FI57594C - Foerfarande foer framstaellning av antiallergiskt verksamma n-(bentstiazol-2-yl)-oxamidsyra-derivat - Google Patents
Foerfarande foer framstaellning av antiallergiskt verksamma n-(bentstiazol-2-yl)-oxamidsyra-derivat Download PDFInfo
- Publication number
- FI57594C FI57594C FI773738A FI773738A FI57594C FI 57594 C FI57594 C FI 57594C FI 773738 A FI773738 A FI 773738A FI 773738 A FI773738 A FI 773738A FI 57594 C FI57594 C FI 57594C
- Authority
- FI
- Finland
- Prior art keywords
- melting point
- mol
- methoxy
- ethyl ester
- benzthiazol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 49
- 230000003266 anti-allergic effect Effects 0.000 title description 4
- -1 benzthiazol-2-yl Chemical group 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 12
- SOWBFZRMHSNYGE-UHFFFAOYSA-N oxamic acid Chemical class NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 150000002912 oxalic acid derivatives Chemical class 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
- 238000002844 melting Methods 0.000 description 62
- 230000008018 melting Effects 0.000 description 62
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 40
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- 238000001819 mass spectrum Methods 0.000 description 20
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 16
- UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical class C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000012043 crude product Substances 0.000 description 13
- 239000002244 precipitate Substances 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 238000001953 recrystallisation Methods 0.000 description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 10
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 10
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 10
- 238000002329 infrared spectrum Methods 0.000 description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 9
- 229910052794 bromium Inorganic materials 0.000 description 9
- 125000004494 ethyl ester group Chemical group 0.000 description 9
- 238000002211 ultraviolet spectrum Methods 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 159000000000 sodium salts Chemical class 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- UYCUMNRCCJNSBR-UHFFFAOYSA-N 2-ethoxy-2-oxoacetic acid;hydrochloride Chemical compound Cl.CCOC(=O)C(O)=O UYCUMNRCCJNSBR-UHFFFAOYSA-N 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 6
- 150000001735 carboxylic acids Chemical class 0.000 description 6
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000007363 ring formation reaction Methods 0.000 description 5
- ZFGBGKKWENABEC-UHFFFAOYSA-N 2-o-tert-butyl 1-o-ethyl oxalate Chemical compound CCOC(=O)C(=O)OC(C)(C)C ZFGBGKKWENABEC-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000004108 freeze drying Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000006798 ring closing metathesis reaction Methods 0.000 description 4
- RXUORKOATDNJFN-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-ylamino)-2-oxoacetic acid Chemical class C1=CC=C2SC(NC(=O)C(=O)O)=NC2=C1 RXUORKOATDNJFN-UHFFFAOYSA-N 0.000 description 3
- YEBCRAVYUWNFQT-UHFFFAOYSA-N 4-methoxy-1,3-benzothiazol-2-amine Chemical compound COC1=CC=CC2=C1N=C(N)S2 YEBCRAVYUWNFQT-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000005809 transesterification reaction Methods 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- NAZDVUBIEPVUKE-UHFFFAOYSA-N 2,5-dimethoxyaniline Chemical compound COC1=CC=C(OC)C(N)=C1 NAZDVUBIEPVUKE-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- DCMUUSUYVZEYNG-UHFFFAOYSA-N 2-methoxy-5-propan-2-ylaniline Chemical compound COC1=CC=C(C(C)C)C=C1N DCMUUSUYVZEYNG-UHFFFAOYSA-N 0.000 description 2
