CA2155830A1 - Substituted azolone derivatives for treating diseases causes by helicobacter - Google Patents
Substituted azolone derivatives for treating diseases causes by helicobacterInfo
- Publication number
- CA2155830A1 CA2155830A1 CA002155830A CA2155830A CA2155830A1 CA 2155830 A1 CA2155830 A1 CA 2155830A1 CA 002155830 A CA002155830 A CA 002155830A CA 2155830 A CA2155830 A CA 2155830A CA 2155830 A1 CA2155830 A1 CA 2155830A1
- Authority
- CA
- Canada
- Prior art keywords
- formula
- dihydro
- pyridinyl
- triazol
- piperazinyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 241000589989 Helicobacter Species 0.000 title claims abstract description 17
- 201000010099 disease Diseases 0.000 title claims abstract description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 4
- VIXWGKYSYIBATJ-UHFFFAOYSA-N pyrrol-2-one Chemical class O=C1C=CC=N1 VIXWGKYSYIBATJ-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 84
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 47
- -1 C1-4alkyloxy Chemical group 0.000 claims abstract description 39
- 239000002253 acid Substances 0.000 claims abstract description 34
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 239000001257 hydrogen Substances 0.000 claims abstract description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 6
- 239000003814 drug Substances 0.000 claims abstract description 5
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 3
- 125000001424 substituent group Chemical group 0.000 claims abstract description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 8
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 5
- 238000004519 manufacturing process Methods 0.000 claims abstract 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 18
- 239000012442 inert solvent Substances 0.000 claims description 16
- 239000002585 base Substances 0.000 claims description 12
- 239000003153 chemical reaction reagent Substances 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 8
- 239000003937 drug carrier Substances 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- JRYBCSFNLJYXGF-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)-1-oxobutan-2-yl]-4-[6-[4-(3,4-dimethoxyphenyl)piperidin-1-yl]pyridin-3-yl]-1,2,4-triazol-3-one Chemical compound N1=CN(C=2C=NC(=CC=2)N2CCC(CC2)C=2C=C(OC)C(OC)=CC=2)C(=O)N1C(CC)C(=O)C1=CC=C(Cl)C=C1 JRYBCSFNLJYXGF-UHFFFAOYSA-N 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- 125000005805 dimethoxy phenyl group Chemical group 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 4
- MJJNRMBAMZFFSO-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)-1-hydroxybutan-2-yl]-4-[4-[4-(6-methoxypyridin-2-yl)piperazin-1-yl]phenyl]-1,2,4-triazol-3-one Chemical compound N1=CN(C=2C=CC(=CC=2)N2CCN(CC2)C=2N=C(OC)C=CC=2)C(=O)N1C(CC)C(O)C1=CC=C(Cl)C=C1 MJJNRMBAMZFFSO-UHFFFAOYSA-N 0.000 claims 1
- AAKXYDGQABCFJM-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)-1-hydroxybutan-2-yl]-4-[4-[4-(6-methoxypyridin-3-yl)piperazin-1-yl]phenyl]-1,2,4-triazol-3-one Chemical compound N1=CN(C=2C=CC(=CC=2)N2CCN(CC2)C=2C=NC(OC)=CC=2)C(=O)N1C(CC)C(O)C1=CC=C(Cl)C=C1 AAKXYDGQABCFJM-UHFFFAOYSA-N 0.000 claims 1
