CN110105194A - A kind of preparation method of pharmaceutical grade ironic citrate - Google Patents
A kind of preparation method of pharmaceutical grade ironic citrate Download PDFInfo
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- CN110105194A CN110105194A CN201910388610.6A CN201910388610A CN110105194A CN 110105194 A CN110105194 A CN 110105194A CN 201910388610 A CN201910388610 A CN 201910388610A CN 110105194 A CN110105194 A CN 110105194A
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
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Abstract
The invention discloses a kind of preparation methods of pharmaceutical grade ironic citrate, the following steps are included: by citric acid, iron oxide is soluble in water, the citric acid, iron oxide, the molar ratio of water is (1.1~3): 1:(40~80), reaction temperature is 75~80 DEG C, reaction time is 1~12h, it is cooled to room temperature, organic solvent is added dropwise, the molar ratio of the organic solvent and the iron oxide is (35~125): 1, 0.1~10h is stirred to react after dripping off, filtering, filter cake organic solvent washing, 40~50 DEG C are dried under reduced pressure 1~12h, obtain the pharmaceutical grade ironic citrate.The preparation method of pharmaceutical grade ironic citrate provided by the invention replaces iron chloride using iron oxide, does not have inorganic salts generation in reaction process, easy to operate, and the ironic citrate component being prepared is consistent, contains 2.5 crystallizations water, specific surface area is in 32.4~39.9m2Between/g, meet the requirement of pharmaceutical grade.
Description
Technical field
The invention belongs to organic chemistry and field of pharmaceutical chemistry technology, and in particular to a kind of preparation of pharmaceutical grade ironic citrate
Method.
Background technique
Ironic citrate is novel phosphate binder, can be used for Patients with Chronic Renal Disease, hemodialysis patients and patients undergoing peritoneal dialysis
Hyperphosphatemia.Ferric ion combination phosphate radical forms ferric phosphate and is excluded in vitro in digestive system, absorbed lemon
Acid, which is converted into bicarbonate radical in liver, can help to solve the metabolic acidosis of patient, and the ferrous iron being partially reduced is absorbed
The content of serum ferritin is improved, afterwards so as to improve the anaemia of patient.The clinical research of Japan, TaiWan, China, the U.S. shows
Ironic citrate has apparent serum phosphate lowering to act on, and compares with clinical commonly used drug sevelamer, and serum phosphate lowering effect is consistent, but has bright
The aobvious dosage for reducing EPO and Intravenous Iron in Maintenance, the reduction calcification index (Ca × P) of immediate stability prevent the excellent of soft tissue calciffication
Gesture, and dosage is small, side effect is lower, good market prospect.The structural formula of ironic citrate is as follows:
Patent CN105985232 discloses a kind of ferrum citricum and preparation method thereof of high-content, with the water of sodium citrate
The reaction of the alcohol solution of solution and ferric trichloride, then by being prepared, synthetic route is as follows:
It is indivisible by simply washing since it has a large amount of salt to generate during the reaction, eventually lead to finished product
The content of middle salt is higher, does not disclose the hydration number and specific surface area of its product.
Patent CN101253186A discloses a kind of pharmaceutical grade ferric organic compounds, its application and preparation method thereof, six water
It closes ferric chloride in aqueous solution and sodium hydroxide reaction prepares iron hydroxide, be then prepared again with citric acid reactions, synthetic route
It is as follows:
Due to that can generate a large amount of salt in iron hydroxide preparation process, desalination is gone by the method washed in technique, and
The iron hydroxide of generation is jelly, and speed is very slow when filtering, and it is long that this certainly will will lead to the production cycle, and can generate
A large amount of waste water, is unfavorable for industrialized production.
In conclusion the synthesis mesh that can all generate a large amount of inorganic salts in the synthesis technology of ironic citrate at present, and have
It is indefinite to mark compound hydration number, and the necessary component of pharmaceutical grade ironic citrate is clear, and itself and the maximum area of food-grade
It is not that specific surface area, the specific surface area of pharmaceutical grade ironic citrate will be far longer than food-grade, therefore, prepares to have and fix
The ironic citrate that molecular composition, specific surface area meet pharmaceutical grade requirement is most important.
