JP2527107C

JP2527107C -

Info

Publication number: JP2527107C
Authority: JP; Japan
Prior art keywords: hydrochloride; ray diffraction; solid dispersion; powder; test
Prior art date: 1998-07-30
Legal status : Expired - Lifetime

Application number

Other languages

English (en)

Japanese (ja)

Publication date

1998-07-30

Links

239000007962 solid dispersion Substances 0.000 claims description 86
239000000969 carrier Substances 0.000 claims description 29
229920000642 polymer Polymers 0.000 claims description 27
239000003814 drug Substances 0.000 claims description 26
229940079593 drugs Drugs 0.000 claims description 25
238000004519 manufacturing process Methods 0.000 claims description 8
230000000052 comparative effect Effects 0.000 description 46
238000002441 X-ray diffraction Methods 0.000 description 45
CGIGDMFJXJATDK-UHFFFAOYSA-N Indometacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 36
238000010828 elution Methods 0.000 description 32
239000002904 solvent Substances 0.000 description 25
238000000634 powder X-ray diffraction Methods 0.000 description 23
239000000843 powder Substances 0.000 description 22
-1 carboxymethyl ethyl Chemical group 0.000 description 21
238000007922 dissolution test Methods 0.000 description 21
229960000905 Indomethacin Drugs 0.000 description 18
238000010586 diagram Methods 0.000 description 18
150000001875 compounds Chemical class 0.000 description 17
239000010419 fine particle Substances 0.000 description 17
229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 description 17
239000003795 chemical substances by application Substances 0.000 description 15
238000002156 mixing Methods 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
239000000243 solution Substances 0.000 description 13
229960001597 Nifedipine Drugs 0.000 description 12
HYIMSNHJOBLJNT-UHFFFAOYSA-N Nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 12
238000000465 moulding Methods 0.000 description 11
AIKVCUNQWYTVTO-UHFFFAOYSA-N 5-O-[2-[benzyl(methyl)amino]ethyl] 3-O-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate;hydron;chloride Chemical compound Cl.COC(=O)C1=C(C)NC(C)=C(C(=O)OCCN(C)CC=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 AIKVCUNQWYTVTO-UHFFFAOYSA-N 0.000 description 10
XIQVNETUBQGFHX-UHFFFAOYSA-N Ditropan Chemical compound C=1C=CC=CC=1C(O)(C(=O)OCC#CCN(CC)CC)C1CCCCC1 XIQVNETUBQGFHX-UHFFFAOYSA-N 0.000 description 10
229960002289 Nicardipine hydrochloride Drugs 0.000 description 10
KPHWPUGNDIVLNH-UHFFFAOYSA-M diclofenac sodium Chemical compound [Na+].[O-]C(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl KPHWPUGNDIVLNH-UHFFFAOYSA-M 0.000 description 10
239000002702 enteric coating Substances 0.000 description 10
238000001125 extrusion Methods 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
229960005434 oxybutynin Drugs 0.000 description 10
239000006069 physical mixture Substances 0.000 description 10
229960001193 Diclofenac Sodium Drugs 0.000 description 9
238000009505 enteric coating Methods 0.000 description 9
238000005259 measurement Methods 0.000 description 9
239000000203 mixture Substances 0.000 description 9
239000004014 plasticizer Substances 0.000 description 9
VUKAUDKDFVSVFT-UHFFFAOYSA-N 2-[6-[4,5-bis(2-hydroxypropoxy)-2-(2-hydroxypropoxymethyl)-6-methoxyoxan-3-yl]oxy-4,5-dimethoxy-2-(methoxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)-5-methoxyoxane-3,4-diol Chemical compound COC1C(OC)C(OC2C(C(O)C(OC)C(CO)O2)O)C(COC)OC1OC1C(COCC(C)O)OC(OC)C(OCC(C)O)C1OCC(C)O VUKAUDKDFVSVFT-UHFFFAOYSA-N 0.000 description 8
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 8
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 8
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 8
229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 description 8
238000000034 method Methods 0.000 description 8
