AU615495B2 - Stabilized medicinal substances, a process for the preparation thereof, and stable medicinal formulations - Google Patents
Stabilized medicinal substances, a process for the preparation thereof, and stable medicinal formulations Download PDFInfo
- Publication number
- AU615495B2 AU615495B2 AU25818/88A AU2581888A AU615495B2 AU 615495 B2 AU615495 B2 AU 615495B2 AU 25818/88 A AU25818/88 A AU 25818/88A AU 2581888 A AU2581888 A AU 2581888A AU 615495 B2 AU615495 B2 AU 615495B2
- Authority
- AU
- Australia
- Prior art keywords
- formula
- active substance
- ramipril
- stabilized
- formulation
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 239000000203 mixture Substances 0.000 title claims description 46
- 238000009472 formulation Methods 0.000 title claims description 13
- 239000000126 substance Substances 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 6
- 229960003401 ramipril Drugs 0.000 claims description 46
- HDACQVRGBOVJII-JBDAPHQKSA-N ramipril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](C[C@@H]2CCC[C@@H]21)C(O)=O)CC1=CC=CC=C1 HDACQVRGBOVJII-JBDAPHQKSA-N 0.000 claims description 45
- 239000013543 active substance Substances 0.000 claims description 42
- 239000000872 buffer Substances 0.000 claims description 12
- 239000011253 protective coating Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 239000011248 coating agent Substances 0.000 claims description 9
- 238000000576 coating method Methods 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 230000001681 protective effect Effects 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000003643 water by type Substances 0.000 claims description 2
- 238000007796 conventional method Methods 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 14
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 14
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 14
- 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 14
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 10
- 239000008108 microcrystalline cellulose Substances 0.000 description 10
- 229940016286 microcrystalline cellulose Drugs 0.000 description 10
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 10
- 239000002775 capsule Substances 0.000 description 9
- 238000000354 decomposition reaction Methods 0.000 description 9
- 238000005469 granulation Methods 0.000 description 9
- 230000003179 granulation Effects 0.000 description 9
- 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 7
- 108010061435 Enalapril Proteins 0.000 description 7
- 229930195725 Mannitol Natural products 0.000 description 7
- 229960000873 enalapril Drugs 0.000 description 7
- GBXSMTUPTTWBMN-XIRDDKMYSA-N enalapril Chemical group C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 GBXSMTUPTTWBMN-XIRDDKMYSA-N 0.000 description 7
- 238000009501 film coating Methods 0.000 description 7
- 239000000594 mannitol Substances 0.000 description 7
- 235000010355 mannitol Nutrition 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 6
- MVPICKVDHDWCJQ-UHFFFAOYSA-N ethyl 3-pyrrolidin-1-ylpropanoate Chemical compound CCOC(=O)CCN1CCCC1 MVPICKVDHDWCJQ-UHFFFAOYSA-N 0.000 description 6
- 239000007888 film coating Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 229940045902 sodium stearyl fumarate Drugs 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 5
- BXRNXXXXHLBUKK-UHFFFAOYSA-N piperazine-2,5-dione Chemical class O=C1CNC(=O)CN1 BXRNXXXXHLBUKK-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000012928 buffer substance Substances 0.000 description 4
- 235000010980 cellulose Nutrition 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- 239000001913 cellulose Substances 0.000 description 4
- 238000007906 compression Methods 0.000 description 4
