CN102579356A - Preparation method of penehyclidine hydrochloride powder injection for injecting - Google Patents
Preparation method of penehyclidine hydrochloride powder injection for injecting Download PDFInfo
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- CN102579356A CN102579356A CN2012100942649A CN201210094264A CN102579356A CN 102579356 A CN102579356 A CN 102579356A CN 2012100942649 A CN2012100942649 A CN 2012100942649A CN 201210094264 A CN201210094264 A CN 201210094264A CN 102579356 A CN102579356 A CN 102579356A
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Abstract
The invention discloses a preparation method of a penehyclidine hydrochloride powder injection for injecting, which belongs to the field of medicinal supplies. The method comprises the following process steps of: dissolving a penehyclidine hydrochloride bulk pharmaceutical into a solution of absolute ethanol-absolute ether, adding an appropriate amount of active carbon for decolorizing, rough filtering for decarbonizing, and filtering with a microporous filtering film of 0.22 mum to obtain an aseptic and clear solution; in an aseptic environment, crystallizing the aseptic and clear solution of the penehyclidine hydrochloride, filtering an obtained crystal, washing, draining and drying; and detecting moisture and content, detecting aseptic state, charging into a sterilized penicillin bottle, covering with a butyl rubber plug, and rolling an aluminum cover to obtain the penehyclidine hydrochloride powder injection. Due to the adoption of the preparation method, a preparation is more stable on the aspects of pH value, relevant substances and content, the toxicity is lower, and the safety and effectiveness of the penehyclidine hydrochloride and the quality of a product are ensured more easily.
Description
Technical field
The present invention relates to a kind of method for preparing of hydrochloride for injection amyl ethyl quin ether, be specifically related to the method for preparing of amyl ethyl quin ether hydrochloride injectable powder, belong to the medical drugs field.
Background technology
Amyl ethyl quin ether hydrochloride is the new selective anticholinergic agent, can get in the brain through blood brain barrier.Its ability blockage of acetylcholine is to the agonism of M-ChR in the brain and nicotine receptor; Therefore, the maincenter poisoning symptom that antagonism organophosphorus poison poisoning preferably causes is like convulsions, maincenter respiratory and circulatory failure and dysphoria etc.Simultaneously, in periphery the agonism of stronger blockage of acetylcholine to m receptor arranged also; Thereby the muscarinic poisoning symptom that antagonism organophosphorus poison (pesticide) poisoning preferably causes is like bronchial muscular spasm and secretions increase, perspiration, curtain coating, myosis and gastrointestinal tract smooth muscle spasm or contraction etc.It can also increase respiratory frequency and respiratory flow, but because these article do not have obvious effect to the M2 receptor, so heart rate is not had obvious influence; The periphery n receptor there is not obvious antagonism.
Amyl ethyl quin ether hydrochloride belongs to the raw material variety that Chengdu Lisite Pharmaceutical Co., Ltd. exclusively has, but has only a kind of dosage form of amyl ethyl quin ether hydrochloride injection at present.Producing and selling and use through for many years find that the amyl ethyl quin ether hydrochloride injection exists pH value and related substance to raise, the weak point that content descends after high temperature sterilize or long-term storage.Find also that simultaneously related substance is high more, then the toxicity of product is strong more, and promptly product related substance and toxicity have very strong dependency.
In order to solve the insecurity and the instability problem of amyl ethyl quin ether hydrochloride injection dosage form; Find through long term test; Recrystallization method can make amyl ethyl quin ether hydrochloride raw material related substance reduce; The hydrochloride for injection amyl ethyl quin ether is processed in the sterilized powder packing can make product more stable, and it is stable that its pH value, related substance and content all keep in a long time.
Through retrieval, not finding as yet at present has solution and the pertinent literature report that proposes to the problems referred to above.
Summary of the invention
The present invention is intended to solve existing amyl ethyl quin ether hydrochloride injection after high temperature sterilize or long-term storage, and its pH value and related substance raise, the problem of content decline, and a kind of method for preparing of hydrochloride for injection amyl ethyl quin ether injectable powder is provided.The hydrochloride for injection amyl ethyl quin ether product that is obtained by this method is more stable aspect pH, content and the related substance, and product quality and drug effect are guaranteed more easily.
