Having -c(=x), Wherein X Is Chalcogen, Bonded Directly To The Lactone Ring Patents (Class 549/322)
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Patent number: 9550745Abstract: Process for preparing 2,2-difluoroethylamine derivatives, wherein compounds of the general formula (IV) are reduced to the corresponding 2,2-difluoroethylamine derivatives of the general formula (III), where the A radical is as defined in the description:Type: GrantFiled: August 22, 2012Date of Patent: January 24, 2017Assignee: BAYER CROPSCIENCE AGInventors: Norbert Lui, Jens-Dietmar Heinrich
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Patent number: 9265706Abstract: The invention relates to the cosmetic use of a compound chosen from the compounds of formula (A) and the salts of same as an agent for depigmenting the skin and/or keratinous appendages.Type: GrantFiled: April 18, 2013Date of Patent: February 23, 2016Assignees: Centre National de la Recherche Scientifique—CNRS, Universite de Rennes 1, Centre Hospitalier Universitaire PontchaillouInventors: Joel Boustie, Marie-Dominique Galibert-Anne, Francoise Lohezic-le Devehat, Marylene Chollet-Krugler, Sophie Tomasi, Nicolas Mouchet, Beatrice Legouin-Gardadennec
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Patent number: 9056848Abstract: Process for preparing sodium or potassium salts of 4-hydroxy-2-oxo-2,5-dihydrofuran-3-carboxylic esters, comprising the reaction of a malonic ester with potassium hydroxide to give the corresponding malonic ester potassium salt of the formula (III) which is then reacted further with a chloroacetic ester to give a compound of the formula (V) followed by a ring closure reaction in which the compound of the formula (V) is reacted with a sodium or potassium alkoxide of the formula ZOR1 where R1, R2, R3 and K are each as defined in the description.Type: GrantFiled: February 29, 2012Date of Patent: June 16, 2015Assignee: BAYER INTELLECTUAL PROPERTY GMBHInventors: Christian Funke, Taraneh Farida, Stefan Beeck, Norbert Lui, Berndt Maiwald
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Publication number: 20150105459Abstract: The invention relates to the cosmetic use of a compound chosen from the compounds of formula (A) and the salts of same as an agent for depigmenting the skin and/or keratinous appendages.Type: ApplicationFiled: April 18, 2013Publication date: April 16, 2015Inventors: Joel Boustie, Marie-Dominique Galibert-Anne, Francoise Lohezic-le Devehat, Marylene Chollet-Krugler, Sophie Tomasi, Nicolas Mouchet, Beatrice Legouin-Gardadennec
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Patent number: 8916330Abstract: The present invention provides a resist composition giving a resist pattern excellent in CD uniformity and focus margin. A chemically amplified photoresist composition comprises a resin (A) and an acid generator (B), and the resin (A) contains, as a part or an entirety thereof, a copolymer (A1) which is obtained by polymerizing at least: a (meth)acrylic monomer (a1) having C5-20 alicyclic hydrocarbon group which becomes soluble in an aqueous alkali solution by the action of an acid; a (meth)acrylic monomer (a2) having a hydroxy group-containing adamantyl group; and a (meth)acrylic monomer (a3) having a lactone ring, and the copolymer (A1) has a weight-average molecular weight of 2500 or more and 5000 or less, and a content of the copolymer (A1) is not less than 50 parts by mass with respect to 100 parts by mass of the resin (A).Type: GrantFiled: June 23, 2010Date of Patent: December 23, 2014Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Takashi Hiraoka
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Patent number: 8883394Abstract: The present invention provides a resist composition giving a resist pattern excellent in CD uniformity and focus margin. A chemically amplified photoresist composition comprises a resin (A) and an acid generator (B), and the resin (A) contains, as a part or an entirety thereof, a copolymer (A1) which is obtained by polymerizing at least: a (meth)acrylic monomer (a1) having C5-20 alicyclic hydrocarbon group which becomes soluble in an aqueous alkali solution by the action of an acid; a (meth)acrylic monomer (a2) having a hydroxy group-containing adamantyl group; and a (meth)acrylic monomer (a3) having a lactone ring, and the copolymer (A1) has a weight-average molecular weight of 2500 or more and 5000 or less, and a content of the copolymer (A1) is not less than 50 parts by mass with respect to 100 parts by mass of the resin (A).Type: GrantFiled: June 23, 2010Date of Patent: November 11, 2014Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Takashi Hiraoka
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Patent number: 8816101Abstract: The invention relates to a mixture comprising protolichesterinic acid or a salt thereof or a diastereoisomer thereof or a derivative thereof, and lichesterinic acid or a salt thereof or an enantiomer thereof or a derivative thereof, for use for stimulating pigmentation of the skin and/or of its appendages. The invention also relates to derivatives of lichesterinic acid of formula (A).Type: GrantFiled: March 4, 2011Date of Patent: August 26, 2014Assignees: Centre National de la Recherche Scientifique—CNRS, Universite de Rennes 1, Centre Hospitalier Universitaire PontchaillouInventors: Joel Boustie, Marie-Dominique Galibert-Anne, Francoise Lohezic-le-Devehat, Marylene Chollet-Krugler, Sophie Tomasi
