JP4932730B2 - バニロイド受容体サブタイプ１（ｖｒ１）受容体を阻害するクロマニル尿素化合物およびその使用 - Google Patents

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Publication number

JP4932730B2

JP4932730B2 JP2007543471A JP2007543471A JP4932730B2 JP 4932730 B2 JP4932730 B2 JP 4932730B2 JP 2007543471 A JP2007543471 A JP 2007543471A JP 2007543471 A JP2007543471 A JP 2007543471A JP 4932730 B2 JP4932730 B2 JP 4932730B2

Authority

JP

Japan

Prior art keywords

alkyl

indazol

dihydro

chromen

methyl

Prior art date

2004-11-24

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.)

Expired - Fee Related

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• 150000001875 compounds Chemical class 0.000 title claims description 351
• 108010025083 TRPV1 receptor Proteins 0.000 title description 29
• 102100029613 Transient receptor potential cation channel subfamily V member 1 Human genes 0.000 title description 16
• 102000005962 receptors Human genes 0.000 title description 4
• 125000000217 alkyl group Chemical group 0.000 claims description 187
• -1 —OR c Chemical group 0.000 claims description 97
• 229910052739 hydrogen Inorganic materials 0.000 claims description 56
• 239000001257 hydrogen Substances 0.000 claims description 56
• 125000001188 haloalkyl group Chemical group 0.000 claims description 38
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 33
• 125000003342 alkenyl group Chemical group 0.000 claims description 33
• 125000003118 aryl group Chemical group 0.000 claims description 27
• 150000002431 hydrogen Chemical class 0.000 claims description 27
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 23
• 125000001424 substituent group Chemical group 0.000 claims description 23
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 21
• 125000001072 heteroaryl group Chemical group 0.000 claims description 19
• 125000002950 monocyclic group Chemical group 0.000 claims description 19
• 125000003545 alkoxy group Chemical group 0.000 claims description 17
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 16
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 15
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
• 229910052736 halogen Inorganic materials 0.000 claims description 14
• 150000002367 halogens Chemical class 0.000 claims description 14
• LNRLQTQYVBBJBO-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-[7-(trifluoromethyl)-3,4-dihydro-2h-chromen-4-yl]urea Chemical compound C1COC2=CC(C(F)(F)F)=CC=C2C1NC(=O)NC1=CC=CC2=C1C=NN2 LNRLQTQYVBBJBO-UHFFFAOYSA-N 0.000 claims description 12
• FAWFVJIDGASJLP-UHFFFAOYSA-N 1-[(1-benzyl-3,4-dihydro-2h-quinolin-2-yl)methyl]-3-(1h-indazol-4-yl)urea Chemical compound C=1C=CC=2NN=CC=2C=1NC(=O)NCC1CCC2=CC=CC=C2N1CC1=CC=CC=C1 FAWFVJIDGASJLP-UHFFFAOYSA-N 0.000 claims description 11
