Preparing Compound Containing A Prostaglandin Nucleus Patents (Class 435/63)
  • Patent number: 8790871
    Abstract: Disclosed herein are methods of detecting and predicting diastolic heart failure and predicting congestive heart failure comprise protease and protease inhibitor profiling.
    Type: Grant
    Filed: April 24, 2007
    Date of Patent: July 29, 2014
    Assignee: MUSC Foundation for Research Development
    Inventors: Francis G. Spinale, Robert E. Stroud, Michael R. Zile
  • Patent number: 8663561
    Abstract: An automated apparatus and method for analyzing liquid samples by forming discrete sample aliquots (boluses) in an elongated conduit which contains a hydrophobic carrier liquid. Aliquots may be analyzed by adding at least one reagent to the sample aliquot that reacts selectively with an analyte contained therein. The reaction product, which is selective for the analyte of interest and proportional to its concentration, is measured with an appropriate detector. Intrinsic sample properties of the sample may also be measured without the need for adding chemical reagents. The invention enables simple and accurate testing of samples using time honored wet-chemical analysis methods in microliter volume regimes while producing remarkably small volumes of waste.
    Type: Grant
    Filed: February 19, 2010
    Date of Patent: March 4, 2014
    Inventor: Charles J. Patton
  • Patent number: 8252599
    Abstract: Sample processing units useful for mixing and purifying materials, such as fluidic materials are provided. A sample processing unit typically includes a container configured to contain a sample comprising magnetically responsive particles, and one or more magnets that are in substantially fixed positions relative to the container. A sample processing unit also generally includes a conveyance mechanism configured to convey the container to and from a position that is within magnetic communication with the magnet, e.g., such that magnetically responsive particles with captured analytes can be retained within the container when other materials are added to and/or removed from the container. Further, a sample processing unit also typically includes a rotational mechanism that is configured to rotate the container, e.g., to effect mixing of sample materials disposed within the container. Related carrier mechanisms, sample processing stations, systems, and methods are also provided.
    Type: Grant
    Filed: August 30, 2011
    Date of Patent: August 28, 2012
    Assignee: Ibis Biosciences, Inc.
    Inventors: Steven A. Hofstadler, Jared J. Drader, Jose R. Gutierrez, Paul J. Gleason, Rex O. Bare, Robert D. Miller, Jeffrey C. Smith
  • Publication number: 20120142047
    Abstract: An assembly capable of capturing and purifying expressed biological products during or at the end of a bioreaction cycle is disclosed wherein a binding resin is kept separated from the contents of the bioreactor allowing capturing, harvesting and purification of biological products in a bioreactor; the invention additionally provides means of removing undesirable metabolic products as well as provides for efficient loading of chromatography columns.
    Type: Application
    Filed: November 29, 2011
    Publication date: June 7, 2012
    Applicant: Therapeutic Proteins, Inc.
    Inventor: Sarfaraz K. Niazi
  • Patent number: 7820386
    Abstract: A method for screening cancer comprises the following steps: (1) providing a test specimen; (2) detecting the methylation state of the CpG sequence in at least one target gene within the genomic DNA of the test specimen, wherein the target genes is consisted of SOX1, PAX1, LMX1A, NKX6-1, WT1 and ONECUT1; and (3) determining whether there is cancer or cancerous pathological change in the specimen based on the presence or absence of the methylation state in the target gene; wherein method for detecting methylation state is methylation-specific PCR (MSP), quantitative methylation-specific PCR (QMSP), bisulfite sequencing (BS), microarrays, mass spectrometer, denaturing high-performance liquid chromatography (DHPLC), and pyrosequencing.
    Type: Grant
    Filed: June 15, 2007
    Date of Patent: October 26, 2010
    Assignee: National Defense Medical Center
    Inventor: Hung-Cheng Lai
  • Patent number: 7695629
    Abstract: The present invention provides methods and apparatus for separating and/or analyzing fluids of interest. According to principles of the present invention, fluid analysis is accomplished with microfluidic devices and may be reported in real-time or near real-time in a subterranean environment. In addition or alternative to oilfield applications, the principles of the present invention contemplate separation in a laboratory or other environment for biological sample separation and analytical chemistry applications. The present invention is capable of separating liquid-liquid mixtures or emulsions in a microfluidic device without fouling.
