CN110283259A - 一种解热镇痛布洛芬-β-环糊精第一面衍生物及其制备方法 - Google Patents
一种解热镇痛布洛芬-β-环糊精第一面衍生物及其制备方法 Download PDFInfo
- Publication number
- CN110283259A CN110283259A CN201910594178.6A CN201910594178A CN110283259A CN 110283259 A CN110283259 A CN 110283259A CN 201910594178 A CN201910594178 A CN 201910594178A CN 110283259 A CN110283259 A CN 110283259A
- Authority
- CN
- China
- Prior art keywords
- brufen
- beta
- face
- cyclodextrin
- antipyretic
- Prior art date
- 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.)
- Granted
Links
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical class OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 title claims abstract description 55
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims abstract description 87
- 229920000858 Cyclodextrin Polymers 0.000 claims abstract description 50
- 239000001116 FEMA 4028 Substances 0.000 claims abstract description 44
- 229960004853 betadex Drugs 0.000 claims abstract description 44
- 235000011175 beta-cyclodextrine Nutrition 0.000 claims abstract description 38
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 30
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims abstract description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims abstract description 13
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims abstract description 11
- 229910000029 sodium carbonate Inorganic materials 0.000 claims abstract description 10
- 230000004048 modification Effects 0.000 claims abstract description 7
- 238000012986 modification Methods 0.000 claims abstract description 7
- 230000004913 activation Effects 0.000 claims abstract description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 96
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 49
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 claims description 18
- -1 CDI Chemical compound 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 10
- 239000012043 crude product Substances 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 7
- 238000000605 extraction Methods 0.000 claims description 7
- 238000003786 synthesis reaction Methods 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 claims description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 claims description 4
- 239000004744 fabric Substances 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 230000001376 precipitating effect Effects 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 239000002221 antipyretic Substances 0.000 abstract description 8
- 230000001754 anti-pyretic effect Effects 0.000 abstract description 7
- 230000000202 analgesic effect Effects 0.000 abstract description 6
- 230000000857 drug effect Effects 0.000 abstract description 4
- 206010000087 Abdominal pain upper Diseases 0.000 abstract description 3
- 206010067484 Adverse reaction Diseases 0.000 abstract description 3
- 206010018910 Haemolysis Diseases 0.000 abstract description 3
- 206010047700 Vomiting Diseases 0.000 abstract description 3
- 230000006838 adverse reaction Effects 0.000 abstract description 3
- 210000002784 stomach Anatomy 0.000 abstract description 3
- 230000008588 hemolysis Effects 0.000 abstract description 2
- 239000013067 intermediate product Substances 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 20
- 239000012074 organic phase Substances 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 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 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical group CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- 229960001680 ibuprofen Drugs 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229960001138 acetylsalicylic acid Drugs 0.000 description 3
- 230000036592 analgesia Effects 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000013268 sustained release Methods 0.000 description 3
- 239000012730 sustained-release form Substances 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 208000031220 Hemophilia Diseases 0.000 description 2
- 208000009292 Hemophilia A Diseases 0.000 description 2
- 206010037660 Pyrexia Diseases 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 239000007853 buffer solution Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000006837 decompression Effects 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 208000031169 hemorrhagic disease Diseases 0.000 description 2