239000002245 particle Substances 0.000 description 8
235000019441 ethanol Nutrition 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
229920002472 Starch Polymers 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 6
XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
238000002844 melting Methods 0.000 description 6
239000007787 solid Substances 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
ZUAAPNNKRHMPKG-UHFFFAOYSA-N acetic acid;butanedioic acid;methanol;propane-1,2-diol Chemical compound OC.CC(O)=O.CC(O)CO.OC(=O)CCC(O)=O ZUAAPNNKRHMPKG-UHFFFAOYSA-N 0.000 description 5
239000006185 dispersion Substances 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
229920000639 hydroxypropylmethylcellulose acetate succinate Polymers 0.000 description 5
YJISHJVIRFPGGN-UHFFFAOYSA-N 5-[5-[3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxy-6-[[3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxymethyl]-3,4-dihydroxyoxan-2-yl]oxy-6-(hydroxymethyl)-2-methyloxane-3,4-diol Chemical compound O1C(CO)C(OC)C(O)C(O)C1OCC1C(OC2C(C(O)C(OC)C(CO)O2)O)C(O)C(O)C(OC2C(OC(C)C(O)C2O)CO)O1 YJISHJVIRFPGGN-UHFFFAOYSA-N 0.000 description 4
229940117841 Methacrylic Acid Copolymer Drugs 0.000 description 4
229940100445 WHEAT STARCH Drugs 0.000 description 4
239000002253 acid Substances 0.000 description 4
229920003145 methacrylic acid copolymer Polymers 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
239000002994 raw material Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 3
ZFXYFBGIUFBOJW-UHFFFAOYSA-N Theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 3
URAYPUMNDPQOKB-UHFFFAOYSA-N Triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 3
229960002622 Triacetin Drugs 0.000 description 3
DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 3
239000002775 capsule Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000001087 glyceryl triacetate Substances 0.000 description 3
235000013773 glyceryl triacetate Nutrition 0.000 description 3
239000008187 granular material Substances 0.000 description 3
229910052742 iron Inorganic materials 0.000 description 3
238000004898 kneading Methods 0.000 description 3
239000007788 liquid Substances 0.000 description 3
229920000609 methyl cellulose Polymers 0.000 description 3
239000001923 methylcellulose Substances 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000001069 triethyl citrate Substances 0.000 description 3
235000013769 triethyl citrate Nutrition 0.000 description 3
LNAZSHAWQACDHT-XIYTZBAFSA-N (2R,3R,4S,5R,6S)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2S,3R,4S,5R,6R)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2R,3R,4S,5R,6R)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 2
BGRJTUBHPOOWDU-NSHDSACASA-N (S)-(-)-sulpiride Chemical compound CCN1CCC[C@H]1CNC(=O)C1=CC(S(N)(=O)=O)=CC=C1OC BGRJTUBHPOOWDU-NSHDSACASA-N 0.000 description 2
RWNNRGBCWXOVAC-UHFFFAOYSA-N 1,4-bis[bis(aziridin-1-yl)phosphoryl]piperazine Chemical compound C1CN1P(N1CCN(CC1)P(=O)(N1CC1)N1CC1)(=O)N1CC1 RWNNRGBCWXOVAC-UHFFFAOYSA-N 0.000 description 2
KRKNYBCHXYNGOX-UHFFFAOYSA-K 2qpq Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
229920000623 Cellulose acetate phthalate Polymers 0.000 description 2
IAKHMKGGTNLKSZ-INIZCTEOSA-N Colchicine Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 description 2
AAOVKJBEBIDNHE-UHFFFAOYSA-N Diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
239000001856 Ethyl cellulose Substances 0.000 description 2
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 2
BAUYGSIQEAFULO-UHFFFAOYSA-L Iron(II) sulfate Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 2
101710032250 MICAL1 Proteins 0.000 description 2
XAPRFLSJBSXESP-UHFFFAOYSA-N Oxycinchophen Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=C(O)C=1C1=CC=CC=C1 XAPRFLSJBSXESP-UHFFFAOYSA-N 0.000 description 2