    Type: Grant
    Filed: February 20, 2009
    Date of Patent: April 13, 2010
    Assignee: Schlumberger Technology Corporation
    Inventors: Philippe Salamitou, Joyce Wong, Bhavani Raghuraman, Jagdish Shah, Ronald E. G. Van Hal, Robert J. Schroeder, Patrick Jean René Tabeling
  • Patent number: 7666609
    Abstract: This invention relates to monoclonal antibodies that recognize an antigen specific to melanocytic lesions. These antibodies are useful in methods of isolating melanoma cells and diagnosing melanocytic lesions. These antibodies are also useful for immunotherapy against melanoma.
    Type: Grant
    Filed: July 26, 2001
    Date of Patent: February 23, 2010
    Assignee: Shanghai CP GuoJian Pharmaceutical Co. Ltd.
    Inventors: Yajun Guo, Jing Ma
  • Patent number: 7608417
    Abstract: A cell electro-physiological sensor includes a sensor chip including a partition board having a first surface and a second surface opposite to the first surface, a member for forming a first region provided on the first surface of the partition board, and a member for forming a second region provided on the second surface of the partition board. The partition board has a through-hole provided therein, the through-hole having a first opening which opens to the first surface, a second opening which opens to the second surface, and a wall. The first region contacts the first opening of the through-hole. The first region is arranged to contain cell suspension. The atomic ratio of carbon at the first surface of the partition board is not greater than 15 atomic percent of the composition of the first surface. The cell electro-physiological sensor causes the cell to be tightly held at the first opening of the through-hole in the partition board, thereby measuring a potential of the cell efficiently.
    Type: Grant
    Filed: November 14, 2005
    Date of Patent: October 27, 2009
    Assignee: Panasonic Corporation
    Inventors: Masaya Nakatani, Hiroshi Ushio, Soichiro Hiraoka, Abdellah Menikh
  • Patent number: 7605144
    Abstract: This invention provides novel compounds selected from the group consisting of a 1,5-substituted pyrimidine derivative or analog and substituted furano-pyrimidone analogs. The compounds are useful to treat or prevent diseases such as cancer.
    Type: Grant
    Filed: October 7, 2003
    Date of Patent: October 20, 2009
    Assignee: Celmed Oncology (USA), Inc.
    Inventors: H. Michael Shepard, Ming Fai Chan, Michael P. Groziak
  • Patent number: 7257243
    Abstract: A method for the analysis of a biological sample for determining a change thereof relative to a healthy biological sample includes creating a first image of the biological sample at a first acquisition modality and creating a second image of the biological samples at a second acquisition modality. The first image is classified on the basis of a first pre-determined parameter, and the second image is classified on the basis of a second pre-determined parameter, the first image being classified independently of the second image. Then, depending on the classification results, it is determined if the biological sample comprises a change relative to a healthy biological sample.
    Type: Grant
    Filed: May 14, 2002
    Date of Patent: August 14, 2007
    Assignee: Fraunhofer-Gesellschaft zur Foerderung der angewandten Forschung e.V.
    Inventors: Robert Schmidt, Thomas Wittenberg, Heinz Gerhaeuser, Klaus Spinnler
  • Patent number: 7217537
    Abstract: A method to increase carotenoid production in carotenogenic microbial host cells is provided by down-regulating or disrupting glycogen synthesis. Disruption of glycogen synthase activity in a carotenogenic microbial host cell significantly increased carotenoid production. Carotenogenic microorganisms are also provided that have been optimized for the production of carotenoid compounds through the down-regulation and/or disruption of glycogen synthase activity.
    Type: Grant
    Filed: September 15, 2005
    Date of Patent: May 15, 2007
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Edward S. Miller, Jr., James M. Odom, Pamela L. Sharpe
  • Patent number: 7169580
    Abstract: A single protein which is the substance of the PGE2 synthesis activity in brain soluble fractions of LPS administered rats has been purified and identified. The protein has an activity of synthesizing PGE2 from PGH2, and further, has an activity of synthesizing PGE2 from arachidonic acid in combination with COX.
    Type: Grant
    Filed: August 25, 2000
    Date of Patent: January 30, 2007
    Assignees: Chugai Seiyaku Kabushiki Kaisha
    Inventors: Ichiro Kudo, Makoto Murakami, Sachiko Oh-ishi
  • Patent number: 7144710
    Abstract: Methods for detecting the inflammatory biomarkers molecule CD 163 in biological samples are provided. Also provided are methods for monitoring the course of an inflammatory process or condition in a patient and compositions and methods for preventing and treating inflammation and inflammatory processes.
