CA1338377C - Composition pharmaceutique stabilisee et sa preparation - Google Patents

Composition pharmaceutique stabilisee et sa preparation

Info

Publication number: CA1338377C
Authority: CA; Canada
Prior art keywords: composition; compound; basic inorganic; sodium; benzimidazole
Prior art date: 1986-02-13
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

Application number

CA000616723A

Other languages

English (en)

Inventor

Tadashi Makino

Tetsuro Tabata

Shin-Ichiro Hirai

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Takeda Pharmaceutical Co Ltd

Original Assignee

Takeda Chemical Industries Ltd

Priority date (The priority date 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 date listed.)

1986-02-13

Filing date

1993-09-14

Publication date

1996-06-11

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=27167671&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CA1338377(C) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1987-02-12 Priority claimed from CA000529605A external-priority patent/CA1327010C/fr

1993-09-14 Application filed by Takeda Chemical Industries Ltd filed Critical Takeda Chemical Industries Ltd

1996-06-11 Application granted granted Critical

1996-06-11 Publication of CA1338377C publication Critical patent/CA1338377C/fr

2007-02-12 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 8
238000004519 manufacturing process Methods 0.000 title description 10
239000000203 mixture Substances 0.000 claims abstract description 55
150000003839 salts Chemical class 0.000 claims abstract description 21
229910017053 inorganic salt Inorganic materials 0.000 claims abstract description 12
239000003381 stabilizer Substances 0.000 claims abstract description 12
SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 claims abstract description 6
239000002702 enteric coating Substances 0.000 claims abstract description 6
238000009505 enteric coating Methods 0.000 claims abstract description 6
230000027119 gastric acid secretion Effects 0.000 claims abstract description 4
230000005764 inhibitory process Effects 0.000 claims abstract description 3
239000008187 granular material Substances 0.000 claims description 38
-1 2-[(2-pyridyl)-methylsulfinyl]benzimidazole compound Chemical class 0.000 claims description 29
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 20
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 16
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 12
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 claims description 10
229910000027 potassium carbonate Inorganic materials 0.000 claims description 10
239000011734 sodium Substances 0.000 claims description 10
229910052708 sodium Inorganic materials 0.000 claims description 10
239000003795 chemical substances by application Substances 0.000 claims description 9
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 8
229910052700 potassium Inorganic materials 0.000 claims description 8
239000011591 potassium Substances 0.000 claims description 8
229910000029 sodium carbonate Inorganic materials 0.000 claims description 8
HBDKFZNDMVLSHM-UHFFFAOYSA-N 2-(pyridin-2-ylmethylsulfinyl)-1h-benzimidazole Chemical class N=1C2=CC=CC=C2NC=1S(=O)CC1=CC=CC=N1 HBDKFZNDMVLSHM-UHFFFAOYSA-N 0.000 claims description 7
229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 6
235000017557 sodium bicarbonate Nutrition 0.000 claims description 6
230000000087 stabilizing effect Effects 0.000 claims description 4
239000003981 vehicle Substances 0.000 claims description 4
239000011230 binding agent Substances 0.000 claims description 3
239000000314 lubricant Substances 0.000 claims description 3
239000003963 antioxidant agent Substances 0.000 claims description 2
239000007931 coated granule Substances 0.000 claims description 2
239000004094 surface-active agent Substances 0.000 claims description 2
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims 1
230000003078 antioxidant effect Effects 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
MJIHNNLFOKEZEW-UHFFFAOYSA-N lansoprazole Chemical compound CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=CC=C2N1 MJIHNNLFOKEZEW-UHFFFAOYSA-N 0.000 claims 1
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 abstract description 5
125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 abstract description 3
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
150000001875 compounds Chemical class 0.000 description 101
125000003545 alkoxy group Chemical group 0.000 description 31
238000006243 chemical reaction Methods 0.000 description 29
125000000217 alkyl group Chemical group 0.000 description 28
239000000460 chlorine Substances 0.000 description 25
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
239000002904 solvent Substances 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
235000013350 formula milk Nutrition 0.000 description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
229910052739 hydrogen Inorganic materials 0.000 description 15
239000001257 hydrogen Substances 0.000 description 15
239000008101 lactose Substances 0.000 description 15
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 13
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 12
239000002585 base Substances 0.000 description 11
239000002775 capsule Substances 0.000 description 11
238000000034 method Methods 0.000 description 11
229920002261 Corn starch Polymers 0.000 description 10
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
239000000654 additive Substances 0.000 description 10
239000008120 corn starch Substances 0.000 description 10
150000002431 hydrogen Chemical class 0.000 description 10
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 10
239000001095 magnesium carbonate Substances 0.000 description 10
229910000021 magnesium carbonate Inorganic materials 0.000 description 10
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
239000002552 dosage form Substances 0.000 description 9
229940093956 potassium carbonate Drugs 0.000 description 9
