SK15732003A3 - Farmaceutické kompozície zahrnujúce liečivá s nízkou rozpustnosťou a/alebo liečivá citlivé na kyselinu a neutralizované kyslé polyméry - Google Patents
Farmaceutické kompozície zahrnujúce liečivá s nízkou rozpustnosťou a/alebo liečivá citlivé na kyselinu a neutralizované kyslé polyméry Download PDFInfo
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- SK15732003A3 SK15732003A3 SK1573-2003A SK15732003A SK15732003A3 SK 15732003 A3 SK15732003 A3 SK 15732003A3 SK 15732003 A SK15732003 A SK 15732003A SK 15732003 A3 SK15732003 A3 SK 15732003A3
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- group
- phenyl
- carbon atoms
- amino
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- 239000003814 drug Substances 0.000 title claims abstract description 203
- 229940079593 drug Drugs 0.000 title claims abstract description 192
- 229920000642 polymer Polymers 0.000 title claims abstract description 121
- 230000002378 acidificating effect Effects 0.000 title claims abstract description 98
- 239000002253 acid Substances 0.000 title claims abstract description 48
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 25
- -1 3,5-bistrifluoromethylbenzyl Chemical group 0.000 claims description 254
- 239000000203 mixture Substances 0.000 claims description 76
- 239000006185 dispersion Substances 0.000 claims description 45
- 238000000034 method Methods 0.000 claims description 32
- 229920002301 cellulose acetate Polymers 0.000 claims description 28
- 230000001965 increasing effect Effects 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 20
- 239000000126 substance Substances 0.000 claims description 19
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 18
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 18
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 18
- 230000000052 comparative effect Effects 0.000 claims description 16
- 229920000639 hydroxypropylmethylcellulose acetate succinate Polymers 0.000 claims description 13
- 239000007787 solid Substances 0.000 claims description 13
- GAMPNQJDUFQVQO-UHFFFAOYSA-N acetic acid;phthalic acid Chemical compound CC(O)=O.OC(=O)C1=CC=CC=C1C(O)=O GAMPNQJDUFQVQO-UHFFFAOYSA-N 0.000 claims description 12
- 125000006626 methoxycarbonylamino group Chemical group 0.000 claims description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 10
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 10
- 125000004494 ethyl ester group Chemical group 0.000 claims description 10
- 125000005591 trimellitate group Chemical group 0.000 claims description 10
- 229920000623 Cellulose acetate phthalate Polymers 0.000 claims description 9
- 239000001913 cellulose Substances 0.000 claims description 9
- 235000010980 cellulose Nutrition 0.000 claims description 9
- 229920002678 cellulose Polymers 0.000 claims description 9
- 229940081734 cellulose acetate phthalate Drugs 0.000 claims description 9
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 9
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 9
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 9
- 229920001479 Hydroxyethyl methyl cellulose Polymers 0.000 claims description 7
- 230000003472 neutralizing effect Effects 0.000 claims description 7
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 6
- IYKJEILNJZQJPU-UHFFFAOYSA-N acetic acid;butanedioic acid Chemical compound CC(O)=O.OC(=O)CCC(O)=O IYKJEILNJZQJPU-UHFFFAOYSA-N 0.000 claims description 5
- 230000002708 enhancing effect Effects 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- IUGYQRQAERSCNH-UHFFFAOYSA-M pivalate Chemical compound CC(C)(C)C([O-])=O IUGYQRQAERSCNH-UHFFFAOYSA-M 0.000 claims description 5
- 229920000058 polyacrylate Polymers 0.000 claims description 5
- 229920002554 vinyl polymer Polymers 0.000 claims description 5
- PLEULVPCZZDBNB-UHFFFAOYSA-N acetic acid;butanedioic acid;phthalic acid Chemical compound CC(O)=O.OC(=O)CCC(O)=O.OC(=O)C1=CC=CC=C1C(O)=O PLEULVPCZZDBNB-UHFFFAOYSA-N 0.000 claims description 4
