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WO2008040236A1 - Dérivés de flavones, procédés de préparation et utilisation de ces derniers - Google Patents

Dérivés de flavones, procédés de préparation et utilisation de ces derniers Download PDF

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Publication number
WO2008040236A1
WO2008040236A1 PCT/CN2007/070724 CN2007070724W WO2008040236A1 WO 2008040236 A1 WO2008040236 A1 WO 2008040236A1 CN 2007070724 W CN2007070724 W CN 2007070724W WO 2008040236 A1 WO2008040236 A1 WO 2008040236A1
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WO
WIPO (PCT)
Prior art keywords
dimethylpropenyl
flavonoid
methoxy
group
dimethoxy
Prior art date
Application number
PCT/CN2007/070724
Other languages
English (en)
Chinese (zh)
Inventor
Shujun Zhang
Hongli Guo
Zheng Liu
Xinjian Chen
Yifeng Nian
Jingshan Shen
Original Assignee
Topharman Shanghai Co., Ltd.
Shanghai Institute Of Materia Medica, Chinese Academy Of Sciences
Qiqihar University
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 Topharman Shanghai Co., Ltd., Shanghai Institute Of Materia Medica, Chinese Academy Of Sciences, Qiqihar University filed Critical Topharman Shanghai Co., Ltd.
Publication of WO2008040236A1 publication Critical patent/WO2008040236A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/08—Drugs for disorders of the urinary system of the prostate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/06—Antiglaucoma agents or miotics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/74—Benzo[b]pyrans, hydrogenated in the carbocyclic ring

