CA2549572A1 - Compositions pharmaceutiques au gout masque comportant une medicament amer et un polymere sensible au ph - Google Patents
Compositions pharmaceutiques au gout masque comportant une medicament amer et un polymere sensible au ph Download PDFInfo
- Publication number
- CA2549572A1 CA2549572A1 CA002549572A CA2549572A CA2549572A1 CA 2549572 A1 CA2549572 A1 CA 2549572A1 CA 002549572 A CA002549572 A CA 002549572A CA 2549572 A CA2549572 A CA 2549572A CA 2549572 A1 CA2549572 A1 CA 2549572A1
- Authority
- CA
- Canada
- Prior art keywords
- drug
- methacrylate
- composition
- polymer
- acrylate
- 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.)
- Abandoned
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- 239000003814 drug Substances 0.000 title claims abstract description 203
- 229940079593 drug Drugs 0.000 title claims abstract description 197
- 229920000642 polymer Polymers 0.000 title claims abstract description 164
- 235000019640 taste Nutrition 0.000 title claims abstract description 115
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 27
- 239000007788 liquid Substances 0.000 claims abstract description 25
- 210000002784 stomach Anatomy 0.000 claims abstract description 17
- 230000002378 acidificating effect Effects 0.000 claims abstract description 13
- 210000003296 saliva Anatomy 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims description 115
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 84
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 78
- 238000000034 method Methods 0.000 claims description 63
- 239000000178 monomer Substances 0.000 claims description 55
- -1 amino alkyl acrylic acid Chemical compound 0.000 claims description 34
- 238000000576 coating method Methods 0.000 claims description 32
- 239000011859 microparticle Substances 0.000 claims description 31
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 30
- 239000011248 coating agent Substances 0.000 claims description 29
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 claims description 26
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical group COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 21
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 claims description 20
- 239000000725 suspension Substances 0.000 claims description 20
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 19
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 19
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 18
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 17
- 239000007910 chewable tablet Substances 0.000 claims description 17
- 229960000590 celecoxib Drugs 0.000 claims description 16
- RZEKVGVHFLEQIL-UHFFFAOYSA-N celecoxib Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 RZEKVGVHFLEQIL-UHFFFAOYSA-N 0.000 claims description 16
- 239000007921 spray Substances 0.000 claims description 16
- 239000006188 syrup Substances 0.000 claims description 16
- 235000020357 syrup Nutrition 0.000 claims description 16
- 229960002626 clarithromycin Drugs 0.000 claims description 15
- AGOYDEPGAOXOCK-KCBOHYOISA-N clarithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@](C)([C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)OC)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 AGOYDEPGAOXOCK-KCBOHYOISA-N 0.000 claims description 15
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical group CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 14
- 229960001668 cefuroxime Drugs 0.000 claims description 14
- JFPVXVDWJQMJEE-IZRZKJBUSA-N cefuroxime Chemical compound N([C@@H]1C(N2C(=C(COC(N)=O)CS[C@@H]21)C(O)=O)=O)C(=O)\C(=N/OC)C1=CC=CO1 JFPVXVDWJQMJEE-IZRZKJBUSA-N 0.000 claims description 14
- 239000000796 flavoring agent Substances 0.000 claims description 14
- 239000011159 matrix material Substances 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 14
- 229960003405 ciprofloxacin Drugs 0.000 claims description 13
- 239000002552 dosage form Substances 0.000 claims description 13
- 238000004945 emulsification Methods 0.000 claims description 13
- 239000007789 gas Substances 0.000 claims description 13
- 125000005397 methacrylic acid ester group Chemical group 0.000 claims description 13
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims description 12
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 claims description 12