• 239000004202 carbamide Substances 0.000 claims description 11
• MCCWMGNDQBQPEC-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-(7-methoxy-2,2-dimethyl-8-propyl-3,4-dihydrochromen-4-yl)urea Chemical compound C1C(C)(C)OC=2C(CCC)=C(OC)C=CC=2C1NC(=O)NC1=CC=CC2=C1C=NN2 MCCWMGNDQBQPEC-UHFFFAOYSA-N 0.000 claims description 9
• YUYRDRHVSPICBY-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-[[1-(2-phenylethyl)-3,4-dihydro-2h-quinolin-2-yl]methyl]urea Chemical compound C=1C=CC=2NN=CC=2C=1NC(=O)NCC1CCC2=CC=CC=C2N1CCC1=CC=CC=C1 YUYRDRHVSPICBY-UHFFFAOYSA-N 0.000 claims description 9
• FGVFFUSBPJFGCF-UHFFFAOYSA-N 1-(8-tert-butyl-3,4-dihydro-2h-chromen-4-yl)-3-(1h-indazol-4-yl)urea Chemical compound C1COC=2C(C(C)(C)C)=CC=CC=2C1NC(=O)NC1=CC=CC2=C1C=NN2 FGVFFUSBPJFGCF-UHFFFAOYSA-N 0.000 claims description 9
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 9
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
• 125000000623 heterocyclic group Chemical group 0.000 claims description 8
• 229910052760 oxygen Inorganic materials 0.000 claims description 8
• TXYBMMZLKHMZII-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-(7-methoxy-2,2,8-trimethyl-3,4-dihydrochromen-4-yl)urea Chemical compound C1C(C)(C)OC2=C(C)C(OC)=CC=C2C1NC(=O)NC1=CC=CC2=C1C=NN2 TXYBMMZLKHMZII-UHFFFAOYSA-N 0.000 claims description 7
• IDVNTJAGOBONHF-UHFFFAOYSA-N 1-(2,2-dibutyl-7-fluoro-3,4-dihydrochromen-4-yl)-3-(1h-indazol-4-yl)urea Chemical compound C12=CC=C(F)C=C2OC(CCCC)(CCCC)CC1NC(=O)NC1=CC=CC2=C1C=NN2 IDVNTJAGOBONHF-UHFFFAOYSA-N 0.000 claims description 7
• WFZDKUJYZFGQSX-UHFFFAOYSA-N 1-(7,8-difluoro-2,2-dimethyl-3,4-dihydrochromen-4-yl)-3-(1h-indazol-4-yl)urea Chemical compound C12=CC=C(F)C(F)=C2OC(C)(C)CC1NC(=O)NC1=CC=CC2=C1C=NN2 WFZDKUJYZFGQSX-UHFFFAOYSA-N 0.000 claims description 7
• FDAPTCFAZHVYLK-UHFFFAOYSA-N 1-isoquinolin-5-yl-3-[7-(trifluoromethyl)-3,4-dihydro-2h-chromen-4-yl]urea Chemical compound N1=CC=C2C(NC(=O)NC3C4=CC=C(C=C4OCC3)C(F)(F)F)=CC=CC2=C1 FDAPTCFAZHVYLK-UHFFFAOYSA-N 0.000 claims description 7
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
• FGXCGGVCKKUACY-UHFFFAOYSA-N 1-(1-benzyl-2,3,4,5-tetrahydro-1-benzazepin-5-yl)-3-(1h-indazol-4-yl)urea Chemical compound C=1C=CC=2NN=CC=2C=1NC(=O)NC(C1=CC=CC=C11)CCCN1CC1=CC=CC=C1 FGXCGGVCKKUACY-UHFFFAOYSA-N 0.000 claims description 6
• BTIBLCUSSWNUOC-UHFFFAOYSA-N 1-(1-benzyl-7-fluoro-3,4-dihydro-2h-quinolin-3-yl)-3-(1h-indazol-4-yl)urea Chemical compound C12=CC(F)=CC=C2CC(NC(=O)NC=2C=3C=NNC=3C=CC=2)CN1CC1=CC=CC=C1 BTIBLCUSSWNUOC-UHFFFAOYSA-N 0.000 claims description 6
