NO120426B - - Google Patents
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- NO120426B NO120426B NO165248A NO16524866A NO120426B NO 120426 B NO120426 B NO 120426B NO 165248 A NO165248 A NO 165248A NO 16524866 A NO16524866 A NO 16524866A NO 120426 B NO120426 B NO 120426B
- Authority
- NO
- Norway
- Prior art keywords
- group
- general formula
- molecular weight
- low molecular
- groups
- Prior art date
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- -1 hydrosulfide ions Chemical class 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 22
- 239000011541 reaction mixture Substances 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 150000002460 imidazoles Chemical class 0.000 claims description 4
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 claims description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 238000011065 in-situ storage Methods 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 239000002798 polar solvent Substances 0.000 claims description 3
- 125000000524 functional group Chemical group 0.000 claims description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 2
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 44
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 238000010992 reflux Methods 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 238000001816 cooling Methods 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 238000003776 cleavage reaction Methods 0.000 description 8
- 230000007017 scission Effects 0.000 description 8
- 239000002026 chloroform extract Substances 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- BVVSUFVLGBJYOR-UHFFFAOYSA-N (2-methyl-1,3-dioxolan-2-yl)methanamine Chemical compound NCC1(C)OCCO1 BVVSUFVLGBJYOR-UHFFFAOYSA-N 0.000 description 2
- HJKLEAOXCZIMPI-UHFFFAOYSA-N 2,2-diethoxyethanamine Chemical compound CCOC(CN)OCC HJKLEAOXCZIMPI-UHFFFAOYSA-N 0.000 description 2
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 2
- RGYNOPLNIDBIGT-UHFFFAOYSA-N 4-(4-chlorophenyl)-3-methyl-1h-imidazole-2-thione Chemical compound N1C(=S)N(C)C(C=2C=CC(Cl)=CC=2)=C1 RGYNOPLNIDBIGT-UHFFFAOYSA-N 0.000 description 2
- OMEMSRAKHTWJCI-UHFFFAOYSA-N CCOC(CN)OCC.N=C=S Chemical compound CCOC(CN)OCC.N=C=S OMEMSRAKHTWJCI-UHFFFAOYSA-N 0.000 description 2
- PLVQZWFZVFASKS-UHFFFAOYSA-N CN1C(=NC(=C1C1=CC=C(C=C1)OC)C)S Chemical compound CN1C(=NC(=C1C1=CC=C(C=C1)OC)C)S PLVQZWFZVFASKS-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000008098 formaldehyde solution Substances 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-M hydrosulfide Chemical compound [SH-] RWSOTUBLDIXVET-UHFFFAOYSA-M 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 150000002540 isothiocyanates Chemical class 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- HDBACITVPQEAGG-UHFFFAOYSA-N 1-fluoro-3-isothiocyanatobenzene Chemical compound FC1=CC=CC(N=C=S)=C1 HDBACITVPQEAGG-UHFFFAOYSA-N 0.000 description 1
- NFIUJHJMCQQYDL-UHFFFAOYSA-N 1-fluoro-4-isothiocyanatobenzene Chemical compound FC1=CC=C(N=C=S)C=C1 NFIUJHJMCQQYDL-UHFFFAOYSA-N 0.000 description 1
- OJWYYSVOSNWCCE-UHFFFAOYSA-N 2-methoxyethyl hypofluorite Chemical compound COCCOF OJWYYSVOSNWCCE-UHFFFAOYSA-N 0.000 description 1