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical group CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 12
- 235000015165 citric acid Nutrition 0.000 claims description 12
- 238000001035 drying Methods 0.000 claims description 12
- 239000006186 oral dosage form Substances 0.000 claims description 12
- 229930006000 Sucrose Natural products 0.000 claims description 11
- 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 claims description 11
- 235000019634 flavors Nutrition 0.000 claims description 11
- 239000003960 organic solvent Substances 0.000 claims description 11
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 11
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 11
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 11
- 239000005720 sucrose Substances 0.000 claims description 11
- 229930186147 Cephalosporin Natural products 0.000 claims description 10
- 229940124587 cephalosporin Drugs 0.000 claims description 10
- 150000001780 cephalosporins Chemical class 0.000 claims description 10
- 229960003276 erythromycin Drugs 0.000 claims description 10
- 230000002209 hydrophobic effect Effects 0.000 claims description 10
- 238000001694 spray drying Methods 0.000 claims description 10
- 238000003860 storage Methods 0.000 claims description 10
- XUBOMFCQGDBHNK-JTQLQIEISA-N (S)-gatifloxacin Chemical compound FC1=CC(C(C(C(O)=O)=CN2C3CC3)=O)=C2C(OC)=C1N1CCN[C@@H](C)C1 XUBOMFCQGDBHNK-JTQLQIEISA-N 0.000 claims description 9
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 claims description 9
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims description 9
- 229960003923 gatifloxacin Drugs 0.000 claims description 9
- 229960001680 ibuprofen Drugs 0.000 claims description 9
- QHVBLSNVXDSMEB-UHFFFAOYSA-N 2-(diethylamino)ethyl prop-2-enoate Chemical compound CCN(CC)CCOC(=O)C=C QHVBLSNVXDSMEB-UHFFFAOYSA-N 0.000 claims description 8
- MJKIORXNEJFOPX-UHFFFAOYSA-N 2-prop-1-en-2-ylpyridine Chemical compound CC(=C)C1=CC=CC=N1 MJKIORXNEJFOPX-UHFFFAOYSA-N 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- MKXZASYAUGDDCJ-SZMVWBNQSA-N LSM-2525 Chemical compound C1CCC[C@H]2[C@@]3([H])N(C)CC[C@]21C1=CC(OC)=CC=C1C3 MKXZASYAUGDDCJ-SZMVWBNQSA-N 0.000 claims description 8
- 229960001985 dextromethorphan Drugs 0.000 claims description 8
- 239000007919 dispersible tablet Substances 0.000 claims description 8
- 239000006185 dispersion Substances 0.000 claims description 8
- 229960004945 etoricoxib Drugs 0.000 claims description 8
- MNJVRJDLRVPLFE-UHFFFAOYSA-N etoricoxib Chemical compound C1=NC(C)=CC=C1C1=NC=C(Cl)C=C1C1=CC=C(S(C)(=O)=O)C=C1 MNJVRJDLRVPLFE-UHFFFAOYSA-N 0.000 claims description 8
- GSDSWSVVBLHKDQ-UHFFFAOYSA-N 9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid Chemical compound FC1=CC(C(C(C(O)=O)=C2)=O)=C3N2C(C)COC3=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-UHFFFAOYSA-N 0.000 claims description 7
- GSDSWSVVBLHKDQ-JTQLQIEISA-N Levofloxacin Chemical compound C([C@@H](N1C2=C(C(C(C(O)=O)=C1)=O)C=C1F)C)OC2=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-JTQLQIEISA-N 0.000 claims description 7
- 229940111134 coxibs Drugs 0.000 claims description 7
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 claims description 7
- 229960003376 levofloxacin Drugs 0.000 claims description 7
- 239000003120 macrolide antibiotic agent Substances 0.000 claims description 7
- 229960001699 ofloxacin Drugs 0.000 claims description 7
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 6
- SPFYMRJSYKOXGV-UHFFFAOYSA-N Baytril Chemical compound C1CN(CC)CCN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 SPFYMRJSYKOXGV-UHFFFAOYSA-N 0.000 claims description 6
- DBAKFASWICGISY-BTJKTKAUSA-N Chlorpheniramine maleate Chemical compound OC(=O)\C=C/C(O)=O.C=1C=CC=NC=1C(CCN(C)C)C1=CC=C(Cl)C=C1 DBAKFASWICGISY-BTJKTKAUSA-N 0.000 claims description 6
- 229940035676 analgesics Drugs 0.000 claims description 6
- 239000000730 antalgic agent Substances 0.000 claims description 6
- 230000001387 anti-histamine Effects 0.000 claims description 6
- 229940124599 anti-inflammatory drug Drugs 0.000 claims description 6
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 6
- 229960004099 azithromycin Drugs 0.000 claims description 6
- MQTOSJVFKKJCRP-BICOPXKESA-N azithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)N(C)C[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 MQTOSJVFKKJCRP-BICOPXKESA-N 0.000 claims description 6
