DE69808297T3 - Oral anzuwendende arzneizubereitungen enthaltend eine benzhydrylpiperazine und eine zyklodextrin - Google Patents
Oral anzuwendende arzneizubereitungen enthaltend eine benzhydrylpiperazine und eine zyklodextrin Download PDFInfo
- Publication number
- DE69808297T3 DE69808297T3 DE69808297T DE69808297T DE69808297T3 DE 69808297 T3 DE69808297 T3 DE 69808297T3 DE 69808297 T DE69808297 T DE 69808297T DE 69808297 T DE69808297 T DE 69808297T DE 69808297 T3 DE69808297 T3 DE 69808297T3
- Authority
- DE
- Germany
- Prior art keywords
- cyclodextrin
- cetirizine
- active ingredient
- pharmaceutical composition
- benzhydrylpiperazine
- 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
- 229920000858 Cyclodextrin Polymers 0.000 title claims abstract description 55
- 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 23
- NWVNXDKZIQLBNM-UHFFFAOYSA-N diphenylmethylpiperazine Chemical compound C1CNCCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 NWVNXDKZIQLBNM-UHFFFAOYSA-N 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
- 150000008640 diphenylmethylpiperazines Chemical class 0.000 claims abstract description 9
- 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 34
- 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 27
- 239000004480 active ingredient Substances 0.000 claims description 15
- 239000008187 granular material Substances 0.000 claims description 5
- 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 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000006188 syrup Substances 0.000 claims description 5
- 235000020357 syrup Nutrition 0.000 claims description 5
- 239000007910 chewable tablet Substances 0.000 claims description 4
- 229960000930 hydroxyzine Drugs 0.000 claims description 4
- 239000006190 sub-lingual tablet Substances 0.000 claims description 4
- 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
- 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 3
- 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 description 2
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 claims description 2
- 229960001705 buclizine Drugs 0.000 claims description 2
- 229950003420 efletirizine Drugs 0.000 claims description 2
- 229960001474 meclozine Drugs 0.000 claims description 2
- ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 0.000 claims description 2
- 229940068682 chewable tablet Drugs 0.000 claims 1
- 229940098466 sublingual tablet Drugs 0.000 claims 1
- 239000013543 active substance Substances 0.000 abstract description 5
- 239000001116 FEMA 4028 Substances 0.000 description 25
- 235000011175 beta-cyclodextrine Nutrition 0.000 description 25
- 229960004853 betadex Drugs 0.000 description 25
- 239000000243 solution Substances 0.000 description 19
- 239000000203 mixture Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 8
- 230000000873 masking effect Effects 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 235000019640 taste Nutrition 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 235000019658 bitter taste Nutrition 0.000 description 6
- 239000002696 acid base indicator Substances 0.000 description 4
- -1 alkyl sulphate Chemical compound 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000010668 complexation reaction Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000796 flavoring agent Substances 0.000 description 4
- 235000019634 flavors Nutrition 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 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-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
- 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
- 229940097362 cyclodextrins Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- 238000001228 spectrum Methods 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
- 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 2
- 229930195725 Mannitol 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
- 238000000862 absorption spectrum Methods 0.000 description 2
- 239000000619 acesulfame-K Substances 0.000 description 2
- 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 2
- 239000000654 additive Substances 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 230000001387 anti-histamine Effects 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- 229960001681 croscarmellose sodium Drugs 0.000 description 2
