IL211335A - Pyrol compounds - Google Patents

Info

Publication number

IL211335A

IL211335A IL211335A IL21133511A IL211335A IL 211335 A IL211335 A IL 211335A IL 211335 A IL211335 A IL 211335A IL 21133511 A IL21133511 A IL 21133511A IL 211335 A IL211335 A IL 211335A

Authority

IL

Israel

Prior art keywords

compound

fluoropyridin

ethyl acetate

fluoro

salt

Prior art date

2008-08-27

Links

• Espacenet
• Global Dossier
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• 150000003233 pyrroles Chemical class 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 319
• 125000005843 halogen group Chemical group 0.000 claims abstract description 114
• 150000003839 salts Chemical group 0.000 claims abstract description 94
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 73
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 17
• -1 1- { 4-Fluoro-5- (2-fluoropyridin-3-yl ) -1- [ ( -methoxypyridin- 2-yl) sulfonyl] -lH-pyrrol-3-yl } -N-methylmethanamine Chemical compound 0.000 claims description 168
• 125000000217 alkyl group Chemical group 0.000 claims description 62
• 208000021302 gastroesophageal reflux disease Diseases 0.000 claims description 36
• 125000003545 alkoxy group Chemical group 0.000 claims description 31
• 208000008469 Peptic Ulcer Diseases 0.000 claims description 20
• 208000011906 peptic ulcer disease Diseases 0.000 claims description 20
• 230000035882 stress Effects 0.000 claims description 19
• 239000003795 chemical substances by application Substances 0.000 claims description 18
• 231100000397 ulcer Toxicity 0.000 claims description 18
• 238000004519 manufacturing process Methods 0.000 claims description 17
• 239000003814 drug Substances 0.000 claims description 15
• 230000002401 inhibitory effect Effects 0.000 claims description 15
• 208000025865 Ulcer Diseases 0.000 claims description 13
• 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims description 13
• 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 13
• 208000000689 peptic esophagitis Diseases 0.000 claims description 13
• 208000000718 duodenal ulcer Diseases 0.000 claims description 12
• 238000011282 treatment Methods 0.000 claims description 11
• 208000005718 Stomach Neoplasms Diseases 0.000 claims description 10
• 206010017758 gastric cancer Diseases 0.000 claims description 10
• 230000002980 postoperative effect Effects 0.000 claims description 10
• 201000011549 stomach cancer Diseases 0.000 claims description 10
• 208000023514 Barrett esophagus Diseases 0.000 claims description 9
• 208000023665 Barrett oesophagus Diseases 0.000 claims description 9
• 208000007882 Gastritis Diseases 0.000 claims description 9
• 206010017866 Gastritis haemorrhagic Diseases 0.000 claims description 9
• 206010020601 Hyperchlorhydria Diseases 0.000 claims description 9
• 206010042220 Stress ulcer Diseases 0.000 claims description 9
• 206010046274 Upper gastrointestinal haemorrhage Diseases 0.000 claims description 9
• 201000008629 Zollinger-Ellison syndrome Diseases 0.000 claims description 9
• 230000037328 acute stress Effects 0.000 claims description 9
• 201000006549 dyspepsia Diseases 0.000 claims description 9
• 208000017215 gastric mucosa-associated lymphoid tissue lymphoma Diseases 0.000 claims description 9
• 201000000052 gastrinoma Diseases 0.000 claims description 9
• 208000007107 Stomach Ulcer Diseases 0.000 claims description 8
• 230000002496 gastric effect Effects 0.000 claims description 8
• 201000005917 gastric ulcer Diseases 0.000 claims description 8
• 238000011321 prophylaxis Methods 0.000 claims description 7
• 230000009858 acid secretion Effects 0.000 claims description 6
• 239000003112 inhibitor Substances 0.000 claims description 6
• 229940126535 potassium competitive acid blocker Drugs 0.000 claims description 6
• JDCBSVKVFVIKHL-UHFFFAOYSA-N 1-[4-fluoro-5-(2-fluoropyridin-3-yl)-1-(4-methylpyridin-2-yl)sulfonylpyrrol-3-yl]-n-methylmethanamine Chemical compound FC=1C(CNC)=CN(S(=O)(=O)C=2N=CC=C(C)C=2)C=1C1=CC=CN=C1F JDCBSVKVFVIKHL-UHFFFAOYSA-N 0.000 claims 1
• 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 68
• 125000001424 substituent group Chemical group 0.000 abstract description 24
• 125000004076 pyridyl group Chemical group 0.000 abstract description 10
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 4
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 2
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 282
• 239000000243 solution Substances 0.000 description 104
• 230000002829 reductive effect Effects 0.000 description 98
• 239000000203 mixture Substances 0.000 description 91
• 238000000034 method Methods 0.000 description 86
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 82
• 239000011541 reaction mixture Substances 0.000 description 60
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 58
• 238000006243 chemical reaction Methods 0.000 description 56
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 48
