Unsaturation In Acid Moiety Patents (Class 560/183)
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Patent number: 6214958Abstract: A continuous process for making a comb-branched copolymer of an acrylic monomer and a polyether macromonomer is disclosed. The process is performed by continuously feeding a reaction zone with a monomer stream that contains an acrylic acid and a polyether macromonomer, and an initiator stream. The comb-branched copolymer made thereby performs better as water reducing agent in cement compared to that made by a batch process.Type: GrantFiled: July 21, 1999Date of Patent: April 10, 2001Assignee: Arco Chemical Technology, L.P.Inventors: Bi Le-Khac, Wei Wang, Edward T. Shawl
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Patent number: 6147036Abstract: A process for reacting certain carboxylic reactants with olefinic compounds then reacting the intermediate prepared thereby with ammonia, a hydrazine or an amine, and/or a reactive metal or reactive metal compound, products prepared thereby and, additive concentrates and lubricating oil and fuel compositions.Type: GrantFiled: March 23, 1998Date of Patent: November 14, 2000Assignee: The Lubrizol CorporationInventor: Mark R. Baker
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Patent number: 6118019Abstract: A 3-alkoxypropionic ester derivative, an olefin polymerization solid catalyst component using the same, an olefin polymerization catalyst using the same, and a process for the preparation of a polyolefin using the same. The 3-alkoxypropionic ester derivative is represented by formula (I): ##STR1## wherein R.sup.1 represents a hydrocarbon group having from 1 to 10 carbon atoms; R.sup.2 represents a hydrocarbon group having from 1 to 20 carbon atoms; R.sup.3 represents a hydrocarbon group having from 1 to 20 carbon atoms; and R.sup.4 represents a branched hydrocarbon group having 3 or more carbon atoms.Type: GrantFiled: December 29, 1998Date of Patent: September 12, 2000Assignee: Showa Denko K.K.Inventors: Masaki Fushimi, Shintaro Inazawa
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Patent number: 6103801Abstract: This invention relates to a process for producing 2-substituted succinate esters of formula (I) by reacting (a) a dicarboxylic compound with a first alcohol R'O[CH'.CH.sub.2 O].sub.x H where x is 0 or an integer from 1-6 in the presence of a catalyst to form a hydrocarbyl ester or, when x=1-6, a hydrocarbyloxy alkylene ester of maleic and/or fumaric acid and (b) the ester from step (a) with an alkaline earth metal alkoxide in the presence of a second alcohol R.OH to form the 2-substituted succinate ester of formula (I). The esters and paint formulations based thereon are also claimed.Type: GrantFiled: February 5, 1998Date of Patent: August 15, 2000Assignee: BP Chemicals LimitedInventors: Benjamin Patrick Gracey, Christopher Hallett
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Patent number: 6025410Abstract: The liquid oligomeric compositions of this invention are made by the Michael addition reaction of acetoacetate functional donor compounds with multifunctional acrylate receptor compounds where the equivalent ratios of multifunctional acrylate to acetoacetate vary from .gtoreq.1:1 to .gtoreq.13.2:1 depending on the functionality of both multifunctional acrylate and acetoacetate. Unuseable gelled or solid oligomer products occur below the claimed ranges. The liquid oligomers of this invention are further crosslinked to make coatings, laminates and adhesives.Type: GrantFiled: September 19, 1997Date of Patent: February 15, 2000Assignee: Ashland Inc.Inventors: Thomas M. Moy, Laurence Dammann, Roman Loza
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Patent number: 5990342Abstract: A surfactant, an emusifier for emulsion polymerization, a dispersant for suspension polymerization and a modifier for modification of resin properties are disclosed, each of these agents being comprised of a novel compound having a dibasic carboxyl group. The compound is represented by Formula (1)[X--O--(R.sup.1 O).sub.m --OC--R.sup.2 --COO].sub.y M (1)where M is a hydrogen atom, a metal atom or a quaternary nitrogen-containing group, y is equal to the valence of M, R.sup.1 is at least one hydrocarbon group, R.sup.2 is a moiety of a dibasic acid or a moiety of its anhydride, m is 0 or an integer of 1 to 1,000, and X is a hydrocarbon group having at least one polymerizable double bond of carbon--ncarbon which may contain an oxygen atom and a fluorine atom.Type: GrantFiled: July 16, 1996Date of Patent: November 23, 1999Assignee: Asahi Denka Kogyo K.K.Inventors: Masahide Tsuzuki, Kaoru Komiya
