JP2008509982A5 - - Google Patents
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- Publication number
- JP2008509982A5 JP2008509982A5 JP2007526578A JP2007526578A JP2008509982A5 JP 2008509982 A5 JP2008509982 A5 JP 2008509982A5 JP 2007526578 A JP2007526578 A JP 2007526578A JP 2007526578 A JP2007526578 A JP 2007526578A JP 2008509982 A5 JP2008509982 A5 JP 2008509982A5
- Authority
- JP
- Japan
- Prior art keywords
- urea
- ureido
- ylphenyl
- benzoic acid
- fluorophenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims 22
- 125000003545 alkoxy group Chemical group 0.000 claims 17
- 150000001875 compounds Chemical class 0.000 claims 17
- 229910052739 hydrogen Inorganic materials 0.000 claims 13
- 239000001257 hydrogen Substances 0.000 claims 13
- 239000004202 carbamide Substances 0.000 claims 10
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 10
- 150000002431 hydrogen Chemical class 0.000 claims 9
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 8
- 125000001153 fluoro group Chemical group F* 0.000 claims 8
- 229910052736 halogen Inorganic materials 0.000 claims 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 125000002619 bicyclic group Chemical group 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 125000004450 alkenylene group Chemical group 0.000 claims 5
- 125000002947 alkylene group Chemical group 0.000 claims 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- -1 oxaazepan-4-ylphenyl Chemical group 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 239000012948 isocyanate Substances 0.000 claims 2
- 150000002513 isocyanates Chemical class 0.000 claims 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims 2
- 150000002825 nitriles Chemical class 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- JUXJZTJLUULZRU-UHFFFAOYSA-N 1,3-bis(4-acetylphenyl)urea Chemical compound C1=CC(C(=O)C)=CC=C1NC(=O)NC1=CC=C(C(C)=O)C=C1 JUXJZTJLUULZRU-UHFFFAOYSA-N 0.000 claims 1
- NLNLEHOVZAHYIG-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)-3-(3-fluoro-4-piperidin-1-ylphenyl)urea Chemical compound FC1=CC(NC(=O)NC=2C=C3OCOC3=CC=2)=CC=C1N1CCCCC1 NLNLEHOVZAHYIG-UHFFFAOYSA-N 0.000 claims 1
- BFRUERPRKIZNKB-UHFFFAOYSA-N 1-(1,3-benzothiazol-6-yl)-3-(4-fluorophenyl)urea Chemical compound C1=CC(F)=CC=C1NC(=O)NC1=CC=C(N=CS2)C2=C1 BFRUERPRKIZNKB-UHFFFAOYSA-N 0.000 claims 1
- UIXCITLDYZBUBG-UHFFFAOYSA-N 1-(1-benzothiophen-2-yl)-3-(2-methylphenyl)urea Chemical compound CC1=CC=CC=C1NC(=O)NC1=CC2=CC=CC=C2S1 UIXCITLDYZBUBG-UHFFFAOYSA-N 0.000 claims 1
- JVBRQEDQTAWFSZ-UHFFFAOYSA-N 1-(1-benzothiophen-2-yl)-3-(4-methylsulfonylphenyl)urea Chemical compound C1=CC(S(=O)(=O)C)=CC=C1NC(=O)NC1=CC2=CC=CC=C2S1 JVBRQEDQTAWFSZ-UHFFFAOYSA-N 0.000 claims 1
- IYQRIUDYNWXIGO-UHFFFAOYSA-N 1-(1-methylindazol-5-yl)-3-[4-(morpholin-4-ylmethyl)phenyl]urea Chemical compound C=1C=C2N(C)N=CC2=CC=1NC(=O)NC(C=C1)=CC=C1CN1CCOCC1 IYQRIUDYNWXIGO-UHFFFAOYSA-N 0.000 claims 1
- GYMHJBJSCBQERO-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-(3-fluoro-4-piperidin-1-ylphenyl)urea Chemical compound FC1=CC(NC(=O)NC=2C=C3OCCOC3=CC=2)=CC=C1N1CCCCC1 GYMHJBJSCBQERO-UHFFFAOYSA-N 0.000 claims 1
- DEJJUOYQOWMNEH-UHFFFAOYSA-N 1-(2,3-dihydro-1-benzofuran-6-yl)-3-(3-fluoro-4-piperidin-1-ylphenyl)urea Chemical compound FC1=CC(NC(=O)NC=2C=C3OCCC3=CC=2)=CC=C1N1CCCCC1 DEJJUOYQOWMNEH-UHFFFAOYSA-N 0.000 claims 1
- RENAWGQIHCWXQF-UHFFFAOYSA-N 1-(2-fluorophenyl)-3-(4-fluorophenyl)urea Chemical compound C1=CC(F)=CC=C1NC(=O)NC1=CC=CC=C1F RENAWGQIHCWXQF-UHFFFAOYSA-N 0.000 claims 1
- TWMYLEWQSBWPQU-UHFFFAOYSA-N 1-(2-thiophen-2-ylethyl)-3-[4-(trifluoromethoxy)phenyl]urea Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NCCC1=CC=CS1 TWMYLEWQSBWPQU-UHFFFAOYSA-N 0.000 claims 1
- XYQFVUJLUJPCQW-UHFFFAOYSA-N 1-(2-thiophen-2-ylethyl)-3-[4-(trifluoromethyl)phenyl]urea Chemical compound C1=CC(C(F)(F)F)=CC=C1NC(=O)NCCC1=CC=CS1 XYQFVUJLUJPCQW-UHFFFAOYSA-N 0.000 claims 1
- ORUYFSZLJGWGPX-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-3-(3-fluoro-4-piperidin-1-ylphenyl)urea Chemical compound C=1C=C(N2CCCCC2)C(F)=CC=1NC(=O)NC1=CC=C(Cl)C(Cl)=C1 ORUYFSZLJGWGPX-UHFFFAOYSA-N 0.000 claims 1
- QHESGFXHFNJGKU-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)-3-(3-fluoro-4-piperidin-1-ylphenyl)urea Chemical compound C=1C=C(N2CCCCC2)C(F)=CC=1NC(=O)NC1=CC(Cl)=CC(Cl)=C1 QHESGFXHFNJGKU-UHFFFAOYSA-N 0.000 claims 1