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Publication number: 20140058021Abstract: A composition, which comprises a) an organic material susceptible to oxidative, thermal or light-induced degradation; and b) a compound of formula I (Formula I) (I) wherein R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 are independently from each other H, C1-C8-alkyl, C4-C8-cycloalkyl, phenyl, C1-C4-alkoxy or halogen; n is 1, 2, 3, or 4; and when n is 1 A is —C(=0)-OR?1, —C(=0)-N(R?2)(R?3), —CN, phenyl, which is unsubstituted or substituted by one or more C1-C8-alkyl, C4-C8-alkoxy, C5-C7-cycloalkyl or halogen, —H or —S02-phenyl; when n is 2 A is —C(=0)-O—Z1—O—C(=0)-, —C(=0)-N(R?1)—Z2—N(R?2)—C(=0)- or piperazine-N,N?-biscarbonyl.Type: ApplicationFiled: April 25, 2012Publication date: February 27, 2014Applicant: BASF SEInventors: Walter Fischer, Abdel-Ilah Basbas, Kai-Uwe Schoning, Cinzia Tartarini, Werner Holzl, Bruno Rotzinger
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Publication number: 20130245268Abstract: Disclosed herein is enantioselective synthetic method comprising reacting an enolisable C4-C50 organic anhydride with a second compound selected from the group consisting of an aldehyde, a ketone, an aldimine, a ketimine or a Michael Acceptor in the presence of a bifunctional organocatalyst. The reaction may find particular utility in the enantioselective synthesis of medicinally relevant heterocycles, such as dihydroisocoumarins and dihydroisoquinolinones.Type: ApplicationFiled: March 13, 2013Publication date: September 19, 2013Applicant: THE PROVOST, FELLOWS, FOUNDATION SCHOLARS, AND THE OTHER MEMBERS OF BOARDInventors: Stephen J. Connon, Sean Tallon, Claudio Cornaggia, Francesco Manoni, Esther Torrente
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Publication number: 20130096209Abstract: The present invention provides edible compositions comprising a compound of the present invention, food products comprising such edible compositions and methods of preparing such food products. The present invention also provides methods of reducing the amount of NaCl in a food product, methods of reducing the sodium intake in a diet, and methods of reducing bitter taste in a food product.Type: ApplicationFiled: April 15, 2011Publication date: April 18, 2013Applicants: Kraft Foods Global Brands LLC, Chromocell CorporationInventors: David Hayashi, William P. Jones, Jane V. Leland, Peter H. Brown, Joseph Gunnet, Daniel Lavery, Louise Slade, Kambiz Shekdar, Jessica Langer
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Publication number: 20120329868Abstract: The invention relates to a mixture comprising protolichesterinic acid or a salt thereof or a diastereoisomer thereof or a derivative thereof, and lichesterinic acid or a salt thereof or an enantiomer thereof or a derivative thereof, for use for stimulating pigmentation of the skin and/or of its appendages. The invention also relates to derivatives of lichesterinic acid of formula (A).Type: ApplicationFiled: March 4, 2011Publication date: December 27, 2012Applicants: Centre National de la Recherche Scientifique - CNRS, Centre Hospitalier Universitaire Pontchaillou, Universite de Rennes 1Inventors: Joel Boustie, Marie-Dominique Galibert-Anne, Francoise Lohezic-le-Devehat, Marylene Chollet-Krugler, Sophie Tomasi
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Publication number: 20120323023Abstract: Process for preparing 2,2-difluoroethylamine derivatives, wherein compounds of the general formula (IV) are reduced to the corresponding 2,2-difluoroethylamine derivatives of the general formula (III), where the A radical is as defined in the description:Type: ApplicationFiled: August 22, 2012Publication date: December 20, 2012Applicant: BAYER CROPSCIENCE AGInventors: Norbert LUI, Jens-Dietmar HEINRICH
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Patent number: 8273904Abstract: Process for preparing 2,2-difluoroethylamine derivatives, wherein compounds of the general formula (IV) are reduced to the corresponding 2,2-difluoroethylamine derivatives of the general formula (III), where the A radical is as defined in the description:Type: GrantFiled: September 5, 2008Date of Patent: September 25, 2012Assignee: Bayer Cropscience AGInventors: Norbert Lui, Jens-Dietmar Heinrich
