CN103641818B - A kind of SM-3997 compound and its production and use - Google Patents
A kind of SM-3997 compound and its production and use Download PDFInfo
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- CN103641818B CN103641818B CN201310394951.7A CN201310394951A CN103641818B CN 103641818 B CN103641818 B CN 103641818B CN 201310394951 A CN201310394951 A CN 201310394951A CN 103641818 B CN103641818 B CN 103641818B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Abstract
The invention discloses a kind of SM-3997 compound, and the preparation method of this compound and purposes.The feature of SM-3997 compound of the present invention is that it exists with the form of crystalline form III, can improve solvability and the stability of original product, be conducive to the preparation of product, use, improve the security of product.
Description
The application is the divisional application of China's No. 201110222442.7 application for a patent for invention, and the applying date of this application is on August 4th, 2011, and denomination of invention is new crystal of SM-3997 and its production and use.
Technical field
The present invention relates to a kind of compound of SM-3997, specifically provide the crystalline form III of this compound, and its production and use.
Background technology
Tandospirone be the 3rd generation anxiolytic medicament and 5-HT
1Aacceptor portion agonist, high selectivity ground combines and exciting postsynaptic 5-HT
1Aacceptor, this receptor mainly concentrate on hippocampus, in, the cerebral limbic system such as interpeduncular nucleus, amygdala and seam gland core, suppress hyperfunction serotonin energy nervous activity, thus play effect antianxity; Meanwhile, by autoreceptor negative feedback mechanism, make 5-HT quantity normalizing, and do not have influence on the 5-HT concentration of synaptic cleft, therefore do not produce the side reaction such as of flaccid muscles, anticonvulsion of benzodiazepines anxiolytic medicament.
There are some researches show, Tandospirone has the angst resistance effect of more highly selective compared with its same analog derivative (as azaspiro ketone, buspirone etc.), and its angst resistance effect and diazepam are suitable, but the toxic side effect such as nervimotion Sexual dysfunction, drug abuse caused by it is less than diazepam.Tandospirone also has certain antidepressant effect, can play therapeutic action better for the patient being mixed with anxiety and depression.At present, SM-3997 (i.e. Tandospirone citrate, structure as shown in Equation 1) has been widely used in the control of clinical anxiety and relative disease thereof, and market outlook are very good.
At present, more research is had to the preparation method of SM-3997, as US4507303, US4818756, JP60087262, CN101362751A, CN101880274A etc., individually disclose the preparation method of Tandospirone and SM-3997, but yet there are no the relevant report of the crystal formation to SM-3997.
Summary of the invention
The object of the present invention is to provide a kind of compound of SM-3997, and preparation method and purposes.
SM-3997 compound provided by the invention, the feature of this compound is that it exists with the form of crystalline form III, in the X-ray powder diffraction of this compound, 2 θ angle of diffraction have characteristic peak at 40.3 ± 0.2,33.4 ± 0.2,11.3 ± 0.2,6.8 ± 0.2 degree of places.
Further, in this compounds X ray powder diffraction, 2 θ angle of diffraction also have characteristic peak at 29.8 ± 0.2,22.9 ± 0.2,18.2 ± 0.2,13.7 ± 0.2 degree of places.
Further, in this compounds X ray powder diffraction, 2 θ angle of diffraction also have characteristic peak at 27.3 ± 0.2,24.3 ± 0.2,22.2 ± 0.2,21.3 ± 0.2,18.0 ± 0.2,15.3 ± 0.2 degree of places.
Wherein, the fusing point of this compound is 166.5-167.5 DEG C.
Wherein, this compound is at 3489 ± 3cm
-1, 3425 ± 3cm
-1, 3218 ± 3cm
-1, 1734 ± 3cm
-1, 1678 ± 3cm
-1there is infrared absorption at place.
Wherein, the differential scanning calorimetric endothermic peak of this compound is respectively at 108 DEG C-127 DEG C, 162 DEG C-177 DEG C and 177 DEG C-220 DEG C.