- 229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 claims description 4
- 229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 claims description 4
- 229920000609 methyl cellulose Polymers 0.000 claims description 4
- 235000010981 methylcellulose Nutrition 0.000 claims description 4
- 239000001923 methylcellulose Substances 0.000 claims description 4
- 238000006386 neutralization reaction Methods 0.000 claims description 4
- NMGBFVPQUCLJGM-UHFFFAOYSA-N 3-ethylphthalic acid Chemical compound CCC1=CC=CC(C(O)=O)=C1C(O)=O NMGBFVPQUCLJGM-UHFFFAOYSA-N 0.000 claims description 3
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical group CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 claims description 3
- FMTQGBMMIVVKSN-UHFFFAOYSA-N acetic acid;terephthalic acid Chemical compound CC(O)=O.OC(=O)C1=CC=C(C(O)=O)C=C1 FMTQGBMMIVVKSN-UHFFFAOYSA-N 0.000 claims description 3
- 239000000872 buffer Substances 0.000 claims description 3
- 229920006218 cellulose propionate Polymers 0.000 claims description 3
- 230000009477 glass transition Effects 0.000 claims description 3
- 230000006872 improvement Effects 0.000 claims description 3
- 229920000193 polymethacrylate Polymers 0.000 claims description 3
- OEXIDSNKGPWFGB-UHFFFAOYSA-N 2-ethyl-3-(3-hydroxypropyl)benzoic acid Chemical compound CCC1=C(CCCO)C=CC=C1C(O)=O OEXIDSNKGPWFGB-UHFFFAOYSA-N 0.000 claims description 2
- CGMMPMYKMDITEA-UHFFFAOYSA-N 2-ethylbenzoic acid Chemical compound CCC1=CC=CC=C1C(O)=O CGMMPMYKMDITEA-UHFFFAOYSA-N 0.000 claims description 2
- GZRANGIRVYGSDJ-UHFFFAOYSA-N acetic acid;pyridine-2,3-dicarboxylic acid Chemical compound CC(O)=O.OC(=O)C1=CC=CN=C1C(O)=O GZRANGIRVYGSDJ-UHFFFAOYSA-N 0.000 claims description 2
- VYGAQHDGEYQIJU-UHFFFAOYSA-N butanedioic acid;phthalic acid Chemical compound OC(=O)CCC(O)=O.OC(=O)C1=CC=CC=C1C(O)=O VYGAQHDGEYQIJU-UHFFFAOYSA-N 0.000 claims description 2
- KQOCPYKMLMTOOP-UHFFFAOYSA-N phthalic acid;propanoic acid Chemical compound CCC(O)=O.OC(=O)C1=CC=CC=C1C(O)=O KQOCPYKMLMTOOP-UHFFFAOYSA-N 0.000 claims description 2
- JZXYXNDNNNMXNG-CTNGQTDRSA-N propan-2-yl (2r,4s)-4-[2-[3,5-bis(trifluoromethyl)phenyl]ethoxycarbonylamino]-2-ethyl-6-(trifluoromethyl)-3,4-dihydro-2h-quinoline-1-carboxylate Chemical compound N([C@H]1C[C@H](N(C2=CC=C(C=C21)C(F)(F)F)C(=O)OC(C)C)CC)C(=O)OCCC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 JZXYXNDNNNMXNG-CTNGQTDRSA-N 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 2
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims 2
- ZNNQGSGPVUYWOS-UHFFFAOYSA-N 2-(3-hydroxypropoxy)benzoic acid Chemical compound OCCCOC1=CC=CC=C1C(O)=O ZNNQGSGPVUYWOS-UHFFFAOYSA-N 0.000 claims 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 claims 1
- VYOVTXWZLJKCDV-UHFFFAOYSA-N acetic acid 2-ethylpyridine-3-carboxylic acid Chemical compound C(C)C1=C(C(=O)O)C=CC=N1.C(C)(=O)O VYOVTXWZLJKCDV-UHFFFAOYSA-N 0.000 claims 1
- WNEFDHCAKLWKAG-UHFFFAOYSA-N acetic acid;2-hydroxybenzoic acid Chemical compound CC(O)=O.OC(=O)C1=CC=CC=C1O WNEFDHCAKLWKAG-UHFFFAOYSA-N 0.000 claims 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 description 738
- 125000000217 alkyl group Chemical group 0.000 description 624
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 343
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 210
- 229910052757 nitrogen Inorganic materials 0.000 description 156
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 138
- 229910052717 sulfur Inorganic materials 0.000 description 133
- 125000003545 alkoxy group Chemical group 0.000 description 128
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 126
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 125
- 229910052799 carbon Inorganic materials 0.000 description 116
- 125000004043 oxo group Chemical group O=* 0.000 description 114
- 229920006395 saturated elastomer Polymers 0.000 description 113
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 108
- 125000000753 cycloalkyl group Chemical group 0.000 description 103
- 125000005843 halogen group Chemical group 0.000 description 102