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Publication number: 20110166301Abstract: The invention provides biodegradable polyesters, polyurethanes, comprising 3-carboxymuconolactone as a structural unit, 3-carboxymuconolactone esters and a process for their production. Polyesters comprising a repeating unit represented by the following formula (I): [wherein R represents a hydrocarbon-based divalent residue which, in the structure, optionally contains a heteroatom without an active hydrogen], polyurethanes comprising the polyester structure; 3-carboxymuconolactone esters; and a process for their production.Type: ApplicationFiled: September 9, 2009Publication date: July 7, 2011Applicants: KABUSHIKI KAISHA TOYOTA JIDOSHOKKI, NAGAOKA UNIVERSITY OF TECHNOLOGY, FORESTRY AND FOREST PRODUCTS RESEARCH INSTITUTEInventors: Hiroaki Takashima, Yusuke Yamamoto, Kohei Mase, Toshihisa Shimo, Tomokuni Abe, Kiyotaka Shigehara, Yoshihiro Katayama, Eiji Masai, Masaya Nakamura, Yuichiro Otsuka, Seiji Ohara
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Publication number: 20100304294Abstract: A salt represented by the formula (I-AA): wherein Q1 and Q2 each independently represent a fluorine atom or a C1-C4 perfluoroalkyl group, X1 represents a single bond etc., Y1 represents a C1-C36 aliphatic hydrocarbon group etc., A1 and A2 independently each represents a C1-C20 aliphatic hydrocarbon group etc., Ar1 represents a (m4+1)-valent C6-C20 aromatic hydrocarbon group which can have one or more substituents, B1 represents a single bond etc., m1 and m2 independently each represents an integer of 0 to 2, m3 represents an integer of 1 to 3, with the proviso that m1 plus m2 plus m3 equals 3, and m4 represents an integer of 1 to 3, and a photoresist composition comprising the salt represented by the formula (I-AA) and a resin comprising a structural unit having an acid-labile group and being insoluble or poorly soluble in an aqueous alkali solution but becoming soluble in an aqueous alkali solution by the action of an acid.Type: ApplicationFiled: May 25, 2010Publication date: December 2, 2010Applicant: SUMITOMO CHEMICAL COMPANY, LIMITEDInventors: Koji ICHIKAWA, Masako Sugihara, Tatsuro Masuyama
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Publication number: 20100190990Abstract: Process for preparing 2,2-difluoroethylamine derivatives, wherein compounds of the general formula (IV) are reduced to the corresponding 2,2-difluoroethylamine derivatives of the general formula (III), where the A radical is as defined in the description:Type: ApplicationFiled: September 5, 2008Publication date: July 29, 2010Applicant: Bayer Cropscience AGInventors: Norbert Lui, Jens-Dietmar Heinrich
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Publication number: 20100105929Abstract: The present invention relates to a process for the preparation of ?-butyrolactones.Type: ApplicationFiled: October 2, 2007Publication date: April 29, 2010Inventors: Peter Kapferer, Norbert Clausen
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Patent number: 6962938Abstract: The present application describes novel spiro-cyclic ?-amino acid derivatives of formula I: or pharmaceutically acceptable salt forms thereof, wherein ring B is a 3-13 membered carbocycle or heterocycle, ring C forms a 3-11 membered spiro-carbocycle or spiro-heterocycleon ring B, and the other variables are defined in the present specification, which are useful as as matrix metalloproteinases (MMP), TNF-? converting enzyme (TACE), and/or aggrecanase inhibitors.Type: GrantFiled: December 18, 2003Date of Patent: November 8, 2005Assignee: Bristol-Myers Squibb Pharma CompanyInventors: Gregory R. Ott, Xiao Tao Chen, Jingwu Duan, Matthew E. Voss
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Patent number: 6828276Abstract: There are described benzoylcyclohexanediones of the formula I, their preparation, and their use as herbicides and plant growth regulators. In this formula (I), C1, C2, C3 are cyclic radicals, X1 is a hetero atom, X2 is a chain of carbon atoms, L is a chain-like element, R1, R2, R3, R4, R5 are various radicals, and Y and Z are monoatomic bridge elements.Type: GrantFiled: August 30, 2001Date of Patent: December 7, 2004Assignee: Aventis CropScience GmbHInventors: Thomas Seitz, Andreas van Almsick, Lothar Willms, Hermann Bieringer, Thomas Auler, Hubert Menne
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Patent number: 6639075Abstract: A lactam-aldehyde compound represented by the formula (I) shown in the specification. The lactam-aldehyde compound may be prepared by subjecting a lactone-imine compound represented by formula (III) shown in the specification to an isomerization reaction. The precursor lactone-imine compound may be prepared by rearrangement of a 3,5-dioxa-12-azawurtzitane compound.Type: GrantFiled: March 7, 2002Date of Patent: October 28, 2003Assignee: National Institute of Advanced Industrial Science and TechnologyInventors: Hiroshi Izumi, Shigeru Futamura
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Publication number: 20030195376Abstract: Processes for the preparation of Venlafaxine (IX) via the novel epoxy-nitrile intermediate (I), which when subjected to hydrogenation forms compound (X), and may subsequently be reduced to yield the desired product (IX). The epoxy-nitrile intermediate (I) itself may be synthesised via various alternative reaction strategies, from a range of starting materials. E.g. 4-methoxy-benzaldehyde (VI), upon treatment with cyclohexyl magnesium bromide yields compound (V). This in turn may be oxidised to yield compound (III), which forms compound (II) on treatment with an (x-keto-halogenation agent. Cyanation of compound (II), then yields the desired epoxy nitrile intermediate (I), from which Venlafaxine (IX) may be synthesised.Type: ApplicationFiled: April 10, 2002Publication date: October 16, 2003Inventors: Dhiraj Mohansinh Rathod, Srinivasan Rengaraju, Milind Moreshwar Gharpure, Nishant Mahendra Patel, Mandar Manohar Deoahar
