DD247000A5 - Verfahren zur herstellung von imidazonderivaten - Google Patents
Verfahren zur herstellung von imidazonderivaten Download PDFInfo
- Publication number
- DD247000A5 DD247000A5 DD85284654A DD28465485A DD247000A5 DD 247000 A5 DD247000 A5 DD 247000A5 DD 85284654 A DD85284654 A DD 85284654A DD 28465485 A DD28465485 A DD 28465485A DD 247000 A5 DD247000 A5 DD 247000A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- group
- radicals
- imidazo
- general formula
- methoxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 19
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 18
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims abstract description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 11
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- -1 hydroxy, phenyl Chemical group 0.000 claims description 96
- 150000001875 compounds Chemical class 0.000 claims description 48
- 239000002253 acid Substances 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 8
- 230000000269 nucleophilic effect Effects 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 6
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 5
- 125000005422 alkyl sulfonamido group Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 4
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 4
- 239000012954 diazonium Substances 0.000 claims description 4
- 150000001989 diazonium salts Chemical class 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 238000006894 reductive elimination reaction Methods 0.000 claims description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- GHDZRAXCPMTNLS-UHFFFAOYSA-N 4h-pyridazin-3-one Chemical compound O=C1CC=CN=N1 GHDZRAXCPMTNLS-UHFFFAOYSA-N 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 8
- 230000002785 anti-thrombosis Effects 0.000 abstract description 5
- 239000003146 anticoagulant agent Substances 0.000 abstract description 5
- 230000002526 effect on cardiovascular system Effects 0.000 abstract description 5
- 230000000144 pharmacologic effect Effects 0.000 abstract description 5
- 206010019280 Heart failures Diseases 0.000 abstract description 4
- 239000003814 drug Substances 0.000 abstract description 2
- 150000002460 imidazoles Chemical class 0.000 abstract 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 74
- 238000002844 melting Methods 0.000 description 69
- 230000008018 melting Effects 0.000 description 69
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 31
- 150000003254 radicals Chemical class 0.000 description 31
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- XQCZBXHVTFVIFE-UHFFFAOYSA-N 2-amino-4-hydroxypyrimidine Chemical compound NC1=NC=CC(O)=N1 XQCZBXHVTFVIFE-UHFFFAOYSA-N 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 14
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000013543 active substance Substances 0.000 description 9
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
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- 239000000203 mixture Substances 0.000 description 8
- KQLHRXQKORXSTC-UHFFFAOYSA-N 3-amino-1h-pyrazin-2-one Chemical compound NC1=NC=CNC1=O KQLHRXQKORXSTC-UHFFFAOYSA-N 0.000 description 7