- 230000006835 compression Effects 0.000 description 4
- OYFJQPXVCSSHAI-QFPUQLAESA-N enalapril maleate Chemical compound OC(=O)\C=C/C(O)=O.C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 OYFJQPXVCSSHAI-QFPUQLAESA-N 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 230000000087 stabilizing effect Effects 0.000 description 4
- MHQJUHSHQGQVTM-HNENSFHCSA-N Octadecyl fumarate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)\C=C/C(O)=O MHQJUHSHQGQVTM-HNENSFHCSA-N 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 150000002431 hydrogen Chemical group 0.000 description 3
- 238000004806 packaging method and process Methods 0.000 description 3
- 230000006641 stabilisation Effects 0.000 description 3
- 238000011105 stabilization Methods 0.000 description 3
- 229940032147 starch Drugs 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 229940071138 stearyl fumarate Drugs 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 3
- UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- 229920000881 Modified starch Polymers 0.000 description 2
- 102000004270 Peptidyl-Dipeptidase A Human genes 0.000 description 2
- 108090000882 Peptidyl-Dipeptidase A Proteins 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229920006318 anionic polymer Polymers 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000001939 inductive effect Effects 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 239000008213 purified water Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- OOSZCNKVJAVHJI-UHFFFAOYSA-N 1-[(4-fluorophenyl)methyl]piperazine Chemical compound C1=CC(F)=CC=C1CN1CCNCC1 OOSZCNKVJAVHJI-UHFFFAOYSA-N 0.000 description 1
- WSVLPVUVIUVCRA-KPKNDVKVSA-N Alpha-lactose monohydrate Chemical compound O.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 WSVLPVUVIUVCRA-KPKNDVKVSA-N 0.000 description 1
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 1
- 101100457021 Caenorhabditis elegans mag-1 gene Proteins 0.000 description 1
- 229920000623 Cellulose acetate phthalate Polymers 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- 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 1
- 229920003148 Eudragit® E polymer Polymers 0.000 description 1
- 229920003134 Eudragit® polymer Polymers 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 206010020772 Hypertension Diseases 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
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 229920003091 Methocel™ Polymers 0.000 description 1
- 101100067996 Mus musculus Gbp1 gene Proteins 0.000 description 1
- VXFJYXUZANRPDJ-WTNASJBWSA-N Trandopril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](C[C@H]2CCCC[C@@H]21)C(O)=O)CC1=CC=CC=C1 VXFJYXUZANRPDJ-WTNASJBWSA-N 0.000 description 1
- 229940081735 acetylcellulose Drugs 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- NEDGUIRITORSKL-UHFFFAOYSA-N butyl 2-methylprop-2-enoate;2-(dimethylamino)ethyl 2-methylprop-2-enoate;methyl 2-methylprop-2-enoate Chemical compound COC(=O)C(C)=C.CCCCOC(=O)C(C)=C.CN(C)CCOC(=O)C(C)=C NEDGUIRITORSKL-UHFFFAOYSA-N 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229920006317 cationic polymer Polymers 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 229940081734 cellulose acetate phthalate Drugs 0.000 description 1
- 239000007931 coated granule Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 229940099112 cornstarch Drugs 0.000 description 1
- -1 diketopiperazine compound Chemical class 0.000 description 1
- 238000007907 direct compression Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000007908 dry granulation Methods 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229960004667 ethyl cellulose Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 229940071826 hydroxyethyl cellulose Drugs 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 229950009810 indolapril Drugs 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229960001021 lactose monohydrate Drugs 0.000 description 1