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Publication number: 20030181506Abstract: An object of the present invention is to provide a pharmaceutical agents for preventing and/or treating the progressive lesion after the organic damage without inhibiting organic function or regeneration function thereof, by selectively suppressing the induction of cytotoxic effector macrophages which are induced into the damaged organs in response to chemokines and cytokines which are expressed depending on the type of damaged organic tissues.Type: ApplicationFiled: December 12, 2002Publication date: September 25, 2003Inventors: Michio Ishibashi, Alain Wagner, Charles Mioskowski, Catherine Sylvain
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Patent number: 6420418Abstract: Compounds of Formula I are antagonists of VLA-4 and/or &agr;4&bgr;7, and as such are useful in the inhibition or prevention of cell adhesion and cell-adhesion mediated pathologies. These compounds may be formulated into pharmaceutical compositions and are suitable for use in the treatment of AIDS-related dementia, allergic conjunctivitis, allergic rhinitis, Alzheimer's disease, asthma, atherosclerosis, autologous bone marrow transplantation, certain types of toxic and immune-based nephritis, contact dermal hypersensitivity, inflammatory bowel disease including ulcerative colitis and Crohn's disease, inflammatory lung diseases, inflammatory sequelae of viral infections, meningitis, multiple sclerosis, multiple myeloma, myocarditis, organ transplantation, psoriasis, pulmonary fibrosis, restenosis, retinitis, rheumatoid arthritis, septic arthritis, stroke, tumor metastasis, uveititis, and type I diabetes.Type: GrantFiled: August 14, 2000Date of Patent: July 16, 2002Assignee: Merck & Co., Inc.Inventors: William K. Hagmann, Stephen E. Delaszlo, George Doherty, Linda L. Chang, Ginger X. Yang
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Publication number: 20020068832Abstract: In industrial production of &ohgr;-hydroxyaliphatic acid being an important intermediate for large cyclic lactone-based perfumes, using dicarboxylate ester which is inexpensive and readily obtainable, a method, with high yield and improved selectively, for making a 2-(&ohgr;-alkoxycarbonylalkanoyl)-4-butanolide and an alkaline metal salt thereof, an ester of &ohgr;-hydroxy-(&ohgr;-3)-ketoaliphatic acid as a novel compound and a derivative thereof, and a method for making the same are provided.Type: ApplicationFiled: November 29, 2001Publication date: June 6, 2002Applicant: Soda Aromatic Co., Ltd.Inventors: Hideaki Takaoka, Sigeru Wada, Nobuhiko Ito, Akio Hasebe, Shinzo Imamura, Hideo Muraoka
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Patent number: 6291688Abstract: A method, with high yield and improved selectively, for making a 2-(&ohgr;-alkoxycarbonylalkanoyl)-4-butanolide and an alkaline metal salt thereof, an ester of &ohgr;-hydroxy-(&ohgr;-3)-ketoaliphatic acid as a novel compound and a derivative thereof, and a method for making the same are provided.Type: GrantFiled: February 24, 1999Date of Patent: September 18, 2001Assignee: Soda Aromatic Co., Ltd.Inventors: Hideaki Takaoka, Sigeru Wada, Nobuhiko Ito, Akio Hasebe, Shinzo Imamura, Hideo Muraoka
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Publication number: 20010008109Abstract: The invention encompasses a compound having the formula: 1Type: ApplicationFiled: January 30, 2001Publication date: July 19, 2001Applicant: Xerox CorporationInventors: Jeffrey H. Banning, Michael B. Meinhardt, Donald R. Titterington, Clifford R. King
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Patent number: 6222049Abstract: 2-(&ohgr;-alkoxycarbonyl alkanoyl)-4-butanolide is produced with a high selectivity and yield through condensation reaction of Y-butyrolactone with a readily available, low-price dicarboxylate as represented by the following general formula: ROOC(CH2)nCOOR wherein n denotes an integer of 8-13, and R denotes an alkyl group or an alkenyl group.Type: GrantFiled: June 23, 1998Date of Patent: April 24, 2001Assignees: Toray Industries, Soda Aromatic Co., Ltd.Inventors: Tetsuya Katou, Go Hata, Takeaki Etoh, Nobuhiko Ito
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Patent number: 6020502Abstract: A method for the fluorination of 1,3-diketones and 1,3-ketoesters is disclosed.Type: GrantFiled: February 21, 1997Date of Patent: February 1, 2000Assignee: BNFL Fluorochemicals Ltd.Inventors: Richard D. Chambers, John Hutchinson, Martin P. Greenhall, John S. Moilliet, Julie Thomson