- PQERDOPEWJNMPK-UHFFFAOYSA-N 3-(2,3-dimethylphenyl)-1h-imidazole-2-thione Chemical compound CC1=CC=CC(N2C(NC=C2)=S)=C1C PQERDOPEWJNMPK-UHFFFAOYSA-N 0.000 description 1
- WTKUSKNQFVDJGV-UHFFFAOYSA-N 3-(2,4-difluorophenyl)-1h-imidazole-2-thione Chemical compound FC1=CC(F)=CC=C1N1C(S)=NC=C1 WTKUSKNQFVDJGV-UHFFFAOYSA-N 0.000 description 1
- MBLFDPTVVARISG-UHFFFAOYSA-N 3-(2,6-dichlorophenyl)-1h-imidazole-2-thione Chemical compound ClC1=CC=CC(Cl)=C1N1C(=S)NC=C1 MBLFDPTVVARISG-UHFFFAOYSA-N 0.000 description 1
- BMCFCDCBHCVAIC-UHFFFAOYSA-N 3-(3-fluorophenyl)-1h-imidazole-2-thione Chemical compound FC1=CC=CC(N2C(NC=C2)=S)=C1 BMCFCDCBHCVAIC-UHFFFAOYSA-N 0.000 description 1
- ZKPXIPSWVWPFDF-UHFFFAOYSA-N 3-(4-bromophenyl)-1h-imidazole-2-thione Chemical compound C1=CC(Br)=CC=C1N1C(=S)NC=C1 ZKPXIPSWVWPFDF-UHFFFAOYSA-N 0.000 description 1
- QJWMVYCYPCPSKK-UHFFFAOYSA-N 3-(4-chlorophenyl)-1h-imidazole-2-thione Chemical compound C1=CC(Cl)=CC=C1N1C(=S)NC=C1 QJWMVYCYPCPSKK-UHFFFAOYSA-N 0.000 description 1
- GWYZXHXGBADGGC-UHFFFAOYSA-N 3-(4-fluorophenyl)-1h-imidazole-2-thione Chemical compound C1=CC(F)=CC=C1N1C(S)=NC=C1 GWYZXHXGBADGGC-UHFFFAOYSA-N 0.000 description 1
- LIEBCNQPMNARMP-UHFFFAOYSA-N 3-(4-methoxyphenyl)-1h-imidazole-2-thione Chemical compound C1=CC(OC)=CC=C1N1C(=S)NC=C1 LIEBCNQPMNARMP-UHFFFAOYSA-N 0.000 description 1
- FQMZFHKIYYCCAX-UHFFFAOYSA-N 3-[3-(trifluoromethyl)phenyl]-1h-imidazole-2-thione Chemical compound FC(F)(F)C1=CC=CC(N2C(NC=C2)=S)=C1 FQMZFHKIYYCCAX-UHFFFAOYSA-N 0.000 description 1
- GEUKXLKPQGIDDE-UHFFFAOYSA-N 3-[4-(trifluoromethyl)phenyl]-1h-imidazole-2-thione Chemical compound C1=CC(C(F)(F)F)=CC=C1N1C(=S)NC=C1 GEUKXLKPQGIDDE-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- VMSZFBSYWXMXRF-UHFFFAOYSA-N 3-isothiocyanatopyridine Chemical compound S=C=NC1=CC=CN=C1 VMSZFBSYWXMXRF-UHFFFAOYSA-N 0.000 description 1
- GUFDFGXJICAQJM-UHFFFAOYSA-N 3-pyridin-3-yl-1h-imidazole-2-thione Chemical compound SC1=NC=CN1C1=CC=CN=C1 GUFDFGXJICAQJM-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- VFASLFCNQYOKKK-UHFFFAOYSA-N 4-(4-chlorophenyl)-3,5-dimethyl-1H-imidazole-2-thione Chemical compound CN1C(=NC(=C1C1=CC=C(C=C1)Cl)C)S VFASLFCNQYOKKK-UHFFFAOYSA-N 0.000 description 1
- CQYXXBUINDPILP-UHFFFAOYSA-N 4-(4-fluorophenyl)-1,3-dihydroimidazole-2-thione Chemical compound C1=CC(F)=CC=C1C1=CNC(S)=N1 CQYXXBUINDPILP-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- VEGBCNLLYGMDKU-UHFFFAOYSA-N 4-methyl-3-pyridin-2-yl-1h-imidazole-2-thione Chemical compound CC1=CNC(=S)N1C1=CC=CC=N1 VEGBCNLLYGMDKU-UHFFFAOYSA-N 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZOQMXJXYIZXROV-UHFFFAOYSA-N CN1C(=NC(=C1C1=CC=C(C=C1)C)C)S Chemical compound CN1C(=NC(=C1C1=CC=C(C=C1)C)C)S ZOQMXJXYIZXROV-UHFFFAOYSA-N 0.000 description 1
- VWFRYOVOGGPBBE-UHFFFAOYSA-N CN1C(=NC(=C1C1=CC=C(C=C1)Cl)C(=O)O)S Chemical compound CN1C(=NC(=C1C1=CC=C(C=C1)Cl)C(=O)O)S VWFRYOVOGGPBBE-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- UYJXRRSPUVSSMN-UHFFFAOYSA-P ammonium sulfide Chemical compound [NH4+].[NH4+].