WO2008090410A2 - Cinnamomi and poria composition and uses thereof - Google Patents
Cinnamomi and poria composition and uses thereof Download PDFInfo
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- WO2008090410A2 WO2008090410A2 PCT/IB2007/004483 IB2007004483W WO2008090410A2 WO 2008090410 A2 WO2008090410 A2 WO 2008090410A2 IB 2007004483 W IB2007004483 W IB 2007004483W WO 2008090410 A2 WO2008090410 A2 WO 2008090410A2
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- composition
- poria
- extracts
- cinnamomi
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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)
- A61K36/54—Lauraceae (Laurel family), e.g. cinnamon or sassafras
-
- 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
- A61K36/06—Fungi, e.g. yeasts
- A61K36/07—Basidiomycota, e.g. Cryptococcus
- A61K36/076—Poria
-
- 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)
- A61K36/65—Paeoniaceae (Peony family), e.g. Chinese peony
-
- 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)
- A61K36/73—Rosaceae (Rose family), e.g. strawberry, chokeberry, blackberry, pear or firethorn
-
- 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
- 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
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
Definitions
- the present invention is related to the making and using of a composition comprising Chinese herbal medicines Hamulus cinnamomi and Poria cocos (Chinese name: Guizhi and Fuling) .
- Cassia Twig is the dried young stem of Cmnamomum cassia Presl (Fam. Lauraceae) .
- the plant is collected in spring or summer. It is dried in the sun after collection and removal of its leaves. It can also be chopped into slides.
- the medicinal preparation has cylindrical body, multi-branched, 30-
- Cinnamomi 75 cm in length, with a thick end of 0.3-1 cm in diameter. It is brown or reddish-brown on the surface, with longitudinal lines, fine wrinkles, dotted with leaf, branch or bud scars. Hard and fragile, it is easily broken. For slices, it is 2-4 mm thick, cut surface showing reddish-brown in the bark area, yellowish-white to pale yellowish-brown in the wood part. It has a characteristic aromatic odor, and is tasted sweet or slightly pungent (especially in the bark) .
- the medicinal preparation is the clean scraps of Cinnamomi without visible impurities.
- the important ingredients of Cinnamomi is cmnamaldehyde and cinamic acid.
- Indian Bread is the dried sclerotium of the fungus, Poria cocos (Fam. Polyporaceae) .
- the plant is collected from July to September. After collection, it was piled up and spread about for air-drying repeatedly until wrinkles appears on the surface and its inner moisture evaporated.
- the whole dried sclerotium is known as "Fulingge”. If the fresh sclerotium is peeled before drying, the separated parts are called "Fulmgpi"
- the outer skin is thin and rough, brown to blackish brown, conspicuously shrivelled and striated.
- the texture is hard and compact. It is odourless, tastes weak and becomes sticky when chewed.
- the medicinal preparation is the clean scraps of Poria without visible impurities. Its important active ingredients are Pachman and Pachymic acid.
- the present invention provides a composition comprising Chinese herbal medicines Ramulus cmnamomi and Poria cocos (Chinese name: Guizhi and Fuling) .
- the herbal composition is formulated into capsule as described in U.S. Patent 7,052,700, which is hereby incorporated by reference .
- the present invention provides a herbal composition comprising Ramulus cmnamomi and Poria cocos, wherein the composition produces 12 peaks when subjected to a method comprising the steps of: a) extracting the composition with an appropriate organic solvent; and b) performing chromatographic analysis.
- the relative retention time ranges for peaks 1-12 as compared to paeoniflo ⁇ n are 0.209-0.314, 0.456-0.683, 0.733-0.999, 0.871-1.306, 0.921-1.382, 0.968-1.451, 1.009-1.514, 1.058-1.587, 1.152-1.728, 1.69-2.536, 1.771-2.657, and 1.943-2.915 respectively.
- the present herbal composition further comprises paeoniflo ⁇ n and paeonol .
- paeoniflo ⁇ n and paeonol Preferably, there are 1.26-1.90% paeomflo ⁇ n and 0.71-1.07% paeonol.
- the present invention provides a composition produced by a method comprising the steps of: (a) preparing Poria powder; (b) preparing extracts of Cortex moutan;
- the present invention also provides a method of producing a composition comprising Ramulus cinnamomi and Poria cocos, the method comprises the steps of: (a) preparing Poria powder; (b) preparing extracts of Cortex moutan; (c) preparing extracts of Ramulus cinnamomi; (d) preparing extracts of Radix paeoniae alba, Semen persicae and Poria; (e) combining the extracts obtained from steps (b) - (d) ; (f) mixing the Poria powder with the extracts obtained from step (e) , and generating fine powders; and (g) mixing the fine powders with inclusion substances comprising extracts of Cortex moutan and Ramulus cinnamomi . [0020] The present invention also provides a pharmaceutical composition comprising a pharmaceutically acceptable carrier and the herbal composition described herein.