- VVURLSLLFBZPPD-UHFFFAOYSA-N 1-(3,5-dimethoxyphenyl)-3-(3-fluoro-4-piperidin-1-ylphenyl)urea Chemical compound COC1=CC(OC)=CC(NC(=O)NC=2C=C(F)C(N3CCCCC3)=CC=2)=C1 VVURLSLLFBZPPD-UHFFFAOYSA-N 0.000 claims 1
- CGCYEPPBGPPQQH-UHFFFAOYSA-N 1-(3-acetylphenyl)-3-[2-(4-chlorophenyl)ethyl]urea Chemical compound CC(=O)C1=CC=CC(NC(=O)NCCC=2C=CC(Cl)=CC=2)=C1 CGCYEPPBGPPQQH-UHFFFAOYSA-N 0.000 claims 1
- XGBFOAJXGNRYMC-UHFFFAOYSA-N 1-(3-chloro-4-fluorophenyl)-3-(3-fluoro-4-piperidin-1-ylphenyl)urea Chemical compound C1=C(Cl)C(F)=CC=C1NC(=O)NC(C=C1F)=CC=C1N1CCCCC1 XGBFOAJXGNRYMC-UHFFFAOYSA-N 0.000 claims 1
- JUZGHGIUMRWRST-UHFFFAOYSA-N 1-(3-chloro-4-morpholin-4-ylphenyl)-3-(4-chlorophenyl)urea Chemical compound C1=CC(Cl)=CC=C1NC(=O)NC(C=C1Cl)=CC=C1N1CCOCC1 JUZGHGIUMRWRST-UHFFFAOYSA-N 0.000 claims 1
- UJHMVWFXDGNNAD-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-(2-thiophen-2-ylethyl)urea Chemical compound ClC1=CC=CC(NC(=O)NCCC=2SC=CC=2)=C1 UJHMVWFXDGNNAD-UHFFFAOYSA-N 0.000 claims 1
- XAFLXKOKDVXRMQ-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-(3-fluoro-4-piperidin-1-ylphenyl)urea Chemical compound C=1C=C(N2CCCCC2)C(F)=CC=1NC(=O)NC1=CC=CC(Cl)=C1 XAFLXKOKDVXRMQ-UHFFFAOYSA-N 0.000 claims 1
- RNCJYUXWPOFCKE-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-(4-ethoxyphenyl)urea Chemical compound C1=CC(OCC)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 RNCJYUXWPOFCKE-UHFFFAOYSA-N 0.000 claims 1
- TVFJHGFDTWKZLP-UHFFFAOYSA-N 1-(3-ethoxyphenyl)-3-(4-fluorophenyl)urea Chemical compound CCOC1=CC=CC(NC(=O)NC=2C=CC(F)=CC=2)=C1 TVFJHGFDTWKZLP-UHFFFAOYSA-N 0.000 claims 1
- RSXXTDFCOBUTQO-UHFFFAOYSA-N 1-(3-ethylphenyl)-3-(2-thiophen-2-ylethyl)urea Chemical compound CCC1=CC=CC(NC(=O)NCCC=2SC=CC=2)=C1 RSXXTDFCOBUTQO-UHFFFAOYSA-N 0.000 claims 1
- HDSLYONGIAZSGL-UHFFFAOYSA-N 1-(3-fluoro-4-piperidin-1-ylphenyl)-3-(3-methoxyphenyl)urea Chemical compound COC1=CC=CC(NC(=O)NC=2C=C(F)C(N3CCCCC3)=CC=2)=C1 HDSLYONGIAZSGL-UHFFFAOYSA-N 0.000 claims 1
- AQFYAQIEPRFVCM-UHFFFAOYSA-N 1-(3-fluoro-4-piperidin-1-ylphenyl)-3-(3-phenoxyphenyl)urea Chemical compound C=1C=C(N2CCCCC2)C(F)=CC=1NC(=O)NC(C=1)=CC=CC=1OC1=CC=CC=C1 AQFYAQIEPRFVCM-UHFFFAOYSA-N 0.000 claims 1
- ZNOJNJGEHJOGDH-UHFFFAOYSA-N 1-(3-fluoro-4-piperidin-1-ylphenyl)-3-(4-methoxyphenyl)urea Chemical compound C1=CC(OC)=CC=C1NC(=O)NC(C=C1F)=CC=C1N1CCCCC1 ZNOJNJGEHJOGDH-UHFFFAOYSA-N 0.000 claims 1
- LZFITTNRDMKEGK-UHFFFAOYSA-N 1-(3-fluoro-4-piperidin-1-ylphenyl)-3-(4-phenoxyphenyl)urea Chemical compound C=1C=C(N2CCCCC2)C(F)=CC=1NC(=O)NC(C=C1)=CC=C1OC1=CC=CC=C1 LZFITTNRDMKEGK-UHFFFAOYSA-N 0.000 claims 1
- BLNBMTXIHKJKIO-UHFFFAOYSA-N 1-(3-fluoro-4-piperidin-1-ylphenyl)-3-(4-pyrrol-1-ylphenyl)urea Chemical compound C=1C=C(N2CCCCC2)C(F)=CC=1NC(=O)NC(C=C1)=CC=C1N1C=CC=C1 BLNBMTXIHKJKIO-UHFFFAOYSA-N 0.000 claims 1
- FIBCPRWYYQGRJX-UHFFFAOYSA-N 1-(3-fluoro-4-piperidin-1-ylphenyl)-3-[3-(2-methoxyethoxy)phenyl]urea Chemical compound COCCOC1=CC=CC(NC(=O)NC=2C=C(F)C(N3CCCCC3)=CC=2)=C1 FIBCPRWYYQGRJX-UHFFFAOYSA-N 0.000 claims 1
- LEDOGRQUJHSGLQ-UHFFFAOYSA-N 1-(3-fluoro-4-piperidin-1-ylphenyl)-3-[3-(2-methylpyrimidin-4-yl)phenyl]urea Chemical compound CC1=NC=CC(C=2C=C(NC(=O)NC=3C=C(F)C(N4CCCCC4)=CC=3)C=CC=2)=N1 LEDOGRQUJHSGLQ-UHFFFAOYSA-N 0.000 claims 1
- FLTBAILOHFPYHB-UHFFFAOYSA-N 1-(3-fluoro-4-piperidin-1-ylphenyl)-3-[3-(2-morpholin-4-ylethoxy)phenyl]urea Chemical compound C=1C=C(N2CCCCC2)C(F)=CC=1NC(=O)NC(C=1)=CC=CC=1OCCN1CCOCC1 FLTBAILOHFPYHB-UHFFFAOYSA-N 0.000 claims 1
- LMANHEWDGCEAGT-UHFFFAOYSA-N 1-(3-fluoro-4-piperidin-1-ylphenyl)-3-[4-(2-methoxyethoxy)phenyl]urea Chemical compound C1=CC(OCCOC)=CC=C1NC(=O)NC(C=C1F)=CC=C1N1CCCCC1 LMANHEWDGCEAGT-UHFFFAOYSA-N 0.000 claims 1
- YIHYKJQGSMZOTM-UHFFFAOYSA-N 1-(3-fluoro-4-piperidin-1-ylphenyl)-3-[4-(2-morpholin-4-ylethoxy)phenyl]urea Chemical compound C=1C=C(N2CCCCC2)C(F)=CC=1NC(=O)NC(C=C1)=CC=C1OCCN1CCOCC1 YIHYKJQGSMZOTM-UHFFFAOYSA-N 0.000 claims 1
- UGDVFYDFTBOZCP-UHFFFAOYSA-N 1-(3-fluoro-4-piperidin-1-ylphenyl)-3-[4-(2-morpholin-4-ylethyl)phenyl]urea Chemical compound C=1C=C(N2CCCCC2)C(F)=CC=1NC(=O)NC(C=C1)=CC=C1CCN1CCOCC1 UGDVFYDFTBOZCP-UHFFFAOYSA-N 0.000 claims 1
