CN1836657A - Polymethoxylated flavones and its preparation method - Google Patents
Polymethoxylated flavones and its preparation method Download PDFInfo
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- CN1836657A CN1836657A CN 200510049423 CN200510049423A CN1836657A CN 1836657 A CN1836657 A CN 1836657A CN 200510049423 CN200510049423 CN 200510049423 CN 200510049423 A CN200510049423 A CN 200510049423A CN 1836657 A CN1836657 A CN 1836657A
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- Prior art keywords
- polymethoxyflavone
- injection
- surfactant
- flavone
- alcohol
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- 229930003944 flavone Natural products 0.000 title abstract description 14
- 235000011949 flavones Nutrition 0.000 title abstract description 14
- 238000002360 preparation method Methods 0.000 title abstract description 7
- 150000002213 flavones Chemical class 0.000 title 1
- 238000002347 injection Methods 0.000 claims abstract description 31
- 239000007924 injection Substances 0.000 claims abstract description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 22
- ULSUXBXHSYSGDT-UHFFFAOYSA-N tangeretin Chemical compound C1=CC(OC)=CC=C1C1=CC(=O)C2=C(OC)C(OC)=C(OC)C(OC)=C2O1 ULSUXBXHSYSGDT-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000004094 surface-active agent Substances 0.000 claims abstract description 15
- OBIOZWXPDBWYHB-UHFFFAOYSA-N Nobiletin Natural products C1=CC(OC)=CC=C1C1=C(OC)C(=O)C2=C(OC)C(OC)=C(OC)C(OC)=C2O1 OBIOZWXPDBWYHB-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000000203 mixture Substances 0.000 claims abstract description 9
- MRIAQLRQZPPODS-UHFFFAOYSA-N nobiletin Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC(=O)C2=C(OC)C(OC)=C(OC)C(OC)=C2O1 MRIAQLRQZPPODS-UHFFFAOYSA-N 0.000 claims abstract description 9
- DGPHAUBUAGDZCS-UHFFFAOYSA-N 2-(2,3-dimethoxyphenyl)-3,5,6,7,8-pentamethoxychromen-4-one Chemical compound COC1=CC=CC(C2=C(C(=O)C3=C(OC)C(OC)=C(OC)C(OC)=C3O2)OC)=C1OC DGPHAUBUAGDZCS-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229930182496 polymethoxyflavone Natural products 0.000 claims description 39
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 12
- -1 senensetin Chemical compound 0.000 claims description 10
- ZEMPKEQAKRGZGQ-AAKVHIHISA-N 2,3-bis[[(z)-12-hydroxyoctadec-9-enoyl]oxy]propyl (z)-12-hydroxyoctadec-9-enoate Chemical class CCCCCCC(O)C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CC(O)CCCCCC)COC(=O)CCCCCCC\C=C/CC(O)CCCCCC ZEMPKEQAKRGZGQ-AAKVHIHISA-N 0.000 claims description 8
- 235000008603 tangeritin Nutrition 0.000 claims description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 5
- 230000001954 sterilising effect Effects 0.000 claims description 2
- 238000004659 sterilization and disinfection Methods 0.000 claims description 2
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 abstract description 13
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 abstract description 13
- 150000002212 flavone derivatives Chemical class 0.000 abstract description 11
- 238000010255 intramuscular injection Methods 0.000 abstract description 3
- 239000007927 intramuscular injection Substances 0.000 abstract description 3
- IECRXMSGDFIOEY-UHFFFAOYSA-N Tangeretin Natural products COC=1C(OC)=C(OC)C(OC)=C(C(C=2)=O)C=1OC=2C1=CC=C(O)C=C1 IECRXMSGDFIOEY-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 238000010253 intravenous injection Methods 0.000 abstract description 2
- LKMNXYDUQXAUCZ-UHFFFAOYSA-N sinensetin Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC(=O)C2=C(OC)C(OC)=C(OC)C=C2O1 LKMNXYDUQXAUCZ-UHFFFAOYSA-N 0.000 abstract 2
- QEWSAPKRFOFQIU-UHFFFAOYSA-N 5-Hydroxy-6,7,3',4'-tetramethoxyflavone Natural products C1=C(OC)C(OC)=CC=C1C1=CC(=O)C2=C(O)C(OC)=C(OC)C=C2O1 QEWSAPKRFOFQIU-UHFFFAOYSA-N 0.000 abstract 1
- 229940090044 injection Drugs 0.000 description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- 238000010790 dilution Methods 0.000 description 6
