Naphthyl Ring System Patents (Class 568/328)
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Patent number: 4871877Abstract: Quinones may be perfluoroalkylated by means of perfluoroalkyltrihydrocarbyl silane using certain active alkali metal salt catalysts and a proton source. The reaction--which is conducted, preferably in a suitable liquid phase reaction medium, most preferably a dipolar aprotic solvent--results in the formation of gem-disubstituted cyclohexadienones in which the gem substitutes are a perfluoroalkyl group and a hydroxyl group. These gem-disubstituted compounds in turn can be readily converted to perfluoroalkyl substituted aromatics, thus circumventing the traditional need for photochlorination followed by halogen exchange using hydrogen fluoride as a means of preparing perfluoroalkyl aromatic compounds.Type: GrantFiled: May 20, 1988Date of Patent: October 3, 1989Assignee: Ethyl CorporationInventor: G. Patrick Stahly
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Patent number: 4864063Abstract: Process for preparing Naproxen via a sequence of stereospecific reactions which comprises: condensation of 1-chloro-2-methoxy-naphthalene with a (S)-2-halo-propionyl halide according to the Friedel-Crafts reaction, ketalization of the thus obtained (S)-2-halo-1-(5'-chloro-6'-methoxy-2'-naphthyl)propan-1-one, rearrangement of said ketal to afford an ester, hydrolysis of the ester and removal of the chlorine atom in 5-position by hydrogenolysis.New (S) 2-halo-1-(5'-chloro-6'-methoxy-2'-naphthyl)propan-1-ones.Type: GrantFiled: December 23, 1987Date of Patent: September 5, 1989Inventors: Oreste Piccolo, Ermanno Valoti, Giuseppina Visentin
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Patent number: 4861915Abstract: Described are crystalline block copolymers displaying high glass transition temperatures, excellent mechanical properties, excellent chemical and thermal stability, and good melt processability. These block polymers contain segments of crystalline poly(aryl ether ketones).Type: GrantFiled: March 29, 1988Date of Patent: August 29, 1989Assignee: Amoco CorporationInventors: Robert A. Clendinning, James E. Harris, George T. Kwiatkowski, Lee P. McMaster, Markus Matzner, Paul A. Winslow
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Patent number: 4839323Abstract: Insoluble complex oxidation catalysts comprising chromium salts bound on an insoluble polymer supports having pendant pyridine groups, that are useful in oxidation reactions such as Tetralin.RTM. to .alpha.-tetralone, ethylbenzene to acetophenone, and 2-methyl-5-ethylpyridine to 2-methyl-5-acetylpyridine. Also disclosed are processes for accomplishing such oxidations utilizing such catalysts.Type: GrantFiled: November 2, 1987Date of Patent: June 13, 1989Assignee: Reilly Tar & Chemical CorporationInventors: Gerald L. Goe, Thomas D. Bailey, James R. Beadle
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Patent number: 4816596Abstract: A process for preparing substituted or unsubstituted trifluoroethoxy- or trifluoroethylthiobenzenes by reaction of a phenol or thiophenol, both of which may be substituted or unsubstituted, with a compound of the formula CF.sub.3 --CH.sub.2 --O--R', where R' is a moiety selected from the group consisting of trifluoroacetyl, methanesulfonyl, paratoluenesulfonyl, trichloromethanesulfonyl and chlorosulfonyl, in the presence of a strong alkaline base and a complexing agent of the formula:N--CHR.sub.1 --CHR.sub.2 --O--(CHR.sub.3 --CHR.sub.4 --O).sub.n --R.sub.5 ].sub.3 (II)wherein n is an integer from 0 to 10 (0 is less than or equal to n is less than or equal to 10), R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which may be identical or different, are selected from the group consisting of a hydrogen atom and an alkyl moiety having from 1 to 4 carbon atoms, and R.sub.5 denotes an alkyl or cycloalkyl moiety having from 1 to 12 carbon atoms, a phenyl moiety or a moiety of the formula: --C.sub.m H.sub.2m --C.sub.6 H.sub.Type: GrantFiled: March 28, 1986Date of Patent: March 28, 1989Assignee: Rhone-Polenc Specialites ChimouesInventor: Bernard Langlois