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Patent number: 5973200Abstract: A process for the free-radical addition of a mercaptan to a nonconjugated olefinic substrate having a terminal carbon-carbon double bond is disclosed. 2-Hydroxy-4-(ethylthio)butanoic acid (HMBA) or methionine can be prepared using this method. The nonconjugated olefinic substrate has the general formula: ##STR1## wherein R is selected from the group consisting of --COOH, --COOR.sup.2, --CONR.sup.3 R.sup.4, --CN and --CCl.sub.3, R.sup.1 is selected from the group consisting of --OH, --OCOR.sup.2, --NHCOR.sup.2 and --NH.sub.2, R.sup.2 is selected from the group consisting of alkyl, cycloalkyl and aryl and R.sup.3 and R.sup.4 are independently selected from the group consisting of --H and R.sup.2.Type: GrantFiled: January 20, 1998Date of Patent: October 26, 1999Assignee: Novus International, Inc.Inventor: Karl E. Koenig
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Patent number: 5892067Abstract: Synthesis of a vinyl terminated polymer by reacting a cationically polymeable monomer in the form of a cyclic ether with an acid chloride in a suitable solvent and in the presence of a Lewis acid. The vinyl-terminated polymers can be polymerized with other appropriate monomers resulting in thermoplastic elastomers having suitable properties for use as binders for explosives and propellants.Type: GrantFiled: June 9, 1997Date of Patent: April 6, 1999Assignee: The United States of America as represented by the Secretary of the NavyInventor: Mostafa A. H. Talukder
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Patent number: 5877334Abstract: A solid phase synthesis method and intermediates useful in the process are disclosed for the preparation of diamino diol and diamino alcohol inhibitors of HIV protease.Type: GrantFiled: July 23, 1996Date of Patent: March 2, 1999Assignee: Abbott LaboratoriesInventor: Gary T. Wang
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Patent number: 5869733Abstract: A process for the preparation of essentially isomerically pure methyl E-2-(2-aryloxymethylenephenyl)crotonates of the formula Ia ##STR1## where R is an aromatic radical and R' is a C.sub.1 -C.sub.3 -alkyl group, which comprises first converting a suitable methyl 2-(2-aryloxymethylenephenyl)-.alpha.-ketoacetate with an alkyl metal compound of the formula IIIM--CH.sub.2 --R' IIIwhere M is a metal ion equivalent into the corresponding methyl 2-(2-aryloxymethylenephenyl)-.alpha.-hydroxybutyrate of the formula IV, subsequently dehydrating IV in the presence of an acid to give a mixture of methyl E- and Z-2-(2-aryloxymethylenephenyl)crotonates and, subsequently, converting this mixture in the presence of a base in an inert polar solvent into the essentially isomerically pure methyl E-2-(2-aryloxymethylenephenyl)crotonate Ia.Type: GrantFiled: October 9, 1997Date of Patent: February 9, 1999Assignee: BASF AktiengesellschaftInventors: Wassilios Grammenos, Norbert Gotz, Hubert Sauter, Klaus Oberdorf
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Patent number: 5834468Abstract: This invention relates to substituted and unsubstituted ???(aryl- and heteroaryl-) alkyl-, alkyloxy-, alkylthio-, oxo-, thio-, and alkylamino!- heteroaryl and aryl!- alkylamino-, aminoalkyl-, alkyloxy-, and alkylthio!- aryl and heteroaryl compounds of the formula ##STR1## and pharmaceutically acceptable salts thereof, which are useful as antagonists of the pain enhancing effects of E-type prostaglandins, to processes for the preparation of such compounds, to pharmaceutical compositions comprising such compounds, and to methods for treating pain comprising the administration of such compounds.Type: GrantFiled: July 2, 1996Date of Patent: November 10, 1998Assignee: Zeneca LimitedInventors: Gloria Anne Breault, John Oldfield, Howard Tucker, Peter Warner
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Patent number: 5834576Abstract: A novel acrylic ester which is represented by general formula (2) ##STR1## wherein R.sub.1 and R.sub.2 independently represent a hydrogen atom or an organic residue, R.sub.3 represents an organic residue, n is a positive number among 1 to 3, and m is a positive number among 1 to 100 and which is applicable to various uses, is obtained by reacting an acrylic ester of general formula (3) ##STR2## wherein R.sub.1 represents a hydrogen atom or an organic residue, and R.sub.3 represents an organic residue, with a cyclic ether compound of general formula (4) ##STR3## wherein R.sub.2 represents a hydrogen atom or an organic residue, and n is a positive number among 1 to 3. Moreover, a novel acrylic acid derivative whose use is even wider is obtained by hydrolyzing the acrylic acid derivative.Type: GrantFiled: February 27, 1996Date of Patent: November 10, 1998Assignee: Nippon Shokubai Co., Ltd.Inventors: Hideaki Nagano, Koichi Nakagawa, Keiji Yurugi, Mitsuaki Makino, Tsuyoshi Hirata, Koichiro Nagare, Yuichi Kita