235000011181 potassium carbonates Nutrition 0.000 description 9
239000000243 solution Substances 0.000 description 9
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
239000001863 hydroxypropyl cellulose Substances 0.000 description 8
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 8
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 7
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
235000017550 sodium carbonate Nutrition 0.000 description 7
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 6
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
229920000168 Microcrystalline cellulose Polymers 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
150000001556 benzimidazoles Chemical class 0.000 description 6
238000009835 boiling Methods 0.000 description 6
238000001816 cooling Methods 0.000 description 6
239000011777 magnesium Substances 0.000 description 6
229910052749 magnesium Inorganic materials 0.000 description 6
235000019359 magnesium stearate Nutrition 0.000 description 6
239000008108 microcrystalline cellulose Substances 0.000 description 6
235000019813 microcrystalline cellulose Nutrition 0.000 description 6
229940016286 microcrystalline cellulose Drugs 0.000 description 6
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
101150041968 CDC13 gene Proteins 0.000 description 5
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 5
229940099408 Oxidizing agent Drugs 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
208000025865 Ulcer Diseases 0.000 description 5
230000001079 digestive effect Effects 0.000 description 5
230000000694 effects Effects 0.000 description 5
230000002140 halogenating effect Effects 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
239000007800 oxidant agent Substances 0.000 description 5
229960003975 potassium Drugs 0.000 description 5
235000007686 potassium Nutrition 0.000 description 5
239000000843 powder Substances 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
231100000397 ulcer Toxicity 0.000 description 5
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical class [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
229930006000 Sucrose Natural products 0.000 description 4
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 4
125000002252 acyl group Chemical group 0.000 description 4
150000001350 alkyl halides Chemical class 0.000 description 4
239000011575 calcium Chemical class 0.000 description 4
229910052791 calcium Inorganic materials 0.000 description 4
239000011248 coating agent Substances 0.000 description 4
230000007423 decrease Effects 0.000 description 4
238000010828 elution Methods 0.000 description 4
HQPMKSGTIOYHJT-UHFFFAOYSA-N ethane-1,2-diol;propane-1,2-diol Chemical compound OCCO.CC(O)CO HQPMKSGTIOYHJT-UHFFFAOYSA-N 0.000 description 4
230000002496 gastric effect Effects 0.000 description 4
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 4
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 4
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 4
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 description 4
229960000381 omeprazole Drugs 0.000 description 4
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
229920001993 poloxamer 188 Polymers 0.000 description 4
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 4
229920000053 polysorbate 80 Polymers 0.000 description 4
239000001267 polyvinylpyrrolidone Substances 0.000 description 4
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 4
239000005720 sucrose Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
229950011585 timoprazole Drugs 0.000 description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical class [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
241000124008 Mammalia Species 0.000 description 3
239000002253 acid Substances 0.000 description 3
230000000996 additive effect Effects 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
125000005083 alkoxyalkoxy group Chemical group 0.000 description 3
230000000767 anti-ulcer Effects 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
229940084030 carboxymethylcellulose calcium Drugs 0.000 description 3
239000012320 chlorinating reagent Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
238000000576 coating method Methods 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 3
238000011049 filling Methods 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
239000007902 hard capsule Substances 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 3
239000000347 magnesium hydroxide Substances 0.000 description 3
229910001862 magnesium hydroxide Inorganic materials 0.000 description 3
235000012254 magnesium hydroxide Nutrition 0.000 description 3
239000000391 magnesium silicate Substances 0.000 description 3
229910052919 magnesium silicate Inorganic materials 0.000 description 3
235000019792 magnesium silicate Nutrition 0.000 description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
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229940088417 precipitated calcium carbonate Drugs 0.000 description 3
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239000007787 solid Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000003860 storage Methods 0.000 description 3
239000003826 tablet Substances 0.000 description 3
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YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
DZKRDHLYQRTDBU-UPHRSURJSA-N (z)-but-2-enediperoxoic acid Chemical compound OOC(=O)\C=C/C(=O)OO DZKRDHLYQRTDBU-UPHRSURJSA-N 0.000 description 2
XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 description 2
PSQZJKGXDGNDFP-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropan-1-ol Chemical compound OCC(F)(F)C(F)(F)F PSQZJKGXDGNDFP-UHFFFAOYSA-N 0.000 description 2
ZXZMHWHCGQSLEI-UHFFFAOYSA-N 2,3-dimethyl-1-oxido-4-(2,2,3,3,3-pentafluoropropoxy)pyridin-1-ium Chemical compound CC1=C(C)[N+]([O-])=CC=C1OCC(F)(F)C(F)(F)F ZXZMHWHCGQSLEI-UHFFFAOYSA-N 0.000 description 2
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WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
