AT394555B - Verfahren zur herstellung neuer iminothiazolidinderivate - Google Patents
Verfahren zur herstellung neuer iminothiazolidinderivate Download PDFInfo
- Publication number
- AT394555B AT394555B AT0124285A AT124285A AT394555B AT 394555 B AT394555 B AT 394555B AT 0124285 A AT0124285 A AT 0124285A AT 124285 A AT124285 A AT 124285A AT 394555 B AT394555 B AT 394555B
- Authority
- AT
- Austria
- Prior art keywords
- general formula
- nitro
- compound
- millimoles
- preparation
- Prior art date
Links
- REGFWZVTTFGQOJ-UHFFFAOYSA-N 4,5-dihydro-1,3-thiazol-2-amine Chemical class NC1=NCCS1 REGFWZVTTFGQOJ-UHFFFAOYSA-N 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 138
- 229910052717 sulfur Inorganic materials 0.000 claims description 106
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 100
- 229910052757 nitrogen Inorganic materials 0.000 claims description 92
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 84
- 238000002360 preparation method Methods 0.000 claims description 80
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 78
- 238000004458 analytical method Methods 0.000 claims description 67
- 238000000034 method Methods 0.000 claims description 62
- 239000000203 mixture Substances 0.000 claims description 60
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 51
- 239000003054 catalyst Substances 0.000 claims description 43
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 38
- 238000009835 boiling Methods 0.000 claims description 35
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 23
- -1 4-amino-2-nitro-phenyl Chemical group 0.000 claims description 19
- 239000007789 gas Substances 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 19
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 17
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 17
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 16
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 16
- 239000007858 starting material Substances 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 150000002540 isothiocyanates Chemical class 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000006239 protecting group Chemical group 0.000 claims description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 229910052763 palladium Inorganic materials 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
- 229910017604 nitric acid Inorganic materials 0.000 claims description 4
- 125000004744 butyloxycarbonyl group Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- YYPCUGJKDYEIHT-UHFFFAOYSA-N 5-chloro-2-(2-imino-1,3-thiazolidin-3-yl)aniline Chemical compound NC1=CC(Cl)=CC=C1N1C(=N)SCC1 YYPCUGJKDYEIHT-UHFFFAOYSA-N 0.000 claims description 2
- NODWSKGWUYQMHV-UHFFFAOYSA-N 5-chloro-2-(2-imino-5-methyl-1,3-thiazolidin-3-yl)aniline Chemical compound N=C1SC(C)CN1C1=CC=C(Cl)C=C1N NODWSKGWUYQMHV-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 2
- 238000004587 chromatography analysis Methods 0.000 claims description 2
- 238000006396 nitration reaction Methods 0.000 claims description 2
- 238000007363 ring formation reaction Methods 0.000 claims description 2
- UTYXZVXUFMZWAX-UHFFFAOYSA-N 2-(2-imino-1,3-thiazolidin-3-yl)-5-methylaniline Chemical compound NC1=CC(C)=CC=C1N1C(=N)SCC1 UTYXZVXUFMZWAX-UHFFFAOYSA-N 0.000 claims 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 230000008030 elimination Effects 0.000 claims 1
- 238000003379 elimination reaction Methods 0.000 claims 1
- 239000012535 impurity Substances 0.000 claims 1
- 125000005948 methanesulfonyloxy group Chemical group 0.000 claims 1
- BCSLXVTXOLLNDU-UHFFFAOYSA-N n-[4-(2-isothiocyanatoethylamino)-3-nitrophenyl]acetamide Chemical compound CC(=O)NC1=CC=C(NCCN=C=S)C([N+]([O-])=O)=C1 BCSLXVTXOLLNDU-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 129
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 112
- 239000013078 crystal Substances 0.000 description 109
- 239000000843 powder Substances 0.000 description 38
- 238000001816 cooling Methods 0.000 description 31
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- 239000011541 reaction mixture Substances 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 20
- 238000004809 thin layer chromatography Methods 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- 239000003208 petroleum Substances 0.000 description 17
- 239000000706 filtrate Substances 0.000 description 16