- the present invention provides a composition comprising Chinese herbal medicines Guizhi and FuIing (Hamulus cinnamomi and Poria cocos) .
- the herbal composition can be formulated into capsule as described in U.S. Patent 7,052,700, the disclosure of which is hereby incorporated by reference.
- the present invention provides a herbal composition comprising Ramulus cinnamomi and Poria cocos, wherein the herbal composition is defined by a 12-peaks fingerprint (Figure 1) obtained by a fingerprinting method comprising the steps of extracting the composition with an appropriate organic solvent, and performing chromatographic analysis.
- the chromatographic analysis is high performance liguid chromatography (HPLC) .
- HPLC high performance liguid chromatography
- the present herbal composition is extracted with the organic solvent methanol, and then subjected to HPLC with a paeoniflo ⁇ n standard according to procedures well-known in the art.
- the relative peak area ranges for peaks 1, 8, 9, and 12 as compared to paeoniflorin are 0.25-0.89, 0.69-1.5, 0.3- 0.85, and 1.56-3.06 respectively.
- the relative retention time ranges for peaks 1-12 as compared to paeoniflorin are 0.209-0.314, 0.456-0.683, 0.733- 0.999, 0.871-1.306, 0.921-1.382, 0.968-1.451, 1.009-1.514, 1.058-1.587, 1.152-1.728, 1.69-2.536, 1.771-2.657, and 1.943- 2.915 respectively.
- the present invention also provides a pharmaceutical composition
- a pharmaceutical composition comprising the herbal composition described herein and a pharmaceutically acceptable carrier.
- the herbal composition can be formulated into a pill, capsule, tablet, suspension, or syrup according to standard procedures.
- compositions for use in accordance with the present invention may include a pharmaceutically acceptable excipient or carrier.
- pharmaceutically acceptable carrier means a non-toxic, inert solid, semi-solid or liquid filler, diluent, encapsulating material or formulation.
- compositions which can serve as pharmaceutically acceptable carriers are sugars such as lactose, glucose, and sucrose; starches such as corn starch and potato starch; cellulose and its derivatives such as sodium carboxymethyl cellulose, ethyl cellulose and cellulose acetate; malt; gelatin; talc; excipients such as cocoa butter and suppository waxes; oils such as peanut oil, cottonseed oil, safflower oil, sesame oil, olive oil, corn oil, and soybean oil; glycols, such as propylene glycol; esters, such as ethyl oleate and ethyl laurate; agar; buffering agents such as magnesium hydroxide and aluminum hydroxide; pyrogen-free water; isotonic saline; Ringer's solution; ethyl alcohol; and phosphate buffer solutions, as well as other non-toxic compatible lubricants such as sodium lauryl sulfate and magnesium stearate, as well as coloring
- the present invention also provides a method of treating a subject having a disease or disorder, comprising the step of administering to the subject an effective amount of the herbal composition disclosed herein.
- the "effective amount" of an agent or composition refers to the amount necessary to elicit a desired biological response.
- the effective amount of the active components of an herb or herbal remedy is the amount necessary to decrease a particular sign and/or symptom.
- One of ordinary skill in the art could readily determine an effective amount of the present herbal composition through conventional methods and techniques.
- the herbal composition of the present invention can be used to treat a variety of disease or disorder.
- a number of applications have been discussed in U.S. Patent 7,052,700.
- the Cinnamomi & Poria capsule can be used to treat primary or secondary dysmenorrhea, dysfunctional uterine bleeding caused by irreglar shedding of endometrim, chronic pelvic inflammations with inflammatory lower abdomen masses or small intramural hysteromyoma, and many other common pelvic disorders.
- Further pharmacological studies, pre-clinical as well as clinical studies using the herbal composition of the present invention can be carried out as described in U.S. Patent 7,052,700.
- inventive pharmaceutical compositions of the present invention can be administered orally.
- pharmaceutical compositions may be delivered to mucous membranes, for example, by inhalation or injection.
- the present inventive pharmaceutical compositions can be administered to humans and/or other animals orally, rectally, parenterally, lntracisternally, intravaginally, intraperitoneally, topically (as by powders, ointments, or drops), bucally, or as an oral or nasal spray.