• MPTPURFMBQGHAG-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-(2,2,8-trimethyl-3,4-dihydrochromen-4-yl)urea Chemical compound C1C(C)(C)OC=2C(C)=CC=CC=2C1NC(=O)NC1=CC=CC2=C1C=NN2 MPTPURFMBQGHAG-UHFFFAOYSA-N 0.000 claims description 6
• PVYNJQODFKXXFR-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-(7-methoxy-2,2-dimethyl-3,4-dihydrochromen-4-yl)urea Chemical compound C1C(C)(C)OC2=CC(OC)=CC=C2C1NC(=O)NC1=CC=CC2=C1C=NN2 PVYNJQODFKXXFR-UHFFFAOYSA-N 0.000 claims description 6
• OSMLRKGCJFBTSO-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-[(1-propyl-3,4-dihydro-2h-quinolin-2-yl)methyl]urea Chemical compound C1CC2=CC=CC=C2N(CCC)C1CNC(=O)NC1=CC=CC2=C1C=NN2 OSMLRKGCJFBTSO-UHFFFAOYSA-N 0.000 claims description 6
• OAGOFYGHRQNIDL-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-[1-[[3-(trifluoromethyl)phenyl]methyl]-3,4-dihydro-2h-quinolin-3-yl]urea Chemical compound FC(F)(F)C1=CC=CC(CN2C3=CC=CC=C3CC(C2)NC(=O)NC=2C=3C=NNC=3C=CC=2)=C1 OAGOFYGHRQNIDL-UHFFFAOYSA-N 0.000 claims description 6
• JUSPWOFSXJZIOC-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-[[1-[[3-(trifluoromethyl)phenyl]methyl]-3,4-dihydro-2h-quinolin-2-yl]methyl]urea Chemical compound FC(F)(F)C1=CC=CC(CN2C3=CC=CC=C3CCC2CNC(=O)NC=2C=3C=NNC=3C=CC=2)=C1 JUSPWOFSXJZIOC-UHFFFAOYSA-N 0.000 claims description 6
• IHTTUOYEOCHAHS-UHFFFAOYSA-N 1-(2,2-diethyl-7-fluoro-3,4-dihydrochromen-4-yl)-3-(1h-indazol-4-yl)urea Chemical compound C12=CC=C(F)C=C2OC(CC)(CC)CC1NC(=O)NC1=CC=CC2=C1C=NN2 IHTTUOYEOCHAHS-UHFFFAOYSA-N 0.000 claims description 6
• FOXQNSKEGIEOEW-UHFFFAOYSA-N 1-(2,2-dimethyl-3,4-dihydrochromen-4-yl)-3-(1h-indazol-4-yl)urea Chemical compound C12=CC=CC=C2OC(C)(C)CC1NC(=O)NC1=CC=CC2=C1C=NN2 FOXQNSKEGIEOEW-UHFFFAOYSA-N 0.000 claims description 6
• DWCDXFFPOOYDNU-UHFFFAOYSA-N 1-(2-tert-butyl-7-fluoro-3,4-dihydro-2h-chromen-4-yl)-3-(1h-indazol-4-yl)urea Chemical compound C12=CC=C(F)C=C2OC(C(C)(C)C)CC1NC(=O)NC1=CC=CC2=C1C=NN2 DWCDXFFPOOYDNU-UHFFFAOYSA-N 0.000 claims description 6
• JPNFDXYNTFZROK-UHFFFAOYSA-N 1-(3,4-dihydro-2h-chromen-2-ylmethyl)-3-(1h-indazol-4-yl)urea Chemical compound C1CC2=CC=CC=C2OC1CNC(=O)NC1=CC=CC2=C1C=NN2 JPNFDXYNTFZROK-UHFFFAOYSA-N 0.000 claims description 6
• QKGZZEPGSFJYIP-UHFFFAOYSA-N 1-(7,8-difluoro-3,4-dihydro-2h-chromen-4-yl)-3-(1h-indazol-4-yl)urea Chemical compound C1COC2=C(F)C(F)=CC=C2C1NC(=O)NC1=CC=CC2=C1C=NN2 QKGZZEPGSFJYIP-UHFFFAOYSA-N 0.000 claims description 6
• AWVYCAFGYUVHBP-UHFFFAOYSA-N 1-(7-fluoro-2,2-dimethyl-3,4-dihydrochromen-4-yl)-3-(1h-indazol-4-yl)urea Chemical compound C12=CC=C(F)C=C2OC(C)(C)CC1NC(=O)NC1=CC=CC2=C1C=NN2 AWVYCAFGYUVHBP-UHFFFAOYSA-N 0.000 claims description 6