- 239000000155 melt Substances 0.000 description 16
- 238000000354 decomposition reaction Methods 0.000 description 15
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 15
- 238000007792 addition Methods 0.000 description 14
- 239000002585 base Substances 0.000 description 14
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 14
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 13
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 13
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 229920006395 saturated elastomer Polymers 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000005984 hydrogenation reaction Methods 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- 229910052794 bromium Inorganic materials 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- KPABMWLSSQTGCB-UHFFFAOYSA-N 3-(4-nitrophenyl)-1,3-thiazolidin-2-imine Chemical compound C1=CC([N+](=O)[O-])=CC=C1N1C(=N)SCC1 KPABMWLSSQTGCB-UHFFFAOYSA-N 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 5
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 5
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 5
- KQIKXMFNGKJNNS-UHFFFAOYSA-N 1-(4-chloro-2-nitroanilino)propan-2-yl thiocyanate Chemical compound N#CSC(C)CNC1=CC=C(Cl)C=C1[N+]([O-])=O KQIKXMFNGKJNNS-UHFFFAOYSA-N 0.000 description 4
- BCFHVANLDDIGCA-UHFFFAOYSA-N 2-(2-nitroanilino)ethyl thiocyanate Chemical compound [O-][N+](=O)C1=CC=CC=C1NCCSC#N BCFHVANLDDIGCA-UHFFFAOYSA-N 0.000 description 4
- GOXGKPRYEQWLSC-UHFFFAOYSA-N 2-(4-chloro-2-nitroanilino)ethyl thiocyanate Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1NCCSC#N GOXGKPRYEQWLSC-UHFFFAOYSA-N 0.000 description 4
- LKHIGLDFTYFCLK-UHFFFAOYSA-N 2-(4-methoxy-2-nitroanilino)ethyl thiocyanate Chemical compound COC1=CC=C(NCCSC#N)C([N+]([O-])=O)=C1 LKHIGLDFTYFCLK-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 3
- VJVCQKOMUMNIGE-UHFFFAOYSA-N 1,3-thiazolidin-2-amine Chemical compound NC1NCCS1 VJVCQKOMUMNIGE-UHFFFAOYSA-N 0.000 description 3
- VYUCHAZYURDQMX-UHFFFAOYSA-N 2-(4-methyl-2-nitroanilino)ethyl thiocyanate Chemical compound CC1=CC=C(NCCSC#N)C([N+]([O-])=O)=C1 VYUCHAZYURDQMX-UHFFFAOYSA-N 0.000 description 3
- BVDQXKRXZIMJMB-UHFFFAOYSA-N 2-(5-chloro-2-nitroanilino)ethyl thiocyanate Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1NCCSC#N BVDQXKRXZIMJMB-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000010970 precious metal Substances 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- RZKKOBGFCAHLCZ-UHFFFAOYSA-N 1,4-dichloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1Cl RZKKOBGFCAHLCZ-UHFFFAOYSA-N 0.000 description 2
- XUKCCLMJUSCHLA-UHFFFAOYSA-N 1-(4-chloro-2-nitroanilino)propan-2-yl methanesulfonate Chemical compound CS(=O)(=O)OC(C)CNC1=CC=C(Cl)C=C1[N+]([O-])=O XUKCCLMJUSCHLA-UHFFFAOYSA-N 0.000 description 2
- FXOPMDNVKBBIMX-UHFFFAOYSA-N 2-(2,4,6-trinitroanilino)ethyl methanesulfonate Chemical compound CS(=O)(=O)OCCNC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O FXOPMDNVKBBIMX-UHFFFAOYSA-N 0.000 description 2
- MMNBVIKAQIGULV-UHFFFAOYSA-N 2-(2,4,6-trinitroanilino)ethyl thiocyanate Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=C(NCCSC#N)C([N+]([O-])=O)=C1 MMNBVIKAQIGULV-UHFFFAOYSA-N 0.000 description 2
- CVJSSXUILQSVBP-UHFFFAOYSA-N 2-(2-chloro-4-nitroanilino)ethyl methanesulfonate Chemical compound CS(=O)(=O)OCCNC1=CC=C([N+]([O-])=O)C=C1Cl CVJSSXUILQSVBP-UHFFFAOYSA-N 0.000 description 2
- XQUWJDXBRWPHAG-UHFFFAOYSA-N 2-(2-chloro-4-nitroanilino)ethyl thiocyanate Chemical compound [O-][N+](=O)C1=CC=C(NCCSC#N)C(Cl)=C1 XQUWJDXBRWPHAG-UHFFFAOYSA-N 0.000 description 2
- PEYGUEIITJNZPS-UHFFFAOYSA-N 2-(2-chloro-6-nitroanilino)ethyl thiocyanate Chemical compound [O-][N+](=O)C1=CC=CC(Cl)=C1NCCSC#N PEYGUEIITJNZPS-UHFFFAOYSA-N 0.000 description 2
- CBQTXIJIOCQRFL-UHFFFAOYSA-N 2-(2-nitroanilino)ethyl methanesulfonate Chemical compound CS(=O)(=O)OCCNC1=CC=CC=C1[N+]([O-])=O CBQTXIJIOCQRFL-UHFFFAOYSA-N 0.000 description 2
- UBUAUPOMEXLEGO-UHFFFAOYSA-N 2-(4-chloro-2-nitroanilino)butan-1-ol Chemical compound CCC(CO)NC1=CC=C(Cl)C=C1[N+]([O-])=O UBUAUPOMEXLEGO-UHFFFAOYSA-N 0.000 description 2
- UNEUXDLHGBETSM-UHFFFAOYSA-N 2-(4-chloro-2-nitroanilino)butyl methanesulfonate Chemical compound CS(=O)(=O)OCC(CC)NC1=CC=C(Cl)C=C1[N+]([O-])=O UNEUXDLHGBETSM-UHFFFAOYSA-N 0.000 description 2
- XOGACIULOYQKCC-UHFFFAOYSA-N 2-(4-chloro-2-nitroanilino)butyl thiocyanate Chemical compound N#CSCC(CC)NC1=CC=C(Cl)C=C1[N+]([O-])=O XOGACIULOYQKCC-UHFFFAOYSA-N 0.000 description 2
