CA2282082C - Microgranules contenant du cisplatine - Google Patents
Microgranules contenant du cisplatine Download PDFInfo
- Publication number
- CA2282082C CA2282082C CA002282082A CA2282082A CA2282082C CA 2282082 C CA2282082 C CA 2282082C CA 002282082 A CA002282082 A CA 002282082A CA 2282082 A CA2282082 A CA 2282082A CA 2282082 C CA2282082 C CA 2282082C
- Authority
- CA
- Canada
- Prior art keywords
- microgranules
- cisplatin
- agent
- coating
- immediate
- 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 - Lifetime
Links
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 title claims abstract description 103
- 229960004316 cisplatin Drugs 0.000 title claims abstract description 103
- 239000000203 mixture Substances 0.000 claims abstract description 24
- 238000002360 preparation method Methods 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 12
- 238000013270 controlled release Methods 0.000 claims abstract description 11
- 239000002246 antineoplastic agent Substances 0.000 claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 238000001959 radiotherapy Methods 0.000 claims abstract description 4
- 239000013066 combination product Substances 0.000 claims abstract description 3
- 229940127555 combination product Drugs 0.000 claims abstract description 3
- 229940126601 medicinal product Drugs 0.000 claims abstract 2
- 239000011248 coating agent Substances 0.000 claims description 35
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical group [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 33
- 238000000576 coating method Methods 0.000 claims description 23
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 23
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 18
- 230000007935 neutral effect Effects 0.000 claims description 17
- 239000011780 sodium chloride Substances 0.000 claims description 17
- 239000000454 talc Substances 0.000 claims description 15
- 229910052623 talc Inorganic materials 0.000 claims description 15
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical group CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 claims description 14
- 239000001069 triethyl citrate Substances 0.000 claims description 14
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 claims description 14
- 235000013769 triethyl citrate Nutrition 0.000 claims description 14
- 239000000725 suspension Substances 0.000 claims description 11
- 229920000642 polymer Polymers 0.000 claims description 10
- 239000004531 microgranule Substances 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims description 8
- 239000011230 binding agent Substances 0.000 claims description 7
- 108010006654 Bleomycin Proteins 0.000 claims description 6
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical group FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims description 6
- 229960001561 bleomycin Drugs 0.000 claims description 6
- OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 claims description 6
- 239000008280 blood Substances 0.000 claims description 6
- 210000004369 blood Anatomy 0.000 claims description 6
- 229960002949 fluorouracil Drugs 0.000 claims description 6
- 239000002245 particle Substances 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 239000004094 surface-active agent Substances 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 5
- 239000010410 layer Substances 0.000 claims description 5
- 239000000314 lubricant Substances 0.000 claims description 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
- 239000004014 plasticizer Substances 0.000 claims description 4
- 238000005507 spraying Methods 0.000 claims description 4
- 239000003381 stabilizer Substances 0.000 claims description 4
- JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 claims description 3
- 230000001476 alcoholic effect Effects 0.000 claims description 3
- VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 claims description 3
- 229960005420 etoposide Drugs 0.000 claims description 3
- 229960003048 vinblastine Drugs 0.000 claims description 3
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 claims description 3
- 229930012538 Paclitaxel Natural products 0.000 claims description 2
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 2
