Benzene Ring Containing Patents (Class 568/705)
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Patent number: 5492917Abstract: Novel compounds of the general structural formula I: ##STR1## have endothelin antagonist activity and are therefore useful in treating cardiovascular disorders, such as hypertension, pulmonary hypertension, postischemic renal failure, vasospasm, cerebral and cardiac ischemia, myocardial infarction, endotoxic shock, inflammatory diseases including Raynaud's disease and asthma.Type: GrantFiled: September 29, 1993Date of Patent: February 20, 1996Assignee: Merck & Co., Inc.Inventors: Ralph A. Rivero, Peter D. Williams, Daniel F. Veber
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Patent number: 5414148Abstract: p-Nitrophenolic compounds, e.g., p-nitrophenol itself, are selectively prepared by (a) reacting a phenolic compound with a nitrosating agent in the presence of sulfuric acid, the concentration of which H.sub.2 SO.sub.4 being at least 60%, (b) oxidizing the p-nitrosophenolic compound thus formed with nitric acid, the concentration of sulfuric acid in the medium of reaction, upon completion of oxidation, being no greater than 80%, and (c) separating the p-nitrophenolic compound which thus precipitates.Type: GrantFiled: May 26, 1994Date of Patent: May 9, 1995Assignee: Rhone-Poulenc ChimieInventors: Pascal Metivier, Laurent Bernard
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Patent number: 5399790Abstract: Compounds such as 1-(4'-nitrophenyl)-2-propen-1-ol are disclosed which are non-steroidal mechanism-based inactivators of rat liver 3.alpha.-hydroxysteroid dehydrogenase. The corresponding ketones are time dependent inactivators of cyclooxygenase (PGH.sub.2 -synthase).Type: GrantFiled: August 30, 1993Date of Patent: March 21, 1995Assignee: Trustees of The University of PennsylvaniaInventors: Trevor M. Penning, Joseph W. Ricigliano
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Patent number: 5393776Abstract: This invention relates to structurally novel acyclic tocotrienol analogs, which are useful for cholesterol/lipid lowering in cases of hypercholesterolemia and hyperlipidemia, and for atherosclerosis. Also provided are pharmaceutical compositions and a method of use employing those compositions.Type: GrantFiled: May 13, 1994Date of Patent: February 28, 1995Assignee: Bristol-Myers Squibb CompanyInventor: Bradley C. Pearce
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Patent number: 5385942Abstract: A quinone derivative useful in the treatment of hepatic diseases defined by the general formula: ##STR1## where X and Y may be the same or different from each other and are each a hydroxyl group, a group represented by the formula --(--OCH.sub.2 --).sub.n --OR.sup.6, wherein n is 0 or 1 and R.sup.6 is a lower alkyl group, or an acyl group.Type: GrantFiled: March 1, 1993Date of Patent: January 31, 1995Assignee: Eisai Co., Ltd.Inventors: Shinya Abe, Yasushi Okamoto, Katsuya Tagami, Shigeki Hibi, Junichi Nagakawa, Kazuo Hirota, Ieharu Hishinuma, Kaname Miyamoto, Takashi Yamanaka, Hiromitsu Yokohama, Tsutomu Yoshimura, Tohru Horie, Yasunori Akita, Koichi Katayama, Isao Yamatsu
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Patent number: 5254685Abstract: A tricyclic compound represented by the general formula (1) and salts thereof. ##STR1## A method for producing the tricyclic compound and salts thereof, and an antimicrobial agent containing the tricyclic compound and salts thereof as an active ingredient are also disclosed.Type: GrantFiled: August 7, 1991Date of Patent: October 19, 1993Assignees: Wakunaga Seiyaku Kabushiki Kaisha, Fujisawa Pharmaceutical Co., Ltd.Inventors: Masaharu Yokomoto, Akira Yazaki, Norihiro Hayashi, Shunso Hatono, Satoshi Inoue, Yasuhiro Kuramoto
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Patent number: 5223614Abstract: Compounds of formula ##STR1## wherein the substituents are defined hereinbelow, useful in the treatment of bronchospasm are described.Type: GrantFiled: October 25, 1990Date of Patent: June 29, 1993Assignee: Boehringer Ingelheim GmbHInventors: Kurt Schromm, Anton Mentrup, Ernst-Otto Renth, Gojko Mualcevic, Werner Traunecker
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Patent number: 5218073Abstract: Polyhydroxy urethanes prepared from reduced sugars of the formula C.sub.x H.sub.2(x+1) O.sub.x where x is 4, 5 and 6 and diisocyanates are disclosed. There is a molar excess of 1.5 and preferably 2.0 of the reduced sugar in the polyhydroxy urethane product and the molecular weight of the product is generally less than 1,500 and preferably less than 1,000.Type: GrantFiled: October 15, 1990Date of Patent: June 8, 1993Assignee: E. I. Du Pont de Nemours and CompaanyInventor: William L. Evans