Summary of the invention
The object of the present invention is to provide a kind of preparation method of pharmaceutical grade ironic citrate, molecular formula is fixed, specific surface area symbol
Pharmaceutical grade requirement is closed, easy to operate, reaction time is short, is suitble to industrialized production.
To achieve the goals above, The technical solution adopted by the invention is as follows:
The first aspect of the invention provides a kind of preparation method of pharmaceutical grade ironic citrate, comprising the following steps:
Citric acid, iron oxide is soluble in water, the citric acid, iron oxide, water molar ratio be (1.1~3): 1:(40
~80), reaction temperature is 75~80 DEG C, and the reaction time is 1~12h, is cooled to room temperature, and organic solvent is added dropwise, described organic molten
The molar ratio of agent and the iron oxide is (35~125): 1, it is stirred to react 0.1~10h after dripping off, filters, filter cake is with organic molten
Agent washing, 40~50 DEG C are dried under reduced pressure 1~12h, obtain the pharmaceutical grade ironic citrate.
The citric acid, iron oxide, water molar ratio be 1.2:1:55.5.
The citric acid is Citric Acid Mono.
The organic solvent is at least one of acetone, dehydrated alcohol, methanol, isopropanol, butanol, tetrahydrofuran.
The specific surface area of the pharmaceutical grade ironic citrate is 32.4~39.9m2/g。
The second aspect of the invention provides a kind of pharmaceutical grade ironic citrate of the method preparation.
Due to the adoption of the above technical scheme, the present invention has the following advantages and beneficial effects:
The preparation method of pharmaceutical grade ironic citrate provided by the invention replaces iron chloride using iron oxide, in reaction process
There is no inorganic salts generation, it is easy to operate, and the ironic citrate component being prepared is consistent, molecular formula determines, contains 2.5 crystallizations
Water, specific surface area is in 32.4~39.9m2Between/g, meet the requirement of pharmaceutical grade.
The preparation method of pharmaceutical grade ironic citrate provided by the invention, by iron oxide and excessive citric acid in aqueous solution
Middle reaction generates ironic citrate, and since excessive citric acid can be dissolved in organic solvent, and ironic citrate does not dissolve in organic solvent, because
Product is precipitated with the immiscible organic solvent of water by being added in this, and excessive citric acid is dissolved in organic solvent and water obtains
Removal, therefore final finished purity is high；Secondly entire reaction is with regard to single step reaction, and easy to operate, the yield of final product is also opposite
Height, and entirely reaction charge ratio is fixed, therefore the ironic citrate component prepared is consistent, and will by way of dropwise addition
Organic solvent is added dropwise in reaction solution, it is found that the specific surface area of final ironic citrate has reached 33m2/ g or more meets pharmaceutical grade
Requirement.
The preparation method of pharmaceutical grade ironic citrate provided by the invention replaces ferric trichloride synthesizing citric acid using iron oxide
Iron only generates product and water during the reaction, environmentally protective, can directly be incited somebody to action with the organic solvent to dissolve each other with water without processing
Product is precipitated.
Detailed description of the invention
Fig. 1 is thermogravimetric analysis (TGA) map of pharmaceutical grade ironic citrate.
Specific embodiment
In order to illustrate more clearly of the present invention, below with reference to preferred embodiment, the present invention is described further.Ability
Field technique personnel should be appreciated that following specifically described content is illustrative and be not restrictive, this should not be limited with this
The protection scope of invention.
The pharmaceutical grade ironic citrate of preparation of the embodiment of the present invention, the requirement for pharmaceutical grade ironic citrate, Japanese Drug are said
Bright book, ironic citrate specific surface area: 32.4~39.9m2/g。
Embodiment 1
A kind of preparation method of pharmaceutical grade ironic citrate is reacted as follows, comprising the following steps:
100g Citric Acid Mono (0.48mol), 63.9g iron oxide (0.4mol), the mixing of 400g water are heated to
Solution is clarified after 75~80 DEG C, insulation reaction 4 hours, stops reaction, reaction solution is cooled to room temperature, and acetone 1260g is added dropwise extremely
It in reaction solution, drips off within about 1 hour, drips off and be stirred at room temperature 1 hour, filter, filter cake 100g acetone washing, 40~50 DEG C of decompressions are dry
Dry 6 hours, obtain light tan solid ferric citrate compounds 105.4g, structural formula FeC6H5O7.2.5H2O, yield 83.8%.
