ZA200507183B - Substituted P-diaminobenzene derivatives - Google Patents
Substituted P-diaminobenzene derivatives Download PDFInfo
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- ZA200507183B ZA200507183B ZA200507183A ZA200507183A ZA200507183B ZA 200507183 B ZA200507183 B ZA 200507183B ZA 200507183 A ZA200507183 A ZA 200507183A ZA 200507183 A ZA200507183 A ZA 200507183A ZA 200507183 B ZA200507183 B ZA 200507183B
- Authority
- ZA
- South Africa
- Prior art keywords
- alk
- cycloalk
- amino
- chloro
- phenyl
- Prior art date
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- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical class NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 39
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 34
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
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- 239000008194 pharmaceutical composition Substances 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 108020001213 potassium channel Proteins 0.000 claims description 15
- 229920006395 saturated elastomer Polymers 0.000 claims description 15
- 102000004257 Potassium Channel Human genes 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
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- 238000011282 treatment Methods 0.000 claims description 11
- -1 5-Chloro-thiophen-2-ylmethyl Chemical group 0.000 claims description 10
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- HBAVDOFSYDZLMI-UHFFFAOYSA-N 2-amino-4-methyl-n-[2-methyl-4-[[4-(trifluoromethyl)phenyl]methylamino]phenyl]pentanamide Chemical compound C1=C(C)C(NC(=O)C(N)CC(C)C)=CC=C1NCC1=CC=C(C(F)(F)F)C=C1 HBAVDOFSYDZLMI-UHFFFAOYSA-N 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 230000036461 convulsion Effects 0.000 claims 2
- PCHKLVYYPQCHED-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]-2-(4-chlorophenyl)acetamide Chemical compound C=1C=C(NC(=O)CC=2C=CC(Cl)=CC=2)C(Cl)=CC=1N(C)CC1=CC=C(Cl)S1 PCHKLVYYPQCHED-UHFFFAOYSA-N 0.000 claims 2
- RIWKCXYUIMTQHW-UHFFFAOYSA-N (2-chlorophenyl)methyl n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]carbamate Chemical compound C=1C=C(NC(=O)OCC=2C(=CC=CC=2)Cl)C(Cl)=CC=1N(C)CC1=CC=C(Cl)S1 RIWKCXYUIMTQHW-UHFFFAOYSA-N 0.000 claims 1
- PIQCXJAFLBNPHH-UHFFFAOYSA-N (4-nitrophenyl)methyl n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]carbamate Chemical compound C=1C=C(NC(=O)OCC=2C=CC(=CC=2)[N+]([O-])=O)C(Cl)=CC=1N(C)CC1=CC=C(Cl)S1 PIQCXJAFLBNPHH-UHFFFAOYSA-N 0.000 claims 1
- FFSFFZPIMVSEAI-UHFFFAOYSA-N 1-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]-3-(2-fluorophenyl)urea Chemical compound C=1C=C(NC(=O)NC=2C(=CC=CC=2)F)C(Cl)=CC=1N(C)CC1=CC=C(Cl)S1 FFSFFZPIMVSEAI-UHFFFAOYSA-N 0.000 claims 1
- XXORMBACYMRYFK-UHFFFAOYSA-N 1-[2-cyclopentyloxy-4-[(4-fluorophenyl)methyl-methylamino]phenyl]-3-ethylurea Chemical compound CCNC(=O)NC1=CC=C(N(C)CC=2C=CC(F)=CC=2)C=C1OC1CCCC1 XXORMBACYMRYFK-UHFFFAOYSA-N 0.000 claims 1
- YNNPZLJSEXYKHU-UHFFFAOYSA-N 1-amino-n-[2-methyl-4-[[4-(trifluoromethyl)phenyl]methylamino]phenyl]cyclopropane-1-carboxamide Chemical compound C=1C=C(NC(=O)C2(N)CC2)C(C)=CC=1NCC1=CC=C(C(F)(F)F)C=C1 YNNPZLJSEXYKHU-UHFFFAOYSA-N 0.000 claims 1
- NHUKLKFWYRPWKW-UHFFFAOYSA-N 2,2,2-trichloro-n-[4-[(5-chlorothiophen-2-yl)methyl-methylamino]-2-methylphenyl]acetamide Chemical compound C=1C=C(NC(=O)C(Cl)(Cl)Cl)C(C)=CC=1N(C)CC1=CC=C(Cl)S1 NHUKLKFWYRPWKW-UHFFFAOYSA-N 0.000 claims 1
- GRPYQETWCYYASI-UHFFFAOYSA-N 2,2-dimethyl-n-[2-methyl-4-[(3-methyl-5-phenyl-1,2-oxazol-4-yl)methylamino]phenyl]propanamide Chemical compound CC1=NOC(C=2C=CC=CC=2)=C1CNC1=CC=C(NC(=O)C(C)(C)C)C(C)=C1 GRPYQETWCYYASI-UHFFFAOYSA-N 0.000 claims 1
- GLHVEYVVFXLYTL-UHFFFAOYSA-N 2,2-dimethyl-n-[2-methyl-4-[(6-phenoxypyridin-3-yl)methylamino]phenyl]propanamide Chemical compound C1=C(NC(=O)C(C)(C)C)C(C)=CC(NCC=2C=NC(OC=3C=CC=CC=3)=CC=2)=C1 GLHVEYVVFXLYTL-UHFFFAOYSA-N 0.000 claims 1
- MYGXIGJESMGAQN-UHFFFAOYSA-N 2,2-dimethylpropyl n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]carbamate Chemical compound C=1C=C(NC(=O)OCC(C)(C)C)C(Cl)=CC=1N(C)CC1=CC=C(Cl)S1 MYGXIGJESMGAQN-UHFFFAOYSA-N 0.000 claims 1
- YXYOLVAXVPOIMA-UHFFFAOYSA-N 2,3-dihydro-1-benzofuran-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2OCCC2=C1 YXYOLVAXVPOIMA-UHFFFAOYSA-N 0.000 claims 1
