CN102229557A - Semihydrate crystal of silodosin, preparation method thereof and medicinal composition containing semihydrate crystal - Google Patents
Semihydrate crystal of silodosin, preparation method thereof and medicinal composition containing semihydrate crystal Download PDFInfo
- Publication number
- CN102229557A CN102229557A CN2010102453370A CN201010245337A CN102229557A CN 102229557 A CN102229557 A CN 102229557A CN 2010102453370 A CN2010102453370 A CN 2010102453370A CN 201010245337 A CN201010245337 A CN 201010245337A CN 102229557 A CN102229557 A CN 102229557A
- Authority
- CN
- China
- Prior art keywords
- crystal
- silodosin
- organic solvent
- semihydrate
- formula
- 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
- 239000013078 crystal Substances 0.000 title claims abstract description 40
- PNCPYILNMDWPEY-QGZVFWFLSA-N silodosin Chemical compound N([C@@H](CC=1C=C(C=2N(CCCO)CCC=2C=1)C(N)=O)C)CCOC1=CC=CC=C1OCC(F)(F)F PNCPYILNMDWPEY-QGZVFWFLSA-N 0.000 title claims abstract description 35
- 229960004953 silodosin Drugs 0.000 title claims abstract description 34
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- 239000000203 mixture Substances 0.000 title claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000003960 organic solvent Substances 0.000 claims abstract description 9
- 239000002775 capsule Substances 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 13
- 238000001035 drying Methods 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 238000009472 formulation Methods 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 2
- 238000013019 agitation Methods 0.000 claims 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 1
- 238000001291 vacuum drying Methods 0.000 claims 1
- 238000000634 powder X-ray diffraction Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 description 10
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 5
- 239000004141 Sodium laurylsulphate Substances 0.000 description 5
- 238000004455 differential thermal analysis Methods 0.000 description 5
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 5
- 230000004580 weight loss Effects 0.000 description 5
- 229920000881 Modified starch Polymers 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000005755 formation reaction Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 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 3
- 229930195725 Mannitol Natural products 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 239000000594 mannitol Substances 0.000 description 3
- 235000010355 mannitol Nutrition 0.000 description 3
- 206010013786 Dry skin Diseases 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
- 206010029216 Nervousness Diseases 0.000 description 2
- DRHKJLXJIQTDTD-OAHLLOKOSA-N Tamsulosine Chemical compound CCOC1=CC=CC=C1OCCN[C@H](C)CC1=CC=C(OC)C(S(N)(=O)=O)=C1 DRHKJLXJIQTDTD-OAHLLOKOSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000008602 contraction Effects 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
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 229940031703 low substituted hydroxypropyl cellulose Drugs 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 229960002613 tamsulosin Drugs 0.000 description 2
- 210000003708 urethra Anatomy 0.000 description 2
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 description 1
- 206010007026 Calculus urethral Diseases 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 229920003081 Povidone K 30 Polymers 0.000 description 1
- 206010060862 Prostate cancer Diseases 0.000 description 1
- 208000004403 Prostatic Hyperplasia Diseases 0.000 description 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
- 206010051482 Prostatomegaly Diseases 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229960002748 norepinephrine Drugs 0.000 description 1
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- QPUMEZIFDXYGPG-UHFFFAOYSA-N piperazine 1H-pyrrole Chemical class N1CCNCC1.N1C=CC=C1 QPUMEZIFDXYGPG-UHFFFAOYSA-N 0.000 description 1
- IENZQIKPVFGBNW-UHFFFAOYSA-N prazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 IENZQIKPVFGBNW-UHFFFAOYSA-N 0.000 description 1
- 229960001289 prazosin Drugs 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000452 restraining effect Effects 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 201000009160 urethral calculus Diseases 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- 238000004457 water analysis Methods 0.000 description 1
Images
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Abstract
Description
Element | Test value (%) | Theoretical value (%) |
C | 59.34 | 59.46 |
H | 6.59 | 6.54 |
N | 8.26 | 8.32 |
F | 11.24 | 11.30 |
Claims (9)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 201010245337 CN102229557B (en) | 2010-08-05 | 2010-08-05 | Semihydrate crystal of silodosin, preparation method thereof and medicinal composition containing semihydrate crystal |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 201010245337 CN102229557B (en) | 2010-08-05 | 2010-08-05 | Semihydrate crystal of silodosin, preparation method thereof and medicinal composition containing semihydrate crystal |