[S-2] UYJXRRSPUVSSMN-UHFFFAOYSA-P 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 229960004365 benzoic acid Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- JGIATAMCQXIDNZ-UHFFFAOYSA-N calcium sulfide Chemical compound [Ca]=S JGIATAMCQXIDNZ-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229960004106 citric acid Drugs 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 230000000911 decarboxylating effect Effects 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 125000004212 difluorophenyl group Chemical group 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229960002598 fumaric acid Drugs 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000006303 iodophenyl group Chemical group 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940098895 maleic acid Drugs 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 229940099690 malic acid Drugs 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- DPLVEEXVKBWGHE-UHFFFAOYSA-N potassium sulfide Chemical compound [S-2].[K+].[K+] DPLVEEXVKBWGHE-UHFFFAOYSA-N 0.000 description 1
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
- C07C331/16—Isothiocyanates
- C07C331/18—Isothiocyanates having isothiocyanate groups bound to acyclic carbon atoms
- C07C331/20—Isothiocyanates having isothiocyanate groups bound to acyclic carbon atoms of a saturated carbon skeleton
-
- 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
- C07D233/84—Sulfur atoms
-
- 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
- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/28—Radicals substituted by nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US50024565A | 1965-10-21 | 1965-10-21 | |
| US72193068A | 1968-04-17 | 1968-04-17 | |
| US72192968A | 1968-04-17 | 1968-04-17 | |
| US72192868A | 1968-04-17 | 1968-04-17 | |
| US87494769A | 1969-11-07 | 1969-11-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO120426B true NO120426B (nl) | 1970-10-19 |
Family
ID=27541791
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO165248A NO120426B (nl) | 1965-10-21 | 1966-10-20 |
Country Status (10)
| Country | Link |
|---|---|
| US (4) | US3622584A (nl) |
| BE (1) | BE688585A (nl) |
| BR (1) | BR6683847D0 (nl) |
| DE (1) | DE1695093A1 (nl) |
| FR (2) | FR1509975A (nl) |
| GB (1) | GB1155580A (nl) |
| IL (1) | IL26729A (nl) |
| NL (3) | NL6614808A (nl) |
| NO (1) | NO120426B (nl) |
| SE (1) | SE345453B (nl) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE428686B (sv) * | 1975-08-11 | 1983-07-18 | Du Pont | Forfarande for framstellning av antiinflammatoriskt aktiva imidazoler |
| US4190666A (en) * | 1975-08-11 | 1980-02-26 | E. I. Du Pont De Nemours And Company | Anti-inflammatory 4,5-diarly-2-(substituted-thio)imidazoles and their corresponding sulfoxides and sulfones |
| US4159338A (en) * | 1977-02-09 | 1979-06-26 | E. I. Du Pont De Nemours And Company | Antiinflammatory-4,5-dicyclic-2-(substituted thio)-imidazoles and their corresponding sulfoxides and sulfones |
| US4182769A (en) * | 1977-02-09 | 1980-01-08 | E. I. Du Pont De Nemours And Company | Anti-inflammatory 1-substituted-4,5-diaryl-2-(substituted-thio) imidazoles and their corresponding sulfoxides and sulfones |
| DE2823197A1 (de) * | 1978-05-24 | 1979-11-29 | Schering Ag | Neue imidazolderivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
| US4199592A (en) * | 1978-08-29 | 1980-04-22 | E. I. Du Pont De Nemours And Company | Antiinflammatory 4,5-diaryl-2-nitroimidazoles |
| US4215135A (en) * | 1979-06-08 | 1980-07-29 | E. I. Du Pont De Nemours And Company | Antiinflammatory 2-substituted-1H-phenanthro[9,10-d]imidazoles |
