CN106397374A - Method for preparing ranitidine hydrochloride compound as drug for treating stomach diseases - Google Patents
Method for preparing ranitidine hydrochloride compound as drug for treating stomach diseases Download PDFInfo
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- CN106397374A CN106397374A CN201610807242.0A CN201610807242A CN106397374A CN 106397374 A CN106397374 A CN 106397374A CN 201610807242 A CN201610807242 A CN 201610807242A CN 106397374 A CN106397374 A CN 106397374A
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- Prior art keywords
- ranitidine hydrochloride
- hydrochloride compound
- ranitidine
- compound
- grain
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
Abstract
The invention discloses a method for preparing a ranitidine hydrochloride compound as a drug for treating stomach diseases and belongs to the technical field of medicine. The X-ray powder diffraction pattern of the prepared compound, measured by using the Cu-K alpha ray, is shown in FIG. 1. The novel crystal-form structure of the ranitidine hydrochloride compound is different form existing crystal-form structures in the prior art. The experimental verification result shows that, the ranitidine hydrochloride compound of the novel crystal-form structure does not easily absorb moisture and is good in stability. The problems in the prior art that ranitidine hydrochloride is not stable after absorbing moisture, being heated or getting in contact with the air so as to cause the phenomena of easy oxidization, easy moisture absorption and color changing, poor stability and the like can be fundamentally solved. Therefore, the ranitidine hydrochloride compound facilitates the manufacture of preparations.
Description
The application is the joyful Pharmaceutical Technology Co., Ltd of applicant Yantai City Chinese, the invention of Wang Yufeng, Li Xianmeng proposition
Patent application（Invention entitled：A kind of treat medicine ranitidine hydrochloride compound of stomach trouble and preparation method thereof, application number
For：201510273209X, the applying date is：On May 26th, 2015）Divisional application.
Technical field
The invention belongs to pharmaceutical technology field, it is related to a kind of preparation of the medicine ranitidine hydrochloride compound treating stomach trouble
Method.
Background technology
Ranitidine is the medicine of most widely used treatment canker at present as Cimetidine.By Britain Ge Lan element
（glaxo）Company develops.1976 by Britain's Price（price）Deng synthesis, Bradshaw in 1979（bradshaw）Illustrate
Its pharmacology, bass tower in 1980（berstad）Report for duodenal ulcer effectively, listing in 1981, in the world more or less a hundred
Countries use.China was produced by Shanghai No.6 Pharmaceutical Factory in 1985.
Ranitidine is a selective bisfentidine, can effectively suppress histamine, pentagastrin and food thorn
The gastric acid secretion causing after swashing, reduces the activity of hydrochloric acid in gastric juice and gastric enzyme, but the secretion on gastrin and sex hormone no affects.Effect ratio
Cimetidine is strong 5～8 times, high to the curative effect of gastric and duodenal ulcer, has the characteristics that quick-acting and long-acting, Small side effects and
Safety.30～90 minutes after single oral 80mg, average Cmax is 165ng/ml, effect lasts 12 hours.
Ranitidine absorbs soon, is not affected by food and antiacid.Oral administration biaavailability is about 50%, t1/2 and is about
2～2.7 hours, slightly long compared with Cimetidine.Gastric acid secretion minimizing 30% that interior energy make pentagastrin to cause is administered orally latter 12 hours.
Intravenous 1mg/kg, instantaneous blood concentration is 3000ng/ml, maintains more than 100ng/ml up to 4 hours；With 0.5ng/ per hour
After kg speed intravenous infusion, 30～60 minutes blood concentration peakings, are proportionate between Cmax and dosage.Major part is arranged from kidney with original shape
Let out, renal clearance is every point of 7.2ml/kg.
Ranitidine hydrochloride heat, wet, air extremely unstable, product is easily oxidized and easy decomposed metamorphic during hyperpyrexia.Due to
Bulk drug is easy to the moisture absorption, leads to variable color, the reason such as stability difference, has had a strong impact on formulation products quality, to the preparation of preparation
Bring difficulty.
