Polyoxy Phenolic Moiety Patents (Class 560/144)
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Patent number: 5463108Abstract: The present invention provides a unique and novel way of producing 4-acetoxystyrene. In this new process, 4-hydroxystyrene is acetylated, in the presence of an acetylation agent, under suitable conditions of temperature and pressure and for a sufficient period of time to form acetoxystyrene.Type: GrantFiled: December 19, 1994Date of Patent: October 31, 1995Assignee: Hoechst Celanese CorporationInventors: James R. Sounik, William W. Wilkison, III, Keith M. Russ, Lynn Massarelli
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Patent number: 5430175Abstract: Caged carboxyl compounds in which a 2-alkoxy-5-nitrophenyl photosensitive group blocks a carboxyl function are disclosed. Preferably the compounds are neuroactive amino acids. The compounds are photolyzable by laser pulses at wavelengths above about nm within about 3 .mu.s and provide a product quantum yield of greater than about 0.2.Type: GrantFiled: November 30, 1993Date of Patent: July 4, 1995Assignee: Cornell Research Foundation, Inc.Inventors: George P. Hess, Barry K. Carpenter, Doraiswamy Ramesh, Raymond Wieboldt
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Patent number: 5391812Abstract: Polyglycolate compounds are provided having the general structure: ##STR1## wherein n is an integer from 2 to about 10; R is C.sub.1-20 linear or branched alkyl, alkoxylated alkyl, cycloalkyl, aryl, alkylaryl, substituted aryl; R' and R" are independently H, C.sub.1-20 alkyl, aryl, C.sub.1-20 alkylaryl, substituted aryl, and NR.sub.3.sup..alpha.+, wherein R.sup..alpha. is C.sub.1-30 alkyl; and L is a leaving group displaceable in a peroxygen bleaching solution by perhydroxide anion. When this compound is combined with a source of peroxygen in aqueous solution, then a plurality of stain removing peracids are formed. Such peracids are formed substantially sequentially beginning with the carbonyl adjacent to the leaving group L. Thus, a first stain removing peracid having the structure ##STR2## will be formed in amounts approaching quantitative yield.Type: GrantFiled: September 25, 1992Date of Patent: February 21, 1995Assignee: The Clorox CompanyInventors: Richard R. Rowland, Ronald A. Fong, Richard J. Wiersema, Alfred G. Zielske
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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: 5380901Abstract: The present invention provides a process for converting a hydrophobic siloxane diacrylate, an aromatic fluorinated diacrylate and a hydrophilic polyethylene glycol diacrylate to their respective multifunctional oligomers. Bis(4-acryloxybutyl)tetramethyldisiloxane, prepared from the corresponding diol, is converted to relatively low viscosity, multifunctional oligomers with the use of DMSO. The hydrophilic monomer, polyethylene glycol 400 diacrylate, formed more viscous, water soluble oligomeric products without the need for a solvent. Characterization of these oligomers by infrared spectroscopy and .sup.1 H NMR supports the assigned structures. Because of the predominant 1,6-arrangement of double bonds in these oligomers, they have a propensity to undergo cyclopolymerization as well as the usual crosslinking associated with the free radical polymerization of multifunctional monomers and oligomers.Type: GrantFiled: January 30, 1992Date of Patent: January 10, 1995Assignee: The United States of America as represented by the Secretary of CommerceInventors: Joseph M. Antonucci, Jeffrey W. Stansbury, Guo-Wei Cheng
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Patent number: 5366517Abstract: A fuel additive composition comprising:(a) a poly(oxyalkylene) hydroxyaromatic ether having the formula: ##STR1## or a fuel-soluble salt thereof; where R.sub.1 and R.sub.2 are each independently hydrogen, hydroxy, lower alkyl having 1 to 6 carbon atoms, or lower alkoxy having 1 to 6 carbon atoms; R.sub.3 and R.sub.4 are each independently hydrogen or lower alkyl having 1 to 6 carbon atoms; R.sub.5 is hydrogen, alkyl having 1 to 30 carbon atoms, phenyl, aralkyl or alkaryl having 7 to 36 carbon atoms, or an acyl group of the formula: ##STR2## where R.sub.6 is alkyl having 1 to 30 carbon atoms, phenyl, or aralkyl or alkaryl having 7 to 36 carbon atoms; n is an integer from 5 to 100; and x is an integer from 0 to 10; and(b) a poly(oxyalkylene) amine having at least one basic nitrogen atom and a sufficient number of oxyalkylene units to render the poly(oxyalkylene) amine soluble in hydrocarbons boiling in the gasoline or diesel fuel range.Type: GrantFiled: December 18, 1992Date of Patent: November 22, 1994Assignee: Chevron Research and Technology CompanyInventor: Richard E. Cherpeck
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Patent number: 5358930Abstract: Described is 2-ethoxy-4-formyl phenyl ester of propionic acid of our invention defined according to the structure: ##STR1## and uses thereof in augmenting or enhancing the aroma of perfume compositions, perfumed articles and colognes.Type: GrantFiled: December 17, 1993Date of Patent: October 25, 1994Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Richard A. Weiss, Richard M. Boden, Olivier J. Gillotin
