Oxygen As Only Ring Hetero Atom Patents (Class 435/123)
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Patent number: 5955621Abstract: The present invention provides new sources of taxanes and other metabolites from members of the order Coniferales that are not in the genus Taxus.Type: GrantFiled: April 24, 1997Date of Patent: September 21, 1999Assignee: The Regents of the University of CaliforniaInventors: Don J. Durzan, Frank Ventimiglia
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Patent number: 5916783Abstract: Taxol is produced from taxol-producing microorganisms. Methods of obtaining he taxol-producing microorganisms are described. Radioactive labelled taxol products and methods for use of the radioactive labelled taxol and for the treatment of leukemia and cancer cells are described.Type: GrantFiled: November 26, 1997Date of Patent: June 29, 1999Assignee: The Research and Development Institute at Montana State UniversityInventors: Andrea Stierle, Donald Stierle, Gary Strobel
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Patent number: 5916784Abstract: The invention is a process for producing N-substituted glucamines, a process for oxidizing an N-substituted glucamine with an oxidizing microbe or extract thereof, and a process for oxidizing an N-substituted glucamine with an oxidizing microbe or extract thereof and reducing the oxidized N-substituted glucamine to an N-substituted-1-deoxynojirimycin. In addition, a one pot process for producing N-substituted-1-deoxynojirimycin from D-glucose is disclosed.Type: GrantFiled: December 27, 1996Date of Patent: June 29, 1999Assignee: G.D. Searle & CompanyInventors: Roy Walter Grabner, Bryan Hayden Landis, Ping Tu Wang, Michael Lee Prunier, Mike G. Scaros
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Patent number: 5908759Abstract: Taxol is produced from taxol-producing microorganisms. Methods of obtaining he taxol-producing microorganisms are described. Radioactive labelled taxol products and methods for use of the radioactive labelled taxol and for the treatment of leukemia and cancer cells are described.Type: GrantFiled: November 26, 1997Date of Patent: June 1, 1999Assignee: The Research and Development Institute at Montana State UniversityInventors: Andrea Stierle, Donald Stierle, Gary Strobel
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Patent number: 5905034Abstract: A process for separating a natural B avermectin from a natural avermectin containing fermentation broth by using an aqueous precipitation. The process comprises extracting natural avermectins from the fermentation broth with a water miscible solvent and adding sufficient water to precipitate the natural B avermetins. Preferably, the water miscible solvent is a C.sub.1 -C.sub.3 alcohol, acetone, or acetonitrile. In addition, an acid, base, salt or surfactant may be added to facilitate the precipitation. This invention provides an isolation technique that substitutes the use of an aqueous precipitation for nonaqueous solvent precipitations. The reduction in use of nonaqueous solvents provides economic, environmental and safety benefits.Type: GrantFiled: July 10, 1997Date of Patent: May 18, 1999Assignee: Pfizer Inc.Inventor: Abdullah R. Ali
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Patent number: 5900367Abstract: The present invention relates to a rapid and simple method for mass production of taxol from the cell culture of Taxus genus plant with a high purity and recovery. The method for mass production of taxol from Taxus genus plant of the present invention, comprises the steps of: (i) organic solvent extraction of biomass from Taxus genus plant to obtain a crude extract; (ii) synthetic adsorbent treatment of the crude extract and filtration to give filtrate; (iii) addition of hexane to the filtrate to precipitate crude taxol; (iv) fractional precipitation of the crude taxol in a mixture of alcohol and water and vacuum drying the precipitate to obtain taxol powder; and, (v) high performance liquid chromatography of the taxol powder. According to the method of the present invention, taxol of over 99% purity can be simply obtained from Taxus genus plant with a high recovery of over 90%.Type: GrantFiled: May 28, 1996Date of Patent: May 4, 1999Assignee: Samyang Genex Co., Ltd.Inventors: Seung-Suh Hong, Bong-Kyu Song, Jin-Hyun Kim, Chang-Bae Lim, Hyun-Soo Lee, Kwang-Wook Kim, In-Seon Kang, Hung-Bok Park