• HZCWTWPZWYWLGJ-UHFFFAOYSA-N 1-(7-fluoro-2,2-dipropyl-3,4-dihydrochromen-4-yl)-3-(1h-indazol-4-yl)urea Chemical compound C12=CC=C(F)C=C2OC(CCC)(CCC)CC1NC(=O)NC1=CC=CC2=C1C=NN2 HZCWTWPZWYWLGJ-UHFFFAOYSA-N 0.000 claims description 6
• FZUXQDIXBAAZHO-UHFFFAOYSA-N 1-(7-tert-butyl-2,2-dimethyl-3,4-dihydrochromen-4-yl)-3-(1h-indazol-4-yl)urea Chemical compound C1C(C)(C)OC2=CC(C(C)(C)C)=CC=C2C1NC(=O)NC1=CC=CC2=C1C=NN2 FZUXQDIXBAAZHO-UHFFFAOYSA-N 0.000 claims description 6
• ACEHCQYIBFFPON-UHFFFAOYSA-N 1-[(1-benzyl-2,3-dihydroindol-2-yl)methyl]-3-(1h-indazol-4-yl)urea Chemical compound C=1C=CC=2NN=CC=2C=1NC(=O)NCC1CC2=CC=CC=C2N1CC1=CC=CC=C1 ACEHCQYIBFFPON-UHFFFAOYSA-N 0.000 claims description 6
• YBHFLNPHBYUHSF-UHFFFAOYSA-N 1-[(1-benzyl-6-fluoro-3,4-dihydro-2h-quinolin-2-yl)methyl]-3-(1h-indazol-4-yl)urea Chemical compound C=1C=CC=2NN=CC=2C=1NC(=O)NCC1CCC2=CC(F)=CC=C2N1CC1=CC=CC=C1 YBHFLNPHBYUHSF-UHFFFAOYSA-N 0.000 claims description 6
• WFTHPKJLXNIKMX-UHFFFAOYSA-N 1-[(4-benzyl-2,3-dihydro-1,4-benzoxazin-2-yl)methyl]-3-(1h-indazol-4-yl)urea Chemical compound C=1C=CC=2NN=CC=2C=1NC(=O)NCC(OC1=CC=CC=C11)CN1CC1=CC=CC=C1 WFTHPKJLXNIKMX-UHFFFAOYSA-N 0.000 claims description 6
• DDMMMYOZYVTAEO-UHFFFAOYSA-N 1-[8-chloro-7-(trifluoromethyl)-3,4-dihydro-2h-chromen-4-yl]-3-(1h-indazol-4-yl)urea Chemical compound C1COC2=C(Cl)C(C(F)(F)F)=CC=C2C1NC(=O)NC1=CC=CC2=C1C=NN2 DDMMMYOZYVTAEO-UHFFFAOYSA-N 0.000 claims description 6
• 125000002619 bicyclic group Chemical group 0.000 claims description 6
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
• CVNOORHKMWKCEI-UHFFFAOYSA-N 1-(1-benzyl-3,4-dihydro-2h-quinolin-4-yl)-3-(1h-indazol-4-yl)urea Chemical compound C=1C=CC=2NN=CC=2C=1NC(=O)NC(C1=CC=CC=C11)CCN1CC1=CC=CC=C1 CVNOORHKMWKCEI-UHFFFAOYSA-N 0.000 claims description 5
• LNCRGVMWIDSWDZ-UHFFFAOYSA-N 1-(1-benzyl-6-tert-butyl-3,4-dihydro-2h-quinolin-3-yl)-3-(1h-indazol-4-yl)urea Chemical compound C1C(NC(=O)NC=2C=3C=NNC=3C=CC=2)CC2=CC(C(C)(C)C)=CC=C2N1CC1=CC=CC=C1 LNCRGVMWIDSWDZ-UHFFFAOYSA-N 0.000 claims description 5
• ADEBLLBBBCQCDI-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-(1-methyl-3,4-dihydro-2h-quinolin-4-yl)urea Chemical compound C12=CC=CC=C2N(C)CCC1NC(=O)NC1=CC=CC2=C1C=NN2 ADEBLLBBBCQCDI-UHFFFAOYSA-N 0.000 claims description 5
• VKINZKIRILCDFD-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-(6-methyl-3,4-dihydro-2h-chromen-4-yl)urea Chemical compound C12=CC(C)=CC=C2OCCC1NC(=O)NC1=CC=CC2=C1C=NN2 VKINZKIRILCDFD-UHFFFAOYSA-N 0.000 claims description 5
• DRKFVZNNQBSDBF-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-(8-morpholin-4-yl-3,4-dihydro-2h-chromen-4-yl)urea Chemical compound C=1C=CC=2NN=CC=2C=1NC(=O)NC1CCOC2=C1C=CC=C2N1CCOCC1 DRKFVZNNQBSDBF-UHFFFAOYSA-N 0.000 claims description 5
