CN1686091A - Composition of aiphenyl hepatanone compound and its use - Google Patents
Composition of aiphenyl hepatanone compound and its use Download PDFInfo
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- CN1686091A CN1686091A CNA2005100248900A CN200510024890A CN1686091A CN 1686091 A CN1686091 A CN 1686091A CN A2005100248900 A CNA2005100248900 A CN A2005100248900A CN 200510024890 A CN200510024890 A CN 200510024890A CN 1686091 A CN1686091 A CN 1686091A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/24—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups
- C07C49/245—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups containing six-membered aromatic rings
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- 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
- A61P31/04—Antibacterial agents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/213—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings
- C07C49/215—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings polycyclic
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Abstract
An application of the diarylheptanoids compound, such as diphenylheptanone, diphenylheptenone and diphenylheptandione, and its medicinal composition in treating the pylorospirobacillus infection and the diseases associated with intestinal or gastric ulcer is disclosed.
Description
Technical field
The invention belongs to the medicinal application technical field, be specifically related to the purposes of diphenyl heptanone class (diarylheptanoids) chemical compound (as: diphenyl heptanone, diphenyl heptenone and diphenyl heptadione) and pharmaceutical composition thereof, particularly in the purposes of pharmaceutical field.
Background technology
Chronic active gastritis, gastric ulcer and duodenal ulcer, gastric MALT lymphoma and gastric tumor are the diseases of serious harm human health and life, and medical research confirms that above disease all infects relevant with helicobacter pylori (Hp).Data shows that the whole world has the population more than 50% to infect helicobacter pylori approximately, and the infection in the developing country is particularly serious, reaches 60-80% among the adult.1994 international cancer research institution (IARC) classify Hp as human I class carcinogen.The infection of all adopting anti-endocrine medicine and antibiotic conjoint therapy to treat Hp both at home and abroad at present, but, produce drug resistance because side effect is big, and patient's toleration is poor, curative effect and application have been subjected to influence.Therefore, seek anti-Hp and infect the research topic that has become people to pay close attention to the new way of its relevant disease with treatment.
Yet, up to now, not relevant for the report of diphenyl heptanone class (diarylheptanoids) chemical compound (as: diphenyl heptanone, diphenyl heptenone and diphenyl heptadione) anti-Helicobacter pylori infection or treatment intestinal, the diseases related aspect of gastric ulcer.
The present invention is on the basis of a large amount of anti-HP screening active ingredients of chemical compound, find that first diphenyl heptanone class (diarylheptanoids) chemical compound (as: diphenyl heptanone, diphenyl heptenone and diphenyl heptadione) has good anti-helicobacter pylori (Hp) effect astoundingly, and the gastric mucosa injury that helicobacter pylori causes is had repair.
The present invention provides the new purposes of diphenyl heptanone class (diarylheptanoids) chemical compound (as: diphenyl heptanone, diphenyl heptenone and diphenyl heptadione) aspect anti-helicobacter pylori.
The invention still further relates to the application of diphenyl neptanone compound in preparation treatment active gastritis, gastric erosion medicine; Application in preparation treatment gastric ulcer (no matter having or not complication such as gastrorrhagia, gastric perforation) medicine; Application in preparation treatment duodenal ulcer medicine.
Summary of the invention
The purpose of this invention is to provide the purposes of a class diphenyl neptanone compound, be meant the purposes of anti-helicobacter pylori aspect especially at anti-pylori.
Another object of the present invention provides the purposes of the pharmaceutical composition of this compounds.
Comprise and have following general formula (I):
In the formula:
(a) R is independently of one another
Wherein X is H or methyl independently of one another;
(b) R
1Be H, methoxyl group or hydroxyl independently of one another;
(c) R
2Be H, methoxyl group or hydroxyl independently of one another;
(d) R
3Be H, methoxyl group or hydroxyl independently of one another;
(e) R
4Be H, methoxyl group or hydroxyl independently of one another;
(f) R
5Be H, methoxyl group or hydroxyl independently of one another;
(g) R
6Be H, methoxyl group or hydroxyl independently of one another;
The present invention further provides the pharmaceutical composition of a kind of anti-Helicobacter pylori infection or treatment intestinal, the diseases related aspect of gastric ulcer, described pharmaceutical composition comprises diphenyl heptanone class (diarylheptanoids) chemical compound and the pharmaceutically acceptable carrier with formula (I) structure for the treatment of effective dose.