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Patent number: 5900366Abstract: A process for the fed batch production of a sophorolipid composition is described, in which culturing takes place of at least one Candida bombicola strain in a culture medium incorporating a sugar and a nitrogen source and said cultured strain is exposed in a reaction zone to a supply of an appropriate substrate under adequate aeration, temperature and pH conditions and at least once the following sequence is performed: a) the strain is continuously supplied with substrate at a supply rate in the reaction zone between 0.Type: GrantFiled: June 18, 1993Date of Patent: May 4, 1999Assignee: Institut Fran.cedilla.ais Du PetroleInventors: Remy Marchal, Jeannine Lemal, Caroline Sulzer, Anne-Marie Davila
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Patent number: 5879929Abstract: Methods for the enzymatic resolution of mixtures of enantiomers, such as .beta.-lactam compounds, which may be employed as intermediates in the preparation of taxanes bearing a C-13 sidechain containing a heterocyclic or cycloalkyl group, the latter useful in the pharmaceutical field.Type: GrantFiled: June 5, 1995Date of Patent: March 9, 1999Assignee: Bristol-Myers Squibb CompanyInventor: Ramesh N. Patel
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Patent number: 5871979Abstract: The present invention relates to a method for mass production of taxol by semi-continuous culture of Taxus genus plant with a high yield. According to the present invention, taxol can be prepared with a high yield, by employing semi-continuous culture of Taxus genus plant cell, which comprises: (i) inoculating Taxus genus plant cell on a medium containing 1 to 10% (w/v) sugar, and incubating it; and, (ii) transferring 1/10 to 1/2 volume of the culture obtained in the step (i) to a fresh medium and repeating the step (i), adding 1 to 10% (w/v) sugar to the remnant culture and incubating to the time of maximum production of taxol.Type: GrantFiled: May 28, 1996Date of Patent: February 16, 1999Assignee: Samyang Genex Co., Ltd.Inventors: Hyung-Kyoon Choi, Tom Lee Adams, Roy William Stahlhut, Sang-Ic Kim, Jeong-Hwan Yun, Bong-Kyu Song, Jin-Hyun Kim, Jun-Seog Song, Seung-Suh Hong, Hyun-Soo Lee
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Patent number: 5861302Abstract: Taxol is produced from taxol-producing micro-organisms. Methods of obtain the taxol-producing microorganisms are described. Radioactive labelled taxol products and methods for use of the radioactive labelled taxol and for the treatment of leukemia and cancer cells are described.Type: GrantFiled: June 10, 1994Date of Patent: January 19, 1999Assignee: The Research and Development Institute at Montana State UniversityInventors: Andrea Stierle, Donald Stierle, Gary Strobel
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Patent number: 5849289Abstract: The antibiotic reuterin is obtained by cultivating strains of Lactobacillus reuteri under controlled conditions. Reuterin has inhibitory activity against Gram positive and Gram negative bacteria, against the yeast, Saccharomyces cerevisiae, and against the protozoan, Trypanosoma cruzi. Reuterin-producing strains are identified by growth inhibition of susceptible microorganisms in the presence of glycerol or glyceraldehyde. Lactobacillus reuteri strains may be used for reducing the number of non-Lactobacillus reuteri bacteria in food items and in the gastrointestinal tracts of animals.Type: GrantFiled: June 7, 1995Date of Patent: December 15, 1998Assignee: Biogaia Biologics ABInventors: Walter J. Dobrogosz, Sven E. Lindgren
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Patent number: 5849568Abstract: A process is disclosed that hydrolyzes, by the action of an epoxide hydrolase of Diplodia gossipina (alternatively named Diplodia gossypina) ATCC 16391 or ATCC 10936, the undesired enantiomer of racemic indene oxide, an epoxide of indan.Type: GrantFiled: February 20, 1996Date of Patent: December 15, 1998Assignee: Merck & Co., Inc.Inventors: Michel M. Chartrain, Chris H. Senanayake, John P. N. Rosazza, Jinyou Zhang
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Patent number: 5811292Abstract: Methods for the enzymatic resolution of mixtures of enantiomers, such as .beta.-lactam compounds, which may be employed as intermediates in the preparation of taxanes such as taxol, the latter useful in the pharmaceutical field.Type: GrantFiled: August 1, 1996Date of Patent: September 22, 1998Assignee: E. R. Squibb & Sons, Inc.Inventors: Ramesh N. Patel, Laszlo J. Szarka, Richard A. Partyka
