CA2294783C - Compositions pharmaceutiques administrables par voie orale, comprenant une substance active et une cyclodextrine - Google Patents
Compositions pharmaceutiques administrables par voie orale, comprenant une substance active et une cyclodextrine Download PDFInfo
- Publication number
- CA2294783C CA2294783C CA002294783A CA2294783A CA2294783C CA 2294783 C CA2294783 C CA 2294783C CA 002294783 A CA002294783 A CA 002294783A CA 2294783 A CA2294783 A CA 2294783A CA 2294783 C CA2294783 C CA 2294783C
- Authority
- CA
- Canada
- Prior art keywords
- cyclodextrin
- active substance
- cetirizine
- pharmaceutical composition
- beta
- 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 - Fee Related
Links
- 229920000858 Cyclodextrin Polymers 0.000 title claims abstract description 60
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 239000013543 active substance Substances 0.000 title claims abstract description 21
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 16
- 150000008640 diphenylmethylpiperazines Chemical class 0.000 claims abstract description 12
- ZKLPARSLTMPFCP-UHFFFAOYSA-N Cetirizine Chemical compound C1CN(CCOCC(=O)O)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZKLPARSLTMPFCP-UHFFFAOYSA-N 0.000 claims description 36
- 229960001803 cetirizine Drugs 0.000 claims description 35
- 239000008187 granular material Substances 0.000 claims description 6
- ZQDWXGKKHFNSQK-UHFFFAOYSA-N hydroxyzine Chemical compound C1CN(CCOCCO)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZQDWXGKKHFNSQK-UHFFFAOYSA-N 0.000 claims description 6
- 239000006188 syrup Substances 0.000 claims description 6
- 235000020357 syrup Nutrition 0.000 claims description 6
- 229940097362 cyclodextrins Drugs 0.000 claims description 5
- 229960000930 hydroxyzine Drugs 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000006190 sub-lingual tablet Substances 0.000 claims description 5
- BAWMMJAUVBLLEE-UHFFFAOYSA-N 2-[2-[4-[bis(4-fluorophenyl)methyl]piperazin-1-yl]ethoxy]acetic acid Chemical compound C1CN(CCOCC(=O)O)CCN1C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 BAWMMJAUVBLLEE-UHFFFAOYSA-N 0.000 claims description 3
- OCJYIGYOJCODJL-UHFFFAOYSA-N Meclizine Chemical compound CC1=CC=CC(CN2CCN(CC2)C(C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)=C1 OCJYIGYOJCODJL-UHFFFAOYSA-N 0.000 claims description 3
- 239000007910 chewable tablet Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical class 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 claims description 2
- MOYGZHXDRJNJEP-UHFFFAOYSA-N buclizine Chemical compound C1=CC(C(C)(C)C)=CC=C1CN1CCN(C(C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)CC1 MOYGZHXDRJNJEP-UHFFFAOYSA-N 0.000 claims description 2
- 229960001705 buclizine Drugs 0.000 claims description 2
- 229940068682 chewable tablet Drugs 0.000 claims description 2
- 229950003420 efletirizine Drugs 0.000 claims description 2
- 229960001474 meclozine Drugs 0.000 claims description 2
- 229940098466 sublingual tablet Drugs 0.000 claims description 2
- QGKBSGBYSPTPKJ-UZMKXNTCSA-N 2,6-di-o-methyl-β-cyclodextrin Chemical compound COC[C@H]([C@H]([C@@H]([C@H]1OC)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COC)[C@H]([C@@H]([C@H]3OC)O)O[C@H]3O[C@H](COC)[C@H]([C@@H]([C@H]3OC)O)O[C@H]3O[C@H](COC)[C@H]([C@@H]([C@H]3OC)O)O[C@H]3O[C@H](COC)[C@H]([C@@H]([C@H]3OC)O)O3)[C@H](O)[C@H]2OC)COC)O[C@@H]1O[C@H]1[C@H](O)[C@@H](OC)[C@@H]3O[C@@H]1COC QGKBSGBYSPTPKJ-UZMKXNTCSA-N 0.000 claims 1
- 229940031576 hydroxypropylbetadex (0.58-0.68 ms) Drugs 0.000 claims 1
- 239000000243 solution Substances 0.000 description 19
