CN101735202B - 盐酸阿齐利特的晶型ⅰ及其制备方法和用途 - Google Patents
盐酸阿齐利特的晶型ⅰ及其制备方法和用途 Download PDFInfo
- Publication number
- CN101735202B CN101735202B CN2009102448755A CN200910244875A CN101735202B CN 101735202 B CN101735202 B CN 101735202B CN 2009102448755 A CN2009102448755 A CN 2009102448755A CN 200910244875 A CN200910244875 A CN 200910244875A CN 101735202 B CN101735202 B CN 101735202B
- Authority
- CN
- China
- Prior art keywords
- azimilide dihydrochloride
- azimilide
- dihydrochloride
- crystal formation
- preparation
- 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.)
- Expired - Fee Related
Links
- 229950001786 azimilide Drugs 0.000 title claims abstract description 52
- 239000013078 crystal Substances 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- MREBEPTUUMTTIA-PCLIKHOPSA-N Azimilide Chemical compound C1CN(C)CCN1CCCCN1C(=O)N(\N=C\C=2OC(=CC=2)C=2C=CC(Cl)=CC=2)CC1=O MREBEPTUUMTTIA-PCLIKHOPSA-N 0.000 title claims abstract 12
- 230000015572 biosynthetic process Effects 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 239000003416 antiarrhythmic agent Substances 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 6
- 239000011259 mixed solution Substances 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 238000000634 powder X-ray diffraction Methods 0.000 claims 1
- 239000000843 powder Substances 0.000 abstract description 8
- 239000000203 mixture Substances 0.000 abstract description 2
- HHPSICLSNHCSNZ-BYEGLACWSA-N 1-[(e)-[5-(4-chlorophenyl)furan-2-yl]methylideneamino]-3-[4-(4-methylpiperazin-1-yl)butyl]imidazolidine-2,4-dione;dihydrochloride Chemical compound Cl.Cl.C1CN(C)CCN1CCCCN1C(=O)N(\N=C\C=2OC(=CC=2)C=2C=CC(Cl)=CC=2)CC1=O HHPSICLSNHCSNZ-BYEGLACWSA-N 0.000 description 41
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- 239000007787 solid Substances 0.000 description 8
- 239000003814 drug Substances 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- 239000002775 capsule Substances 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 235000019359 magnesium stearate Nutrition 0.000 description 5
- 238000005303 weighing Methods 0.000 description 5
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 4
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 4
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 4
- 229960003943 hypromellose Drugs 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- 229940016286 microcrystalline cellulose Drugs 0.000 description 4
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 4
- 239000008108 microcrystalline cellulose Substances 0.000 description 4
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 229940032147 starch Drugs 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- 238000001291 vacuum drying Methods 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- YIVHSXTUXAMGOX-UHFFFAOYSA-N Cl.Cl.C(CO)(=O)NC(=O)N Chemical compound Cl.Cl.C(CO)(=O)NC(=O)N YIVHSXTUXAMGOX-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- ALOBUEHUHMBRLE-UHFFFAOYSA-N Ibutilide Chemical compound CCCCCCCN(CC)CCCC(O)C1=CC=C(NS(C)(=O)=O)C=C1 ALOBUEHUHMBRLE-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 102000004257 Potassium Channel Human genes 0.000 description 2
- 229960005260 amiodarone Drugs 0.000 description 2
- IYIKLHRQXLHMJQ-UHFFFAOYSA-N amiodarone Chemical compound CCCCC=1OC2=CC=CC=C2C=1C(=O)C1=CC(I)=C(OCCN(CC)CC)C(I)=C1 IYIKLHRQXLHMJQ-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 229960004053 ibutilide Drugs 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 108020001213 potassium channel Proteins 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011122 softwood Substances 0.000 description 2
- ZBMZVLHSJCTVON-UHFFFAOYSA-N sotalol Chemical compound CC(C)NCC(O)C1=CC=C(NS(C)(=O)=O)C=C1 ZBMZVLHSJCTVON-UHFFFAOYSA-N 0.000 description 2
- 229960002370 sotalol Drugs 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 206010047302 ventricular tachycardia Diseases 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 206010003658 Atrial Fibrillation Diseases 0.000 description 1
- 229910016523 CuKa Inorganic materials 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 102000013975 Delayed Rectifier Potassium Channels Human genes 0.000 description 1
- 108010050556 Delayed Rectifier Potassium Channels Proteins 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 206010049418 Sudden Cardiac Death Diseases 0.000 description 1
- 206010042600 Supraventricular arrhythmias Diseases 0.000 description 1
- 240000006474 Theobroma bicolor Species 0.000 description 1
- 206010047281 Ventricular arrhythmia Diseases 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 206010061592 cardiac fibrillation Diseases 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000002447 crystallographic data Methods 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 238000002050 diffraction method Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229960002994 dofetilide Drugs 0.000 description 1
