The Additional Ring Is Six-membered Patents (Class 568/743)
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Patent number: 10919828Abstract: A process for producing cannabidiol from hemp and cannabis plants is disclosed. The steps of the process include the steps of: plant conditioning and size reduction, infusing with an extraction agent, separating a solid biomass and a liquid phase, treating the liquid phase with a removal agent, decarboxylation, removal of impurities; and color removal. The resulting cannabidiol conversion efficiency is over 90% and a TCH content within the legal limits for commercial cannabidiol.Type: GrantFiled: February 14, 2020Date of Patent: February 16, 2021Inventors: Aicardo Roa-Espinosa, Joaquin Camilo Perez-Mahecha, Michelle H Pham, Charles Kevin Jepson
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Publication number: 20150141707Abstract: A method comprising a step of stirring a composition containing a biphenol compound represented by the formula (1): wherein, R1 and R2 represent each independently an alkyl group having 1 to 3 carbon atoms, and m and n represent each independently an integer of 0 to 2, a secondary alcohol and a nickel catalyst, for producing a hydroxyphenylcyclohexanol compound represented by the formula (2): wherein, R1, R2, m and n represent the same meaning as described above, with the proviso that the above-described secondary alcohol has a different structure from that of the hydroxyphenylcyclohexanol compound represented by the above-described formula (2).Type: ApplicationFiled: April 8, 2013Publication date: May 21, 2015Applicant: Sumitomo Chemical Company, LimitedInventors: Takeshi Hara, Yoshihiko Iwanaga
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Publication number: 20140256830Abstract: Provided herein are methods and compositions comprising resorcinol derivatives for the use of treating, regulating or preventing a skin condition characterized by oxidative stress or a degenerative process. Methods of preventing, lightening or reducing the appearance of visible discontinuities of the skin resulting from skin pigmentation, skin aging, or other disorders are also disclosed.Type: ApplicationFiled: March 6, 2014Publication date: September 11, 2014Inventors: Andrew W. HINMAN, Dana Davis, Viktoria Kheifets
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Publication number: 20140221469Abstract: The present invention relates to the use of phytocannabinoids in the treatment of cancer. More particularly it relates to the use of phytocannabinoids in the treatment of tumour cell invasion and cell migration or metastases. Cancers, where invasion and cell migration plays a key role in prognosis include brain tumours, more particularly gliomas, and most particularly Glioblastoma multiforme (GBM) and breast cancers. The phytocannabinoids tetrahydrocannabivarin (THCV) and cannabidivarin (CBDV) alone or in combination with each other and/or other phytocannabinoids, particularly cannabidiol (CBD), tetrahydrocannabinol (THC) and cannabigerol (CBG) or their respective acids are of particular use.Type: ApplicationFiled: September 10, 2012Publication date: August 7, 2014Applicants: Otsuka Pharmaceutical Co., Ltd., GW Pharma LimitedInventors: Ruth Alexandra Ross, Daniela Parolaro
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Patent number: 8791274Abstract: Provided are a complex prepared from ammonium salt-containing ligands and having such an equilibrium structural formula that the metal center takes a negative charge of 2 or higher, and a method for preparing polycarbonate via copolymerization of an epoxide compound and carbon dioxide using the complex as a catalyst. When the complex is used as a catalyst for copolymerizing an epoxide compound and carbon dioxide, it shows high activity and high selectivity and provides high-molecular weight polycarbonate, and thus easily applicable to commercial processes. In addition, after forming polycarbonate via carbon dioxide/epoxide copolymerization using the complex as a catalyst, the catalyst may be separately recovered from the copolymer.Type: GrantFiled: March 5, 2012Date of Patent: July 29, 2014Assignee: SK Innovation Co., Ltd.Inventors: Myungahn Ok, Jisu Jeong, BunYeoul Lee, S. Sujith, Anish Cyriac, JaeKi Min, JongEon Seong
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Publication number: 20140051751Abstract: Environmentally-friendly alternatives to organometallic antifoulants that are efficacious at preventing biofouling by organisms such as the zebra mussel. Preferred antifoulant compositions utilize compounds having a Lipophilic-Amide-Spacer-ElectroNegative (“LASEN”) structural motif, such as capsaicin, and compounds having a TetraHydroCannibinoid (“THC”) structural motif. The antifoulant compositions are non-toxic, and effective.Type: ApplicationFiled: October 25, 2013Publication date: February 20, 2014Applicants: The Board of Regents of the University of Texas System, University of North Texas Health Science Center at Fort WorthInventors: John A. Schetz, Robert F. McMahon
