CN104945397B - Medicine Tropiseiron hydrochloride compound for the treatment of nausea and vomiting and preparation method thereof - Google Patents
Medicine Tropiseiron hydrochloride compound for the treatment of nausea and vomiting and preparation method thereof Download PDFInfo
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- CN104945397B CN104945397B CN201510455371.3A CN201510455371A CN104945397B CN 104945397 B CN104945397 B CN 104945397B CN 201510455371 A CN201510455371 A CN 201510455371A CN 104945397 B CN104945397 B CN 104945397B
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- China
- Prior art keywords
- hydrochloride compound
- navoban
- soz
- medicine
- vomiting
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- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- -1 hydrochloride compound Chemical class 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 239000003814 drug Substances 0.000 title claims abstract description 10
- 206010047700 Vomiting Diseases 0.000 title claims abstract description 9
- 229940079593 drug Drugs 0.000 title description 2
- 239000013078 crystal Substances 0.000 claims abstract description 11
- 230000005260 alpha ray Effects 0.000 claims abstract description 5
- 238000005259 measurement Methods 0.000 claims abstract description 5
- UIVFDCIXTSJXBB-ITGUQSILSA-N tropisetron Chemical compound C1=CC=C[C]2C(C(=O)O[C@H]3C[C@H]4CC[C@@H](C3)N4C)=CN=C21 UIVFDCIXTSJXBB-ITGUQSILSA-N 0.000 claims description 32
- 229960003688 tropisetron Drugs 0.000 claims description 32
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- 239000011259 mixed solution Substances 0.000 claims description 11
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 6
- 229910017488 Cu K Inorganic materials 0.000 claims description 4
- 229910017541 Cu-K Inorganic materials 0.000 claims description 4
- 238000010586 diagram Methods 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- 239000012043 crude product Substances 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 238000001291 vacuum drying Methods 0.000 claims description 3
- 238000010792 warming Methods 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 239000012535 impurity Substances 0.000 abstract description 5
- 238000005516 engineering process Methods 0.000 abstract description 3
- 238000010521 absorption reaction Methods 0.000 abstract 1
- 238000000634 powder X-ray diffraction Methods 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 13
- 239000000463 material Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000004806 packaging method and process Methods 0.000 description 4
- 238000012552 review Methods 0.000 description 4
- 238000007789 sealing Methods 0.000 description 4
- 238000004088 simulation Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 238000005070 sampling Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 210000002856 peripheral neuron Anatomy 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 210000003818 area postrema Anatomy 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000003518 presynaptic effect Effects 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 230000001515 vagal effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
- C07D451/06—Oxygen atoms
- C07D451/12—Oxygen atoms acylated by aromatic or heteroaromatic carboxylic acids, e.g. cocaine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Abstract
The invention discloses a kind of medicine Tropiseiron hydrochloride compound treating nausea and vomiting and preparation method thereof originally, belong to pharmaceutical technology field.Described Tropiseiron hydrochloride compound is crystal, uses the X ray powder diffraction pattern that Cu K alpha ray measurement obtains as shown in Figure 1.Compared with prior art, purity is high, good fluidity for Tropiseiron hydrochloride compound of the present invention, and good stability is difficult to moisture absorption, and impurity content is low.
Description
Technical field
The invention belongs to pharmaceutical technology field, relate to a kind of medicine Tropiseiron hydrochloride compound treating nausea and vomiting and preparation method thereof.
Background technology
Navoban (Soz) is selectivity peripheral neurons and central nervous system's 5-seretonine receptor 5 antagonist, can selectively block vomiting reflex maincenter, the excitement of peripheral neurons presynaptic 5-seretonine receptor 5, act on 5-seretonine receptor 5 of the vagal activity of incoming nervus centralis area postrema, can prevent and treat the nausea and vomiting caused by chemotherapy, not cause extrapyramidal system untoward reaction.