- 238000001819 mass spectrum Methods 0.000 description 7
- 239000000829 suppository Substances 0.000 description 7
- 238000002211 ultraviolet spectrum Methods 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- MFEFTTYGMZOIKO-UHFFFAOYSA-N 5-azacytosine Chemical compound NC1=NC=NC(=O)N1 MFEFTTYGMZOIKO-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- YSKUZVBSHIWEFK-UHFFFAOYSA-N ammelide Chemical compound NC1=NC(O)=NC(O)=N1 YSKUZVBSHIWEFK-UHFFFAOYSA-N 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- XQJAHBHCLXUGEP-UHFFFAOYSA-N 2-bromo-1-(4-methoxyphenyl)ethanone Chemical compound COC1=CC=C(C(=O)CBr)C=C1 XQJAHBHCLXUGEP-UHFFFAOYSA-N 0.000 description 4
- BFNNILAMSKQDRN-UHFFFAOYSA-N 2h-1,2,4-triazin-5-one Chemical compound O=C1C=NNC=N1 BFNNILAMSKQDRN-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
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- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 4
- GEWRKGDRYZIFNP-UHFFFAOYSA-N 1h-1,3,5-triazine-2,4-dione Chemical compound OC1=NC=NC(O)=N1 GEWRKGDRYZIFNP-UHFFFAOYSA-N 0.000 description 3
- OIWAVYDCTUEOEC-UHFFFAOYSA-N 1h-imidazo[1,2-a][1,3,5]triazine-2,4-dione Chemical compound O=C1NC(=O)NC2=NC=CN21 OIWAVYDCTUEOEC-UHFFFAOYSA-N 0.000 description 3
- OQCZUWSXPMWUJM-UHFFFAOYSA-N 1h-imidazo[2,1-f][1,2,4]triazine-2,4-dione Chemical compound O=C1NC(=O)NN2C=CN=C21 OQCZUWSXPMWUJM-UHFFFAOYSA-N 0.000 description 3
- BDTRIDKONHOQQN-UHFFFAOYSA-N 4h-pyrimidin-5-one Chemical compound O=C1CN=CN=C1 BDTRIDKONHOQQN-UHFFFAOYSA-N 0.000 description 3
- JPMJNVODBLZHLR-UHFFFAOYSA-N 5h-imidazo[1,2-b]pyridazin-6-one Chemical compound N1C(=O)C=CC2=NC=CN21 JPMJNVODBLZHLR-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 241000700198 Cavia Species 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 3
- 230000036772 blood pressure Effects 0.000 description 3
- 230000003177 cardiotonic effect Effects 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
- 239000008298 dragée Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000002883 imidazolyl group Chemical group 0.000 description 3
- 210000005240 left ventricle Anatomy 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000006261 methyl amino sulfonyl group Chemical group [H]N(C([H])([H])[H])S(*)(=O)=O 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- 239000000047 product Substances 0.000 description 3
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 2
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 description 2
- GCDKIYGVQTVYNB-UHFFFAOYSA-N 2-(2,4-dimethoxyphenyl)-1h-imidazo[1,2-a]pyrimidin-7-one Chemical compound COC1=CC(OC)=CC=C1C(N1)=CN2C1=NC(=O)C=C2 GCDKIYGVQTVYNB-UHFFFAOYSA-N 0.000 description 2
- UUTKQXFHUWNWPS-UHFFFAOYSA-N 2-(2-methoxy-4-methylsulfonylphenyl)-7h-imidazo[1,2-a]pyrazin-8-one Chemical compound COC1=CC(S(C)(=O)=O)=CC=C1C1=CN(C=CNC2=O)C2=N1 UUTKQXFHUWNWPS-UHFFFAOYSA-N 0.000 description 2
- VADWFIJNKIREJX-UHFFFAOYSA-N 2-(4-methoxyphenyl)-6H-imidazo[1,2-c]pyrimidin-5-one Chemical compound COC1=CC=C(C=C1)C=1N=C2N(C(NC=C2)=O)C=1 VADWFIJNKIREJX-UHFFFAOYSA-N 0.000 description 2
- BNURDKGNDGBHGP-UHFFFAOYSA-N 2-(4-methoxyphenyl)-7h-imidazo[1,2-a]pyrazin-8-one Chemical group C1=CC(OC)=CC=C1C1=CN(C=CNC2=O)C2=N1 BNURDKGNDGBHGP-UHFFFAOYSA-N 0.000 description 2