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Publication number: 20140027671Abstract: To provide a liquid crystal composition satisfying at least one characteristic such as high maximum temperature of nematic phase, low minimum temperature thereof, small viscosity, suitable optical anisotropy, large negative dielectric anisotropy and specific resistance, high stability to ultraviolet light and heat; a liquid crystal composition having a suitable balance regarding at least two thereof; and an AM device including the composition.Type: ApplicationFiled: July 19, 2013Publication date: January 30, 2014Inventors: YASUYUKI GOTOH, TEIZI SATOU, MAIKO MATSUKUMA, CHIKAHIDE KANADANI, YOSHIMASA FURUSATO
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Patent number: 8575230Abstract: Environmentally-friendly alternatives to organometallic antifoulants that are efficacious at preventing biofouling by organisms such as the zebra mussel. Preferred antifoulant compositions utilize compounds having a Lipophilic-Amide-Spacer-ElectroNegative (“LASEN”) structural motif, such as capsaicin, and compounds having a TetraHydroCannibinoid (“THC”) structural motif. The antifoulant compositions are non-toxic, and effective.Type: GrantFiled: April 16, 2008Date of Patent: November 5, 2013Assignees: University of North Texas Health Science Center at Fort Worth, The Board of Regents of the University of Texas SystemInventors: John A. Schetz, Robert F. McMahon
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Publication number: 20130209483Abstract: The disclosure relates to cannabinoid derivative compounds, pharmaceutical compositions made thereof, and methods for treating various diseases and disorders including cancer.Type: ApplicationFiled: November 30, 2012Publication date: August 15, 2013Applicant: SUTTER WEST BAY HOSPITALSInventor: SUTTER WEST BAY HOSPITALS
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Patent number: 8507733Abstract: Provided are a complex prepared from ammonium salt-containing ligands and having such an equilibrium structural formula that the metal center takes a negative charge of 2 or higher, and a method for preparing polycarbonate via copolymerization of an epoxide compound and carbon dioxide using the complex as a catalyst. When the complex is used as a catalyst for copolymerizing an epoxide compound and carbon dioxide, it shows high activity and high selectivity and provides high-molecular weight polycarbonate, and thus easily applicable to commercial processes. In addition, after forming polycarbonate via carbon dioxide/epoxide copolymerization using the complex as a catalyst, the catalyst may be separately recovered from the copolymer.Type: GrantFiled: March 5, 2012Date of Patent: August 13, 2013Assignee: SK Innovation Co., Ltd.Inventors: Myungahn Ok, Jisu Jeong, BunYeoul Lee, Sujith S., Anish Cyriac, JaeKi Min, JongEon Seong
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Publication number: 20130203984Abstract: In a process for oxidizing a hydrocarbon to a product comprising at least one of the corresponding hydroperoxide, alcohol, ketone, carboxylic acid and dicarboxylic acid, the hydrocarbon is contacted with an oxygen-containing compound in at least one oxidation zone in the presence of a catalyst comprising a cyclic imide having an imide group of formula (I): wherein X represents an oxygen atom, a hydroxyl group, or an acyloxy group and wherein the oxygen-containing compound supplied to said at least one oxidation zone has a water content of less than or equal to 0.6% by weight of the oxygen-containing compound.Type: ApplicationFiled: August 16, 2011Publication date: August 8, 2013Inventors: Christopher L. Becker, Jihad M. Dakka, Franisco M. Benitez, Edmund J. Mozeleski
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Patent number: 8420637Abstract: The present invention provides a method of treating glaucoma or ocular hypertension which comprises applying to the eye of a person in need thereof an amount sufficient to treat glaucoma or ocular hypertension of a compound of formula I wherein Y, Q, Z, R, R1 and R2 are as defined in the specification. The present invention further comprises pharmaceutical compositions, e.g. ophthalmic compositions, including said compound of formula I.Type: GrantFiled: September 22, 2009Date of Patent: April 16, 2013Assignee: Allergan, Inc.Inventors: June Chen, Simon Pettit, Hans Fliri
