WO2008014722A1 - Flavonoïdes prényle, préparation et utilisation de ces composés - Google Patents

Flavonoïdes prényle, préparation et utilisation de ces composés Download PDF

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Publication number
WO2008014722A1
WO2008014722A1 PCT/CN2007/070375 CN2007070375W WO2008014722A1 WO 2008014722 A1 WO2008014722 A1 WO 2008014722A1 CN 2007070375 W CN2007070375 W CN 2007070375W WO 2008014722 A1 WO2008014722 A1 WO 2008014722A1
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natural number
ring
glc
alkyl
reaction
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PCT/CN2007/070375
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English (en)
Chinese (zh)
Inventor
Jingshan Shen
Shujun Zhang
Hongli Guo
Xinjian Chen
Yifeng Nian
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Topharman Shanghai Co., Ltd.
Shanghai Institute Of Materia Medica, Chinese Academy Of Sciences
Qiqihar University
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Publication of WO2008014722A1 publication Critical patent/WO2008014722A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
    • C07H17/06—Benzopyran radicals
    • C07H17/065—Benzo[b]pyrans
    • C07H17/07—Benzo[b]pyran-4-ones
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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
    • 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
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
    • C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
    • C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
    • C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones

Definitions

  • the present invention relates to a prenyl flavonoid derivative, a preparation method and use thereof. Background technique
  • Isopentenyl flavonoids have a wide range of biological activities, such as antibacterial, antitumor, anti-HIV, anti-oxidant and inhibition of some enzymes, such as inhibition of phosphodiesterase. Although isopentenyl flavonoids are not widely distributed in plants, they have received extensive attention due to their high content, diverse structure and biological activity in some plants, such as epimedium.
  • Epimedium is the general name for Epimedi, a variety of plants of the genus Epimedium, also known as “Fairy Spleen”, which is a commonly used ingredient in the prescription of traditional Chinese medicine nourishing and strong agent. Many varieties of this genus have medicinal use in China. "Shen Nong's Herbal Classic” is listed as a Chinese product, and all previous generations of the grass have been recorded, which is a strong and strong medicine. In the “Compendium of Materia Medica”, it is said that it has the merits of "Yi Jing Qi, Jian Lu Gu, Bu Kuang Kuang, Qiang Xin” Effective. There have been many studies on the chemical constituents and pharmacological effects of the raw drug Epimedium or its extract. It has been found that icariin can be used to treat sexual dysfunction (CN1282584A). Summary of the invention
  • An object of the present invention is to provide a prenyl flavonoid derivative having good PDE5 inhibitory activity and a process for producing the same.
  • the present invention provides a prenyl flavonoid derivative as shown in Formula I:
  • ring A is a pentokeose or a hexacarbose (eg, D-xylose, D-ribose, L-arabinose, D-glucose, D-galactose, L-rhamnose, etc.) or Disaccharides (eg, sesame, gentian, sugar, etc.).
  • the saccharide compound and the flavonoid ring together constitute a compound of formula (I).
  • R is a substituent of a hydroxyl group on the A ring, and may be selected from any of H, C0C m H 2m+1 (m is a natural number of 1 - 6), and C m H 2m+1 (m is a natural number of 1 - 6) n represents the number of substituents, which is any natural number from 1 to 7;
  • ⁇ can be selected from H, C "C 6 alkyl, C 3 - C s cycloalkyl, C 2 - C 6 alkenyl, C Any one of 2 - C 6 fatty acyl or C 7 - C 12 aroyl;
  • R 2 may be selected from any of ! or ⁇ - ⁇ alkyl;
  • R 3 may be selected from H, dC 6 Any of the alkyl groups.
  • the above isopentenyl derivative is represented by the formulas IA, I IA, II IA, IVA, VA, VIA:
  • VIA which may be selected from the group consisting of H, C "C 6 alkyl, C 3 - C s cycloalkyl, C 2 - chain ⁇ , c 2 -c 6 fatty acyl: or C 7 _C 12 aroyl acyl
  • R 2 may be selected from any one of !! or - alkyl
  • R 3 may be selected from any of H, C "C 6 alkyl.
  • R 4 , R 5 , R 6 , R 7 , R s , ⁇ and ⁇ . may be selected from any of H, C0C m H 2m+1 (m is a natural number of 1 -6), C m H 2m+1 (m is a natural number of 1 -6) .
  • the A ring is a five-carbon ring sugar, a six carbon ring Sugar (eg D-xylose, D-ribose, L-arabinose, D-glucose, D-galactose, L-rhamnose, etc.) or disaccharides (eg: rutose, gentiobiose, bismuth) Sugar, etc.).
  • the saccharide compound and the flavonoid ring together constitute a compound of formula (I).
