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WO1998002041A1 - Composition therapeutique provenant de la canne a sucre et ses utilisations therapeutiques - Google Patents

Composition therapeutique provenant de la canne a sucre et ses utilisations therapeutiques Download PDF

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Publication number
WO1998002041A1
WO1998002041A1 PCT/US1997/013427 US9713427W WO9802041A1 WO 1998002041 A1 WO1998002041 A1 WO 1998002041A1 US 9713427 W US9713427 W US 9713427W WO 9802041 A1 WO9802041 A1 WO 9802041A1
Authority
WO
WIPO (PCT)
Prior art keywords
bercedin
extract
heating
sugar cane
patients
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/US1997/013427
Other languages
English (en)
Inventor
Gonzalo A. Bermudez
Arturo E. Bermudez
Fernando J. Bermudez
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BIOCELL RESEARCH Inc
Original Assignee
BIOCELL RESEARCH 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 BIOCELL RESEARCH Inc filed Critical BIOCELL RESEARCH Inc
Priority to AU39012/97A priority Critical patent/AU3901297A/en
Priority to EP97936309A priority patent/EP0880318A4/fr
Publication of WO1998002041A1 publication Critical patent/WO1998002041A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
    • 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
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/88—Liliopsida (monocotyledons)
    • A61K36/899—Poaceae or Gramineae (Grass family), e.g. bamboo, corn or sugar cane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • C07H1/06—Separation; Purification
    • C07H1/08—Separation; Purification from natural products
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Definitions

