CN102229557B - 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
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- CN102229557B CN102229557B CN 201010245337 CN201010245337A CN102229557B CN 102229557 B CN102229557 B CN 102229557B CN 201010245337 CN201010245337 CN 201010245337 CN 201010245337 A CN201010245337 A CN 201010245337A CN 102229557 B CN102229557 B CN 102229557B
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- 239000013078 crystal Substances 0.000 title claims abstract description 45
- 229960004953 silodosin Drugs 0.000 title claims abstract description 32
- 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 32
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- 239000000203 mixture Substances 0.000 title abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 206010013786 Dry skin Diseases 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000012452 mother liquor Substances 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 abstract description 2
- 238000000634 powder X-ray diffraction Methods 0.000 abstract 1
- 239000002775 capsule Substances 0.000 description 12
- 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
- 238000005755 formation reaction 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
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-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
- 239000000843 powder Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 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
- 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
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 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
- 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
- 238000009472 formulation Methods 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
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- Medicinal Preparation (AREA)
Abstract
The invention relates to semihydrate crystal of silodosin, a preparation method thereof and a medicinal composition containing the semihydrate crystal. The semihydrate crystal is prepared by crystallizing under the combined action of an organic solvent and water. The crystal form of the semihydrate crystal is represented by an X-ray powder diffraction figure of the semihydrate crystal.
Description
Technical field
The present invention relates to silodosin or formula (I) 2,3-dihydro-1-(3-hydroxypropyl)-5-[(2R)-2-[2-[2-(2,2,2-trifluoro ethoxy) phenoxy group] ethylamino-] propyl group]-semihydrate crystal, the preparation method of 1H-indoles-7-methane amide and comprise its pharmaceutical composition.
Background technology
Silodosin (silodosin), 2,3-dihydro-1-(3-hydroxypropyl)-5-[(2R)-2-[2-[2-(2,2, the 2-trifluoro ethoxy) phenoxy group] ethylamino-] propyl group]-1H-indoles-7-methane amide, be a kind of indoline-like compound of replacement, its molecular structural formula is as follows:
Silodosin is a kind of α
1-adrenoceptor antagonists, contraction has optionally restraining effect to the urethra smooth muscle, and be of great use be used for the treatment of per urethram tissue stop up relevant, urinate that the control nervous disorders is relevant, the urethral function obstruction relevant and by dysuric medical compounds due to prostatomegaly, urethrostenosis, urethral calculus, prostate cancer, nervous bladder, the disease of the lower urinary tract, it can not cause the hypopiesia of strong hypotensive activity or a straight property.Its selectively acting to urethra is higher 12 times than Prazosin respectively, and is higher 7.5 times than Tamsulosin; In addition, silodosin can obviously suppress the human prostate contraction that norepinephrine causes, drug effect and Tamsulosin are suitable, and stronger than piperazine azoles.
Silodosin has in US Patent No. 5387603 in the treatment dysuric purposes relevant with benign prostatic hyperplasia with it and describes.The preparation method of silodosin is disclosed in the Chinese patent 200580037040.2.Chinese patent 03824796.8 has been described silodosin α, β, three kinds of crystal formations of γ and preparation method thereof first.
In view of the pharmacological properties of this compound, obtain that purity is good, stability preferably this compound be very important and significant.In addition, as activeconstituents, with addition of pharmaceutically acceptable auxiliary material or vehicle, there is not yet report for the preparation of the dysuric pharmaceutical preparation for the treatment of with silodosin semihydrate crystal.
Summary of the invention
The present invention has now developed a kind of formula (I) compound, 2,3-dihydro-1-(3-hydroxypropyl)-5-[(2R)-2-[2-[2-(2,2, the 2-trifluoro ethoxy) phenoxy group] ethylamino-] propyl group]-1H-indoles-7-methane amide (silodosin) semihydrate crystal and preparation method, the method acquisition silodosin semihydrate can be very definite, that circulation ratio is fabulous crystal.This kind method has good stability, and is easy and simple to handle, cost is low and the characteristics such as economic environmental protection.
More specifically, the present invention relates to formula (I) compound crystal, it characterizes with following x-ray diffractogram of powder, uses diffractometer to measure, and represents with spacing d, 2 θ angles, intensity:
The invention still further relates to the preparation method of formula (I) compound crystal, the method is characterized in that, is to obtain formula (I) compound crystal after preparation and the drying under organic solvent and the water acting in conjunction.
The invention still further relates to and comprise as the semihydrate crystal of the silodosin of activeconstituents and the drug regimen of one or more suitable inert non-toxic vehicle.In the pharmaceutical composition of the present invention, what can mention more especially is to be suitable for oral formulation, tablet, capsule.
The performance test of silodosin semihydrate
1, ultimate analysis
| 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 |
Result's demonstration, test value is consistent with theoretical value.
2, thermal weight loss and differential thermal analysis
Get the sample for preparing by the inventive method and carry out thermal weight loss and differential thermal analysis.The sample for preparing of this law without weightlessness, does not namely contain planar water and volatile solvent in the sample before 0 ℃ as a result, 60～102 ℃ of weightlessness approximately 2.1%, this with sample in contain 0.5 molecular crystal water the result be consistent (theoretical value 1.98%).Differential thermal analysis result shows: this product has endotherm(ic)peak between 80～90 ℃, contains crystal water or recrystallisation solvent in the interpret sample.
3, weight loss on drying and water analysis
To be dried to constant weight at 65 ℃ with the sample that the inventive method prepares, the weight of less loss is 1.95%, and measuring its water content according to the Ka Shi aquametry simultaneously is that 1.93%, two kind of result is consistent, shows and only contains moisture in the sample, does not contain other solvents.
Comprehensive ultimate analysis, thermal weight loss and differential thermal analysis result can determine to contain in the sample 0.5 molecular crystal water.
Description of drawings
Fig. 1 is the X-ray diffractogram of silodosin semihydrate crystal, and described ordinate zou shows the intensity of X ray, represent with Kcps, X-coordinate be shown as 2 θ (°).
Fig. 2 is the thermal weight loss (TG graphic representation) of silodosin semihydrate crystal, and described ordinate zou is shown as part by weight (%) expression, and X-coordinate is shown as temperature ℃.
Fig. 3 is the differential thermal analysis (DSC graphic representation) of the crystal formation of silodosin semihydrate, and described ordinate zou is shown as compensation power (mW/mg) expression, and X-coordinate is shown as temperature ℃.
Embodiment
Following embodiment is explanation content of the present invention better, but the invention is not restricted to following example.
Embodiment 1: the preparation of the semihydrate crystal of silodosin
Get this product 1g with 2ml ethanol heating for dissolving after, remove by filter insolubles, stir and slowly drip 30ml water to crystalline solid in the mother liquor and separate out fully down, and continue to stir 30 minutes.Filter to collect the solid that obtains, in lower 50 ℃ of dryings of vacuum 12 hours to constant weight, obtain the 950mg crystal, purity 99.3%.The gained crystal formation characterizes with following x-ray diffractogram of powder, uses diffractometer to measure, and represents with spacing d, 2 θ angles, intensity and intensity:
Embodiment 2: the preparation of the semihydrate crystal of silodosin
Get this product 1g with 2ml ethyl acetate heating for dissolving after, remove by filter insolubles, stir lower slowly dripping in the mother liquor and add water to solid and separate out, add 5ml water after solid is separated out, and continue to stir 0.5 hour.Filter to collect the solid that obtains, in lower 50 ℃ of dryings of vacuum 12 hours to constant weight, obtain the 930mg crystal, purity 99.5%.