- KIHBGTRZFAVZRV-UHFFFAOYSA-N 2-hydroxyoctadecanoic acid Chemical class CCCCCCCCCCCCCCCCC(O)C(O)=O KIHBGTRZFAVZRV-UHFFFAOYSA-N 0.000 description 2
- YGTQMKDQJDDBMP-UHFFFAOYSA-N 2-methoxy-N,N-dimethyl-5-(5-oxo-6H-imidazo[1,2-c]pyrimidin-2-yl)benzenesulfonamide Chemical compound CN(S(=O)(=O)C=1C=C(C=CC=1OC)C=1N=C2N(C(NC=C2)=O)C=1)C YGTQMKDQJDDBMP-UHFFFAOYSA-N 0.000 description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 2
- GICKXGZWALFYHZ-UHFFFAOYSA-N 3,N(4)-ethenocytosine Chemical class O=C1NC=CC2=NC=CN12 GICKXGZWALFYHZ-UHFFFAOYSA-N 0.000 description 2
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- MDNCKZUZBIDASU-UHFFFAOYSA-N 3-methoxy-n-methyl-4-(7-oxo-1h-imidazo[1,2-a]pyrimidin-2-yl)benzenesulfonamide Chemical compound COC1=CC(S(=O)(=O)NC)=CC=C1C(N1)=CN2C1=NC(=O)C=C2 MDNCKZUZBIDASU-UHFFFAOYSA-N 0.000 description 2
- SVXNJCYYMRMXNM-UHFFFAOYSA-N 5-amino-2h-1,2,4-triazin-3-one Chemical compound NC=1C=NNC(=O)N=1 SVXNJCYYMRMXNM-UHFFFAOYSA-N 0.000 description 2
- KEXCUMNTOVMAKW-UHFFFAOYSA-N 6-(4-hydroxyphenyl)-1h-imidazo[2,1-f][1,2,4]triazin-4-one Chemical compound C1=CC(O)=CC=C1C1=CN(NC=NC2=O)C2=N1 KEXCUMNTOVMAKW-UHFFFAOYSA-N 0.000 description 2
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
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- NCBIKKPEAVQULG-UHFFFAOYSA-N [3-methoxy-4-(8-oxo-7h-imidazo[1,2-a]pyrazin-2-yl)phenyl] methanesulfonate Chemical compound COC1=CC(OS(C)(=O)=O)=CC=C1C1=CN(C=CNC2=O)C2=N1 NCBIKKPEAVQULG-UHFFFAOYSA-N 0.000 description 2
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- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
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- 239000003054 catalyst Substances 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
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- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 2
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- 150000004682 monohydrates Chemical class 0.000 description 2
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- 239000000546 pharmaceutical excipient Substances 0.000 description 2
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- IBIFDJBSJZMADP-UHFFFAOYSA-N [3-methoxy-4-(5-oxo-6H-imidazo[1,2-c]pyrimidin-2-yl)phenyl] methanesulfonate Chemical compound COC1=C(C=CC(=C1)OS(=O)(=O)C)C=1N=C2N(C(NC=C2)=O)C1 IBIFDJBSJZMADP-UHFFFAOYSA-N 0.000 description 1
- JQQLVLNPAMJCOI-UHFFFAOYSA-N [3-methoxy-4-(6-oxo-5h-imidazo[1,2-b]pyridazin-2-yl)phenyl] methanesulfonate Chemical compound COC1=CC(OS(C)(=O)=O)=CC=C1C1=CN(NC(=O)C=C2)C2=N1 JQQLVLNPAMJCOI-UHFFFAOYSA-N 0.000 description 1
- AJLAAKVCTYFGLM-UHFFFAOYSA-N [3-methoxy-4-(7-oxo-1h-imidazo[1,2-a]pyrimidin-2-yl)phenyl] methanesulfonate Chemical compound COC1=CC(OS(C)(=O)=O)=CC=C1C(N1)=CN2C1=NC(=O)C=C2 AJLAAKVCTYFGLM-UHFFFAOYSA-N 0.000 description 1
- IMSUQBUDUDJRAD-UHFFFAOYSA-N [3-methoxy-4-(8-oxo-7h-imidazo[1,2-d][1,2,4]triazin-2-yl)phenyl] methanesulfonate Chemical compound COC1=CC(OS(C)(=O)=O)=CC=C1C1=CN(C=NNC2=O)C2=N1 IMSUQBUDUDJRAD-UHFFFAOYSA-N 0.000 description 1
