CN100338038C - 阿立派唑的新晶型及其制备方法 - Google Patents
阿立派唑的新晶型及其制备方法 Download PDFInfo
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- CN100338038C CN100338038C CNB2004100793813A CN200410079381A CN100338038C CN 100338038 C CN100338038 C CN 100338038C CN B2004100793813 A CNB2004100793813 A CN B2004100793813A CN 200410079381 A CN200410079381 A CN 200410079381A CN 100338038 C CN100338038 C CN 100338038C
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- Prior art keywords
- aripiprazole
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- crystal
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- 238000002360 preparation method Methods 0.000 title claims abstract description 33
- 229960004372 aripiprazole Drugs 0.000 claims abstract description 100
- CEUORZQYGODEFX-UHFFFAOYSA-N Aripirazole Chemical compound ClC1=CC=CC(N2CCN(CCCCOC=3C=C4NC(=O)CCC4=CC=3)CC2)=C1Cl CEUORZQYGODEFX-UHFFFAOYSA-N 0.000 claims abstract description 98
- 239000013078 crystal Substances 0.000 claims abstract description 94
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 41
- 239000000843 powder Substances 0.000 claims abstract description 13
- 239000003814 drug Substances 0.000 claims abstract description 7
- 201000000980 schizophrenia Diseases 0.000 claims abstract description 4
- 230000004580 weight loss Effects 0.000 claims abstract description 3
- 229960000935 dehydrated alcohol Drugs 0.000 claims description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 230000015572 biosynthetic process Effects 0.000 claims description 12
- 238000009413 insulation Methods 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 8
- 238000001035 drying Methods 0.000 claims description 8
- 238000002329 infrared spectrum Methods 0.000 claims description 8
- 239000012046 mixed solvent Substances 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- 238000001228 spectrum Methods 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- 239000002775 capsule Substances 0.000 claims description 6
- 230000006837 decompression Effects 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 230000001476 alcoholic effect Effects 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 238000010521 absorption reaction Methods 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 4
- 239000002245 particle Substances 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- 229960001701 chloroform Drugs 0.000 claims description 2
- 230000003068 static effect Effects 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 abstract description 25
- 238000010438 heat treatment Methods 0.000 abstract description 25
- 230000008025 crystallization Effects 0.000 abstract description 24
- 238000002411 thermogravimetry Methods 0.000 abstract 1
- 238000003756 stirring Methods 0.000 description 16
- 239000000126 substance Substances 0.000 description 13
- 238000005755 formation reaction Methods 0.000 description 11
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 238000007710 freezing Methods 0.000 description 7
- 230000008014 freezing Effects 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000000967 suction filtration Methods 0.000 description 7
- 239000008194 pharmaceutical composition Substances 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- 229920002472 Starch Polymers 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000000634 powder X-ray diffraction Methods 0.000 description 5
- 229940032147 starch Drugs 0.000 description 5
- 239000008107 starch Substances 0.000 description 5
- 235000019698 starch Nutrition 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 239000012043 crude product Substances 0.000 description 3
- 229960004756 ethanol Drugs 0.000 description 3
- 235000011194 food seasoning agent Nutrition 0.000 description 3
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
- -1 quinoline ketone Chemical class 0.000 description 3
- 239000008109 sodium starch glycolate Substances 0.000 description 3
- 229940079832 sodium starch glycolate Drugs 0.000 description 3
- 229920003109 sodium starch glycolate Polymers 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- UXQBDXJXIVDBTF-UHFFFAOYSA-N 7-[4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butoxy]-3,4-dihydro-1h-quinolin-2-one;hydrate Chemical compound O.ClC1=CC=CC(N2CCN(CCCCOC=3C=C4NC(=O)CCC4=CC=3)CC2)=C1Cl UXQBDXJXIVDBTF-UHFFFAOYSA-N 0.000 description 2
- 239000004278 EU approved seasoning Substances 0.000 description 2