    Type: Grant
    Filed: March 27, 2001
    Date of Patent: December 5, 2006
    Assignee: Trustees of Dartmouth College
    Inventors: Paul M. Guyre, Peter M. Morganelli, Nicholas J. Goulding
  • Patent number: 6846807
    Abstract: Development of colorectal neoplasia in a patient subject or predisposed to colorectal neoplasia is reduced by the steps of (a) determining a patient is subject or predisposed to colorectal neoplasia; and (b) enterically delivering into the gut of the person an effective amount of an aminoglycoside antibiotic having poor gut absorption, whereby the development of the colorectal neoplasia is reduced as compared with otherwise similar non-treated patients.
    Type: Grant
    Filed: July 25, 2003
    Date of Patent: January 25, 2005
    Assignee: Board of Regents, The University of Texas System
    Inventors: Jonathan Graff, Matthew Wieduwilt
  • Patent number: 6713268
    Abstract: Methods to identify agents having ocular hypotensive activity which have reduced or absent ability to stimulate iridial hyperpigmentation are disclosed. The methods reside in part in detecting the ability of a test compound to interact with the FP receptor.
    Type: Grant
    Filed: June 26, 2001
    Date of Patent: March 30, 2004
    Assignee: Allergan, Inc.
    Inventors: David F. Woodward, Licheng Shi, Achim H-P Krauss, Clayton S. Spada, Sheila Mac Neil, Linda C. Smith-Thomas
  • Publication number: 20030064493
    Abstract: Isolated PGE synthase, provided from encoding nucleic acid. Methods of production and use. Assays for modulators, especially inhibitors, of PGE synthase activity.
    Type: Application
    Filed: March 28, 2002
    Publication date: April 3, 2003
    Inventors: Per-Johan Jakobsson, Bengt Samuelsson, Ralf Morgenstern, Anthony Ford-Hutchinson, Joseph Mancini
  • Publication number: 20020031522
    Abstract: Overexpression of a CRAF1 (CD40 receptor-associated factor 1) gene truncated by 323 to about 414 amino acids at the amino inhibits CD40-mediated cell activation, and is used to treat conditions characterized by an unwanted level of CD40-mediated intracellular signaling.
    Type: Application
    Filed: March 10, 1997
    Publication date: March 14, 2002
    Inventors: DAVID BALTIMORE, GENHONG CHENG, ZHENG-SHENG YE, SETH LEDERMAN, AILEEN CLEARY
  • Patent number: 6261766
    Abstract: This invention relates to the detection of prostate-specific antigen (PSA) in female breast tumor extract as a prognostic or predictive indicator for breast carcinoma. The presence of prostate-specific antigen in breast tumours is associated with earlier disease stage, younger women and better survival. PSA is associated with tumors which have estrogen and/or progersterone receptors.
    Type: Grant
    Filed: September 26, 2000
    Date of Patent: July 17, 2001
    Assignee: Nordion International, Inc.
    Inventor: Eleftherios Diamandis
  • Patent number: 6214628
    Abstract: In accordance with the present invention, a method of conducting an assay of a sample containing an analyte of interest includes the step of forming a mixture so as to bring a metal-ligand complex into interactive proximity with the sample containing the analyte of interest. The mixture is irradiated with electromagnetic light energy so as to cause emission of light indicative of the analyte of interest. The emitted light is measured, and the measurement of the emitted light is utilized to measure the analyte of interest. The metal-ligand complex can be [Re(bcp)(CO)3(4-COOHPy)]+, [Os(phen)2(aphen)]2+, [Os(tpy)(triphos)]2+, [Os(tppz)2]2+, and [Os(ttpy)2]2+, or the like. Also, the present invention is directed to a metal-ligand complex of the formula [Re(bcp)(CO)3(4-COOHPy)]+.