- 239000012895 dilution Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 5
- 238000001990 intravenous administration Methods 0.000 description 5
- 241000589220 Acetobacter Species 0.000 description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 4
- 238000011085 pressure filtration Methods 0.000 description 4
- 239000002510 pyrogen Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000005303 weighing Methods 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 229960000935 dehydrated alcohol Drugs 0.000 description 3
- 229940093181 glucose injection Drugs 0.000 description 3
- 239000008354 sodium chloride injection Substances 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000001093 anti-cancer Effects 0.000 description 2
- 229960004756 ethanol Drugs 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000008215 water for injection Substances 0.000 description 2
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 206010002198 Anaphylactic reaction Diseases 0.000 description 1
- 101100248253 Arabidopsis thaliana RH40 gene Proteins 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 206010017533 Fungal infection Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 241001093501 Rutaceae Species 0.000 description 1
- 206010039966 Senile dementia Diseases 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 230000036783 anaphylactic response Effects 0.000 description 1
- 208000003455 anaphylaxis Diseases 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 230000002949 hemolytic effect Effects 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 206010025482 malaise Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Abstract
The polymethoxyl flavone injection includes polymethoxyl flavone, alcohol and surfactant, and the polymethoxyl flavone is mixture of two or more of nobiletin, tangeretin, sinensetin, heptamethoxyl flavone and isotangeretin. The present invention solves the solubility and stability problem of polymethoxyl flavone injection, and the polymethoxyl flavone injection has high safety, coincides with medicine standard and suitable for intramuscular injection and intravenous injection. The present invention also discloses the preparation process of the polymethoxyl flavone injection.
Description
Technical field
The present invention relates to field of pharmaceutical preparations, specifically polymethoxyflavone injection and preparation method thereof.
Background technology
Polymethoxyflavone is to extract a kind of mixture that obtains from the fruit of rutaceae.Its main component is Nobiletin (Nobiletin, 5,6,7,8,3`, 4`-hexa methoxy flavone) and tangeritin (tangeretin, 5,6,7,8,4`-pentamethoxyl flavone), in addition, also have senensetin (senensetin, 5,6,7,3`, 4`-pentamethoxyl flavone), Heptamethoxyflavone (heptamethoxyflavone, 3,5,6,7,8,3`, 4`-Heptamethoxyflavone), isosenensetin (isosenensetin, 5,7,8,3`, 4`-pentamethoxyl flavone) etc. (structural formula is as follows).According to pertinent literature report, polymethoxyflavone has multiple medicinal functions such as anti-fungal infection, treatment hypertension and diabetes, prevention and treatment chronic rheumatism, anticancer, treatment senile dementia, fat-reducing.
The Nobiletin tangeritin
The Heptamethoxyflavone senensetin
The isosenensetin
At Chinese patent " anticancer medicine composition of citrus multimethoxy flavone and preparation thereof " (publication number CN1436528A, open day: disclose a kind of polymethoxyflavone injection on August 20th, 2003), become injection with propylene glycol with 5: 1 proportional arrangement of w/v by polymethoxyflavone.Though polymethoxyflavone can be dissolved in the propylene glycol, but understanding generation in a short period of time behind the dilute with water precipitates and can't inject, and fully be that the solution of solvent should not be directly as injection with alcohol, so this technical scheme, because poor stability, do not meet medicinal standard, be unwell to commercial production.