Therefore, it is necessary to develop a kind of ranitidine hydrochloride noval chemical compound, fundamentally solve ranitidine hydrochloride meet wet,
Heat, air unstable, product is easily oxidized, easy moisture absorption variable color, stability difference the problems such as, be the preparation provides convenient of preparation.
Content of the invention
The goal of the invention of the present invention is to provide a kind of medicine ranitidine hydrochloride compound treating stomach trouble and its preparation
Method.
In order to realize the purpose of the present invention, the technical scheme of employing is：
A kind of medicine ranitidine hydrochloride compound treating stomach trouble is it is characterised in that described ranitidine hydrochloride compound
The X-ray powder diffraction figure being obtained using Cu-K alpha ray measurement is as shown in Figure 1.
A kind of method of the medicine ranitidine hydrochloride compound preparing treatment stomach trouble of the present invention, comprises the steps：Will
Ranitidine hydrochloride solid dissolving is in methanol solution；It is initially charged the mixed solvent of ethanol, acetone, stirring while adding, control temperature
20-25 DEG C of degree, growing the grain 0.5-1 hour；Then acetone, the mixed solvent of 2,4- lutidines, growing the grain 1-2 hour are added
Afterwards, lower the temperature, be then kept stirring for speed 120-150 rev/min stirring and crystallizing, growing the grain 2-3 hour；Filter, be dried to obtain hydrochloric acid
Ranitidine crystalline compounds.
Preferably, the volume of described methanol solution is 8-10 times of ranitidine hydrochloride weight.
Preferably, the temperature of described methanol solution is 20-25 DEG C.
Preferably, the volume total amount being initially charged the mixed solvent of ethanol, acetone is the 10-12 of ranitidine hydrochloride weight
Times, ethanol is 1.5 with the volume ratio of acetone:1.
Preferably, adding acetone, the volume total amount of the mixed solvent of 2,4- lutidines is ranitidine hydrochloride
12-25 times of weight, the volume ratio of acetone and 2,4- lutidines is 3:2.
Preferably, described cooling is to be cooled to -5 DEG C with 10-15 DEG C/h of speed.
Preferably, described drying condition is 40-50 DEG C, drying under reduced pressure.
Below technical scheme is made further explanation：
The present invention passes through to change the crystallization condition of ranitidine hydrochloride, prepares a kind of new ranitidine hydrochloride compound, leads to
Cross the X-ray powder diffraction figure obtaining using Cu-K alpha ray measurement as shown in Figure 1.
The preparation method of the present invention, finely controls to crystallization condition, has obtained a kind of new crystalline compounds.The present invention is led to
Cross the control to temperature, mixing speed etc., thus the crystallization process of stricter control solution.
In ranitidine hydrochloride crystallization process, add the mixed of two kinds of solvents formation in the methanol solution of ranitidine hydrochloride
Bonding solvent, then pass through gradient crystallization, growing the grain, the means such as slow cooling, stirring, thus control the crystallization of ranitidine hydrochloride
Journey.Simultaneously by the way of gradient crystallization, organic solvent carries out slow cooling after adding, the speed of cooling be with 10-15 DEG C/
The speed of hour is cooled to -5 DEG C.Strict control by multiple crystallization and to Crystallization Process, has obtained a kind of new hydrochloric acid
Ranitidine compound.
Through it is experimentally confirmed that prepared by the present invention ranitidine hydrochloride compound is difficult moisture absorption, good stability, from basic
On solve ranitidine hydrochloride and meet that wet, hot, air is unstable, product is easily oxidized, easy moisture absorption variable color, and stability difference etc. is asked
Topic, is that the preparation of preparation provides conveniently.
Brief description
Fig. 1 is the X-ray powder diffraction collection of the ranitidine hydrochloride compound of the embodiment of the present invention 1 preparation.
