WO2004060626A1 - Agglomeration d'une biomasse d'if permettant l'extraction de taxanes et d'autres produits naturels - Google Patents

Agglomeration d'une biomasse d'if permettant l'extraction de taxanes et d'autres produits naturels Download PDF

Info

Publication number
WO2004060626A1
WO2004060626A1 PCT/US2003/041824 US0341824W WO2004060626A1 WO 2004060626 A1 WO2004060626 A1 WO 2004060626A1 US 0341824 W US0341824 W US 0341824W WO 2004060626 A1 WO2004060626 A1 WO 2004060626A1
Authority
WO
WIPO (PCT)
Prior art keywords
yew
pellet
pellets
biomass
inch
Prior art date
Application number
PCT/US2003/041824
Other languages
English (en)
Inventor
Rex T. Gallagher
Edward M. Desimone
Brian A. Bucher
Christopher D. Howe
Barry S. Hand
Original Assignee
Natural Pharmaceuticals Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Natural Pharmaceuticals Inc. filed Critical Natural Pharmaceuticals Inc.
Priority to CA002512170A priority Critical patent/CA2512170A1/fr
Priority to AU2003303565A priority patent/AU2003303565A1/en
Priority to EP03815018A priority patent/EP1594668A4/fr
Publication of WO2004060626A1 publication Critical patent/WO2004060626A1/fr
Priority to US11/173,477 priority patent/US20060127510A1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
    • C07D305/14—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/13—Coniferophyta (gymnosperms)
    • A61K36/15—Pinaceae (Pine family), e.g. pine or cedar

