CN103142513B - A kind of injection racemization 2-(Alpha-hydroxy amyl group) benzoate freeze-dried powder and preparation method thereof - Google Patents
A kind of injection racemization 2-(Alpha-hydroxy amyl group) benzoate freeze-dried powder and preparation method thereof Download PDFInfo
- Publication number
- CN103142513B CN103142513B CN201310097200.9A CN201310097200A CN103142513B CN 103142513 B CN103142513 B CN 103142513B CN 201310097200 A CN201310097200 A CN 201310097200A CN 103142513 B CN103142513 B CN 103142513B
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- China
- Prior art keywords
- alpha
- benzoate
- racemization
- amyl group
- hours
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- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 230000006340 racemization Effects 0.000 title claims abstract description 46
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 239000000843 powder Substances 0.000 title claims abstract description 18
- 238000002347 injection Methods 0.000 title claims abstract description 16
- 239000007924 injection Substances 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title abstract description 39
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 10
- 239000002671 adjuvant Substances 0.000 claims abstract description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- 239000000243 solution Substances 0.000 claims description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 7
- 239000012467 final product Substances 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 claims description 5
- 239000011780 sodium chloride Substances 0.000 claims description 5
- 239000008215 water for injection Substances 0.000 claims description 5
- 239000012530 fluid Substances 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 238000004806 packaging method and process Methods 0.000 claims description 4
- 238000007789 sealing Methods 0.000 claims description 4
- 238000010792 warming Methods 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- 239000004411 aluminium Substances 0.000 claims description 3
- 239000012528 membrane Substances 0.000 claims description 3
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 claims description 3
- 235000010234 sodium benzoate Nutrition 0.000 claims description 3
- 239000004299 sodium benzoate Substances 0.000 claims description 3
- 229920005549 butyl rubber Polymers 0.000 claims description 2
- 238000005516 engineering process Methods 0.000 abstract description 8
- 239000003513 alkali Substances 0.000 abstract description 5
- 239000003814 drug Substances 0.000 abstract description 4
- 229940050390 benzoate Drugs 0.000 description 24
- HJXMNVQARNZTEE-UHFFFAOYSA-N Butylphthalide Chemical compound C1=CC=C2C(CCCC)OC(=O)C2=C1 HJXMNVQARNZTEE-UHFFFAOYSA-N 0.000 description 20
- 229950005197 butylphthalide Drugs 0.000 description 10
- 239000000203 mixture Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- JGSARLDLIJGVTE-UHFFFAOYSA-N 3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
- 235000010235 potassium benzoate Nutrition 0.000 description 3
- 239000004300 potassium benzoate Substances 0.000 description 3
- 229940103091 potassium benzoate Drugs 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000013558 reference substance Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 241000700159 Rattus Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- -1 anilino- Chemical group 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- WIHIUTUAHOZVLE-UHFFFAOYSA-N 1,3-diethoxypropan-2-ol Chemical group CCOCC(O)COCC WIHIUTUAHOZVLE-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical group [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000011575 calcium Chemical group 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010812 external standard method Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 1
- 229960000367 inositol Drugs 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Chemical group 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Chemical group 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
Landscapes
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Description
Principal agent | 50g |
Sodium hydroxide | (regulate pH9.5) in right amount |
Inspection item | Embodiment 1 | Embodiment 2 | Embodiment 3 | Embodiment 4 |
Outward appearance | Not full | Full, solid | Full, solid | Full, solid |