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Patent number: 5283352Abstract: Catechol compounds of formula I ##STR1## where R.sub.1, R.sub.2, R.sub.3 and X are as described herein are effective Catechol-O-methyltransferase inhibitors.Type: GrantFiled: December 7, 1992Date of Patent: February 1, 1994Assignee: Orion-yhtyma OyInventors: Reijo J. Backstrom, Kalevi E. Heinola, Erkki J. Honkanen, Seppo K. Kaakkola, Pekka J. Kairisalo, Inge-Britt Y. Linden, Pekka I. Mannisto, Erkki A. O. Nissinen, Pentti Pohto, Aino K. Pippuri, Jarmo J. Pystynen
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Patent number: 5274175Abstract: A method for producing 4-acetoxystyrene by heating 4-acetoxyphenylmethylcarbinol, with an acid catalyst, at a temperature of from about 85.degree. C. to about 300.degree. C. under a pressure of from about 0.1 mm HgA to about 760 mm HgA for from about 0.2 minutes to about 10 minutes. The process also provides for the solventless (neat) hydrogenation of 4-acetoxyacetophenone to produce 4-acetoxyphenylmethylcarbinol. The reaction proceeds by heating at 54.degree. C. to 120.degree. C. with an excess of hydrogen in the presence of a Pd/C or activated nickel such as Raney Nickel catalyst in the absence of a solvent. The 4-acetoxyphenylmethylcarbinol may then be dehydrated to 4-acetoxystyrene. The later may be polymerized to poly(4-acetoxystyrene) and hydrolyzed to poly(4-hydroxystyrene).Type: GrantFiled: June 10, 1993Date of Patent: December 28, 1993Assignee: Hoechst Celanese CorporationInventors: Bakulesh N. Shah, Dung Q. Tran, Donna L. Keene
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Patent number: 5274174Abstract: A method for producing 4-acetoxystyrene by heating 4-acetoxyphenylmethylcarbinol, with an acid catalyst, at a temperature of from about 85.degree. C. to about 300.degree. C. under a pressure of from about 0.1 mm HgA to about 760 mm HgA for from about 0.2 minutes to about 10 minutes. The process also provides for the solventless (neat) hydrogenation of 4-acetoxyacetophenone to produce 4-acetoxyphenylmethylcarbinol. The reaction proceeds by heating at 54.degree. C. to 120.degree. C. with an excess of hydrogen in the presence of a Pd/C or activated nickel such as Raney Nickel catalyst in the absence of a solvent. The 4-acetoxyphenylmethylcarbinol may then be dehydrated to 4-acetoxystyrene. The later may be polymerized to poly(4-acetoxystyrene) and hydrolyzed to poly(4-hydroxystyrene).Type: GrantFiled: June 10, 1993Date of Patent: December 28, 1993Assignee: Hoechst Celanese CorporationInventors: Bakulesh N. Shah, Dung Q. Tran, Donna L. Keene
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Patent number: 5274176Abstract: A process for the production of substituted vinylbenzenes of the general formula: ##STR1## wherein R is a lower alkyl group having 1 to 4 C atoms, R.sub.1 is hydrogen or an acetyl group and R.sub.2 is hydrogen, a lower alkyl group having 1 to 4 C atoms or a benzyl group. A trialkylhydroquinone is cyclized with an aldehyde to an acetal and the latter is pyrolized to the endproduct. The substituted vinylbenzenes are valuable intermediate products in the synthesis of antioxidants.Type: GrantFiled: October 21, 1992Date of Patent: December 28, 1993Assignee: Lonza Ltd.Inventors: Aleksander Warm, David Laffan
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Patent number: 5214193Abstract: A bisphenol monoester represented by the formula (I): ##STR1## wherein R.sup.1 is hydrogen or alkyl, R.sup.2 and R.sup.3 are each alkyl, and R.sup.4 is alkyl, alkenyl or phenyl, is produced by continuous two step reactions in which an aldehyde R.sup.1 -CHO and 2,4-dialkylphenol are subjected to a condensation reaction in a C.sub.6 -C.sub.10 aliphatic or C.sub.6 -C.sub.12 aromatic hydrocarbon solvent, and then a resulting bisphenol compound dissolved in the solvent is subjected to an esterification with a carboxylic acid R.sup.4 --COOH or its derivative. Prior to the esterification, the organic layer containing the bisphenol compound is subjected to a dehydration treatment, thereby enabling the two steps to proceed continuously without isolating the intermediate bisphenol compound. A purification process for the bisphenol monoester of the formula (I) is also disclosed in which the monoester is purified from a mixed solvent comprising a C.sub.6 -C.sub.12 aromatic hydrocarbon solvent and a C.sub.1 -C.sub.Type: GrantFiled: February 12, 1992Date of Patent: May 25, 1993Assignee: Sumitomo Chemical Company, LimitedInventors: Kikumitsu Inoue, Manji Sasaki, Kazuaki Yamamoto, Shinichi Yachigo