- 229960004841 cefadroxil Drugs 0.000 claims description 6
- NBFNMSULHIODTC-CYJZLJNKSA-N cefadroxil monohydrate Chemical compound O.C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=C(O)C=C1 NBFNMSULHIODTC-CYJZLJNKSA-N 0.000 claims description 6
- 229940106164 cephalexin Drugs 0.000 claims description 6
- ZAIPMKNFIOOWCQ-UEKVPHQBSA-N cephalexin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=CC=C1 ZAIPMKNFIOOWCQ-UEKVPHQBSA-N 0.000 claims description 6
- 229940046978 chlorpheniramine maleate Drugs 0.000 claims description 6
- 229960001193 diclofenac sodium Drugs 0.000 claims description 6
- 229960000740 enrofloxacin Drugs 0.000 claims description 6
- 239000012530 fluid Substances 0.000 claims description 6
- 229960003907 linezolid Drugs 0.000 claims description 6
- TYZROVQLWOKYKF-ZDUSSCGKSA-N linezolid Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCOCC1 TYZROVQLWOKYKF-ZDUSSCGKSA-N 0.000 claims description 6
- 229940057995 liquid paraffin Drugs 0.000 claims description 6
- OGJPXUAPXNRGGI-UHFFFAOYSA-N norfloxacin Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 OGJPXUAPXNRGGI-UHFFFAOYSA-N 0.000 claims description 6
- 229960001180 norfloxacin Drugs 0.000 claims description 6
- 229950000033 proxetil Drugs 0.000 claims description 6
- JGMJQSFLQWGYMQ-UHFFFAOYSA-M sodium;2,6-dichloro-n-phenylaniline;acetate Chemical compound [Na+].CC([O-])=O.ClC1=CC=CC(Cl)=C1NC1=CC=CC=C1 JGMJQSFLQWGYMQ-UHFFFAOYSA-M 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- ZGABHKCDMREPPH-UHFFFAOYSA-N 1-phenylbut-1-en-2-amine Chemical class CCC(N)=CC1=CC=CC=C1 ZGABHKCDMREPPH-UHFFFAOYSA-N 0.000 claims description 4
- SJIXRGNQPBQWMK-UHFFFAOYSA-N 2-(diethylamino)ethyl 2-methylprop-2-enoate Chemical compound CCN(CC)CCOC(=O)C(C)=C SJIXRGNQPBQWMK-UHFFFAOYSA-N 0.000 claims description 4
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 claims description 4
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 4
- WVNIWWGCVMYYJZ-UHFFFAOYSA-N 2-ethenyl-4-methylpyridine Chemical compound CC1=CC=NC(C=C)=C1 WVNIWWGCVMYYJZ-UHFFFAOYSA-N 0.000 claims description 4
- XUGNJOCQALIQFG-UHFFFAOYSA-N 2-ethenylquinoline Chemical class C1=CC=CC2=NC(C=C)=CC=C21 XUGNJOCQALIQFG-UHFFFAOYSA-N 0.000 claims description 4
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical group CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 claims description 4
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 4
- DPZYLEIWHTWHCU-UHFFFAOYSA-N 3-ethenylpyridine Chemical compound C=CC1=CC=CN=C1 DPZYLEIWHTWHCU-UHFFFAOYSA-N 0.000 claims description 4
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 claims description 4
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims description 4
- VJOWMORERYNYON-UHFFFAOYSA-N 5-ethenyl-2-methylpyridine Chemical compound CC1=CC=C(C=C)C=N1 VJOWMORERYNYON-UHFFFAOYSA-N 0.000 claims description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 4
- PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 claims description 4
- 239000007900 aqueous suspension Substances 0.000 claims description 4
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical group CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 claims description 4
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical group CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 claims description 4
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 claims description 4
- UFPFGARGLHWVFO-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate;piperidine Chemical compound C1CCNCC1.CCOC(=O)C(C)=C UFPFGARGLHWVFO-UHFFFAOYSA-N 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 235000003599 food sweetener Nutrition 0.000 claims description 4
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 claims description 4
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- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical group CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 claims description 4
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical group C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 claims description 4
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical group CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 claims description 4
