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WO2004009106A1 - Preparation extraite de stephania tetrandra s.moor et utilisation de cette derniere - Google Patents

Preparation extraite de stephania tetrandra s.moor et utilisation de cette derniere Download PDF

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Publication number
WO2004009106A1
WO2004009106A1 PCT/CN2002/000505 CN0200505W WO2004009106A1 WO 2004009106 A1 WO2004009106 A1 WO 2004009106A1 CN 0200505 W CN0200505 W CN 0200505W WO 2004009106 A1 WO2004009106 A1 WO 2004009106A1
Authority
WO
WIPO (PCT)
Prior art keywords
preparation
acid
tetrandrine
powder
solid
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/CN2002/000505
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English (en)
Chinese (zh)
Inventor
Zhimin Wang
Zuguang Ye
Aihua Liang
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.)
Institute of Materia Medica of CACMS
Original Assignee
Institute of Chinese Materia Medica of China Academy of Traditional Chinese Medicine CATCM
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 Institute of Chinese Materia Medica of China Academy of Traditional Chinese Medicine CATCM filed Critical Institute of Chinese Materia Medica of China Academy of Traditional Chinese Medicine CATCM
Priority to CNB028293363A priority Critical patent/CN1282466C/zh
Priority to PCT/CN2002/000505 priority patent/WO2004009106A1/fr
Priority to AU2002318715A priority patent/AU2002318715A1/en
Publication of WO2004009106A1 publication Critical patent/WO2004009106A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/59—Menispermaceae (Moonseed family), e.g. hyperbaena or coralbead
    • 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
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia

Definitions

  • the invention relates to a preparation prepared from powder and self-protection and its use.
  • the present invention also relates to one of the main ingredients of the preparation, the use of tetrandrine in the preparation of a medicament for increasing the level of white blood cells. Background technique
  • Tumors are one of the diseases with a high mortality rate in humans, and their incidence is increasing year by year.
  • Chemotherapy and radiation therapy are currently the main methods for clinical treatment of tumors.
  • the resistance to chemotherapeutic drugs can make tumor tissues regain their sensitivity to chemotherapeutic drugs, or can make chemotherapeutic drugs easily enter cells and increase the cumulative concentration of chemotherapeutic drugs in cells, or they have antitumor effects, and Chemotherapy drugs work synergistically to enhance sensitization chemotherapy.
  • Fangfangji is the dried root of Fangfangchi (Stephenia tetrandra S. Moor), which is also known as Fangfang and downed arch. Beginning in "Shen Nong's Materia Medica”. The taste is bitter and cold. Go to the bladder and lung meridians. It has the effects of diuresis and swelling, expelling wind and relieving pain. For water Swelling athlete's foot, unfavorable urination, eczema, sore, rheumatic pain, hypertension.
  • the total alkaloids in tetrandrine account for about 0.5-5% of the root, mainly including tetrandrine (also known as tetrandrine, tetrandrine), tetrandrine (fangchinoline, also known as tetrandrine), Normantine, haggingchin C, menisine, menisidine, cyclanoline, berbamine, oxidized tetrandrine Oxofangchirine, stephanthrine, fenfangjine A, B, C, D, (+) — 2—N—methyl tetrandrine, (+) — 2—N—methyl tetrandrine ( (+) -N-methyltetrandrine), 2,2'- ⁇ , ⁇ -dimethylchlorotrandrine and the like.
  • tetrandrine and tetrandrine are predominant in the roots, accounting for 50-80% of the total alkaloids.
  • Tetrandrine is used clinically to treat silicosis, hypertension, and coronary heart disease.
  • the body alkaloids of Fangfang total alkaloids have been shown to have analgesic effects (Zhao Yi, Fangyanhusuo, scopolamine components, analgesic effect, Chinese Medical Journal, 1955, 41 (10), 931-935).
  • tetrandrine can reverse the resistance of chemotherapy-resistant drugs such as vincristine, doxorubicin and other tumor cells (KB cells, etc.) in vitro (Ye Switzerlanduang et al.
  • the present inventors devoted themselves to the development of new pharmacological uses of alkaloids. As a result, it was found that from the powder of Fangfang and its genus or Batumi iMenispermum dauricum DC.) Or hair Extracts from plants such as Cydea barbata (Wall.) Miers), which mainly contain tetrandrine and tetrandrine have chemosensitization, radiosensitization, and increase leukocyte levels and antiallergic effects. In addition, the inventors of the present invention also found that tetrandrine has an effect of increasing leukocyte levels.
  • step (1) filtering the liquid in step (1), drying and pulverizing the solid to obtain powder 1;
  • step (3) the alcohol solution in step (3) is concentrated, left, and filtered to obtain solid 2;
  • the preparation mainly contains tetrandrine of molecular formula (I) and tetrandrine of molecular formula (II).
  • the molar ratio of the two is 9: 1 to 6: 4, and the total content of the two is greater than 50%.
  • the preparation of the present invention can be used for the preparation of a chemotherapeutic sensitization, a radiotherapy sensitization, an increase in the level of white blood cells, or an antiallergic drug.
  • tetrandrine has the effect of increasing the level of white blood cells in the body, so it can be used to prepare drugs that increase the level of white blood cells.
  • the experimental research of the present inventors has shown that the preparation of the present invention has a more effective effect of reversing the multidrug resistance of tumor tissues to chemotherapeutic drugs than the application of tetrandrin alone, and the effect of increasing the concentration of chemotherapeutic drugs in tumor cells Combined with chemotherapeutic drugs, it has a sensitizing or synergistic effect on chemotherapeutic drugs; the preparation of the present invention is used in advance, and then radiation treatment is performed on tumor patients, showing that the preparation has the effect of improving the comprehensive curative effect of radiation therapy without any occurrence The toxic and side effects of which are better for squamous cell carcinoma; the preparation of the present invention, tetrandrine and its salt have a strong effect on increasing the level of leukocytes in low levels of leukocytes of immunosuppressed animals, and the increase range is 100 The
  • the preparation of the present invention is obtained by the following method:
  • step (1) filtering the liquid of step (1), drying and pulverizing the solid to obtain powder 1;
  • step (3) the alcohol solution in step (3) is concentrated, left, and filtered to obtain solid 2;
  • the preparation mainly contains tetrandrine of molecular formula (I) and tetrandrine of molecular formula (II), and the molar ratio of the two is 9.8: 0.2-6: 4, and the total content of the two is more than 50%, preferably The ratio is 9.5: 0.5 to 8: 2, more preferably 9: 1 to 8: 2, and most preferably 8.5: 1.5 to 6.5: 3.5.
  • the method further comprises the following steps:
  • step (5) The precipitate obtained in step (5) is dissolved in alcohol, and an equivalent amount of a pharmaceutically acceptable acid is added to form a salt, and the mixture is allowed to stand and filtered.
  • a pharmaceutically acceptable acid is preferably 0.1 to 4.5, more preferably From 1.75 to 2.5, preferred inorganic acids include, for example, hydrobromic acid, hydrochloric acid, and sulfuric acid; preferred organic acids include, for example, methanesulfonic acid, tartaric acid, maleic acid, and citric acid. The most preferred acid is hydrochloric acid.
  • the dilute acid used in step (1) of the method is preferably dilute sulfuric acid; the base used is preferably calcium oxide and calcium hydroxide.
  • the preparation of the present invention may also contain berbamine, oxotetrandrine, oxofangchinoline, and the like.
  • the quantitative analysis of each component in the preparation of the present invention can be performed by a method known to those skilled in the art, and usually chromatography is used, such as high performance liquid chromatography.
  • the preparations of the present invention have various pharmacological activities, and tetrandrine has the effect of increasing the body's white blood cell level, so they can be used to prepare drugs with corresponding pharmacological activities, which are used for chemosensitization , Radiation sensitization, elevated white blood cell levels, or anti-allergy.
  • the pharmaceutical preparation can be prepared according to methods known to those skilled in the art, and can be For tablets, pills, powders, suspensions, emulsions, syrups, capsules, sterile injection solutions and other common dosage forms.
  • the pharmaceutical preparation of the present invention can be administered by various routes including oral, transdermal, subcutaneous, intravenous and intramuscular administration, and the dosage is usually in the range of 0.02-1.5 g / day depending on the weight and symptoms of the subject to be administered.