The gained crystal formation characterizes with following x-ray diffractogram of powder, uses diffractometer to measure, and represents with spacing d, 2 θ angles, intensity:
Embodiment 3: capsule 1
Prescription:
Silodosin semihydrate crystal 2 .0g
N.F,USP MANNITOL 66.5g
Pregelatinized Starch 30.0g
Magnesium Stearate 1.0g
Sodium lauryl sulphate 0.5g
According to above prescription, by comprising 1000 capsules of 2.0mg silodosin semihydrate crystal in the ordinary method preparation capsule.
Embodiment 4: capsule 2
Prescription:
Silodosin semihydrate crystal 2 .0g
Microcrystalline Cellulose 56.5g
Lactose 40.0g
Magnesium Stearate 0.5g
Sodium lauryl sulphate 1.0g
According to above prescription, by comprising 1000 capsules of 2.0mg silodosin semihydrate crystal in the ordinary method preparation capsule.
Embodiment 5: capsule 3
Prescription:
Silodosin semihydrate crystal 4 .0g
Lactose 63.5g
Pregelatinized Starch 30.0g
Talcum powder 0.5g
Sodium lauryl sulphate 2.0g
According to above prescription, by comprising 1000 capsules of 4.0mg silodosin semihydrate crystal in the ordinary method preparation capsule.
Embodiment 6: tablet 1
Prescription:
Silodosin semihydrate crystal 2 .0g
N.F,USP MANNITOL 59.0g
Pregelatinized Starch 30.0g
Low-substituted hydroxypropyl cellulose 5.0g
HPMC E50 2.0g
Magnesium Stearate 1.0g
Sodium lauryl sulphate 1.0g
According to above prescription, by comprising 1000 capsules of 2.0mg silodosin semihydrate crystal in the ordinary method preparation tablet.
Embodiment 7: tablet 2
Prescription:
Silodosin semihydrate crystal 4 .0g
N.F,USP MANNITOL 56.0g
Pregelatinized Starch 30.0g
Low-substituted hydroxypropyl cellulose 5.0g
PVP K30 2.0g
Talcum powder 1.0g
Sodium lauryl sulphate 2.0g
According to above prescription, by comprising 1000 capsules of 4.0mg silodosin semihydrate crystal in the ordinary method preparation tablet.
Claims (3)
1.2,3-dihydro-1-(3-hydroxypropyl)-5-[(2R)-2-[2-[2-(2,2,2-trifluoro ethoxy) phenoxy group] and ethylamino-] propyl group]-crystal of the compound shown in the formula (I) of 1H-indoles-7-methane amide semihydrate
It is characterized in that using diffractometer to measure, the spacing d in the following table, 2 θ angles, intensity represent:
2. the preparation method of formula according to claim 1 (I) compound crystal, it is characterized in that; get this product 1g with 2ml ethanol heating for dissolving after; remove by filter insolubles; stir and slowly drip 30ml water to crystalline solid in the mother liquor and separate out fully down; and continue to stir 30 minutes; filter and collect the solid that obtains; in lower 50 ℃ of dryings of vacuum 12 hours to constant weight; obtain the 950mg crystal; purity 99.3%, the gained crystal formation represents with spacing d, 2 θ angles and intensity to use diffractometer to measure:
3. one kind is used for the treatment of dysuric pharmaceutical composition, and it comprises silodosin semihydrate crystal claimed in claim 1 and pharmaceutically acceptable auxiliary material as activeconstituents.
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 |
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| Publication Number | Publication Date |
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| CN102229557A CN102229557A (en) | 2011-11-02 |
| CN102229557B true CN102229557B (en) | 2013-03-27 |
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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 |
|---|
| "Urodynamic Effects of Silodosin, a New a1A-Adrenoceptor Selective Antagonist, for the Treatment of Benign Prostatic Hyperplasia";Tomonori Yamanishi et al.;《Neurourology and Urodynamics》;20100515;第29卷;第558-562页 * |
| Tomonori Yamanishi et al.."Urodynamic Effects of Silodosin, a New a1A-Adrenoceptor Selective Antagonist, for the Treatment of Benign Prostatic Hyperplasia".《Neurourology and Urodynamics》.2010,第29卷第558-562页. |
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