Specific embodiment
Below by specific embodiment, the content of the invention of the present invention is described in further detail, but does not therefore limit
Determine present disclosure.
Embodiment 1：The preparation method of ranitidine hydrochloride compound, step is as follows：
By ranitidine hydrochloride solid dissolving in 20 DEG C of volumes be ranitidine hydrochloride weight 8 times of methanol solutions in；It is initially charged
Volume total amount is 10 times of ethanol of ranitidine hydrochloride weight, the mixed solvent of acetone, and ethanol with the volume ratio of acetone is
1.5:1, stirring while adding, control 20 DEG C of temperature, growing the grain 0.5 hour；Then adding volume total amount is ranitidine hydrochloride weight
12 times of acetone of amount, the mixed solvent of 2,4- lutidines, the volume ratio of acetone and 2,4- lutidines is 3:2, support
After brilliant 1 hour, it is cooled to -5 DEG C with 10 DEG C/h of speed, is then kept stirring for speed 120 revs/min of stirring and crystallizing, growing the grains
2 hours；Filter, 40 DEG C, drying under reduced pressure obtain ranitidine hydrochloride crystalline compounds.
The X-ray powder diffraction that the ranitidine hydrochloride compound crystal preparing is obtained using Cu-K alpha ray measurement
Figure is as shown in Figure 1.
Embodiment 2：The preparation method of ranitidine hydrochloride compound, step is as follows：
By ranitidine hydrochloride solid dissolving in 22.5 DEG C of volumes be ranitidine hydrochloride weight 9 times of methanol solutions in；First plus
Entering volume total amount is 11 times of ethanol of ranitidine hydrochloride weight, the mixed solvent of acetone, and ethanol with the volume ratio of acetone is
1.5:1, stirring while adding, control 22.5 DEG C of temperature, growing the grain 0.75 hour；Then adding volume total amount is ranitidine hydrochloride
18.5 times of acetone of weight, the mixed solvent of 2,4- lutidines, the volume ratio of acetone and 2,4- lutidines is 3:
2, growing the grain, after 1.5 hours, is cooled to -5 DEG C with 12.5 DEG C/h of speed, is then kept stirring for 135 revs/min of stirrings of speed
Crystallization, growing the grain 2.5 hours；Filter, 45 DEG C, drying under reduced pressure obtain ranitidine hydrochloride crystalline compounds.
The X-ray powder diffraction figure of the crystal that the ranitidine hydrochloride compound crystal preparing is prepared with embodiment 1
The characteristic peak of spectrum is identical.
Embodiment 3：The preparation method of ranitidine hydrochloride compound, step is as follows：
By ranitidine hydrochloride solid dissolving in 25 DEG C of volumes be ranitidine hydrochloride weight 10 times of methanol solutions in；It is initially charged
Volume total amount is 12 times of ethanol of ranitidine hydrochloride weight, the mixed solvent of acetone, and ethanol with the volume ratio of acetone is
1.5:1, stirring while adding, control 25 DEG C of temperature, growing the grain 1 hour；Then adding volume total amount is ranitidine hydrochloride weight
25 times of acetone, the mixed solvent of 2,4- lutidines, the volume ratio of acetone and 2,4- lutidines is 3:2, growing the grain 2
After hour, it is cooled to -5 DEG C with 15 DEG C/h of speed, be then kept stirring for 150 revs/min of stirring and crystallizing of speed, growing the grain 3 little
When；Filter, 50 DEG C, drying under reduced pressure obtain ranitidine hydrochloride crystalline compounds.
The X-ray powder diffraction figure of the crystal that the ranitidine hydrochloride compound crystal preparing is prepared with embodiment 1
The characteristic peak of spectrum is identical.