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Patent number: 5756321Abstract: Methods for the enzyme catalyzed acylation of primary and secondary alcohols using an enol ester as the acyl donor are described. The acylation occurs in organic media, and is enantioselective for racemic or prochiral alcohols. The reaction is irreversible, and produces unreactive by-products.Type: GrantFiled: February 20, 1996Date of Patent: May 26, 1998Assignee: Hoechst AktiengesellschaftInventors: Manfred Schudok, Gerhard Kretzschmar
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Patent number: 5753471Abstract: A process for the biotechnological preparation of alcohols, aldehydes and carboxylic acids by oxidation of compounds of the formula R.sup.1 --C(CH.sub.3).dbd.CR.sup.2 R.sup.3, where R.sup.1, R.sup.2 and R.sup.3 have the meanings indicated in the description, with the aid of microorganisms is described.Type: GrantFiled: December 28, 1995Date of Patent: May 19, 1998Assignee: BASF AktiengesellschaftInventors: Uwe Pressler, Friedhelm Balkenhohl, Bernhard Hauer, Wolfgang Ladner, Ursula Schnell, Horst Ralf Staudenmaier
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Patent number: 5744333Abstract: Processes for the extraction of taxol and derivatives thereof from roots of plants of the genus Taxus are described.Type: GrantFiled: June 7, 1995Date of Patent: April 28, 1998Assignee: Indena SPAInventors: Ermanno Cociancich, Roberto Pace
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Patent number: 5739016Abstract: An enzymatic hydrolysis method for the preparation of compounds useful as intermediates in the preparation of taxanes such as taxol, wherein one or more C-13 acyloxy-bearing taxanes are contacted with an enzyme or microorganism capable of hydrolyzing said acyloxy groups to hydroxyl groups.Type: GrantFiled: May 19, 1995Date of Patent: April 14, 1998Assignee: Bristol-Myers Squibb CompanyInventors: Ronald L. Hanson, Ramesh N. Patel, Laszlo J. Szarka
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Patent number: 5736366Abstract: Process for obtaining 10-deacetylbaccatin III from various parts of the yew (Taxus sp.) by extracting, with a suitable organic solvent, the aqueous solution obtained after treatment with water of the appropriate part of the yew or by adsorption of the aqueous solution on an appropriate substrate and desorption of 10-deacetylbaccatin III with a suitable solvent and then selective crystallization of 10-deacetylbaccatin III.Type: GrantFiled: June 7, 1995Date of Patent: April 7, 1998Assignee: Rhone-Poulenc Rorer S.A.Inventor: Rodolphe Margraff
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Patent number: 5712130Abstract: There is disclosed a process for the isolation of the hypolipaemic active substance lovastatin from a sample, e.g. fermentation broth, mycelium or filtrate of Aspergillus terreus (ATCC 20542) or Aspergillus oryzae (ATCC 74135) by extraction with butyl acetate. Simultaneously with the concentration of the extract, lactonisation takes place. There follows a direct crystallization of lovastatin in the lactone form from butyl acetate.Type: GrantFiled: December 5, 1995Date of Patent: January 27, 1998Assignee: KRKA tovarna zdravil, p.oInventors: Pavica Hajko, Tanja Vesel, Ivan Radez, Miroslav Pokorny
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Patent number: 5705372Abstract: The present invention relates to a novel enzymatic process for the preparation of flavors, in particular of the ionones and C.sub.6 to C.sub.10 aldehydes. The invention discloses a process for the preparation of optically active alpha ionone, beta ionone, C.sub.6 aldehydes such as n-hexanal, trans-2-hexanal, C.sub.10 aldehydes such as trans-2, cis-4-decadidienal, and trans-2, trans-4-decadienal. The invention also relates to a process for the production of alcohols, particularly C.sub.6 and C.sub.10 alcohols.Type: GrantFiled: June 12, 1995Date of Patent: January 6, 1998Assignee: BFA LaboratoriesInventors: Jean-Marc Belin, Benoit Dumont, Fran.cedilla.oise Ropert