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Patent number: 4814340Abstract: The present invention relates to novel aromatic alkane derivatives represented by the following general formula (I): ##STR1## wherein Ar stands for a substituted or unsubstituted phenyl or naphtyl group, R.sup.1 stands for a methyl, ethyl or isopropyl group and R.sup.2 stands for a hydrogen atom or a methyl group, or R.sup.1 and R.sup.2 together with the carbon to which they are attached jointly represent a substituted or unsubstituted cycloalkyl group, and R.sup.3 stands for a fundamental group of an alcohol which is usually used in a form of R.sup.3 OH as to natural or synthetic pyrethroids, and also to processes for the preparation of these compounds and the uses of these compounds.These compounds of the present invention have excellent insecticidal and acaricidal activities while the toxicities of these compounds are very low.Type: GrantFiled: November 6, 1986Date of Patent: March 21, 1989Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Nakatani Kiyoshi, Satoshi Numata, Kenji Kodaka, Kengo Oda, Shiro Shiraishi, Takatoshi Udagawa
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Patent number: 4803013Abstract: Novel halogenated naphthalene derivatives of the formula ##STR1## where X is F or Br, and a process for making the same are disclosed. Insulating oils are also disclosed which essentially comprise such a fluorine-containing compound and commonly used hydrocarbon insulating oils. The additive is highly conductive to improved dielectric constant, dielectric loss, hydrogen gas absorptivity, fluidity and viscosity characteristics.Type: GrantFiled: March 16, 1988Date of Patent: February 7, 1989Assignee: Nippon Oil Co., Ltd.Inventor: Nobuo Yokoyama
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Patent number: 4790870Abstract: This invention relates to aryloxy optionally oxo-substituted indane or tetralin derivatives having herbicidal activity and to the use of such compounds to control the growth of noxious plants, i.e., weeds.Type: GrantFiled: May 1, 1987Date of Patent: December 13, 1988Assignee: PPG Industries, Inc.Inventors: David A. Hunt, James A. Schwindeman
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Patent number: 4782057Abstract: A benzo[h]cinnoline compound of the formula: ##STR1## wherein each of X and Y is hydrogen, halogen, trifluoromethyl, hydroxy, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, amino, alkanoylamido having 2 to 4 carbon atoms, nitro, cyano, alkanoyl having 2 to 4 carbon atoms; Ar is phenyl or pyridyl which may be optionally substituted by at least one substituent selected from the group consisting of halogen, trifluoromethyl, hydroxy, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, amino, alkanoylamido having 2 to 4 carbon atoms, nitro and cyano; and the bond position indicated by dotted line is single bond or double bond, a method of preparing said compound and a pharmaceutical composition containing said compound.Since these compounds possess high affinity for benzodiazepine receptor and antianxiety activity, they are useful as neutralizers to an excess dose of antianxiety agents or as antianxiety agents.Type: GrantFiled: March 25, 1986Date of Patent: November 1, 1988Assignee: Yoshitomi Pharmaceutical Industries, Ltd.Inventors: Tetsuya Tahara, Minoru Kawakami, Shuzo Takehara, Masamitsu Sakamori
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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: 4749804Abstract: Pharmaceutically useful optically active .alpha.-arylalkanoic acids or esters, ortho esters, or amides thereof are stereoselectively prepared by contacting an aryl magnesium Grignard reagent with an optically active .alpha.-substituted acyl halide to form the optically active aryl .alpha.-substituted alkyl ketone, which is ketalized and rearranged to the desired optically active .alpha.-arylalkanoic acid or the corresponding ester, ortho ester or amide. In an alternate embodiment, the aryl .alpha.-substituted alkyl ketone is reduced to the corresponding alkanol, which is rearranged to the .alpha.-arylalkanal. The alkanal so produced is converted to the desired optically active .alpha.-arylalkanoic acid by conventional methods.Type: GrantFiled: June 10, 1986Date of Patent: June 7, 1988Assignee: Syntex (U.S.A.) Inc.Inventor: George C. Schloemer
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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: 4736061Abstract: Process for preparing Naproxen via a sequence of stereospecific reactions which comprises: condensation of 1-chloro-2-methoxy-naphthalene with a (S)-2-halo-propionyl halide according to the Friedel-Crafts reaction, ketalization of the thus obtained (S)-2-halo-1-(5'-chloro-6'-methoxy-2'-naphthyl)-propan-1-one, rearrangement of said ketal to afford an ester, hydrolysis of the ester and removal of the chlorine atom in 5-position by hydrogenolysis.New (S) 2-halo-1-(5'-chloro-6'-methoxy-2'-naphthyl)-propan-1-ones.Type: GrantFiled: May 10, 1985Date of Patent: April 5, 1988Assignee: Blaschim S.p.A.Inventors: Oreste Piccolo, Ermanno Valoti, Giuseppina Visentin
