CN105708812A - 5-(2-fluorophenyl)-N-methyl-1-(3-pyridylsulfonyl)-1H-pyrrole-3-methylamine freeze-dried powder injection and preparation method thereof - Google Patents
5-(2-fluorophenyl)-N-methyl-1-(3-pyridylsulfonyl)-1H-pyrrole-3-methylamine freeze-dried powder injection and preparation method thereof Download PDFInfo
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- CN105708812A CN105708812A CN201410712609.1A CN201410712609A CN105708812A CN 105708812 A CN105708812 A CN 105708812A CN 201410712609 A CN201410712609 A CN 201410712609A CN 105708812 A CN105708812 A CN 105708812A
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Abstract
The invention discloses a freeze-dried powder injection of vonoprazan (5-(2-fluorophenyl)-N-methyl-1-(3-pyridylsulfonyl)-1H-pyrrole-3-methylamine) inorganic or organic acid salt and a preparation method thereof. A self-made vonoprazan inorganic or organic acid salt, an antioxidant, a stabilizer, a pH value regulator and injection activated carbon are adopted. The method consists of: firstly adding the stabilizer and the antioxidant into 90% water for injection, cooling the water for injection to a temperature below 25DEG C, adding the vonoprazan inorganic or organic acid salt and performing stirring to dissolve it, adjusting the pH value to 5.0-7.0, adding injection activated carbon and carrying out 60DEG C heat preservation adsorption for 30min, then adding water for injection to set the volume to a full dosage, carrying out filtering, filling, and freeze-drying in a freeze-drying box for about 24h, then taking the product out, conducting capping, labeling and packaging, thus obtaining the vonoprazan freeze-dried powder injection. The vonoprazan inorganic or organic acid salt freeze-dried powder injection prepared by the method provided by the invention can be redissolved with 0.9% sodium chloride or 5% glucose, and has the characteristics of uniform content, qualified solution clarity and good stability, and is suitable for industrial production.
Description
Technical field
The invention belongs to field of pharmaceutical preparations, particularly relate to a kind of fluorine pula with treatment gastric acid related disease effect and praise (5-(2-fluorophenyl)-N-methyl isophthalic acid-(3-pyridyl sulfonyl)-1H-pyrroles's-3-first ammonia) freeze-dried powder of organic or inorganic hydrochlorate and preparation method.
Background technology
Gastric acid related disease is a class disease most commonly seen in digestive system disease, refer to that a class is due to gastroxia, or gastric acid is especially sensitive and that the cause general name of a class digestive tract disease, common are gastroesophageal reflux disease, the digestive system disease that peptic ulcer, Zollinger-Ellison Syndrome and non-steroidal anti-inflammatory drug cause.PPI is the class medicine that current Acidinhibitor is the strongest, such as omeprazole, lansoprazole, pantoprazole, rabeprazole etc..Owing to PPI also exists nocturnal acid rebound phenomenon, thus affecting therapeutic effect.
5-(2-fluorophenyl)-N-methyl isophthalic acid-(3-pyridyl sulfonyl)-1H-pyrroles-3-first ammonia fumarate (TAK438) be Takeda Pharmaceutical Company Limited develop a kind of potassium ion competitiveness acid blocker (P-CAB), experiment in vitro research shows this compound inhibitor proton pump (H+, ATPase) ability is 400 times of lansoprazole, can effective gastric acid secretion inhibiting, the advantage with persistent period length, but the fumarate poorly water-soluble of this compound, animal oral administration biaavailability only 10%, limit this compound and play its acid suppression and the effect for the treatment of gastric acid related disease.
Summary of the invention
For solve fluorine pula praise fumarate poorly water-soluble, animal oral administration biaavailability only 10% problem, praised by fluorine pula and prepare freeze-dried powder after making into acetic acid, methanesulfonic acid, sulphuric acid, phosphate respectively.Stability problem is praised, it has been found that in prescription, add certain proportion antioxidant, for instance sodium sulfite can improve the stability that fluorine pula is praised, it is prevented that its oxidation Decomposition for solving fluorine pula.It addition, be additionally added acidity or alkaline pH adjuster that this product can be adjusted to physiology tolerance interval.Lyophilized injectable powder of the present invention can be optionally added other conventional excipients.