- FGZBTCDIPNGYRC-UHFFFAOYSA-N 4-(trifluoromethyl)-1,3-benzothiazol-2-amine Chemical compound C1=CC=C2SC(N)=NC2=C1C(F)(F)F FGZBTCDIPNGYRC-UHFFFAOYSA-N 0.000 description 2
- XPYJFCKUPMJFHE-UHFFFAOYSA-N 4-nitro-1,3-benzothiazol-2-amine Chemical compound C1=CC=C2SC(N)=NC2=C1[N+]([O-])=O XPYJFCKUPMJFHE-UHFFFAOYSA-N 0.000 description 2
- KZHGPDSVHSDCMX-UHFFFAOYSA-N 6-methoxy-1,3-benzothiazol-2-amine Chemical compound COC1=CC=C2N=C(N)SC2=C1 KZHGPDSVHSDCMX-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- XLLAVRBEOFTKRD-UHFFFAOYSA-N CCOC(C(NC1=NC(C(OC)=CC=C2C(C)(C)C)=C2S1)=O)=O Chemical compound CCOC(C(NC1=NC(C(OC)=CC=C2C(C)(C)C)=C2S1)=O)=O XLLAVRBEOFTKRD-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- FULZLIGZKMKICU-UHFFFAOYSA-N N-phenylthiourea Chemical class NC(=S)NC1=CC=CC=C1 FULZLIGZKMKICU-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical class COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- JQWLWTCFGLPVHG-UHFFFAOYSA-N ethyl 2-(1,3-benzothiazol-2-ylamino)-2-oxoacetate Chemical compound C1=CC=C2SC(NC(=O)C(=O)OCC)=NC2=C1 JQWLWTCFGLPVHG-UHFFFAOYSA-N 0.000 description 2
- MEAXWFLNCMDQBF-UHFFFAOYSA-N ethyl 2-[(4,7-dimethoxy-1,3-benzothiazol-2-yl)amino]-2-oxoacetate Chemical compound COC1=CC=C(C2=C1N=C(S2)NC(C(=O)OCC)=O)OC MEAXWFLNCMDQBF-UHFFFAOYSA-N 0.000 description 2
- RXVQPQVWAPDCAG-UHFFFAOYSA-N ethyl 2-[(4-methoxy-5,7-dimethyl-1,3-benzothiazol-2-yl)amino]-2-oxoacetate Chemical compound COC1=C(C=C(C2=C1N=C(S2)NC(C(=O)OCC)=O)C)C RXVQPQVWAPDCAG-UHFFFAOYSA-N 0.000 description 2
- MFWFMJDTMVACSZ-UHFFFAOYSA-N ethyl 2-[(4-methoxy-7-propan-2-yl-1,3-benzothiazol-2-yl)amino]-2-oxoacetate Chemical compound C(C)(C)C1=CC=C(C=2N=C(SC21)NC(C(=O)OCC)=O)OC MFWFMJDTMVACSZ-UHFFFAOYSA-N 0.000 description 2
- PADBSRUOCMRQIY-UHFFFAOYSA-N ethyl 2-[(4-methyl-1,3-benzothiazol-2-yl)amino]-2-oxoacetate Chemical compound C1=CC=C2SC(NC(=O)C(=O)OCC)=NC2=C1C PADBSRUOCMRQIY-UHFFFAOYSA-N 0.000 description 2
- KPCJPDQPKYCQTM-UHFFFAOYSA-N ethyl 2-[(4-nitro-1,3-benzothiazol-2-yl)amino]-2-oxoacetate Chemical compound [N+](=O)([O-])C1=CC=CC2=C1N=C(S2)NC(C(=O)OCC)=O KPCJPDQPKYCQTM-UHFFFAOYSA-N 0.000 description 2
- PJSRKRXCAFTOAC-UHFFFAOYSA-N ethyl 2-[(5,6-dimethoxy-1,3-benzothiazol-2-yl)amino]-2-oxoacetate Chemical compound COC=1C(=CC2=C(N=C(S2)NC(C(=O)OCC)=O)C1)OC PJSRKRXCAFTOAC-UHFFFAOYSA-N 0.000 description 2
- WVIUMEASFPCKQZ-UHFFFAOYSA-N ethyl 2-[(5-chloro-4-methoxy-1,3-benzothiazol-2-yl)amino]-2-oxoacetate Chemical compound ClC=1C=CC2=C(N=C(S2)NC(C(=O)OCC)=O)C1OC WVIUMEASFPCKQZ-UHFFFAOYSA-N 0.000 description 2
- PKHDHMQIXQLXBS-UHFFFAOYSA-N ethyl 2-[(6-methoxy-5,7-dimethyl-1,3-benzothiazol-2-yl)amino]-2-oxoacetate Chemical compound COC1=C(C2=C(N=C(S2)NC(C(=O)OCC)=O)C=C1C)C PKHDHMQIXQLXBS-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- DQMWMUMCNOJLSI-UHFFFAOYSA-N n-carbamothioylbenzamide Chemical compound NC(=S)NC(=O)C1=CC=CC=C1 DQMWMUMCNOJLSI-UHFFFAOYSA-N 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- ZLGQKHQZDDTIFW-UHFFFAOYSA-N (2,5-dimethoxyphenyl)thiourea Chemical compound COC1=CC=C(OC)C(NC(N)=S)=C1 ZLGQKHQZDDTIFW-UHFFFAOYSA-N 0.000 description 1
- HXUWZZBFOMIUAU-UHFFFAOYSA-N (2-chloro-5-methoxyphenyl)thiourea Chemical compound COC1=CC=C(Cl)C(NC(N)=S)=C1 HXUWZZBFOMIUAU-UHFFFAOYSA-N 0.000 description 1