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Patent number: 4731484Abstract: New compounds which are 4,4'-bis(trihaloacetyl) derivatives of aromatic compounds have been prepared by reacting an aromatic compound with a haloacetyl halide in the presence of a Friedel-Crafts catalyst, e.g. AlCl.sub.3, in a suitable solvent. The compounds are useful in preparing polycarbonates, polyesters, polyamides, polyketones and polyurethanes.Type: GrantFiled: April 30, 1986Date of Patent: March 15, 1988Assignee: The Dow Chemical CompanyInventor: Marlin E. Walters
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Patent number: 4724267Abstract: Bis(haloacylaromatic) compounds have been made by a new process in which monohaloacylated aromatic compounds have been reacted by a coupling reaction. These bis(haloacylaromatic) compounds can be employed as monomers in the preparation of polyesters and polyamides which have easy processability. The monohaloacylated compound is coupled by reacting two moles of the monomer with a carbon or sulfur compound containing at least two halogen atoms in the presence of a Friedel-Crafts catalyst.Type: GrantFiled: May 23, 1986Date of Patent: February 9, 1988Assignee: The Dow Chemical CompanyInventors: George M. St. George, Marlin E. Walters
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Patent number: 4720591Abstract: Chloro-olefins which contain a group of the formula ##STR1## where Y is chlorine or hydrogen, which are prepared by a process in which a trichloromethyl compound which contains a group of the general formula ##STR2## where X is hydrogen or an organic radical, is reduced with a chromium(II) salt in an aqueous medium.Type: GrantFiled: December 12, 1986Date of Patent: January 19, 1988Assignee: BASF AktiengesellschaftInventors: Eberhard Steckhan, Reinhard Wolf, Hermann Puetter
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Patent number: 4692447Abstract: The tricyclic dihydropyridazinone derivatives having formula I ##STR1## are endowed with interesting hypotensive, vasodilating, antiaggregant, antithrombotic and cytoprotective properties and are therefore useful in human or veterinary medicine.Type: GrantFiled: July 22, 1985Date of Patent: September 8, 1987Assignee: Boehringer Biochemia Robin, S.p.A.Inventors: Giorgio Cignarella, Carmelo A. Gandolfi, Odoardo Tofanetti, Piervitto Cipolla, Sergio Tognella
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Patent number: 4681952Abstract: A process for the preparation of 2,2-dimethyl-3-arylcyclopropanecarboxylic acid or ester of the formula ##STR1## in which Ar is naphthyl or the radical ##STR2## R.sup.1 is H or C.sub.1 -C.sub.4 -alkyl, Z is oxygen, sulphur, or 1,2-ethenediyl, andR.sup.2 represents hydrogen, halogen, cyano, nitro or trialkylsilyl or a radical, which is optionally substituted by halogen, from the series comprising alkyl, cycloalkyl, alkenyl, alkoxy, alkylenedioxy, alkylthio, alkylsulphinyl, alkylsulphonyl, dialkylamino, phenyl and phenoxy,comprising reacting a 1-aryl-1-halogeno-2,2-dimethyl-3-butanone of the formula ##STR3## in which X.sup.1 is chlorine or bromine, with a base in the presence of a diluent at a temperature between about -20.degree. and +150.degree. C., thereby to form a 2,2-dimethyl-3-arylcyclobutanone of the formula ##STR4## and reacting such 2,2-dimethyl-3-arylcyclobutanone with chlorine or bromine in the presence of an inert diluent at a temperature between about -30.degree. and +50.degree. C.Type: GrantFiled: November 7, 1984Date of Patent: July 21, 1987Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Dieter Arlt, Manfred Jautelat
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Patent number: 4656192Abstract: New tropolone derivatives of the general formula: ##STR1## wherein R.sup.1 represents H or an alkyl group, R.sup.2 represents an alkyl, aryl, aralkyl or heterocyclic group and R.sup.3 represents an alkoxyl, aryl or heterocyclic group or a group of the formula: ##STR2## or R.sup.2 and R.sup.3 may form together a part of a heterocyclic group, their metal complex salts, processes for the preparation thereof and the use thereof as anti-tumor agents.Type: GrantFiled: June 14, 1984Date of Patent: April 7, 1987Assignee: Mect CorporationInventor: Masatoshi Yamato