- 125000001072 heteroaryl group Chemical group 0.000 description 101
- 125000001424 substituent group Chemical group 0.000 description 101
- 229910052736 halogen Inorganic materials 0.000 description 95
- 125000003118 aryl group Chemical group 0.000 description 90
- 229910052760 oxygen Inorganic materials 0.000 description 89
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 81
- 239000001301 oxygen Substances 0.000 description 81
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 78
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 76
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 75
- 239000011593 sulfur Substances 0.000 description 75
- 125000003342 alkenyl group Chemical group 0.000 description 74
- 125000000623 heterocyclic group Chemical group 0.000 description 74
- 150000001721 carbon Chemical group 0.000 description 73
- 125000005842 heteroatom Chemical group 0.000 description 73
- 125000004093 cyano group Chemical group *C#N 0.000 description 69
- 150000001875 compounds Chemical class 0.000 description 67
- 125000004429 atom Chemical group 0.000 description 66
- 229910052739 hydrogen Inorganic materials 0.000 description 66
- 239000001257 hydrogen Substances 0.000 description 65
- 239000003354 cholesterol ester transfer protein inhibitor Substances 0.000 description 60
- 150000002367 halogens Chemical class 0.000 description 59
- 150000002431 hydrogen Chemical group 0.000 description 58
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 56
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 52
- 125000004434 sulfur atom Chemical group 0.000 description 51
- 125000004414 alkyl thio group Chemical group 0.000 description 48
- 125000001188 haloalkyl group Chemical group 0.000 description 46
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 46
- 125000004433 nitrogen atom Chemical group N* 0.000 description 43
- 125000002252 acyl group Chemical group 0.000 description 41
- 125000000304 alkynyl group Chemical group 0.000 description 41
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 33
- GILIYJDBJZWGBG-UHFFFAOYSA-N 1,1,1-trifluoropropan-2-ol Chemical compound CC(O)C(F)(F)F GILIYJDBJZWGBG-UHFFFAOYSA-N 0.000 description 30
- 125000000392 cycloalkenyl group Chemical group 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 26
- 125000000262 haloalkenyl group Chemical group 0.000 description 25
- 125000004430 oxygen atom Chemical group O* 0.000 description 25
- 125000001153 fluoro group Chemical group F* 0.000 description 24
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 23
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 23
- 125000003282 alkyl amino group Chemical group 0.000 description 22
- 125000003710 aryl alkyl group Chemical group 0.000 description 22
- 125000004438 haloalkoxy group Chemical group 0.000 description 22
- 150000003254 radicals Chemical class 0.000 description 22
- 229940125881 cholesteryl ester transfer protein inhibitor Drugs 0.000 description 21
- 125000005647 linker group Chemical group 0.000 description 21
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 21
- 125000002947 alkylene group Chemical group 0.000 description 20
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 19
- 125000006343 heptafluoro propyl group Chemical group 0.000 description 18
- 150000004678 hydrides Chemical class 0.000 description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 16
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 15
- 125000006350 alkyl thio alkyl group Chemical group 0.000 description 15
- 125000004103 aminoalkyl group Chemical group 0.000 description 15
- 125000002619 bicyclic group Chemical group 0.000 description 15
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 15
- 239000003795 chemical substances by application Substances 0.000 description 15
- 125000004104 aryloxy group Chemical group 0.000 description 14
- 150000003839 salts Chemical group 0.000 description 13
- 150000001356 alkyl thiols Chemical class 0.000 description 12
