Additional Ring Containing Patents (Class 568/807)
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Patent number: 6765117Abstract: An improved method is described for making 9-deoxy-PGF1-type compounds. In contrast to the prior art, the method is stereoselective and requires fewer steps than the known methods for making these compounds. The invention also relates to novel intermediates prepared during the synthesis of the 9-deoxy-PGF1-type compounds.Type: GrantFiled: July 1, 2002Date of Patent: July 20, 2004Assignee: United Therapeutic CorporationInventors: Robert M. Moriarty, Raju Penmasta, Liang Guo, Munagala S. Rao, James P. Staszewski
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Patent number: 6700025Abstract: An improved method is described for making 9-deoxy-PGF1-type compounds. In contrast to the prior art, the method is stereoselective and requires fewer steps than the known methods for making these compounds.Type: GrantFiled: January 5, 2001Date of Patent: March 2, 2004Assignee: United Therapeutics CorporationInventors: Robert M. Moriarty, Hitesh Batra
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Patent number: 6689922Abstract: The invention concerns novel bi-aromatic compounds having the formula: which are analogs of vitamin D, the process of preparing them, as well as their use in pharmaceutical compositions in human or veterinary medicine, particularly in dermatology, cancer treatment, treatment of auto-immune diseases, and in organ or tissue transplants. Cosmetic compositions and methods of use are also included.Type: GrantFiled: July 26, 2001Date of Patent: February 10, 2004Assignee: Galderma Research & Development S.N.C.Inventor: Jean-Michel Bernardon
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Patent number: 6646170Abstract: The present invention relates to novel ether compounds, compositions comprising ether compounds, and methods useful for treating and preventing cardiovascular diseases, dyslipidemias, dysproteinemias, and glucose metabolism disorders comprising administering a composition comprising an ether compound. The compounds, compositions, and methods of the invention are also useful for treating and preventing Alzheimer's Disease, Syndrome X, peroxisome proliferator activated receptor-related disorders, septicemia, thrombotic disorders, obesity, pancreatitis, hypertension, renal disease, cancer, inflammation, and impotence. In certain embodiments, the compounds, compositions, and methods of the invention are useful in combination therapy with other therapeutics, such as hypocholesterolemic and hypoglycemic agents.Type: GrantFiled: April 26, 2002Date of Patent: November 11, 2003Assignee: Esperion Therapeutics, Inc.Inventors: Jean-Louis Henri Dasseux, Carmen Daniela Oniciu
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Publication number: 20030195259Abstract: The invention relates, as novel and useful industrial products, to triaromatic compounds, which are vitamin D analogues, of general formula (I): 1Type: ApplicationFiled: December 10, 2002Publication date: October 16, 2003Inventors: Jean-Michel Bernardon, Thibaud Biadatti
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Patent number: 6610889Abstract: Methods and compositions are provided for the direct catalytic asymmetric aldol reaction of aldehydes with donor molecules selected from ketones and nitroalkyl compounds. The reactions employ as catalyst a Group 2A or Group 2B metal complex of a ligand of formula I, as defined further herein.Type: GrantFiled: October 31, 2001Date of Patent: August 26, 2003Assignee: The Board of Trustees of the Leland Stanford Junior UniversityInventors: Barry M. Trost, Hisanaka Ito
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Publication number: 20030139478Abstract: A antimicrobial compound, compositions containing the same, and method of using the same for reducing the presence of microorganism on a substrate or in a fluid environment comprising an antimicrobial effective carrier and at least one antimicrobial compounds including non-halogenated hydroxyalkyl-substituted phenol compounds.Type: ApplicationFiled: December 13, 2002Publication date: July 24, 2003Inventors: D. Scott Harper, Robert A. Coburn, Andre Soshinsky, Marianne D. Huntley
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Patent number: 6506946Abstract: The present invention provides a process for producing an acetylenediol continuously by reacting a ketone with acetylene in the presence of an alkali catalyst, which process comprises continuously feeding, into a first-stage reactor, a reaction solvent, an alkali catalyst, a ketone and acetylene to give rise to a reaction, continuously introducing the reaction mixture into a second-stage reactor, and continuously feeding a fresh portion of the same ketone into the second-stage reactor to give rise to a reaction.Type: GrantFiled: June 12, 2002Date of Patent: January 14, 2003Assignee: Maruzen Petrochemical Co., Ltd.Inventors: Hideki Omori, Goro Sawada, Hideo Fukuda, Kazuhiro Imanishi, Tomohiko Sato
