CN105418471A - Synthetic method of carbocisteine - Google Patents
Synthetic method of carbocisteine Download PDFInfo
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- CN105418471A CN105418471A CN201510983800.4A CN201510983800A CN105418471A CN 105418471 A CN105418471 A CN 105418471A CN 201510983800 A CN201510983800 A CN 201510983800A CN 105418471 A CN105418471 A CN 105418471A
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- Prior art keywords
- crystallization
- reaction
- cysteine hydrochloride
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- GBFLZEXEOZUWRN-VKHMYHEASA-N S-carboxymethyl-L-cysteine Chemical compound OC(=O)[C@@H](N)CSCC(O)=O GBFLZEXEOZUWRN-VKHMYHEASA-N 0.000 title claims abstract description 11
- 238000010189 synthetic method Methods 0.000 title claims abstract description 7
- 229960004399 carbocisteine Drugs 0.000 title abstract 2
- 238000006243 chemical reaction Methods 0.000 claims abstract description 36
- 238000002425 crystallisation Methods 0.000 claims abstract description 35
- 230000008025 crystallization Effects 0.000 claims abstract description 35
- 238000000034 method Methods 0.000 claims abstract description 24
- 239000000463 material Substances 0.000 claims abstract description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 35
- 229960001305 cysteine hydrochloride Drugs 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- QIJRTFXNRTXDIP-UHFFFAOYSA-N (1-carboxy-2-sulfanylethyl)azanium;chloride;hydrate Chemical compound O.Cl.SCC(N)C(O)=O QIJRTFXNRTXDIP-UHFFFAOYSA-N 0.000 claims description 16
- 238000013019 agitation Methods 0.000 claims description 15
- 239000008213 purified water Substances 0.000 claims description 15
- 238000003756 stirring Methods 0.000 claims description 15
- 238000005406 washing Methods 0.000 claims description 15
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 14
- 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 12
- 239000012043 crude product Substances 0.000 claims description 12
- 238000007254 oxidation reaction Methods 0.000 claims description 12
- 238000012856 packing Methods 0.000 claims description 12
- 239000011734 sodium Substances 0.000 claims description 12
- 229910052708 sodium Inorganic materials 0.000 claims description 12
- 238000000703 high-speed centrifugation Methods 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 10
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims description 9
- 239000000047 product Substances 0.000 claims description 9
- -1 cysteine hydrochloride anhydride Chemical class 0.000 claims description 7
- 239000013078 crystal Substances 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 5
- 239000006210 lotion Substances 0.000 claims description 5
- 239000012452 mother liquor Substances 0.000 claims description 5
- 238000010791 quenching Methods 0.000 claims description 5
- 239000002994 raw material Substances 0.000 claims description 5
- LEVWYRKDKASIDU-IMJSIDKUSA-N L-cystine Chemical compound [O-]C(=O)[C@@H]([NH3+])CSSC[C@H]([NH3+])C([O-])=O LEVWYRKDKASIDU-IMJSIDKUSA-N 0.000 claims description 4
- 230000036571 hydration Effects 0.000 claims description 4
- 238000006703 hydration reaction Methods 0.000 claims description 4
- 235000021050 feed intake Nutrition 0.000 claims description 3
- 238000006722 reduction reaction Methods 0.000 claims description 3
- 238000004042 decolorization Methods 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 10
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 5
- 238000005265 energy consumption Methods 0.000 abstract description 2
- 238000005580 one pot reaction Methods 0.000 abstract description 2
- 230000009979 protective mechanism Effects 0.000 abstract 2
- 239000000243 solution Substances 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000006386 neutralization reaction Methods 0.000 description 4
- 206010013786 Dry skin Diseases 0.000 description 3
- 239000012670 alkaline solution Substances 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 206010062717 Increased upper airway secretion Diseases 0.000 description 2
- 206010036790 Productive cough Diseases 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 208000026435 phlegm Diseases 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 206010006458 Bronchitis chronic Diseases 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 208000007451 chronic bronchitis Diseases 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 208000024794 sputum Diseases 0.000 description 1
- 210000003802 sputum Anatomy 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/26—Separation; Purification; Stabilisation; Use of additives
- C07C319/28—Separation; Purification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a synthetic method of carbocisteine, wherein a two-pot reaction process in the prior art is changed into a one-pot reaction process, thereby simplifying the process and reducing devices. A low-temperature nitrogen protective process is changed into a normal-temperature nitrogen-free protective process, thereby reducing material and energy consumptions. A two-step crystallization process is changed into a one-step crystallization process, thereby reducing processes and devices and increasing the yield.