Detailed description of the invention
Praising below by fluorine pula and prepare freeze-dried powder after making into acetic acid, methanesulfonic acid, sulphuric acid, phosphate respectively, carry out technical study, the present invention will be further described for embodiment:
The preparation of freeze-dried powder is praised in fluorine pula
Embodiment 1
Prescription
Method for making: method is first to join in 90% water for injection by mannitol, sodium sulfite, and water for injection is cooled to less than 25 degree, addition fluorine pula is praised and is stirred and makes it dissolve, adjust pH value to 4.0-5.0, add needle-use activated carbon 60 degree and be incubated and adsorb 30min, then inject and use water constant volume, cross 0.22 micron membrane filter, fill, every 2mL, enter freeze drying box lyophilizing, lyophilization cycle is about 24 hours, and outlet rolls lid, labeling, packs and obtains fluorine pula and praise freeze-dried powder.
Embodiment 2
Prescription
Method for making: method is first to join in 90% water for injection by mannitol, sodium sulfite, and water for injection is cooled to less than 25 degree, addition fluorine pula is praised and is stirred and makes it dissolve, adjust pH value to 4.0-5.0, add needle-use activated carbon 60 degree and be incubated and adsorb 30min, then inject and use water constant volume, cross 0.22 micron membrane filter, fill, every 2mL, enter freeze drying box lyophilizing, lyophilization cycle is about 24 hours, and outlet rolls lid, labeling, packs and obtains fluorine pula and praise freeze-dried powder.
Embodiment 3
Prescription
Method for making: method is first to join in 90% water for injection by mannitol, sodium pyrosulfite, and water for injection is cooled to less than 25 degree, addition fluorine pula is praised and is stirred and makes it dissolve, adjust pH value to 4.0-5.0, add needle-use activated carbon 60 degree and be incubated and adsorb 30min, then inject and use water constant volume, cross 0.22 micron membrane filter, fill, every 2mL, enter freeze drying box lyophilizing, lyophilization cycle is about 24 hours, and outlet rolls lid, labeling, packs and obtains fluorine pula and praise freeze-dried powder.
Embodiment 4
Prescription
Method for making: method is first to join in 90% water for injection by lactose, sodium sulfite, and water for injection is cooled to less than 25 degree, addition fluorine pula is praised and is stirred and makes it dissolve, adjust pH value to 4.5-5.5, add needle-use activated carbon 60 degree and be incubated and adsorb 30min, then inject and use water constant volume, cross 0.22 micron membrane filter, fill, every 2mL, enter freeze drying box lyophilizing, lyophilization cycle is about 24 hours, and outlet rolls lid, labeling, packs and obtains fluorine pula and praise freeze-dried powder.
Embodiment 5
Prescription
Method for making: method is first to join in 90% water for injection by lactose, sodium pyrosulfite, and water for injection is cooled to less than 25 degree, addition fluorine pula is praised and is stirred and makes it dissolve, adjust pH value to 5.0-7.0, add needle-use activated carbon 60 degree and be incubated and adsorb 30min, then inject and use water constant volume, cross 0.22 micron membrane filter, fill, every 2mL, enter freeze drying box lyophilizing, lyophilization cycle is about 24 hours, and outlet rolls lid, labeling, packs and obtains fluorine pula and praise freeze-dried powder.
Embodiment 6
Prescription
Method for making: method is first to join in 90% water for injection by sodium chloride, sodium thiosulfate, and water for injection is cooled to less than 25 degree, addition fluorine pula is praised and is stirred and makes it dissolve, adjust pH value to 5.5, add needle-use activated carbon 60 degree insulation and adsorb 30min, then inject and use water constant volume, cross 0.22 micron membrane filter, fill, every 2mL, enter freeze drying box lyophilizing, lyophilization cycle is about 24 hours, and outlet rolls lid, labeling, packs and obtains fluorine pula and praise freeze-dried powder.