Summary of the invention
The objective of the invention is to overcome the deficiencies in the prior art, a kind of good stability is provided, meet many methoxies flavone injection of medicinal standard.
The invention provides a kind of many methoxies flavone injection, a kind of preparation method also is provided simultaneously.
The invention discloses a kind of polymethoxyflavone injection, comprise following component: polymethoxyflavone, alcohol, surfactant; Wherein said polymethoxyflavone is any two or more the mixture among Nobiletin, tangeritin, senensetin, Heptamethoxyflavone, the isosenensetin.In order to reach medicinal standard, Polymethoxylated general flavone content should be more than 80%.
Polymethoxyflavone is a kind of material that is insoluble in water owing to its structural reason, and almost insoluble in water, the dissolubility in alcohol is better.But its alcoholic solution precipitation promptly occurs after by the dilution of a certain amount of water in a short period of time, and is that the solution of solvent should not be directly as injection fully with alcohol.Therefore the form administration of polymethoxyflavone with injection must to be solved the problem of its dissolubility in aqueous solution and stability.
Find through overtesting, alcohol and surfactant are share, not only can increase the dissolubility of polymethoxyflavone in water greatly, and can make polymethoxyflavone in water stably the form with solution exist more than 4 hours, injection at this moment, can can not satisfy intravenous requirement owing to the problem of polymethoxyflavone on the instability on the physical property (separating out precipitation) causes safely.
Wherein polymethoxyflavone is 1 with the w/v of alcohol: 0.01-0.1.
The consumption of alcohol is decided on the kind of alcohol in the prescription, if use ethanol, its consumption adds more than the ethanol 1ml for the 100mg polymethoxyflavone, is advisable with 1ml; If with 1, the 2-propylene glycol, its consumption adds 1 for the 100mg polymethoxyflavone, more than the 2-propylene glycol 3ml, is advisable with 3ml.
Wherein the weight part ratio of polymethoxyflavone and surfactant is 1: 4-60.
Alcohol will be used in certain proportion with surfactant and polymethoxyflavone, could guarantee that the physical property of its aqueous solution keeps stable in the long time, and wherein the ratio of surfactant and polymethoxyflavone is crucial.By weight, the ratio of polymethoxyflavone and surfactant should be 1: 4-60.Because surfactant concentrations is crossed conference and is caused hemolytic, the hidden danger of specific safeties such as anaphylaxis, so, the consumption of control surface activating agent.The kind of surfactant is selected also very important, with HLB being advisable between 13～19, as tween 80, polyoxyethylene hydrogenated Oleum Ricini (RH60 with BASF is good).
Polymethoxyflavone injection disclosed by the invention, dissolubility is good, and the maintenance in the long time of its aqueous solution is stable, can satisfy intravenous needs, and have good safety.
The invention also discloses a kind of method for preparing the polymethoxyflavone injection, may further comprise the steps: after surfactant, pure and mild polymethoxyflavone are mixed in hermetic container, placing 35～70 ℃ water-bath to heat, is good with 45～60 ℃, makes it molten entirely.Take out, place at room temperature more than half an hour, standby.Above solution is after removing operations such as thermal source, filtration and sterilization and reaching the requirement of injection, and confession intramuscular injection or intravenous injection are faced with behind the preceding water for injection or sodium chloride for injection solution or glucose for injection solution dilution that adds proper proportion according to circumstances in packing.
After testing, the every index of polymethoxyflavone injection of the present invention's preparation all meets the pharmacy standard.
In practical clinical, the consumption of polymethoxyflavone is decided on the kind of the disease that will prevent or treat.
The specific embodiment
Embodiment 1:
Take by weighing polyoxyethylene hydrogenated Oleum Ricini (RH60) but 180 restrain in hermetic container, add 400 milliliters of dehydrated alcohol, be mixed into liquid condition under the room temperature, mixture 30 grams that add Nobiletin, tangeritin, senensetin, Heptamethoxyflavone, isosenensetin again, after container was airtight, 50 ℃ of water-baths made it molten entirely.Take out, room temperature was placed 45 minutes.The needle-use activated carbon that adds liquid gross weight 0.1% then, stirring at room 20 minutes after No. 4 core filter sticks filtrations, does not have Mycoderma pressure filtration with 0.22 μ ф 300mm, after prediction content and pyrogen are qualified, aseptic subpackaged 1000 bottles.Face with preceding with after the 5ml water for injection dilution, can supply intramuscular injection.