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 2
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 2
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical group 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 claims description 2
- 229960001592 paclitaxel Drugs 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 claims description 2
- 229920000053 polysorbate 80 Polymers 0.000 claims description 2
- 229940068968 polysorbate 80 Drugs 0.000 claims description 2
- 239000011253 protective coating Substances 0.000 claims description 2
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims description 2
- WFWLQNSHRPWKFK-ZCFIWIBFSA-N tegafur Chemical compound O=C1NC(=O)C(F)=CN1[C@@H]1OCCC1 WFWLQNSHRPWKFK-ZCFIWIBFSA-N 0.000 claims description 2
- 229960001674 tegafur Drugs 0.000 claims description 2
- WROUWQQRXUBECT-UHFFFAOYSA-N 2-ethylacrylic acid Chemical compound CCC(=C)C(O)=O WROUWQQRXUBECT-UHFFFAOYSA-N 0.000 claims 1
- RYYCJUAHISIHTL-UHFFFAOYSA-N 5-azaorotic acid Chemical compound OC(=O)C1=NC(=O)NC(=O)N1 RYYCJUAHISIHTL-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 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 claims 1
- 238000009096 combination chemotherapy Methods 0.000 claims 1
- 229920003145 methacrylic acid copolymer Polymers 0.000 claims 1
- 238000011275 oncology therapy Methods 0.000 claims 1
- 229950000193 oteracil Drugs 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 238000009472 formulation Methods 0.000 abstract description 11
- 238000002560 therapeutic procedure Methods 0.000 abstract description 8
- 230000001093 anti-cancer Effects 0.000 abstract description 5
- 239000012736 aqueous medium Substances 0.000 abstract description 3
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 20
- 239000002904 solvent Substances 0.000 description 17
- 229920003134 Eudragit® polymer Polymers 0.000 description 16
- 229920001030 Polyethylene Glycol 4000 Polymers 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000004480 active ingredient Substances 0.000 description 12
- 239000008213 purified water Substances 0.000 description 11
- 238000001990 intravenous administration Methods 0.000 description 10
- 229910052697 platinum Inorganic materials 0.000 description 10
- 238000005303 weighing Methods 0.000 description 10
- 241000282472 Canis lupus familiaris Species 0.000 description 9
- 230000036470 plasma concentration Effects 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 8
- 206010028980 Neoplasm Diseases 0.000 description 7
- 206010029155 Nephropathy toxic Diseases 0.000 description 7
- 239000012895 dilution Substances 0.000 description 7
- 238000010790 dilution Methods 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 231100000417 nephrotoxicity Toxicity 0.000 description 7
- 230000007694 nephrotoxicity Effects 0.000 description 7
- 230000002035 prolonged effect Effects 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 201000011510 cancer Diseases 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 239000007972 injectable composition Substances 0.000 description 4
- 210000003734 kidney Anatomy 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- 230000002588 toxic effect Effects 0.000 description 4
- 231100000419 toxicity Toxicity 0.000 description 4
- 230000001988 toxicity Effects 0.000 description 4
- 229920003163 Eudragit® NE 30 D Polymers 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 238000001802 infusion Methods 0.000 description 3
- 231100000682 maximum tolerated dose Toxicity 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 206010047700 Vomiting Diseases 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229940041181 antineoplastic drug Drugs 0.000 description 2
- 210000001185 bone marrow Anatomy 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 230000001079 digestive effect Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 description 2
- 239000012456 homogeneous solution Substances 0.000 description 2
- 230000036571 hydration Effects 0.000 description 2
- 238000006703 hydration reaction Methods 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 231100000027 toxicology Toxicity 0.000 description 2
- 230000008673 vomiting Effects 0.000 description 2