- 239000000203 mixture Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 238000010521 absorption reaction Methods 0.000 description 10
- 235000019658 bitter taste Nutrition 0.000 description 10
- 238000000034 method Methods 0.000 description 9
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- 239000004480 active ingredient Substances 0.000 description 7
- -1 alkoxy radical Chemical class 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
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- 238000012360 testing method Methods 0.000 description 6
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- 239000007788 liquid Substances 0.000 description 4
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- 229910002016 Aerosil® 200 Inorganic materials 0.000 description 3
- 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 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
- 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 3
- 229930195725 Mannitol Natural products 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000000739 antihistaminic agent Substances 0.000 description 3
- 238000006073 displacement reaction Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 3
- 239000000594 mannitol Substances 0.000 description 3
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- 238000002156 mixing Methods 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- WBZFUFAFFUEMEI-UHFFFAOYSA-M Acesulfame k Chemical compound [K+].CC1=CC(=O)[N-]S(=O)(=O)O1 WBZFUFAFFUEMEI-UHFFFAOYSA-M 0.000 description 2
- 229920002785 Croscarmellose sodium Polymers 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229930006000 Sucrose Natural products 0.000 description 2
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 230000001387 anti-histamine Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
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- 230000002209 hydrophobic effect Effects 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- STZCRXQWRGQSJD-GEEYTBSJSA-M methyl orange Chemical compound [Na+].C1=CC(N(C)C)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 STZCRXQWRGQSJD-GEEYTBSJSA-M 0.000 description 2
- 229940012189 methyl orange Drugs 0.000 description 2
- 229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 2
- 239000001253 polyvinylpolypyrrolidone Substances 0.000 description 2
- 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- UZKBSZSTDQSMDR-UHFFFAOYSA-N 1-[(4-chlorophenyl)-phenylmethyl]piperazine Chemical group C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)N1CCNCC1 UZKBSZSTDQSMDR-UHFFFAOYSA-N 0.000 description 1
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 239000005449 Avicel CE Substances 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- 239000001116 FEMA 4028 Substances 0.000 description 1
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 description 1
- 240000004670 Glycyrrhiza echinata Species 0.000 description 1
- 235000001453 Glycyrrhiza echinata Nutrition 0.000 description 1
- 235000006200 Glycyrrhiza glabra Nutrition 0.000 description 1
- 235000017382 Glycyrrhiza lepidota Nutrition 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- ILRKKHJEINIICQ-OOFFSTKBSA-N Monoammonium glycyrrhizinate Chemical compound N.O([C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@H]1CC[C@]2(C)[C@H]3C(=O)C=C4[C@@H]5C[C@](C)(CC[C@@]5(CC[C@@]4(C)[C@]3(C)CC[C@H]2C1(C)C)C)C(O)=O)C(O)=O)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O ILRKKHJEINIICQ-OOFFSTKBSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- HVWGGPRWKSHASF-UHFFFAOYSA-N Sulfuric acid, monooctadecyl ester Chemical compound CCCCCCCCCCCCCCCCCCOS(O)(=O)=O HVWGGPRWKSHASF-UHFFFAOYSA-N 0.000 description 1
