CN107432864A - A kind of (S)-Esomeprazole aseptic powdery and preparation method thereof - Google Patents
A kind of (S)-Esomeprazole aseptic powdery and preparation method thereof Download PDFInfo
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- CN107432864A CN107432864A CN201610362634.0A CN201610362634A CN107432864A CN 107432864 A CN107432864 A CN 107432864A CN 201610362634 A CN201610362634 A CN 201610362634A CN 107432864 A CN107432864 A CN 107432864A
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- esomeprazole
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/19—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles lyophilised, i.e. freeze-dried, solutions or dispersions
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/4015—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil having oxo groups directly attached to the heterocyclic ring, e.g. piracetam, ethosuximide
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/02—Inorganic compounds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
- A61K47/183—Amino acids, e.g. glycine, EDTA or aspartame
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
Abstract
The invention discloses pyrrolidine acetamide aseptic powdery of 2 oxo of a kind of (S) 4 hydroxyl 1 and preparation method thereof；The aseptic powdery contains the supplementary material of following percentage by weight：(S) pyrrolidine acetamide 50% ~ 59% of 4 hydroxyl, 2 oxo 1, L serines 20% ~ 25%, mannitol 10% ~ 17%, sodium glutamate 5% ~ 7%, sodium hydrogensulfite 5% ~ 10%, phenmethylol 1% ~ 3%.The present invention utilizes specific excipient composition, so that the pyrrolidine acetamide aseptic powdery of 2 oxo of (S) 4 hydroxyl 1 prepared has solid shape, without spray bottle phenomenon in freeze-drying process, and product stability is good, particulate matter substantially reduces reduction, and pain is lighter in patient injection procedure, good patient compliance, be advantageous to improve the security that medicine uses, reduce adverse drug reaction.
Description
Technical field
The invention belongs to pharmaceutical field, and in particular to a kind of (S)-Esomeprazole aseptic powdery and its system
Preparation Method.
Background technology
Levo-oxiracetam chemical name is：(S)-Esomeprazole, it is white micro-crystals sprills, melts
135~136 DEG C of point, -36 ° of optical activity (C=1.00in water), the dissolubility of levo-oxiracetam is substantially better than raceme.Change
It is as follows to learn structural formula：
The medicine listed in 1987 in Italy, and the formulation of listing is tablet, 800mg；Capsule, 800mg；Parenteral solution, 1g/5ml.
It is domestic at present there was only oxiracetam capsule and parenteral solution listing, and main active used is racemic modification.Ye Lei etc. is in public affairs
The number of opening is obvious to the promoting wakening gone into a coma caused by alcoholism to mention levo-oxiracetam in the A patents of CN 103735545, and right
Rotation Oxiracetam does not act on substantially, and the awake effect of above-mentioned rush of levo-oxiracetam is 2 times of racemization Oxiracetam；Left-handed Aura
The western smooth promoting wakening to stupor caused by wound, anesthesia is notable.Peak etc. is opened in the A of Publication No. CN 103599101 patent
Disclose levo-oxiracetam has substantially to traumatic brain injury learning and memory in rats cognition dysfunction caused by hydraulic pressure and freely falling body
Improvement result, its drug effect is far above dextrorotation Oxiracetam.And 200mg/kg levo-oxiracetams and 400mg/kg Oxiracetams
Effect it is suitable.Pharmacokinetic study results are shown：Levo-oxiracetam and dextrorotation Oxiracetam nothing in beasle dog body are obvious
Chiral inversion.Beasle dog single intravenous injection gives after left-handed and 2 multiple doses racemization Oxiracetams levo-oxiracetam in blood plasma
The equal no significant difference of main pharmacokinetic parameters.The result of the tests such as safe pharmacology, anxious malicious, long poison show, in isodose level
Under, levo-oxiracetam is with Oxiracetam to animal subject or the toxicity no significant difference of cell.Above-mentioned preclinical result of study
Show, levo-oxiracetam is the main active that drug effect is played in Oxiracetam body, and exclusive use this product, which can reduce clinic, to be made
With dosage, potential toxicity is reduced.
But existing (S)-Esomeprazole aseptic powdery exists without solid shape, is not easy to form bone
Frame, easily occur spray bottle phenomenon in freeze-drying process, and the problem of product stability difference be present, it is necessary to dissolve in before Clinical practice
In 5% glucose injection or 0.9% 100~250ml of sodium chloride injection, preparing, which turns into drip-feed solution, uses, and is prepared into
After drip-feed solution, with the extension of standing time, its particulate matter increases, and this just brings to clinical use
Very big potential safety hazard.In addition, also there is injection process in existing (S)-Esomeprazole aseptic powdery
Pain is obvious, the problems such as patient's poor compliance.