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Patent number: 5210279Abstract: A continuous process for the production of diacetate derivatives of aromatic compounds, comprising feeding at any convenient temperature an oxygen-containing gas and feedstock comprising a diisopropyl ring substituted aromatic compound and the recycled monoisopropyl-monoacetate derivative thereof, to an oxidizer operated, for example, at from about 10.degree. C. to about 150.degree. C. and oxygen partial pressures of from about 0.05 to 10 atmospheres to form an oxidizer product comprising the mono- and dihydroperoxides of the feedstock, feeding the oxidizer product to a rearrangement-esterification zone containing acetic anhydride at from about 0.degree. C. to 150.degree. C. to form an ester product comprising the diacetate and monoisopropyl-monoacetate derivatives of the feedstock, distilling the ester product to separate the diacetate and monoisopropyl-monoacetate derivatives, and recycling the monoisopropyl-monoacetate derivative back to the oxidizer.Type: GrantFiled: July 12, 1990Date of Patent: May 11, 1993Assignee: Eastman Kodak CompanyInventors: Dale E. Van Sickle, Brad W. Overturf
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Patent number: 5210278Abstract: A process for preparing a substituted styrene by reacting a bisarylalkyl ether in the presence of an acid catalyst is disclosed. The process is preferably used for the preparation of 4-acetoxystyrene from 4,4'-(oxydiethylidene)bisphenol diacetate and 4-methoxystyrene from 4,4'-(oxydiethylidene)bisphenol dimethyl ether. A process for preparing a bisarylalkyl ether by reacting a corresponding arylalkanol in the presence of an acid catalyst is also disclosed.Type: GrantFiled: August 25, 1992Date of Patent: May 11, 1993Assignee: Hoechst Celanese CorporationInventors: Mohammad Aslam, Brad L. Smith, George Kvakovszky
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Patent number: 5183928Abstract: A hydroquinone monocarboxylate, e.g., hydroquinone monoacetate, is facilely prepared by disproportionating/reacting a stoichiometric excess of a hydroquinone dicarboxylate, e.g., hydroquinone diacetate, with hydroquinone, optionally in the presence of a strong acid/transesterification catalyst.Type: GrantFiled: February 26, 1988Date of Patent: February 2, 1993Assignee: Rhone-Poulenc Specialities ChimiquesInventor: Serge Ratton
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Patent number: 5177252Abstract: Esters having the general formula ##STR1## where X is a halogen, the sum of the atomic masses of the halogen atoms on the phenyl ring is at least 90, n is 1-5, Y is an alkyl, ether, ester, aldehyde, ketone, acetal, ketal, cyano, or nitro substituent, m is 0-2, Z is an ester linkage --OCO-- or --CO.sub.2 --, R' is a haloalkyl group containing at least one F atom and containing halogen atoms in place of greater than 60% of the hydrogen atoms of the corresponding unhalogenated alkyl group, with the sum of the atomic masses of the halogen atoms on said R' group being greater than 135 and the compound as a whole containing at least two types of halogen atoms, and p is 1-3, constitute high density flotation fluids and lubricants for inertial instruments such as gyroscopes and accelerometers, and for electrical contacts. Synthetic methods are disclosed for production of such fluids from available starting materials.Type: GrantFiled: April 11, 1990Date of Patent: January 5, 1993Assignee: The Charles Stark Draper Laboratory, Inc.Inventor: John R. Williams
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Patent number: 5144059Abstract: The compound of the formula ##STR1## (wherein R, R.sub.1 and R.sub.2 have the meanings given in the description), salts thereof with pharmaceutically acceptable organic or inorganic acids, process and intermediates for the preparation thereof and a pharmaceutical composition containing said compound are described.The compounds of formula I and the salts thereof are useful in the treatment of heart and renal diseases.Type: GrantFiled: April 20, 1990Date of Patent: September 1, 1992Assignee: Simes Societa Italiana Medicinali E. Sintetici S.A.Inventors: Cesare Casagrande, Francesco Santangelo
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Patent number: 5136084Abstract: A novel process for the acetylation of a mono-substituted phenol or a mono-substituted naphthol is disclosed which comprises reacting the said mono-substituted phenol or the said mono-substituted naphthol respectively with vinyl acetate at a temperature of not more than 160.degree. C.Type: GrantFiled: June 14, 1991Date of Patent: August 4, 1992Assignee: San Fu Chemical Co., Ltd.Inventors: Shu-Chung Lin, Min-Hon Rei
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Patent number: 5041616Abstract: Disclosed is a process for the preparation of alkyl aryl ketones, cycloalkyl aryl ketones and diaryl ketones by contacting an aromatic compound with an aliphatic, cycloaliphatic or aromatic carboxylic acid in the presence of a catalytic amount of an organic sulfonic acid while removing the water of reaction as an azeotrope from the reaction mixture.Type: GrantFiled: August 29, 1990Date of Patent: August 20, 1991Assignee: Eastman Kodak CompanyInventor: Charles E. Sumner, Jr.