Chemical compound diphenyl heptanone class of the present invention (diarylheptanoids) chemical compound, in vivo, in the outer test, all shown good anti-helicobacter pylori effect, and the gastric mucosa injury that helicobacter pylori causes is had repair had significant inhibition helicobacter pylori (Hp) activity; And, to the eradication rate of helicobacter pylori, obviously being better than popular at present " triple therapy ", the utmost point promises to be new anti-helicobacter pylori or treats intestinal, the diseases related aspect of gastric ulcer medicine.
Diphenyl heptanone class (diarylheptanoids) chemical compound wide material sources not only can adopt general chemical extraction, separation method from zingiberaceous plant, also can utilize the raw material of industry to make through existing methodology of organic synthesis.Concrete separation method and synthetic method are disclosed in the following document:
1.Chen，J.；Karchesy，J.J.；Gonzalez-Laredo，R.F.Phenolic?diarylheptenones?from?Alnus?rubrabark，Planta?Med.1998，64(1)，74-75.
2.Ali，M.S.；Tezuka，Y.；Banskota，A.H.；Kadota，S.Blepharocalyxins?C-E，three?new?dimericdiarylheptanoids，and?related?compounds?from?the?seeds?of?Alpinia?blepharocalyx，J.Nat.Prod.2001，64(4)，491-496.
3.Ali，M.S.；Tezuka，Y.；Banskota，A.H.；Kadota，S.Six?new?diarylheptanoids?from?the?seeds?ofAlpinia?blepharocalyx，J.Nat.Prod.2001，64(3)，289-293.
4.Solladié，G.；Ziani-Chérif，C.；Jesser，F.Asymmetric?synthesis?of(-)(R)yashabushiketol，Tetrahedron?Lett.1992，33，931-934.
5.Miyashita，M.；Hoshino，M.；Yoshikoshi，A.An?expedient?synthesis?of?natural?diarylheptanoidsusing?the?organicselenium-mediated?reduction?of?epoxy?ketone，Chem.Lett.1990，791-794.
6.Zhao，H.；Wu，Y.L.Chiral?synthesis?of?yashabushiketol，Chin.Chem.Lett.1994，5，367-370.。
The concrete chemical compound of the present invention is
Table 1:
The physical property of part of compounds of the present invention and data:
Chemical compound 1: molecular weight: 282, molecular formula is: C
19H
22O
2, its character is a white, needle-shaped crystals, mp.48.5-49.5 ℃, be soluble in ethanol,
Chemical compound 2: molecular weight: 342, molecular formula is: C
21H
26O
4, its character is a colorless oil, is soluble in ethanol,
Chemical compound 3: molecular weight: 342, molecular formula is: C
20H
24O
4, its character is colourless acicular crystal mp.60.0-61.5 ℃, is soluble in ethanol,
Chemical compound 4: molecular weight: 312, molecular formula is: C
20H
24O
3, its character is a colorless oil, is soluble in ethanol,
Chemical compound 5: molecular weight: 312, molecular formula is: C
20H
24O
2, its character is a colorless oil, is soluble in ethanol,
Chemical compound 6: molecular weight: 298, molecular formula is: C
19H
22O
3, its character is a colorless oil, is soluble in ethanol,
Chemical compound 7: molecular weight: 244, molecular formula is: C
19H
20O, its character is a colorless oil, is soluble in ethanol,
Chemical compound 8: molecular weight: 310, molecular formula is: C
20H
22O
3, its character is a colorless oil, is soluble in ethanol,
Chemical compound 9: molecular weight: 870, molecular formula is: C
19H
20O
2, its character is a colorless oil, is soluble in ethanol,
Chemical compound 10: molecular weight: 296, molecular formula is: C
19H
20O
3, its character is a colorless oil, is soluble in ethanol,
Chemical compound 11: molecular weight: 356, molecular formula is: C
21H
24O
5, its character is a colorless oil, is soluble in ethanol,
Chemical compound 12: molecular weight: 326, molecular formula is: C
20H
22O
4, its character is a light yellow oil, is soluble in ethanol,
Chemical compound 13: molecular weight: 398, molecular formula is: C
22H
26O
6, its character is a light yellow oil, is soluble in ethanol,
Chemical compound 14: molecular weight: 398, molecular formula is: C
22H
26O
6, its character is a light yellow oil, is soluble in ethanol,
Chemical compound 15: molecular weight: 326, molecular formula is: C
20H
22O
4, its character is a light yellow oil, is soluble in ethanol,
Chemical compound 16: molecular weight: 280, molecular formula is: C
19H
20O
2, its character is a colorless oil, is soluble in ethanol,
Chemical compound 17: molecular weight: 326, molecular formula is: C
20H
22O
4, its character is a colorless oil, is soluble in ethanol.