Concrete technical scheme of the present invention is following:
For realizing the foregoing invention purpose, the concrete technical scheme that the present invention adopts is:
A kind of method for preparing of hydrochloride for injection amyl ethyl quin ether injectable powder, it is characterized in that: processing step is following:
A, amyl ethyl quin ether hydrochloride is dissolved in dehydrated alcohol-absolute ether, heating makes its dissolving, after adding pin again and stirring decolouring with activated carbon, and first coarse filtration decarburization, the filtering with microporous membrane of reuse 0.22 μ m obtains clear liquid;
B, under gnotobasis, the clear liquid of step B is carried out recrystallization, through filtration under diminished pressure, wash, drain, 105 ℃ of dryings, pulverize and obtain the amyl ethyl quin ether hydrochloride aseptic powder, the encapsulation back is subsequent use;
The preparation of C, hydrochloride for injection amyl ethyl quin ether injectable powder
A, vial handle: vial use ultrasonic waves for cleaning, and after the pure water rinsing, the flushing of reuse water for injection, 4 hours inner dryings and sterilization must clean, aseptic, dry, apyrogenic vials; The condition of said sterilization and mode are: 180 ℃ of 1.5h or 320 ℃ of 5min of tunnel type dry heat sterilization.
B, plug handle: with plug with dilute hydrochloric acid boil wash after, with the purified water flushing,, clean the back silication again with the water for injection rinsing, remove thermal source, then with 121 ℃ of the steam 40min that sterilizes, 120 ℃ of oven dry, subsequent use.
C, bottling: after the aseptic powder that steps A is made adopts volume quantitative or screw rod metering; Quantitatively powder is divided in the vial of treated mistake through racking machine; Plug with treated mistake covers on bottleneck simultaneously, through lamp inspection, labeling, sampling, check, promptly obtains product.
The weight ratio of the said dehydrated alcohol-absolute ether of steps A is 1:0.5～1:10.
The weight ratio of the said amyl ethyl quin ether hydrochloride of steps A and dehydrated alcohol-absolute ether is 1:1～1:30.
The temperature of the said heating for dissolving of steps A is: 40 ℃～80 ℃.
The said baking temperature of step a is 50～120 ℃, adopts constant temperature forced air drying or drying under reduced pressure.
Useful technique effect of the present invention shows:
With respect to prior art: because aseptic for guaranteeing in amyl ethyl quin ether hydrochloride injection production process; Pass through high temperature sterilize; Through aseptic filtration; Therefore resulting product is all unstable because of its pH value, related substance and content after high temperature sterilize or long-term the placement, and makes product quality can not get effective assurance.
And adopt the inventive method in preparation hydrochloride for injection amyl ethyl quin ether injectable powder process, to adopt recrystallizing technology; Owing to avoided high temperature sterilize; The injectable powder that makes simultaneously exists with solid forms, thereby in long-term put procedure, effectively reduces the touch opportunity between material; Thereby reduced the speed of reaction, guaranteed the stable of its pH value, related substance and content.
Show through effect experiment: the amyl ethyl quin ether hydrochloride injectable powder that the present invention makes is consistent with the drug effect of its injection; Toxicological test proves that also the acute toxicity of injectable powder is superior to injection simultaneously.
The quality of safety, effectiveness and the product of the amyl ethyl quin ether hydrochloride powder ampoule agent for injection that is made by the inventive method is guaranteed more easily.
Below in conjunction with experiment the present invention made and to further specify:
Test 1: the contrast of related substance behind the recrystallization
Related substance before and after the amyl ethyl quin ether hydrochloride raw material recrystallization is detected, and behind the discovery recrystallization, related substance obviously descends, and sees table 1 for details.
Table 1 recrystallization result of the test
Result of the test shows: related substance obviously reduces behind the recrystallization.