- VAWRJMKHAJYUEY-UHFFFAOYSA-N (2-methoxy-5-propan-2-ylphenyl)thiourea Chemical compound C(C)(C)C=1C=CC(=C(C1)NC(=S)N)OC VAWRJMKHAJYUEY-UHFFFAOYSA-N 0.000 description 1
- FLGZBEKWHFRZNP-UHFFFAOYSA-N (2-nitrophenyl)thiourea Chemical compound NC(=S)NC1=CC=CC=C1[N+]([O-])=O FLGZBEKWHFRZNP-UHFFFAOYSA-N 0.000 description 1
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- VMKQIIHXIOEFLH-UHFFFAOYSA-N (3,4-dimethoxyphenyl)thiourea Chemical compound COC1=CC=C(NC(N)=S)C=C1OC VMKQIIHXIOEFLH-UHFFFAOYSA-N 0.000 description 1
- BORWHVXHJVKJAB-UHFFFAOYSA-N (3-chloro-2-methoxyphenyl)thiourea Chemical compound COC1=C(Cl)C=CC=C1NC(N)=S BORWHVXHJVKJAB-UHFFFAOYSA-N 0.000 description 1
- SEMNHAXMORNHNR-UHFFFAOYSA-N (5-chloro-2-methoxyphenyl)thiourea Chemical compound COC1=CC=C(Cl)C=C1NC(N)=S SEMNHAXMORNHNR-UHFFFAOYSA-N 0.000 description 1
- RLHOIKPZBFJZLO-UHFFFAOYSA-N (5-tert-butyl-2-methoxyphenyl)thiourea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(N)=S RLHOIKPZBFJZLO-UHFFFAOYSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- XGNXYCFREOZBOL-UHFFFAOYSA-N 1,3-benzodioxol-5-amine Chemical compound NC1=CC=C2OCOC2=C1 XGNXYCFREOZBOL-UHFFFAOYSA-N 0.000 description 1
- FEDOVBDZDYIYDD-UHFFFAOYSA-N 1,3-benzodioxol-5-ylthiourea Chemical compound NC(=S)NC1=CC=C2OCOC2=C1 FEDOVBDZDYIYDD-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- VBLXCTYLWZJBKA-UHFFFAOYSA-N 2-(trifluoromethyl)aniline Chemical compound NC1=CC=CC=C1C(F)(F)F VBLXCTYLWZJBKA-UHFFFAOYSA-N 0.000 description 1
- QTXKVMGIDGCTFD-UHFFFAOYSA-N 2-[(4-methoxy-1,3-benzothiazol-2-yl)amino]-2-oxoacetic acid Chemical compound COC1=CC=CC2=C1N=C(S2)NC(C(=O)O)=O QTXKVMGIDGCTFD-UHFFFAOYSA-N 0.000 description 1
- UIXZQUZEUFVSDG-UHFFFAOYSA-N 2-[(5-methoxy-1,3-benzothiazol-2-yl)amino]-2-oxoacetic acid Chemical compound COC=1C=CC2=C(N=C(S2)NC(C(=O)O)=O)C1 UIXZQUZEUFVSDG-UHFFFAOYSA-N 0.000 description 1
- QXEDZSMKQDXWQA-UHFFFAOYSA-N 2-[(6-methoxy-1,3-benzothiazol-2-yl)amino]-2-oxoacetic acid Chemical compound COC1=CC=C2N=C(NC(=O)C(O)=O)SC2=C1 QXEDZSMKQDXWQA-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- HQJBYCPQFNTCNM-UHFFFAOYSA-N 2-methoxy-3,5-dimethylaniline Chemical compound COC1=C(C)C=C(C)C=C1N HQJBYCPQFNTCNM-UHFFFAOYSA-N 0.000 description 1
- GVBHRNIWBGTNQA-UHFFFAOYSA-N 2-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=CC=C1N GVBHRNIWBGTNQA-UHFFFAOYSA-N 0.000 description 1
- DTYBRSLINXBXMP-UHFFFAOYSA-N 2-methoxy-5-phenylaniline Chemical compound C1=C(N)C(OC)=CC=C1C1=CC=CC=C1 DTYBRSLINXBXMP-UHFFFAOYSA-N 0.000 description 1
- LGDHZCLREKIGKJ-UHFFFAOYSA-N 3,4-dimethoxyaniline Chemical compound COC1=CC=C(N)C=C1OC LGDHZCLREKIGKJ-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- GVDOKYBXIQWKJG-UHFFFAOYSA-N 4,7-dimethoxy-1,3-benzothiazol-2-amine Chemical compound COC1=CC=C(OC)C2=C1N=C(N)S2 GVDOKYBXIQWKJG-UHFFFAOYSA-N 0.000 description 1
- XWPDPFLBSAPRCO-UHFFFAOYSA-N 4-(chloromethoxy)aniline Chemical compound NC1=CC=C(OCCl)C=C1 XWPDPFLBSAPRCO-UHFFFAOYSA-N 0.000 description 1
- OEQQFQXMCPMEIH-UHFFFAOYSA-N 4-chloro-1,3-benzothiazol-2-amine Chemical compound C1=CC=C2SC(N)=NC2=C1Cl OEQQFQXMCPMEIH-UHFFFAOYSA-N 0.000 description 1
- OXQVZAIGQSSWCS-UHFFFAOYSA-N 4-chloro-7-methoxy-1,3-benzothiazol-2-amine Chemical compound COC1=CC=C(Cl)C2=C1SC(N)=N2 OXQVZAIGQSSWCS-UHFFFAOYSA-N 0.000 description 1
- HUPGZEYAAFYLSC-UHFFFAOYSA-N 4-methoxy-3,5-dimethylaniline Chemical compound COC1=C(C)C=C(N)C=C1C HUPGZEYAAFYLSC-UHFFFAOYSA-N 0.000 description 1
