CN107857779A - A kind of method for preparing high-purity phosphoric acid l-ornidazole ester disodium - Google Patents
A kind of method for preparing high-purity phosphoric acid l-ornidazole ester disodium Download PDFInfo
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- CN107857779A CN107857779A CN201610840670.3A CN201610840670A CN107857779A CN 107857779 A CN107857779 A CN 107857779A CN 201610840670 A CN201610840670 A CN 201610840670A CN 107857779 A CN107857779 A CN 107857779A
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- Prior art keywords
- phosphoric acid
- ester disodium
- ornidazole ester
- ornidazole
- stirring
- Prior art date
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 title claims abstract description 118
- 229960002313 ornidazole Drugs 0.000 title claims abstract description 62
- 229910000147 aluminium phosphate Inorganic materials 0.000 title claims abstract description 59
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 title claims abstract description 58
- 150000002148 esters Chemical class 0.000 title claims abstract description 58
- 238000000034 method Methods 0.000 title claims abstract description 13
- 239000003960 organic solvent Substances 0.000 claims abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000008213 purified water Substances 0.000 claims abstract description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 42
- 238000003756 stirring Methods 0.000 claims description 36
- 239000000047 product Substances 0.000 claims description 25
- 239000012065 filter cake Substances 0.000 claims description 24
- 238000001914 filtration Methods 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 239000003610 charcoal Substances 0.000 claims description 12
- 239000000706 filtrate Substances 0.000 claims description 12
- 239000013078 crystal Substances 0.000 claims description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 9
- 238000005360 mashing Methods 0.000 claims description 7
- 238000005406 washing Methods 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- 239000012043 crude product Substances 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 2
- 238000001953 recrystallisation Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims 1
- 239000012535 impurity Substances 0.000 abstract description 7
- 238000000746 purification Methods 0.000 abstract description 4
- 230000015556 catabolic process Effects 0.000 abstract description 2
- 238000002425 crystallisation Methods 0.000 abstract description 2
- 230000008025 crystallization Effects 0.000 abstract description 2
- 238000006731 degradation reaction Methods 0.000 abstract description 2
- 239000003643 water by type Substances 0.000 description 10
- 239000011259 mixed solution Substances 0.000 description 5
- IPWKIXLWTCNBKN-UHFFFAOYSA-N Madelen Chemical compound CC1=NC=C([N+]([O-])=O)N1CC(O)CCl IPWKIXLWTCNBKN-UHFFFAOYSA-N 0.000 description 4
- 238000010792 warming Methods 0.000 description 4
- YZEUHQHUFTYLPH-UHFFFAOYSA-N 2-nitroimidazole Chemical group [O-][N+](=O)C1=NC=CN1 YZEUHQHUFTYLPH-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000007605 air drying Methods 0.000 description 2
- 150000003851 azoles Chemical class 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- FFYTTYVSDVWNMY-UHFFFAOYSA-N 2-Methyl-5-nitroimidazole Chemical class CC1=NC=C([N+]([O-])=O)N1 FFYTTYVSDVWNMY-UHFFFAOYSA-N 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 229940058965 antiprotozoal agent against amoebiasis and other protozoal diseases nitroimidazole derivative Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229960000282 metronidazole Drugs 0.000 description 1
- VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical class [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6503—Five-membered rings
- C07F9/6506—Five-membered rings having the nitrogen atoms in positions 1 and 3
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Abstract
The invention provides a kind of process for purification for how obtaining higher purity phosphoric acid l-ornidazole ester disodium, dissolved by using appropriate purified water, appropriate organic solvent crystallization is added dropwise again, can effectively suppress degradation impurity residual, obtains high-purity phosphoric acid l-ornidazole ester disodium and stability is more preferable.
Description
Technical field
The invention belongs to chemicals crystallization technique field, more particularly to one kind prepares high-purity phosphoric acid l-ornidazole ester two
The method of sodium.
Background technology
Ornidazole is nitro imidazole derivatives, is a kind of medicine of strength anaerobe resistant and antigen insect infection, Ye Shiji
The effect of being newly made after metronidazole is higher, the course for the treatment of is shorter, tolerance is more preferable, is distributed wider array of third generation nitroimidazole in vivo
Analog derivative.
In the further research to Ornidazole, it has been found that, after Ornidazole use, a certain degree of maincenter poison can be produced
Property, and its single levo-enantiomer maincenter toxicity will be well below its raceme, this has guided one for the research of Ornidazole
New direction.The research of laevo-ornidazole and its derivative turns into a new focus.
Phosphoric acid l-ornidazole ester disodium, Chinese chemical name are the chloro- 1- of -3- (2- methyl-5-nitro -1H- imidazoles -1- bases)
Propane -2- base sodium phosphates, molecular formula C7H9ClN3Na2O6P, molecular weight are about 342.97, phosphoric acid l-ornidazole ester disodium knot
Structure formula is as follows：
N can represent 1~7.
