659Abstract: Polyhydroxy-substituted benz, phenylacet and mandelamidines, amidates, amidoximes and hydroxyamidoximes--ribonucleotide reductase inhibitors, and free radical scavengers.Type: GrantFiled: May 23, 1983Date of Patent: November 18, 1986Inventors: Bartholomeus van't Riet, Howard L. Elford, Galen L. Wampler
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Patent number: 4614609Abstract: Chiral smectic compounds having a high response rate and being superior as a ferroelectric liquid crystalline material, and chiral smectic mixtures containing the same are provided, which compounds being expressed by the formula ##STR1## wherein X represents --CH.sub.2 --, --O-- or --CO--; n represents 0, 1 or 2; when X represents --CH.sub.2 --, Y represents R--, R--CO--, ROCO--, ##STR2## wherein R represents an alkyl group having 1 to 18 carbon atoms, and when X represents --O-- or --CO--, Y represents R; and * represents a symbol indicating an optically active carbon atom.Type: GrantFiled: May 24, 1984Date of Patent: September 30, 1986Assignee: Chisso CorporationInventors: Hiromichi Inoue, Shinichi Saito, Kanetsugu Terashima, Takashi Inukai, Kenji Furukawa
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Patent number: 4613682Abstract: The vapor phase reaction of phenolic compounds with organic halides to form aromatic ethers is catalyzed by metal oxides. The halide value of the organic halide is retained as hydrogen halide which can be reacted with a halide acceptor such as methanol to form methyl halide and water.Type: GrantFiled: August 19, 1985Date of Patent: September 23, 1986Assignee: The Dow Chemical CompanyInventor: Kathryn A. Eickholt
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Patent number: 4600528Abstract: New decalin-carbonitriles of the formula I ##STR1## wherein R.sup.1 is an alkyl group with 1-10 C atoms, it being possible for up to two CH.sub.2 groups to be replaced by O atoms, Z is --CH.sub.2 CH.sub.2 --, --CO--O--, --O--CO--, --O--CH.sub.2 --, --CH.sub.2 O-- or a single bond, A is 1,4-phenylene, 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, 1,4-bicyclo(2,2,2)octylene, pyrimidine-2,5-diyl or a single bond, and R.sup.2 is an alkyl group with 1 to 10 C atoms, it being possible for up to two CH.sub.2 groups to be replaced by O atoms, or is F, Cl, Br, CN, --O--COR.sup.3 or --COOR.sup.3, or, if at least one of the groups Z and A is not a single bond, can also be H and R.sup.3 is alkyl of 1 to 6 C atoms, and the acid addition salts of basic compounds of this type, are suitable for use as components of liquid crystal dielectrics.Type: GrantFiled: June 1, 1984Date of Patent: July 15, 1986Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: Rudolf Eidenschink, Georg Weber
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Patent number: 4595763Abstract: Aromatic hydroxyl- or thiol-containing compounds are methylated by contacting with methyl trichloroacetate at elevated temperatures in the presence of an initiator.Type: GrantFiled: June 27, 1983Date of Patent: June 17, 1986Assignee: The Dow Chemical CompanyInventors: James M. Renga, Pen-Chung Wang
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Patent number: 4594195Abstract: Compounds of formula (I) ##STR1## and acid addition salts thereof, wherein R.sup.1 is hydrogen, hydroxy, alkoxy, aryloxy, aralkoxy, heteroaryloxy or heteroaralkoxy; andone of R.sup.2, R.sup.3 and R.sup.4 is hydrogen and the others are the same or different and each is hydrogen, alkyl, aryl, aralkyl, heteroaryl or heteroaralkyl; orR.sup.2 is hydrogen and ##STR2## is mono- or bi-cyclic amino, inhibit enterotoxin-induced secretion into the small intestine and are, therefore, useful in treating enterotoxin induced diarrhoea in humans and scours in animals.Type: GrantFiled: December 21, 1984Date of Patent: June 10, 1986Assignee: Beecham Group p.l.c.Inventors: Peter M. Newsome, Noel A. Mullan, John P. Marshall
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Patent number: 4589914Abstract: Herbicidally effective diphenyl ether compounds of the formula: ##STR1## where, for example, X is a halogen atom or a nitro group, R.sup.1 is a hydrogen atom or a chlorine, bromine or iodine atom, and R.sup.2 is a group --OR.sup.3 wherein R.sup.3 is an alkyl group containing from 1 to 12 carbon atoms.Type: GrantFiled: March 27, 1984Date of Patent: May 20, 1986Assignee: Imperial Chemical Industries PLCInventor: David Cartwright