- VPDHGDARLFQHGR-UHFFFAOYSA-N [4-(4-oxo-1h-imidazo[2,1-f][1,2,4]triazin-6-yl)phenyl] methanesulfonate Chemical compound C1=CC(OS(=O)(=O)C)=CC=C1C1=CN(NC=NC2=O)C2=N1 VPDHGDARLFQHGR-UHFFFAOYSA-N 0.000 description 1
- CGWYCSMCCPYRIM-UHFFFAOYSA-N [4-(5-oxo-6H-imidazo[1,2-c]pyrimidin-2-yl)phenyl] methanesulfonate Chemical compound CS(=O)(=O)OC1=CC=C(C=C1)C=1N=C2N(C(NC=C2)=O)C1 CGWYCSMCCPYRIM-UHFFFAOYSA-N 0.000 description 1
- HINGTRKWSFXWOX-UHFFFAOYSA-N [4-(5-oxo-6h-imidazo[1,2-d][1,2,4]triazin-2-yl)phenyl] methanesulfonate Chemical compound C1=CC(OS(=O)(=O)C)=CC=C1C1=CN2C(=O)NN=CC2=N1 HINGTRKWSFXWOX-UHFFFAOYSA-N 0.000 description 1
- GANMOBNECHFURE-UHFFFAOYSA-N [4-(7-oxo-1h-imidazo[1,2-a]pyrimidin-2-yl)phenyl] methanesulfonate Chemical compound C1=CC(OS(=O)(=O)C)=CC=C1C(N1)=CN2C1=NC(=O)C=C2 GANMOBNECHFURE-UHFFFAOYSA-N 0.000 description 1
- XCLYZCMODQMEIC-UHFFFAOYSA-N [4-(8-oxo-7h-imidazo[1,2-d][1,2,4]triazin-2-yl)phenyl] methanesulfonate Chemical compound C1=CC(OS(=O)(=O)C)=CC=C1C1=CN(C=NNC2=O)C2=N1 XCLYZCMODQMEIC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000004872 arterial blood pressure Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 229910052794 bromium Inorganic materials 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
- 210000001715 carotid artery Anatomy 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- OKKJLVBELUTLKV-MICDWDOJSA-N deuteriomethanol Chemical compound [2H]CO OKKJLVBELUTLKV-MICDWDOJSA-N 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 210000004731 jugular vein Anatomy 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 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
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- XITDNZSVAFBFTB-UHFFFAOYSA-N n-[2-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-5-methoxyphenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC(OC)=CC=C1C1=CN(N=C(Cl)C=C2)C2=N1 XITDNZSVAFBFTB-UHFFFAOYSA-N 0.000 description 1
- DYXZJLUAORFLRS-UHFFFAOYSA-N n-[3-methoxy-4-(8-oxo-7h-imidazo[1,2-a]pyrazin-2-yl)phenyl]methanesulfonamide Chemical compound COC1=CC(NS(C)(=O)=O)=CC=C1C1=CN(C=CNC2=O)C2=N1 DYXZJLUAORFLRS-UHFFFAOYSA-N 0.000 description 1
- GHXRHVHKILRYBT-UHFFFAOYSA-N n-[4-(5,7-dioxo-1h-imidazo[1,2-a]pyrimidin-2-yl)-3-methoxyphenyl]methanesulfonamide Chemical compound COC1=CC(NS(C)(=O)=O)=CC=C1C1=CN2C(=O)CC(=O)N=C2N1 GHXRHVHKILRYBT-UHFFFAOYSA-N 0.000 description 1
- XAGSATBMMAMREL-UHFFFAOYSA-N n-[4-(5,7-dioxo-1h-imidazo[1,2-a]pyrimidin-2-yl)phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=CN2C(=O)CC(=O)N=C2N1 XAGSATBMMAMREL-UHFFFAOYSA-N 0.000 description 1
- YTPZTGKUPDDNGW-UHFFFAOYSA-N n-[4-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-3-methoxyphenyl]acetamide Chemical compound COC1=CC(NC(C)=O)=CC=C1C1=CN(N=C(Cl)C=C2)C2=N1 YTPZTGKUPDDNGW-UHFFFAOYSA-N 0.000 description 1
- QKKMOXOURZBYNE-UHFFFAOYSA-N n-[4-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-3-methoxyphenyl]methanesulfonamide Chemical compound COC1=CC(NS(C)(=O)=O)=CC=C1C1=CN(N=C(Cl)C=C2)C2=N1 QKKMOXOURZBYNE-UHFFFAOYSA-N 0.000 description 1
- IWHZUHKWTXFGBY-UHFFFAOYSA-N n-[4-(6-chloroimidazo[1,2-b]pyridazin-2-yl)phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=CN(N=C(Cl)C=C2)C2=N1 IWHZUHKWTXFGBY-UHFFFAOYSA-N 0.000 description 1
