NO841754L - Fremgangsmaate ved fremstilling av nye fluoralkoksyforbindelser - Google Patents
Fremgangsmaate ved fremstilling av nye fluoralkoksyforbindelserInfo
- Publication number
- NO841754L NO841754L NO841754A NO841754A NO841754L NO 841754 L NO841754 L NO 841754L NO 841754 A NO841754 A NO 841754A NO 841754 A NO841754 A NO 841754A NO 841754 L NO841754 L NO 841754L
- Authority
- NO
- Norway
- Prior art keywords
- methoxy
- residue
- hydrogen
- methyl
- pyridyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 114
- 238000000034 method Methods 0.000 title claims description 30
- JVTSHOJDBRTPHD-UHFFFAOYSA-N 2,2,2-trifluoroacetaldehyde Chemical compound FC(F)(F)C=O JVTSHOJDBRTPHD-UHFFFAOYSA-N 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 73
- 239000001257 hydrogen Substances 0.000 claims abstract description 73
- 150000003839 salts Chemical class 0.000 claims abstract description 48
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 38
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 23
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 19
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 13
- 239000011737 fluorine Substances 0.000 claims abstract description 13
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 11
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical group 0.000 claims abstract description 9
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims abstract description 6
- QPAXMPYBNSHKAK-UHFFFAOYSA-N chloro(difluoro)methane Chemical group F[C](F)Cl QPAXMPYBNSHKAK-UHFFFAOYSA-N 0.000 claims abstract description 3
- -1 alkyl radical Chemical class 0.000 claims description 53
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 20
- 238000002360 preparation method Methods 0.000 claims description 18
- 229910052740 iodine Inorganic materials 0.000 claims description 17
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 16
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 16
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 16
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 16
- 239000007858 starting material Substances 0.000 claims description 15
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 9
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 claims description 8
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000001556 benzimidazoles Chemical class 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- OMYYXOJVDCRZBD-UHFFFAOYSA-N 2-[(4-methoxy-3-methylpyridin-2-yl)methylsulfanyl]-6-(1,1,2,2-tetrafluoroethoxy)-1h-benzimidazole Chemical compound COC1=CC=NC(CSC=2NC3=CC=C(OC(F)(F)C(F)F)C=C3N=2)=C1C OMYYXOJVDCRZBD-UHFFFAOYSA-N 0.000 claims description 3
- CFILDZXKPBMVNO-UHFFFAOYSA-N 2-[(4-methoxy-3-methylpyridin-2-yl)methylsulfanyl]-6-(2,2,2-trifluoroethoxy)-1h-benzimidazole Chemical compound COC1=CC=NC(CSC=2NC3=CC=C(OCC(F)(F)F)C=C3N=2)=C1C CFILDZXKPBMVNO-UHFFFAOYSA-N 0.000 claims description 3
- IWECCZBOLCDNSE-UHFFFAOYSA-N 2-[(4-methoxypyridin-2-yl)methylsulfinyl]-6-(1,1,2,2-tetrafluoroethoxy)-1h-benzimidazole Chemical compound COC1=CC=NC(CS(=O)C=2NC3=CC(OC(F)(F)C(F)F)=CC=C3N=2)=C1 IWECCZBOLCDNSE-UHFFFAOYSA-N 0.000 claims description 3
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 3
