FI68230C - Analogifoerfarande foer framstaellning av terapeutiskt verksamma acyl-bensimidazol-2-derivat - Google Patents
Analogifoerfarande foer framstaellning av terapeutiskt verksamma acyl-bensimidazol-2-derivat Download PDFInfo
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- FI68230C FI68230C FI772521A FI772521A FI68230C FI 68230 C FI68230 C FI 68230C FI 772521 A FI772521 A FI 772521A FI 772521 A FI772521 A FI 772521A FI 68230 C FI68230 C FI 68230C
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- methyl
- acid
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- 150000001875 compounds Chemical class 0.000 claims description 95
- 239000000203 mixture Substances 0.000 claims description 68
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 52
- -1 acetoxymethyl Chemical group 0.000 claims description 49
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 40
- 238000006243 chemical reaction Methods 0.000 claims description 39
- 239000002253 acid Substances 0.000 claims description 36
- 150000003839 salts Chemical class 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 34
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 238000002360 preparation method Methods 0.000 claims description 20
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- AGZPIOULIKYWNV-UHFFFAOYSA-N 1-[2-(hydroxymethyl)-1,6-dimethylbenzimidazol-5-yl]butan-1-one Chemical compound C1=C(C)C(C(=O)CCC)=CC2=C1N(C)C(CO)=N2 AGZPIOULIKYWNV-UHFFFAOYSA-N 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 7
- 238000011065 in-situ storage Methods 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 150000003254 radicals Chemical class 0.000 claims description 6
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 125000001589 carboacyl group Chemical group 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 239000002841 Lewis acid Substances 0.000 claims description 2
- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 150000007517 lewis acids Chemical class 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 2
- 101000995861 Arabidopsis thaliana Regulatory protein NPR1 Proteins 0.000 claims 1
- 101000600885 Homo sapiens Serine/threonine-protein kinase NIM1 Proteins 0.000 claims 1
- RYXPMWYHEBGTRV-UHFFFAOYSA-N Omeprazole sodium Chemical compound [Na+].N=1C2=CC(OC)=CC=C2[N-]C=1S(=O)CC1=NC=C(C)C(OC)=C1C RYXPMWYHEBGTRV-UHFFFAOYSA-N 0.000 claims 1
- 102100037345 Serine/threonine-protein kinase NIM1 Human genes 0.000 claims 1
- 239000013522 chelant Substances 0.000 claims 1
- 239000000700 radioactive tracer Substances 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 143
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 131
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 131
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 117
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 111
- 239000000243 solution Substances 0.000 description 107
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 90
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 66
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 61
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 53
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 51
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 50
- 229910052938 sodium sulfate Inorganic materials 0.000 description 43
- 235000011152 sodium sulphate Nutrition 0.000 description 43
- 239000007858 starting material Substances 0.000 description 41
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 40
- 238000003756 stirring Methods 0.000 description 40
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 38
- 239000000284 extract Substances 0.000 description 33
- 239000000155 melt Substances 0.000 description 32
- 239000000706 filtrate Substances 0.000 description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 25
- 238000001816 cooling Methods 0.000 description 25
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 24
