WO2008028336A1 - Composition pharmaceutique à base de scutellareine et de scutellarine ou de baicaline ayant un effet antitumoral synergique - Google Patents

Composition pharmaceutique à base de scutellareine et de scutellarine ou de baicaline ayant un effet antitumoral synergique Download PDF

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Publication number
WO2008028336A1
WO2008028336A1 PCT/CN2006/002267 CN2006002267W WO2008028336A1 WO 2008028336 A1 WO2008028336 A1 WO 2008028336A1 CN 2006002267 W CN2006002267 W CN 2006002267W WO 2008028336 A1 WO2008028336 A1 WO 2008028336A1
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WO
WIPO (PCT)
Prior art keywords
wild
yellow
yuan
tumor
scutellariae
Prior art date
Application number
PCT/CN2006/002267
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English (en)
Chinese (zh)
Inventor
Yixin Wu
Original Assignee
Shanghai Gloriayx Biopharmaceuticals Co., Ltd
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
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Application filed by Shanghai Gloriayx Biopharmaceuticals Co., Ltd filed Critical Shanghai Gloriayx Biopharmaceuticals Co., Ltd
Priority to PCT/CN2006/002267 priority Critical patent/WO2008028336A1/fr
Publication of WO2008028336A1 publication Critical patent/WO2008028336A1/fr

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Classifications

    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • 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
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents

Definitions

  • the present invention relates to a pharmaceutical composition having a synergistic antitumor effect, and in particular to a pharmaceutical composition having a synergistic antitumor effect containing a xanthone compound.
  • the invention also relates to methods of preparation and pharmaceutical use of the compositions. Background technique
  • Chemotherapy is short for "chemical drug treatment.”
  • the current concept of chemotherapy is generally understood as “the treatment of tumors", that is, the use of anti-tumor chemicals, and the use of certain measures and protocols to treat tumors.
  • common chemotherapeutic drugs such as vincristine, cisplatin, methotrexate, cyclophosphamide, 5-fluorouracil (5-Fu) can produce local pain, venous thromboembolism, myelosuppression, and gastrointestinal reactions. , peripheral neuropathy and other toxic side effects.
  • cisplatin is clinically used in combination with 5-Fu, bleomycin or epipodophyllotoxin to treat esophageal cancer.
  • “Synergistic Effect” refers to the sum of the effects of the two drugs when they are used in combination with the two drugs when they are used alone. According to the principle of medium effect (Joseph R. Bertino, Ting-Chao Chou, Chemotherapy: Synergism and Antagonism, Encyclopedia of Cancer, 1996, Academic Press, Inc.), the effect of the combination of the two drugs can be achieved through the "combination index” (Combination) Index, CI) to judge:
  • CI ⁇ 1 When CI ⁇ 1 , it is synergistic, CI - 1 is additive; when CI > 1, it is antagonistic.
  • the transplanted tumor strains in mice are: mouse melanoma cell line B16, mouse fibrosarcoma cell line M5076 and other solid tumors. (solid tumor) tumor strain; mouse leukemia cell line L1210 and other blood tumor tumor strains.
  • a person of ordinary skill in the art uses a tumor tumor strain as an in vivo test model for transplanted tumors: a mouse animal test using mouse melanoma cell line B16 as an in vivo test model for solid tumors.
  • the tumor weight or tumor volume inhibition rate was used as an observation index; the mouse animal test of mouse leukemia cell line L1210 was used as an in vivo test model for blood tumors, and the life extension rate of tumor-bearing animals was used as an observation index.
  • the results of the in vitro and in vivo tests are combined to determine whether the substance to be tested has an antitumor effect.
  • Wild scutellariae, wild scutellariae and astragalus are all flavonoids, which can be extracted from plants such as Scutellaria barbata and Astragalus.
  • the molecular weight of wild scutellariae is 286, and the molecular formula is C 15 H 1G 0 6 .
  • the structural formula is as follows -
  • the advent of the present invention is based on the discovery that: wild scutellariae has a synergistic effect on wild scutellaria or scutellaria, which can significantly enhance its cytotoxic activity against tumor cells; contains wild scutellaria and wild scutellaria and/or jaundice
  • the pharmaceutical composition has an enhanced anti-tumor effect and is more effective than a pharmaceutical composition containing only a single wild scutellaria, wild scutellaria or scutellaria.
  • one aspect of the present invention relates to the use of wild xanthine in the preparation of an antitumor agent having synergistic effects on a compound of the following formula (I):
  • R 2 represents hydrogen or a hydroxyl group
  • Another aspect of the invention relates to a pharmaceutical composition having a synergistic anti-tumor effect, comprising a wild xanthine and a compound of formula (I), wherein the wild xanthine and the compound of formula (I) are moles
  • concentration ratio is from 2:1 to 1:4.
  • the present invention also relates to a method of preparing the above pharmaceutical composition and the use of the above pharmaceutical composition for the preparation of an antitumor medicament.
  • the present inventors have found that when the wild scutellariae of the present invention is administered simultaneously with wild scutellaria or scutellaria, the antitumor activity can be significantly enhanced and has a synergistic effect. Thereby reducing the amount and reducing its toxic side effects. Therefore, the wild scutellariae of the present invention and wild scutellaria or scutellaria can be used for the preparation of a synergistic drug against tumors.
  • the wild scutellariae, wild scutellaria or scutellariae of the present invention are naturally occurring and can be isolated from certain plants such as Scutellaria barbata and Radix Scutellariae.
  • the wild scutellariae, wild scutellaria or scutellariae of the present invention can also be obtained commercially or by common synthetic techniques, microbial techniques, and animal and plant cells in the art. f
  • the chemicals used to isolate or synthesize the wild xanthine, wild xanthine or xanthine of the present invention include solvents, reagents, catalysts, protecting group reagents, deprotecting group reagents.
  • the separation and synthesis may also include the step of adding or removing a suitable protecting group to ultimately obtain the desired wild xanthine, wild xanthine or xanthine.
  • Methods for the preparation of the synthetic chemical transformation and group protection (deprotection) of the wild xanthine, wild xanthine or xanthine of the present invention are well known to those skilled in the art, see R.