- the present example provides a herbal composition comprising Cinnamomi & Poria in capsule form (Cinnamomi & Poria capsule) .
- Cinnamomi & Poria capsule The process of making Cinnamomi & Poria capsule has been described in U.S. Patent 7,052,700, which is hereby incorporated by reference.
- the Cinnamomi & Poria capsule contains yellowish brown granule which tasted slightly bitter.
- each capsule containing 0.31 g of the granule can be stored for 24 months at room temperature.
- Step 1 Weigh (50%-90% of the formulation quantity) Porta
- Step 3 Sterilize the Poria powder by microwave. This is designated as Poria Powder.
- Step 6 Collect the liquid distillate.
- the Liquid Distillate is refrigerated, filtered and cool dried to achieve a extract.
- the dried extract is designated as Paeonol.
- Step 8 Extract Solid Residue I with 80 ⁇ 95% ethanol twice (3-5 times volume for the first time and 2-4 times for the second). Boil for 1 ⁇ 3 hours each time.
- Step 9 Combine the ethanol extracts This is Extract I.
- Step 10 Extract the solid residue with water twice (5-7 times volume for the first time and 3-5 times for the second). Boil for 1 ⁇ 3 hours each time.
- Step 11 Combine the aqueous extracts. This is Extract II.
- Step 12 Weigh Ramulus cinnamomi.
- Step 15 Extract Solid Residue II with 80—95% ethanol twice (3—5 times volume for the first time and 2 ⁇ 4 times for the second). Boil for 1 ⁇ 3 hours each time.
- Step 19 Weigh Radix paeoniae alba, Semen persicae, and PoHa (10%-50% of the formulation quantity) .
- Step 20 Add 3—5 times of 80—95% ethanol and leave at room temperature for
- Step 25 Combine Extract I (Step 9), III (Step 16) and V (Step 22). Concentrate under vacuum till no ethanol smell. This is Liquid A.
- Step 26 Combine Extract II (Step 11), IV (Step 18) and VI (Step 24). Concentrate under vacuum. This is Liquid B.
- Step 27 Combine Liquid A and B. Concentrate under vacuum till the relative density equal to 1.15-1.35(60— 9O 0 C). The concentrated liquid extract is designated as Semisolid Extract.
- Step 28 Weigh ⁇ -cyclodextrin and add into 2—3 times of water. Heat the ⁇ - cyclodextrin solution to 50— 7O 0 C.
- Step 29 Dissolve the total paeonol extract from Step 6 into 4 ⁇ 6 times of 80-95% ethanol.
- Step 30 Add the paeonol solution into the ⁇ -cyclodextrin solution.
- Step 31 Grind for 10—30 minutes.
- Step 32 Then place into refrigerator for 12—36 hours.
- Step 35 Weigh ⁇ -cyclodextrin and add into 4-6 times of 10—30 % ethanol solution. Add the all volatile oil from Step 13 into the ⁇ -cyclodextrin solutionunder continuous stirring Step 36: Keep grind for 20—40 minutes.
- Step 37 Then place into refrigerator for 12-36 hours.
- Step 38 Filter under vacuum.
- Step 39 Dry at 40— 6O 0 C.
- the resulted white powder is Inclusion Substance II.
- Step 40 Mix the Poria Powder with all the Semisolid Extract.
- Step 41 Dry the mixture at 70— 100 0 C, and grind into fine powders
- Step 42 Mix Fine Powder I with Inclusion Substances I and Inclusion Substances II.
- Step 43 Add 50 ⁇ 80% ethanol solution to make a dough-like mass.
- Step 44 Pass the wet material through a 16-24mesh sieve to obtain the granules.
- Step 45 Dry the granules at 40 ⁇ 6O 0 C.
- Step 46 Pass the dried granules through the sieve again.
- Step 47 Mix the dried granules well. This is Final Granules.
- Poria fine powder needs to be screened by 100 meshes of screen (inner diameter 150 ⁇ 6.6 ⁇ m.)
- the concentration of crude paeonol should be no less than 90%.
- Creamed extractive the creamed extractive is dark brown in color. Its relative density should be 1.15-1.35 (60 ⁇ 70 0 C), and the content of paeoniflorin should be 1.36-2.04%
- Capsules clean, not sticky or mutilated in shape. Differences in content should be no more than ⁇ 10% (0.31 g/capsule) . Dissolving time is within 30 minutes. Water content should be no more than 7.0%. Content of paeoniflorin is at 1.26-1.90% and paeonol 0.71-1.07%.