Phosphoric acid l-ornidazole ester disodium easily produces catabolite using high temperature is refined, causes product purity not improve,
Still using low-temperature purifying method process be found surprisingly that such a method can be good at suppress catabolite generation and crystal formation more
It is stable to be not likely to produce impurity.The content of the invention
It is an object of the invention to provide the refined preparation method of phosphoric acid l-ornidazole ester disodium.
Phosphoric acid l-ornidazole ester disodium mentioned by the present invention refines preparation method through the following steps that realizing：
Phosphoric acid l-ornidazole ester disodium crude product is taken, purified water is added, lower stirring and dissolving, adds medical charcoal, stir 0-30 minutes, mistake
Filter, filtrate cooling, is slowly added dropwise organic solvent, adds crystal seed, stirring and crystallizing 4~12 hours, filters, and the mashing of filter cake acetone is washed
Wash, drain, filter cake is put in 25 DEG C~30 DEG C of air dry oven and dried 2~8 hours, obtains phosphoric acid l-ornidazole ester disodium and refines
Product.
The use of purified water is measured as phosphoric acid l-ornidazole ester disodium 1~10 again in above-mentioned refined preparation method（W/W）Times
Amount.
The use of organic solvent is measured as phosphoric acid l-ornidazole ester disodium 2~100 again in above-mentioned refined preparation method（W/W）
Measure again.
Organic solvent is acetone, ethanol, methanol, isopropanol, n-butanol, the one of normal propyl alcohol in above-mentioned refined preparation method
Kind or two kinds of solvents mixed with arbitrary proportion.
The addition of activated carbon is the 0.01-5% of purifying water volume in above-mentioned refined preparation method（W/V）.
Dissolving, dropping temperature are -10~60 DEG C in process for purification mentioned in the present invention.
Recrystallization temperature is -10~30 DEG C in process for purification mentioned in the present invention.
The process for purification method of phosphoric acid l-ornidazole ester disodium provided by the invention is easy, is easy to commercial Application, and can have
The generation that effect suppresses degradation impurity improves product purity, stability and yield.
The present invention is described in further detail with reference to embodiment, it should be understood that the scope of the present invention is non-to be only limitted to this
The scope of a little embodiments.
Embodiment 1：The preparation of phosphoric acid l-ornidazole ester disodium highly finished product
Phosphoric acid l-ornidazole ester disodium 20g is taken, adds 30ml purified waters, at room temperature stirring and dissolving, adds 0.3g medical charcoal, stirring
30 minutes, filtering, filtrate was cooled to 10 DEG C, and 380ml acetone is slowly added dropwise, and adds crystal seed, stirring and crystallizing 4~12 hours, filters,
Filter cake is beaten with acetone and washed, and is drained, and filter cake is put in 25 DEG C~30 DEG C of air dry oven and dried 2~8 hours, obtains the left Austria of phosphoric acid
Nitre azoles ester disodium highly finished product 18.2g.Yield is 91.0%.
Embodiment 2：The preparation of phosphoric acid l-ornidazole ester disodium highly finished product
Phosphoric acid l-ornidazole ester disodium 20g is taken, adds 100ml purified waters, is warming up to 40 DEG C of stirring and dissolvings, adds 1g medical charcoal,
Stirring 30 minutes, filtering, 360ml acetone is slowly added dropwise into filtrate, adds crystal seed, be cooled to 10 DEG C, stirring and crystallizing 4~12 is small
When, filtering, filter cake is beaten with acetone and washed, and is drained, and filter cake is put in 25 DEG C~30 DEG C of air dry oven and dried 2~8 hours, obtains
Phosphoric acid l-ornidazole ester disodium highly finished product 16.4g.Yield is 82.0%
Embodiment 3：The preparation of phosphoric acid l-ornidazole ester disodium highly finished product
Take 30ml purified waters to be cooled to 5 DEG C, add phosphoric acid l-ornidazole ester disodium 20g, stirring and dissolving, add 0.3g medical charcoal,
Stirring 30 minutes, filtering, 5 DEG C of filtrate temperature control, 160ml acetone is slowly added dropwise, adds crystal seed, stirring and crystallizing 4~12 hours, mistake
Filter, filter cake are beaten with acetone and washed, drained, and filter cake is put in 25 DEG C~30 DEG C of air dry oven and dried 2~8 hours, obtains phosphoric acid
L-ornidazole ester disodium highly finished product 17.8g.Yield is 89.0%
Embodiment 4：The preparation of phosphoric acid l-ornidazole ester disodium highly finished product
Phosphoric acid l-ornidazole ester disodium 20g is taken, adds 30ml purified waters, at room temperature stirring and dissolving, adds 0.5g medical charcoal, stirring
30 minutes, filtering, filtrate was cooled to 10 DEG C, the mixed solution of 100ml acetone and ethanol is slowly added dropwise（V/V=1:1）, add brilliant
Kind, stirring and crystallizing 4~12 hours, filtering, filter cake acetone mashing washing, drain, filter cake puts 25 DEG C~30 DEG C of forced air drying
Dried 2~8 hours in case, obtain phosphoric acid l-ornidazole ester disodium highly finished product 17.3g.Yield is 86.5%.
Embodiment 5：The preparation of phosphoric acid l-ornidazole ester disodium highly finished product
Phosphoric acid l-ornidazole ester disodium 20g is taken, adds 20ml purified waters, at room temperature stirring and dissolving, adds 0.2g medical charcoal, stirring
30 minutes, filtering, filtrate was warming up to 50 DEG C, the mixed solution of 200ml acetone and methanol is slowly added dropwise（V/V=2:1）, add brilliant
Kind, 10 DEG C are cooled to, stirring and crystallizing 4~12 hours, filtering, filter cake acetone mashing washing, is drained, filter cake puts 25 DEG C~30 DEG C
Air dry oven in dry 2~8 hours, obtain phosphoric acid l-ornidazole ester disodium highly finished product 15.6g.Yield is 78.0%.
Embodiment 6：The preparation of phosphoric acid l-ornidazole ester disodium highly finished product
Phosphoric acid l-ornidazole ester disodium 20g is taken, adds 20ml purified waters, at room temperature stirring and dissolving, adds 0.3g medical charcoal, stirring
30 minutes, filtering, filtrate was warming up to 50 DEG C, the mixed solution of 200ml acetone and isopropanol is slowly added dropwise（V/V=2:1）, add
Crystal seed, 10 DEG C are cooled to, stirring and crystallizing 4~12 hours, filtering, filter cake acetone mashing washing, is drained, filter cake puts 25 DEG C~30
DEG C air dry oven in dry 2~8 hours, obtain phosphoric acid l-ornidazole ester disodium highly finished product 17.9g.Yield is 89.5%.
Embodiment 7：The preparation of phosphoric acid l-ornidazole ester disodium highly finished product
Phosphoric acid l-ornidazole ester disodium 20g is taken, adds 40ml purified waters, at room temperature stirring and dissolving, adds 0.1g medical charcoal, stirring
30 minutes, filtering, filtrate was cooled to 10 DEG C, and 390ml ethanol is slowly added dropwise, and adds crystal seed, stirring and crystallizing 4~12 hours, filters,
Filter cake is beaten with acetone and washed, and is drained, and filter cake is put in 25 DEG C~30 DEG C of air dry oven and dried 2~8 hours, obtains the left Austria of phosphoric acid
Nitre azoles ester disodium highly finished product 18.0g.Yield is 90.0%.
Embodiment 8：The preparation of phosphoric acid l-ornidazole ester disodium highly finished product
Take 40ml purified waters to be cooled to 5 DEG C, add phosphoric acid l-ornidazole ester disodium 20g, stirring and dissolving, add 0.6g medical charcoal,
Stirring 30 minutes, filtering, 5 DEG C of filtrate temperature control, 180ml isopropanols are slowly added dropwise, add crystal seed, stirring and crystallizing 4~12 hours, mistake
Filter, filter cake are beaten with acetone and washed, drained, and filter cake is put in 25 DEG C~30 DEG C of air dry oven and dried 2~8 hours, obtains phosphoric acid
L-ornidazole ester disodium highly finished product 17.4g.Yield is 87.0%
Embodiment 9：The preparation of phosphoric acid l-ornidazole ester disodium highly finished product
Phosphoric acid l-ornidazole ester disodium 20g is taken, adds 60ml purified waters, at room temperature stirring and dissolving, adds 1.2g medical charcoal, stirring
30 minutes, filtering, filtrate was warming up to 50 DEG C, the mixed solution of 260ml ethanol and isopropanol is slowly added dropwise（V/V=2:1）, add
Crystal seed, 10 DEG C are cooled to, stirring and crystallizing 4~12 hours, filtering, filter cake acetone mashing washing, is drained, filter cake puts 25 DEG C~30
DEG C air dry oven in dry 2~8 hours, obtain phosphoric acid l-ornidazole ester disodium highly finished product 16.6g.Yield is 83.0%.
Embodiment 10：The preparation of phosphoric acid l-ornidazole ester disodium highly finished product
Phosphoric acid l-ornidazole ester disodium 20g is taken, adds 50ml purified waters, at room temperature stirring and dissolving, adds 0.5g medical charcoal, stirring
30 minutes, filtering, filtrate was cooled to 10 DEG C, the mixed solution of 100ml ethanol and methanol is slowly added dropwise（V/V=1:1）, add brilliant
Kind, stirring and crystallizing 4~12 hours, filtering, filter cake acetone mashing washing, drain, filter cake puts 25 DEG C~30 DEG C of forced air drying
Dried 2~8 hours in case, obtain phosphoric acid l-ornidazole ester disodium highly finished product 17.8g.Yield is 89.0%.