  • This invention relates to compositions derived from extracts of sugar cane, which are useful to treat a variety of pathological conditions in humans and other mammals.
  • the present invention is based on the unexpected discovery that saccharide- containing extracts of sugar cane prepared according to the methods of the invention are effective for the treatment of a wide variety of pathological conditions.
  • sugar cane and extracts thereof have not been recognized as containing therapeutically beneficial components.
  • oligosaccharide or other carbohydrate moieties present on the surface of biological entities such as extracellular matrix, cells, or viruses.
  • lectins or lectin-like molecules are involved; these molecules (usually proteins) specifically recognize, and bind with high affinity to, particular sugar or oligosaccharide moieties, thereby implementing a particular binding or recognition function.
  • Less specific adhesive interactions between surface components may also involve sugar or oligosaccharide moieties.
  • Adhesive interactions may involve monosaccharides, oligosaccharides having highly stereospecific structures, or polysaccharides containing different substitutent side- chain sugars.
  • the interactions are primarily electrostatic, and may be between different sugar moieties, sugars and protein components, or combinations thereof. It has been suggested that drugs that interfere with these interactions may be useful as anti- inflammatory and anti-infectious agents (Sharon et al. , Scientific American, Jan., 1993, p. 82).
  • the treatment methods and compositions of the present invention exert their effect primarily via an anti- adhesive mechanism. That is, it is believed that a beneficial effect is achieved by interfering with specific interactions between cell-surface lectin-type molecules that may be present on one entity, and the corresponding sugar or oligosaccharide moieties recognized by such lectins that may be present on another entity.
  • One entity may be a pathogenic microorganism such as a virus or bacterium, and the other entity may be a cell, such as, for example, a skin or mucosal cell.
  • one entity may be a cancer cell, virus infected cell, or a pathogenic microorganism and the other entity may be normal tissue or a component of the extracellular matrix or environment.
  • the hygroscopicity of the composition of the present invention is believed to contribute to its beneficial therapeutic and preventive properties. Prior to the present invention, there would have been no reason to believe that extracts of sugar cane, particularly those prepared according to the invention, would exhibit beneficial anti-adhesive properties.
  • the present invention provides therapeutic compositions , preferably derived from sugar cane, which contain primarily saccharide and a ino acid components and are useful for treatment of a variety of pathological conditions in mammals, including humans.
  • the precise nature of the active principle(s) is not yet known; nonetheless, it is believed that heat polymerization of one or more components of the sugar cane extract is required to develop the therapeutic activity of the composition.
  • the pathological conditions that may be treated according to the invention encompass those caused by .Inflammation, by bacterial, viral (including retroviral), or fungal infection, or by toxins, including without limitation dermic lesions produced by Hansen's disease, diabetic foot ulcers, diabetic gangrene, perineal necrotizing cellulitis, intestinal fistula, rectum-perineal fistula, eviscerations, decubital and vascular source ulcers, acne, and infection with herpes simplex, herpes genitalis, influenza and cold viruses, Hepatitis A and B, and human immunodeficiency virus (HIV).
  • the invention provides methods for preparing compositions useful in anti-adhesive therapies, comprising the steps of:
  • the invention provides methods for treatment of pathological conditions in humans, which comprise administering effective amounts for treating the conditions of the anti-adhesive compositions.
  • Administration of the anti-adhesive compositions of the present invention may be achieved by any effective route, including topical, oral, enteral, intravenous, intramuscular, subcutaneous, transmucosal, and by-inhalation routes.
  • the preferred mode of administration depends upon the condition being treated. For example, for treating skin lesions or wounds, a topical route is preferred; while treatment of a systemic viral infection is preferably achieved using oral or intravenous administration.
  • pharmaceutical formulations comprising the compositions described above in conjunction with pharmaceutically acceptable carriers and/or excipients.
  • the invention provides methods for purifying one or more active components from the anti-adhesive compositions and methods for testing the efficacy of purified components (and combinations thereof) in treating different pathological conditions.
  • compositions and methods for treating a broad range of pathological conditions in animals preferably mammals, and most preferably, humans.
  • compositions are preferably derived from sugar cane by extraction and heating of the extract in a non-fermentation process, which is described in more detail below.
  • the methods involve administering to affected individuals or applying to the affected organ or tissue effective amounts of the therapeutic compositions of the invention for a sufficient time to achieve a beneficial clinical result.
  • an "effective amount" of the compound for treating a pathological condition according to the present invention is an amount that results in measurable amelioration of at least one symptom or parameter of the condition.
  • An effective amount for treating the condition can be determined by experimentation known in the art, such as by establishing a matrix of dosages and frequencies and comparing a group of experimental units or subjects to each point in the matrix. The exact amount to be administered to a patient may vary depending on the nature of the disorder, the severity of the disorder, and the physical condition of the patient.
  • a measurable or significant amelioration of any symptom or parameter may be determined by assay as known in the particular field, or determined by a physician skilled in the art, or reported by the patient to the physician. It will be understood that any clinically or subclinically significant attenuation of any symptom or parameter pursuant to treatment according to the present invention is within the scope of the invention. Clinically significant attenuation means perceptible to the patient and/or to the physician.
  • pathological condition refers to any dysfunction in a normal physiological function or disruption in general health of the individual.
  • the pathological conditions that may be treated using the compositions of the present invention encompass those caused by inflammation, by bacterial, viral, or fungal infection, or by toxins, as well as other pathological conditions such as burns and other wounds.