- WHAPHGMDUORJFL-UHFFFAOYSA-N 4-methoxy-5,7-dimethyl-1,3-benzothiazol-2-amine Chemical compound COC1=C(C)C=C(C)C2=C1N=C(N)S2 WHAPHGMDUORJFL-UHFFFAOYSA-N 0.000 description 1
- CPKIXPBVHIJAIR-UHFFFAOYSA-N 4-methoxy-6-nitro-1,3-benzothiazol-2-amine Chemical compound COC1=CC([N+]([O-])=O)=CC2=C1N=C(N)S2 CPKIXPBVHIJAIR-UHFFFAOYSA-N 0.000 description 1
- KUZPSPIMIBWVAW-UHFFFAOYSA-N 4-methoxy-7-phenyl-1,3-benzothiazol-2-amine Chemical compound C1=2SC(N)=NC=2C(OC)=CC=C1C1=CC=CC=C1 KUZPSPIMIBWVAW-UHFFFAOYSA-N 0.000 description 1
- HTLWMPOLPFBJLS-UHFFFAOYSA-N 4-methoxy-7-propan-2-yl-1,3-benzothiazol-2-amine Chemical compound NC=1SC2=C(N=1)C(=CC=C2C(C)C)OC HTLWMPOLPFBJLS-UHFFFAOYSA-N 0.000 description 1
- KJRDZJGBIBLGKB-UHFFFAOYSA-N 5,6-dimethoxy-1,3-benzothiazol-2-amine Chemical compound C1=C(OC)C(OC)=CC2=C1SC(N)=N2 KJRDZJGBIBLGKB-UHFFFAOYSA-N 0.000 description 1
- IODWHFFPQHUDAG-UHFFFAOYSA-N 5,6-dimethyl-1,3-benzothiazol-2-amine Chemical compound C1=C(C)C(C)=CC2=C1SC(N)=N2 IODWHFFPQHUDAG-UHFFFAOYSA-N 0.000 description 1
- WBSMIPLNPSCJFS-UHFFFAOYSA-N 5-chloro-2-methoxyaniline Chemical compound COC1=CC=C(Cl)C=C1N WBSMIPLNPSCJFS-UHFFFAOYSA-N 0.000 description 1
- GCIRICTXAJBAHX-UHFFFAOYSA-N 5-chloro-4-methoxy-1,3-benzothiazol-2-amine Chemical compound COC1=C(Cl)C=CC2=C1N=C(N)S2 GCIRICTXAJBAHX-UHFFFAOYSA-N 0.000 description 1
- OMIHQJBWAPWLBO-UHFFFAOYSA-N 5-methoxy-1,3-benzothiazol-2-amine Chemical compound COC1=CC=C2SC(N)=NC2=C1 OMIHQJBWAPWLBO-UHFFFAOYSA-N 0.000 description 1
- DLTLFDQLMFMTRQ-UHFFFAOYSA-N 5-tert-butyl-2-methoxyaniline Chemical compound COC1=CC=C(C(C)(C)C)C=C1N DLTLFDQLMFMTRQ-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- KOYJWFGMEBETBU-UHFFFAOYSA-N 6-ethoxy-1,3-benzothiazol-2-amine Chemical compound CCOC1=CC=C2N=C(N)SC2=C1 KOYJWFGMEBETBU-UHFFFAOYSA-N 0.000 description 1
- KFFGZKCROJZIMK-UHFFFAOYSA-N 6-methoxy-5,7-dimethyl-1,3-benzothiazol-2-amine Chemical compound NC=1SC2=C(N=1)C=C(C(=C2C)OC)C KFFGZKCROJZIMK-UHFFFAOYSA-N 0.000 description 1
- GPNAVOJCQIEKQF-UHFFFAOYSA-N 6-nitro-1,3-benzothiazol-2-amine Chemical compound C1=C([N+]([O-])=O)C=C2SC(N)=NC2=C1 GPNAVOJCQIEKQF-UHFFFAOYSA-N 0.000 description 1
- CLFYPDRIWLKZOS-UHFFFAOYSA-N 7-chloro-4-methoxy-1,3-benzothiazol-2-amine Chemical compound COC1=CC=C(Cl)C2=C1N=C(N)S2 CLFYPDRIWLKZOS-UHFFFAOYSA-N 0.000 description 1
- NBSMJUGPGWBQHM-UHFFFAOYSA-N 7-tert-butyl-4-methoxy-1,3-benzothiazol-2-amine Chemical compound COC1=CC=C(C(C)(C)C)C2=C1N=C(N)S2 NBSMJUGPGWBQHM-UHFFFAOYSA-N 0.000 description 1
- PZASAAIJIFDWSB-CKPDSHCKSA-N 8-[(1S)-1-[8-(trifluoromethyl)-7-[4-(trifluoromethyl)cyclohexyl]oxynaphthalen-2-yl]ethyl]-8-azabicyclo[3.2.1]octane-3-carboxylic acid Chemical compound FC(F)(F)C=1C2=CC([C@@H](N3C4CCC3CC(C4)C(O)=O)C)=CC=C2C=CC=1OC1CCC(C(F)(F)F)CC1 PZASAAIJIFDWSB-CKPDSHCKSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- NLNBJEDYJHJJIV-UHFFFAOYSA-N C1=CC=C2C(=C1)N=C(S2)N(C(=O)C(=O)N)N Chemical compound C1=CC=C2C(=C1)N=C(S2)N(C(=O)C(=O)N)N NLNBJEDYJHJJIV-UHFFFAOYSA-N 0.000 description 1
- AHXVXFGTRGUIKA-UHFFFAOYSA-N COC1=C(C=C(C=C1)C2=CC=CC=C2)NC(=S)NC(=O)C3=CC=CC=C3 Chemical compound COC1=C(C=C(C=C1)C2=CC=CC=C2)NC(=S)NC(=O)C3=CC=CC=C3 AHXVXFGTRGUIKA-UHFFFAOYSA-N 0.000 description 1
- RPCXIOOYFULISR-UHFFFAOYSA-N COC1=C2C(=CC(=C1)[N+](=O)[O-])SC(=N2)NC(=O)C(=O)N Chemical compound COC1=C2C(=CC(=C1)[N+](=O)[O-])SC(=N2)NC(=O)C(=O)N RPCXIOOYFULISR-UHFFFAOYSA-N 0.000 description 1
- OKLFBJCPTAGNRY-UHFFFAOYSA-N COC1=CC=CC2=C1N=C(S2)NC(C(=O)OCC)=O Chemical compound COC1=CC=CC2=C1N=C(S2)NC(C(=O)OCC)=O OKLFBJCPTAGNRY-UHFFFAOYSA-N 0.000 description 1