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical class C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 claims description 2
- RBGGMTQEVZWWLW-UHFFFAOYSA-N 1-methoxybenzimidazole Chemical compound C1=CC=C2N(OC)C=NC2=C1 RBGGMTQEVZWWLW-UHFFFAOYSA-N 0.000 claims description 2
- AQQUVYVCRJAMKM-UHFFFAOYSA-N 2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-6-(trifluoromethoxy)-1h-benzimidazole Chemical compound COC1=C(C)C=NC(CS(=O)C=2NC3=CC=C(OC(F)(F)F)C=C3N=2)=C1C AQQUVYVCRJAMKM-UHFFFAOYSA-N 0.000 claims description 2
- JAJVJKRIHGUXJX-UHFFFAOYSA-N 2-[(4-methoxy-3-methylpyridin-2-yl)methylsulfinyl]-6-(2,2,2-trifluoroethoxy)-1h-benzimidazole Chemical compound COC1=CC=NC(CS(=O)C=2NC3=CC=C(OCC(F)(F)F)C=C3N=2)=C1C JAJVJKRIHGUXJX-UHFFFAOYSA-N 0.000 claims description 2
- LDDGEZLWYOZBAQ-UHFFFAOYSA-N 2-[(4-methoxy-5-methylpyridin-2-yl)methylsulfinyl]-6-(trifluoromethoxy)-1h-benzimidazole Chemical compound C1=C(C)C(OC)=CC(CS(=O)C=2NC3=CC=C(OC(F)(F)F)C=C3N=2)=N1 LDDGEZLWYOZBAQ-UHFFFAOYSA-N 0.000 claims description 2
- YFDAYUXSRDTCHE-UHFFFAOYSA-N 2-[2-[[2-(1h-benzimidazol-2-yl)-1h-pyridin-2-yl]methylsulfanylmethyl]-1h-pyridin-2-yl]-1h-benzimidazole Chemical class N1C=CC=CC1(C=1NC2=CC=CC=C2N=1)CSCC1(C=2NC3=CC=CC=C3N=2)NC=CC=C1 YFDAYUXSRDTCHE-UHFFFAOYSA-N 0.000 claims description 2
- KNEMGJDWGUTNJX-UHFFFAOYSA-N 5,6-bis(difluoromethoxy)-2-[(4-methoxy-3-methylpyridin-2-yl)methylsulfinyl]-1h-benzimidazole Chemical compound COC1=CC=NC(CS(=O)C=2NC3=CC(OC(F)F)=C(OC(F)F)C=C3N=2)=C1C KNEMGJDWGUTNJX-UHFFFAOYSA-N 0.000 claims description 2
- KAUGJJICAPARHM-UHFFFAOYSA-N 6-(difluoromethoxy)-5-methoxy-2-[(4-methoxy-3-methylpyridin-2-yl)methylsulfinyl]-1h-benzimidazole Chemical compound COC1=CC=NC(CS(=O)C=2NC3=CC(OC)=C(OC(F)F)C=C3N=2)=C1C KAUGJJICAPARHM-UHFFFAOYSA-N 0.000 claims description 2
- 150000004675 formic acid derivatives Chemical class 0.000 claims description 2
- 150000004987 o-phenylenediamines Chemical class 0.000 claims description 2
- 150000003222 pyridines Chemical class 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- QUNAPURTLGQPAG-UHFFFAOYSA-N 2-[(4-methoxy-3-methylpyridin-2-yl)methylsulfinyl]-6-(1,1,2,2-tetrafluoroethoxy)-1h-benzimidazole Chemical compound COC1=CC=NC(C[S+]([O-])C=2NC3=CC=C(OC(F)(F)C(F)F)C=C3N=2)=C1C QUNAPURTLGQPAG-UHFFFAOYSA-N 0.000 claims 1
- WKIKQLQKPRSSCQ-UHFFFAOYSA-N 2-[(4-methoxypyridin-2-yl)methylsulfinyl]-6-(trifluoromethoxy)-1h-benzimidazole Chemical compound COC1=CC=NC(CS(=O)C=2NC3=CC=C(OC(F)(F)F)C=C3N=2)=C1 WKIKQLQKPRSSCQ-UHFFFAOYSA-N 0.000 claims 1
- 235000004431 Linum usitatissimum Nutrition 0.000 claims 1
- 240000006240 Linum usitatissimum Species 0.000 claims 1
- 235000004426 flaxseed Nutrition 0.000 claims 1
- 210000002784 stomach Anatomy 0.000 abstract description 9
- 230000001681 protective effect Effects 0.000 abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 40
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 36
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- 239000000243 solution Substances 0.000 description 33
- 238000000354 decomposition reaction Methods 0.000 description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
- 239000000203 mixture Substances 0.000 description 19