- LXFVOULRFBVUGC-UHFFFAOYSA-N 1-(3-fluoro-4-piperidin-1-ylphenyl)-3-[4-(morpholin-4-ylmethyl)phenyl]urea Chemical compound C=1C=C(N2CCCCC2)C(F)=CC=1NC(=O)NC(C=C1)=CC=C1CN1CCOCC1 LXFVOULRFBVUGC-UHFFFAOYSA-N 0.000 claims 1
- LEVNKKAIINEFLZ-UHFFFAOYSA-N 1-(3-fluoro-4-piperidin-1-ylphenyl)-3-[4-(morpholine-4-carbonyl)phenyl]urea Chemical compound C=1C=C(N2CCCCC2)C(F)=CC=1NC(=O)NC(C=C1)=CC=C1C(=O)N1CCOCC1 LEVNKKAIINEFLZ-UHFFFAOYSA-N 0.000 claims 1
- IDTFCAUUORLWOP-UHFFFAOYSA-N 1-(3-fluoro-4-piperidin-1-ylphenyl)-3-[4-(trifluoromethyl)phenyl]urea Chemical compound C=1C=C(N2CCCCC2)C(F)=CC=1NC(=O)NC1=CC=C(C(F)(F)F)C=C1 IDTFCAUUORLWOP-UHFFFAOYSA-N 0.000 claims 1
- SPRREMVJUIABPB-UHFFFAOYSA-N 1-(4,6-difluoro-1,3-benzothiazol-2-yl)-3-(4-fluorophenyl)urea Chemical compound C1=CC(F)=CC=C1NC(=O)NC1=NC2=C(F)C=C(F)C=C2S1 SPRREMVJUIABPB-UHFFFAOYSA-N 0.000 claims 1
- XVRMXMQXBFZMNK-UHFFFAOYSA-N 1-(4-acetylphenyl)-3-(1-benzothiophen-2-yl)urea Chemical compound C1=CC(C(=O)C)=CC=C1NC(=O)NC1=CC2=CC=CC=C2S1 XVRMXMQXBFZMNK-UHFFFAOYSA-N 0.000 claims 1
- WZWJXMVMKODUKV-UHFFFAOYSA-N 1-(4-acetylphenyl)-3-(2-thiophen-2-ylethyl)urea Chemical compound C1=CC(C(=O)C)=CC=C1NC(=O)NCCC1=CC=CS1 WZWJXMVMKODUKV-UHFFFAOYSA-N 0.000 claims 1
- PWWHZOQXRNMTRH-UHFFFAOYSA-N 1-(4-acetylphenyl)-3-(3-chlorophenyl)urea Chemical compound C1=CC(C(=O)C)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 PWWHZOQXRNMTRH-UHFFFAOYSA-N 0.000 claims 1
- GCFNQQSTIWCXQI-UHFFFAOYSA-N 1-(4-acetylphenyl)-3-(4-bromophenyl)urea Chemical compound C1=CC(C(=O)C)=CC=C1NC(=O)NC1=CC=C(Br)C=C1 GCFNQQSTIWCXQI-UHFFFAOYSA-N 0.000 claims 1
- UAUZMDODFFNVLK-UHFFFAOYSA-N 1-(4-acetylphenyl)-3-(4-chlorophenyl)urea Chemical compound C1=CC(C(=O)C)=CC=C1NC(=O)NC1=CC=C(Cl)C=C1 UAUZMDODFFNVLK-UHFFFAOYSA-N 0.000 claims 1
- LPHLTXDENVFIFV-UHFFFAOYSA-N 1-(4-acetylphenyl)-3-(4-fluorophenyl)urea Chemical compound C1=CC(C(=O)C)=CC=C1NC(=O)NC1=CC=C(F)C=C1 LPHLTXDENVFIFV-UHFFFAOYSA-N 0.000 claims 1
- XKWCNKLCTJNILQ-UHFFFAOYSA-N 1-(4-acetylphenyl)-3-[3-(6-methoxypyridin-2-yl)phenyl]urea Chemical compound COC1=CC=CC(C=2C=C(NC(=O)NC=3C=CC(=CC=3)C(C)=O)C=CC=2)=N1 XKWCNKLCTJNILQ-UHFFFAOYSA-N 0.000 claims 1
- HZAUXMLGDZGWSL-UHFFFAOYSA-N 1-(4-acetylphenyl)-3-[4-(morpholin-4-ylmethyl)phenyl]urea Chemical compound C1=CC(C(=O)C)=CC=C1NC(=O)NC(C=C1)=CC=C1CN1CCOCC1 HZAUXMLGDZGWSL-UHFFFAOYSA-N 0.000 claims 1
- MGLCGFOXGUKYEK-UHFFFAOYSA-N 1-(4-acetylphenyl)-3-[4-(morpholine-4-carbonyl)phenyl]urea Chemical compound C1=CC(C(=O)C)=CC=C1NC(=O)NC1=CC=C(C(=O)N2CCOCC2)C=C1 MGLCGFOXGUKYEK-UHFFFAOYSA-N 0.000 claims 1
- ZVFDWRDGTDFQDX-UHFFFAOYSA-N 1-(4-benzoylphenyl)-3-(4-fluorophenyl)urea Chemical compound C1=CC(F)=CC=C1NC(=O)NC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 ZVFDWRDGTDFQDX-UHFFFAOYSA-N 0.000 claims 1
- AFAJUVLPTHBGBV-UHFFFAOYSA-N 1-(4-butanoylphenyl)-3-(4-fluorophenyl)urea Chemical compound C1=CC(C(=O)CCC)=CC=C1NC(=O)NC1=CC=C(F)C=C1 AFAJUVLPTHBGBV-UHFFFAOYSA-N 0.000 claims 1
- CSNXMKVKRTZYNY-UHFFFAOYSA-N 1-(4-butanoylphenyl)-3-(4-piperidin-1-ylphenyl)urea Chemical compound C1=CC(C(=O)CCC)=CC=C1NC(=O)NC1=CC=C(N2CCCCC2)C=C1 CSNXMKVKRTZYNY-UHFFFAOYSA-N 0.000 claims 1
- RDKSSLNOBXGBKC-UHFFFAOYSA-N 1-(4-butanoylphenyl)-3-[4-(morpholine-4-carbonyl)phenyl]urea Chemical compound C1=CC(C(=O)CCC)=CC=C1NC(=O)NC1=CC=C(C(=O)N2CCOCC2)C=C1 RDKSSLNOBXGBKC-UHFFFAOYSA-N 0.000 claims 1
- IZHKUKPBDUZXPQ-UHFFFAOYSA-N 1-(4-butylphenyl)-3-(2-thiophen-2-ylethyl)urea Chemical compound C1=CC(CCCC)=CC=C1NC(=O)NCCC1=CC=CS1 IZHKUKPBDUZXPQ-UHFFFAOYSA-N 0.000 claims 1
- KXFJKWDLKTUVAT-UHFFFAOYSA-N 1-(4-chloro-2-hydroxyphenyl)-3-(3-fluoro-4-piperidin-1-ylphenyl)urea Chemical compound OC1=CC(Cl)=CC=C1NC(=O)NC(C=C1F)=CC=C1N1CCCCC1 KXFJKWDLKTUVAT-UHFFFAOYSA-N 0.000 claims 1
- TXUXJSJVLGJQBP-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-(1-methylindazol-5-yl)urea Chemical compound C=1C=C2N(C)N=CC2=CC=1NC(=O)NC1=CC=C(Cl)C=C1 TXUXJSJVLGJQBP-UHFFFAOYSA-N 0.000 claims 1
- GOTKACBYTSNYTK-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-(2-thiophen-2-ylethyl)urea Chemical compound C1=CC(Cl)=CC=C1NC(=O)NCCC1=CC=CS1 GOTKACBYTSNYTK-UHFFFAOYSA-N 0.000 claims 1
- KACJXLXAPNNLPU-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-(3-fluoro-4-morpholin-4-ylphenyl)urea Chemical compound C=1C=C(N2CCOCC2)C(F)=CC=1NC(=O)NC1=CC=C(Cl)C=C1 KACJXLXAPNNLPU-UHFFFAOYSA-N 0.000 claims 1