- AFRIITXJFGWUIR-UHFFFAOYSA-N 2-(4-chlorophenyl)-n-[4-[(5-chlorothiophen-2-yl)methyl-methylamino]-2-methylphenyl]acetamide Chemical compound C=1C=C(NC(=O)CC=2C=CC(Cl)=CC=2)C(C)=CC=1N(C)CC1=CC=C(Cl)S1 AFRIITXJFGWUIR-UHFFFAOYSA-N 0.000 claims 1
- PRGUIBZYEJEARJ-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[2-methyl-4-[(4-methyl-2-phenylpyrimidin-5-yl)methylamino]phenyl]acetamide Chemical compound C=1C=C(NC(=O)CC=2C=CC(F)=CC=2)C(C)=CC=1NCC(C(=N1)C)=CN=C1C1=CC=CC=C1 PRGUIBZYEJEARJ-UHFFFAOYSA-N 0.000 claims 1
- UYMDMWMYTNGODR-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[2-methyl-4-[[6-(4-methylphenoxy)pyridin-3-yl]methylamino]phenyl]acetamide Chemical compound C1=CC(C)=CC=C1OC(N=C1)=CC=C1CNC(C=C1C)=CC=C1NC(=O)CC1=CC=C(F)C=C1 UYMDMWMYTNGODR-UHFFFAOYSA-N 0.000 claims 1
- DNHDTULZZSOSBN-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[2-methyl-4-[[6-(trifluoromethyl)pyridin-3-yl]methylamino]phenyl]acetamide Chemical compound C=1C=C(NC(=O)CC=2C=CC(F)=CC=2)C(C)=CC=1NCC1=CC=C(C(F)(F)F)N=C1 DNHDTULZZSOSBN-UHFFFAOYSA-N 0.000 claims 1
- WJLXTOBWTZRKRD-UHFFFAOYSA-N 2-methylpropyl n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCC(C)C)=CC=C1N(C)CC1=CC=C(Cl)S1 WJLXTOBWTZRKRD-UHFFFAOYSA-N 0.000 claims 1
- YMRUQXQUIXXZSF-UHFFFAOYSA-N 2-phenylmethoxyethyl n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]carbamate Chemical compound C=1C=C(NC(=O)OCCOCC=2C=CC=CC=2)C(Cl)=CC=1N(C)CC1=CC=C(Cl)S1 YMRUQXQUIXXZSF-UHFFFAOYSA-N 0.000 claims 1
- FUWZLYDFJFRKGG-UHFFFAOYSA-N 3,3-dimethyl-n-[2-methyl-4-[(2-phenylpyrimidin-5-yl)methylamino]phenyl]butanamide Chemical compound C1=C(NC(=O)CC(C)(C)C)C(C)=CC(NCC=2C=NC(=NC=2)C=2C=CC=CC=2)=C1 FUWZLYDFJFRKGG-UHFFFAOYSA-N 0.000 claims 1
- NJUKIJYUAQHUKN-UHFFFAOYSA-N 3,3-dimethyl-n-[2-methyl-4-[[6-(4-methylphenoxy)pyridin-3-yl]methylamino]phenyl]butanamide Chemical compound C1=CC(C)=CC=C1OC(N=C1)=CC=C1CNC1=CC=C(NC(=O)CC(C)(C)C)C(C)=C1 NJUKIJYUAQHUKN-UHFFFAOYSA-N 0.000 claims 1
- FJHHRZVGLKCHRZ-UHFFFAOYSA-N 3,3-dimethyl-n-[2-methyl-4-[[6-(trifluoromethyl)pyridin-3-yl]methylamino]phenyl]butanamide Chemical compound C1=C(NC(=O)CC(C)(C)C)C(C)=CC(NCC=2C=NC(=CC=2)C(F)(F)F)=C1 FJHHRZVGLKCHRZ-UHFFFAOYSA-N 0.000 claims 1
- SJAIYFDQCITQLJ-UHFFFAOYSA-N 3-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]-1-methyl-1-propylurea Chemical compound C1=C(Cl)C(NC(=O)N(C)CCC)=CC=C1N(C)CC1=CC=C(Cl)S1 SJAIYFDQCITQLJ-UHFFFAOYSA-N 0.000 claims 1
- NKRSJPBJRWPWTO-UHFFFAOYSA-N 3-chloropropyl n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]carbamate Chemical compound C=1C=C(NC(=O)OCCCCl)C(Cl)=CC=1N(C)CC1=CC=C(Cl)S1 NKRSJPBJRWPWTO-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- JJAIPKWIFQODBY-UHFFFAOYSA-N [4-[(4-tert-butylphenyl)methyl-methylamino]-2-(trifluoromethyl)phenyl]carbamic acid Chemical compound C(C)(C)(C)C1=CC=C(CN(C2=CC(=C(C=C2)NC(O)=O)C(F)(F)F)C)C=C1 JJAIPKWIFQODBY-UHFFFAOYSA-N 0.000 claims 1
- XJZHWYPJRSSMJW-UHFFFAOYSA-N [4-[(5-bromothiophen-2-yl)methylamino]-2-(trifluoromethyl)phenyl]carbamic acid Chemical compound C1=C(C(F)(F)F)C(NC(=O)O)=CC=C1NCC1=CC=C(Br)S1 XJZHWYPJRSSMJW-UHFFFAOYSA-N 0.000 claims 1
- FKESDIGRMWCZGD-UHFFFAOYSA-N [4-[methyl-[(4-propan-2-ylphenyl)methyl]amino]-2-(trifluoromethyl)phenyl]carbamic acid Chemical compound C(C)(C)C1=CC=C(CN(C2=CC(=C(C=C2)NC(O)=O)C(F)(F)F)C)C=C1 FKESDIGRMWCZGD-UHFFFAOYSA-N 0.000 claims 1
- QIUJJJVRYWFJPB-UHFFFAOYSA-N benzyl n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]carbamate Chemical compound C=1C=C(NC(=O)OCC=2C=CC=CC=2)C(Cl)=CC=1N(C)CC1=CC=C(Cl)S1 QIUJJJVRYWFJPB-UHFFFAOYSA-N 0.000 claims 1
- GFLUXUNNWRGAJS-UHFFFAOYSA-N but-2-ynyl n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCC#CC)=CC=C1N(C)CC1=CC=C(Cl)S1 GFLUXUNNWRGAJS-UHFFFAOYSA-N 0.000 claims 1
- NTCMMLFINXWYDI-UHFFFAOYSA-N but-3-enyl n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]carbamate Chemical compound C=1C=C(NC(=O)OCCC=C)C(Cl)=CC=1N(C)CC1=CC=C(Cl)S1 NTCMMLFINXWYDI-UHFFFAOYSA-N 0.000 claims 1
- RRBPKGFPYVBTPQ-UHFFFAOYSA-N butyl n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCCCC)=CC=C1N(C)CC1=CC=C(Cl)S1 RRBPKGFPYVBTPQ-UHFFFAOYSA-N 0.000 claims 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- AMWAUBYTNYONBR-UHFFFAOYSA-N ethyl n-[2-chloro-4-[(4-propan-2-ylphenyl)methylamino]phenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCC)=CC=C1NCC1=CC=C(C(C)C)C=C1 AMWAUBYTNYONBR-UHFFFAOYSA-N 0.000 claims 1