- 238000000344 low-energy electron-beam lithography Methods 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229960001855 mannitol Drugs 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000001777 nootropic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 229940100467 polyvinyl acetate phthalate Drugs 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 229940074545 sodium dihydrogen phosphate dihydrate Drugs 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229940071117 starch glycolate Drugs 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; 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
- A61K9/14—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
- A61K9/1629—Organic macromolecular compounds
- A61K9/1652—Polysaccharides, e.g. alginate, cellulose derivatives; Cyclodextrin
-
- 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
- A61K9/2072—Pills, tablets, discs, rods characterised by shape, structure or size; Tablets with holes, special break lines or identification marks; Partially coated tablets; Disintegrating flat shaped forms
- A61K9/2077—Tablets comprising drug-containing microparticles in a substantial amount of supporting matrix; Multiparticulate tablets
- A61K9/2081—Tablets comprising drug-containing microparticles in a substantial amount of supporting matrix; Multiparticulate tablets with microcapsules or coated microparticles according to A61K9/50
-
- 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
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5005—Wall or coating material
- A61K9/5021—Organic macromolecular compounds
- A61K9/5036—Polysaccharides, e.g. gums, alginate; Cyclodextrin
- A61K9/5042—Cellulose; Cellulose derivatives, e.g. phthalate or acetate succinate esters of hydroxypropyl methylcellulose
- A61K9/5047—Cellulose ethers containing no ester groups, e.g. hydroxypropyl methylcellulose
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biophysics (AREA)
- Polymers & Plastics (AREA)
- Gastroenterology & Hepatology (AREA)
- Immunology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3739690 | 1987-11-24 | ||
| DE19873739690 DE3739690A1 (de) | 1987-11-24 | 1987-11-24 | Stabilisierte arzneistoffe, verfahren zu ihrer herstellung sowie stabile arzneizubereitungen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2581888A AU2581888A (en) | 1989-05-25 |
| AU615495B2 true AU615495B2 (en) | 1991-10-03 |
Family
ID=6341084
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU25818/88A Expired AU615495B2 (en) | 1987-11-24 | 1988-11-23 | Stabilized medicinal substances, a process for the preparation thereof, and stable medicinal formulations |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US5151433A (forum.php) |
| EP (1) | EP0317878B1 (forum.php) |
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| FI94339C (fi) | 1989-07-21 | 1995-08-25 | Warner Lambert Co | Menetelmä farmaseuttisesti käyttökelpoisen /R-(R*,R*)/-2-(4-fluorifenyyli)- , -dihydroksi-5-(1-metyylietyyli)-3-fenyyli-4-/(fenyyliamino)karbonyyli/-1H-pyrroli-1-heptaanihapon ja sen farmaseuttisesti hyväksyttävien suolojen valmistamiseksi |
| US6300361B1 (en) | 1990-07-25 | 2001-10-09 | Novartis Ag | Stabilized pharmaceutical compositions comprising acid donors |
| TW483763B (en) * | 1994-09-02 | 2002-04-21 | Astra Ab | Pharmaceutical composition comprising of ramipril and dihydropyridine compound |
| EA000818B1 (ru) * | 1995-12-27 | 2000-04-24 | Жансен Фармасетика Н.В. | Биоадгезивная твердая дозированная лекарственная форма |
| SE9903028D0 (sv) | 1999-08-27 | 1999-08-27 | Astra Ab | New use |