  • dermic lesions produced by Hansen's disease, diabetic foot ulcers, diabetic gangrene, perineal necrotizing cellulitis, intestinal fistula, rectum-perineal fistula, eviscerations, decubital and vascular source ulcers, acne, and infection with herpes simplex, herpes genitalis, influenza and cold viruses, Hepatitis A and B, and human immunodeficiency virus (HIV) or its complications such as from opportunistic infections, pneumocystis carinii, tuberculosis, toxoplasmosis, mycosis fungoides, cytomegalovirus, etc.
  • HIV human immunodeficiency virus
  • compositions of the present invention may be prepared by the following procedure:
  • the cane including an intact bark and medulla, is introduced into a sugar mill (trapiche). The cane is thoroughly macerated to produce a liquid extract and a fibrous residue, called bagasse. The liquid is separated from the bagasse and by mechanical means and filtered, and the bagasse is discarded.
  • Heating step *** The liquid extract is transferred to a heating chamber, such as an oven, in which it is maintained quiescent at a temperature of between about 60- 70°C for 30-60 min, preferably 45 min. During this step remaining impurities rise to the top and are skimmed off. The temperature range and heating time are chosen to allow the impurities to rise to the surface.
  • Heating step 2 The heated liquid extract is then heated at temperatures between about 130-165°C, preferably 140-160°C and most preferably 150°C, for a 24-hour period. During this time, the extract is subjected to constant and uniform agitation, which is e.g. achieved using mechanical but gentle means such as a spoon which may be made of wood, metal or another heat resistant material, stirring at a mixing rate of 20-25/RPM; preferably, this is done in an open container most preferably one made of heat-cured laurel wood. In the process, a considerable fraction of the water component of the extract evaporates. The evaporation process is monitored visually and proceeds until the extract has a semisolid or solid consistency and color similar to that of honey. The color of the product is light brown. It is important that the extract reach a temperature of at least 150°C (its boiling point at sea level).
  • the resulting solid designated Bercedin, has the following chemical composition: component weight % (grams) carbohydrate (mono-, oligo- and 90 polysaccharides) lectin and other amino acid 0.6 containing molecules calcium 0.3 iron 0.51 phosphorus 0.57 thiamines 0.02 niacin 0.42 carotenes 0.17 riboflavin 0.17 ash 0.10 nonash impurities 0.20 fiber 0.20 water 6.74
  • the present invention encompasses pharmaceutical formulations comprising
  • the formulations include liquid dosage forms having a physiologically acceptable carrier, such as, for example, phosphate buffered saline or deionized water.
  • a physiologically acceptable carrier such as, for example, phosphate buffered saline or deionized water.
  • Bercedin is highly soluble in water and can be easily dissolved at concentrations of 10-100% (w/v).
  • the pharmaceutical formulations may also contain excipients, including preservatives and stabilizers, that are well-known in the art.
  • Bercedin or its derivatives can be formed into topical dosage forms such as creams, ointments, sprays, and the like. Bercedin can also be formed into solid oral or non-oral dosage units such as, for example, tablets, capsules, powders, and suppositories, and may additionally include excipients, including without limitation lubricant(s), plasticizer(s), colorant(s), absorption enhancer(s), bactericide(s), and the like. Modes of administration include topical, oral and enteral, intravenous, intramuscular, subcutaneous, transmucosal
  • a topical route is preferred.
  • an oral or transdermal route is used (i.e., via solid or liquid oral formulations, or skin patches, respectively).
  • systemic infections such as, e.g., HIV
  • oral or intravenous administration may be used.
  • the amount of the agent to be administered may also depend upon the mode of administration.
  • formulations containing Bercedin, preferably 100% Bercedin, if desired in granular or powder form may be applied to an affected area between one and three times a day.
  • compositions may contain between about 10% and about 100% (w/v) Bercedin.
  • the dosages for oral, mucosal, or intravenous systemic administration may range from about 20 to about 40 g of active ingredient (i.e. Bercedin) per patient per day, preferably about 30 g/patient/day. Topical and systemic administration can be used conjointly in which case the systemically delivered dosage can be decreased, if desired.
  • a method for treating infection comprises administering, in addition to Bercedin, other conventional bioactive substances that may act additively or synergistically with Bercedin to achieve a therapeutic effect.
  • Antibiotics that can be used in conjunction with Bercedin in the methods and compositions of the present invention include without limitation penicillins (such as ampicillin, amoxicillin, methicillin, and the like), cephalosporins, aminoglycosides (such as streptomycin, neomycin, kanamycin, gentamicin, and the like), tetracyclines, chloramphenicol, and vancomycin.
  • a method for treating HIV infection comprises a 60-day treatment regimen in which the following are administered in combination (though not necessarily simultaneously as will be explained below): Oral Bercedin (30 g/day); Vitamin C (1 g/day) preferably intravenously; Streptomycin sulfate (3 g/day, 1 g being administered preferably orally every 8 hours); and a multi-vitamin supplement including trace elements, such as Supradyn (Roche) 1/day. It is believed that this treatment specifically acts on intestinal HIV target cells that are thought to act as reservoirs for the virus, and thereby reduce viral burden.
  • the vitamin C is preferably administered substantially simultaneously with Bercedin (e.g.
  • Treatment commences when symptoms appear, and is continued at least until they are eliminated (or for 45-60 days).
  • Topical application of Bercedin can be combined with systemic administration each following the regimen described above.
  • treatment with Bercedin results in decrease of the duration and severity of the flare up and, often, avoidance of recurrence.
  • hepatitis A or B systemic administration of 30g/day (orally) for two months has consistently resulted in elimination of the hepatitis A and in avoidance of relapses in the case of hepatitis B for prolonged periods of time (a total of 8 patients have been treated for hepatitis B, and none have experienced recurrence: two have been followed for 12 years, one for 11 years, and 3 for six years).
  • Bercedin may be administered orally preventively during the influenza season, or therapeutically upon appearance of symptoms (treatment may be stopped after 3 days but is preferably continued for 7 days or longer). Scores of patients treated therapeutically report an immediate decrease in the duration and severity of influenza symptoms (aches, congestion, fatigue, fever) with the condition lasting only 3-4 days.