- 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 2
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 238000004458 analytical method 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
- 238000009776 industrial production Methods 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 2
- 239000008108 microcrystalline cellulose Substances 0.000 description 2
- 229940016286 microcrystalline cellulose Drugs 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 235000002566 Capsicum Nutrition 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
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 239000006002 Pepper Substances 0.000 description 1
- 235000016761 Piper aduncum Nutrition 0.000 description 1
- 235000017804 Piper guineense Nutrition 0.000 description 1
- 244000203593 Piper nigrum Species 0.000 description 1
- 235000008184 Piper nigrum Nutrition 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- 230000000561 anti-psychotic effect Effects 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007891 compressed tablet Substances 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000000881 depressing effect Effects 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 238000007908 dry granulation Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000009472 formulation Methods 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
- 238000000227 grinding Methods 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 239000007935 oral tablet Substances 0.000 description 1
- 229940096978 oral tablet Drugs 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000009637 wintergreen oil Substances 0.000 description 1
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (19)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB2004100793813A CN100338038C (zh) | 2004-10-14 | 2004-10-14 | 阿立派唑的新晶型及其制备方法 |
Applications Claiming Priority (1)
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---|---|---|---|
CNB2004100793813A CN100338038C (zh) | 2004-10-14 | 2004-10-14 | 阿立派唑的新晶型及其制备方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1760183A CN1760183A (zh) | 2006-04-19 |
CN100338038C true CN100338038C (zh) | 2007-09-19 |
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CNB2004100793813A Expired - Lifetime CN100338038C (zh) | 2004-10-14 | 2004-10-14 | 阿立派唑的新晶型及其制备方法 |
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CN (1) | CN100338038C (zh) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103172563B (zh) * | 2011-12-26 | 2015-03-25 | 北京京卫燕康药物研究所有限公司 | 小粒径的晶型i阿立哌唑的工业化制备 |
US10913721B2 (en) * | 2016-02-19 | 2021-02-09 | Nanjing Noratech Pharmaceuticals Co., Ltd | Crystalline form of aripiprazole |
CN106674103B (zh) * | 2016-12-08 | 2022-04-08 | 万全万特制药江苏有限公司 | 一种阿立哌唑新晶型α的制备方法 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1463191A (zh) * | 2001-09-25 | 2003-12-24 | 大塚制药株式会社 | 低吸湿性阿立哌唑药物及其制备方法 |
-
2004
- 2004-10-14 CN CNB2004100793813A patent/CN100338038C/zh not_active Expired - Lifetime
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1463191A (zh) * | 2001-09-25 | 2003-12-24 | 大塚制药株式会社 | 低吸湿性阿立哌唑药物及其制备方法 |
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CN1760183A (zh) | 2006-04-19 |
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Legal Events
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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 | ||
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TR01 | Transfer of patent right |
Effective date of registration: 20181228 Address after: 401221 No. 2 Yanjiahua South Third Branch Road, Changshou District, Chongqing Co-patentee after: Chongqing Pharmaceutical Research Institute Co., Ltd. Patentee after: Chongqing Medical Institute Pharmaceutical Co., Ltd. Address before: 400061 Tu Shan Road, South Bank district, Chongqing, No. 565 Patentee before: Chongqing Pharmaceutical Research Institute Co., Ltd. |
|
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20200417 Address after: 401221, No. 3, No. 1 South Road, Changshou chemical industry park, Chongqing Co-patentee after: CHONGQING PHARMACEUTICAL RESEARCH INSTITUTE Co.,Ltd. Patentee after: CHONGQING CARELIFE PHARMACEUTICAL Co.,Ltd. Address before: 401221 No. 2 Yanjiahua South Third Branch Road, Changshou District, Chongqing Co-patentee before: CHONGQING PHARMACEUTICAL RESEARCH INSTITUTE Co.,Ltd. Patentee before: Chongqing Medical Institute Pharmaceutical Co., Ltd. |