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ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
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UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
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VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
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AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
241000283973 Oryctolagus cuniculus Species 0.000 description 2
241000577979 Peromyscus spicilegus Species 0.000 description 2
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229920001214 Polysorbate 60 Polymers 0.000 description 2
241000700159 Rattus Species 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
FZSZUDXAPZXBME-UHFFFAOYSA-N [3-methyl-4-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl]methanol Chemical compound CC1=C(OCC(F)(F)C(F)(F)F)C=CN=C1CO FZSZUDXAPZXBME-UHFFFAOYSA-N 0.000 description 2
YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 2
IYKJEILNJZQJPU-UHFFFAOYSA-N acetic acid;butanedioic acid Chemical compound CC(O)=O.OC(=O)CCC(O)=O IYKJEILNJZQJPU-UHFFFAOYSA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
230000002411 adverse Effects 0.000 description 2
229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
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238000005303 weighing Methods 0.000 description 2
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125000004423 acyloxy group Chemical group 0.000 description 1
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150000001412 amines Chemical class 0.000 description 1
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KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
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159000000007 calcium salts Chemical class 0.000 description 1
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125000001309 chloro group Chemical group Cl* 0.000 description 1
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239000012141 concentrate Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
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238000000354 decomposition reaction Methods 0.000 description 1
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YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
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239000000706 filtrate Substances 0.000 description 1
210000001156 gastric mucosa Anatomy 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
239000003485 histamine H2 receptor antagonist Substances 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
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238000010348 incorporation Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
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UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
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XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
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229940057383 magnesium carbonate 20 mg Drugs 0.000 description 1
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HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
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IEMCVIDXBSZEIX-UHFFFAOYSA-K magnesium sodium carbonate hydroxide Chemical compound C([O-])([O-])=O.[Na+].[OH-].[Mg+2] IEMCVIDXBSZEIX-UHFFFAOYSA-K 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
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150000002739 metals Chemical class 0.000 description 1
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QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
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150000007530 organic bases Chemical class 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
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NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
AAZYNPCMLRQUHI-UHFFFAOYSA-N propan-2-one;2-propan-2-yloxypropane Chemical compound CC(C)=O.CC(C)OC(C)C AAZYNPCMLRQUHI-UHFFFAOYSA-N 0.000 description 1
230000002633 protecting effect Effects 0.000 description 1
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
SHNUBALDGXWUJI-UHFFFAOYSA-N pyridin-2-ylmethanol Chemical class OCC1=CC=CC=N1 SHNUBALDGXWUJI-UHFFFAOYSA-N 0.000 description 1
KEYZUMLVDCHSTP-UHFFFAOYSA-N pyridin-2-ylmethyl acetate Chemical class CC(=O)OCC1=CC=CC=N1 KEYZUMLVDCHSTP-UHFFFAOYSA-N 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
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PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 1
235000010378 sodium ascorbate Nutrition 0.000 description 1
229960005055 sodium ascorbate Drugs 0.000 description 1
229940001593 sodium carbonate Drugs 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 1
NYCVSSWORUBFET-UHFFFAOYSA-M sodium;bromite Chemical compound [Na+].[O-]Br=O NYCVSSWORUBFET-UHFFFAOYSA-M 0.000 description 1
RCOSUMRTSQULBK-UHFFFAOYSA-N sodium;propan-1-olate Chemical compound [Na+].CCC[O-] RCOSUMRTSQULBK-UHFFFAOYSA-N 0.000 description 1
241000894007 species Species 0.000 description 1
238000005507 spraying Methods 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
229940032147 starch Drugs 0.000 description 1
238000003756 stirring Methods 0.000 description 1
230000001629 suppression Effects 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
150000003608 titanium Chemical class 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
229910009112 xH2O Inorganic materials 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA000616723A 1986-02-13 1993-09-14 Composition pharmaceutique stabilisee et sa preparation Expired - Lifetime CA1338377C (fr)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
JP2956786		1986-02-13
JP29567/1986		1986-02-13
JP38059/1986		1986-02-21
JP3805986		1986-02-21
CA000529605A CA1327010C (fr)	1986-02-13	1987-02-12	Compositions pharmaceutiques contenant un compose anti-ulcereux de type benzimidazole et sa production