Definitions

  • the present invention relates to a flavonoid derivative, a preparation method and use thereof. Background technique
  • Sildenafil citrate was developed by Pfizer and was the first oral medication to treat ED in March 1998. Clinically, there are side effects such as headache and facial flushing and visual disturbance.
  • Epimedium is a commonly used ingredient in the prescription of traditional Chinese medicine tonic strongeners. There have been many studies on the chemical constituents and pharmacological effects of the raw drug Epimedium or its extract. There are dozens of compounds from which the structure has been isolated, including icariin (5-hydroxy-4'-methoxy-8-(3,3-dimethylpropenyl) flavonoid-7- ⁇ - ⁇ -glucose-3-aL-rhamnoside), icariin-1 (3,5-dihydroxy-4'-methoxy-8-(3,3-dimethylpropenyl) flavonoid-7 -PD-glucoside), Baoji-I (5,7-dihydroxy-4'-methoxy-8-(3,3-dimethylpropenyl)flavon-3-aL-rhamnoside) , icariin (3,5,7-trihydroxy-4'-methoxy-8-(3,3-dimethylpropenyl) flavonoid), nobate icariin (3,5,7
  • the present invention provides a flavonoid derivative having the general formula 1:
  • And 17 are each independently selected from H, C r C 6 alkyl or C 2 -C, I
  • R 2 is selected from H, C r C 6 alkyl, C 2 -C 6 fatty acyl, C 7 -C 12 hydrocarbyl or c 7 -c 12
  • R 3 and R4 are each independently selected from C r C 6 alkyl group, or they are 3 ⁇ 4 atoms and form a pyrrolidine, piperidine or piperazine together;
  • R 5 is selected from the group consisting of H, C r C 6 alkyl, C 2 -C 6 fatty acyl, C 7 -C 12 hydrocarbyl, C 7 -C 12 aroyl, C3 ⁇ 4CHOC3 ⁇ 4, C3 ⁇ 4(CHX)mC3 ⁇ 4YGn, CH 2 CONHC3 ⁇ 4C3 ⁇ 4NGn, C3 ⁇ 4COOM Or CH 2 CON(CH 2 CH 2 ) 2 YGn , wherein
  • R 6 is selected from
  • Ri, R 2 and R 5 may not be H, Ac or C 3 ⁇ 4 at the same time;
  • R 6 is an isopentenyl group, and cannot be C3 ⁇ 4 at the same time;
  • R 6 is an isopentenyl group, and cannot be independently C3 ⁇ 4.
  • the present invention also provides a method for preparing the above-mentioned flavonoid derivative having the general formula 1 as follows: acylation reaction and alkoxylation reaction of icariin or noxanthine; or
  • Compound 2 was prepared alkoxylated, 2, wherein, Ra, Rb are each independently selected from C r C 6 alkyl or C 2 -C 6 aliphatic acyl group; a glycoside or beans Po - I alkoxylation Thereafter, the rhamnose is removed by hydrolysis under acidic conditions and acylated.
  • the present invention still further provides the use of the above-mentioned flavonoid derivative having the formula 1 for the preparation of a medicament for preventing and treating dysfunction and for treating diseases associated with vascular contraction.
  • These compounds can be used to treat or prevent a variety of vascular disorders in mammals, including humans, including male (male) erectile dysfunction, female (female) sexual dysfunction, premature labor, dysmenorrhea, sexual prostatic hyperplasia, and bladder.
  • the present invention also provides an intermediate compound for preparing the above-mentioned flavonoid derivative of the general formula 1, as shown in Formula 2:
  • Ra and Rb are each independently selected from a C r C 6 alkyl group or a C 2 - C 6 fatty acyl group.
  • the present invention further provides a method for preparing the compound of the above formula 2 as follows:
  • the flavonoid derivative of the formula 1 provided by the present invention has high activity and high selectivity for inhibition of PDE5, and has remarkable therapeutic effects and small toxic side effects.
  • the invention is implemented as follows:
  • the present invention provides a process for the preparation of a compound of formula (1). Also included are any new intermediates in the preparation process and methods for their preparation, such as the compounds of formula (2) below and methods for their preparation.
  • Synthetic route 1 formula (1) compound can be obtained from icariin [3,5,7-trihydroxy-4'-methoxy-8-(3,3-dimethylpropenyl) flavonoid] or Epimedhasin [3,5,7,4'-tetrahydroxy-8-(3,3-dimethylpropenyl)flavone] is obtained by acylation and then alkoxylation reaction, or collateral After the alkaloid or the saponin is alkoxylated, the acylation reaction is carried out.
  • the acylating reagent used in the acylation reaction of the present invention may be an acid anhydride (e.g., acetic anhydride or the like), an acid chloride (e.g., acetyl chloride, benzoyl chloride, cinnamoyl chloride, etc.), and the solvent is an anhydrous organic solvent (e.g., CH 2 C1 2 , CH 3 C1, dioxane, tetrahydrofuran, hydrazine, hydrazine-dimethylformamide, pyridine, etc.), the catalyst can be anhydrous pyridine, 4-( ⁇ , ⁇ -dimethylamino)pyridine And triethylamine, etc., the acylation reaction temperature is 0-80 ° C, and the reaction time is 0.5-24 hours.
  • an acid anhydride e.g., acetic anhydride or the like
  • an acid chloride e.g., acetyl chloride, benzoy
  • the alkoxylation reagent used in the alkoxylation reaction in the present invention may be a halogenated hydrocarbon (e.g., Methyl iodide, ethyl iodide, ethyl bromide, bromopropane, benzyl chloride, etc.), sulfate (such as: dimethyl sulfate, diethyl sulfate, etc.), the solvent is an anhydrous organic solvent (such as: Oxytetracycline, tetrahydrofuran,