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 230000037406 food intake Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 239000000594 mannitol Substances 0.000 description 2
- 235000010355 mannitol Nutrition 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
- 238000002156 mixing Methods 0.000 description 2
- 150000003077 polyols Chemical class 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
- 239000007787 solid Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 2
- GBBSUAFBMRNDJC-MRXNPFEDSA-N (5R)-zopiclone Chemical compound C1CN(C)CCN1C(=O)O[C@@H]1C2=NC=CN=C2C(=O)N1C1=CC=C(Cl)C=N1 GBBSUAFBMRNDJC-MRXNPFEDSA-N 0.000 description 1
- UZKBSZSTDQSMDR-UHFFFAOYSA-N 1-[(4-chlorophenyl)-phenylmethyl]piperazine Chemical class 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
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 description 1
- 244000303040 Glycyrrhiza glabra Species 0.000 description 1
- 235000006200 Glycyrrhiza glabra Nutrition 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 235000019501 Lemon oil Nutrition 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
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- HVWGGPRWKSHASF-UHFFFAOYSA-N Sulfuric acid, monooctadecyl ester Chemical compound CCCCCCCCCCCCCCCCCCOS(O)(=O)=O HVWGGPRWKSHASF-UHFFFAOYSA-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
- 238000002835 absorbance Methods 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 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
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 239000000599 controlled substance Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000002242 deionisation method Methods 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 239000007941 film coated tablet Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- LPLVUJXQOOQHMX-QWBHMCJMSA-N glycyrrhizinic acid Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@@H]1C([C@H]2[C@]([C@@H]3[C@@]([C@@]4(CC[C@@]5(C)CC[C@@](C)(C[C@H]5C4=CC3=O)C(O)=O)C)(C)CC2)(C)CC1)(C)C)C(O)=O)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O LPLVUJXQOOQHMX-QWBHMCJMSA-N 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
- 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
- 239000010501 lemon oil Substances 0.000 description 1
- 235000011477 liquorice Nutrition 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 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
- 230000002980 postoperative effect Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 230000009747 swallowing Effects 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 230000001225 therapeutic 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
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 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
- 235000005282 vitamin D3 Nutrition 0.000 description 1
- 239000011647 vitamin D3 Substances 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 229940021056 vitamin d3 Drugs 0.000 description 1
- 229960000820 zopiclone Drugs 0.000 description 1
Classifications
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- 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
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- 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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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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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- A—HUMAN NECESSITIES
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- 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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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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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
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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
- A61P25/18—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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
-
- 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)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nanotechnology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Medical Informatics (AREA)