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Patent number: 5808085Abstract: A highly efficient and practical means has been developed which enables compounds of the formula: ##STR1## wherein R.sup.1 is lower alkoxy, lower alkylamino, di-(loweralkyl) amino, or the monovalent radical A--NR.sup.3, wherein A is lower alkyl or A is R.sup.4 R.sup.5 NC(O)CH.sub.2 wherein, for example, R.sup.4 is hydrogen or alkyl and R.sup.5 is hydrogen, alkyl or a substituted alkyl, or R.sup.5 is R.sup.6 R.sup.7 N-Alk wherein R.sup.6 and R.sup.7 each is hydrogen or lower alkyl and Alk is a divalent alkyl radical; R.sup.3 is, for example, benzyl, alkyl or a substituted alkyl; and R.sup.2 is, inter alia, alkyl, cycloalkyl, 1H-imidazol-4-yl, 4-thiazolyl or 2-amino-4-thiazolyl; to be prepared through the kinetic resolution of a compound of the formula: ##STR2## wherein R.sup.1 is as defined herein, R.sup.2 is as defined herein, and B is lower alkyl. These compounds are useful intermediates in the synthesis of renin inhibiting compounds.Type: GrantFiled: December 17, 1996Date of Patent: September 15, 1998Assignee: Boehringer Ingelheim (Canada) Ltd.Inventor: Murray Douglas Bailey
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Patent number: 5792876Abstract: A process is described for producing acetals comprising reacting an aldehyde or a ketone with an alcohol in the presence of a titanium compound having an acetylacetone as a ligand, or in the presence of a compound selected from the group consisting of stannous chloride dihydrate, cerium chloride hexahydrate and bismuth chloride. The process can be used in the synthesis of unstable acetals or when water exists in the reaction mixture, and therefore the process can be used for a wide variety of applications.Type: GrantFiled: November 6, 1996Date of Patent: August 11, 1998Assignee: Kuraray Co., Ltd.Inventors: Hideharu Iwasaki, Masahiko Kitayama, Takashi Onishi
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Patent number: 5777150Abstract: A compound of the formula (I) or its pharmaceutically acceptable salt or ester: ##STR1## wherein each of ##STR2## which are the same or different, is an aryl group or a heteroaromatic ring group; A is a C.sub.3-8 linear saturated or unsaturated aliphatic hydrocarbon group which may have substituent(s) selected from the group consisting of a lower alkyl group, a hydroxyl group, a lower alkoxy group, a carboxyl group, an aryl group and an aralkyl group; Q is a single bond or a group of the formula --CO--O--, --O--CO--, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --OCH.sub.2 --, --SCH.sub.2 --, --CH.sub.2 O-- or --CH.sub.2 S--; each of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 which are the same or different, is a hydrogen atom, a halogen atom, a lower alkyl group, a hydroxyl group, a lower alkoxy group, or an aryl or heteroaromatic ring group which may have substituent(s) selected from the group consisting of a halogen atom, a lower alkyl group and a lower alkoxy group; each of R.sup.5, R.sup.6 and R.sup.Type: GrantFiled: August 13, 1996Date of Patent: July 7, 1998Assignee: Banyu Pharmaceutical Co., Ltd.Inventors: Takashi Nomoto, Masahiro Hayashi, Jun Shibata, Yoshikazu Iwasawa, Morihiro Mitsuya, Yoshiaki Iida, Katsumasa Nonoshita, Yasufumi Nagata
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Patent number: 5777142Abstract: Compositions comprising unsaturated hydroxycarboxylic compounds, a process for reacting olefinic compounds with carboxylic reagents and products prepared by the process. The compositions containing the hydroxycarboxylic compounds and the products of the process are useful as intermediates for preparing additives for lubricants and fuels.Type: GrantFiled: August 22, 1995Date of Patent: July 7, 1998Assignee: The Lubrizol CorporationInventors: Paul E. Adams, Mark R. Baker, Jeffry G. Dietz
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Patent number: 5760278Abstract: A stabilization method of a vinyl compound with hydroxy group of an improved stability is achieved by preventing it from being denatured on storage, transportation, manufacturing process while maintaining its reactivity. A composition containing the vinyl compound with hydroxy group of an improved stability is obtained by the described stabilization method. The stabilization method is characterized by coexisting a vinyl compound with hydroxy group of formula (1), a primary antioxidant, alcohol and/or water, ##STR1## wherein R is a hydrogen atom or an organic residue, X is a --CN group, a --COR.sub.0 group or a --COOR.sub.0 group, and R.sub.0 is a hydrogen atom or an organic residue. In this stabilization method, not less than 50 ppm of alcohol and/or water is added with respect to the vinyl compound with hydroxy group. The stabilization method may be achieved by coexisting the above-defined vinyl compound with hydroxy group, the primary antioxidant and organic acid.Type: GrantFiled: September 9, 1996Date of Patent: June 2, 1998Assignee: Nippon Shokubai Co., Ltd.Inventors: Koichi Nakagawa, Mitsuaki Makino, Yuichi Kita