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Patent number: 4640708Abstract: Compounds of the formula ##STR1## wherein: R.sup.5 is a bicyclic aryl or nitrogen-containing heteroaryl ring system such as naphthyl, quinolyl, isoquinolyl or tetrahydroisoquinolyl, optionally substituted by a wide variety of groups;R.sup.4 and R.sup.1 are preferably hydrogen but may be other groups andR.sup.2 and R.sup.3 are selected from alkyl, haloalkyl, alkenyl, haloalkenyl and alkynyl, show high general grass-killing activity with good selectivity to many broad-leaf crops and in some instances selectivity to small-grain cereals. Processes for the preparation of compounds of formula I, intermediates in the preparation of compounds I and the herbicidal properties of compounds I are described.Type: GrantFiled: March 20, 1984Date of Patent: February 3, 1987Assignee: ICI Australia LimitedInventors: Graham J. Bird, Graeme J. Farquharson, Keith G. Watson
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Patent number: 4614747Abstract: This invention relates to novel compounds having pharmaceutical activity and having the general structure ##STR1## wherein the Z, R.sub.1, R.sub.2, R.sub.3, R.sub.4, n and m are defined within.Type: GrantFiled: November 29, 1984Date of Patent: September 30, 1986Assignee: USV Pharmaceutical Corp.Inventors: Bernard Loev, Howard Jones, Wan-kit Chan
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Patent number: 4605758Abstract: Pharmaceutically useful optically active .alpha.-arylalkanoic acids or esters, ortho esters, or amides thereof are stereoselectively prepared by contacting an aryl magnesium Grignard reagent with an optically active .alpha.-substituted acyl halide to form the optically active aryl .alpha.-substituted alkyl ketone, which is ketalized and rearranged to the desired optically active .alpha.-arylalkanoic acid or the corresponding ester, ortho ester or amide. In an alternate embodiment, the aryl .alpha.-substituted alkyl ketone is reduced to the corresponding alkanol, which is rearranged to the .alpha.-arylalkanal. The alkanal so produced is converted to the desired optically active .alpha.-arylalkanoic acid by conventional methods.Type: GrantFiled: April 23, 1984Date of Patent: August 12, 1986Assignee: Syntex Pharmaceuticals International Ltd.Inventor: George C. Schloemer
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Patent number: 4599362Abstract: The present invention relates to 2-arylethyl ether or thioether derivatives represented by the following general formula [I]: ##STR1## wherein Ar stands for an aryl group, R.sup.1 stands for straight or branched chain alkyl group of 1 to 6 carbons, R.sup.2 stands for a hydrogen atom, or a methyl or ethyl group, R.sup.3 stands for a halogen atom, or a methyl or methoxyl group, R.sup.4 stands for a hydrogen or halogen atom, or a lower alkyl or lower alkoxy group, and n is an integer of 1 or 2 with the proviso that when n is 2, the groups R.sup.4 may be the same or different, and Y stands for an oxygen or sulfur atom, and also to processes for the preparation of these ethers or thioethers and a use of these ethers or thioethers.These compounds of the present invention have excellent insecticidal and acaricidal activities while the toxicity of these compounds are very low.Type: GrantFiled: November 18, 1983Date of Patent: July 8, 1986Assignee: Mitsuitoatsu Chemicals, Inc.Inventors: Kiyoshi Nakatani, Satoshi Numata, Tsuneo Inoue, Akira Hosono, Kengo Oda, Yutaka Kubota, Hajime Tachibana, Takatoshi Udagawa, Masatoshi Gohbara
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Patent number: 4592876Abstract: Arylglyoxals which are new compounds, active as hypoglycemic agents.Type: GrantFiled: July 16, 1984Date of Patent: June 3, 1986Assignee: American Cyanamid CompanyInventors: Middleton B. Floyd, Jr., Vern G. DeVries
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Patent number: 4584294Abstract: The invention relates to fused tricyclic lactams and related compounds which are useful as angiotensin converting enzyme inhibitors and as antihypertensives.Type: GrantFiled: November 7, 1984Date of Patent: April 22, 1986Assignee: Merck & Co., Inc.Inventor: William V. Ruyle
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Patent number: 4581380Abstract: New 2,6-disubstituted derivatives of naphthalene have the formula ##STR1## wherein n is 1 or 2,R.sub.1 to R.sub.4 are hydrogen or CH.sub.3,R.sub.5 is ##STR2## (iv) 2-oxazolinyl, wherein m is 0 or 1, R.sub.6 is hydrogen, alkyl, OR.sub.9 wherein R.sub.9 is H, alkyl or ##STR3## wherein R.sub.10 is alkyl or aryl, or R.sub.6 is ##STR4## when m=1, r' and r" representing H, alkyl, mono- or poly-hydroxyalkyl, aryl or a heterocycle when taken together, R.sub.7 is H or alkyl, R.sub.8 is H, alkyl and the acetal of said compounds, and the salts of the compounds of formula I. These compounds are usefully employed in the pharmaceutical and cosmetic fields.Type: GrantFiled: November 28, 1984Date of Patent: April 8, 1986Assignee: Groupement Economique dite: Centre National de Recherches Dermatologiques C.I.R.D.Inventors: Braham Shroot, Jacques Eustache, Martine Bouclier