The content of the invention
In view of this, it is an object of the invention to provide a kind of (S)-Esomeprazole aseptic powdery and its
Preparation method, there is solid shape, in freeze-drying process without spray bottle phenomenon, and product stability is good, and preparing, which turns into vein, drips
After noting solution, particulate matter is reduced, and pain is lighter in injection process, good patient compliance.
To reach above-mentioned purpose, the present invention provides following technical scheme：
A kind of (S)-Esomeprazole aseptic powdery, the aseptic powdery contain following percentage by weight
Supplementary material：(S)-Esomeprazole 50%~59%, Serine 20%~25%, mannitol 10%~17%,
Sodium glutamate 5%~7%, sodium hydrogensulfite 5%~10%, phenmethylol 1%~3%.
Further, the aseptic powdery contains the supplementary material of following percentage by weight：(S) -4- hydroxyls -2- OXo-1-pyrrolidine acetyl
Amine 52%, Serine 22%, mannitol 12%, sodium glutamate 6%, sodium hydrogensulfite 6%, phenmethylol 2%.
The preparation method of above-mentioned (S)-Esomeprazole aseptic powdery, comprises the following steps：
(1) concentrated compounding：The supplementary material of recipe quantity is placed in container, adds 10 times of (S)-Esomeprazole
The sterilized water for injection stirring of parts by weight, after dissolving, adds the needle-use activated carbon of mass fraction 0.1%, stirs 30min, then
Filtered with 0.45 micron of miillpore filter, collect filtrate, it is standby；
(2) it is dilute to match somebody with somebody：Sterilized water for injection is added into filtrate to 1000 times of filtrate volume, with 0.1mol/L hydrochloric acid or
0.1mol/L sodium hydroxide adjusts pH value to 3.2~3.6, then with 0.22 micron of miillpore filter aseptic filtration, takes filtrate to close
It is filling after lattice to be sub-packed in sterile glass vials, it is standby；
(3) it is freeze-dried：The above-mentioned decoction being sub-packed in sterile glass vials is put in freeze drier and is freeze-dried；
(4) lid is rolled：Aluminium-plastic combined cover needs once purged sterilizing, drying, then carries out rolling lid, produces.
Further, it is in the step (3), the step of freeze-drying：Temperature is refrigerated to -40 DEG C rapidly, whole process is protected
Hold 180 minutes；Then drying is vacuumized, is warming up to -10 DEG C with 15 DEG C/h, -10 DEG C of constant temperature are kept for 120 minutes；With 5 DEG C/
Hour is warming up to 0 DEG C, 0 DEG C of constant temperature 320 minutes；10 DEG C are warming up to 5 DEG C/h, 10 DEG C of constant temperature 240 minutes；With 10 DEG C/
Hour is warming up to 30 DEG C, 30 DEG C of constant temperature 60 minutes, while preceding case vacuum drop reaches 10Pa/10 timesharing, freezes and terminates.
The beneficial effects of the present invention are：
The present invention utilizes specific excipient composition so that (S)-Esomeprazole aseptic powdery of preparation
With solid shape, without spray bottle phenomenon in freeze-drying process, and product stability is good, dissolves in glucose injection or sodium chloride
Parenteral solution is prepared after turning into drip-feed solution, and particulate matter substantially reduces reduction, and pain is lighter in patient injection procedure,
Good patient compliance, be advantageous to improve the security that medicine uses, reduce adverse drug reaction.
Embodiment
In order that the purpose of the present invention, technical scheme and beneficial effect are clearer, the preferred embodiments of the present invention will be entered below
The detailed description of row.