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Patent number: 5200535Abstract: The invention provides cyclohexanone derivatives of the general formula ##STR1## in which n represents an integer from 0 to 5; each R represents a halogen atom, nitro, cyano, hydroxyl, alkyl, haloalkyl, alkoxy, haloalkoxy, amino, alkylamino, dialkylamino, alkoxycarbonyl, carboxyl, alkanoyl, alkylthio, alkylsulphinyl, alkylsulphonyl, carbamoyl, alkylamido, cycloalkyl or phenyl group; R.sup.1, R.sup.2 and R.sup.3 independently represent a hydrogen atom or an alkyl group; R.sup.6 and R.sup.7 together represent a single carbon-carbon bond or an epoxy group; and R.sup.8 represents a hydrogen atom or a hydroxyl group; with the proviso that when R.sup.6 and R.sup.7 together represent an epoxy group then R.sup.8 represents a hydrogen atom; and a process for their preparation. Compounds of formula I are useful as intermediates in the preparation of certain fungicidally active cyclopentane derivatives.Type: GrantFiled: August 19, 1991Date of Patent: April 6, 1993Assignee: Shell Research LimitedInventor: Paul H. Briner
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Patent number: 5164515Abstract: A novel class of protecting compounds, particularly for amino acids, is based on 2,2 di nitrophenyl ethan- groups, particularly the groups wherein the nitro is in the para position. The ethyl group may be substituted, e.g. by an alkyl group, in the l- position. Preferred compounds include the alcohol or halide which are suitable for protecting acid functional groups, and esters, including activated and substituted esters, particularly the succinimidyl ester, for protecting amine groups. The invention includes methods of manufacture and use, together with protected amino acids.Type: GrantFiled: February 20, 1990Date of Patent: November 17, 1992Assignee: Wendstone Chemicals PLCInventor: Robert Ramage
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Patent number: 5143915Abstract: A compound of the formula ##STR1## (symbols defined in the specification), its 3,4-dihydropyrimidine tautomer form and pharmaceutically acceptable salts thereof have calcium entry blocking activity. A process of preparation, pharmaceutical composition and method of using the compound to reduce blood pressure are also provided.Type: GrantFiled: July 25, 1990Date of Patent: September 1, 1992Assignee: E. R. Squibb & Sons, Inc.Inventors: George C. Rovnyak, Spencer D. Kimball
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Patent number: 5136096Abstract: The bis-homotris compounds 4-amino-4-[1-(3-hydroxypropyl)]-1,7-heptanediol and 4-[1-(3-aminopropyl)]-4-[1-(3-hydroxypropyl)]-1, 7-heptanediol, and organic synthetic methods for their preparation are described. Unique multifunctional aminotriols, as well as their percursors, quaternary nitroalkanes are disclosed as building blocks for unimolecular micelles, as well as new series of cascade polymers. The quaternary nitro compounds which are disclosed allow the synthesis of a new aminotriol containing a quaternary carbon.Type: GrantFiled: March 26, 1991Date of Patent: August 4, 1992Assignee: University of South FloridaInventors: George R. Newkome, Charles N. Moorefield
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Patent number: 5064564Abstract: The present invention discloses an optically active compound represented by the following general formula (I): ##STR1## wherein R.sup.1 represents an alkyl, alkoxyl, or alkoxyalkanoyloxy group which has 1 to 18 carbon atoms and may be substituted with fluorine, chlorine, or cyano group; R.sup.2 represents an alkyl group having 1 to 18 carbon atoms; ##STR2## m is 0 or 1; Y represents a single bond, --CH.sub.2 O--, or --COO--; Z represents a single bond or --COO--; and C* and C** each independently represents an asymmetric carbon atom of the (R) and (S) configuration, an intermediate therefor being represented by the following general formula (II): ##STR3## wherein R.sup.2 represents an alkyl group having 1 to 18 carbon atoms, n is 0 or 1, and C* and C** each independently represents an asymmetric carbon atom of the (R) or (S) configuration, a process for producing the intermediate, and a liquid-crystal compound using the optically active compound.Type: GrantFiled: December 20, 1990Date of Patent: November 12, 1991Assignees: Dainippon Ink and Chemicals, Inc., Sagami Chemical Research CenterInventors: Sadao Takehara, Takeshi Kuriyama, Toru Fujisawa, Kayoko Nakamura, Tamejiro Hiyama, Kusumoto, Tetsuo, Akiko Nakayama