- CZMDEJFFFFUWNT-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-(3-fluoro-4-piperidin-1-ylphenyl)urea Chemical compound C=1C=C(N2CCCCC2)C(F)=CC=1NC(=O)NC1=CC=C(Cl)C=C1 CZMDEJFFFFUWNT-UHFFFAOYSA-N 0.000 claims 1
- AFESQBQGMRQPJV-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-(3-fluoro-4-pyrrolidin-1-ylphenyl)urea Chemical compound C=1C=C(N2CCCC2)C(F)=CC=1NC(=O)NC1=CC=C(Cl)C=C1 AFESQBQGMRQPJV-UHFFFAOYSA-N 0.000 claims 1
- CEQBJLQGCDDUCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-(3-pyrazol-1-ylphenyl)urea Chemical compound C1=CC(Cl)=CC=C1NC(=O)NC1=CC=CC(N2N=CC=C2)=C1 CEQBJLQGCDDUCY-UHFFFAOYSA-N 0.000 claims 1
- LDENYLOBHSGDFQ-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-(4-ethoxyphenyl)urea Chemical compound C1=CC(OCC)=CC=C1NC(=O)NC1=CC=C(Cl)C=C1 LDENYLOBHSGDFQ-UHFFFAOYSA-N 0.000 claims 1
- QRARSYHMOSMDLP-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-(4-piperidin-1-ylphenyl)urea Chemical compound C1=CC(Cl)=CC=C1NC(=O)NC1=CC=C(N2CCCCC2)C=C1 QRARSYHMOSMDLP-UHFFFAOYSA-N 0.000 claims 1
- GPELLUQEAIOOFT-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-(4-pyrazol-1-ylphenyl)urea Chemical compound C1=CC(Cl)=CC=C1NC(=O)NC1=CC=C(N2N=CC=C2)C=C1 GPELLUQEAIOOFT-UHFFFAOYSA-N 0.000 claims 1
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- FEOCWWBYAPFFOF-UHFFFAOYSA-N ethyl 2-[4-[(4-fluorophenyl)carbamoylamino]phenyl]acetate Chemical compound C1=CC(CC(=O)OCC)=CC=C1NC(=O)NC1=CC=C(F)C=C1 FEOCWWBYAPFFOF-UHFFFAOYSA-N 0.000 claims 1
- LQIGNEFYRGFEDC-UHFFFAOYSA-N ethyl 2-chloro-4-[(4-ethoxycarbonylphenyl)carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=C(C(=O)OCC)C(Cl)=C1 LQIGNEFYRGFEDC-UHFFFAOYSA-N 0.000 claims 1
- SKEVEEGSJFZINO-UHFFFAOYSA-N ethyl 2-chloro-4-[(4-fluorophenyl)carbamoylamino]benzoate Chemical compound C1=C(Cl)C(C(=O)OCC)=CC=C1NC(=O)NC1=CC=C(F)C=C1 SKEVEEGSJFZINO-UHFFFAOYSA-N 0.000 claims 1
- NZCPJZPQSHPVJP-UHFFFAOYSA-N ethyl 3-[(4-ethoxycarbonylphenyl)carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=CC(C(=O)OCC)=C1 NZCPJZPQSHPVJP-UHFFFAOYSA-N 0.000 claims 1
- ARNPJTWYVZQXNP-UHFFFAOYSA-N ethyl 3-[(4-fluorophenyl)carbamoylamino]benzoate Chemical compound CCOC(=O)C1=CC=CC(NC(=O)NC=2C=CC(F)=CC=2)=C1 ARNPJTWYVZQXNP-UHFFFAOYSA-N 0.000 claims 1
- WBPAFUYWRGKQSG-UHFFFAOYSA-N ethyl 4-(1,3-benzothiazol-6-ylcarbamoylamino)benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=C(N=CS2)C2=C1 WBPAFUYWRGKQSG-UHFFFAOYSA-N 0.000 claims 1
- APQFMDQPXNKLIK-UHFFFAOYSA-N ethyl 4-(1h-indol-5-ylcarbamoylamino)benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=C(NC=C2)C2=C1 APQFMDQPXNKLIK-UHFFFAOYSA-N 0.000 claims 1
- SLPNRBSFKWMCLO-UHFFFAOYSA-N ethyl 4-(1h-indol-6-ylcarbamoylamino)benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=C(C=CN2)C2=C1 SLPNRBSFKWMCLO-UHFFFAOYSA-N 0.000 claims 1
- MWOQTMMZHFJCJJ-UHFFFAOYSA-N ethyl 4-[(1-oxo-2,3-dihydroinden-5-yl)carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=C(C(=O)CC2)C2=C1 MWOQTMMZHFJCJJ-UHFFFAOYSA-N 0.000 claims 1
- PAKLYGYPZZDNHP-UHFFFAOYSA-N ethyl 4-[(2,4,6-trifluorophenyl)carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=C(F)C=C(F)C=C1F PAKLYGYPZZDNHP-UHFFFAOYSA-N 0.000 claims 1
- LDWCZSHKVJNSDS-UHFFFAOYSA-N ethyl 4-[(2,4-difluorophenyl)carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=C(F)C=C1F LDWCZSHKVJNSDS-UHFFFAOYSA-N 0.000 claims 1
- YRGLBYFSDMQLGB-UHFFFAOYSA-N ethyl 4-[(2-chloro-4-fluorophenyl)carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=C(F)C=C1Cl YRGLBYFSDMQLGB-UHFFFAOYSA-N 0.000 claims 1
- SIDAXTZGQQRWLY-UHFFFAOYSA-N ethyl 4-[(2-chlorophenyl)carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=CC=C1Cl SIDAXTZGQQRWLY-UHFFFAOYSA-N 0.000 claims 1
- VBTZVXMYIIFSRH-UHFFFAOYSA-N ethyl 4-[(2-fluorophenyl)carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=CC=C1F VBTZVXMYIIFSRH-UHFFFAOYSA-N 0.000 claims 1
- UCURJVGAHFXOGM-UHFFFAOYSA-N ethyl 4-[(3,4-difluorophenyl)carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=C(F)C(F)=C1 UCURJVGAHFXOGM-UHFFFAOYSA-N 0.000 claims 1
- HEBDWBCMYBFGHJ-UHFFFAOYSA-N ethyl 4-[(3-acetylphenyl)carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=CC(C(C)=O)=C1 HEBDWBCMYBFGHJ-UHFFFAOYSA-N 0.000 claims 1