- 239000002904 solvent Substances 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 235000011121 sodium hydroxide Nutrition 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 239000013543 active substance Substances 0.000 description 10
- 239000003814 drug Substances 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 9
- 238000009835 boiling Methods 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 229910017604 nitric acid Inorganic materials 0.000 description 8
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 7
- 239000005457 ice water Substances 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 230000003902 lesion Effects 0.000 description 5
- 235000015497 potassium bicarbonate Nutrition 0.000 description 5
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 5
- 239000011736 potassium bicarbonate Substances 0.000 description 5
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 150000003568 thioethers Chemical class 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000000370 acceptor Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 4
- JCBJVAJGLKENNC-UHFFFAOYSA-M potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- FSKBGJJQSWUWKX-UHFFFAOYSA-N 2-[(4-methoxy-3-methylpyridin-2-yl)methylsulfanyl]-6-(trifluoromethoxy)-1h-benzimidazole Chemical compound COC1=CC=NC(CSC=2NC3=CC=C(OC(F)(F)F)C=C3N=2)=C1C FSKBGJJQSWUWKX-UHFFFAOYSA-N 0.000 description 3
- VTSXVHVTPWBBNM-UHFFFAOYSA-N 2-[(4-methoxypyridin-2-yl)methylsulfanyl]-6-(1,1,2,2-tetrafluoroethoxy)-1h-benzimidazole Chemical compound COC1=CC=NC(CSC=2NC3=CC(OC(F)(F)C(F)F)=CC=C3N=2)=C1 VTSXVHVTPWBBNM-UHFFFAOYSA-N 0.000 description 3
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
- UIUCDMJOXYLFHF-UHFFFAOYSA-N 5-(1,1,2,2-tetrafluoroethoxy)-1,3-dihydrobenzimidazole-2-thione Chemical compound FC(F)C(F)(F)OC1=CC=C2NC(S)=NC2=C1 UIUCDMJOXYLFHF-UHFFFAOYSA-N 0.000 description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 208000025865 Ulcer Diseases 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 230000002496 gastric effect Effects 0.000 description 3
- 230000000968 intestinal effect Effects 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 150000002902 organometallic compounds Chemical class 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000011321 prophylaxis Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- 230000028327 secretion Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 150000003462 sulfoxides Chemical class 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- 231100000397 ulcer Toxicity 0.000 description 3
- YNQJHJPRQAPKHH-UHFFFAOYSA-N (4-methoxy-5-methylpyridin-2-yl)methanol Chemical compound COC1=CC(CO)=NC=C1C YNQJHJPRQAPKHH-UHFFFAOYSA-N 0.000 description 2
- ITQCXTOQWOFOGH-UHFFFAOYSA-N 1,2-bis(difluoromethoxy)benzene Chemical compound FC(F)OC1=CC=CC=C1OC(F)F ITQCXTOQWOFOGH-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- GFYHSKONPJXCDE-UHFFFAOYSA-N 2,3,5-trimethylpyridine Chemical compound CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 2
- FDNDPEVBJHZSAQ-UHFFFAOYSA-N 2-(chloromethyl)-4-methoxy-5-methylpyridine;hydrochloride Chemical compound Cl.COC1=CC(CCl)=NC=C1C FDNDPEVBJHZSAQ-UHFFFAOYSA-N 0.000 description 2
