CN102757378A - Preparation method of carbazochrome sodium sulfonate - Google Patents
Preparation method of carbazochrome sodium sulfonate Download PDFInfo
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- CN102757378A CN102757378A CN2012102330825A CN201210233082A CN102757378A CN 102757378 A CN102757378 A CN 102757378A CN 2012102330825 A CN2012102330825 A CN 2012102330825A CN 201210233082 A CN201210233082 A CN 201210233082A CN 102757378 A CN102757378 A CN 102757378A
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- sodium sulfonate
- purified water
- carbazochrome sodium
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- 229960004353 carbazochrome sodium sulfonate Drugs 0.000 title claims abstract description 28
- HLFCZZKCHVSOAP-WXIWBVQFSA-M sodium;(5e)-5-(carbamoylhydrazinylidene)-1-methyl-6-oxo-2,3-dihydroindole-2-sulfonate Chemical compound [Na+].NC(=O)N\N=C/1C(=O)C=C2N(C)C(S([O-])(=O)=O)CC2=C\1 HLFCZZKCHVSOAP-WXIWBVQFSA-M 0.000 title claims abstract description 28
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- 238000006243 chemical reaction Methods 0.000 claims abstract description 45
- 239000008213 purified water Substances 0.000 claims abstract description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 29
- 238000001035 drying Methods 0.000 claims abstract description 15
- 238000005406 washing Methods 0.000 claims abstract description 13
- 238000003756 stirring Methods 0.000 claims abstract description 12
- 238000001291 vacuum drying Methods 0.000 claims abstract description 11
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims abstract description 9
- 238000002425 crystallisation Methods 0.000 claims abstract description 9
- 230000008025 crystallization Effects 0.000 claims abstract description 9
- 229960002631 carbazochrome Drugs 0.000 claims abstract description 7
- 238000004090 dissolution Methods 0.000 claims abstract description 6
- 238000010438 heat treatment Methods 0.000 claims abstract description 6
- 239000007787 solid Substances 0.000 claims abstract description 6
- 238000001816 cooling Methods 0.000 claims abstract description 3
- 230000001105 regulatory effect Effects 0.000 claims abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 210000004907 gland Anatomy 0.000 claims description 7
- 150000007857 hydrazones Chemical class 0.000 claims description 7
- 238000009413 insulation Methods 0.000 claims description 7
- 235000010265 sodium sulphite Nutrition 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 5
- 238000007670 refining Methods 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- -1 Carbazochrome Sodium Sulfonates Chemical class 0.000 claims 2
- 229910052708 sodium Inorganic materials 0.000 claims 2
- 239000011734 sodium Substances 0.000 claims 2
- 238000000034 method Methods 0.000 abstract description 9
- 239000002994 raw material Substances 0.000 abstract description 6
- XSXCZNVKFKNLPR-SDQBBNPISA-N carbazochrome Chemical compound NC(=O)N/N=C/1C(=O)C=C2N(C)CC(O)C2=C\1 XSXCZNVKFKNLPR-SDQBBNPISA-N 0.000 abstract description 5
- 239000013078 crystal Substances 0.000 abstract description 5
- 230000008901 benefit Effects 0.000 abstract description 2
- 239000007795 chemical reaction product Substances 0.000 abstract description 2
- 238000004042 decolorization Methods 0.000 abstract 3
- 238000001914 filtration Methods 0.000 abstract 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 abstract 1
- 229940030225 antihemorrhagics Drugs 0.000 abstract 1
- 229960005070 ascorbic acid Drugs 0.000 abstract 1
- 235000010323 ascorbic acid Nutrition 0.000 abstract 1
- 239000011668 ascorbic acid Substances 0.000 abstract 1
- 239000003712 decolorant Substances 0.000 abstract 1
- 239000000706 filtrate Substances 0.000 abstract 1
- 238000007710 freezing Methods 0.000 abstract 1
- 230000008014 freezing Effects 0.000 abstract 1
- 239000002874 hemostatic agent Substances 0.000 abstract 1
- 230000002439 hemostatic effect Effects 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 229940001607 sodium bisulfite Drugs 0.000 abstract 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 230000002792 vascular Effects 0.000 abstract 1
- RPHLQSHHTJORHI-UHFFFAOYSA-N Adrenochrome Chemical compound O=C1C(=O)C=C2N(C)CC(O)C2=C1 RPHLQSHHTJORHI-UHFFFAOYSA-N 0.000 description 4
- 208000032843 Hemorrhage Diseases 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000000740 bleeding effect Effects 0.000 description 3
- 210000004204 blood vessel Anatomy 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000012423 maintenance Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 229960005139 epinephrine Drugs 0.000 description 2