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- 239000000605 aspartame Substances 0.000 claims description 3
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- 238000000975 co-precipitation Methods 0.000 claims description 3
- 235000013355 food flavoring agent Nutrition 0.000 claims description 3
- 239000007970 homogeneous dispersion Substances 0.000 claims description 3
- 229940065472 octyl acrylate Drugs 0.000 claims description 3
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 claims description 3
- 239000012074 organic phase Substances 0.000 claims description 3
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- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical class [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 2
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- 229910052786 argon Inorganic materials 0.000 claims description 2
- 239000001569 carbon dioxide Substances 0.000 claims description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 235000019204 saccharin Nutrition 0.000 claims description 2
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 claims description 2
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- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 claims description 2
- 235000002906 tartaric acid Nutrition 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 1
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- 230000000873 masking effect Effects 0.000 abstract description 43
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- KEJCWVGMRLCZQQ-YJBYXUATSA-N Cefuroxime axetil Chemical compound N([C@@H]1C(N2C(=C(COC(N)=O)CS[C@@H]21)C(=O)OC(C)OC(C)=O)=O)C(=O)\C(=N/OC)C1=CC=CO1 KEJCWVGMRLCZQQ-YJBYXUATSA-N 0.000 description 51
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- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229960005489 paracetamol Drugs 0.000 description 1
- 239000013618 particulate matter Substances 0.000 description 1
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- 239000007971 pharmaceutical suspension Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
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- 229960002796 polystyrene sulfonate Drugs 0.000 description 1
- 239000011970 polystyrene sulfonate Substances 0.000 description 1
- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 235000019423 pullulan Nutrition 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- VMXUWOKSQNHOCA-LCYFTJDESA-N ranitidine Chemical compound [O-][N+](=O)/C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-LCYFTJDESA-N 0.000 description 1
- 229960000620 ranitidine Drugs 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- DZZWHBIBMUVIIW-DTORHVGOSA-N sparfloxacin Chemical compound C1[C@@H](C)N[C@@H](C)CN1C1=C(F)C(N)=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F DZZWHBIBMUVIIW-DTORHVGOSA-N 0.000 description 1
- 229960004954 sparfloxacin Drugs 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 210000002438 upper gastrointestinal tract Anatomy 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 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
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1635—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
Landscapes
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
La présente invention a trait à des compositions pharmaceutiques comportant des polymères sensible au pH utilisés pour masquer le goût de médicaments très amers. Le polymère sensible au pH agit comme un enrobage entérique inverse, qui est soluble dans la plage de pH acide comprise entre 1,0 et 3,0 présente dans l'estomac mais est insoluble dans la plage de pH comprise entre 3,5 et 7 assurant ainsi l'inhibition de la libération du médicament amer au niveau du pH de la salive et également au niveau du pH du milieu de reconstitution dans le cas des liquides buccaux.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/IN2003/000392 WO2005055987A1 (fr) | 2003-12-15 | 2003-12-15 | Compositions pharmaceutiques au gout masque comportant une medicament amer et un polymere sensible au ph |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2549572A1 true CA2549572A1 (fr) | 2005-06-23 |
Family
ID=34674529
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002549572A Abandoned CA2549572A1 (fr) | 2003-12-15 | 2003-12-15 | Compositions pharmaceutiques au gout masque comportant une medicament amer et un polymere sensible au ph |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP1694302A1 (fr) |