As shown in Figure 1, Fig. 1 is thermogravimetric analysis (TGA) map of pharmaceutical grade ironic citrate.Contain 2.5 in sample as can be drawn from Figure 1
A crystallization water, first step are dehydration peak, and second step is caused by the degradation of sample.1H NMR (400MHz,D2O), δ
2.69 (d, J=71.4Hz, 4H).IR (KBr tabletting, cm-1), 3424.14 (ν-OH), 1617.24 (ν as COO-), 1382.49
(ν s COO-), 851.69 (δ Fe-O).
Embodiment 2
A kind of preparation method of pharmaceutical grade ironic citrate, comprising the following steps:
100g Citric Acid Mono (0.48mol), 63.9g iron oxide (0.4mol), the mixing of 400g water are heated to
75~80 DEG C, insulation reaction 4 hours, solution clarification stopped reaction, reaction solution is cooled to room temperature, dehydrated alcohol is added dropwise
1240g is dripped off into reaction solution, is dripped off and be stirred at room temperature 1 hour for about 1 hour, and filtering, filter cake is washed with 100g dehydrated alcohol, and 40
~50 DEG C are dried under reduced pressure 6 hours, obtain light tan solid ferric citrate compounds 103.2g, structural formula FeC6H5O7.2.5H2O,
Yield 82%.
Embodiment 3
A kind of preparation method of pharmaceutical grade ironic citrate, comprising the following steps:
100g Citric Acid Mono (0.48mol), 63.9g iron oxide (0.4mol), the mixing of 400g water are heated to
75~80 DEG C, insulation reaction 4 hours, solution clarification stopped reaction, reaction solution is cooled to room temperature, methanol 1270g is added dropwise extremely
It in reaction solution, drips off within about 1 hour, drips off and be stirred at room temperature 1 hour, filter, filter cake is washed with 100g methanol, and 40~50 DEG C of decompressions are dry
Dry 6 hours, obtain light tan solid ferric citrate compounds 100.1g, structural formula FeC6H5O7.2.5H2O, yield 79.6%.
Comparative example 1
Referring to the condition of patent CN105985232:
Under room temperature, it will be filtered after ferric trichloride (257g, 0.952mol) stirring and dissolving with 95% ethyl alcohol of 1.54L,
Filtrate is added in reaction flask, by sodium citrate (140g, 0.476mol) with after 350ml pure water dissolution filter, is slowly added into
In 95% ethanol solution of ferric trichloride, about 1h is added.50 DEG C or so are warming up to, insulation reaction 3h.Stop reaction, by reaction solution
It is cooled to room temperature, filters, washing 2 times is stirred at room temperature with pure water 200ml in filter cake, and filtering obtains ironic citrate crude product wet feed 90g.
