Abstract: The invention relates to a method for the production of 2-coumarone or substituted 2-coumarones, whereby cyclohexanone or substituted cyclohexanone is reacted with a carboxyl-containing acylating agent a) to give methyl 2-(2-oxo-cyclohexyl)-2-hydroxyacetate or substituted methyl 2-(2-oxo-cyclohexyl)-2-hydroxyacetates, which are either a1) directly converted to 2-coumarone or substituted 2-coumarones by means of catalytic gas-phase dehydrogenation, or a2) dehydrated by means of azeotropic distillation under basic conditions, or by use of a strong acid, or a strongly acidic ion exchanger to a mixture of methyl 2-oxocyclohexylidenacetate and the enol-lactone of the 2-oxocyclohexylidenacetic acid, or a mixture of substituted methyl 2-oxocyclohexylidenacetate and the enol-lactone of the substituted 2-oxocyclohexylidenacetic acid, which is finally converted in turn by catalytic gas-phase dehydrogenation to 2-coumarone, or substituted 2-coumarones, or b) are directly converted under acidic or basic conditions into a
Type:
Application
Filed:
November 15, 2002
Publication date:
September 11, 2003
Inventors:
Michael Stanek, Peter Hildebrand, Curt Zimmermann, Marianne Castelijns
Abstract: Novel carbohydrate-based compounds with an attached ring system that have antimicrobial or cytostatic activity. The compounds are administered to humans and animals for the treatment or amelioration of bacterial, fungal, viral or protozoal infections or tumors.
Type:
Application
Filed:
October 15, 2001
Publication date:
August 21, 2003
Inventors:
Benedikt Sas, Johan Van der Eycken, Johan Van hemel, Petra Blom, Jan Vandenkerckhove, Bart Ruttens
Abstract: The present invention is directed to compounds, pharmaceutical compositions, and methods for modulating processes mediated by AR and PR. More particularly, the invention relates to nonsteroidal compounds and compositions that are high affinity, high specificity agonists, partial agonists (i.e., partial activators and/or tissue-specific activators) and antagonists for AR and PR. Also provided are methods of making such compounds and pharmaceutical compositions, as well as critical intermediates used in their synthesis.
Type:
Application
Filed:
November 18, 2002
Publication date:
July 10, 2003
Inventors:
Lin Zhi, Christopher Tegley, Barbara Pio, Cornelis Arjan Van Oerveren, Mehrnouch Motamedi, Esther Martinborough, Sarah West, Robert Higuchi, Lawrence G. Hamann, Luc Farmer
Abstract: The invention relates to a process for the enantioselective preparation of tolterodine and analogues and salts thereof comprises the steps of:
a) enantioselectively reducing the carbonyl function in a compound of formula (II):
wherein R1, R2 and R3 independently of each other are hydrogen, methyl, methoxy, hydroxy, hydroxymethyl, carbamoyl, sulphamoyl or halogen, to form an enantiomerically enriched compound of formula (IIIa) or (IIIb):
wherein R1, R2 and R3 are as defined above;
b) subjecting the compound of formula (IIIa) or (IIb) to a sigmatropic rearrangement to form a corresponding enantiomerically enriched compound of formula (IVa) or (IVb):
wherein R1, R2 and R3 are as defined above;
c) subjecting the compound of formula (IVa) or (IVb) to a Baeyer-Villiger oxidation to form a corresponding enantiomerically enriched compound of the general formula (Va) or (Vb):
wherein R1, R2 and R3 are as defined above;
d) converting the compou
Abstract: The present invention discloses new and useful compounds including methyl p-hydroxyphenyllactate, its analogues, chemical derivatives and chemically related compounds and their use as antitumor and immune suppressive agents, as inhibitors of proliferative cell growth and as prophylactic agents to inhibit and prevent cancer and non-malignant cell growth.
Abstract: The invention relates to a flavonoid ester. This flavonoid ester results from the reaction product of at least one flavonoid selected from the group consisting of a flavonoid with a ketone group in the 4-position, a salt, ester or ether of such a flavonoid, and a C-heteroside and/or O-heteroside derivative of such a flavonoid, with the proviso that this flavonoid contains at least one free alcohol group, with an organic monoacid having from 3 to 30 carbon atoms. These flavonoid esters constitute useful active principles for the manufacture of cosmetic, dermopharmaceutical, pharmaceutical, dietetic or agri-foodstuff compositions.