- 230000023597 hemostasis Effects 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 102000016359 Fibronectins Human genes 0.000 description 1
- 108010067306 Fibronectins Proteins 0.000 description 1
- 229920002683 Glycosaminoglycan Polymers 0.000 description 1
- 206010018910 Haemolysis Diseases 0.000 description 1
- 240000000203 Salix gracilistyla Species 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000023555 blood coagulation Effects 0.000 description 1
- 230000004856 capillary permeability Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000008588 hemolysis Effects 0.000 description 1
- 230000002607 hemopoietic effect Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 229910000108 silver(I,III) oxide Inorganic materials 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention relates to a preparation method of carbazochrome sodium sulfonate, belonging to the technical field of preparation of vascular hemostatics. The method comprises the following steps: raw materials dissolution and reaction: putting purified water, carbazochrome, sodium bisulfite and ascorbic acid into a reaction tank, heating while stirring until the solid substances are completely dissolved, and continuing keeping the temperature to react, thereby obtaining a reaction solution; decolorization and separation: adding a decolorant into the reaction solution, keeping the temperature while stirring for decolorization, after finishing decolorization, carrying out centrifugal filtration, washing residues with purified water, carrying out centrifugal drying, and merging the centrifugal filtrates to obtain a solution to be crystallized; crystallization: regulating the pH value of the solution to be crystallized with an alkaline matter, freezing to cooling, and standing to precipitate crystals; and refinement: carrying out centrifugal filtration on the crystals, washing, carrying out centrifugal drying, and drying in a vacuum drying oven to obtain the carbazochrome sodium sulfonate. The invention has the advantages of accessible reaction raw material, short reaction steps, mild reaction conditions, high reaction yield (up to more than 90%), better reaction product quality and high purity (up to more than 99%), and is convenient and simple to operate.
Description
Technical field
The invention belongs to blood vessel hemostasis type field of medicine preparing technology, be specifically related to the preparation method of Carbazochrome Sodium Sulfonate
Background technology
Carbazochrome Sodium Sulfonate can be developed by day Honda limit pharmacy strain formula the earliest, is recorded into Pharmacopeia of Japan the 12 edition (1992) by Japanese health ministry at present.
Carbazochrome Sodium Sulfonate can strengthen capillary vessel elasticity; Reduce the permeability of capillary vessel, promote the retraction effect of capillary vessel fracture end, stablize the acidic mucopolysaccharide in capillary vessel and the surrounding tissue; Significantly shorten the bleeding time; Promoting the activity and the dissolving of fibronectin of zymoplasm, and then make the bleeding part form thrombus and reach hemostasis, is that capillary permeability increases and effective styptic of the profuse bleeding that the multiple hemorrhage and a variety of causes that produces causes.And Carbazochrome Sodium Sulfonate does not contain the bigcatkin willow acid groups, does not have generation " haemolysis " problem, does not influence hemopoietic function, simultaneously; Nonirritant, drug safety, but life-time service are water-soluble strong; Toxicity is extremely low, does not influence blood coagulation mechanism, and onset is rapid, persistent; Applied widely, be a kind of blood vessel styptic of new generation, be a kind of blood vessel reinforcer that has clinical value, the clinical demand amount is big.
are no lack of the method about synthetic Carbazochrome Sodium Sulfonate in document." Revised Structure of the Adrenochrome Sulfonate; Ac-17 and Ac-44 " literary composition that Mitsutaka Kawazu etc. delivers provides a kind of method of synthetic Carbazochrome Sodium Sulfonate, and this method is raw material with suprarenin, and cyclization generates adrenochrome under the effect of silver suboxide; Adrenochrome and Urea,amino-replace the generation carbazochrome; Carbazochrome and weakly alkaline reductive agent react and generate Carbazochrome Sodium Sulfonate, and this compound method step is more, and use more valuable reagent in the reaction; Operation is also complicated, therefore is not suitable for suitability for industrialized production.