- UODFFWGYSJVFCZ-UHFFFAOYSA-N 2-(chloromethyl)-4-methoxypyridine Chemical compound COC1=CC=NC(CCl)=C1 UODFFWGYSJVFCZ-UHFFFAOYSA-N 0.000 description 2
- PBDFBZPTRXMFBL-UHFFFAOYSA-N 2-(chloromethyl)-4-methoxypyridine;hydrochloride Chemical compound Cl.COC1=CC=NC(CCl)=C1 PBDFBZPTRXMFBL-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- NQYANFAPNZYLCA-UHFFFAOYSA-N 2-[(3-methylpyridin-2-yl)methylsulfanyl]-6-(1,1,2,2-tetrafluoroethoxy)-1h-benzimidazole Chemical compound CC1=CC=CN=C1CSC1=NC2=CC=C(OC(F)(F)C(F)F)C=C2N1 NQYANFAPNZYLCA-UHFFFAOYSA-N 0.000 description 2
- CJKBWPVBQKUARO-UHFFFAOYSA-N 2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfanyl]-6-(1,1,2,2-tetrafluoroethoxy)-1h-benzimidazole Chemical compound COC1=C(C)C=NC(CSC=2NC3=CC(OC(F)(F)C(F)F)=CC=C3N=2)=C1C CJKBWPVBQKUARO-UHFFFAOYSA-N 0.000 description 2
- FGGLBZJAVPSKQY-UHFFFAOYSA-N 2-[(4-methoxy-3-methylpyridin-2-yl)methylsulfinyl]-6-(trifluoromethoxy)-1h-benzimidazole Chemical compound COC1=CC=NC(CS(=O)C=2NC3=CC=C(OC(F)(F)F)C=C3N=2)=C1C FGGLBZJAVPSKQY-UHFFFAOYSA-N 0.000 description 2
- ULJDHENNWLMFBJ-UHFFFAOYSA-N 2-[(4-methoxy-5-methylpyridin-2-yl)methylsulfanyl]-6-(1,1,2,2-tetrafluoroethoxy)-1h-benzimidazole Chemical compound C1=C(C)C(OC)=CC(CSC=2NC3=CC=C(OC(F)(F)C(F)F)C=C3N=2)=N1 ULJDHENNWLMFBJ-UHFFFAOYSA-N 0.000 description 2
- MYVOKHHYLAQNCN-UHFFFAOYSA-N 2-[(4-methoxypyridin-2-yl)methylsulfanyl]-6-(2,2,2-trifluoroethoxy)-1h-benzimidazole Chemical compound COC1=CC=NC(CSC=2NC3=CC(OCC(F)(F)F)=CC=C3N=2)=C1 MYVOKHHYLAQNCN-UHFFFAOYSA-N 0.000 description 2
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 2
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- 150000002739 metals Chemical class 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- GUCOPPBIPNYWRV-UHFFFAOYSA-N n-[2-nitro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(OC(F)(F)C(F)F)C=C1[N+]([O-])=O GUCOPPBIPNYWRV-UHFFFAOYSA-N 0.000 description 1
- GLVCSHDYSVIDOR-UHFFFAOYSA-N n-[3,4-bis(difluoromethoxy)phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(OC(F)F)C(OC(F)F)=C1 GLVCSHDYSVIDOR-UHFFFAOYSA-N 0.000 description 1
- UFLSHCCECIDOQI-UHFFFAOYSA-N n-[3-(difluoromethoxy)-4-methoxyphenyl]acetamide Chemical compound COC1=CC=C(NC(C)=O)C=C1OC(F)F UFLSHCCECIDOQI-UHFFFAOYSA-N 0.000 description 1
- UIRBAARIPFMQLX-UHFFFAOYSA-N n-[4,5-bis(difluoromethoxy)-2-nitrophenyl]acetamide Chemical compound CC(=O)NC1=CC(OC(F)F)=C(OC(F)F)C=C1[N+]([O-])=O UIRBAARIPFMQLX-UHFFFAOYSA-N 0.000 description 1
- APPKNBWGBWXVQA-UHFFFAOYSA-N n-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(OC(F)(F)C(F)F)C=C1 APPKNBWGBWXVQA-UHFFFAOYSA-N 0.000 description 1
- XWJZCTFTYLPSMG-UHFFFAOYSA-N n-[4-(2,2,2-trifluoroethoxy)phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(OCC(F)(F)F)C=C1 XWJZCTFTYLPSMG-UHFFFAOYSA-N 0.000 description 1
- YZAFOMJODXAJQD-UHFFFAOYSA-N n-[4-(difluoromethoxy)phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(OC(F)F)C=C1 YZAFOMJODXAJQD-UHFFFAOYSA-N 0.000 description 1
- RNAQYXPBRBVEBQ-UHFFFAOYSA-N n-[4-[chloro(difluoro)methoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(OC(F)(F)Cl)C=C1 RNAQYXPBRBVEBQ-UHFFFAOYSA-N 0.000 description 1