- test was carried out according to the HPLC method (Chinese Pharmacopoeia 2000 Ed, Vol. One, Appendix VI D) and the requirements for fingerprints .
- Sample Preparation Take the content of the samples for Weight Variation Test, mix thoroughly, and grind into fine powder. Weigh accurately about 0.25 g of the mixture and add 25 ml of 50% methanol. Sonicate the mixture for 30 min, and then filter. Discard the first part of the filtrate. Collect the rest filtrate as the test solution. Assay
- the HPLC chromatogram of any batch of Cinnamomi & Poria composition should have the 13 characteristic peaks.
- the relative retention time of the 13 peaks and the relative peak area of Peaks 1, 8, 9 and 12 should be in the specified range.
- HPLC data from ten different batches of Cinnamomi & Poria capsules have been confirmed to display the fingerprint profile presented herein.
- the fingerprint profile presented herein is different from the ones shown in U.S. Patent 7,052,700.
- the aqueous samples for HPLC were prepared by water reflux extraction. The contents of 3 Cinnamomi & Poria capsules were mixed with 200 ml distilled water for heat reflux for 30 mm (start timing at boiling) . The solution was cooled down, centrifuged for 10 mm, and filtered with a 0.45 ⁇ m filtration membrane. The first part of the filtrate was discarded and the rest of the filtrate was taken as the test solution. Consequently, the ⁇ 700 patent presents four chromatograms, i.e. one for water-soluble components, two for lipid-soluble components (of different chromatographic conditions and detection wavelengths), and one for gas Chromatography. The first three chromatograms exhibit poor reproducibility and have some peaks overlapping with each other.
- this processing method has been changed to use 50% methanol to extract the sample.
- the content of the samples for Weight Variation Test was mixed thoroughly and grinded into fine powder. Twenty five ml of methanol was added to 0.25 g of the mixture, which was then sonicated for 30 mm and then filtered. The first part of the filtrate was discarded, and the rest of the filtrate was collected as the test solution. It was found that extraction with 50% methanol resulted in more peaks, revealing not only more components of the Cinnamomi & Poria capsules, but also shows lipid-soluble and volatile components in the product. Therefore, the current method produces only one chromatogram, which can be used in combination with other quality control procedures to control the quality of the Cinnamomi & Poria capsules .
- the difference between these two methods is that the former method of water reflux extraction extracted components that were mainly water-soluble, and the major peaks in the chromatogram were the water-soluble compounds in the product.
- the method of the instant invention uses 50% methanol as the extraction solvent to extract more water- soluble components, lipid-soluble components as well as the volatile compound paeonol, and these compounds can be presented in one chromatogram that shows a higher paeonol peak based on equal sample amount.
- the evaluation parameters for the fingerprints of Traditional Chinese medicines are usually the ratios of the retention time and area of the characteristic peaks to those of the references.
- the relative retention time and peak area of each peak are used for the characterization of the fingerprint.
- the relative retention time and relative peak area of the feature peaks are specified.
- Such evaluation parameters can eliminate variations caused by differences in instruments, columns, mobile phase and environment that can change the retention time and peak area. Therefore, these parameters can be used objectively and comprehensively to represent the actual conditions of the constituents in and the internal quality of the product.
- the fingerprint characteristics presented herein are unique to the Cinnamomi & Poria Capsule of the present invention.
- the characteristic peaks of the fingerprint reveal constituents of every batch of Cinnamomi & Poria Capsule processed according to the disclosed manufacturing procedure.
- the current fingerprint standard was derived from optimization of assay conditions and data collected from many batches. Results from repeated assays of the same batch, as well as data from ten different batches (Tables 2-3) show that the current method can accurately fingerprint Cinnamomi & Poria Capsule with good reproducibility. The results also show that the constituents' contents are similar in different batches, the relative retention time and peak area of all the characteristic peaks being m the specified range.