Definitions

  • the present invention is directed to making Yew pellets from Yew tree material.
  • the process comprising the steps of (i) adding from about 1% to about 20% w/w water to ground Yew tree material; and (ii) compressing the Yew tree material in a die to form a pellet.
  • the resulting pellet has a final moisture content of less than 10% by weight.
  • the Yew pellets produced herein are suitable for extracting taxane molecules from the pellets.
  • Yew trees contain a family of natural diterpenoid compounds called taxanes.
  • taxanes in particular, taxol
  • taxol has been developed as a major anticancer drug which successfully treats a number of human cancers.
  • the name taxol was given to the compound by the original discoverers of this material. Subsequently the name was registered as a trademark, and the compound is now referred to in the scientific literature as 'Paclitaxel.'
  • a large body of scientific and industry publications still refer to the natural compound as taxol.
  • U.S. Patent 6,375,447 is directed to a feed pellet mill that has one inlet for the feed, one outlet for the pellet, and one outlet for water expressed from the forming pellet. This allows for excess water to be removed from the biomass as the pellet is being formed.
  • U.S. Patent 4,613,339 is directed to a process that pelletizes spent sorghum residue, "bagasse,” by storing and then pelletizing the residue.
  • U.S. Patents 5,682,683 and 5,728,447 describes process for forming pellets of grains and cereals with a waved-brick structure, providing the pellet with better handling properties.
  • Paclitaxel was initially discovered in the bark of the Pacific Yew tree.
  • a number of patents described processes for removing the bark from the trunk-wood of the tree.
  • U.S. Patent 3,826,433 describes a process for separating the bark from the shipped wood through steam, mechanical compression, milling, and screening.
  • U.S. Patent Application US2002/0114853 describes the use of pelletization in the extraction of a variety of compounds (including taxanes) using selective extraction of components using acidic and basic solvents from Taxus yunnaneusis bark, or Yew tree needles.
  • Other patents that are relevant to extractions from biomass may use powdered, pulverized, or shredded material (See U.S. Patents 6,1751,035 Bl, 6,264,998 Bl, 6,392,070 B 1).
  • Yew is a name ascribed to a number of trees which are Taxus species; Taxus being the main genus in the family Taxaceae. Originally isolated from the bark of the Pacific Yew (Taxus brevifolia) collected from Washington State, beginning in 1962, taxol was subsequently reported as occurring in two other Taxus species, including Taxus baccata (European Yew) and Taxus cuspidata (Japanese Yew), in 1971. Following intensive investigations, taxol was further reported to occur in a number of other Taxus species and cultivars.
  • Taxus globosa (Mexican Yew), Taxus floridana (Florida Yew), Taxus canadensis (Canadian Yew), Taxus wallichiana (Himalayan Yew), Taxus yunnanensis, Taxus chinensis, and also a number of ornamental hybrids, such as Taxus media cultivars, e.g.: T.media 'Densiformis', T.media ⁇ icksii', T.media 'Brownii', T.media 'Dark Green Spreader', T.media 'Runyan', T.media 'Wardii', T.media 'Tautonii', Tcuspidata 'Capitata', etc.
  • Taxus media cultivars e.g.: T.media 'Densiformis', T.media ⁇ icksii', T.media 'Brownii', T.media 'Dark Green Spreader
  • Yew biomass material may be derived from any Taxus species, including but not limited to the species and cultivars described above.
  • Other Taxus species for use in the present invention are identified in: Chadwick, L.C. and Keen, R.A. May 1986, "A study of the Genus Taxus", Res. Bull. 1086, Ohio Agricultural Research and Development Center; Appendino, G. 1995, "The Phytochemistry of the Yew Tree”: Phytochemistry, Natural Products Reports 12(4): 349-360; Convention On International Trade in Endangered Species of Wild Fauna and Flora: Eleventh meeting of the Plants Committee, LangKawi (Malaysia), 3-7 September 2001, Document PCI 1 DOC.
  • the starting material for this invention may be derived from a plant material selected from the group of plants commonly referred to as Yew trees. Suitable plants of this group are species of Taxus. Among Taxus species, Taxus x media cultivars are preferred. For example, preferred cultivars include, but are not limited to, T.media 'Hicksii' or T.media 'Dark Green Spreader'. While it is convenient to use certain parts of the Yew tree in this invention, the Yew biomass for pelletization can be derived from the whole plant or from separated parts such as wood, stems, roots, leaves (needles), seeds, or any combination thereof. The material to be pelletized are derived from the bark or the needles are used. In one preferred embodiment, the material to be pelletized is dry ground yew tree root biomass (powder).
  • the large-scale processing of Yew tree biomass typically involves some kind of size- reduction processing. This is done to produce a more-or-less homogeneous ground powder which can be extracted with organic solvents in suitable, large-volume containers. Problems arise with handling the ground biomass material, particularly with transportation, safety, and ease and efficiency of solvent extractions. Solvent extraction problems arise from poor solvent contact due to channeling, 'clumping', or poor solvent circulation.
  • pellets can be readily made from ground biomass materials using commercially available pelletizing mills.