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Patent number: 5744635Abstract: A method for prerparing compounds of formula (I), wherein R is an optionally substituted alkenyl or alkynyl radical having up to 8 carbon atoms, or an optionally substituted mono- or polycyclic aryl or heteroaryl radical, and R.sub.1 and R.sub.2 are an alkyl radical having up to 4 carbon atoms. According to the method, a compound of the formula (II), wherein X is a halogen atom, is exposed to an organometallic compound of the formula (III): RZ, wherein R has the same meaning as before and Z is a metal or metal derivative. Alternatively, a compound of formula (II'), wherein Z' is a metal or metal derivative, is exposed to a compound of the formula (III'): RX', wherein X' is a nucleophilic reaction leaving group.Type: GrantFiled: October 3, 1995Date of Patent: April 28, 1998Assignee: Roussel UclafInventors: Jean-Louis Brayer, David Michael Hodgson, Ian Christopher Richards, Jason Witherington
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Patent number: 5705678Abstract: A novel oxotitanium complex represented by general formula (I) is disclosed: ##STR1## wherein R.sup.1 and R.sup.2 may be the same or different and each represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom, a phenyl group, a substituted phenyl group, a trialkylsilyl group, a monoalkyldiphenylsilyl group, a dialkylmonophenylsilyl group, a triphenylsilyl group, a substituted triphenylsilyl group, or a lower alkoxycarbonyl group, provided that R.sup.1 and R.sup.2 may be bonded to each other to form a hydrocarbon ring or a substituted hydrocarbon ring in cooperation with the carbon atoms to which R.sup.1 and R.sup.2 are bonded; R.sup.3 and R.sup.4 may be the same or different and each represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a benzoyl group, a benzenesulfonyl group, or a halogen atom, provided that R.sup.3 and R.sup.Type: GrantFiled: December 30, 1996Date of Patent: January 6, 1998Assignee: Takasago International CorporationInventors: Takeshi Nakai, Dai Kitamoto, Noboru Sayo
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Patent number: 5703270Abstract: A vinyl compound having a hydroxy group of the formula (1) ##STR1## wherein R is a hydrogen atom or an organic residue, X is a --CN group, a --COR.sub.0 group or a --COOR.sub.0 group and R.sub.0 is a hydrogen atom or an organic residue, is prepared by reacting a vinyl compound of the formula (2) ##STR2## wherein X is a --CN group, a --COR.sub.0 group or a --COOR.sub.0 group and R.sub.0 is a hydrogen atom or an organic residue, with an aldehyde series compound in the presence of a tertiary amine compound, and water in a sufficient amount for forming an aqueous phase upon the completion of the reaction. In this method, since the aqueous phase is formed upon the completion of the reaction, the organic phase including the vinyl compound having a hydroxy group and the aqueous phase including the tertiary amine compound can be easily separated.Type: GrantFiled: February 22, 1995Date of Patent: December 30, 1997Assignee: Nippon Shokubai Co., Ltd.Inventors: Koichi Nakagawa, Mitsuaki Makino, Yuichi Kita
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Patent number: 5696067Abstract: Compositions comprising hydroxyl group containing acylated nitrogen compounds, a process for reacting certain carboxylic reactants with olefinic compounds then reacting the product prepared thereby with ammonia, a hydrazine or an amine, products prepared thereby and lubricating oil and fuel compositions.Type: GrantFiled: April 15, 1996Date of Patent: December 9, 1997Assignee: The Lubrizol CorporationInventors: Paul E. Adams, Mark R. Baker, Jeffry G. Dietz
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Patent number: 5691444Abstract: A crystalline polylactone is produced having reactive acrylate end groups. When incorporated into a thermosetting resin which includes reactive C.dbd.CH.sub.2 sites, the present functionalized polylactone acts as a toughener, greatly increasing the impact resistance of the final cured product. Also disclosed are carboxyl-bearing polylactones as tougheners for epoxy resin systems.Type: GrantFiled: December 6, 1995Date of Patent: November 25, 1997Assignee: Clemson UniversityInventors: Shalaby W. Shalaby, Lance A. Monroe
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Patent number: 5686545Abstract: A liquid resin having a number average molecular weight of 10,000 to 200,000 and a viscosity, measured at 50.degree. C., of 500 to 30,000 cps, obtained by the copolymerization of a composition containing(a) 35 to 98% by weight of a monomer of the formula,CH.sub.2 =C(R.sup.1)COOR.sup.2wherein R.sup.1 is hydrogen or methyl and R.sup.2 is a hydrocarbon group having 4 to 22 carbon atoms,(b) 2 to 40% by weight of a polymerizable unsaturated carboxylic acid, and(c) 0 to 60% by weight of other polymerizable vinyl monomer.Type: GrantFiled: August 5, 1996Date of Patent: November 11, 1997Assignee: Toyo Ink Manufacturing Co., Ltd.Inventors: Miki Kawashima, Kunio Horiuchi