- 206010065553 Bone marrow failure Diseases 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 206010059024 Gastrointestinal toxicity Diseases 0.000 description 1
- ZPLQIPFOCGIIHV-UHFFFAOYSA-N Gimeracil Chemical compound OC1=CC(=O)C(Cl)=CN1 ZPLQIPFOCGIIHV-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 206010028817 Nausea and vomiting symptoms Diseases 0.000 description 1
- 206010029350 Neurotoxicity Diseases 0.000 description 1
- 208000007452 Plasmacytoma Diseases 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 229930006000 Sucrose Natural products 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
- 206010044221 Toxic encephalopathy Diseases 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- XKMRRTOUMJRJIA-UHFFFAOYSA-N ammonia nh3 Chemical compound N.N XKMRRTOUMJRJIA-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- 238000011888 autopsy Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000036765 blood level Effects 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 229920001688 coating polymer Polymers 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 238000004891 communication Methods 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
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007850 degeneration Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000035619 diuresis Effects 0.000 description 1
- 208000000718 duodenal ulcer Diseases 0.000 description 1
- 210000001198 duodenum Anatomy 0.000 description 1
- 238000010218 electron microscopic analysis Methods 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 235000012631 food intake Nutrition 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 231100000414 gastrointestinal toxicity Toxicity 0.000 description 1
- 229950009822 gimeracil Drugs 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000007902 hard capsule Substances 0.000 description 1
- 230000002489 hematologic effect Effects 0.000 description 1
- 230000002008 hemorrhagic effect Effects 0.000 description 1
- 210000003405 ileum Anatomy 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 210000004877 mucosa Anatomy 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 208000013435 necrotic lesion Diseases 0.000 description 1
- 231100000228 neurotoxicity Toxicity 0.000 description 1
- 230000007135 neurotoxicity Effects 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000008016 pharmaceutical coating Substances 0.000 description 1
- 210000001187 pylorus Anatomy 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005563 spheronization Methods 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
- 210000001541 thymus gland Anatomy 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
- 210000005239 tubule Anatomy 0.000 description 1
- 210000002700 urine Anatomy 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
- A61K9/14—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
- A61K9/167—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction with an outer layer or coating comprising drug; with chemically bound drugs or non-active substances on their surface
- A61K9/1676—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction with an outer layer or coating comprising drug; with chemically bound drugs or non-active substances on their surface having a drug-free core with discrete complete coating layer containing drug
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/24—Heavy metals; Compounds thereof
- A61K33/243—Platinum; Compounds 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
- A61K9/48—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
- A61K9/5073—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 having two or more different coatings optionally including drug-containing subcoatings
- A61K9/5078—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 having two or more different coatings optionally including drug-containing subcoatings with drug-free core
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Inorganic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9701545A FR2759293B1 (fr) | 1997-02-11 | 1997-02-11 | Microgranules contenant du cisplatine, procede de fabrication, preparation pharmaceutique et utilisation en polychimiotherapie ou en association avec une radiotherapie |
| FR97/01545 | 1997-02-11 | ||