A kind of compound method that Zhu Baoquan etc. (" newly organized medicine synthesizes handbook, 181～184 pages) provide, this compound method is starting raw material with suprarenin; Through electrolytic oxidation generation adrenochrome, to follow and Urea,amino-replacement generation carbazochrome, carbazochrome and weakly alkaline reductive agent react and the generation Carbazochrome Sodium Sulfonate; The same step of compound method is more; Use electrolytic oxidation in the reaction, operation is also complicated, therefore is not suitable for suitability for industrialized production equally
Summary of the invention
task of the present invention is a kind of raw material that helps obtaining is provided and need not to use valuable reagent, helps shortening reactions step and ensure the stationarity of reaction and be of value to and improve reaction yield and ensure purity and use the preparation method who satisfies the Carbazochrome Sodium Sulfonate that industrial amplification production requires.
Task of the present invention is accomplished like this, and a kind of preparation method of Carbazochrome Sodium Sulfonate may further comprise the steps:
A) material dissolution reaction: get purified water, suprarenal gland plain color hydrazone, sodium sulfite anhy 96 and xitix in a retort, heat while stirring, treat that solids dissolves the continued insulation reaction fully, obtains reaction solution;
B) decolouring separates, and in reaction solution, adds discoloring agent, keeps temperature to stir decolouring, after decolouring finishes, gets rid of filter, with purified water washing residue, dries, and merges and gets rid of filtrating, obtains liquid to be crystallized;
C) crystallization, with the pH value that alkaline matter is regulated liquid to be crystallized, frozen cooling leaves standstill, and separates out xln;
D) refining, earlier xln is got rid of filter, wash again and dry, and be placed on drying in the vacuum drying oven, obtain Carbazochrome Sodium Sulfonate.
in a concrete embodiment of the present invention, steps A) described in the parts by weight of purified water, suprarenal gland plain color hydrazone, sodium sulfite anhy 96 and xitix be respectively 50-100 part, 10-15 part, 5-12 part and 0.5-5 part.
in another concrete embodiment of the present invention, steps A) described in the temperature of heating be 60-90 ℃, the temperature of described continuation insulation reaction is 60-90 ℃, the time is 20-60min.
in another concrete embodiment of the present invention, step B) described in the holding temperature of insulated and stirred be 60-90 ℃, the time is 20-60min.
In another concrete embodiment of the present invention, the add-on of described discoloring agent is the 0.15-0.16%. of the weight of said reaction solution
Also have among the concrete embodiment of the present invention, described discoloring agent is a medicinal carbon.
more of the present invention and among concrete embodiment, step C) described in alkaline matter be that mass percent concentration is the sodium hydroxide solution of 5-20%; Described pH value is 5-8; Described refrigerated temperature is 0-10 ℃; The said time of leaving standstill is 8-16h.
in of the present invention and then concrete embodiment, step D) described in washing be meant earlier and use washing with acetone again with the purified water washing.
of the present invention again more and among concrete embodiment, step D) described in the vacuum tightness of vacuum drying oven be-0.08～-0.095MPa; Described drying temperature is 50-80 ℃, and be 6-10h time of drying.
in again of the present invention and then concrete embodiment, described purified water is the purified water that meets the Chinese Pharmacopoeia standard.
The advantage of
technical scheme provided by the invention is: this method reaction raw materials is easy to get; Reactions step is brief; Reaction conditions is gentle and easy to operate simple; Reaction yield is higher to be reached more than 90%; Reaction product quality is good, and the purity height can reach more than 99%.
Embodiment
can be expressly understood technical spirit of the present invention and beneficial effect more for the inspector that the makes Patent Office especially public; The applicant general elaborates with the mode of embodiment below; But the description to embodiment all is not the restriction to the present invention program, any according to the present invention design done only for pro forma but not substantial equivalent transformation all should be regarded as technical scheme category of the present invention.