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Patent number: 5576405Abstract: A liquid resin having a number average molecular weight of 10,000 to 200,000 and a viscosity, measured at 50.degree. C., of 500 to 30,000 cps, obtained by the copolymerization of a composition containing(a) 35 to 98% by weight of a monomer of the formula,CH.sub.2 .dbd.C(R.sup.1)COOR.sup.2wherein R.sup.1 is a hydrogen or methyl and R.sup.2 is a hydrocarbon group having 4 to 22 carbon atoms,(b) 2 to 40% by weight of a polymerizable unsaturated carboxylic acid, and(c) 0 to 60% by weight of other polymerizable vinyl monomer.Type: GrantFiled: June 8, 1994Date of Patent: November 19, 1996Assignee: Toyo Ink Manufacturing Co., Ltd.Inventors: Miki Kawashima, Kunio Horiuchi
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Patent number: 5574182Abstract: An ester is caused to act on a 2-substituted-3-hydroxycarboxylic acid ester as a racemate in the presence of hydrolase under substantially anhydrous conditions to effect a transesterification resulting in the resolution.The compound thus resolved is converted to an optically active 2,6-cis-2,5,6-substituted-1,3-dioxan-4-one and the resulting compound is recrystallized to give optically active 5,6-anti-2,5,6-substituted-1,3-dioxan-4-one and 5,6-syn-2,5,6-substituted-1,3-dioxan-4-one. Thus an optically active compound having plural chiral centers.Further, an optically active 2,5,6-substituted-1,3-dioxan-4-one obtained by transesterification and recrystallization is reacted with an alcohol to produce an optically active 2-substituted-3-hydroxycarboxylic acid ester.Type: GrantFiled: January 30, 1995Date of Patent: November 12, 1996Assignee: Chisso CorporationInventors: Kazutoshi Miyazawa, Naoyuki Yoshida
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Patent number: 5557007Abstract: Novel unsaturated polylactone acrylates are produced by the reaction of an unsaturated polylactone, such as that produced in the reaction of a lactone with tetrahydrobenzyl alcohol, and a lower-alkyl acrylate under transesterification conditions. The unsaturated polylactone acrylate product may be subsequently epoxidized to form novel 3,4-epoxy polylactone acrylates.Type: GrantFiled: September 28, 1990Date of Patent: September 17, 1996Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: James P. Stanley
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Patent number: 5512698Abstract: This invention relates to a novel synthesis of 4-amino-5-hexenoic acid by thermal rearrangements, and to the novel intermediates produced thereby.Type: GrantFiled: April 11, 1995Date of Patent: April 30, 1996Assignee: Merrell Pharmaceuticals Inc.Inventor: Patrick Casara
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Patent number: 5491261Abstract: Di-, tri- and poly-perfluoroalkyl-substituted alcohols and acids and derivatives thereof are described which are prepared from perfluoroalkyl iodides and di-, tri- or polyallyl alcohols or acids. These compounds contain two or more perfluoroalkyl-iodoalkyl or perfluoroalkyl-alkenyl groups and one or two alcohol or acid groups or derivatized alcohol or acid functions. They can be reacted with isocyanates, epoxy compounds, anhydrides, acids or acid derivatives to prepare a great variety of oil- and water-repellent compositions which are useful for oil- and water-repellent treatment of textiles, glass, paper, leather and other substrates.Type: GrantFiled: July 1, 1994Date of Patent: February 13, 1996Assignee: Ciba-Geigy CorporationInventors: Marlon Haniff, Robert Falk, Ted Deisenroth, Karl F. Mueller
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Patent number: 5466396Abstract: The present invention is directed to novel compounds having the formula: ##STR1## wherein R is a C.sub.8 -C.sub.24 substituted or unsubstituted alkyl or alkenyl group;m is 1 to 3;n is 1 to 5; andx is hydrogen or a C.sub.1 to C.sub.3 hydrocarbon.The compounds are mild and good foaming compounds which can be used in both personal washing bars and liquids.Type: GrantFiled: November 19, 1993Date of Patent: November 14, 1995Assignee: Lever Brothers CompanyInventors: Stephen A. Madison, Michael Massaro, Gail B. Rattinger, Christine Wenzel
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Patent number: 5434267Abstract: Process for the preparation of compounds of the formula (I) ##STR1## in which R.sup.1, R.sup.2, R.sup.3, X and n have the meaning given in the description, by reacting acetates with carbon monoxide in the presence of a basic auxiliary, followed by alkylation. The products are intermediates for fungicidal acrylates.Type: GrantFiled: March 14, 1994Date of Patent: July 18, 1995Assignee: Bayer AktiengesellschaftInventors: Helmut Kraus, Alexander Klausener, Hans-Joachim Diehr
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Patent number: 5420334Abstract: The present invention is directed to compounds which inhibit farnesyl-protein transferase (FPTase) and the farnesylation of the oncogene protein Ras. The invention is further directed to chemotherapeutic compositions containing the compounds of this invention and methods for inhibiting famesyl-protein transferase and the famesylation of the oncogene protein Ras.Type: GrantFiled: April 4, 1994Date of Patent: May 30, 1995Assignee: Merck & Co., Inc.Inventors: Sheo B. Singh, Gerald F. Bills, Russell B. Lingham, Isabel Martin, Keith C. Silverman, Jack L. Smith
