WO2013060258A1 - Clavatine a-c, son procédé de préparation et composition pharmaceutique et son utilisation - Google Patents
Clavatine a-c, son procédé de préparation et composition pharmaceutique et son utilisation Download PDFInfo
- Publication number
- WO2013060258A1 WO2013060258A1 PCT/CN2012/083360 CN2012083360W WO2013060258A1 WO 2013060258 A1 WO2013060258 A1 WO 2013060258A1 CN 2012083360 W CN2012083360 W CN 2012083360W WO 2013060258 A1 WO2013060258 A1 WO 2013060258A1
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- WIPO (PCT)
- Prior art keywords
- pharmaceutical composition
- compound
- acceptable salt
- preparation
- pharmacologically acceptable
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Classifications
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- 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
- A61K36/11—Pteridophyta or Filicophyta (ferns)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/20—Spiro-condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/10—Spiro-condensed systems
Definitions
- the present invention relates to the field of pharmaceutical technology, and in particular, the present invention relates to a class of stone pine alkaloid compounds: Streptococcus alkaloid AC (1-3), a pharmaceutically acceptable salt thereof, a preparation method thereof, and a compound containing the same Pharmaceutical compositions, and the use of such compounds in the preparation of acetylcholinesterase inhibitor drugs, in the preparation of a medicament for the treatment of Alzheimer's disease, and in the preparation of a medicament for the prevention of memory and cognitive decline in the elderly.
- Streptococcus alkaloid AC 1-3
- a pharmaceutically acceptable salt thereof a preparation method thereof
- a compound containing the same Pharmaceutical compositions, and the use of such compounds in the preparation of acetylcholinesterase inhibitor drugs, in the preparation of a medicament for the treatment of Alzheimer's disease, and in the preparation of a medicament for the prevention of memory and cognitive decline in the elderly.
- AD Alzheimer's disease
- AD Alzheimer's disease
- the patient's brain function is gradually declining, memory, abstract thinking ability and language expression decline, inconvenience and other functional disorders, affecting nervous system function, not only bring pain to patients, but also bring many problems to family and society. .
- AD is a central nervous system degenerative disease characterized by progressive cognitive and memory impairment. It has become the leading cause of death after cardiovascular disease and cancer in developed countries.
- the main drugs for treating AD include cholinergic drugs, neuronal cell metabolism enhancers, antioxidants, calcium ion antagonists, nerve growth factors, estrogens, anti-inflammatory drugs, and anti-beta amyloid drugs.
- the most successful method for the treatment of this disease in the clinic is to improve the symptoms of AD patients by increasing the level of cholinergic neurotransmitter-acetylcholine in the central nervous system.
- Acetylcholinesterase inhibitor specifically inhibits acetylcholinesterase (AChE)
- AChE acetylcholinesterase
- the hydrolysis of acetylcholine increases the level of acetylcholine in the brain and becomes the first-line drug for the treatment of AD.
- Clinically effective drugs such as tacrine, alexin, isgen, galantamine and huperzine A are all acetylcholinesterase inhibitors.
- the famous natural product, huperzine A is an alkaloid extracted from the Chinese fern phylum (Huperzia serrata (Thunb) Trev., Huperziaceae), which is reversible.
- a specific inhibitor of cholinesterase which has a selective inhibitory effect on acetylcholinesterase, and has low toxicity and long duration of action. It has been developed as one of the safest and most effective drugs for the treatment of benign memory disorders and Alzheimer's disease. The successful development of a world-class new drug pioneered in China has also enabled us to see the hope of finding new active ingredients from natural products and developing new drugs.
- Lycopodium japonicum Thunb. is a Lycopodiaceae stone pine plant. It is a traditional Chinese medicine commonly used in China. Its main functions are phlegm dehumidification, sturdy muscles, and it is used for joint pain and flexion and extension. It is found in folk and clinical use that it has a cholinergic side reaction that enhances myocardial contractility, excitatory smooth muscle, and muscle contraction and convulsions, suggesting that it may contain chemical components that have an effect on the cholinergic system.