• BWUZDTXKQFBCBM-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-(8-piperidin-1-yl-3,4-dihydro-2h-chromen-4-yl)urea Chemical compound C=1C=CC=2NN=CC=2C=1NC(=O)NC1CCOC2=C1C=CC=C2N1CCCCC1 BWUZDTXKQFBCBM-UHFFFAOYSA-N 0.000 claims description 5
• CHVBTEZXWRYVOG-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-[7-(trifluoromethoxy)-3,4-dihydro-2h-chromen-4-yl]urea Chemical compound C1COC2=CC(OC(F)(F)F)=CC=C2C1NC(=O)NC1=CC=CC2=C1C=NN2 CHVBTEZXWRYVOG-UHFFFAOYSA-N 0.000 claims description 5
• XKXJVTYDGSUSKI-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-[8-(trifluoromethoxy)-3,4-dihydro-2h-chromen-4-yl]urea Chemical compound C1COC=2C(OC(F)(F)F)=CC=CC=2C1NC(=O)NC1=CC=CC2=C1C=NN2 XKXJVTYDGSUSKI-UHFFFAOYSA-N 0.000 claims description 5
• CRCCQJDITKRXDH-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-[8-(trifluoromethyl)-3,4-dihydro-2h-chromen-4-yl]urea Chemical compound C1COC=2C(C(F)(F)F)=CC=CC=2C1NC(=O)NC1=CC=CC2=C1C=NN2 CRCCQJDITKRXDH-UHFFFAOYSA-N 0.000 claims description 5
• UMVFAVGJJHKXRM-UHFFFAOYSA-N 1-(2,3-dihydro-1-benzofuran-2-ylmethyl)-3-(1h-indazol-4-yl)urea Chemical compound C1C2=CC=CC=C2OC1CNC(=O)NC1=CC=CC2=C1C=NN2 UMVFAVGJJHKXRM-UHFFFAOYSA-N 0.000 claims description 5
• JCIVLZGCUOMREG-UHFFFAOYSA-N 1-(3,4-dihydro-2h-chromen-4-yl)-3-(1h-indazol-4-yl)urea Chemical compound C1COC2=CC=CC=C2C1NC(=O)NC1=CC=CC2=C1C=NN2 JCIVLZGCUOMREG-UHFFFAOYSA-N 0.000 claims description 5
• LRSVHBILTQOERP-UHFFFAOYSA-N 1-(6-chloro-7-methyl-3,4-dihydro-2h-chromen-4-yl)-3-(1h-indazol-4-yl)urea Chemical compound C1=2C=C(Cl)C(C)=CC=2OCCC1NC(=O)NC1=CC=CC2=C1C=NN2 LRSVHBILTQOERP-UHFFFAOYSA-N 0.000 claims description 5
• WDXRHDBNVFLNOA-UHFFFAOYSA-N 1-(6-fluoro-3,4-dihydro-2h-chromen-4-yl)-3-(1h-indazol-4-yl)urea Chemical compound C12=CC(F)=CC=C2OCCC1NC(=O)NC1=CC=CC2=C1C=NN2 WDXRHDBNVFLNOA-UHFFFAOYSA-N 0.000 claims description 5
• OMIRFNXDMYBLLF-UHFFFAOYSA-N 1-(7-tert-butyl-3,4-dihydro-2h-chromen-4-yl)-3-(1h-indazol-4-yl)urea Chemical compound C1COC2=CC(C(C)(C)C)=CC=C2C1NC(=O)NC1=CC=CC2=C1C=NN2 OMIRFNXDMYBLLF-UHFFFAOYSA-N 0.000 claims description 5
• CJHZOBWTVLHNPM-UHFFFAOYSA-N 1-(7-tert-butyl-3,4-dihydro-2h-chromen-4-yl)-3-quinolin-8-ylurea Chemical compound C1=CN=C2C(NC(=O)NC3C4=CC=C(C=C4OCC3)C(C)(C)C)=CC=CC2=C1 CJHZOBWTVLHNPM-UHFFFAOYSA-N 0.000 claims description 5
• NVMRZBHUMZFLEI-UHFFFAOYSA-N 1-(8-cyclohexyl-3,4-dihydro-2h-chromen-4-yl)-3-(1h-indazol-4-yl)urea Chemical compound C=1C=CC=2NN=CC=2C=1NC(=O)NC(C1=CC=C2)CCOC1=C2C1CCCCC1 NVMRZBHUMZFLEI-UHFFFAOYSA-N 0.000 claims description 5
• QMDUKTOFGWQLLH-UHFFFAOYSA-N 1-[1-benzyl-7-(trifluoromethoxy)-3,4-dihydro-2h-quinolin-3-yl]-3-(1h-indazol-4-yl)urea Chemical compound C12=CC(OC(F)(F)F)=CC=C2CC(NC(=O)NC=2C=3C=NNC=3C=CC=2)CN1CC1=CC=CC=C1 QMDUKTOFGWQLLH-UHFFFAOYSA-N 0.000 claims description 5