Pharmacological testing:
1. the effect of external anti-helicobacter pylori:
With the diphenyl neptanone compound of doses, join in the quantitative separately nutrient agar, mix homogeneously pours into into aseptic flat board, inoculation 10
7CFU/mL is in the helicobacter pylori of logarithmic growth, and little aerobic cultivation is after 5 days, and blind scraping is transferred in the no medicine culture medium.37 ℃ of little aerobic cultivations 4-5 days, observation had or not the helicobacter pylori growth, to record minimum bactericidal concentration (MBC) separately.
The effect of the external antagonism helicobacter pylori (Hp) of table 2. diphenyl heptanone of the present invention class (diarylheptanoids) chemical compound
| Sample | Minimum bactericidal concentration (MBCs) (μ g/mL) to different Hp bacterial strains | ||
| ??Hp-Sydneystrain1(Hp，SS1) | ??Hp-F44 | Hp-Hu Dong | |
| Positive control (metronidazole) chemical compound 1-6 chemical compound 7-15 chemical compound 16-17 | ??1.0 ??12.5 ??12.5 ??25.0 | ??1.0 ??25.0 ??12.5 ??25.0 | ??1.0 ??12.5 ??25.0 ??25.0 |
Wherein (Hp SS1) is reference culture to Hp-Sydney strain 1; Hp-F44 and Hp-Hu Dong are clinical strains.
2.5-pharmacology test in the hydroxyl-1, the mice body of 7-diphenyl-3-heptanone (chemical compound 1):
Secondary C
5750 of BL/6 mices, body weight 20-25g irritates stomach with the dense helicobacter pylori of certain bacterium (Hp SS1), realizes intravital Hp field planting.The mice of Hp field planting is divided into blank group, positive drug matched group and 5-hydroxyl-1,7-diphenyl-3-heptanone (100mg/kg) group.Totally six groups, 10 every group.The triple therapy that positive controls adopts current doctor trained in Western medicine to use: with omeprazole 5.2mg/kg, clarithromycin 65mg/kg and metronidazole 104mg/kg unite use; The blank group is a control solvent.Every group of oral administration, and implemented successive administration 14 days.Stop administration after 30 days, in sterilizing room, dissect mice, do following the inspection:
(1) rapid urease test and bacterial cultivation: the eradication rate of checking helicobacter pylori (Hp).
(2) histological examination: check the recovery situation of the mice gastric mucosa damage (comprising erosion, glandular hyperplasia and formation adenoma etc.) that Helicobacter pylori infection causes, promptly effective treatment rate.
Table 35-hydroxyl-1, pharmacology result in the body of 7-diphenyl-3-heptanone
| Group | Hp eradication rate (%) | Effective treatment rate (%) |
| Positive controls blank group 5-hydroxyl-1,7-diphenyl-3-heptanone | 60 0 100 | 30 parts are recovered, 70 still have moderate and severe glandular hyperplasia 100 stomach pylorus mucosal epithelium glandular hyperplasias, form adenoma, karyokinesis is seen more.80 basic recoveries normally, 20 still have slight glandular hyperplasia. |
3.1, pharmacology test in the mice body of 7-diphenyl-4-teracrylic acid-ketone (chemical compound 7):
Secondary C
5750 of BL/6 mices, body weight 20-25g irritates stomach with the dense helicobacter pylori of certain bacterium (Hp-F44), realizes intravital Hp field planting.The mice of Hp field planting is divided into blank group, positive drug matched group and 1,7-diphenyl-4-teracrylic acid-ketone group (100mg/kg) group.Totally six groups, 10 every group.The triple therapy that positive controls adopts current doctor trained in Western medicine to use: with omeprazole 5.2mg/kg, clarithromycin 65mg/kg and metronidazole 104mg/kg unite use; The blank group is a control solvent.Every group of oral administration, and implemented successive administration 14 days.Stop administration after 30 days, in sterilizing room, dissect mice, do following the inspection:
(1) rapid urease test and bacterial cultivation: the eradication rate of checking helicobacter pylori (Hp).