- 238000004090 dissolution Methods 0.000 description 12
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 12
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 11
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 11
- 239000004815 dispersion polymer Substances 0.000 description 11
- 125000005452 alkenyloxyalkyl group Chemical group 0.000 description 10
- 125000005164 aryl thioalkyl group Chemical group 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 10
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 10
- 125000005347 halocycloalkyl group Chemical group 0.000 description 10
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 10
- 239000003208 petroleum Substances 0.000 description 10
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 10
- 125000003396 thiol group Chemical class [H]S* 0.000 description 10
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 description 9
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 9
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 9
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 description 9
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 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 description 8
- 125000005140 aralkylsulfonyl group Chemical group 0.000 description 8
- 125000005160 aryl oxy alkyl group Chemical group 0.000 description 8
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 8
- 125000005356 cycloalkylalkenyl group Chemical group 0.000 description 8
- 125000005326 heteroaryloxy alkyl group Chemical group 0.000 description 8
- 125000005150 heteroarylsulfinyl group Chemical group 0.000 description 8
- 125000005844 heterocyclyloxy group Chemical group 0.000 description 8
- 239000003112 inhibitor Substances 0.000 description 8
- 229960004592 isopropanol Drugs 0.000 description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 7
- 125000003435 aroyl group Chemical group 0.000 description 7
- 125000005135 aryl sulfinyl group Chemical group 0.000 description 7
- 125000002837 carbocyclic group Chemical group 0.000 description 7
- 125000004181 carboxyalkyl group Chemical group 0.000 description 7
- 125000000000 cycloalkoxy group Chemical group 0.000 description 7
- 125000005149 cycloalkylsulfinyl group Chemical group 0.000 description 7
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 125000000232 haloalkynyl group Chemical group 0.000 description 7
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 description 7
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 6
- 102000012336 Cholesterol Ester Transfer Proteins Human genes 0.000 description 6
- 108010061846 Cholesterol Ester Transfer Proteins Proteins 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000000278 alkyl amino alkyl group Chemical group 0.000 description 6
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 6
- 125000005216 haloheteroaryl group Chemical group 0.000 description 6
- 125000005553 heteroaryloxy group Chemical group 0.000 description 6
- 125000004449 heterocyclylalkenyl group Chemical group 0.000 description 6
- 230000002209 hydrophobic effect Effects 0.000 description 6
- 125000001624 naphthyl group Chemical group 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 125000004450 alkenylene group Chemical group 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 description 5
- 150000003857 carboxamides Chemical class 0.000 description 5
- 230000008878 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 125000004663 dialkyl amino group Chemical group 0.000 description 5
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 description 5
- 125000003106 haloaryl group Chemical group 0.000 description 5
- 125000004415 heterocyclylalkyl group Chemical group 0.000 description 5
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 5
- 125000001544 thienyl group Chemical group 0.000 description 5