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Publication number: 20120172339Abstract: Novel resorcinol derivatives and methods of preparation and use are presented. These compounds can stimulate angiogenesis as a biological function triggered by the activation of one cannabinoid receptor distinct from CB1 and CB2. Thus, these compounds are specific ligands for one cannabinoid receptor distinct from CB1 and CB2. The invented compounds, when administered in a therapeutically effective amount to an individual or animal, results in a sufficiently high level of that compound in the individual or animal to cause a physiological response. The physiological response may be useful to treat a number of physiological conditions.Type: ApplicationFiled: July 9, 2010Publication date: July 5, 2012Applicant: Northeastern UniversityInventors: Alexandros Makriyannis, Spyridon P. Nikas, Shariku O. Alapafuja
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Publication number: 20120165575Abstract: Provided are a complex prepared from ammonium salt-containing ligands and having such an equilibrium structural formula that the metal center takes a negative charge of 2 or higher, and a method for preparing polycarbonate via copolymerization of an epoxide compound and carbon dioxide using the complex as a catalyst. When the complex is used as a catalyst for copolymerizing an epoxide compound and carbon dioxide, it shows high activity and high selectivity and provides high-molecular weight polycarbonate, and thus easily applicable to commercial processes. In addition, after forming polycarbonate via carbon dioxide/epoxide copolymerization using the complex as a catalyst, the catalyst may be separately recovered from the copolymer.Type: ApplicationFiled: March 5, 2012Publication date: June 28, 2012Applicant: SK ENERGY CO., LTD.Inventors: Myungahn OK, Jisu Jeong, BunYeoul Lee, Sujith S., Anish Cyriac, JaeKi Min, JongEon Seong
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Publication number: 20120127633Abstract: A metal electrolytic capacitor capable of quickly absorbing and immobilizing a belching vapor of a driving electrolyte and widely reducing leakage when an explosion-proof valve operates. An aluminum electrolytic capacitor body is configured by housing a capacitor element in a cylindrical aluminum case, a pair of leads extend from the capacitor body, an explosion-proof valve is formed on a top panel portion of the metal case, a cylindrical cap as a casing is attached from above to the capacitor body, a plurality of small openings are formed on a top panel portion (bottom portion) of the cap, and an absorbent or a mixture of an absorbent and a water molecular compound wrapped in a permeable fiber material, such as unwoven fabric and filter paper, is placed in a space between the cap and the top panel portion of the capacitor body.Type: ApplicationFiled: June 2, 2010Publication date: May 24, 2012Inventors: Koichi Mori, Mitsuru Nozue, Minoru Yagi
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Patent number: 7884133Abstract: Cannabinoid derivatives are known for their function in the central as well as peripheral nervous system. Disclosed are some novel (+)-cannabidiol (CBD) derivatives of the general formula (I) having selective activity in the peripheral, but not in the central nervous system. Use of (+)-CBD derivatives as analgesics, anti-inflammatory and anti-diarrheal agents is also disclosed.Type: GrantFiled: September 8, 2004Date of Patent: February 8, 2011Assignees: Yissum Research Development Company of the Hebrew University of Jerusalem, Ariel Ltd.Inventors: Raphael Mechoulam, Ester Fride
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Publication number: 20100256256Abstract: Environmentally-friendly alternatives to organometallic antifoulants that are efficacious at preventing biofouling by organisms such as the zebra mussel. Preferred antifoulant compositions utilize compounds having a Lipophilic-Amide-Spacer-ElectroNegative (“LASEN”) structural motif, such as capsaicin, and compounds having a TetraHydroCannibinoid (“THC”) structural motif. The antifoulant compositions are non-toxic, and effective.Type: ApplicationFiled: April 16, 2008Publication date: October 7, 2010Inventors: John A. Schetz, Robert F. McMahon
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Publication number: 20100204312Abstract: This disclosure provides compositions and method useful for treating cell proliferative disorders including cancer. The disclosure provides cannabidiol derivatives and compositions thereof either alone or in combination with THC or a derivative thereof.Type: ApplicationFiled: May 16, 2008Publication date: August 12, 2010Applicant: CALIFORNIA PACIFIC MEDICAL CENTERInventors: Sean D. McAllister, Pierre-Yves Desprez