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Patent number: 5981782Abstract: The present invention provides a catalyst which exhibits a high catalytic activity and allows asymmetric reaction in a high asymmetric yield to obtain a reaction product having a high optical purity. The present invention also provides a process for the preparation of an optically active 4-methyl-2-oxetanone having a high optical purity useful as starting material of polymer in a high yield in a short period in the presence of the foregoing catalyst. A novel ruthenium-iodo-optically active phosphine complex is provided, represented by the following general formula (1):Ru--I.sub.2 --(R.sup.1 -BINAP) (1)wherein R.sup.1 -BINAP represents an optically active tertiary phosphine represented by the following general formula (2): ##STR1## wherein R.sup.1 represents an aryl group which may have a substituent selected from the group consisting of a C.sub.1-4 lower alkyl group, a C.sub.1-4 lower alkoxy group, a C.sub.1-4 lower alkylamino group, and a halogen atom or a C.sub.3-8 cycloalkyl group.Type: GrantFiled: November 4, 1997Date of Patent: November 9, 1999Assignee: Takasago International CorporationInventors: Yoshiki Okeda, Yoji Hori, Toshimitsu Hagiwara
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Patent number: 5972237Abstract: Heterocyclic compounds IR.sup.1 --X--L (I)whereL is a cyclic carbamate residue, a lactonoxy residue or a lactam residue,X is an oxygen-containing group ##STR1## where A is a linker, and R.sup.1 is an organic radical or a group L,are used as activators for inorganic peroxy compounds, in particular as cold bleach activators or optical brighteners in detergents, cleaners and bleaches and in disinfectants.Type: GrantFiled: November 17, 1997Date of Patent: October 26, 1999Assignee: BASF AktiengesellschaftInventors: Reinhard Muller, Thomas Wehlage, Wolfgang Trieselt, Alfred Oftring, Elisabeth Kappes, Gunter Oetter, Dieter Boeckh, Roland Ettl, Albert Hettche
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Patent number: 5936124Abstract: A synthesis of fluoxetine is disclosed. The process begins with a lower alkyl ester of 3-benzoylpropionic acid, which is reduced in the presence of a chiral ligand to produce the corresponding .gamma.-hydroxy ester, and the ester is cleaved. The free acid is then condensed with the alcohol to form a .gamma.-lactone, which is treated with ammonia to provide the .gamma.-hydroxy amide. The amide undergoes a Hoffman rearrangement to provide a 2-oxo-1,3 oxazine, which is reduced to 3-(methylamino)-1-phenyl-1-propanol. The alcohol is deprotonated and reacted with a 4-chloro- or 4-fluoro benzotrifluoride to provide fluoxetine free base.Type: GrantFiled: June 22, 1998Date of Patent: August 10, 1999Assignee: Sepacor Inc.Inventors: James Wallace Hilborn, Alex Roger Jurgens, Chris Hugh Senanayake
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Patent number: 5849217Abstract: An optically active compound represented by the formula R.sub.1 --A.sub.1 --A.sub.2 --X.sub.1 --A.sub.3 --(CH.sub.2).sub.p --L--A.sub.4 --R.sub.2, in which R.sub.1 is F, CN or straight chain, branched or cyclic alkyl and R.sub.2 is H, F, CH or straight chain or branched alkyl; A.sub.3 is 1,4-phenylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl, pyrazine-2,5-diyl, pyridazine-3,6-diyl, 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, 1,3-ditiane-2,5-diyl, thiophene-2,5-diyl, thiazole-2,5-diyl, thiaziazole-2,5-diyl, benzoxazole-2,5-diyl, benzoxazole-2,6-diyl, benzothiazole-2,5-diyl, benzothiazole-2,6-diyl, benzofuran-2,5-diyl, benzofuran-2,6-diyl, quinoxaline-2,6-diyl, quinoline-2,6-diyl, 2,6-naphthylene, indane-2,5-diyl, 2-alkylindane-2,5-diyl, indanone-2,6-diyl, 2-alkylindane-2,6-diyl, coumarane-2,5-diyl and 2-alkylcoumarane-2,5-diyl; A.sub.1, A.sub.2 and A.sub.4 are single bond or A.sub.3 ; X.sub.1 ' is a single bond, --COO--, --OCO--, --CH.sub.2 O--, --OCH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH-- or --C.tbd.Type: GrantFiled: November 13, 1996Date of Patent: December 15, 1998Assignee: Canon Kabushiki KaishaInventors: Shinichi Nakamura, Takao Takiguchi, Takashi Iwaki, Takeshi Togano, Yoko Kosaka
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Patent number: 5808106Abstract: 2-(.omega.-alkoxycarbonyl alkanoyl)-4-butanolide can be produced unexpectedly with a high selectivity and yield through condensation reaction of .gamma.-butyrolactone with a highly available, lo.omega.-price dicarboxylate as represented by the following general formula:ROOC(CH2)nCOOR(where n denotes an integer of 7-13, and R denotes an alkyl group or an alkenyl group). Furthermore, a long-chain .omega.-hydroxycarboxylic acid can be produced by subjecting 2-(.omega.-alkoxycarbonyl alkanoyl)-4-butanolide to hydrolysis and decarboxylation and reducing the carbonyl groups in the resultant product into methylene groups.Type: GrantFiled: April 30, 1997Date of Patent: September 15, 1998Inventors: Tetsuya Katou, Go Hata, Takeaki Etoh, Nobuhiko Ito