Experimental example 1
1. hot test
Three batches of the ranitidine hydrochloride compound that Example 1 prepares 101,102,103, simulation listing packaging, put
In sealing clean container, place 10 days at a temperature of 40 ± 2 DEG C, sampled in the 5th day and the 10th day, by stability high spot reviews item
Mesh is detected, result of the test was compared with 0 day.
2. high humility test
Three batches of the ranitidine hydrochloride compound that Example 1 prepares 101,102,103, simulation listing packaging, put
In sealing clean container, place 10 days under conditions of 25 ± 2 DEG C of relative humidity 90% ± 5%, sampled in the 5th day and the 10th day,
Detected by stability high spot reviews project, result of the test compared 3. strong illumination tests with 0 day
Three batches of the ranitidine hydrochloride compound that Example 1 prepares 101,102,103, simulation listing packaging, put
In sealing clean container, it is placed in illumination for placing 10 days under conditions of 4500lx, sampled in the 5th day and the 10th day, by stability
High spot reviews project is detected, result was compared with 0 day, and result is as shown in table 1.
Table 1 high temperature, high humidity, the illumination impact result of the test to ranitidine hydrochloride compound
Result shows：The ranitidine hydrochloride compound that the present invention prepares, its stability is good, in high temperature, high humidity, strong
Under illumination condition, all keep stable performance.The ranitidine hydrochloride compound of other embodiments of the present invention preparation is affected
Factor Experiment, has obtained identical experimental result.
Experimental example 2：Acceleration study
Three batches 201,202,203 of the ranitidine hydrochloride compound of Example 2 gained, simulation listing packaging, put close
In envelope clean container, place 6 months under the conditions of 42 DEG C, 80%RH, during testing, sample one respectively at 1,2,3,6 the end of month
Secondary, each stability high spot reviews project is tested.Result of the test is as shown in table 2：
Table 2 ranitidine hydrochloride compound of the present invention each stability high spot reviews item-test result
Result shows：The ranitidine hydrochloride compound that the present invention prepares, accelerated result of the test understands, its stability
Well.Acceleration study is carried out to the ranitidine hydrochloride compound of other embodiments preparation, has obtained identical experimental result.
Experimental example 3：Moisture absorption comparative test
1 instrument and reagent
1.1 instrument
PL203 electronic balance, LRH-250-S constant temperature and humidity incubator, HH-400SD testing chamber for medicine stability；
1.2 reagent
Investigational agent：The ranitidine hydrochloride compound that embodiment 1 prepares；
Comparative example 1：Singapore's imported raw material ranitidine hydrochloride（Manufacturer：GlaxoWellcome Manufacturing
Pte Ltd）；
Comparative example 2：Domestic raw material ranitidine hydrochloride（Manufacturer：Changzhou Kangpu Pharmaceutical Co., Ltd.）
2 methods
Bottom is taken to fill the glass desicator of salt supersaturated solution（For ensureing salting liquid saturation, drier bottom should have excessive
Salt exists）, the built-in measuring cup of drier, place 48h in insulating box to constant humidity.Take sample about 2g, put in measuring cup, accurate title
Fixed, bottle cap is opened, puts into drier top, put 25 DEG C of constant temperature and humidity incubators or 20 DEG C of stability examinations by different temperatures requirement
Preserve in tryoff, 3 parts of operation repetitive, weigh respectively in different time, calculate the hydroscopicity of different time.
Computing formula：Hydroscopicity=（Medicinal powder weight-moisture absorption prodrug grain weight amount after moisture absorption）/ moisture absorption prodrug grain weight amount × 100%.
Result is as shown in table 3：
Table 3 present invention is compared in the hydroscopicity of different time with comparative example 1,2
According to above-mentioned experiment, the hygroscopicity of the ranitidine hydrochloride compound of present invention preparation is less than prior art, that is, should
The stability of compound is higher than prior art.