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Patent number: 6486355Abstract: Disclosed is a composition, a method of making and a method of using critical clusters for asymmetric synthesis using substantially optically-pure chiral solvent molecules in a supercritical fluid. The solvent molecules are capable of forming a multipoint hydrogen bonded solvate as they encage at least one solute molecule. The encaged solute molecule is capable of reacting to form an optically active chiral center. In another aspect, there is disclosed a method of directing the position of bonding between a solute molecule and a ligand involving encaging the solute molecule and the ligand with polar solvent molecules in a supercritical fluid under conditions of temperature and pressure sufficient to change electric charge distribution in the solute molecule.Type: GrantFiled: February 23, 2000Date of Patent: November 26, 2002Assignee: Brookhaven Science Associates LLCInventor: Richard A. Ferrieri
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Publication number: 20020128478Abstract: This invention relates to a process for the Heck coupling reaction where heterogeneous palladium catalysts are used to activate aryl halides for a carbon-carbon coupling with olefins in the presence a base and an aprotic solvent to produce aryl-olefin compounds. The process, in particular, provides for the use of aryl chlorides substituted with electron-withdrawing or electron-donating group for the cross coupling with olefins.Type: ApplicationFiled: March 4, 2002Publication date: September 12, 2002Inventors: Shane W. Krska, Thorsten S. Rosner, Yongkui Sun
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Patent number: 6433196Abstract: Citalopram can be industrially and economically produced and at a high yield by reacting a compound of the following formula [VI] with 3-(dimethylamino)propyl chloride in the presence of at least one of N,N,N′,N′-tetramethylethylenediamine and 1,3-dimethyl-2-imidazolidinone and a condensing agent. The compound of the following formula [III], which is a key compound for the production of citalopram, can be easily produced by subjecting the compound of the following formula [II] to reduction and cyclization.Type: GrantFiled: September 5, 2000Date of Patent: August 13, 2002Assignee: Sumika Fine Chemicals Co., Ltd.Inventors: Tetsuya Ikemoto, Wei-Guo Gao, Nobuhiro Arai, Masami Igi
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Patent number: 6342642Abstract: The present invention provides novel 1,4-diaryl-2-fluoro-1-buten-3-ol compounds of the structural formula I a method for the preparation of those formula I compounds, and the use of those formula I compounds in the preparation of 1,4-diaryl-2-fluoro-1,3-butadiene compounds of formula II and 1,4-diaryl-2-fluoro-2-butene compounds of formula IIIType: GrantFiled: August 13, 2001Date of Patent: January 29, 2002Assignee: BASF AktiengesellschaftInventors: Yulin Hu, David Allen Hunt
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Patent number: 6207835Abstract: Arylmetal compounds are prepared by deprotonation of aromatics which have a hydrogen atom in the ortho position relative to a halogen atom or a trifluoromethoxy group, using a suitable base or by halogen-metal exchange of haloaromatics using a suitable metalating reagent. The arylmetal compounds are prepared in a continuous-flow reactor. The arylmetal compound can be further reacted with an electrophilic reagent.Type: GrantFiled: December 17, 1999Date of Patent: March 27, 2001Assignee: Merck KGaAInventors: Volker Reiffenrath, Hans Christian Stiasny
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Patent number: 6197994Abstract: The present invention relates to silica gel supported bis-cinchona alkaloid compounds of the formula: wherein Q is dihydroquininyl or dihydroquinindinyl; X is a compound having 4 carbon atoms; and R is methoxy, ethoxy or methyl; and methods of preparation and use thereof. The silica gel supported bis-cinchona alkaloid derivatives of this invention are useful re-useable catalysts for preparing vicinal diols by asymmetric dihydroxylation of olefins.Type: GrantFiled: May 4, 1999Date of Patent: March 6, 2001Assignee: Korea Institute of Science and TechnologyInventors: Choong Eui Song, Jung Woon Yang