Under room temperature, ironic citrate crude product wet feed 90g and pure water 270g are added in reaction flask, are heated to 50 ± 5
DEG C, suspension is cooled to room temperature by agitator treating 1h, and 30 points of washing is stirred at room temperature with 95% ethyl alcohol 30ml in filtering, filter cake
Clock, filtering, 50 ± 5 DEG C of filter cake dry 4h obtain ironic citrate 70g.Iron content is 23.2%, moisture 1.65%, specific surface area
For 6.5m2/g。
Comparative example 2
Referring to the condition of patent CN101253186:
Under room temperature, dissolution is mixed in 550g ferric chloride (FeCl36H2O), 1100ml pure water, and sodium hydrate aqueous solution is added dropwise
(244g sodium hydroxide is dissolved in pure water 1100ml), control reaction temperature are lower than 40 DEG C, drip off, and are cooled to 30 DEG C hereinafter, filtering, filter
With pure water 2500ml agitator treating 3 times, iron hydroxide wet feed and pure water 100ml are mixed evenly cake for filtering, and 490g is added
Citric acid is heated to 90-100 DEG C, insulation reaction 30 minutes, stops reaction, reaction solution is cooled to 30 DEG C hereinafter, mistake
Filter, filtrate are added into reaction flask, and acetone 3500ml is added dropwise, drips off within about 20 minutes, continue stirring 10 minutes, filtering, and filter cake is used
1400ml acetone agitator treating 3 times, filtering, filter cake obtain ironic citrate 251g in 25 ± 5 DEG C of vacuum drying 48h.Iron content is
16.1%, moisture 27.5%, specific surface area 13.5m2/g。
Ferric citrate compounds and commercially available ferric citrate compounds prepared by Examples 1 to 3 and comparative example 1~2
Sigma-F3388, the molecular formula of traditional Chinese medicines -20150714, iron content (titration), moisture (cassette, according to 2015 editions Chinese Pharmacopoeias:
0832 aquametry is measured), specific surface area (being measured according to national standard GB/T19587-2004) it is as shown in table 1:
Methods For The Determination of Iron: taking this product 1g or so, accurately weighed, set tool plug triangle iodine flask in, add 5ml hydrochloric acid,
30ml water after dissolving by heating and cooling down, adds 4g potassium iodide, closes bottle stopper at once, place 15min in the dark.Add water 100ml, uses
0.1mol/L sodium thiosulfate titrating solution titrates free-iodine (making indicator solution with starch), while making blank test.Every thio sulphur of 1ml
Sour sodium titrating solution (0.1mol/L) is equivalent to the iron of 5.585mg.
Table 1 analyzes the result of ironic citrate prepared by the present invention and comparative example, commercially available ironic citrate
Can be seen that ferric citrate compounds prepared by Examples 1 to 3 from the data in table 1 has molecular formula fixation bright
True feature, and comparative example 1, comparative example 2, commercially available Sigma-F3388, -20150714 molecular formula of traditional Chinese medicines are uncertain, embodiment
The ferric citrate compounds iron content of 1~3 preparation is higher, is greater than comparative example 2, commercially available Sigma-F3388, traditional Chinese medicines-
20150714 iron content, the ferric citrate compounds moisture of Examples 1 to 3 preparation is compared with comparative example 2, commercially available Sigma-
F3388, the moisture content of traditional Chinese medicines -20150714 are low, and the specific surface area of the ferric citrate compounds of Examples 1 to 3 preparation meets
The requirement of pharmaceutical grade ironic citrate, and the ratio table of comparative example 1, comparative example 2, commercially available Sigma-F3388, traditional Chinese medicines -20150714
Area does not meet the requirement of pharmaceutical grade ironic citrate.
Ferric citrate compounds prepared by Examples 1 to 3 and comparative example 1~2 are subjected to accelerated test, to the outer of sample
Sight, moisture, iron content, specific surface area are investigated, and data are as shown in table 2, from the data in table 2 can be seen that embodiment 1~
3 done samples have good stability, and appearance is unchanged, and other parameters are also unchanged；And prepared by comparative example 1~2
Sample, stability is poor, and appearance color is deepened, and other parameters also have a greater change.
The stability test of 2 product of table
Embodiment 4
A kind of preparation method of pharmaceutical grade ironic citrate, comprising the following steps:
100g Citric Acid Mono (0.48mol), 63.9g iron oxide (0.4mol), the mixing of 400g water are heated to
Solution is clarified after 75~80 DEG C, insulation reaction 4 hours, stops reaction, reaction solution is cooled to room temperature, and isopropanol 960g is added dropwise
It into reaction solution, dripping off within about 1 hour, drips off and be stirred at room temperature 1 hour, filter, filter cake is washed with 100g isopropanol, and 40~50 DEG C
It is dried under reduced pressure 6 hours, obtains light tan solid ferric citrate compounds 94.7g, structural formula FeC6H5O7.2.5H2O, yield
75.3%%.Iron content is 19.25%, moisture 15.65%, specific surface area 32.5m2/g。
Embodiment 5
A kind of preparation method of pharmaceutical grade ironic citrate, comprising the following steps:
100g Citric Acid Mono (0.48mol), 63.9g iron oxide (0.4mol), the mixing of 400g water are heated to
Solution is clarified after 75~80 DEG C, insulation reaction 4 hours, stops reaction, reaction solution is cooled to room temperature, and butanol 2368g is added dropwise extremely
It in reaction solution, drips off within about 1 hour, drips off and be stirred at room temperature 1 hour, filter, filter cake is washed with 100g butanol, and 40~50 DEG C of decompressions are dry
Dry 6 hours, obtain light tan solid ferric citrate compounds 90.4g, structural formula FeC6H5O7.2.5H2O, yield 71.8%%.