| JP (1) | JP2007518670A (fr) |
| CN (1) | CN1878539B (fr) |
| AU (1) | AU2003292509B2 (fr) |
| CA (1) | CA2549572A1 (fr) |
| WO (1) | WO2005055987A1 (fr) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2003288707B2 (en) * | 2003-12-15 | 2007-08-02 | Council Of Scientific & Industrial Research | Taste masked pharmaceutical composition comprising pH sensitive polymer |
| JP2009035505A (ja) * | 2007-08-01 | 2009-02-19 | Takada Seiyaku Kk | レボフロキサシン錠剤 |
| JP5563841B2 (ja) * | 2010-02-05 | 2014-07-30 | 沢井製薬株式会社 | 薬物の不快な味をマスキングした経口医薬組成物 |
| JP5915014B2 (ja) * | 2010-07-30 | 2016-05-11 | 大正製薬株式会社 | 内服液剤 |
| CN102188406B (zh) * | 2011-05-12 | 2015-02-25 | 黑龙江大学 | 盐酸左氧氟沙星掩味微胶囊的生产方法 |
| CN103501768B (zh) | 2011-06-17 | 2016-11-09 | 赢创罗姆有限公司 | 具有抗乙醇影响抗性的抗胃酸的药物或营养组合物 |
| CN102344520B (zh) * | 2011-07-12 | 2015-04-22 | 华东理工大学 | 两种pH敏感再生型聚合物、其制备方法和形成的再生型两水相体系及应用 |
| CN102302472B (zh) * | 2011-09-08 | 2012-08-01 | 河南迪冉生物科技有限公司 | 恩诺沙星微囊及其制备方法 |
| CN103191680B (zh) * | 2013-03-26 | 2016-02-24 | 厦门大学 | 一种pH敏感的复合中空微球及其制备方法 |
| MA41107B1 (fr) | 2014-12-05 | 2025-01-31 | Aragon Pharmaceuticals, Inc. | Compositions anti-cancéreuses |
| LT3226843T (lt) | 2014-12-05 | 2021-08-10 | Aragon Pharmaceuticals, Inc. | Priešvėžinės kompozicijos |
| PT3226842T (pt) * | 2014-12-05 | 2020-12-23 | Aragon Pharmaceuticals Inc | Composições anticancerígenas |
| US11576941B2 (en) | 2016-06-21 | 2023-02-14 | Laila Nutraceuticals | Taste masking formulation for bitter natural compounds |
| US11707499B2 (en) * | 2016-09-08 | 2023-07-25 | Laila Nutraceuticals | Odor masking formulations for natural compounds |
| CN114209661B (zh) * | 2022-02-21 | 2022-04-29 | 北京罗诺强施医药技术研发中心有限公司 | 呈细粒形式的固体药物组合物 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS528795B2 (fr) * | 1971-12-30 | 1977-03-11 | ||
| JPS5432436B2 (fr) * | 1972-05-13 | 1979-10-15 | ||
| US4389330A (en) * | 1980-10-06 | 1983-06-21 | Stolle Research And Development Corporation | Microencapsulation process |
| FR2514261B1 (fr) * | 1981-10-08 | 1986-08-22 | Aec Chim Organ Biolog | Nouvelle composition pour l'enrobage des aliments et des medicaments et granules ainsi enrobes |
| US5286489A (en) * | 1985-08-26 | 1994-02-15 | The Procter & Gamble Company | Taste masking compositions |
| US4760093A (en) | 1986-10-21 | 1988-07-26 | American Home Products Corporation (Del.) | Spray dried acetaminophen |
| US5445830A (en) * | 1989-07-25 | 1995-08-29 | Otsuka Pharmaceutical Co., Ltd. | Highly absorbable pharmaceutical composition |
| CN1023766C (zh) * | 1990-04-09 | 1994-02-16 | 沈阳药学院 | 制备无味药物微囊的喷雾干燥工艺 |
| GB9015822D0 (en) * | 1990-07-18 | 1990-09-05 | Beecham Group Plc | Compositions |
| US5851538A (en) * | 1995-12-29 | 1998-12-22 | Advanced Polymer Systems, Inc. | Retinoid formulations in porous microspheres for reduced irritation and enhanced stability |
| JP2001518490A (ja) * | 1997-10-03 | 2001-10-16 | エラン コーポレーシヨン ピーエルシー | 味遮蔽された製剤 |
| DE19918435A1 (de) * | 1998-07-23 | 2000-01-27 | Roehm Gmbh | Überzugs- und Bindemittel für orale oder dermale Arzneiformen |
| BR0011345A (pt) * | 1999-06-11 | 2002-04-23 | Ranbaxy Lab Ltd | Composições com sabor mascarado |
| ITMI20012572A1 (it) * | 2001-12-06 | 2003-06-06 | Istituto Biochimico Italiano | Microgranuli di acido ursodesossicolico |
| AU2003288707B2 (en) * | 2003-12-15 | 2007-08-02 | Council Of Scientific & Industrial Research | Taste masked pharmaceutical composition comprising pH sensitive polymer |
-
2003
- 2003-12-15 WO PCT/IN2003/000392 patent/WO2005055987A1/fr not_active Ceased
- 2003-12-15 JP JP2005511660A patent/JP2007518670A/ja active Pending
- 2003-12-15 CA CA002549572A patent/CA2549572A1/fr not_active Abandoned
- 2003-12-15 CN CN200380110830XA patent/CN1878539B/zh not_active Expired - Fee Related
- 2003-12-15 AU AU2003292509A patent/AU2003292509B2/en not_active Ceased
- 2003-12-15 EP EP03768091A patent/EP1694302A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| AU2003292509A1 (en) | 2005-06-29 |
| JP2007518670A (ja) | 2007-07-12 |
| WO2005055987A1 (fr) | 2005-06-23 |
| CN1878539B (zh) | 2010-06-23 |
| CN1878539A (zh) | 2006-12-13 |
| AU2003292509B9 (en) | 2005-06-29 |
| EP1694302A1 (fr) | 2006-08-30 |
| AU2003292509B2 (en) | 2007-08-02 |
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