CN104829675A - Chemical compound, crystal form, and preparation methods and applications of chemical compound and crystal form - Google Patents
Chemical compound, crystal form, and preparation methods and applications of chemical compound and crystal form Download PDFInfo
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- CN104829675A CN104829675A CN201510232749.3A CN201510232749A CN104829675A CN 104829675 A CN104829675 A CN 104829675A CN 201510232749 A CN201510232749 A CN 201510232749A CN 104829675 A CN104829675 A CN 104829675A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
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Abstract
The invention disclose a chemical compound as shown in Formula I in the specification, wherein R1, R2 and R3 are selected from methyl, ethyl, propyl, butyl, amyl or hexyl. The invention further discloses a crystal form of the chemical compound, preparation methods and applications of the chemical compound and the crystal form. The chemical compound or the crystal form of the chemical compound has an inhibition effect on cell multiplication of a leukemia cell line MV4-11, and a new choice for screening a drug for treatment or prevention of leukemia in clinic is provided.
Description
Technical field
The present invention relates to a kind of compound and crystal formation and preparation method thereof and purposes.
Background technology
Motherwort Herb begins to be loaded in Shennong's Herbal, original name motherwort, is listed in top grade.Be referred to as in Compendium of Material Medica " panacea of blood man ", curing mainly " threatened abortion is had difficult labour, retention of placenta, bruise, blood wind, blood pain, metrorrhagia and metrostaxis, hematuria ", is gynaecology's multiparity key medicine.
Main containing compositions such as alkaloid, terpenoid, flavones, iridoid glycoside, benzyl carbinol glycosides, volatile oil, peptide class and fatty acids in Motherwort Herb, the mainly alkaloid that its activity research is more and diterpenes:
(1) alkaloid: mainly comprise stachydrine, syringic acid.delta.-guanidinobutyl ester, Motherwort Herb pyridine and leonurinine etc.;
(2) diterpene: increase its study of active components in recent years, wherein Leoheteronin A and the obvious acetylcholine esterase inhibition activity of Leopersin G, have good prospect in treatment alzheimer's disease; Prehispanolone is a kind of thrombocyte antagonizes factor, can anticoagulant; The cerebral cortex cells of leojaponin to injured with glucose deprivation has provide protection; The labdane type diterpenoids that Khan obtains has anti-inflammatory action etc.
In prior art, from Motherwort Herb, extract the compound obtained be mainly terpenoid, alkaloid etc., as: Chinese patent CN 103211809 A discloses extraction from Motherwort Herb and obtains formula A compound, has anticoagulant effect; Chinese patent CN 103553919 A discloses extraction from Motherwort Herb and obtains formula B compound, has certain enhancement to coagulation function; Chinese patent CN104086559 A discloses extraction from Motherwort Herb and obtains formula C compound, has the effect of platelet aggregation-against.
At present, there are no the relevant report of the compounds of this invention and crystal formation thereof, more there are no the relevant report of its preparation method and purposes.
Summary of the invention
The object of the present invention is to provide a kind of compound and crystal formation, this compound and crystal formation inhibited to Leukemia Cell Lines MV4-11 cell proliferation.
Compound shown in formula I provided by the invention:
Wherein, R
1, R
2, R
3be selected from methyl, ethyl, propyl group, butyl, amyl group or hexyl respectively.