Iron content is 19.1%, moisture 15.7%, specific surface area 32.7m2/g。
Embodiment 6
A kind of preparation method of pharmaceutical grade ironic citrate, comprising the following steps:
100g Citric Acid Mono (0.48mol), 63.9g iron oxide (0.4mol), the mixing of 400g water are heated to
Solution is clarified after 75~80 DEG C, insulation reaction 4 hours, stops reaction, reaction solution is cooled to room temperature, and tetrahydrofuran is added dropwise
2016g is dripped off into reaction solution, is dripped off and be stirred at room temperature 1 hour for about 1 hour, and filtering, filter cake is washed with 100g tetrahydrofuran, and 40
~50 DEG C are dried under reduced pressure 6 hours, obtain light tan solid ferric citrate compounds 92.1g, structural formula FeC6H5O7.2.5H2O is received
Rate 73.2%.Iron content is 19.3%, moisture 15.5%, specific surface area 32.4m2/g。
Embodiment 7
A kind of preparation method of pharmaceutical grade ironic citrate, comprising the following steps:
125g Citric Acid Mono (0.6mol), 63.9g iron oxide (0.4mol), the mixing of 400g water are heated to
Solution is clarified after 75~80 DEG C, insulation reaction 4 hours, stops reaction, reaction solution is cooled to room temperature, and acetone 1260g is added dropwise extremely
It in reaction solution, drips off within about 1 hour, drips off and be stirred at room temperature 1 hour, filter, filter cake 100g acetone washing, 40~50 DEG C of decompressions are dry
Dry 6 hours, obtain light tan solid ferric citrate compounds 105.3g, structural formula FeC6H5O7.2.5H2O, yield
83.7%%.Iron content is 19.1%, moisture 15.4%, specific surface area 32.8m2/g。
Embodiment 8
A kind of preparation method of pharmaceutical grade ironic citrate, comprising the following steps:
166.7g Citric Acid Mono (0.8mol), 63.9g iron oxide (0.4mol), the mixing of 400g water are heated to
Solution is clarified after 75~80 DEG C, insulation reaction 4 hours, stops reaction, reaction solution is cooled to room temperature, and acetone 1260g is added dropwise extremely
It in reaction solution, drips off within about 1 hour, drips off and be stirred at room temperature 1 hour, filter, filter cake 100g acetone washing, 40~50 DEG C of decompressions are dry
Dry 6 hours, obtain light tan solid ferric citrate compounds 106.1g, structural formula FeC6H5O7.2.5H2O, yield 84.3%.
Iron content is 19.0%, moisture 15.6%, specific surface area 32.7m2/g。
Embodiment 9
A kind of preparation method of pharmaceutical grade ironic citrate, comprising the following steps:
250g Citric Acid Mono (1.2mol), 63.9g iron oxide (0.4mol), the mixing of 400g water are heated to
Solution is clarified after 75~80 DEG C, insulation reaction 4 hours, stops reaction, reaction solution is cooled to room temperature, and acetone 1260g is added dropwise extremely
It in reaction solution, drips off within about 1 hour, drips off and be stirred at room temperature 1 hour, filter, filter cake 100g acetone washing, 40~50 DEG C of decompressions are dry
Dry 6 hours, obtain light tan solid ferric citrate compounds 106.6g, structural formula FeC6H5O7.2.5H2O, yield 84.7%.
Iron content is 18.8%, moisture 15.5%, specific surface area 32.9m2/g。
Ferric citrate compounds prepared by embodiment 4~9 are subjected to accelerated test, the appearance of sample, moisture, iron are contained
Amount, specific surface area are investigated, and data are as shown in table 3, can be seen that the done sample of embodiment 4~9 from the data in table 3
It has good stability, appearance is unchanged, and other parameters are also unchanged；And sample prepared by comparative example 1~2, stability
Poor, appearance color is deepened, and other parameters also have a greater change.