- VCFIPLIOFQZJNR-UHFFFAOYSA-N 2-(4-chloro-2-nitroanilino)ethyl methanesulfonate Chemical compound CS(=O)(=O)OCCNC1=CC=C(Cl)C=C1[N+]([O-])=O VCFIPLIOFQZJNR-UHFFFAOYSA-N 0.000 description 2
- YAVYIHSPRHJVQV-UHFFFAOYSA-N 2-(4-methyl-2-nitroanilino)ethyl methanesulfonate Chemical compound CC1=CC=C(NCCOS(C)(=O)=O)C([N+]([O-])=O)=C1 YAVYIHSPRHJVQV-UHFFFAOYSA-N 0.000 description 2
- YKTPZHLIRGSOOQ-UHFFFAOYSA-N 2-(4-nitroanilino)ethyl methanesulfonate Chemical compound CS(=O)(=O)OCCNC1=CC=C([N+]([O-])=O)C=C1 YKTPZHLIRGSOOQ-UHFFFAOYSA-N 0.000 description 2
- DMVILZQGIAHCMW-UHFFFAOYSA-N 2-(5-chloro-2-nitroanilino)ethyl methanesulfonate Chemical compound CS(=O)(=O)OCCNC1=CC(Cl)=CC=C1[N+]([O-])=O DMVILZQGIAHCMW-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- NFZFOQJLIDDTOG-UHFFFAOYSA-N 2-[2-nitro-4-(trifluoromethyl)anilino]ethyl methanesulfonate Chemical compound CS(=O)(=O)OCCNC1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O NFZFOQJLIDDTOG-UHFFFAOYSA-N 0.000 description 2
- SKHMBVOFVAGPKK-UHFFFAOYSA-N 2-[2-nitro-4-(trifluoromethyl)anilino]ethyl thiocyanate Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC=C1NCCSC#N SKHMBVOFVAGPKK-UHFFFAOYSA-N 0.000 description 2
- HBFBARYGMHNEFF-UHFFFAOYSA-N 3-(2,4,6-trinitrophenyl)-1,3-thiazolidin-2-imine Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1N1C(=N)SCC1 HBFBARYGMHNEFF-UHFFFAOYSA-N 0.000 description 2
- BDOJKFPYPZCQIZ-UHFFFAOYSA-N 3-(2-nitrophenyl)-1,3-thiazolidin-2-imine Chemical compound [O-][N+](=O)C1=CC=CC=C1N1C(=N)SCC1 BDOJKFPYPZCQIZ-UHFFFAOYSA-N 0.000 description 2
- IRQCLAYDHXZFEB-UHFFFAOYSA-N 3-(4-methoxy-2-nitrophenyl)-1,3-thiazolidin-2-imine;hydrochloride Chemical compound Cl.[O-][N+](=O)C1=CC(OC)=CC=C1N1C(=N)SCC1 IRQCLAYDHXZFEB-UHFFFAOYSA-N 0.000 description 2
- IEWFNLPQJULCCL-UHFFFAOYSA-N 4-chloro-n-[2-[2-(4-chloro-2-nitroanilino)ethyldisulfanyl]ethyl]-2-nitroaniline Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1NCCSSCCNC1=CC=C(Cl)C=C1[N+]([O-])=O IEWFNLPQJULCCL-UHFFFAOYSA-N 0.000 description 2
- HDQYGJFUTKXEDE-UHFFFAOYSA-N 5-chloro-2-(2-imino-1,3-thiazolidin-3-yl)aniline;dihydrochloride Chemical compound Cl.Cl.NC1=CC(Cl)=CC=C1N1C(=N)SCC1 HDQYGJFUTKXEDE-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- HXVBMNABPGSSIN-UHFFFAOYSA-N [amino-[2-(4-nitroanilino)ethylsulfanyl]methylidene]azanium;methanesulfonate Chemical compound CS([O-])(=O)=O.NC(=[NH2+])SCCNC1=CC=C([N+]([O-])=O)C=C1 HXVBMNABPGSSIN-UHFFFAOYSA-N 0.000 description 2
- 230000001430 anti-depressive effect Effects 0.000 description 2
- 230000003556 anti-epileptic effect Effects 0.000 description 2
- 230000000648 anti-parkinson Effects 0.000 description 2
- 239000001961 anticonvulsive agent Substances 0.000 description 2
- 239000000935 antidepressant agent Substances 0.000 description 2
- 229940005513 antidepressants Drugs 0.000 description 2
- 239000000939 antiparkinson agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003245 coal Substances 0.000 description 2
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 2
- OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- OGHGUGKRYWXUOX-UHFFFAOYSA-N methyl 4-(2-imino-1,3-thiazolidin-3-yl)-3-nitrobenzoate Chemical compound [O-][N+](=O)C1=CC(C(=O)OC)=CC=C1N1C(=N)SCC1 OGHGUGKRYWXUOX-UHFFFAOYSA-N 0.000 description 2
- OQWHGRYUMLZMPC-UHFFFAOYSA-N methyl 4-(2-methylsulfonyloxyethylamino)-3-nitrobenzoate Chemical compound COC(=O)C1=CC=C(NCCOS(C)(=O)=O)C([N+]([O-])=O)=C1 OQWHGRYUMLZMPC-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- ATLZGQJPRLSBPZ-UHFFFAOYSA-N n-[4-(2-hydroxyethylamino)-3-nitrophenyl]acetamide Chemical compound CC(=O)NC1=CC=C(NCCO)C([N+]([O-])=O)=C1 ATLZGQJPRLSBPZ-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 230000002048 spasmolytic effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000001984 thiazolidinyl group Chemical group 0.000 description 2
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 2
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 1
- QSELWVPMRTWLSU-UHFFFAOYSA-N 1-(2-aminophenyl)-4,5-dihydroimidazol-2-amine Chemical class NC1=CC=CC=C1N1C(=N)NCC1 QSELWVPMRTWLSU-UHFFFAOYSA-N 0.000 description 1
- CJCVJKRGKCLXRH-UHFFFAOYSA-N 1-(2-nitrophenyl)-4,5-dihydroimidazol-2-amine Chemical class [O-][N+](=O)C1=CC=CC=C1N1C(=N)NCC1 CJCVJKRGKCLXRH-UHFFFAOYSA-N 0.000 description 1