Embodiment 1:
A) material dissolution reaction; 50 parts of the purified water that takes by weighing by weight, 10 parts of suprarenal gland plain color hydrazones, 8 parts of sodium sulfite anhy 96s and xitix are dropped in the retort for 1 part; Heat while stirring, when Heating temperature was 60 ℃, solids dissolved fully; Continuation obtains reaction solution at 60 ℃ of following insulation reaction 30min;
B) decolouring separates, to by steps A) to add discoloring agent in the reaction solution that obtains be medicinal carbon, the add-on of medicinal carbon be reaction solution weight 0.15%; In 60 ℃ of stirring decolouring 60min, after decolouring finishes, get rid of filter in temperature maintenance; Wash residue with purified water; Dry, merge and get rid of filtrating, obtain liquid to be crystallized;
C) crystallization, using mass percent is that 5% sodium hydroxide solution will be by step B) pH regulator to 5.5 of the liquid to be crystallized that obtains, there is crystal to separate out, under 0-2 ℃, lower the temperature and leave standstill 8h, separate out the mass crystallization body;
D) refining; Earlier to by step C) xln that obtains gets rid of filter, more successively with purified water and washing with acetone and drying, and be placed on vacuum tightness be-vacuum drying oven of 0.08MPa in vacuum-drying; Drying temperature is 60 ℃; Time is 8h, obtains Carbazochrome Sodium Sulfonate, the steps A of present embodiment), B) and D) in the purified water mentioned be the purified water that meets the Chinese Pharmacopoeia standard.
Embodiment 2:
A) material dissolution reaction; 80 parts of the purified water that takes by weighing by weight, 12 parts of suprarenal gland plain color hydrazones, 10 parts of sodium sulfite anhy 96s and xitix are dropped in the retort for 5 parts; Heat while stirring, when Heating temperature was 70 ℃, solids dissolved fully; Continuation obtains reaction solution at 70 ℃ of following insulation reaction 60min;
B) decolouring separates, to by steps A) to add discoloring agent in the reaction solution that obtains be medicinal carbon, the add-on of medicinal carbon be reaction solution weight 0.16%; In 70 ℃ of stirring decolouring 60min, after decolouring finishes, get rid of filter in temperature maintenance; Wash residue with purified water; Dry, merge and get rid of filtrating, obtain liquid to be crystallized;
C) crystallization, using mass percent is that 10% sodium hydroxide solution will be by step B) pH regulator to 6.5 of the liquid to be crystallized that obtains, there is crystal to separate out, under 2-4 ℃, lower the temperature and leave standstill 12h, separate out the mass crystallization body;
D) refining; Earlier to by step C) xln that obtains gets rid of filter, more successively with purified water and washing with acetone and drying, and be placed on vacuum tightness be-vacuum drying oven of 0.09MPa in vacuum-drying; Drying temperature is 80 ℃; Time is 6h, obtains Carbazochrome Sodium Sulfonate, the steps A of present embodiment), B) and D) in the purified water mentioned be the purified water that meets the Chinese Pharmacopoeia standard.
Embodiment 3:
A) material dissolution reaction; 100 parts of the purified water that takes by weighing by weight, 15 parts of suprarenal gland plain color hydrazones, 12 parts of sodium sulfite anhy 96s and xitix are dropped in the retort for 3 parts; Heat while stirring, when Heating temperature was 90 ℃, solids dissolved fully; Continuation obtains reaction solution at 90 ℃ of following insulation reaction 20min;
B) decolouring separates, to by steps A) to add discoloring agent in the reaction solution that obtains be medicinal carbon, the add-on of medicinal carbon be reaction solution weight 0.155%; In 90 ℃ of stirring decolouring 40min, after decolouring finishes, get rid of filter in temperature maintenance; Wash residue with purified water; Dry, merge and get rid of filtrating, obtain liquid to be crystallized;
C) crystallization, using mass percent is that 20% sodium hydroxide solution will be by step B) pH regulator to 6.0 of the liquid to be crystallized that obtains, there is crystal to separate out, under 4-6 ℃, lower the temperature and leave standstill 12h, separate out the mass crystallization body;
D) refining; Earlier to by step C) xln that obtains gets rid of filter, more successively with purified water and washing with acetone and drying, and be placed on vacuum tightness be-vacuum drying oven of 0.095MPa in vacuum-drying; Drying temperature is 50 ℃; Time is 10h, obtains Carbazochrome Sodium Sulfonate, the steps A of present embodiment), B) and D) in the purified water mentioned be the purified water that meets the Chinese Pharmacopoeia standard.