Type:
Grant
Filed:
April 10, 2001
Date of Patent:
October 29, 2002
Assignee:
Coletica
Inventors:
Eric Perrier, Anne-Marie Mariotte, Ahcène Boumendjel, Delphine Bresson-Rival
Abstract: Protecting groups derived from a halogenated coumarin group, a quinoline-2-one group, a xanthene group, a thioxanthene group, a selenoxanthene group, or an anthracene group are described. The protecting groups is photolabile and can be removed by irradiating the group with light, such as flash photolysis with ultraviolet radiation or pulsed infrared radiation.
Type:
Grant
Filed:
November 20, 1998
Date of Patent:
October 29, 2002
Assignee:
The Regents of the University of California
Abstract: Provided is a process for producing an isocoumarin-3-yl-acetic acid derivative, characterized by reacting a homophthalic acid derivative represented by a formula: 1
Abstract: Described are bicyclic lactones, both fused ring lactones defined according to the generic structure:
and spiro lactones defined according to the generic structure:
uses thereof in augmenting, enhancing or imparting aromas in or to perfume compositions, perfumed articles, colognes and perfumed polymers; processes for preparing such bicyclic lactones and intermediates therefor.
In the structure:
Z is one of the moieties:
one of R1 or R3 is methyl and the other is hydrogen; and R4, R5, R6, R7, R8 and R9 are hydrogen or nonadjacent C1-C3 alkyl.
Type:
Grant
Filed:
November 10, 2000
Date of Patent:
October 8, 2002
Assignee:
International Flavors & Fragrances Inc.
Inventors:
Richard A. Weiss, Mark A. Sprecker, Marie R. Hanna, Charles E. J. Beck, Harold W. Jackson
Abstract: A process for the preparation of 3-isochromanone which comprises contacting an o-xylene-&agr;,&agr;′-dihalide with carbon monoxide, in the presence of a catalyst and a hindered amine base in a liquid medium comprising water and a tertiary alcohol.
Type:
Application
Filed:
March 16, 2001
Publication date:
October 3, 2002
Inventors:
Raymond Vincent Heavon Jones, Alan John Whitton, Jennifer Ann White, David John Ritchie, Robin Fieldhouse, Kirstin Maccormick, Logan Thomson Nisbet, Paul Richard Evans, Colin John Bennie
Abstract: The present invention provides a variety of methods that are based on stereoselective epoxidation of an olefin by an epoxidizing agent derived from a reaction between an oxidizing agent and a chiral ketone. For example, present invention provides methods for producing an epoxide from an olefin, for increasing a relative concentration of at least one stereoisomer of an olefin, and for stereoselectively producing an &agr;-acyloxy carbonyl compound.
Type:
Application
Filed:
January 7, 2002
Publication date:
September 19, 2002
Applicant:
Colorado State University Research Foundation
Abstract: An organic light emitting display is provided which comprises as an emitting layer a fluorescent dye having at least one amine moiety substituted with two aryl groups. Also provided are new fluorescent compounds having N-aryl substituents which exhibit reduced pH sensitivity and enhanced stability to protonation.
Type:
Application
Filed:
March 6, 2001
Publication date:
September 12, 2002
Applicant:
International Business Machines Corporation
Inventors:
Sally Ann Swanson, Gregory Michael Wallraff
Abstract: Disclosed are new organometallic complex molecules having light-emitting and electron-transporting characteristics. Also disclosed is organic EL (electroluminescent) devices using these organometallic complex molecules as electron-transporting materials. The organometallic complex molecules are used to form a light-emitting layer with or without doping of another light-emitting material. The organometallic complex molecules can also be used in an electron-transporting layer of the organic EL device. The organic EL devices incorporating the organometallic complex molecules have high thermal stability.
Type:
Grant
Filed:
March 31, 2000
Date of Patent:
May 7, 2002
Assignee:
LG Chem, Ltd.
Inventors:
Kongkyeom Kim, Sehwan Son, Okhee Kim, Seok-Hee Yoon, Hyo-Seok Kim, Jaesoon Bae, Youn-Gu Lee
Abstract: Protecting groups derived from a halogenated coumarin group, a quinoline-2-one group, a xanthene group, a thioxanthene group, a selenoxanthene group, or an anthracene group are described. The protecting groups is photolabile and can be removed by irradiating the group with light, such as flash photolysis with ultraviolet radiation or pulsed infrared radiation.