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Patent number: 7674922Abstract: The present invention relates to a process for preparation of a delta-9-tetrahydrocannabinol compound or derivative thereof involving treating a first intermediate compound with an organoaluminum-based Lewis acid catalyst, under conditions effective to produce the delta-9-tetrahydrocannabinol compound or derivative thereof. Another aspect of the present invention relates to a process for preparation of a cannabidiol or cannabidiolate compound involving reacting a first starting compound with a second starting compound in the presence of a metal triflate catalyst, under conditions effective to form the cannabidiol or cannabidiolate compound. The present invention also relates to a compound of the formula: where R8, R9, and R10 are the same or different and independently selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or halo, with R1, R2, and R3 defined herein.Type: GrantFiled: September 28, 2006Date of Patent: March 9, 2010Assignee: Albany Molecular Research, Inc.Inventors: David C. Burdick, Steven J. Collier, Frédéric Jos, Betina Biolatto, Bernhard J. Paul, Harold Meckler, Mark A. Helle, Alicia J. Habershaw
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Patent number: 7618966Abstract: The present invention provides a method of treating glaucoma or ocular hypertension which comprises applying to the eye of a person in need thereof an amount sufficient to treat glaucoma or ocular hypertension of a compound of formula I wherein Y, Q, Z, R, R1 and R2 are as defined in the specification. The present invention further comprises pharmaceutical compositions, e.g. ophthalmic compositions, including said compound of formula I.Type: GrantFiled: April 24, 2006Date of Patent: November 17, 2009Assignee: Allergan, Inc.Inventors: June Chen, Simon Pettit, Hans Fliri
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Patent number: 7129381Abstract: The present invention relates to glucopyranosyl-oxybenzylbenzene derivatives represented by the general formula: wherein R1 represents a hydrogen atom, a hydroxy group, a substituted or unsubstituted amino group, a carbamoyl group, a substituted or unsubstituted(lower alkyl) group, a substituted or unsubstituted(lower alkoxy) group etc.; R2 represents a hydrogen atom or a lower alkyl group; and R3 represents a substituted or unsubstituted(lower alkyl) group, a substituted or unsubstituted(lower alkoxy) group, a substituted or unsubstituted(lower alkylthio) group etc., or pharmaceutically acceptable salts thereof, which have an inhibitory activity in human SGLT2 and are useful as agents for the prevention or treatment of a disease associated with hyperglycemia such as diabetes, diabetic complication or obesity, pharmaceutical compositions comprising the same and intermediates thereof.Type: GrantFiled: November 2, 2004Date of Patent: October 31, 2006Assignee: Kissei Pharmaceutical Co., Ltd.Inventors: Hideki Fujikura, Toshihiro Nishimura, Nobuhiko Fushimi, Kazuya Tatani, Norihiko Kikuchi, Kenji Katsuno, Masayuki Isaji
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Patent number: 7045665Abstract: The present invention relates to benzylphenol derivatives represented by the general formula: wherein R11 represents a hydrogen atom or a protected hydroxy(lower alkyl) group; and R12 represents a lower alkyl group, a lower alkoxy group, a lower alkylthio group, a protected hydroxy(lower alkyl) group, a protected hydroxy(lower alkoxy) group, a protected hydroxy(lower alkylthio) group, a lower alkoxy-substituted (lower alkyl) group, a lower alkoxy-substituted (lower alkoxy) group or a lower alkoxy-substituted (lower alkylthio) group; with the proviso that R12 is not a methyl group, an ethyl group, an isopropyl group, a tert-butyl group or a methoxy group when R11 is a hydrogen atom, or a salt thereof, which are used as intermediates for making glucopyranosyloxybenzylbenzene compounds having inhibitory activity in human SGLT2 and are useful in treating diseases associated with hyperglycemia, such as diabetes.Type: GrantFiled: October 7, 2004Date of Patent: May 16, 2006Assignee: Kissei Pharmaceutical Co., Ltd.Inventors: Hideki Fujikura, Nobuhiko Fushimi, Toshihiro Nishimura, Kazuya Tatani, Kenji Katsuno, Masahiro Hiratochi, Yoshiki Tokutake, Masayuki Isaji