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Patent number: 5700669Abstract: An enzymatic hydrolysis method, wherein one or more C-7 sugar, preferably C-7 xylosyl-bearing taxanes are contacted with an enzyme or microorganism capable of hydrolyzing said sugar groups to hydroxyl groups.Type: GrantFiled: April 12, 1995Date of Patent: December 23, 1997Assignee: Bristol-Myers Squibb CompanyInventors: Ronald L. Hanson, Ramesh N. Patel, Laszlo J. Szarka
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Patent number: 5686298Abstract: An enzymatic reduction method, particularly a stereoselective enzymatic reduction method, for the preparation of compounds useful as intermediates in the preparation of taxanes.Type: GrantFiled: February 1, 1995Date of Patent: November 11, 1997Assignee: E. R. Squibb & Sons, Inc.Inventors: Ramesh N. Patel, Amit Banerjee, Clyde G. McNamee, John K. Thottathil, Laszlo J. Szarka
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Patent number: 5679563Abstract: Actinomadura roseorufa mutants characterized by the ability to produce by fermentation UK-61,689, an acidic polycyclic ether anticoccidial antibiotic previously available only by selective acid hydrolysis of UK-58,852; and Actinomadura roseorufa having the identifying characteristics of ATCC 53,666, ATCC 53,665, ATCC 53,664 and ATCC 53,674.Type: GrantFiled: June 6, 1995Date of Patent: October 21, 1997Assignee: Pfizer Inc.Inventor: Edward J. Tynan, III
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Patent number: 5677155Abstract: A process for preparing the sex pheromone of Lymantria dispar L. effectively which comprises the steps of reacting 1-bromodecane and propargyl alcohol tetrahydropyranylether in the presence of sodium hydroxide to give 1-tetrahydropyranyloxy-2-tridecyne, treating the tetrahydropyranyloxy-2-tridecyne with p-toluenesulfonic acid to give 2-tridecyn-1-ol, catalystic-hydrogenating the 2-tridecyn-1-ol in the presence of Lindlar catalyst to give (Z)-2-tridecen-1-ol, oxidizing the (Z)-2-tridecen-1-ol with peroxide to give (.+-.)-cis-2,3-epoxy-1-tridecanol, reacting the (.+-.Type: GrantFiled: October 25, 1995Date of Patent: October 14, 1997Assignee: Nitto Denko Co., Ltd.Inventors: Eiichiro Fukusaki, Tetsuo Omata, Shuji Senda
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Patent number: 5672504Abstract: A microorganism or a preparation thereof is permitted to act on a mixture of enantiomers of an epoxide such as 3-chlorostyrene oxide and the product optically active epoxide is recovered. The microorganism able to produce an optically active (S)-epoxide from the mixture of enantiomers of the epoxide include, for example, a microorganism strain belonging to the genus Candida, the genus Rhodosporidium, the genus Rhodococcus and the genus Nosardioides. Examples of the microorganism capable of producing an optically active (R)-epoxide from said mixture include a microorganism strain belonging to the genus Trichosporon, the genus Geotrichum, the genus Corynebacterium, the genus Micrococcus and the genus Brevibacterium. The objective optically active epoxide can efficiently be obtained with ease and simplicity from the corresponding mixture of enantiomers of the epoxide.Type: GrantFiled: October 25, 1995Date of Patent: September 30, 1997Assignee: Daicel Chemical Industries, Ltd.Inventors: Akinobu Matsuyama, Yoshinori Kobayashi
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Patent number: 5665576Abstract: A method for the production of taxanes such as taxol. The method includes inducing formation of callus cells by contacting an explant tissue with a liquid medium without complete submergence of the tissue in the medium. The callus cells formed are employed in a liquid suspension cell culture to produce one or more taxanes.Type: GrantFiled: June 7, 1995Date of Patent: September 9, 1997Assignee: E. R. Squibb & Sons, Inc.Inventors: Paul M. Cino, Steven R. Schwarz, Dana L. Cazzulino
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Patent number: 5642587Abstract: A method for accelerating the growth of Taxus X media `Hicksii` and related Taxus species to enhance the production and recovery of taxol and Taxotere from plant tissues is described. The method includes the steps of increasing the production of biomass by cycling growth periods of Taxus plants within a greenhouse or other enclosed structure, harvests of plant parts and cold storage of the remaining unharvested plants to break dormancy and condition the plant for the next cycle of growth and harvest. After at least several cycles, entire plants are harvested for extraction from all plant parts while other plants are saved for stock plants or reforesting. The collected plant material is prepared for extraction of taxol or Taxotere, compounds used in the treatment of cancer.Type: GrantFiled: August 22, 1995Date of Patent: July 1, 1997Assignee: GRoW International Corp.Inventors: Harry W. Janes, Gerald E. Gore, Wayne K. Wittman, Harry T. Roman