Test 2: the contrast of content, related substance and pH value before and after the sterilization of amyl ethyl quin ether hydrochloride injection
Prescription: (specification: 1ml: 1mg)
Amyl ethyl quin ether hydrochloride 0.1g
Water for injection adds to 100ml
The preparation of test specimen: take by weighing amyl ethyl quin ether hydrochloride 0.1g, add the dissolving of 80ml water for injection, regulate pH=4.52, add to the full amount of water for injection again, survey pH=4.56, content=99.4%, related substance 0.02% with the 0.1mol/L hydrochloric acid solution.Medicinal liquid is loaded in the 100ml volumetric flask of clean dry behind 0.22 μ m membrane filtration, and sealing compound seals, and is subsequent use.
Sterilize by following three conditions
1. 100 ℃, 30 minutes
2. 115 ℃, 20 minutes
3. 121 ℃, 15 minutes
The result sees table 2 for details
Table 2 high temperature sterilize is to the influence of amyl ethyl quin ether hydrochloride injection quality
Note: the labelled amount that content is meant, its acceptability limit interval is 90%-110% of a labelled amount.
The result: experimental study shows the raising along with sterilising conditions, and amyl ethyl quin ether hydrochloride injection pH value raises, and content descends, and related substance raises.
Test 3: amyl ethyl quin ether hydrochloride injection and the contrast of aseptic powder injection stability
The hydrochloride for injection amyl ethyl quin ether sample of getting the preparation of amyl ethyl quin ether hydrochloride injection and this law carries out accelerated test and long-term stable experiment.
The accelerated test condition: get test sample and put in the clean container, relative humidity 75% ± 5% was placed 6 months under 40 ℃ ± 2 ℃ temperature, in 1st month, 2 months, 3 months and 6th month pick test.
The long term test condition: 25% ± 2 ℃ of temperature, the condition held that relative humidity is 65% ± 10 ℃ 72 months is taken a sample to check respectively at 12 months, 24 months, 36 months, 48 months, and the result sees table 3, table 4 respectively
Table 3 accelerated test result
Table 4 long-term test results
Note: the labelled amount that content is meant, its acceptability limit interval is 90%-110% of a labelled amount.
Result: show that by stability experiment research variation is all taking place aspect pH value, content and the related substance passing amyl ethyl quin ether hydrochloride injection in time.And injection is all being stablized aspect pH value, content and the related substance with amyl ethyl quin ether hydrochloride.
Test 4: the concordance of drug effect this preparation of proof and former preparation drug effect
The hydrochloride for injection amyl ethyl quin ether that adopts the present invention to produce is done pharmacological testing; Injection all has obvious inhibitory action with amyl ethyl quin ether hydrochloride to the autonomous contraction of the Cavia porcellus stomach that exsomatizes, ileum, colon, gallbladder, bladder as a result; Spastic contraction to above-mentioned isolated organ, anesthetized animal, the clear-headed above-mentioned organ of animal due to the acetylcholine (Ach) all has tangible relexation; In the spastic contraction to above-mentioned organ due to the Ach, ED during the relexation of stomach exsomatized
50Big than atropine, then strong to stripped bladder effect than atropine, all the other effects and atropine zero differences.But anesthetized animal and clear-headed animal, the hydrochloride for injection amyl ethyl quin ether is strong than atropine to the relexation of stomach, ileum, colon, the spastic contraction of gallbladder.The relexation in the contraction of body cystospasm property of stripped bladder, anesthetized animal and clear-headed animal (intramuscular administration) obviously is better than atropine due to the Ach of hydrochloride for injection amyl ethyl quin ether.There is not significant difference with the amyl ethyl quin ether hydrochloride injection.Show that this preparation technology does not influence drug effect, consistent with former injection drug effect.
test 5: acute toxicity test shows that this preparation is superior to former preparation.
Behind rat, mice intramuscular injection hydrochloride for injection amyl ethyl quin ether or the amyl ethyl quin ether hydrochloride injection; Nervous, uneasy, activity minute occurring respectively at 3-5 minute, 15-20 increases; When intramuscular injection is heavy dose of, dyspnea and tic can occur, cyanosis occur individually and die from respiratory failure.The animal of dead animal and survival execution after 7 days, the equal no abnormality seen of gross necropsy, the result sees table 5 for details
Table 5 The acute toxicity tests
Test shows: hydrochloride for injection amyl ethyl quin ether mice LD
50With rat LD
50Apparently higher than the amyl ethyl quin ether hydrochloride injection, show that acute toxicity is superior to the amyl ethyl quin ether hydrochloride injection.