Embodiment 2:
But take by weighing 600 gram tween 80s in hermetic container, add 1000 milliliters of dehydrated alcohol, be mixed into liquid condition under the room temperature, add Nobiletin, tangeritin, senensetin's mixture 100 grams again, after container was airtight, 70 ℃ of water-baths made it molten entirely.Take out, room temperature was placed 60 minutes.The needle-use activated carbon that adds liquid gross weight 0.5% then, stirring at room 15 minutes after No. 4 core filter sticks filtrations, does not have Mycoderma pressure filtration with 0.22 μ ф 300mm, after prediction content and pyrogen are qualified, aseptic subpackaged 1000 bottles.Face with preceding with after the dilution of 100ml 0.9% sodium chloride injection or 5% glucose injection, but injection for intravenous.
Embodiment 3:
Take by weighing polyoxyethylene hydrogenated Oleum Ricini (RH40) but 400 restrain in hermetic container, add 1,1500 milliliters of 2-propylene glycol, be mixed into liquid condition under the room temperature, add mixture 50 grams of senensetin, Heptamethoxyflavone again, after container was airtight, 35 ℃ of water-baths made it molten entirely.Take out, room temperature was placed 70 minutes.The needle-use activated carbon that adds liquid gross weight 0.3% then, stirring at room 30 minutes after No. 4 core filter sticks filtrations, does not have Mycoderma pressure filtration with 0.22 μ ф 300mm, after prediction content and pyrogen are qualified, aseptic subpackaged 1000 bottles.Face with preceding with after the dilution of 100ml 0.9% sodium chloride injection or 5% glucose injection, but injection for intravenous.
Embodiment 4:
Take by weighing polyoxyethylene hydrogenated Oleum Ricini (60) but 300 restrain in hermetic container, add 500 milliliters of dehydrated alcohol, be mixed into liquid condition under the room temperature, add Nobiletin, isosenensetin's mixture 10 grams again, after container was airtight, 50 ℃ of water-baths made it molten entirely.Take out, room temperature was placed 45 minutes.The needle-use activated carbon that adds liquid gross weight 0.4% then, stirring at room 25 minutes after No. 4 core filter sticks filtrations, does not have Mycoderma pressure filtration with 0.22 μ ф 300mm, after prediction content and pyrogen are qualified, aseptic subpackaged 1000 bottles.Face with preceding with after the dilution of 100ml0.9% sodium chloride injection or 5% glucose injection, but injection for intravenous.
Claims (7)
1. a polymethoxyflavone injection comprises following component: polymethoxyflavone, alcohol, surfactant; Wherein said polymethoxyflavone is any two or more the mixture among Nobiletin, tangeritin, senensetin, Heptamethoxyflavone, the isosenensetin.
2. polymethoxyflavone injection according to claim 1 is characterized in that the described polymethoxyflavone and the w/v of alcohol are 1: 0.01-0.1.
3. polymethoxyflavone injection according to claim 1, the weight part ratio that it is characterized in that described polymethoxyflavone and surfactant is 1: 4-60.
4. according to claim 1,2 described polymethoxyflavone injections, it is characterized in that described alcohol is ethanol or propylene glycol.
5. according to claim 1,3 described polymethoxyflavone injections, it is characterized in that described surfactant is selected from the HLB value and is 13-19.
6. polymethoxyflavone injection according to claim 5 is characterized in that described surfactant is a polyoxyethylene hydrogenated Oleum Ricini.