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Patent number: 4985198Abstract: A tooth-adhesive compound is expressed in terms of the following general formula: ##STR1## wherein R.sub.1 is a hydrogen atom or a methyl group, andR.sub.2 may or may not be present; and if present, R.sub.2 is an alkylene group having 1 to 4 carbon atoms or a --CH.sub.2 --CH.sub.2).sub..eta. O--CH.sub.2 --CH.sub.2 -- group in which n=1 or 2, and a substituent containing R.sub.1 and R.sub.2 is located at the o-, m- or p-position with respect to the carboxyl group bonded to the phenyl group.Type: GrantFiled: March 7, 1989Date of Patent: January 15, 1991Assignee: G-C Dental Industrial Corp.Inventors: Tadashi Hirasawa, Ikuro Harashima
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Patent number: 4970331Abstract: Vinyl ethers having a carboxyl group in a form of salt are stable and is usable as materials for fluorine-containing copolymers. The vinyl ethers can provide sable monomer compositions by mixing with vinyl ethers having a free carboxyl group when the former vinyl ethers are present in an amount of not less than 1% by mole of the latter vinyl ethers. The fluorine-containing copolymer prepared by copolymerizing fluoroolefins with the vinyl ethers are useful as aqueous coatings particularly electro dip coatings.Type: GrantFiled: March 9, 1988Date of Patent: November 13, 1990Assignee: Daikin Industries, Ltd.Inventors: Tatsushiro Yoshimura, Nobuyuki Tomihashi, Tsutomu Terada, Masayuki Yamana, Kazuhiro Nakai, Takayuki Araki
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Patent number: 4959391Abstract: Phenol derivatives of the formula ##STR1## wherein A and B have the same or different meanings and each represent one of the groups --C.tbd.C--, cis--CH.dbd.CH-- or trans--CH.dbd.CH--, R.sub.1 is hydrogen, an optionally substituted alkyl or phenyl group or a cycloalkyl group, R.sub.2 is hydrogen, methyl or ethyl, R.sub.3 represents hydrogen, acetyl or propionyl, R.sub.4 has the same meaning as R.sub.3 or represents an alkyl group, R.sub.5 is a carboxylic or a hydroxy group or a functional derivative of such groups or R.sub.5 is a nitrile group and R.sub.6 is hydrogen, an alkyl group or the group OR.sub.4 which specifically inhibit 5-lipoxygenase and are useful in pharmaceutical compositions for prophylaxis and treatment of diseases due to the action of leukotrienes. The compounds are prepared by reacting suitable acetylene compounds or metal derivatives thereof with alkyl or aryl halides or by means of Wittig reactions optionally followed by transforming the member R.sub.Type: GrantFiled: July 14, 1988Date of Patent: September 25, 1990Assignee: Gruenenthal GmbHInventors: Oswald K. Zimmer, Werner P. Vollenberg, Gerriet K. H. Loschen, Werner Winter, Erwin O. Kiesewetter, Ulrich G. P. Seippl
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Patent number: 4956123Abstract: Fluorine-containing aromatic derivatives are produced by the reaction of di(haloacyl)peroxide represented by the general formula: ##STR1## (wherein X stands for a fluorine, chlorine, or hydrogen atom and n for an integer of the value of 1 to 10) with aromatic unsaturated monomers represented by the general formula: ##STR2## (wherein Y stands for hydrogen atom, methyl, ethyl, propyl, acetyl, propionyl, acetyloxy, propionyloxy, methoxy, ethoxy, propoxy, vinyl, isopropenyl, or nitro group, or a halogen atom, R.sup.1 for hydrogen atom, methyl, ethyl, propyl, or butyl group, R.sup.2 for hydrogen atom, methyl or phenyl group, and m for an integer of the value of 1 to 5).Type: GrantFiled: September 14, 1988Date of Patent: September 11, 1990Assignee: Nippon Oils & Fats Company, Ltd.Inventors: Hideo Sawada, Michio Kobayashi, Masato Yoshida
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Patent number: 4956477Abstract: Compounds having the formula: ##STR1## wherein T is a polycycloalkylidene group (e.g., adamant-2-ylidene); R is a C.sub.1-20 alkyl, aralkyl or cycloalkyl group; and Y is a fluorescent chromophore (e.g., m-phenylene), produced by reacting a compound having the formula: ##STR2## with an R-ylating agent (e.g., R.sub.2 SO.sub.4) in the presence of an alkali metal alkoxide in a polar aprotic solvent. Also, compounds having the formula: ##STR3## are produced by reacting a compound having the formula: ##STR4## wherein X is an electronegative leaving group (e.g., a halogen anion such as chloride ion) in the presence of a Lewis base (e.g., a trialkyl-amine) dissolved in an aprotic organic solvent (e.g., benzene or toluene). Also, compounds having the formula ##STR5## are produced by reacting a compound of the formula ##STR6## with a tetra-O-acylated-O-hexopyranoside halide, then hydrolyzing off the protective acyl groups.Type: GrantFiled: September 22, 1989Date of Patent: September 11, 1990