- 239000002244 precipitate Substances 0.000 description 24
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 23
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
- 239000003208 petroleum Substances 0.000 description 22
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 21
- 239000012286 potassium permanganate Substances 0.000 description 21
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 20
- 229910000564 Raney nickel Inorganic materials 0.000 description 20
- 239000007868 Raney catalyst Substances 0.000 description 19
- 239000003054 catalyst Substances 0.000 description 19
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- 239000012299 nitrogen atmosphere Substances 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 239000005909 Kieselgur Substances 0.000 description 14
- 238000001704 evaporation Methods 0.000 description 14
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 13
- 230000008020 evaporation Effects 0.000 description 13
- 239000000725 suspension Substances 0.000 description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 11
- 150000001340 alkali metals Chemical class 0.000 description 11
- 229910021529 ammonia Inorganic materials 0.000 description 11
- 238000010438 heat treatment Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 10
- 229910052783 alkali metal Inorganic materials 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 229910000029 sodium carbonate Inorganic materials 0.000 description 10
- 238000011282 treatment Methods 0.000 description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
- 125000004093 cyano group Chemical group *C#N 0.000 description 9
- 125000004122 cyclic group Chemical group 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 235000017557 sodium bicarbonate Nutrition 0.000 description 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
- 159000000000 sodium salts Chemical class 0.000 description 9
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 9
- YZGQDNOIGFBYKF-UHFFFAOYSA-N Ethoxyacetic acid Chemical compound CCOCC(O)=O YZGQDNOIGFBYKF-UHFFFAOYSA-N 0.000 description 8
- 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 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 8
- 238000005984 hydrogenation reaction Methods 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- 230000002378 acidificating effect Effects 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 230000001590 oxidative effect Effects 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- IMSLKRAVPGHJON-UHFFFAOYSA-N 5-butanoyl-1,6-dimethylbenzimidazole-2-carboxylic acid Chemical compound C1=C(C)C(C(=O)CCC)=CC2=C1N(C)C(C(O)=O)=N2 IMSLKRAVPGHJON-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 230000003301 hydrolyzing effect Effects 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 description 6
- 235000010755 mineral Nutrition 0.000 description 6
- 239000011707 mineral Substances 0.000 description 6
- 229910017604 nitric acid Inorganic materials 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
- IMZHEOIOBUYAKR-UHFFFAOYSA-N (5-butanoyl-1,6-dimethylbenzimidazol-2-yl)methyl acetate Chemical compound C1=C(C)C(C(=O)CCC)=CC2=C1N(C)C(COC(C)=O)=N2 IMZHEOIOBUYAKR-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 230000003266 anti-allergic effect Effects 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- WFNJKISRXLEQLJ-UHFFFAOYSA-N ethyl 5-butanoyl-1,6-dimethylbenzimidazole-2-carboxylate Chemical compound C1=C(C)C(C(=O)CCC)=CC2=C1N(C)C(C(=O)OCC)=N2 WFNJKISRXLEQLJ-UHFFFAOYSA-N 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical group O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 5
- QUIAPSGBAXIITH-UHFFFAOYSA-N 1-[2-(ethoxymethyl)-1,6-dimethylbenzimidazol-5-yl]butan-1-ol Chemical compound C1=C(C)C(C(O)CCC)=CC2=C1N(C)C(COCC)=N2 QUIAPSGBAXIITH-UHFFFAOYSA-N 0.000 description 4