- UGJZRTBEADDGRO-UHFFFAOYSA-N n-[4-chloro-3-(difluoromethoxy)-2-nitrophenyl]acetamide Chemical compound CC(=O)NC1=CC=C(Cl)C(OC(F)F)=C1[N+]([O-])=O UGJZRTBEADDGRO-UHFFFAOYSA-N 0.000 description 1
- BBULBKJDQUAZLY-UHFFFAOYSA-N n-[5-(difluoromethoxy)-4-methoxy-2-nitrophenyl]acetamide Chemical compound COC1=CC([N+]([O-])=O)=C(NC(C)=O)C=C1OC(F)F BBULBKJDQUAZLY-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229940039748 oxalate Drugs 0.000 description 1
- 229960002369 oxyphencyclimine Drugs 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000005009 perfluoropropyl group Chemical group FC(C(C(F)(F)F)(F)F)(F)* 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000002831 pharmacologic agent Substances 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
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- SHNUBALDGXWUJI-UHFFFAOYSA-N pyridin-2-ylmethanol Chemical class OCC1=CC=CC=N1 SHNUBALDGXWUJI-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000011552 rat model Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000002271 resection Methods 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- MOODSJOROWROTO-UHFFFAOYSA-N salicylsulfuric acid Chemical compound OC(=O)C1=CC=CC=C1OS(O)(=O)=O MOODSJOROWROTO-UHFFFAOYSA-N 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- KEAYESYHFKHZAL-IGMARMGPSA-N sodium-23 atom Chemical compound [23Na] KEAYESYHFKHZAL-IGMARMGPSA-N 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229940086735 succinate Drugs 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- IWOKCMBOJXYDEE-UHFFFAOYSA-N sulfinylmethane Chemical compound C=S=O IWOKCMBOJXYDEE-UHFFFAOYSA-N 0.000 description 1
- 229940071103 sulfosalicylate Drugs 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- GKCBAIGFKIBETG-UHFFFAOYSA-N tetracaine Chemical compound CCCCNC1=CC=C(C(=O)OCCN(C)C)C=C1 GKCBAIGFKIBETG-UHFFFAOYSA-N 0.000 description 1
- 229960002372 tetracaine Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 239000003860 topical agent Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
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
- C07D401/12—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
- Steroid Compounds (AREA)
- Medicinal Preparation (AREA)
- Diaphragms For Electromechanical Transducers (AREA)
- Investigating Or Analyzing Materials By The Use Of Ultrasonic Waves (AREA)
- Heat Treatment Of Sheet Steel (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH240183 | 1983-05-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO841754L true NO841754L (no) | 1984-11-05 |
Family
ID=4232920
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO841754A NO841754L (no) | 1983-05-03 | 1984-05-02 | Fremgangsmaate ved fremstilling av nye fluoralkoksyforbindelser |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4555518A (el) |
| EP (1) | EP0134400B1 (el) |
| JP (2) | JPS59206379A (el) |
| KR (1) | KR840009098A (el) |
| AT (1) | ATE87311T1 (el) |
| AU (1) | AU579316B2 (el) |
| DE (1) | DE3486109D1 (el) |
| DK (1) | DK217184A (el) |
| ES (2) | ES8604927A1 (el) |
| FI (1) | FI841759A (el) |
| GR (1) | GR79849B (el) |
| HU (1) | HU195220B (el) |
| IL (1) | IL71664A (el) |
| NO (1) | NO841754L (el) |
| NZ (1) | NZ208023A (el) |
| PT (1) | PT78518B (el) |