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Patent number: 5789603Abstract: A method is provided for the preparation of 2-acetyl-.gamma.-butyrolactone by condensing .gamma.-butyrolactone with an acetic acid ester in the presence of a strongly basic condensation agent, followed by protonation of the initially formed enolate, wherein the .gamma.-butyrolactone, the acetic acid ester and the condensation agent are fed continuously into the reaction zone in a ratio of from 1.0 to 6.0 parts by mols of acetic acid ester and from 0.9 to 1.6 parts by mols of the strongly basic substance per part by mols of .gamma.-butyrolactone, and wherein the reaction mixture formed by condensation is withdrawn from the reaction zone, either batchwise or continuously, and protonated.Type: GrantFiled: February 24, 1997Date of Patent: August 4, 1998Assignee: Huels AktiengesellschaftInventors: Guenther Koehler, Wilfried Uhlenbrock
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Patent number: 5670661Abstract: The present invention relates to a process for producing lactones starting from cyclic ketones which comprises an oxidation reaction which is performed in the presence of an optionally substituted cycloaliphatic peracid or of an optionally substituted aliphatic peracid that is immiscible with water. The process allows to obtain high selectivity, does not entail the use of dangerous reagents, and allows excellent economic advantages.Type: GrantFiled: April 16, 1996Date of Patent: September 23, 1997Assignee: Industrie Chimiche Caffaro S.p.A.Inventors: Livius Cotarca, Roberto Bianchini
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Patent number: 5593827Abstract: The compound N-(.beta.-ketocaproyl)L-homoserine lactone is shown to be an autoinducer that enhances gene expression in a wide variety of microorganisms. Use can be made of this property for diagnostic purposes, e.g., when gene expression causes bioluminescence or antibiotic production, or to promote bacterial growth. The invention claims use for these purposes of the compound and analogs of formula (I) where n is 2 or 3, each of X and Y is O, S or NH, and R is optionally-substituted C1-C12 alkyl or acyl. Some of these are also claimed as new compounds.Type: GrantFiled: October 18, 1993Date of Patent: January 14, 1997Assignee: The University of NottinghamInventors: Barrie W. Bycroft, Paul Williams, Gordon S. A. B. Stewart, Siri R. Chhabra, Paul Stead, Michael K. Winson, Philip J. Hill, Catherine E. D. Rees, Nigel J. Bainton
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Patent number: 5532386Abstract: A process for preparing compounds of the formula I ##STR1## where: Y inter alia is ##STR2## where R.sup.3 is hydrogen or a C.sub.1 -C.sub.10 - hydrocarbon radical. R.sup.1 and R.sup.2, inter alia, are each, independently of one another, hydrogen, a C.sub.1 -C.sub.20 -hydrocarbon radical which optionally carries inert substituents or heteroaryl, wherein a compound of the formula II ##STR3## where Z is ##STR4## is reacted in the presence of catalytic amounts of a carbonic ester and of a nitrogenous base at from 100.degree. to 250.degree. C. under a pressure of from 0.01 to 100 bar.Type: GrantFiled: March 1, 1995Date of Patent: July 2, 1996Assignee: BASF AktiengesellschaftInventor: Rolf Fischer
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Patent number: 5453516Abstract: A process for preparing 5-membered ring heterocycles of the general formula I ##STR1## where R.sup.1 is methyl or hydroxyethyl,R.sup.2,R.sup.3,R.sup.4,R.sup.5 and R.sup.6 are hydrogen, C.sub.1 - to C.sub.12 -alkyl, C.sub.2 - to C.sub.12 -alkenyl, aryl, C.sub.3 - to C.sub.8 -cycloalkyl, C.sub.1 - to C.sub.12 -alkoxy, halogen, C.sub.2 - to C.sub.20 -alkoxycarbonylalkyl, C.sub.2 - to C.sub.20 -alkylcarbonyloxy, formyl, C.sub.2 - to C.sub.20 -formylalkyl, benzoyl or --CH(OR.sup.3)(OR.sup.5), or R.sup.3 and R.sup.5 together are a C.sub.2 - to C.sub.7 -alkylene chain which is unsubstituted or monosubstituted to pentasubstituted by R.sup.4 or a .dbd.CH--CH.dbd.CH--CH.dbd. unit which is unsubstituted or monosubstituted to tetrasubstituted by R.sup.4,X is oxygen or N--R.sup.4by reacting 5-membered ring heterocycles of the general formula II ##STR2## where R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and X have the abovementioned meanings and Y is hydrogen, acetyl or C.sub.2 - to C.sub.Type: GrantFiled: December 13, 1993Date of Patent: September 26, 1995Assignee: BASF AktiengesellschaftInventors: Rolf Fischer, Rolf Pinkos
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Patent number: 5395553Abstract: Liquid crystalline compounds having an optically active .gamma.-lactone ring of the general formula (A): ##STR1## wherein R.sup.1 is a group selected from the class consisting of ##STR2## n and e are each independently 0 or 1, R.sup.3 is an alkyl group having 1 to 15 carbon atoms or an alkenyl group having 2 to 15 carbon atoms, said alkyl and alkenyl groups having each optionally one or more asymmetric carbon atoms, X and Y are each hydrogen atom, a halogen atom or a cyano group, R.sup.2 is an alkyl group having 1 to 15 carbon atoms or an alkenyl group having 2 to 15 carbon atoms, said alkyl and alkenyl groups having each optionally one or more asymmetric carbon atoms, and * means an asymmetric carbon atom, a liquid crystal composition containing the same and an element for opto-electronics devices comprising the liquid crystal composition.Type: GrantFiled: January 12, 1994Date of Patent: March 7, 1995Assignee: Daiso Co., Ltd.Inventors: Kazuhiko Sakaguchi, Tohru Kitamura