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Patent number: 6150413Abstract: Novel pharmaceutically/cosmetically-active triaromatic compounds have the structural formula (I): ##STR1## and are useful for the treatment of a wide variety of disease states, whether human or veterinary, for example dermatological, rheumatic, respiratory, cardiovascular, bone and ophthalmological disorders, as well as for the treatment of mammalian skin and hair conditions/disorders.Type: GrantFiled: May 26, 1998Date of Patent: November 21, 2000Assignee: Centre International de Recherches DermatologiquesInventors: Jean-Michel Bernardon, Philippe Nedoncelle
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Patent number: 6121330Abstract: The novel 5-hydroxy-alkyl-substituted phenyls are prepared by either reacting the corresponding benzaldehydes with the Grignard compounds and subsequently reducing the other functional groups or by reducing the corresponding benzoic esters by customary methods to give the corresponding hydroxyl compounds. The 5-hydroxy-alkyl-substituted phenyls are suitable for use as active compounds in medicaments, in particular for the treatment of dyslipidaemia.Type: GrantFiled: September 2, 1999Date of Patent: September 19, 2000Assignee: Bayer AktiengesellschaftInventors: Matthias Muller-Gliemann, Rolf Angerbauer, Arndt Brandes, Michael Logers, Carsten Schmeck, Gunter Schmidt, Klaus-Dieter Bremm, Hilmar Bischoff, Delf Schmidt
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Patent number: 6046354Abstract: A novel glycerol derivative, a process for preparing the same, and a process for preparing a triazole derivative. An optically active 2-arylglycerol derivative which is novel and useful as a synthetic intermediate of medicament is provided, and furthermore, (R)-2-(2,4-difluorophenyl)-3-(1H-1,2,4-triazole-1-yl)-propane-1,2-diol, which is useful as an antifungal agent, is prepared.Type: GrantFiled: August 31, 1998Date of Patent: April 4, 2000Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventors: Yoshihiko Yasohara, Kenji Miyamoto, Noriyuki Kizaki, Shigeru Kawano, Junzo Hasegawa
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Patent number: 6025531Abstract: A process for preparing an optically active alcohol by reacting a prochiral ketone corresponding to the optically active alcohol and an acid with a mixture of (1) a boron-containing compound selected from the group consisting of i) a borane compound which is obtained from an optically active .beta.-aminoalcohol and a boron hydride; or obtained from the optically active .beta.-aminoalcohol, a metal borohydride and an acid and ii) an optically active oxazaborolidine and (2) a metal borohydride; and a process for preparing an optically active amine by reacting an oxime derivative and an acid with a mixture of (1) a boron-containing compound selected from the group consisting of i) a borane compound which is obtained from an optically active .beta.-aminoalcohol and a boron hydride, or obtained from said optically active .beta.-aminoalcohol, a metal borohydride and an acid and ii) an optically active oxazaborolidine, and (2) a metal borohydride.Type: GrantFiled: June 3, 1998Date of Patent: February 15, 2000Assignee: Sumitomo Chemical Company, LimitedInventors: Yukio Yoneyoshi, Naoto Konya, Gohfu Suzukamo
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Patent number: 6015926Abstract: An efficient method for the preparation of key intermediate, in the synthesis of (-)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-ben zoxazin-2-one, a reverse transcriptase inhibitor is achieved using a chiral addition reaction to the 4-chloro-2-trifluoromethylketoaniline with an organozinc complex to give the desired alcohol. This instant method has broad applicability in the chiral addition to any prochiral ketone.Type: GrantFiled: May 11, 1998Date of Patent: January 18, 2000Assignee: Merck & Co., Inc.Inventors: Cheng Yi Chen, Lushi Tan, Richard D. Tillyer
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Patent number: 5986095Abstract: A process is described for preparing a compound of the formula or the S-enantiomer thereof,wherein:R is alkyl, aryl, cycloalkyl, aralkyl, or cycloalkylalkyl,R.sup.1 is halogen;R.sup.2 is halogen, alkyl, cycloalkyl, aryl or ##STR1## wherein the process comprises treating the associated racemic alcohol with an acylatingagent ##STR2## (wherein L is a leaving group) and an enzyme or microorganism capable of enantioselective acylation. This process may also be used to isolate the unreacted R- or S-alcohol. The acylated product may be enantioselectively hydrolyzed with a lipase or lipase-supplying microorganism to the S- or R-alcohol. Compounds prepared by this invention are useful antipsychotic agents or useful intermediates therefor.Type: GrantFiled: January 6, 1992Date of Patent: November 16, 1999Assignee: E.R. Squibb & Sons, Inc.Inventors: Ronald L. Hanson, Ramesh N. Patel, Laszlo J. Szarka