  • the wild scutellariae of the present invention may be administered simultaneously or non-simultaneously with wild scutellaria or scutellaria; it may be administered by the intestinal or parenteral route.
  • Formulations for enteral administration include, but are not limited to, capsules, tablets, emulsions, aqueous suspensions, colloidal solutions, solutions, microcapsules, pills, troches, granules, powders.
  • Pharmaceutically acceptable carriers commonly used in tablets include lactose and corn starch. A lubricant such as magnesium stearate is usually added.
  • Pharmaceutically acceptable carriers commonly used in capsules include lactose and dried corn starch.
  • compositions of the present invention When formulated as an oral suspension and/or emulsion, the pharmaceutical compositions of the present invention may be suspended or dissolved in an oily phase and combined with an emulsifying or suspending agent. If desired, some sweeteners and/or flavoring agents and/or coloring agents may also be added.
  • Formulations for parenteral administration include injections, creams, ointments, patches or sprays.
  • Parenteral routes of administration include subcutaneous, intradermal, arterial, venous, intramuscular, joint, synovial, sternal, intrathecal, intralesional, intracranial injection or instillation.
  • Other routes of administration may include topical, rectal, nasal, buccal, vaginal, sublingual, mucosal, tracheal or urethral.
  • the pharmaceutical composition of the present invention can also be administered by aerosol inhalation or implantation or accumulation.
  • the pharmaceutical composition of the present invention can be formulated into a sterile injectable preparation such as a sterile aqueous phase or an oil phase suspension.
  • This suspension can be prepared by a conventional method in the art using a suitable dispersing or wetting agent (e.g., Tween 80), a suspending agent, or the like. It may also be an aqueous solution or suspension in a non-toxic diluent or solvent for parenteral administration, such as a solution in 1,3-butanediol.
  • suitable dispersing or wetting agent e.g., Tween 80
  • a suspending agent e.g., a suspending agent
  • It may also be an aqueous solution or suspension in a non-toxic diluent or solvent for parenteral administration, such as a solution in 1,3-butanediol.
  • Related useful carriers or solvents include mannitol, water, Ringer's solution, isotonic sodium chloride, and the
  • bland fixed oils are often used as a vehicle for solvents or suspending agents, and thus a wide variety of mild, fixed oils including synthetic mono- or diglycerides are suitable.
  • Fatty acids such as oleic acid and its glyceride derivatives (such as olive oil or castor oil, especially It is a polyoxyethylene derivative thereof or the like which can be used for the preparation of the injection.
  • the oil solution or suspension may also contain a long chain ethanol diluent or dispersant or carboxymethyl cellulose or similar other dispersing agents which are commonly used in the preparation of pharmaceutically acceptable emulsions and/or suspending agents.
  • Other surfactants commonly used in preparations such as
  • Tweens or Spans and/or other similar emulsifiers or bioavailability enhancers and the like are also useful in the preparation of the pharmaceutical compositions of the present invention.
  • compositions of the present invention can be formulated as a suppository for rectal administration by mixing the pharmaceutical compositions of the present invention with a suitable non-irritating excipient which is solid at room temperature and liquid at the rectal temperature.
  • a suitable non-irritating excipient which is solid at room temperature and liquid at the rectal temperature.
  • excipients include, but are not limited to, cocoa butter, beeswax, and polyethylene.
  • the topical preparation (e.g., ointment) of the pharmaceutical composition of the present invention can be directly used for the affected area.
  • Such topical formulations contain the active ingredient together with pharmaceutically acceptable carriers including, but not limited to, mineral oil, liquid petroleum, white petroleum, propylene glycol, polyoxyethylene or polyoxypropylene compound, emulsified wax or water.
  • the pharmaceutical composition of the present invention can also be formulated as a lotion or an oil.
  • Suitable carriers include, but are not limited to, mineral oil, sorbitol monostearate, polysorbate 60, cetyl ester, cetyl alcohol, 2-octadecyl alcohol, benzyl alcohol or water.
  • the pharmaceutical composition of the present invention can also be formulated into an enema or the like for local administration in the rectum. Topical transdermal patches are also within the scope of the invention.
  • compositions of the present invention may also be administered by nasal spray or by inhalation, i.e., using benzyl alcohol or other preservatives, absorption enhancers, fluorocarbons, and/or other solubilizing or dispersing agents, according to conventional methods in the art.
  • a salt solution was prepared.
  • the pharmaceutical compositions of the invention may also be administered by implantation.
  • the effect of the pharmaceutical composition of the present invention can be sustained and time-released in the body of the administered subject by the implantation method.
  • implant administration can also be administered in local tissue and organ localization (Negrin et al., Biomaterials 22 (6): 563, 2001).