- UJHAKAHMBMEMNW-UHFFFAOYSA-N ethyl n-[2-chloro-4-[(5-chlorothiophen-2-yl)methylamino]phenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCC)=CC=C1NCC1=CC=C(Cl)S1 UJHAKAHMBMEMNW-UHFFFAOYSA-N 0.000 claims 1
- UVHHGQGCILHVPA-UHFFFAOYSA-N ethyl n-[2-chloro-4-[methyl-[(4-methylsulfanylphenyl)methyl]amino]phenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCC)=CC=C1N(C)CC1=CC=C(SC)C=C1 UVHHGQGCILHVPA-UHFFFAOYSA-N 0.000 claims 1
- PXJYWPAJYQOYAU-UHFFFAOYSA-N ethyl n-[2-chloro-4-[methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]phenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCC)=CC=C1N(C)CC1=CC=C(C(F)(F)F)C=C1 PXJYWPAJYQOYAU-UHFFFAOYSA-N 0.000 claims 1
- MTYCZZYJZDRZKZ-UHFFFAOYSA-N ethyl n-[2-cyano-4-[(4-propan-2-ylphenyl)methylamino]phenyl]carbamate Chemical compound C1=C(C#N)C(NC(=O)OCC)=CC=C1NCC1=CC=C(C(C)C)C=C1 MTYCZZYJZDRZKZ-UHFFFAOYSA-N 0.000 claims 1
- QYUKOZHZSRWMNG-UHFFFAOYSA-N ethyl n-[2-cyclopentyloxy-4-[(4-methoxyphenyl)methylamino]phenyl]carbamate Chemical compound C1=C(OC2CCCC2)C(NC(=O)OCC)=CC=C1NCC1=CC=C(OC)C=C1 QYUKOZHZSRWMNG-UHFFFAOYSA-N 0.000 claims 1
- HIFLWUPIVYIOKB-UHFFFAOYSA-N ethyl n-[2-methoxy-4-[(3-methylthiophen-2-yl)methylamino]phenyl]carbamate Chemical compound C1=C(OC)C(NC(=O)OCC)=CC=C1NCC1=C(C)C=CS1 HIFLWUPIVYIOKB-UHFFFAOYSA-N 0.000 claims 1
- DBGKFRUFUABFLM-UHFFFAOYSA-N ethyl n-[2-methoxy-4-[(4-propan-2-ylphenyl)methylamino]phenyl]carbamate Chemical compound C1=C(OC)C(NC(=O)OCC)=CC=C1NCC1=CC=C(C(C)C)C=C1 DBGKFRUFUABFLM-UHFFFAOYSA-N 0.000 claims 1
- GPLMHGDAOVFNCU-UHFFFAOYSA-N ethyl n-[2-methyl-4-[(4-propan-2-ylphenyl)methylamino]phenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCC)=CC=C1NCC1=CC=C(C(C)C)C=C1 GPLMHGDAOVFNCU-UHFFFAOYSA-N 0.000 claims 1
- FJGJSYHAKOHFMZ-UHFFFAOYSA-N ethyl n-[2-methyl-4-[[4-(trifluoromethyl)phenyl]methylamino]phenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCC)=CC=C1NCC1=CC=C(C(F)(F)F)C=C1 FJGJSYHAKOHFMZ-UHFFFAOYSA-N 0.000 claims 1
- XYIVNKLPSJLTHT-UHFFFAOYSA-N ethyl n-[4-(1,3-benzodioxol-5-ylmethylamino)-2-propan-2-yloxyphenyl]carbamate Chemical compound C1=C(OC(C)C)C(NC(=O)OCC)=CC=C1NCC1=CC=C(OCO2)C2=C1 XYIVNKLPSJLTHT-UHFFFAOYSA-N 0.000 claims 1
- LBPNSUIVYSELKA-UHFFFAOYSA-N ethyl n-[4-(1-benzothiophen-2-ylmethylamino)-2-chlorophenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCC)=CC=C1NCC1=CC2=CC=CC=C2S1 LBPNSUIVYSELKA-UHFFFAOYSA-N 0.000 claims 1
- MBZCXPYDDKNMKD-UHFFFAOYSA-N ethyl n-[4-(1-benzothiophen-2-ylmethylamino)-2-methylphenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCC)=CC=C1NCC1=CC2=CC=CC=C2S1 MBZCXPYDDKNMKD-UHFFFAOYSA-N 0.000 claims 1
- DTOYTZIERSGENB-UHFFFAOYSA-N ethyl n-[4-(1-benzothiophen-3-ylmethylamino)-2-cyclopentyloxyphenyl]carbamate Chemical compound CCOC(=O)NC1=CC=C(NCC=2C3=CC=CC=C3SC=2)C=C1OC1CCCC1 DTOYTZIERSGENB-UHFFFAOYSA-N 0.000 claims 1
- XDKSFHCRKBLVPN-UHFFFAOYSA-N ethyl n-[4-[(2,4-difluorophenyl)methylamino]-2-methoxyphenyl]carbamate Chemical compound C1=C(OC)C(NC(=O)OCC)=CC=C1NCC1=CC=C(F)C=C1F XDKSFHCRKBLVPN-UHFFFAOYSA-N 0.000 claims 1
- DHNIHGLWXHLYGU-UHFFFAOYSA-N ethyl n-[4-[(3-fluoro-2-methylphenyl)methylamino]-2-(2-phenylethoxy)phenyl]carbamate Chemical compound C1=C(OCCC=2C=CC=CC=2)C(NC(=O)OCC)=CC=C1NCC1=CC=CC(F)=C1C DHNIHGLWXHLYGU-UHFFFAOYSA-N 0.000 claims 1
- DDLKIMUNVILAIR-UHFFFAOYSA-N ethyl n-[4-[(3-fluoro-2-methylphenyl)methylamino]-2-phenylmethoxyphenyl]carbamate Chemical compound C1=C(OCC=2C=CC=CC=2)C(NC(=O)OCC)=CC=C1NCC1=CC=CC(F)=C1C DDLKIMUNVILAIR-UHFFFAOYSA-N 0.000 claims 1
- CVTJQRXEUAZWTQ-UHFFFAOYSA-N ethyl n-[4-[(3-fluoro-2-methylphenyl)methylamino]-2-propan-2-yloxyphenyl]carbamate Chemical compound C1=C(OC(C)C)C(NC(=O)OCC)=CC=C1NCC1=CC=CC(F)=C1C CVTJQRXEUAZWTQ-UHFFFAOYSA-N 0.000 claims 1
- IMLUDSPLHDRIPO-UHFFFAOYSA-N ethyl n-[4-[(3-fluorophenyl)methylamino]-2-methoxyphenyl]carbamate Chemical compound C1=C(OC)C(NC(=O)OCC)=CC=C1NCC1=CC=CC(F)=C1 IMLUDSPLHDRIPO-UHFFFAOYSA-N 0.000 claims 1