Test 6: it is consistent that long term toxicity test is shown in former preparation
Rat and Canis familiaris L. difference intramuscular injection hydrochloride for injection amyl ethyl quin ether or amyl ethyl quin ether hydrochloride injection 0.68,3.28,13.50 and 0.015,0.9mg/kg; Every day 1 time; Continuous 12 all administrations; Occur some common cholinolytics reactions after 1 week, along with administration time prolongs, above-mentioned reaction does not have obviously and increases the weight of; After drug withdrawal a couple of days to disappearing in 2 weeks, in the administration phase with 1 week of drug withdrawal after behavioral activity, appetite and body weight, feces character, hematology and blood biochemistry checking, system's postmortem and histological examination all do not have obvious change.Hydrochloride for injection amyl ethyl quin ether and amyl ethyl quin ether hydrochloride injection long term toxicity test show no significant difference.
Test shows: the hydrochloride for injection amyl ethyl quin ether is consistent with amyl ethyl quin ether hydrochloride injection long term toxicity.
The specific embodiment
Embodiment 1
A, get amyl ethyl quin ether hydrochloride 100g, add dehydrated alcohol-absolute ether (1:2) 600ml, be heated to 78 ℃ and make dissolving, add pin and stir with activated carbon 0.2g, first coarse filtration decarburization, the filtering with microporous membrane of reuse 0.22 μ m obtains clear liquid;
B, under gnotobasis, the clear liquid of step B is carried out recrystallization, through filtration under diminished pressure, wash, drain, 105 ℃ of dryings, pulverize and obtain the amyl ethyl quin ether hydrochloride aseptic powder with dehydrated alcohol-absolute ether (1:2) 300ml, the encapsulation back is subsequent use;
The preparation of C, hydrochloride for injection amyl ethyl quin ether injectable powder
A, vial are handled: vial is used ultrasonic waves for cleaning, and after the pure water rinsing, 320 ℃ of 5min of tunnel type dry heat sterilization are adopted in the flushing of reuse water for injection, get clean, aseptic, dry, apyrogenic vial;
B, plug handle: with plug with dilute hydrochloric acid boil wash after, with the purified water flushing,, clean the back silication again with the water for injection rinsing, remove thermal source, then with 121 ℃ of the steam 40min that sterilizes, 120 ℃ of oven dry, subsequent use.
C, bottling: after the aseptic powder that steps A is made adopts volume quantitative or screw rod metering; Quantitatively powder is divided in the vial of treated mistake through racking machine; Plug with treated mistake covers on bottleneck simultaneously, through lamp inspection, labeling, sampling, check, promptly obtains product.
Embodiment 2
A, get amyl ethyl quin ether hydrochloride 100g, add dehydrated alcohol-absolute ether (1:2) 700ml, be heated to 75 ℃ and make dissolving, add pin and stir with activated carbon 0.3g, first coarse filtration decarburization, the filtering with microporous membrane of reuse 0.22 μ m obtains clear liquid;
B, under gnotobasis, the clear liquid of step B is carried out recrystallization, through filtration under diminished pressure, wash, drain, 105 ℃ of dryings, pulverize and obtain the amyl ethyl quin ether hydrochloride aseptic powder with dehydrated alcohol-absolute ether (1:2) 300ml, the encapsulation back is subsequent use;
The preparation of C, hydrochloride for injection amyl ethyl quin ether injectable powder
A, vial are handled: vial is used ultrasonic waves for cleaning, and after the pure water rinsing, the flushing of reuse water for injection, 180 ℃ of sterilization 1.5h get clean, aseptic, dry, apyrogenic vial;
B, plug handle: with plug with dilute hydrochloric acid boil wash after, with the purified water flushing,, clean the back silication again with the water for injection rinsing, remove thermal source, then with 121 ℃ of the steam 40min that sterilizes, 120 ℃ of oven dry, subsequent use.