Abstract: The present invention is directed to novel methods for identifying small molecule ligands that are capable of binding with high affinity to a biological target molecule of interest. High affinity binding ligands identified by the described methods find use, for example, as small molecule lead compounds that may they themselves be, or may give rise to, novel therapeutic drugs. More specifically, the subject invention is directed to methods for identifying a ligand that binds to a target biological molecule of interest, wherein a population of small organic compounds are selected and then “pre-screened” to identify those that are capable of binding to the molecular target.
Type:
Grant
Filed:
March 27, 1998
Date of Patent:
February 5, 2002
Assignee:
The Regents of the University of California
Abstract: Method for identifying a drug lead compound that inhibits binding of target bioogical molecules (TBM) by contacting TBM with members of a library of candidate cross-linked target binding fragments (CXBF), each CXBF having at least two candidate target bindig fragments (CTBF), which are inhibitors of binding, linked to a cross-linker, and selecting CXBF that inhibit the binding of the TBM to a greater extent than either of the individual CTBF linked to said cross-linker, wherein the library of CXBF is produced by: (a) screening a population of CTBF capable of being chemically cross-linked by a cross-linker to identify a subpopulation of the CTBF that inhibit binding of the TBM; and (b) chemically cross-linking members of the subpopulation of CTBF or structurally related analogs thereof with a cross-linker to provide a library of CXBF, wherein at least one linking group comprises an oxime ether linking group.
Type:
Grant
Filed:
March 26, 1999
Date of Patent:
February 5, 2002
Assignee:
The Regents of the University of California
Abstract: The invention relates to a process for the enantioselective preparation of tolterodine and analogues and salts thereof comprises the steps of:
Abstract: The invention relates to a flavonoid ester. This flavonoid ester results from the reaction product of at least one flavonoid selected from the group consisting of a flavonoid with a ketone group in the 4-position, a salt, ester or ether of such a flavonoid, and a C-heteroside and/or O-heteroside derivative of such a flavonoid, with the proviso that this flavonoid contains at least one free alcohol group, with an organic monoacid having from 3 to 30 carbon atoms. These flavonoid esters constitute useful active principles for the manufacture of cosmetic, dermopharmaceutical, pharmaceutical, dietetic or agri-foodstuff compositions.
Type:
Grant
Filed:
July 10, 1998
Date of Patent:
May 22, 2001
Assignee:
Coletica
Inventors:
Eric Perrier, Anne-Marie Mariotte, Ahcéne Boumendjel, Delphine Bresson-Rival
Abstract: The enzyme substrate according to this invention has within its molecule both a group to be cleaved by an enzyme reaction and a group that forms a strongly fluorescent coumarin derivative through intramolecular lactonization when cleaved by the enzyme reaction. Furthermore, the method for determining an enzyme activity according to this invention comprises conducting the enzyme reaction by the use of the enzyme substrate of the invention and determining the enzyme activity by means of the measurement of fluorescence of the coumarin derivative formed.
Abstract: Novel fluorescent substrates of human cytochrome P450 enzymes are provided. Also provided are methods for their manufacture and use. These substrates are useful in assessing cytochrome P450 enzyme activity and in selecting compounds which inhibit cytochrome P450 enzyme activity and, in particular, for identifying potential adverse drug interactions which are mediated by inhibition of cytochrome P450 enzyme activity. The compounds are particularly useful for assessing cytochrome P450 CYP3A enzyme activity.
Abstract: The present invention intends to provide a method for producing 3-isochromanones represented by formula (II) useful as a synthetic starting material of medicals or agricultural chemicals and the cyano compound represented by formula (I) by an industrially advantageous method in a high yield.
Disclosed herein is a method for manufacturing a 3-isochromanone represented by the following formula (II):
(wherein R2, R3, R4 and R5 each independently represents a hydrogen atom, a halogen atom, an alkyl group or an alkoxy group),
said method is characterized by comprising the steps of:
hydrolyzing a cyano compound represented by formula (I):
(wherein R1 represents a hydrogen atom, an alkyl group or an aryl group, and R2, R3, R4 and R5 have the same meanings as defined above) and subjecting the hydrolyzate to intra-molecular cyclization.