| US4232029A (en) * | 1978-11-03 | 1980-11-04 | American Home Products Corporation | 1-Hydroxyimidazole-5-methanamine derivatives |
| DE2856909A1 (de) * | 1978-12-28 | 1980-07-17 | Schering Ag | Neue imidazolderivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
| DE3025484A1 (de) * | 1980-07-03 | 1982-02-04 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Neue imidazol-derivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
| US4338453A (en) * | 1980-09-17 | 1982-07-06 | The Upjohn Company | Aminoalkyl-1,2,4-triazoles |
| US4372964A (en) * | 1980-10-30 | 1983-02-08 | E. I. Du Pont De Nemours And Company | Antiinflammatory 4,5-diaryl-1H-imidazole-2-methanols |
| US4330552A (en) * | 1980-11-06 | 1982-05-18 | E. I. Du Pont De Nemours And Company | Antiinflammatory 4,5-diaryl-2-arylthioimidazoles |
| US4482775A (en) * | 1982-09-22 | 1984-11-13 | Chemical Research & Licensing Company | Isomerization of C4 alkenes |
| US4992459A (en) * | 1983-04-12 | 1991-02-12 | Smithkline Beecham Corporation | Dopamine-β-hydroxylase inhibitors |
| US4532331A (en) * | 1983-04-12 | 1985-07-30 | Smithkline Beckman Corporation | 1-Benzyl-2-aminomethyl imidazole derivatives |
| US4772723A (en) * | 1983-04-12 | 1988-09-20 | Smithkline Beckman Corporation | Dopamine β-hydroxylase inhibitors |
| US4863944A (en) * | 1983-04-12 | 1989-09-05 | Smithkline Beckman Corporation | Dopamine-β-hydroxylase inhibitors |
| PT78388B (en) * | 1983-04-12 | 1986-09-15 | Smithkline Beckman Corp | Dopamine-beta-hydroxylase inhibitors |
| US4532250A (en) * | 1983-11-23 | 1985-07-30 | American Hospital Supply Corporation | 5-Heteroarylimidazol-2-ones having cardiotonic activity |
| JPS61110266A (ja) * | 1984-11-05 | 1986-05-28 | Omron Tateisi Electronics Co | カード発行方法 |
| DE3508665A1 (de) * | 1985-03-12 | 1986-09-18 | Hoechst Ag, 6230 Frankfurt | Heterocyclische sulfide und ihre anwendung als immunmodulatoren |
| US4634711A (en) * | 1985-08-02 | 1987-01-06 | Smithkline Beckman Corporation | Pyridylalkyl imidazole-2-thiols |
| US4719223A (en) * | 1985-10-31 | 1988-01-12 | Smithkline Beckman Corporation | Imidazolethiol dopamine-beta-hydroxylase inhibitors |
| US4743613A (en) * | 1986-04-08 | 1988-05-10 | Smithkline Beckman Corporation | Ester prodrugs of dopamine-β-hydroxylase, inhibitors, composition containing them, and method of using them to inhibit dopamine-β-hydroxylase activity |
| US5057613A (en) * | 1986-05-06 | 1991-10-15 | Merrell Dow Pharmaceuticals | Novel thione dopamine beta hydroxylase inhibitors |
| IL82401A0 (en) * | 1986-05-06 | 1987-11-30 | Merrell Dow Pharma | Dopamine beta hydroxy-lase inhibiting imidazole derivatives and pharmaceutical compositions containing them |
| US4882348A (en) * | 1987-12-29 | 1989-11-21 | Smithkline Beckman Corporation | 2-(aminoalkylthio)imidazoles as dopamine-β-hydroxylase inhibitors |
| US4935438A (en) * | 1987-12-29 | 1990-06-19 | Smithkline Beckman Corporation | Dopamine-β-hydroxylase inhibitors |
| JPH03501730A (ja) * | 1987-12-31 | 1991-04-18 | スミスクライン・ベックマン・コーポレイション | １‐アラルキル‐１，２‐ジヒドロピリミジン‐２‐チオン類 |
| US4876266A (en) * | 1987-12-31 | 1989-10-24 | Smithkline Beckman Corporation | 1-aralkyl-2-mercaptoimidazolines as DBH inhibitors |