Embodiment 7
Prescription
Method for making: method is first to join in 90% water for injection by glucose, sodium sulfite, and water for injection is cooled to less than 25 degree, addition fluorine pula is praised and is stirred and makes it dissolve, adjust pH value to 5.5, add needle-use activated carbon 60 degree insulation and adsorb 30min, then inject and use water constant volume, cross 0.22 micron membrane filter, fill, every 2mL, enter freeze drying box lyophilizing, lyophilization cycle is about 24 hours, and outlet rolls lid, labeling, packs and obtains fluorine pula and praise freeze-dried powder.
Embodiment 8
Prescription
Method for making: method is first to join in 90% water for injection by sorbitol, sodium thiosulfate, and water for injection is cooled to less than 25 degree, addition fluorine pula is praised and is stirred and makes it dissolve, adjust pH value to 5.5, add needle-use activated carbon 60 degree insulation and adsorb 30min, then inject and use water constant volume, cross 0.22 micron membrane filter, fill, every 2mL, enter freeze drying box lyophilizing, lyophilization cycle is about 24 hours, and outlet rolls lid, labeling, packs and obtains fluorine pula and praise freeze-dried powder.
Embodiment 9
Prescription
Method for making: method is first to join in 90% water for injection by glucose, sodium thiosulfate, and water for injection is cooled to less than 25 degree, addition fluorine pula is praised and is stirred and makes it dissolve, adjust pH value to 5.5, add needle-use activated carbon 60 degree insulation and adsorb 30min, then inject and use water constant volume, cross 0.22 micron membrane filter, fill, every 2mL, enter freeze drying box lyophilizing, lyophilization cycle is about 24 hours, and outlet rolls lid, labeling, packs and obtains fluorine pula and praise freeze-dried powder.
Embodiment 10
Prescription
Method for making: method is first to join in 90% water for injection by glucose, sodium thiosulfate, and water for injection is cooled to less than 25 degree, addition fluorine pula is praised and is stirred and makes it dissolve, adjust pH value to 5.5, add needle-use activated carbon 60 degree insulation and adsorb 30min, then inject and use water constant volume, cross 0.22 micron membrane filter, fill, every 2mL, enter freeze drying box lyophilizing, lyophilization cycle is about 24 hours, and outlet rolls lid, labeling, packs and obtains fluorine pula and praise freeze-dried powder.
Embodiment 11
Prescription
Method for making: method is first to join in 90% water for injection by glucose, sodium pyrosulfite, and water for injection is cooled to less than 25 degree, addition fluorine pula is praised and is stirred and makes it dissolve, adjust pH value to 5.5, add needle-use activated carbon 60 degree insulation and adsorb 30min, then inject and use water constant volume, cross 0.22 micron membrane filter, fill, every 2mL, enter freeze drying box lyophilizing, lyophilization cycle is about 24 hours, and outlet rolls lid, labeling, packs and obtains fluorine pula and praise freeze-dried powder.
Embodiment 12
Prescription
Method for making: method is first to join in 90% water for injection by lactose, sodium thiosulfate, and water for injection is cooled to less than 25 degree, addition fluorine pula is praised and is stirred and makes it dissolve, adjust pH value to 5.5, add needle-use activated carbon 60 degree insulation and adsorb 30min, then inject and use water constant volume, cross 0.22 micron membrane filter, fill, every 2mL, enter freeze drying box lyophilizing, lyophilization cycle is about 24 hours, and outlet rolls lid, labeling, packs and obtains fluorine pula and praise freeze-dried powder.
Embodiment 13
Prescription
Method for making: method is first to join in 90% water for injection by mannitol, sodium sulfite, and water for injection is cooled to less than 25 degree, addition fluorine pula is praised and is stirred and makes it dissolve, adjust pH value to 4.0-5.0, add needle-use activated carbon 60 degree and be incubated and adsorb 30min, then inject and use water constant volume, cross 0.22 micron membrane filter, fill, every 2mL, enter freeze drying box lyophilizing, lyophilization cycle is about 24 hours, and outlet rolls lid, labeling, packs and obtains fluorine pula and praise freeze-dried powder.