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Patent number: 5380936Abstract: This invention relates to a novel synthesis of 4-amino-5-hexenoic acid by thermal rearrangements, and to the novel intermediates produced thereby.Type: GrantFiled: January 19, 1994Date of Patent: January 10, 1995Assignee: Merrell Dow Pharmaceuticals Inc.Inventor: Patrick Casara
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Patent number: 5369109Abstract: The present invention provides optically active esters of 7-substituted 3,5-difunctionalized 6-heptenoic acids represented by the following formula: ##STR1## wherein R is a substituted or unsubstituted aromatic group, a substituted or unsubstituted heteroaromatic group or a substituted vinyl group;Ar is a condensed aromatic group;X.sup.1 and Y.sup.1 are not the same and each is a hydrogen atom or a hydroxyl group; andX.sup.2 and Y.sup.2 are not the same and each is a hydrogen atom or a hydroxyl group or enantiomers thereof.Type: GrantFiled: June 17, 1993Date of Patent: November 29, 1994Assignee: Sagami Chemical Research CenterInventors: Tamejiro Hiyama, Tatsuya Minami, Takeshi Hanamoto, Guntoori B. Reddy
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Patent number: 5354874Abstract: Acyclic terpene compounds useful as intermediates for producing sarcophytol A which have an anti-carcinogenic promotor activity and anti-tumor activity, which compounds are shown by the general formula (I): ##STR1##Type: GrantFiled: November 30, 1993Date of Patent: October 11, 1994Assignee: Mitsubishi Kasei CorporationInventors: Hisao Takayanagi, Yasunori Kitano, Yasuhiro Morinaka
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Patent number: 5332857Abstract: Variously substituted 3,5-dihydroxy-6,8-nonadienoic acids and esters, are blood cholesterol lowering agents and so are useful in the prevention and treatment of cardiovascular diseases such as atherosclerosis.Type: GrantFiled: July 6, 1992Date of Patent: July 26, 1994Assignee: Pfizer Inc.Inventors: Peter A. McCarthy, Frederick J. Walker
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Patent number: 5312814Abstract: .alpha.- Phosphonocarboxylate compounds are provided which inhibit the enzyme squalene synthetase and thereby inhibit cholesterol biosynthesis. These compounds have the formula ##STR1## wherein R.sup.1 is a lipophilic group which contains at least 7 carbons and is substituted alkyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted arylalkyl or optionally substituted aryl;Z is H, halogen, hydroxy, hydroxyalkyl or lower alkyl;R.sup.2 and R.sup.3 are independently H, metal ion or other pharmaceutically acceptable cation, or a prodrug ester;R.sup.4 is H, metal ion or other pharmaceutically acceptable cation, lower alkyl, lower alkenyl, arylalkyl, aryl or a prodrug ester.Type: GrantFiled: December 9, 1992Date of Patent: May 17, 1994Assignee: Bristol-Myers Squibb Co.Inventors: Scott A. Biller, David R. Magnin
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Patent number: 5312950Abstract: A method for the purification of alcohols from organic soluble impurities has been discovered comprising treating the crude alcohol with a cyclic anhydride followed by an aqueous base and extracting the corresponding half-ester into aqueous solution leaving the impurities in organic solution. This method is particularly useful for the separation of chiral, nonracemic alcohols from the corresponding antipodal ester (the mixture resulting from an enzymatic kinetic resolution) because the separation is non-chromatographic and the enantiomeric integrity of the products is maintained.Type: GrantFiled: August 31, 1993Date of Patent: May 17, 1994Assignee: Eastman Kodak CompanyInventor: Neil W. Boaz
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Patent number: 5310946Abstract: A process for preparing a compound containing (a) peroxyacetal lactone, (b) peroxyacetal lactol or (c) peroxycacetal ether functionality comprising oxygenating in the presence of one or more oxidizing metal catalysts a compound containing (i) hydroperoxy alkene carboxylic acid, (ii) hydroperoxy alkene aldehyde, (iii) hydroperoxy alkene keto, (iv) hydroperoxy alkene alcohol functionality or (v) dialkyl acetals of compounds in (ii) and (iii) above. For example (I).fwdarw.(II) wherein n=1,2 or 3; m=0, 1, 2,; p=0, 1, 2 or 3; R.sup.5 =--COOH, --C(O)R, --CROH, (.alpha.), where R is H, alkyl, aryl or arylalkyl; R.sup.1 are independently alkyl, arylalkyl or each R.sup.1 together with the group --O--C--O-- to which they are attached form a cyclic acetal; X=CR.sup.2 R .sup.3, O, S, SO, SO.sub.2 where R.sup.2 and R.sup.Type: GrantFiled: March 26, 1992Date of Patent: May 10, 1994Assignee: Rhone-Poulenc Rorer S.A.Inventors: Richard K. Haynes, Simone C. Vonwiller