  • topical application of the compositions of the present invention to unhealed wounds of varying causes consistently resulted in: a) Prevention and/or reduction in bacterial contamination of the wound; b) Rapid granulation; c) Increased vascularization of the wound; d) Expulsion or centralization of the necrotic threads or threads that are in an early stage of necrosis; e) An increase in the protein level from 100 ⁇ g to 500 ⁇ g within 24 hrs after initial application; and f) An increase in the hemoglobin level from 50 ⁇ g to 150 ⁇ g.
  • compositions of the present invention results in proliferation of the microvasculature, reactivation of interstitial elements such as fibroblasts, reticulocytes, and collagen, and increase in granulation threads.
  • interstitial elements such as fibroblasts, reticulocytes, and collagen
  • epithelial proliferation through the depth of the lesion to form a basal epithelial layer.
  • the present invention encompasses the identification of active ingredients and/or combinations of ingredients in Bercedin, as well as the elucidation of critical proportions of one or more ingredients. This type of analysis enables the optimization of different formulations comprising Bercedin and Bercedin derivatives for treating different pathological conditions.
  • Bercedin is subjected to fractionation and purification using methods well-known in the art of natural product biochemistry, including without limitation: crystallization; distillation (including fractional and steam distillation); filtration; centrifugation; differential extraction (using organic and aqueous solutions, including acids and bases); and chromatography, including molecular sizing, partition, countercurrent distribution, high-pressure liquid (using reverse-phase and silica-based resins), ion-exchange, and adsorption chromatography (using lipophilic or hydrophobic phases, or solid-phase lectins).
  • fractions are collected and analyzed for (i) their physical- chemical nature and (ii) their bioactivity.
  • spectroscopic methods may be used, such as, for example, mass spectrometry (MS) (including high-resolution electrospray MS, laser desorption methods, time-of- flight methods, and fast-action bombardment using a variety of matrices); high-resolution nuclear magnetic resonance spectrometry (including proton, carbon, and nitrogen modes); infrared; ultraviolet; and visible spectrometry.
  • MS mass spectrometry
  • high-resolution electrospray MS including high-resolution electrospray MS, laser desorption methods, time-of- flight methods, and fast-action bombardment using a variety of matrices
  • high-resolution nuclear magnetic resonance spectrometry including proton, carbon, and nitrogen modes
  • infrared ultraviolet
  • ultraviolet ultraviolet
  • visible spectrometry visible spectrometry
  • Bioactivity of different fractions can be monitored by in vivo or in vitro methods.
  • culture systems well-known in the art can be used to quantify bacterial or viral infectivity.
  • a stock culture of a particular bacterium or virus is mixed with the fraction being tested, after which the mixture is contacted with a suitable host cell, and infection is monitored by cytopathology or lysis of the host cell.
  • in vivo animal model systems can be used to monitor tumor cell invasiveness.
  • a defined amount of tumor cells are contacted with the fraction being tested, after which the mixture is introduced into an animal (into, e.g., a subcutaneous or peritoneal site) and the appearance of metastatic tumors is monitored.
  • animal into, e.g., a subcutaneous or peritoneal site
  • Other model systems are well-known in the art for monitoring, e.g. , wound healing, effect of toxins, and the like.
  • Bercedin derivatives for different therapeutic purposes.
  • a particular oligosaccharide component may be more active (on a weight percentage basis) than unfractionated Bercedin for promoting wound healing; accordingly, this derivative would be formulated at an appropriate concentration into a topical cream or spray for clinical use.
  • the patients were administered the regimen described above as preferred for treating HIV infection for two months.
  • Diarrhea was inhibited after three or four days from the start of the treatment without the use of any anti-cholinergics; the patients then recovered from dehydration due to the diarrhea by normal consumption of liquids. Fever also disappeared after three or four days in the absence of anti-fever medication. Body weight increased by 15 to 35 pounds (in some cases more) within a time period of two months.
  • Example 3 Reverse seroconversion in an HTV-infected individual subsequent to Bercedin treatment
  • JAM a 35-year old female, was admitted for an ectopic pregnancy. During surgery, she was given three units of blood. After this time, she showed the following symptoms: diarrhea, insomnia, fatigue, night sweats, weight loss of 3 kg body weight and nervous perturbation.
  • a micro-ELISA gave a highly positive result.
  • the sample was sent to the
  • HTL 3 Antibody (by Abbott) 0.863 positive strong and positive Western Blot (+. + .).
  • the sample was taken the patient was considered clinically asymptomatic.
  • the patient has remained asymptomatic since the time of treatment (nine years).
  • the reversal of the micro-ELISA titer strongly suggests that the treatment according to the invention dramatically reduced any HIV infection.
  • HIV-negative and HIV-positive patients Prior to enrolling in the study, HIV-negative and HIV-positive patients receive a general physical examination and blood will be drawn for a CBC, ESR, lymphocyte panel, bDNA viral load, and chemistry screen with lipids. A routine urinalysis will also be performed. Inclusion criteria include: more than 18 years of age; for normal subjects, HIV negative and in apparent good health; for HIV-positive subjects, having a detectable viral load by bDNA evaluation and having CD4+ lymphocyte counts below 500 cells/mm 3 .
  • Exclusion criteria include: use of AZT or other anti-retroviral medications, including protease inhibitors; use of prophylactic antibiotics other than Trimethoprim/sulfanemethoxazole; hepatitis or known significant liver abnormality (detected by physical exam, history, or serum GGt, ALT, and AST enzyme levels); renal abnormalities (detected by physical exam, history, serum BUN and creatinine levels, or urinalysis); pregnancy or breast-feeding; diabetes or volatile blood glucose and triglycerides; and pancreatitis.
  • prophylactic antibiotics other than Trimethoprim/sulfanemethoxazole
  • hepatitis or known significant liver abnormality detected by physical exam, history, or serum GGt, ALT, and AST enzyme levels
  • renal abnormalities detected by physical exam, history, serum BUN and creatinine levels, or urinalysis
  • pregnancy or breast-feeding diabetes or volatile blood glucose and trigly

