CS270560B2 - Method of biologically active compounds solubilization - Google Patents

Method of biologically active compounds solubilization Download PDF

Info

Publication number: CS270560B2
Authority: CS; Czechoslovakia
Prior art keywords: solubilizing agent; active compound; active; polyethoxylated; felodipine
Prior art date: 1986-04-11

Application number

CS872587A

Other languages

Czech (cs)

English (en)

Other versions

CS258787A2 (en

Inventor

Karl-Erik L Falk

Sven M Hugosson

Adam Rosinski

John A Sjorgen

Original Assignee

Haessle Ab

Priority date (The priority date 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 date listed.)

1986-04-11

Filing date

1987-04-10

Publication date

1990-07-12

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=20364135&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CS270560(B2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1987-04-10 Application filed by Haessle Ab filed Critical Haessle Ab

1989-11-14 Publication of CS258787A2 publication Critical patent/CS258787A2/cs

1990-07-12 Publication of CS270560B2 publication Critical patent/CS270560B2/cs

Links

238000000034 method Methods 0.000 title claims description 32
150000001875 compounds Chemical class 0.000 title claims description 31
238000005063 solubilization Methods 0.000 title description 4
230000007928 solubilization Effects 0.000 title description 4
239000002904 solvent Substances 0.000 claims description 39
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
230000008569 process Effects 0.000 claims description 17
239000013543 active substance Substances 0.000 claims description 13
125000001931 aliphatic group Polymers 0.000 claims description 8
125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 claims description 8
239000004359 castor oil Substances 0.000 claims description 6
235000019438 castor oil Nutrition 0.000 claims description 6
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 6
239000008389 polyethoxylated castor oil Substances 0.000 claims description 6
229920001223 polyethylene glycol Polymers 0.000 claims description 6
230000002035 prolonged effect Effects 0.000 claims description 6
-1 aliphatic alcohols Chemical class 0.000 claims description 5
150000002148 esters Chemical class 0.000 claims description 5
239000007787 solid Substances 0.000 claims description 5
230000003381 solubilizing effect Effects 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 4
239000007788 liquid Substances 0.000 claims description 4
150000002170 ethers Chemical class 0.000 claims description 3
150000002314 glycerols Chemical class 0.000 claims description 2
108010039491 Ricin Proteins 0.000 claims 1
239000003921 oil Substances 0.000 claims 1
239000000203 mixture Substances 0.000 description 61
RZTAMFZIAATZDJ-HNNXBMFYSA-N 5-o-ethyl 3-o-methyl (4s)-4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)[C@@H]1C1=CC=CC(Cl)=C1Cl RZTAMFZIAATZDJ-HNNXBMFYSA-N 0.000 description 25
229960003580 felodipine Drugs 0.000 description 25
239000004480 active ingredient Substances 0.000 description 23
238000013270 controlled release Methods 0.000 description 18
238000009472 formulation Methods 0.000 description 16
HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 14
229960001597 nifedipine Drugs 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
230000000052 comparative effect Effects 0.000 description 10
239000000499 gel Substances 0.000 description 10
230000036470 plasma concentration Effects 0.000 description 10
239000000126 substance Substances 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
238000010521 absorption reaction Methods 0.000 description 9
239000002775 capsule Substances 0.000 description 9
239000008187 granular material Substances 0.000 description 9
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239000008101 lactose Substances 0.000 description 8
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UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 7
238000013268 sustained release Methods 0.000 description 7