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Patent number: 5298655Abstract: The present invention is directed to farnesyl pyrophosphate analogs which inhibit farnesyl-protein transferase (FTase) and the farnesylation of the oncogene protein Ras. The invention is further directed to chemotherapeutic compositions containing the compounds of this invention, and methods for inhibiting farnesyl-protein transferase and the farnesylation of the oncogene protein Ras.Type: GrantFiled: September 27, 1991Date of Patent: March 29, 1994Assignee: Merck & Co., Inc.Inventors: Neville J. Anthony, Ta-Jyh Lee, Robert L. Smith, Gerald E. Stokker
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Patent number: 5294646Abstract: The invention relates to new N-alkyl-N-(meth)acryloyloxyalkylcarboxamides of aromatic carboxylic acids and aromatic carboxylic acid anhydrides, their preparation and formulations of these compounds for use as adhesives for the treatment of dental hard substance.Type: GrantFiled: June 25, 1992Date of Patent: March 15, 1994Assignee: Bayer AktiengesellschaftInventors: Michael Muller, Wolfgang Podszun, Werner Finger, Jens Winkel
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Patent number: 5292839Abstract: Novel unsaturated peroxyketals useful as molecular weight regulators in polymerization reactions are disclosed. Also disclosed are a polymerization process employing these novel unsaturated peroxyketals as molecular weight regulators, polymers and oligomers made by this process and articles of manufacture comprising one or more polymers or oligomers made by this process. These molecular weight regulating peroxyketals provide the ability to introduce an epoxy functionality to the oligomer or polymer as well as an additional functionality, in a manner which gives a higher monomer conversion and less by-products than with comparable chain transfer regulators.Type: GrantFiled: April 28, 1993Date of Patent: March 8, 1994Assignee: Akzo N.V.Inventors: Luc L. T. Vertommen, John Meijer, Bernard J. Maillard
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Patent number: 5276021Abstract: Compounds which are useful as inhibitors of cholesterol biosynthesis and thus as hypocholesterolemic agents are provided which have the structure ##STR1## wherein R is OH, or salts thereof or lower alkoxy;R.sup.x is H or alkyl;X is --CH.sub.2 --, --CH.sub.2 --CH.sub.2 --, --CH.dbd.CH--, --C.tbd.C--, --CH.sub.2 CH.sub.2 CH.sub.2 -- or --CH.sub.2 O-- (where O is linked to Z);Z is a hydrophobic anchor, such as ##STR2## wherein the dotted lines represent optional double bonds.Type: GrantFiled: December 19, 1991Date of Patent: January 4, 1994Assignee: E. R. Squibb & Sons, Inc.Inventors: Donald S. Karanewsky, Michael C. Badia, Scott A. Biller, Eric M. Gordon, Michael J. Sofia
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Patent number: 5272069Abstract: This invention relates to methods for producing optically active hydroxyesters and also to methods for producing and purifying optically active five-membered ring lactones.More specifically, the invention provides methods for efficiently, safely, and selectively producing and purifying optically active (R)-hydroxyester (shown by formula 1) and optically active (S)-hydroxyester (shown by formula 2) in high state of purity at ordinary temperature.The invention also relates to application of the interconvertible optically active (R)-five-membered ring lacton (shown by formula 5).They are intermediates for synthesizing various medicines, agricultural chemicals, and biologically active substances, however especially useful for synthesizing pheromone of a noxious insect, Popillia japonica Newman. ##STR1## (Here, R.sub.1 denotes --C.tbd.C--R.sub.3 or --C.dbd.C--R.sub.3 ; R.sub.2 and R.sub.3 denote straight chain or branched alkyl groups containing 1 to 10 carbon atoms; R.sub.Type: GrantFiled: December 27, 1990Date of Patent: December 21, 1993Assignee: Nitto Denko Co. Ltd.Inventors: Eiichiro Fukusaki, Shuji Senda, Yutaka Nakazono, Tetsuo Omata, Ken Hibino, Hiromichi Ota, Takeshi Sugai
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Patent number: 5268511Abstract: A two step process, each of the steps being novel, for the production of trifluorovinyl ethers by reaction of a siloxane with selected acyl fluorides or carboxylic anhydrides, is disclosed. Also disclosed is a novel silyl ester intermediate.Type: GrantFiled: March 27, 1992Date of Patent: December 7, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventor: William B. Farnham
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Patent number: 5258138Abstract: A process for stabilizing an ethylenically unsaturated monomer or oligomer from premature polymerization is disclosed whereby a stabilizing amount of an amine, preferably a substituted hindered amine, in combination with phenothiazine or other related heterocyclic moiety is added to said polymerizable monomer or oligomer. The ethylenically unsaturated monomer or oligomer encompass vinyl monomers or oligomers bearing at least one polymerizable moiety. The combination of substituted hindered amine plus phenothiazine inhibits premature polymerization in the liquid and/or vapor phase.Type: GrantFiled: October 2, 1992Date of Patent: November 2, 1993Assignee: Ciba-Geigy CorporationInventors: Leslie R. Gatechair, Raymond Seltzer, James L. Hyun