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Patent number: 4577025Abstract: A method for the preparation of an ester of .alpha.-thio-.alpha.-aromatic propionic acid derivatives of the formula: ##STR1## wherein R.sup.1 is alkyl, phenyl or benzothiazolyl, R.sup.2 is alkyl and Ar is an aromatic substituent.The method comprises reacting an ester of .alpha.-chloro-.alpha.-thiopropionic acid of the formula: ##STR2## with an aromatic compound of the formula ARH, in the presence of a Lewis acid. The method provides good reactivity and positional selectivity in the Friedel-Crafts reaction. Many esters of the formula (2) are useful as pharmaceuticals, agricultural chemicals, perfumes or their intermediates.Type: GrantFiled: August 26, 1983Date of Patent: March 18, 1986Assignee: Nissan Chemical Industries, Ltd.Inventors: Kazutaka Arai, Yoshio Ohara, Yashio Takakuwa, Toyoko Iizumi
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Patent number: 4542237Abstract: .alpha.-Arylalkanoic acids or esters, orthoesters or amides thereof are prepared by forming an .alpha.-hydroxy ketal or thioketal of an aryl alkyl ketone, activating the .alpha.-hydroxy substituent with an esterifying agent to form the corresponding ketal or thioketal ester substrate, wherein the ester group is sufficiently labile to non-catalytically disassociate from the substrate in a protic or dipolar, aprotic solvent, maintaining the ester substrate in contact with the protic or dipolar, aprotic solvent or mixtures thereof for a time sufficient to form the corresponding .alpha.-arylakanoic acid or ester, orthoester or amide thereof, and optionally concomitantly or sequentially hydrolyzing any ester, orthoester or amide formed to the corresponding .alpha.-arylalkanoic acid.Type: GrantFiled: June 7, 1983Date of Patent: September 17, 1985Assignee: Syntex Pharmaceuticals International LimitedInventor: George C. Schloemer
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Patent number: 4539419Abstract: Compounds of the formula ##STR1## wherein R is hydrogen or lower alkyl, X is hydrogen or halogen, and A is the group ##STR2## wherein R.sub.1 is hydrogen, acyl or lower alkyl, R.sub.2 is hydrogen or lower alkyl, m is an integer from 2 to 4, n is an integer from 1 to 3, and t is an integer from 1 to 5, provided that R.sub.1 is adjacent to --(CH.sub.2).sub.m [O(CH.sub.2).sub.m ].sub.n O--, and, when R.sub.2 is hydrogen, salts thereof with pharmaceutically acceptable bases, are described. The compounds of formula I are useful as agents for the treatment of allergic conditions.Type: GrantFiled: May 2, 1983Date of Patent: September 3, 1985Assignee: Hoffmann-La Roche Inc.Inventor: Ronald A. LeMahieu
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Patent number: 4481372Abstract: Described is a novel process for preparing allyl alpha and beta ionones defined according to the structure: ##STR1## wherein one of the dashed lines represents a carbon-carbon double bond and the other of the dashed lines represents a carbon-carbon single bond; and wherein the wavy lines represent the cis or trans juxtaposition of the acyl and cyclohexenyl rings about the carbon-carbon double bond which is alpha to the acyl moiety, and intermediates used in said process defined according to the structure: ##STR2## wherein the wavy lines and dashed lines are defined supra and wherein R.sub.1 represents hydrogen or allyl and Z represents methyl or OR.sub.2 and wherein R.sub.2 represents methyl or ethyl.Type: GrantFiled: September 30, 1982Date of Patent: November 6, 1984Assignee: International Flavors & Fragrances Inc.Inventors: Richard M. Boden, Steven D. Temes, Theodore J. Tyszkiewicz
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Patent number: 4464300Abstract: There are presented benzazepines of the formula ##STR1## wherein either R.sup.1 is hydrogen, lower alkyl, 4-pyridyl or the group --(CH.sub.2).sub.n --NR.sup.6 R.sup.7 and R.sup.2 and R.sup.3 together are an additional bond or R.sup.1 and R.sup.2 together are the oxo group and R.sup.3 is hydrogen or lower alkyl, R.sup.4 is phenyl, o-halophenyl or 2-pyridyl, R.sup.5 is halogen or nitro and either R.sup.6 is hydrogen or lower alkyl and R.sup.7 is hydrogen, lower alkyl, lower alkenyl or lower alkynyl or R.sup.6 and R.sup.7 together with the nitrogen atom are 4-(lower alkyl)-1-piperazinyl or 4-morpholinyl and n is the number 0 or 1, and their pharmaceutically acceptable acid additions salts.The compounds possess interesting psychotropic properties, i.e., pronounced anxiolytic properties have been established in the case of certain representative members of this class of substance.Type: GrantFiled: July 15, 1982Date of Patent: August 7, 1984Assignee: Hoffmann-La Roche Inc.Inventors: Rene Borer, Max Gerecke, Emilio Kyburz