| JP4870888B2 (ja) * | 1999-08-30 | 2012-02-08 | サノフィ−アベンティス・ドイチュラント・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | 心血管の病態の予防におけるレニン−アンギオテンシン系阻害剤の使用 |
| US20030225124A1 (en) * | 1999-08-31 | 2003-12-04 | Spiridon Spireas | Stable formulations of ACE inhibitors, and methods for preparation thereof |
| FR2824477B1 (fr) * | 2001-05-09 | 2005-09-09 | Ethypharm Lab Prod Ethiques | Granules enrobes a base d'inhibiteur de l'enzyme de conversion de l'anfiotensine, leur procede de preparation et comprimes orodispersibles contenant les granules enrobes |
| CA2357982A1 (en) * | 2001-09-28 | 2003-03-28 | Bernard Charles Sherman | Solid compositions comprising ramipril |
| EP1467717A1 (en) * | 2002-01-15 | 2004-10-20 | Ranbaxy Laboratories Limited | Stable pharmaceutical compositions comprising ace inhibitor(s) |
| GB0301471D0 (en) * | 2003-01-22 | 2003-02-19 | Biochemie Gmbh | Organic compounds |
| EP1653929A1 (en) * | 2003-01-22 | 2006-05-10 | Sandoz AG | Solid pharmaceutical composition comprising ramipril |
| US20050069586A1 (en) * | 2003-06-26 | 2005-03-31 | Julia Hrakovsky | Stable pharmaceutical compositions of 2-aza-bicyclo [3.3.0]-octane-3-carboxylic acid derivatives |
| US6869963B2 (en) * | 2003-07-11 | 2005-03-22 | Sandoz Ag | Stable pharmaceutical compositions containing an ACE inhibitor |
| EP1694308A1 (en) * | 2003-10-30 | 2006-08-30 | Lupin Ltd. | Stable formulations of ace inhibitors and methods for preparation thereof |
| GB2394660A (en) * | 2003-12-17 | 2004-05-05 | Niche Generics Ltd | Stabilisation of pharmaceutical compositions comprising ACE inhibitor by absence of acidic excipients having large specific surface area, eg silicon dioxide |
| GB2411355B (en) * | 2004-02-27 | 2006-02-22 | Niche Generics Ltd | Pharmaceutical composition |
| EA011862B1 (ru) * | 2004-03-24 | 2009-06-30 | Актавис Груп Хф. | Композиции рамиприла |
| US20060045911A1 (en) * | 2004-08-27 | 2006-03-02 | Sun Pharmaceutical Industries Ltd. | Stable pharmaceutical formulations |
| KR20070085759A (ko) * | 2004-11-05 | 2007-08-27 | 킹 파머슈티칼스 리서치 앤드 디벨로프먼트 아이엔씨 | 개별적으로 코팅된 안정화된 라미프릴 입자, 조성물 및방법 |
| US20080096979A1 (en) * | 2004-11-08 | 2008-04-24 | Rubicon Research Pvt. Ltd. | Aqueous Pharmaceutical Coating |
| GB0518129D0 (en) * | 2005-09-06 | 2005-10-12 | Arrow Int Ltd | Ramipril formulation |
| KR100679166B1 (ko) | 2005-10-04 | 2007-02-06 | 신풍제약주식회사 | 안정성이 증진된 약제학적 조성물 및 그의 제조방법 |
| US20070098782A1 (en) * | 2005-10-28 | 2007-05-03 | Selamine Limited | Ramipril Formulation |
| GB2431579A (en) * | 2005-10-28 | 2007-05-02 | Arrow Int Ltd | Ramipril formulations |
| RU2008142623A (ru) * | 2006-03-28 | 2010-05-10 | Джелесис, Инк. (Us) | Способ и лекарственный препарат для повышения набухаемости гидрогеля и/или продолжительности его действия в желудке у животного организма, способ и лекарственный препарат для доставки лекарственного средства |
| US20070232680A1 (en) * | 2006-04-04 | 2007-10-04 | Vijayabhaskar Bolugoddu | Preparation of ramipril and stable pharmaceutical compositions |
| EP1901739A2 (en) * | 2006-04-19 | 2008-03-26 | Teva Pharmaceutical Industries Ltd | Stable pharmaceutical compositions of 2-aza-bicyclo[3.3.0]-octane-3-carboxylic acid derivatives |
| BRPI0621739A2 (pt) * | 2006-06-02 | 2011-12-20 | Teva Pharma | formulação estável que consiste em drogas sensìveis à umectação e seu procedimento de fabricação |
| US20070281000A1 (en) * | 2006-06-02 | 2007-12-06 | Michael Fox | Stable formulation comprising moisture sensitive drug/s and manufacturing procedure thereof |
| PT1864677E (pt) * | 2006-06-02 | 2008-03-13 | Teva Pharma | Formulação estável compreendendo um fármaco sensível à humidade e processo para a sua produção |
| US20100035955A1 (en) * | 2006-06-30 | 2010-02-11 | Panagiotis Keramidas | Stabilised Composition Comprising ACE Inhibitors |