  • R is a substituent of a hydroxyl group on the ring A, and is selected from any one of H, C0C m H 2m+1 (m is a natural number of 1 - 6), and C m H 2m+1 (m is a natural number of 1 - 6) n represents the number of substituents, which is any natural number from 1 to 7;
  • ⁇ can be selected from H, C "C 6 alkyl, C 3 -C S cycloalkyl, C -C 6 alkenyl, C 2 -C Any of 6 fatty acyl groups or C 7 -C 12 aroyl groups.
  • the present invention also provides a process for producing the above isopentenyl derivative:
  • the above isopentenyl derivative is obtained by an acylation reaction or an alkylation reaction from a phenolic hydroxyl group on a flavonoid ring or an alcoholic hydroxyl group on a saccharide ring.
  • the acylating reagent includes an acid anhydride and an acid chloride; the reaction solvent is anhydrous pyridine or dichloromethane; and the catalyst includes pyridine, triethylamine and 4-(anthracene, fluorenyl-dimethylamino)pyridine.
  • the alkylating agent comprises methyl iodide, ethyl bromide or dimethyl sulfate and diethyl sulfate;
  • the reaction solvent is acetone or hydrazine, hydrazine-dimethylformamide;
  • the catalyst is potassium carbonate, Sodium hydroxide and potassium hydroxide.
  • the present invention also provides a medicament for treating or preventing a disease associated with cGMP-specific phosphodiesterase V, which comprises a compound of the formula I and a pharmaceutically acceptable salt thereof.
  • the above medicament contains any one or more of the compounds represented by formula IA, I IA, I I IA, IVA, VA or VIA and pharmaceutically acceptable salts thereof.
  • the above medicaments contain a compound of the formula IA and a pharmaceutically acceptable salt thereof, wherein the compound of the formula IA includes the following specifically specified conditions: ⁇ selected from H or CH 3 , and R 2 is selected from H or CH 3 , 11 3 ( 3 ⁇ 4 , R 4 , R 5 , R 6 and R 7 are H; or Ri, R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are both H.
  • the compound of formula I provided by the present invention is a novel selective PDE5 inhibitor which promotes penile erection in normal rats and has no significant difference compared to sildenafil.
  • the inhibitory activity of the compound of formula I provided by the present invention on PDE6 is much weaker than that of PDE5.
  • Activity, which has strong selectivity for PDE5 predicts that the side effects of visually impaired compounds are smaller than sildenafil.
  • the present inventors isolated from Epimedium extract (purchased in Chengdu Mudu Biotechnology Co., Ltd. on December 13, 2003, the plant material is mainly Epimedium, and the content of icariin is about 14.2%). Icyl glycoside-1, icariin-C, baumannin-1, baumannin-11, icariin, and esculentin, and icariin -I was structurally modified and found to be effective in inhibiting phosphodiesterase V (PDE5).
  • PDE5 phosphodiesterase V
  • 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, Bladder outlet obstruction, incontinence, unstable and variant Prinzmetal angina, hypertension, pulmonary hypertension, congestive heart failure, renal failure, atherosclerosis, stroke, peripheral vascular disease, Raynaud's disease, inflammatory disease, bronchitis , chronic asthma, allergic asthma, allergic rhinitis, glaucoma, and diseases characterized by bowel movements (eg, irritable bowel syndrome).
  • bowel movements eg, irritable bowel syndrome
  • Icariin and icariin-I are isolated and extracted from the extract of Epimedium by an organic solvent or a mixed solvent of an organic solvent and water.
  • Organic solvents which may be used include alcohols such as methanol, ethanol, butanol, etc., halogenated hydrocarbons such as dichloromethane, chloroform, etc., ethers such as diethyl ether, ketones such as acetone, esters such as ethyl acetate, hydrocarbons such as petroleum. Ether, n-hexane, etc.
  • Icariin-I can also be obtained from the hydrolysis of icariin.
  • the catalyst used in the hydrolysis includes sulfuric acid, p-toluenesulfonic acid, hydrochloric acid, phosphoric acid, acetic acid, etc.
  • the solvents used include methanol, ethanol, DMF and Water, etc.
  • Preferred compounds of the invention include:
  • the present invention provides a process for the preparation of a compound of formula (I). Also, the present invention also includes any novel intermediates in the preparation process and a process for the preparation thereof, such as a compound of the following formula (II) and a process for the preparation thereof.
  • the phenolic hydroxyl group on the flavonoid ring or the alcoholic hydroxyl group on the sugar ring is subjected to an acylation reaction or an alkyl group.
  • the flavonoid derivative obtained by the reaction, the acylating reagent comprises an acid anhydride and an acid chloride, preferably acetic anhydride
  • the solvent mainly comprises anhydrous pyridine, anhydrous triethylamine, anhydrous dichloromethane, anhydrous chloroform, anhydrous dioxane and Anhydrous tetrahydrofuran or the like, preferably anhydrous pyridine or anhydrous dichloromethane