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Patent number: 5336809Abstract: A new process for the preparation of 1-fluorocyclopropyl methyl ketone of the formula ##STR1## which process comprises a) in a first step, reacting 2-acetyl-2-chloro-4-butanolide of the formula ##STR2## with an addition product of triethylamine and hydrogen fluoride of the formula(C.sub.2 H.sub.5).sub.3 N.multidot.n HFin whichn represents the numbers 1, 2 or 3,in the presence of a diluent at a temperature between 20.degree. C. and 120.degree. C. andb) in a second step, reacting the resulting 2-acetyl-2-fluoro-4-butanolide of the formula ##STR3## with a nucleophilic agent in the presence of a diluent at a temperature between 50.degree. C. and 200.degree. C.New halogenoketones of the formula ##STR4## in which Hal represents chlorine or bromine.Type: GrantFiled: March 2, 1993Date of Patent: August 9, 1994Assignee: Bayer AktiengesellschaftInventors: Stefan Bohm, Albrecht Marhold
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Patent number: 5322942Abstract: Optically active lactones are described, such as an intermediate lactone having the formula ##STR1## where R and R.sup.2 are each independently alkyl with 1 to 6 carbon atoms, cycloalkyl with 6 to 10 carbon atoms, aryl with 6 to 10 carbon atoms, or arylalkyl with 7 to 19 carbon atoms, R.sup.4 is H or C.sub.1-6 alkyl, and Ar is a homo- or heteroaromatic ring with 5 or 6 ring atoms being optionally substituted by C.sub.1-6 alkyl or alkoxy groups, halogen atoms, cyano or nitro groups. Such optically active, intermediate lactones are prepared from L-aspartic acid, and can be readily converted to (+)-pilocarpine and its analogues by hydrolysis, reduction, and hydrogenation, such as to an optically active lactone having the formula ##STR2## which is (+)-pilocarpine when R is ethyl, R.sup.4 is H, and Ar is 1-methylimidazol-5-yl.Type: GrantFiled: June 3, 1991Date of Patent: June 21, 1994Assignee: Regents of the University of CaliforniaInventors: Henry Rapoport, Jeffrey M. Dener, Lin-hau Zhang
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Patent number: 5308540Abstract: Liquid crystalline compounds having an optionally active .gamma.-lactone ring of the formula: ##STR1## wherein R.sup.1 is a group selected from the group consisting of ##STR2## n and e are each independently 0 or 1; R.sup.3 is an alkyl group having 1 to 15 carbon atoms; R.sup.2 is a group of the formula: --(CO).sub.m --R.sup.4 ; m is 0 or 1; R.sup.4 is hydrogen atom or an alkyl having 1 to 15 carbon atoms; and the symbol * is an asymmetric carbon atom, and an intermediate thereof, and process for the production of the same.Type: GrantFiled: July 16, 1992Date of Patent: May 3, 1994Assignee: Daiso Co., Ltd.Inventors: Kazuhiko Sakaguchi, Naoya Kasai, Yoshikazu Takehira, Tohru Kitamura, Yutaka Shiomi
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Patent number: 5308539Abstract: A ferroelectric liquid crystal composition including: at least one optically active compound of the formula (I): ##STR1## where R.sup.1 and R.sup.2 are, the same or different, a straight or branched chain alkyl group having 1 to 15 carbon atoms, k represents an integer of 0 or 1, and * represents an asymmetric carbon atom; andat least one compound selected from the group consisting of: compounds of the formula (II): ##STR2## where R.sup.3 and R.sup.4 are a straight or branched chain alkyl or alkoxy group having 1-15 carbon atoms, ##STR3## and ##STR4## each represents ##STR5## X represents --O--, --CO-- or a single bond, m and n are independently an integer of 0 or 1; compounds of the formula (III): ##STR6## where R.sup.5 and R.sup.6 are, the same or different, a straight or branched chain alkyl or alkoxy group having 1-15 carbon atoms, and p is an integer of 0 or 1;said ferroelectric liquid crystal composition exhibiting at least nematic phase, smectic A phase and smectic C phase.Type: GrantFiled: January 17, 1992Date of Patent: May 3, 1994Assignees: Sharp Kabushiki Kaisha, Daiso Co., Ltd.Inventors: Mitsuhiro Koden, Tomoaki Kuratate, Tohru Kitamura, Kazuhiko Sakaguchi, Yutaka Shiomi
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Patent number: 5185349Abstract: Novel lactone and lactam compounds which are useful to lower blood cholesterol levels in a patient, said compounds containing an arylcarboxamide or arylthiocarboxamide moiety.Type: GrantFiled: March 8, 1991Date of Patent: February 9, 1993Assignee: Warner-Lambert CompanyInventor: Corinne E. Augelli-Szafran