- LCEODKNUZATZLW-UHFFFAOYSA-N ethyl n-[4-[(3-methoxyphenyl)methylamino]-2-phenylmethoxyphenyl]carbamate Chemical compound C1=C(OCC=2C=CC=CC=2)C(NC(=O)OCC)=CC=C1NCC1=CC=CC(OC)=C1 LCEODKNUZATZLW-UHFFFAOYSA-N 0.000 claims 1
- QCEHDLKQWVGPFI-UHFFFAOYSA-N ethyl n-[4-[(4-chlorophenyl)methylamino]-2-methylphenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCC)=CC=C1NCC1=CC=C(Cl)C=C1 QCEHDLKQWVGPFI-UHFFFAOYSA-N 0.000 claims 1
- NWLXPWFNBKJVKX-UHFFFAOYSA-N ethyl n-[4-[(4-fluorophenyl)methyl-methylamino]-2-propan-2-yloxyphenyl]carbamate Chemical compound C1=C(OC(C)C)C(NC(=O)OCC)=CC=C1N(C)CC1=CC=C(F)C=C1 NWLXPWFNBKJVKX-UHFFFAOYSA-N 0.000 claims 1
- XKSCLMWYIAIGGH-UHFFFAOYSA-N ethyl n-[4-[(4-methylsulfanylphenyl)methylamino]-2-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(NC(=O)OCC)=CC=C1NCC1=CC=C(SC)C=C1 XKSCLMWYIAIGGH-UHFFFAOYSA-N 0.000 claims 1
- FUOWMPZQNQMKQJ-UHFFFAOYSA-N ethyl n-[4-[(4-methylsulfanylphenyl)methylamino]-2-phenylmethoxyphenyl]carbamate Chemical compound C1=C(OCC=2C=CC=CC=2)C(NC(=O)OCC)=CC=C1NCC1=CC=C(SC)C=C1 FUOWMPZQNQMKQJ-UHFFFAOYSA-N 0.000 claims 1
- KKLHNPWQODPAQP-UHFFFAOYSA-N ethyl n-[4-[(4-tert-butylphenyl)methyl-methylamino]-2-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(NC(=O)OCC)=CC=C1N(C)CC1=CC=C(C(C)(C)C)C=C1 KKLHNPWQODPAQP-UHFFFAOYSA-N 0.000 claims 1
- JHNNJXNHEUWQQI-UHFFFAOYSA-N ethyl n-[4-[(4-tert-butylphenyl)methylamino]-2-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(NC(=O)OCC)=CC=C1NCC1=CC=C(C(C)(C)C)C=C1 JHNNJXNHEUWQQI-UHFFFAOYSA-N 0.000 claims 1
- CZIYBKSESQHEMY-UHFFFAOYSA-N ethyl n-[4-[(5-bromothiophen-2-yl)methylamino]-2-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(NC(=O)OCC)=CC=C1NCC1=CC=C(Br)S1 CZIYBKSESQHEMY-UHFFFAOYSA-N 0.000 claims 1
- BNRZQCLVVKMSIW-UHFFFAOYSA-N ethyl n-[4-[(5-bromothiophen-2-yl)methylamino]-2-chlorophenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCC)=CC=C1NCC1=CC=C(Br)S1 BNRZQCLVVKMSIW-UHFFFAOYSA-N 0.000 claims 1
- URCRJUUPLVVVDL-UHFFFAOYSA-N ethyl n-[4-[(5-chlorothiophen-2-yl)methyl-methylamino]-2-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(NC(=O)OCC)=CC=C1N(C)CC1=CC=C(Cl)S1 URCRJUUPLVVVDL-UHFFFAOYSA-N 0.000 claims 1
- AKLXLTKONNDHHV-UHFFFAOYSA-N ethyl n-[4-[(5-chlorothiophen-2-yl)methylamino]-2-(6-methoxypyridin-3-yl)phenyl]carbamate Chemical compound C1=C(C=2C=NC(OC)=CC=2)C(NC(=O)OCC)=CC=C1NCC1=CC=C(Cl)S1 AKLXLTKONNDHHV-UHFFFAOYSA-N 0.000 claims 1
- JBIFACVOFRVYLT-UHFFFAOYSA-N ethyl n-[4-[(5-chlorothiophen-2-yl)methylamino]-2-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(NC(=O)OCC)=CC=C1NCC1=CC=C(Cl)S1 JBIFACVOFRVYLT-UHFFFAOYSA-N 0.000 claims 1
- XXUITLDPXQQWMX-UHFFFAOYSA-N ethyl n-[4-[(5-chlorothiophen-2-yl)methylamino]-2-cyanophenyl]carbamate Chemical compound C1=C(C#N)C(NC(=O)OCC)=CC=C1NCC1=CC=C(Cl)S1 XXUITLDPXQQWMX-UHFFFAOYSA-N 0.000 claims 1
- PPNRDWUDMHIESH-UHFFFAOYSA-N ethyl n-[4-[(5-chlorothiophen-2-yl)methylamino]-2-iodophenyl]carbamate Chemical compound C1=C(I)C(NC(=O)OCC)=CC=C1NCC1=CC=C(Cl)S1 PPNRDWUDMHIESH-UHFFFAOYSA-N 0.000 claims 1
- BHONFRQFLYRMJR-UHFFFAOYSA-N ethyl n-[4-[(5-chlorothiophen-2-yl)methylamino]-2-pyridin-3-ylphenyl]carbamate Chemical compound C1=C(C=2C=NC=CC=2)C(NC(=O)OCC)=CC=C1NCC1=CC=C(Cl)S1 BHONFRQFLYRMJR-UHFFFAOYSA-N 0.000 claims 1
- HWRLUDVUXQLMIH-UHFFFAOYSA-N ethyl n-[4-[(5-chlorothiophen-2-yl)methylamino]-2-pyridin-4-ylphenyl]carbamate Chemical compound C1=C(C=2C=CN=CC=2)C(NC(=O)OCC)=CC=C1NCC1=CC=C(Cl)S1 HWRLUDVUXQLMIH-UHFFFAOYSA-N 0.000 claims 1
- PCPKDKGFFJFEJT-UHFFFAOYSA-N ethyl n-[4-[(5-chlorothiophen-2-yl)methylamino]-2-quinolin-3-ylphenyl]carbamate Chemical compound C1=C(C=2C=C3C=CC=CC3=NC=2)C(NC(=O)OCC)=CC=C1NCC1=CC=C(Cl)S1 PCPKDKGFFJFEJT-UHFFFAOYSA-N 0.000 claims 1
- KPERHISRLWKTQA-UHFFFAOYSA-N ethyl n-[4-[(5-chlorothiophen-2-yl)methylamino]-2-quinolin-5-ylphenyl]carbamate Chemical compound C1=C(C=2C3=CC=CN=C3C=CC=2)C(NC(=O)OCC)=CC=C1NCC1=CC=C(Cl)S1 KPERHISRLWKTQA-UHFFFAOYSA-N 0.000 claims 1
- NIEWPONKIRMTPH-UHFFFAOYSA-N ethyl n-[4-[(6-methoxy-1-benzothiophen-2-yl)methylamino]-2-methylphenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCC)=CC=C1NCC1=CC2=CC=C(OC)C=C2S1 NIEWPONKIRMTPH-UHFFFAOYSA-N 0.000 claims 1
- KLNBESIFXRZEPF-UHFFFAOYSA-N ethyl n-[4-[[3-fluoro-4-(trifluoromethyl)phenyl]methylamino]-2-methylphenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCC)=CC=C1NCC1=CC=C(C(F)(F)F)C(F)=C1 KLNBESIFXRZEPF-UHFFFAOYSA-N 0.000 claims 1