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Patent number: 4962198Abstract: The invention relates to a generally applicable process for the hydroxylation of electrophilic aromatic compounds, according to which the electrophilic aromatic compounds are reacted with organic hydroperoxides in the presence of bases.Type: GrantFiled: July 7, 1989Date of Patent: October 9, 1990Assignee: Bayer AktiengesellschaftInventors: Mieczyslaw Makosza, Krzysztof Sienkiewicz
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Patent number: 4940822Abstract: Compounds of the formula: ##STR1## wherein R.sup.1 is hydrogen, halo, halo-substituted alkyl, alkyl, cycloalkyl, aralkyl, aryl, heterocyclic, alkoxy, alkaryl, aryloxy, thioalkoxy, nitro, or N,N-dialkylamino are prepared by reacting 1-bromo-4-(trifluoromethyl)benzene with n-butyl lithium; reacting the product with a benzaldehyde of the formula: ##STR2## to produce a novel intermediate such as lithium 4-(trifluoromethyl)-.alpha.-]4-(trifluoromethyl)phenyl]benzenemethanol, and then reacting the lithium product with an acid or acid salt.Type: GrantFiled: November 4, 1988Date of Patent: July 10, 1990Assignee: Warner-Lambert CompanyInventors: James G. Davidson, III, Brian S. Swierenga
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Patent number: 4933505Abstract: A method of controlling the diastereoselectivity of the nitroaldol reaction by the use of titanium, zirconium and aluminum based Lewis acids is disclosed. In a preferred embodiment, the reaction of lithium nitronate anion with aldehydes in THF/CH.sub.2 Cl.sub.2 at reduced temperature in the presence of isopropoxy titanium trichloride (TiCl.sub.3 (OPr.sup.i)) yields nitro alcohols enriched in the erythro diastereomer. Erythro-threo ratios of 11.2:1-3.4:1 for aromatic aldehydes and 3.8:1-1:1 for aliphatic aldehydes are typically obtained.Type: GrantFiled: August 5, 1988Date of Patent: June 12, 1990Assignee: Northwestern UniversityInventors: Anthony G. M. Barrett, Christopher D. Spilling
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Patent number: 4868327Abstract: A novel method for preparing 2-phenyl-1, 3-propanediol and its dicarbamate is disclosed which readily lends itself to commercial production.Type: GrantFiled: June 3, 1987Date of Patent: September 19, 1989Assignee: Carter-Wallace, Inc.Inventor: Frank J. Stiefel
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Patent number: 4808632Abstract: The present invention relates to compounds of formula (I)ArCH.sub.2 R.sup.1 (I)or a monomethyl or a monoethyl ether thereof (the compound of formula (I) including these ethers may contain no more than 30 carbon atoms in total); ethers, esters thereof; acid addition salts thereof; wherein Ar is a fluoranthene or substituted fluoranthene ring system; R.sup.1 contains not more than eight carbon atoms and is a group ##STR1## wherein m is 0 or 1; R.sup.5 is hydrogen;R.sup.6 and R.sup.7 are the same or different and each is hydrogen or C.sub.1-3 alkyl optionally substituted by hydroxy;R.sup.8 and R.sup.9 are the same or different and each is hydrogen or C.sub.1-3 alkyl; ##STR2## is a five- or six-membered saturated carbocyclic ring; R.sup.10 is hydrogen, methyl or hydroxymethyl;R.sup.11, R.sup.12 and R.sup.13 are the same or different and each is hydrogen or methyl;R.sup.14 is hydrogen, methyl, hydroxy, or hydroxymethyl.Type: GrantFiled: July 30, 1987Date of Patent: February 28, 1989Assignee: Burroughs Wellcome Co.Inventor: Kenneth W. Bair
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Patent number: 4778935Abstract: Fluorinated nitroalcohols of the formula (I) ##STR1## process for their preparation by reaction of fluoronitroalkane of the formula (II) ##STR2## with a carbonyl compound of the formula (III) ##STR3## fluorinated aminoalcohols of the formula (IV) ##STR4## and a process for their preparation by hydrogentation of compounds of the formula (I).Type: GrantFiled: November 6, 1986Date of Patent: October 18, 1988Assignee: Bayer AktiengesellschaftInventors: Albert K. Beck, Dieter Seebach