Embodiment 1
The prescription of (S)-Esomeprazole aseptic powdery of embodiment 1 is as shown in the table：
| Prescription | Percentage by weight |
| (S)-Esomeprazole | 50% |
| Serine | 24% |
| Mannitol | 15% |
| Sodium glutamate | 5% |
| Sodium hydrogensulfite | 5% |
| Phenmethylol | 1% |
The preparation method of (S)-Esomeprazole aseptic powdery of embodiment 1, comprises the following steps：
(1) concentrated compounding：The supplementary material of recipe quantity is placed in container, adds 10 times of (S)-Esomeprazole
The sterilized water for injection stirring of parts by weight, after dissolving, adds the needle-use activated carbon of mass fraction 0.1%, stirs 30min, then
Filtered with 0.45 micron of miillpore filter, collect filtrate, it is standby；
(2) it is dilute to match somebody with somebody：Sterilized water for injection is added into filtrate to 1000 times of filtrate volume, with 0.1mol/L hydrochloric acid or
0.1mol/L sodium hydroxide adjusts pH value to 3.2~3.6, then with 0.22 micron of miillpore filter aseptic filtration, takes filtrate to close
It is filling after lattice to be sub-packed in sterile glass vials, it is standby；
(3) it is freeze-dried：The above-mentioned decoction being sub-packed in sterile glass vials is put in freeze drier, is rapidly refrigerated to temperature
- 40 DEG C, whole process is kept for 180 minutes；Then drying is vacuumized, is warming up to -10 DEG C with 15 DEG C/h, -10 DEG C of constant temperature are kept
120 minutes；0 DEG C is warming up to 5 DEG C/h, 0 DEG C of constant temperature 320 minutes；10 DEG C are warming up to 5 DEG C/h, 10 DEG C of constant temperature 240
Minute；30 DEG C are warming up to 10 DEG C/h, 30 DEG C of constant temperature 60 minutes, while preceding case vacuum drop reaches 10Pa/10 timesharing, freezes
Dry and hard beam；
(4) lid is rolled：Aluminium-plastic combined cover needs once purged sterilizing, drying, then carries out rolling lid, produces.
Embodiment 2
The prescription of (S)-Esomeprazole aseptic powdery of embodiment 2 is as shown in the table：
| Prescription | Percentage by weight |
| (S)-Esomeprazole | 52% |
| Serine | 22% |
| Mannitol | 12% |
| Sodium glutamate | 6% |
| Sodium hydrogensulfite | 6% |
| Phenmethylol | 2% |
The preparation method of (S)-Esomeprazole aseptic powdery of embodiment 2 is same as Example 1.
Embodiment 3
The prescription of (S)-Esomeprazole aseptic powdery of embodiment 3 is as shown in the table：
| Prescription | Percentage by weight |
| (S)-Esomeprazole | 53% |
| Serine | 20% |
| Mannitol | 10% |
| Sodium glutamate | 6% |
| Sodium hydrogensulfite | 8% |
| Phenmethylol | 3% |
The preparation method of (S)-Esomeprazole aseptic powdery of embodiment 3 is same as Example 1.
Comparative example 1
(S)-Esomeprazole aseptic powdery of comparative example 1 does not add sodium hydrogensulfite, remaining component
And preparation method is same as Example 2.
Comparative example 2
(S)-Esomeprazole aseptic powdery of comparative example 2 does not add phenmethylol, remaining component and system
Preparation Method is same as Example 2.
First, character observation：
(S)-Esomeprazole aseptic powdery made from embodiment 1-3 is sampled, investigation project is examined
Test, investigate project：Character, visible foreign matters, pH, relevant material, content, sterility test.
From character observation result, (S)-Esomeprazole aseptic powdery has made from embodiment 1-3
Solid shape, without spray bottle phenomenon in freeze-drying process, product impurity is few, and indices meet production requirement.
2nd, particulate matter is investigated：
(S)-Esomeprazole aseptic powdery made from embodiment 2 and comparative example 1 is used into 250ml respectively
0.9% sodium chloride injection and the dilution of 5% glucose injection, preparation turn into drip-feed solution, reference Chinese Pharmacopoeia 2015
Year the 4th method of particulate matter inspection technique first (light blockage method) of version, its particulate matter was determined respectively at 0,4,8,12 hour,
The number of capacitive particulate, result of the test not see the table below in each sign loading amount of calculating：
Result is investigated from particulate matter, the product stability of embodiment 2 is substantially better than comparative example 1, dissolves in glucose note
To penetrate liquid or sodium chloride injection is prepared after turning into drip-feed solution, the particulate matter of embodiment 2 is considerably less than comparative example 1,
With the extension of standing time, the particulate matter of embodiment 2 does not almost increase, and the particulate matter of comparative example 1 is notable
Increase increases.
3rd, injection pain sense is tested：
(S)-Esomeprazole aseptic powdery made from embodiment 2 and comparative example 2 is used into physiology salt respectively
Water dissolved dilution, experimental white mouse is then taken, be subcutaneously injected, whether observation small white mouse can occur writhing response, according to mouse
The probability that writhing response occurs judges the power of pain in injection process, each to repeat 30 experiments, and result of the test see the table below：
| Sample | Experiment sample (mouse) | Generation writhing response number of individuals | Writhing response incidence |
| Embodiment 2 | 30 | 5 | 16.7% |
| Comparative example 2 | 30 | 24 | 80% |
(S)-Esomeprazole aseptic powder as made from injection pain sense results showed that embodiment 2
Pain is markedly less than comparative example 2 in last injection process.