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000529605A Division CA1327010C (fr)	1986-02-13	1987-02-12	Compositions pharmaceutiques contenant un compose anti-ulcereux de type benzimidazole et sa production

Publications (1)

Publication Number	Publication Date
CA1338377C true CA1338377C (fr)	1996-06-11

Family

ID=27167671

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CA000616724A Expired - Lifetime CA1338399C (fr)	1986-02-13	1993-09-14	Composition pharmaceutique stabilisee et sa preparation
CA000616723A Expired - Lifetime CA1338377C (fr)	1986-02-13	1993-09-14	Composition pharmaceutique stabilisee et sa preparation

Family Applications Before (1)

Application Number	Title	Priority Date	Filing Date
CA000616724A Expired - Lifetime CA1338399C (fr)	1986-02-13	1993-09-14	Composition pharmaceutique stabilisee et sa preparation

Country Status (1)

Country	Link
CA (2)	CA1338399C (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6077541A (en) *	1997-11-14	2000-06-20	Andrx Pharmaceuticals, Inc.	Omeprazole formulation
US6174548B1 (en)	1998-08-28	2001-01-16	Andrx Pharmaceuticals, Inc.	Omeprazole formulation
US6733778B1 (en)	1999-08-27	2004-05-11	Andrx Pharmaceuticals, Inc.	Omeprazole formulation

1993
- 1993-09-14 CA CA000616724A patent/CA1338399C/fr not_active Expired - Lifetime
- 1993-09-14 CA CA000616723A patent/CA1338377C/fr not_active Expired - Lifetime

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6077541A (en) *	1997-11-14	2000-06-20	Andrx Pharmaceuticals, Inc.	Omeprazole formulation
US6096340A (en) *	1997-11-14	2000-08-01	Andrx Pharmaceuticals, Inc.	Omeprazole formulation
US6780435B2 (en)	1997-11-14	2004-08-24	Andrx Pharmaceuticals, Inc.	Omeprazole formulation
US6174548B1 (en)	1998-08-28	2001-01-16	Andrx Pharmaceuticals, Inc.	Omeprazole formulation
US6855336B2 (en)	1998-08-28	2005-02-15	Andrx Pharmaceuticals, Inc.	Omeprazole formulation
US6733778B1 (en)	1999-08-27	2004-05-11	Andrx Pharmaceuticals, Inc.	Omeprazole formulation

Also Published As

Publication number	Publication date
CA1338399C (fr)	1996-06-18

Publication	Publication Date	Title
US5879708A (en)	1999-03-09	Stabilized pharmaceutical composition
US5045321A (en)	1991-09-03	Stabilized pharmaceutical composition and its production
US6749864B2 (en)	2004-06-15	Stabilized pharmaceutical composition
HK1002021B (en)	1998-07-24	Stabilized pharmaceutical composition and its production
JPH0338247B2 (fr)	1991-06-10
EP0208452B1 (fr)	1991-09-18	Dérivés de pyridine, leur préparation et utilisation
RS50071B (sr)	2009-01-22	Novi oblik soli pantoprazola
JP2762998B2 (ja)	1998-06-11	医薬固形組成物用安定化剤および安定化方法
CA1338377C (fr)	1996-06-11	Composition pharmaceutique stabilisee et sa preparation
JPH0825905B2 (ja)	1996-03-13	医薬固形組成物用安定化剤および安定化方法
US20040248940A1 (en)	2004-12-09	Salt of (s)-pantoprazole and its hydrates
JPH04502460A (ja)	1992-05-07	胃酸抑制効果を有する化合物およびその製法
KR950007211B1 (ko)	1995-07-04	안전화된 약제 조성물 및 항궤양 약제 조성물의 안정화 방법
AU641465B2 (en)	1993-09-23	2((2-pyridinyl)methyl) sulfinyl)-1H-Benzimidazole derivatives