- GAYMQGPGTVLOQU-UHFFFAOYSA-N ethyl n-[4-[methyl-[(4-methylsulfanylphenyl)methyl]amino]-2-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(NC(=O)OCC)=CC=C1N(C)CC1=CC=C(SC)C=C1 GAYMQGPGTVLOQU-UHFFFAOYSA-N 0.000 claims 1
- IMUOXPRZLBQDQK-UHFFFAOYSA-N ethyl n-[4-[methyl-[(4-propan-2-ylphenyl)methyl]amino]-2-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(NC(=O)OCC)=CC=C1N(C)CC1=CC=C(C(C)C)C=C1 IMUOXPRZLBQDQK-UHFFFAOYSA-N 0.000 claims 1
- LUCIULMHEDDUDH-UHFFFAOYSA-N ethyl n-[4-[methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(NC(=O)OCC)=CC=C1N(C)CC1=CC=C(C(F)(F)F)C=C1 LUCIULMHEDDUDH-UHFFFAOYSA-N 0.000 claims 1
- JLNYLDRCNCLJQY-UHFFFAOYSA-N hexyl n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCCCCCC)=CC=C1N(C)CC1=CC=C(Cl)S1 JLNYLDRCNCLJQY-UHFFFAOYSA-N 0.000 claims 1
- ZWBZSWWTAABAAW-UHFFFAOYSA-N methyl 3-[4-[(5-chlorothiophen-2-yl)methyl-methylamino]-2-methylanilino]-3-oxopropanoate Chemical compound C1=C(C)C(NC(=O)CC(=O)OC)=CC=C1N(C)CC1=CC=C(Cl)S1 ZWBZSWWTAABAAW-UHFFFAOYSA-N 0.000 claims 1
- GIOTXFVSHZODRM-UHFFFAOYSA-N methyl 4-[[3-methyl-4-(propoxycarbonylamino)anilino]methyl]benzoate Chemical compound C1=C(C)C(NC(=O)OCCC)=CC=C1NCC1=CC=C(C(=O)OC)C=C1 GIOTXFVSHZODRM-UHFFFAOYSA-N 0.000 claims 1
- ZRCLMLJAAYQKFH-UHFFFAOYSA-N methyl n-[4-(1-benzothiophen-2-ylmethylamino)-2-methoxyphenyl]carbamate Chemical compound C1=C(OC)C(NC(=O)OC)=CC=C1NCC1=CC2=CC=CC=C2S1 ZRCLMLJAAYQKFH-UHFFFAOYSA-N 0.000 claims 1
- DSPRNVSQYVZCFI-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]-2,2,2-trifluoroacetamide Chemical compound C=1C=C(NC(=O)C(F)(F)F)C(Cl)=CC=1N(C)CC1=CC=C(Cl)S1 DSPRNVSQYVZCFI-UHFFFAOYSA-N 0.000 claims 1
- RJIRJOHWLZOJNX-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]-2-(3-methoxyphenyl)acetamide Chemical compound COC1=CC=CC(CC(=O)NC=2C(=CC(=CC=2)N(C)CC=2SC(Cl)=CC=2)Cl)=C1 RJIRJOHWLZOJNX-UHFFFAOYSA-N 0.000 claims 1
- KNCNOLISTQSDIB-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]-2-(4-chlorophenyl)propanamide Chemical compound C=1C=C(Cl)C=CC=1C(C)C(=O)NC(C(=C1)Cl)=CC=C1N(C)CC1=CC=C(Cl)S1 KNCNOLISTQSDIB-UHFFFAOYSA-N 0.000 claims 1
- QQMOLIHEOHSEJW-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]-2-(4-fluorophenyl)acetamide Chemical compound C=1C=C(NC(=O)CC=2C=CC(F)=CC=2)C(Cl)=CC=1N(C)CC1=CC=C(Cl)S1 QQMOLIHEOHSEJW-UHFFFAOYSA-N 0.000 claims 1
- NHGMMGIROLDGFV-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]-2-(4-methoxyphenyl)acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)NC1=CC=C(N(C)CC=2SC(Cl)=CC=2)C=C1Cl NHGMMGIROLDGFV-UHFFFAOYSA-N 0.000 claims 1
- BBUDPNLKZNMXMQ-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]-2-phenylacetamide Chemical compound C=1C=C(NC(=O)CC=2C=CC=CC=2)C(Cl)=CC=1N(C)CC1=CC=C(Cl)S1 BBUDPNLKZNMXMQ-UHFFFAOYSA-N 0.000 claims 1
- HJUMLZPJCRCVMP-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]-2-thiophen-2-ylacetamide Chemical compound C=1C=C(NC(=O)CC=2SC=CC=2)C(Cl)=CC=1N(C)CC1=CC=C(Cl)S1 HJUMLZPJCRCVMP-UHFFFAOYSA-N 0.000 claims 1
- WREHPYPXQIMPCQ-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]-3,3-dimethylbutanamide Chemical compound C=1C=C(NC(=O)CC(C)(C)C)C(Cl)=CC=1N(C)CC1=CC=C(Cl)S1 WREHPYPXQIMPCQ-UHFFFAOYSA-N 0.000 claims 1
- QOJZWSIRHHMUND-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]-3-cyclohexylpropanamide Chemical compound C=1C=C(NC(=O)CCC2CCCCC2)C(Cl)=CC=1N(C)CC1=CC=C(Cl)S1 QOJZWSIRHHMUND-UHFFFAOYSA-N 0.000 claims 1
- XEQYECZAIUQLSF-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]-3-phenylpropanamide Chemical compound C=1C=C(NC(=O)CCC=2C=CC=CC=2)C(Cl)=CC=1N(C)CC1=CC=C(Cl)S1 XEQYECZAIUQLSF-UHFFFAOYSA-N 0.000 claims 1
- ZXIJIODJNIISBC-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]butanamide Chemical compound C1=C(Cl)C(NC(=O)CCC)=CC=C1N(C)CC1=CC=C(Cl)S1 ZXIJIODJNIISBC-UHFFFAOYSA-N 0.000 claims 1
- ICTXQIPJUUCOJP-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]cyclobutanecarboxamide Chemical compound C=1C=C(NC(=O)C2CCC2)C(Cl)=CC=1N(C)CC1=CC=C(Cl)S1 ICTXQIPJUUCOJP-UHFFFAOYSA-N 0.000 claims 1
- IEWASZTYXBKWSP-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]cyclohexanecarboxamide Chemical compound C=1C=C(NC(=O)C2CCCCC2)C(Cl)=CC=1N(C)CC1=CC=C(Cl)S1 IEWASZTYXBKWSP-UHFFFAOYSA-N 0.000 claims 1