- AKVUGASBDNDLPM-UHFFFAOYSA-N 1-(4-chloro-2-nitroanilino)ethanol Chemical compound ClC1=CC(=C(NC(C)O)C=C1)[N+](=O)[O-] AKVUGASBDNDLPM-UHFFFAOYSA-N 0.000 description 1
- XVONMMVMTMGHJV-UHFFFAOYSA-N 1-(4-chloro-2-nitroanilino)propan-2-ol Chemical compound CC(O)CNC1=CC=C(Cl)C=C1[N+]([O-])=O XVONMMVMTMGHJV-UHFFFAOYSA-N 0.000 description 1
- HJRJRUMKQCMYDL-UHFFFAOYSA-N 1-chloro-2,4,6-trinitrobenzene Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=C(Cl)C([N+]([O-])=O)=C1 HJRJRUMKQCMYDL-UHFFFAOYSA-N 0.000 description 1
- PWKNBLFSJAVFAB-UHFFFAOYSA-N 1-fluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1F PWKNBLFSJAVFAB-UHFFFAOYSA-N 0.000 description 1
- WFQDTOYDVUWQMS-UHFFFAOYSA-N 1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1 WFQDTOYDVUWQMS-UHFFFAOYSA-N 0.000 description 1
- XFQSQNIUFIONHC-UHFFFAOYSA-N 2-(2-chloro-4-nitroanilino)ethanol Chemical compound OCCNC1=CC=C([N+]([O-])=O)C=C1Cl XFQSQNIUFIONHC-UHFFFAOYSA-N 0.000 description 1
- ZCDAQUOUYFPEKC-UHFFFAOYSA-N 2-(2-chloro-6-nitroanilino)ethanol Chemical compound OCCNC1=C(Cl)C=CC=C1[N+]([O-])=O ZCDAQUOUYFPEKC-UHFFFAOYSA-N 0.000 description 1
- REVVOIWACNAYPU-UHFFFAOYSA-N 2-(2-chloro-6-nitroanilino)ethyl methanesulfonate Chemical compound CS(=O)(=O)OCCNC1=C(Cl)C=CC=C1[N+]([O-])=O REVVOIWACNAYPU-UHFFFAOYSA-N 0.000 description 1
- CFGJTTRRLQRAIU-UHFFFAOYSA-N 2-(2-hydroxyethylamino)-3-nitrobenzoic acid Chemical compound OCCNC1=C(C(O)=O)C=CC=C1[N+]([O-])=O CFGJTTRRLQRAIU-UHFFFAOYSA-N 0.000 description 1
- OEBVEWXYFAYQFN-UHFFFAOYSA-N 2-(2-imino-1,3-thiazolidin-3-yl)-5-(trifluoromethyl)aniline;dihydrochloride Chemical compound Cl.Cl.NC1=CC(C(F)(F)F)=CC=C1N1C(=N)SCC1 OEBVEWXYFAYQFN-UHFFFAOYSA-N 0.000 description 1
- SNNLALDJSQLIMG-UHFFFAOYSA-N 2-(2-imino-1,3-thiazolidin-3-yl)-5-methoxyaniline;dihydrochloride Chemical compound Cl.Cl.NC1=CC(OC)=CC=C1N1C(=N)SCC1 SNNLALDJSQLIMG-UHFFFAOYSA-N 0.000 description 1
- IFKBTNYTKQHRNQ-UHFFFAOYSA-N 2-(2-imino-1,3-thiazolidin-3-yl)-5-methylaniline;dihydrochloride Chemical compound Cl.Cl.NC1=CC(C)=CC=C1N1C(=N)SCC1 IFKBTNYTKQHRNQ-UHFFFAOYSA-N 0.000 description 1
- XZRYNBISKDQVDB-UHFFFAOYSA-N 2-(2-imino-1,3-thiazolidin-3-yl)aniline;dihydrochloride Chemical compound Cl.Cl.NC1=CC=CC=C1N1C(=N)SCC1 XZRYNBISKDQVDB-UHFFFAOYSA-N 0.000 description 1
- LFOUYKNCQNVIGI-UHFFFAOYSA-N 2-(2-nitroanilino)ethanol Chemical compound OCCNC1=CC=CC=C1[N+]([O-])=O LFOUYKNCQNVIGI-UHFFFAOYSA-N 0.000 description 1
- BKLMJXCMMSVECP-UHFFFAOYSA-N 2-(4-acetamido-2-nitroanilino)ethyl methanesulfonate Chemical compound CC(=O)NC1=CC=C(NCCOS(C)(=O)=O)C([N+]([O-])=O)=C1 BKLMJXCMMSVECP-UHFFFAOYSA-N 0.000 description 1
- BVAUDUIVYIQJQE-UHFFFAOYSA-N 2-(4-acetamido-2-nitroanilino)ethyl thiocyanate Chemical compound CC(=O)NC1=CC=C(NCCSC#N)C([N+]([O-])=O)=C1 BVAUDUIVYIQJQE-UHFFFAOYSA-N 0.000 description 1
- SCZQUWZLEIYDBD-UHFFFAOYSA-N 2-(4-methyl-2-nitroanilino)ethanol Chemical compound CC1=CC=C(NCCO)C([N+]([O-])=O)=C1 SCZQUWZLEIYDBD-UHFFFAOYSA-N 0.000 description 1
- VPRLWNAMKBZKRR-UHFFFAOYSA-N 2-(4-nitroanilino)ethanol Chemical compound OCCNC1=CC=C([N+]([O-])=O)C=C1 VPRLWNAMKBZKRR-UHFFFAOYSA-N 0.000 description 1
- LKYIEUZKAAJMSD-UHFFFAOYSA-N 2-(5-chloro-2-nitroanilino)ethanol Chemical compound OCCNC1=CC(Cl)=CC=C1[N+]([O-])=O LKYIEUZKAAJMSD-UHFFFAOYSA-N 0.000 description 1
- NJZCRXQWPNNJNB-UHFFFAOYSA-N 2-[2-nitro-4-(trifluoromethyl)anilino]ethanol Chemical compound OCCNC1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O NJZCRXQWPNNJNB-UHFFFAOYSA-N 0.000 description 1
- JCBPETKZIGVZRE-UHFFFAOYSA-N 2-aminobutan-1-ol Chemical compound CCC(N)CO JCBPETKZIGVZRE-UHFFFAOYSA-N 0.000 description 1
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 description 1
- UPXNPMMVKQLAOQ-UHFFFAOYSA-N 2-anilinoethyl thiocyanate Chemical compound S(C#N)CCNC1=CC=CC=C1 UPXNPMMVKQLAOQ-UHFFFAOYSA-N 0.000 description 1
- KOJQVFGFFJKILZ-UHFFFAOYSA-N 2-hydroxy-4-(2-imino-1,3-thiazolidin-3-yl)benzoic acid;hydrobromide Chemical compound Br.C1=C(O)C(C(=O)O)=CC=C1N1C(=N)SCC1 KOJQVFGFFJKILZ-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- YHIZUYWYSOEPEH-UHFFFAOYSA-N 3-(2-chloro-4-nitrophenyl)-1,3-thiazolidin-2-imine;hydrochloride Chemical compound Cl.ClC1=CC([N+](=O)[O-])=CC=C1N1C(=N)SCC1 YHIZUYWYSOEPEH-UHFFFAOYSA-N 0.000 description 1
- RNUNUWNYNNLQBE-UHFFFAOYSA-N 3-(2-chloro-6-nitrophenyl)-1,3-thiazolidin-2-imine;hydrochloride Chemical compound Cl.[O-][N+](=O)C1=CC=CC(Cl)=C1N1C(=N)SCC1 RNUNUWNYNNLQBE-UHFFFAOYSA-N 0.000 description 1
