CN104945397A - Tropisetron hydrochloride medicine compound for treating nausea and vomit as well as preparation method thereof - Google Patents
Tropisetron hydrochloride medicine compound for treating nausea and vomit as well as preparation method thereof Download PDFInfo
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- CN104945397A CN104945397A CN201510455371.3A CN201510455371A CN104945397A CN 104945397 A CN104945397 A CN 104945397A CN 201510455371 A CN201510455371 A CN 201510455371A CN 104945397 A CN104945397 A CN 104945397A
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- preparation
- nausea
- medicine
- hydrochloride compound
- tropiseiron
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- 229960003674 tropisetron hydrochloride Drugs 0.000 title claims abstract description 34
- 238000002360 preparation method Methods 0.000 title claims abstract description 23
- 239000003814 drug Substances 0.000 title claims abstract description 18
- XIEGSJAEZIGKSA-LUNMCBQDSA-N tropisetron hydrochloride Chemical compound Cl.C1=CC=C2C(C(=O)O[C@H]3C[C@H]4CC[C@@H](C3)N4C)=CNC2=C1 XIEGSJAEZIGKSA-LUNMCBQDSA-N 0.000 title claims abstract 5
- 150000001875 compounds Chemical class 0.000 title abstract description 15
- 206010028813 Nausea Diseases 0.000 title abstract 2
- 230000008693 nausea Effects 0.000 title abstract 2
- 210000004916 vomit Anatomy 0.000 title abstract 2
- 230000008673 vomiting Effects 0.000 title abstract 2
- -1 tropisetron hydrochloride compound Chemical class 0.000 claims abstract description 25
- 239000013078 crystal Substances 0.000 claims abstract description 11
- 229910017488 Cu K Inorganic materials 0.000 claims abstract description 5
- 229910017541 Cu-K Inorganic materials 0.000 claims abstract description 5
- 238000005259 measurement Methods 0.000 claims abstract description 5
- 238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
- 206010047700 Vomiting Diseases 0.000 claims description 14
- 238000002156 mixing Methods 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 11
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 11
- 229960001701 chloroform Drugs 0.000 claims description 11
- 238000003756 stirring Methods 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 5
- 230000005260 alpha ray Effects 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 239000012043 crude product Substances 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
- 229940079593 drug Drugs 0.000 abstract description 2
- 239000012535 impurity Substances 0.000 abstract 1
- ZNRGQMMCGHDTEI-ITGUQSILSA-N tropisetron Chemical compound C1=CC=C2C(C(=O)O[C@H]3C[C@H]4CC[C@@H](C3)N4C)=CNC2=C1 ZNRGQMMCGHDTEI-ITGUQSILSA-N 0.000 description 27
- 238000012360 testing method Methods 0.000 description 11
- 239000000463 material Substances 0.000 description 5
- 239000000126 substance 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
- 238000005070 sampling Methods 0.000 description 4
- 238000007789 sealing Methods 0.000 description 4
- 238000004088 simulation Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000005286 illumination Methods 0.000 description 2
- 210000002856 peripheral neuron Anatomy 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 229960003688 tropisetron Drugs 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 238000010521 absorption reaction Methods 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
- 238000004364 calculation method Methods 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000005516 engineering process Methods 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
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003518 presynaptic effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000002269 spontaneous effect Effects 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 tropisetron hydrochloride medicine compound for treating nausea and vomit as well as a preparation method thereof, and belongs to the technical field of medicines. The tropisetron hydrochloride compound is a crystal of which the X-ray powder diffraction pattern is obtained through Cu-K[alpha] ray measurement and shown in the Figure 1. Compared with the prior art, the tropisetron hydrochloride compound is high in purity, good in fluidity and stability, unlikely to moisture and low in impurity content.
Description
Technical field
The invention belongs to medical art, relate to a kind of medicine Tropiseiron hydrochloride compound for the treatment of nausea and vomiting and preparation method thereof.
Background technology
Tropisetron hydrochloride is selectivity peripheral neurons and central nervous system 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 importing nervus centralis area postrema into, can the nausea and vomiting that caused by chemotherapy of Prevention and Curation, do not cause extrapyramidal system untoward reaction.
In prior art, for the crystal formation of Tropisetron hydrochloride, had many research, but the water absorbability of foreign matter content, stability and crystal formation is still undesirable, brings difficulty also to while have impact on self stability the preparation of preparation.