- YNRDQRGPSYNJOZ-UHFFFAOYSA-N COC=1C=CC2=C(N=C(S2)NC(C(=O)OCC)=O)C=1 Chemical compound COC=1C=CC2=C(N=C(S2)NC(C(=O)OCC)=O)C=1 YNRDQRGPSYNJOZ-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-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
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241000206672 Gelidium Species 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-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
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 206010070835 Skin sensitisation Diseases 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- FVXFFFHGYOYYQX-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]thiourea Chemical compound NC(=S)NC1=CC=CC=C1C(F)(F)F FVXFFFHGYOYYQX-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000002365 anti-tubercular Effects 0.000 description 1
- 229940121383 antituberculosis agent Drugs 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- SEGBQNJGOCXIGC-FHERZECASA-N benzyl n-[(2s)-1-[(4-hydroxyoxolan-3-yl)amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound N([C@@H](CC(C)C)C(=O)NC1C(COC1)O)C(=O)OCC1=CC=CC=C1 SEGBQNJGOCXIGC-FHERZECASA-N 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000000160 carbon, hydrogen and nitrogen elemental analysis Methods 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000006727 cell loss Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 239000003433 contraceptive agent Substances 0.000 description 1
- 230000002254 contraceptive effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000017858 demethylation Effects 0.000 description 1
- 238000010520 demethylation reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- FZCIDVLCVJDVBP-UHFFFAOYSA-N ethyl 2-([1,3]dioxolo[4,5-f][1,3]benzothiazol-6-ylamino)-2-oxoacetate Chemical compound O1COC2=CC3=C(N=C(S3)NC(C(=O)OCC)=O)C=C21 FZCIDVLCVJDVBP-UHFFFAOYSA-N 0.000 description 1
- AQSYEQIPXFEXCQ-UHFFFAOYSA-N ethyl 2-[(4-chloro-7-methoxy-1,3-benzothiazol-2-yl)amino]-2-oxoacetate Chemical compound ClC1=CC=C(C2=C1N=C(S2)NC(C(=O)OCC)=O)OC AQSYEQIPXFEXCQ-UHFFFAOYSA-N 0.000 description 1
- ARCBXODZEFFVFW-UHFFFAOYSA-N ethyl 2-[(4-methoxy-7-phenyl-1,3-benzothiazol-2-yl)amino]-2-oxoacetate Chemical compound C=12SC(NC(=O)C(=O)OCC)=NC2=C(OC)C=CC=1C1=CC=CC=C1 ARCBXODZEFFVFW-UHFFFAOYSA-N 0.000 description 1
- OTBBWVDTIPZLJN-UHFFFAOYSA-N ethyl 2-[(5,6-dimethyl-1,3-benzothiazol-2-yl)amino]-2-oxoacetate Chemical compound CC=1C(=CC2=C(N=C(S2)NC(C(=O)OCC)=O)C1)C OTBBWVDTIPZLJN-UHFFFAOYSA-N 0.000 description 1
- SMTXEVLYROUGMC-UHFFFAOYSA-N ethyl 2-[(6-methoxy-1,3-benzothiazol-2-yl)amino]-2-oxoacetate Chemical compound C1=C(OC)C=C2SC(NC(=O)C(=O)OCC)=NC2=C1 SMTXEVLYROUGMC-UHFFFAOYSA-N 0.000 description 1
- NZILSSCNFHBUCO-UHFFFAOYSA-N ethyl 2-[(6-nitro-1,3-benzothiazol-2-yl)amino]-2-oxoacetate Chemical compound C1=C([N+]([O-])=O)C=C2SC(NC(=O)C(=O)OCC)=NC2=C1 NZILSSCNFHBUCO-UHFFFAOYSA-N 0.000 description 1
- FSMPMFMUVQDADP-UHFFFAOYSA-N ethyl 2-[(7-chloro-4-methoxy-1,3-benzothiazol-2-yl)amino]-2-oxoacetate Chemical compound ClC1=CC=C(C=2N=C(SC21)NC(C(=O)OCC)=O)OC FSMPMFMUVQDADP-UHFFFAOYSA-N 0.000 description 1
- RZMZBHSKPLVQCP-UHFFFAOYSA-N ethyl 2-amino-2-oxoacetate Chemical compound CCOC(=O)C(N)=O RZMZBHSKPLVQCP-UHFFFAOYSA-N 0.000 description 1
- MNEGOSANAHVLCW-UHFFFAOYSA-N ethyl 2-oxo-2-[[4-(trifluoromethyl)-1,3-benzothiazol-2-yl]amino]acetate Chemical compound FC(C1=CC=CC2=C1N=C(S2)NC(C(=O)OCC)=O)(F)F MNEGOSANAHVLCW-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012458 free base Substances 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