Claims (1)
1. a kind of method of the medicine ranitidine hydrochloride compound preparing treatment stomach trouble is it is characterised in that comprise the steps：
By ranitidine hydrochloride solid dissolving in methanol solution；It is initially charged the mixed solvent of ethanol, acetone, stirring while adding, control
Temperature 20-25 DEG C, growing the grain 0.5-1 hour；Then acetone, the mixed solvent of 2,4- lutidines, growing the grain 1-2 hour are added
Afterwards, lower the temperature, be then kept stirring for speed 120-150 rev/min stirring and crystallizing, growing the grain 2-3 hour；Filter, be dried to obtain hydrochloric acid
Ranitidine crystalline compounds；
X-ray powder diffraction figure such as Fig. 1 that described prepared ranitidine hydrochloride compound is obtained using Cu-K alpha ray measurement
Shown.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610807242.0A CN106397374A (en) | 2015-05-26 | 2015-05-26 | Method for preparing ranitidine hydrochloride compound as drug for treating stomach diseases |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510273209.XA CN104817523B (en) | 2015-05-26 | 2015-05-26 | A kind of medicine ranitidine hydrochloride compound treating gastropathy and preparation method thereof |
| CN201610807242.0A CN106397374A (en) | 2015-05-26 | 2015-05-26 | Method for preparing ranitidine hydrochloride compound as drug for treating stomach diseases |
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| CN201510273209.XA Division CN104817523B (en) | 2015-05-26 | 2015-05-26 | A kind of medicine ranitidine hydrochloride compound treating gastropathy and preparation method thereof |
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| CN106397374A true CN106397374A (en) | 2017-02-15 |
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| CN201610823327.8A Active CN106432149B (en) | 2015-05-26 | 2015-05-26 | A kind of method for the medicine ranitidine hydrochloride compound for preparing treatment stomach trouble |
| CN201610823158.8A Active CN106432147B (en) | 2015-05-26 | 2015-05-26 | A kind of method for the medicine ranitidine hydrochloride compound for preparing treatment stomach trouble |
| CN201510273209.XA Active CN104817523B (en) | 2015-05-26 | 2015-05-26 | A kind of medicine ranitidine hydrochloride compound treating gastropathy and preparation method thereof |
| CN201610823211.4A Active CN106432148B (en) | 2015-05-26 | 2015-05-26 | A kind of preparation method for the medicine ranitidine hydrochloride compound for treating stomach trouble |
| CN201610807242.0A Withdrawn CN106397374A (en) | 2015-05-26 | 2015-05-26 | Method for preparing ranitidine hydrochloride compound as drug for treating stomach diseases |
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| CN201610823327.8A Active CN106432149B (en) | 2015-05-26 | 2015-05-26 | A kind of method for the medicine ranitidine hydrochloride compound for preparing treatment stomach trouble |
| CN201610823158.8A Active CN106432147B (en) | 2015-05-26 | 2015-05-26 | A kind of method for the medicine ranitidine hydrochloride compound for preparing treatment stomach trouble |
| CN201510273209.XA Active CN104817523B (en) | 2015-05-26 | 2015-05-26 | A kind of medicine ranitidine hydrochloride compound treating gastropathy and preparation method thereof |
| CN201610823211.4A Active CN106432148B (en) | 2015-05-26 | 2015-05-26 | A kind of preparation method for the medicine ranitidine hydrochloride compound for treating stomach trouble |