Further, described compound is such as formula shown in II:
Present invention also offers the preparation method of compound shown in formula II, it comprises the following steps:
A, get Motherwort Herb medicinal material, after adding extraction using alcohol, except desolventizing, obtain ethanol extract;
B, by ethanol extract water-dispersion, use ethyl acetate, n-butanol extraction successively, combined ethyl acetate part, except desolventizing, obtain ethyl acetate extract;
C, get ethyl acetate extract, adopt silica gel column chromatography, successively with sherwood oil: acetone=100:1,50:1,25:1,10:1,5:1 is that eluent carries out gradient elution, get sherwood oil: elutriant during acetone=5:1, follow the trail of according to thin layer, merge the elutriant containing similar compositions, recycling design, obtains component G;
D, get component G, adopt anti-phase polystyrene type resin column chromatography, successively with methyl alcohol: water=50:50,75:25,85:15,95:5 is that eluent carries out gradient elution, collect methyl alcohol: elutriant during water=85:15 and/or 95:5, follow the trail of according to thin layer, merge the elutriant containing similar compositions, recycling design, obtains component G7;
E, get component G7, adopt alkaline silica gel column chromatography, successively with sherwood oil: acetone=15:1,10:1,8:1 is that eluent carries out gradient elution, collect sherwood oil: elutriant during acetone=8:1, follow the trail of according to thin layer, merge the elutriant containing similar compositions, recycling design, obtains component G7-4;
F, get component G7-4, peroxidation aluminium column chromatography, with sherwood oil: ethyl acetate=20:1 is that eluent carries out wash-out, follow the trail of according to thin layer, collect the elutriant containing target compound;
G, get elutriant containing target compound, recycling design, through Preparative TLC, obtains target components, then adopts reverse phase liquid preparative chromatography, and with 93%v/v methanol aqueous solution wash-out, collect target compound, recycling design, to obtain final product.
Further,
In step a, the weightmeasurement ratio of Motherwort Herb medicinal material and ethanol is 1:8 ~ 24kg/L, and described ethanol is 95%v/v ethanol;
In step b, the weightmeasurement ratio of ethanol extract and water is 1.2:8kg/L, and the volume ratio of water, ethyl acetate, propyl carbinol is 1:1 ~ 6:1 ~ 6;
In step c, the condition of gradient elution is as follows:
In steps d, the condition of gradient elution is as follows:
In step e, the condition of gradient elution is as follows:
In step f, the weightmeasurement ratio of component G7-4 and eluent is 1:600g/mL.
Further,
In steps d, polystyrene type resin is MCI gel CHP 20P;
In step g, the developping agent of Preparative TLC is sherwood oil: acetone=5:1.
The crystal formation of compound shown in formula II provided by the invention, this crystal formation is oblique system, and spacer is P2
1, unit cell parameters is
, α=90.00 °,
, β=97.2458 (13) °,
, γ=90.00 °, Z=4, unit cell volume is
.
Present invention also offers the preparation method of above-mentioned crystal formation, it comprises the following steps:
1., according to above-mentioned method, compound shown in formula II is obtained;
2., compound shown in modus ponens II, add methyl alcohol, be placed on and be equipped with in the moisture eliminator of siccative, be placed to crystallize out, obtain the crystal formation of compound shown in formula II.
Further, step 2. in, the weightmeasurement ratio of compound and methyl alcohol shown in formula II is 1:0.01 ~ 0.1mg/ml.
Further, described siccative is selected from discolour silica gel.
Above-claimed cpd or the purposes of its crystal formation in preparation treatment or prevention leukemia medicament.
A kind of pharmaceutical composition provided by the invention, it be with above-claimed cpd or its crystal formation, pharmacy acceptable salt, hydrate or solvate for activeconstituents, add the preparation that pharmaceutically conventional auxiliary material or complementary composition prepare.
Further, described preparation is through gastrointestinal absorption preparation or injection formulations.
Compound provided by the invention or its crystal formation, inhibited to Leukemia Cell Lines MV4-11 cell proliferation, for screening treatment clinically or preventing leukemia medicament to provide a kind of selection newly.
The present invention can adopt preparation technique means or the pharmaceutical methods of this area routine, crystal formation of the present invention is prepared into suitable medicine type, comprise: tablet, injection, tincture, suppository, capsule, paste (ointment, ointment), ophthalmic preparation, pill, implant, syrup, mist agent (aerosol, powder inhalation, sprays), film, granule, oral solution (oral suspensions, Orally taken emulsion), powder, aural preparations, nasal formulations, lotion (irrigation, enema), liniment (paint, liniment), gelifying agent, patch etc., be preferably tablet, capsule, ophthalmic preparation.Wherein, described tablet is selected from lozenge, Sublingual tablet, mouth paster, chewable tablet, dispersible tablet, fuse, effervescent tablet, slow releasing tablet, controlled release tablet, enteric coated tablet etc.; Described injection is selected from injection, transfusion, freeze-dried powder, emulsion, implant, microball preparation, pellet preparations etc.; Described capsule is selected from hard capsule, soft capsule, slow releasing capsule, controlled release capsule and enteric coated capsule etc.; Described ophthalmic preparation is selected from eye drops, eye wash, intraocular injection solution, Eye ointments, eye ointment, gel for eye, eye mask agent, eye pill, intraocular intercalating agent etc.; Described pill is selected from dripping pill, sugar-pill etc.; Described granule is selected from mix suspension grain, effervescent granule, enteric coated particles, slow-releasing granules, controlled release granule etc.; Described aural preparations is selected from ear drop, ear lotion, ear sprays, ear ointment, ear ointment, ear gelifying agent, earplug, ear powder, ear pill etc.; Described nasal formulations is selected from nasal drop, nasal douche, nasal spray, nose ointment, gel for nose, nose powder, powder nose inhalant, nose stylus etc.