- 239000008187 granular material Substances 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 210000003630 histaminocyte Anatomy 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 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
- 239000008101 lactose Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- AEVHVVDLIHWAGR-UHFFFAOYSA-N methyl 2-amino-2-oxoacetate Chemical compound COC(=O)C(N)=O AEVHVVDLIHWAGR-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- VQDHCBNTGMHIRX-UHFFFAOYSA-N n'-(1,3-benzothiazol-2-yl)oxamide Chemical compound C1=CC=C2SC(NC(=O)C(=O)N)=NC2=C1 VQDHCBNTGMHIRX-UHFFFAOYSA-N 0.000 description 1
- LNZFAJIMQDIJAR-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylcarbamothioyl)benzamide Chemical compound C=1C=C2OCOC2=CC=1NC(=S)NC(=O)C1=CC=CC=C1 LNZFAJIMQDIJAR-UHFFFAOYSA-N 0.000 description 1
- RQLQKROEEJIYGG-UHFFFAOYSA-N n-[(2,5-dimethoxyphenyl)carbamothioyl]benzamide Chemical compound COC1=CC=C(OC)C(NC(=S)NC(=O)C=2C=CC=CC=2)=C1 RQLQKROEEJIYGG-UHFFFAOYSA-N 0.000 description 1
- SDAGLOUNULVBNM-UHFFFAOYSA-N n-[(2-chloro-5-methoxyphenyl)carbamothioyl]benzamide Chemical compound COC1=CC=C(Cl)C(NC(=S)NC(=O)C=2C=CC=CC=2)=C1 SDAGLOUNULVBNM-UHFFFAOYSA-N 0.000 description 1
- DAOGSRUHYYZJHT-UHFFFAOYSA-N n-[(5-chloro-2-methoxyphenyl)carbamothioyl]benzamide Chemical compound COC1=CC=C(Cl)C=C1NC(=S)NC(=O)C1=CC=CC=C1 DAOGSRUHYYZJHT-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
- ACLZYRNSDLQOIA-UHFFFAOYSA-N o-tolylthiourea Chemical compound CC1=CC=CC=C1NC(N)=S ACLZYRNSDLQOIA-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003883 ointment base Substances 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 229940116357 potassium thiocyanate Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical group CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 231100000370 skin sensitisation Toxicity 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 239000000814 tuberculostatic agent Substances 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
- C07D277/82—Nitrogen atoms
-
- 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
- C07D317/44—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 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—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 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring 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 atoms of the carbocyclic ring
- C07D317/66—Nitrogen atoms not forming part of a nitro radical
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pulmonology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Immunology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762656468 DE2656468A1 (de) | 1976-12-14 | 1976-12-14 | N-(benzthiazol-2-yl)-oxamidsaeure- derivate und verfahren zu ihrer herstellung |
| DE2656468 | 1976-12-14 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI773738A7 FI773738A7 (fi) | 1978-06-15 |
| FI57594B FI57594B (fi) | 1980-05-30 |
| FI57594C true FI57594C (fi) | 1980-09-10 |
Family
ID=5995427
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI773738A FI57594C (fi) | 1976-12-14 | 1977-12-12 | Foerfarande foer framstaellning av antiallergiskt verksamma n-(bentstiazol-2-yl)-oxamidsyra-derivat |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS5377058A (cs) |
| AR (1) | AR216496A1 (cs) |