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Patent number: 4719236Abstract: The present invention relates to compounds of formula (I)ArCH.sub.2 R.sup.1 (I)or a monomethyl or a monoethyl ether thereof (the compound of formula (I) including these ethers may contain no more than 30 carbon atoms in total); ethers, esters thereof; acid additon salts thereof; wherein Ar is a perylene or substituted perylene ring system; R.sup.1 contains not more than eight carbon carbon atoms and is a group ##STR1## wherein m is 0 or 1;R.sup.5 is hydrogen;R.sup.6 and R.sup.7 are the same or different and each is hydrogen or C.sub.1-3 alkyl optionally substituted by hydroxy;R.sup.8 and R.sup.9 are the same or different and each is hydrogen or C.sub.1-3 alkyl; ##STR2## is a five- or six-membered saturated carbocyclic ring; R.sup.10 is hydrogen, methyl or hydroxymethyl;R.sup.11, R.sup.12 and R.sup.13 are the same or different and each is hydrogen or methyl; R.sup.14 is hydrogen, methyl, hydroxy, or hydroxymethyl.Type: GrantFiled: October 17, 1984Date of Patent: January 12, 1988Assignee: Burroughs Wellcome Co.Inventor: Kenneth W. Bair
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Patent number: 4594459Abstract: Prepare p-isopropenyl phenol and other alkenyl aromatic compounds by contacting a dihydroxydiphenyl alkane or a related substituted diaromatic alkane with an alkaline catalyst and at least one gas under supercritical conditions such that p-isopropenyl phenol or the corresponding related alkenyl aromatic compound is produced.Type: GrantFiled: March 25, 1985Date of Patent: June 10, 1986Assignee: The Dow Chemical CompanyInventor: Kimio Inoue
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Patent number: 4581377Abstract: Compounds of formula I below are useful as anti-inflammatory, analgesic and/or anti-pyretic agents: ##STR1## in which R.sup.1 is hydrogen, nitro, amino, hydroxyl, alkoxy of one to four carbon atoms, alkyl of one to four carbon atoms or halogen; R.sup.2 is hydrogen or alkyl of one to four carbon atoms; is a saturated or unsaturated bond; A is CO, CHOH, C(R.sup.5)OH or CHOCOR.sup.6, where R.sup.5 and R.sup.6 are alkyl of one to four carbon atoms; B is alkyl of one to twelve carbon atoms; and X is H.sub.2 or O.Type: GrantFiled: November 7, 1984Date of Patent: April 8, 1986Assignee: Nippon Shinyaku Co., Ltd.Inventors: Yoshihisa Shibata, Yoshihiko Yoshimoto
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Patent number: 4581178Abstract: Low valent transition metal complexes containing small cone angle phosphine or arsine ligands efficiently catalyze addition of aldehydes to compounds or groups having a C--H bond activated by a nitro or nitrile group, to provide nitroalcohols or cyanohydrins, respectively.Type: GrantFiled: February 28, 1985Date of Patent: April 8, 1986Assignee: E. I. Du Pont de Nemours and CompanyInventor: David Milstein
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Patent number: 4532344Abstract: The present invention relates to compounds of formula (I) ##STR1## wherein Ar is a fluoranthene or substituted fluoranthene ring system; R.sup.1 is a C.sub.1-3 alkylene moiety; R.sup.2 is hydrogen or a C.sub.1-6 alkyl group; R.sup.3 is a hydroxy C.sub.1-6 alkyl group; R.sup.4 and R.sup.5 are the same or different and are hydrogen, C.sub.1-6 alkyl or hydroxy C.sub.1-6 alkyl, esters thereof derived from condensation of carboxylic acids and hydroxyl groups of R.sup.3, R.sup.4, and R.sup.5 ;Acid addition salts thereof, which have been found useful for the treatment of tumors in mammals.Type: GrantFiled: May 23, 1983Date of Patent: July 30, 1985Assignee: Burroughs Wellcome Co.Inventor: Kenneth W. Bair
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Patent number: 4520007Abstract: Compounds having blood-anticoagulant properties of the general molecular formula: ##STR1## in which Z represents a halogen atom, preferably a chlorine atom, and n is 0, 1 or 2 and R.sup.Type: GrantFiled: June 14, 1983Date of Patent: May 28, 1985Assignee: Shell Oil CompanyInventors: Ian D. Entwistle, Peter Boehm
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Patent number: 4517311Abstract: 2'-Substituted-spiro[benzofuran-2(3H),1'-cycloalkanes] and methods of praparing same are described. On the aromatic portion of the benzofuran ring, there may be a substituent or substituents including halogen, amino, lower-alkyl-substituted amino, lower alkyl, lower alkoxy, hydroxy and nitro. The substituents at the 2-position of the cycloalkane ring are --(CH.sub.2).sub.n NR.sup.1 R.sup.2 where n is 0, 1 or 2 and R.sup.1 and R.sup.2 are each independently hydrogen and alkyl of 1-3 carbons. These compounds are useful as antidepressants and analgesics.Various other compounds which are useful as intermediates for preparing the aforementioned compounds and methods for preparing same are also described.Type: GrantFiled: September 13, 1982Date of Patent: May 14, 1985Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventors: Edward J. Glamkowski, Michael C. Jones, deceased, by Herbert Jones, administrator