  • the catalyst includes pyridine, triethylamine and 4-(anthracene, fluorenyl-dimethylamino)pyridine, etc., preferably pyridine
  • the reaction temperature is generally 10 ° C - 25 .
  • the reaction time is generally 1-12 hours; alkylating agents include halogenated hydrocarbons (such as: methyl iodide, ethyl bromide, etc.) and sulfates (dimethyl dimethyl sulfate and diethyl sulfate, etc.), the solvent is acetone and ⁇ , ⁇ -dimethylformamide, etc., the catalyst is an inorganic base (such as: potassium carbonate, sodium carbonate, potassium hydroxide and sodium hydroxide, etc.), the reaction temperature is generally 25 ° C-60 ° C, the reaction time is generally 2-20 hours.
  • alkylating agents include halogenated hydrocarbons (such as: methyl iodide, ethyl bromide, etc.) and sulfates (dimethyl dimethyl sulfate and diethyl sulfate, etc.)
  • the solvent is acetone and ⁇ , ⁇ -dimethylformamide, etc.
  • the catalyst is an
  • the present invention provides a prenyl flavonoid derivative prepared for the treatment or prevention of erectile dysfunction, female sexual dysfunction, premature labor, dysmenorrhea, benign prostatic hyperplasia, bladder outlet obstruction, incontinence, instability and variation of Pr inzme Ta l angina pectoris, hypertension, pulmonary hypertension, congestive heart failure, renal failure, atherosclerosis, stroke, peripheral vascular disease, Raynaud's disease, inflammatory disease, bronchitis, chronic asthma, allergic asthma, allergic rhinitis Use of glaucoma, and human (or animal) drugs characterized by diseases of intestinal peristalsis (eg, irritable bowel syndrome).
  • intestinal peristalsis eg, irritable bowel syndrome
  • 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 bovine retina was 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. In the presence of different inhibitor concentrations and a small amount of substrate, 10 is added.
  • the test compound was suspended in 0.5% methylcellulose and orally administered to rats at a single dose of 200 mg/kg. After administration, the intracavernosal pressure (ICP) and arterial blood pressure (MBp) of the rat's penis were continuously observed within 3 hours. The ICP and MBp changes were analyzed before and after treatment by Chart data processing software. The ratio of ICP to MBp was used to evaluate the effect of drugs on nerve stimulation-induced erection. Finally, t-test was performed with SPSS10.0 software. Three or more rats were assigned to each group, and for the other two groups, only an equal amount of 0.5% methylcellulose or 20 mg/kg of sildenafil citrate was administered as a negative control group and The positive control group, the results are shown in the following table:
  • TPN1258 200 25. 70 ⁇ 2. 6 32. 39 ⁇ 5. 1
  • the 1 H-NMR of the present invention was carried out on a Mercury-400 nuclear magnetic resonance spectrometer (Varian), and the observation frequency of -R was 400.144 MHz.
  • Mass spectrometry was performed on a MAT-95 mass spectrometer (Thermo Finnigan) with an ionization mode of EI 70V, a source temperature of 200 ° C, and an LR resolution of 1000.
  • High pressure liquid chromatography Agilent 1100 series, analytical column: ZORBAX Eel ipse XDB-C8 4.6 x 150 mm, semi-preparative column: GL Sciences Inertsil PREP-ODS 10 250 mm.
  • icariin-I 3.3 g was added to a 1 liter flask, and dissolved in 500 liters of acetone, followed by the addition of 17.4 g of potassium carbonate and 6.0 liters of dimethyl sulfate, and the mixture was heated (40 ° C) for 11 hours, and cooled to room temperature. The reaction liquid was filtered, and the solid was washed with acetone. The filtrate was concentrated under reduced pressure.
  • icariin-1 50 liters of acetone, 1 gram of anhydrous potassium carbonate, 0.125 g of potassium iodide and 0.5 liter of ethyl bromide were added to a 100 liter flask, and heated under nitrogen (40 C). 20 hours. After the reaction, the reaction solution was concentrated, 1M dilute hydrochloric acid was added thereto to adjust the pH of about 7, and extracted with ethyl acetate, the organic phase was washed with saturated brine, dried over anhydrous 2,804, filtered and concentrated, the product was recrystallized from methanol to give 0.19 g, Yield: 88%.
  • Example 9 compound 12 g of the Example 9 compound, 1 liter of methanol and 100 ⁇ l of potassium hydroxide solution (2 mol/liter) were sequentially added to a 10 liter round bottom flask, and stirred at room temperature for 0.5 h. After completion of the reaction the reaction mixture was added to saturated ammonium chloride solution, the organic phase was washed with saturated brine and extracted three times with ethyl acetate, dried over anhydrous after 2804, filtered and concentrated, the product was recrystallized from methanol to give 8 milligrams, Yield: 92%.