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Patent number: 4939174Abstract: The invention involves the formation of a prodrug from a fatty acid carrier and a neuroactive drug. The prodrug is stable in the environment of both the stomach and the bloodstream and may be delivered by ingestion. The prodrug passes readily through the blood brain barrier. Once in the central nervous system, the prodrug is hydrolyzed into the fatty acid carrier and the drug to release the drug.In a preferred embodiment, the carrier is 4,7,10,13,16,19 docosahexa-enoic acid and the drug is dopamine. Both are normal components of the central nervous system. The covalent bond between the drug and the carrier preferably is an amide bond, which bond may survive the conditions in the stomach. Thus, the prodrug may be ingested and will not be hydrolyzed completely into the carrier molecule and drug molecule in the stomach.Type: GrantFiled: February 26, 1988Date of Patent: July 3, 1990Inventor: Victor E. Shashoua
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Patent number: 4935522Abstract: A method for producing ethyl 2-[4'-(6"-chloro-2"-benzoxazolyloxy)phenoxy]propanoate by reacting a hydroxyaromatic ketone derivative with a 2-substituted propanoic ester under basic conditions and thereafter oxidizing the intermediate with subsequent hydrolysis and reaction with 2,6-dichlorobenzoxazole.Type: GrantFiled: March 21, 1988Date of Patent: June 19, 1990Assignee: Hoechst Celanese CorporationInventors: Varadaraj Elongo, Kenneth G. Davenport
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Patent number: 4933324Abstract: The invention involves the formation of a prodrug from a fatty acid carrier and a neuroactive drug. The prodrug is stable in the environment of both the stomach and the bloodstream and may be delivered by ingestion. The prodrug passes readily through the blood brain barrier. Once in the central nervous system, the prodrug is hydrolyzed into the fatty acid carrier and the drug to release the drug.In a preferred embodiment, the carrier is 4, 7, 10, 13, 16, 19 docosahexa-enoic acid and the drug is dopamine. Both are normal components of the central nervous system. The covalent bond between the drug and the carrier preferably is an amide bond, which bond may survive the conditions in the stomach. Thus, the prodrug may be digested and will not be hydrolyzed completely into the carrier molecule and drug molecule in the stomach.Type: GrantFiled: February 24, 1989Date of Patent: June 12, 1990Inventor: Victor E. Shashoua
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Patent number: 4927956Abstract: 3-substituted-4-hydroxy- and 4-acetoxystyrene compounds, especially 3,5-di(methyl, bromo or chloro)-4-acetoxystyrene as well as a process for its preparation. 2,6-dimethylphenol is acylated with acetic anhydride and HF catalyzed to produce 3,5-dimethyl-4-hydroxy-acetophenone. After subsequent esterification with acetic anhydride and catalyzed hydrogenation to form 1-(3',5'-dimethyl-4'-acetoxyphenyl)ethanol, this intermediate is then dehydrated with an acid and a polymerization inhibitor to produce 3,5-dimethyl-4-acetoxystyrene.Type: GrantFiled: June 2, 1989Date of Patent: May 22, 1990Assignee: Hoechst Celanese CorporationInventors: Richard Vicari, Mohammad Aslam, Wilson B. Ray, Kenneth G. Davenport, Ralph Dammel, Juergen Lingnau, Karl-Friedrich Doessel
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Patent number: 4917817Abstract: An optically active functional compound represented by the following formula (1) is disclosed: ##STR1## wherein R denotes an alkyl group having 1-14 carbon atoms; -X- denotes ##STR2## denotes a single bond, ##STR3## n=0, 1 or 2; and C* denotes an asymmetric carbon atom. The compound of the formula (1) may be produced through an optically active compound of the following formula (2) or (3): ##STR4## The compounds of the above formulas (1)-(3) are all characterized by a trifluoromethyl group providing a large spontaneous polarization attached to an asymmetric carbon atom.Type: GrantFiled: July 21, 1988Date of Patent: April 17, 1990Assignee: Canon Kabushiki KaishaInventors: Hiroyuki Nohira, Masanao Kamei, Hideki Kanazawa, Tetsuya Abe, Yoko Yamada, Yuko Etoh
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Patent number: 4908476Abstract: A method for synthesizing 2-(4-hydroxyphenoxy)alkanoic acids by reacting a hydroxyaromatic ketone derivative with a 2-substituted alkanoic acid under basic conditions and thereafter oxidizing the intermediate with subsequent hydrolysis.Type: GrantFiled: March 21, 1988Date of Patent: March 13, 1990Assignee: Hoechst Celanese CorporationInventors: Varadaraj Elango, Kenneth G. Davenport
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Patent number: 4900476Abstract: An asymmetric synthesis for Vitamin E in an optically active pure form for 4-(2,5-diloweralkanoyloxy)-3,4,6-trimethylphenyl-butan-2-one and intermediates therein.Type: GrantFiled: January 30, 1989Date of Patent: February 13, 1990Assignee: Hoffmann-La Roche Inc.Inventors: Ka-kong Chan, Gabriel G. Saucy