| ZA (1) | ZA843288B (el) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZW4585A1 (en) * | 1984-04-19 | 1985-11-20 | Hoffmann La Roche | Imidazole derivatives |
| IL75400A (en) * | 1984-06-16 | 1988-10-31 | Byk Gulden Lomberg Chem Fab | Dialkoxypyridine methyl(sulfinyl or sulfonyl)benzimidazoles,processes for the preparation thereof and pharmaceutical compositions containing the same |
| GB8417194D0 (en) * | 1984-07-05 | 1984-08-08 | Boots Co Plc | Therapeutic agents |
| JPS6150979A (ja) * | 1984-08-16 | 1986-03-13 | Takeda Chem Ind Ltd | ピリジン誘導体およびその製造法 |
| JPS6150978A (ja) * | 1984-08-16 | 1986-03-13 | Takeda Chem Ind Ltd | ピリジン誘導体およびその製造法 |
| DE3430513A1 (de) * | 1984-08-18 | 1986-02-27 | Wella Ag, 6100 Darmstadt | Haarfaerbemittel mit diamino-tetrafluorethoxybenzolen sowie neue diamino-tetrafluorethoxybenzole |
| IL76839A (en) * | 1984-10-31 | 1988-08-31 | Byk Gulden Lomberg Chem Fab | Picoline derivatives,processes for the preparation thereof and pharmaceutical compositions containing the same |
| US4738975A (en) * | 1985-07-02 | 1988-04-19 | Takeda Chemical Industries, Ltd. | Pyridine derivatives, and use as anti-ulcer agents |
| JPS6261978A (ja) * | 1985-09-12 | 1987-03-18 | Otsuka Pharmaceut Co Ltd | ５−フルオロ−１ｈ−ベンズイミダゾ−ル誘導体 |
| DE3621215A1 (de) * | 1986-06-25 | 1988-01-07 | Bayer Ag | Fluorhaltige o-phenylendiamine und o-aminophenole |
| JPH0643426B2 (ja) * | 1986-07-25 | 1994-06-08 | 東京田辺製薬株式会社 | イミダゾ〔４，５−ｂ〕ピリジン誘導体、その製造法及びそれを含有する抗潰瘍剤 |
| FI96860C (fi) * | 1987-06-17 | 1996-09-10 | Eisai Co Ltd | Analogiamenetelmä lääkeaineena käytettävän pyridiinijohdannaisen valmistamiseksi |
| DK171989B1 (da) * | 1987-08-04 | 1997-09-08 | Takeda Chemical Industries Ltd | Fremgangsmåde til fremstilling af 2-(2-pyridylmethylsulfinyl)-benzimidazoler |
| JPH03504497A (ja) * | 1988-05-25 | 1991-10-03 | ビイク グルデン ロンベルク ヒエーミツシエ フアブリーク ゲゼルシヤフト ミツト ベシユレンクテル ハフツング | 新規フルオルアルコキシ化合物 |
| US5223515A (en) * | 1988-08-18 | 1993-06-29 | Takeda Chemical Industries, Ltd. | Injectable solution containing a pyridyl methylsulfinylbenzimidazole |
| AT391693B (de) * | 1988-11-15 | 1990-11-12 | Cl Pharma | Verfahren zur herstellung von 3-5-dimethyl-4methoxypyridinderivaten sowie neues zwischenprodukt hierfuer |
| IE64199B1 (en) * | 1988-12-22 | 1995-07-12 | Haessle Ab | Compound with gastric acid inhibitory effect and process for its preparation |
| SE8804629D0 (sv) | 1988-12-22 | 1988-12-22 | Ab Haessle | New therapeutically active compounds |
| SE8804628D0 (sv) | 1988-12-22 | 1988-12-22 | Ab Haessle | New compounds |
| US4965269A (en) * | 1989-12-20 | 1990-10-23 | Ab Hassle | Therapeutically active chloro substituted benzimidazoles |
| US5049674A (en) | 1989-12-20 | 1991-09-17 | Aktiebolaget Hassle | Therapeutically active fluoro substituted benzimidazoles |
| US5274099A (en) * | 1989-12-20 | 1993-12-28 | Aktiebolaget Hassle | Therapeutically active fluoro substituted benzimidazoles |
| EP0731801B1 (de) | 1993-12-01 | 2001-10-24 | Byk Gulden Lomberg Chemische Fabrik GmbH | Substituierte aminoalkylaminopyridine |
| ATE262332T1 (de) * | 1995-09-21 | 2004-04-15 | Pharma Pass Ii Llc | Lansoprazolhaltige arzneizusammensetzung und herstellungsverfahren |