(2) histological examination: check the recovery situation of the mice gastric mucosa damage (comprising erosion, glandular hyperplasia and formation adenoma etc.) that Helicobacter pylori infection causes, promptly effective treatment rate.
Pharmacology result in the table 41, the body of 7-diphenyl-4-teracrylic acid-ketone
| Group | Hp eradication rate (%) | Effective treatment rate (%) |
| Positive controls blank group 5-hydroxyl-1,7-diphenyl-3-heptanone | 60 0 100 | 30 parts are recovered, 70 still have moderate and severe glandular hyperplasia 100 stomach pylorus mucosal epithelium glandular hyperplasias, form adenoma, karyokinesis is seen more.90 basic recoveries normally, 10 still have the moderate glandular hyperplasia. |
Pharmacology test in the mice body of pharmaceutical composition (oral liquid):
Secondary C
5750 of BL/6 mices, body weight 20-25g irritates stomach with the dense helicobacter pylori of certain bacterium (Hp SS1), realizes intravital Hp field planting.The mice of Hp field planting is divided into blank group, positive drug matched group and 0.6% oral liquid (15mL/kg) group.Totally six groups, 10 every group.The triple therapy that positive controls adopts current doctor trained in Western medicine to use: with omeprazole 5.2mg/kg, clarithromycin 65mg/kg and metronidazole 104mg/kg unite use; The blank group is a control solvent.Every group of oral administration, and implemented successive administration 14 days.Stop administration after 30 days, in sterilizing room, dissect mice, do following the inspection:
(1) rapid urease test and bacterial cultivation: the eradication rate of checking helicobacter pylori (Hp).
(2) histological examination: check the recovery situation of the mice gastric mucosa damage (comprising erosion, glandular hyperplasia and formation adenoma etc.) that Helicobacter pylori infection causes, promptly effective treatment rate.
Pharmacology result in the body of table 5 oral liquid
| Group | Hp eradication rate (%) | Effective treatment rate (%) |
| Positive controls blank group 5-hydroxyl-1,7-diphenyl-3-heptanone | 60 0 100 | 30 parts are recovered, 70 still have moderate and severe glandular hyperplasia 100 stomach pylorus mucosal epithelium glandular hyperplasias, form adenoma, karyokinesis is seen more.80 recover normal, and 20 still have slight glandular hyperplasia. |
2. pharmaceutical composition:
Compositions of the present invention comprises The compounds of this invention and the acceptable carrier pharmaceutically in the safety, effective dosage ranges.
" safety, effective dose " refers to: the amount of chemical compound is enough to obviously improve the state of an illness, and is unlikely to produce serious adverse.The safety of chemical compound, effective dose are determined according to concrete conditions such as age of treatment target, the state of an illness, the courses of treatment.Compositions of the present invention should comprise the chemical compound of 0.1wt% (percentage by weight) to 99.9wt%, and the best is 0.5% to 10% and acceptable carrier (carrier the best is 90% to 99.5%) pharmaceutically.
" pharmaceutically acceptable carrier " refers to: one or more compatibility solids or liquid filler or gelatinous mass, they are suitable for the people uses, and enough purity and enough low toxicity must be arranged." compatibility " referred to herein as each component energy and chemical compound of the present invention and blending mutually between them in the compositions, and the drug effect of not obvious reduction chemical compound.Pharmaceutically acceptable carrier part example has sugar (as glucose, sucrose, lactose etc.), starch is (as corn starch, potato starch etc.), cellulose and derivant thereof are (as sodium carboxymethyl cellulose, ethyl cellulose sodium, cellulose ethanoate etc.), gelatin, Talcum, kollag is (as stearic acid, magnesium stearate), calcium sulfate, vegetable oil is (as Oleum Glycines, Oleum sesami, Oleum Arachidis hypogaeae semen, the Fructus Canarii albi wet goods), polyhydric alcohol is (as propylene glycol, glycerol, mannitol, sorbitol etc.), emulsifying agent (as tween ), wetting agent (as sodium lauryl sulphate), coloring agent, flavoring agent, stabilizing agent, antioxidant, antiseptic, apirogen water etc.Compositions of the present invention depends on the selection of carrier and the administering mode of chemical compound can be made into general medicinal tablet, granule, capsule, oral liquid formulations and general medical injection preparation.