  • Suitable large-scale pelletizing machinery is available from various sources, which include California Pellet Mill Co, Crawfordsville, Indiana; Sprout-Bauer, Muney, PA; Bliss Industries, Ponca City, OK.
  • very large and heavy duty machinery is used for the process of pelletizing biomass materials such as hay, alfalfa, etc.
  • the machinery used usually involves engines that can range in capacity up to 10 tons/hour throughput which utilize massive engines of several hundred HP.
  • the associated drying and mass transporting systems involve large facilities and equipment, often including large storage sheds, silos, semitrailer and rail wagon transportation, etc.
  • Suitable methods of harvesting and processing yew biomass material is provided in PCT Appl. No. , entitled "Harvesting Yew Biomass for Extraction of Taxanes and Other Natural
  • pelletized Yew biomass materials over non-pelletized materials
  • advantages of using pelletized Yew biomass materials over non-pelletized materials include but are not limited to the following: (i) ease of bulk handling; (ii) shipping/ transportation / storage; (iii) freedom from dust (cleaner, safety factor, environmental factor, reduced product loss); (iv) greater density of solids leads to less volume required in shipping and storage; (v) greater density of solids requires smaller processing vessel volumes; (vi) non-packing nature of pellets resists volume-unloading issues after transport (flour can pack into a cement); (vii) larger size of pellets allows for greater range of equipment use in processing (larger filters); (viii) uniform size-diameter distribution vs.
  • pelletizing ground powdered Yew biomass offers substantial advantages in the handling, processing and, most importantly, extraction of taxanes and other material products from the biomass.
  • efficiency and ease of solvent extraction is a major advantage in processing the pelletized Yew biomass.
  • the present invention provides a process for manufacturing pelletized Yew material without significant reduction of the available taxane content in the biomass. Also, such process does not adversely impact the extraction process, such that additional purification and/or extraction steps are required.
  • the present invention provides stable pellets from ground, dried Yew roots, at both the laboratory scale and at the industrial scale. No significant loss/degradation of extractable paclitaxel resulting from the present pelletization process was observed. IV. SUMMARY OF THE INVENTION
  • Another object of the present invention is to provide an efficient and economical process for producing Yew pellets from Yew tree material, including ground material (powder).
  • Another object of the present invention is to provide a process for making pellets from Yew tree material (including powdered material) which are easily handled, stored, and used.
  • a further object of the present invention is to provide a process for making Yew pellets from Yew tree material (including powdered material) wherein the resulting pellets have appropriate amounts of water for the extraction process.
  • a further object of the present invention is to provide a process for making Yew pellets with appropriate amounts of water to minimize undesirable microbal growth of the pelletized material.
  • a pelletized product is produced from, for example, a finely ground pelletizable Yew tree material, or a mixture of finely ground Yew tree materials and water, by pressing the material through appropriate die openings in a commercial or laboratory scale pelletizer such as, for example, a California pellet mill, or a Bliss pellet mill. While the invention may be utilized in the processing of various raw materials, it has been found especially useful in producing a pelletized Yew from a finely ground material. V. DETAILED DESCRIPTION OF THE INVENTION
  • the resulting pellet is a product of a controlled manufacturing process.
  • variations in the amount of water or liquid in the raw material will have a marked effect both on the ability to form the material into pellets and on the strength and integrity of the pellets formed.
  • the present invention provides a process that forms a stable Yew pellet for transportation and extraction of taxanes and other natural products contained therein.
  • the present invention is suitable for pelletizing Yew biomass at different scales, including but not limited to: (i) Laboratory/Pilot Scale Pelletizing Runs; and (ii) Industrial- Scale/Large-Scale Pelletizing Runs. A description of each type of run is described below.
  • the Yew pellets produced herein are suitable for extracting taxane molecules from the pellets. Laboratory / Pilot-Scale Pelletizing Runs
  • Pelletizing may be carried out on Taxus media x "Densiformis" ground root material.
  • pellets can be made with a California Pellet Mill ("CPM"), Crawfordsville, IN. This pelletizing mill comprises dies having 1/8" and 3/16"extrusion holes.
  • the mill speed may be adjusted to prevent the temperature from exceeding 200°F, preferably less than 180°F, more preferably 140°F to 160°F. Water can be added to the powdered biomass material before pelletization.
  • Other adjustments to the pellet mill can be made to facilitate the pelletization process, such adjustments are known to those skilled in the art.
  • Pellets can be made using a CPM pellet mill.
  • a large CPM pellet mill can pelletize approximately 55 metric tons of 'Densiformis' roots biomass during a one-day run.