229960000278 Theophylline Drugs 0.000 description 2
SGTNSNPWRIOYBX-UHFFFAOYSA-N Verapamil Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 description 2
229930003270 Vitamin B Natural products 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K [O-]P([O-])([O-])=O Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
239000003242 anti bacterial agent Substances 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
229940081734 cellulose acetate phthalate Drugs 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
229960003529 diazepam Drugs 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
235000019325 ethyl cellulose Nutrition 0.000 description 2
229920001249 ethyl cellulose Polymers 0.000 description 2
OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 description 2
238000009472 formulation Methods 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000001863 hydroxypropyl cellulose Substances 0.000 description 2
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 2
229940071676 hydroxypropylcellulose Drugs 0.000 description 2
VZCYOOQTPOCHFL-UPHRSURJSA-L maleate(2-) Chemical compound [O-]C(=O)\C=C/C([O-])=O VZCYOOQTPOCHFL-UPHRSURJSA-L 0.000 description 2
239000000463 material Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000010452 phosphate Substances 0.000 description 2
229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
235000018102 proteins Nutrition 0.000 description 2
108090000623 proteins and genes Proteins 0.000 description 2
102000004169 proteins and genes Human genes 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
229940086735 succinate Drugs 0.000 description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 2
229960004940 sulpiride Drugs 0.000 description 2
229920002554 vinyl polymer Polymers 0.000 description 2
235000019156 vitamin B Nutrition 0.000 description 2
239000011720 vitamin B Substances 0.000 description 2
NYRVBYLXLHGXDP-UTLKBRERSA-N (1S)-1-[(3,4,5-trimethoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol;hydrate;hydrochloride Chemical compound O.Cl.COC1=C(OC)C(OC)=CC(C[C@H]2C3=CC(O)=C(O)C=C3CCN2)=C1 NYRVBYLXLHGXDP-UTLKBRERSA-N 0.000 description 1
LUEWUZLMQUOBSB-FSKGGBMCSA-N (2S,3S,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-6-[(2R,3S,4R,5S,6S)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(2R,4R,5S,6R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@@H](O[C@@H]2[C@H](O[C@@H](OC3[C@H](O[C@@H](O)[C@@H](O)[C@H]3O)CO)[C@@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O LUEWUZLMQUOBSB-FSKGGBMCSA-N 0.000 description 1
DKSZLDSPXIWGFO-BLOJGBSASA-N (4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-ol;phosphoric acid;hydrate Chemical compound O.OP(O)(O)=O.OP(O)(O)=O.C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC.C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC DKSZLDSPXIWGFO-BLOJGBSASA-N 0.000 description 1
NWXMGUDVXFXRIG-WESIUVDSSA-N (4S,4aS,5aS,6S,12aR)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical compound C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]4(O)C(=O)C3=C(O)C2=C1O NWXMGUDVXFXRIG-WESIUVDSSA-N 0.000 description 1
WLRMANUAADYWEA-NWASOUNVSA-N (S)-timolol maleate Chemical compound OC(=O)\C=C/C(O)=O.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1 WLRMANUAADYWEA-NWASOUNVSA-N 0.000 description 1
WUCVJSHZYUGIOG-UHFFFAOYSA-N 1-(1H-inden-4-yloxy)-3-(propan-2-ylamino)propan-2-ol;1-(3H-inden-4-yloxy)-3-(propan-2-ylamino)propan-2-ol;dihydrochloride Chemical compound Cl.Cl.CC(C)NCC(O)COC1=CC=CC2=C1CC=C2.CC(C)NCC(O)COC1=CC=CC2=C1C=CC2 WUCVJSHZYUGIOG-UHFFFAOYSA-N 0.000 description 1
FGSJNNQVSUVTPW-UHFFFAOYSA-N 1-(2-methoxyphenyl)propan-2-yl-methylazanium;chloride Chemical compound Cl.CNC(C)CC1=CC=CC=C1OC FGSJNNQVSUVTPW-UHFFFAOYSA-N 0.000 description 1