- DJAHMPXLUFGXNE-UHFFFAOYSA-N 3-(2-methoxyphenyl)-1,3-thiazolidin-2-imine;hydrobromide Chemical compound Br.COC1=CC=CC=C1N1C(=N)SCC1 DJAHMPXLUFGXNE-UHFFFAOYSA-N 0.000 description 1
- UTWISASMOKPPHY-UHFFFAOYSA-N 3-(2-nitrophenyl)-1,3-thiazolidin-2-imine;hydrochloride Chemical compound Cl.[O-][N+](=O)C1=CC=CC=C1N1C(=N)SCC1 UTWISASMOKPPHY-UHFFFAOYSA-N 0.000 description 1
- DFFRTMCNTRXIAG-UHFFFAOYSA-N 3-(4-bromophenyl)-1,3-thiazolidin-2-imine;hydrobromide Chemical compound Br.C1=CC(Br)=CC=C1N1C(=N)SCC1 DFFRTMCNTRXIAG-UHFFFAOYSA-N 0.000 description 1
- NMRHYPCLBFJZCY-UHFFFAOYSA-N 3-(4-chloro-2-nitrophenyl)-1,3-thiazolidin-2-imine Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1N1C(=N)SCC1 NMRHYPCLBFJZCY-UHFFFAOYSA-N 0.000 description 1
- FOFRERBOXGZCPP-UHFFFAOYSA-N 3-(4-chloro-2-nitrophenyl)-1,3-thiazolidin-2-imine;hydrobromide Chemical compound Br.[O-][N+](=O)C1=CC(Cl)=CC=C1N1C(=N)SCC1 FOFRERBOXGZCPP-UHFFFAOYSA-N 0.000 description 1
- LEKUJDPEDWSGAF-UHFFFAOYSA-N 3-(4-chloro-2-nitrophenyl)-1,3-thiazolidin-2-imine;hydrochloride Chemical compound Cl.[O-][N+](=O)C1=CC(Cl)=CC=C1N1C(=N)SCC1 LEKUJDPEDWSGAF-UHFFFAOYSA-N 0.000 description 1
- CTWCVSHNPIMBCY-UHFFFAOYSA-N 3-(4-chloro-2-nitrophenyl)-5-methyl-1,3-thiazolidin-2-imine;hydrochloride Chemical compound Cl.N=C1SC(C)CN1C1=CC=C(Cl)C=C1[N+]([O-])=O CTWCVSHNPIMBCY-UHFFFAOYSA-N 0.000 description 1
- VBRIHOKQMDCSGR-UHFFFAOYSA-N 3-(4-chlorophenyl)-1,3-thiazolidin-2-imine;hydrobromide Chemical compound Br.C1=CC(Cl)=CC=C1N1C(=N)SCC1 VBRIHOKQMDCSGR-UHFFFAOYSA-N 0.000 description 1
- ZMCXMGSXJDGNLB-UHFFFAOYSA-N 3-(4-methoxyphenyl)-1,3-thiazolidin-2-imine;hydrobromide Chemical compound Br.C1=CC(OC)=CC=C1N1C(=N)SCC1 ZMCXMGSXJDGNLB-UHFFFAOYSA-N 0.000 description 1
- DMZCMULOFCQPPX-UHFFFAOYSA-N 3-(4-methyl-2-nitrophenyl)-1,3-thiazolidin-2-imine Chemical compound [O-][N+](=O)C1=CC(C)=CC=C1N1C(=N)SCC1 DMZCMULOFCQPPX-UHFFFAOYSA-N 0.000 description 1
- GRHOCVPNEHAAFA-UHFFFAOYSA-N 3-(4-methyl-2-nitrophenyl)-1,3-thiazolidin-2-imine;hydrochloride Chemical compound Cl.[O-][N+](=O)C1=CC(C)=CC=C1N1C(=N)SCC1 GRHOCVPNEHAAFA-UHFFFAOYSA-N 0.000 description 1
- AIFJNNXXKQXQRC-UHFFFAOYSA-N 3-(5-chloro-2-nitrophenyl)-1,3-thiazolidin-2-imine;hydrochloride Chemical compound Cl.[O-][N+](=O)C1=CC=C(Cl)C=C1N1C(=N)SCC1 AIFJNNXXKQXQRC-UHFFFAOYSA-N 0.000 description 1
- IUKRHFQEUKHRIH-UHFFFAOYSA-N 3-[2-nitro-4-(trifluoromethyl)phenyl]-1,3-thiazolidin-2-imine Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC=C1N1C(=N)SCC1 IUKRHFQEUKHRIH-UHFFFAOYSA-N 0.000 description 1
- AXWZRNCAUJIFJR-UHFFFAOYSA-N 3-[2-nitro-4-(trifluoromethyl)phenyl]-1,3-thiazolidin-2-imine;hydrochloride Chemical compound Cl.[O-][N+](=O)C1=CC(C(F)(F)F)=CC=C1N1C(=N)SCC1 AXWZRNCAUJIFJR-UHFFFAOYSA-N 0.000 description 1
- SVZPZPVPDGBZEW-UHFFFAOYSA-N 3-[4-chloro-3-(trifluoromethyl)phenyl]-1,3-thiazolidin-2-imine;hydrobromide Chemical compound Br.C1=C(Cl)C(C(F)(F)F)=CC(N2C(SCC2)=N)=C1 SVZPZPVPDGBZEW-UHFFFAOYSA-N 0.000 description 1
- ZOFWPWSERHORAG-UHFFFAOYSA-N 3-chloro-2-(2-imino-1,3-thiazolidin-3-yl)aniline;ethanesulfonic acid Chemical compound CCS(O)(=O)=O.NC1=CC=CC(Cl)=C1N1C(=N)SCC1 ZOFWPWSERHORAG-UHFFFAOYSA-N 0.000 description 1
- JMNZXDXRTPJQRC-UHFFFAOYSA-N 3-phenyl-1,3-thiazolidin-2-imine Chemical compound N=C1SCCN1C1=CC=CC=C1 JMNZXDXRTPJQRC-UHFFFAOYSA-N 0.000 description 1
- IBRMDPYUGVPKNC-UHFFFAOYSA-N 4-(2-imino-1,3-thiazolidin-3-yl)aniline Chemical compound C1=CC(N)=CC=C1N1C(=N)SCC1 IBRMDPYUGVPKNC-UHFFFAOYSA-N 0.000 description 1
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 1
- ADQKGKJCYIUMOE-UHFFFAOYSA-N 4-chloro-2-(2-imino-1,3-thiazolidin-3-yl)aniline;dihydrochloride Chemical compound Cl.Cl.NC1=CC=C(Cl)C=C1N1C(=N)SCC1 ADQKGKJCYIUMOE-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
- QFMJFXFXQAFGBO-UHFFFAOYSA-N 4-methoxy-2-nitroaniline Chemical compound COC1=CC=C(N)C([N+]([O-])=O)=C1 QFMJFXFXQAFGBO-UHFFFAOYSA-N 0.000 description 1
- ASPDJZINBYYZRU-UHFFFAOYSA-N 5-amino-2-chlorobenzotrifluoride Chemical compound NC1=CC=C(Cl)C(C(F)(F)F)=C1 ASPDJZINBYYZRU-UHFFFAOYSA-N 0.000 description 1
- BUJRSTOLFPCBTN-UHFFFAOYSA-N 5-chloro-2-(2-imino-5-methyl-1,3-thiazolidin-3-yl)aniline;dihydrochloride Chemical compound Cl.Cl.N=C1SC(C)CN1C1=CC=C(Cl)C=C1N BUJRSTOLFPCBTN-UHFFFAOYSA-N 0.000 description 1
- YCMCVFWMBIEKPA-UHFFFAOYSA-N 5-chloro-2-(2-imino-5-methyl-1,3-thiazolidin-3-yl)aniline;ethanesulfonic acid Chemical compound CCS(O)(=O)=O.CCS(O)(=O)=O.N=C1SC(C)CN1C1=CC=C(Cl)C=C1N YCMCVFWMBIEKPA-UHFFFAOYSA-N 0.000 description 1