  • the supernatant is decanted and discarded
  • the lower turbid liquid was filtered with a filter cloth to obtain about 2 kg of precipitate, dried, crushed (10-40 mesh sieve), heated under reflux with 95% ethanol, poured out of the alcohol solution, concentrated, left, filtered, and the obtained solid was dissolved in In ammonia-based ethanol, it is left to precipitate, and the obtained crystals are dissolved in ethanol, a predetermined amount of acid is added, and the solution is allowed to stand and filtered to obtain the desired preparation.
  • Example 2 Ten grams of the solid obtained from ammoniacal ethanol was taken and recrystallized from acetone to obtain 5 grams of white needle-like crystals of tetrandrine with a purity of more than 98%.
  • Example 2 Ten grams of the solid obtained from ammoniacal ethanol was taken and recrystallized from acetone to obtain 5 grams of white needle-like crystals of tetrandrine with a purity of more than 98%.
  • mice Preparation and Tetrandrine's whitening effect on cyclophosphamide-induced low leukocytes in mice.
  • the mice were injected intraperitoneally with an antitumor drug cyclophosphamide 75mg / kg.
  • the number of white blood cells in peripheral blood decreased significantly.
  • the preparation obtained in Example A was orally or intramuscularly injected once a day for 3 consecutive days. The results are shown in Table 1, Table 2 and Table. 3.
  • the tetrandrin and the preparation can obviously inhibit the leukocyte decrease caused by cyclophosphamide, which shows that it has a certain attenuating effect on the toxic and side effects of the low leukocyte caused by cyclophosphamide.
  • mice were inoculated with S 18 .
  • the preparation obtained in Example A was orally or intramuscularly injected, and the animals received 6Q Co irradiation (500 rad, 1 minute 56 seconds) on the second day after the administration, and then continued the administration.
  • the non-administration group was the model group, and the non-irradiated normal control group was set up.
  • the results showed that the peripheral blood leukocytes of the model group were significantly lower than normal after irradiation, and the preparation obtained in Example 1 A 25 mg kg and 100 mg / kg was orally administered to the peripheral blood on the 3rd and 7th day after radiotherapy, respectively.
  • When administered by injection it also has a certain degree of promotion effect on peripheral blood leukocytes, and the promotion rate is as high as 59%.
  • the results are shown in Table 4.
  • tumor cells are resistant to anti-tumor drugs.
  • the drug concentration in tumor cells is reduced, so that the tumor cells cannot be inhibited.
  • Grow. We use the sensitive strain S 18 .
  • the preparation obtained in Example A and daunorubicin are administered in combination, the daunorubicin concentration in drug-resistant cells can be significantly increased, which is close to the drug concentration level in sensitive cells.
  • the results are shown in the table. 8. It can be seen that the preparation can increase the concentration of anticancer drugs in tumor cells, so that it can reach the level of inhibiting the growth of tumor cells.
  • the analgesic effect of the preparation obtained in A of Example 1 was observed using a warm-induced pain model and a chemical peritonitis model.
  • the results showed that: in the mouse tail-flick test, the preparation was given once by intramuscular injection at doses of 5 mg / kg and 10 mg / kg, both of which could prolong the warm-induced tail tail latency of mice, indicating that the preparation caused pain by warming Has a certain analgesic effect.
  • the inhibitory effect of the preparation on chemical peritonitis pain was observed using a model of writhing response caused by acetic acid.
  • the MTT method was used to determine the in vitro half inhibitory concentration of the preparation on various tumor cells. The results are shown in Table 11.
  • Example 10 Give the lung cancer patient the preparation obtained in Example A in Example 1 100-300 mg / times intravenously or intravenously 2 hours before radiotherapy, or take a small dose of radiation treatment 2 days after taking the preparation tablet in advance, each time the tumor volume is radiated 150-160 rads, 5 times a week, with a total radiation of 1500-3000 rads; 5 days of medication, 5 days of discontinuation, tablets of its preparation taken orally during the discontinuation period, 300 mg / time, 300- 600 mg / day.
  • the total effective rate for the treatment of advanced lung cancer is more than 60%, and all patients have no obvious side effects of radiotherapy.
  • Example 10 The total effective rate for the treatment of advanced lung cancer is more than 60%, and all patients have no obvious side effects of radiotherapy.
  • the administration group was injected with the preparation obtained in Example 1 A intraperitoneally 30 minutes before inflammation. Evans blue was injected intravenously. After 6 hours, the balloon was washed with Hank's solution, the cell fluid was collected, the number of cells was counted, and the OD of the cystic fluid was measured with a spectrophotometer.
  • Example 12 Dissolve 50 g of the preparation obtained in Example 1 with water for injection, add 2 g of sodium sulfite and water for injection to 1000 ml, and filter with No. 3 vertical melting glass funnel or other filter media (such as ultra-microfiltration membranes) To clear, potting, sterilization, you can. Each pack contains 50 nig of preparation.
  • Example 12 Dissolve 50 g of the preparation obtained in Example 1 with water for injection, add 2 g of sodium sulfite and water for injection to 1000 ml, and filter with No. 3 vertical melting glass funnel or other filter media (such as ultra-microfiltration membranes) To clear, potting, sterilization, you can. Each pack contains 50 nig of preparation.
  • Example 12 Dissolve 50 g of the preparation obtained in Example 1 with water for injection, add 2 g of sodium sulfite and water for injection to 1000 ml, and filter with No. 3 vertical melting glass funnel or other filter media (such as ultra-microfiltration membranes) To clear, potting, sterilization, you can. Each
  • Example 13 To 300 g of the preparation obtained in Example A was added an appropriate amount of lactose and microcrystalline fiber. Vitamine, polyethylene glycol 3000, sodium carboxymethyl starch, dry compressed granules, add an appropriate amount of magnesium stearate, press into 1000 tablets, sterilize, and coat with film. Each tablet contains 300 mg of preparation.
  • Example 13 To 300 g of the preparation obtained in Example A was added an appropriate amount of lactose and microcrystalline fiber. Vitamine, polyethylene glycol 3000, sodium carboxymethyl starch, dry compressed granules, add an appropriate amount of magnesium stearate, press into 1000 tablets, sterilize, and coat with film. Each tablet contains 300 mg of preparation.
  • Example 13 To 300 g of the preparation obtained in Example A was added an appropriate amount of lactos
  • Example 14 300 g of the S IJ preparation obtained in Example 1 was added with an appropriate amount of auxiliary materials such as lactose, microcrystalline cellulose and the like, and then pressed and granulated, and then sterilized and gelatinized to make 1000 granules. Each capsule contains 300 mg of preparation.
  • auxiliary materials such as lactose, microcrystalline cellulose and the like