Description
Technical field
The present invention relates to a kind of method of synthesizing production S-carboxymethylcysteine.
Background technology
S-carboxymethylcysteine is a kind of safe, rapid, efficient, applied widely, expelling phlegm for arresting cough medicine that side effect is little, is mainly used in thick sputum, dys-expectoration and phlegm that the disease such as chronic bronchitis, bronchial asthma causes and blocks the sick treatment such as tracheae.
The production technique of S-carboxymethylcysteine is more, different starting raw materials can be used to carry out obtained the finished product by different operational paths, but the most direct building-up reactions closes reaction with cysteine hydrochloride and Mono Chloro Acetic Acid for raw material carries out carboxylic under weak basic condition, existing conventional technique is neutralized into neutral to weakly alkaline solution respectively with alkali by cysteine hydrochloride and Mono Chloro Acetic Acid, again the two is carried out under weak basic condition carboxylic and close reaction, configuration neutralization reaction and carboxylic is needed to close reaction two-step process equipment, and, cysteine hydrochloride is neutralized into neutral to weakly alkaline solution, oxidizable generation Gelucystine, therefore need to carry out neutralization reaction under low temperature and logical nitrogen protection, in addition, existing conventional technique needs to carry out twice crystallization purifying just can produce qualified product,
In sum, there is the deficiencies such as complex process, configuration device are many, severe reaction conditions, not easy to operate, productive rate is on the low side in prior art.
Summary of the invention
Object of the present invention solves prior art exactly and there is the deficiencies such as complex process, configuration device are many, severe reaction conditions, not easy to operate, productive rate is on the low side.
Technical scheme of the present invention is:
Synthesize a method of producing S-carboxymethylcysteine, it is characterized in that comprising the following steps:
(1) feed intake dissolving
In retort, add purified water, under agitation drop into cysteine hydrochloride monohydrate 250 kilograms or cysteine hydrochloride anhydride, Mono Chloro Acetic Acid, be stirred to whole dissolving.
(2) carboxylic closes reaction
Hydro-oxidation sodium solution is flowed in retort, control adds speed and opens water quench, control reacting liquid temperature is 15-35 DEG C, stream adds to after reacting liquid pH value reaches 7.5-9.5 and reacts 0.5-1.5 hour, halfcystine is detected by color reaction, as then added Mono Chloro Acetic Acid for the positive, continuing reaction at pH7.5-9.5 and detecting halfcystine after 0.5 hour, till feminine gender.
(3) decolorization filtering
In reaction solution, add concentrated hydrochloric acid adjust ph to 6-7, be heated to 60-70 DEG C, add gac 2-3 kilogram, stir decolouring and use metre filter while hot in crystallizer after 0.5-1.5 hour.
(4) in and crystallization
Under agitation to stream in crystallizer to add in concentrated hydrochloric acid and destainer to separating out mass crystallization, and continuing stream, to add concentrated hydrochloric acid just entirely molten to crystallization, flow hydro-oxidation sodium solution immediately to pH value 2.5-2.7, crystallization more than 4 hours is left standstill after being cooled to room temperature, under agitation minute adjustment pH2.7-3.1, leaves standstill crystallization more than 4 hours.
(5) centrifugally crystalline substance is washed
Crystal solution is discharged to the centrifugal 15-30 of whizzer high speed minute must to wet crude product, mother liquor focuses on rear discharge, wet crude product is added purified water to stir pulp, stirring is discharged to whizzer high speed centrifugation 15-30 minute after washing brilliant 20-40 minute, each under the low speed purified water even drip washing crystallization 2-4 is all over qualified to chlorine ion concentration, last high speed centrifugation 15-30 minute must wet fine work, and washing lotion focuses on rear discharge.
(6) dry packing
Within dry 6-8 hour, must fine work be done for 70-80 DEG C in the fine work that will wet input vacuum drier, be cooled to after below 35 DEG C and sieve, undertaken packing to obtain finished product by packing specifications.
Cysteine hydrochloride one hydration or cysteine hydrochloride anhydride are outside marketable material, can also be for starting raw material is through the cysteine hydrochloride reaction solution obtained by reduction reaction with Gelucystine.
Cysteine hydrochloride one hydration or cysteine hydrochloride anhydride or cysteine hydrochloride reaction solution and chloroacetic mol ratio are 1 ︰ 1.0-1.1.