- Molecular Biology (AREA)
- Pulmonology (AREA)
- Biophysics (AREA)
- Biotechnology (AREA)
- General Engineering & Computer Science (AREA)
- Physiology (AREA)
- Nutrition Science (AREA)
- Crystallography & Structural Chemistry (AREA)
- Immunology (AREA)
- Zoology (AREA)
- Anesthesiology (AREA)
- Psychiatry (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE9700572 | 1997-07-03 | ||
| BE9700572A BE1011251A3 (fr) | 1997-07-03 | 1997-07-03 | Compositions pharmaceutiques administrables par voie orale, comprenant une substance active et une cyclodextrine. |
| 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 (3)
| Publication Number | Publication Date |
|---|---|
| DE69808297D1 DE69808297D1 (de) | 2002-10-31 |
| DE69808297T2 DE69808297T2 (de) | 2003-04-17 |
| DE69808297T3 true DE69808297T3 (de) | 2006-01-19 |
Family
ID=3890611
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69808297T Expired - Lifetime DE69808297T3 (de) | 1997-07-03 | 1998-07-02 | Oral anzuwendende arzneizubereitungen enthaltend eine benzhydrylpiperazine und eine zyklodextrin |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US6455533B1 (https=) |
| EP (1) | EP0994710B2 (https=) |
| JP (2) | JP2002508773A (https=) |
| KR (1) | KR100551510B1 (https=) |
| CN (1) | CN1150900C (https=) |
| AT (1) | ATE224717T1 (https=) |
| AU (1) | AU727140B2 (https=) |
| BE (1) | BE1011251A3 (https=) |
| BR (1) | BR9810495A (https=) |
| CA (1) | CA2294783C (https=) |
| DE (1) | DE69808297T3 (https=) |
| DK (1) | DK0994710T4 (https=) |
| ES (1) | ES2184293T5 (https=) |
| ID (1) | ID23806A (https=) |
| IL (1) | IL133397A (https=) |
| NZ (1) | NZ501820A (https=) |
| PL (1) | PL192348B1 (https=) |
| PT (1) | PT994710E (https=) |
| RU (1) | RU2192863C2 (https=) |
| WO (1) | WO1999001133A1 (https=) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0028575D0 (en) * | 2000-11-23 | 2001-01-10 | Elan Corp Plc | Oral pharmaceutical compositions containing cyclodextrins |
| KR20030094244A (ko) * | 2001-02-05 | 2003-12-11 | 알.피.쉐러 테크놀러지즈 인코포레이티드 | 약리학적 활성제의 맛을 감소시키기 위한 방법 및 조성물 |
| PL212123B1 (pl) * | 2002-01-15 | 2012-08-31 | Ucb Farchim Sa | Doustna kompozycja farmaceutyczna |
| WO2003084511A1 (en) * | 2002-04-04 | 2003-10-16 | Pfizer Products Inc. | Palatable chewable tablet |
| EP1771161B1 (en) * | 2004-07-22 | 2010-04-21 | Bend Research, 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 |
| WO2007144902A1 (en) * | 2006-06-12 | 2007-12-21 | 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 |
| EP2178521B1 (en) * | 2007-07-11 | 2014-01-15 | 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 |
| EP2067469A1 (en) | 2007-11-06 | 2009-06-10 | Teva Pharmaceutical Industries Ltd. | Chewable formulations |
| CN102143737A (zh) * | 2008-09-05 | 2011-08-03 | 麦克内尔-Ppc股份有限公司 | 制备西替利嗪片剂的方法 |
| DK2468281T3 (en) | 2009-08-19 | 2016-03-21 | Eisai R&D Man Co Ltd | Quinolinderivatholdig pharmaceutical composition |
| WO2011110939A2 (en) * | 2010-03-11 | 2011-09-15 | Rubicon Research Private Limited | Pharmaceutical compositions of substituted benzhydrylpiperazines |
| HK1161509A2 (en) * | 2010-06-04 | 2012-07-27 | 全球药物科技有限公司 | 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 |
| WO2012037117A1 (en) | 2010-09-13 | 2012-03-22 | Bev-Rx, Inc. | Aqueous drug delivery system comprising off - flavor masking agent |
| JP6038128B2 (ja) | 2011-06-03 | 2016-12-07 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | レンバチニブ化合物に対する甲状腺癌対象及び腎臓癌対象の反応性を予測及び評価するためのバイオマーカー |
| RU2589833C2 (ru) * | 2013-12-12 | 2016-07-10 | Общество С Ограниченной Ответственностью "Фарма Старт" | Твердая лекарственная форма препарата седативного и снотворного действия |
| PT3122330T (pt) * | 2014-03-27 | 2018-11-13 | Ucb Farchim Sa | Composições farmacêuticas compreendendo levocetirizina |
| PT3524595T (pt) | 2014-08-28 | 2022-09-19 | Eisai R&D Man Co Ltd | Derivado de quinolina altamente puro e método para produção do mesmo |
| AU2016224583B2 (en) | 2015-02-25 | 2021-06-03 | Eisai R&D Management Co., Ltd. | Method for suppressing bitterness of quinoline derivative |
| KR102662228B1 (ko) | 2015-03-04 | 2024-05-02 | 머크 샤프 앤드 돔 코포레이션 | 암을 치료하기 위한 pd-1 길항제 및 vegfr/fgfr/ret 티로신 키나제 억제제의 조합 |