Abstract: The invention discloses a fluorescent bead that can be used for determining the temperature and/or metabolic state of a single cell contained in a cell/tissue sample. The fluorescent bead contains at least one temperature-sensitive fluorophore. The invention also includes methods of monitoring cellular metabolism and methods of diagnosing abnormal metabolism of a cell.
Abstract: The present invention provides novel haloenol lactones that are effective as active site inhibitors of cholesterol esterase. By inhibiting cholesterol esterase the inhibitors of the present invention provide a new approach to the treatment of hypercholesterolemia through limiting the bioavailability of dietary cholesterol.
Abstract: The present invention relates to a compound represented by general formula (I) or a pharmaceutically acceptable salt or ester thereof: ##STR1## wherein each of R.sup.1 and R.sup.2 is independently a hydrogen atom, a C.sub.1 -C.sub.16 alkyl group, a C.sub.2 -C.sub.10 alkenyl group, a C.sub.3 -C.sub.6 alkynyl group, a C.sub.6 -C.sub.12 aryl group, a C.sub.7 -C.sub.15 aralkyl group or a heterocyclic group which is not substituted, a C.sub.1 -C.sub.16 alkyl group, a C.sub.2 -C.sub.10 alkenyl group, a C.sub.3 -C.sub.6 alkynyl group, a C.sub.6 -C.sub.12 aryl group, a C.sub.7 -C.sub.15 aralkyl group or a heterocyclic group which has substituent(s), or a group represented by --Y--R.sup.3 (provided that when R.sup.2 is a hydrogen atom, R.sup.1 is not a methyl group or an acetyl group; when R.sup.2 is an acetyl group, R.sup.1 is not a methyl group), an antifungal agent containing it as an active ingredient and an antifungal composition containing it and an azole type antifungal agent.
Abstract: Good yields and selectivities are achieved in a process for preparing an isochroman-3-one of the formula (I) ##STR1## by reacting a 1,3-dihydroisobenzofuran of the formula (II) ##STR2## with carbon monoxide at a CO pressure of from 0.1 to 20 MPa in the presence of an ionic halide, a palladium catalyst and a dipolar aprotic solvent.
Type:
Grant
Filed:
January 27, 1999
Date of Patent:
December 14, 1999
Assignee:
Clariant GmbH
Inventors:
Holger Geissler, Daniel Decker, Peter Gross
Abstract: Fluorescent enzyme substrates are provided. The substrates are derivatives of coumarin having an enzyme cleavable group at position 7 and a hydrophilic amide group at position 4. The compounds are highly water soluble, stable at ambient and reduced temperatures and fluoresce upon cleavage by an enzyme.
Type:
Grant
Filed:
March 10, 1998
Date of Patent:
December 7, 1999
Assignee:
Abbott Laboratories
Inventors:
Jeffrey B. Huff, Barbara T. Merchant, Carolyn R. Mullen, Seshagiri R. Tata Venkata
Abstract: This invention relates to compounds that are antagonists of dopamine D4 receptors, and to methods of treating psychosis and schizophrenia using a compound that is an antagonist of dopamine D4 receptors.
Type:
Grant
Filed:
August 8, 1997
Date of Patent:
June 29, 1999
Assignee:
Warner-Lambert Company
Inventors:
David Thomas Connor, Stephen Joseph Johnson, Suzanne Ross Kesten, Steven Robert Miller, Paul Charles Unangst, Lawrence David Wise
Abstract: Viral and bacterial contaminants present in biological solutions are inactivated by mixing one of a novel class of photosensitizer with said solution and irradiating the mixture.
Type:
Grant
Filed:
June 5, 1995
Date of Patent:
February 9, 1999
Assignee:
Baxter International Inc.
Inventors:
Sang Chul Park, Raymond P. Goodrich, Jr., Nagender Yerram, Samuel O. Sowemimo-Coker, Matthew S. Platz, Brian M. Aquila
Abstract: The instant invention is concerned with acetylphenols which are useful as antiobesity and antidiabetic compounds. Compositions and methods for the use of the compounds in the treatment of diabetes and obesity and for lowering or modulating triglyceride levels and cholesterol levels or raising high density lipoprotein levels or for increasing gut motility or for treating atherosclerosis are also disclosed.
Type:
Grant
Filed:
January 31, 1997
Date of Patent:
January 12, 1999
Assignee:
Merck & Co., Inc.