7. prepare polymethoxyflavone injection as claimed in claim 1, may further comprise the steps: after surfactant, pure and mild polymethoxyflavone are mixed in hermetic container, place 35～70 ℃ water-bath to heat, make it molten entirely; Take out, place more than half an hour at room temperature; Remove thermal source, filter, sterilization.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200510049423 CN1836657A (en) | 2005-03-23 | 2005-03-23 | Polymethoxylated flavones and its preparation method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200510049423 CN1836657A (en) | 2005-03-23 | 2005-03-23 | Polymethoxylated flavones and its preparation method |
Publications (1)
| Publication Number | Publication Date |
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| CN1836657A true CN1836657A (en) | 2006-09-27 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 200510049423 Pending CN1836657A (en) | 2005-03-23 | 2005-03-23 | Polymethoxylated flavones and its preparation method |
Country Status (1)
| Country | Link |
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| CN (1) | CN1836657A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101947215A (en) * | 2010-06-21 | 2011-01-19 | 澳门大学 | Application of flavonoid compound in tangerine peel to preparation of medicament for inhibiting angiogenesis |
| CN102579424A (en) * | 2012-01-20 | 2012-07-18 | 李康 | Application of hesperetin in preparation process of drugs for treating allergic asthma |
| CN102846595A (en) * | 2012-09-21 | 2013-01-02 | 沈阳药科大学 | Application of flavonoid compound WX-03 in relaxation of vascular smooth muscles |
| CN103127053A (en) * | 2011-11-22 | 2013-06-05 | 沈阳药科大学 | Medical application of 6-[2-(dimethylamino)ethoxy]flavone |
| CN107510693A (en) * | 2017-09-22 | 2017-12-26 | 上海华堇生物技术有限责任公司 | The medicinal usage of demethylnobiletin |
| EP3769622A1 (en) * | 2019-07-23 | 2021-01-27 | Karl-Franzens-Universität Graz | Antimycotic |
| CN112601461A (en) * | 2018-08-01 | 2021-04-02 | 弗门尼舍有限公司 | Polymethoxylated flavones as sweetness enhancers |
-
2005
- 2005-03-23 CN CN 200510049423 patent/CN1836657A/en active Pending
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101947215A (en) * | 2010-06-21 | 2011-01-19 | 澳门大学 | Application of flavonoid compound in tangerine peel to preparation of medicament for inhibiting angiogenesis |
| CN103127053A (en) * | 2011-11-22 | 2013-06-05 | 沈阳药科大学 | Medical application of 6-[2-(dimethylamino)ethoxy]flavone |
| CN103127053B (en) * | 2011-11-22 | 2014-05-21 | 沈阳药科大学 | Medical application of 6-[2-(dimethylamino)ethoxy]flavone |
| CN102579424A (en) * | 2012-01-20 | 2012-07-18 | 李康 | Application of hesperetin in preparation process of drugs for treating allergic asthma |
| CN102846595A (en) * | 2012-09-21 | 2013-01-02 | 沈阳药科大学 | Application of flavonoid compound WX-03 in relaxation of vascular smooth muscles |
| CN102846595B (en) * | 2012-09-21 | 2013-08-28 | 沈阳药科大学 | Application of flavonoid compound WX-03 in relaxation of vascular smooth muscles |
| CN107510693A (en) * | 2017-09-22 | 2017-12-26 | 上海华堇生物技术有限责任公司 | The medicinal usage of demethylnobiletin |
| CN112601461A (en) * | 2018-08-01 | 2021-04-02 | 弗门尼舍有限公司 | Polymethoxylated flavones as sweetness enhancers |
| CN112601461B (en) * | 2018-08-01 | 2021-10-22 | 弗门尼舍有限公司 | Polymethoxylated flavones as sweetness enhancers |
| EP3769622A1 (en) * | 2019-07-23 | 2021-01-27 | Karl-Franzens-Universität Graz | Antimycotic |
| WO2021013930A1 (en) | 2019-07-23 | 2021-01-28 | Karl-Franzens-Universität Graz | Antimycotic |
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Open date: 20060927 |