Feed intake dissolving, carboxylic close reaction and decolouring three step process carry out in same equipment.
beneficial effect of the present invention:
(1) two pots of reaction process are changed into one pot reaction technique
Existing conventional technique is neutralized into neutral to weakly alkaline solution respectively with alkali by cysteine hydrochloride and Mono Chloro Acetic Acid, again the two is carried out under weak basic condition carboxylic and close reaction, configuration neutralization reaction and carboxylic is needed to close reaction two-step process equipment, present invention process neutralization reaction and carboxylic conjunction reaction two-step process is incorporated in same equipment to carry out, simplify technique, decrease equipment.
(2) technique is protected by low temperature nitrogen to change normal temperature nitrogen-less protection technique into
Eliminating in existing technique must by 0-5 DEG C of low-temp reaction of chilled brine cooling and nitrogen protection processing condition, changes into and reacting at the normal temperature of 15-35 DEG C and nitrogen-less protection, eliminate the consumption of nitrogen and chilled brine, reduce material consumption and energy consumption.
(3) two-step crystallization technique is changed into One-step crystallization technique
In existing technique be with in concentrated hydrochloric acid and destainer crystallization after centrifuging obtain thick product, again by crude product diluted hydrochloric acid dissolution, with in sodium hydroxide solution and recrystallizing and refining, change into now, by direct salt adding excessive acid in destainer hydrochloric acid and after crystallization, the crude product of solution modeling, crystallization is adjusted back again with sodium hydroxide solution, obtain product after centrifuging, decrease operation and equipment, and improve productive rate.
Embodiment
Below in conjunction with specific embodiment, the present invention is described in further detail.
Embodiment 1
In retort, add purified water 600 liters, under agitation drop into cysteine hydrochloride monohydrate 250 kilograms, Mono Chloro Acetic Acid 140 kilograms, be stirred to whole dissolving; Hydro-oxidation sodium solution is flowed in retort, control adds speed and opens water quench, controlling reacting liquid temperature is 30 DEG C, stream adds to after reacting liquid pH value reaches 8.5 and reacts 1 hour, detecting halfcystine by color reaction is the weak positive, add Mono Chloro Acetic Acid 1.5 kilograms, hydro-oxidation sodium solution is adjusted pH8.5 to continue reaction and is detected halfcystine after 0.5 hour for negative; In reaction solution, add concentrated hydrochloric acid adjust ph to 6.5, be heated to 65 DEG C, add gac 2 kilograms, stir decolouring and after 1 hour, use metre filter while hot in crystallizer; Under agitation to stream in crystallizer to add in concentrated hydrochloric acid and destainer to separating out mass crystallization, and continuing stream, to add concentrated hydrochloric acid just entirely molten to crystallization, flow hydro-oxidation sodium solution immediately to pH value 2.6, after being cooled to room temperature, leave standstill crystallization 12 hours, under agitation minute adjustment pH2.9, leaves standstill crystallization 6 hours; Crystal solution is discharged to the whizzer high speed centrifugal 20 minutes crude products that must wet, mother liquor focuses on rear discharge, wet crude product is added purified water 500 liters of pulps that stir, stirring is discharged to whizzer high speed centrifugation 20 minutes after washing brilliant 30 minutes, use the even drip washing crystallization of purified water 90 liters 3 times qualified to chlorine ion concentration under the low speed at every turn, last high speed centrifugation must wet fine work for 20 minutes, and washing lotion focuses on rear discharge; The fine work that will wet drops into 75 DEG C of dryings in vacuum drier must do fine work in 7 hours, is cooled to after below 33 DEG C and sieves, undertaken packing to obtain finished product 230 kilograms by packing specifications.
Embodiment 2
In retort, add purified water 620 liters, under agitation drop into cysteine hydrochloride anhydride 225 kilograms, Mono Chloro Acetic Acid 140 kilograms, be stirred to whole dissolving; Hydro-oxidation sodium solution is flowed in retort, control adds speed and opens water quench, controlling reacting liquid temperature is 30 DEG C, stream adds to after reacting liquid pH value reaches 8.5 and reacts 1 hour, detecting halfcystine by color reaction is the weak positive, add Mono Chloro Acetic Acid 2 kilograms, hydro-oxidation sodium solution is adjusted pH8.5 to continue reaction and is detected halfcystine after 0.5 hour for negative; In reaction solution, add concentrated hydrochloric acid adjust ph to 6.5, be heated to 70 DEG C, add gac 2 kilograms, stir decolouring and after 0.5 hour, use metre filter while hot in crystallizer; Under agitation to stream in crystallizer to add in concentrated hydrochloric acid and destainer to separating out mass crystallization, and continuing stream, to add concentrated hydrochloric acid just entirely molten to crystallization, flow hydro-oxidation sodium solution immediately to pH value 2.6, after being cooled to room temperature, leave standstill crystallization 10 hours, under agitation minute adjustment pH2.9, leaves standstill crystallization 8 hours; Crystal solution is discharged to the whizzer high speed centrifugal 20 minutes crude products that must wet, mother liquor focuses on rear discharge, wet crude product is added purified water 500 liters of pulps that stir, stirring is discharged to whizzer high speed centrifugation 20 minutes after washing brilliant 30 minutes, use the even drip washing crystallization of purified water 90 liters 3 times qualified to chlorine ion concentration under the low speed at every turn, last high speed centrifugation must wet fine work for 20 minutes, and washing lotion focuses on rear discharge; The fine work that will wet drops into 75 DEG C of dryings in vacuum drier must do fine work in 7 hours, is cooled to after below 33 DEG C and sieves, undertaken packing to obtain finished product 233 kilograms by packing specifications.