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Patent number: 4497966Abstract: Nitrophenylalkanols are prepared by hydroxyalkylation of nitrotoluene(s) by the reaction with an aldehyde in the presence of a solid catalyst prepared by depositing an alkali metal compound on an alumina support.Type: GrantFiled: September 7, 1983Date of Patent: February 5, 1985Assignee: Shell Oil CompanyInventors: Robert van Helden, Petrus A. Kramer
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Patent number: 4482736Abstract: Herbicidally active compounds of the formula ##STR1## in which R.sup.1 represents a hydrogen or chlorine atom,R.sup.2 represents a hydrogen atom, a cyano group, an optionally substituted radical selected from alkyl, aryl, alkanoyl, benzoyl, alkoxycarbonyl, alkenoxycarbonyl, alkinoxycarbonyl, aralkoxycarbonyl and aryloxycarbonyl, or a radical of the general formula--COOM,in whichM represents a hydrogen atom, one equivalent of an alkali metal ion or alkaline earth metal ion or optionally substituted ammonium, andR.sup.3 represents a cyano group or a radical of the general formula ##STR2## wherein Y represents an oxygen or sulphur atom or an imino (NH) or alkylimino (Nalkyl) group,R.sup.4 and R.sup.5 independently of each other represent a hydrogen atom or a methyl group,n is 0 or 1 andZ represents an optionally substituted radical,Novel intermediates therefor are also shown.Type: GrantFiled: July 14, 1983Date of Patent: November 13, 1984Assignee: Bayer AktiengesellschaftInventors: Heinz Forster, Ludwig Eue, Robert Schmidt
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Patent number: 4465833Abstract: A novel ethynylation process is disclosed which provides an expanded series of novel ethylnyl-terminated aromatic compounds having base sensitive substituents and which facilitates the economic preparation of prior art ethynyl-substituted aromatic compounds.Type: GrantFiled: October 15, 1980Date of Patent: August 14, 1984Assignees: Hughes Aircraft Company, Hughes Aircraft CompanyInventors: Kreisler S. Y. Lau, Robert H. Boschan
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Patent number: 4435605Abstract: The invention is a process for the preparation of a 2-phenylethyl alcohol which comprises contacting an aromatic aldehyde with carbon monoxide and hydrogen in a solvent comprising an oxygenated polar hydrocarbon and water, in the presence of a catalytic amount of a catalyst comprising a cobalt compound, a ruthenium salt and an iodine salt, at elevated temperatures and a pressure of between 600 and 45,000 psi.Type: GrantFiled: August 27, 1982Date of Patent: March 6, 1984Assignee: The Dow Chemical CompanyInventors: Susan B. Butts, George E. Hartwell
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Patent number: 4379765Abstract: There are presented compounds of the formulas ##STR1## wherein R.sub.1 is hydrogen or lower alkyl; R.sub.2 and R.sub.3 are selected from the group consisting of hydrogen, lower alkyl, C.sub.2 to C.sub.7 carboxylic acids, hydroxy C.sub.2 to C.sub.7 alkyl, C.sub.2 to C.sub.7 carboxylic acid esters and amides and the group COR.sub.11 wherein R.sub.11 is alkoxy, amino or mono- lower alkyl amino; R.sub.6 is nitro or halo and R.sub.5 is hydrogen or halo,and the pharmaceutically acceptable salts thereof.The pyrazolobenzazepines are useful as anxiolytic and sedative agents.Also provided are processes and intermediates in the production of the above pyrazolobenzazepines.Type: GrantFiled: July 23, 1981Date of Patent: April 12, 1983Assignee: Hoffmann-La Roche Inc.Inventors: George F. Field, Rodney I. Fryer, Eugene J. Trybulski, Armin Walser
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Patent number: 4374293Abstract: Allylbenzene is converted to indene by means of a tungsten-containing catalyst.Type: GrantFiled: August 14, 1981Date of Patent: February 15, 1983Assignee: The Standard Oil Co.Inventors: J. D. Burrington, R. K. Grasselli, C. T. Kartisek
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Patent number: 4327228Abstract: A process for the preparation of 3-dimethylamino-1-phenyl-(m-chlorophenyl)propan-2-ol and its salts which comprises the Raney nickel catalysed reduction of 3-nitro-1-phenyl-(1-m-chlorophenyl)propan-2-ol with simultaneous or subsequent dimethylation and thereafter, if desired, salification.Type: GrantFiled: June 3, 1980Date of Patent: April 27, 1982Assignee: Beecham Group LimitedInventor: Paul Smith