The reaction yield of the foregoing description 1 to 3 all reaches more than 90%, and the purity of the Carbazochrome Sodium Sulfonate that obtains is all more than 99%
Claims (10)
1.
A kind of preparation method of Carbazochrome Sodium Sulfonate is characterized in that may further comprise the steps:
A) material dissolution reaction: get purified water, suprarenal gland plain color hydrazone, sodium sulfite anhy 96 and xitix in a retort, heat while stirring, treat that solids dissolves the continued insulation reaction fully, obtains reaction solution;
B) decolouring separates, and in reaction solution, adds discoloring agent, keeps temperature to stir decolouring, after decolouring finishes, gets rid of filter, with purified water washing residue, dries, and merges and gets rid of filtrating, obtains liquid to be crystallized;
C) crystallization, with the pH value that alkaline matter is regulated liquid to be crystallized, frozen cooling leaves standstill, and separates out xln;
D) refining, earlier xln is got rid of filter, wash again and dry, and be placed on drying in the vacuum drying oven, obtain Carbazochrome Sodium Sulfonate.
2. the preparation method of
Carbazochrome Sodium Sulfonate according to claim 1 is characterized in that steps A) described in the parts by weight of purified water, suprarenal gland plain color hydrazone, sodium sulfite anhy 96 and xitix be respectively 50-100 part, 10-15 part, 5-12 part and 0.5-5 part.
3. the preparation method of
Carbazochrome Sodium Sulfonate according to claim 1 is characterized in that steps A) described in the temperature of heating be 60-90 ℃, the temperature of described continuation insulation reaction is 60-90 ℃, the time is 20-60min.
4. the preparation method of
Carbazochrome Sodium Sulfonate according to claim 1 is characterized in that step B) described in the holding temperature of insulated and stirred be 60-90 ℃, the time is 20-60min.
5. the preparation method of
Carbazochrome Sodium Sulfonate according to claim 1, the add-on that it is characterized in that described discoloring agent is the 0.15-0.16% of the weight of said reaction solution.
6.
is characterized in that according to the preparation method of claim 1 or 5 described Carbazochrome Sodium Sulfonates described discoloring agent is a medicinal carbon.
7. the preparation method of
Carbazochrome Sodium Sulfonate according to claim 1 is characterized in that step C) described in alkaline matter be that mass percent concentration is the sodium hydroxide solution of 5-20%; Described pH value is 5-8; Described refrigerated temperature is 0-10 ℃; The said time of leaving standstill is 8-16h.
8. the preparation method of
Carbazochrome Sodium Sulfonate according to claim 1 is characterized in that step D) described in washing be meant earlier and use washing with acetone again with the purified water washing.
9. the preparation method of
Carbazochrome Sodium Sulfonate according to claim 1 is characterized in that step D) described in the vacuum tightness of vacuum drying oven be-0.08～-0.095MPa; Described drying temperature is 50-80 ℃, and be 6-10h time of drying.
10.