Abstract
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Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
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JP2009532916A JP5328656B2 (en) | 2006-10-18 | 2007-10-17 | Cinnamomi and poria compositions and uses thereof |
EP07872088.5A EP2073825B1 (en) | 2006-10-18 | 2007-10-17 | Cinnamomi and poria composition and uses thereof |
US12/376,601 US8067040B2 (en) | 2006-10-18 | 2007-10-17 | Cinnamomi and poria composition and uses thereof |
CN200780027994.4A CN101495129B (en) | 2006-10-18 | 2007-10-17 | Cinnamomi and poria composition and uses thereof |
CA2659442A CA2659442C (en) | 2006-10-18 | 2007-10-17 | Cinnamomi and poria composition and uses thereof |
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US82994506P | 2006-10-18 | 2006-10-18 | |
US60/829,945 | 2006-10-18 |
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WO2008090410A2 true WO2008090410A2 (en) | 2008-07-31 |
WO2008090410A3 WO2008090410A3 (en) | 2008-11-13 |
WO2008090410A4 WO2008090410A4 (en) | 2009-01-22 |
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PCT/IB2007/004483 WO2008090410A2 (en) | 2006-10-18 | 2007-10-17 | Cinnamomi and poria composition and uses thereof |
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US (1) | US8067040B2 (en) |
EP (1) | EP2073825B1 (en) |
JP (1) | JP5328656B2 (en) |
KR (1) | KR101545356B1 (en) |
CN (1) | CN101495129B (en) |
CA (1) | CA2659442C (en) |
HU (1) | HUE035045T2 (en) |
MY (1) | MY164475A (en) |
WO (1) | WO2008090410A2 (en) |
Cited By (4)
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US7691387B2 (en) | 2000-09-13 | 2010-04-06 | Jiangsu Kanion Pharmaceutical Co., Ltd | Cinnamomi and poria composition, method to prepare same and uses thereof |
US8067040B2 (en) | 2006-10-18 | 2011-11-29 | Jiangsu Kanion Pharmaceuticals, Co. Ltd. | Cinnamomi and poria composition and uses thereof |
CN104374839A (en) * | 2014-10-31 | 2015-02-25 | 荣昌制药(淄博)有限公司 | Detection method for specific chromatogram of traditional-Chinese-medicine composition for treating irregular menstruation |
CN109632978A (en) * | 2018-11-01 | 2019-04-16 | 广州卡马生物科技有限公司 | A kind of Poria cocos reference extract and its preparation method and application |
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US8067040B2 (en) | 2006-10-18 | 2011-11-29 | Jiangsu Kanion Pharmaceuticals, Co. Ltd. | Cinnamomi and poria composition and uses thereof |
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2007
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Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
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US7691387B2 (en) | 2000-09-13 | 2010-04-06 | Jiangsu Kanion Pharmaceutical Co., Ltd | Cinnamomi and poria composition, method to prepare same and uses thereof |
US8119141B2 (en) | 2000-09-13 | 2012-02-21 | Jiangsu Kanion Pharmaceutical Co. Ltd. | Cinnamomi and poria composition, method to prepare same and uses thereof |
US8067040B2 (en) | 2006-10-18 | 2011-11-29 | Jiangsu Kanion Pharmaceuticals, Co. Ltd. | Cinnamomi and poria composition and uses thereof |
CN104374839A (en) * | 2014-10-31 | 2015-02-25 | 荣昌制药(淄博)有限公司 | Detection method for specific chromatogram of traditional-Chinese-medicine composition for treating irregular menstruation |
CN104374839B (en) * | 2014-10-31 | 2016-03-23 | 荣昌制药(淄博)有限公司 | A kind of detection method for the treatment of irregular menstruation Chinese medicine composition feature |
CN109632978A (en) * | 2018-11-01 | 2019-04-16 | 广州卡马生物科技有限公司 | A kind of Poria cocos reference extract and its preparation method and application |
CN109632978B (en) * | 2018-11-01 | 2021-12-21 | 广州科曼生物科技有限公司 | Poria cocos contrast extract as well as preparation method and application thereof |
Also Published As
Publication number | Publication date |
---|---|
US8067040B2 (en) | 2011-11-29 |
KR101545356B1 (en) | 2015-08-18 |
CN101495129A (en) | 2009-07-29 |
JP5328656B2 (en) | 2013-10-30 |
WO2008090410A4 (en) | 2009-01-22 |
KR20090067135A (en) | 2009-06-24 |
WO2008090410A3 (en) | 2008-11-13 |
EP2073825B1 (en) | 2017-04-05 |
HUE035045T2 (en) | 2018-05-02 |
MY164475A (en) | 2017-12-29 |
CA2659442C (en) | 2015-12-22 |
US20100183660A1 (en) | 2010-07-22 |
CN101495129B (en) | 2014-01-15 |
CA2659442A1 (en) | 2008-07-31 |
JP2010506899A (en) | 2010-03-04 |
EP2073825A4 (en) | 2013-04-17 |
EP2073825A2 (en) | 2009-07-01 |
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