| AT (1) | AT360523B (cs) |
| AU (1) | AU510730B2 (cs) |
| BE (1) | BE861794A (cs) |
| CS (1) | CS203179B2 (cs) |
| DD (1) | DD133329A5 (cs) |
| DE (1) | DE2656468A1 (cs) |
| ES (1) | ES465034A1 (cs) |
| FI (1) | FI57594C (cs) |
| FR (1) | FR2374317A1 (cs) |
| GB (1) | GB1538822A (cs) |
| HU (1) | HU175340B (cs) |
| NL (1) | NL7713580A (cs) |
| SE (1) | SE7714074L (cs) |
| SU (1) | SU680647A3 (cs) |
| ZA (1) | ZA777236B (cs) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2676775A (en) * | 1949-10-24 | 1954-04-27 | Gustav O Schulz | Electric flatiron cord holder |
| DE3017976A1 (de) * | 1980-05-10 | 1981-11-19 | Dr. Karl Thomae Gmbh, 7950 Biberach | Substituierte 2-amino-5-halogen-benzothiazole, verfahen zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| US4321372A (en) | 1980-06-16 | 1982-03-23 | Pfizer Inc. | Antiulcer thiazol-2-ylcarbamoyl-carboxylic acids, esters and amides |
| DE3027527A1 (de) | 1980-07-19 | 1982-02-18 | Basf Ag, 6700 Ludwigshafen | Neue oxamidsaeure-derivate, verfahren zu ihrer herstellung und diese enthaltende therapeutische mittel |
| GB2090826B (en) * | 1981-01-09 | 1985-06-12 | Usv Pharma Corp | New heterocyclic compounds useful as anti-allergie agents |
| DE3135250A1 (de) * | 1981-09-05 | 1983-03-17 | Basf Ag, 6700 Ludwigshafen | Tricyclische thiazolyloxamate, verfahren zu ihrer herstellung und diese enthaltende therapeutische mittel |
| US4826860A (en) * | 1987-03-16 | 1989-05-02 | Warner-Lambert Company | Substituted 2-aminobenzothiazoles and derivatives useful as cerebrovascular agents |
| FI91859C (fi) * | 1987-06-17 | 1994-08-25 | Eisai Co Ltd | Analogiamenetelmä antiallergisena aineena aktiivisen bentsotiatsolijohdannaisen valmistamiseksi |
| BR0112395A (pt) * | 2000-06-21 | 2003-07-08 | Hoffmann La Roche | Derivados de benzotiazol |
| US7087761B2 (en) | 2003-01-07 | 2006-08-08 | Hoffmann-La Roche Inc. | Cyclization process for substituted benzothiazole derivatives |
| JP4668265B2 (ja) | 2004-05-24 | 2011-04-13 | エフ．ホフマン−ラ ロシュ アーゲー | ４−ヒドロキシ−４−メチル−ピペリジン−１−カルボン酸（４−メトキシ−７−モルホリン−４−イル−ベンゾチアゾール−２−イル）−アミド |
| US7459563B2 (en) | 2004-11-05 | 2008-12-02 | Hoffmann-La Roche Inc. | Process for the preparation of isonicotinic acid derivatives |
| EP1863818B1 (en) | 2005-03-23 | 2010-03-10 | F.Hoffmann-La Roche Ag | Acetylenyl-pyrazolo-pvrimidine derivatives as mglur2 antagonists |
| ES2340321T3 (es) | 2005-09-27 | 2010-06-01 | F.Hoffmann-La Roche Ag | Oxadiazolilpirazolo-pirimidinas, como antagonistas de mglur2. |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4150140A (en) * | 1976-12-23 | 1979-04-17 | The Upjohn Company | Benzothiazolyl oxanic acids, esters and salts |
-
1976
- 1976-12-14 DE DE19762656468 patent/DE2656468A1/de not_active Withdrawn
-
1977
- 1977-12-03 HU HU77BO1695A patent/HU175340B/hu unknown
- 1977-12-05 ZA ZA00777236A patent/ZA777236B/xx unknown
- 1977-12-07 GB GB50911/77A patent/GB1538822A/en not_active Expired
- 1977-12-07 SU SU772550552A patent/SU680647A3/ru active
- 1977-12-07 AR AR270289A patent/AR216496A1/es active
- 1977-12-07 CS CS778173A patent/CS203179B2/cs unknown
- 1977-12-08 NL NL7713580A patent/NL7713580A/xx not_active Application Discontinuation
- 1977-12-08 DD DD7700202483A patent/DD133329A5/xx unknown
- 1977-12-08 AU AU31377/77A patent/AU510730B2/en not_active Expired
- 1977-12-12 SE SE7714074A patent/SE7714074L/xx not_active Application Discontinuation
- 1977-12-12 FI FI773738A patent/FI57594C/fi not_active IP Right Cessation