Finally illustrate, preferred embodiment above is merely illustrative of the technical solution of the present invention and unrestricted, although by above-mentioned
The present invention is described in detail for preferred embodiment, it is to be understood by those skilled in the art that can in form and
Various changes are made in details to it, without departing from claims of the present invention limited range.
Claims (4)
- A kind of 1. (S)-Esomeprazole aseptic powdery, it is characterised in that：The aseptic powdery contains the supplementary material of following percentage by weight：(S)-Esomeprazole 50% ~ 59%, Serine 20% ~ 25%, mannitol 10% ~ 17%, sodium glutamate 5% ~ 7%, sodium hydrogensulfite 5% ~ 10%, phenmethylol 1% ~ 3%.
- 2. (S)-Esomeprazole aseptic powdery according to claim 1, it is characterised in that：The aseptic powdery contains the supplementary material of following percentage by weight：(S)-Esomeprazole 52%, Serine 22%, mannitol 12%, sodium glutamate 6%, sodium hydrogensulfite 6%, phenmethylol 2%.
- 3. the preparation method of (S)-Esomeprazole aseptic powdery described in claim 1 or 2, it is characterised in that：Comprise the following steps：（1）Concentrated compounding：The supplementary material of recipe quantity is placed in container, add the sterilized water for injection stirring of 10 times of parts by weight of (S)-Esomeprazole, after dissolving, add the needle-use activated carbon of mass fraction 0.1%, stir 30min, then filtered with 0.45 micron of miillpore filter, collect filtrate, it is standby；（2）It is dilute to match somebody with somebody：Sterilized water for injection is added into filtrate to 1000 times of filtrate volume, pH value is adjusted to 3.2 ~ 3.6 with 0.1mol/L hydrochloric acid or 0.1mol/L sodium hydroxide, it is filling after taking filtrate qualified to be sub-packed in sterile glass vials then with 0.22 micron of miillpore filter aseptic filtration, it is standby；（3）Freeze-drying：The above-mentioned decoction being sub-packed in sterile glass vials is put in freeze drier and is freeze-dried；（4）Roll lid：Aluminium-plastic combined cover needs once purged sterilizing, drying, then carries out rolling lid, produces.
- 4. the preparation method of (S)-Esomeprazole aseptic powdery according to claim 2, it is characterised in that：The step（3）In, it is the step of freeze-drying：Temperature is refrigerated to -40 DEG C rapidly, whole process is kept for 180 minutes；Then drying is vacuumized, is warming up to -10 DEG C with 15 DEG C/h, -10 DEG C of constant temperature are kept for 120 minutes；0 DEG C is warming up to 5 DEG C/h, 0 DEG C of constant temperature 320 minutes；10 DEG C are warming up to 5 DEG C/h, 10 DEG C of constant temperature 240 minutes；30 DEG C are warming up to 10 DEG C/h, 30 DEG C of constant temperature 60 minutes, while preceding case vacuum drop reaches 10Pa/10 timesharing, freezes and terminates.
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| CN201610362634.0A CN107432864A (en) | 2016-05-26 | 2016-05-26 | A kind of (S)-Esomeprazole aseptic powdery and preparation method thereof |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008150080A1 (en) * | 2007-06-04 | 2008-12-11 | Dong-A Pharm. Co., Ltd. | Injectable ready to use solutions comprising human chorionic gonadotropin |
| CN101396358A (en) * | 2007-09-25 | 2009-04-01 | 广东世信药业有限公司 | Oxiracetam injection |
| CN101766597A (en) * | 2008-12-31 | 2010-07-07 | 北京利乐生制药科技有限公司 | Injection preparation with levo-oxiracetam as active component |
-
2016
- 2016-05-26 CN CN201610362634.0A patent/CN107432864A/en not_active Withdrawn
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008150080A1 (en) * | 2007-06-04 | 2008-12-11 | Dong-A Pharm. Co., Ltd. | Injectable ready to use solutions comprising human chorionic gonadotropin |
| CN101396358A (en) * | 2007-09-25 | 2009-04-01 | 广东世信药业有限公司 | Oxiracetam injection |
| CN101766597A (en) * | 2008-12-31 | 2010-07-07 | 北京利乐生制药科技有限公司 | Injection preparation with levo-oxiracetam as active component |
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Application publication date: 20171205 |