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Patent number: 6867335Abstract: The present invention relates to process wherein (+)-2-carene epoxide is coupled with a compound X—Y that contains nucleophilic and electrophilic moieties, to produce a compound of formula (5). The reaction mixture consists essentially of a source of (+)-2-carene epoxide, compound X—Y, optionally an inert solvent and optionally a pH buffer. No acid catalyst is used in the process.Type: GrantFiled: May 9, 2002Date of Patent: March 15, 2005Assignee: Johnson Matthey Public Limited CompanyInventors: Michael Casner, Theodore Maurice Resnick, Lee Jonathan Silverberg
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Patent number: 6828460Abstract: The present invention relates to the use of certain resorcinol derivatives as skin lightening agents.Type: GrantFiled: December 21, 2001Date of Patent: December 7, 2004Assignee: Pfizer Inc.Inventors: Andrew Francis Browning, Eric William Collington, Martin James Procter, Joanna Victoria Geden
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Patent number: 6563009Abstract: Cannabinoids have been found to have antioxidant properties, unrelated to NMDA receptor antagonism. This new found property makes the cannabinoids useful in the treatment and prophylaxis of wide variety of oxidation associated diseases, such as ischemic, age-related, inflammatory and autoimmune diseases. The cannabinoids are found to have particular application as neuroprotuctants, for example in limiting neurological damage following ischemic insults, such as stroke and trauma, or in the treatment of neurodegenerative diseases, such as Alzheimer's disease, Parkinson's disease and HIV dementia. Nonpsychoactive cannabinoids, such as cannabidoil, are particularly advantageous to use because they avoid toxicity that is encountered with psychoactive cannabinoids at high doses useful in the method of the present invention.Type: GrantFiled: March 8, 2002Date of Patent: May 13, 2003Assignee: Virginia Commonwealth UniversityInventors: George Kunos, Billy Martin, Raj Razdan
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Publication number: 20020128524Abstract: A method of purifying dihydroxydiphenyl (1), 1Type: ApplicationFiled: March 5, 2002Publication date: September 12, 2002Inventors: Silke Kratschmer, Hans Deml
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Publication number: 20020032352Abstract: The present invention relates to an improved process for preparing 4-substituted resorcinol derivatives, and intermediate compounds useful in the preparation of such resorcinol derivatives.Type: ApplicationFiled: March 8, 2001Publication date: March 14, 2002Inventors: Stuart Edward Bradley, John Kitchin, Graham Michael Wynne
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Patent number: 5618871Abstract: Novel compounds of the formula I and formula II ##STR1## in which R and R.sub.1, independently of one another, are hydrogen or C.sub.1 -C.sub.4 alkyl or together with the carbon atom to which they are attached form a 3,4-dehydrocyclohexylidene ring,R.sub.2 is hydrogen, C.sub.1 -C.sub.8 alkyl or C.sub.5 -C.sub.6 cycloalkyl,R.sub.3 is C.sub.1 -C.sub.8 alkyl or C.sub.5-C.sub.6 cycloalkyl,R.sub.4, R.sub.5 and R.sub.6, independently of one another, are hydrogen or C.sub.1-C.sub.4 alkyl, R.sub.4, R.sub.5 and R.sub.6 together containing 1 to 4 carbon atoms, andR.sub.7 and R.sub.8 are hydrogen or together an additional direct bond, are described for use as stabilizers for organic materials against thermal, oxidative or light-induced degradation.Type: GrantFiled: February 3, 1995Date of Patent: April 8, 1997Assignee: Ciba-Geigy CorporationInventor: Peter Nesvadba
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Patent number: 5420361Abstract: The production of cis-dihydrodiol compounds of the formula ##STR1## where n is 0 or 1 (preferably 0) by the microbial oxidation of a diphenylaceylene compound of the formula ##STR2## using a mutant of a Pseudomonas bacteria at 25.degree. to 35.degree. C. and pH 6-8 is disclosed. The cis-dihydrodiol compound is in turn treated with an aqueous solution of a base to produce a corresponding 3-hydroxydiphenylacetylene compound or with an aqueous solution of an acid to produce a corresponding 2-hydroxyacetylene compound.Type: GrantFiled: May 10, 1994Date of Patent: May 30, 1995Assignee: Bio-Technical ResourcesInventor: Alan D. Grund
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Patent number: 5420363Abstract: An optically active tri-substituted methane compound having, as substituents, an aromatic ring group and a phenyl group having hydroxyl group at ortho or para position can be obtained by allowing a phenol compound unsubstituted at the ortho- or/and para-position to react with an optically active secondary carbinol compound having an aromatic ring group at the alpha-position in the presence of tri-substituted phosphine and diazodicarboxylate or diazodicarboxamide. These and other optically active tri-substituted methane compounds are useful as active ingredients for medicines or as intermediate compounds for preparing medicines.Type: GrantFiled: June 27, 1994Date of Patent: May 30, 1995Assignee: Takeda Chemical Industries, Ltd.Inventors: Mitsuru Shiraishi, Shoji Fukumoto