- LZVVDQVORKVUSB-UHFFFAOYSA-N 5-butanoyl-1,6-dimethylbenzimidazole-2-carbaldehyde Chemical compound C1=C(C)C(C(=O)CCC)=CC2=C1N(C)C(C=O)=N2 LZVVDQVORKVUSB-UHFFFAOYSA-N 0.000 description 4
- PDQHWNXMXSPSPN-UHFFFAOYSA-N 5-butanoyl-6-methyl-1h-benzimidazole-2-carboxylic acid Chemical compound C1=C(C)C(C(=O)CCC)=CC2=C1N=C(C(O)=O)N2 PDQHWNXMXSPSPN-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000000427 antigen Substances 0.000 description 4
- 102000036639 antigens Human genes 0.000 description 4
- 108091007433 antigens Proteins 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 150000003568 thioethers Chemical class 0.000 description 4
- 125000004953 trihalomethyl group Chemical group 0.000 description 4
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 3
- YEVPHFIFGUWSMG-UHFFFAOYSA-N 1-(4-chloro-3-nitrophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 YEVPHFIFGUWSMG-UHFFFAOYSA-N 0.000 description 3
- CCZYTPDGSKQGJZ-UHFFFAOYSA-N 1-[2-(hydroxymethyl)-6-methyl-1h-benzimidazol-5-yl]butan-1-one Chemical compound C1=C(C)C(C(=O)CCC)=CC2=C1N=C(CO)N2 CCZYTPDGSKQGJZ-UHFFFAOYSA-N 0.000 description 3
- OSOUNOBYRMOXQQ-UHFFFAOYSA-N 1-chloro-3-methylbenzene Chemical compound CC1=CC=CC(Cl)=C1 OSOUNOBYRMOXQQ-UHFFFAOYSA-N 0.000 description 3
- IJMCBJOIYIYBMR-UHFFFAOYSA-N 2-(chloromethyl)-2-nitro-1-phenylbutan-1-one Chemical compound CCC(CCl)([N+]([O-])=O)C(=O)C1=CC=CC=C1 IJMCBJOIYIYBMR-UHFFFAOYSA-N 0.000 description 3
- MWFJMXGEHRFRLN-UHFFFAOYSA-N 4-chloro-2-methyl-2-nitro-1-phenylbutan-1-one Chemical compound ClCCC(C)([N+]([O-])=O)C(=O)C1=CC=CC=C1 MWFJMXGEHRFRLN-UHFFFAOYSA-N 0.000 description 3
- GRNUQNSPBUFODU-UHFFFAOYSA-N 4-chloro-3-nitro-1-phenylbutan-1-one Chemical compound [O-][N+](=O)C(CCl)CC(=O)C1=CC=CC=C1 GRNUQNSPBUFODU-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 206010002198 Anaphylactic reaction Diseases 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 206010020751 Hypersensitivity Diseases 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 208000026935 allergic disease Diseases 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 230000036783 anaphylactic response Effects 0.000 description 3
- 208000003455 anaphylaxis Diseases 0.000 description 3
- 239000007900 aqueous suspension Substances 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 3
- FFYPMLJYZAEMQB-UHFFFAOYSA-N diethyl pyrocarbonate Chemical compound CCOC(=O)OC(=O)OCC FFYPMLJYZAEMQB-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- OONMKRWGOWNJHC-UHFFFAOYSA-N ethyl 5-butanoyl-6-methyl-1h-benzimidazole-2-carboxylate Chemical compound C1=C(C)C(C(=O)CCC)=CC2=C1N=C(C(=O)OCC)N2 OONMKRWGOWNJHC-UHFFFAOYSA-N 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 229910001385 heavy metal Inorganic materials 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 150000002736 metal compounds Chemical class 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
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- 238000005809 transesterification reaction Methods 0.000 description 1
- DWCSXQCXXITVKE-UHFFFAOYSA-N triethyloxidanium Chemical compound CC[O+](CC)CC DWCSXQCXXITVKE-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- AAPLIUHOKVUFCC-UHFFFAOYSA-N trimethylsilanol Chemical compound C[Si](C)(C)O AAPLIUHOKVUFCC-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/12—Radicals substituted by oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/14—Decongestants or antiallergics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
- C07C49/807—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen all halogen atoms bound to the ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
- C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pulmonology (AREA)
- Neurology (AREA)
- Ophthalmology & Optometry (AREA)
- Communicable Diseases (AREA)
- Psychiatry (AREA)
- Oncology (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU75684A LU75684A1 (is") | 1976-08-27 | 1976-08-27 | |