SQUNAWUMZGQQJD-UHFFFAOYSA-N 1-(4-ethylphenyl)-2-methyl-3-(piperidin-1-yl)propan-1-one Chemical compound C1=CC(CC)=CC=C1C(=O)C(C)CN1CCCCC1 SQUNAWUMZGQQJD-UHFFFAOYSA-N 0.000 description 1
NBGBEUITCPENLJ-UHFFFAOYSA-N 1-[4-(4-amino-6,7-dimethoxyquinazolin-2-yl)-1,4-diazepan-1-yl]butan-1-one;hydron;chloride Chemical compound Cl.C1CN(C(=O)CCC)CCCN1C1=NC(N)=C(C=C(OC)C(OC)=C2)C2=N1 NBGBEUITCPENLJ-UHFFFAOYSA-N 0.000 description 1
MHWLWQUZZRMNGJ-UHFFFAOYSA-N 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid Chemical compound C1=C(C)N=C2N(CC)C=C(C(O)=O)C(=O)C2=C1 MHWLWQUZZRMNGJ-UHFFFAOYSA-N 0.000 description 1
GJSURZIOUXUGAL-UHFFFAOYSA-N 2-((2,6-Dichlorophenyl)imino)imidazolidine Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 description 1
FDJCVHVKXFIEPJ-JCNFZFLDSA-N 2-[2,3-dihydro-1H-inden-2-yl-[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]amino]acetic acid;hydron;chloride Chemical compound Cl.C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N(CC(O)=O)C1CC2=CC=CC=C2C1)CC1=CC=CC=C1 FDJCVHVKXFIEPJ-JCNFZFLDSA-N 0.000 description 1
FIVHOHCAXWQPGC-UHFFFAOYSA-N 2-[2-(4-chlorophenoxy)acetyl]oxyethyl-dimethylazanium;chloride Chemical compound Cl.CN(C)CCOC(=O)COC1=CC=C(Cl)C=C1 FIVHOHCAXWQPGC-UHFFFAOYSA-N 0.000 description 1
UDKCHVLMFQVBAA-UHFFFAOYSA-M 2-carboxyphenolate;2-hydroxyethyl(trimethyl)azanium Chemical compound C[N+](C)(C)CCO.OC1=CC=CC=C1C([O-])=O UDKCHVLMFQVBAA-UHFFFAOYSA-M 0.000 description 1
MOPLNORNVJBUJK-UHFFFAOYSA-N 2-cyclohexyl-2-hydroxy-2-phenylacetic acid;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(O)(C(=O)O)C1CCCCC1 MOPLNORNVJBUJK-UHFFFAOYSA-N 0.000 description 1
KTNROWWHOBZQGK-UHFFFAOYSA-N 3-[2-(ethylamino)-1-hydroxyethyl]phenol;hydron;chloride Chemical compound [Cl-].CC[NH2+]CC(O)C1=CC=CC(O)=C1 KTNROWWHOBZQGK-UHFFFAOYSA-N 0.000 description 1
ZPMVNZLARAEGHB-UHFFFAOYSA-N 4-(dibenzo[1,2-a:1',2'-e][7]annulen-11-ylidene)-1-methylpiperidin-1-ium;chloride Chemical compound Cl.C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 ZPMVNZLARAEGHB-UHFFFAOYSA-N 0.000 description 1
MBGGBVCUIVRRBF-UHFFFAOYSA-N 4-[2-(benzenesulfinyl)ethyl]-1,2-diphenylpyrazolidine-3,5-dione Chemical compound O=C1N(C=2C=CC=CC=2)N(C=2C=CC=CC=2)C(=O)C1CCS(=O)C1=CC=CC=C1 MBGGBVCUIVRRBF-UHFFFAOYSA-N 0.000 description 1
ICBCZMIEENEERJ-UHFFFAOYSA-N 4-butyl-1,2-diphenylpyrazolidine-3,5-dione;2-(4-chlorophenoxy)-N-[2-(diethylamino)ethyl]acetamide Chemical compound CCN(CC)CCNC(=O)COC1=CC=C(Cl)C=C1.O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 ICBCZMIEENEERJ-UHFFFAOYSA-N 0.000 description 1
JWZZKOKVBUJMES-UHFFFAOYSA-N 4-{1-hydroxy-2-[(propan-2-yl)amino]ethyl}benzene-1,2-diol Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
FYBXRCFPOTXTJF-RFVHGSKJSA-N 5-[(2R)-3-(tert-butylamino)-2-hydroxypropoxy]-3,4-dihydro-1H-quinolin-2-one;hydrochloride Chemical compound Cl.N1C(=O)CCC2=C1C=CC=C2OC[C@H](O)CNC(C)(C)C FYBXRCFPOTXTJF-RFVHGSKJSA-N 0.000 description 1
XXDAXBZYUXLDRD-SBSPUUFOSA-N 5-[2-[(2R)-3-(tert-butylamino)-2-hydroxypropyl]sulfanyl-1,3-thiazol-4-yl]thiophene-2-carboxamide;hydrochloride Chemical compound Cl.S1C(SC[C@H](O)CNC(C)(C)C)=NC(C=2SC(=CC=2)C(N)=O)=C1 XXDAXBZYUXLDRD-SBSPUUFOSA-N 0.000 description 1
VXLCNTLWWUDBSO-UHFFFAOYSA-N 6-chloro-3-ethyl-1,1-dioxo-3,4-dihydro-2H-1$l^{6},2,4-benzothiadiazine-7-sulfonamide Chemical compound ClC1=C(S(N)(=O)=O)C=C2S(=O)(=O)NC(CC)NC2=C1 VXLCNTLWWUDBSO-UHFFFAOYSA-N 0.000 description 1
GSNOZLZNQMLSKJ-UHFFFAOYSA-N 7-(Diethylamino)-5-methyl-s-triazolo(1,5-a)pyrimidine Chemical compound CCN(CC)C1=CC(C)=NC2=NC=NN12 GSNOZLZNQMLSKJ-UHFFFAOYSA-N 0.000 description 1
239000005541 ACE inhibitor Substances 0.000 description 1
229960003965 ANTIEPILEPTICS Drugs 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
229960003830 Acebutolol Hydrochloride Drugs 0.000 description 1
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