    Type: Grant
    Filed: January 14, 1998
    Date of Patent: April 10, 2001
    Inventors: Joseph R. Lakowicz, Felix Castellano, Zakir Murtaza
  • Patent number: 6083501
    Abstract: A drug for prevention and therapy of diseases caused by fibrinoid formation or thrombus formation, as well as a model animal of fibrinoid formation or thrombus formation in the lung is disclosed. The drug for preventing and treating diseases caused by fibrinoid formation or thrombus formation in the lung according to the present invention comprises an inhibitor of interleukin 6 as an effective ingredient. The model animal of the diseases caused by fibrinoid formation or thrombus formation in the lung is a rat in which fibrinoid formation or thrombus formation actually occurs by induction with interleukin 6.
    Type: Grant
    Filed: March 14, 1996
    Date of Patent: July 4, 2000
    Assignee: Toray Industries, Inc.
    Inventors: Masayuki Miyata, Reiji Kasukawa, Masanobu Naruto, Nobutaka Ida, Yu-ichiro Sato, Katsuaki Kojima, Nobuo Ida
  • Patent number: 6051395
    Abstract: A method and compound for detecting low levels of microorganisms in biological samples is disclosed. In the method, an antibiotic is conjugated to a detectable label. This antibiotic/label conjugate is then introduced into a sample containing biological material. The antibiotic binds to target microorganism where the label allows for detection of localized concentrations of the antibiotic. A compound to accomplish this method is also described. This compound is an antibiotic conjugated to a fluorescent dye. This dye has an excitation and emission wavelength that are not interfered by substances typically found in biological samples.
    Type: Grant
    Filed: December 4, 1998
    Date of Patent: April 18, 2000
    Assignee: Biometric Imaging, Inc.
    Inventor: Richard M. Rocco
  • Patent number: 5945295
    Abstract: This invention relates to a method to assess food spoilage ex vivo by quantification of prostanoid compounds and their metabolites produced by a noncyclooxygenase free radical catalyzed mechanism.
    Type: Grant
    Filed: December 22, 1997
    Date of Patent: August 31, 1999
    Assignees: Vanderbilt University, Lipoprotein Diagnostics, Inc.
    Inventors: L. Jackson Roberts, II, Jason D. Morrow, Eric H. Kuhrts
  • Patent number: 5925531
    Abstract: The present invention provides immortalized human bone marrow endothelial cells which are useful for the study of tumor metastasis. In particular, the human bone marrow endothelial cell lines provided by the invention provide an in vitro model system for screening compounds for the ability to reduce, prevent, or inhibit the metastasis of cancer cells to bone tissue.
    Type: Grant
    Filed: October 23, 1997
    Date of Patent: July 20, 1999
    Assignee: The Regents of the University of Michigan
    Inventor: Kenneth J. Pienta
  • Patent number: 5858696
    Abstract: This invention relates to a method to assess oxidative stress in vivo by quantification of prostaglandin F.sub.2 -like compounds and their metabolites produced by a noncyclooxygenase free radical catalyzed mechanism.
    Type: Grant
    Filed: August 18, 1997
    Date of Patent: January 12, 1999
    Assignee: Vanderbilt University
    Inventors: L. Jackson Roberts, II, Jason D. Morrow
  • Patent number: 5840494
    Abstract: This invention provides a method of determining the stage of prostate cancer in a human subject using a sample of peripheral blood from a human subject. The invention uses reverse transcriptase-PCR to detect the mRNA encoding prostate specific antigen (PSA) in circulating cells expressing PSA. The invention further uses digoxigenin enhancement of the resultant cDNA signal. The method has an overall sensitivity capable of detecting one PSA expressing cell per 100,000 cells. The method produced no false positives and had a superior detection selectivity for patients with nonlocalized prostate cancer.
    Type: Grant
    Filed: April 18, 1997
    Date of Patent: November 24, 1998
    Assignee: The Trustees of Columbia University in the City of New York
    Inventors: Aaron E. Katz, Ralph Buttyan, Anthony Raffo, Carl A. Olsson
  • Patent number: 5700654
    Abstract: This invention relates to a method to assess oxidative stress in vivo by quantification of prostaglandin F.sub.2 -like compounds and their metabolites produced by a noncyclooxygenase free radical catalyzed mechanism.
    Type: Grant
    Filed: September 12, 1994
    Date of Patent: December 23, 1997
    Assignee: Vanderbilt Unversity
    Inventors: L. Jackson Roberts, Jason D. Morrow
  • Patent number: 5508170
    Abstract: The invention is a stable liquid thromboplastin reagent used for measuring the performance of the coagulation system, with a shelf life of greater than 16 months, and a method of producing this reagent.