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
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  • Natural Medicines & Medicinal Plants (AREA)
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  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Genetics & Genomics (AREA)
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  • Animal Behavior & Ethology (AREA)
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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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Abstract

Compositions thérapeutiques provenant de la canne à sucre et destinées à traiter une variété de conditions pathologiques chez les animaux et plus particulièrement chez les humains, y compris celles causées par les inflammations, les infections bactériennes, virales ou fongiques, les toxines, les traumatismes tels que les brûlures, et autres. Des procédés de préparation de ces compositions thérapeutiques sont également décrits, ainsi que des formulations pharmaceutiques les comprenant, des procédés de traitement d'états pathologiques et des procédés de purification des constituants actifs à partir de ces compositions.
PCT/US1997/013427 1996-07-17 1997-07-11 Composition therapeutique provenant de la canne a sucre et ses utilisations therapeutiques Ceased WO1998002041A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU39012/97A AU3901297A (en) 1996-07-17 1997-07-11 Therapeutic composition from sugar cane and therapeutic uses thereof
EP97936309A EP0880318A4 (fr) 1996-07-17 1997-07-11 Composition therapeutique provenant de la canne a sucre et ses utilisations therapeutiques

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US2187596P 1996-07-17 1996-07-17
US60/021,875 1996-07-17

Publications (1)

Publication Number Publication Date
WO1998002041A1 true WO1998002041A1 (fr) 1998-01-22

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ID=21806627

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1997/013427 Ceased WO1998002041A1 (fr) 1996-07-17 1997-07-11 Composition therapeutique provenant de la canne a sucre et ses utilisations therapeutiques

