JP2008532925A5 - - Google Patents
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- JP2008532925A5 JP2008532925A5 JP2007543471A JP2007543471A JP2008532925A5 JP 2008532925 A5 JP2008532925 A5 JP 2008532925A5 JP 2007543471 A JP2007543471 A JP 2007543471A JP 2007543471 A JP2007543471 A JP 2007543471A JP 2008532925 A5 JP2008532925 A5 JP 2008532925A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- indazol
- dihydro
- chromen
- ylurea
- 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.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims 89
- 150000001875 compounds Chemical class 0.000 claims 41
- 125000001424 substituent group Chemical group 0.000 claims 18
- 125000001188 haloalkyl group Chemical group 0.000 claims 17
- 229910052739 hydrogen Inorganic materials 0.000 claims 16
- 239000001257 hydrogen Substances 0.000 claims 16
- 125000003342 alkenyl group Chemical group 0.000 claims 14
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 13
- 125000001072 heteroaryl group Chemical group 0.000 claims 11
- 150000002431 hydrogen Chemical class 0.000 claims 11
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 9
- 208000035475 disorder Diseases 0.000 claims 9
- 239000008194 pharmaceutical composition Substances 0.000 claims 8
- 125000003118 aryl group Chemical group 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000004438 haloalkoxy group Chemical group 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- -1 —OR c Chemical group 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 208000002193 Pain Diseases 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 5
- 125000002619 bicyclic group Chemical group 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 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 3
- 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 3
- 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 3
- 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 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 3
- 239000004202 carbamide Substances 0.000 claims 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 3
- MASAFVZAJXRZCN-UHFFFAOYSA-N 1-(7-tert-butyl-3,4-dihydro-2h-chromen-4-yl)-3-(3-methylisoquinolin-5-yl)urea Chemical compound C1COC2=CC(C(C)(C)C)=CC=C2C1NC(=O)NC1=C2C=C(C)N=CC2=CC=C1 MASAFVZAJXRZCN-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- 206010020751 Hypersensitivity Diseases 0.000 claims 2
- 206010065390 Inflammatory pain Diseases 0.000 claims 2
- NPRMHFLQUOEODW-UHFFFAOYSA-N OC(=O)n1ncc2c(NC(=O)NC3CN(Cc4ccccc4)c4cc(F)ccc4C3)cccc12 Chemical compound OC(=O)n1ncc2c(NC(=O)NC3CN(Cc4ccccc4)c4cc(F)ccc4C3)cccc12 NPRMHFLQUOEODW-UHFFFAOYSA-N 0.000 claims 2
- 108010025083 TRPV1 receptor Proteins 0.000 claims 2
- 102100029613 Transient receptor potential cation channel subfamily V member 1 Human genes 0.000 claims 2
- 206010046543 Urinary incontinence Diseases 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
- 208000026935 allergic disease Diseases 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 230000009610 hypersensitivity Effects 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 230000003349 osteoarthritic effect Effects 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- YHBYJDDRADGNLJ-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinolin-2-ylmethylurea Chemical compound N1C(CCC2=CC=CC=C12)CNC(N)=O YHBYJDDRADGNLJ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- JTXYTPNMHVUMPB-UHFFFAOYSA-N 1-(1-ethylindazol-4-yl)-3-(7-fluoro-2,2-dimethyl-3,4-dihydrochromen-4-yl)urea Chemical compound C1C(C)(C)OC2=CC(F)=CC=C2C1NC(=O)NC1=C2C=NN(CC)C2=CC=C1 