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Patent number: 4861798Abstract: Compounds of the formulae ##STR1## wherein n=6-11, M is hydrogen or a pharmaceutically acceptable cation, R is hydrogen or C.sub.1 -C.sub.6 alkyl optionally substituted by a carboxyl group and X.sub.a, X.sub.b and X.sub.c each independently represent hydrogen or a variety of substituent groups are potent inhibitors of 5-lipoxygenase.Type: GrantFiled: December 22, 1987Date of Patent: August 29, 1989Assignee: Bristol-Myers CompanyInventors: Kenneth M. Tramposch, Fred C. Zusi, Suresh A. Marathe
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Patent number: 4841097Abstract: Disclosed herein are dialkanoyloxybenzylidene dialkanoate represented by the formula ##STR1## wherein X.sup.1 and X.sup.2 represent respectively alkanoyloxy group and a pharmaceutical composition in dosage unit form which comprises a dosage effective for the treatment of inflammatory disease of the dialkanoyloxybenzylidene dialkanoate as an active ingredient thereof.Type: GrantFiled: April 13, 1988Date of Patent: June 20, 1989Assignee: Kureha Kagaku Kogyo Kabushiki KaishaInventors: Hitoshi Takita, Fumihiko Kimura, Sakuo Noda, Yutaka Mukaida, Toyohiko Nitta, Hidetoshi Kobayashi
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Patent number: 4835304Abstract: Esters having the general formula: ##STR1## where X is a halogen, n is 1-5, Y is an alkyl, ether, ester, or nitro substituent, m is 0-2, Z is an ester linkage --OCO-- or --CO.sub.2 --, R' is a haloalkyl group, and p is 1-3, constitute high density flotation fluids for inertial instruments such as gyroscopes and accelerometers. Synthetic methods are disclosed for production of such fluids from available starting materials.Type: GrantFiled: May 1, 1987Date of Patent: May 30, 1989Assignee: Charles Stark Draper LaboratoryInventor: John R. Williams
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Patent number: 4814110Abstract: The present invention provides a method of esterifying dihydroxybenzene starting materials to synthesize unsymmetrical diesters in high yield. Many of the resultant unsymmetrical diesters are useful in dry bleaching compositions. The method can be practiced by selectively monoacylating a dihydroxybenzene starting material with an acid anhydride to form an intermediate monoester having the structure ##STR1## which is then acylated to form a diester reaction product having the structure ##STR2## wherein R.sub.1 is greater than R.sub.3 (and both R.sub.1 and R.sub.3 are alkyl groups) and X is a substituent group which does not participate in the esterification (or which can have a protecting group thereon).Type: GrantFiled: July 9, 1986Date of Patent: March 21, 1989Assignee: The Clorox CompanyInventors: Ronald A. Fong, Richard R. Rowland
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Patent number: 4806677Abstract: Hardeners are described for synthetic resins which contain groups which are capable of ester or amide formation and, if appropriate, polymerizable double bonds. The new hardeners, which allow lower crosslinking temperatures, are products (A) of the Michael addition of compounds (B), containing Michael addition-capable ester groups, to compounds (C) which contain at least two Michael addition-capable double bonds, the products (A) having an average of at least one polymerization-capable double bond and at least two transesterification- or transamidation-capable ester groups per molecule and the compound (B) representing products of the reaction of (b1) CH-active alkyl esters and (b2) polyisocyanates.Type: GrantFiled: January 29, 1987Date of Patent: February 21, 1989Assignee: Hoechst AGInventors: Gerd Walz, Helmut Plum
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Patent number: 4776875Abstract: Compounds of the formula ##STR1## in which R.sub.1 and R.sub.2 denote alkyl, OH, CF.sub.3 or cyanoethyl, A preferably denotes --COOH, R.sub.3 denotes inter alia alkoxycarbonylalkoxy, fairly high-molecular (>C.sub.12) alkoxy, alkylcarbonylalkoxy or nitrobenzyloxy, are valuable herbicides and growth regulators.Type: GrantFiled: March 26, 1986Date of Patent: October 11, 1988Assignee: Hoechst AktiengesellschaftInventors: Heinz J. Loher, Klaus Bauer, Hermann Bieringer
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Patent number: 4766256Abstract: Novel melt-spinnable anisotropic-melt-forming polyesters from certain disubstituted hydroquinones and terephthalic acid have high glass transition temperatures.Type: GrantFiled: June 18, 1987Date of Patent: August 23, 1988Assignee: E. I. Du Pont de Nemours and CompanyInventor: Robert S. Irwin