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Patent number: 5968908Abstract: The invention is novel analogs of 9-cis-retinoic acid which are useful for the treatment and prevention of coronary artery disease and to protect against premature atherosclerosis by increasing HDL levels. The invention includes processes for preparing the novel 9-cis-retinoic acid analogs.Type: GrantFiled: November 14, 1995Date of Patent: October 19, 1999Assignee: American Cyanamid CompanyInventors: Joseph William Epstein, Feng Ling Qing, Gary Harold Birnberg, Adam Matthew Gilbert
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Patent number: 5935986Abstract: There are described compounds of the general formula I ##STR1## in which the index and the substituents have the following meanings: n is 0, 1, 2, 3 or 4;R is nitro, cyano, halogen,unsubstituted or substituted alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy orin the event that n is greater than 1 additionally an unsubstituted or substituted bridge which is bonded to two adjacent ring atoms;R.sup.1, R.sup.2 are alkyl;R.sup.3 is a substituted pyrazole ?sic! or triazole ?sic! radical of the formulae A.1 to A.3 ##STR2## where the bond marked .circle-solid. is the bond to the oxygen, processes for their preparation, and their use.Type: GrantFiled: November 20, 1997Date of Patent: August 10, 1999Assignee: BASF AktiengesellschaftInventors: Bernd Muller, Reinhard Kirstgen, Hartmann Konig, Michael Rack, Klaus Oberdorf, Franz Rohl, Hubert Sauter, Gisela Lorenz, Eberhard Ammermann, Siegfried Strathmann, Volker Harries
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Patent number: 5876631Abstract: The present invention generally relates to the formation of organic gels by dissolving organic gelling agents in organic solvents. The aryl cyclohexanol gelling agents employed in this invention are not structurally related to previously known gellation agents and they exhibit potent gellation activity, for example, from 0.2-5%, by weight, of gelling agent is able to immobilize a variety of organic solvents. The gels formed range from optically transparent to slightly translucent, and complete fluidity can be restored by either increasing the temperature (reversible) or by chemical treatment (irreversible).Type: GrantFiled: June 25, 1997Date of Patent: March 2, 1999Assignee: Baylor UniversityInventor: Charles M. Garner
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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: 5780692Abstract: A process for producing a benzhydrol compound (II) which comprises hydrogenating a benzophenone compound (I) in the presence of a hydrogenation catalyst consisting of a transition metal complex, a base and an optically active diamine compound: ##STR1## wherein R.sup.1 to R.sup.10 each represents H, OH, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkanoyl, etc., R.sup.2 and R.sup.3, and R.sup.8 and R.sup.9 may form --CH.dbd.CH--CH.dbd.CH--, or any two of R.sup.1 to R.sup.9 adjacent to each other may be bonded to thereby form --OCH.sub.2 O-- or --(CH.sub.2).sub.3 --. By using this process, optically active benzhydrol compounds which have a high purity and are useful as, for example, intermediates in the synthesis of drugs can be produced by simple procedures.Type: GrantFiled: December 24, 1996Date of Patent: July 14, 1998Assignee: Takasago International CorporationInventors: Minzo Sakaguchi, Takashi Imai, Takashi Miura, Tetsuro Yamazaki
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Patent number: 5663207Abstract: Gem-Dichlorocyclopropanes (Analog II derivatives) which demonstrate antiproliferative activity toward MCF-7 cells, in vitro and are generally not reversed by estradiol or having intrinsic estrogenicity (except the hydroxyphenyl derivative Compound 30). In general the cyclopropane compounds have the formula: ##STR1## or any pharmaceutically acceptable salt thereof. X is selected from a group consisting of hydrogen and halogen atoms. The group R.sub.1 may he a hydrogen atom, an alkyl group, an acyl group, or an arylalkyl group. The group R.sub.2 may be a hydrogen atom, an unsubstituted aryl group or a substituted aryl group. The group R.sub.3 may be a hydrogen atom, an alkyl group, a cycloalkyl group, a substituted aryl group or an unsubstituted aryl group. The group R.sub.4 may be a hydrogen atom, an unsubstituted aryl group or a substituted aryl group. The R.sub.4 is absent when R.sub.Type: GrantFiled: January 20, 1995Date of Patent: September 2, 1997Assignee: Research Corporation TechnologiesInventors: Robert A. Magarian, Joseph T. Pento, May T. Griffin