The present invention is through a large amount of experimental studies, and obtained a kind of Tropisetron hydrochloride crystalline compounds being different from prior art, the purity of this Tropiseiron hydrochloride compound is high, good fluidity, good stability, not easily water absorbability, foreign matter content is low, and the preparation for preparation brings conveniently.
In prior art, for the crystal formation of Tropisetron hydrochloride, had many research, but the water absorbability of foreign matter content, stability and crystal formation is still undesirable, brings difficulty also to while have impact on self stability the preparation of preparation.
The present invention is through a large amount of experimental studies, and obtained a kind of Tropisetron hydrochloride crystalline compounds being different from prior art, the purity of this Tropiseiron hydrochloride compound is high, good fluidity, good stability, not easily water absorbability, foreign matter content is low, and the preparation for preparation brings conveniently.
Summary of the invention
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 the preparation method proposing this Tropiseiron hydrochloride compound.
In order to realize object of the present invention, the technical scheme of employing is:
Treat a medicine Tropiseiron hydrochloride compound for nausea and vomiting, described Tropiseiron hydrochloride compound is crystal, and the X-ray powder diffraction pattern that the measurement of use Cu-K alpha-ray obtains as shown in Figure 1.
The invention still further relates to the preparation method of this Tropisetron hydrochloride crystalline compounds, comprise the following steps:
(1) Tropisetron hydrochloride crude product is joined in the mixing solutions of water, acetonitrile, heat up, be stirred to and dissolve completely;
(2) under the effect of sound field, the mixing solutions of ethanol, trichloromethane, hexanaphthene is added while stirring;
(3) after the mixing solutions of ethanol, trichloromethane, hexanaphthene adds, under the effect of sound field, cooling, growing the grain 2 hours, washing, vacuum-drying, obtains Tropiseiron hydrochloride compound.
Wherein the volume of the mixing solutions of water, acetonitrile described in step (1) is 4 times of Tropisetron hydrochloride weight, and the volume ratio of water, acetonitrile is 3:1; Step is warming up to 30 DEG C described in (1); Sound field frequency described in step (2) is 30KHz, output rating is 45W; The volume of the mixing solutions of ethanol, trichloromethane, hexanaphthene described in step (2) is 8 times of Tropisetron hydrochloride weight, and the volume ratio of ethanol, trichloromethane, hexanaphthene is 1:2:1; Described in step (2), stirring velocity is 150 revs/min, and adding speed is 100 ml/min; Sound field frequency described in step (3) is 25KHz, output rating is 40W; Cooling described in step (3) refers to and is cooled to-5 DEG C with 10 DEG C/h.
Below technical scheme of the present invention is made further explanation:
The polymorphism of solid chemical is the spontaneous phenomenon that a kind of general material exists, this phenomenon refers to that a kind of solid chemical can exist 2 kinds or two or more crystal form state, be also called the polymorphic state of material, the polymorphic state of material is also referred to as " paramorphism " phenomenon.Although its chemical nature of allomorphous solid matter is identical, its physico-chemical property may be different.For " paramorphism medicine " that physico-chemical property is different, also can show the curative effect of different disease preventing and treating clinically, directly affect application and the clinical effectiveness of medicine.
Accompanying drawing explanation
Fig. 1 is the X-ray powder diffraction pattern that the Tropisetron hydrochloride crystalline compounds for preparing of embodiment 1 uses the measurement of Cu-K alpha-ray and obtains.
Embodiment
The specific embodiment of the present invention is only limitted to explain further and the present invention is described, does not limit Composition of contents of the present invention.
embodiment 1:the preparation of Tropisetron hydrochloride crystalline compounds
(1) joined by Tropisetron hydrochloride crude product in the mixing solutions of water that volume is 4 times of Tropisetron hydrochloride weight, acetonitrile, the volume ratio of water, acetonitrile is 3:1, is warming up to 30 DEG C, is stirred to and dissolves completely;
(2) frequency be 30KHz, under output rating is the sound field of 45W, add the mixing solutions of ethanol that volume is Tropisetron hydrochloride weight 8 times, trichloromethane, hexanaphthene while stirring, the volume ratio of ethanol, trichloromethane, hexanaphthene is 1:2:1, stirring velocity is 150 revs/min, and adding speed is 100 ml/min;
(3) after the mixing solutions of ethanol, trichloromethane, hexanaphthene adds, frequency be 25KHz, under output rating is the sound field of 40W, be cooled to-5 DEG C with 10 DEG C/h, growing the grain 2 hours, washing, vacuum-drying, obtains Tropiseiron hydrochloride compound.