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Patent number: 5356976Abstract: Compounds of formula I ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.4 n-alkyl, isopropyl, s-butyl, cyclopentyl, cyclohexyl or .alpha.-methylbenzyl, R.sub.2 is C.sub.4 -C.sub.18 tert-alkyl or .alpha.,.alpha.-dimethylbenzyl, R.sub.3 is C.sub.1 -C.sub.28 alkyl, and R.sub.4 s methyl or ethyl, with the proviso that the --CHR.sub.3 R.sub.4 group contains at least 4 carbon atoms, are suitable for stabilizing organic material which is susceptible to degradation induced by heat, oxidation or actinic light.Type: GrantFiled: July 12, 1993Date of Patent: October 18, 1994Assignee: Ciba-Geigy CorporationInventors: Paul Dubs, Rita Pitteloud
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Patent number: 5245089Abstract: Provided is a process for alkylating aromatic compounds in the presence of mixed oxides of titanium and gallium which have been found to be highly active catalysts for the alkylation of aromatics with alkyl esters, alcohols, olefins and ethers. When the alkyl acceptor is a phenol, the catalysts provide high reaction rates and high selectivity for ortho alkylated products.Type: GrantFiled: October 23, 1992Date of Patent: September 14, 1993Assignee: Eastman Kodak CompanyInventors: Gether Irick, Jr., Leslie S. LaForce
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Patent number: 5233097Abstract: Certain crystalline titanoaluminosilicate molecular sieve compositions having titanium, aluminum, and silicon present as framework tetrahedral oxide units are particularly effective in hydroxylating the aromatic nucleus of aromatic compounds using hydrogen peroxide, even where the hydrogen peroxide is used at concentrations of 10 weight percent or less. The variant where the exchangeable hydrogens of the titanoaluminosilicate are replaced by an alkali or alkaline earth metal cation is particularly favored because of the concomitant increase in selectivity. Excellent utilization of hydrogen peroxide often is observed, even when the hydroxylation is effected at temperatures under about 60.degree. C.Type: GrantFiled: October 15, 1992Date of Patent: August 3, 1993Assignee: UOPInventors: Laszlo T. Nemeth, Eric M. Hyatt, Thomas P. Malloy
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Patent number: 5177245Abstract: Provided is a process for preparing optionally-substituted cyclohexenylhydroquinones starting from cyclohexanone.Type: GrantFiled: November 25, 1991Date of Patent: January 5, 1993Assignee: Eastman Kodak CompanyInventors: Dewey W. Fuller, Jr., Gether Irick, Jr.
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Patent number: 5149888Abstract: The phenols and phenol ethers, e.g., phenol itself, are effectively hydroxylated by reacting hydrogen peroxide therewith, in the presence of a catalytically effective amount of titanium dioxide.Type: GrantFiled: February 28, 1990Date of Patent: September 22, 1992Assignee: Rone-Poulenc ChimieInventors: Michel Costantini, Eric Garcin, Michel Gubelmann, Jean-Michel Popa
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Patent number: 5146008Abstract: A process for the synthesis of phenyl substituted aromatic diols, obtained by dehydrogenation of the corresponding substituted cyclohexyl derivatives in the presence of a palladium supported catalyst, said palladium supported catalyst being prepared by a process which comprises treating a palladium hydrolysis compound with reducing agents.Type: GrantFiled: March 19, 1991Date of Patent: September 8, 1992Assignee: Himont italia S.r.l.Inventors: Andrea Gardano, Alfredo Coassolo, Francesco Casagrande, Marco Foa, Larry L. Chapoy
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Patent number: 4996377Abstract: Aliphatically substituted fluorobenzenes of the general formula I ##STR1## where R is an aliphatic or cycloaliphatic radical, n is 2, 3 or 4 and X is hydrogen, fluorine, chlorine or bromine, are prepared by diazotization of the corresponding aniline derivative of the general formula II ##STR2## in the presence of tetrafluoboric acid and decomposition of the resulting diazonium tetrafluoborate of the general formula III ##STR3## by a process in which the decomposition reaction is carried out simultaneously with the diazotization reaction, in the presence of elemental copper and/or copper(I) and/or copper(II) salts and at from -15.degree. to 80.degree. C.Type: GrantFiled: February 21, 1990Date of Patent: February 26, 1991Assignee: BASF AktiengesellschaftInventors: Jochen Wild, Albrecht Harreus, Norbert Goetz