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KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
239000000969 carrier Substances 0.000 description 6
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238000004090 dissolution Methods 0.000 description 6
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235000019322 gelatine Nutrition 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
210000002381 plasma Anatomy 0.000 description 6
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235000013855 polyvinylpyrrolidone Nutrition 0.000 description 6
ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 5
239000001856 Ethyl cellulose Substances 0.000 description 5
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235000019325 ethyl cellulose Nutrition 0.000 description 5
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239000003814 drug Substances 0.000 description 4
MVPICKVDHDWCJQ-UHFFFAOYSA-N ethyl 3-pyrrolidin-1-ylpropanoate Chemical compound CCOC(=O)CCN1CCCC1 MVPICKVDHDWCJQ-UHFFFAOYSA-N 0.000 description 4
239000007903 gelatin capsule Substances 0.000 description 4
229940031705 hydroxypropyl methylcellulose 2910 Drugs 0.000 description 4
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239000001993 wax Substances 0.000 description 4
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 3
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
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239000002202 Polyethylene glycol Substances 0.000 description 3
229920002690 Polyoxyl 40 HydrogenatedCastorOil Polymers 0.000 description 3
YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
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229920003176 water-insoluble polymer Polymers 0.000 description 3
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PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 2
229930105110 Cyclosporin A Natural products 0.000 description 2
108010036949 Cyclosporine Proteins 0.000 description 2
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
LTMHDMANZUZIPE-AMTYYWEZSA-N Digoxin Natural products O([C@H]1[C@H](C)O[C@H](O[C@@H]2C[C@@H]3[C@@](C)([C@@H]4[C@H]([C@]5(O)[C@](C)([C@H](O)C4)[C@H](C4=CC(=O)OC4)CC5)CC3)CC2)C[C@@H]1O)[C@H]1O[C@H](C)[C@@H](O[C@H]2O[C@@H](C)[C@H](O)[C@@H](O)C2)[C@@H](O)C1 LTMHDMANZUZIPE-AMTYYWEZSA-N 0.000 description 2
IIUZTXTZRGLYTI-UHFFFAOYSA-N Dihydrogriseofulvin Natural products COC1CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 IIUZTXTZRGLYTI-UHFFFAOYSA-N 0.000 description 2
UXWOXTQWVMFRSE-UHFFFAOYSA-N Griseoviridin Natural products O=C1OC(C)CC=C(C(NCC=CC=CC(O)CC(O)C2)=O)SCC1NC(=O)C1=COC2=N1 UXWOXTQWVMFRSE-UHFFFAOYSA-N 0.000 description 2
229920002907 Guar gum Polymers 0.000 description 2
DDUHZTYCFQRHIY-UHFFFAOYSA-N Negwer: 6874 Natural products COC1=CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-UHFFFAOYSA-N 0.000 description 2
CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical compound N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 description 2
229920002700 Polyoxyl 60 hydrogenated castor oil Polymers 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
239000008280 blood Substances 0.000 description 2
239000001506 calcium phosphate Substances 0.000 description 2
229910000389 calcium phosphate Inorganic materials 0.000 description 2
235000011010 calcium phosphates Nutrition 0.000 description 2
230000000747 cardiac effect Effects 0.000 description 2
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239000007931 coated granule Substances 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
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LTMHDMANZUZIPE-PUGKRICDSA-N digoxin Chemical compound C1[C@H](O)[C@H](O)[C@@H](C)O[C@H]1O[C@@H]1[C@@H](C)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@@H]3C[C@@H]4[C@]([C@@H]5[C@H]([C@]6(CC[C@@H]([C@@]6(C)[C@H](O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)C[C@@H]2O)C)C[C@@H]1O LTMHDMANZUZIPE-PUGKRICDSA-N 0.000 description 2
229960005156 digoxin Drugs 0.000 description 2
LTMHDMANZUZIPE-UHFFFAOYSA-N digoxine Natural products C1C(O)C(O)C(C)OC1OC1C(C)OC(OC2C(OC(OC3CC4C(C5C(C6(CCC(C6(C)C(O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)CC2O)C)CC1O LTMHDMANZUZIPE-UHFFFAOYSA-N 0.000 description 2