• OYIBXDLVXGTAGZ-UHFFFAOYSA-N 1-[[1-(cyclohexylmethyl)-3,4-dihydro-2h-quinolin-2-yl]methyl]-3-(1h-indazol-4-yl)urea Chemical compound C=1C=CC=2NN=CC=2C=1NC(=O)NCC1CCC2=CC=CC=C2N1CC1CCCCC1 OYIBXDLVXGTAGZ-UHFFFAOYSA-N 0.000 claims description 5
• OQDKWISVFFMYFI-UHFFFAOYSA-N 1-isoquinolin-5-yl-3-[[1-(2-phenylethyl)-3,4-dihydro-2h-quinolin-2-yl]methyl]urea Chemical compound C=1C=CC2=CN=CC=C2C=1NC(=O)NCC1CCC2=CC=CC=C2N1CCC1=CC=CC=C1 OQDKWISVFFMYFI-UHFFFAOYSA-N 0.000 claims description 5
• 125000000304 alkynyl group Chemical group 0.000 claims description 5
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
• JMWGHUKAPWWMPG-UHFFFAOYSA-N 1-(1-benzyl-3,4-dihydro-2h-quinolin-3-yl)-3-(1h-indazol-4-yl)urea Chemical compound C=1C=CC=2NN=CC=2C=1NC(=O)NC(CC1=CC=CC=C11)CN1CC1=CC=CC=C1 JMWGHUKAPWWMPG-UHFFFAOYSA-N 0.000 claims description 4
• FCWIBYQHRCBDSA-UHFFFAOYSA-N 1-(1-benzyl-6-fluoro-3,4-dihydro-2h-quinolin-4-yl)-3-(1h-indazol-4-yl)urea Chemical compound C1CC(NC(=O)NC=2C=3C=NNC=3C=CC=2)C2=CC(F)=CC=C2N1CC1=CC=CC=C1 FCWIBYQHRCBDSA-UHFFFAOYSA-N 0.000 claims description 4
• AYMSYYHWAONOKI-UHFFFAOYSA-N 1-(1-benzyl-6-methoxy-3,4-dihydro-2h-quinolin-4-yl)-3-(1h-indazol-4-yl)urea Chemical compound C1CC(NC(=O)NC=2C=3C=NNC=3C=CC=2)C2=CC(OC)=CC=C2N1CC1=CC=CC=C1 AYMSYYHWAONOKI-UHFFFAOYSA-N 0.000 claims description 4
• SFXDORUIZFRXSG-UHFFFAOYSA-N 1-(1-benzyl-6-tert-butyl-3,4-dihydro-2h-quinolin-4-yl)-3-(1h-indazol-4-yl)urea Chemical compound C1CC(NC(=O)NC=2C=3C=NNC=3C=CC=2)C2=CC(C(C)(C)C)=CC=C2N1CC1=CC=CC=C1 SFXDORUIZFRXSG-UHFFFAOYSA-N 0.000 claims description 4
• ITFPFVZGWFKJMG-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-[1-methyl-7-(trifluoromethyl)-3,4-dihydro-2h-quinolin-4-yl]urea Chemical compound C12=CC=C(C(F)(F)F)C=C2N(C)CCC1NC(=O)NC1=CC=CC2=C1C=NN2 ITFPFVZGWFKJMG-UHFFFAOYSA-N 0.000 claims description 4
• BSWNUMOXKJBAEC-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-[[1-(3-phenylpropyl)-3,4-dihydro-2h-quinolin-2-yl]methyl]urea Chemical compound C=1C=CC=2NN=CC=2C=1NC(=O)NCC1CCC2=CC=CC=C2N1CCCC1=CC=CC=C1 BSWNUMOXKJBAEC-UHFFFAOYSA-N 0.000 claims description 4
• XFXAXIXVJKIEKT-UHFFFAOYSA-N 1-[1-(cyclohexylmethyl)-6-methoxy-3,4-dihydro-2h-quinolin-4-yl]-3-(1h-indazol-4-yl)urea Chemical compound C1CC(NC(=O)NC=2C=3C=NNC=3C=CC=2)C2=CC(OC)=CC=C2N1CC1CCCCC1 XFXAXIXVJKIEKT-UHFFFAOYSA-N 0.000 claims description 4
• RMURSGKDSRERHP-UHFFFAOYSA-N 1-[7-(3,3-dimethylbutyl)-1-methyl-3,4-dihydro-2h-quinolin-4-yl]-3-(1h-indazol-4-yl)urea Chemical compound C12=CC=C(CCC(C)(C)C)C=C2N(C)CCC1NC(=O)NC1=CC=CC2=C1C=NN2 RMURSGKDSRERHP-UHFFFAOYSA-N 0.000 claims description 4
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