Further, in this compounds X ray powder diffraction, the relative intensity value of 2 θ angle of diffraction characteristic peaks is:
Further preferably, this compounds X ray powder diffraction as shown in Figure 1.
Present invention also offers a kind of method preparing above-mentioned SM-3997 compound, its operation steps is as follows:
A) SM-3997 is dissolved in the water, the obtained SM-3997 aqueous solution;
B) cooling crystallization is left standstill;
C) isolation of crystalline, dry, to obtain final product;
Wherein, in step b) Crystallization Process in, need leave standstill.
Wherein, the 3-15 that in the described SM-3997 aqueous solution, the consumption (volume) of water is SM-3997 solid weight doubly, is preferably 4-8 doubly, most preferably is 6 times.
Wherein, step a) described dissolution process suitably heats, and preferred Heating temperature is that room temperature is to solvent boiling point.
Present invention also offers above-claimed cpd preparation treatment with serotonin or/and norepinephrine (NA) re-uptake relative disease medicine in purposes.
Wherein, described medicine is the medicine for the treatment of central nervous system disease, be preferably Cure of depression, anxiety disorder, Phobias, agoraphobia, post-traumatic stress disorder, premenstrua anxiety disorder, fibromyalgia, ADHD (Attention Deficit Hyperactivity Disorder), obsessional idea and behavior integration disease, autism, autism, schizophrenia, fat, bulimia nervosa or shortage, Tourette syndrome, vasomotion sexflush, Cocaine or alcohol addiction, sexual dysfunction, borderline personality disorder, chronic fatigue syndrome, the urinary incontinence, pain, Shy Drager syndromes, Raynaud syndrome, the medicine of Parkinson's disease or epilepsy.
Further, above-mentioned SM-3997 compound is preparing the purposes in serotonin conditioning agent.
Wherein, described serotonin conditioning agent is the medicine for the treatment of anxiety disorder, dysthymia disorders or insomnia.
Present invention also offers a kind of pharmaceutical composition, it is activeconstituents by above-claimed cpd, adds the preparation that pharmaceutically acceptable auxiliary material or complementary composition are prepared from.
Pharmaceutically acceptable carrier of the present invention is the usual excipients for the preparation of above-mentioned preparation well known in the art or auxiliary material.The vehicle that oral preparations or external preparation are commonly used or auxiliary material include but are not limited to weighting agent (thinner), lubricant (glidant or antitack agent), dispersion agent, wetting agent, tackiness agent, conditioning agent, solubilizing agent, oxidation inhibitor, fungistat, emulsifying agent, disintegrating agent etc.Tackiness agent, such as syrup, gum arabic, gelatin, sorbyl alcohol, tragacanth, cellulose and its derivates (as Microcrystalline Cellulose, Xylo-Mucine, ethyl cellulose or HPMC etc.), gelatine size, syrup, starch slurry or polyvinylpyrrolidone etc.; Weighting agent, such as lactose, Icing Sugar, dextrin, starch and derivative thereof, cellulose and its derivates, inorganic calcium salt (as calcium sulfate, calcium phosphate, secondary calcium phosphate, precipitated calcium carbonate etc.), sorbyl alcohol or glycine; Lubricant, such as micropowder silica gel, Magnesium Stearate, talcum powder, aluminium hydroxide, boric acid, hydrogenated vegetable oil, polyoxyethylene glycol; Disintegrating agent, such as starch and derivative thereof (as sodium starch glycolate, Explotab, pregelatinized Starch, modified starch, hydroxypropylated starch, W-Gum etc.), polyvinylpyrrolidone or Microcrystalline Cellulose; Wetting agent, such as sodium lauryl sulphate, water or alcohol etc.
The vehicle that injection of the present invention is conventional or auxiliary material include but are not limited to: oxidation inhibitor, such as S-WAT, sodium bisulfite, Sodium Pyrosulfite, dibutyl benzoic acid etc.; Fungistat, such as 0.5% phenol, 0.3% cresols, 0.5% trichloro-butyl alcohol; Conditioning agent, such as hydrochloric acid, Citric Acid, potassium hydroxide (sodium), Sodium Citrate and buffer reagent (comprising phosphoric acid dioxy sodium and Sodium phosphate dibasic etc.); Emulsifying agent, such as Tween-80, do not have that sour sorb is smooth, pluronic gram F-68, lecithin, fabaceous lecithin; Solubilizing agent, such as tween-80, bile, glycerine etc.