  • the resulting pellets can be l A inch in diameter.
  • Preferably the resulting moisture content in the pellets can be approximately 5 to 6 wt% water.
  • Pellets can also be made using a Bliss Hammer Mill.
  • the Yew ground material biomass can be dried in a rotating drum and ground further by using this mill.
  • the pelletizing can be done in two Sprout pelletizers with smaller dies.
  • the dies can have 1/4" holes with tapered relief.
  • the throat length for compression can be 1 1/4" long.
  • Water can be added to the Yew ground material before pelletization.
  • Each pelletizer mill can process 3,500 lb ground biomass/hr. Each mill may consume 200 A at 460N 3 phase.
  • the biomass after reaching the appropriate conditions of size and content, are first harvested.
  • the Yew tree material may be ground by conventional means. Suitable equipment for harvesting the tops of yew plants include those developed by Dr. Peter Felker (Texas A&M University - Kingsville) using a flail harvester (http://www.newuses.orR EG/EG-19/19harvester.html'). or http://www.woodyciOps.org/ mechconf/mclaughl. html).
  • the harvesting is directed to the roots of the Taxus plant.
  • the roots may be piled on a concrete slab, and washed using a high pressure hose and a shovel or other suitable device to turn the mass over.
  • the roots may be dried through an alfalfa drier and then ground by conventional means.
  • approximately 5% to 6% w/w water is added to the Yew biomass.
  • the water content should be carefully monitored. Too much water in the pellets could encourage microbial growth, which is undesirable. Also, excess water may adversely affect the taxane extraction process, causing a reduction in the extraction efficiency.
  • the water content may be controlled by a water or steam bleed steam. This is more desirable.
  • the following ranges of water may be added to the Yew tree material: from about 0.25% to about 0.5%; about 0.5% to about 1.0%; about 1.0% to 1.5%; 1.5% to about 2.0%; 2.0% to about 3.0%; 3.0% to about 4.0%; 4.0% to about 5.0%; 5.0% to about 6.0%; 6.0% to about 7.0%; about 7.0% to about 8.0%; 8.0% to about 9.0%; about 10.0% to about 11.0%; about 11.0% to about 12.0%; about 12.0% to about 13.0%; about 13.0% to about 14.0%; about 14.0% to about 15.0%; about 15.0% about to 20.0%.
  • Other ranges of water include: about 1% to about 5%; about 5% to about 10%; about 10% to about 15%; about 15% to about 20%.
  • the pellets are made using a CPM pellet mill.
  • the speed/capacity of the CPM Pelletizing Mill is affected by the moisture content of the wetted biomass.
  • the normal capacity rating of the CPM laboratory pelletizing mill is about 125 lbs/hr. However, if the moisture content of the wetted biomass is about 30% to about 36% by weight, an additional 30-60 lbs/hr additional capacity may be achieved. If the moisture content of the wetted biomass is too low, it will plug the dies. Conversely, if the materials are too wet, unpelletized material will flush out the die.
  • the ground solids may be wetted using either water or steam, and then pelletized to a diameter of about 4 to 6 mm (3/16 to 1/4 inch). This diameter is preferred for further processing the biomass. Smaller diameters may clog the dies, increase the processing temperature, and also increase the wear on the dies. After the pellets are formed, they may be allowed to cool, and then transported. The pellets formed from the process of the present invention show no loss of taxanes over the course of this treatment.
  • the finished pellets can be stored or used as desired.
  • the pellets be substantially cylindrical or parallelepiped.
  • the maximum cross section of each individual pellet should be about 3/16 to about 1/4 inch.
  • the invention in its broadest aspects contemplates producing pellets of any suitable configuration.
  • the pellets may be cube-shaped.
  • the bulk density of pellets produced in the present invention can be at least 30 lbs/ft. 3 , up to 50 lbs/ft. 3
  • the bulk density of the resulting pellet may include the following ranges: about 30 lbs/ft. 3 to about 35 lbs/ft. 3 ; about 35 lbs/ft. 3 to about 40 lbs/ft. 3 ; about 40 lbs/ft. 3 to about 45 lbs/ft. 3 ; about 45 lbs/ft. 3 to about 50 lbs/ft. 3 Equipment Used for Pelletizing
  • taxane or taxane molecule include but are not limited to a molecule that contains a basic baccatin III structure with a (2R,3S)-C 6 H 5 CH(Rx)CH(OH)C(0)- group forming an ester with the hydroxyl group located at the C-13 position of the basic baccatin III structure.
  • the group represented by Rx can be an amino group, a salt of an amino group (e.g., an ammonium salt), an amino group which is protected with an amino protecting group, or a substituent which may be converted into an amino group.
  • Various isomers, homologues, and analogues of the basic baccatin III structure, and of the (2R,3S)-C 6 H 5 CH(Rx)CH(OH)C(0)- group also are included in the definition of a taxane molecule.
  • a 10-deacetylbaccatin III structure is contemplated within the scope of a taxane molecule.
  • a taxane or taxane molecule include, but are not limited to, primary taxanes, for example taxol A (paclitaxel), taxol B (cephalomanninc), taxol C, taxol D, taxol E, taxol F, and taxol G.
  • the definition of a taxane or taxane molecule includes docetaxel (TAXOTERE ® ). (See, e.g., PCT Ser. Appl. No. PCT/US03/105566, which is incorporated herein by reference).