Obviously, according to foregoing of the present invention, according to ordinary technical knowledge and the customary means of this area, not departing under the present invention's above-mentioned basic fundamental thought prerequisite, the amendment of other various ways, replacement or change can also be made.
The embodiment of form by the following examples, is described in further detail foregoing of the present invention again.But this should be interpreted as that the scope of the above-mentioned theme of the present invention is only limitted to following example.All technology realized based on foregoing of the present invention all belong to scope of the present invention.
Accompanying drawing explanation
Fig. 1 is the single crystal diffraction structure iron of formula II compound crystal form.
Embodiment
The raw material used in the specific embodiment of the invention, equipment are known product, obtain by buying commercially available prod.
Embodiment 1
(1) experiment material:
1. medicinal material
Motherwort Herb picks up from Wenjiang District, Chengdu, Sichuan, is accredited as the herb of labiate Motherwort Herb Leonurus japonicus Houtt. through identification and assessment of Chinese medicines teaching and research room of Chengdu University of Traditional Chinese Medicine professor Li Min.
2. reagent and filler
Column chromatography silica gel, 200 ~ 300 orders (SILVER REAGENT), are purchased from Qingdao Haiyang silica-gel drier factory;
Alkaline silica gel, 300-400 order (SILVER REAGENT), is purchased from Shanghai Sheng Ya Chemical Co., Ltd.;
Tlc silica gel G, GF
254with H (chemical pure), be purchased from Qingdao Haiyang silica-gel drier factory;
Chromatography (neutrality) aluminum oxide, 100 order ~ 200 orders (chemical pure), are purchased from land, Shanghai all chemical reagent factories.
MCI gel CHP 20P, is anti-phase polystyrene type resin, is purchased from Mitsubishi chemical company by 75 ~ 150 μm;
Sephadex LH-20 dextrane gel, is purchased from Amersham company of Sweden;
GF
254silica gel Preparative TLC, is purchased from Yantai Jiang You silica gel development corporation, Ltd.;
Chromatogram methyl alcohol, 4L/ bottle, is purchased from Fisher company of the U.S.;
The analytical reagent such as sherwood oil, ethyl acetate, propyl carbinol, acetone, methyl alcohol, are purchased from Chengdu Ke Long chemical reagent factory.
3. laboratory apparatus
Cometro 6000 high performance liquid chromatograph (U.S. Cometro);
Waters Synapt G
2hDMS high resolution flight time mass spectrum (U.S. Waters);
Bruker-AVIII-600 nuclear magnetic resonance analyser (Switzerland Bruker);
Perkin-Elmer Spectrum One FT-IR infrared spectrometer (U.S. PerkinElmer);
Xcalibur, Atlas, Gemini ultra diffractometer single crystal diffractometer (U.S. Agilent)
BP211D 100,000/electronic balance (Switzerland Sartorius);
R-210 rotatory evaporator (Switzerland BUCHI);
DZG-6050 type vacuum drying oven (the gloomy letter in Shanghai).