| US6312712B1 (en) | 1999-08-26 | 2001-11-06 | Robert R. Whittle | Method of improving bioavailability |
| 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 |
| US6316020B1 (en) | 1999-08-26 | 2001-11-13 | Robert R. Whittle | Pharmaceutical formulations |
| US6268385B1 (en) | 1999-08-26 | 2001-07-31 | Robert R. Whittle | Dry blend pharmaceutical formulations |
| 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 |
| US6262086B1 (en) | 1999-08-26 | 2001-07-17 | Robert R. Whittle | Pharmaceutical unit dosage form |
| US6312723B1 (en) | 1999-08-26 | 2001-11-06 | Robert R. Whittle | Pharmaceutical unit dosage form |
| US6326384B1 (en) | 1999-08-26 | 2001-12-04 | Robert R. Whittle | Dry blend pharmaceutical unit dosage form |
| US6780880B1 (en) | 1999-08-26 | 2004-08-24 | Robert R. Whittle | FT-Raman spectroscopic measurement |
| ES2171116B1 (es) * | 2000-04-14 | 2003-08-01 | Esteve Quimica Sa | Procedimiento para la obtencion de derivados de (((piridil sustituido)metil)tio)bencimidazol. |
| US20020064555A1 (en) * | 2000-09-29 | 2002-05-30 | Dan Cullen | Proton pump inhibitor formulation |
| US20030228363A1 (en) * | 2002-06-07 | 2003-12-11 | Patel Mahendra R. | Stabilized pharmaceutical compositons containing benzimidazole compounds |
| CA2510849A1 (en) * | 2002-12-19 | 2004-07-08 | Teva Pharmaceutical Industries Ltd | Solid states of pantoprazole sodium, processes for preparing them and processes for preparing known pantoprazole sodium hydrates |
| US7439367B2 (en) * | 2003-01-15 | 2008-10-21 | Cipla Limited | Pharmaceutical process and compounds prepared thereby |
| US20040235904A1 (en) * | 2003-03-12 | 2004-11-25 | Nina Finkelstein | Crystalline and amorphous solids of pantoprazole and processes for their preparation |
| MXPA05013316A (es) | 2003-06-10 | 2006-03-17 | Teva Pharma | Proceso para preparar bencimidazoles 2[-(piridinil)metil]sulfinil-sustituidos y derivados clorados novedosos de pantoprazol. |
| US20060024362A1 (en) | 2004-07-29 | 2006-02-02 | Pawan Seth | Composition comprising a benzimidazole and process for its manufacture |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4045564A (en) * | 1974-02-18 | 1977-08-30 | Ab Hassle | Benzimidazole derivatives useful as gastric acid secretion inhibitors |
| SE416649B (sv) * | 1974-05-16 | 1981-01-26 | Haessle Ab | Forfarande for framstellning av foreningar som paverkar magsyrasekretionen |
| LU77125A1 (el) * | 1977-04-12 | 1979-01-18 | ||
| LU77115A1 (el) * | 1977-04-12 | 1979-01-18 | ||
| SE7804231L (sv) * | 1978-04-14 | 1979-10-15 | Haessle Ab | Magsyrasekretionsmedel |
| IT1119096B (it) * | 1978-06-05 | 1986-03-03 | Sankyo Co | Derivati della benzotiazocina e della benzotiazonina particolarmente utili come medicamenti e procedimento per la loro preparazione |
| CH642359A5 (en) * | 1978-10-02 | 1984-04-13 | Ciba Geigy Ag | Benzimidazole derivatives |
| US4359465A (en) * | 1980-07-28 | 1982-11-16 | The Upjohn Company | Methods for treating gastrointestinal inflammation |
| CH644116A5 (de) * | 1980-08-21 | 1984-07-13 | Hoffmann La Roche | Imidazolderivate. |
| IL66340A (en) * | 1981-08-13 | 1986-08-31 | Haessle Ab | Pharmaceutical compositions comprising pyridylmethyl-thiobenzimidazole derivatives,certain such novel derivatives and their preparation |