- OIRDTQYFTABQOQ-UHTZMRCNSA-N Vidarabine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O OIRDTQYFTABQOQ-UHTZMRCNSA-N 0.000 description 1
- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 1
- QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 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
- 230000009471 action Effects 0.000 description 1
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- 150000001299 aldehydes Chemical group 0.000 description 1
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- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 1
- 229940125715 antihistaminic agent Drugs 0.000 description 1
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- 210000000617 arm Anatomy 0.000 description 1
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- 125000004429 atom Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 235000011175 beta-cyclodextrine Nutrition 0.000 description 1
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- 239000000599 controlled substance Substances 0.000 description 1
- 229960001681 croscarmellose sodium Drugs 0.000 description 1
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 1
- 238000002242 deionisation method Methods 0.000 description 1
- NWVNXDKZIQLBNM-UHFFFAOYSA-N diphenylmethylpiperazine Chemical compound C1CNCCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 NWVNXDKZIQLBNM-UHFFFAOYSA-N 0.000 description 1
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- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 description 1
- 229960000991 ketoprofen Drugs 0.000 description 1
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- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
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- 230000000144 pharmacologic effect Effects 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- 229960002695 phenobarbital Drugs 0.000 description 1
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- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
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- 229910021653 sulphate ion Inorganic materials 0.000 description 1
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- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- 229940125725 tranquilizer Drugs 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- ZSCDBOWYZJWBIY-UHFFFAOYSA-N trimipramine Chemical compound C1CC2=CC=CC=C2N(CC(CN(C)C)C)C2=CC=CC=C21 ZSCDBOWYZJWBIY-UHFFFAOYSA-N 0.000 description 1
- 229960002431 trimipramine Drugs 0.000 description 1
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- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 description 1
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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
- A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
- A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
-
- 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
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6949—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
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- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
- A61K9/0056—Mouth soluble or dispersible forms; Suckable, eatable, chewable coherent forms; Forms rapidly disintegrating in the mouth; Lozenges; Lollipops; Bite capsules; Baked products; Baits or other oral forms for animals
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
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- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
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- A—HUMAN NECESSITIES