| PCT/FR1998/000251 WO1998034599A1 (fr) | 1997-02-11 | 1998-02-10 | Microgranules contenant du cisplatine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2282082A1 CA2282082A1 (fr) | 1998-08-13 |
| CA2282082C true CA2282082C (fr) | 2005-10-18 |
Family
ID=9503556
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002282082A Expired - Lifetime CA2282082C (fr) | 1997-02-11 | 1998-02-10 | Microgranules contenant du cisplatine |
Country Status (24)
| Country | Link |
|---|---|
| US (2) | US6458389B1 (h) |
| EP (1) | EP0971702B1 (h) |
| JP (1) | JP4549445B2 (h) |
| KR (1) | KR100471672B1 (h) |
| AR (1) | AR011133A1 (h) |
| AT (1) | ATE255409T1 (h) |
| BG (1) | BG64247B1 (h) |
| BR (1) | BR9807319A (h) |
| CA (1) | CA2282082C (h) |
| DE (1) | DE69820239T2 (h) |
| DK (1) | DK0971702T3 (h) |
| EA (1) | EA001760B1 (h) |
| ES (1) | ES2210726T3 (h) |
| FR (1) | FR2759293B1 (h) |
| HU (1) | HU225425B1 (h) |
| IL (1) | IL131326A (h) |
| IN (1) | IN187998B (h) |
| NO (1) | NO323230B1 (h) |
| NZ (1) | NZ337216A (h) |
| PL (1) | PL191631B1 (h) |
| PT (1) | PT971702E (h) |
| TW (1) | TW561055B (h) |
| WO (1) | WO1998034599A1 (h) |
| ZA (1) | ZA981123B (h) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US20050096304A1 (en) * | 1998-09-08 | 2005-05-05 | David White | Method of treating cancer using dithiocarbamate derivatives |
| FR2790668B1 (fr) * | 1999-03-12 | 2002-07-26 | D B F | Granules contenant une substance vegetale et leur procede de preparation |
| CA2374356C (fr) * | 1999-05-17 | 2012-01-03 | D.B.F. | Granules contenant une substance vegetale et leur procede de preparation |
| WO2005034923A1 (en) * | 2003-10-10 | 2005-04-21 | Ethypharm | Sustained-release microgranules containing gingko biloba extract and the process for manufacturing these |
| FR2861990B1 (fr) * | 2003-11-10 | 2006-02-10 | Nouveaux Produits Pharma | Comprimes faiblement doses a reseau de polymeres |
| JP2008520696A (ja) * | 2004-11-18 | 2008-06-19 | ブリストル−マイヤーズ スクイブ カンパニー | イキサベピロンを含む腸溶性被覆ビーズおよびその製造 |
| KR20070092972A (ko) * | 2004-12-10 | 2007-09-14 | 테무릭크 가부시키가이샤 | 전이암 치료제 및 암 전이 억제제 |
| US9107824B2 (en) | 2005-11-08 | 2015-08-18 | Insmed Incorporated | Methods of treating cancer with high potency lipid-based platinum compound formulations administered intraperitoneally |
| FR2918566B1 (fr) | 2007-07-11 | 2009-10-09 | Pierre Fabre Medicament Sa | Composition pharmaceutique stable d'un sel hydrosoluble de vinflunine. |
| FR2918567B1 (fr) * | 2007-07-11 | 2012-08-03 | Pf Medicament | Composition pharmaceutique stable d'un sel hydrosoluble de vinorelbine. |
| CA2699224C (en) * | 2007-09-21 | 2014-12-16 | Evonik Roehm Gmbh | Ph-dependent controlled release pharmaceutical composition for non-opioids with resistance against the influence of ethanol |
| US9700520B2 (en) * | 2007-09-21 | 2017-07-11 | Evonik Roehm Gmbh | PH-dependent controlled release pharmaceutical opioid composition with resistance against the influence of ethanol |
| PL2230932T3 (pl) * | 2008-01-10 | 2017-09-29 | Evonik Röhm Gmbh | Powlekany preparat farmaceutyczny lub nutraceutyczny o zwiększonym uwalnianiu substancji aktywnej w jelicie grubym |
| KR20100103565A (ko) * | 2008-01-10 | 2010-09-27 | 에보니크 룀 게엠베하 | 촉진되고 조절된 활성 물질 방출을 갖는 코팅된 제약학적 또는 건강기능성 제제 |
| DK177529B1 (en) * | 2009-10-23 | 2013-09-08 | Bio Bedst Aps | Liposomes with improved storage stability |
| CA2688202C (en) * | 2009-12-11 | 2012-11-13 | Bj Services Company | Viscoelastic fluids containing hydroxyethyl cellulose |
| EP2371356B1 (en) * | 2010-03-12 | 2012-12-19 | Phoeme GmbH | Multi-particle pharmaceutical formulation for colon absorption |
| US8070047B1 (en) * | 2010-12-02 | 2011-12-06 | Rohm And Haas Electronic Materials Llc | Flux composition and method of soldering |
| EP2892524B1 (en) | 2012-09-04 | 2020-11-25 | Eleison Pharmaceuticals, LLC | Preventing pulmonary recurrence of cancer with lipid-complexed cisplatin |
| US10335390B2 (en) | 2014-09-05 | 2019-07-02 | Symbiomix Therapeutics, Llc | Secnidazole for use in the treatment of bacterial vaginosis |
| WO2016169042A1 (en) * | 2015-04-24 | 2016-10-27 | Genedia Biotech Co. Ltd. | Combination therapies for bladder cancer |
| US11253501B2 (en) | 2015-06-01 | 2022-02-22 | Lupin Inc. | Secnidazole formulations and use in treating bacterial vaginosis |