- GTFNEWRWVYJMGD-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]cyclopentanecarboxamide Chemical compound C=1C=C(NC(=O)C2CCCC2)C(Cl)=CC=1N(C)CC1=CC=C(Cl)S1 GTFNEWRWVYJMGD-UHFFFAOYSA-N 0.000 claims 1
- QVVCRTNUUALZJM-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]cyclopropanecarboxamide Chemical compound C=1C=C(NC(=O)C2CC2)C(Cl)=CC=1N(C)CC1=CC=C(Cl)S1 QVVCRTNUUALZJM-UHFFFAOYSA-N 0.000 claims 1
- KTVYZDPJAAPEAD-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]pentanamide Chemical compound C1=C(Cl)C(NC(=O)CCCC)=CC=C1N(C)CC1=CC=C(Cl)S1 KTVYZDPJAAPEAD-UHFFFAOYSA-N 0.000 claims 1
- UWLQXWWVEUDTNY-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methylamino]phenyl]-2,2,2-trifluoroacetamide Chemical compound C1=C(Cl)C(NC(=O)C(F)(F)F)=CC=C1NCC1=CC=C(Cl)S1 UWLQXWWVEUDTNY-UHFFFAOYSA-N 0.000 claims 1
- YFDSOWUYPDFCDA-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methylamino]phenyl]-2,2-dimethylpropanamide Chemical compound C1=C(Cl)C(NC(=O)C(C)(C)C)=CC=C1NCC1=CC=C(Cl)S1 YFDSOWUYPDFCDA-UHFFFAOYSA-N 0.000 claims 1
- LDARJHDVQXQBCR-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methylamino]phenyl]-2,3-dihydro-1,4-benzodioxine-6-carboxamide Chemical compound S1C(Cl)=CC=C1CNC(C=C1Cl)=CC=C1NC(=O)C1=CC=C(OCCO2)C2=C1 LDARJHDVQXQBCR-UHFFFAOYSA-N 0.000 claims 1
- GZPCNLCZYOCMLW-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methylamino]phenyl]-2-(3-methoxyphenyl)acetamide Chemical compound COC1=CC=CC(CC(=O)NC=2C(=CC(NCC=3SC(Cl)=CC=3)=CC=2)Cl)=C1 GZPCNLCZYOCMLW-UHFFFAOYSA-N 0.000 claims 1
- QPWADJHNRLEIQB-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methylamino]phenyl]-2-(4-chlorophenyl)acetamide Chemical compound S1C(Cl)=CC=C1CNC(C=C1Cl)=CC=C1NC(=O)CC1=CC=C(Cl)C=C1 QPWADJHNRLEIQB-UHFFFAOYSA-N 0.000 claims 1
- BLZIGMLBKKOBNU-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methylamino]phenyl]-2-(4-methoxyphenyl)acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)NC(C(=C1)Cl)=CC=C1NCC1=CC=C(Cl)S1 BLZIGMLBKKOBNU-UHFFFAOYSA-N 0.000 claims 1
- BCGYFDWDTFWDIR-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methylamino]phenyl]-2-phenoxyacetamide Chemical compound S1C(Cl)=CC=C1CNC(C=C1Cl)=CC=C1NC(=O)COC1=CC=CC=C1 BCGYFDWDTFWDIR-UHFFFAOYSA-N 0.000 claims 1
- AEOSUEWFLMVAFB-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methylamino]phenyl]-2-phenylacetamide Chemical compound S1C(Cl)=CC=C1CNC(C=C1Cl)=CC=C1NC(=O)CC1=CC=CC=C1 AEOSUEWFLMVAFB-UHFFFAOYSA-N 0.000 claims 1
- OOFJORNTRHEEFY-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methylamino]phenyl]-2-thiophen-2-ylacetamide Chemical compound S1C(Cl)=CC=C1CNC(C=C1Cl)=CC=C1NC(=O)CC1=CC=CS1 OOFJORNTRHEEFY-UHFFFAOYSA-N 0.000 claims 1
- GBUJVXQGXXEWHN-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methylamino]phenyl]-3,3-dimethylbutanamide Chemical compound C1=C(Cl)C(NC(=O)CC(C)(C)C)=CC=C1NCC1=CC=C(Cl)S1 GBUJVXQGXXEWHN-UHFFFAOYSA-N 0.000 claims 1
- UHHGGSIKLWJNOT-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methylamino]phenyl]-3-cyclohexylpropanamide Chemical compound S1C(Cl)=CC=C1CNC(C=C1Cl)=CC=C1NC(=O)CCC1CCCCC1 UHHGGSIKLWJNOT-UHFFFAOYSA-N 0.000 claims 1
- PDZFLRVABUEWSZ-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methylamino]phenyl]butanamide Chemical compound C1=C(Cl)C(NC(=O)CCC)=CC=C1NCC1=CC=C(Cl)S1 PDZFLRVABUEWSZ-UHFFFAOYSA-N 0.000 claims 1
- WMRAUBJGYGJYFV-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methylamino]phenyl]cyclobutanecarboxamide Chemical compound S1C(Cl)=CC=C1CNC(C=C1Cl)=CC=C1NC(=O)C1CCC1 WMRAUBJGYGJYFV-UHFFFAOYSA-N 0.000 claims 1
- PABXVNVCLLFEJC-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methylamino]phenyl]cyclohexanecarboxamide Chemical compound S1C(Cl)=CC=C1CNC(C=C1Cl)=CC=C1NC(=O)C1CCCCC1 PABXVNVCLLFEJC-UHFFFAOYSA-N 0.000 claims 1
- AOFLYATWZBSEOS-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methylamino]phenyl]cyclopentanecarboxamide Chemical compound S1C(Cl)=CC=C1CNC(C=C1Cl)=CC=C1NC(=O)C1CCCC1 AOFLYATWZBSEOS-UHFFFAOYSA-N 0.000 claims 1
- HMSYDJFUVJCDSK-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methylamino]phenyl]pentanamide Chemical compound C1=C(Cl)C(NC(=O)CCCC)=CC=C1NCC1=CC=C(Cl)S1 HMSYDJFUVJCDSK-UHFFFAOYSA-N 0.000 claims 1