  • halogenated hydrocarbon e.g., Methyl iodide, ethyl iodide, ethyl bromide, bromopropane, benzyl chloride, etc.
  • sulfate such as: dimethyl sulfate, diethyl sulfate, etc.
  • the solvent is an anhydrous organic solvent (such as: Oxytetracycl
  • the alkoxylation reaction is 20-80 ° C, and the reaction time is 0.5-24 hours.
  • Synthetic route 2 will be Baoji-I [5,7-dihydroxy-4'-methoxy-8-(3,3-dimethylpropenyl) flavonoid _3_ a _L-rhamnoside] methoxy Basicization (methods such as alkoxylation of Synthetic Line 1), followed by acid hydrolysis to remove rhamnose (acids used in acid hydrolysis include sulfuric acid, p-toluenesulfonic acid, hydrochloric acid, phosphoric acid, acetic acid, etc.), and then A corresponding compound is obtained by acylation by the aforementioned method.
  • the alkoxylation reaction (method as described above) is then carried out with a halide (e.g., epichlorohydrin, ethyl chloroacetate or ethyl bromoacetate, etc.) to give the corresponding compound.
  • a halide e.g., epichlorohydrin, ethyl chloroacetate or ethyl bromoacetate, etc.
  • Ra, Rb may each independently be selected from the group consisting of C r C 6 alkyl and C 2 -C 6 fatty acyl.
  • the raw material compounds of the present invention can be obtained from the raw drug Epimedium, or the extract of Epimedium extract through an organic solvent or an organic solvent.
  • the mixed solvent of water is extracted into extracts of different solvents (the plant material is mainly Epimedium sinensis, and the content of icariin is about 14.2%), and various extracts are separated.
  • the separation and extraction section is as described in the patent CN200610029522.X. detailed description
  • Human platelets purchased from the blood bank of the Shanghai Blood Center.
  • the enzyme used in the enzyme inhibition activity test was a method similar to that reported in the literature (Thrombosis Res. 1991, 62, 31 and J. Biol. Chem. 1997, 272, 2714), and the human platelets were appropriately treated and separated by FPLC. The enzyme required for the test. Once the enzyme is isolated, the enzyme inhibition activity test is carried out immediately. The enzyme inhibition test is performed by directly detecting the GMP scintillation proximity assay using the TRKQ7100 kit. This is roughly the case, and the ⁇ is added in the presence of different inhibitor concentrations and a small amount of substrate.
  • TPN1353 4.11 > ⁇ 10" 7 The present invention designs and synthesizes a novel class of flavonoid derivatives which have good inhibitory activity against PDE5 and can be used as a medicament for preventing sexual dysfunction and diseases related to vascular contraction.
  • the structure is relatively simple and easy to prepare.
  • the invention will be further illustrated by the following specific examples, without limiting the invention.
  • NMR was performed on a Mercury-400 NMR spectrometer (Varian), and the frequency of observation of ifi NMR was 400.144 MHz.
  • the general abbreviations are as follows: s, singlet; d, doublet; t, triplet; q, quartet; m, multiplet; br, broad; mass spectrometry on MAT-95 mass spectrometer (Thermo Finnigan) Complete, ionization mode EI 70V, source temperature 200 ° C, LR resolution 1000; room temperature refers to 20-25 ° C.
  • TPN1366 3,7-Diacetoxy-5-hydroxy-4'-methoxy-8-(3,3-dimethylpropenyl)flavonoid
  • Example 11 3,5,4'-Trimethoxy-7-(N,N-diethyl-ethylenediamineacetamidooxy)-8-(3,3-dimethyl Propylene-based flavonoids (TPN1350) 0.014 g of the compound obtained in Example 10, 0.043 mL of hydrazine, hydrazine-diethylethylenediamine and 1.5 mL of absolute ethanol were successively added to a 25 mL flask, and the mixture was stirred at 70 ° C for 18 hours, and concentrated to room temperature and concentrated directly. The title compound (0.015 g, 96%) was obtained.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Urology & Nephrology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Endocrinology (AREA)
  • Reproductive Health (AREA)
  • Vascular Medicine (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Gynecology & Obstetrics (AREA)
  • Pulmonology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention porte sur des dérivés de flavones, des procédés de préparation et des utilisations de ces derniers. L'invention concerne des dérivés de flavones de la formule I et des procédés de préparation desdits dérivés de flavones de la formule I. Les dérivés de flavones de la formule I peuvent être utilisés dans la préparation de produits pharmaceutiques destinés à prévenir et à traiter les troubles et dysfonctionnements sexuels et à améliorer la vasoconstriction.
PCT/CN2007/070724 2006-09-20 2007-09-18 Dérivés de flavones, procédés de préparation et utilisation de ces derniers WO2008040236A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CNA2006101162691A CN101148444A (zh) 2006-09-20 2006-09-20 黄酮衍生物、制备方法及应用
CN200610116269.1 2006-09-20