- HRJWEXGKRQHQLA-UHFFFAOYSA-N 5-chloro-2-(4-ethyl-2-imino-1,3-thiazolidin-3-yl)aniline;dihydrochloride Chemical compound Cl.Cl.CCC1CSC(=N)N1C1=CC=C(Cl)C=C1N HRJWEXGKRQHQLA-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 244000248349 Citrus limon Species 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 241000410737 Verasper moseri Species 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000007513 acids Chemical class 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
- 230000000202 analgesic effect Effects 0.000 description 1
- QFFVPLLCYGOFPU-UHFFFAOYSA-N barium chromate Chemical compound [Ba+2].[O-][Cr]([O-])(=O)=O QFFVPLLCYGOFPU-UHFFFAOYSA-N 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- LGUHADBEXWHGIZ-UHFFFAOYSA-N butyl n-diazocarbamate Chemical compound CCCCOC(=O)N=[N+]=[N-] LGUHADBEXWHGIZ-UHFFFAOYSA-N 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical class CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
- ADWOEDKDBINMIV-UHFFFAOYSA-N ethanesulfonic acid;2-(2-imino-1,3-thiazolidin-3-yl)-5-methoxyaniline Chemical compound CCS(O)(=O)=O.CCS(O)(=O)=O.NC1=CC(OC)=CC=C1N1C(=N)SCC1 ADWOEDKDBINMIV-UHFFFAOYSA-N 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 125000005905 mesyloxy group Chemical group 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- KMMOAXMICGWZKX-UHFFFAOYSA-N methyl 3-amino-4-(2-imino-1,3-thiazolidin-3-yl)benzoate;dihydrochloride Chemical compound Cl.Cl.NC1=CC(C(=O)OC)=CC=C1N1C(=N)SCC1 KMMOAXMICGWZKX-UHFFFAOYSA-N 0.000 description 1
- HWHRGHUTXYZWEL-UHFFFAOYSA-N methyl 4-(2-imino-1,3-thiazolidin-3-yl)-3,5-dinitrobenzoate Chemical compound [O-][N+](=O)C1=CC(C(=O)OC)=CC([N+]([O-])=O)=C1N1C(=N)SCC1 HWHRGHUTXYZWEL-UHFFFAOYSA-N 0.000 description 1
- UCFBMJIHUMXEBD-UHFFFAOYSA-N methyl 4-(2-imino-1,3-thiazolidin-3-yl)-3-nitrobenzoate;hydrochloride Chemical compound Cl.[O-][N+](=O)C1=CC(C(=O)OC)=CC=C1N1C(=N)SCC1 UCFBMJIHUMXEBD-UHFFFAOYSA-N 0.000 description 1
- UANMWPWYANJDGT-UHFFFAOYSA-N methyl 4-chloro-2,6-dinitrobenzoate Chemical compound COC(=O)C1=C([N+]([O-])=O)C=C(Cl)C=C1[N+]([O-])=O UANMWPWYANJDGT-UHFFFAOYSA-N 0.000 description 1
- CNJJSTPBUHAEFH-UHFFFAOYSA-N methyl 4-fluoro-3-nitrobenzoate Chemical compound COC(=O)C1=CC=C(F)C([N+]([O-])=O)=C1 CNJJSTPBUHAEFH-UHFFFAOYSA-N 0.000 description 1
- MBBGZJAXJCMWOJ-UHFFFAOYSA-N n-(2-bromoethyl)-4-methoxy-2-nitroaniline Chemical compound COC1=CC=C(NCCBr)C([N+]([O-])=O)=C1 MBBGZJAXJCMWOJ-UHFFFAOYSA-N 0.000 description 1
- NRTFGZUFGUXFKM-UHFFFAOYSA-N n-(2-bromoethyl)-n-(4-methoxy-2-nitrophenyl)-4-methylbenzenesulfonamide Chemical compound [O-][N+](=O)C1=CC(OC)=CC=C1N(CCBr)S(=O)(=O)C1=CC=C(C)C=C1 NRTFGZUFGUXFKM-UHFFFAOYSA-N 0.000 description 1
- KLHCAOSRFFAKQV-UHFFFAOYSA-N n-(4-fluoro-3-nitrophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(F)C([N+]([O-])=O)=C1 KLHCAOSRFFAKQV-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical class [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-OUBTZVSYSA-N potassium-40 Chemical compound [40K] ZLMJMSJWJFRBEC-OUBTZVSYSA-N 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D277/18—Nitrogen atoms
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P25/24—Antidepressants
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU841581A HU191408B (en) | 1984-04-25 | 1984-04-25 | Process for preparing new imino-thiazolidine derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ATA124285A ATA124285A (de) | 1991-10-15 |
| AT394555B true AT394555B (de) | 1992-05-11 |
Family
ID=10955127
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT0124285A AT394555B (de) | 1984-04-25 | 1985-04-25 | Verfahren zur herstellung neuer iminothiazolidinderivate |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4665083A (d) |
| JP (1) | JPS6127974A (d) |
| AT (1) | AT394555B (d) |
| BE (1) | BE902249A (d) |
| CA (1) | CA1246086A (d) |
| CH (1) | CH664564A5 (d) |
| CS (1) | CS255884B2 (d) |
| DD (1) | DD231790A5 (d) |
| DE (1) | DE3514843A1 (d) |
| DK (1) | DK183585A (d) |
| ES (3) | ES8608499A1 (d) |
| FI (1) | FI82454C (d) |
| FR (1) | FR2563519B1 (d) |
| GB (1) | GB2159814B (d) |
| GR (1) | GR851006B (d) |
| HU (1) | HU191408B (d) |
| IT (1) | IT1208532B (d) |
| NL (1) | NL8501184A (d) |
| NO (1) | NO164417C (d) |
| PH (1) | PH20995A (d) |
| PL (3) | PL145084B1 (d) |