• 238000010898 silica gel chromatography Methods 0.000 description 46
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 45
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 44
• 239000012044 organic layer Substances 0.000 description 44
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 42
• 239000003480 eluent Substances 0.000 description 42
• 239000010410 layer Substances 0.000 description 42
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 41
• OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 40
• 239000003921 oil Substances 0.000 description 40
• 235000019198 oils Nutrition 0.000 description 40
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 36
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 33
• 239000002904 solvent Substances 0.000 description 32
• 238000005160 1H NMR spectroscopy Methods 0.000 description 29
• 230000000694 effects Effects 0.000 description 26
• 239000007787 solid Substances 0.000 description 25
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 24
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 22
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
• 235000017557 sodium bicarbonate Nutrition 0.000 description 21
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 21
• JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 20
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 20
• UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 20
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
• 239000012312 sodium hydride Substances 0.000 description 20
• 229910000104 sodium hydride Inorganic materials 0.000 description 20
• 239000000725 suspension Substances 0.000 description 19
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
• 238000002360 preparation method Methods 0.000 description 18
• GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 17
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 17
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 16
• 229920006395 saturated elastomer Polymers 0.000 description 16
• VFTFKUDGYRBSAL-UHFFFAOYSA-N 15-crown-5 Chemical compound C1COCCOCCOCCOCCO1 VFTFKUDGYRBSAL-UHFFFAOYSA-N 0.000 description 15
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
• 239000002585 base Substances 0.000 description 15
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 14
• 125000001153 fluoro group Chemical group F* 0.000 description 14
• 239000000126 substance Substances 0.000 description 14
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 14
• 238000012360 testing method Methods 0.000 description 14
• MVEAAGBEUOMFRX-UHFFFAOYSA-N ethyl acetate;hydrochloride Chemical compound Cl.CCOC(C)=O MVEAAGBEUOMFRX-UHFFFAOYSA-N 0.000 description 13
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
• 239000003153 chemical reaction reagent Substances 0.000 description 12
• 239000012230 colorless oil Substances 0.000 description 12
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
• CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 12
• OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 11
• 102100021904 Potassium-transporting ATPase alpha chain 1 Human genes 0.000 description 11
• 108010083204 Proton Pumps Proteins 0.000 description 11
• 238000001816 cooling Methods 0.000 description 11
• 229910052731 fluorine Inorganic materials 0.000 description 11
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 10
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
• 229940079593 drug Drugs 0.000 description 10
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
• 150000002430 hydrocarbons Chemical group 0.000 description 10
• 229940126409 proton pump inhibitor Drugs 0.000 description 10
• 239000000612 proton pump inhibitor Substances 0.000 description 10
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
• 238000005481 NMR spectroscopy Methods 0.000 description 9
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
• 230000002378 acidificating effect Effects 0.000 description 9
• 230000009471 action Effects 0.000 description 9
• 239000012300 argon atmosphere Substances 0.000 description 9
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
• 239000001530 fumaric acid Substances 0.000 description 9
• 229940002612 prodrug Drugs 0.000 description 9
• 239000000651 prodrug Substances 0.000 description 9
• 210000002784 stomach Anatomy 0.000 description 9
• 239000003826 tablet Substances 0.000 description 9
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
• CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 8
• 101150041968 CDC13 gene Proteins 0.000 description 8
• FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 8
• 229920002678 cellulose Polymers 0.000 description 8
• 239000001913 cellulose Substances 0.000 description 8
• 235000010980 cellulose Nutrition 0.000 description 8
• 239000012046 mixed solvent Substances 0.000 description 8
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