- LQTVLFPZPOSZNJ-UHFFFAOYSA-N n-[4-(6-oxo-5h-imidazo[1,2-b]pyridazin-2-yl)phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=CN(NC(=O)C=C2)C2=N1 LQTVLFPZPOSZNJ-UHFFFAOYSA-N 0.000 description 1
- PRDPOXQNUJKBBR-UHFFFAOYSA-N n-[4-(7-oxo-1h-imidazo[1,2-a]pyrimidin-2-yl)phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C(N1)=CN2C1=NC(=O)C=C2 PRDPOXQNUJKBBR-UHFFFAOYSA-N 0.000 description 1
- PXITUJKTGLJEJF-UHFFFAOYSA-N n-[4-(8-oxo-7h-imidazo[1,2-a]pyrazin-2-yl)phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=CN(C=CNC2=O)C2=N1 PXITUJKTGLJEJF-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
- 125000002071 phenylalkoxy group Chemical group 0.000 description 1
- WKFBZNUBXWCCHG-UHFFFAOYSA-N phosphorus trifluoride Chemical compound FP(F)F WKFBZNUBXWCCHG-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 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
- 229940072033 potash Drugs 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- ILJOYZVVZZFIKA-UHFFFAOYSA-M sodium;1,1-dioxo-1,2-benzothiazol-3-olate;hydrate Chemical compound O.[Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 ILJOYZVVZZFIKA-UHFFFAOYSA-M 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000009495 sugar coating Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843446812 DE3446812A1 (de) | 1984-12-21 | 1984-12-21 | Neue imidazoderivate, ihre herstellung und diese verbindungen enthaltende arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD247000A5 true DD247000A5 (de) | 1987-06-24 |
Family
ID=6253512
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD85284654A DD247000A5 (de) | 1984-12-21 | 1985-12-18 | Verfahren zur herstellung von imidazonderivaten |
Country Status (15)
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8719368D0 (en) * | 1987-08-15 | 1987-09-23 | Wellcome Found | Heterocyclic compounds |
| GB8804016D0 (en) * | 1988-02-22 | 1988-03-23 | Boots Co Plc | Therapeutic agents |
| PH27291A (en) * | 1989-01-31 | 1993-05-04 | Takeda Chemical Industries Ltd | Imidazolpyrimidazines their production and use |
| EP0440119A1 (en) * | 1990-01-31 | 1991-08-07 | Takeda Chemical Industries, Ltd. | Imidazopyridazine compounds, their production and use |
| TW221689B (enrdf_load_stackoverflow) * | 1991-08-27 | 1994-03-11 | Otsuka Pharma Co Ltd | |
| TW304878B (enrdf_load_stackoverflow) * | 1993-09-21 | 1997-05-11 | Takeda Pharm Industry Co Ltd | |
| US7709468B2 (en) | 2005-09-02 | 2010-05-04 | Abbott Laboratories | Imidazo based heterocycles |
| US7723336B2 (en) | 2005-09-22 | 2010-05-25 | Bristol-Myers Squibb Company | Fused heterocyclic compounds useful as kinase modulators |
| EP1964841A1 (en) * | 2007-02-28 | 2008-09-03 | sanofi-aventis | Imidazo[1,2-a]azine and their use as pharmaceuticals |
| US7868001B2 (en) | 2007-11-02 | 2011-01-11 | Hutchison Medipharma Enterprises Limited | Cytokine inhibitors |
| WO2009100375A1 (en) | 2008-02-06 | 2009-08-13 | Bristol-Myers Squibb Company | Substituted imidazopyridazines useful as kinase inhibitors |
| MX2012004340A (es) * | 2009-10-16 | 2012-11-23 | Rib X Pharmaceuticals Inc | Compuestos antimicrobianos y metodos para fabricar y utilizar los mismos. |