| US5300519A (en) * | 1988-07-06 | 1994-04-05 | The University Of Sheffield | Immunosuppressive agents |
| US5359139A (en) * | 1991-03-18 | 1994-10-25 | Albemarle Corporation | Tertiary amine treatment |
| US5393913A (en) * | 1993-03-03 | 1995-02-28 | Rhone-Poulenc Inc. | N-formylanilines |
| US6365616B1 (en) * | 1998-08-31 | 2002-04-02 | Sentron Medical, Inc. | Methimazole derivatives and tautomeric cyclic thiones to treat autoimmune diseases |
| EP1112072A2 (en) * | 1998-08-31 | 2001-07-04 | Sentron Medical, Inc. | Methimazole derivatives and tautomeric cyclic thiones to treat autoimmune diseases |
| US20020142974A1 (en) * | 1998-09-11 | 2002-10-03 | Leonard D. Kohn | Immune activation by double-stranded polynucleotides |
| DE10107683A1 (de) * | 2001-02-19 | 2002-08-29 | Merckle Gmbh Chem Pharm Fabrik | 2-Thio-substituierte Imidazolderivate und ihre Verwendung in der Pharmazie |
| FR2831822A1 (fr) * | 2001-11-07 | 2003-05-09 | Inst Nat Sante Rech Med | Utilisation therapeutique de derives 4-mercapto- ou 4-seleno-imidazoles |
| US20070167456A1 (en) * | 2004-08-11 | 2007-07-19 | Lommen Guy R E | Mercaptoimidazoles as ccr2 receptor antagonists |
| US10392381B2 (en) * | 2014-07-18 | 2019-08-27 | Ohio University | Prevention and treatment of non-alcoholic fatty liver disease |
| DE102022119618B3 (de) | 2022-08-04 | 2023-12-28 | Hans Schröder, Maschinenbau, Gesellschaft mit beschränkter Haftung | Schwenkbiegemaschine zur Erzeugung eines Hohlumschlags an einem Blech und Blechbiegeverfahren |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2585388A (en) * | 1948-11-17 | 1952-02-12 | Lilly Co Eli | Preparation of 2-mercaptoimidazoles |
-
1966
- 1966-10-20 FR FR80818A patent/FR1509975A/fr not_active Expired
- 1966-10-20 IL IL26729A patent/IL26729A/xx unknown
- 1966-10-20 DE DE19661695093 patent/DE1695093A1/de active Pending
- 1966-10-20 SE SE14303/66A patent/SE345453B/xx unknown
- 1966-10-20 BE BE688585D patent/BE688585A/xx unknown
- 1966-10-20 GB GB46982/66A patent/GB1155580A/en not_active Expired
- 1966-10-20 NL NL6614808A patent/NL6614808A/xx unknown
- 1966-10-20 NO NO165248A patent/NO120426B/no unknown
- 1966-10-30 BR BR183847/66A patent/BR6683847D0/pt unknown
-
1967
- 1967-01-19 FR FR91767A patent/FR6115M/fr not_active Expired
-
1968
- 1968-04-17 US US721929A patent/US3622584A/en not_active Expired - Lifetime
- 1968-04-17 US US721928A patent/US3488423A/en not_active Expired - Lifetime
- 1968-04-17 US US721930A patent/US3505350A/en not_active Expired - Lifetime
-
1969
- 1969-11-07 US US874947A patent/US3629473A/en not_active Expired - Lifetime
-
1971
- 1971-09-03 NL NL7112160A patent/NL7112160A/xx unknown
- 1971-09-03 NL NL7112161A patent/NL7112161A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1155580A (en) | 1969-06-18 |
| US3488423A (en) | 1970-01-06 |
| FR1509975A (fr) | 1968-01-19 |
| US3505350A (en) | 1970-04-07 |
| BR6683847D0 (pt) | 1973-12-04 |
| US3622584A (en) | 1971-11-23 |
| FR6115M (nl) | 1968-06-17 |
| IL26729A (en) | 1970-10-30 |
| NL7112161A (nl) | 1971-12-27 |
| US3629473A (en) | 1971-12-21 |
| NL7112160A (nl) | 1971-12-27 |
| DE1695093A1 (de) | 1970-12-10 |
| SE345453B (nl) | 1972-05-29 |
| NL6614808A (nl) | 1967-04-24 |
| BE688585A (nl) | 1967-04-20 |
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