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Patent number: 5183908Abstract: This invention relates to an improved process for the preparation of 3-acyl-5-alkyldihydro-2(3H)-furanones according to the following reaction scheme: ##STR1## wherein R and R.sub.1 are hydrogen or alkyl and R.sub.2 is a hydrocarbon or -O-hydrocarbon radical of from 1 to 20 carbon atoms and X is a leaving group.Type: GrantFiled: February 27, 1990Date of Patent: February 2, 1993Assignee: Henkel CorporationInventors: A. Frederick Elsasser, Thomas J. Korte
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Patent number: 5140011Abstract: The compounds of the formula ##STR1## wherein A, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the significance given in claim 1, in the form of optically pure diastereomers, mixtures of diastereomers, diastereomeric racemates or mixtures of diastereomeric racemates as well as pharmaceutically usable salts thereof inhibit the activity of the natural enzyme renin and can accordingly be used in the form of pharmaceutical preparations in the control or prevention of high blood pressure and cardiac insufficiency.Type: GrantFiled: March 29, 1990Date of Patent: August 18, 1992Assignee: Hoffmann-La Roche, Inc.Inventors: Quirico Branca, Hans P. Marki, Werner Neidhart, Henri Ramuz, Wolfgang Wostl
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Patent number: 5099036Abstract: Disclosed are .alpha.-(.omega.-Cyanoalkanoyl)-.gamma.-butyrolactone represented by the formula: ##STR1## wherein n represents an integer of 7 to 11, and a method for producing the same, which comprises reacting .omega.-cyano fatty acid ester represented by the formula:NC--(CH.sub.2).sub.n --COOR (II)wherein R represents an alkyl group having 1 to 4 carbon atoms and n has the same meaning as in the above, with .gamma.-butyrolactone in the presence of alkali metal alcoholate represented by the formula:R'OM (III)wherein R' represents an alkyl group having 1 to 4 carbon atoms and M represents an alkali metal.Type: GrantFiled: March 11, 1991Date of Patent: March 24, 1992Assignees: Ube Industries, Ltd., Soda Aromaic Co., Ltd.Inventors: Hiroshi Yoshida, Noboru Kakeya, Masanori Kashiwagi
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Patent number: 5072008Abstract: The invention concerns a novel process for the stereospecific manufacture of novel hydroxymethyl lactols of the formula I by a one step reduction of a corresponding lactone carboxylic ester of the formula II (many of which esters are novel) using a reducing agent such as diisobutylaluminium hydride at about ambient temperature. The lactols of formula I are intermediates for the production of pharmacologically active 1,3-dioxane alkenoic acids useful in the treatment of certain cardiovascular and pulmonary medical conditions. Certain of the esters of formula II are novel and are also included in the invention.Type: GrantFiled: June 14, 1989Date of Patent: December 10, 1991Assignee: Imperial Chemical Industries PLCInventor: Gregory D. Harris
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Patent number: 5032611Abstract: Disclosed in the present invention are: a substance F-0368 or salts thereof having the following structural formula ##STR1## a method for production of the substance F-0368 or salts thereof, wherein an F-0368-substance-producing-microorganism belonging to a genus Kitasatosporia is cultured, and the substance F-0368 is isolated and collected from the cultured substance; a method for production of the substance F-0368 or salts thereof, wherein 3-methyl-4-lower alkoxy carbonyl-2(5H)-furanone represented by the following general formula is subjected to hydrolytic reaction ##STR2## (where: R represents a straight or branched lower alkyl group having 1 to 6 carbon atoms); a composition which consists essentially of the substance F-0368 or salt thereof, a diluent permissible in the agricultural chemicals, and a carrier or an excipient; a preventive agent for plant diseases such as rice blast disease and bacterial leaf blight disease, which consists essentially of an effective amount of the substance F-0368 or saltsType: GrantFiled: March 8, 1989Date of Patent: July 16, 1991Assignee: Kaken Pharmaceutical Co., Ltd.Inventors: Ryusuke Taguchi, Hideo Sugawara, Yukio Miyazaki, Taku Mizuno, Masahide Nomura, Machiko Sugiyama, Hideo Saito, Goro Yabuta, Akiya Furuichi, Yasuhiko Hamazaki, Katsuhiro Nakamura
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Patent number: 5023351Abstract: Disclosed are .alpha.-(.omega.-Cyanoalkanoyl)-.gamma.-butyrolactone represented by the formula: ##STR1## wherein n represents an integer of 7 to 11, and a method for producing the same, which comprises reacting .omega.-cyano fatty acid ester represented by the formula:NC--(CH.sub.2).sub.n --COOR (II)wherein R represents an alkyl group having 1 to 4 carbon atoms and n has the same meaning as in the above, with .gamma.-butyrolactone in the presence of alkali metal alcoholate represented by the formula:R'OM (III)wherein R' represents an alkyl group having 1 to 4 carbon atoms and M represents an alkali metal.Type: GrantFiled: May 29, 1990Date of Patent: June 11, 1991Assignee: Ube Industries, Ltd.Inventors: Hiroshi Yoshida, Noboru Kakeya, Masanori Kashiwagi