- UGRMITBWUVWUEB-UHFFFAOYSA-N 1-$l^{1}-oxidanyl-3-methylbenzene Chemical group CC1=CC=CC([O])=C1 UGRMITBWUVWUEB-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 125000004423 acyloxy group Chemical group 0.000 description 4
- 125000005055 alkyl alkoxy group Chemical group 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 125000001691 aryl alkyl amino group Chemical group 0.000 description 4
- 125000001769 aryl amino group Chemical group 0.000 description 4
- 150000001504 aryl thiols Chemical class 0.000 description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229960003276 erythromycin Drugs 0.000 description 4
- XUFQPHANEAPEMJ-UHFFFAOYSA-N famotidine Chemical compound NC(N)=NC1=NC(CSCCC(N)=NS(N)(=O)=O)=CS1 XUFQPHANEAPEMJ-UHFFFAOYSA-N 0.000 description 4
- 229960001596 famotidine Drugs 0.000 description 4
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 230000002496 gastric effect Effects 0.000 description 4
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 description 4
- 125000004447 heteroarylalkenyl group Chemical group 0.000 description 4
- 125000005368 heteroarylthio group Chemical group 0.000 description 4
- 230000000147 hypnotic effect Effects 0.000 description 4
- 230000000968 intestinal effect Effects 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 235000015424 sodium Nutrition 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000001632 sodium acetate Substances 0.000 description 4
- 235000017281 sodium acetate Nutrition 0.000 description 4
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Classifications
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- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
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- 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
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
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- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
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- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
- A61K31/405—Indole-alkanecarboxylic acids; Derivatives thereof, e.g. tryptophan, indomethacin
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
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- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
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- A61K9/146—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic macromolecular compounds
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
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- Veterinary Medicine (AREA)
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- Inorganic Chemistry (AREA)
- Molecular Biology (AREA)
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- Organic Chemistry (AREA)
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- Diabetes (AREA)
- Obesity (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Quinoline Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Polymerisation Methods In General (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US30025601P | 2001-06-22 | 2001-06-22 | |
PCT/IB2002/001710 WO2003000292A1 (en) | 2001-06-22 | 2002-05-08 | Pharmaceutical compositions comprising low-solubility and/or acid-sensitive drugs and neutralized acidic polymers |
Publications (1)
Publication Number | Publication Date |
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SK15732003A3 true SK15732003A3 (sk) | 2005-01-03 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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SK1573-2003A SK15732003A3 (sk) | 2001-06-22 | 2002-05-08 | Farmaceutické kompozície zahrnujúce liečivá s nízkou rozpustnosťou a/alebo liečivá citlivé na kyselinu a neutralizované kyslé polyméry |
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US (3) | US20030054038A1 (et) |
EP (1) | EP1399190B1 (et) |
JP (1) | JP2004534822A (et) |
KR (1) | KR20040011549A (et) |
CN (1) | CN1545421A (et) |
AT (1) | ATE480226T1 (et) |
BG (1) | BG108488A (et) |
BR (1) | BR0210530A (et) |
CA (1) | CA2450762A1 (et) |
CO (1) | CO5540325A2 (et) |