    Type: Grant
    Filed: June 3, 1994
    Date of Patent: April 16, 1996
    Assignee: Akzo Nobel N.V.
    Inventors: James R. Butler, Juan L. Torres, Rajesh Sharma
  • Patent number: 5434086
    Abstract: Cystic fibrosis (CF), a lethal genetic disease associated with a defect in Cl transport, is caused by mutations in the gene coding for cystic fibrosis transmembrane conductance regulator (CFTR). Surprisingly, not only wild type CFTR, but several naturally-occurring CFTR mutants carrying a defect in the first nucleotide binding fold (NFB1) all expressed cAMP-activatable Cl currents. Treatment of the CFTR mutants with appropriate concentrations of methylxanthine phosphodiesterase inhibitor (which increases cAMP levels) activated Cl conductance to near wild type levels. The present invention thus provides a new avenue for treating cystic fibrosis by the administration of therapeutically effective amounts of compounds which elevate cAMP levels. Dosage and patient responsiveness to treatment, as well as relative efficacies of the compounds being or to be administered can also be determined in accordance with the methods of present invention.
    Type: Grant
    Filed: December 9, 1993
    Date of Patent: July 18, 1995
    Assignee: The Regents of the University of Michigan
    Inventors: Francis S. Collins, Mitchell L. Drumm, David C. Dawson, Daniel J. Wilkinson
  • Patent number: 5403724
    Abstract: A process for production of 15-alpha-hydroxyprostaglandin intermediates of formula I ##STR1## wherein X is CH.sub.2,A is trans --CH.dbd.CH--B is ethylenedioxy or 2,2-dimethylpropylenedioxy,R.sub.1 is benzoyl, andR.sub.2 is ##STR2## by treating a ketone of formula II ##STR3## wherein A, B, X, R.sub.1 and R.sub.2 have the meanings indicated above, with a culture of Candida solani (NCYC 41) and isolating the resulting 15-alpha-hydroxyprostaglandin intermediate.
    Type: Grant
    Filed: January 3, 1994
    Date of Patent: April 4, 1995
    Assignee: Schering Aktiengesellschaft
    Inventors: Karl Petzoldt, Helmut Dahl, Werner Skuballa
  • Patent number: 5372935
    Abstract: An alkaline solution containing a complex of C.sub.30 H.sub.31 ClN.sub.6 is used as a specific indicator for detecting the presence of Candida spp. When Candida yeast bodies are introduced into the indicator solution, the yeast bodies are stained and form a blue or violet precipitate.
    Type: Grant
    Filed: June 29, 1993
    Date of Patent: December 13, 1994
    Assignee: Pearl Medical Science, Inc.
    Inventor: Charles L. Capps
  • Patent number: 5358853
    Abstract: The invention is a stable liquid thromboplastin reagent used for measuring the performance of the coagulation system, with a shelf life of greater than 16 months, and a method of producing this reagent.
    Type: Grant
    Filed: August 3, 1992
    Date of Patent: October 25, 1994
    Assignee: Akzo AV
    Inventors: James R. Butler, Juan L. Torres, Rajesh Sharma
  • Patent number: 4885246
    Abstract: New intermediate, an optically active (1S,5R)-7,7-alkylenedioxy-2-alkoxycarbonylbicyclo[3.3.0]octan-3-one which is useful for the synthesis of an optically active carbacyclin. This intermediate is prepared, as a non-reduced compound, from a racemic compound, (1SR,5RS)-7,7-alkylenedioxy-2-alkoxycarbonyl-cis-bicyclo[3.3.0]octan-3-one , by treatment of the racemic compound with a microorganism. The microorganism has an ability of specifically reducing the keto group of the (1R,5S) epimer of the racemic compound.
    Type: Grant
    Filed: December 19, 1988
    Date of Patent: December 5, 1989
    Assignee: Nisshin Flour Milling Co., Ltd.
    Inventors: Kenji Mori, Masahiro Tsuji
  • Patent number: 4539333
    Abstract: Prostacyclin, its salts, biosynthesis and synthesis thereof, pharmaceutical formulations containing them, and their use in medicine.
    Type: Grant
    Filed: May 10, 1977
    Date of Patent: September 3, 1985
    Assignee: Burroughs Wellcome Co.