The stability test of 3 product of table
The above is only presently preferred embodiments of the present invention, is not intended to limit the present invention in any form, though
So the present invention has been disclosed as a preferred embodiment, and however, it is not intended to limit the invention, any technology people for being familiar with this patent
Member without departing from the scope of the present invention, when the technology contents using above-mentioned prompt make it is a little change or be modified to
The equivalent embodiment of equivalent variations, but anything that does not depart from the technical scheme of the invention content, it is right according to the technical essence of the invention
Any simple modification, equivalent change and modification made by above embodiments, in the range of still falling within the present invention program.
Claims (6)
1. a kind of preparation method of pharmaceutical grade ironic citrate, it is characterised in that: the following steps are included:
Citric acid, iron oxide is soluble in water, the citric acid, iron oxide, water molar ratio be (1.1~3): 1:(40~
80), reaction temperature is 75~80 DEG C, and the reaction time is 1~12h, is cooled to room temperature, and organic solvent, the organic solvent is added dropwise
Molar ratio with the iron oxide is (35~125): 1, it is stirred to react 0.1~10h after dripping off, filters, filter cake organic solvent
Washing, 40~50 DEG C are dried under reduced pressure 1~12h, obtain the pharmaceutical grade ironic citrate.
2. the preparation method of pharmaceutical grade ironic citrate according to claim 1, it is characterised in that: the citric acid, oxidation
Iron, water molar ratio be 1.2:1:55.5.
3. the preparation method of pharmaceutical grade ironic citrate according to claim 1, it is characterised in that: the citric acid is a water
Citric acid.
4. the preparation method of pharmaceutical grade ironic citrate according to claim 1, it is characterised in that: the organic solvent is third
At least one of ketone, dehydrated alcohol, methanol, isopropanol, butanol, tetrahydrofuran.
5. the preparation method of pharmaceutical grade ironic citrate according to claim 1, it is characterised in that: the pharmaceutical grade citric acid
The specific surface area of iron is 32.4~39.9m2/g。
6. a kind of pharmaceutical grade ironic citrate of method preparation described in any one of claim 1 to 5.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101253186A (en) * | 2005-08-18 | 2008-08-27 | 环亚有限公司 | Ferric organic compounds, uses thereof and methods of making same |
| US20120238622A1 (en) * | 2011-01-18 | 2012-09-20 | Japan Tobacco Inc. | Iron (iii) citrate, substantially free of beta-iron hydroxide oxide |
| CN105985232A (en) * | 2015-02-02 | 2016-10-05 | 安徽省新星药物开发有限责任公司 | Ferric citrate with high iron content and preparation method therefor |
| CN107108443A (en) * | 2014-12-17 | 2017-08-29 | 拜欧弗印度制药有限公司 | The improved method for synthesizing ferric organic compounds |
| US20180222836A1 (en) * | 2015-08-05 | 2018-08-09 | Lupin Limited | Process for the Preparation of Pharmaceutical Grade Ferric Citrate |
-
2019
- 2019-05-10 CN CN201910388610.6A patent/CN110105194A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101253186A (en) * | 2005-08-18 | 2008-08-27 | 环亚有限公司 | Ferric organic compounds, uses thereof and methods of making same |
| US20120238622A1 (en) * | 2011-01-18 | 2012-09-20 | Japan Tobacco Inc. | Iron (iii) citrate, substantially free of beta-iron hydroxide oxide |
| CN107108443A (en) * | 2014-12-17 | 2017-08-29 | 拜欧弗印度制药有限公司 | The improved method for synthesizing ferric organic compounds |
| CN105985232A (en) * | 2015-02-02 | 2016-10-05 | 安徽省新星药物开发有限责任公司 | Ferric citrate with high iron content and preparation method therefor |
| US20180222836A1 (en) * | 2015-08-05 | 2018-08-09 | Lupin Limited | Process for the Preparation of Pharmaceutical Grade Ferric Citrate |
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| 李本高 等: "《现代工业水处理技术与应用》", 30 June 2004, 中国石化出版社 * |
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Application publication date: 20190809 |