229940085304 dihydropyridine derivative selective calcium channel blockers with mainly vascular effects Drugs 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
DDUHZTYCFQRHIY-RBHXEPJQSA-N griseofulvin Chemical compound COC1=CC(=O)C[C@@H](C)[C@@]11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-RBHXEPJQSA-N 0.000 description 2
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235000010417 guar gum Nutrition 0.000 description 2
239000000665 guar gum Substances 0.000 description 2
229960002154 guar gum Drugs 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
230000000968 intestinal effect Effects 0.000 description 2
239000012528 membrane Substances 0.000 description 2
238000002156 mixing Methods 0.000 description 2
ADIMAYPTOBDMTL-UHFFFAOYSA-N oxazepam Chemical compound C12=CC(Cl)=CC=C2NC(=O)C(O)N=C1C1=CC=CC=C1 ADIMAYPTOBDMTL-UHFFFAOYSA-N 0.000 description 2
229960004535 oxazepam Drugs 0.000 description 2
229960002036 phenytoin Drugs 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000000600 sorbitol Substances 0.000 description 2
235000010356 sorbitol Nutrition 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
230000002459 sustained effect Effects 0.000 description 2
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 2
239000000230 xanthan gum Substances 0.000 description 2
235000010493 xanthan gum Nutrition 0.000 description 2
229940082509 xanthan gum Drugs 0.000 description 2
YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 1
RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 1
GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical group OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
229920000945 Amylopectin Polymers 0.000 description 1
229940127291 Calcium channel antagonist Drugs 0.000 description 1
229920000623 Cellulose acetate phthalate Polymers 0.000 description 1
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244000007835 Cyamopsis tetragonoloba Species 0.000 description 1
239000001828 Gelatine Substances 0.000 description 1
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 1
MHQJUHSHQGQVTM-HNENSFHCSA-N Octadecyl fumarate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)\C=C/C(O)=O MHQJUHSHQGQVTM-HNENSFHCSA-N 0.000 description 1
BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
229920002701 Polyoxyl 40 Stearate Polymers 0.000 description 1
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 1
229930006000 Sucrose Natural products 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
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229960000074 biopharmaceutical Drugs 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
229960001714 calcium phosphate Drugs 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
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RZTAMFZIAATZDJ-UHFFFAOYSA-N felodipine Chemical group CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC(Cl)=C1Cl RZTAMFZIAATZDJ-UHFFFAOYSA-N 0.000 description 1
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230000035699 permeability Effects 0.000 description 1
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229920000915 polyvinyl chloride Polymers 0.000 description 1
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239000002244 precipitate Substances 0.000 description 1
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OKODKVMXHLUQSW-JITBQSAISA-M sodium;(e)-4-hydroxy-4-oxobut-2-enoate;octadecanoic acid Chemical compound [Na+].OC(=O)\C=C\C([O-])=O.CCCCCCCCCCCCCCCCCC(O)=O OKODKVMXHLUQSW-JITBQSAISA-M 0.000 description 1
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208000019553 vascular disease Diseases 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1617—Organic compounds, e.g. phospholipids, fats
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Biophysics (AREA)
Molecular Biology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Medicinal Preparation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Saccharide Compounds (AREA)