As shown in Figure 1, its purity of high-performance liquid chromatogram determination is 99.9% to the X-ray powder diffraction pattern that the measurement of use Cu-K alpha-ray obtains.
experimental example 1, fluidity test
The mobility of this experimental example to the Tropisetron hydrochloride crystal that the embodiment of the present invention 1 obtains detects.
Method: according to the embodiment of the present invention 1 method continuous production 6 batches of Tropisetron hydrochlorides (batch: 1,2,3,4,5 and 6), sample from 6 batches of obtained Tropisetron hydrochlorides respectively, adopt fixed funnel method, funnel is placed in the suitable height on graph paper, Tropisetron hydrochloride crystal is freely flowed down from flare opening, until the cone top formed contacts with flare opening, measure hypotenuse and the horizontal angle (slope of repose θ) of Tropisetron hydrochloride accumulation horizon.The results are shown in Table 1:
The fluidity test result of table 1, Tropisetron hydrochloride
From the interpretation of table 1, the mobility of Tropisetron hydrochloride crystal of the present invention is fine.
experimental example 2: influence factor is tested
1, high temperature test
The Tropisetron hydrochloride crystalline compounds that Example 1 prepares, simulation listing packaging, puts in sealing clean container, place 10 days at 40 ± 2 DEG C of temperature, in the 5th day and sampling in the 10th day, detect by stability high spot reviews project, test-results compared with 0 day.
2, high humidity test
The Tropisetron hydrochloride crystalline compounds that Example 1 prepares, simulation listing packaging, put in sealing clean container, place 10 days under the condition of 25 ± 2 DEG C of relative humidity 90% ± 5%, in the 5th day and sampling in the 10th day, detect by stability high spot reviews project, test-results compared with 0 day.
3, strong illumination test
The Tropisetron hydrochloride crystalline compounds that Example 1 prepares, simulation listing packaging, puts in sealing clean container, being placed in illumination is place 10 days under the condition of 4500lx, in the 5th day and sampling in the 10th day, detect by stability high spot reviews project, result compared with 0 day.The results are shown in Table 2
Table 2 influence factor test-results
Result shows: the Tropisetron hydrochloride crystalline compounds that the present invention prepares, and its stability is good, and under high temperature, high humidity, high light conditions, equal retention is stablized.
experimental example 3: Acceleration study
The Tropisetron hydrochloride 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 relative humidity 70% ± 5% condition, at duration of test respectively at 1,2,3,6 sampling at the end of month once, each stability high spot reviews project is tested.The results are shown in Table 3.
Table 3 accelerated test result
Result shows: the Tropisetron hydrochloride crystalline compounds that the present invention prepares, known through accelerated test result, its good stability, and total assorted content is low.
experimental example 4: wettability test
1 instrument
PL203 electronic balance, LRH-250-S fixed temperature and humidity incubator, HH-400SD testing chamber for medicine stability;
2 methods
Get the glass desicator (for ensureing that salts solution is saturated, excessive salt should be had bottom moisture eliminator to exist) that bottom fills salt supersaturated solution, the built-in weighing bottle of moisture eliminator, places 48h to constant humidity in thermostat container.The Tropisetron hydrochloride crystalline compounds that Example 1 prepares and marketable material, each 2g, put in weighing bottle, accurately weighed, bottle cap is opened, puts into moisture eliminator top, put in 25 DEG C of fixed temperature and humidity incubators or 20 DEG C of stability test casees by differing temps requirement and preserve, parallel running 3 parts, weighs respectively at different time, calculates the rate of moisture absorption of different time.
Calculation formula:
result is as table 4:
Table 4 hygroscopicity test results
According to above-mentioned experiment, the water absorbability of Tropisetron hydrochloride crystalline compounds prepared by the present invention is low, good stability.
Claims (9)
1. treat a medicine Tropiseiron hydrochloride compound for nausea and vomiting, it is characterized in that: described Tropiseiron hydrochloride compound is crystal, the X-ray powder diffraction pattern that the measurement of use Cu-K alpha-ray obtains as shown in Figure 1.