  • a "basic baccatin III structure” means a compound having the formula as shown in the aforementioned application, where each of Ri, R 2 , R 4 , R 7 , Rio and R ⁇ 3 independently is hydrogen, an alkyl group, an acyl group, an aryl group, an arylalkyl group, a vinyl group, an ether group, an ester group, a glycoside group, an oxo group, or a hydroxyl protecting group.
  • baccatin III which has the formula as shown in the aforementioned application
  • 10-deacetylbaccatin III which has the formula as shown in the aforementioned application, where Ac is an acetyl group (CH 3 C(0)-), and Bz is a benzoyl group (PhC(O)- or C 6 H 5 C(0)-).
  • the present invention is directed to a process for making Yew pellets comprising the following steps: (a) adding from about 1% to about 20% w/w water to ground Yew tree material; and (b) compressing the wetted Yew tree material in a die to form a pellet whereby by the resulting pellet has a final moisture content less than 10% by weight.
  • the Yew tree material is ground into a powder.
  • the Yew material is derived from roots.
  • the process of the present invention provides a resulting pellet having a bulk density from about SOlbs/ft 3 to about 501bs/ft 3 .
  • the present process provides a resulting pellet having a final diameter from about 1/16 inch to about 1 inch, or from about 3/16 inch to about l A inch or the final diameter is VA inch.
  • the diameter of the extrusion holes of the die is from about 1/16 inch to about 1 inch, or from about 3/16 inch to about inch.
  • the temperature of the resulting pellet as it emerges from the die is from about 100°F to about 212°F, or from about less than 180°F or from about 130°F to about 160°F.
  • the present invention is directed to a Yew pellet having a final moisture content less than 10% by weight.
  • the pellet has a final moisture content from about 1% to about 6% by weight, or from about 4% to about 6% by weight.
  • the pellet of the present invention has a final bulk density from about 30 lbs/ft 3 to about 50 lbs/ft 3 .
  • the diameter of the pellet is from about 1/16 inch to about 1 inch or 3/16 inch to about l A inch or V ⁇ inch. Turning the pellet mill to higher throughput can reduce the quality of the pellets. Also, as the thickness of the die is increased, the resulting pellets become harder and the capacity and ability of the mill to run are adversely affected.
  • the die is made of high carbon steel. Carbon steel is more preferable than chrome or stainless steel dies.
  • additives can be important with powered biomass materials. In the case of ground root biomass, the use of additives is less important, and in some instance is not required. With Yew tops, for example, it is advantageous to use binder additives to facilitate production of pellets suitable for extraction.
  • binder additives may include, but are not limited to, guar gum, starches, vegetable oils, alginates, xanthan gums, locust bean gum and other suitable binders.
  • the die is first purged with oats, forming pelletized oats.
  • the wetted biomass was run through a CPM 'CL3' Laboratory pellet mill. This mill had a 3 HP motor (220 Volts). The temperature of the resulting pellets were approximately 160° F. The pellets were dark in color, ranging in length of about . inch tol inch. 6. After 20 minutes, the moisture content of the pellets was approximately 10.3%.
  • the bulk density of the pellets was 39 lb./ft 3 '
  • the bulk density of the biomass powder was approximately 18 lbs/ ft 3 '
  • additives can be used to facilitate production of pellets suitable for taxane extraction.
  • the following examples describe an additive (Guar Gum) that can be added to the wetted biomass.
  • Each pelletizing run followed the general protocol shown in Example 1. To evaluate the amount of fines, the die was heated beforehand.
  • Rate Capacity 145 lb/hr.
  • Wgt fines 95 g; wgt of pellets 2000 g;
  • HPLC analysis showed good recovery of total taxanes approximately (approximately 0.02% w/w) for both pellets and non-pellets. HPLC analysis also showed good recovery of paclitaxel (approximately 0.01% w/w) for both pellets and non-pellets. These tests showed no significant loss/degradation of extractable paclitaxel as a result of the pelletization process.
  • pellet production may be accomplished continuously or in separate batches.
  • operating parameters may be varied, depending on many factors. These factors include available materials, economic considerations and energy needs of specific consumers. However, it is to be understood that these and other factors can be made by those skilled in the art without distracting from the sprit and scope of the invention.
  • the present invention is described as having, including, or comprising specific components, or where processes are described as having, including, or comprising specific process steps, it is contemplated that the present invention also consists essentially of, or consists of, the recited components or processing steps. Further, it should be understood that the order of steps or order for performing certain actions are immaterial so long as the invention remains operable. Moreover, two or more steps or actions may be conducted simultaneously so long as the invention remains operable. Also, one or more steps or elements may be omitted from the claimed invention, or the invention described herein suitably may be practiced in the absence of any component or step which is not specifically disclosed herein, so long as the invention remains operable.