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Patent number: 5637484Abstract: This invention relates to a method of producing a taxane-type diterpene(s) wherein tissues or cells of a plant which produces taxane-type diterpene(s) are cultured in the presence of at least one member selected from the group consisting of jasmonic acids, wherein the tissues or the cells of the plant are cultured by controlling the oxygen concentration in a gas phase in a culture vessel to less than the oxygen concentration in the atmosphere from the initial stage of the culture, or by controlling the dissolved oxygen concentration in a fluid medium which is in contact with the tissue or the cell to less than the saturated dissolved oxygen concentration at that temperature from the initial stage of the culture, while oxygenic gas containing 0.Type: GrantFiled: July 14, 1995Date of Patent: June 10, 1997Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Yukihito Yukimune, Yasuhiro Hara, Yosuke Higashi, Naoto Ohnishi, Homare Tabata, Chuzo Suga, Kouichi Matsubara
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Patent number: 5620875Abstract: Taxol, an antineoplastic drug, has shown cytotoxic activity against numerous malignant tumors including: breast cancer, colon cancer, ovarian cancer, and skin cancer. Taxol is found in many species of yew including: slow-growing Taxus brevifolia and faster-growing Taxus media X Hicksii. Yew tree cuttings were cultured and the medium was extracted weekly, bi-weekly, and tri-weekly over a period of nine weeks. Taxol and other taxanes were separated through a multi-step procedure using hexane extractions, C-18 Sep Pak cartridges, and high performance liquid chromatography (HPLC). The concentration of the taxanes was then calculated. Taxol and other taxanes can continue to be transferred into a culture medium and extracted over a nine-week period. There is a higher yield when extracted weekly.Type: GrantFiled: February 17, 1995Date of Patent: April 15, 1997Assignee: University of PortlandInventors: Angela Hoffman, Courtney C. J. Voelker, Alyssa T. Franzen
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Patent number: 5605819Abstract: A process is disclosed that quantitatively bioconverts indene to (1S,2R)-indene oxide and (1S,2R)-indandiol, by the action of fungal haloperoxidase followed by various chemical step(s), e.g., adjusting the pH.Type: GrantFiled: May 19, 1995Date of Patent: February 25, 1997Assignee: Merck & Co., Inc.Inventors: Michel M. Chartrain, Neal C. Connors, George M. Garrity, Roger C. Olewinski, Jr., Thomas R. Verhoeven, Jinyou Zhang
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Patent number: 5589348Abstract: The invention relates to an improved enzymatic method for determining the concentration of an analyte in a sample body fluid. The improvement comprises a coupled enzyme reaction scheme comprising the in situ generation of reduced nicotinamide coenzyme, with either simultaneous or subsequent re-oxidation of coenzyme by an analyte substrate and substrate specific enzymes. The change in absorbance due to the reoxidation of coenzyme is proportional to the concentration of analyte in the reaction mixture.Type: GrantFiled: March 22, 1994Date of Patent: December 31, 1996Assignee: Hoffmann-La Roche Inc.Inventors: Richard A. Kaufman, John M. Konopka, Henry J. Rosenfeld, Janine E. Sabo
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Patent number: 5585505Abstract: The invention is directed to a hatching agent for hatching the species and patho types of nematodes causing potation sickness, which nematodes comprise Globodera pallida, from the cysts thereof, with a molecular weight of 498, a component C.sub.27 H.sub.30 O.sub.9 and the structure of formula (a) and the derivatives, esters and salts thereof.Type: GrantFiled: June 1, 1994Date of Patent: December 17, 1996Assignee: B.V. Chemische Pharmaceutische Industrie "Luxan"Inventors: Johan G. Mulder, Pieter Diepenhorst, Pieter Plieger, Ingrid E. M. Br uggemann-Rotgans