| AU2007291602B2 (en) * | 2006-08-28 | 2012-09-06 | Sanofi-Aventis Deutschland Gmbh | Methods of lowering glucose levels |
| GB0624084D0 (en) * | 2006-12-01 | 2007-01-10 | Selamine Ltd | Ramipril amino acid salts |
| GB0624090D0 (en) * | 2006-12-01 | 2007-01-10 | Selamine Ltd | Ramipril amine salts |
| GB0624087D0 (en) * | 2006-12-01 | 2007-01-10 | Selamine Ltd | Ramipril combination salt |
| PL382311A1 (pl) * | 2007-04-27 | 2008-11-10 | Zakłady Farmaceutyczne POLPHARMA Spółka Akcyjna | Kompozycja farmaceutyczna o polepszonej stabilności zawierająca inhibitor acetylocholinoesterazy lub farmaceutycznie dopuszczalną jego sól oraz sposób jej wytwarzania |
| JP2011515445A (ja) | 2008-03-28 | 2011-05-19 | フエルレル インターナショナル，ソシエダッド アノニマ | 心臓血管疾患の予防のためのカプセル剤 |
| WO2010030735A2 (en) * | 2008-09-11 | 2010-03-18 | Aethos Pharmaceuticals, Inc. | Stabilized coating for pharmaceutical formulations |
| TR200906322A2 (tr) | 2009-08-17 | 2011-07-21 | Bi̇lgi̇ç Mahmut | Çözünürlük ve stabilite özellikleri geliştirilmiş granüller. |
| ES2364011B1 (es) | 2009-11-20 | 2013-01-24 | Gp Pharm, S.A. | Cápsulas de principios activos farmacéuticos y ésteres de ácidos grasos poliinsaturados para el tratamiento de enfermedades cardiovasculares. |
| UA113977C2 (xx) | 2012-02-17 | 2017-04-10 | Фармацевтична композиція з покращеною стабільністю | |
| PL227900B1 (pl) | 2012-11-15 | 2018-01-31 | Adamed Spolka Z Ograniczona Odpowiedzialnoscia | Kompozycja farmaceutyczna zawierająca inhibitor ACE i bloker kanałów wapniowych, sposób jej wytwarzania i jednostka dawkowania zawierająca tę kompozycję |
| HUP1300496A2 (hu) | 2013-08-16 | 2015-03-02 | Egis Gyogyszergyar Nyilvanosan Muekoedoe Reszvenytarsasag | Stabil kombinációs gyógyszerkészítmény |
| TWI668285B (zh) * | 2015-12-31 | 2019-08-11 | 長興材料工業股份有限公司 | 可熱聚合之組合物、由此形成之組成液及其用途 |
| EP3275432A1 (en) | 2016-07-25 | 2018-01-31 | H e x a l Aktiengesellschaft | Dosage form with ace inhibitor |
| HRP20241424T1 (hr) | 2020-02-10 | 2024-12-20 | Adamed Pharma S.A. | Pripravak koji sadrži ramipril i indapamid |
| CN115068434B (zh) * | 2022-08-03 | 2023-05-09 | 昆山龙灯瑞迪制药有限公司 | 一种雷米普利片的制备方法 |
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- 1988-11-15 DE DE8888119014T patent/DE3869919D1/de not_active Expired - Lifetime
- 1988-11-15 ES ES198888119014T patent/ES2033400T3/es not_active Expired - Lifetime
- 1988-11-15 EP EP88119014A patent/EP0317878B1/de not_active Expired - Lifetime
- 1988-11-22 PH PH37849A patent/PH27416A/en unknown
- 1988-11-22 JP JP63293761A patent/JPH0768140B2/ja not_active Expired - Lifetime
- 1988-11-22 HU HU885992A patent/HU202100B/hu unknown
- 1988-11-22 FI FI885398A patent/FI93693C/fi not_active IP Right Cessation
- 1988-11-22 NZ NZ227032A patent/NZ227032A/en unknown
- 1988-11-22 ZA ZA888734A patent/ZA888734B/xx unknown
- 1988-11-22 US US07/274,598 patent/US5151433A/en not_active Expired - Lifetime
- 1988-11-23 CA CA000583952A patent/CA1338344C/en not_active Expired - Lifetime
- 1988-11-23 IE IE350588A patent/IE61173B1/en not_active IP Right Cessation
- 1988-11-23 AU AU25818/88A patent/AU615495B2/en not_active Expired
- 1988-11-23 NO NO885213A patent/NO176550C/no unknown
- 1988-11-23 IL IL88460A patent/IL88460A0/xx not_active IP Right Cessation
- 1988-11-23 KR KR1019880015400A patent/KR970004908B1/ko not_active Expired - Lifetime
- 1988-11-23 PT PT89061A patent/PT89061B/pt not_active IP Right Cessation
- 1988-11-23 CN CN88108057A patent/CN1028962C/zh not_active Expired - Lifetime
- 1988-11-23 DK DK653688A patent/DK168423B1/da not_active IP Right Cessation
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Owner name: AVENTIS PHARMA DEUTSCHLAND GMBH Free format text: FORMER OWNER WAS: HOECHST AKTIENGESELLSCHAFT |