- the technical scheme of the present invention attempts to conduct intensive studies on trace alkaloids in Strutgrass, and it is expected to find a novel active ingredient having a novel structure and having an acetylcholinesterase inhibitory action.
- the technical problem to be solved by the present invention is to provide a new class of compounds of the type: Streptococcus grass AC (l-3) and its pharmacologically acceptable salts.
- Another aspect of the invention relates to a process for the preparation of the compound ergic acid A-C (1-3). Still another aspect of the invention relates to a pharmaceutical composition comprising a pharmaceutically effective amount of the compound Asparticillin A-C (1-3) as an active ingredient and a carrier commonly used in the pharmaceutical field.
- Still another aspect of the present invention relates to a compound of sylvestreine AC (1-3) and a composition thereof for use in the preparation of an acetylcholinesterase inhibitor drug, in the preparation of a medicament for treating Alzheimer's disease, and for preparing anti-middle-age memory and cognition The application of drugs with reduced ability.
- compositions of the compounds of the invention can be prepared according to methods well known in the art.
- the compound of the present invention may be combined with one or more solid or liquid pharmaceutical excipients and/or adjuvants to provide a suitable administration form or dosage form for use as a medicament.
- the compound of the present invention or a pharmaceutical composition containing the same may be administered in a unit dosage form, which may be enterally or parenterally, such as oral, intravenous, intramuscular, subcutaneous, intraperitoneal, nasal, oral mucosa, The sputum, lungs and respiratory tract, skin, vagina, rectum, etc., are preferably administered orally.
- a unit dosage form which may be enterally or parenterally, such as oral, intravenous, intramuscular, subcutaneous, intraperitoneal, nasal, oral mucosa, The sputum, lungs and respiratory tract, skin, vagina, rectum, etc., are preferably administered orally.
- the dosage form can be a liquid dosage form, a solid dosage form or a semi-solid dosage form.
- Liquid dosage forms can be solutions (including true and colloidal solutions), emulsions (including o/w, w/o and double emulsions), suspensions, injections (including water injections, powder injections and infusions), eye drops Agents, nasal drops, lotions and tinctures.
- the solid dosage form can be a tablet (including ordinary tablets, enteric coated tablets, Tablets, dispersible tablets, chewable tablets, effervescent tablets, orally disintegrating tablets), capsules (including hard capsules, soft capsules, enteric capsules), granules, powders, pellets, dropping pills, suppositories, films, Patch, gas (powder) spray, spray, etc.; semi-solid dosage form may be ointment, gel, paste, and the like.
- the compounds of the present invention can be formulated into common preparations, sustained release preparations, controlled release preparations, targeted preparations, and various microparticle delivery systems.
- the diluent may be starch, dextrin, sucrose, glucose, lactose, mannitol, sorbitol, xylitol, microcrystalline cellulose, calcium sulfate, calcium hydrogen phosphate, calcium carbonate, etc.
- the humectant may be water, ethanol, or different Propyl alcohol, etc.
- the binder may be starch paddle, dextrin, sugar paddle, honey, glucose solution, microcrystalline cellulose, gum arabic paddle, gelatin paddle, sodium carboxymethylcellulose, methylcellulose, hydroxypropyl Methyl cellulose, ethyl cellulose, acrylic resin, carbomer, polyvinylpyrrolidone, polyethylene glycol, etc.
- disintegrant can be dry starch, microcrystalline cellulose, calcium sulfate, calcium hydrogen phosphate, calcium carbonate, etc.
- the humectant may be water, ethanol, or different Propyl alcohol, etc.
- the binder may be starch paddle
- Tablets may also be further formulated into coated tablets, such as sugar coated tablets, film coated tablets, enteric coated tablets, or bilayer tablets and multilayer tablets.
- carriers for example, diluents and absorbents such as glucose, lactose, and lakes. Powder, cocoa butter, hydrogenated vegetable oil, polyvinylpyrrolidone, lauric acid polyethylene glycol glyceride, kaolin, talcum powder, etc.; binders such as acacia, tragacanth, gelatin, ethanol, honey, liquid sugar, Rice paste or batter; etc.; disintegrating agents, such as agar powder, dried starch, alginate, sodium dodecylsulfonate, methylcellulose, ethylcellulose, and the like.
- diluents and absorbents such as glucose, lactose, and lakes.
- Powder cocoa butter, hydrogenated vegetable oil, polyvinylpyrrolidone, lauric acid polyethylene glycol glyceride, kaolin, talcum powder, etc.
- binders such as acacia, tragacanth, gelatin, ethanol, honey, liquid sugar,
- the carrier are, for example, polyethylene glycol, lecithin, cocoa butter, higher alcohols, esters of higher alcohols, gelatin, semi-synthetic glycerides and the like.
- the active ingredient of the present invention In order to encapsulate the drug delivery unit, the active ingredient of the present invention
- A-C (1-3) is mixed with the various carriers described above, and the mixture thus obtained is placed in a hard gelatin capsule or soft capsule.
- the active ingredient of the compound of the present invention can also be formulated into a microcapsule, suspended in an aqueous medium to form a suspension, or can be enclosed in a hard capsule or used as an injection.
- the compound of the present invention is prepared as an injectable preparation, such as a solution, a suspension solution, an emulsion, a lyophilized powder injection, and the preparation may be aqueous or non-aqueous.
- an injectable preparation such as a solution, a suspension solution, an emulsion, a lyophilized powder injection
- the preparation may be aqueous or non-aqueous.
- One or more pharmaceutically acceptable carriers, diluents, binders, lubricants, preservatives, surfactants or dispersing agents may be included.
- the diluent may be selected from the group consisting of water, ethanol, polyethylene glycol, 1, 3-propanediol, ethoxylated isostearyl alcohol, polyoxylated isostearyl alcohol, polyoxyethylene sorbitan fatty acid ester, and the like.
- an appropriate amount of sodium chloride, glucose or glycerin may be added to the preparation for injection, and a usual solubilizer, a buffer, a pH adjuster or the like may be added. These excipients are commonly used in the art.
- coloring agents may also be added to the pharmaceutical preparations as needed.
- the therapeutic effect is enhanced, and the medicament or the pharmaceutical composition of the present invention can be Administration is by any known method of administration.
- the dosage of the pharmaceutical composition of the compound of the present invention depends on a number of factors, such as the nature and severity of the disease to be prevented or treated, the sex, age, weight, personality and individual response of the patient or animal, the route of administration, the number of administrations, For therapeutic purposes, the therapeutic dose of the present invention can vary widely. In general, the dosage of the pharmaceutical ingredient of the present invention is well known to those skilled in the art.
- the prophylactic or therapeutic effect of the present invention can be accomplished by appropriately adjusting the amount of the actual drug contained in the final formulation of the compound composition of the present invention to achieve its therapeutically effective amount.
- the compound of the present invention is administered in a daily dose ranging from 0.001 to 10 mg/kg body weight in 2-4 divided doses.
- the compounds or compositions of this invention may be administered alone or in combination with other therapeutic or symptomatic agents and adjusted in dosage.
- HMBC heteronuclear multi-bond correlation (a two-dimensional nuclear magnetic resonance spectrum for determining the relationship between long-range hydrogen and carbon in a molecule)
- HSQC heteronuclear single quantum correlation (a two-dimensional nuclear magnetic resonance spectrum for determining the direct relationship between hydrogen and carbon in a molecule)
- ROESY Rotating Coordinate System Ovhaus Spectrum (a two-dimensional nuclear magnetic resonance spectrum for determining the spatial relationship of hydrogen atoms in a molecule)
- Fig.1 Extraction and separation of glutinous grass and preparation of acetaminophen AC (1-3)Fig.2 X-ray single crystal diffraction results of acetaminophen AC (1-3) (molecular ellipsoid)
- the plant of the genus Pinus sylvestris mainly contains components such as alkaloids, terpenoids, organic acids, flavonoids and strontium, and the grasses of the genus Struts are a common plant of the genus Pinus sylvestris. There is no thorough and thorough research.
- the extracted acid water was adjusted to pH 10 with saturated sodium bicarbonate solution (18 L), extracted with chloroform until the chloroform layer was reacted without alkaloids (4 times, 150 L each time), and the chloroform layer was concentrated to give a total alkaloid 135 g (recorded as B). ).
- the total alkaloid is chromatographed on an alkaline silica gel column (200-300 mesh, pH 8-9).
- Test Example 1 Determination of AChE Inhibitory Activity of Strenicin A-C (1-3)
- Acetylcholinesterase hydrolyzes acetylcholine to produce choline and acetic acid. Choline can react with sulfhydryl chromogenic reagent to form TNB (symmetric trinitrobenzene, Sym-Trinitrobenzene) yellow compound, which is colorimetrically quantified according to color depth. The amount of hydrolysate choline can reflect the activity of cholinesterase. Experimental materials and instruments required:
- reagent composition includes: reagent one: l mol / L standard application solution; reagent two: substrate; test Agent three: developer solution; reagent four: inhibitor; reagent five: transparent agent; reagent six: stabilizer; reagent seven: normal saline.
- AC(l-3) has significant acetylcholinesterase inhibitory activity, and its activity is equivalent to or stronger than the positive control substance Huperlin A (HupA).
- Huperlin A Huperlin A
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Abstract
La présente invention a trait à 3 alcaloïdes (clavatine A-C) isolés de Lycopodium japonicum Thunb., à un sel pharmacodynamiquement acceptable de ceux-ci et à leur procédé de préparation. L'invention a également trait à une composition pharmaceutique contenant cette classe de composés et à l'utilisation de cette classe de composés dans la préparation de médicaments inhibiteurs de l'acétylcholinestérase, de médicaments destinés à traiter la maladie d'Alzheimer et de médicaments permettant de résister à des maladies liées à un déclin de la mémoire et de la capacité cognitive de personnes d'âge mûr et de personnes âgées.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2011103254504A CN103059043A (zh) | 2011-10-24 | 2011-10-24 | 伸筋草碱a-c、其制法和其药物组合物与用途 |
CN201110325450.4 | 2011-10-24 |
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Publication Number | Publication Date |
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WO2013060258A1 true WO2013060258A1 (fr) | 2013-05-02 |
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PCT/CN2012/083360 WO2013060258A1 (fr) | 2011-10-24 | 2012-10-23 | Clavatine a-c, son procédé de préparation et composition pharmaceutique et son utilisation |
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CN (1) | CN103059043A (fr) |
WO (1) | WO2013060258A1 (fr) |
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CN103446136B (zh) * | 2013-09-23 | 2015-12-02 | 温州成桥科技有限公司 | Lycojaponicumin A在制备抗肺癌转移药物中的应用 |
CN103463060B (zh) * | 2013-09-23 | 2015-08-19 | 南京广康协生物医药技术有限公司 | Lycojaponicumin C在制备治疗子宫内膜癌药物中的应用 |
CN103463042B (zh) * | 2013-09-23 | 2015-07-08 | 南京广康协生物医药技术有限公司 | Lycojaponicumin A在制备治疗前列腺癌药物中的应用 |
CN103463077B (zh) * | 2013-09-23 | 2015-11-25 | 顾祥茂 | Lycojaponicumin C在制备促胰岛素分泌药物中的应用 |
CN103463029B (zh) * | 2013-09-23 | 2015-07-08 | 南京广康协生物医药技术有限公司 | Lycojaponicumin B在制备抗人体真菌药物中的应用 |
CN103463048B (zh) * | 2013-09-23 | 2015-08-19 | 南京广康协生物医药技术有限公司 | Lycojaponicumin A在制备促进小肠蠕动药物中的应用 |
CN103463027B (zh) * | 2013-09-23 | 2015-08-19 | 南京广康协生物医药技术有限公司 | Lycojaponicumin A在治疗喉癌药物中的应用 |
CN103463056B (zh) * | 2013-09-23 | 2015-08-19 | 南京广康协生物医药技术有限公司 | Lycojaponicumin A在制备治疗舌癌药物中的应用 |
CN103463044B (zh) * | 2013-09-23 | 2015-12-09 | 李淑兰 | Lycojaponicumin A在制备治疗皮肤癌药物中的应用 |
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