In addition, also activeconstituents can be prepared requirement with pharmaceutically acceptable slow-released carrier or controlled release carrier by it to be mixed, again according to the preparation method of sustained-release preparation well known in the art, as added retarding agent dressing or making micropill again by after active principle microcapsules, comprise sustained release pellet or controlled release micro pill etc.; Described slow controlled release carrier includes but are not limited to and oilly mixes agent, hydrophilic colloid or dressing retarding agent etc., described oilly mixes any one or its combination that agent is selected from glyceryl monostearate, hydrogenated castor oil, Dormant oils, polysiloxane or dimethyl siloxane; Described hydrophilic colloid is selected from any one or its combination of Xylo-Mucine, hydroxypropylcellulose, Vltra tears, PVP, gum arabic, tragacanth or carbopol; Described dressing retarding agent is selected from any one or its combination of ethyl cellulose (EC), HPMC (HMPC), polyvinylpyrrolidone (PVP), cellulose acetate-phthalate (CAP), acrylic resin.
Wherein, in the preferred technical solution of the present invention, the dosage form of described composition be selected from tablet, suspension, capsule, granule, pill, powder, pill, syrup, mixture, distillate medicinal water, effervescent, paste, emulsion, medicinal tea, pulvis, injection (injection), transfusion, gelifying agent, emplastrum, plaster, creme, ointment, liniment, lotion, suppository, basting agent, paste, solidifying paste any one.
SM-3997 compound described in the present invention all refers to the SM-3997 compound existed with crystalline state crystalline form III form.
Accompanying drawing explanation
The X-ray powder diffraction of Fig. 1 SM-3997 crystalline form III;
The DSC collection of illustrative plates of Fig. 2 SM-3997 crystalline form III;
The infared spectrum of Fig. 3 SM-3997 crystalline form III;
Fig. 4 prepares the X-ray powder diffraction of gained SM-3997 according to the open method of document (CN101362751B embodiment 4, CN101880274A);
Embodiment
The preparation of embodiment 1 SM-3997 compound
SM-3997 500g is placed in 3000ml water, is heated to 80 DEG C of dissolvings; As required, add gac and carry out desolventing technology; After filtration, the lower standing crystallize out of mother liquor cooling.Collecting by filtration crystal, drying under reduced pressure, the SM-3997 compound of obtained white, yield is 91%.
Described compound Crystallization Process in need to leave standstill.
In the present invention, the add-on of preferred gac is the 1wt.%-5wt.% of SM-3997 weight.
The detection method of crystal of the present invention comprises:
1, X powder diffraction test
1) sample preparation: directly take sample and make X diffraction experiment.
2) test apparatus: X ' Pert Pro MPD Philips X-ray powder diffractometer
(penetrating source CuK α, graphite monochromator, useful range: 5-50 ° of 2 θ).
3) test conditions: CuK α radiation, graphite monochromator, pipe pressure 40KV, pipe stream 35mA, 2 θ sweep limit 5-50 °, sweep velocity 9 °/point, step-length 0.03 °.Slit condition: launching slit is 0.5 °, and accepting slit is 1mm.
2, melting point test
Huge sky, Tianjin is used to send out YRT-3 type drug melting point instrument; Test conditions is: pre-temperature 155 DEG C, heat-up rate 1 DEG C/min.
3, differential scanning calorimetery (DSC) test
Use DSC Q100 analyser, initial temperature is set to 30 DEG C, and final temperature is set to 260 DEG C, and temperature rise rate is set to 10 DEG C/min (10K/min).
4, infrared measurement test
Use instrument is ThermoFisher Nicolet 6700 Fourier transformation infrared spectrometer, and uses paraffin oil to stick with paste the detection of legal system sheet.