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Patent number: 4990687Abstract: 4-Methyl-2-cyclohexylphenol can be prepared by alkylation of p-cresol with cyclohexanol or cyclohexene by performing the reaction in the liquid phase in the presence of 1-10% by weight, based on the amount of p-cresol, of a large pore, acidic zeolite.Type: GrantFiled: November 13, 1989Date of Patent: February 5, 1991Assignee: Bayer AktiengesellschaftInventors: Alfons Klein, Helmut Fiege, Lothar Puppe, Werner Jeblick
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Patent number: 4985589Abstract: A method is provided for converting 4-substituted biphenyls, such as 4-hydroxybiphenyl, to the corresponding 3,4'-dihydroxybiphenyl utilizing mutant strains of Alcaligenes eutrophus or Pseudomonas putida. Hydroxylation of the unsubstituted biphenyl ring to the corresponding (1S-cis)-3-(4-hydroxyphenyl)-3,5-cyclohexadiene-1,2-diol and its conversion to the corresponding triacetate, followed by treatment in base to form 3,4'-dihydroxybiphenyl is also provided.Type: GrantFiled: August 1, 1990Date of Patent: January 15, 1991Assignee: General Electric CompanyInventors: Bruce F. Johnson, Frank J. Mondello
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Patent number: 4978811Abstract: Ortho-aromatic diaryl ethers, such as o-biphenylyl phenyl ether, are hydrolyzed to corresponding phenolic compounds, such as o-phenylphenol and phenol, when contacted with water in the presence of ceria or thoria at a temperature of between about 250.degree. C. and 700.degree. C.Type: GrantFiled: April 1, 1988Date of Patent: December 18, 1990Assignee: The Dow Chemical CompanyInventors: Robert A. Koster, Philip J. Brondsema, Willis J. Pennington, William C. Sumner, Susan E. Vilmer
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Patent number: 4978789Abstract: A process for producing an alkenyl substituted aromatic compound having the general formula (I): ##STR1## wherein Ar represents an aromatic ring, R.sup.1 represents an alkenyl group having 2 to 8 carbon atoms, p is 1, 2, or 3 provided that R.sup.1 may be the same or different when p is 2 or 3, R.sup.2 represents an alkyl group having 1 to 8 carbon atoms, q is 0, 1, or 2 provided that R.sup.2 may be the same or different when q is 2, X represents --OH or --NR.sup.3 R.sup.4 wherein R.sup.3 and R.sup.4 independently represent hydrogen or an alkyl group having 1 to 2 carbon atoms, n is 1 or 2, provided that the sum of p and q is 1, 2, or 3 comprising the step of catalytically dehydrogenating an alkyl substituted aromatic compound having the general formula (III): ##STR2## wherein R.sup.5 represents an alkyl group having 2 to 8 carbon atoms and Ar, R.sup.2, X, p, q, and n are the same as defined above, n is 1 or 2, provided that R.sup.Type: GrantFiled: July 10, 1989Date of Patent: December 18, 1990Inventors: Katsuo Taniguchi, Shigeki Fujikawa, Yoshito Kurano
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Patent number: 4894487Abstract: This invention relates to a novel preparation process of 4-(4-hydroxyphenyl)-cyclohexanol, which comprises subjecting 4-(4-hydroxphenyl)-3-cyclohexen-1-ol to reduction. 4-(4-Hydroxyphenyl)-cyclohexanol is a compound useful as a monomer for liquid crystalline polyesters and the like.Type: GrantFiled: August 4, 1988Date of Patent: January 16, 1990Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Tohru Miura, Masayuki Furuya, Teruyuki Nagata
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Patent number: 4891424Abstract: 4-Aralkyl-2-nitro-2'-hydroxy-3',5'-dialkyl (or cumyl)-azobenzenes are made by coupling the corresponding diazotized 4-aralkyl-o-nitroaniline with the corresponding phenol. These azobenzene intermediates are used to prepare the corresponding 2H-benzotriazole UV absorber stabilizers substituted on the 5-position of the benzo ring by an aralkyl group, preferably alpha,alpha-dimethylbenzyl.Type: GrantFiled: April 1, 1988Date of Patent: January 2, 1990Assignee: Ciba-Geigy CorporationInventors: Raymond Seltzer, Roland A. E. Winter
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Patent number: 4877907Abstract: A novel compound, 4-(4-hydroxyphenyl)-3-cyclohexene-1-ol, and a novel preparation process of 4,4'-biphenol by using the novel compound as the raw material.4-(4-Hydroxyphenyl)-3-cyclohexene-1-ol can be obtained by conducting a thermal decomposition reaction of 4,4-bis(4-hydroxyphenyl)cyclohexanol. 4,4'-Biphenol can be industrially manufactured by conducting a dehydrogenation reaction of 4-(4-hydroxyphenyl)-3-cyclohexene-1-ol.Type: GrantFiled: April 14, 1989Date of Patent: October 31, 1989Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Tohru Miura, Teruyuki Nagata, Koju Okazaki, Masayuki Furuya, Emiko Nishida