- IXTMWRCNAAVVAI-UHFFFAOYSA-N dofetilide Chemical compound C=1C=C(NS(C)(=O)=O)C=CC=1CCN(C)CCOC1=CC=C(NS(C)(=O)=O)C=C1 IXTMWRCNAAVVAI-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000000890 drug combination Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical class CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000002600 fibrillogenic effect Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 230000003907 kidney function Effects 0.000 description 1
- 229960001375 lactose Drugs 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000008297 liquid dosage form Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- GVALZJMUIHGIMD-UHFFFAOYSA-H magnesium phosphate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O GVALZJMUIHGIMD-UHFFFAOYSA-H 0.000 description 1
- 229910000400 magnesium phosphate tribasic Inorganic materials 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000005405 multipole Effects 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- -1 polyoxyethylene Polymers 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000306 qrs interval Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
Images
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (4)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2009102448755A CN101735202B (zh) | 2009-12-17 | 2009-12-17 | 盐酸阿齐利特的晶型ⅰ及其制备方法和用途 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2009102448755A CN101735202B (zh) | 2009-12-17 | 2009-12-17 | 盐酸阿齐利特的晶型ⅰ及其制备方法和用途 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN101735202A CN101735202A (zh) | 2010-06-16 |
CN101735202B true CN101735202B (zh) | 2012-05-30 |
Family
ID=42459280
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN2009102448755A Expired - Fee Related CN101735202B (zh) | 2009-12-17 | 2009-12-17 | 盐酸阿齐利特的晶型ⅰ及其制备方法和用途 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN101735202B (zh) |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5462940A (en) * | 1991-08-14 | 1995-10-31 | Norwich Eaton Pharmaceuticals, Inc. | 4-oxocyclic ureas useful as antiarrhythmic and antifibrillatory agents |
CN1298403A (zh) * | 1998-04-29 | 2001-06-06 | 宝洁公司 | 1,3-二取代-4-氧代环状脲的制备方法 |
-
2009
- 2009-12-17 CN CN2009102448755A patent/CN101735202B/zh not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5462940A (en) * | 1991-08-14 | 1995-10-31 | Norwich Eaton Pharmaceuticals, Inc. | 4-oxocyclic ureas useful as antiarrhythmic and antifibrillatory agents |
CN1298403A (zh) * | 1998-04-29 | 2001-06-06 | 宝洁公司 | 1,3-二取代-4-氧代环状脲的制备方法 |
Non-Patent Citations (3)
Title |
---|
张翌.盐酸阿齐利特的合成.《中国优秀博硕士学位论文全文数据库(硕士)工程科技Ⅰ辑》.2007,(第5期),第23页第10段、第11段,第42页第6段及附录19. * |
张翌等.盐酸阿齐利特的合成.《中国药物化学杂志》.2006,第16卷(第4期),第232页第1栏第1段,第226页第1段. * |
郑其萍等.盐酸阿齐利特合成工艺的改进.《华西药学杂志》.2009,第24卷(第1期),第52页第1段,第53页第1栏第2段. * |
Also Published As
Publication number | Publication date |
---|---|
CN101735202A (zh) | 2010-06-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP2930169B1 (en) | Crystal form of chidamide, preparation method and use thereof | |
CN102219783B (zh) | 盐酸维拉佐酮及其组合物 | |
CN101735202B (zh) | 盐酸阿齐利特的晶型ⅰ及其制备方法和用途 | |
CN101735206B (zh) | 盐酸阿齐利特的晶型ⅳ及其制备方法和用途 | |
CN101735203B (zh) | 盐酸阿齐利特的晶型ⅱ及其制备方法和用途 | |
CN101735205B (zh) | 盐酸阿齐利特的晶型ⅴ及其制备方法和用途 | |
CN101735204B (zh) | 盐酸阿齐利特的晶型ⅲ及其制备方法和用途 | |
CN101774937A (zh) | N-[2-(7-甲氧基-1-萘基)乙基]乙酰胺及其组合物 | |
CN102304088B (zh) | 一种伊伐布雷定化合物、制备方法及其药物组合物 | |
CN102351881B (zh) | 一种稳定的盐酸左氧氟沙星化合物 | |
CN101735040B (zh) | 索法酮的晶型ⅲ及其制备方法和用途 | |
CN101735039B (zh) | 索法酮的晶型ⅱ及其制备方法和用途 | |
CN101781192B (zh) | 索法酮的晶型ⅵ及其制备方法和用途 | |
CN101735038B (zh) | 索法酮的晶型ⅰ及其制备方法和用途 | |
CN101781194B (zh) | 索法酮的晶型ⅴ及其制备方法和用途 | |
CN101792385B (zh) | 索法酮的晶型ⅷ及其制备方法和用途 | |
CN101817742B (zh) | 索法酮的晶型ⅹ及其制备方法和用途 | |
CN101817741B (zh) | 索法酮的晶型ⅸ及其制备方法和用途 | |
CN102120745B (zh) | 一种盐酸氯吡格雷的晶型ⅰ及其制备方法和用途 | |
CN101891703A (zh) | 一种非布司他的晶体、制备方法及在药物中的应用 | |
CN104447671A (zh) | 雏菊叶龙胆酮单晶及其制备方法与应用 | |
CN102010424B (zh) | (S)-α,α-[(2-氯苯基)-(4,5,6,7-四氢噻吩并[3,2-c]吡啶-5-基)]-N′-(二甲基)甲叉基)乙酰肼的晶型Ⅲ及其制备方法 | |
CN101781193B (zh) | 索法酮的晶型ⅳ及其制备方法和用途 | |
CN101781195B (zh) | 索法酮的晶型ⅶ及其制备方法和用途 | |
CN102120746A (zh) | 一种盐酸氯吡格雷晶型ⅱ及其制备方法和用途 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
C56 | Change in the name or address of the patentee | ||
CP01 | Change in the name or title of a patent holder |
Address after: 300193 Tianjin City, Nankai District Anshan West Road No. 308 Patentee after: Tianjin Institute of Pharmaceutical Research Co.,Ltd. Address before: 300193 Tianjin City, Nankai District Anshan West Road No. 308 Patentee before: Tianjin Institute of Pharmaceutical Research |
|
DD01 | Delivery of document by public notice |
Addressee: Bai Mei Document name: payment instructions |
|
DD01 | Delivery of document by public notice | ||
DD01 | Delivery of document by public notice |
Addressee: Bai Mei Document name: Patent termination notice |
|
DD01 | Delivery of document by public notice | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20120530 Termination date: 20211217 |
|
CF01 | Termination of patent right due to non-payment of annual fee |