The preparation method of SM-3997 used in the present invention is as follows:
SM-3997 is prepared with reference to existing document (CN101362751B embodiment 4, CN101880274A):
Method 1: by Tandospirone alkali 300g, Citric Acid 164g, ethanol 3600ml adds in reactor, is warmed up to 80 DEG C, refluxes 30 minutes, lets cool to room temperature, leaves standstill, suction filtration, with absolute ethanol washing, dry, obtains SM-3997 430g.Recording its fusing point according to fusing point test method of the present invention is 169-170 DEG C, and salify productive rate is 95%, and X powder diffraction collection of illustrative plates as shown in Figure 4.
Method 2: by Tandospirone alkali 100g, Citric Acid 55g, ethyl acetate 800ml add in reactor, reacts 2 hours, suction filtration, washing, dry, obtains SM-3997 143g.Recording its fusing point according to fusing point test method of the present invention is 169-171 DEG C, and salify productive rate is 95%, and X powder diffraction collection of illustrative plates as shown in Figure 4.
Detect obtained SM-3997 compound according to the method described above, recording its fusing point is 166.5-167.5 DEG C, and powder X-ray diffraction is shown in Fig. 1, and diffraction related data is see table 1, and DSC is shown in Fig. 2, and IR is shown in Fig. 3.
The X-ray powder diffraction data of table 1 SM-3997 crystalline form III
The preparation of embodiment 2 SM-3997 compound
Prepare SM-3997 compound according to the method for embodiment 1, its condition is see table 2.Under each condition, the crystal of gained is through powder X-ray diffraction, determines that it is SM-3997 crystalline form III, and adopting fusing point test method of the present invention to record its fusing point is 166.5-167.5 DEG C.
The preparation of table 2 crystalline form III
Beneficial effect of the present invention is proved below by way of concrete test example.
The solvability comparative studies of test example 1 SM-3997 compound of the present invention and currently available products
Take trial-product 2g, be placed in the 20ml water of 25 ± 2 DEG C, in powerful jolting 10 second every 1 minute, observe the dissolving situation in 3 minutes.As without visual visible particles of solute, be namely considered as dissolving completely; If there is visual visible particles of solute, add 5 times of water gagings, repeat aforementioned operation, until dissolve completely.Record total water consumption and time.The results are shown in Table 3.
Wherein, SM-3997 compound is prepared by the embodiment of the present invention 1, and SM-3997 currently available products prepares with reference to the disclosed method of existing document (CN101362751B embodiment 4, CN101880274A).
The solvability comparative studies of table 3 crystalline form III and currently available products
From table 3, compared with SM-3997 currently available products, the water-soluble of the compounds of this invention has some improvement.
The study on the stability of test example 2 SM-3997 compound of the present invention and currently available products
Study on the stability condition comprises:
1. thermal destruction: get trial-product and be about 200mg, is placed in 60 DEG C of loft drier and places;
2. photodegradation: get trial-product and be about 200mg, being placed in illumination is that the environment of 4500 ± 500lx is placed;
3. high humidity degraded: get trial-product 200mg, be placed in and be placed with KNO
3in the moisture eliminator of saturated solution, room temperature is placed.Study on the stability the results are shown in Table 4.
Wherein, SM-3997 compound is prepared by the embodiment of the present invention 1, and SM-3997 currently available products prepares with reference to the disclosed method of existing document (CN101362751B embodiment 4, CN101880274A).
The study on the stability of table 4 crystalline form III and currently available products
From table 4, SM-3997 currently available products is to the less stable of light, heat, and particularly under strong illumination, in product, impurity significantly increases: irradiate 5 days, dopant species is increased to 13, purity drop 0.3%; Irradiate 10 days, dopant species is increased to 14, purity drop 0.63%; Compared with SM-3997 currently available products, the stability of crystalline form III is better, and crystalline form III is under accelerated stability test, and dopant species is without obvious increase, and purity is without obvious reduction, shows that crystalline form III significantly improves the stability of SM-3997.