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Patent number: 4873374Abstract: A novel compound, 4-(4-hydroxyphenyl)-3-cyclohexene-1-ol, and a novel preparation process of 4,4'-biphenol by using the novel compound as the raw material.4-(4-Hydroxyphenyl)-3-cyclohexene-1-ol can be obtained by conducting a thermal decomposition reaction of 4,4-bis(4-hydroxyphenyl)cyclohexanol. 4,4'-Biphenol can be industrially manufactured by conducting a dehydrogenation reaction of 4-(4-hydroxyphenyl)-3-cyclohexene-1-ol.Type: GrantFiled: April 6, 1988Date of Patent: October 10, 1989Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Tohru Miura, Teruyuki Nagata, Koju Okazaki, Masayuki Furuya, Emiko Nishida
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Patent number: 4871470Abstract: Cyclohexane derivatives of formula I ##STR1## wherein R is an alkyl group which has 1-12 C atoms and in which one or two non-adjacent CH.sub.2 groups can also be replaced by O, --CO--O-- or --OCO--,A.sup.1 and A.sup.2 each independently of one another are trans-1,4-cyclohexylene or unsubstituted or fluorine-substituted 1,4-phenylene, and one of the groups A.sup.1 and A.sup.2 can also be a single bond,X is --CN, halogen, OH, --COOR.sup.1, --OOCR.sup.1, --COR.sup.1, --OR.sup.1 or R.sup.1 andR.sup.1 is an alkyl group which has 1-12 C atoms and in which one or two CH.sub.2 groups can also be replaced by O, but excluding direct links between two O atoms,with the proviso that, in the case of X=CN, A.sup.2 is trans-1,4-cyclohexylene or fluorine-substituted, 1,4-phenylene, are suitable as components of liquid-crystalline phases.Type: GrantFiled: October 30, 1987Date of Patent: October 3, 1989Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: Andreas Wachtler, Joachim Krause, Rudolf Eidenschink, Georg Weber
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Patent number: 4739098Abstract: Retinoid-like activity is exhibited by compounds of the formula ##STR1## where n is 0-5 and A is H, lower alkyl, or --COOH or ester or amide thereof, --CH.sub.2 OH or an ether or ester derivative, or --CHO or an acetal derivative, or a pharmaceutically acceptable salt.Type: GrantFiled: September 22, 1986Date of Patent: April 19, 1988Assignee: Allergan, Inc.Inventor: Roshantha A. S. Chandraratna
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Patent number: 4643844Abstract: Perfume compositions and perfumed articles containing dihydro- and/or tetrahydro-1-naphthol derivatives of the formula ##STR1## wherein the dotted lines represent carbon-carbon single or double bonds with the proviso that no more than one of them is a double bond and wherein R.sub.1, R.sub.2 and R.sub.3 independently are methyl groups or hydrogen atoms; said naphthol derivatives have a very natural leather-like odor.Type: GrantFiled: February 26, 1985Date of Patent: February 17, 1987Assignee: 501 Naarden International N.V.Inventors: Nicolaas L. J. M. Broekhof, Antonius J. A. van der Weerdt, Jogchum Hofma
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Patent number: 4628127Abstract: A process for producing 2,4-di-substituted phenols wherein an olefin is reacted with phenol in the presence of a heterogeneous catalyst comprising an aluminum phenoxide bonded to an acidic solid polymeric resin to preferably form 2,4-di-substituted phenol. A process for preparing a heterogeneous catalyst and a heterogeneous catalyst having the structure(Resin --A--).sub.m Al(--OC.sub.6 R.sub.5).sub.n (11)wherein Resin is a solid polymeric resin having acidic functional groups A, m is 1 or 2, n is 2 or 3 and the R are independently selected from H, alkyl, cycloalkyl, and aralkyl. Preferably, a styrene-divinylbenzene polymeric resin of a macroreticular structure is used for the alkylation process and A is --SO.sub.3 --.Type: GrantFiled: June 25, 1985Date of Patent: December 9, 1986Assignee: Ethyl CorporationInventors: Silas W. Holmes, Edward A. Burt, Dixie E. Goins
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Patent number: 4620938Abstract: New hydroterphenyls of formula IR.sup.1 --Cy--Cy--Ph--R.sup.2 Iwherein R.sup.1 is alkyl; R.sup.2 is H, F, Cl, Br, I, OH, CN, alkyl, --O-alkyl, --COOR.sup.3 or --O--CO--R.sup.3 ; R.sup.3 is H, alkyl, --Cy-alkyl, --Ph-alkyl, --Ph--O-alkyl, --Ph--CN or --Ph--F; Cy is 1,4-cyclohexylene; and Ph is 1,4-phenylene; can be used as dielectrics for electrooptical display elements.Type: GrantFiled: April 5, 1985Date of Patent: November 4, 1986Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: Michael Romer, Joachim Krause, Rudolf Eidenschink, Georg Weber