| LU75684 | 1976-08-27 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI772521A7 FI772521A7 (fi) | 1978-02-28 |
| FI68230B FI68230B (fi) | 1985-04-30 |
| FI68230C true FI68230C (fi) | 1985-08-12 |
Family
ID=19728336
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI772521A FI68230C (fi) | 1976-08-27 | 1977-08-25 | Analogifoerfarande foer framstaellning av terapeutiskt verksamma acyl-bensimidazol-2-derivat |
Country Status (32)
| Country | Link |
|---|---|
| US (3) | US4141982A (is") |
| JP (1) | JPS5328172A (is") |
| AR (6) | AR224610A1 (is") |
| AT (1) | AT359060B (is") |
| AU (1) | AU517209B2 (is") |
| BE (1) | BE858157A (is") |
| CA (1) | CA1098526A (is") |
| CH (8) | CH631973A5 (is") |
| DD (1) | DD132735A5 (is") |
| DE (1) | DE2737462A1 (is") |
| DK (1) | DK381277A (is") |
| ES (7) | ES461906A1 (is") |
| FI (1) | FI68230C (is") |
| FR (1) | FR2362841A1 (is") |
| GB (2) | GB1595914A (is") |
| GR (1) | GR72908B (is") |
| HK (1) | HK93784A (is") |
| HU (2) | HU180700B (is") |
| IE (1) | IE45665B1 (is") |
| IL (1) | IL52820A (is") |
| LU (1) | LU75684A1 (is") |
| MY (1) | MY8500936A (is") |
| NL (1) | NL7709471A (is") |
| NO (1) | NO148488C (is") |
| NZ (1) | NZ185035A (is") |
| OA (1) | OA05753A (is") |
| PL (4) | PL112665B1 (is") |
| PT (1) | PT66947B (is") |
| SE (1) | SE434397B (is") |
| SG (1) | SG70784G (is") |
| SU (7) | SU882410A3 (is") |
| ZA (1) | ZA775182B (is") |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4312873A (en) * | 1978-09-29 | 1982-01-26 | Syntex (U.S.A.) Inc. | 5(6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity |
| US4322431A (en) * | 1979-02-09 | 1982-03-30 | Ciba-Geigy Corporation | Pharmaceutical preparations containing benzimidazole 2-derivatives |
| US4492708A (en) * | 1982-09-27 | 1985-01-08 | Eli Lilly And Company | Antiviral benzimidazoles |
| EP0277402B1 (en) * | 1987-02-03 | 1991-09-11 | W.R. Grace & Co.-Conn. | Biocide |
| JPH04197628A (ja) * | 1990-11-28 | 1992-07-17 | Sekisui Chem Co Ltd | 壁パネルの製造方法 |
| US5216003A (en) * | 1992-01-02 | 1993-06-01 | G. D. Searle & Co. | Diacid-containing benzimidazole compounds for treatment of neurotoxic injury |
| FR2751649B1 (fr) * | 1996-07-26 | 1998-08-28 | Adir | Nouveaux derives de benzimidazole, de benzoxazole et de benzothiazole, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| RU2430091C1 (ru) * | 2010-03-15 | 2011-09-27 | Учреждение Российской академии наук Институт химии и химической технологии Сибирского отделения РАН (ИХХТ СО РАН) | Способ получения 2,2-дизамещенных-4,5-бензо-циклопентадииминов-1,3 |
| US9663703B2 (en) | 2014-04-25 | 2017-05-30 | James George Clements | Method and compositions for enhanced oil recovery |
| CN109467512B (zh) * | 2018-12-18 | 2021-06-08 | 苏州开元民生科技股份有限公司 | 一种3,4-二氨基-二苯甲酮的合成方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB766749A (en) | 1954-01-11 | 1957-01-23 | Aschaffenburger Zellstoffwerke | Benzimidazole cobalamines and process for their preparation and separation |
| US3318889A (en) * | 1963-10-14 | 1967-05-09 | S B Penick & Company | 2-benzimidazole carbamates |
| DE1923481A1 (de) * | 1969-05-08 | 1970-11-12 | Hoechst Ag | Verfahren zur Herstellung von Amiden und Estern der 1-Hydroxy-benzimidazol-2-carbonsaeure |
| NL7013343A (is") * | 1969-09-26 | 1971-03-30 | ||
| BE759237A (fr) * | 1969-11-21 | 1971-05-01 | Montedison Spa | Procede de preparation d'amides a partir de composes heterocycliques azotes |
| BE792402A (fr) * | 1971-12-07 | 1973-06-07 | Ciba Geigy | Composes heterocycliques azotes et medicaments anthelminthiqueset antimicrobiens qui en contiennent |
| US4026936A (en) * | 1975-08-07 | 1977-05-31 | Hoffmann-La Roche Inc. | Anthelmintic pyridine and thiazole substituted benzimidazole carbamates |
-
1976
- 1976-08-27 LU LU75684A patent/LU75684A1/xx unknown
-
1977
- 1977-08-01 HU HU77CI1761A patent/HU180700B/hu unknown
- 1977-08-01 HU HU811133A patent/HU186765B/hu unknown
- 1977-08-18 US US05/825,630 patent/US4141982A/en not_active Expired - Lifetime