- GEUIQJWDQZWGRE-UHFFFAOYSA-N n-[2-methoxy-4-[(4-propan-2-ylphenyl)methylamino]phenyl]butanamide Chemical compound C1=C(OC)C(NC(=O)CCC)=CC=C1NCC1=CC=C(C(C)C)C=C1 GEUIQJWDQZWGRE-UHFFFAOYSA-N 0.000 claims 1
- TUXZGMKFRZJZSM-UHFFFAOYSA-N n-[2-methoxy-4-[[4-(trifluoromethyl)phenyl]methylamino]phenyl]butanamide Chemical compound C1=C(OC)C(NC(=O)CCC)=CC=C1NCC1=CC=C(C(F)(F)F)C=C1 TUXZGMKFRZJZSM-UHFFFAOYSA-N 0.000 claims 1
- JSYCSVLZYSFSBB-UHFFFAOYSA-N n-[2-methyl-4-[[4-(trifluoromethyl)phenyl]methylamino]phenyl]-2-morpholin-4-ylacetamide Chemical compound C=1C=C(NC(=O)CN2CCOCC2)C(C)=CC=1NCC1=CC=C(C(F)(F)F)C=C1 JSYCSVLZYSFSBB-UHFFFAOYSA-N 0.000 claims 1
- NDZPOHAYEUWMTA-UHFFFAOYSA-N n-[2-methyl-4-[[4-(trifluoromethyl)phenyl]methylamino]phenyl]-2-piperidin-1-ylacetamide Chemical compound C=1C=C(NC(=O)CN2CCCCC2)C(C)=CC=1NCC1=CC=C(C(F)(F)F)C=C1 NDZPOHAYEUWMTA-UHFFFAOYSA-N 0.000 claims 1
- AQDSFYZMSFHLTN-UHFFFAOYSA-N n-[2-methyl-4-[[4-(trifluoromethyl)phenyl]methylamino]phenyl]-2-pyrrolidin-1-ylacetamide Chemical compound C=1C=C(NC(=O)CN2CCCC2)C(C)=CC=1NCC1=CC=C(C(F)(F)F)C=C1 AQDSFYZMSFHLTN-UHFFFAOYSA-N 0.000 claims 1
- WGJUXKMIFGCNDM-UHFFFAOYSA-N n-[2-methyl-4-[[4-(trifluoromethyl)phenyl]methylamino]phenyl]butanamide Chemical compound C1=C(C)C(NC(=O)CCC)=CC=C1NCC1=CC=C(C(F)(F)F)C=C1 WGJUXKMIFGCNDM-UHFFFAOYSA-N 0.000 claims 1
- LJRXFNXMIQEJIO-UHFFFAOYSA-N n-[4-[(4-tert-butylphenyl)methylamino]-2-methoxyphenyl]butanamide Chemical compound C1=C(OC)C(NC(=O)CCC)=CC=C1NCC1=CC=C(C(C)(C)C)C=C1 LJRXFNXMIQEJIO-UHFFFAOYSA-N 0.000 claims 1
- QXLDJYKVHQGGIE-UHFFFAOYSA-N n-[4-[(5-bromothiophen-2-yl)methylamino]-2-methoxyphenyl]butanamide Chemical compound C1=C(OC)C(NC(=O)CCC)=CC=C1NCC1=CC=C(Br)S1 QXLDJYKVHQGGIE-UHFFFAOYSA-N 0.000 claims 1
- PUWKCSUQTQBIRA-UHFFFAOYSA-N n-[4-[(5-chlorothiophen-2-yl)methyl-methylamino]-2-methylphenyl]-2,2-dimethylpropanamide Chemical compound C=1C=C(NC(=O)C(C)(C)C)C(C)=CC=1N(C)CC1=CC=C(Cl)S1 PUWKCSUQTQBIRA-UHFFFAOYSA-N 0.000 claims 1
- BYMZSQYOOFBETO-UHFFFAOYSA-N n-[4-[(5-chlorothiophen-2-yl)methyl-methylamino]-2-methylphenyl]-2-(3-methoxyphenyl)acetamide Chemical compound COC1=CC=CC(CC(=O)NC=2C(=CC(=CC=2)N(C)CC=2SC(Cl)=CC=2)C)=C1 BYMZSQYOOFBETO-UHFFFAOYSA-N 0.000 claims 1
- XFEGTPTVEMIAHI-UHFFFAOYSA-N n-[4-[(5-chlorothiophen-2-yl)methyl-methylamino]-2-methylphenyl]-2-(4-fluorophenyl)acetamide Chemical compound C=1C=C(NC(=O)CC=2C=CC(F)=CC=2)C(C)=CC=1N(C)CC1=CC=C(Cl)S1 XFEGTPTVEMIAHI-UHFFFAOYSA-N 0.000 claims 1
- BBSKYLLMPFIUPS-UHFFFAOYSA-N n-[4-[(5-chlorothiophen-2-yl)methyl-methylamino]-2-methylphenyl]-2-(4-methoxyphenyl)acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)NC1=CC=C(N(C)CC=2SC(Cl)=CC=2)C=C1C BBSKYLLMPFIUPS-UHFFFAOYSA-N 0.000 claims 1
- LVTRCLBSFHCSJM-UHFFFAOYSA-N n-[4-[(5-chlorothiophen-2-yl)methyl-methylamino]-2-methylphenyl]-2-phenylacetamide Chemical compound C=1C=C(NC(=O)CC=2C=CC=CC=2)C(C)=CC=1N(C)CC1=CC=C(Cl)S1 LVTRCLBSFHCSJM-UHFFFAOYSA-N 0.000 claims 1
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- ZANNEMGAMBXAJH-UHFFFAOYSA-N n-[4-[(5-chlorothiophen-2-yl)methyl-methylamino]-2-methylphenyl]-3-phenylpropanamide Chemical compound C=1C=C(NC(=O)CCC=2C=CC=CC=2)C(C)=CC=1N(C)CC1=CC=C(Cl)S1 ZANNEMGAMBXAJH-UHFFFAOYSA-N 0.000 claims 1
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- VCUGNXTWGUQSIK-UHFFFAOYSA-N n-[4-[(5-chlorothiophen-2-yl)methyl-methylamino]-2-methylphenyl]pentanamide Chemical compound C1=C(C)C(NC(=O)CCCC)=CC=C1N(C)CC1=CC=C(Cl)S1 VCUGNXTWGUQSIK-UHFFFAOYSA-N 0.000 claims 1
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- TXYYXEJXGQEJQO-UHFFFAOYSA-N n-[4-[(5-chlorothiophen-2-yl)methylamino]-2-iodophenyl]-2-(4-fluorophenyl)acetamide Chemical compound C1=CC(F)=CC=C1CC(=O)NC(C(=C1)I)=CC=C1NCC1=CC=C(Cl)S1 TXYYXEJXGQEJQO-UHFFFAOYSA-N 0.000 claims 1
- NFTGAJLMMXINJN-UHFFFAOYSA-N n-[4-[(5-chlorothiophen-2-yl)methylamino]-2-methoxyphenyl]butanamide Chemical compound C1=C(OC)C(NC(=O)CCC)=CC=C1NCC1=CC=C(Cl)S1 NFTGAJLMMXINJN-UHFFFAOYSA-N 0.000 claims 1
- ZNDKCOPIFNSNSB-UHFFFAOYSA-N n-[4-[(6-chloropyridin-3-yl)methylamino]-2-methylphenyl]-2-(4-fluorophenyl)acetamide Chemical compound C=1C=C(NC(=O)CC=2C=CC(F)=CC=2)C(C)=CC=1NCC1=CC=C(Cl)N=C1 ZNDKCOPIFNSNSB-UHFFFAOYSA-N 0.000 claims 1