Inventors:
Alan D. Adams, Gregory D. Berger, Jeffrey P. Bergman, Joel P. Berger, Wei Han, Mark D. Leibowitz, David E. Moller, Conrad Santini, Soumya P. Sahoo, Richard L. Tolman, Jonthan R. Young
Abstract: A process for preparing compounds useful as intermediates used for preparing lubricant and fuel additives. The intermediates include the products prepared by the process and dilactones.
Type:
Grant
Filed:
December 18, 1997
Date of Patent:
January 5, 1999
Assignee:
The Lubrizol Corporation
Inventors:
Jeffery G. Dietz, Mark R. Baker, Paul E. Adams
Abstract: The present invention comprises 6,8-difluoro-7-hydroxycoumarins and derivatives of 6,8-difluoro-7-hydroxycoumarins, including reactive dyes, dye-conjugates and enzyme substrates. These fluorine-substituted fluorescent dyes typically possess greater photostability and lower pH sensitivity in the physiological pH range than their nonfluorinated analogs, exhibit less fluorescence quenching when conjugated to a substance, possess absorption and emission spectra that closely match those of their nonfluorinated analogs, and also exhibit higher quantum yields than their nonfluorinated analogs.
Type:
Grant
Filed:
November 15, 1996
Date of Patent:
November 3, 1998
Assignee:
Molecular Probes, Inc.
Inventors:
Kyle R. Gee, Richard P. Haugland, Wei-Chuan Sun
Abstract: Hydroxybenzaldehydes, for example salicylaldehyde, are prepared in high yields by oxidizing the corresponding hydroxybenzyl alcohols, e.g., saligenol, with molecular oxygen or an oxygen-containing gas, in liquid phase, in an aqueous reaction medium containing an alkali, in the presence of (i) a catalytically effective amount of a platinum catalyst and (ii) a cocatalytically effective amount of boron and bismuth compounds.
Abstract: Viral and bacterial contaminants present in biological solutions are inactivated by mixing one of a novel class of photosensitizer with said solution and irradiating the mixture.
Type:
Grant
Filed:
April 21, 1995
Date of Patent:
August 4, 1998
Assignee:
Baxter International Inc.
Inventors:
Sang Chul Park, Raymond P. Goodrich, Jr., Nagender Yerram, Samuel O. Sowemimo-Coker, Matthew S. Platz, Brian M. Aquila
Abstract: A process for preparing compounds useful as intermediates used for preparing lubricant and fuel additives. The intermediates include the products prepared by the process and dilactones.
Type:
Grant
Filed:
April 10, 1997
Date of Patent:
July 28, 1998
Assignee:
The Lubrizol Corporation
Inventors:
Jeffry G. Dietz, Mark R. Baker, Paul E. Adams
Abstract: A process for preparing compounds useful as intermediates used for preparing lubricant and fuel additives. The intermediates include the products prepared by the process and dilactones.
Type:
Grant
Filed:
November 21, 1996
Date of Patent:
April 14, 1998
Assignee:
The Lubrizol Corporation
Inventors:
Jeffry G. Dietz, Mark R. Baker, Paul E. Adams
Abstract: New retinoid compounds, as coumarin retinoids and/or purine retinoids and compositions thereof, are provided which exhibit therapeutic and/or biological activity on cancer or precancer cells, as well as to methods of use of same.
Type:
Grant
Filed:
June 7, 1995
Date of Patent:
February 10, 1998
Assignee:
Institute of Materia Medica, an institute of the Chinese Academy of Medical Sciences
Abstract: The present invention provides for novel reagents whose fluorescence increases in the presence of particular proteases. The reagents comprise a characteristically folded peptide backbone each end of which is conjugated to a fluorophore. When the folded peptide is cleaved, as by digestion with a protease, the fluorophores provide a high intensity fluorescent signal at a visible wavelength. Because of their high fluorescence signal in the visible wavelengths, these protease indicators are particularly well suited for detection of protease activity in biological samples, in particular in frozen tissue sections. Thus this invention also provides for methods of detecting protease activity in situ in frozen sections.
Abstract: The present invention relates to compounds of formula I which are 4-hydroxy-benzopyran-2-ones and 4-hydroxy-cycloalkyl?b!pyran-2-ones useful for inhibiting a retrovirus in a mammalian cell infected with said retrovirus. ##STR1## Wherein R.sub.10 and R.sub.