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Patent number: 5248809Abstract: A process for preparing a polymerizable compound of the formula: ##STR1## or a polymerizable compound of the formula: ##STR2## is provided. These formed compounds are useful for the preparation of an acrylic resin which is low in viscosity and capable of forming a coating with excellent flexibility, weather resistance and water resistance.Type: GrantFiled: November 7, 1989Date of Patent: September 28, 1993Assignee: Nippon Paint Co., Ltd.Inventors: Ryozo Takagawa, Hisaki Tanabe, Yoshio Eguchi, Koichi Tsutsui
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Patent number: 5241081Abstract: The invention relates to new N-alkyl-N-(meth)acryloyloxyalkylcarboxamides of aromatic carboxylic acids and aromatic carboxylic acid anhydrides, their preparation and formulations of these compounds for use as adhesives for the treatment of dental hard substance.Type: GrantFiled: August 9, 1991Date of Patent: August 31, 1993Assignee: Bayer AktiengesellschaftInventors: Michael Muller, Wolfgang Podszun, Werner Finger, Jens Winkel
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Patent number: 5214195Abstract: The present invention provides new allyl esters of the general formula:X--CH.sub.2 --CR.sup.1 .dbd.CR.sup.2 --CO--Y--R.sup.3 --A (I)wherein R.sup.1 and R.sup.2, which can be the same or different, are hydrn or halogen atoms or alkyl or aryl radicals, R.sup.3 is a linking grouping (spacer), X is an acyloxy radical in which acyl in the acyloxy radical is the residue of an aliphatic carboxylic acid or is the radical RCO-- in which R is an organic radical, Y is an oxygen or sulphur atom or especially an --NH-- group and A is a grouping which can react with a solid carrier material F, which contains appropriate functional groups B, either after selective deblocking or directly, whereby A and B are atom groupings which react with one another with condensation and/or addition and formation of a linkage between the solid carrier material and the radical X--CH.sub.2 --CR.sup.1 .dbd.CR.sup.2 --CO--Y--R.sup.3 --.The present invention also provides processes for the preparation of these new allyl esters.Type: GrantFiled: August 31, 1990Date of Patent: May 25, 1993Assignee: Orpegen Medizinisch-Molekular Biologische Forschungsgesellschaft mbHInventors: Horst Kung, Winfried Kosch, Joachim Marz
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Patent number: 5206389Abstract: These acrylates are those of formulae: ##STR1## where R=C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.12 cycloalkyl, aryl, arylalkyl or alkylaryl; Y=C.sub.1 -C.sub.12 alkyl, C.sub.6 -C.sub.12 aryl, heterocyclic radical whose ring contains from 5 to 10 members and whose heteroatom is chosen from N, O and S, an alkylaryl in which the alkyl part contains from 1 to 4 carbon atoms, Y not being able to denote 1,4-phenylene when R denotes methyl; and Z=hydrocarbon radical containing at least 2 C forming with O and the 2 adjacent Cs a ring containing from 4 to 8 members.To prepare them, an acrylate of formula CH.sub.2 .dbd.CH--COOR is reacted with a dialdehyde OHC--Y--CHO in the presence of an effective quantity of at least one functionalisation catalyst.The invention also relates to the preparation of new polymers and copolymers from the said acrylates.Type: GrantFiled: June 27, 1991Date of Patent: April 27, 1993Assignee: AtochemInventors: Marie-Christine Berthe, Paul Caubere, Yves Fort
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Patent number: 5187279Abstract: (-)-Swainsonine is prepared by the steps of first reacting a compound having the formula: ##STR1## wherein each R.sub.2 is lower alkyl, with (4-carbalkoxybutyl) triphenylphosphonium bromide in a strong base to obtain an alcohol having the formula: ##STR2## wherein R.sub.2 is as defined above and R is C.sub.1 -C.sub.8 alkyl; the alcohol is then reacted with methanesulfonyl chloride or p-toluenesulfonyl chloride or benzenesulfonyl chloride in the presence of a tertiary amine to obtain the corresponding sulfonate. Heating the sulfonate with an azide in an organic solvent yields an imine having the formula: ##STR3## wherein R.sub.2 and R are ad defined above. Treating the imine with an inorganic base, in aqueous alcohol provides upon acidification, the corresponding acid. Heating the acid at reflux temperature in organic solvent, yields an enamide having the formula: ##STR4## wherein R.sub.2 is as defined above.Type: GrantFiled: August 14, 1991Date of Patent: February 16, 1993Inventors: Jin K. Cha, Richard B. Bennett, III