| BR112017027227B1 (pt) | 2015-06-16 | 2023-12-12 | Eisai R&D Management Co., Ltd | Agente anti-câncer |
| JP6553726B2 (ja) | 2015-08-20 | 2019-07-31 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 腫瘍治療剤 |
| JP6581320B2 (ja) | 2017-02-08 | 2019-09-25 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 腫瘍治療用医薬組成物 |
| EP3624800A4 (en) | 2017-05-16 | 2021-02-17 | 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 |
| AU2021217209A1 (en) * | 2020-02-03 | 2022-09-29 | Kenvue Brands Llc | A single layer chewable tablet comprising cetirizine |
| EP4247331B1 (en) | 2020-11-18 | 2025-10-08 | 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 |
| US5206025A (en) * | 1989-05-24 | 1993-04-27 | Rhone-Poulenc Sante | Porous pharmaceutical form and its preparation |
| FR2647343B1 (fr) | 1989-05-24 | 1994-05-06 | Rhone Poulenc Sante | Nouvelle forme pharmaceutique poreuse et sa preparation |
| DE10199031I2 (de) † | 1992-09-24 | 2004-09-23 | Sepracor Inc | Verwendung von (-) Cetrizin zur Behandlung allergischer Rhinitis und Asthma. |
| TW401300B (en) * | 1992-12-25 | 2000-08-11 | Senju Pharma Co | Antiallergic composition for ophthalmic or nasal use |
| JPH09509143A (ja) * | 1993-12-01 | 1997-09-16 | ビイク グルデン ロンベルク ヒェーミッシェ ファブリーク ゲゼルシャフト ミット ベシュレンクテル ハフツング | 置換アミノアルキルアミノピリジン |
| 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 |
| EP1771161B1 (en) * | 2004-07-22 | 2010-04-21 | Bend Research, 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 NZ NZ501820A patent/NZ501820A/xx unknown
- 1998-07-02 JP JP50598499A patent/JP2002508773A/ja not_active Withdrawn
- 1998-07-02 KR KR1019997012573A patent/KR100551510B1/ko not_active Expired - Fee Related
- 1998-07-02 AT AT98931849T patent/ATE224717T1/de active
- 1998-07-02 CA CA002294783A patent/CA2294783C/fr not_active Expired - Fee Related
- 1998-07-02 RU RU99128065/14A patent/RU2192863C2/ru not_active IP Right Cessation
- 1998-07-02 BR BR9810495-0A patent/BR9810495A/pt not_active Application Discontinuation
- 1998-07-02 DE DE69808297T patent/DE69808297T3/de not_active Expired - Lifetime
- 1998-07-02 ES ES98931849T patent/ES2184293T5/es not_active Expired - Lifetime
- 1998-07-02 IL IL13339798A patent/IL133397A/xx not_active IP Right Cessation
- 1998-07-02 WO PCT/BE1998/000100 patent/WO1999001133A1/fr not_active Ceased
- 1998-07-02 AU AU82015/98A patent/AU727140B2/en not_active Expired
- 1998-07-02 PT PT98931849T patent/PT994710E/pt unknown
- 1998-07-02 EP EP98931849A patent/EP0994710B2/fr not_active Expired - Lifetime
- 1998-07-02 PL PL337794A patent/PL192348B1/pl not_active IP Right Cessation
- 1998-07-02 CN CNB988067641A patent/CN1150900C/zh 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
- 1998-07-02 DK DK98931849T patent/DK0994710T4/da active
-
2007
- 2007-01-12 JP JP2007004722A patent/JP2007091760A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CN1150900C (zh) | 2004-05-26 |
| EP0994710A1 (fr) | 2000-04-26 |
| EP0994710B2 (fr) | 2005-09-21 |
| US6455533B1 (en) | 2002-09-24 |
| PT994710E (pt) | 2003-02-28 |
| DK0994710T4 (da) | 2005-10-17 |
| IL133397A (en) | 2005-07-25 |
| NZ501820A (en) | 2000-10-27 |
| CA2294783C (fr) | 2006-11-14 |
| PL192348B1 (pl) | 2006-10-31 |
| JP2002508773A (ja) | 2002-03-19 |
| ES2184293T3 (es) | 2003-04-01 |
| BR9810495A (pt) | 2000-09-12 |
| KR20010014398A (ko) | 2001-02-26 |
| EP0994710B1 (fr) | 2002-09-25 |
| DE69808297D1 (de) | 2002-10-31 |
| CA2294783A1 (fr) | 1999-01-14 |
| RU2192863C2 (ru) | 2002-11-20 |
| ES2184293T5 (es) | 2006-01-16 |
| HK1029060A1 (en) | 2001-03-23 |
| DK0994710T3 (da) | 2003-01-20 |
| WO1999001133A1 (fr) | 1999-01-14 |
| BE1011251A3 (fr) | 1999-06-01 |
| IL133397A0 (en) | 2001-04-30 |
| DE69808297T2 (de) | 2003-04-17 |
| ID23806A (id) | 2000-05-11 |
| ATE224717T1 (de) | 2002-10-15 |
| US20020032217A1 (en) | 2002-03-14 |
| JP2007091760A (ja) | 2007-04-12 |
| PL337794A1 (en) | 2000-09-11 |
| AU8201598A (en) | 1999-01-25 |
| AU727140B2 (en) | 2000-12-07 |
| CN1261799A (zh) | 2000-08-02 |
| KR100551510B1 (ko) | 2006-02-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8363 | Opposition against the patent | ||
| 8366 | Restricted maintained after opposition proceedings | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: UCB FARCHIM S.A., BULLE, CH |