- LGWMNYOKMADBBG-UHFFFAOYSA-N ethyl 4-[(3-chloro-4-fluorophenyl)carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=C(F)C(Cl)=C1 LGWMNYOKMADBBG-UHFFFAOYSA-N 0.000 claims 1
- CYVYCDVRLVZJEI-UHFFFAOYSA-N ethyl 4-[(3-chlorophenyl)carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 CYVYCDVRLVZJEI-UHFFFAOYSA-N 0.000 claims 1
- BWJMOOIEZAIDQB-UHFFFAOYSA-N ethyl 4-[(3-fluoro-4-piperidin-1-ylphenyl)carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC(C=C1F)=CC=C1N1CCCCC1 BWJMOOIEZAIDQB-UHFFFAOYSA-N 0.000 claims 1
- KVXMNXYDSOBVIQ-UHFFFAOYSA-N ethyl 4-[(3-fluorophenyl)carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=CC(F)=C1 KVXMNXYDSOBVIQ-UHFFFAOYSA-N 0.000 claims 1
- GTEYFMXYOAMRLE-UHFFFAOYSA-N ethyl 4-[(4-acetylphenyl)carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=C(C(C)=O)C=C1 GTEYFMXYOAMRLE-UHFFFAOYSA-N 0.000 claims 1
- BDKSFIXEFIZUBX-UHFFFAOYSA-N ethyl 4-[(4-benzoylphenyl)carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 BDKSFIXEFIZUBX-UHFFFAOYSA-N 0.000 claims 1
- OIBDWDFYLRGLNQ-UHFFFAOYSA-N ethyl 4-[(4-butanoylphenyl)carbamoylamino]benzoate Chemical compound C1=CC(C(=O)CCC)=CC=C1NC(=O)NC1=CC=C(C(=O)OCC)C=C1 OIBDWDFYLRGLNQ-UHFFFAOYSA-N 0.000 claims 1
- DOZVXMMXOZVXMD-UHFFFAOYSA-N ethyl 4-[(4-butoxycarbonylphenyl)carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCCCC)=CC=C1NC(=O)NC1=CC=C(C(=O)OCC)C=C1 DOZVXMMXOZVXMD-UHFFFAOYSA-N 0.000 claims 1
- XQMAQFNMWHCRPQ-UHFFFAOYSA-N ethyl 4-[(4-chlorophenyl)carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=C(Cl)C=C1 XQMAQFNMWHCRPQ-UHFFFAOYSA-N 0.000 claims 1
- AHDLDMGQJFXSBH-UHFFFAOYSA-N ethyl 4-[(4-ethoxycarbonylphenyl)carbamoylamino]-2-methoxybenzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=C(C(=O)OCC)C(OC)=C1 AHDLDMGQJFXSBH-UHFFFAOYSA-N 0.000 claims 1
- KOAKPJSGWYVHGH-UHFFFAOYSA-N ethyl 4-[(4-ethoxycarbonylphenyl)carbamoylamino]-3-methoxybenzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=C(C(=O)OCC)C=C1OC KOAKPJSGWYVHGH-UHFFFAOYSA-N 0.000 claims 1
- KPCPWCOJCNAPSX-UHFFFAOYSA-N ethyl 4-[(4-fluoro-2-methylphenyl)carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=C(F)C=C1C KPCPWCOJCNAPSX-UHFFFAOYSA-N 0.000 claims 1
- GNMDKUSDCVGCCS-UHFFFAOYSA-N ethyl 4-[(4-fluoro-3-methoxyphenyl)carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=C(F)C(OC)=C1 GNMDKUSDCVGCCS-UHFFFAOYSA-N 0.000 claims 1
- GIOJOZUVJQCQBM-UHFFFAOYSA-N ethyl 4-[(4-fluoro-3-methylphenyl)carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=C(F)C(C)=C1 GIOJOZUVJQCQBM-UHFFFAOYSA-N 0.000 claims 1
- AGAHKRHRDYFBAH-UHFFFAOYSA-N ethyl 4-[(4-fluorophenyl)carbamoylamino]-3-hydroxybenzoate Chemical compound OC1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=C(F)C=C1 AGAHKRHRDYFBAH-UHFFFAOYSA-N 0.000 claims 1
- NVFZNTUOXHQSPO-UHFFFAOYSA-N ethyl 4-[(4-fluorophenyl)carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=C(F)C=C1 NVFZNTUOXHQSPO-UHFFFAOYSA-N 0.000 claims 1
- TYHPBHLAXUWVDL-UHFFFAOYSA-N ethyl 4-[(4-imidazol-1-ylphenyl)carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=C(N2C=NC=C2)C=C1 TYHPBHLAXUWVDL-UHFFFAOYSA-N 0.000 claims 1
- AJHBMLNHWSRQNL-UHFFFAOYSA-N ethyl 4-[(4-methylsulfanylphenyl)carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=C(SC)C=C1 AJHBMLNHWSRQNL-UHFFFAOYSA-N 0.000 claims 1
- GZWOVIZUQZEDGL-UHFFFAOYSA-N ethyl 4-[(4-pentoxycarbonylphenyl)carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCCCCC)=CC=C1NC(=O)NC1=CC=C(C(=O)OCC)C=C1 GZWOVIZUQZEDGL-UHFFFAOYSA-N 0.000 claims 1
- CCHPQPXIPIEUPY-UHFFFAOYSA-N ethyl 4-[(4-phenoxycarbonylphenyl)carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=C(C(=O)OC=2C=CC=CC=2)C=C1 CCHPQPXIPIEUPY-UHFFFAOYSA-N 0.000 claims 1
- AJWWIQMPRRKLKN-UHFFFAOYSA-N ethyl 4-[(4-propanoylphenyl)carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=C(C(=O)CC)C=C1 AJWWIQMPRRKLKN-UHFFFAOYSA-N 0.000 claims 1
- DPDQWRGMCIXKBB-UHFFFAOYSA-N ethyl 4-[(4-propoxycarbonylphenyl)carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCCC)=CC=C1NC(=O)NC1=CC=C(C(=O)OCC)C=C1 DPDQWRGMCIXKBB-UHFFFAOYSA-N 0.000 claims 1
- SAIUAYATIGVZCO-UHFFFAOYSA-N ethyl 4-[(6-chloropyridin-3-yl)carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=C(Cl)N=C1 SAIUAYATIGVZCO-UHFFFAOYSA-N 0.000 claims 1