CR (1) | CR7171A (et) |
CZ (1) | CZ20033457A3 (et) |
DE (1) | DE60237602D1 (et) |
EA (1) | EA200301250A1 (et) |
EC (1) | ECSP034913A (et) |
EE (1) | EE200400033A (et) |
HU (1) | HUP0400264A2 (et) |
IL (1) | IL158991A0 (et) |
IS (1) | IS7047A (et) |
MA (1) | MA27039A1 (et) |
MX (1) | MXPA03011933A (et) |
NO (1) | NO20035699D0 (et) |
OA (1) | OA12624A (et) |
PL (1) | PL368587A1 (et) |
SK (1) | SK15732003A3 (et) |
TN (1) | TNSN03137A1 (et) |
WO (1) | WO2003000292A1 (et) |
ZA (1) | ZA200308989B (et) |
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-
2002
- 2002-05-08 BR BR0210530-6A patent/BR0210530A/pt not_active IP Right Cessation
- 2002-05-08 TN TNPCT/IB2002/001710A patent/TNSN03137A1/en unknown
- 2002-05-08 JP JP2003506934A patent/JP2004534822A/ja active Pending
- 2002-05-08 EP EP02730571A patent/EP1399190B1/en not_active Expired - Lifetime
- 2002-05-08 CA CA002450762A patent/CA2450762A1/en not_active Abandoned
- 2002-05-08 AT AT02730571T patent/ATE480226T1/de not_active IP Right Cessation
- 2002-05-08 EA EA200301250A patent/EA200301250A1/ru unknown
- 2002-05-08 SK SK1573-2003A patent/SK15732003A3/sk unknown
- 2002-05-08 MX MXPA03011933A patent/MXPA03011933A/es not_active Application Discontinuation
- 2002-05-08 OA OA1200300325A patent/OA12624A/en unknown
- 2002-05-08 EE EEP200400033A patent/EE200400033A/et unknown
- 2002-05-08 DE DE60237602T patent/DE60237602D1/de not_active Expired - Lifetime
- 2002-05-08 CN CNA028163338A patent/CN1545421A/zh active Pending
- 2002-05-08 IL IL15899102A patent/IL158991A0/xx unknown
- 2002-05-08 CZ CZ20033457A patent/CZ20033457A3/cs unknown
- 2002-05-08 WO PCT/IB2002/001710 patent/WO2003000292A1/en not_active Application Discontinuation
- 2002-05-08 HU HU0400264A patent/HUP0400264A2/hu unknown
- 2002-05-08 KR KR10-2003-7016765A patent/KR20040011549A/ko not_active Application Discontinuation
- 2002-05-08 PL PL02368587A patent/PL368587A1/xx not_active Application Discontinuation
- 2002-06-17 US US10/175,566 patent/US20030054038A1/en not_active Abandoned
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2003
- 2003-11-19 ZA ZA200308989A patent/ZA200308989B/en unknown
- 2003-11-20 IS IS7047A patent/IS7047A/is unknown
- 2003-11-27 CR CR7171A patent/CR7171A/es not_active Application Discontinuation
- 2003-12-11 MA MA27436A patent/MA27039A1/fr unknown
- 2003-12-15 CO CO03109223A patent/CO5540325A2/es not_active Application Discontinuation
- 2003-12-18 EC EC2003004913A patent/ECSP034913A/es unknown
- 2003-12-19 NO NO20035699A patent/NO20035699D0/no not_active Application Discontinuation
- 2003-12-22 BG BG108488A patent/BG108488A/bg unknown
-
2005
- 2005-08-26 US US11/213,118 patent/US8147872B2/en not_active Expired - Fee Related
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2006
- 2006-06-05 US US11/422,133 patent/US8173142B2/en active Active
Also Published As
Publication number | Publication date |
---|---|
MA27039A1 (fr) | 2004-12-20 |
ECSP034913A (es) | 2004-01-28 |
TNSN03137A1 (en) | 2005-12-23 |
BG108488A (bg) | 2005-01-31 |
EE200400033A (et) | 2004-06-15 |
DE60237602D1 (de) | 2010-10-21 |
EA200301250A1 (ru) | 2004-06-24 |
EP1399190A1 (en) | 2004-03-24 |
EP1399190B1 (en) | 2010-09-08 |
KR20040011549A (ko) | 2004-02-05 |
US8173142B2 (en) | 2012-05-08 |
WO2003000292A1 (en) | 2003-01-03 |
CN1545421A (zh) | 2004-11-10 |
HUP0400264A2 (hu) | 2004-08-30 |
US20030054038A1 (en) | 2003-03-20 |
CO5540325A2 (es) | 2005-07-29 |
IL158991A0 (en) | 2004-05-12 |
US8147872B2 (en) | 2012-04-03 |
CR7171A (es) | 2004-02-23 |
OA12624A (en) | 2006-06-12 |
ATE480226T1 (de) | 2010-09-15 |
MXPA03011933A (es) | 2004-03-26 |
JP2004534822A (ja) | 2004-11-18 |
US20060003011A1 (en) | 2006-01-05 |
IS7047A (is) | 2003-11-20 |
PL368587A1 (en) | 2005-04-04 |
US20060204577A1 (en) | 2006-09-14 |
ZA200308989B (en) | 2004-11-19 |
CZ20033457A3 (cs) | 2004-09-15 |
BR0210530A (pt) | 2004-06-22 |
NO20035699D0 (no) | 2003-12-19 |
CA2450762A1 (en) | 2003-01-03 |
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