    Inventor: Salvador Moncada
  • Patent number: 4247635
    Abstract: A process for the preparation of a 15 .alpha.-hydroxyprostaglandin intermediate of the formula ##STR1## wherein R.sub.1 is phenoxymethyl, phenoxymethyl substituted on the phenyl moiety by halogen or trifluoromethyl, or alkyl of 1-5 carbon atoms, andR.sub.2 is hydrogen, acetyl, benzoyl or p-phenylbenzoyl,which comprises stereospecifically microbiologically reducing a corresponding 15-ketone of the formula ##STR2## with a strain of the microorganism Kloeckera, Saccharomyces or Hansenula.
    Type: Grant
    Filed: December 5, 1979
    Date of Patent: January 27, 1981
    Assignee: Schering Aktiengesellschaft
    Inventors: Klaus Kieslich, Bernd Raduchel, Werner Skubalia, Helmut Vorbruggen, Helmut Dahl
  • Patent number: 4202822
    Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the F.sub.1 series.
    Type: Grant
    Filed: December 8, 1977
    Date of Patent: May 13, 1980
    Assignee: American Cyanamid Company
    Inventor: Allan Wissner
  • Patent number: 4197245
    Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the A.sub.1 series.
    Type: Grant
    Filed: December 8, 1977
    Date of Patent: April 8, 1980
    Assignee: American Cyanamid Company
    Inventor: Allan Wissner
  • Patent number: 4172839
    Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the F.sub.2 series.
    Type: Grant
    Filed: December 8, 1977
    Date of Patent: October 30, 1979
    Assignee: American Cyanamid Company
    Inventor: Allan Wissner
  • Patent number: 4170597
    Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the E.sub.2 series.
    Type: Grant
    Filed: December 8, 1977
    Date of Patent: October 9, 1979
    Assignee: American Cyanamid Company
    Inventor: Allan Wissner
  • Patent number: 4164446
    Abstract: Novel 18.xi.-, 19.xi.- and 20.xi.-hydroxy-prostaglandin derivatives of the formula I ##STR1## wherein the dotted line in the position 8-12 indicates the optional presence of a double bond, the waved lines in position 15 indicate that the hydroxyl group and the group R.sub.4 are either in .alpha.- or .beta.-position and Z represents a --CH.sub.2 CH.sub.2 -- or a cis --CH.dbd.CH--group, and wherein R represents one of the groups: ##STR2## (wherein the waved lines indicate that the hydroxyl groups are either in .alpha.- or .beta.-position and R.sub.1 represents a hydrogen atom, a methyl or ehtyl group), R.sub.2 represents either an oxygen atom or a hydrogen atom and an .alpha.- or .beta.-hydroxyl group, R.sub.3 represents a hydrogen atom or a hydroxyl group and R.sub.4 represents a hydrogen atom or a methyl group, with the proviso that when simultaneously, R.sub.1, R.sub.3 and R.sub.4 each represents a hydrogen atom, R.sub.
    Type: Grant
    Filed: September 9, 1977
    Date of Patent: August 14, 1979
    Assignee: Gist Brocades N.V.
    Inventors: Arthur F. Marx, Jean Doodewaard
  • Patent number: RE30287
    Abstract: Novel 18 -, 19 - and 20 -hydroxy-prostaglandin derivatives of the formula I ##STR1## wherein the dotted line in the position 8-12 indicates the optional presence of a double bond, the waved lines in position 15 indicate that the hydroxyl group and the group R.sub.4 are either in .alpha.- or .beta.-position and Z represents a --CH.sub.2 CH.sub.2 -- or a cis --CH.dbd.CH-- group, and wherein R represents one of the groups: ##STR2## (wherein the waved lines indicate that the hydroxyl groups are either in .alpha.- or .beta.-position and R.sub.1 represents a hydrogen atom, a methyl or ethyl group), R.sub.2 represents either an oxygen atom or a hydrogen atom and an .alpha.- or .beta.-hydroxyl group, R.sub.3 represents a hydrogen atom or a hydroxyl group and R.sub.4 represents a hydrogen atom or a methyl group, with the proviso that when simultaneously, R.sub.1, R.sub.3 and R.sub.4 each represents a hydrogen atom, R.sub.
    Type: Grant
    Filed: October 26, 1978
    Date of Patent: May 27, 1980
    Assignee: Gist-Brocades N.V.
    Inventors: Arthur F. Marx, Jean Doodewaard