C, bottling: after the aseptic powder that steps A is made adopts volume quantitative or screw rod metering; Quantitatively powder is divided in the vial of treated mistake through racking machine; Plug with treated mistake covers on bottleneck simultaneously, through lamp inspection, labeling, sampling, check, promptly obtains product.
Embodiment 3
A, get amyl ethyl quin ether hydrochloride 100g, add dehydrated alcohol-absolute ether (1:10) 100ml, be heated to 40 ℃ and make dissolving, add pin and stir with activated carbon 0.2g, first coarse filtration decarburization, the filtering with microporous membrane of reuse 0.22 μ m obtains clear liquid;
B, under gnotobasis, the clear liquid of step B is carried out recrystallization, through filtration under diminished pressure, wash, drain, 105 ℃ of dryings, pulverize and obtain the amyl ethyl quin ether hydrochloride aseptic powder with dehydrated alcohol-absolute ether (1:10) 400ml, the encapsulation back is subsequent use;
The preparation of C, hydrochloride for injection amyl ethyl quin ether injectable powder
A, vial are handled: vial is used ultrasonic waves for cleaning, and after the pure water rinsing, 320 ℃ of 5min of tunnel type dry heat sterilization are adopted in the flushing of reuse water for injection, get clean, aseptic, dry, apyrogenic vial;
B, plug handle: with plug with dilute hydrochloric acid boil wash after, with the purified water flushing,, clean the back silication again with the water for injection rinsing, remove thermal source, then with 121 ℃ of the steam 40min that sterilizes, 120 ℃ of oven dry, subsequent use.
C, bottling: after the aseptic powder that steps A is made adopts volume quantitative or screw rod metering; Quantitatively powder is divided in the vial of treated mistake through racking machine; Plug with treated mistake covers on bottleneck simultaneously, through lamp inspection, labeling, sampling, check, promptly obtains product.
Embodiment 4
A, get amyl ethyl quin ether hydrochloride 100g, add dehydrated alcohol-absolute ether (1:0.5) 3000ml, be heated to 40 ℃ and make dissolving, add pin and stir with activated carbon 0.2g, first coarse filtration decarburization, the filtering with microporous membrane of reuse 0.22 μ m obtains clear liquid;
B, under gnotobasis, the clear liquid of step B is carried out recrystallization, through filtration under diminished pressure, wash, drain, 105 ℃ of dryings, pulverize and obtain the amyl ethyl quin ether hydrochloride aseptic powder with dehydrated alcohol-absolute ether (1:0.5) 300ml, the encapsulation back is subsequent use;
The preparation of C, hydrochloride for injection amyl ethyl quin ether injectable powder
A, vial are handled: vial is used ultrasonic waves for cleaning, and after the pure water rinsing, 320 ℃ of 5min of tunnel type dry heat sterilization are adopted in the flushing of reuse water for injection, get clean, aseptic, dry, apyrogenic vial;
B, plug handle: with plug with dilute hydrochloric acid boil wash after, with the purified water flushing,, clean the back silication again with the water for injection rinsing, remove thermal source, then with 121 ℃ of the steam 40min that sterilizes, 120 ℃ of oven dry, subsequent use.
C, bottling: after the aseptic powder that steps A is made adopts volume quantitative or screw rod metering; Quantitatively powder is divided in the vial of treated mistake through racking machine; Plug with treated mistake covers on bottleneck simultaneously, through lamp inspection, labeling, sampling, check, promptly obtains product.