According to the preparation method of claim 1 or 2 or 8 described Carbazochrome Sodium Sulfonates, it is characterized in that described purified water is the purified water that meets the Chinese Pharmacopoeia standard
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103145603A (en) * | 2013-03-15 | 2013-06-12 | 湖北济生医药有限公司 | Carbazochrome sodium sulfonate compound and medical composition thereof |
| CN104127388A (en) * | 2014-02-21 | 2014-11-05 | 杭州长典医药科技有限公司 | Special ultrafine carbazochrome sodium sulfonate powder freeze-dried preparation and preparation method thereof |
| CN104473864A (en) * | 2014-11-25 | 2015-04-01 | 陈长潭 | Carbazochrome sodium sulfonate semisolid preparation and preparation method thereof |
| CN104926710A (en) * | 2015-05-26 | 2015-09-23 | 成都天台山制药有限公司 | Carbazochrome sodium sulfonate and preparing method thereof |
| CN106632173A (en) * | 2016-12-28 | 2017-05-10 | 李玉成 | K2(C6H7O6)(HSO4) as well as preparation method and application thereof |
| CN106699704A (en) * | 2016-12-28 | 2017-05-24 | 李玉成 | Hydrogen sulfate sodium ascorbate as well as preparation method and application thereof |
| CN111848489A (en) * | 2020-06-28 | 2020-10-30 | 江苏吴中医药集团有限公司 | Preparation process of fluidized carbazochrome sodium sulfonate |
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| JPH11343282A (en) * | 1998-05-28 | 1999-12-14 | Tanabe Seiyaku Co Ltd | Preparation of carbazochrome sulfonic acid derivatives |
| EP0665009B1 (en) * | 1992-10-14 | 2000-02-16 | Nippon Shinyaku Company, Limited | Crystalline condition dislocating method |
| CN1557302A (en) * | 2004-01-15 | 2004-12-29 | 肖广常 | Carbazochrome Sodium Sulfonate infusion and its preparation method |
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2012
- 2012-07-06 CN CN2012102330825A patent/CN102757378A/en active Pending
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|---|---|---|---|---|
| EP0665009B1 (en) * | 1992-10-14 | 2000-02-16 | Nippon Shinyaku Company, Limited | Crystalline condition dislocating method |
| JPH11343282A (en) * | 1998-05-28 | 1999-12-14 | Tanabe Seiyaku Co Ltd | Preparation of carbazochrome sulfonic acid derivatives |
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Non-Patent Citations (1)
| Title |
|---|
| MITSUTAKA KAWAZU，等: "Revised structure of the adrenochrome sulfonate, Ac-17 and Ac-44", 《JOURNAL OF HETEROCYCLIC CHEMISTRY》, vol. 10, no. 6, 31 December 1973 (1973-12-31), pages 1059 - 1061 * |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103145603A (en) * | 2013-03-15 | 2013-06-12 | 湖北济生医药有限公司 | Carbazochrome sodium sulfonate compound and medical composition thereof |
| CN103145603B (en) * | 2013-03-15 | 2014-12-17 | 湖北济生医药有限公司 | Carbazochrome sodium sulfonate compound and medical composition thereof |
| CN104127388A (en) * | 2014-02-21 | 2014-11-05 | 杭州长典医药科技有限公司 | Special ultrafine carbazochrome sodium sulfonate powder freeze-dried preparation and preparation method thereof |
| CN104473864A (en) * | 2014-11-25 | 2015-04-01 | 陈长潭 | Carbazochrome sodium sulfonate semisolid preparation and preparation method thereof |
| CN104473864B (en) * | 2014-11-25 | 2017-02-22 | 陈长潭 | Carbazochrome sodium sulfonate semisolid preparation and preparation method thereof |
| CN104926710A (en) * | 2015-05-26 | 2015-09-23 | 成都天台山制药有限公司 | Carbazochrome sodium sulfonate and preparing method thereof |
| CN106632173A (en) * | 2016-12-28 | 2017-05-10 | 李玉成 | K2(C6H7O6)(HSO4) as well as preparation method and application thereof |
| CN106699704A (en) * | 2016-12-28 | 2017-05-24 | 李玉成 | Hydrogen sulfate sodium ascorbate as well as preparation method and application thereof |
| CN111848489A (en) * | 2020-06-28 | 2020-10-30 | 江苏吴中医药集团有限公司 | Preparation process of fluidized carbazochrome sodium sulfonate |
| CN111848489B (en) * | 2020-06-28 | 2022-05-20 | 江苏吴中医药集团有限公司 | Preparation process of fluidized carbazochrome sodium sulfonate |
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