Publications (2)
Publication Number | Publication Date |
---|---|
CN102229557A true CN102229557A (en) | 2011-11-02 |
CN102229557B CN102229557B (en) | 2013-03-27 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CN 201010245337 Active CN102229557B (en) | 2010-08-05 | 2010-08-05 | Semihydrate crystal of silodosin, preparation method thereof and medicinal composition containing semihydrate crystal |
Country Status (1)
Country | Link |
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CN (1) | CN102229557B (en) |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1694867A (en) * | 2002-09-06 | 2005-11-09 | 橘生药品工业株式会社 | Crystal for oral solid drug and oral solid drug for dysuria treatment containing the same |
CN101048376A (en) * | 2004-10-27 | 2007-10-03 | 橘生药品工业株式会社 | Indoline compound and process for producing the same |
CN101412690A (en) * | 2008-12-01 | 2009-04-22 | 巢杰 | Medicinal acid addition salt of silodosin, and preparation and medicament use thereof |
-
2010
- 2010-08-05 CN CN 201010245337 patent/CN102229557B/en active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1694867A (en) * | 2002-09-06 | 2005-11-09 | 橘生药品工业株式会社 | Crystal for oral solid drug and oral solid drug for dysuria treatment containing the same |
CN101048376A (en) * | 2004-10-27 | 2007-10-03 | 橘生药品工业株式会社 | Indoline compound and process for producing the same |
CN101412690A (en) * | 2008-12-01 | 2009-04-22 | 巢杰 | Medicinal acid addition salt of silodosin, and preparation and medicament use thereof |
Non-Patent Citations (2)
Title |
---|
《Neurourology and Urodynamics》 20100515 Tomonori Yamanishi et al. "Urodynamic Effects of Silodosin, a New a1A-Adrenoceptor Selective Antagonist, for the Treatment of Benign Prostatic Hyperplasia" 第558-562页 1-9 第29卷, * |
TOMONORI YAMANISHI ET AL.: ""Urodynamic Effects of Silodosin, a New a1A-Adrenoceptor Selective Antagonist, for the Treatment of Benign Prostatic Hyperplasia"", 《NEUROUROLOGY AND URODYNAMICS》, vol. 29, 15 May 2010 (2010-05-15), pages 558 - 562 * |
Also Published As
Publication number | Publication date |
---|---|
CN102229557B (en) | 2013-03-27 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C53 | Correction of patent of invention or patent application | ||
CB02 | Change of applicant information |
Address after: 210009 Room 1520, 15th Floor, Building A, Science and Technology Innovation Building, Nanjing Tech University, No. 5 Xin Model Road, Gulou District, Jiangsu Province Applicant after: Zou Qiaogen Address before: 8, building 26, 210009 Ma Jia street, Gulou District, Nanjing, Jiangsu Applicant before: Zou Qiaogen |
|
EE01 | Entry into force of recordation of patent licensing contract |
Assignee: NANJING HEALTHNICE MEDICAL TECHNOLOGY Co.,Ltd. Assignor: Zou Qiaogen Contract record no.: 2012320000065 Denomination of invention: Semihydrate crystal of silodosin, preparation method thereof and medicinal composition containing semihydrate crystal License type: Exclusive License Open date: 20111102 Record date: 20120209 |
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ASS | Succession or assignment of patent right |
Owner name: NANJING HEALTHNICE MEDICAL TECHNOLOGY CO., LTD. Free format text: FORMER OWNER: ZOU QIAOGEN Effective date: 20121011 |
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C41 | Transfer of patent application or patent right or utility model | ||
TA01 | Transfer of patent application right |
Effective date of registration: 20121011 Address after: 15, building 210009, A building, 5 new model road, Gulou District, Nanjing, Jiangsu Applicant after: NANJING HEALTHNICE MEDICAL TECHNOLOGY Co.,Ltd. Address before: 210009 Room 1520, 15th Floor, Building A, Science and Technology Innovation Building, Nanjing Tech University, No. 5 Xin Model Road, Gulou District, Jiangsu Province Applicant before: Zou Qiaogen |
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C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
CP03 | Change of name, title or address |
Address after: 210009, A15 building, 5 new model road, Jiangsu, Nanjing Patentee after: NANJING HEALTHNICE PHARMACEUTICAL TECHNOLOGY CO.,LTD. Address before: 15, building 210009, A building, 5 new model road, Gulou District, Nanjing, Jiangsu Patentee before: NANJING HEALTHNICE MEDICAL TECHNOLOGY Co.,Ltd. |
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CP03 | Change of name, title or address | ||
TR01 | Transfer of patent right |
Effective date of registration: 20180514 Address after: 210009 A15 building, science and technology innovation building, 5 new model road, Nanjing, Jiangsu. Co-patentee after: NANJING HEALTHNICE PHARMACEUTICAL CO.,LTD. Patentee after: NANJING HEALTHNICE PHARMACEUTICAL TECHNOLOGY CO.,LTD. Address before: 210009 A15 building, science and technology innovation building, 5 new model road, Nanjing, Jiangsu. Patentee before: NANJING HEALTHNICE PHARMACEUTICAL TECHNOLOGY CO.,LTD. |
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TR01 | Transfer of patent right |