- GVYUYGGJBOPNPO-UHFFFAOYSA-N ethyl 4-[(6-fluoro-1,3-benzothiazol-2-yl)carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=NC2=CC=C(F)C=C2S1 GVYUYGGJBOPNPO-UHFFFAOYSA-N 0.000 claims 1
- DXBGGXIHUWFGQI-UHFFFAOYSA-N ethyl 4-[(6-methoxypyridin-3-yl)carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=C(OC)N=C1 DXBGGXIHUWFGQI-UHFFFAOYSA-N 0.000 claims 1
- SNVIHCGKYVDOFN-UHFFFAOYSA-N ethyl 4-[(6-morpholin-4-ylpyridin-3-yl)carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=C(N2CCOCC2)N=C1 SNVIHCGKYVDOFN-UHFFFAOYSA-N 0.000 claims 1
- IRENAQZVUJHUAH-UHFFFAOYSA-N ethyl 4-[2-(1-methylpyrrol-2-yl)ethylcarbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NCCC1=CC=CN1C IRENAQZVUJHUAH-UHFFFAOYSA-N 0.000 claims 1
- QUOJIWNRBBUPRU-UHFFFAOYSA-N ethyl 4-[[3-(1,3-oxazol-5-yl)phenyl]carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=CC(C=2OC=NC=2)=C1 QUOJIWNRBBUPRU-UHFFFAOYSA-N 0.000 claims 1
- LHNLQNCBECZTDA-UHFFFAOYSA-N ethyl 4-[[3-(2-methylpyrimidin-4-yl)phenyl]carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=CC(C=2N=C(C)N=CC=2)=C1 LHNLQNCBECZTDA-UHFFFAOYSA-N 0.000 claims 1
- HBBKGFIWFLKKLU-UHFFFAOYSA-N ethyl 4-[[4-(1,1,2,2-tetrafluoroethoxy)phenyl]carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=C(OC(F)(F)C(F)F)C=C1 HBBKGFIWFLKKLU-UHFFFAOYSA-N 0.000 claims 1
- DHLBHBAONQVVCR-UHFFFAOYSA-N ethyl 4-[[4-(1,3-oxazol-5-yl)phenyl]carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=C(C=2OC=NC=2)C=C1 DHLBHBAONQVVCR-UHFFFAOYSA-N 0.000 claims 1
- GFFFUDJOHZOVMJ-UHFFFAOYSA-N ethyl 4-[[4-(1h-pyrazol-5-yl)phenyl]carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=C(C2=NNC=C2)C=C1 GFFFUDJOHZOVMJ-UHFFFAOYSA-N 0.000 claims 1
- OSWPKSIANACMJB-UHFFFAOYSA-N ethyl 4-[[4-(2-ethoxy-2-oxoethyl)phenyl]carbamoylamino]benzoate Chemical compound C1=CC(CC(=O)OCC)=CC=C1NC(=O)NC1=CC=C(C(=O)OCC)C=C1 OSWPKSIANACMJB-UHFFFAOYSA-N 0.000 claims 1
- FAQDLJBNGDFYMA-UHFFFAOYSA-N ethyl 4-[[4-(2-methylpropoxycarbonyl)phenyl]carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=C(C(=O)OCC(C)C)C=C1 FAQDLJBNGDFYMA-UHFFFAOYSA-N 0.000 claims 1
- FPFQEESCIWMZKS-UHFFFAOYSA-N ethyl 4-[[4-(2-methylpyrimidin-4-yl)phenyl]carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=C(C=2N=C(C)N=CC=2)C=C1 FPFQEESCIWMZKS-UHFFFAOYSA-N 0.000 claims 1
- JKLQCJYMCQGKRK-UHFFFAOYSA-N ethyl 4-[[4-(4,5-dihydro-1,3-oxazol-2-yl)phenyl]carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=C(C=2OCCN=2)C=C1 JKLQCJYMCQGKRK-UHFFFAOYSA-N 0.000 claims 1
- CGZPONNDMBJAHJ-UHFFFAOYSA-N ethyl 4-[[4-(thiadiazol-4-yl)phenyl]carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=C(C=2N=NSC=2)C=C1 CGZPONNDMBJAHJ-UHFFFAOYSA-N 0.000 claims 1
- QMCYNBAMYIZSCQ-UHFFFAOYSA-N ethyl 4-methyl-2-[(4-methylsulfanylphenyl)carbamoylamino]-1,3-thiazole-5-carboxylate Chemical compound CC1=C(C(=O)OCC)SC(NC(=O)NC=2C=CC(SC)=CC=2)=N1 QMCYNBAMYIZSCQ-UHFFFAOYSA-N 0.000 claims 1
- JMCJHSGHUSDBMI-UHFFFAOYSA-N ethyl 6-[(4-ethoxycarbonylphenyl)carbamoylamino]pyridine-3-carboxylate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=C(C(=O)OCC)C=N1 JMCJHSGHUSDBMI-UHFFFAOYSA-N 0.000 claims 1
- 210000001035 gastrointestinal tract Anatomy 0.000 claims 1
- 230000036543 hypotension Effects 0.000 claims 1
- 208000026278 immune system disease Diseases 0.000 claims 1
- 206010027175 memory impairment Diseases 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- NRGLZGBNZJGZKI-UHFFFAOYSA-N methyl 2-[(4-ethoxycarbonylphenyl)carbamoylamino]-1,3-thiazole-5-carboxylate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=NC=C(C(=O)OC)S1 NRGLZGBNZJGZKI-UHFFFAOYSA-N 0.000 claims 1
- BVSQCSILUMBZQS-UHFFFAOYSA-N methyl 2-[(4-ethoxycarbonylphenyl)carbamoylamino]thiophene-3-carboxylate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=C(C(=O)OC)C=CS1 BVSQCSILUMBZQS-UHFFFAOYSA-N 0.000 claims 1
- ILZREKGNTSOUAX-UHFFFAOYSA-N methyl 3-[(4-ethoxycarbonylphenyl)carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=CC(C(=O)OC)=C1 ILZREKGNTSOUAX-UHFFFAOYSA-N 0.000 claims 1
- PFWFFNFPPYAMLK-UHFFFAOYSA-N methyl 4-[(4-fluorophenyl)carbamoylamino]-3-hydroxybenzoate Chemical compound OC1=CC(C(=O)OC)=CC=C1NC(=O)NC1=CC=C(F)C=C1 PFWFFNFPPYAMLK-UHFFFAOYSA-N 0.000 claims 1
- JMOUJOMNIUZYGP-UHFFFAOYSA-N methyl 4-[(4-fluorophenyl)carbamoylamino]-3-methylbenzoate Chemical compound CC1=CC(C(=O)OC)=CC=C1NC(=O)NC1=CC=C(F)C=C1 JMOUJOMNIUZYGP-UHFFFAOYSA-N 0.000 claims 1