Solubility (5) | Jog is instant | Jog is instant | Jog is instant | Jog is instant |
Claims (1)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201310097200.9A CN103142513B (en) | 2013-03-25 | 2013-03-25 | A kind of injection racemization 2-(Alpha-hydroxy amyl group) benzoate freeze-dried powder and preparation method thereof |
CN201510695852.1A CN105343014B (en) | 2013-03-25 | 2013-03-25 | Injection racemization 2- (Alpha-hydroxy amyl) benzoate freeze-dried powder and preparation method thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201310097200.9A CN103142513B (en) | 2013-03-25 | 2013-03-25 | A kind of injection racemization 2-(Alpha-hydroxy amyl group) benzoate freeze-dried powder and preparation method thereof |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CN201510695852.1A Division CN105343014B (en) | 2013-03-25 | 2013-03-25 | Injection racemization 2- (Alpha-hydroxy amyl) benzoate freeze-dried powder and preparation method thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
CN103142513A CN103142513A (en) | 2013-06-12 |
CN103142513B true CN103142513B (en) | 2016-01-20 |
Family
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Family Applications (2)
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CN201510695852.1A Active CN105343014B (en) | 2013-03-25 | 2013-03-25 | Injection racemization 2- (Alpha-hydroxy amyl) benzoate freeze-dried powder and preparation method thereof |
CN201310097200.9A Active CN103142513B (en) | 2013-03-25 | 2013-03-25 | A kind of injection racemization 2-(Alpha-hydroxy amyl group) benzoate freeze-dried powder and preparation method thereof |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
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CN201510695852.1A Active CN105343014B (en) | 2013-03-25 | 2013-03-25 | Injection racemization 2- (Alpha-hydroxy amyl) benzoate freeze-dried powder and preparation method thereof |
Country Status (1)
Country | Link |
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CN (2) | CN105343014B (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104415020A (en) * | 2013-08-28 | 2015-03-18 | 云南昊邦制药有限公司 | Hydroxypentyl benzoate injection and preparation method thereof |
CN104414981A (en) * | 2013-08-28 | 2015-03-18 | 云南昊邦制药有限公司 | Freeze-dried hydroxyl-pentyl benzoate preparation for injection and preparation method of freeze-dried hydroxyl-pentyl benzoate preparation for injection |
CN108703953A (en) * | 2018-08-27 | 2018-10-26 | 海南皇隆制药股份有限公司 | A kind of injection benzene sulphur is along atracurium freeze drying powder injection and preparation method thereof |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1382682A (en) * | 2002-05-09 | 2002-12-04 | 中国医学科学院药物研究所 | 2-(alpha-hydroxypentyl) benzoate and its preparing process and usage |
CN1523003A (en) * | 2003-09-01 | 2004-08-25 | 北京天衡药物研究院 | Novel 2-(alpha-hydroxyl amyl) and its preparing method and use |
CN1594270A (en) * | 2004-06-17 | 2005-03-16 | 北京天衡药物研究院 | Novel L-2-(alpha-hydroxy pentyl)benzoate and its preparation method and use |
CN101054346A (en) * | 2006-04-13 | 2007-10-17 | 温建波 | Preparation method and use for a set of novel compound and composition thereof |
CN101627984A (en) * | 2008-07-14 | 2010-01-20 | 中国医学科学院药物研究所 | Application of 2-(alpha- hydroxyl amyl) potassium benzoate in preventing and/or treating senile dementia |
-
2013
- 2013-03-25 CN CN201510695852.1A patent/CN105343014B/en active Active
- 2013-03-25 CN CN201310097200.9A patent/CN103142513B/en active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1382682A (en) * | 2002-05-09 | 2002-12-04 | 中国医学科学院药物研究所 | 2-(alpha-hydroxypentyl) benzoate and its preparing process and usage |
CN1523003A (en) * | 2003-09-01 | 2004-08-25 | 北京天衡药物研究院 | Novel 2-(alpha-hydroxyl amyl) and its preparing method and use |
CN1594270A (en) * | 2004-06-17 | 2005-03-16 | 北京天衡药物研究院 | Novel L-2-(alpha-hydroxy pentyl)benzoate and its preparation method and use |
CN101054346A (en) * | 2006-04-13 | 2007-10-17 | 温建波 | Preparation method and use for a set of novel compound and composition thereof |
CN101627984A (en) * | 2008-07-14 | 2010-01-20 | 中国医学科学院药物研究所 | Application of 2-(alpha- hydroxyl amyl) potassium benzoate in preventing and/or treating senile dementia |
Also Published As
Publication number | Publication date |
---|---|
CN105343014B (en) | 2018-08-24 |
CN105343014A (en) | 2016-02-24 |
CN103142513A (en) | 2013-06-12 |
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