In sum, SM-3997 new crystal of the present invention, can improve solvability and the stability of original product, advantageously in preparation, the use of product, improves the security of product.
Claims (18)
1. SM-3997 compound, it is characterized in that: this compound exists with the form of crystalline form III, in the X-ray powder diffraction of this compound, 2 θ angle of diffraction have characteristic peak at 40.3 ± 0.2,33.4 ± 0.2,11.3 ± 0.2,6.8 ± 0.2,29.8 ± 0.2,22.9 ± 0.2,18.2 ± 0.2,13.7 ± 0.2,27.3 ± 0.2,24.3 ± 0.2,22.2 ± 0.2,21.3 ± 0.2,18.0 ± 0.2,15.3 ± 0.2 degree of places.
2. SM-3997 compound according to claim 1, is characterized in that: in the X-ray powder diffraction of this compound, has powder X-ray diffraction peak figure feature substantially as shown in Figure 1.
3. according to SM-3997 compound according to claim 1 or claim 2, it is characterized in that: the fusing point of described compound is 166.5-167.5 DEG C.
4. SM-3997 compound according to claim 3, is characterized in that: described compound has DSC collection of illustrative plates substantially as shown in Figure 2.
5. according to SM-3997 compound according to claim 1 or claim 2, it is characterized in that: the infared spectrum of described compound is at 3489 ± 3cm
-1, 3425 ± 3cm
-1, 3218 ± 3cm
-1, 1734 ± 3cm
-1, 1678 ± 3cm
-1there is infrared absorption at place.
6. according to SM-3997 compound according to claim 1 or claim 2, it is characterized in that: described compound has infared spectrum feature substantially as shown in Figure 3.
7. the preparation method of the SM-3997 compound described in any one of claim 1-6, it is characterized in that, operation steps is as follows:
A) SM-3997 is dissolved in the water, the obtained SM-3997 aqueous solution;
B) cooling crystallization;
C) isolation of crystalline, dry, to obtain final product;
Wherein, in step b) Crystallization Process in, need leave standstill.
8. preparation method according to claim 7, it is characterized in that: step a) described in the SM-3997 aqueous solution consumption cumulative volume of water be the 3-15 of SM-3997 solid weight doubly, wherein, described volume unit is milliliter, and described solid weight unit is gram.
9. preparation method according to claim 8, it is characterized in that: step a) described in the SM-3997 aqueous solution consumption cumulative volume of water be the 4-8 of SM-3997 solid weight doubly, wherein, described volume unit is milliliter, and described solid weight unit is gram.
10. preparation method according to claim 9, it is characterized in that: step a) described in the SM-3997 aqueous solution consumption cumulative volume of water be 6 times of SM-3997 solid weight, wherein, described volume unit is milliliter, and described solid weight unit is gram.
11. preparation methods according to claim 7, is characterized in that: step a) described in dissolution process suitably heat.
12. preparation methods according to claim 11, is characterized in that: step a) described in dissolution process Heating temperature be that room temperature is to solvent boiling point.
13. 1 kinds of pharmaceutical compositions, is characterized in that: described pharmaceutical composition as activeconstituents, adds the preparation that pharmaceutically acceptable auxiliary material or complementary composition are prepared from by the SM-3997 compound described in any one of claim 1-6.
14. pharmaceutical compositions according to claim 13, is characterized in that: the dosage form of described composition be selected from tablet, suspension, capsule, granule, pill, powder, pill, syrup, mixture, distillate medicinal water, effervescent, paste, emulsion, medicinal tea, pulvis, injection, transfusion, gelifying agent, plaster, creme, liniment, lotion, suppository, basting agent, paste any one.
15. pharmaceutical compositions according to claim 14, is characterized in that: described paste be selected from emplastrum, solidifying paste, ointment any one.
SM-3997 compound described in 16. any one of claim 1-6 preparation treatment with serotonin (5-HT) or/and norepinephrine (NA) re-uptake relative disease medicine in application.
17. application according to claim 16, is characterized in that: described medicine is used for the treatment of central nervous system disease.