- YPNFUKKEEXQSEP-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)-1-hydroxybutan-2-yl]-4-[6-[4-(3,4-dimethoxyphenyl)piperazin-1-yl]pyridin-3-yl]-1,2,4-triazol-3-one Chemical compound N1=CN(C=2C=NC(=CC=2)N2CCN(CC2)C=2C=C(OC)C(OC)=CC=2)C(=O)N1C(CC)C(O)C1=CC=C(Cl)C=C1 YPNFUKKEEXQSEP-UHFFFAOYSA-N 0.000 claims 1
- NAFYYBHOBSFJJP-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)-1-hydroxybutan-2-yl]-4-[6-[4-(3-hydroxyphenyl)piperazin-1-yl]pyridin-3-yl]-1,2,4-triazol-3-one Chemical compound N1=CN(C=2C=NC(=CC=2)N2CCN(CC2)C=2C=C(O)C=CC=2)C(=O)N1C(CC)C(O)C1=CC=C(Cl)C=C1 NAFYYBHOBSFJJP-UHFFFAOYSA-N 0.000 claims 1
- DHANJABGGMUXMI-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)-1-hydroxybutan-2-yl]-4-[6-[4-(3-methoxyphenyl)piperazin-1-yl]pyridin-3-yl]-1,2,4-triazol-3-one Chemical compound N1=CN(C=2C=NC(=CC=2)N2CCN(CC2)C=2C=C(OC)C=CC=2)C(=O)N1C(CC)C(O)C1=CC=C(Cl)C=C1 DHANJABGGMUXMI-UHFFFAOYSA-N 0.000 claims 1
- YJDGYHMBGVLBNS-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)-1-oxobutan-2-yl]-4-[6-[4-(3,4-dimethoxyphenyl)piperazin-1-yl]pyridin-3-yl]-1,2,4-triazol-3-one Chemical compound N1=CN(C=2C=NC(=CC=2)N2CCN(CC2)C=2C=C(OC)C(OC)=CC=2)C(=O)N1C(CC)C(=O)C1=CC=C(Cl)C=C1 YJDGYHMBGVLBNS-UHFFFAOYSA-N 0.000 claims 1
- WCNBVZMLANSQAW-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)-1-oxobutan-2-yl]-4-[6-[4-(3-hydroxyphenyl)piperazin-1-yl]pyridin-3-yl]-1,2,4-triazol-3-one Chemical compound N1=CN(C=2C=NC(=CC=2)N2CCN(CC2)C=2C=C(O)C=CC=2)C(=O)N1C(CC)C(=O)C1=CC=C(Cl)C=C1 WCNBVZMLANSQAW-UHFFFAOYSA-N 0.000 claims 1
- RIUKGHVZMNVFEK-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)-1-oxobutan-2-yl]-4-[6-[4-(3-methoxyphenyl)piperazin-1-yl]pyridin-3-yl]-1,2,4-triazol-3-one Chemical compound N1=CN(C=2C=NC(=CC=2)N2CCN(CC2)C=2C=C(OC)C=CC=2)C(=O)N1C(CC)C(=O)C1=CC=C(Cl)C=C1 RIUKGHVZMNVFEK-UHFFFAOYSA-N 0.000 claims 1
- RTOMPAHBCCEBET-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)-1-oxobutan-2-yl]-4-[6-[4-(4-methoxyphenyl)piperazin-1-yl]pyridin-3-yl]-1,2,4-triazol-3-one Chemical compound N1=CN(C=2C=NC(=CC=2)N2CCN(CC2)C=2C=CC(OC)=CC=2)C(=O)N1C(CC)C(=O)C1=CC=C(Cl)C=C1 RTOMPAHBCCEBET-UHFFFAOYSA-N 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 230000009466 transformation Effects 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 14
- 239000000203 mixture Substances 0.000 description 96
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 53
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- 239000000243 solution Substances 0.000 description 42
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 39
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 37
- 239000000543 intermediate Substances 0.000 description 34
- 239000000047 product Substances 0.000 description 33
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 23
- 239000003480 eluent Substances 0.000 description 23
- 239000011541 reaction mixture Substances 0.000 description 23
- 238000003756 stirring Methods 0.000 description 22
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- 239000002244 precipitate Substances 0.000 description 18
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 17
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 238000004440 column chromatography Methods 0.000 description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 14
- 230000000694 effects Effects 0.000 description 13
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 13
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 12