Embodiment 14
Prescription
Method for making: method is first to join in 90% water for injection by mannitol, sodium sulfite, and water for injection is cooled to less than 25 degree, addition fluorine pula is praised and is stirred and makes it dissolve, adjust pH value to 4.0-5.0, add needle-use activated carbon 60 degree and be incubated and adsorb 30min, then inject and use water constant volume, cross 0.22 micron membrane filter, fill, every 2mL, enter freeze drying box lyophilizing, lyophilization cycle is about 24 hours, and outlet rolls lid, labeling, packs and obtains fluorine pula and praise freeze-dried powder.
Embodiment 15
Prescription
Method for making: method is first to join in 90% water for injection by mannitol, sodium pyrosulfite, and water for injection is cooled to less than 25 degree, addition fluorine pula is praised and is stirred and makes it dissolve, adjust pH value to 4.0-5.0, add needle-use activated carbon 60 degree and be incubated and adsorb 30min, then inject and use water constant volume, cross 0.22 micron membrane filter, fill, every 2mL, enter freeze drying box lyophilizing, lyophilization cycle is about 24 hours, and outlet rolls lid, labeling, packs and obtains fluorine pula and praise freeze-dried powder.
Embodiment 16
Prescription
Method for making: method is first to join in 90% water for injection by lactose, sodium sulfite, and water for injection is cooled to less than 25 degree, addition fluorine pula is praised and is stirred and makes it dissolve, adjust pH value to 4.5-5.5, add needle-use activated carbon 60 degree and be incubated and adsorb 30min, then inject and use water constant volume, cross 0.22 micron membrane filter, fill, every 2mL, enter freeze drying box lyophilizing, lyophilization cycle is about 24 hours, and outlet rolls lid, labeling, packs and obtains fluorine pula and praise freeze-dried powder.
Embodiment 17
Prescription
Method for making: method is first to join in 90% water for injection by lactose, sodium pyrosulfite, and water for injection is cooled to less than 25 degree, addition fluorine pula is praised and is stirred and makes it dissolve, adjust pH value to 5.0-7.0, add needle-use activated carbon 60 degree and be incubated and adsorb 30min, then inject and use water constant volume, cross 0.22 micron membrane filter, fill, every 2mL, enter freeze drying box lyophilizing, lyophilization cycle is about 24 hours, and outlet rolls lid, labeling, packs and obtains fluorine pula and praise freeze-dried powder.
Embodiment 18
Prescription
Method for making: method is first to join in 90% water for injection by sodium chloride, sodium thiosulfate, and water for injection is cooled to less than 25 degree, addition fluorine pula is praised and is stirred and makes it dissolve, adjust pH value to 5.5, add needle-use activated carbon 60 degree insulation and adsorb 30min, then inject and use water constant volume, cross 0.22 micron membrane filter, fill, every 2mL, enter freeze drying box lyophilizing, lyophilization cycle is about 24 hours, and outlet rolls lid, labeling, packs and obtains fluorine pula and praise freeze-dried powder.
Embodiment 19
Prescription
Method for making: method is first to join in 90% water for injection by glucose, sodium sulfite, and water for injection is cooled to less than 25 degree, addition fluorine pula is praised and is stirred and makes it dissolve, adjust pH value to 5.5, add needle-use activated carbon 60 degree insulation and adsorb 30min, then inject and use water constant volume, cross 0.22 micron membrane filter, fill, every 2mL, enter freeze drying box lyophilizing, lyophilization cycle is about 24 hours, and outlet rolls lid, labeling, packs and obtains fluorine pula and praise freeze-dried powder.
Embodiment 20
Prescription
Method for making: method is first to join in 90% water for injection by sorbitol, sodium thiosulfate, and water for injection is cooled to less than 25 degree, addition fluorine pula is praised and is stirred and makes it dissolve, adjust pH value to 5.5, add needle-use activated carbon 60 degree insulation and adsorb 30min, then inject and use water constant volume, cross 0.22 micron membrane filter, fill, every 2mL, enter freeze drying box lyophilizing, lyophilization cycle is about 24 hours, and outlet rolls lid, labeling, packs and obtains fluorine pula and praise freeze-dried powder.