| PT (1) | PT80336B (d) |
| SE (1) | SE464813B (d) |
| SU (3) | SU1366058A3 (d) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3442757A1 (de) * | 1984-11-23 | 1986-05-28 | Wella Ag, 6100 Darmstadt | Verwendung von 2-nitroanilinderivaten in haarfaerbemitteln und neue 2-nitroanilinderivate |
| US4867782A (en) * | 1988-07-01 | 1989-09-19 | Ici Americas Inc. | Novel herbicidal 2-sulfonyliminothiazolidines |
| US5266701A (en) * | 1988-07-01 | 1993-11-30 | Ici Americas Inc. | Process for production of 2-iminothiazolidines and oxazolidines |
| US5240918A (en) * | 1992-03-24 | 1993-08-31 | Egis Gyogyszergyar | 2-(substituted imino)-thiazolidines and process for the preparation thereof |
| US5463069A (en) * | 1992-12-04 | 1995-10-31 | Sumitomo Chemical Company, Limited | Process of producing 2-iminothiazoline derivatives and process of producing their intermediates |
| JP2009501775A (ja) * | 2005-07-21 | 2009-01-22 | ベタゲノン・エイビー | 癌治療におけるチアゾール誘導体およびアナログの使用 |
| WO2010086613A1 (en) | 2009-01-30 | 2010-08-05 | Betagenon Ab | Compounds useful as inhibitors as ampk |
| JP2016526538A (ja) | 2013-06-20 | 2016-09-05 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 殺ダニ剤及び殺虫剤としてのアリールスルフィド誘導体及びアリールスルホキシド誘導体 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3775425A (en) * | 1970-06-23 | 1973-11-27 | Ciba Geigy Corp | 2-amino-4-phenyl-thiazoles and their addition salts |
| US3898340A (en) * | 1970-04-15 | 1975-08-05 | Bayer Ag | Aryliminothiazolidine compositions and methods |
| US4029803A (en) * | 1976-05-03 | 1977-06-14 | Merck & Co., Inc. | Method of treatment with 2-iminothiazolidines and thiazolines |
| EP0128736A1 (en) * | 1983-06-07 | 1984-12-19 | Yamanouchi Pharmaceutical Co., Ltd. | Novel 2-guanidinothiazoline compounds, their preparation, and their use as intermediates |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB690238A (en) * | 1949-08-23 | 1953-04-15 | Knoll Ag | Process of producing 3, 4-dimethyl-5-phenyl-2-iminothiazolidine |
| DE841149C (de) * | 1949-11-01 | 1952-06-13 | Knoll Ag | Verfahren zur Herstellung von 3, 4-Dimethyl-5-phenyl-2-iminothiazolidin |
| DE910650C (de) * | 1951-09-14 | 1954-05-03 | Knoll Ag | Verfahren zur Herstellung von 2-Amino-í¸ -thiazolinen bzw. Thiazolidon-(2)-imiden undderen Salzen |
| US3297708A (en) * | 1965-10-06 | 1967-01-10 | American Cyanamid Co | Method of preparing thiazolidines |
| FR1510014A (fr) * | 1966-12-05 | 1968-01-19 | Aquitaine Petrole | Préparation de dithiolannes |
| SU465792A3 (ru) * | 1968-11-06 | 1975-03-30 | Хиноин Гиогисцер-Ес Вегиесцети Термекек Гиара Рт (Фирма) | Способ получени гетероциклических соединений |
| US3671537A (en) * | 1969-06-05 | 1972-06-20 | Gyogyszerkutato Intezet | Certain 3-(2,6-dichlorophenyl)-2-iminothiazolidines |
| DE2655369A1 (de) * | 1976-12-03 | 1978-06-08 | Schering Ag | 5-(subst. phenyl)-oxazolidinone und deren schwefelanaloga sowie verfahren zu deren herstellung |
| HU180240B (en) * | 1978-04-21 | 1983-02-28 | Gyogyszerkutato Intezet | Process for producing new,substituted 1,3-diaryl-2-iminoimidasolidines and 2-imino-hexahydro-pyrimidines |
| US4348393A (en) * | 1978-06-09 | 1982-09-07 | Delalande S.A. | N-Aryl oxazolidinones, oxazolidinethiones, pyrrolidinones, pyrrolidines and thiazolidinones |
-
1984
- 1984-04-25 HU HU841581A patent/HU191408B/hu not_active IP Right Cessation
-
1985
- 1985-04-22 BE BE1/011242A patent/BE902249A/fr not_active IP Right Cessation
- 1985-04-23 CH CH1736/85A patent/CH664564A5/de not_active IP Right Cessation
- 1985-04-23 ES ES542469A patent/ES8608499A1/es not_active Expired
- 1985-04-23 PT PT80336A patent/PT80336B/pt not_active IP Right Cessation
- 1985-04-23 FI FI851606A patent/FI82454C/fi not_active IP Right Cessation
- 1985-04-24 DD DD85275516A patent/DD231790A5/de not_active IP Right Cessation
- 1985-04-24 FR FR8506223A patent/FR2563519B1/fr not_active Expired
- 1985-04-24 IT IT8520482A patent/IT1208532B/it active
- 1985-04-24 DE DE19853514843 patent/DE3514843A1/de active Granted
- 1985-04-24 NL NL8501184A patent/NL8501184A/nl not_active Application Discontinuation
- 1985-04-24 PH PH32179A patent/PH20995A/en unknown
- 1985-04-24 GB GB08510457A patent/GB2159814B/en not_active Expired
- 1985-04-24 CA CA000480005A patent/CA1246086A/en not_active Expired
- 1985-04-24 JP JP8660885A patent/JPS6127974A/ja active Granted
- 1985-04-24 DK DK183585A patent/DK183585A/da not_active Application Discontinuation