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Patent number: 5658927Abstract: Diphenylcyclopropyl analogs in which one or more of the phenyl rings includes alkoxy substituents including a dialkylaminoalkoxy group, an unsubstituted piperazine alkoxy group, a substituted piperazine alkoxy group, an unsubstituted piperidine alkoxy group, and a substituted piperidine alkoxy group, and which may have one or two alkyl groups bonded to the cyclopropane. The compounds are useful as antiestrogens and anti-tumor agents.Type: GrantFiled: June 7, 1995Date of Patent: August 19, 1997Assignee: Research Corporation TechnologiesInventors: Robert A. Magarian, Joseph T. Pento, Lynette Overacre
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Patent number: 5658951Abstract: Diphenylcyclopropyl analogs in which one or more of the phenyl rings includes alkoxy substituents including a dialkylaminoalkoxy group, an unsubstituted piperazine alkoxy group, a substituted piperazine alkoxy group, an unsubstituted piperidine alkoxy group, and a substituted piperidine alkoxy group, and which may have one or two alkyl groups bonded to the cyclopropane. The compounds are useful as antiestrogens and anti-tumor agents.Type: GrantFiled: June 7, 1995Date of Patent: August 19, 1997Assignee: Research Corporation TechnologiesInventors: Robert A. Magarian, Joseph T. Pento, Lynette Overacre
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Patent number: 5658914Abstract: Diphenylcyclopropyl analogs in which one or more of the phenyl rings includes alkoxy substituents including a dialkylaminoalkoxy group, an unsubstituted piperazine alkoxy group, a substituted piperazine alkoxy group, an unsubstituted piperidine alkoxy group, and a substituted piperidine alkoxy group, and which may have one or two alkyl groups bonded to the cyclopropane. The compounds are useful as antiestrogens and anti-tumor agents.Type: GrantFiled: June 7, 1995Date of Patent: August 19, 1997Assignee: Research Corporation TechnologiesInventors: Robert A. Magarian, Joseph T. Pento, Lynette Overacre
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Patent number: 5656619Abstract: Abstract of the Disclosure: Diphenylheteroalkyl derivatives of the formula I ##STR1## where A and R.sup.1 -R.sup.6 have the meanings specified in the description, and the preparation thereof are described.The substances are suitable for controlling diseases and as cosmetic agents.Type: GrantFiled: June 6, 1995Date of Patent: August 12, 1997Assignee: BASF AktiengesellschaftInventors: Bernd Janssen, Hans-Heiner Wuest
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Patent number: 5608088Abstract: A process for producing 3,4-caranediol of the formula [I] includes subjecting 3,4-epoxycarane, which is obtained by epoxidizing 3-carene under specific conditions, to a hydration reaction in the presence of a base catalyst in aqueous ethanol under pressure to obtain 3,4-caranediol.Type: GrantFiled: September 8, 1995Date of Patent: March 4, 1997Assignee: Sumitomo Chemical Company, LimitedInventors: Keisuke Watanabe, Noboru Yamamoto, Atsushi Kaetsu, Yoshimi Yamada
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Patent number: 5563292Abstract: Novel compounds of Formula 1 ##STR1## or a pharmaceutically acceptable salt or solvate thereof are disclosed. Also disclosed are pharmaceutical compositions containing compounds of Formula 1. Methods of treating allergy, inflammation and hyperproliferative skin diseases with compounds of Formula 1 are also disclosed.Type: GrantFiled: April 2, 1992Date of Patent: October 8, 1996Assignee: Schering CorporationInventors: Neng-Yang Shih, Pietro Mangiaracina
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Patent number: 5397802Abstract: Gem-Dichlorocyclopropanes (Analog II derivatives) which demonstrate antiproliferative activity toward MCF-7 cells, in vitro and are generally not reversed by estradiol or having intrinsic estrogenicity (except the hydroxyphenyl derivative Compound 30). In general the cyclopropane compounds have the formula: ##STR1## or any pharmaceutically acceptable salt thereof. X is selected from a group consisting of hydrogen and halogen atoms. The group R.sub.1 may be a hydrogen atom, an alkyl group, an acyl group, or an arylalkyl group. The group R.sub.2 may be a hydrogen atom, an unsubstituted aryl group or a substituted aryl group. The group R.sub.3 may be a hydrogen atom, an alkyl group, a cycloalkyl group, a substituted aryl group or an unsubstituted aryl group. The group R.sub.4 may be a hydrogen atom, an unsubstituted aryl group or a substituted aryl group. The R.sub.4 is absent when R.sub.Type: GrantFiled: February 22, 1993Date of Patent: March 14, 1995Assignee: Research Corporation Technologies, Inc.Inventors: Robert A. Magarian, Joseph T. Pento, May T. Griffin