Embodiment 21
Prescription
Method for making: method is first to join in 90% water for injection by glucose, sodium thiosulfate, and water for injection is cooled to less than 25 degree, addition fluorine pula is praised and is stirred and makes it dissolve, adjust pH value to 5.5, add needle-use activated carbon 60 degree insulation and adsorb 30min, then inject and use water constant volume, cross 0.22 micron membrane filter, fill, every 2mL, enter freeze drying box lyophilizing, lyophilization cycle is about 24 hours, and outlet rolls lid, labeling, packs and obtains fluorine pula and praise freeze-dried powder.
Embodiment 22
Prescription
Method for making: method is first to join in 90% water for injection by glucose, sodium thiosulfate, and water for injection is cooled to less than 25 degree, addition fluorine pula is praised and is stirred and makes it dissolve, adjust pH value to 5.5, add needle-use activated carbon 60 degree insulation and adsorb 30min, then inject and use water constant volume, cross 0.22 micron membrane filter, fill, every 2mL, enter freeze drying box lyophilizing, lyophilization cycle is about 24 hours, and outlet rolls lid, labeling, packs and obtains fluorine pula and praise freeze-dried powder.
Embodiment 23
Prescription
Method for making: method is first to join in 90% water for injection by glucose, sodium pyrosulfite, and water for injection is cooled to less than 25 degree, addition fluorine pula is praised and is stirred and makes it dissolve, adjust pH value to 5.5, add needle-use activated carbon 60 degree insulation and adsorb 30min, then inject and use water constant volume, cross 0.22 micron membrane filter, fill, every 2mL, enter freeze drying box lyophilizing, lyophilization cycle is about 24 hours, and outlet rolls lid, labeling, packs and obtains fluorine pula and praise freeze-dried powder.
Embodiment 24
Prescription
Method for making: method is first to join in 90% water for injection by lactose, sodium thiosulfate, and water for injection is cooled to less than 25 degree, addition fluorine pula is praised and is stirred and makes it dissolve, adjust pH value to 5.5, add needle-use activated carbon 60 degree insulation and adsorb 30min, then inject and use water constant volume, cross 0.22 micron membrane filter, fill, every 2mL, enter freeze drying box lyophilizing, lyophilization cycle is about 24 hours, and outlet rolls lid, labeling, packs and obtains fluorine pula and praise freeze-dried powder.
According to the present invention, advantageously, described fluorine pula is praised inorganic or acylate freeze-dried powder dissolubility in glucose injection and chloride injection equal solvent is good, compatibility stability is good, it is suitable for intravenous drip or intravenous injection, special solvent or cosolvent need not be used, and solution clarity meets the requirements.In addition, also there is good stability, effect duration length, store the advantages such as convenient transportation.
The fluorine pula that the present invention prepares is praised inorganic or its Clinical practice compatibility stability of acylate freeze-dried powder good, is suitable for intravenous drip.Its experimental result is shown in following table:
Acetate freeze-dried powder (lot number: 20140101) and 5% glucose compatibility stability experiment are praised in fluorine pula
Acetate freeze-dried powder (lot number: 20140101) and 0.9% sodium chloride compatibility stability experiment are praised in fluorine pula
Acetate freeze-dried powder is praised through study on the stability in the fluorine pula that the present invention prepares, it was demonstrated that good stability, and its effect duration can reach 2 years.
High temperature Acceleration study: sample is placed in 40 ± 2 DEG C, in the climatic chamber of relative humidity 75%, respectively at the 1st, 2,3,6 months period sampling measurings, and with 0 month results contrast, result is shown in following table:
Room temperature keeps sample investigation experiment: sample is placed in 25 DEG C, in the climatic chamber of relative humidity 60 ± 10%, respectively at the 3rd, 6,9,12,18,24 months period sampling measurings, and with 0 month results contrast, result is shown in following table:
Claims (10)
1. inorganic or acylate freeze-dried powder is praised in the fluorine pula described in a following structure
In formula, HA is acetic acid, methanesulfonic acid, sulphuric acid, phosphoric acid;
It is characterized in that: this freeze-dried powder is praised inorganic or acylate by fluorine pula, antioxidant, freeze-dried excipient, pH value regulator form, wherein the molar ratio with antioxidant is praised in fluorine pula is 1:0.5 ~ 1:1.5, and it is 1:1 ~ 1:5 that the molar ratio with freeze-dried excipient is praised in fluorine pula.