Embodiment 3
In retort, add purified water 150 liters, under agitation drop into Gelucystine 171 kilograms for starting raw material is through the cysteine hydrochloride reaction solution obtained by reduction reaction, Mono Chloro Acetic Acid 140 kilograms, be stirred to whole dissolving; In retort, flow hydro-oxidation sodium solution, control add speed and open water quench, controlling reacting liquid temperature is 30 DEG C, and stream adds to reacting liquid pH value and reaches 8.5 rear reaction 1 hour, detects halfcystine for being feminine gender by color reaction; In reaction solution, add concentrated hydrochloric acid adjust ph to 6.5, be heated to 70 DEG C, add gac 3 kilograms, stir decolouring and after 0.5 hour, use metre filter while hot in crystallizer; Under agitation to stream in crystallizer to add in concentrated hydrochloric acid and destainer to separating out mass crystallization, and continuing stream, to add concentrated hydrochloric acid just entirely molten to crystallization, flow hydro-oxidation sodium solution immediately to pH value 2.6, after being cooled to room temperature, leave standstill crystallization 10 hours, under agitation minute adjustment pH2.9, leaves standstill crystallization 8 hours; Crystal solution is discharged to the whizzer high speed centrifugal 20 minutes crude products that must wet, mother liquor focuses on rear discharge, wet crude product is added purified water 550 liters of pulps that stir, stirring is discharged to whizzer high speed centrifugation 20 minutes after washing brilliant 30 minutes, use the even drip washing crystallization of purified water 80 liters 4 times qualified to chlorine ion concentration under the low speed at every turn, last high speed centrifugation must wet fine work for 20 minutes, and washing lotion focuses on rear discharge; The fine work that will wet drops into 75 DEG C of dryings in vacuum drier must do fine work in 7 hours, is cooled to after below 33 DEG C and sieves, undertaken packing to obtain finished product 227 kilograms by packing specifications.
Claims (4)
1. a synthetic method for S-carboxymethylcysteine, is characterized in that, comprises the steps:
(1) feed intake dissolving
In retort, add purified water, under agitation drop into cysteine hydrochloride monohydrate or cysteine hydrochloride anhydride, Mono Chloro Acetic Acid, be stirred to whole dissolving;
(2) carboxylic closes reaction
Stream hydro-oxidation sodium solution in the retort in step (1), control adds speed and opens water quench, control reacting liquid temperature is 15-35 DEG C, add to after reacting liquid pH value reaches 7.5-9.5 until stream and react 0.5-1.5 hour, halfcystine is detected by color reaction, as then added Mono Chloro Acetic Acid for the positive, continuing reaction at pH7.5-9.5 and detecting halfcystine after 0.5 hour, till feminine gender;
(3) decolorization filtering
In the reaction solution in step (2), add concentrated hydrochloric acid adjust ph to 6-7, be heated to 60-70 DEG C, add gac, stir decolouring and use metre filter while hot in crystallizer after 0.5-1.5 hour;
(4) in and crystallization
Under agitation add concentrated hydrochloric acid to stream in the crystallizer in step (3), in and destainer to crystallization, and continuing stream, to add concentrated hydrochloric acid just entirely molten to crystallization, flow hydro-oxidation sodium solution immediately to pH value 2.5-2.7, crystallization more than 4 hours is left standstill after being cooled to room temperature, under agitation minute adjustment pH2.7-3.1, leaves standstill crystallization more than 4 hours, obtains crystal solution;
(5) centrifugally crystalline substance is washed
Crystal solution in step (3) is discharged to the centrifugal 15-30 of whizzer high speed minute must to wet crude product, mother liquor focuses on rear discharge, wet crude product is added purified water to stir pulp, stirring is discharged to whizzer high speed centrifugation 15-30 minute after washing brilliant 20-40 minute, rise even drip washing crystallization 2-4 all over qualified to chlorine ion concentration with purified water 80-100 under the low speed at every turn, last high speed centrifugation 15-30 minute must wet fine work, and washing lotion focuses on rear discharge;
(6) dry packing
Within dry 6-8 hour, must fine work be done for 70-80 DEG C in the fine work that will wet input vacuum drier, be cooled to after below 35 DEG C and sieve, undertaken packing to obtain finished product by packing specifications.