- 1977-08-19 DE DE19772737462 patent/DE2737462A1/de not_active Ceased
- 1977-08-22 PT PT66947A patent/PT66947B/pt unknown
- 1977-08-23 DD DD7700200697A patent/DD132735A5/xx unknown
- 1977-08-24 OA OA56266A patent/OA05753A/xx unknown
- 1977-08-25 FR FR7725938A patent/FR2362841A1/fr active Granted
- 1977-08-25 PL PL1977213906A patent/PL112665B1/pl unknown
- 1977-08-25 PL PL1977206452A patent/PL108853B1/pl unknown
- 1977-08-25 GB GB17219/80A patent/GB1595914A/en not_active Expired
- 1977-08-25 FI FI772521A patent/FI68230C/fi not_active IP Right Cessation
- 1977-08-25 PL PL1977211468A patent/PL110215B1/pl unknown
- 1977-08-25 CA CA285,456A patent/CA1098526A/en not_active Expired
- 1977-08-25 GB GB35710/77A patent/GB1595913A/en not_active Expired
- 1977-08-25 CH CH1040177A patent/CH631973A5/de not_active IP Right Cessation
- 1977-08-25 PL PL1977200449A patent/PL105527B1/pl not_active IP Right Cessation
- 1977-08-25 IL IL52820A patent/IL52820A/xx unknown
- 1977-08-26 AT AT620677A patent/AT359060B/de not_active IP Right Cessation
- 1977-08-26 SU SU772513755A patent/SU882410A3/ru active
- 1977-08-26 AU AU28255/77A patent/AU517209B2/en not_active Expired
- 1977-08-26 IE IE1779/77A patent/IE45665B1/en unknown
- 1977-08-26 BE BE180470A patent/BE858157A/xx not_active IP Right Cessation
- 1977-08-26 NL NL7709471A patent/NL7709471A/xx not_active Application Discontinuation
- 1977-08-26 NO NO772962A patent/NO148488C/no unknown
- 1977-08-26 SE SE7709615A patent/SE434397B/xx not_active IP Right Cessation
- 1977-08-26 NZ NZ185035A patent/NZ185035A/xx unknown
- 1977-08-26 ES ES461906A patent/ES461906A1/es not_active Expired
- 1977-08-26 DK DK381277A patent/DK381277A/da not_active Application Discontinuation
- 1977-08-26 GR GR54237A patent/GR72908B/el unknown
- 1977-08-26 ZA ZA00775182A patent/ZA775182B/xx unknown
- 1977-08-27 JP JP10312777A patent/JPS5328172A/ja active Granted
- 1977-08-29 AR AR268986A patent/AR224610A1/es active
-
1978
- 1978-06-26 SU SU782627856A patent/SU745365A3/ru active
- 1978-07-13 ES ES471686A patent/ES471686A1/es not_active Expired
- 1978-07-13 ES ES471688A patent/ES471688A1/es not_active Expired
- 1978-07-13 ES ES471687A patent/ES471687A1/es not_active Expired
- 1978-07-13 ES ES471689A patent/ES471689A1/es not_active Expired
- 1978-07-13 ES ES471690A patent/ES471690A1/es not_active Expired
- 1978-11-16 SU SU782685604A patent/SU923368A3/ru active
- 1978-11-16 SU SU782685605A patent/SU843744A3/ru active
- 1978-11-16 SU SU782685606A patent/SU831074A3/ru active
- 1978-11-20 US US05/962,426 patent/US4213993A/en not_active Expired - Lifetime
-
1979
- 1979-01-15 SU SU792707652A patent/SU784766A3/ru active
- 1979-01-15 SU SU792708672A patent/SU888819A3/ru active
- 1979-01-18 AR AR275218A patent/AR230990A1/es active
- 1979-01-18 AR AR275221A patent/AR225889A1/es active
- 1979-01-18 AR AR275220A patent/AR231536A1/es active
- 1979-01-18 AR AR275219A patent/AR222318A1/es active
- 1979-01-18 AR AR275222A patent/AR227621A1/es active
- 1979-04-02 ES ES79479189A patent/ES479189A0/es active Granted
- 1979-12-28 US US06/107,980 patent/US4344957A/en not_active Expired - Lifetime
-
1981
- 1981-09-30 CH CH630581A patent/CH631974A5/de not_active IP Right Cessation
- 1981-10-01 CH CH630481A patent/CH632749A5/de not_active IP Right Cessation
- 1981-10-13 CH CH653881A patent/CH631975A5/de not_active IP Right Cessation
- 1981-10-13 CH CH653681A patent/CH632253A5/de not_active IP Right Cessation
-
1982
- 1982-03-23 CH CH177582A patent/CH634305A5/de not_active IP Right Cessation
- 1982-07-27 CH CH455682A patent/CH637121A5/de not_active IP Right Cessation
- 1982-07-27 CH CH455582A patent/CH637120A5/de not_active IP Right Cessation
-
1984
- 1984-10-05 SG SG707/84A patent/SG70784G/en unknown
- 1984-11-29 HK HK937/84A patent/HK93784A/xx unknown
-
1985
- 1985-12-30 MY MY936/85A patent/MY8500936A/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: CIBA-GEIGY AG |