- 1977-12-13 FR FR7737467A patent/FR2374317A1/fr active Granted
- 1977-12-13 AT AT890777A patent/AT360523B/de not_active IP Right Cessation
- 1977-12-13 BE BE183407A patent/BE861794A/xx unknown
- 1977-12-14 ES ES465034A patent/ES465034A1/es not_active Expired
- 1977-12-14 JP JP15041777A patent/JPS5377058A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| BE861794A (fr) | 1978-06-13 |
| FR2374317B1 (cs) | 1980-11-07 |
| JPS5377058A (en) | 1978-07-08 |
| ATA890777A (de) | 1980-06-15 |
| HU175340B (hu) | 1980-07-28 |
| AT360523B (de) | 1981-01-12 |
| ZA777236B (en) | 1978-11-29 |
| GB1538822A (en) | 1979-01-24 |
| CS203179B2 (en) | 1981-02-27 |
| SU680647A3 (ru) | 1979-08-15 |
| FR2374317A1 (fr) | 1978-07-13 |
| FI57594B (fi) | 1980-05-30 |
| AU3137777A (en) | 1979-06-14 |
| FI773738A7 (fi) | 1978-06-15 |
| ES465034A1 (es) | 1978-09-01 |
| SE7714074L (sv) | 1978-06-15 |
| DE2656468A1 (de) | 1978-06-15 |
| DD133329A5 (de) | 1978-12-27 |
| AR216496A1 (es) | 1979-12-28 |
| NL7713580A (nl) | 1978-06-16 |
| AU510730B2 (en) | 1980-07-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FI57594C (fi) | Foerfarande foer framstaellning av antiallergiskt verksamma n-(bentstiazol-2-yl)-oxamidsyra-derivat | |
| CA1102802A (en) | Benzothiazine derivatives | |
| US6310099B1 (en) | Certain 5-alkyl-2-arylaminophenylacetic acids and derivatives | |
| FI91063B (fi) | Menetelmä kinoloniyhdisteiden valmistamiseksi | |
| US5223513A (en) | Quinoline derivatives, their production and use | |
| CZ20032696A3 (cs) | Thiohydantoiny a jejich použití při léčení cukrovky | |
| NO177300B (no) | Analogifremgangsmåte for fremstilling av et kinolinderivat og mellomprodukter | |
| US3455924A (en) | Dianisylimidazoles | |
| JPH09301958A (ja) | 新規ピリミジン化合物及び抗ロタウイルス剤 | |
| US4572910A (en) | Triazolo[1,5-c]pyrimidines substituted by nitrogen-containing heterocyclic rings | |
| NO794135L (no) | Substituerte 4(3h)-kinazolinoner, fremgangsmaate ved fremstilling og anvendelse av disse | |
| US3538086A (en) | 4-oxo-4h-pyrimido 2,1-b benzothiazoles | |
| OZEKI et al. | Studies on antiallergy agents. III. Synthesis of 2-anilino-1, 6-dihydro-6-oxo-5-pyrimidinecarboxylic acids and related compounds | |
| HU180240B (en) | Process for producing new,substituted 1,3-diaryl-2-iminoimidasolidines and 2-imino-hexahydro-pyrimidines | |
| Zinnes et al. | 1, 2-Benzothiazines. 6. 3-Carbamoyl-4-hydroxy-2H-1, 2-benzothiazine 1, 1-dioxides as antiinflammatory agents | |
| US3726875A (en) | 1,3(2h,4h)-dioxoisoquinoline-4-carboxylate esters and process therefor | |
| EP0592664A1 (en) | Novel diphenylthyazole derivative | |
| EP0102175A1 (en) | 5-Oxo-5H-(1)benzopyrano(2,3-b)pyridine derivatives, their production and use | |
| US4968708A (en) | Imidazo[2,1-B]benzothiazole compounds and antiulcer compositions containing the same | |
| US3944581A (en) | 5-Substituted-2,4-diphenylpyrimidines | |
| FI67706C (fi) | Foerfarande foer framstaellning av terapeutiskt anvaendbara n-5-tetrazolyl)-1-oxo-1h-tiazolo(3,2-a)pyrimidin-2-karboxyl atr | |
| US5063229A (en) | Imidazolo [1,2-a]pyrimidines and medical use thereof | |
| US4254118A (en) | 1-Oxo-5H-pyrimido[2,1-c][1,4]benzthiazine-2-carboxylic acid esters | |
| EP0041630B1 (en) | New 3h-naphtho(1,2-d)imidazoles, the process for preparing them, the compounds for use as antiinflammatory agents and compositions containing them | |
| IE42746B1 (en) | Fused pyrimidine-4-(3h)-ones and preparation thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: BOEHRINGER MANNHEIM GMBH |