- 229920000858 Cyclodextrin Polymers 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 125000005843 halogen group Chemical group 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- 239000003826 tablet Substances 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 229960001701 chloroform Drugs 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000007868 Raney catalyst Substances 0.000 description 6
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 6
- 229910000564 Raney nickel Inorganic materials 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- 241000590002 Helicobacter pylori Species 0.000 description 4
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- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
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- 239000002202 Polyethylene glycol Substances 0.000 description 4
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- 239000008103 glucose Substances 0.000 description 4
- 229940037467 helicobacter pylori Drugs 0.000 description 4
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- BETBCTULGKILCZ-UHFFFAOYSA-N 2-(3-bromophenyl)-1,3-thiazole Chemical compound BrC1=CC=CC(C=2SC=CN=2)=C1 BETBCTULGKILCZ-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
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- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
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- SBQLYHNEIUGQKH-UHFFFAOYSA-N omeprazole Chemical compound N1=C2[CH]C(OC)=CC=C2N=C1S(=O)CC1=NC=C(C)C(OC)=C1C SBQLYHNEIUGQKH-UHFFFAOYSA-N 0.000 description 1
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- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
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- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- NTGBUUXKGAZMSE-UHFFFAOYSA-N phenyl n-[4-[4-(4-methoxyphenyl)piperazin-1-yl]phenyl]carbamate Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(NC(=O)OC=3C=CC=CC=3)=CC=2)CC1 NTGBUUXKGAZMSE-UHFFFAOYSA-N 0.000 description 1
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- 229910052700 potassium Inorganic materials 0.000 description 1
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
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- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
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- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
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- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
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- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/70—One oxygen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP93200474.0 | 1993-02-19 | ||
| EP93200474 | 1993-02-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2155830A1 true CA2155830A1 (en) | 1994-09-01 |
Family
ID=8213653
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002155830A Abandoned CA2155830A1 (en) | 1993-02-19 | 1994-02-09 | Substituted azolone derivatives for treating diseases causes by helicobacter |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US5650411A (en, 2012) |
| EP (1) | EP0684821A1 (en, 2012) |
| JP (1) | JPH08506821A (en, 2012) |
| CN (1) | CN1118138A (en, 2012) |
| AP (1) | AP435A (en, 2012) |