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- 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
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nanotechnology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- General Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Physiology (AREA)
- Biophysics (AREA)
- Biotechnology (AREA)
- Immunology (AREA)
- Medical Informatics (AREA)
- Nutrition Science (AREA)
- Crystallography & Structural Chemistry (AREA)
- Pulmonology (AREA)
- Zoology (AREA)
- Psychiatry (AREA)
- Anesthesiology (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE9700572A BE1011251A3 (fr) | 1997-07-03 | 1997-07-03 | Compositions pharmaceutiques administrables par voie orale, comprenant une substance active et une cyclodextrine. |
| BE9700572 | 1997-07-03 | ||
| PCT/BE1998/000100 WO1999001133A1 (fr) | 1997-07-03 | 1998-07-02 | Compositions pharmaceutiques administrables par voie orale, comprenant une substance active et une cyclodextrine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2294783A1 CA2294783A1 (fr) | 1999-01-14 |
| CA2294783C true CA2294783C (fr) | 2006-11-14 |
Family
ID=3890611
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002294783A Expired - Fee Related CA2294783C (fr) | 1997-07-03 | 1998-07-02 | Compositions pharmaceutiques administrables par voie orale, comprenant une substance active et une cyclodextrine |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US6455533B1 (enExample) |
| EP (1) | EP0994710B2 (enExample) |
| JP (2) | JP2002508773A (enExample) |
| KR (1) | KR100551510B1 (enExample) |
| CN (1) | CN1150900C (enExample) |
| AT (1) | ATE224717T1 (enExample) |
| AU (1) | AU727140B2 (enExample) |
| BE (1) | BE1011251A3 (enExample) |
| BR (1) | BR9810495A (enExample) |
| CA (1) | CA2294783C (enExample) |
| DE (1) | DE69808297T3 (enExample) |
| DK (1) | DK0994710T4 (enExample) |
| ES (1) | ES2184293T5 (enExample) |
| ID (1) | ID23806A (enExample) |
| IL (1) | IL133397A (enExample) |
| NZ (1) | NZ501820A (enExample) |
| PL (1) | PL192348B1 (enExample) |
| PT (1) | PT994710E (enExample) |
| RU (1) | RU2192863C2 (enExample) |
| WO (1) | WO1999001133A1 (enExample) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0028575D0 (en) * | 2000-11-23 | 2001-01-10 | Elan Corp Plc | Oral pharmaceutical compositions containing cyclodextrins |
| US20040213839A1 (en) * | 2001-02-05 | 2004-10-28 | Andrew Favara | Methods and compositions for reducing the taste of pharmaceutically active agents |
| NZ534039A (en) * | 2002-01-15 | 2006-08-31 | Ucb Farchim S | Formulations of pharmaceutical compositions for oral administration |
| PL372904A1 (en) * | 2002-04-04 | 2005-08-08 | Pfizer Products Inc. | Palatable chewable tablet |
| CA2574602A1 (en) * | 2004-07-22 | 2006-02-02 | Pfizer Products Inc. | Taste masking formulation comprising the drug in a dissolution-retarded form and/or cyclodextrin in a dissolution-enhanced form |
| US20060147518A1 (en) * | 2004-12-30 | 2006-07-06 | Pierre Fabre Medicament | Stable solid dispersion of a derivative of vinca alkaloid and process for manufacturing it |
| US20060198885A1 (en) * | 2005-02-22 | 2006-09-07 | Sun Pharmaceutical Industries Ltd. | Oral pharmaceutical composition |
| US20070086974A1 (en) * | 2005-10-06 | 2007-04-19 | Gawande Rahul S | Cetirizine compositions |
| US20090269393A1 (en) * | 2006-06-12 | 2009-10-29 | Jubliant Organosys Limited | Chewable Bilayer Tablet Formulation |
| JP2008143807A (ja) * | 2006-12-07 | 2008-06-26 | Sato Pharmaceutical Co Ltd | 感冒薬カプセル剤及びその製造方法 |
| EP2550967A1 (en) * | 2007-07-11 | 2013-01-30 | Fertin Pharma A/S | Compressed chewing gum tablet comprising taste-masking agent |