Type:
Grant
Filed:
August 4, 1995
Date of Patent:
November 11, 1997
Assignee:
Pharmacia & Upjohn Company
Inventors:
Paul Kosta Tomich, Michael John Bohanon, Steven Ronald Turner, Joseph Walter Strohbach, Suvit Thaisrivongs, Richard C. Thomas, Karen Rene Romines, Chih-Ping Yang, Paul Adrian Aristoff, Harvey Irving Skulnick, Paul D. Johnson, Ronald B. Gammill, Qingwei Zhang, Gordon L. Bundy, David John Anderson, Lee S. Banitt
Abstract: The invention provides lanthanide chelates capable of intense luminescence. The celates comprise a lanthanide chelator covalently joined to a coumarin-like or quinolone-like sensitizer. Exemplary sensitzers include 2- or 4-quinolones, 2- or 4-coumarins, or derivatives thereof e.g. carbostyril 124 (7-amino-4-methyl-2-quinolone), coumarin 120 (7-amino-4-methyl-2-coumarin), coumarin 124 (7-amino-4-(trifluoromethyl)-2-coumarin), aminomethyltrimethylpsoralen, etc.The chelates form high affinity complexes with lanthanides, such as terbium or europium, through chelator groups, such as DTPA. The chelates may be coupled to a wide variety of compounds to create specific labels, probes, diagnostic and/or therapeutic reagents, etc. The chelates find particular use in resonance energy transfer between chelate-lanthanide complexes and another luminescent agent, often a fluorescent non-metal based resonance energy acceptor.
Type:
Grant
Filed:
June 29, 1994
Date of Patent:
April 22, 1997
Assignee:
The Regents of the University of California
Abstract: Modulators of neurotransmitter release including substituted guanidines, N"-aminoguanidines, and N,N'N",N'"-tetrasubstituted hydrazinedicarboximidamides, and pharmaceutical compositions thereof are disclosed. Also disclosed are methods involving the use of such neurotransmitter release modulators for the treatment or prevention of pathophysiologic conditions characterized by the release of excessive or inappropriate levels of neurotransmitters. Also disclosed are screening assays for compounds which selectively inhibit glutamate release. Also disclosed are methods of blocking voltage sensitive sodium and calcium channels in mammalian nerve cells.
Type:
Grant
Filed:
June 5, 1995
Date of Patent:
March 25, 1997
Assignee:
Cambridge NeuroScience, Inc.
Inventors:
Stanley M. Goldin, Subbarao Katragadda, Lain-Yen Hu, N. Laxma Reddy, James B. Fischer, Andrew G. Knapp, Lee D. Margolin
Abstract: Conjugates of fluorescent labels with specific, selective, and high affinity ligands for receptors have been synthesized and used to directly measure binding to receptors.
Type:
Grant
Filed:
March 2, 1994
Date of Patent:
November 19, 1996
Assignee:
Pharmaceutical Discovery Corporation
Inventors:
R. Tyler McCabe, Christopher A. Rhodes, Bruce F. DeCosta
Abstract: Compounds having the Formula I: ##STR1## are inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating angina, cerebral spasm, glomerular nephritis, hepatitis, endotoxemia, uveitis, and allograft rejection and in preventing the formation of atherosclerotic plaques.
Type:
Grant
Filed:
February 15, 1995
Date of Patent:
November 19, 1996
Assignee:
Merck Frosst Canada, Inc.
Inventors:
Richard Friesen, Yves Ducharme, Daniel Dube', Carole Lepine, Daniel Delorme, Pierre Hamel
Abstract: An optically active (S)- or (R)-pentane compound of the general formula (11): ##STR1## wherein R.sub.11, R.sub.12 and R.sub.13 independently represent a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, R.sub.14 represents a hydroxy, protected hydroxy or oxo group, if R.sub.14 is an oxo group, the ring denoting benzene in the above formula (11) is benzoquinone, R.sub.15 represents a hydrogen atom, hydroxy or acyloxy group, R.sub.16 represents a hydroxy or acyloxy group, and the chiral central carbon marked with a symbol * in said formula (11) alternatively has one of an R-configuration and an S-configuration, is disclosed. Further, intermediate products of the compound of the formula (11) are also disclosed. Still further, a process for manufacturing the above compounds is disclosed. The compound of the formula (11) is easily synthesized from an easily available optically active starting material.