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Hematology (AREA)
  • Organic Chemistry (AREA)
  • Alternative & Traditional Medicine (AREA)
  • Oncology (AREA)
  • Botany (AREA)
  • Medical Informatics (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La présente invention concerne une préparation extraite de Stephania tetrandra S.Moor et son utilisation pour préparer un médicament permettant d'accroître la sensibilité à la chimiothérapie ou d'augmenter l'effet de la chimiothérapie, d'améliorer la sensibilité à la radiothérapie, d'accroître le nombre des leucocytes dans le corps, ledit médicament ayant des effets antinéoplastiques et antianaphylactiques. Ladite préparation est principalement constituée de tétrandrine et de fangchinoline selon le rapport 9 :1 et 8 :2 (moles) obtenu avec le procédé suivant : (1) on extrait la poudre ou une partie de Stephania tetrandra S.Moor avec de l'acide dilué puis on récupère l'extrait d'acide froid; on lave ensuite à l'eau l'extrait aqueux récupéré; et on mélange l'extrait d'acide froid et l'extrait aqueux, qu'on ajuste avec une base à un pH compris entre 10 et 12, et on garde le mélange pendant 24 heures; (2) on filtre le fluide de l'étape (1) qu'on déshydrate sous forme solide et qu'on réduit en poudre (P); (3) on chauffe la poudre (P) avec reflux dans de l'alcool pendant 30 minutes; (4) on concentre l'alcool issu de l'étape (3), on le garde, on le filtre pour former un solide (S); on dissout le solide (S) dans de l'ammoniac éthanol chauffé, où il reste le temps de la cristallisation. Cette invention concerne également l'utilisation de tétrandrine et de son sel pharmaceutiquement acceptable pour préparer un médicament servant à améliorer le nombre de leucocytes dans le corps.
PCT/CN2002/000505 2002-07-18 2002-07-18 Preparation extraite de stephania tetrandra s.moor et utilisation de cette derniere Ceased WO2004009106A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
CNB028293363A CN1282466C (zh) 2002-07-18 2002-07-18 自粉防己提取的制备物及其用途
PCT/CN2002/000505 WO2004009106A1 (fr) 2002-07-18 2002-07-18 Preparation extraite de stephania tetrandra s.moor et utilisation de cette derniere
AU2002318715A AU2002318715A1 (en) 2002-07-18 2002-07-18 Preparation extracted from stephania tetrandra s. moor and the use thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/CN2002/000505 WO2004009106A1 (fr) 2002-07-18 2002-07-18 Preparation extraite de stephania tetrandra s.moor et utilisation de cette derniere