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Patent number: 5571704Abstract: A process for the preparation of the compounds of formula ##STR1## (wherein R has the meanings reported in the specification) by enzymatic transesterification of enantiomeric mixtures is described.These compounds are intermediates useful in the synthesis of Diltiazem.Type: GrantFiled: March 14, 1995Date of Patent: November 5, 1996Assignee: Zambon Group S.p.A.Inventors: Luca Ghirotto, Stefano Servi, Claudio Fuganti, Angelo Gentile, Claudi o Giordano
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Patent number: 5567614Abstract: Methods for the enzymatic resolution of mixtures of enantiomers, such as .beta.-lactam compounds, which may be employed as intermediates in the preparation of taxanes such as taxol, the latter useful in the pharmaceutical field.Type: GrantFiled: May 23, 1994Date of Patent: October 22, 1996Assignee: E.R. Squibb & Sons, Inc.Inventors: Ramesh N. Patel, Laszlo J. Szarka, Richard Partyka
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Patent number: 5561055Abstract: The present invention relates to a biologically pure culture of a novel bacteria of genus Erwinia, which is isolated from Taxus canadensis, and wherein said bacteria of genus Erwinia is characterized by the production of paclitaxel and related taxanes in a fermentative or respiratory type of metabolism from simple semi-synthetic or synthetic culture media. Also, the present invention relates to a method of bacterial mass production of paclitaxel and related taxanes which comprises the steps of: a) culturing the bacteria of genus Erwinia of the present invention in a growth-supporting nutrient medium capable of promoting growth and reproduction of said bacteria, and wherein said culturing is effected for a time sufficient to allow production of paclitaxel and related taxanes; and b) isolating said produced paclitaxel and related taxanes from said culturing medium of step a).Type: GrantFiled: May 5, 1995Date of Patent: October 1, 1996Assignee: BCM Developpement Inc.Inventors: Michel Pag e, Nathalie Landry
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Patent number: 5547866Abstract: The present invention provides haploid cells and their derivatives which are cultured in vitro to produce taxanes and other metabolites that evolve from the isoprenoid biosynthesis pathway.Type: GrantFiled: July 20, 1994Date of Patent: August 20, 1996Assignee: The Regents of the University of CaliforniaInventors: Don J. Durzan, Frank F. Ventimiglia
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Patent number: 5529911Abstract: Granules containing salinomycin are prepared that are free-flowing, dust-free, and have unrestricted bioavailability of salinomycin. The granules are produced by fermenting a culture broth with a salinomycin producing microorganism to a residual fat content of about 24 to 30% by dry weight broth, adding to the fermented broth a cellulose ether and an anticaking agent, and spray drying the broth while adding a flow auxiliary to produce granules containing 10 to 26% by weight salinomycin. The granules also contain, based on the weight of the broth being fermented, 30 to 40% anticaking agent and flow auxiliary in a ratio of 3:1 to 9:1 and 0.5 to 2% cellulose ether. The anticaking agent is preferably a calcium carbonate such as chalk or a silica of natural origin such as diatomaceous earth, talc, or kaolin. The flow auxiliary is preferably a synthetic or precipitated silica.Type: GrantFiled: August 19, 1994Date of Patent: June 25, 1996Assignee: Hoechst AktiengesellschaftInventor: Rolf Hohl
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Patent number: 5523219Abstract: An enzymatic hydrolysis method, wherein one or more C-10 acyloxy-bearing taxanes are contacted with an enzyme or microorganism capable of hydrolyzing said acyloxy groups to hydroxyl groups. Also provided is an enzymatic esterification method, wherein one or more C-10 hydroxyl-bearing taxanes are contacted with an acylating agent and an enzyme or microorganism capable of esterifying said hydroxyl groups to form acyloxy groups.Type: GrantFiled: June 15, 1993Date of Patent: June 4, 1996Assignee: Bristol-Myers Squibb CompanyInventors: Ronald L. Hanson, Ramesh N. Patel, Laszlo J. Szarka