| US20100260818A1 (en) * | 2007-07-11 | 2010-10-14 | Fertin Pharma A/S | Stable medicated chewing gum comprising cyclodextrin inclusion complex |
| WO2009054432A1 (ja) * | 2007-10-26 | 2009-04-30 | Daiichi Sankyo Company, Limited | 口腔内速崩壊性医薬組成物およびその製造方法 |
| US8138192B2 (en) * | 2007-10-31 | 2012-03-20 | Genebiology, Inc. | Injectable meclizine formulations and methods |
| WO2009061465A1 (en) * | 2007-11-06 | 2009-05-14 | Teva Pharmaceutical Industries Ltd. | Chewable formulations |
| ES2564056T3 (es) * | 2008-09-05 | 2016-03-17 | Johnson & Johnson Consumer Inc. | Método para hacer pastillas de cetirizina |
| WO2011110939A2 (en) | 2010-03-11 | 2011-09-15 | Rubicon Research Private Limited | Pharmaceutical compositions of substituted benzhydrylpiperazines |
| WO2011150859A1 (en) * | 2010-06-04 | 2011-12-08 | Comprehensive Drug Enterprises Ltd | Oral meclizine aqueous formulations with taste flavoring agent |
| CN101905027A (zh) * | 2010-07-27 | 2010-12-08 | 北京华禧联合科技发展有限公司 | 含米格列奈钙和环糊精的口服药用组合物 |
| AU2011302293B2 (en) | 2010-09-13 | 2015-11-26 | Bev-Rx, Inc. | Aqueous drug delivery system comprising off - flavor masking agent |
| US9945862B2 (en) | 2011-06-03 | 2018-04-17 | Eisai R&D Management Co., Ltd. | Biomarkers for predicting and assessing responsiveness of thyroid and kidney cancer subjects to lenvatinib compounds |
| RU2589833C2 (ru) * | 2013-12-12 | 2016-07-10 | Общество С Ограниченной Ответственностью "Фарма Старт" | Твердая лекарственная форма препарата седативного и снотворного действия |
| DK3122330T3 (en) * | 2014-03-27 | 2018-10-22 | Ucb Farchim Sa | Pharmaceutical compositions comprising levocetirizine |
| IL302218B2 (en) | 2014-08-28 | 2024-10-01 | Eisai R&D Man Co Ltd | Methods for manufacturing high-purity lenvatinib and its derivatives |
| JP6792546B2 (ja) | 2015-02-25 | 2020-11-25 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | キノリン誘導体の苦味抑制方法 |
| AU2015384801B2 (en) | 2015-03-04 | 2022-01-06 | Eisai R&D Management Co., Ltd. | Combination of a PD-1 antagonist and a VEGFR/FGFR/RET tyrosine kinase inhibitor for treating cancer |
| EP3311841B1 (en) | 2015-06-16 | 2021-07-28 | PRISM BioLab Co., Ltd. | Anticancer agent |
| CN108135894B (zh) | 2015-08-20 | 2021-02-19 | 卫材R&D管理有限公司 | 肿瘤治疗剂 |
| RU2750539C2 (ru) | 2017-02-08 | 2021-06-29 | Эйсай Ар Энд Ди Менеджмент Ко., Лтд. | Фармацевтическая композиция для лечения опухоли |
| AU2018269996A1 (en) | 2017-05-16 | 2019-11-21 | Eisai R&D Management Co., Ltd. | Treatment of hepatocellular carcinoma |
| KR102110304B1 (ko) * | 2017-06-30 | 2020-05-14 | 한미약품 주식회사 | 레보세티리진 및 몬테루카스트를 포함하는 안정성 및 복약순응도가 향상된 복합 츄어블정 및 그 제조방법 |
| EP4099977A1 (en) * | 2020-02-03 | 2022-12-14 | Johnson & Johnson Consumer Inc. | A single layer chewable tablet comprising cetirizine |
| WO2022106923A1 (en) | 2020-11-18 | 2022-05-27 | BioPharma Synergies, S. L. | Orodispersible powder composition comprising an antihistamine compound |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK154078C (da) * | 1981-02-06 | 1989-05-22 | Ucb Sa | Analogifremgangsmaade til fremstilling af 2-(2-(4-(diphenyl-methyl)-1-piperazinyl)ethoxy)-acetamider eller syreadditionssalte heraf |
| JPS58177949A (ja) * | 1982-04-12 | 1983-10-18 | Takeda Chem Ind Ltd | ランカシジン群抗生物質包接化合物 |
| JPS60204712A (ja) * | 1984-03-29 | 1985-10-16 | Ss Pharmaceut Co Ltd | 塩酸メクリジンの安定化液状組成物 |
| JPS63243031A (ja) † | 1987-03-28 | 1988-10-07 | Tokyo Tanabe Co Ltd | 胆汁酸の固形製剤 |
| FR2647343B1 (fr) * | 1989-05-24 | 1994-05-06 | Rhone Poulenc Sante | Nouvelle forme pharmaceutique poreuse et sa preparation |
| US5206025A (en) * | 1989-05-24 | 1993-04-27 | Rhone-Poulenc Sante | Porous pharmaceutical form and its preparation |