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Patent number: 4439418Abstract: A topical cosmetic preparation for the treatment of seborrhea containing an antiseborrheically effective amount of at least one compound having the formula ##STR1## wherein Ar represents a member selected from the group consisting of phenyl, phenyl substituted with at least one group selected from the group consisting of alkyl having from 1 to 4 carbon atoms, alkoxy having from 1 to 4 carbon atoms, hydroxy and halo, naphthyl and heteroaromatic radical having from 4 to 5 carbon atoms in the cycle, and R represents a member selected from the group consisting of hydrogen, alkyl having from 1 to 4 carbon atoms, alkanoyl having from 1 to 4 carbon atoms, aryl and arylcarbonyl, where aryl has the same meaning as Ar, as an antiseborrheic, and further containing conventional vehicles and additives. The invention also relates to the process for reducing sebaceous cell sebum production employing said topical cosmetic preparation.Type: GrantFiled: December 9, 1981Date of Patent: March 27, 1984Assignee: Henkel KGaAInventors: Hinrich Moller, Siegfried Wallat, Friedhelm Bartnik
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Patent number: 4436666Abstract: Enol derivatives of 2-aryl-1,3-cycloalkanedione compounds exhibit outstanding herbicidal and acarcidal activity.Type: GrantFiled: September 22, 1978Date of Patent: March 13, 1984Assignee: Union Carbide CorporationInventor: Thomas N. Wheeler
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Patent number: 4420639Abstract: 4-(6'-Methoxy-2'-naphthyl) butan-2-one is described as having anti-inflammatory activity and an improved therapeutic ratio.Type: GrantFiled: November 12, 1981Date of Patent: December 13, 1983Assignee: Beecham Group LimitedInventors: Anthony W. Lake, Carl J. Rose
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Patent number: 4412995Abstract: Compounds of the formula ##STR1## where R is hydrogen, methyl, ethyl, propyl, 2-propenyl or 2-propynyl; and R' is hydrogen or fluoro possess anti-inflammatory activity. The compounds where R is H are prepared by reacting a compound of the formula ##STR2## with (1H,3H)-pyrimidine-2,4,5,6-tetrone. The compounds where R is other than hydrogen are prepared by reacting a compound where R is hydrogen with the appropriate alkylating agent.Type: GrantFiled: January 13, 1982Date of Patent: November 1, 1983Assignee: Sterling Drug Inc.Inventors: Malcolm R. Bell, John L. Herrmann, Jr.
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Patent number: 4382959Abstract: 4-(6-Methoxy-2-naphthyl)-3-hydroxybutan-2-one and 4-(6-methoxy-2-naphthyl)buta-2,3-diol have good degrees of anti-inflammatory and analgesic activity coupled with an advantageous therapeutic ratio based on gastric irritancy and are non-oestrogenic. Their preparation and use are described.Type: GrantFiled: April 13, 1981Date of Patent: May 10, 1983Assignee: Beecham Group LimitedInventor: Alexander C. Goudie
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Patent number: 4341906Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, benzyl, benzoyl, alkanoyl of 1 to 5 carbon atoms or --CO--(CH.sub.2).sub.p --NR'R" wherein p is 0 or an integer from 1 to 4; each of R' and R" when taken individually is hydrogen or alkyl of 1 to 4 carbon atoms; R' and R" when taken together with the nitrogen to which they are attached form a 5- or 6-membered heterocyclic ring selected from piperidino, pyrollo, pyrrolidino, morpholino and N-alkylpiperazino having from 1 to 4 carbon atoms in the alkyl group;R.sub.2 is selected from hydrogen, alkanoyl of 1 to 6 carbon atoms and benzoyl;R.sub.3 is selected from hydrogen, methyl and ethyl;R.sub.4 is selected from hydrogen, alkyl of 1 to 6 carbon atoms and benzyl;Z is selected from:(a) alkylene having from one to nine carbon atoms;(b) -(alk.sub.1).sub.m -X-(alk.sub.2).sub.n - wherein each of (alk.sub.1) and (alk.sub.2) is alkylene having from 1 to 9 carbon atoms, with the proviso that the summation of carbon atoms in (alk.sub.1) plus (alk.sub.Type: GrantFiled: December 22, 1980Date of Patent: July 27, 1982Assignee: Pfizer Inc.Inventors: Thomas H. Althuis, Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