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Patent number: 5395985Abstract: A compound represented by the general formula (I) and a separating agent comprising the same: ##STR1## wherein Ar and Ar' are each an aromatic group; and the positional relationship of the two substituents on the central benzene ring may be any of ortho, meta and para.The above compound is effective in the separation and purification of many compounds to and enables the provision of various compounds (such as intermediates of drugs) which are useful in the field of fine chemicals, particularly optically active substances, at high purities and in large amounts.Type: GrantFiled: March 4, 1994Date of Patent: March 7, 1995Assignee: Daicel Chemical Industries, Ltd.Inventor: Fumio Toda
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Patent number: 5393885Abstract: Compounds of the formula ##STR1## in which R.sub.1 is halogen, C.sub.1 -C.sub.3 alkyl, halo-C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, halo-C.sub.1 -C.sub.3 alkoxy or cyano and/or two substituents R.sub.1 which are bonded to adjacent C atoms of the phenyl ring together are --O--CH.sub.2 --O--; R.sub.2 is hydrogen, halogen or methyl;R.sub.3 is fluorine, chlorine, bromine or C.sub.1 -C.sub.3 alkyl; R.sub.4 is hydrogen or C.sub.1 -C.sub.3 alkyl;either R.sub.5 is hydrogen, C.sub.1 -C.sub.4 alkyl, ##STR2## --COCO--R.sub.8,--CO--R.sub.9 or S(O).sub.m --N(R.sub.10)--COO--R.sub.11 andR.sub.6 is C.sub.1 -C.sub.6 alkyl, halo-C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.6 alkenyl, halo-C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.5 alkynyl, halo-C.sub.3 -C.sub.5 alkynyl, C.sub.1 -C.sub.3 alkoxy-C.sub.1 -C.sub.3 alkyl, C.sub.3 -C.sub.6 cycloalkyl, unsubstituted or substituted phenyl; or R.sub.5 and R.sub.6 together are --(CH.sub.2).sub.4 -- or --(CH.sub.2).sub.5 --; R.sub.7 is hydrogen, halogen or C.sub.1 -C.sub.3 alkyl; R.Type: GrantFiled: February 22, 1994Date of Patent: February 28, 1995Assignee: Ciba-Geigy CorporationInventor: Friedrich Karrer
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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: 5349105Abstract: Retinoid like activity is exhibited by compounds of the formula ##STR1## where R.sub.1 -R.sub.4 independently are hydrogen, lower alkyl, cycloalkyl or lower alkenyl, A and B independently are hydrogen, lower alkyl, cycloalkyl, lower alkenyl, SR* or OR* where R* is lower alkyl, cycloalkyl or lower alkenyl; Y is lower alkenyl, lower alkynyl, lower cycloalkyl, lower branched chain alkyl or (CH.sub.2).sub.n where n is 0-6; and Z is H, --COOH or a pharmaceutically acceptable salt, ester or amide thereof, --CH.sub.2 OH or an ether or ester derivative, or --CHO or an acetal derivative, or --COR' or a ketal derivative where R' is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons.Type: GrantFiled: March 17, 1993Date of Patent: September 20, 1994Assignee: Allergan, Inc.Inventor: Roshantha A. S. Chandraratna
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Patent number: 5336815Abstract: Preparation of vinyl glycols (I) ##STR1## (R.sup.1 to R.sup.6 =H, a carbo-organic radical, optionally substituted) in which an unsaturated diol of formula II ##STR2## is isomerized in the presence of a rhenium catalyst under neutral conditions. The compounds (I) serve as intermediates for the preparation of active substances and for the preparation of polymers.Type: GrantFiled: April 29, 1993Date of Patent: August 9, 1994Assignee: BASF AktiengesellschaftInventors: Rainer Becker, Walter Gramlich, Michael Huellmann, Hans-Ulrich Scholz
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Patent number: 5326898Abstract: Compounds of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 independently are hydrogen, lower alkyl of 1 to 6 carbons, halogen or lower alkoxy of 1 to 6 carbons; R.sub.5 and R.sub.5 ' independently are hydrogen or lower alkyl of 1 to 6 carbons; Y is oxygen or sulfur; Z is n-alkyl having 2 to 10 carbons, cyclo or branch-chained alkyl of 3 to 10 carbons, and straight chain alkenyl having 2 to 10 carbons, or cyclo or branched chained alkenyl of 3 to 10 carbons, and the Z-Y substituent is in a 1,2 (ortho) or 1,3 (meta) position on the phenyl ring relative to the ethene moiety; A is (CH.sub.2).sub.n where n is 0-5, lower branched chain alkyl having 3 to 6 carbons, cycloalkyl having 3 to 6 carbons, alkenyl having 2 to 6 carbons and 1 or 2 double bonds, alkynyl having 2 to 6 carbons and 1 or 2 triple bonds; B is COOH or a pharmaceutically acceptable salt thereof, COOR.sub.8, CONR.sub.9 R.sub.10, --CH.sub.2 OH, CH.sub.2 OR.sub.11, CH.sub.2 OCOR.sub.11, CHO, CH(OR.sub.12).sub.2, CHOR.sub.Type: GrantFiled: February 11, 1992Date of Patent: July 5, 1994Assignee: Allergan, Inc.Inventor: Roshantha A. S. Chandraratna