| IE57646B1 (en) * | 1983-12-16 | 1993-02-10 | Wyeth John & Brother Ltd | Derivatives of imidazoquinolines and analogues thereof |
| GB8526154D0 (en) * | 1985-02-06 | 1985-11-27 | Kotobuki Seiyaku Co Ltd | 2-substituted cyclo-heptoimidazoles |
| KR950001015B1 (ko) * | 1986-01-10 | 1995-02-07 | 닛뽕 케미화 가부시끼가이샤 | 술폭시드 유도체의 제조방법 |
| FR2597478B1 (fr) * | 1986-04-21 | 1988-12-16 | Esteve Labor Dr | Benzimidazoles et imidazopyridines sulfonamides, leur preparation et leur application en tant que medicaments. |
| EP0251536A1 (en) * | 1986-06-24 | 1988-01-07 | FISONS plc | Benzimidazoles, their production, formulation and use as gastric acid secretion inhibitors |
| JPH0643426B2 (ja) * | 1986-07-25 | 1994-06-08 | 東京田辺製薬株式会社 | イミダゾ〔４，５−ｂ〕ピリジン誘導体、その製造法及びそれを含有する抗潰瘍剤 |
-
1984
- 1984-04-27 IL IL71664A patent/IL71664A/xx not_active IP Right Cessation
- 1984-04-27 HU HU864147A patent/HU195220B/hu unknown
- 1984-04-30 AU AU27500/84A patent/AU579316B2/en not_active Ceased
- 1984-05-01 US US06/606,872 patent/US4555518A/en not_active Expired - Fee Related
- 1984-05-01 DK DK217184A patent/DK217184A/da not_active Application Discontinuation
- 1984-05-02 NZ NZ208023A patent/NZ208023A/en unknown
- 1984-05-02 JP JP59087967A patent/JPS59206379A/ja active Granted
- 1984-05-02 PT PT78518A patent/PT78518B/pt unknown
- 1984-05-02 NO NO841754A patent/NO841754L/no unknown
- 1984-05-02 GR GR74557A patent/GR79849B/el unknown
- 1984-05-03 FI FI841759A patent/FI841759A/fi not_active Application Discontinuation
- 1984-05-03 ES ES532149A patent/ES8604927A1/es not_active Expired
- 1984-05-03 DE DE8484104993T patent/DE3486109D1/de not_active Expired - Lifetime
- 1984-05-03 KR KR1019840002392A patent/KR840009098A/ko not_active Application Discontinuation
- 1984-05-03 EP EP84104993A patent/EP0134400B1/de not_active Expired - Lifetime
- 1984-05-03 ZA ZA843288A patent/ZA843288B/xx unknown
- 1984-05-03 AT AT84104993T patent/ATE87311T1/de not_active IP Right Cessation
-
1985
- 1985-07-12 ES ES545145A patent/ES8603866A1/es not_active Expired
-
1992
- 1992-03-24 JP JP4065838A patent/JPH0586037A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| PT78518B (de) | 1986-07-14 |
| AU2750084A (en) | 1984-11-08 |
| JPH0587508B2 (el) | 1993-12-16 |
| IL71664A (en) | 1987-11-30 |
| JPS59206379A (ja) | 1984-11-22 |
| KR840009098A (ko) | 1984-12-24 |
| PT78518A (de) | 1984-06-01 |
| EP0134400A2 (de) | 1985-03-20 |
| ES545145A0 (es) | 1986-01-16 |
| DE3486109D1 (de) | 1993-04-29 |
| FI841759A0 (fi) | 1984-05-03 |
| HU195220B (en) | 1988-04-28 |
| EP0134400A3 (en) | 1985-12-11 |
| JPH0586037A (ja) | 1993-04-06 |
| AU579316B2 (en) | 1988-11-24 |
| EP0134400B1 (de) | 1993-03-24 |
| US4555518A (en) | 1985-11-26 |
| DK217184D0 (da) | 1984-05-01 |
| NZ208023A (en) | 1987-07-31 |
| DK217184A (da) | 1984-11-04 |
| ES8603866A1 (es) | 1986-01-16 |
| IL71664A0 (en) | 1984-07-31 |
| ZA843288B (en) | 1984-12-24 |
| FI841759A (fi) | 1984-11-04 |
| GR79849B (el) | 1984-10-31 |
| ATE87311T1 (de) | 1993-04-15 |
| ES8604927A1 (es) | 1986-03-01 |
| ES532149A0 (es) | 1986-03-01 |
| JPH0572391B2 (el) | 1993-10-12 |
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