CS872587A 1986-04-11 1987-04-10 Method of biologically active compounds solubilization CS270560B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
SE8601624A SE8601624D0 (sv)	1986-04-11	1986-04-11	New pharmaceutical preparations

Publications (2)

Publication Number	Publication Date
CS258787A2 CS258787A2 (en)	1989-11-14
CS270560B2 true CS270560B2 (en)	1990-07-12

Family

ID=20364135

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS872587A CS270560B2 (en)	1986-04-11	1987-04-10	Method of biologically active compounds solubilization

Country Status (34)

Country	Link
US (1)	US4803081A (hu)
EP (1)	EP0249587B1 (hu)
JP (1)	JPH0778016B2 (hu)
KR (2)	KR870009720A (hu)
CN (1)	CN1025150C (hu)
AT (1)	ATE76288T1 (hu)
AU (1)	AU602677B2 (hu)
CA (1)	CA1304294C (hu)
CS (1)	CS270560B2 (hu)
CY (1)	CY1826A (hu)
DD (1)	DD263231A5 (hu)
DE (1)	DE3779183D1 (hu)
DK (1)	DK173033B1 (hu)
DZ (1)	DZ1067A1 (hu)
EG (1)	EG18265A (hu)
ES (1)	ES2031929T3 (hu)
FI (1)	FI91826C (hu)
GR (1)	GR3005286T3 (hu)
HK (1)	HK26795A (hu)
HU (1)	HU204699B (hu)
IE (1)	IE59419B1 (hu)
IS (1)	IS1553B (hu)
MY (1)	MY101553A (hu)
NO (1)	NO174795B (hu)
NZ (1)	NZ219633A (hu)
PH (1)	PH22494A (hu)
PL (1)	PL265078A1 (hu)
PT (1)	PT84663B (hu)
SE (1)	SE8601624D0 (hu)
SG (1)	SG4295G (hu)
SU (1)	SU1743332A3 (hu)
UA (1)	UA12336A (hu)
YU (1)	YU47258B (hu)
ZA (1)	ZA871911B (hu)

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1986
- 1986-04-11 SE SE8601624A patent/SE8601624D0/xx unknown
1987
- 1987-03-10 PH PH35003A patent/PH22494A/en unknown
- 1987-03-12 YU YU40787A patent/YU47258B/sh unknown
- 1987-03-16 NZ NZ219633A patent/NZ219633A/xx unknown
- 1987-03-16 AU AU70043/87A patent/AU602677B2/en not_active Expired
- 1987-03-16 ZA ZA871911A patent/ZA871911B/xx unknown
- 1987-03-22 EG EG171/87A patent/EG18265A/xx active
- 1987-03-23 NO NO871199A patent/NO174795B/no unknown
- 1987-03-25 ES ES198787850098T patent/ES2031929T3/es not_active Expired - Lifetime
- 1987-03-25 EP EP87850098A patent/EP0249587B1/en not_active Expired - Lifetime
- 1987-03-25 AT AT87850098T patent/ATE76288T1/de not_active IP Right Cessation
- 1987-03-25 DE DE8787850098T patent/DE3779183D1/de not_active Expired - Lifetime
- 1987-03-26 DK DK198701549A patent/DK173033B1/da not_active IP Right Cessation
- 1987-04-03 US US07/034,500 patent/US4803081A/en not_active Expired - Lifetime
- 1987-04-07 MY MYPI87000450A patent/MY101553A/en unknown
- 1987-04-07 CA CA000533985A patent/CA1304294C/en not_active Expired - Lifetime
- 1987-04-07 DZ DZ870056A patent/DZ1067A1/fr active
- 1987-04-09 DD DD87301670A patent/DD263231A5/de unknown
- 1987-04-09 PL PL1987265078A patent/PL265078A1/xx unknown
- 1987-04-09 IE IE92587A patent/IE59419B1/en not_active IP Right Cessation
- 1987-04-10 IS IS3214A patent/IS1553B/is unknown
- 1987-04-10 CS CS872587A patent/CS270560B2/cs not_active IP Right Cessation
- 1987-04-10 PT PT84663A patent/PT84663B/pt unknown
- 1987-04-10 UA UA4202349A patent/UA12336A/uk unknown
- 1987-04-10 FI FI871585A patent/FI91826C/fi not_active IP Right Cessation
- 1987-04-10 JP JP62087250A patent/JPH0778016B2/ja not_active Expired - Lifetime
- 1987-04-10 CN CN87102758A patent/CN1025150C/zh not_active Expired - Lifetime
- 1987-04-10 SU SU874202349A patent/SU1743332A3/ru active
- 1987-04-10 HU HU871622A patent/HU204699B/hu unknown
- 1987-04-10 KR KR870003416A patent/KR870009720A/ko not_active Withdrawn
- 1987-07-06 KR KR1019870007169A patent/KR950002147B1/ko not_active Expired - Lifetime
1992
- 1992-07-29 GR GR920401616T patent/GR3005286T3/el unknown
1995
- 1995-01-11 SG SG4295A patent/SG4295G/en unknown
- 1995-03-02 HK HK26795A patent/HK26795A/xx not_active IP Right Cessation
- 1995-12-01 CY CY182695A patent/CY1826A/xx unknown