In prior art, for the crystal formation of Navoban (Soz), there is many research, but the hygroscopicity of impurity content, stability and crystal formation is the most undesirable, brought difficulty also to while have impact on self stability the preparation of preparation.
The present invention, through substantial amounts of experimental study, has prepared a kind of Navoban (Soz) crystalline compounds being different from prior art, and the purity of this Tropiseiron hydrochloride compound is high, good fluidity, good stability, it is difficult to hygroscopicity, impurity content is low, and the preparation for preparation brings conveniently.
Summary of the invention
The primary goal of the invention of the present invention is to propose a kind of Tropiseiron hydrochloride compound；
Second goal of the invention of the present invention is to propose the preparation method of this Tropiseiron hydrochloride compound.
In order to realize the purpose of the present invention, the technical scheme of employing is:
A kind of medicine Tropiseiron hydrochloride compound treating nausea and vomiting, described Tropiseiron hydrochloride compound is crystal, uses the X-ray powder diagram that Cu-K alpha ray measurement obtains as shown in Figure 1.
The invention still further relates to the preparation method of this Navoban (Soz) crystalline compounds, comprise the following steps:
(1) being joined by Navoban (Soz) crude product in the mixed solution of water, acetonitrile, heat up, stirring is to being completely dissolved；
(2) under the effect of sound field, the mixed solution of ethanol, chloroform, hexamethylene is added while stirring；
(3) after ethanol, chloroform, the mixed solution of hexamethylene add, under the effect of sound field, cooling, growing the grain 2 hours, washing, vacuum drying, obtain Tropiseiron hydrochloride compound.
Wherein volume is Navoban (Soz) weight 4 times of the mixed solution of water, acetonitrile described in step (1), water, the volume ratio of acetonitrile are 3:1；Step is warming up to 30 DEG C described in (1)；Sound field frequency described in step (2) is 30KHz, output is 45W；Volume is Navoban (Soz) weight 8 times of the mixed solution of ethanol, chloroform, hexamethylene described in step (2), ethanol, chloroform, the volume ratio of hexamethylene are 1:2:1；Described in step (2), mixing speed is 150 revs/min, and adding speed is 100 ml/min；Sound field frequency described in step (3) is 25KHz, output is 40W；Cooling described in step (3) refers to be cooled to-5 DEG C with 10 DEG C/h.
Below technical scheme is made further explanation:
The polymorphism of solid chemical is the natural phenomena that a kind of universal material exists, this phenomenon refers to that a kind of solid chemical can exist 2 kinds or two or more crystal form state, being also called the polymorphic state of material, the polymorphic state of material is also referred to as " allomorphism " phenomenon.Although its chemical nature of allomorphous solid matter is identical, but its physicochemical property is probably different.For " allomorphism medicine " that physicochemical property is different, the curative effect of different disease preventing and treating can also be shown clinically, directly affect application and the clinical effectiveness of medicine.
In prior art, for the crystal formation of Navoban (Soz), there is many research, but the hygroscopicity of impurity content, stability and crystal formation is the most undesirable, brought difficulty also to while have impact on self stability the preparation of preparation.
The present invention, through substantial amounts of experimental study, has prepared a kind of Navoban (Soz) crystalline compounds being different from prior art, and the purity of this Tropiseiron hydrochloride compound is high, good fluidity, good stability, it is difficult to hygroscopicity, impurity content is low, and the preparation for preparation brings conveniently.
Accompanying drawing explanation
Fig. 1 is the X-ray powder diagram that the Navoban (Soz) crystalline compounds that embodiment 1 prepares uses Cu-K alpha ray measurement to obtain.
Detailed description of the invention
The detailed description of the invention of the present invention is only limitted to be explained further and the present invention is described, is not construed as limiting present disclosure.