(2) extraction of medicinal material: take Motherwort Herb medicinal material 20Kg, pulverizes, adds 95% ethanol (3 × 160L) and extract 72 hours, extract 3 times, and extracting solution after decompression and solvent recovery, obtains ethanol extract 1.2Kg after merging;
(3) separation and purification of composition:
1., take Motherwort Herb medicinal material 20kg, pulverize, add 95%v/v ethanol 160L and extract 3 times, after extracting solution decompression and solvent recovery, obtain ethanol extract 1.2kg;
2., by ethanol extract (1.2kg) water (8.0L) dispersion, ethyl acetate (6 × 8.0L), propyl carbinol (6 × 8.0L) is used to extract successively, combined ethyl acetate part, decompression and solvent recovery, obtains ethyl acetate extract 400g;
3. ethyl acetate extract (400g), is got, adopt silica gel column chromatography, according to table 1 successively with sherwood oil: acetone=100:1,50:1,25:1,10:1,5:1,3:1,2:1,1:1,0:1 is that eluent carries out gradient elution, get elutriant when eluent is sherwood oil-acetone (5:1), follow the trail of according to thin layer, merge the elutriant containing similar compositions, recycling design, obtains component G;
The gradient elution program of table 1, ethyl acetate extract
Get component G (12.5g), adopt anti-phase polystyrene type resin (MCI gel CHP 20P) column chromatography, according to table 2 successively with methyl alcohol: water=50:50,75:25,85:15,95:5,100:0 is that eluent carries out gradient elution, get eluent be methanol-water (85:15) and methanol-water (95:5) time elutriant, follow the trail of in conjunction with thin layer, merge the elutriant containing similar compositions, recycling design, obtains component G7;
The gradient elution program of table 2, component G
Get component G7 (1.2g), adopt the method for alkaline silica gel column chromatography, according to table 3 successively with sherwood oil: acetone=15:1,10:1,8:1,5:1 is that eluent carries out gradient elution, get elutriant when eluent is sherwood oil-acetone (8:1), follow the trail of in conjunction with thin layer, merge the elutriant containing similar compositions, recycling design, obtains component G7-4;
The gradient elution program of table 3, component G7
Get component G7-4 (0.5g), by aluminum oxide column chromatography, with petroleum ether-ethyl acetate (20:1) wash-out (300mL), adopt thin layer to follow the trail of, collect the elutriant containing target compound;
Get the elutriant containing target compound, recycling design, then obtain target components through the method for Preparative TLC (developping agent is sherwood oil: acetone=5:1), then adopt reverse phase liquid preparative chromatography, with 93%v/v methanol aqueous solution wash-out, collection retention time is t
rthe target product of=75min, recycling design, obtains compound solid shown in formula II, and its name is called (24S)-4,28-beans steroid diene-24-alcohol-3-ketone;
4. compound solid 10mg shown in modus ponens II, is placed in the glass sample bottle of 2ml, adds 0.4ml methyl alcohol, subsequently sample bottle is put into the moisture eliminator that discolour silica gel is housed, and places until separate out colorless needles, obtains the crystal formation of compound shown in formula II.
(4) Structural Identification of composition: clear crystal; Without blackening, iodine displaing yellow, sprays 10% ethanol solution of sulfuric acid displaing amaranth at 105 DEG C; By HRESIMS m/z 427.3593 [M+H]
+with 449.3406 [M+Na]
+, can determine that molecular formula is C
29h
46o
2.
(5) proton nmr spectra (
1h-NMR): Bruker-AVIII 600spectrometer measures, and data are in table 4.
Table 4,
1h-NMR (600MHz) and
13c NMR (150MHz) nuclear magnetic data (solvent: CDCl
3; δ: ppm; J:Hz)
(6) carbon-13 nmr spectra (
13c-NMR): Bruker-AVIII600spectrometer measures, and data are in table 4.
(7) single crystal diffraction data are in table 5.
Table 5, single crystal diffraction data of the present invention
Compound
1h NMR and
13c NMR can find out that compound is sterols parent nucleus, has 29 carbon atoms, 5 methyl, wherein 2 unimodal methyl (δ
h1.17,0.70), 3 bimodal methyl (δ
h0.92,0.89,0.87).Simultaneously containing a pair terminal double link, hydrogen spectrum signal δ
h5.81 (J=17.4,10.8Hz), 5.19 (J=17.4,1.2Hz), 5.14 (J=10.8,1.2Hz), carbon spectrum signal δ
c142.7,113.2.In conjunction with δ in carbon spectrum and hydrogen spectrum
c199.9, the quaternary carbon signal of 171.9,124.0 and low field proton signal δ
h5.72 (1H, s, H-4), can infer containing α, beta unsaturated ketone structure fragment.In addition, according to δ
cthe quaternary carbon signal of 77.9 can be found out containing tertiary alcohol structure.Shown by 2D-NMR experiment, saringosterone (the Z.Naturforsch.C.2003 reported in this compound and document, 58 (5-6): 333 – 336) there is identical two dimensional structure, but for saringosterone, in compound, C-24 reaches 9.8ppm to high field displacement.Therefore, infer that its C-24 configuration is contrary, namely 24 is S configuration.
Absolute configuration is determined in further employing X-ray single crystal diffraction experiment, as shown in Figure 1; The structure of this compound is defined as (24S)-4,28-beans steroid diene-24-alcohol-3-ketone.
In order to beneficial effect of the present invention is described, the invention provides following test example:
Test example 1
(1) experiment material:
1. medicine
Test-compound: (24S)-4,28-beans steroid diene-24-alcohol-3-ketone, is configured to the stock solution of 1mg/mL ,-10 DEG C of preservations, becomes 25 μ g/mL before use with normal saline dilution, 50 μ g/mL and 100 μ g/mL with DMSO.
2. reagent
Tetrazolium bromide (MTT).
Dimethyl sulfoxide (DMSO) (DMSO), cell grade, 100ml/ bottle, is purchased from Sigma-Aldrich company.
4. cell
Human leukaemia cell system MV4-11 is purchased from Chinese Academy of Medical Sciences's Blood Research Institute.
5. laboratory apparatus
Electronic balance (ESJ120-4 type, Longteng Electronic Weighing Instrument Co., Ltd., Shenyang); Water-bath, cryogenic refrigerator etc.
(2) experimental technique:
Cell cultures: MV4-11 cell containing 200ml/L foetal calf serum IMDM nutrient solution in, 37 DEG C, volume fraction 5%CO
2, cultivate under saturated humidity condition, choose logarithmic phase cell and test.
Body outer cell proliferation Inhibition test: MV4-11 cell about 2 × 10 in vegetative period of taking the logarithm respectively
4/ mL, is added in 96 orifice plates.Set up 3 concentration groups, be respectively 25 μ g/mL, 50 μ g/mL and 100 μ g/mL, control group adds the solvent of same concentration, cultivates respectively, calculates IC
50value.
3. experimental result and evaluation:
Found by research: the compounds of this invention (24S)-4,28-beans steroid diene-24-alcohol-3-ketone is inhibited to Leukemia Cell Lines MV4-11 cell proliferation, its IC
50value is 47.9 μ g/mL.
In sum, compound provided by the invention or its crystal formation, inhibited to Leukemia Cell Lines MV4-11 cell proliferation, for screening treatment clinically or preventing leukemia medicament to provide a kind of selection newly.
Claims (10)
1. compound shown in formula I:
Wherein, R
1, R
2, R
3be selected from methyl, ethyl, propyl group, butyl, amyl group or hexyl respectively.
2. compound according to claim 1, is characterized in that: described compound is such as formula shown in II:
3. the preparation method of compound shown in formula II, is characterized in that: it comprises the following steps:
A, get Motherwort Herb medicinal material, after adding extraction using alcohol, except desolventizing, obtain ethanol extract;
B, by ethanol extract water-dispersion, use ethyl acetate, n-butanol extraction successively, combined ethyl acetate part, except desolventizing, obtain ethyl acetate extract;
C, get ethyl acetate extract, adopt silica gel column chromatography, successively with sherwood oil: acetone=100:1,50:1,25:1,10:1,5:1 is that eluent carries out gradient elution, get sherwood oil: elutriant during acetone=5:1, follow the trail of according to thin layer, merge the elutriant containing similar compositions, recycling design, obtains component G;
D, get component G, adopt anti-phase polystyrene type resin column chromatography, successively with methyl alcohol: water=50:50,75:25,85:15,95:5 is that eluent carries out gradient elution, collect methyl alcohol: elutriant during water=85:15 and/or 95:5, follow the trail of according to thin layer, merge the elutriant containing similar compositions, recycling design, obtains component G7;
E, get component G7, adopt alkaline silica gel column chromatography, successively with sherwood oil: acetone=15:1,10:1,8:1 is that eluent carries out gradient elution, collect sherwood oil: elutriant during acetone=8:1, follow the trail of according to thin layer, merge the elutriant containing similar compositions, recycling design, obtains component G7-4;
F, get component G7-4, peroxidation aluminium column chromatography, with sherwood oil: ethyl acetate=20:1 is that eluent carries out wash-out, follow the trail of according to thin layer, collect the elutriant containing target compound;
G, get elutriant containing target compound, recycling design, through Preparative TLC, obtains target components, then adopts reverse phase liquid preparative chromatography, and with 93%v/v methanol aqueous solution wash-out, collect target compound, recycling design, to obtain final product.
4. preparation method according to claim 3, is characterized in that:
In step a, the weightmeasurement ratio of Motherwort Herb medicinal material and ethanol is 1:8 ~ 24kg/L, and described ethanol is 95%v/v ethanol;
In step b, the weightmeasurement ratio of ethanol extract and water is 1.2:8kg/L, and the volume ratio of water, ethyl acetate, propyl carbinol is 1:1 ~ 6:1 ~ 6;
In step c, the condition of gradient elution is as follows:
In steps d, the condition of gradient elution is as follows:
In step e, the condition of gradient elution is as follows:
In step f, the weightmeasurement ratio of component G7-4 and eluent is 1:600g/mL.
5. preparation method according to claim 3, is characterized in that:
In steps d, polystyrene type resin is MCI gel CHP 20P;
In step g, the developping agent of Preparative TLC is sherwood oil: acetone=5:1.
6. the crystal formation of compound shown in formula II, is characterized in that: this crystal formation is oblique system, and spacer is P2
1, unit cell parameters is
α=90.00 °,
β=97.2458 (13) °,
γ=90.00 °, Z=4, unit cell volume is
7. the preparation method of claim 6 crystal formation, is characterized in that: it comprises the following steps:
1., according to the method described in claim 3 ~ 5 any one, compound shown in formula II is obtained;
2., compound shown in modus ponens II, add methyl alcohol, be placed on and be equipped with in the moisture eliminator of siccative, be placed to crystallize out, obtain the crystal formation of compound shown in formula II.
8. preparation method according to claim 7, is characterized in that: step 2. in, the weightmeasurement ratio of compound and methyl alcohol shown in formula II is 1:0.01 ~ 0.1mg/ml.
9. compound described in claim 1 or 2 or the purposes of its crystal formation in preparation treatment or prevention leukemia medicament.
10. a pharmaceutical composition, it is characterized in that: it be with compound described in claim 1 or 2 or its crystal formation, pharmacy acceptable salt, hydrate or solvate for activeconstituents, add the preparation that pharmaceutically conventional auxiliary material or complementary composition prepare.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104086559A (en) * | 2014-07-09 | 2014-10-08 | 成都中医药大学 | Crystal form of diterpenoid compound |
| WO2015034010A1 (en) * | 2013-09-04 | 2015-03-12 | 学校法人常翔学園 | Intranuclear receptor liver x receptor agonist |
-
2015
- 2015-05-08 CN CN201510232749.3A patent/CN104829675B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015034010A1 (en) * | 2013-09-04 | 2015-03-12 | 学校法人常翔学園 | Intranuclear receptor liver x receptor agonist |
| CN104086559A (en) * | 2014-07-09 | 2014-10-08 | 成都中医药大学 | Crystal form of diterpenoid compound |
Non-Patent Citations (2)
| Title |
|---|
| CESAR A. N.CATALAN ET AL.: ""Synthesis of (24R)- and (24S)-5,28-stigmastadien-3β-ol and determination of the stereochemistry of their 24-hydroxy analogs, the saringosterols"", 《JOURNAL OF ORGANIC CHEMISTRY》 * |
| TAKASHI IIDA ET AL.: ""Biomimetic oxidation of unactivated carbons in steroids by a model of cytochrome P-450, oxorutheniumporphyrinate complex"", 《LIPIDS》 * |
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