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Patent number: 4322442Abstract: 1-Halo-1-propyn-3-ols of the formula ##STR1## in which R is optionally substituted phenyl, pyridyl, furyl, thienyl or pyrazolyl,R' is optionally substituted phenyl, andX is halogen,which possess fungicidal properties.Type: GrantFiled: September 8, 1980Date of Patent: March 30, 1982Assignee: Bayer AktiengesellschaftInventors: Gerhard Jager, Erich Klauke, Wilhelm Brandes, Paul-Ernst Frohberger
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Patent number: 4299992Abstract: The invention relates to a new process for the selective hydroxymethylation of substituted ortho- or paranitrotoluenes of the general formula (I) ##STR1## in order to prepare nitrophenylalkanols of the general formula (II) ##STR2## In the above formulae the nitro group is attached to the benzene ring in ortho or para position related to the methyl group or the hydroxyalkyl side chain, respectively, X stands for hydrogen, fluorine or an alkyl, alkoxy or nitro group, and n is 1, 2 or 3.According to the process of the invention the starting substance is hydroxymethylated with an excess of formaldehyde at a temperature above room temperature in dimethyl formamide and in the presence of a strong base. The reaction is performed in dimethyl formamide containing 0.1 to 1% by weight of water, and the reaction is directed to the formation of the required end-product by properly adjusting the temperature and the amount of formaldehyde and the base with respect to the starting compound of the general formula (I).Type: GrantFiled: May 20, 1980Date of Patent: November 10, 1981Assignees: Reanal Finomvegyszergyar, Budapesti Muszaki EgyetemInventors: Antal Tungler, Tibor Mathe, Jozsef Petro, Zoltan Bende
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Patent number: 4290961Abstract: Catalytic reduction of carbonyl compounds by transfer of hydrogen from alcohols to aliphatic, alicyclic, aromatic, homo- and heterocyclic ketones or aldehydes, catalyzed by rhodium or iridium complexes, characterized in that a primary or secondary alcohol of formula (I) or a glycol: ##STR1## is reacted with a ketonic compound of formula (II): ##STR2## in which R and R' and, respectively, R" and R'", optionally linked with each other according to homo- or heterocycles, indifferently represent a hydrogen atom or a hydrocarbyl group having up to 30 atoms of carbon, also substituted, provided that at least one of symbols R" and/or R'" is different respectively from R and/or R', in the presence of a complex catalyst of rhodium or of iridium selected from those having formulas (III) and (IV): ##STR3## wherein: M is selected from Rh and Ir;Chel is a chelating bidentate nitrogenous compound;L-L is a molecule of a preferably non-conjugated diolefin or two molecules of a monoolefin;X.sup.Type: GrantFiled: March 7, 1980Date of Patent: September 22, 1981Assignee: Montedison S.p.A.Inventors: Giovanni Mestroni, Grazia Zassinovich, Annamaria Camus
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Patent number: 4283565Abstract: There is described an essentially two step process for the preparation of benzylalcohols including those benzylalcohols having substituents on the benzyene ring by reaction of a substituted or unsubstituted benzyl halide with a formate typically an alkali or alkaline earth metal formate to form the corresponding substituted or unsubstituted benzyl formate. In the second step of the process the benzyl formate is contacted with an alcohol whereby the same is converted into the desired benzylalcohol. Both steps can be performed employing catalysts. Described in the specification is the realization of the desired product in exceptionally high yields in a short period of time whereby the process is characterized by high space-time yields.Type: GrantFiled: December 29, 1978Date of Patent: August 11, 1981Assignee: Dynamit Nobel AGInventors: Gunther Bernhardt, Gerhard Daum
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Patent number: 4224244Abstract: Novel 9-phenyl 5,6-dimethyl-nona-2,4,6,8-tetraenoic acid, tetraenal or tetraenol derivatives useful as anti-tumor agents.Type: GrantFiled: May 9, 1979Date of Patent: September 23, 1980Assignee: Hoffmann-La Roche Inc.Inventors: Werner Bollag, Rudolf Ruegg, Gottlieb Ryser