| CA2988761A1 (en) | 2015-06-12 | 2016-12-15 | Vaxart, Inc. | Formulations for small intestinal delivery of rsv and norovirus antigens |
| TWI795462B (zh) | 2017-11-17 | 2023-03-11 | 日商鹽野義製藥股份有限公司 | 光安定性及溶出性優異的醫藥製劑 |
| EP3785716A4 (en) * | 2018-04-24 | 2022-03-02 | Shionogi & Co., Ltd | SOLID FORMULATION WITH EXCELLENT STABILITY |
| CN112236146B (zh) * | 2018-04-24 | 2025-04-15 | 盐野义制药株式会社 | 稳定性优良的固体制剂 |
| US12280037B2 (en) | 2020-09-22 | 2025-04-22 | Evofem Biosciences, Inc. | Method and pharmaceutical composition for treating or preventing trichomoniasis and uses thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| DE3172570D1 (en) * | 1981-03-11 | 1985-11-14 | Mirko Beljanski | Serpentine, alstonine and sempervirine drugs for the specific inhibition of tumurous and cancerous cells |
| IT1153974B (it) * | 1982-09-23 | 1987-01-21 | Erba Farmitalia | Composizioni farmacologiche a base di cisplatino e metodo per il loro ottenimento |
| DE3421468A1 (de) * | 1984-06-08 | 1985-12-19 | Dr. Rentschler Arzneimittel Gmbh & Co, 7958 Laupheim | Lipidnanopellets als traegersystem fuer arzneimittel zur peroralen anwendung |
| DE3523454A1 (de) * | 1985-07-01 | 1987-01-08 | Eberhard Prof Dr Nuernberg | Formkoerper |
| US4925674A (en) * | 1988-08-25 | 1990-05-15 | Himedics, Inc. | Amoxicillin microencapsulated granules |
| US5399363A (en) * | 1991-01-25 | 1995-03-21 | Eastman Kodak Company | Surface modified anticancer nanoparticles |
| JPH05294839A (ja) * | 1992-04-20 | 1993-11-09 | Biomaterial Universe Kk | シスプラチン含有生体内分解吸収性高分子の微小球お よびその製造法 |
| US5795882A (en) * | 1992-06-22 | 1998-08-18 | Bone Care International, Inc. | Method of treating prostatic diseases using delayed and/or sustained release vitamin D formulations |
| JPH07112932A (ja) * | 1993-08-27 | 1995-05-02 | Mitsui Toatsu Chem Inc | 徐放性医薬製剤 |
| JPH0789849A (ja) * | 1993-09-20 | 1995-04-04 | Fujisawa Pharmaceut Co Ltd | 徐放性製剤 |
| JPH0859460A (ja) * | 1994-08-22 | 1996-03-05 | Tanaka Kikinzoku Kogyo Kk | 抗ガン剤内包キトサンミクロスフェア及びその製造法 |
| US5637319A (en) * | 1995-03-01 | 1997-06-10 | Takada; Kanji | Controlled-release preparations |
| US5614206A (en) * | 1995-03-07 | 1997-03-25 | Wright Medical Technology, Inc. | Controlled dissolution pellet containing calcium sulfate |
| AU714992B2 (en) * | 1996-08-23 | 2000-01-13 | Alza Corporation | Liposomes containing a cisplatin compound |
-
1997
- 1997-02-11 FR FR9701545A patent/FR2759293B1/fr not_active Expired - Lifetime
-
1998
- 1998-02-10 WO PCT/FR1998/000251 patent/WO1998034599A1/fr active IP Right Grant
- 1998-02-10 DK DK98908157T patent/DK0971702T3/da active
- 1998-02-10 KR KR10-1999-7007263A patent/KR100471672B1/ko not_active Expired - Fee Related
- 1998-02-10 CA CA002282082A patent/CA2282082C/fr not_active Expired - Lifetime
- 1998-02-10 DE DE69820239T patent/DE69820239T2/de not_active Expired - Lifetime
- 1998-02-10 EP EP98908157A patent/EP0971702B1/fr not_active Expired - Lifetime
- 1998-02-10 PL PL335107A patent/PL191631B1/pl not_active IP Right Cessation
- 1998-02-10 NZ NZ337216A patent/NZ337216A/xx not_active IP Right Cessation
- 1998-02-10 JP JP53389798A patent/JP4549445B2/ja not_active Expired - Lifetime
- 1998-02-10 PT PT98908157T patent/PT971702E/pt unknown
- 1998-02-10 ES ES98908157T patent/ES2210726T3/es not_active Expired - Lifetime
- 1998-02-10 IL IL13132698A patent/IL131326A/xx not_active IP Right Cessation
- 1998-02-10 US US09/367,270 patent/US6458389B1/en not_active Expired - Lifetime
- 1998-02-10 EA EA199900734A patent/EA001760B1/ru not_active IP Right Cessation
- 1998-02-10 IN IN337DE1998 patent/IN187998B/en unknown
- 1998-02-10 HU HU0001719A patent/HU225425B1/hu not_active IP Right Cessation
- 1998-02-10 TW TW087101722A patent/TW561055B/zh not_active IP Right Cessation
- 1998-02-10 AT AT98908157T patent/ATE255409T1/de active
- 1998-02-10 BR BR9807319-2A patent/BR9807319A/pt not_active Application Discontinuation
- 1998-02-11 AR ARP980100613A patent/AR011133A1/es active IP Right Grant
- 1998-02-11 ZA ZA981123A patent/ZA981123B/xx unknown
-
1999
- 1999-08-10 BG BG103647A patent/BG64247B1/bg unknown
- 1999-08-11 NO NO19993881A patent/NO323230B1/no not_active IP Right Cessation
-
2002
- 2002-07-25 US US10/200,998 patent/US20030017210A1/en not_active Abandoned
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