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Publication Number Publication Date
WO2008040236A1 true WO2008040236A1 (fr) 2008-04-10

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101928328A (zh) * 2009-06-17 2010-12-29 李毅林 一种rgd肽-淫羊藿黄酮结合物、及其制备方法和应用
CN112574160A (zh) * 2020-12-07 2021-03-30 武汉轻工大学 一种高良姜素衍生物及其制备方法和应用
CN115399405A (zh) * 2022-11-01 2022-11-29 四川合泰新光生物科技有限公司 一种宝藿苷i葡聚糖包合物的用途

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CN102167690B (zh) * 2011-03-14 2014-04-02 暨南大学 一种淫羊藿苷苷元衍生物及其制备方法和应用
CN103160553B (zh) * 2011-12-19 2014-11-19 中国科学院大连化学物理研究所 一种制备宝霍苷i纯品的方法
CN103570694B (zh) * 2012-07-23 2017-05-03 厦门鹭佳生物科技有限公司 淫羊藿素及其衍生物的制备及其在肿瘤治疗中的应用
CN103265591B (zh) * 2013-05-24 2016-04-20 四川大学 淫羊藿苷衍生物及其制备方法和用途
CN103265593B (zh) * 2013-05-24 2016-03-16 四川大学 淫羊藿苷衍生物
CN104387430B (zh) * 2014-10-27 2017-03-15 广东东阳光药业有限公司 淫羊藿苷类化合物及其应用
CN106117189B (zh) * 2016-06-15 2019-02-01 张帆 乙酰基白杨素Mannich碱衍生物及其用途
CN109265502A (zh) * 2018-10-29 2019-01-25 广东金骏康生物技术有限公司 异戊二烯基黄酮化合物、衍生物、药物组合物及其应用
CN111620920B (zh) * 2019-06-10 2023-11-07 四川福生源科技有限公司 一种用于治疗肿瘤的黄酮衍生物及其应用
CN111494360B (zh) * 2020-04-29 2021-02-12 陕西师范大学 朝藿定c治疗糖尿病肝损伤的药物应用
CN112375059A (zh) * 2021-01-05 2021-02-19 遵义医科大学 一种淫羊藿素甲基化结构修饰化合物及其制备方法和应用

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CN1179422A (zh) * 1996-09-27 1998-04-22 阿迪尔公司 新黄酮化合物、制备它们的方法以及含有它们的药物组合物
CN1634910A (zh) * 2004-11-11 2005-07-06 中国药科大学 注射用淫羊藿总黄酮的制备方法

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1179422A (zh) * 1996-09-27 1998-04-22 阿迪尔公司 新黄酮化合物、制备它们的方法以及含有它们的药物组合物
CN1634910A (zh) * 2004-11-11 2005-07-06 中国药科大学 注射用淫羊藿总黄酮的制备方法

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101928328A (zh) * 2009-06-17 2010-12-29 李毅林 一种rgd肽-淫羊藿黄酮结合物、及其制备方法和应用
CN112574160A (zh) * 2020-12-07 2021-03-30 武汉轻工大学 一种高良姜素衍生物及其制备方法和应用
CN112574160B (zh) * 2020-12-07 2022-09-30 武汉轻工大学 一种高良姜素衍生物及其制备方法和应用
CN115399405A (zh) * 2022-11-01 2022-11-29 四川合泰新光生物科技有限公司 一种宝藿苷i葡聚糖包合物的用途
CN115399405B (zh) * 2022-11-01 2023-03-14 四川合泰新光生物科技有限公司 一种宝藿苷i葡聚糖包合物的用途

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