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Patent number: 4219679Abstract: Aromatic nitroacetylene compounds wherein both the nitro and acetylene groups are directly connected to aromatic ring carbon atoms are hydrogenated at high conversion levels to selectively reduce the nitro function using an unsupported cobalt polysulfide catalyst. Of particular interest is the preparation of aminophenylacetylenes from nitrophenylacetylene.Type: GrantFiled: November 6, 1978Date of Patent: August 26, 1980Assignee: Gulf Research & Development CompanyInventors: Anatoli Onopchenko, Edward T. Sabourin, Charles M. Selwitz
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Patent number: 4217452Abstract: The invention relates to a new synthesis for the preparation of tetracyclic compounds of the general formula: ##STR1## as well as the pharmaceutically acceptable salts thereof, in which: n is the number 1 or 2,m is the number 1, if n=2 and the number 2, if n=1,R.sub.1 and R.sub.2 stand for hydrogen, hydroxy, halogen, lower alkyl (1-4 C), lower alkoxy (1-4 C) or trifluoromethyl andR.sub.3 represents hydrogen, alkyl (1-6 C), aralkyl (7-10 C) or an amino alkyl group (1-6 C), in which the nitrogen atom has been substituted by two alkyl groups (1-4 C), or the nitrogen atom forms part of a heterocyclic 5- or 6-membered ring,having valuable biological properties.Type: GrantFiled: December 27, 1976Date of Patent: August 12, 1980Assignee: Akzona IncorporatedInventor: Jacques Olivie
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Patent number: 4216341Abstract: Nitroaromatic hydroxy substituted acetylene compounds wherein both the nitro and acetylene groups are directly connected to aromatic ring carbon atoms are hydrogenated in an inert solvent to selectively reduce the nitro function over a ruthenium disulfide catalyst. Of particular interest is the preparation of aminophenylacetylene from nitrophenyl hydroxy substituted acetylene.Type: GrantFiled: November 6, 1978Date of Patent: August 5, 1980Assignee: Gulf Research & Development CompanyInventors: Anatoli Onopchenko, Edward T. Sabourin, Charles M. Selwitz
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Patent number: 4215226Abstract: Aromatic nitroacetylene compounds wherein both the nitro and acetylene groups are directly connected to aromatic ring carbon atoms are hydrogenated in dilute concentration in an inert solvent at high conversion levels to selectively reduce the nitro function using an unsupported ruthenium disulfide catalyst. Of particular interest is the preparation of an aminophenylacetylene from a nitrophenylacetylene.Type: GrantFiled: November 6, 1978Date of Patent: July 29, 1980Assignee: Gulf Research & Development CompanyInventors: Anatoli Onopchenko, Edward T. Sabourin, Charles M. Selwitz
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Patent number: 4204078Abstract: Nitrophenylacetylene and certain precursors to nitrophenylacetylene are prepared in improved yields by reacting a nitrobromobenzene with a substituted terminal acetylene compound containing at least three carbon atoms and a hydroxy group on the carbon atom adjacent to the acetylene group in the presence of a dialkyl or trialkyl amine solvent and a catalyst system consisting of a palladium complex containing two halogen moieties and two tri-substituted phosphine moieties and some excess trisubstituted phosphine compounds.Type: GrantFiled: September 13, 1978Date of Patent: May 20, 1980Assignee: Gulf Research & Development CompanyInventors: Edward T. Sabourin, Charles M. Selwitz
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Patent number: 4189611Abstract: Substituted dioxolanes are provided having the formula ##STR1## wherein R.sup.1 and R.sup.2 are H or a phenyl group substituted with up to 5 substituents of lower alkyl or nitro, with the proviso that at least one of R.sup.1 and R.sup.2 is a phenyl group having an orthonitro substituent; and R.sup.3 and R.sup.4 are each H or lower alkyl. These dioxolanes, as well as appropriate dioxanes, are used to intercalate a polyoxymethylene polymer to make such a polymer having thermally stable but photochemically sensitive and degradable random linkages ##STR2## in the chain where n is 0 or 1, R.sup.3 and R.sup.4 are H or lower alkyl and at least one of R.sup.1 and R.sup.2 is a phenyl group with an orthonitro substituent. By exposing a film of the polymer to light through a transparency followed by heating or a heated treatment with base, a relief image of the copy on the transparency is obtained.Type: GrantFiled: June 8, 1978Date of Patent: February 19, 1980Assignee: E. I. Du Pont de Nemours and CompanyInventor: Donnie J. Sam