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Patent number: 5288928Abstract: There is disclosed a process for the asymmetrical hydrogenation of (E)-2-methyl-3-phenyl-2-propen-1-ol of formula ##STR1## wherein R.sub.1 is as defined herein, to give compounds of formula ##STR2## The catalyst is a neutral or cationic rhodium complex of a chiral atropisomeric phosphine.Type: GrantFiled: July 20, 1992Date of Patent: February 22, 1994Assignee: Ciba-Geigy CorporationInventors: Emil A. Broger, Yvo Crameri, Hans P. Isenring, Albert Pfiffner
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Patent number: 5284975Abstract: A method of preparing an .alpha.-d-phenylalkylbenzyl carbinol by the reaction of a phenylbenzyl ketone with an alkali metal enolate of an amide to form an aldol adduct, which is reduced and purified to form an .alpha.-d-phenylalkylbenzyl carbinol, wherein the carbinol so produced possesses analgesic activity. In an embodiment of the invention, a phenylbenzyl ketone is reacted with an alkali metal enolate of an amide to form an aldol adduct, which is reacted with an alkali metal salt of a secondary amine to form a dianion; the dianion is alkylated with an alkyl halide to form an .alpha.-isomer of an aldol adduct, which is reduced and purified to form an .alpha.-d-phenylalkylbenzyl carbinol possessing analgesic activity.Type: GrantFiled: October 8, 1992Date of Patent: February 8, 1994Assignee: Mallinckrodt Specialty Chemicals CompanyInventor: Jacob Mathew
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Patent number: 5281576Abstract: Described are aryl oxabicyclooctane derivatives and phenyl norbornane derivatives defined according to the structures: ##STR1## wherein N is an integer selected from the group consisting of 1 and 2, processes for preparing same, perfumery uses thereof and intermediates used in said processes which intermediates are defined according to the structures: ##STR2## wherein M is 0, 1 or 2 and X is chloro or bromo. Also described are the by-products having the structure: ##STR3## wherein P is 1 or 2 and uses thereof in perfumery.Type: GrantFiled: November 25, 1992Date of Patent: January 25, 1994Assignee: International Flavors & Fragrances Inc.Inventors: Anubhav P. S. Narula, John J. De Virgilio
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Patent number: 5276211Abstract: Described are aryl oxabicyclooctane derivatives and phenyl norbornane derivatives defined according to the structures: ##STR1## wherein N is an integer selected from the group consisting of 1 and 2, processes for preparing same, perfumery uses thereof and intermediates used in said processes which intermediates are defined according to the structures: ##STR2## wherein M is 0, 1 or 2 and X is chloro or bromo. Also described are the by-products having the structure: ##STR3## wherein P is 1 or 2 and uses thereof in perfumery.Type: GrantFiled: March 11, 1993Date of Patent: January 4, 1994Assignee: International Flavors & Fragrances Inc.Inventors: Anubhav P. S. Narula, John J. De Virgilio
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Patent number: 5262571Abstract: A process of synthesizing enantiomerically pure compounds defined by Formula V, ##STR1## which are useful as chiral auxiliaries is disclosed. The process comprises, first, combining a base of Formula Y.sup.- Z.sup.+ (Formula I), wherein Y.sup.- is an organic anion and Z.sup.+ is an inorganic cation, with a compound of Formula II, ##STR2## wherein R.sub.1 is a C.sub.1 -C.sub.4 alkyl group and R.sub.2 is the same as R.sub.1, or wherein R.sub.1 and R.sub.2 together form cyclopentane or cyclohexane, and wherein R.sub.3 is a substituted or unsubstituted aryl group, to form a compound defined by Formula III, ##STR3## then: (b) reacting the compound of Formula III with a cyclic epoxide defined by Formula IV, ##STR4## wherein n is 1, 2, or 3, to form a racemic mixture of a compound defined by Formula V.Type: GrantFiled: March 20, 1992Date of Patent: November 16, 1993Assignee: North Carolina State UniversityInventors: Daniel L. Comins, James M. Salvador