  • Timed release techniques can also be used in the administration of the pharmaceutical compositions of the present invention, such as Timed release capsules based on polymer technology, sustained release techniques and formulation wrapping techniques (eg, polymers and liposomes).
  • Patches are also included within the scope of the present invention. It includes a base layer (e.g., a polymer, cloth, yarn, and bandage) and a pharmaceutical composition of the present invention. One side of the base layer may be provided with a protective layer to prevent the active ingredient from flowing out.
  • the patch may further contain a binder for immobilization, and the latter may be a natural or synthetic substance which temporarily adheres to the skin when it comes into contact with the skin of the subject to be administered.
  • the adhesive can be waterproof.
  • the "pharmaceutically acceptable carrier” does not impair the pharmaceutical activity of the pharmaceutical composition of the present invention, and its effective amount, i.e., the amount which can function as a pharmaceutical carrier, is not toxic to the human body.
  • “Pharmaceutically acceptable carrier” includes but is not limited to: Ion exchange materials, alumina, aluminum stearate, lecithin, self-emulsifying drug delivery systems (SEDDS) such as d- ⁇ -vitamin E polyethylene glycol 1000 succinate, Tweens or other similar polymerization media a surfactant for pharmaceutical preparations, a serum protein such as human serum albumin, a buffer substance such as phosphate, glycine, sorbic acid, potassium sorbate, a mixture of fatty acid partial glycerides of a plant, water, a salt, an electrolyte such as sulphate , dibasic hydrogen phosphate, potassium hydrogen phosphate, sodium chloride, zinc salt, silica gel, magnesium silicate, and the like.
  • Drug delivery can be used to promote the pharmaceutical combination of the present invention.
  • WO93/23033 discloses the dosage of Astragalus membranaceus as an apoptosis inducing agent.
  • the dosage can be adjusted according to the route of administration, the condition and the age of the patient.
  • the general oral dosage is: Astragalus 100-6000 mg/day/ People, take 1-3 times; when administered orally, it can be used in an amount of 1-100 mg / day / person. There have been no reports on the clinical antitumor doses of wild scutellariae and wild scutellaria and their appropriate routes of administration.
  • Example 1 The synergistic effect of wild scutellariae combined with wild scutellaria and astragalus on growth inhibition of human tumor cell lines in vitro
  • Cells of various human tumor cell lines were suspended in a cell culture medium containing 10% (small) bovine fetal serum, and seeded at 5 x 103 / well in a 96-well cell culture dish. After 24 hours of cultivation, it was added to the wild yellow glutinous rice (Kunming Fengshan Progressive Medicine Research Co., Ltd.) and mixed with wild sorghum (Kunming Longjin Pharmaceutical Co., Ltd.) or Huangqi (Sichuan Superman Phytochemical Development Co., Ltd.) at different concentration ratios. Add to the culture solution. MTT assay was performed after 72 hours of culture.
  • CI CalcuSyn statistical software and combination drug index Value
  • mice B16 melanoma cell line was cultured for two generations in vitro, it was inoculated subcutaneously into the test animal female C57BL/6 (body weight of about 20 g) with 2 ⁇ 10 6 cells/only.
  • the rats were randomized on the second day after inoculation and started to be administered at 0.1 ml/10 g body weight.
  • Wild Huangyuan Karlming Fengshanjian Pharmaceutical Research Co., Ltd.
  • Wild Astragalus Karlming Longjin Pharmaceutical Co., Ltd.
  • the body weight of the animals was measured before administration, and the body weight of the animals was weighed on the 15th day after the test, and the tumor tissue was removed and weighed.
  • the combination of wild scutellariae and wild scutellariae has a synergistic effect in the vicinity of 1:0.5 ⁇ 1:4 concentration ratio, and the synergistic effect in the vicinity of the concentration ratio of 1:1 ⁇ 1:4 is more obvious. It can be seen that the results of the animal test clearly support the results of the in vitro test.
  • Wild Huang Yuan wild yellow ⁇ yuan
  • wild yellow ⁇ wild ⁇
  • mice B16 melanoma cell line was cultured for two generations in vitro
  • the mouse C57BL/6 (body weight of about 20 g) was inoculated subcutaneously with 2 x 106 cells/only in the experimental animals.
  • the rats were randomized on the second day after inoculation and started to be administered at 0.1 ml/10 g body weight.
  • Yehuang Huangyuan Karlming Fengshanjian Pharmaceutical Research Co., Ltd.
  • Huangqi Suduan Superman Phytochemical Development Co., Ltd.
  • the body weight of the animals was measured before administration, and the body weight of the animals was weighed on the 15th day after the test, and the tissue was removed and weighed.
  • Wild scutellariae and Astragalus membranaceus have a synergistic effect in the vicinity of 1:0.5 ⁇ 1:4 concentration ratio, and the synergistic effect in the vicinity of the concentration ratio of 1:1 ⁇ 1:4 is more obvious. It can be seen that the results of the animal test clearly support the results of the in vitro test.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Molecular Biology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