• 125000000168 pyrrolyl group Chemical group 0.000 description 8
• 238000003786 synthesis reaction Methods 0.000 description 8
• JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 7
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
• 125000003118 aryl group Chemical group 0.000 description 7
• 229910052801 chlorine Inorganic materials 0.000 description 7
• 125000001309 chloro group Chemical group Cl* 0.000 description 7
• 150000002170 ethers Chemical class 0.000 description 7
• 239000000706 filtrate Substances 0.000 description 7
• 229930195733 hydrocarbon Natural products 0.000 description 7
• 239000007788 liquid Substances 0.000 description 7
• 230000035484 reaction time Effects 0.000 description 7
• 239000000741 silica gel Substances 0.000 description 7
• 229910002027 silica gel Inorganic materials 0.000 description 7
• PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 6
• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 6
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 6
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
• 102000004190 Enzymes Human genes 0.000 description 6
• 108090000790 Enzymes Proteins 0.000 description 6
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
• WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 6
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
• 241000700159 Rattus Species 0.000 description 6
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
• KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 6
• 229930006000 Sucrose Natural products 0.000 description 6
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
• 150000003983 crown ethers Chemical class 0.000 description 6
• 238000010511 deprotection reaction Methods 0.000 description 6
• 229940088598 enzyme Drugs 0.000 description 6
• 230000008029 eradication Effects 0.000 description 6
• 239000008187 granular material Substances 0.000 description 6
• 229910052740 iodine Inorganic materials 0.000 description 6
• 230000036961 partial effect Effects 0.000 description 6
• 239000000843 powder Substances 0.000 description 6
• 125000006239 protecting group Chemical group 0.000 description 6
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
• UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 6
• 229960004793 sucrose Drugs 0.000 description 6
• 229920003169 water-soluble polymer Polymers 0.000 description 6
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 5
• VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 5
• 229930182555 Penicillin Natural products 0.000 description 5
• 239000002202 Polyethylene glycol Substances 0.000 description 5
• 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 5
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 5
• 150000001408 amides Chemical class 0.000 description 5
• 125000003277 amino group Chemical group 0.000 description 5
• 230000003115 biocidal effect Effects 0.000 description 5
• 230000015572 biosynthetic process Effects 0.000 description 5
• 239000011575 calcium Substances 0.000 description 5
• 229910052791 calcium Inorganic materials 0.000 description 5
• 239000002775 capsule Substances 0.000 description 5
• 239000007884 disintegrant Substances 0.000 description 5
• LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 5
• 239000011777 magnesium Chemical class 0.000 description 5
• 229910052749 magnesium Inorganic materials 0.000 description 5
• 235000010355 mannitol Nutrition 0.000 description 5
• 238000005259 measurement Methods 0.000 description 5
• 229910052751 metal Inorganic materials 0.000 description 5
• 239000002184 metal Substances 0.000 description 5
• 229940049954 penicillin Drugs 0.000 description 5
• 239000000546 pharmaceutical excipient Substances 0.000 description 5
• 229920001223 polyethylene glycol Polymers 0.000 description 5
• 239000000047 product Substances 0.000 description 5
• 239000011734 sodium Substances 0.000 description 5
• 229910052708 sodium Inorganic materials 0.000 description 5
• 229940083542 sodium Drugs 0.000 description 5
• 229910000029 sodium carbonate Inorganic materials 0.000 description 5
• 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 description 4
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 4
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
• 206010063655 Erosive oesophagitis Diseases 0.000 description 4
• 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 4
• 229920003134 Eudragit® polymer Polymers 0.000 description 4
• 241000590002 Helicobacter pylori Species 0.000 description 4
• 241000282414 Homo sapiens Species 0.000 description 4
• 229920002153 Hydroxypropyl cellulose Polymers 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
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical class [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
• TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
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