Claims (5)
1. the method for preparing of a hydrochloride for injection amyl ethyl quin ether injectable powder, it is characterized in that: processing step is following:
A, amyl ethyl quin ether hydrochloride is dissolved in dehydrated alcohol-absolute ether, heating makes its dissolving, after adding pin again and stirring decolouring with activated carbon, and first coarse filtration decarburization, the filtering with microporous membrane of reuse 0.22 μ m obtains clear liquid;
B, under gnotobasis, the clear liquid of step B is carried out recrystallization, through filtration under diminished pressure, wash, drain, 105 ℃ of dryings, pulverize and obtain the amyl ethyl quin ether hydrochloride aseptic powder, the encapsulation back is subsequent use;
The preparation of C, hydrochloride for injection amyl ethyl quin ether injectable powder
A, vial handle: vial use ultrasonic waves for cleaning, and after the pure water rinsing, the flushing of reuse water for injection, 4 hours inner dryings and sterilization must clean, aseptic, dry, apyrogenic vials; The condition of said sterilization and mode are: 180 ℃ of 1.5h or 320 ℃ of 5min of tunnel type dry heat sterilization;
B, plug handle: with plug with dilute hydrochloric acid boil wash after, with the purified water flushing,, clean the back silication again with the water for injection rinsing, remove thermal source, then with 121 ℃ of the steam 40min that sterilizes, 120 ℃ of oven dry, subsequent use;
C, bottling: after the aseptic powder that steps A is made adopts volume quantitative or screw rod metering; Quantitatively powder is divided in the vial of treated mistake through racking machine; Plug with treated mistake covers on bottleneck simultaneously, through lamp inspection, labeling, sampling, check, promptly obtains product.
2. the method for preparing of hydrochloride for injection amyl ethyl quin ether injectable powder according to claim 1, it is characterized in that: the weight ratio of the said dehydrated alcohol-absolute ether of steps A is 1:0.5～1:10.
3. the method for preparing of hydrochloride for injection amyl ethyl quin ether injectable powder according to claim 1, it is characterized in that: the weight ratio of the said amyl ethyl quin ether hydrochloride of steps A and dehydrated alcohol-absolute ether is 1:1～1:30.
4. the method for preparing of hydrochloride for injection amyl ethyl quin ether injectable powder according to claim 1, it is characterized in that: the temperature of the said heating for dissolving of steps A is: 40 ℃～80 ℃.
5. the method for preparing of hydrochloride for injection amyl ethyl quin ether injectable powder according to claim 1, it is characterized in that: the said baking temperature of step a is 50～120 ℃, adopts constant temperature forced air drying or drying under reduced pressure.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102702187A (en) * | 2011-06-29 | 2012-10-03 | 成都自豪药业有限公司 | New crystal form of penehyclidine hydrochloride and preparation method of new crystal form |
| CN111377920A (en) * | 2018-12-27 | 2020-07-07 | 银谷制药有限责任公司 | Method for refining quinine compound containing quaternary ammonium group |
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| CN101461807A (en) * | 2009-01-15 | 2009-06-24 | 成都力思特制药股份有限公司 | Application of penehyclidine hydrochloride in preparing medicament for treating haemorrhagic shock |
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| CN101234107A (en) * | 2007-01-30 | 2008-08-06 | 成都力思特制药股份有限公司 | Pharmaceutical composition containing (3S, 2'S)-3-(2'-hydroxy-2'-cyclopentyl-2'-phenylethoxy) quinuclidine hydrochloride and uses thereof |
| CN101461807A (en) * | 2009-01-15 | 2009-06-24 | 成都力思特制药股份有限公司 | Application of penehyclidine hydrochloride in preparing medicament for treating haemorrhagic shock |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102702187A (en) * | 2011-06-29 | 2012-10-03 | 成都自豪药业有限公司 | New crystal form of penehyclidine hydrochloride and preparation method of new crystal form |
| CN111377920A (en) * | 2018-12-27 | 2020-07-07 | 银谷制药有限责任公司 | Method for refining quinine compound containing quaternary ammonium group |
| CN111377920B (en) * | 2018-12-27 | 2021-10-26 | 银谷制药有限责任公司 | Method for refining quinine compound containing quaternary ammonium group |
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Effective date of registration: 20210517 Address after: 121013 No. 55 Songshan Street, Taihe District, Jinzhou City, Liaoning Province Patentee after: Jinzhou Aohong Pharmaceutical Co.,Ltd. Address before: 610063 Jinjiang Industrial Development Zone, Sichuan, Chengdu Patentee before: CHENGDU LIST PHARMACEUTICAL Co.,Ltd. |
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