Embodiment 1 :The preparation of Navoban (Soz) crystalline compounds
(1) being joined by Navoban (Soz) crude product in the water of 4 times that volume is Navoban (Soz) weight, the mixed solution of acetonitrile, water, the volume ratio of acetonitrile are 3:1, are warming up to 30 DEG C, and stirring is to being completely dissolved；
(2) frequency be 30KHz, output be 45W sound field under, adding volume while stirring is the ethanol of Navoban (Soz) weight 8 times, chloroform, the mixed solution of hexamethylene, ethanol, chloroform, the volume ratio of hexamethylene are 1:2:1, mixing speed is 150 revs/min, and adding speed is 100 ml/min；
(3) after ethanol, chloroform, the mixed solution of hexamethylene add, frequency be 25KHz, output be 40W sound field under, be cooled to-5 DEG C with 10 DEG C/h, growing the grain 2 hours, washing, vacuum drying, obtain Tropiseiron hydrochloride compound.
Use the X-ray powder diagram that Cu-K alpha ray measurement obtains as it is shown in figure 1, its purity of high-performance liquid chromatogram determination is 99.9%.
Experimental example
1
, fluidity test
The mobility of the Navoban (Soz) crystal that the embodiment of the present invention 1 prepares is detected by this experimental example.
Method: prepare 6 batches of Navoban (Soz)s (batch: 1,2,3,4,5 and 6) continuously according to the method for the embodiment of the present invention 1, sample from 6 batches of prepared Navoban (Soz)s respectively, use fixed funnel method, the suitable height that funnel is placed on graph paper, Navoban (Soz) crystal is made freely to flow down from bell mouth, until the cone top formed contacts with bell mouth, measure hypotenuse and the horizontal angle (θ angle of repose) of Navoban (Soz) accumulation horizon.The results are shown in Table 1:
Table 1, the fluidity test result of Navoban (Soz)
From the interpretation of table 1, the mobility of the Navoban (Soz) crystal of the present invention is fine.
Experimental example
2
: influence factor tests
1, hot test
The Navoban (Soz) crystalline compounds that Example 1 prepares, simulation listing packaging, put in sealing clean container, place 10 days at a temperature of 40 ± 2 DEG C, in sampling in the 5th day and the 10th day, detecting by stability high spot reviews project, result of the test compared with 0 day.
2, high humility test
The Navoban (Soz) crystalline compounds that Example 1 prepares, simulation listing packaging, put in sealing clean container, place 10 days under conditions of 25 ± 2 DEG C of relative humiditys 90% ± 5%, in sampling in the 5th day and the 10th day, detecting by stability high spot reviews project, result of the test compared with 0 day.
3, strong illumination test
The Navoban (Soz) crystalline compounds that Example 1 prepares, simulation listing packaging, put in sealing clean container, being placed in illumination is to place 10 days under conditions of 4500lx, in sampling in the 5th day and the 10th day, detecting by stability high spot reviews project, result compared with 0 day.The results are shown in Table 2
Table 2 influence factor's result of the test
Result shows: the Navoban (Soz) crystalline compounds that the present invention prepares, and its stability is good, under high temperature, high humidity, high light conditions, all keeps stable performance.
Experimental example
3
: Acceleration study
The Navoban (Soz) crystalline compounds that Example 1 prepares 3 batches and marketable material, simulation listing packaging, put in sealing clean container, in 40 DEG C ± 2 DEG C, place 6 months under the conditions of relative humidity 70% ± 5%, sample once respectively at 1,2,3,6 the end of month during testing, each stability high spot reviews project is tested.The results are shown in Table 3.
Table 3 accelerated test result
Result shows: the Navoban (Soz) crystalline compounds that the present invention prepares, and accelerated result of the test understands, and its good stability, total miscellaneous content is low.