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Patent number: 4180679Abstract: There are provided substituted dinitrotoluenes and methods of preparation thereof, said dinitrotoluenes being useful as intermediates for the preparation of certain herbicidal 2,6-dinitroanilines.Type: GrantFiled: August 22, 1978Date of Patent: December 25, 1979Assignee: American Cyanamid CompanyInventor: Inder P. Kapoor
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Patent number: 4130574Abstract: A method for increasing the hydrogen:carbon ratio of an organic compound is disclosed. The organic compound can be one having any of the following functions: hydroxyl, carbonyl, epoxide, acetal, ketal, hemiacetal and hemiketal. The method involves introducing the organic compound and a silicon hydride into a liquid which is either chemically inert or acidic and introducing BF.sub.3 into the liquid to produce a reaction product having a higher hydrogen:carbon ratio than the starting organic compound. Examples of organic compound starting materials disclosed include undecanal, benzaldehyde, p-methylbenzaldehyde, p-chlorobenzaldehyde, p-methoxybenzaldehyde, p-cyanobenzaldehyde, p-nitrobenzaldehyde, 2-undecanone, cyclohexanone, 2-methylcyclohexanone, adamantanone, p-cyanoacetophenone, fluorenone, 1-naphthaldehyde, p-nitroacetophenone, fructose and cotton.Type: GrantFiled: August 1, 1977Date of Patent: December 19, 1978Assignee: University of ToledoInventor: James L. Fry
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Patent number: 4128588Abstract: Nitrophenyl hydroxy substituted acetylene, which can be converted to nitrophenylacetylene is prepared by reacting a nitrobromobenzene with a substituted terminal acetylene compound containing at least three carbon atoms and a hydroxy group on the carbon atom adjacent to the acetylene group in the presence of a dialkyl or trialkyl amine solvent and a catalyst system consisting of a palladium complex containing two halogen moities and two tri-substituted phosphine moieties. A cuprous iodide promoter is also employed in the reaction sequence.Type: GrantFiled: October 11, 1977Date of Patent: December 5, 1978Assignee: Gulf Research & Development CompanyInventors: Edward T. Sabourin, Charles M. Selwitz
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Patent number: 4118487Abstract: Azol-1-ylmethanes substituted on the methane carbon atom by (a) phenyl or lower alkyl and (b) by a biphenyl-4-yl, 4-phenoxyphenyl, 4-phenylthiophenyl, 4-phenylsulfinylphenyl or 4-phenylsulfonylphenyl group are antimycotic and antibacterial agents. The compounds, of which (biphenyl-4-yl)phenyl-imidazol-1-ylmethane is a typical example, are prepared from the correspondingly substituted carbinol through treatment with thionyl-bis-azole or from the correspondingly substituted methyl halide with the azole or a derivative thereof.Type: GrantFiled: December 5, 1975Date of Patent: October 3, 1978Assignee: Bayer AktiengesellschaftInventors: Erik Regel, Wilfried Draber, Karl Heinz Buchel, Manfred Plempel
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Patent number: 4107206Abstract: The present invention relates to novel biologically active tricyclic compounds of the general formula: ##STR1## and salts thereof, IN WHICHR.sub.1 and R.sub.2 stand for hydroge, alkyl or alkenyl, an optionally substituted aralkyl group or an acyl group orR.sub.1 + r.sub.2 together with the nitrogen atom represent a heterocyclic 5- or 6-membered ring, andX and Y stand for hydrogen, hydroxy, halogen, alkyl or alkoxy of 1-6 carbon atoms, nitro, trifluoromethyl or an acyloxy group,Which compounds have valuable biological activities, particularly anorectic activity.Type: GrantFiled: October 26, 1976Date of Patent: August 15, 1978Assignee: Akzona IncorporatedInventors: Colin Leslie Hewett, David Samuel Savage
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Patent number: 4096337Abstract: The disclosure relates to novel 15-(3-aryl- or 3-aralkyl-cyclobutyl, -cyclopentyl and -cyclohexyl)-.omega.-pentanor prostaglandin analogues, for example 9.alpha.,11.alpha.,15.alpha.-trihydroxy-15-(trans-3-phenylcyclobutyl)-16,1 7,18,19,20-pentanor-5-cis,13-trans-prostadienoic acid, to pharmaceutical or veterinary compositions containing such a compound, and to a method of inducing luteolysis in animals by orally administering such a compound.Type: GrantFiled: June 1, 1976Date of Patent: June 20, 1978Assignee: Imperial Chemical Industries LimitedInventor: Peter Robert Marsham