- 1985-04-24 NO NO851638A patent/NO164417C/no unknown
- 1985-04-24 SE SE8501988A patent/SE464813B/sv not_active IP Right Cessation
- 1985-04-25 PL PL1985257822A patent/PL145084B1/pl unknown
- 1985-04-25 US US06/726,867 patent/US4665083A/en not_active Expired - Fee Related
- 1985-04-25 GR GR851006A patent/GR851006B/el unknown
- 1985-04-25 AT AT0124285A patent/AT394555B/de not_active IP Right Cessation
- 1985-04-25 SU SU853884105A patent/SU1366058A3/ru active
- 1985-04-25 CS CS853049A patent/CS255884B2/cs unknown
- 1985-04-25 PL PL1985257821A patent/PL144860B1/pl unknown
- 1985-04-25 PL PL1985253089A patent/PL144821B1/pl unknown
-
1986
- 1986-01-31 ES ES551481A patent/ES8701741A1/es not_active Expired
- 1986-01-31 ES ES551480A patent/ES8702391A1/es not_active Expired
- 1986-03-05 SU SU864027048A patent/SU1549480A3/ru active
- 1986-03-05 SU SU864027053A patent/SU1375132A3/ru active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3898340A (en) * | 1970-04-15 | 1975-08-05 | Bayer Ag | Aryliminothiazolidine compositions and methods |
| US3775425A (en) * | 1970-06-23 | 1973-11-27 | Ciba Geigy Corp | 2-amino-4-phenyl-thiazoles and their addition salts |
| US4029803A (en) * | 1976-05-03 | 1977-06-14 | Merck & Co., Inc. | Method of treatment with 2-iminothiazolidines and thiazolines |
| EP0128736A1 (en) * | 1983-06-07 | 1984-12-19 | Yamanouchi Pharmaceutical Co., Ltd. | Novel 2-guanidinothiazoline compounds, their preparation, and their use as intermediates |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH650782A5 (de) | Carbostyrilverbindungen, verfahren zu deren herstellung und arzneimittel, welche diese enthalten. | |
| DE1695478A1 (de) | Sulfonamidotryptamine | |
| AT394555B (de) | Verfahren zur herstellung neuer iminothiazolidinderivate | |
| DE69132689T2 (de) | Biologisch aktive amine | |
| DE69530988T2 (de) | Benzimidazolderivate mit dopaminerger wirkung | |
| DE1954584A1 (de) | Verfahren zur Herstellung von neuen heterocyclischen Verbindungen | |
| DE68915310T2 (de) | Verfahren zur Herstellung von enantiomerischen homogenen Aminopyrrolidinyl-naphthyridin- und Quinoloncarbonsäuren. | |
| CH646156A5 (de) | Schwefelhaltige benzimidazol-derivate und verfahren zu ihrer herstellung. | |
| CH630383A5 (de) | Verfahren zur herstellung von cyclischen derivaten von 1,4-benzoxazin und 1,4-benzothiazin. | |
| DE69519315T2 (de) | Aminoalkyl Benzoxazolinone und Benzothiazolinone, Verfahren zu deren Herstellung und sie enthaltende Zusammensetzungen | |
| CH622491A5 (en) | Process for the preparation of novel hydroxypropylamines | |
| DE3784795T2 (de) | Verfahren zur herstellung von 5,6-substituierten-2,4-chinazolindiaminen und zwischenprodukten. | |
| DE3320102A1 (de) | Neue, in 2-stellung substituierte derivate der 4-hydroxy-3-chinolincarbonsaeure, deren herstellung, deren verwendung als arzneimittel, die sie enthaltenden zusammensetzungen und erhaltene zwischenprodukte | |
| DE2844497C2 (de) | Phenoxyalkanolamin-Derivate und Verfahren zu deren Herstellung | |
| DE3642497A1 (de) | Substituierte aminopropionsaeureamide, verfahren zu ihrer herstellung, diese enthaltende mittel und ihre verwendung sowie die bei der herstellung anfallenden neuen zwischenprodukte | |
| CH628041A5 (de) | Verfahren zur herstellung neuer 4-hydroxy-2h-naphtho(2,1-e)-1,2-thiazin-3-carboxamid-1,1-dioxyde. | |
| DE69713128T2 (de) | 4-(1-piperazinyl)benzosäurederivate, verfahren zu ihrer herstellung und ihre therapeutischen verwendungen | |
| DE2065854C3 (de) | Verfahren zur Herstellung von 2,3,5,6-Tetrahydroimidazo- eckige Klammer auf 2,1-b] -thiazol | |
| DE2709720A1 (de) | N-substituierte 2-arylamino-imidazoline-(2), verfahren zu deren herstellung und neue hydroxylamine als zwischenprodukte | |
| AT333751B (de) | Verfahren zur herstellung von neuen anilinobenzothiazolderivaten und ihren salzen | |
| US4002620A (en) | 2-Anilino-4H-3,1-benzothiazines | |
| DE2136325C3 (de) | 2-(Indanyl-4'-amino) Delta hoch 2imidazolin, seine physiologisch unbedenklichen Säureadditionssalze, Verfahren zu ihrer Herstellung sowie Arzneimittel | |
| DE2626128A1 (de) | N-substituierte benzimidazolin-2-one und verfahren zu deren herstellung | |
| CH630245A5 (en) | Feed additives | |
| DE2212693A1 (de) | Dihydro-2-aminoisochinoline und Verfahren zu deren Herstellung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ELJ | Ceased due to non-payment of the annual fee |