Experimental example
4
: wettability test
1 instrument
PL203 electronic balance, LRH-250-S constant temperature and humidity incubator, HH-400SD testing chamber for medicine stability；
2 methods
Take bottom and fill the glass desicator (for ensureing that saline solution is saturated, should be with the presence of the salt of excess bottom exsiccator) of salt supersaturated solution, the built-in weighing botle of exsiccator, in calorstat, place 48h to constant humidity.Navoban (Soz) crystalline compounds that Example 1 prepares and marketable material, each 2g, put in weighing botle, accurately weighed, bottle cap is opened, puts into exsiccator top, preserve in putting 25 DEG C of constant temperature and humidity incubators or 20 DEG C of stability test casees by different temperatures requirement, operation repetitive 3 parts, weighs respectively at different time, calculates the hydroscopicity of different time.
Computing formula:Result such as table 4:
Table 4 hygroscopicity test results
According to above-mentioned experiment, the hygroscopicity of Navoban (Soz) crystalline compounds prepared by the present invention is low, good stability.
Claims (2)
1. the medicine Tropiseiron hydrochloride compound treating nausea and vomiting, it is characterised in that described Tropiseiron hydrochloride compound is crystal, uses the X-ray powder diagram that Cu-K alpha ray measurement obtains as shown in Figure 1.
The preparation method of the medicine Tropiseiron hydrochloride compound for the treatment of nausea and vomiting the most according to claim 1, it is characterised in that comprise the following steps:
(1) being joined by Navoban (Soz) crude product in the water of 4 times that volume is Navoban (Soz) weight, the mixed solution of acetonitrile, water, the volume ratio of acetonitrile are 3:1, are warming up to 30 DEG C, and stirring is to being completely dissolved；
(2) frequency be 30KHz, output be 45W sound field under, while stirring add volume be the ethanol of Navoban (Soz) weight 8 times, chloroform, the mixed solution of hexamethylene, ethanol, chloroform, the volume ratio of hexamethylene are 1:2:1；Mixing speed is 150 revs/min, and adding speed is 100 ml/min；
(3) after ethanol, chloroform, the mixed solution of hexamethylene add, frequency be 25KHz, output be 40W sound field under, be cooled to-5 DEG C with 10 DEG C/h, growing the grain 2 hours, washing, vacuum drying, obtain Tropiseiron hydrochloride compound.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510455371.3A CN104945397B (en) | 2015-07-30 | 2015-07-30 | Medicine Tropiseiron hydrochloride compound for the treatment of nausea and vomiting and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510455371.3A CN104945397B (en) | 2015-07-30 | 2015-07-30 | Medicine Tropiseiron hydrochloride compound for the treatment of nausea and vomiting and preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104945397A CN104945397A (en) | 2015-09-30 |
| CN104945397B true CN104945397B (en) | 2016-08-24 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| CN201510455371.3A Active CN104945397B (en) | 2015-07-30 | 2015-07-30 | Medicine Tropiseiron hydrochloride compound for the treatment of nausea and vomiting and preparation method thereof |
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Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105193729A (en) * | 2015-10-08 | 2015-12-30 | 杨献美 | Pharmaceutical tropisetron hydrochloride composition dry suspension for treating nausea and vomiting both caused by chemotherapy |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100503601C (en) * | 2007-04-02 | 2009-06-24 | 北京成宇化工有限公司 | Process of preparing troipisetron |
| CN102532128B (en) * | 2010-12-17 | 2014-11-12 | 北大方正集团有限公司 | Synthetic method of tropisetron and prepare method of hydrochloric acid tropisetron |
| CN102584815A (en) * | 2011-01-14 | 2012-07-18 | 湖南康普医药研究院 | Method for preparing tropisetron hydrochloride on large scale |
| CN102351857B (en) * | 2011-08-23 | 2013-06-12 | 天津市汉康医药生物技术有限公司 | Tropiseiron hydrochloride compound |
| CN102367252A (en) * | 2011-11-03 | 2012-03-07 | 天津市汉康医药生物技术有限公司 | Tropisetron hydrochloride compound |
| CN103360386B (en) * | 2013-07-18 | 2015-08-19 | 珠海金鸿药业股份有限公司 | A kind of Tropiseiron hydrochloride compound and preparation method thereof and the pharmaceutical composition containing this compound |
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