Abstract

L'invention concerne un procédé permettant de fabriquer des pastilles à base de bois d'if à partir d'un matériau provenant de l'if. Le procédé décrit dans cette invention comprend les étapes qui consistent (i) à ajouter au matériau provenant de l'if de 1 % environ à 20 % environ en poids d'eau; et (ii) à compresser ce matériau dans une matrice afin de former une pastille. La pastille ainsi obtenue présente une teneur en humidité finale inférieure à 10 % en poids. Les pastilles à base de bois d'if produites selon ce mode de réalisation conviennent à l'extraction des molécules de taxanes contenues dans les pastilles.
PCT/US2003/041824 2002-12-31 2003-12-30 Agglomeration d'une biomasse d'if permettant l'extraction de taxanes et d'autres produits naturels WO2004060626A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CA002512170A CA2512170A1 (fr) 2002-12-31 2003-12-30 Agglomeration d'une biomasse d'if permettant l'extraction de taxanes et d'autres produits naturels
AU2003303565A AU2003303565A1 (en) 2002-12-31 2003-12-30 Pelletizing yew biomass for extraction of taxanes and other natural products
EP03815018A EP1594668A4 (fr) 2002-12-31 2003-12-30 Agglomeration d'une biomasse d'if permettant l'extraction de taxanes et d'autres produits naturels
US11/173,477 US20060127510A1 (en) 2003-12-30 2005-06-30 Harvesting and pelletizing yew biomass for extraction of taxanes and other natural products

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US43743402P 2002-12-31 2002-12-31
US60/437,434 2002-12-31

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US11/173,477 Continuation-In-Part US20060127510A1 (en) 2003-12-30 2005-06-30 Harvesting and pelletizing yew biomass for extraction of taxanes and other natural products

Publications (1)

Publication Number Publication Date
WO2004060626A1 true WO2004060626A1 (fr) 2004-07-22

Family

ID=32713183

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2003/041824 WO2004060626A1 (fr) 2002-12-31 2003-12-30 Agglomeration d'une biomasse d'if permettant l'extraction de taxanes et d'autres produits naturels

Country Status (4)

Country Link
EP (1) EP1594668A4 (fr)
AU (1) AU2003303565A1 (fr)
CA (1) CA2512170A1 (fr)
WO (1) WO2004060626A1 (fr)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5942241A (en) * 1995-06-09 1999-08-24 Euro-Celtique, S.A. Formulations and methods for providing prolonged local anesthesia