| AU (1) | AU675508B2 (en, 2012) |
| CA (1) | CA2155830A1 (en, 2012) |
| FI (1) | FI953899A0 (en, 2012) |
| HU (1) | HUT73662A (en, 2012) |
| IL (1) | IL108703A (en, 2012) |
| LT (1) | LT3214B (en, 2012) |
| MX (1) | MX9401294A (en, 2012) |
| NO (1) | NO953254L (en, 2012) |
| NZ (1) | NZ261854A (en, 2012) |
| PL (1) | PL174836B1 (en, 2012) |
| RU (1) | RU2128659C1 (en, 2012) |
| TW (1) | TW279864B (en, 2012) |
| WO (1) | WO1994018978A1 (en, 2012) |
| ZA (1) | ZA941137B (en, 2012) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5703236A (en) * | 1993-12-21 | 1997-12-30 | Schering Corporation | Tetrahydrofuran antifungals |
| WO1995027704A1 (en) * | 1994-04-06 | 1995-10-19 | Janssen Pharmaceutica N.V. | Anti-helicobacter ester and carbamate derivatives of azolones |
| US5639754A (en) * | 1994-07-12 | 1997-06-17 | Janssen Pharmaceutica N.V. | Urea and thiourea derivatives of azolones |
| US5637592A (en) * | 1994-07-12 | 1997-06-10 | Janssen Pharmaceutica N.V. | Acyl derivatives of azolones |
| US5607932A (en) * | 1994-07-12 | 1997-03-04 | Janssen Pharmaceutica N.V. | Heterocyclic derivatives of azolones |
| CA2160423A1 (en) * | 1994-11-02 | 1996-05-03 | Hemant N. Joshi | Salts of nefazodone having improved dissolution rates |
| GB9524754D0 (en) * | 1995-12-04 | 1996-04-24 | Symmetricom Inc | Mobile position determination |
| US6432947B1 (en) * | 1997-02-19 | 2002-08-13 | Berlex Laboratories, Inc. | N-heterocyclic derivatives as NOS inhibitors |
| DE69826883T2 (de) | 1997-10-27 | 2005-02-03 | Neurosearch A/S | Heteroaryl diazacycloalkane als cholinergische ligande für nikotin-acetylcholin-rezeptoren |
| RU2145975C1 (ru) * | 1999-07-19 | 2000-02-27 | Тверская медакадемия | Способ культивирования helicobacter pylori |
| US6312723B1 (en) | 1999-08-26 | 2001-11-06 | Robert R. Whittle | Pharmaceutical unit dosage form |
| US6262086B1 (en) | 1999-08-26 | 2001-07-17 | Robert R. Whittle | Pharmaceutical unit dosage form |
| US6262085B1 (en) | 1999-08-26 | 2001-07-17 | Robert R. Whittle | Alkoxy substituted Benzimidazole compounds, pharmaceutical preparations containing the same, and methods of using the same |
| US6780880B1 (en) | 1999-08-26 | 2004-08-24 | Robert R. Whittle | FT-Raman spectroscopic measurement |
| US6316020B1 (en) | 1999-08-26 | 2001-11-13 | Robert R. Whittle | Pharmaceutical formulations |
| US6369087B1 (en) * | 1999-08-26 | 2002-04-09 | Robert R. Whittle | Alkoxy substituted benzimidazole compounds, pharmaceutical preparations containing the same, and methods of using the same |
| US6312712B1 (en) | 1999-08-26 | 2001-11-06 | Robert R. Whittle | Method of improving bioavailability |
| US6268385B1 (en) | 1999-08-26 | 2001-07-31 | Robert R. Whittle | Dry blend pharmaceutical formulations |
| US6326384B1 (en) | 1999-08-26 | 2001-12-04 | Robert R. Whittle | Dry blend pharmaceutical unit dosage form |
| US8013156B2 (en) * | 2003-03-19 | 2011-09-06 | Exelixis, Inc. | Tie-2 modulators and methods of use |
| CN105622463B (zh) | 2006-12-26 | 2019-02-22 | 兰休斯医疗成像公司 | 用于使心脏神经支配成像的配体 |
| CN102234267A (zh) * | 2010-04-21 | 2011-11-09 | 中国科学院上海药物研究所 | 新型三氮唑类抗真菌化合物、其药物组合物及其制备方法和用途 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT311956B (de) * | 1971-06-07 | 1973-12-10 | Boehringer Sohn Ingelheim | Verfahren zur Herstellung neuer Phenylimidazolidinonderivate und ihrer Salze |