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Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105055396A (en) * | 2015-09-17 | 2015-11-18 | 青岛华之草医药科技有限公司 | Ranitidine hydrochloride composition freeze-dried powder injection for treating stomach illness |
| CN107382922A (en) * | 2017-08-03 | 2017-11-24 | 江苏汉斯通药业有限公司 | The preparation method of high-transmittance ranitidine hydrochloride |
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|---|---|---|---|---|
| US4521431A (en) * | 1980-10-01 | 1985-06-04 | Glaxo Group Limited | Aminoalkyl furan derivative |
| ES8706656A1 (en) * | 1985-10-23 | 1987-07-16 | Chemica Sa | Ranitidine hydrochloride prepn. |
| US5621120A (en) * | 1994-05-13 | 1997-04-15 | Ranbaxy Laboratories Limited | Process for the manufacture of form 1 ranitidine hydrochloride |
| WO1999065890A1 (en) * | 1998-06-17 | 1999-12-23 | Russinsky Limited | Ranitidine adduct |
| CN1724526A (en) * | 2005-07-11 | 2006-01-25 | 石药集团中诺药业（石家庄）有限公司 | Synthesis method of ranitidine alkali and its hydrochloride |
| CN102010389A (en) * | 2009-09-04 | 2011-04-13 | 江苏汉斯通药业有限公司 | Method for preparing ranitidine hydrochloride |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1048984C (en) * | 1991-12-20 | 2000-02-02 | 多坎化学有限公司 | Preparation of form 1 ranitidine hydrochloride |
| CA2120874E (en) * | 1994-04-08 | 2002-01-08 | Keshava Murthy | Form of form 1 ranitidine |
| KR0152469B1 (en) * | 1995-07-13 | 1998-10-15 | 이승웅 | Process for manufacturing form -ñ‹ ranitidine hydrochloride |
| WO1997035853A1 (en) * | 1996-03-25 | 1997-10-02 | Hoechst Marion Roussel, Inc. | Process for the preparation of form 1 ranitidine hydrochloride |
| US20020151729A1 (en) * | 1997-02-26 | 2002-10-17 | Cheng Wen J. | Novel process for the preparation of form 1 ranitidine hydrochloride |
| MX345168B (en) * | 2010-06-02 | 2017-01-19 | Laboratorios Senosiain S A De C V * | Process for preparing ranitidine hydrochloride form 2. |
-
2015
- 2015-05-26 CN CN201610823327.8A patent/CN106432149B/en active Active
- 2015-05-26 CN CN201610823158.8A patent/CN106432147B/en active Active
- 2015-05-26 CN CN201510273209.XA patent/CN104817523B/en active Active
- 2015-05-26 CN CN201610823211.4A patent/CN106432148B/en active Active
- 2015-05-26 CN CN201610807242.0A patent/CN106397374A/en not_active Withdrawn
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| US4521431A (en) * | 1980-10-01 | 1985-06-04 | Glaxo Group Limited | Aminoalkyl furan derivative |
| ES8706656A1 (en) * | 1985-10-23 | 1987-07-16 | Chemica Sa | Ranitidine hydrochloride prepn. |
| US5621120A (en) * | 1994-05-13 | 1997-04-15 | Ranbaxy Laboratories Limited | Process for the manufacture of form 1 ranitidine hydrochloride |
| WO1999065890A1 (en) * | 1998-06-17 | 1999-12-23 | Russinsky Limited | Ranitidine adduct |
| CN1724526A (en) * | 2005-07-11 | 2006-01-25 | 石药集团中诺药业（石家庄）有限公司 | Synthesis method of ranitidine alkali and its hydrochloride |
| CN102010389A (en) * | 2009-09-04 | 2011-04-13 | 江苏汉斯通药业有限公司 | Method for preparing ranitidine hydrochloride |
Non-Patent Citations (1)
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| 黄龙祥，等: "盐酸雷尼替丁精制方法的改进", 《中国医药工业杂志》 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN106432149B (en) | 2018-04-17 |
| CN106432147A (en) | 2017-02-22 |
| CN104817523B (en) | 2016-11-09 |
| CN106432149A (en) | 2017-02-22 |
| CN106432148B (en) | 2018-04-17 |
| CN106432148A (en) | 2017-02-22 |
| CN106432147B (en) | 2018-04-17 |
| CN104817523A (en) | 2015-08-05 |
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Inventor after: Zhu Kongxi Inventor after: Wang Yufeng Inventor before: Wang Yufeng |
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Application publication date: 20170215 |
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