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Patent number: 5516676Abstract: Compounds useful as intermediates in the preparation of taxanes such as taxol are prepared by contacting one or more C-13 acyloxy-bearing taxanes with an enzyme or microorganism capable of hydrolyzing said acyloxy groups to hydroxyl groups. In a preferred embodiment the microorganism is Nocardioides albus ATCC55424, Nocardioides albus ATCC55425 or Nocardioides luteus ATCC55426 or the hydrolase enzyme is isolated from the microorganisms.Type: GrantFiled: June 15, 1993Date of Patent: May 14, 1996Assignee: Bristol-Myers Squibb CompanyInventors: Ronald L. Hanson, Ramesh N. Patel, Laszlo J. Szarka
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Process for the isolation and purification of taxol and taxanes from Taxus using methanol or acetone
Patent number: 5478736Abstract: A process for the separation of taxanes, particularly taxol, cephalomannine, baccatin III and deacetylbaccatin III, from ornamental yew tissue is described. The process involves a specific solvent mixture of water and 50 to 95 percent by volume methanol, ethanol or acetone and treatment of the resulting extract using activated carbon, preferably charcoal. The taxanes are preferably separated from the crude extract by a normal phase chromatographic step which preferably is through vacuum and then medium pressure column chromatographic separation, using inexpensive silica gel as an absorbent. The silica gel is regenerated by heating in a furnace above about 500.degree. C. to remove adsorbed organic materials.Type: GrantFiled: August 26, 1994Date of Patent: December 26, 1995Assignee: Board of Trustees operating Michigan State UniversityInventor: Muraleedharan G. Nair -
Patent number: 5439806Abstract: Carboxylates of polar, hydrophilic alcohols of the formula ##STR1## in which R is an unbranched or branched organic radical which contains, as polar members between aliphatic or araliphatic hydrocarbon bridges, ether oxygens, amine nitrogen groups or a mixture of ether and amine groups which can be incorporated into a cyclic structure, where the total length does not exceed 20 members and where, in the case of polyethylene glycol [(CH.sub.2 --CH.sub.2 --O).sub.n ], n indicates the number of the members and is defined as any integer, and R' is an aliphatic or araliphatic radical which has at least one functional group, are suitable as protective groups since they can be introduced selectively into functional groups of organic compounds and eliminated specifically by lipases.Type: GrantFiled: April 12, 1994Date of Patent: August 8, 1995Assignee: Hoechst AktiengesellschaftInventors: Horst Kunz, Gnther Braum, Peter Braun
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Patent number: 5439678Abstract: The antibiotic reuterin is obtained by cultivating strains of Lactobacillus reuteri under controlled conditions. Reuterin has inhibitory activity against Gram positive and Gram negative bacteria, against the yeast, Saccharomyces cerevisiae, and against the protozoan, Trypanosoma cruzi. Reuterin producing strains are identified by growth inhibition of suspectible microorganisms in the presence of glycerol or glyceraldehyde.Type: GrantFiled: March 16, 1994Date of Patent: August 8, 1995Assignee: Biogaia Biologics ABInventors: Walter J. Dobrogosz, Sven E. Lindgren
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Patent number: 5429941Abstract: A process is disclosed by which a 1-benzyl-1-hydrocarbyl alkene substrate is catalytically converted to an epoxide. The catalyst is a monoclonal antibody or paratope-containing molecule that binds to the substrate as well as to an N-benzyl-N-hydrocarbylpiperidinium compound that is an analog to the substrate. The chemical reaction is carried out in an aqueous medium using a peroxycarboximic acid as the oxidant.Type: GrantFiled: January 24, 1994Date of Patent: July 4, 1995Inventors: Richard A. Lerner, Andreas Koch, Jean-Louis Reymond
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Patent number: 5418152Abstract: An acidic polycyclic ether antibiotic, having structure established by X-ray crystallography, is formed by fermentation of a novel microorganism, Actinomadura sp. ATCC 55080. This novel antibiotic is useful as an anticoccidial in poultry, in the prevention and treatment of swine dysentery and as a growth promotant in cattle and swine.Type: GrantFiled: March 12, 1993Date of Patent: May 23, 1995Assignee: Pfizer IncInventors: Walter P. Cullen, John P. Dirlam, Hiroshi Maeda, Junsuke Tone
