CN100364533C - Pyrolidone hydrochloride drip pill and its preparation method - Google Patents
Pyrolidone hydrochloride drip pill and its preparation method Download PDFInfo
- Publication number
- CN100364533C CN100364533C CNB2005100660017A CN200510066001A CN100364533C CN 100364533 C CN100364533 C CN 100364533C CN B2005100660017 A CNB2005100660017 A CN B2005100660017A CN 200510066001 A CN200510066001 A CN 200510066001A CN 100364533 C CN100364533 C CN 100364533C
- Authority
- CN
- China
- Prior art keywords
- pioglitazone hydrochloride
- polyethylene glycol
- pioglitazone
- substrate
- hydrochloride
- 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.)
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Links
- 239000006187 pill Substances 0.000 title claims abstract description 46
- 238000002360 preparation method Methods 0.000 title abstract description 29
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 title description 23
- GHUUBYQTCDQWRA-UHFFFAOYSA-N Pioglitazone hydrochloride Chemical compound Cl.N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 GHUUBYQTCDQWRA-UHFFFAOYSA-N 0.000 claims abstract description 97
- 229960002827 pioglitazone hydrochloride Drugs 0.000 claims abstract description 97
- 239000000758 substrate Substances 0.000 claims abstract description 44
- 239000000203 mixture Substances 0.000 claims abstract description 14
- 239000002994 raw material Substances 0.000 claims abstract 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 83
- 239000002202 Polyethylene glycol Substances 0.000 claims description 82
- -1 polyoxyethylene stearate Polymers 0.000 claims description 36
- 150000002148 esters Chemical class 0.000 claims description 28
- 229920002472 Starch Polymers 0.000 claims description 25
- HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 claims description 25
- 235000019698 starch Nutrition 0.000 claims description 25
- 239000008107 starch Substances 0.000 claims description 25
- 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 claims description 22
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 22
- 239000011734 sodium Substances 0.000 claims description 22
- 229910052708 sodium Inorganic materials 0.000 claims description 22
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 14
- 229960005095 pioglitazone Drugs 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 10
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- 239000000839 emulsion Substances 0.000 claims description 4
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
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- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 2
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- 229940023488 pill Drugs 0.000 description 35
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 34
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 27
- 229920001983 poloxamer Polymers 0.000 description 27
- 229960000502 poloxamer Drugs 0.000 description 27
- 229920000858 Cyclodextrin Polymers 0.000 description 20
- 239000001116 FEMA 4028 Substances 0.000 description 20
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound 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 description 20
- 235000011175 beta-cyclodextrine Nutrition 0.000 description 20
- 229960004853 betadex Drugs 0.000 description 20
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- 229940125396 insulin Drugs 0.000 description 17
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 16
- 238000012360 testing method Methods 0.000 description 16
- 239000008194 pharmaceutical composition Substances 0.000 description 13
- 238000002474 experimental method Methods 0.000 description 12
- 239000004615 ingredient Substances 0.000 description 12
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- 239000000969 carrier Substances 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 239000001828 Gelatine Substances 0.000 description 8
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 8
- 239000004141 Sodium laurylsulphate Substances 0.000 description 8
- 235000021355 Stearic acid Nutrition 0.000 description 8
- 229920000159 gelatin Polymers 0.000 description 8
- 235000019322 gelatine Nutrition 0.000 description 8
- 235000011187 glycerol Nutrition 0.000 description 8
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 8
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 8
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 8
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 8
- 239000008117 stearic acid Substances 0.000 description 8
- 238000009472 formulation Methods 0.000 description 7
- IYFATESGLOUGBX-YVNJGZBMSA-N Sorbitan monopalmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O IYFATESGLOUGBX-YVNJGZBMSA-N 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
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- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
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- 229940123464 Thiazolidinedione Drugs 0.000 description 4
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- YZFWTZACSRHJQD-UHFFFAOYSA-N ciglitazone Chemical compound C=1C=C(CC2C(NC(=O)S2)=O)C=CC=1OCC1(C)CCCCC1 YZFWTZACSRHJQD-UHFFFAOYSA-N 0.000 description 4
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- 230000036541 health Effects 0.000 description 4
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- GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 4
- 229960001641 troglitazone Drugs 0.000 description 4
- GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 4
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 description 3
- 241000790917 Dioxys <bee> Species 0.000 description 3
- 239000003472 antidiabetic agent Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 150000002632 lipids Chemical class 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 3
- MVDXXGIBARMXSA-PYUWXLGESA-N 5-[[(2r)-2-benzyl-3,4-dihydro-2h-chromen-6-yl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound S1C(=O)NC(=O)C1CC1=CC=C(O[C@@H](CC=2C=CC=CC=2)CC2)C2=C1 MVDXXGIBARMXSA-PYUWXLGESA-N 0.000 description 2
- 229940123208 Biguanide Drugs 0.000 description 2
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- 208000013016 Hypoglycemia Diseases 0.000 description 2
- 102000000536 PPAR gamma Human genes 0.000 description 2
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- 238000010521 absorption reaction Methods 0.000 description 2
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- 150000004283 biguanides Chemical class 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
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- 230000000857 drug effect Effects 0.000 description 2
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Landscapes
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
The substrate title | Effective ingredient (%) | Rounding rate (%) | Dissolve scattered time limit (minute) | The ball method of double differences different (%) | Hardness |
Polyethylene Glycol 1000 | 50.0 | 64 | <30 | >10 | + |
Polyethylene Glycol 4000 | 50.0 | 72 | <30 | >10 | + |
Polyethylene Glycol 6000 | 50.0 | 73 | <30 | >10 | ++ |
Polyethylene Glycol 10000 | 50.0 | 76 | <30 | >10 | ++ |
Polyethylene Glycol 20000 | 50.0 | 75 | <30 | >10 | ++ |
Span 40 | 50.0 | 72 | <30 | >10 | ++ |
Polyoxyethylene stearate 40 esters | 50.0 | 76 | <30 | >10 | ++ |
Poloxamer | 50.0 | 76 | <30 | >10 | ++ |
Sodium lauryl sulphate | 50.0 | 73 | >30 | >10 | + |
Stearic acid | 50.0 | 62 | >30 | >10 | ++ |
Sodium stearate | 50.0 | 63 | >30 | >10 | ++ |
Glycerin gelatine | 50.0 | 61 | >30 | >10 | + |
Lac | 50.0 | 65 | >30 | >10 | + |
The substrate title | Effective ingredient (%) | Rounding rate (%) | Dissolve scattered time limit (minute) | The ball method of double differences different (%) | Hardness |
Polyethylene Glycol 1000 | 25.0 | 66 | <30 | >10 | + |
Polyethylene Glycol 4000 | 25.0 | 85 | <30 | <10 | +++ |
Polyethylene Glycol 6000 | 25.0 | 87 | <30 | <10 | +++ |
Polyethylene Glycol 10000 | 25.0 | 91 | <30 | <10 | +++ |
Polyethylene Glycol 20000 | 25.0 | 90 | <30 | <10 | +++ |
Span 40 | 25.0 | 82 | <30 | >10 | ++ |
Polyoxyethylene stearate 40 esters | 25.0 | 89 | <30 | <10 | ++ |
Poloxamer | 25.0 | 85 | <30 | <10 | +++ |
Sodium lauryl sulphate | 25.0 | 76 | <30 | >10 | ++ |
Stearic acid | 25.0 | 73 | >30 | >10 | +++ |
Sodium stearate | 25.0 | 71 | >30 | >10 | +++ |
Glycerin gelatine | 25.0 | 75 | >30 | >10 | +++ |
Lac | 25.0 | 74 | >30 | >10 | +++ |
The substrate title | Effective ingredient (%) | Rounding rate (%) | Dissolve scattered time limit (minute) | The ball method of double differences different (%) | Hardness |
Polyethylene Glycol 1000 | 10.0 | 75 | <30 | >10 | + |
Polyethylene Glycol 4000 | 10.0 | 87 | <30 | <10 | +++ |
Polyethylene Glycol 6000 | 10.0 | 91 | <30 | <10 | +++ |
Polyethylene Glycol 10000 | 10.0 | 89 | <30 | <10 | +++ |
Polyethylene Glycol 20000 | 10.0 | 91 | <30 | <10 | +++ |
Span | 10.0 | 85 | <30 | >10 | +++ |
Polyoxyethylene stearate 40 esters | 10.0 | 91 | <30 | <10 | ++ |
Poloxamer | 10.0 | 85 | <30 | <10 | +++ |
Sodium lauryl sulphate | 10.0 | 78 | <30 | >10 | +++ |
Stearic acid | 10.0 | 75 | >30 | >10 | +++ |
Sodium stearate | 10.0 | 73 | >30 | >10 | +++ |
Glycerin gelatine | 10.0 | 76 | >30 | >10 | +++ |
Lac | 10.0 | 77 | >30 | >10 | +++ |
The substrate title | Effective ingredient (%) | Rounding rate (%) | Dissolve scattered time limit (minute) | The ball method of double differences different (%) | Hardness |
Polyoxyethylene stearate 40 esters: Polyethylene Glycol=1: 1 | 50 | 84 | <30 | >10 | ++ |
Poloxamer: Polyethylene Glycol=1: 1 | 50 | 83 | <30 | >10 | ++ |
Carboxymethyl starch sodium: Polyethylene Glycol=1: 1 | 50 | 81 | <30 | >10 | ++ |
Betacyclodextrin: Polyethylene Glycol=1: 1 | 50 | 82 | <30 | >10 | + |
The substrate title | Effective ingredient (%) | Rounding rate (%) | Dissolve scattered time limit (minute) | The ball method of double differences different (%) | Hardness |
Polyoxyethylene stearate 40 esters: Polyethylene Glycol=1: 1 | 25 | 85 | <30 | <10 | +++ |
Poloxamer: Polyethylene Glycol=1: 1 | 25 | 87 | <30 | <10 | +++ |
Carboxymethyl starch sodium: Polyethylene Glycol=1: 1 | 25 | 85 | <30 | >10 | ++ |
Betacyclodextrin: Polyethylene Glycol=1: 1 | 25 | 87 | <30 | >10 | ++ |
The substrate title | Effective ingredient (%) | Rounding rate (%) | Dissolve scattered time limit (minute) | The ball method of double differences different (%) | Hardness |
Polyoxyethylene stearate 40 esters: Polyethylene Glycol=1: 1 | 10 | 91 | <30 | <10 | +++ |
Poloxamer: Polyethylene Glycol=1: 1 | 10 | 91 | <30 | <10 | +++ |
Carboxymethyl starch sodium: Polyethylene Glycol=1: 1 | 10 | 89 | <30 | <10 | +++ |
Betacyclodextrin: Polyethylene Glycol=1: 1 | 10 | 87 | <30 | >10 | +++ |
The substrate title | Effective ingredient (%) | Rounding rate (%) | Dissolve scattered time limit (minute) | The ball method of double differences different (%) | Hardness |
Polyoxyethylene stearate 40 esters: Polyethylene Glycol=1: 5 | 50 | 88 | <30 | 10 | +++ |
Poloxamer: Polyethylene Glycol=1: 5 | 50 | 91 | <30 | <10 | +++ |
Carboxymethyl starch sodium: Polyethylene Glycol=1: 5 | 50 | 89 | <30 | <10 | +++ |
Betacyclodextrin: Polyethylene Glycol=1: 5 | 50 | 89 | <30 | <10 | ++ |
The substrate title | Effective ingredient (%) | Rounding rate (%) | Dissolve scattered time limit (minute) | The ball method of double differences different (%) | Hardness |
Polyoxyethylene stearate 40 esters: Polyethylene Glycol=1: 5 | 25 | 86 | <30 | <10 | +++ |
Poloxamer: Polyethylene Glycol=1: 5 | 25 | 91 | <30 | <10 | +++ |
Carboxymethyl starch sodium: Polyethylene Glycol=1: 5 | 25 | 91 | <30 | <10 | +++ |
Betacyclodextrin: Polyethylene Glycol=1: 5 | 25 | 90 | <30 | <10 | +++ |
The substrate title | Effective ingredient (%) | Rounding rate (%) | Dissolve scattered time limit (minute) | The ball method of double differences different (%) | Hardness |
Polyoxyethylene stearate 40 esters: Polyethylene Glycol=1: 5 | 10 | 90 | <30 | <10 | +++ |
Poloxamer: Polyethylene Glycol=1: 5 | 10 | 92 | <30 | <10 | +++ |
Carboxymethyl starch sodium: Polyethylene Glycol=1: 5 | 10 | 92 | <30 | <10 | +++ |
Betacyclodextrin: Polyethylene Glycol=1: 5 | 10 | 89 | <30 | <10 | +++ |
The substrate title | Effective ingredient (%) | Rounding rate (%) | Dissolve scattered time limit (minute) | The ball method of double differences different (%) | Hardness |
Polyoxyethylene stearate 40 esters: Polyethylene Glycol=1: 10 | 50 | 88 | <30 | <10 | +++ |
Poloxamer: Polyethylene Glycol=1: 10 | 50 | 91 | <30 | <10 | +++ |
Carboxymethyl starch sodium: Polyethylene Glycol=1: 10 | 50 | 87 | <30 | <10 | +++ |
Betacyclodextrin: Polyethylene Glycol=1: 10 | 50 | 89 | <30 | >10 | +++ |
The substrate title | Effective ingredient (%) | Rounding rate (%) | Dissolve scattered time limit (minute) | The ball method of double differences different (%) | Hardness |
Polyoxyethylene stearate 40 esters: Polyethylene Glycol=1: 10 | 25 | 92 | <30 | <10 | +++ |
Poloxamer: Polyethylene Glycol=1: 10 | 25 | 91 | <30 | <10 | +++ |
Carboxymethyl starch sodium: Polyethylene Glycol=1: 10 | 25 | 89 | <30 | <10 | +++ |
Betacyclodextrin: Polyethylene Glycol=1: 10 | 25 | 90 | <30 | <10 | +++ |
The substrate title | Effective ingredient (%) | Rounding rate (%) | Dissolve scattered time limit (minute) | The ball method of double differences different (%) | Hardness |
Polyoxyethylene stearate 40 esters: Polyethylene Glycol=1: 10 | 10 | 91 | <30 | <10 | +++ |
Poloxamer: Polyethylene Glycol=1: 10 | 10 | 91 | <30 | <10 | +++ |
Carboxymethyl starch sodium: Polyethylene Glycol=1: 10 | 10 | 90 | <30 | <10 | +++ |
Betacyclodextrin: Polyethylene Glycol=1: 10 | 10 | 92 | <30 | <10 | +++ |
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CNB2005100660017A CN100364533C (en) | 2005-04-19 | 2005-04-19 | Pyrolidone hydrochloride drip pill and its preparation method |
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CN100364533C true CN100364533C (en) | 2008-01-30 |
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CN101912363A (en) * | 2010-07-29 | 2010-12-15 | 蔡海德 | Dissolving ultrafiltration-spray drying-molecule dispersion coating-hydration palletizing-freeze drying method for preparing liposome combination medicine |
CN102228457B (en) * | 2011-04-25 | 2013-07-24 | 刘树芹 | Pharmaceutical composition for treating diabetes and complication thereof |
CN103432128B (en) * | 2013-08-26 | 2015-11-18 | 中国人民解放军第150中心医院 | A kind of compound formulation of pioglitazone hydrochloride sustained-release pellet preparations medicated layer |
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CN1424041A (en) * | 2002-12-19 | 2003-06-18 | 中国人民解放军第二军医大学 | Kakonein preparations and their production |
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CN1424041A (en) * | 2002-12-19 | 2003-06-18 | 中国人民解放军第二军医大学 | Kakonein preparations and their production |
Non-Patent Citations (2)
Title |
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新编药物学. 陈新谦等,617,人民卫生出版社. 2004 * |
药剂学. 奚念朱,285-287,人民卫生出版社. 1994 * |
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