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- XETNUEHTWCZNAQ-UHFFFAOYSA-N n-[4-[[6-(4-cyanophenoxy)pyridin-3-yl]methylamino]-2-methylphenyl]-2-(4-fluorophenyl)acetamide Chemical compound C=1C=C(NC(=O)CC=2C=CC(F)=CC=2)C(C)=CC=1NCC(C=N1)=CC=C1OC1=CC=C(C#N)C=C1 XETNUEHTWCZNAQ-UHFFFAOYSA-N 0.000 claims 1
- QYNJALBPNQXKOG-UHFFFAOYSA-N phenyl n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]carbamate Chemical compound C=1C=C(NC(=O)OC=2C=CC=CC=2)C(Cl)=CC=1N(C)CC1=CC=C(Cl)S1 QYNJALBPNQXKOG-UHFFFAOYSA-N 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
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- BWNNQSDXPGZXIU-UHFFFAOYSA-N propyl n-[2-bromo-4-[(5-bromothiophen-2-yl)methyl-methylamino]phenyl]carbamate Chemical compound C1=C(Br)C(NC(=O)OCCC)=CC=C1N(C)CC1=CC=C(Br)S1 BWNNQSDXPGZXIU-UHFFFAOYSA-N 0.000 claims 1
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- AFEGKGPOQWHFQJ-UHFFFAOYSA-N propyl n-[2-chloro-4-[(5-chlorothiophen-2-yl)methylamino]phenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCCC)=CC=C1NCC1=CC=C(Cl)S1 AFEGKGPOQWHFQJ-UHFFFAOYSA-N 0.000 claims 1
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- CPKOTQLROKZIHS-UHFFFAOYSA-N propyl n-[2-cyano-4-[methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]phenyl]carbamate Chemical compound C1=C(C#N)C(NC(=O)OCCC)=CC=C1N(C)CC1=CC=C(C(F)(F)F)C=C1 CPKOTQLROKZIHS-UHFFFAOYSA-N 0.000 claims 1
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- PINFNGLHVSTBBG-UHFFFAOYSA-N propyl n-[2-methyl-4-[methyl-[(4-methylsulfanylphenyl)methyl]amino]phenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCCC)=CC=C1N(C)CC1=CC=C(SC)C=C1 PINFNGLHVSTBBG-UHFFFAOYSA-N 0.000 claims 1
- GOJPEGLCQDFVPT-UHFFFAOYSA-N propyl n-[2-methyl-4-[methyl-[(4-propan-2-ylphenyl)methyl]amino]phenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCCC)=CC=C1N(C)CC1=CC=C(C(C)C)C=C1 GOJPEGLCQDFVPT-UHFFFAOYSA-N 0.000 claims 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/42—Radicals substituted by singly-bound nitrogen atoms having hetero atoms attached to the substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/58—Radicals substituted by nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA200300441 | 2003-03-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200507183B true ZA200507183B (en) | 2007-03-28 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200507183A ZA200507183B (en) | 2003-03-21 | 2004-03-18 | Substituted P-diaminobenzene derivatives |
Country Status (9)
| Country | Link |
|---|---|
| KR (1) | KR20050115919A (is) |
| CN (1) | CN1761464A (is) |
| AR (1) | AR043652A1 (is) |
| CL (1) | CL2004000575A1 (is) |
| EA (1) | EA200501499A1 (is) |
| IS (1) | IS7991A (is) |
| NZ (1) | NZ541945A (is) |
| UA (1) | UA81019C2 (is) |
| ZA (1) | ZA200507183B (is) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103073455B (zh) | 2011-10-25 | 2015-08-19 | 中国科学院上海药物研究所 | 一类新型的kcnq钾通道激动剂、其制备方法和用途 |
| CN105017085B (zh) | 2014-04-28 | 2018-06-29 | 中国科学院上海药物研究所 | 一类kcnq钾通道激动剂、其制备方法和用途 |
| CN108707087B (zh) | 2018-06-29 | 2020-10-16 | 河北医科大学 | 一种4-(对三氟甲基苄基)-3-氟-1,2,4三苯胺衍生物及其药物组合物与用途 |
| KR102643653B1 (ko) * | 2020-11-13 | 2024-03-06 | 기초과학연구원 | 신규한 아미노방향족 화합물 또는 이의 약학적으로 허용가능한 염 및 이를 유효성분으로 포함하는 신경퇴행성 질환의 예방 또는 치료용 약학적 조성물 |
| CN114672483B (zh) * | 2022-05-31 | 2022-09-02 | 上海百力格生物技术有限公司 | 超声法核酸探针制备方法 |
-
2004
- 2004-03-18 CN CNA2004800075074A patent/CN1761464A/zh active Pending
- 2004-03-18 EA EA200501499A patent/EA200501499A1/ru unknown
- 2004-03-18 NZ NZ541945A patent/NZ541945A/en unknown
- 2004-03-18 UA UAA200509094A patent/UA81019C2/uk unknown
- 2004-03-18 AR ARP040100905A patent/AR043652A1/es unknown
- 2004-03-18 ZA ZA200507183A patent/ZA200507183B/en unknown
- 2004-03-18 KR KR1020057017581A patent/KR20050115919A/ko not_active Application Discontinuation
- 2004-03-19 CL CL200400575A patent/CL2004000575A1/es unknown
-
2005
- 2005-08-18 IS IS7991A patent/IS7991A/is unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AR043652A1 (es) | 2005-08-03 |
| UA81019C2 (en) | 2007-11-26 |
| IS7991A (is) | 2005-08-18 |
| EA200501499A1 (ru) | 2006-02-24 |
| KR20050115919A (ko) | 2005-12-08 |
| CL2004000575A1 (es) | 2005-01-21 |
| CN1761464A (zh) | 2006-04-19 |
| NZ541945A (en) | 2009-02-28 |
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