| JP6274723B2 (ja) | 2009-10-16 | 2018-02-07 | メリンタ セラピューティクス，インコーポレイテッド | 抗微生物性化合物および抗微生物性化合物の製造方法および使用方法 |
| CN107922418A (zh) | 2015-03-11 | 2018-04-17 | 梅琳塔治疗公司 | 抗微生物化合物及制备和使用所述化合物的方法 |
| WO2017020944A1 (en) * | 2015-07-31 | 2017-02-09 | Universite De Nantes | Novel fused pyrimidinone and triazinone derivatives, their process of preparation and their therapeutic uses as antifungal and/or antiparasitic agents |
| WO2017193016A1 (en) | 2016-05-06 | 2017-11-09 | Melinta Therapeutics, Inc. | Antimicrobials and methods of making and using same |
| CN115970757B (zh) * | 2022-08-18 | 2024-07-09 | 四川大学 | 一种非茂稀土金属碳氢官能团化反应催化剂及其制备方法和应用 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA839398B (en) * | 1982-12-27 | 1985-08-28 | Lilly Co Eli | Substituted imidazopyrimidines-pyrazines,and-triazines |
| GB8305245D0 (en) * | 1983-02-25 | 1983-03-30 | Fujisawa Pharmaceutical Co | Imidazo-heterocyclic compounds |
| DE3347290A1 (de) * | 1983-12-28 | 1985-07-11 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue 2-phenyl-imidazole, ihre herstellung und diese verbindungen enthaltende arzneimittel |
| MC1673A1 (fr) * | 1984-06-27 | 1986-06-03 | Wellcome Found | Derives aryliques de composes imidazoliques,leur preparation et leur emploi pour la preparation des medicaments |
-
1984
- 1984-12-21 DE DE19843446812 patent/DE3446812A1/de not_active Withdrawn
-
1985
- 1985-12-16 EP EP85116026A patent/EP0185346A3/de not_active Withdrawn
- 1985-12-18 DD DD85284654A patent/DD247000A5/de unknown
- 1985-12-19 FI FI855081A patent/FI855081A7/fi not_active Application Discontinuation
- 1985-12-19 DK DK592685A patent/DK592685A/da not_active Application Discontinuation
- 1985-12-19 PT PT81715A patent/PT81715B/pt unknown
- 1985-12-20 NO NO855197A patent/NO855197L/no unknown
- 1985-12-20 AU AU51543/85A patent/AU5154385A/en not_active Abandoned
- 1985-12-20 PH PH33228A patent/PH21839A/en unknown
- 1985-12-20 GR GR853127A patent/GR853127B/el unknown
- 1985-12-20 JP JP60287603A patent/JPS61152684A/ja active Pending
- 1985-12-20 ES ES550240A patent/ES8703471A1/es not_active Expired
- 1985-12-20 ZA ZA859730A patent/ZA859730B/xx unknown
- 1985-12-20 HU HU854934A patent/HUT40438A/hu unknown
- 1985-12-20 NZ NZ214663A patent/NZ214663A/en unknown
-
1986
- 1986-06-24 ES ES556493A patent/ES8707239A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| EP0185346A2 (de) | 1986-06-25 |
| ES8707239A1 (es) | 1987-07-16 |
| NZ214663A (en) | 1988-02-12 |
| ZA859730B (en) | 1987-08-26 |
| FI855081A7 (fi) | 1986-06-22 |
| PT81715B (de) | 1987-10-15 |
| PH21839A (en) | 1988-03-17 |
| HUT40438A (en) | 1986-12-28 |
| DK592685A (da) | 1986-06-22 |
| PT81715A (de) | 1986-01-01 |
| GR853127B (enrdf_load_stackoverflow) | 1986-04-22 |
| DE3446812A1 (de) | 1986-06-26 |
| JPS61152684A (ja) | 1986-07-11 |
| DK592685D0 (da) | 1985-12-19 |
| ES556493A0 (es) | 1987-07-16 |
| EP0185346A3 (de) | 1987-09-02 |
| ES8703471A1 (es) | 1987-02-16 |
| NO855197L (no) | 1986-06-23 |
| AU5154385A (en) | 1986-07-17 |
| ES550240A0 (es) | 1987-02-16 |
| FI855081A0 (fi) | 1985-12-19 |
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