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Patent number: 4328356Abstract: Esters of arylacetic acids, more particularly lower alcohol esters of arylacetic acids, including those substituted on the methylene group, are prepared by rearrangement of the corresponding alpha-halo-alkylarylketones with Ag compounds in lower alcohols and in an acid medium. From the alkyl esters so prepared, their respective free acids can be obtained, if desired, by various means such as hydrolysis or the shift with mineral acids of the alkaline salts prepared by reaction with alkali, etc.Type: GrantFiled: February 15, 1980Date of Patent: May 4, 1982Assignee: Montedison S.p.A.Inventors: Claudio Giordano, Francesco Casagrande
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Patent number: 4326055Abstract: This invention is directed to 5,6,7,8-tetrahydro-naphthyl or indanyl stilbene derivatives which are useful as tumor inhibiting agents, in the treatment of neoplasms, dermatological conditions and rheumatic illnesses.Type: GrantFiled: December 15, 1978Date of Patent: April 20, 1982Assignee: Hoffmann-La Roche Inc.Inventor: Peter Loeliger
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Patent number: 4301166Abstract: The invention relates to hydroxyethyl-azole compounds and methods for their preparation. Also included in the invention are compositions containing said hydroxyethyl-azole compounds and methods for the use of said compounds and compositions as antimycotic agents.Type: GrantFiled: November 9, 1979Date of Patent: November 17, 1981Assignee: Bayer AktiengesellschaftInventors: Erik Regel, Karl H. Buchel, Ingo Haller, Manfred Plempel
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Patent number: 4301081Abstract: The invention includes novel alkali metal complex compounds (and processes for their preparation) which are useful, inter alia for the hydrogenation of alkali metals at room temperature or below room temperature to form hydrides or nitrides.Type: GrantFiled: January 28, 1980Date of Patent: November 17, 1981Assignee: Studiengesellschaft Kohle mbHInventor: Borislav Bogdanovic
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Patent number: 4283352Abstract: In a method for the production of .alpha.-tetralone wherein tetralin is oxidized in the absence of a catalyst at a temperature of from 50.degree. to 100.degree. C. to an extent that the conversion of tetralin into tetralin hydroperoxide is 25 to 35 percent by weight, thereby producing a solution of tetralin hydroperoxide in tetralin, and wherein an inorganic metal salt is added to said solution to decompose the tetralin hydroperoxide to .alpha.-tetralone, the improvement comprising adding to said solution, as said inorganic metal salt, a mixture of at least one water-soluble inorganic iron salt and at least one water-soluble inorganic copper salt at a temperature of from 0.degree. to 90.degree. C.Type: GrantFiled: January 3, 1979Date of Patent: August 11, 1981Assignee: Kureha Kagaku Kogyo Kabushiki KaishaInventors: Takashi Yamauchi, Hirofumi Nanbu
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Patent number: 4282354Abstract: In general, materials having the structure ##STR1## wherein A represents phenylene, napthylene, anthracenediyl, and dibenzothien-diyl;R.sub.1 and R.sub.2, which may be the same or different when taken alone represent hydrogen, cyano, alkylcarbonyl and arylcarbamoyl, arylcarbonyl, cyanoaryl;R.sub.1 and R.sub.2, when taken together, represent sufficient atoms to form substituted and unsubstituted radicals selected from the group consisting of furanylidene, fluorenylidene, pyrimidinylidene, thiazolidinylidene, pyrrolinyl, and indenyl, isoxazolinylidene, pyrazolinylidene and indanylidene, wherein said substituents are selected from the group consisting of hydrogen, cyano, aryl, oxo, thioxo, nitro, alkyl, nitroaryl, carbamoyl and cyanoalkyl; andalkyl represents an alkyl group having from one to six carbon atoms; aryl represents an aromatic nucleus selected from the group consisting of benzene, napthalene or anthracene, are useful in electrophoretic migration imaging processes.Type: GrantFiled: April 18, 1979Date of Patent: August 4, 1981Assignee: Eastman Kodak CompanyInventors: James A. Van Allan, Louis J. Rossi, Melvin S. Bloom, Michael T. Regan, Hal E. Wright, Joseph Y. Kaukeinen
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Patent number: 4276226Abstract: Aromatic diketones and diesters are provided of the formula ##STR1## wherein R is independently methyl or chloro; R' is independently hydrogen or R; R.sup.2 is 1,4-phenylene, 1,3-phenylene, 2,6-naphthylene, 4,4'-biphenylene, or 4,4'-biphenylene ether; and R.sup.3 is hydrogen or ##STR2## where R.sup.4 is a hydrocarbon group of 1-10 carbon atoms.Type: GrantFiled: July 23, 1979Date of Patent: June 30, 1981Assignee: E. I. Du Pont de Nemours and CompanyInventors: Robert A. Clement, Burton C. Anderson