- GXWOZLUDXOONHR-UHFFFAOYSA-N methyl 4-[(4-fluorophenyl)carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NC(=O)NC1=CC=C(F)C=C1 GXWOZLUDXOONHR-UHFFFAOYSA-N 0.000 claims 1
- OUYGAKBMUFDONT-UHFFFAOYSA-N methyl 5-[(4-ethoxycarbonylphenyl)carbamoylamino]furan-2-carboxylate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=C(C(=O)OC)O1 OUYGAKBMUFDONT-UHFFFAOYSA-N 0.000 claims 1
- LURCDYPZSKUGII-UHFFFAOYSA-N methyl 6-[(4-ethoxycarbonylphenyl)carbamoylamino]pyridine-3-carboxylate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=C(C(=O)OC)C=N1 LURCDYPZSKUGII-UHFFFAOYSA-N 0.000 claims 1
- RYTXFKPJABIZJS-UHFFFAOYSA-N methyl 6-[(4-fluorophenyl)carbamoylamino]pyridine-3-carboxylate Chemical compound N1=CC(C(=O)OC)=CC=C1NC(=O)NC1=CC=C(F)C=C1 RYTXFKPJABIZJS-UHFFFAOYSA-N 0.000 claims 1
- 230000001730 monoaminergic effect Effects 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 201000007620 paralytic ileus Diseases 0.000 claims 1
- VLHQFLDQFIIVQA-UHFFFAOYSA-N pentyl 4-[(4-fluorophenyl)carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCCCCC)=CC=C1NC(=O)NC1=CC=C(F)C=C1 VLHQFLDQFIIVQA-UHFFFAOYSA-N 0.000 claims 1
- 206010034674 peritonitis Diseases 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- YKIDTZMERLJXEY-UHFFFAOYSA-N phenyl 4-[(4-fluorophenyl)carbamoylamino]benzoate Chemical compound C1=CC(F)=CC=C1NC(=O)NC1=CC=C(C(=O)OC=2C=CC=CC=2)C=C1 YKIDTZMERLJXEY-UHFFFAOYSA-N 0.000 claims 1
- 230000002035 prolonged effect Effects 0.000 claims 1
- VYKHVKJJPHJKGC-UHFFFAOYSA-N propyl 4-[(4-fluorophenyl)carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCCC)=CC=C1NC(=O)NC1=CC=C(F)C=C1 VYKHVKJJPHJKGC-UHFFFAOYSA-N 0.000 claims 1
- 208000020016 psychiatric disease Diseases 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 230000000306 recurrent effect Effects 0.000 claims 1
- 230000001850 reproductive effect Effects 0.000 claims 1
- 208000017443 reproductive system disease Diseases 0.000 claims 1
- 230000000241 respiratory effect Effects 0.000 claims 1
- 210000002345 respiratory system Anatomy 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 230000002784 sclerotic effect Effects 0.000 claims 1
- 230000036303 septic shock Effects 0.000 claims 1
- 230000000391 smoking effect Effects 0.000 claims 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 238000001356 surgical procedure Methods 0.000 claims 1
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
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| US60226804P | 2004-08-16 | 2004-08-16 | |
| PCT/GB2005/050131 WO2006018662A2 (en) | 2004-08-16 | 2005-08-16 | Aryl urea derivatives for treating obesity |
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| JP2008509982A JP2008509982A (ja) | 2008-04-03 |
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| WO (1) | WO2006018662A2 (enExample) |
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| US20080009477A1 (en) * | 2004-11-04 | 2008-01-10 | Neurogen Corporation | Arylalkyl Ureas As Cb1 Antagonists |
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| CN101253152A (zh) * | 2005-09-02 | 2008-08-27 | 安斯泰来制药株式会社 | 作为rock抑制剂的酰胺衍生物 |
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| WO2009035951A2 (en) * | 2007-09-11 | 2009-03-19 | Arete Therapeutics, Inc. | Soluble epoxide hydrolase inhibitors |
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| BRPI1004176A2 (pt) * | 2010-10-25 | 2015-08-11 | Univ Rio De Janeiro | Compostos aril e/ou hetero aril uréias funcionalizados; processo de síntese desses composto; composição farmacêutica contendo tais compostos e usos |
| WO2012120056A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Tetrasubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| WO2012120054A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| WO2012120055A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2766349B1 (de) | 2011-03-08 | 2016-06-01 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2683704B1 (de) | 2011-03-08 | 2014-12-17 | Sanofi | Verzweigte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| US8461179B1 (en) | 2012-06-07 | 2013-06-11 | Deciphera Pharmaceuticals, Llc | Dihydronaphthyridines and related compounds useful as kinase inhibitors for the treatment of proliferative diseases |