Also Published As

Publication number	Publication date
IS3214A7 (is)	1987-10-12
FI871585L (fi)	1987-10-12
JPH0778016B2 (ja)	1995-08-23
IS1553B (is)	1994-08-10
CN1025150C (zh)	1994-06-29
NO871199D0 (no)	1987-03-23
HK26795A (en)	1995-03-10
PH22494A (en)	1988-09-12
EP0249587A1 (en)	1987-12-16
NO174795C (hu)	1994-07-13
AU7004387A (en)	1987-10-15
YU40787A (sh)	1992-09-07
EG18265A (en)	1992-12-30
FI91826C (fi)	1994-08-25
CN87102758A (zh)	1987-10-21
ATE76288T1 (de)	1992-06-15
HU204699B (en)	1992-02-28
KR890001521A (ko)	1989-03-27
MY101553A (en)	1991-12-17
KR870009720A (ko)	1987-11-30
NO871199L (no)	1987-10-12
IE870925L (en)	1987-10-11
DK154987A (da)	1987-10-12
FI91826B (fi)	1994-05-13
PL265078A1 (en)	1988-07-21
AU602677B2 (en)	1990-10-25
US4803081A (en)	1989-02-07
ZA871911B (en)	1987-12-30
KR950002147B1 (ko)	1995-03-14
NO174795B (no)	1994-04-05
CY1826A (en)	1995-12-01
PT84663A (en)	1987-05-01
GR3005286T3 (hu)	1993-05-24
UA12336A (uk)	1996-12-25
DD263231A5 (de)	1988-12-28
SU1743332A3 (ru)	1992-06-23
DK173033B1 (da)	1999-11-29
SG4295G (en)	1995-06-16
HUT43786A (en)	1987-12-28
PT84663B (pt)	1989-11-30
EP0249587B1 (en)	1992-05-20
SE8601624D0 (sv)	1986-04-11
JPS62242613A (ja)	1987-10-23
FI871585A0 (fi)	1987-04-10
YU47258B (sh)	1995-01-31
DE3779183D1 (de)	1992-06-25
CS258787A2 (en)	1989-11-14
DK154987D0 (da)	1987-03-26
CA1304294C (en)	1992-06-30
NZ219633A (en)	1989-11-28
IE59419B1 (en)	1994-02-23
DZ1067A1 (fr)	2004-09-13
ES2031929T3 (es)	1993-01-01

Publication	Publication Date	Title
CS270560B2 (en)	1990-07-12	Method of biologically active compounds solubilization
EP0311582B1 (en)	1993-01-13	Pharmaceutical preparation with extended release of a dihydropyridine and a beta-adrenoreceptor antagonist and a process for the preparation thereof
US4404183A (en)	1983-09-13	Sustained release pharmaceutical composition of solid medical material
SK153497A3 (en)	1998-04-08	Three-phase pharmaceutical form with constant and controlled release of amorphous active ingredient for single daily application
KR19990044653A (ko)	1999-06-25	다리페나신을 함유하는 약학 제제
JP3110794B2 (ja)	2000-11-20	１，４−ジヒドロピリジン誘導体を含有する製剤
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Date	Code	Title	Description
2000-06-30	IF00	In force as of 2000-06-30 in czech republic
2002-08-14	MK4A	Patent expired	Effective date: 20020410