2. inorganic or acylate freeze-dried powder is praised in fluorine pula according to claim 1, it is characterised in that it is acetic acid, methanesulfonic acid, sulphuric acid, phosphoric acid that its acid group is praised in fluorine pula.
3. inorganic or acylate freeze-dried powder is praised in fluorine pula according to claim 1, it is characterised in that described freeze-dried excipient is mannitol, lactose, glucose, sorbitol, sodium chloride.
4. inorganic or acylate freeze-dried powder is praised in fluorine pula according to claim 1, it is characterised in that described antioxidant is sodium sulfite, sodium sulfite, sodium pyrosulfite, sodium thiosulfate.
5. inorganic or acylate freeze-dried powder is praised in fluorine pula according to claim 1, it is characterised in that pH value regulator is acetic acid, methanesulfonic acid, hydrochloric acid and phosphoric acid.
6. inorganic or acylate freeze-dried powder is praised in fluorine pula according to claim 1, it is characterised in that: this injection pH ranges for 4.0-8.5.
7. freeze-dried powder according to claim 3, it is characterised in that described pH value range is 4.5-7.5.
8. freeze-dried powder according to claim 4, it is characterised in that described pH value range is 5.0-7.0.
9. inorganic or acylate freeze-dried powder is praised in fluorine pula according to claim 1, it is characterized in that, its production method comprises the following steps: method is first by stabilizer, antioxidant joins in 90% water for injection, addition fluorine pula praises inorganic or acylate and stirring makes it dissolve, adjust pH value to 5.0-7.0, add needle-use activated carbon 60 degree insulation absorption 30min, inject again and use water constant volume, filter, fill, enter freeze drying box lyophilizing, lyophilization cycle is about 24 hours, outlet, roll lid, labeling, pack and obtain fluorine pula and praise inorganic or acylate freeze-dried powder.
10. the present invention is used for erosive esophagitis, gastric ulcer, duodenal ulcer, helicobacter pylori eradication indication, and treats the relevant disease caused due to hyperchlorhydria.
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CN201410712609.1A CN105708812A (en) | 2014-12-02 | 2014-12-02 | 5-(2-fluorophenyl)-N-methyl-1-(3-pyridylsulfonyl)-1H-pyrrole-3-methylamine freeze-dried powder injection and preparation method thereof |
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CN201410712609.1A CN105708812A (en) | 2014-12-02 | 2014-12-02 | 5-(2-fluorophenyl)-N-methyl-1-(3-pyridylsulfonyl)-1H-pyrrole-3-methylamine freeze-dried powder injection and preparation method thereof |
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CN101300229A (en) * | 2005-08-30 | 2008-11-05 | 武田药品工业株式会社 | 1-heterocyclylsulfonyl, 2-aminomethyl, 5- (hetero-) aryl substituted 1-h-pyrrole derivatives as acid secretion inhibitors |
CN102038648A (en) * | 2009-10-23 | 2011-05-04 | 丽珠医药集团股份有限公司 | Powder injection for treating peptic ulcers and preparation method thereof |
CN102470126A (en) * | 2009-07-09 | 2012-05-23 | 拉夸里亚创药株式会社 | Acid pump antagonist for treatment of diseases associated with abnormal gastrointestinal movement |
CN103951652A (en) * | 2014-04-18 | 2014-07-30 | 潍坊博创国际生物医药研究院 | Water soluble salts of organic acid 5-(2-fluorophenyl)-N-methyl-1-(3-pyridyl sulfonyl)-1H-pyrrole-3-methylamine and injection and preparation method thereof |
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- 2014-12-02 CN CN201410712609.1A patent/CN105708812A/en active Pending
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CN101300229A (en) * | 2005-08-30 | 2008-11-05 | 武田药品工业株式会社 | 1-heterocyclylsulfonyl, 2-aminomethyl, 5- (hetero-) aryl substituted 1-h-pyrrole derivatives as acid secretion inhibitors |
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