Country Status (5)

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EP (1) EP0880318A4 (fr)
AR (1) AR004429A1 (fr)
AU (1) AU3901297A (fr)
CA (1) CA2232297A1 (fr)
WO (1) WO1998002041A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000021546A1 (fr) 1998-10-09 2000-04-20 Mitsui Sugar Co., Ltd Prophylactiques/medicaments pour l'infection, agents anti-endotoxine, adjuvants de vaccin et promoteurs de croissance
WO2000035468A1 (fr) * 1998-12-14 2000-06-22 Biocell Research, Inc. Procedes visant a ameliorer la croissance de la volaille et d'en reduire la colonisation bacterienne
JP2003063975A (ja) * 2001-08-28 2003-03-05 National Agricultural Research Organization コクシジウムによって引き起こされるヒトまたは動物の病気に対する予防治療剤及びコクシジウムの軽感染に対するヒトまたは動物の免疫のためのアジュバント剤

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5055455A (en) * 1988-09-28 1991-10-08 Brigham And Women's Hospital Capsular polysaccharide adhesin antigen, preparation, purification and use
US5547674A (en) * 1995-04-14 1996-08-20 University Of Southern California Pharmaceutical preparations derived from European mistletoe

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Publication number Priority date Publication date Assignee Title
DE4138192A1 (de) * 1990-08-30 1993-05-27 Karin Omlor Mittel auf pflanzlicher basis, zur erneuerung der haut bei frischen brandverletzungen, zur reinigung unreiner haut, zur bekaempfung von krampfadern, zum abklingen von schwellungen bei verletzungen, zum abklingen von schwellungen und juckreiz bei insektenstichen, bei aeusserlicher anwendung

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5055455A (en) * 1988-09-28 1991-10-08 Brigham And Women's Hospital Capsular polysaccharide adhesin antigen, preparation, purification and use
US5547674A (en) * 1995-04-14 1996-08-20 University Of Southern California Pharmaceutical preparations derived from European mistletoe

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP0880318A4 *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000021546A1 (fr) 1998-10-09 2000-04-20 Mitsui Sugar Co., Ltd Prophylactiques/medicaments pour l'infection, agents anti-endotoxine, adjuvants de vaccin et promoteurs de croissance
JP2000297046A (ja) * 1998-10-09 2000-10-24 Mitsui Sugar Co Ltd 感染予防治療剤、抗エンドトキシン剤、ワクチンワクチンアジュバント剤および成長促進剤
US7150885B2 (en) * 1998-10-09 2006-12-19 Mitsui Sugar Co., Ltd. Preventives/remedies for infection, anti-endtoxin agents, vaccine adjuvants and growth promoters
US7368136B2 (en) 1998-10-09 2008-05-06 Mitsui Sugar Co., Ltd. Preventives or remedies for infection, anti-endotoxin agents, vaccine adjuvants and growth promoters
US7416745B2 (en) 1998-10-09 2008-08-26 Mitsui Sugar Co. Ltd Preventives or remedies for infection, anti-endotoxin agents, vaccine adjuvants and growth promoters
EP1120118B1 (fr) * 1998-10-09 2010-05-26 Mitsui Sugar Co., Ltd. Prophylactiques/medicaments pour l'infection, agents anti-endotoxine, adjuvants de vaccin et promoteurs de croissance
WO2000035468A1 (fr) * 1998-12-14 2000-06-22 Biocell Research, Inc. Procedes visant a ameliorer la croissance de la volaille et d'en reduire la colonisation bacterienne
JP2003063975A (ja) * 2001-08-28 2003-03-05 National Agricultural Research Organization コクシジウムによって引き起こされるヒトまたは動物の病気に対する予防治療剤及びコクシジウムの軽感染に対するヒトまたは動物の免疫のためのアジュバント剤

Also Published As

Publication number Publication date
EP0880318A4 (fr) 1999-07-28
CA2232297A1 (fr) 1998-01-22
AR004429A1 (es) 1998-12-16
AU3901297A (en) 1998-02-09
EP0880318A1 (fr) 1998-12-02

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