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Patent number: 4761495Abstract: The present invention is directed to a composition and method relating to the preparation of aspartyl peptides having the general formula: ##STR1## where the radical-NHR represents an amino acid or peptide group. In the method, a .beta.-monoester of aspartic acid having the general formula: ##STR2## where R.sub.1 represents a hydrocarbon-containing radical, is reacted with a .beta.-dicarbonyl compound, preferably ethylacetoacetate to protect the aspartyl amino group and form an enamine. The enamine is then coupld to an amino acid or peptide, following which any protecting groups are removed to yield .alpha.-aspartyl peptides without any .beta.-isomer. In its composition aspects, the present invention is directed to novel enamines resulting from reaction of the .beta.-monoester of aspartic acid with a .beta.-dicarbonyl compound.Type: GrantFiled: January 11, 1985Date of Patent: August 2, 1988Assignee: Isochem S.A.Inventors: Didier Wirth, Dominique Gibert, Annie Boutin
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Patent number: 4760087Abstract: Phenol derivatives of the formula ##STR1## wherein A and B have the same or different meanings and each represent one of the groups --C.tbd.C--, cis--CH.dbd.CH-- or trans--CH.dbd.CH--, R.sub.1 is hydrogen, an optionally substituted alkyl or phenyl group or a cycloalkyl group, R.sub.2 is hydrogen, methyl or ethyl, R.sub.3 represents hydrogen, acetyl or propionyl, R.sub.4 has the same meaning as R.sub.3 or represents an alkyl group, R.sub.5 is a carboxylic or a hydroxy group or a functional derivative of such groups or R.sub.5 is a nitrile group and R.sub.6 is hydrogen, an alkyl group or the group OR.sub.4 which specifically inhibit 5-lipoxygenase and are useful in pharmaceutical compositions for prophylaxis and treatment of diseases due to the action of leukotrienes. The compounds are prepared by reacting suitable acetylene compounds or metal derivatives thereof with alkyl or aryl halides or by means of Wittig reactions optionally followed by transforming the member R.sub.Type: GrantFiled: May 13, 1986Date of Patent: July 26, 1988Assignee: Gruenenthal GmbHInventors: Oswald K. Zimmer, Werner P. Vollenberg, Gerriet K. H. Loschen, Werner Winter, Erwin Kiesewetter, Ulrich G. P. Seipp
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Patent number: 4758591Abstract: Disclosed herein are dialkanoyloxybenzylidene dialkanoate represented by the formula, ##STR1## wherein X.sup.1 and X.sup.2 represent respectively alkanoyloxy group and a pharmaceutical composition in dosage unit form which comprises a dosage effective for the treatment of inflammatory disease of the dialkanoyloxybenzylidene dialkanoate as an active ingredient thereof.Type: GrantFiled: December 13, 1984Date of Patent: July 19, 1988Assignee: Kureha Kagaku Kogyo Kabushiki KaishaInventors: Hitoshi Takita, Fumihiko Kimura, Sakuo Noda, Yutaka Mukaida, Toyohiko Nitta
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Patent number: 4745212Abstract: Isocyanates containing ester and/or amide groups are produced by reacting (a) an isocyanatocarboxylic acid chloride with (b) an organic compound containing a silylated alcoholic group and/or silylated phenolic hydroxyl group and/or silylated amino group which compound contains no other group which is reactive with isocyanate and chlorocarbonyl groups under the reaction conditions. The reaction of (a) with (b) is carried out at a temperature of from -20.degree. to 150.degree. C. This process makes it possible to produce the desired isocyanates with a high degree of selectivity.Type: GrantFiled: October 8, 1987Date of Patent: May 17, 1988Assignee: Bayer AktiengesellschaftInventors: Werner Mormann, Edith Hissmann
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Patent number: 4739097Abstract: Compounds of the general formula I ##STR1## in which R is a hydrogen or halogen atom, a cyanide or an alkyl group having 1-4 carbon atoms andR.sub.1 is a hydrogen or halogen atom, nitro, alkyl, alkoxy, aryl, aryloxy, acyl or alkoxycarbonyl group,are prepared by esterifying two adjacent OH groups to give the cyclic carbonate, esterifying the free OH group with (meth)acrylic acid and selectively hydrolyzing the carbonate. The compounds are free of polyunsaturated impurities and can be used for preparing purely linear polymers.Type: GrantFiled: August 13, 1986Date of Patent: April 19, 1988Assignee: Hoechst AktiengesellschaftInventors: Juergen Sander, Arnold Schneller
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Patent number: 4727182Abstract: Monohalohydroquinone monocarboxylates are selectively prepared by halogenating a hydroquinone monocarboxylate, or admixture thereof with a hydroquinine dicarboxylate and a minor amount of hydroquinone, with a chlorine, bromine or sulfuryl halide halogenating agent; such monocarboxylates are facilely converted into the corresponding dicarboxylates by acylation. Both the monocarboxylates, e.g., monochlorohydroquinone monoacetate, and dicarboxylates, e.g., monochlorohydroquinone diacetate, are useful organic intermediates.Type: GrantFiled: June 25, 1985Date of Patent: February 23, 1988Assignee: Rhone-Poulenc Specialites ChimiquesInventor: Serge Ratton