| ES2489297B1 (es) * | 2013-01-22 | 2015-06-10 | Consejo Superior De Investigaciones Científicas (Csic) | Benzotiazoles sustituidos y sus aplicaciones terapeuticas para el tratamiento de enfermedades humanas |
| WO2015027160A2 (en) * | 2013-08-22 | 2015-02-26 | Northeastern University | Allosteric modulators of the cannibinoid 1 receptor |
| GB201401886D0 (en) | 2014-02-04 | 2014-03-19 | Lytix Biopharma As | Neurodegenerative therapies |
| WO2015162216A1 (en) * | 2014-04-24 | 2015-10-29 | Universita' Degli Studi Di Siena | Biaryl amide or urea derivatives as trpv1 ligands |
| CZ305633B6 (cs) * | 2014-08-13 | 2016-01-13 | Univerzita Hradec Králové | Deriváty benzothiazolylmočoviny, způsob jejich přípravy a jejich použití |
| WO2016049774A1 (en) * | 2014-10-03 | 2016-04-07 | The Royal Institution For The Advancement Of Learning/Mcgill University | Urea and bis-urea based compounds and analogues thereof useful in the treatment of androgen receptor mediated diseases or disorders |
| JP2018516992A (ja) | 2015-06-12 | 2018-06-28 | アクソファント サイエンシーズ ゲーエムベーハーＡｘｏｖａｎｔ Ｓｃｉｅｎｃｅｓ Ｇｍｂｈ | レム睡眠行動障害の予防および処置のために有用なジアリールおよびアリールヘテロアリール尿素誘導体 |
| CN108472285A (zh) | 2015-07-15 | 2018-08-31 | 阿速万科学有限责任公司 | 用于预防和治疗与神经退行性疾病相关联的幻觉的二芳基和芳基杂芳基脲衍生物 |
| AU2017228398A1 (en) | 2016-03-03 | 2018-10-18 | Cornell University | Small molecule IRE1-alpha inhibitors |
| RS60825B1 (sr) | 2016-03-17 | 2020-10-30 | Hoffmann La Roche | Aktivnost derivata 5-etiol-4-metil-pirazol-3-karboksamida kao agonista taar-a |
| JP7455581B2 (ja) * | 2017-05-12 | 2024-03-26 | リサーチ トライアングル インスティテュート | Ｃｂ１アロステリック・モジュレーターとしてのジアリール尿素 |
| KR102708177B1 (ko) | 2018-01-31 | 2024-09-23 | 데시페라 파마슈티칼스, 엘엘씨. | 위장관 기질 종양의 치료를 위한 병용 요법 |
| CN118903436A (zh) | 2018-01-31 | 2024-11-08 | 德西费拉制药有限责任公司 | 治疗肥大细胞增多症的组合疗法 |
| US20240317727A1 (en) * | 2018-12-11 | 2024-09-26 | Duke University | Compositions and methods for the treatment of cancer |
| WO2020126968A2 (en) * | 2018-12-20 | 2020-06-25 | Bayer Aktiengesellschaft | Urea derivatives |
| IL330104A (en) | 2019-03-11 | 2026-08-01 | Deciphera Pharmaceuticals Llc | Crystalline forms of rifatinib |
| CN114269719A (zh) * | 2019-06-28 | 2022-04-01 | Rti国际 | 作为cb1变构调节剂的脲衍生物 |
| HRP20260411T1 (hr) | 2019-08-12 | 2026-05-08 | Deciphera Pharmaceuticals, Llc | Ripretinib za liječenje gastrointestinalnih stromalnih tumora |
| FI4084779T3 (fi) | 2019-12-30 | 2024-12-16 | Deciphera Pharmaceuticals Llc | 1-(4-bromi-5-(1-etyyli-7-(metyyliamino)-2-okso-1,2-dihydro-1,6-naftyridin-3-yyli)-2-fluorifenyyli)-3-fenyyliurean koostumuksia |
| WO2021222637A1 (en) * | 2020-04-30 | 2021-11-04 | United States Government As Represented By The Department Of Veterans Affairs | Krüppel-like factor 15 (klf15) small molecule agonists in kidney disease |
| US11779572B1 (en) | 2022-09-02 | 2023-10-10 | Deciphera Pharmaceuticals, Llc | Methods of treating gastrointestinal stromal tumors |
| WO2024246857A1 (en) * | 2023-06-02 | 2024-12-05 | Innopharmascreen Inc. | Urea compounds, compositions, and methods for treating asthma and parkinson's disease |
| WO2025085745A1 (en) | 2023-10-18 | 2025-04-24 | Gen1E Lifesciences Inc. | Modulators of extracellular signal-regulated kinase |
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| US4088768A (en) * | 1975-05-06 | 1978-05-09 | Eli Lilly And Company | N-heterocyclic ureas as immune regulants |
| DK41193D0 (da) * | 1993-04-07 | 1993-04-07 | Neurosearch As | Ionkanalaabnere |
| AU2003226929A1 (en) * | 2002-11-25 | 2004-06-18 | 7Tm Pharma A/S | Novel benzamide compounds for use in mch receptor related disorders |
| CA2575764A1 (en) * | 2004-10-27 | 2006-05-11 | Neurogen Corporation | Diaryl ureas as cb1 antagonists |
-
2005
- 2005-08-16 US US11/660,405 patent/US20080261952A1/en not_active Abandoned
- 2005-08-16 EP EP05772020A patent/EP1786422A2/en not_active Withdrawn
- 2005-08-16 JP JP2007526578A patent/JP2008509982A/ja active Pending
- 2005-08-16 WO PCT/GB2005/050131 patent/WO2006018662A2/en not_active Ceased
-
2012
- 2012-02-17 US US13/399,517 patent/US20120214808A1/en not_active Abandoned
- 2012-02-23 JP JP2012037806A patent/JP2012140445A/ja not_active Withdrawn
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