L'invention concerne une composition pharmaceutique ayant un effet antitumoral synergique, comprenant de la scutellareine et de la scutellarine ou de la baicaline. L'invention concerne également le procédé de préparation de cette composition pharmaceutique, ainsi que l'utilisation de cette dernière dans la fabrication d'un médicament.
PCT/CN2006/002267 2006-09-04 2006-09-04 Composition pharmaceutique à base de scutellareine et de scutellarine ou de baicaline ayant un effet antitumoral synergique WO2008028336A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/CN2006/002267 WO2008028336A1 (fr) 2006-09-04 2006-09-04 Composition pharmaceutique à base de scutellareine et de scutellarine ou de baicaline ayant un effet antitumoral synergique

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PCT/CN2006/002267 WO2008028336A1 (fr) 2006-09-04 2006-09-04 Composition pharmaceutique à base de scutellareine et de scutellarine ou de baicaline ayant un effet antitumoral synergique

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009140886A1 (fr) * 2008-05-22 2009-11-26 昆明制药集团股份有限公司 Dérivé de scutellarine, procédé d'élaboration, composition pharmaceutique, et utilisation correspondante
WO2009140887A1 (fr) * 2008-05-22 2009-11-26 昆明制药集团股份有限公司 Dérivé de scutellarine, procédé d'élaboration, composition pharmaceutique, et utilisation correspondante
CN102391336A (zh) * 2011-09-30 2012-03-28 昆明制药集团股份有限公司 一种化合物、其制备方法及用途
CN102838645A (zh) * 2012-09-26 2012-12-26 昆明制药集团股份有限公司 一种具有药物用途的多酚羟基黄酮化合物及其制备方法
CN112107574A (zh) * 2020-09-30 2020-12-22 郑州大学 柳穿鱼黄素在制备抗食管癌药物中的应用
CN114601863A (zh) * 2020-12-03 2022-06-10 山东益康药业股份有限公司 一种组合物在制备治疗人前列腺癌药物中的应用

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1679604A (zh) * 2005-02-01 2005-10-12 吴一心 抗肿瘤的协同药物组合物
CN1875958A (zh) * 2005-04-29 2006-12-13 吴一心 协同抗肿瘤的野黄芩甙元和黄芩甙药物组合物

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1679604A (zh) * 2005-02-01 2005-10-12 吴一心 抗肿瘤的协同药物组合物
CN1875958A (zh) * 2005-04-29 2006-12-13 吴一心 协同抗肿瘤的野黄芩甙元和黄芩甙药物组合物

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
XU GUANG ET AL.: "INHIBITION OF PROTEIN KINASE C BY SCUTELLAREIN AND ITS ANALOGUES", ACTA ACADEMIAE MEDICINALE SHANGHAI, vol. 20, no. 3, 1993, pages 187 - 191 *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009140886A1 (fr) * 2008-05-22 2009-11-26 昆明制药集团股份有限公司 Dérivé de scutellarine, procédé d'élaboration, composition pharmaceutique, et utilisation correspondante
WO2009140887A1 (fr) * 2008-05-22 2009-11-26 昆明制药集团股份有限公司 Dérivé de scutellarine, procédé d'élaboration, composition pharmaceutique, et utilisation correspondante
CN102391336A (zh) * 2011-09-30 2012-03-28 昆明制药集团股份有限公司 一种化合物、其制备方法及用途
CN102391336B (zh) * 2011-09-30 2015-04-22 昆明制药集团股份有限公司 一种化合物、其制备方法及用途
CN102838645A (zh) * 2012-09-26 2012-12-26 昆明制药集团股份有限公司 一种具有药物用途的多酚羟基黄酮化合物及其制备方法
CN102838645B (zh) * 2012-09-26 2015-06-17 昆药集团股份有限公司 一种具有药物用途的多酚羟基黄酮化合物及其制备方法
CN112107574A (zh) * 2020-09-30 2020-12-22 郑州大学 柳穿鱼黄素在制备抗食管癌药物中的应用
CN114601863A (zh) * 2020-12-03 2022-06-10 山东益康药业股份有限公司 一种组合物在制备治疗人前列腺癌药物中的应用

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