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Patent number: 4701282Abstract: This invention provides smoking compositions which contain a .beta.-hydroxy-.gamma.-ketoester compound as a flavorant-release additive.In one of its embodiments, this invention provides tobacco compositions which contain a flavorant-release additive such as dodecyl 3-hydroxy-2,2,3-trimethyl-4-oxopentanoate: ##STR1## Under cigarette smoking conditions the above illustrated .beta.-hydroxy-.gamma.-keto ester pyrolyzes into 2,3-butanedione and other products which enhance the flavor of the mainstream smoke and the aroma of sidestream smoke.Type: GrantFiled: August 30, 1985Date of Patent: October 20, 1987Assignee: Philip Morris IncorporatedInventors: W. Geoffrey Chan, Yoram Houminer
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Patent number: 4695657Abstract: A process for the preparation of compounds containing a difluoromethylene group in a position .alpha. to an oxygen atom. An alcohol or a phenol is brought into contact with trifluoroacetic acid or a halide or anhydride thereof in anhydrous liquid hydrofluoric acid, in the presence of boron trifluoride, in a quantity such that the absolute pressure of boron trifluoride is at least about one bar. The compounds obtained according to the invention are used as synthesis intermediates in the pharmaceutical, plant-protection, and dye industries, as anesthetics and as additives for lubricating oils.Type: GrantFiled: December 17, 1985Date of Patent: September 22, 1987Assignee: Rhone-Poulenc Specialites ChimiquesInventor: Michel Desbois
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Patent number: 4692546Abstract: Acyloxy aromatic carboxylic acids, e.g., 4-acetoxybenzoic acid, are prepared by oxidizing with oxygen an acyloxy aromatic ketone, e.g., 4-acetoxyacetophenone in the presence of manganese cations and a lower-carboxylic acid anhydride as catalyst and a co-reductant or promoter. The acyloxy aromatic ketone may be prepared by acylating a hydroxy aromatic ketone, e.g., 4-hydroxyacetophenone, which has the effect of "masking" the hydroxyl group of the ketone in a manner necessary to effect the subsequent transition-metal catalyzed oxidation of the ketone to the acyloxy aromatic carboxylic acid.Type: GrantFiled: September 25, 1985Date of Patent: September 8, 1987Assignee: Celanese CorporationInventor: Kenneth G. Davenport
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Patent number: 4689427Abstract: The present invention is directed to novel hydroquinone derivatives which are useful as intermediates for the manufacture of (R,R,R)-.alpha.-tocopherol (natural vitamin E) as well as of racemic .alpha.-tocopherol. The invention is also directed to a process for the preparation of the hydroquinone derivatives of the invention.Type: GrantFiled: November 15, 1985Date of Patent: August 25, 1987Assignee: Hoffmann-La Roche Inc.Inventor: Marquard Imfeld
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Patent number: 4670604Abstract: 4-Acylresorcinol ethers of the formula ##STR1## in which R.sub.1 is lower alkyl, R.sub.2 is fluorinated lower alkyl, R.sub.3 is hydrogen, lower alkoxy, trifluoromethyl or halogen, alk is an alkylene or hydroxyalkylene radical which is uninterrupted or interrupted by oxygen, one of the radicals R.sub.4, R.sub.5 and R.sub.7 is a group of the formula --NH--C(.dbd.O)--R.sub.8, a radical R.sub.4 or R.sub.5 which differs from this is a radical R.sub.9 and a radical R.sub.7 which differs from this is a radical R.sub.10, R.sub.6 is hydrogen, lower alkyl, trifluoromethyl, halogen, carboxyl which is free, esterified or amidated, cyano or lower alkanoyl, R.sub.8 is carboxyl which is free, esterified or amidated or 5-tetrazolyl, R.sub.9 is hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl and R.sub.10 is hydrogen, lower alkyl, lower alkoxy, halogen, trifluoromethyl, cyano or carboxyl which is free, esterified or amidated, and their salts have antiallergic and antiinflammatory properties.Type: GrantFiled: November 22, 1985Date of Patent: June 2, 1987Assignee: Ciba-Geigy CorporationInventors: Andreas Beck, Alfred Sallmann, Robert W. Lang, Paul Wenk
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Patent number: 4665216Abstract: A process is provided for producing N-acyl-acyloxy aromatic amine, such as 4-acetoxyacetanilide by reacting a hydroxy-aromatic ketoxime with a carboxylic acid anhydride, e.g. acetic anhydride, in the presence of phosphoric or oxalic acid as a Beckmann rearrangement catalyst. Preferably the ketoxime is prepared by reacting a hydroxy aromatic ketone such as 4-hydroxyacetophone with a hydroxyl amine salt, and the ketone is obtained by the Fries rearrangement of a phenolic ester, e.g. phenyl acetate or the Friedel-Crafts acylation of a phenolic compound, e.g. phenol, with an acylating agent, e.g. acetic acid.Type: GrantFiled: March 12, 1985Date of Patent: May 12, 1987Assignee: Celanese CorporationInventors: Theodore Horlenko, James H. George