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Patent number: 5413928Abstract: A process for extracting enhanced amounts of a plant secondary metabolite from plant tissue with limited loss of tissue viability by reversibly permeabilizing the tissue membrane is disclosed.Type: GrantFiled: June 21, 1991Date of Patent: May 9, 1995Assignee: Worcester Polytechnic InstituteInventors: Pamela J. Weathers, Ronald D. Cheetham, Alexander DiIorio
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Patent number: 5407816Abstract: This invention is directed to methods for the enhanced production and recovery of taxol and taxanes by cell cultures of Taxus species.Type: GrantFiled: April 24, 1992Date of Patent: April 18, 1995Assignee: Phyton Catalytic, Inc.Inventors: Venkataraman Bringi, Prakash G. Kadkade, Christopher L. Prince, Barry F. Schubmehl, Eugene J. Kane, Braden Roach
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Patent number: 5403728Abstract: The invention refers to a new microbial process for preparing .beta.,.delta.-dihydroxy-7-[1,2,6,7,8,8a-hexahydro-2.6-dimethyl-8-(2-methy l-butyryloxy)-naphthalen-1-yl]-heptanoic acid .delta.-lactone of formula (I) and .beta.,.delta.-dihydroxy-7-[1,2,6,7,8,8a-hexahydro-2.6-dimethyl-8-(2-methy lbutyryloxy)-naphtalen-1-yl]-heptanoic acid of formula (II), ##STR1## by the aerobic fermentation of the submerged culture of an imperfect fungus strain biosynthesizing the above compounds, in a nutrient medium containing utilizable carbon and nitrogen sources as well as mineral salts, and by isolating the product of formula (I), which comprises cultivating a strain of the new Aspergillus obscurus fungus species producing the above compound(s) of formulas (I) and/or (II), in a temperature range of 25.degree. to 30.degree. C. and, if desired, separating the product(s) formed from the fermentation broth, then isolating it in the lactone form of formula (I) and, if desired, purifying the same.Type: GrantFiled: June 17, 1993Date of Patent: April 4, 1995Assignee: BIOGAL Gyogyszergyar RTInventors: Antonia Jekkel, Eva Ilkoy, Istvan M. Szabo, Gabor Ambrus, Attila Andor, Ilona Varga, Imre Moravcsik, Istvan Szabo, Janos Erdei, Kalman Polya, Andras Kiss, Laszlo Cseke, Karoly Nagy, Mihaly Kaszas, Lajos Kiss, Istvan Magyi, Edit Halasz, Gyorgy Santha
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Patent number: 5380654Abstract: 2,3-Epoxypropyl ethers valuable as intermediates for preparing medicaments and the like are prepared from the corresponding allyl ethers by means of epoxide-producing microorganisms belonging to Nocardia, Brevibacterium, Corynebacterium, Pseudomonas, Rhodococcus, Arthrobacter or Micrococcus.Type: GrantFiled: January 19, 1993Date of Patent: January 10, 1995Assignee: Japan Energy CorporationInventors: Keizo Furuhashi, Motoyoshi Takagi
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Patent number: 5376539Abstract: 2,3-Epoxypropyl ethers valuable as intermediates for preparing medicaments and the like are prepared from the corresponding allyl ethers by means of epoxide-producing microorganisms belonging to Nocardia, Brevibacterium, Corynebacterium, Pseudomonas, Rhodococcus, Arthrobacter or Micrococcus.Type: GrantFiled: October 2, 1992Date of Patent: December 27, 1994Assignee: Nippon Mining Co., Ltd.Inventors: Keizo Furuhashi, Motoyoshi Takagi
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Patent number: 5372940Abstract: The invention is drawn to a new enzyme that selectively hydrolyzes D-pantolactone in D,L-pantolactone and has the following characteristics:(a) action: acts on pantolactone to produce the corresponding acid;(b) specificity for substrate: acts specifically on D-pantolactone but not on L-pantolactone;(c) pH stability: stable at pH5-9;(d) optimal pH: 7.0-7.5;(e) optimal temperature: ca. 50.degree. C.; and(f) effect of various metal ions or inhibitors: inhibited by Cd.sup.2+, Hg.sup.2+ or Cu.sup.2+ EDTA, as well as a process for the preparation thereof. The enzyme is preferably produced by cultivating the microorganisms of the genera Fusarium, Cylindrocarpon, and Gibberella, and most preferably the microorganism Fusarium oxysporum IFO 5942.Type: GrantFiled: June 2, 1992Date of Patent: December 13, 1994Assignee: Fuji Yakuhin Kogyo Kabushiki KaishaInventors: Keiji Sakamoto, Hideaki Yamada, Sakayu Shimizu