| AR208414A1 (es) * | 1974-11-07 | 1976-12-27 | Rhone Poulenc Ind | Procedimiento para obtener nuevos derivados de la((acil-4piperazinil-1)carboniloxi-5 pirrolinona-2) |
| US4724239A (en) * | 1985-09-16 | 1988-02-09 | Morgan Lee R | Method of treating chemical ulcers with N,N'-diacetylcystine, N-acetyl homocysteine and N-acetyl cysteine |
| CA1292472C (en) * | 1985-12-03 | 1991-11-26 | Alfonsus Guilielmus Knaeps | Derivatives of ¬¬4-¬4-(4-phenyl-1-piperazinyl)- phenoxymethyl|-1,3-dioxolan-2-yl|methyl|-1h-imidazoles and 1h-1,2,4-triazoles |
| US4791111A (en) * | 1985-12-23 | 1988-12-13 | Janssen Pharmaceutica, N.V. | [[4-[4-(4-phenyl-1-piperazinyl)phenoxymethyl]-1,3-dioxolan-2-yl]methyl]-1H-imidazoles and 1H-1,2,4-triazoles having anti-microbial properties |
| CA1331757C (en) * | 1988-02-29 | 1994-08-30 | Janssen Pharmaceutica Naamloze Vennootschap | 5-lipoxygenase inhibiting 4-(4-phenyl-1-piperazinyl)phenols |
| CA2076257A1 (en) * | 1991-09-13 | 1993-03-14 | Jan Heeres | 4-¬4-¬4-(4-hydroxyphenyl)-1- piperazinyl|phenyl|-5-methyl-3h -1,2,4-triazol-3-one derivatives |
-
1994
- 1994-02-02 TW TW083100854A patent/TW279864B/zh active
- 1994-02-09 EP EP94907534A patent/EP0684821A1/en not_active Withdrawn
- 1994-02-09 CA CA002155830A patent/CA2155830A1/en not_active Abandoned
- 1994-02-09 AU AU61081/94A patent/AU675508B2/en not_active Ceased
- 1994-02-09 US US08/491,960 patent/US5650411A/en not_active Expired - Fee Related
- 1994-02-09 WO PCT/EP1994/000380 patent/WO1994018978A1/en not_active Application Discontinuation
- 1994-02-09 JP JP6518613A patent/JPH08506821A/ja active Pending
- 1994-02-09 NZ NZ261854A patent/NZ261854A/en unknown
- 1994-02-09 CN CN94191221A patent/CN1118138A/zh active Pending
- 1994-02-09 PL PL94310348A patent/PL174836B1/pl unknown
- 1994-02-09 RU RU95122796A patent/RU2128659C1/ru active
- 1994-02-09 HU HU9501923A patent/HUT73662A/hu unknown
- 1994-02-18 MX MX9401294A patent/MX9401294A/es unknown
- 1994-02-18 LT LTIP1874A patent/LT3214B/lt not_active IP Right Cessation
- 1994-02-18 AP APAP/P/1994/000622A patent/AP435A/en active
- 1994-02-18 IL IL108703A patent/IL108703A/en not_active IP Right Cessation
- 1994-02-18 ZA ZA941137A patent/ZA941137B/xx unknown
-
1995
- 1995-08-18 FI FI953899A patent/FI953899A0/fi unknown
- 1995-08-18 NO NO953254A patent/NO953254L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN1118138A (zh) | 1996-03-06 |
| LTIP1874A (en) | 1994-09-25 |
| HUT73662A (en) | 1996-09-30 |
| WO1994018978A1 (en) | 1994-09-01 |
| HU9501923D0 (en) | 1995-09-28 |
| TW279864B (en, 2012) | 1996-07-01 |
| PL174836B1 (pl) | 1998-09-30 |
| LT3214B (en) | 1995-04-25 |
| AU6108194A (en) | 1994-09-14 |
| IL108703A (en) | 1998-01-04 |
| JPH08506821A (ja) | 1996-07-23 |
| PL310348A1 (en) | 1995-12-11 |
| FI953899A7 (fi) | 1995-08-18 |
| EP0684821A1 (en) | 1995-12-06 |
| NO953254L (no) | 1995-09-11 |
| MX9401294A (es) | 1994-08-31 |
| NZ261854A (en) | 1997-04-24 |
| FI953899A0 (fi) | 1995-08-18 |
| NO953254D0 (no) | 1995-08-18 |
| AU675508B2 (en) | 1997-02-06 |
| ZA941137B (en) | 1995-10-25 |
| IL108703A0 (en) | 1994-05-30 |
| AP9400622A0 (en) | 1994-04-30 |
| AP435A (en) | 1995-11-17 |
| RU2128659C1 (ru) | 1999-04-10 |
| US5650411A (en) | 1997-07-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |