CN101613323B - Method for synthesizing medicinal sulfadiazine silver - Google Patents
Method for synthesizing medicinal sulfadiazine silver Download PDFInfo
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- CN101613323B CN101613323B CN2009101621018A CN200910162101A CN101613323B CN 101613323 B CN101613323 B CN 101613323B CN 2009101621018 A CN2009101621018 A CN 2009101621018A CN 200910162101 A CN200910162101 A CN 200910162101A CN 101613323 B CN101613323 B CN 101613323B
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- sodium
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- silver
- sulfadiazine
- trifluoromethanesulfonic acid
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- UEJSSZHHYBHCEL-UHFFFAOYSA-N silver(1+) sulfadiazinate Chemical compound [Ag+].C1=CC(N)=CC=C1S(=O)(=O)[N-]C1=NC=CC=N1 UEJSSZHHYBHCEL-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 238000000034 method Methods 0.000 title claims abstract description 21
- 230000002194 synthesizing effect Effects 0.000 title abstract 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 claims abstract description 32
- 229960004306 sulfadiazine Drugs 0.000 claims abstract description 30
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 claims abstract description 30
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- 239000000843 powder Substances 0.000 claims abstract description 19
- 229910001961 silver nitrate Inorganic materials 0.000 claims abstract description 16
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000003054 catalyst Substances 0.000 claims abstract description 5
- 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 claims description 25
- 229910052708 sodium Inorganic materials 0.000 claims description 25
- 239000011734 sodium Substances 0.000 claims description 25
- HGJLYMGBCAKBLK-UHFFFAOYSA-N sodium;trifluoromethanesulfonic acid Chemical compound [Na].OS(=O)(=O)C(F)(F)F HGJLYMGBCAKBLK-UHFFFAOYSA-N 0.000 claims description 11
- -1 silver ions Chemical class 0.000 claims description 10
- 229910052709 silver Inorganic materials 0.000 claims description 9
- 239000004332 silver Substances 0.000 claims description 9
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 6
- 238000007689 inspection Methods 0.000 claims description 6
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 5
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 239000003507 refrigerant Substances 0.000 claims description 2
- UDGAQHHZTADYTO-UHFFFAOYSA-N sodium;4-amino-n-pyrimidin-2-ylbenzenesulfonamide Chemical compound [Na+].C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 UDGAQHHZTADYTO-UHFFFAOYSA-N 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 24
- JLDCNMJPBBKAHH-UHFFFAOYSA-N sodium;(4-aminophenyl)sulfonyl-pyrimidin-2-ylazanide Chemical compound [Na+].C1=CC(N)=CC=C1S(=O)(=O)[N-]C1=NC=CC=N1 JLDCNMJPBBKAHH-UHFFFAOYSA-N 0.000 abstract description 13
- 238000003786 synthesis reaction Methods 0.000 abstract description 12
- 150000003839 salts Chemical class 0.000 abstract description 6
- 238000001035 drying Methods 0.000 abstract description 4
- 229960001182 sulfadiazine sodium Drugs 0.000 abstract 3
- UZUODNWWWUQRIR-UHFFFAOYSA-L disodium;3-aminonaphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].C1=CC=C(S([O-])(=O)=O)C2=CC(N)=CC(S([O-])(=O)=O)=C21 UZUODNWWWUQRIR-UHFFFAOYSA-L 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 5
- 239000001103 potassium chloride Substances 0.000 description 5
- 235000011164 potassium chloride Nutrition 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- 239000008213 purified water Substances 0.000 description 4
- 230000009286 beneficial effect Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 229960001701 chloroform Drugs 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- AZLIIAMTCHKNJJ-UHFFFAOYSA-N potassium;trifluoromethanesulfonic acid Chemical compound [K].OS(=O)(=O)C(F)(F)F AZLIIAMTCHKNJJ-UHFFFAOYSA-N 0.000 description 1
- 238000013094 purity test Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 150000003297 rubidium Chemical class 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 238000005382 thermal cycling Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention provides a method for synthesizing medicinal sulfadiazine silver. The method comprises the steps of allowing silver nitrate solution and sulfadiazine sodium solution which are fed and stirred simultaneously to react in a reaction tank, standing, draining, centrifugally drying and obtaining a sulfadiazine silver product, wherein the synthesis reaction temperature of silver nitrate and sulfadiazine sodium is 45 to 55 DEG C, and trifluoromethanesulfonic acid (salt) catalysts are used in the process of utilizing sulfadiazine powder and sodium hydroxide to prepare the sulfadiazine sodium.
Description
Technical field
The present invention relates to a kind of compound method of medicinal Sulfadiazine Silver.
Background technology
Sulfadiazine Silver is white or off-white color crystalline powder, meets light or meets hot perishable.These article are all insoluble in water, ethanol, trichloromethane or ether.Sulfadiazine Silver records in " second one of Chinese pharmacopoeia version in 2005, its classification is a disulfonamide.At present, the purity of the medicament prodn of the Sulfadiazine Silver on the market is about about 98%.For this purity, also has the space of rising.In addition, the working method of Sulfadiazine Silver is that Sulphadiazine Sodium powder and sodium hydroxide react the generation Suthogen with 1: 1 ratio, and Suthogen reacts in 1: 1 ratio with Silver Nitrate and generates Sulfadiazine Silver afterwards.In actual production, in order to improve the utilization ratio of comparatively expensive Silver Nitrate, usually with the excessive 10%mol of Sulphadiazine Sodium.After reaction finished, this excessive part can't reclaim, and can only stay in the waste liquid and was dropped.
Summary of the invention
In order to overcome the above problems, the invention provides the method for a kind of synthetic drug with Sulfadiazine Silver.
The object of the present invention is to provide the method for a kind of synthetic drug, comprising with Sulfadiazine Silver: in the presence of trifluoromethanesulfonic acid (salt) as catalyzer, make silver nitrate solution and Sulphadiazine Sodium sodium solution with etc. mol ratio react 45-55 ℃ temperature.
In a kind of concrete mode, the temperature of reaction of Silver Nitrate and Suthogen is 45-55 ℃.Term " trifluoromethanesulfonic acid (salt) " is meant trifluoromethanesulfonic acid or fluoroform sulphonate.
In the present invention, operable catalyzer can be selected from trifluoromethanesulfonic acid, trifluoromethanesulfonic acid potassium, trifluoromethanesulfonic acid sodium.In a kind of embodiment of the present invention, used catalyzer is a trifluoromethanesulfonic acid sodium.
In a kind of embodiment of the present invention, catalyst consumption is the 0.1%-1%mol based on the Sulphadiazine Sodium powder, preferred 0.3%mol-0.8%mol, more preferably 0.5%-0.6%mol.
In a kind of embodiment of the present invention, temperature of reaction is preferably 48-52 ℃.
In a kind of embodiment of the present invention; After building-up reactions 30 minutes; Filter is done before the step, adopts the step of one or more middle inspections, and the step of said middle inspection is: leave standstill this synthetic liquid and sink until throw out; Whether after treating that upper solution is refrigerant, getting the upper solution check wherein has unprecipitated silver ions.
In a kind of embodiment of the present invention, the silver ions in the solution adopts chloride soln to detect.
Preferably, the silver ions in the solution adopts 10%HCl solution to detect.
Preferably, the whiz step is that centrifugal material is extremely done, and drying is 8 hours under 80-90 ℃.
Adopt compound method of the present invention, reactant is reacted with the basic mol ratio that equates, and reaction is complete basically, thereby avoided the waste and the environmental pollution that cause because of Sulphadiazine Sodium is excessive.
Embodiment
In the present invention, term " trifluoromethanesulfonic acid (salt) " is meant trifluoromethanesulfonic acid or fluoroform sulphonate.Wherein, under the situation of using salt, be preferably an alkali metal salt, for example sylvite, sodium salt, lithium salts, rubidium salt.Consider from the cost angle, be preferably sylvite and sodium salt.
In the present invention, earlier Sulphadiazine Sodium is converted into sodium salt or sylvite, and then in the presence of catalyzer, reacts with Silver Nitrate; When Sulphadiazine Sodium is converted to sodium salt; Preferred use sodium salt catalyzer, and when Sulphadiazine Sodium is converted to sylvite, preferably use the sylvite catalyzer.But, for above-mentioned any situation, all can use trifluoromethanesulfonic acid, because it can be converted into corresponding salt under reaction conditions.
Employed Sulphadiazine Sodium powder among the present invention: healthy pharmaceutcal corporation, Ltd provides by Shandong.
Employed Silver Nitrate among the present invention: ltd provides by Beijing chemical industry technology.
Sodium hydroxide used in the present invention: ltd provides by Beijing chemical industry technology.
Purified water: utilize the CS-industry flushing high purity water equipment of making by Suzhou City's innovation atmosphere water treatment ltd to produce.
Use trifluoromethanesulfonic acid sodium to be based on following principle as catalyzer among the present invention: the reversibility of sulfonation reaction is very useful in the organic synthesis field, and easy combine and this associative key is also opened easily between trifluoromethanesulfonic acid sodium and the Sulphadiazine Sodium powder be described; In reaction process of the present invention; Nucleophilic substitution takes place in the nitrogen at trifluoromethane sulfonic acid root negative ion attack Sulphadiazine Sodium molecule middle part, because this trifluoromethanesulfonic acid negative ion is left away easily; The carrying out of be beneficial to and the reaction of sodium hydroxide is beneficial to the carrying out of this building-up process thus.
Reach following examples below with reference to accompanying drawings and describe the present invention, but this embodiment is merely illustration purpose, and should not be construed as restriction the present invention.
Embodiment 1
Step 1: the preparation of silver nitrate solution
In dissolving vessel, 16.4kg (96 moles) Silver Nitrate is dissolved in the 135kg purified water, open steam valve; Silver nitrate solution is heated to 80 ℃; Be 30min heat-up time, and vapor pressure is controlled in the 0.2Mpa, closes cap relief valve after dissolving fully for silver nitrate solution; Filter, the Silver Nitrate after will filtering is then filtrated subsequent use among the header tank I that squeezes into synthesis tank.
Step 2: the preparation of Sulphadiazine Sodium sodium solution
3.85kg (96 moles) sodium hydroxide is added the 200kg purified water in dissolving vessel, make it fully be dissolved into sodium hydroxide solution; 24.0kg (96 moles) Sulphadiazine Sodium powder is added in the above-mentioned sodium hydroxide solution; Add trifluoromethanesulfonic acid sodium simultaneously, its consumption is 0.1%mol based on the consumption of Sulphadiazine Sodium powder, fully stirs; Be heated to 80 ℃; Be 30min heat-up time, and until Sulphadiazine Sodium powder dissolving position, the pH value of the Sulphadiazine Sodium sodium solution that generate this moment is 6.8-7.5; The Sulphadiazine Sodium sodium solution that filtered while hot generates is squeezed into filtrating among the header tank II of synthesis tank subsequent use.
Step 3: synthetic
Silver nitrate solution and Sulphadiazine Sodium solution sodium solution are put into to synthesis tank through the transfer lime of header tank I and II respectively simultaneously; The stirring of filtrating limit is put on the limit; Until two kinds of filtratings all mix and composition deposition till (generated time is 30min), temperature of reaction is 45 ℃.At this moment, measure with the precision test paper of 5.5-9.0, the pH value is 7.0 to 7.5; Leave standstill to the throw out sinking, after upper solution is limpid, get whether inspection also has unprecipitated silver ions in the upper solution; After middle inspection was qualified, it was dried to utilize drainer to filter, and filtrating enters floor drain.
The mensuration of silver ions in the solution: get upper solution 10ml with the filter paper filtering after, place tube comparison tubes, add 1ml 10%HCl, solution does not have the milkiness phenomenon then to be explained and not to have silver ions.
Step 4: wash centrifugal
The Sulfadiazine Silver of filtering after doing is added purified water, clean repeatedly three times.Afterwards, Sulfadiazine Silver is put into whizzer dewater, dry the back and dry (each centrifugation time is 20 minutes) for three times again with pure water drip washing.
Step 5: drying
It is dry that Sulfadiazine Silver after centrifugal is put into the thermal cycling baking oven, and drying temperature is 80-90 ℃, 8 hours time.
Embodiment 2
According to preparing Sulfadiazine Silver with embodiment 1 identical mode, the consumption of the trifluoromethanesulfonic acid sodium that just in the step of producing Suthogen, uses is the consumption 0.3%mol of Sulphadiazine Sodium powder, and the temperature of reaction in synthesis step is 55 ℃.
Embodiment 3
According to preparing Sulfadiazine Silver with embodiment 1 identical mode, the consumption of the trifluoromethanesulfonic acid sodium that just in the step of producing Suthogen, uses is the consumption 0.5%mol of Sulphadiazine Sodium powder, and the temperature of reaction in synthesis step is 49 ℃.
Embodiment 4
According to preparing Sulfadiazine Silver with embodiment 1 identical mode, the consumption of the trifluoromethanesulfonic acid sodium that just in the step of producing Suthogen, uses is the consumption 0.8%mol of Sulphadiazine Sodium powder, and the temperature of reaction in synthesis step is 52 ℃.
Embodiment 5
According to preparing Sulfadiazine Silver with embodiment 1 identical mode, the consumption of the trifluoromethanesulfonic acid sodium that just in the step of producing Suthogen, uses is the consumption 0.6%mol of Sulphadiazine Sodium powder, and the temperature of reaction in synthesis step is 49 ℃.
Embodiment 6
According to preparing Sulfadiazine Silver with embodiment 1 identical mode, the consumption of the trifluoromethanesulfonic acid sodium that just in the step of producing Suthogen, uses is the consumption 1%mol of Sulphadiazine Sodium powder, and the temperature of reaction in synthesis step is 45 ℃.
Comparative example 1
According to preparing Sulfadiazine Silver, just in the step of producing Suthogen, do not use catalyzer, and the temperature of reaction in synthesis step is 25 ℃ of normal temperature with embodiment 1 identical mode.
Comparative example 2
According to preparing Sulfadiazine Silver with embodiment 1 identical mode, just the consumption of Silver Nitrate is 15kg, and the usage quantity of sodium hydroxide is 3.75kg, and in the step of producing Suthogen, does not use catalyzer, and the temperature of reaction in synthesis step is 25 ℃ of normal temperature.
Evaluation of result
Product to gained carries out the test of pH value and detects its purity and productive rate, and the result lists in the table 1.Wherein:
The pH meter that uses is acidometer (model: PHS-4cT is available from Shanghai precision instrumentation ltd);
Purity testing: 2005 editions three ones (appendix IVA) measure according to Chinese Pharmacopoeia;
Wherein, the productive rate of product is to calculate with respect to the consumption of Sulphadiazine Sodium powder.
Table 1
Conclusion: under suitable temperature, can prepare the higher product of purity, under 48 to 52 ℃ of preferred temperature, can make product gas purity reach 98.5 to 98.8%; Productive rate can reach more than 97.3%; That is, productive rate has nearly improved 10%, not only is very beneficial for medicinal use; And practiced thrift cost, have more economic benefit.
The above is merely the preferred embodiments of the present invention, is not limited to the present invention, and for a person skilled in the art, the present invention can have various changes and variation.All within spirit of the present invention and principle, any modification of being done, be equal to replacement, improvement etc., all should be included within protection scope of the present invention.
Claims (9)
1. a synthetic drug is characterized in that with the method for Sulfadiazine Silver, in the presence of trifluoromethanesulfonic acid or fluoroform sulphonate as catalyzer, make silver nitrate solution and Sulphadiazine Sodium sodium solution with etc. mol ratio react 45-55 ℃ temperature.
2. method according to claim 1, wherein, said trifluoromethanesulfonic acid or fluoroform sulphonate are trifluoromethanesulfonic acid sodium or trifluoromethanesulfonic acid.
3. method according to claim 1, wherein, said Suthogen is transformed and is got by the Sulphadiazine Sodium powder, and said catalyst consumption is the 0.1%-1%mol of said Sulphadiazine Sodium powder.
4. method according to claim 3, wherein, said catalyst consumption is the 0.3%-0.8%mol of Sulphadiazine Sodium powder.
5. method according to claim 4, wherein, said catalyst consumption is the 0.5%-0.6%mol of Sulphadiazine Sodium powder.
6. synthetic drug according to claim 1 is with the method for Sulfadiazine Silver, and wherein, temperature of reaction is 48-52 ℃.
7. method according to claim 1, wherein, said method comprises the dried step of filter; Wherein, after building-up reactions 30 minutes, filter is done before the step; Adopt the step of one or more middle inspections; The step of inspection is in said: leave standstill this synthetic liquid and sink until throw out, treat that upper solution is refrigerant after, whether get upper solution check wherein has unprecipitated silver ions.
8. method according to claim 7, wherein, the silver ions in the solution adopts chloride soln to detect.
9. method according to claim 8, wherein, the silver ions in the solution adopts 10%HCl solution to detect.
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| CN2009101621018A CN101613323B (en) | 2009-08-04 | 2009-08-04 | Method for synthesizing medicinal sulfadiazine silver |
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| CN2009101621018A CN101613323B (en) | 2009-08-04 | 2009-08-04 | Method for synthesizing medicinal sulfadiazine silver |
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| CN101613323B true CN101613323B (en) | 2012-06-13 |
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| CN110833632B (en) * | 2019-08-20 | 2022-04-12 | 北京派尔特医疗科技股份有限公司 | A kind of polydopamine film and its preparation method and application |
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Non-Patent Citations (2)
| Title |
|---|
| 李海鹏 等.磺胺嘧啶在室温固相中的成盐和配位反应.《暨南大学学报（自然科学版）》.1996,第17卷(第3期),第70-74页. * |
| 腊蕾 等.微乳液反应法制备磺胺嘧啶银均匀微晶及其最佳处方评价.《广东药学院学报》.2001,第17卷(第3期),第173-174,177页. * |
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