| CA2145410A1 (en) † | 1992-09-24 | 1994-03-31 | Nancy M. Gray | Compositions for treating allergic disorders using (-) cetirizine |
| TW401300B (en) * | 1992-12-25 | 2000-08-11 | Senju Pharma Co | Antiallergic composition for ophthalmic or nasal use |
| ES2166811T3 (es) * | 1993-12-01 | 2002-05-01 | Byk Gulden Lomberg Chem Fab | Amino-alquil-amino-piridinas sustituidas. |
| US5866179A (en) | 1996-05-03 | 1999-02-02 | Avant-Garde Technologies & Products S.A. | Medicated chewing gum and a process for preparation thereof |
| GB0028575D0 (en) * | 2000-11-23 | 2001-01-10 | Elan Corp Plc | Oral pharmaceutical compositions containing cyclodextrins |
| CA2574602A1 (en) * | 2004-07-22 | 2006-02-02 | Pfizer Products Inc. | Taste masking formulation comprising the drug in a dissolution-retarded form and/or cyclodextrin in a dissolution-enhanced form |
-
1997
- 1997-07-03 BE BE9700572A patent/BE1011251A3/fr not_active IP Right Cessation
-
1998
- 1998-07-02 IL IL13339798A patent/IL133397A/xx not_active IP Right Cessation
- 1998-07-02 AU AU82015/98A patent/AU727140B2/en not_active Expired
- 1998-07-02 RU RU99128065/14A patent/RU2192863C2/ru not_active IP Right Cessation
- 1998-07-02 PL PL337794A patent/PL192348B1/pl not_active IP Right Cessation
- 1998-07-02 JP JP50598499A patent/JP2002508773A/ja not_active Withdrawn
- 1998-07-02 DE DE69808297T patent/DE69808297T3/de not_active Expired - Lifetime
- 1998-07-02 CN CNB988067641A patent/CN1150900C/zh not_active Expired - Lifetime
- 1998-07-02 ES ES98931849T patent/ES2184293T5/es not_active Expired - Lifetime
- 1998-07-02 CA CA002294783A patent/CA2294783C/fr not_active Expired - Fee Related
- 1998-07-02 WO PCT/BE1998/000100 patent/WO1999001133A1/fr not_active Ceased
- 1998-07-02 DK DK98931849T patent/DK0994710T4/da active
- 1998-07-02 AT AT98931849T patent/ATE224717T1/de active
- 1998-07-02 KR KR1019997012573A patent/KR100551510B1/ko not_active Expired - Fee Related
- 1998-07-02 NZ NZ501820A patent/NZ501820A/xx unknown
- 1998-07-02 BR BR9810495-0A patent/BR9810495A/pt not_active Application Discontinuation
- 1998-07-02 PT PT98931849T patent/PT994710E/pt unknown
- 1998-07-02 EP EP98931849A patent/EP0994710B2/fr not_active Expired - Lifetime
- 1998-07-02 US US09/446,735 patent/US6455533B1/en not_active Expired - Lifetime
- 1998-07-02 ID IDW991729A patent/ID23806A/id unknown
-
2007
- 2007-01-12 JP JP2007004722A patent/JP2007091760A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE69808297D1 (de) | 2002-10-31 |
| AU727140B2 (en) | 2000-12-07 |
| KR100551510B1 (ko) | 2006-02-13 |
| PT994710E (pt) | 2003-02-28 |
| NZ501820A (en) | 2000-10-27 |
| CA2294783A1 (fr) | 1999-01-14 |
| EP0994710A1 (fr) | 2000-04-26 |
| US20020032217A1 (en) | 2002-03-14 |
| JP2002508773A (ja) | 2002-03-19 |
| ES2184293T5 (es) | 2006-01-16 |
| DK0994710T4 (da) | 2005-10-17 |
| JP2007091760A (ja) | 2007-04-12 |
| PL337794A1 (en) | 2000-09-11 |
| ID23806A (id) | 2000-05-11 |
| DE69808297T3 (de) | 2006-01-19 |
| AU8201598A (en) | 1999-01-25 |
| US6455533B1 (en) | 2002-09-24 |
| CN1261799A (zh) | 2000-08-02 |
| KR20010014398A (ko) | 2001-02-26 |
| DK0994710T3 (da) | 2003-01-20 |
| EP0994710B1 (fr) | 2002-09-25 |
| IL133397A0 (en) | 2001-04-30 |
| PL192348B1 (pl) | 2006-10-31 |
| BE1011251A3 (fr) | 1999-06-01 |
| CN1150900C (zh) | 2004-05-26 |
| BR9810495A (pt) | 2000-09-12 |
| WO1999001133A1 (fr) | 1999-01-14 |
| ES2184293T3 (es) | 2003-04-01 |
| IL133397A (en) | 2005-07-25 |
| RU2192863C2 (ru) | 2002-11-20 |
| EP0994710B2 (fr) | 2005-09-21 |
| ATE224717T1 (de) | 2002-10-15 |
| DE69808297T2 (de) | 2003-04-17 |
| HK1029060A1 (en) | 2001-03-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20150702 |