The specific embodiment
The method of the pharmaceutical composition of diphenyl neptanone compound of the present invention adopts general medicinal tablets, granule, capsule, oral liquid formulations compound method to make.The proportioning content of the compositions of following embodiment all by weight percentage.
Medicinal tablets (3.9%): select the diphenyl neptanone compound and the additives mix homogeneously of following amount for use, as binding agent, wet granulation is dried with 10% pregelatinized Starch slurry, adds an amount of magnesium stearate and mixes, and is pressed into tablet.5-hydroxyl-1,7-diphenyl-3-heptanone (chemical compound 1) 7.5g; Hyprolose 120g; Micropowder silica gel 30g; Pregelatinized Starch 20g; Magnesium stearate is an amount of; Make 1000.
Medicinal tablets (9.7%): 5-hydroxyl-1,7-diphenyl-3-heptanone (chemical compound 1) 18g; Hyprolose 120g; Micropowder silica gel 30g; Pregelatinized Starch 20g; Magnesium stearate is an amount of; Mix homogeneously, as binding agent, wet granulation is dried with 10% pregelatinized Starch slurry, adds an amount of magnesium stearate and mixes, and is pressed into 1000.
Granule (3.3%): 5-hydroxyl-1,7-diphenyl-3-heptanone (chemical compound 1) 15g; Sucrose 250g; Hyprolose 120g; Micropowder silica gel 30g; Citric acid, sodium bicarbonate are an amount of; With above-mentioned constituent mix homogeneously, make wetting agent with an amount of 70% ethanol, wet granulation sieves, oven dry, 200 bags of granules are made in packing.
Capsule (8%): 5-hydroxyl-1,7-diphenyl-3-heptanone (chemical compound 1) 15g; Hyprolose 120g; Micropowder silica gel 30g; Citric acid, sodium bicarbonate are an amount of; With above-mentioned constituent mix homogeneously, make wetting agent with an amount of 70% ethanol, wet granulation sieves, and oven dry adds an amount of magnesium stearate, mix homogeneously, 1000 hard capsules are made in packing.
Capsule (96%): at 85g 5-hydroxyl-1, add citric acid, sodium bicarbonate, an amount of mix homogeneously of magnesium stearate in the 7-diphenyl-3-heptanone (chemical compound 1), be milled into 300-400 order granule, 500 hard capsules are made in packing.
Oral liquid (0.1%): it is an amount of to get distilled water, adds the 8g Tween-80 and makes solution, adds 5-hydroxyl-1 again, 7-diphenyl-3-heptanone (chemical compound 1) 1g heats while stirring and makes dissolving, in addition, sucrose 8g, antiseptic is dissolved in distilled water in right amount, under agitation slowly add in the above-mentioned solution, adding distil water is to 1000mL, and mixing cools off, filter, be packed as 100, sterilization makes 0.1% oral liquid.
Oral liquid (0.6%): it is an amount of to get distilled water, adds the 50g Tween-80 and makes solution, adds 5-hydroxyl-1 again, 7-diphenyl-3-heptanone (chemical compound 1) 6g heats while stirring and makes dissolving, in addition, sucrose 50g, antiseptic is dissolved in distilled water in right amount, under agitation slowly add in the above-mentioned solution, adding distil water is to 1000mL, and mixing cools off, filter, be packed as 100, sterilization makes 0.6% oral liquid.
Oral liquid (10%): it is an amount of to get distilled water, adds the 600g Tween-80 and makes solution, adds 5-hydroxyl-1 again, 7-diphenyl-3-heptanone (chemical compound 1) 100g heats while stirring and makes dissolving, in addition, sucrose 100g, antiseptic is dissolved in distilled water in right amount, under agitation slowly add in the above-mentioned solution, adding distil water is to 1000mL, and mixing cools off, filter, be packed as 100, sterilization makes 10% oral liquid.
Concentrated solution (40% oral liquid): get the 280g Tween-80, add 1,7-diphenyl-4-teracrylic acid-ketone (chemical compound 7) 200g, stirring makes mix homogeneously, in addition, antiseptic is dissolved in distilled water in right amount, under agitation slowly add in the said mixture, adding distil water is to 500mL, and mixing cools off, filter, be packed as 50, sterilization makes concentrated solution.