2. the synthetic method of S-carboxymethylcysteine as claimed in claim 1, it is characterized in that: cysteine hydrochloride one hydration or cysteine hydrochloride anhydride are outside marketable material, can also be for starting raw material is through the cysteine hydrochloride reaction solution obtained by reduction reaction with Gelucystine.
3. the synthetic method of S-carboxymethylcysteine as claimed in claim 2, is characterized in that: cysteine hydrochloride one hydration or cysteine hydrochloride anhydride or cysteine hydrochloride reaction solution and chloroacetic mol ratio are 1 ︰ 1.0-1.1.
4. the synthetic method of S-carboxymethylcysteine as claimed in claim 1, is characterized in that: reaction is closed in the dissolving that feeds intake, carboxylic and decolouring three step process carries out in same equipment.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510983800.4A CN105418471B (en) | 2015-12-24 | 2015-12-24 | A kind of synthetic method of carbocisteine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510983800.4A CN105418471B (en) | 2015-12-24 | 2015-12-24 | A kind of synthetic method of carbocisteine |
Publications (2)
| Publication Number | Publication Date |
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| CN105418471A true CN105418471A (en) | 2016-03-23 |
| CN105418471B CN105418471B (en) | 2017-09-05 |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106083673A (en) * | 2016-06-29 | 2016-11-09 | 罗江晨明生物制品有限公司 | A kind of preparation technology of carbocisteine |
| CN106565565A (en) * | 2016-10-19 | 2017-04-19 | 武汉远大弘元股份有限公司 | Preparation method of carbocisteine |
| CN110452142A (en) * | 2019-09-10 | 2019-11-15 | 云鹏医药集团有限公司 | A kind of preparation method of high-purity S- (carboxymethyl)-cysteine |
| CN111138326A (en) * | 2019-12-31 | 2020-05-12 | 宁波市远发生物工程有限公司 | Preparation method of S-carboxymethyl-L-cysteine |
| WO2021102918A1 (en) * | 2019-11-29 | 2021-06-03 | 武汉远大弘元股份有限公司 | Method for preparing carbocisteine |
| CN115160197A (en) * | 2021-04-01 | 2022-10-11 | 广东众生药业股份有限公司 | Preparation method of carbocisteine bulk drug |
| CN116143674A (en) * | 2022-12-20 | 2023-05-23 | 云鹏医药集团有限公司 | Synthesis method of high-purity carbocisteine |
| CN116239507A (en) * | 2022-12-22 | 2023-06-09 | 峨眉山市龙腾生物科技有限公司 | Preparation process of carbocisteine |
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106083673A (en) * | 2016-06-29 | 2016-11-09 | 罗江晨明生物制品有限公司 | A kind of preparation technology of carbocisteine |
| CN106083673B (en) * | 2016-06-29 | 2017-11-03 | 罗江晨明生物制品有限公司 | A kind of preparation technology of carbocisteine |
| CN106565565A (en) * | 2016-10-19 | 2017-04-19 | 武汉远大弘元股份有限公司 | Preparation method of carbocisteine |
| CN106565565B (en) * | 2016-10-19 | 2018-08-03 | 武汉远大弘元股份有限公司 | A kind of preparation method of carbocisteine |
| CN110452142A (en) * | 2019-09-10 | 2019-11-15 | 云鹏医药集团有限公司 | A kind of preparation method of high-purity S- (carboxymethyl)-cysteine |
| WO2021102918A1 (en) * | 2019-11-29 | 2021-06-03 | 武汉远大弘元股份有限公司 | Method for preparing carbocisteine |
| CN111138326A (en) * | 2019-12-31 | 2020-05-12 | 宁波市远发生物工程有限公司 | Preparation method of S-carboxymethyl-L-cysteine |
| CN115160197A (en) * | 2021-04-01 | 2022-10-11 | 广东众生药业股份有限公司 | Preparation method of carbocisteine bulk drug |
| CN116143674A (en) * | 2022-12-20 | 2023-05-23 | 云鹏医药集团有限公司 | Synthesis method of high-purity carbocisteine |
| CN116239507A (en) * | 2022-12-22 | 2023-06-09 | 峨眉山市龙腾生物科技有限公司 | Preparation process of carbocisteine |
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