18. application according to claim 17, described central nervous system disease is selected from dysthymia disorders, anxiety disorder, Phobias, agoraphobia, post-traumatic stress disorder, premenstrua anxiety disorder, fibromyalgia, ADHD (Attention Deficit Hyperactivity Disorder), obsessional idea and behavior integration disease, autism, autism, schizophrenia, fat, bulimia nervosa or shortage, Tourette syndrome, vasomotion sexflush, Cocaine or alcohol addiction, sexual dysfunction, borderline personality disorder, chronic fatigue syndrome, the urinary incontinence, pain, Shy Drager syndromes, Raynaud syndrome, Parkinson's disease or epileptic condition.
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| CN201310394951.7A CN103641818B (en) | 2011-08-04 | 2011-08-04 | A kind of SM-3997 compound and its production and use |
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| CN201310394951.7A CN103641818B (en) | 2011-08-04 | 2011-08-04 | A kind of SM-3997 compound and its production and use |
| CN201110222442.7A CN102344442B (en) | 2011-08-04 | 2011-08-04 | Novel crystal form of tandospirone citrate and preparation method and application thereof |
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| CN103755687B (en) * | 2013-12-25 | 2015-10-21 | 四川科瑞德制药有限公司 | Hydrochloric acid Tandospirone crystalline form I and preparation method thereof |
| CN106349226A (en) * | 2014-06-06 | 2017-01-25 | 四川科瑞德制药股份有限公司 | L-tartaric acid tandospirone compound |
| CN106349227A (en) * | 2014-06-06 | 2017-01-25 | 四川科瑞德制药股份有限公司 | Tandospirone oxalate compound |
| CN106397410B (en) * | 2015-07-30 | 2021-03-26 | 四川科瑞德制药股份有限公司 | 5-hydroxytryptamine receptor agonist and preparation method and application thereof |
| CN106397411B (en) * | 2015-07-30 | 2021-03-26 | 四川科瑞德制药股份有限公司 | 5-hydroxytryptamine receptor agonist and preparation method and application thereof |
| CN106397413B (en) * | 2015-07-30 | 2021-03-26 | 四川科瑞德制药股份有限公司 | 5-hydroxytryptamine receptor agonist and preparation method and application thereof |
| CN106397412A (en) * | 2015-07-30 | 2017-02-15 | 四川科瑞德制药股份有限公司 | 5-hydroxytryptamine receptor agonists, a preparing method thereof and uses of the receptor agonists |
| CN106749196B (en) * | 2015-11-25 | 2020-07-03 | 四川科瑞德制药股份有限公司 | 5-hydroxytryptamine receptor agonist |
| CN106905302B (en) * | 2015-12-22 | 2020-07-31 | 四川科瑞德制药股份有限公司 | Azaspiroanone compound and preparation method thereof |
| CN113121507A (en) * | 2019-12-30 | 2021-07-16 | 北大医药股份有限公司 | Stable crystal form of tandospirone citrate and preparation method thereof |
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| CN101362751A (en) * | 2007-08-10 | 2009-02-11 | 成都市律凯医药科技有限公司 | Tandospirone citrate, preparation method thereof, formulations and quality control method |
| CN101880274A (en) * | 2010-06-28 | 2010-11-10 | 北大国际医院集团西南合成制药股份有限公司 | Method for preparing tandospirone and analogues of tandospirone |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4507303A (en) * | 1981-12-22 | 1985-03-26 | Sumitomo Chemical Company, Limited | Succinimide derivatives, compositions and method of use |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101362751A (en) * | 2007-08-10 | 2009-02-11 | 成都市律凯医药科技有限公司 | Tandospirone citrate, preparation method thereof, formulations and quality control method |
| CN101880274A (en) * | 2010-06-28 | 2010-11-10 | 北大国际医院集团西南合成制药股份有限公司 | Method for preparing tandospirone and analogues of tandospirone |
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| CN103641818A (en) | 2014-03-19 |
| CN102344442B (en) | 2014-08-13 |
| CN102344442A (en) | 2012-02-08 |
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