Abstract

Ll'invention concerne des flavonoïdes prényle, la préparation et l'utilisation de ces composés. Ces flavonoïdes prényle sont représentés par la formule I, dans laquelle le cycle A est un glucide à 5 ou 6 cycles de carbone ou un disaccharide, R est un substitut de hydroxy sur le cycle A sélectionné dans H,COCmH2m+1(m est un entier naturel compris entre 1 et 6) et CmH2m+1(m est un entier naturel compris entre 1 et 6), n est un entier naturel compris entre 1 et 7, R1 est sélectionné dans H,C1-C6alkyle,C3-C8cycloalkyle,C2-C6alkényle, C2-C6acyle ou C7-C12aroyle;R2 et R3 sont sélectionnés dans H ou C1-C6alkyle. cette invention concerne aussi un processus de préparation des composés susmentionnés. Cette invention concerne aussi un médicament comprenant les composés susmentionnés et leurs sel pharmaceutiquement acceptables. Ce médicament est utilisé pour soigner ou prévenir les maladies relevant de cGMP-PDE V
PCT/CN2007/070375 2006-07-28 2007-07-27 Flavonoïdes prényle, préparation et utilisation de ces composés WO2008014722A1 (fr)

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CNA200610029522XA CN101113157A (zh) 2006-07-28 2006-07-28 异戊烯基黄酮衍生物、制备方法及其用途
CN200610029522.X 2006-07-28

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Cited By (1)

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US11377466B2 (en) 2018-08-10 2022-07-05 Whitehead Institute For Biomedical Research Analogs of the natural product icariin

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CN102093450B (zh) * 2010-12-24 2013-09-04 台州市黄岩源宏医化科技有限公司 脱水淫羊藿糖苷化合成淫羊藿单甙的方法
CN103622947A (zh) * 2012-08-26 2014-03-12 鲁南制药集团股份有限公司 淫羊藿苷元在制备治疗哮喘药物中的用途
CN104387358B (zh) * 2014-10-27 2016-08-24 广东东阳光药业有限公司 淫羊藿苷类化合物及其应用
CN104447913B (zh) * 2014-11-06 2017-05-31 四川大学 功能化淫羊藿苷衍生物及其制备方法与应用
CN108486196A (zh) * 2015-05-20 2018-09-04 佛山市金骏康健康科技有限公司 一种淫羊藿次苷i或淫羊藿次苷c的制备方法
CN109369748A (zh) * 2018-10-29 2019-02-22 广东金骏康生物技术有限公司 一种淫羊藿次苷ⅰ类化合物、衍生物、药物组合物及其应用
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
CN109320570A (zh) * 2018-10-29 2019-02-12 广东金骏康生物技术有限公司 一种淫羊藿次苷ⅰ类化合物、衍生物、可药用盐及应用
CN109369747A (zh) * 2018-10-29 2019-02-22 广东金骏康生物技术有限公司 淫羊藿次苷ⅰ化合物及其衍生物、药物组合物及其制备方法和应用
CN110317208B (zh) * 2019-05-15 2023-02-17 北京东方百奥医药开发有限公司 一种淫羊藿素衍生物的制备方法和医药用途
CN115073409A (zh) * 2021-03-12 2022-09-20 中国海洋大学 一种新型淫羊霍素衍生物及其制备方法和应用
CN114605483B (zh) * 2022-04-06 2024-01-30 贵州汇腾科技有限公司 一种淫羊藿次苷ⅰ的制备工艺

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