Embodiment 11：The refined front and rear relevant material of phosphoric acid l-ornidazole ester disodium compares
Take respectively and refine front and rear phosphoric acid l-ornidazole ester disodium, with its related impurities of high effective liquid chromatography for measuring.It the results are shown in Table 1.
The refined front and rear relevant substance-measuring result of the phosphoric acid l-ornidazole ester disodium of table 1
| Phosphoric acid l-ornidazole ester disodium crude product | Embodiment 1 | Embodiment 7 | |
| Impurity A | 5.326min(0.29%) | 5.285min (0.01%) | 5.963min(0.02%) |
| Other lists are miscellaneous | 9.764min(0.07%) | 5.285min (0.01%) | 5.963min(0.01%) |
| Total matter | 0.36% | 0.02% | 0.03% |
After refined, the impurity in phosphoric acid l-ornidazole ester disodium crude product substantially reduces.
Embodiment 12：The stability data of phosphoric acid l-ornidazole ester disodium highly finished product
Phosphoric acid l-ornidazole ester disodium of the present invention is taken, puts placement 6 under the conditions of 15 DEG C of temperature, relative humidity (RH) 65%
Month, sampled and detect in 1st month, the 2nd month, the 3rd month and the 6th the end of month, and compare in 0 day detection data, it the results are shown in Table
2。
The phosphoric acid l-ornidazole ester disodium study on the stability data of table 2
Through investigating, present invention gained phosphoric acid l-ornidazole ester disodium accelerates to place, and impurity shows that it is stable almost without increase sign
Property is good.
Claims (7)
1. a kind of phosphoric acid l-ornidazole ester disodium refines preparation method, specific method is：Phosphoric acid l-ornidazole ester disodium crude product, adds
Enter purified water, lower stirring and dissolving, add medical charcoal, stir 0-30 minutes, filtering, filtrate cooling, organic solvent is slowly added dropwise, adds
Enter crystal seed, stirring and crystallizing 4~12 hours, filtering, filter cake acetone mashing washing, drain, filter cake puts 25 DEG C~30 DEG C of air blast
Dried 2~8 hours in drying box, obtain phosphoric acid l-ornidazole ester disodium highly finished product.
It is 2. as claimed in claim 1, it is characterised in that the addition of purified water is 1~10 times of phosphoric acid l-ornidazole ester disodium（W/
W）.
It is 3. as claimed in claim 1, it is characterised in that organic solvent addition is 2~100 times of phosphoric acid l-ornidazole ester disodium（W/
W）.
It is 4. as claimed in claim 1, it is characterised in that the addition of activated carbon is the 0.01-5% of purifying water volume（W/V）.
It is 5. as claimed in claim 1, it is characterised in that organic solvent used is acetone, ethanol, methanol, isopropanol, n-butanol, just
One kind of propyl alcohol or two kinds of solvents mixed with arbitrary proportion.
It is 6. as claimed in claim 1, it is characterised in that dissolving, organic solvent temperature to be added dropwise as -10~60 DEG C.
It is 7. as claimed in claim 1, it is characterised in that recrystallization temperature is -10~30 DEG C.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610840670.3A CN107857779A (en) | 2016-09-22 | 2016-09-22 | A kind of method for preparing high-purity phosphoric acid l-ornidazole ester disodium |
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Family
ID=61698714
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| CN201610840670.3A Pending CN107857779A (en) | 2016-09-22 | 2016-09-22 | A kind of method for preparing high-purity phosphoric acid l-ornidazole ester disodium |
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Cited By (2)
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| CN109748934A (en) * | 2019-02-14 | 2019-05-14 | 扬子江药业集团南京海陵药业有限公司 | A kind of phosphoric acid l-ornidazole ester disodium heptahydrate crystal form and preparation method thereof |
| CN114075242A (en) * | 2020-08-12 | 2022-02-22 | 扬子江药业集团南京海陵药业有限公司 | Industrial production method of levoornidazole disodium phosphate |
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| CN109748934B (en) * | 2019-02-14 | 2021-05-11 | 扬子江药业集团南京海陵药业有限公司 | Levoornidazole disodium phosphate heptahydrate crystal form and preparation method thereof |
| CN114075242A (en) * | 2020-08-12 | 2022-02-22 | 扬子江药业集团南京海陵药业有限公司 | Industrial production method of levoornidazole disodium phosphate |
| CN114075242B (en) * | 2020-08-12 | 2024-02-06 | 扬子江药业集团南京海陵药业有限公司 | Industrial production method of disodium salt of left ornidazole phosphate |
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