2. the preparation method of the medicine Tropiseiron hydrochloride compound for the treatment of nausea and vomiting according to claim 1, is characterized in that comprising the following steps:
(1) Tropisetron hydrochloride crude product is joined in the mixing solutions of water, acetonitrile, heat up, be stirred to and dissolve completely;
(2) under the effect of sound field, the mixing solutions of ethanol, trichloromethane, hexanaphthene is added while stirring;
(3) after the mixing solutions of ethanol, trichloromethane, hexanaphthene adds, under the effect of sound field, cooling, growing the grain 2 hours, washing, vacuum-drying, obtains Tropiseiron hydrochloride compound.
3. the preparation method of the medicine Tropiseiron hydrochloride compound for the treatment of nausea and vomiting according to claim 2, it is characterized in that: the volume of the mixing solutions of water, acetonitrile described in step (1) is 4 times of Tropisetron hydrochloride weight, the volume ratio of water, acetonitrile is 3:1.
4. the preparation method of the medicine Tropiseiron hydrochloride compound for the treatment of nausea and vomiting according to claim 2, is characterized in that: step is warming up to 30 DEG C described in (1).
5. the preparation method of the medicine Tropiseiron hydrochloride compound for the treatment of nausea and vomiting according to claim 2, is characterized in that: sound field frequency described in step (2) is 30KHz, output rating is 45W.
6. the preparation method of the medicine Tropiseiron hydrochloride compound for the treatment of nausea and vomiting according to claim 2, it is characterized in that: the volume of the mixing solutions of ethanol, trichloromethane, hexanaphthene described in step (2) is 8 times of Tropisetron hydrochloride weight, the volume ratio of ethanol, trichloromethane, hexanaphthene is 1:2:1.
7. the preparation method of the medicine Tropiseiron hydrochloride compound for the treatment of nausea and vomiting according to claim 2, is characterized in that: described in step (2), stirring velocity is 150 revs/min, and adding speed is 100 ml/min.
8. the preparation method of the medicine Tropiseiron hydrochloride compound for the treatment of nausea and vomiting according to claim 2, is characterized in that: sound field frequency described in step (3) is 25KHz, output rating is 40W.
9. the preparation method of the medicine Tropiseiron hydrochloride compound for the treatment of nausea and vomiting according to claim 2, is characterized in that: cooling described in step (3) refers to and is cooled to-5 DEG C with 10 DEG C/h.
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 true CN104945397A (en) | 2015-09-30 |
| CN104945397B 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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| Country | Link |
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Cited By (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 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101033225A (en) * | 2007-04-02 | 2007-09-12 | 北京成宇化工有限公司 | Process of preparing troipisetron |
| CN102351857A (en) * | 2011-08-23 | 2012-02-15 | 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 |
| CN102532128A (en) * | 2010-12-17 | 2012-07-04 | 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 |
| CN103360386A (en) * | 2013-07-18 | 2013-10-23 | 珠海金鸿药业股份有限公司 | Tropisetron hydrochloride compound, its preparation method, and pharmaceutical composition containing the same |
-
2015
- 2015-07-30 CN CN201510455371.3A patent/CN104945397B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101033225A (en) * | 2007-04-02 | 2007-09-12 | 北京成宇化工有限公司 | Process of preparing troipisetron |
| CN102532128A (en) * | 2010-12-17 | 2012-07-04 | 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 |
| CN102351857A (en) * | 2011-08-23 | 2012-02-15 | 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 |
| CN103360386A (en) * | 2013-07-18 | 2013-10-23 | 珠海金鸿药业股份有限公司 | Tropisetron hydrochloride compound, its preparation method, and pharmaceutical composition containing the same |
Cited By (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 |
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| CN104945397B (en) | 2016-08-24 |
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Effective date of registration: 20160719 Address after: 264000 Shandong Province, Yantai City Economic and Technological Development Zone Industry odd Road No. 2, Room 102 on the right side of the vertical snow garden Simon Applicant after: YANTAI LANYANGZHICAO PHARMACEUTICAL BIOTECHNOLOGY Co.,Ltd. Applicant after: Song Changhai Address before: 108, room 2, building 266109, Qingdao blue bio Pharmaceutical Industrial Park, 368 Hedong Road, Hedong District, Qingdao, Shandong Applicant before: QINGDAO LANSHENGYANG PHARMACEUTICAL AND BIOTECHNOLOGY Co.,Ltd. |
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