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WO2004009106A1 true WO2004009106A1 (fr) 2004-01-29

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CN (1) CN1282466C (fr)
AU (1) AU2002318715A1 (fr)
WO (1) WO2004009106A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102382119A (zh) * 2011-10-19 2012-03-21 陕西省西安植物园 一种汉防已甲素和汉防已乙素的提取方法

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN100396686C (zh) * 2006-08-03 2008-06-25 西安皓天生物工程技术有限责任公司 一种汉防己甲素和汉防己乙素的制备方法
CN101288695B (zh) * 2007-04-16 2011-09-21 中国科学院成都生物研究所 粉防己生物碱的制备工艺
CN103330827B (zh) * 2013-07-08 2015-04-08 宋海平 用于治疗放疗引起的白细胞减少的中药组合物
CN103432134B (zh) * 2013-07-25 2016-01-20 合肥七星医药科技有限公司 升高白细胞及治疗再生障碍性贫血的异粉防己碱药物及其制剂
CN107126461B (zh) * 2017-05-12 2020-08-04 山东省立医院 一种水溶性防己提取物的制备工艺
CN111153909B (zh) * 2020-01-17 2022-05-17 石药集团江西金芙蓉药业股份有限公司 一种粉防己中甲、乙素双模板分子印迹提纯方法

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CN1198331A (zh) * 1997-05-07 1998-11-11 史庆丰 治疗三叉神经痛的药物
US6218541B1 (en) * 1999-06-28 2001-04-17 Cba, International, Inc. Method for extracting bisbenzylisoquinolines

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CN1198331A (zh) * 1997-05-07 1998-11-11 史庆丰 治疗三叉神经痛的药物
US6218541B1 (en) * 1999-06-28 2001-04-17 Cba, International, Inc. Method for extracting bisbenzylisoquinolines

Non-Patent Citations (2)

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Title
SUN GUI-RONG: "Protective effect of tetrandrine on pancreatic islet cells damaged by alloxan in rats", ACTA PHYSIOLOGICA SINICA, vol. 46, no. 2, February 1994 (1994-02-01), pages 161 - 167 *
ZHANG QIU-XIA ET AL.: "Deterination of physostigmine sallicylate eye-drops by orthogonal function spectrophotometric method", CHINESE JOURNAL OF HOSPITAL PHARMACY, vol. 15, no. 9, September 1995 (1995-09-01), pages 406 - 407, 432 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102382119A (zh) * 2011-10-19 2012-03-21 陕西省西安植物园 一种汉防已甲素和汉防已乙素的提取方法
CN102382119B (zh) * 2011-10-19 2014-06-25 陕西省西安植物园 一种汉防已甲素和汉防已乙素的提取方法

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CN1658890A (zh) 2005-08-24
CN1282466C (zh) 2006-11-01
AU2002318715A1 (en) 2004-02-09

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