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Patent number: 4275071Abstract: Imidazole derivatives of the formula I and pharmaceutically acceptable acid addition salts thereof are provided: ##STR1## In the formula, R.sub.4 1- or 2-naphthyl, optionally substituted with Cl, Br, or I; 1,2,3,4-tetrahydro-6-naphthyl; 3-duryl, optionally 6-substituted by Cl, Br, I, NO.sub.2, CH.sub.3 or benzyl; mesityl, phenyl 2-, 3- or 4-substituted by OH, NH.sub.2, NO.sub.2, CH.sub.3 CONH, phenyl, phenoxy, cyclohexyl, phenylthio, benzylthio, C.sub.1 -C.sub.6 alkyl or C.sub.1 C.sub.6 alkylthio; 4-bibenzylyl; 3,4-dihydroxyphenyl,n=0, 1 or 2 and(a) R=H, alkyl having 1 to 6 carbon atoms or phenyl R.sub.1 =H, alkyl having 1 to 6 carbon atoms or phenyl one of R.sub.2 and R.sub.3 =H the other of R.sub.2 and R.sub.3 =H, OH, benzoyloxy, C.sub.2 -C.sub.7 alkanoyloxy, N-(C.sub.1 -C.sub.6 alkyl)-carbamoyloxy, N,N-[di-(C.sub.1 C.sub.6)alkyl]-carbamoyloxy, but if R.sub.2 =R.sub.3 =H then R=R.sub.1 =H, or(b) R=H, C.sub.1 -C.sub.6 alkyl, phenyl R.sub.1 =H, C.sub.1 -C.sub.6 alkyl, phenyl R.sub.2 +R.sub.Type: GrantFiled: July 10, 1979Date of Patent: June 23, 1981Assignee: Recordati S.A.Inventors: Dante Nardi, Alberto Tajano, Maria J. Magistretti
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Patent number: 4270005Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, benzyl, benzoyl, alkanoyl of 1 to 5 carbon atoms or --CO--(CH.sub.2).sub.p --NR'R" wherein p is 0 or an integer from 1 to 4; each of R' and R" when taken individually is hydrogen or alkyl of 1 to 4 carbon atoms; R' and R" when taken together with the nitrogen to which they are attached form a 5- or 6-membered heterocyclic ring selected from piperidino, pyrollo, pyrrolidino, morpholino and N-alkylpiperazino having from 1 to 4 carbon atoms in the alkyl group;R.sub.2 is selected from hydrogen, alkanoyl of 1 to 6 carbon atoms and benzoyl;R.sub.3 is selected from hydrogen, methyl and ethyl;R.sub.4 is selected from hydrogen, alkyl of 1 to 6 carbon atoms and benzyl;Z is selected from:(a) alkylene having from one to nine carbon atoms;(b) --(alk.sub.1).sub.m --X--(alk.sub.2).sub.n -- wherein each of (alk.sub.1) and (alk.sub.2) is alkylene having from 1 to 9 carbon atoms, with the proviso that the summation of carbon atoms in (alk.sub.1) plus (alk.sub.Type: GrantFiled: September 24, 1979Date of Patent: May 26, 1981Assignee: Pfizer Inc.Inventors: Thomas H. Althuis, Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
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Patent number: 4247709Abstract: The present invention relates to a process for the preparation of 4-(6.sup.1 -methoxy-2.sup.1 -naphthyl)butan-2-one and to certain compounds for use in that process.British Pat. Spec. No. 1,474,377 discloses inter alia that 4-(6.sup.1 -methoxy-2.sup.1 -naphthyl) butan-2-one possesses useful anti-inflammatory activity. A particularly favored process has now been discovered that can be used to produce 4-(6.sup.1 -methoxy-2.sup.1 -naphthyl) butan-2-one in particularly good yield.The present invention provides a process for the preparation of 4-(6.sup.1 -methoxy-2.sup.1 -naphthyl)butan-2-one which process comprises the hydrogenation of a compound of the formula (I): ##STR1## wherein Ar is a 6-methoxy-2-naphthyl group; X and Y are each hydrogen atoms or together represent a second bond between the carbon atoms to which they are attached; and R is a group such that --CO.sub.2 R represents an ester group convertible by hydrogenation to a CO.sub.2 H group.Type: GrantFiled: December 26, 1978Date of Patent: January 27, 1981Assignee: Beecham Group LimitedInventors: Carl J. Rose, David Miller
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Patent number: 4243682Abstract: 4-(6-Substituted naphthyl)butan-2-ols,-butan-2-ones,-pentan-2-ols and -pentan-2-ones bearing a fluoro group in the naphthyl ring, and pro-drugs thereof, are anti-inflammatory agents. A typical embodiment is 4-(4-fluoro-6-methoxy-2-naphthyl)-butan-2-one.Type: GrantFiled: October 23, 1978Date of Patent: January 6, 1981Assignee: Beecham Group LimitedInventors: Alexander C. Goudie, Laramie M. Gaster
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Patent number: 4231965Abstract: 2-Nitrobenzofurans in which the furan ring is either fused to or substituted by a fused bicyclic system, which are active as antimicrobial agents, processes for their use and intermediates therefor are described.Type: GrantFiled: March 5, 1979Date of Patent: November 4, 1980Assignee: Riker Laboratories, Inc.Inventors: Robert A. Scherrer, Richard M. Stern