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63295800A (ja) * 1987-05-22 1988-12-02 株式会社　ヤマトランス パルプを利用した木材粉末成形品とその製造法
FR2696462B1 (fr) * 1992-10-05 1994-11-25 Rhone Poulenc Rorer Sa Procédé d'obtention de la désacétyl-10 baccatine III.
AU5516596A (en) * 1995-04-29 1996-11-21 Samyang Genex Co., Ltd. A method for mass production of taxol from taxus genus plant
US6375447B1 (en) * 1998-09-29 2002-04-23 Cq Inc. Apparatus for dewatering and pelletizing particulate fuel

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5942241A (en) * 1995-06-09 1999-08-24 Euro-Celtique, S.A. Formulations and methods for providing prolonged local anesthesia
US6514516B1 (en) * 1995-06-09 2003-02-04 Euro-Celtique, S.A. Formulations and methods for providing prolonged local anesthesia

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP1594668A4 *

Also Published As

Publication number Publication date
CA2512170A1 (fr) 2004-07-22
EP1594668A4 (fr) 2006-06-07
EP1594668A1 (fr) 2005-11-16
AU2003303565A1 (en) 2004-07-29

Similar Documents

Publication Publication Date Title
US10213788B2 (en) Method for processing whole hemp stalks to form dry hemp product comprising cannabinoid oil
AU2010254227B2 (en) Pellets and briquettes from compacted biomass
JP6407506B2 (ja) 固形燃料の製造方法及び固形燃料
JP2007237026A (ja) バイオマスを用いた機能製品の製造法
RU97108692A (ru) Способ получения добавки к кормам для животных на основе ферментационного бульона
JPWO2005122787A1 (ja) カプシノイド含有トウガラシ乾燥物およびその乾燥方法
CA3009554A1 (fr) Methode de traitement de tiges entieres de chanvre pour former un produit de chanvre sec comprenant de l'huile de cannabinoide
EP1594668A1 (fr) Agglomeration d'une biomasse d'if permettant l'extraction de taxanes et d'autres produits naturels
CN101869586A (zh) 一种高纯度紫杉醇及其衍生物的提取方法
KR101131870B1 (ko) 수분 함유체의 건조방법 및 고체연료의 제조방법
US10154680B2 (en) Lubricant and binding agent for the production of feedstuff and the like and system and method for use of same
US20060127510A1 (en) Harvesting and pelletizing yew biomass for extraction of taxanes and other natural products
US20070196550A1 (en) Edible product
US8007838B2 (en) Process for producing a stable concentrated dietary supplement and supplement produced thereby
EP2698417A1 (fr) Combustible solide, en particulier pour l'industrie énergétique et son procédé de production
US6444730B1 (en) Mixture of a vegetable residue and a water-absorbing polymer product
JP3105066B2 (ja) 粒状有機質肥料組成物
WO2004060868A2 (fr) Recolte de biomasse d'if pour une extraction de taxanes et d'autres produits naturels
US8715765B2 (en) Process of treating biomass
CN107880913A (zh) 一种沼渣机制炭及其制备方法
Bani et al. Potential of papaya seeds as a heterogenous catalyst in biodiesel synthesis
CN103667357A (zh) 一种提高沼气发酵量的添加剂的制备方法
US20230212617A1 (en) Methods and preparation for hemp biodegradable absorbent
CN102060290A (zh) 一种利用生物质燃烧法生产富勒烯的方法
Rostocki et al. Methods for Treatment of Animal and Plant-Based Biomass Waste

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BW BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NI NO NZ OM PH PL PT RO RU SD SE SG SK SL TJ TM TN TR TT TZ UA UG US UZ VN YU ZA ZM ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): BW GH GM KE LS MW MZ SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LU MC NL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
WWE Wipo information: entry into national phase

Ref document number: 2512170

Country of ref document: CA

WWE Wipo information: entry into national phase

Ref document number: 11173477

Country of ref document: US

WWE Wipo information: entry into national phase

Ref document number: 2003815018

Country of ref document: EP

WWP Wipo information: published in national office

Ref document number: 2003815018

Country of ref document: EP

WWP Wipo information: published in national office

Ref document number: 11173477

Country of ref document: US

NENP Non-entry into the national phase

Ref country code: JP

WWW Wipo information: withdrawn in national office

Country of ref document: JP