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Patent number: 5227543Abstract: Osmium-catalyzed methods of addition to an olefin are discussed. In the method of asymmetric dihydroxylation of the present invention, an olefin, a chiral ligand, an organic solvent, water, an oxidant, an osmium-containing compound and an organic soluble anion are combined. The presence of the organic soluble anion allows the asymmetric dihydroxylation reaction to occur rapidly and the amount of olefin that is diydroxylated is high with concomitantly less chiral ligand and osmium-containing catalyst than previously achieved.Type: GrantFiled: October 10, 1991Date of Patent: July 13, 1993Assignee: Massachusetts Institute of TechnologyInventors: K. Barry Sharpless, Wihelm K. Amberg
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Patent number: 5202503Abstract: Novel benzonitriles, benzaldehydes and benzyl alcohols of the formula I ##STR1## where R.sup.1 is methyl or ethyl, R.sup.2 is alkyl, alkenyl, cycloalkyl, cycloalkenyl, bicycloalkyl, bicycloalkenyl, or C.sub.1 -C.sub.5 -alkyl-substituted cycloalkyl, cycloalkenyl, bicycloalkyl or bicycloalkenyl, X is hydrogen, chlorine or fluorine and Z is --CN, CHO or ##STR2## where R.sup.3 is hydrogen, cyano, C.sub.2 -C.sub.4 -alkynyl, C.sub.2 -C.sub.4 -alkenyl or C.sub.1 -C.sub.4 -alkyl, with the proviso that R.sup.2 is not --CH.sub.2 --CH.dbd.CH--B when B is hydrogen, alkyl or alkenyl and at the same time R.sup.1 is methyl and Z is ##STR3## and with the proviso that R.sup.2 is not methyl or ethyl when R.sup.1 is methyl and at the same time Z is ##STR4## and furthermore with the proviso that R.sup.2 is not methyl when R.sup.1 is methyl or ethyl and at the same time Z is --CN or --CHO.Type: GrantFiled: November 12, 1991Date of Patent: April 13, 1993Assignee: BASF AktiengesellschaftInventors: Bernd Wolf, Hans Theobald, Norbert Goetz
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Patent number: 5187286Type: GrantFiled: March 25, 1991Date of Patent: February 16, 1993Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Buchmann, Josef Heindl, Wolfgang Frohlich, Roland Ekerdt
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Patent number: 5177245Abstract: Provided is a process for preparing optionally-substituted cyclohexenylhydroquinones starting from cyclohexanone.Type: GrantFiled: November 25, 1991Date of Patent: January 5, 1993Assignee: Eastman Kodak CompanyInventors: Dewey W. Fuller, Jr., Gether Irick, Jr.
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Patent number: 5169993Abstract: The invention provides cyclohexenol derivatives of the general formula ##STR1## in which n represents an integer from 0 to 5; each R represents a halogen atom, nitro, cyano, hydroxyl, alkyl, haloalkyl, alkoxy, haloalkoxy, amino, alkylamino, dialkylamino, alkoxycarbonyl, carboxyl, alkanoyl, alkylthio, alkylsulphinyl, alkylsulphonyl, carbamoyl, alkylamido, cycloalkyl or phenyl group; and R.sup.1, R.sup.2 and R.sup.3 independently represent a hydrogen atom or an alkyl group, with the provisos that when R.sup.1, R.sup.2 and R.sup.3 all represent a hydrogen atom then n is not 0 and, when R.sup.1, R.sup.2 and R.sup.3 all represent a hydrogen atom and n is 1, R does not represent a fluorine atom substituted at the 4-position of the phenyl ring; and a process for their preparation. Compounds of formula I are useful as intermediates in the preparation of certain fungicidal active cyclopentane derivatives.Type: GrantFiled: August 19, 1991Date of Patent: December 8, 1992Assignee: Shell Research LimitedInventor: Paul H. Briner
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Patent number: 5151548Abstract: Benzene derivatives of the general formula ##STR1## where Hal is halogen, R.sup.1 is a hydrocarbon radical of 1 to 18 carbon atoms, R.sup.2 is hydrogen or alkyl of 1 to 6 carbon atoms and X is hydrogen or halogen, are prepared by a process in which a toluene derivative of the general formula ##STR2## is electrochemically oxidized in the presence of an acid of the formula R.sup.2 --COOH (III). Novel benzene derivatives of the general formula ##STR3## where R.sup.3 is hydrogen or an R.sup.2 --CO-- radical but R.sup.1 cannot be methyl if X is hydrogen, and of the general formula ##STR4## where R.sup.4 is a branched or cyclic alkyl radical of 3 to 12 carbon atoms, but R.sup.4 cannot be isopropyl if X is hydrogen. The compounds of formulas IV and VI are intermediates for crop protecting agents, e.g. pyrethroids.Type: GrantFiled: June 12, 1989Date of Patent: September 29, 1992Assignee: BASF AktiengesellschaftInventors: Dieter Hermeling, Dieter Degner, Albrecht Harreus, Norbert Goetz, Jochen Wild, Hans Theobald, Bernd Wolf