- 230000002008 hemorrhagic effect Effects 0.000 description 2
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- BXVGCNQIUDNXRC-UHFFFAOYSA-N 2-[2-methyl-4-(2-methylpropyl)phenyl]acetic acid Chemical compound CC(C)CC1=CC=C(CC(O)=O)C(C)=C1 BXVGCNQIUDNXRC-UHFFFAOYSA-N 0.000 description 1
- HUJKNQNWWPEXLW-UHFFFAOYSA-N 2-methylpropylbenzene;propanoic acid Chemical compound CCC(O)=O.CC(C)CC1=CC=CC=C1 HUJKNQNWWPEXLW-UHFFFAOYSA-N 0.000 description 1
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 206010013935 Dysmenorrhoea Diseases 0.000 description 1
- 206010018873 Haemoconcentration Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 210000001772 blood platelet Anatomy 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002678 macrocyclic compounds Chemical class 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 230000036407 pain Effects 0.000 description 1
- 229960005489 paracetamol Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002510 pyrogen Substances 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 230000006103 sulfonylation Effects 0.000 description 1
- 238000005694 sulfonylation reaction Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
Classifications
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid
-
- 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
- A61K47/50—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6949—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
- A61K47/6951—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes using cyclodextrin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Biochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- Molecular Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Description
Claims (7)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201910594178.6A CN110283259B (zh) | 2019-07-03 | 2019-07-03 | 一种解热镇痛布洛芬-β-环糊精第一面衍生物及其制备方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201910594178.6A CN110283259B (zh) | 2019-07-03 | 2019-07-03 | 一种解热镇痛布洛芬-β-环糊精第一面衍生物及其制备方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN110283259A true CN110283259A (zh) | 2019-09-27 |
CN110283259B CN110283259B (zh) | 2021-12-10 |
Family
ID=68021771
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201910594178.6A Expired - Fee Related CN110283259B (zh) | 2019-07-03 | 2019-07-03 | 一种解热镇痛布洛芬-β-环糊精第一面衍生物及其制备方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN110283259B (zh) |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20100048734A1 (en) * | 2008-08-22 | 2010-02-25 | Ma Peter X | Hydrophilic copolymers and assemblies containing the same |
CN101991540A (zh) * | 2009-08-27 | 2011-03-30 | 杭州赛利药物研究所有限公司 | 一种布洛芬注射剂及其制备方法 |
GB201121476D0 (en) * | 2010-12-15 | 2012-01-25 | Reckitt Benckiser Healthcare Int Ltd | Novel pharmaceutical formulation |
CN104203255A (zh) * | 2012-01-31 | 2014-12-10 | 天蓝制药公司 | 用于传递治疗剂的基于环糊精的聚合物 |
CN108774290A (zh) * | 2018-07-10 | 2018-11-09 | 宁夏医科大学 | 白藜芦醇-羧烷基型环糊精衍生物及其制备方法 |
CN109825284A (zh) * | 2019-01-23 | 2019-05-31 | 东莞理工学院 | 一种乙二胺-β-环糊精修饰的Mn掺杂ZnS量子点及其制备方法和应用 |
-
2019
- 2019-07-03 CN CN201910594178.6A patent/CN110283259B/zh not_active Expired - Fee Related
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20100048734A1 (en) * | 2008-08-22 | 2010-02-25 | Ma Peter X | Hydrophilic copolymers and assemblies containing the same |
CN101991540A (zh) * | 2009-08-27 | 2011-03-30 | 杭州赛利药物研究所有限公司 | 一种布洛芬注射剂及其制备方法 |
GB201121476D0 (en) * | 2010-12-15 | 2012-01-25 | Reckitt Benckiser Healthcare Int Ltd | Novel pharmaceutical formulation |
CN104203255A (zh) * | 2012-01-31 | 2014-12-10 | 天蓝制药公司 | 用于传递治疗剂的基于环糊精的聚合物 |
CN108774290A (zh) * | 2018-07-10 | 2018-11-09 | 宁夏医科大学 | 白藜芦醇-羧烷基型环糊精衍生物及其制备方法 |
CN109825284A (zh) * | 2019-01-23 | 2019-05-31 | 东莞理工学院 | 一种乙二胺-β-环糊精修饰的Mn掺杂ZnS量子点及其制备方法和应用 |
Non-Patent Citations (2)
Title |
---|
DEEPALI V等: "《Synthesis and Pharmacological Evaluation of Cyclodextrin Conjugate Prodrugs of Ibuprofen》", 《INDIAN JOURNAL OF PHARMACEUTICAL SCIENCES》 * |
SHI JIE WEI 等: "《Regioselective synthesis, stability and release behaviors of the secondary 5-fluorouracil acetic acid/β-cyclodextrin conjugate for colon delivery》", 《JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY》 * |
Also Published As
Publication number | Publication date |
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CN110283259B (zh) | 2021-12-10 |
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Granted publication date: 20211210 |