Above embodiment illustrates The compounds of this invention, preparation of compositions method and The pharmacological results, but can make various modifications and variation to this to one skilled in the art, and not deviating from the spirit and scope of the present invention, appending claims covers all such modifications in the scope of the invention.
Claims (6)
1, the following compositions of forming by active ingredient hexichol neptanone compound 0.1% (percentage by weight) to 99.9% (percentage by weight) and pharmaceutically acceptable carrier of a kind of structural formula
In the formula:
(a) R is independently of one another
Or
Wherein X is H or methyl independently of one another;
(b) R
1Be H, methoxyl group or hydroxyl independently of one another;
(c) R
2Be H, methoxyl group or hydroxyl independently of one another;
(d) R
3Be H, methoxyl group or hydroxyl independently of one another;
(e) R
4Be H, methoxyl group or hydroxyl independently of one another;
(f) R
5Be H, methoxyl group or hydroxyl independently of one another;
(g) R
6Be H, methoxyl group or hydroxyl independently of one another.
2, diphenyl neptanone compound compositions according to claim 1 is characterized in that its pharmaceutically acceptable carrier is by weight percentage 90% to 99.5%.
3, diphenyl neptanone compound compositions according to claim 1, it is characterized in that active ingredient diphenyl neptanone compound the best be 0.5% to 10% with pharmaceutically acceptable carrier be 90% to 99.5%.
4, the purposes of diphenyl neptanone compound compositions as claimed in claim 1 is for using in the anti-pylori medicine of preparation.
5, diphenyl neptanone compound compositions purposes as claimed in claim 3 is characterized in that using in the preparation medicine for anti Helicobacter pylori.
6, diphenyl neptanone compound compositions purposes according to claim 3 is characterized in that using in preparation prevention, treatment intestinal, gastric ulcer medicine.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100248900A CN100531725C (en) | 2005-04-05 | 2005-04-05 | Composition of aiphenyl hepatanone compound and its use |
| PCT/CN2006/000596 WO2006105728A1 (en) | 2005-04-05 | 2006-04-04 | Diarylheptanoids, preparation and the use thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100248900A CN100531725C (en) | 2005-04-05 | 2005-04-05 | Composition of aiphenyl hepatanone compound and its use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1686091A true CN1686091A (en) | 2005-10-26 |
| CN100531725C CN100531725C (en) | 2009-08-26 |
Family
ID=35304132
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2005100248900A Expired - Fee Related CN100531725C (en) | 2005-04-05 | 2005-04-05 | Composition of aiphenyl hepatanone compound and its use |
Country Status (2)
| Country | Link |
|---|---|
| CN (1) | CN100531725C (en) |
| WO (1) | WO2006105728A1 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007071721A3 (en) * | 2005-12-22 | 2007-09-07 | Boehringer Ingelheim Int | Ginger extract for inhibiting human drug transporters |
| WO2007071708A3 (en) * | 2005-12-22 | 2007-09-07 | Boehringer Ingelheim Int | Ginger fraction for inhibiting human cyp enzymes |
| CN100389762C (en) * | 2006-06-21 | 2008-05-28 | 天津大学 | Use of 5-hydroxy-1-(4- hydroxyphenyl)-7-phynyl-3-heptanone |
-
2005
- 2005-04-05 CN CNB2005100248900A patent/CN100531725C/en not_active Expired - Fee Related
-
2006
- 2006-04-04 WO PCT/CN2006/000596 patent/WO2006105728A1/en not_active Application Discontinuation
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007071721A3 (en) * | 2005-12-22 | 2007-09-07 | Boehringer Ingelheim Int | Ginger extract for inhibiting human drug transporters |
| WO2007071708A3 (en) * | 2005-12-22 | 2007-09-07 | Boehringer Ingelheim Int | Ginger fraction for inhibiting human cyp enzymes |
| JP2009520003A (en) * | 2005-12-22 | 2009-05-21 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ginger fraction for inhibiting human CYP enzyme |
| CN100389762C (en) * | 2006-06-21 | 2008-05-28 | 天津大学 | Use of 5-hydroxy-1-(4- hydroxyphenyl)-7-phynyl-3-heptanone |
Also Published As
| Publication number | Publication date |
|---|---|
| CN100531725C (en) | 2009-08-26 |
| WO2006105728A1 (en) | 2006-10-12 |
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