JTXYTPNMHVUMPB-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- WXWCVKMJZSOKCO-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-(7-methoxy-2-phenyl-3,4-dihydro-2h-chromen-4-yl)urea Chemical compound O1C2=CC(OC)=CC=C2C(NC(=O)NC=2C=3C=NNC=3C=CC=2)CC1C1=CC=CC=C1 WXWCVKMJZSOKCO-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- POLTYCBJHGMTBT-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-[1-(3-phenylpropyl)-7-(trifluoromethyl)-3,4-dihydro-2h-quinolin-3-yl]urea Chemical compound C12=CC(C(F)(F)F)=CC=C2CC(NC(=O)NC=2C=3C=NNC=3C=CC=2)CN1CCCC1=CC=CC=C1 POLTYCBJHGMTBT-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- HHBRVBWBJRXBFF-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-[[1-(pyridin-2-ylmethyl)-3,4-dihydro-2h-quinolin-2-yl]methyl]urea Chemical compound C=1C=CC=2NN=CC=2C=1NC(=O)NCC1CCC2=CC=CC=C2N1CC1=CC=CC=N1 HHBRVBWBJRXBFF-UHFFFAOYSA-N 0.000 claims 1
- NLELPKGKSYREII-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-[[1-(trifluoromethylsulfonyl)-3,4-dihydro-2h-quinolin-2-yl]methyl]urea Chemical compound C1CC2=CC=CC=C2N(S(=O)(=O)C(F)(F)F)C1CNC(=O)NC1=CC=CC2=C1C=NN2 NLELPKGKSYREII-UHFFFAOYSA-N 0.000 claims 1
- NHWCANILDANDRT-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-[[1-[[2-(trifluoromethyl)phenyl]methyl]-3,4-dihydro-2h-quinolin-2-yl]methyl]urea Chemical compound FC(F)(F)C1=CC=CC=C1CN1C2=CC=CC=C2CCC1CNC(=O)NC1=CC=CC2=C1C=NN2 NHWCANILDANDRT-UHFFFAOYSA-N 0.000 claims 1
- UBUYYVLKHWWBOU-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-[[1-[[4-(trifluoromethyl)phenyl]methyl]-3,4-dihydro-2h-quinolin-2-yl]methyl]urea Chemical compound C1=CC(C(F)(F)F)=CC=C1CN1C2=CC=CC=C2CCC1CNC(=O)NC1=CC=CC2=C1C=NN2 UBUYYVLKHWWBOU-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- MMSMTMQGZFFWET-UHFFFAOYSA-N 1-(2,2-diethyl-7-fluoro-3,4-dihydrochromen-4-yl)-3-(1-methylindazol-4-yl)urea Chemical compound C12=CC=C(F)C=C2OC(CC)(CC)CC1NC(=O)NC1=CC=CC2=C1C=NN2C MMSMTMQGZFFWET-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- GYTCPWPDOHESAY-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-3-ylmethyl)-3-(1h-indazol-4-yl)urea Chemical compound C1OC2=CC=CC=C2OC1CNC(=O)NC1=CC=CC2=C1C=NN2 GYTCPWPDOHESAY-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- HNYUSGJGGMMXFW-UHFFFAOYSA-N 1-(2-ethylindazol-4-yl)-3-(7-fluoro-2,2-dimethyl-3,4-dihydrochromen-4-yl)urea Chemical compound C1C(C)(C)OC2=CC(F)=CC=C2C1NC(=O)NC1=CC=CC2=NN(CC)C=C21 HNYUSGJGGMMXFW-UHFFFAOYSA-N 0.000 claims 1
- BUGPFPKBJAUVIJ-UHFFFAOYSA-N 1-(2-tert-butyl-7-fluoro-3,4-dihydro-2h-chromen-4-yl)-3-(1-methylindazol-4-yl)urea Chemical compound C1C(C(C)(C)C)OC2=CC(F)=CC=C2C1NC(=O)NC1=C2C=NN(C)C2=CC=C1 BUGPFPKBJAUVIJ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- NADXNPJWRMMDRM-UHFFFAOYSA-N 1-(3,4-dihydro-2h-1,4-benzoxazin-2-ylmethyl)-3-(1h-indazol-4-yl)urea Chemical compound C1NC2=CC=CC=C2OC1CNC(=O)NC1=CC=CC2=C1C=NN2 NADXNPJWRMMDRM-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- KNVHRZOGCSRXTA-UHFFFAOYSA-N 1-(3,4-dihydro-2h-chromen-3-yl)-3-isoquinolin-5-ylurea Chemical compound N1=CC=C2C(NC(NC3CC4=CC=CC=C4OC3)=O)=CC=CC2=C1 KNVHRZOGCSRXTA-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- VQJCSJIAIWNJSO-UHFFFAOYSA-N 1-(6-chloro-7-methyl-3,4-dihydro-2h-chromen-4-yl)-3-isoquinolin-5-ylurea Chemical compound N1=CC=C2C(NC(=O)NC3CCOC=4C=C(C(=CC=43)Cl)C)=CC=CC2=C1 VQJCSJIAIWNJSO-UHFFFAOYSA-N 0.000 claims 1
- MJMAJBXEOLLLDS-UHFFFAOYSA-N 1-(6-chloro-7-methyl-3,4-dihydro-2h-chromen-4-yl)-3-quinolin-5-ylurea Chemical compound C1=CC=C2C(NC(=O)NC3CCOC=4C=C(C(=CC=43)Cl)C)=CC=CC2=N1 MJMAJBXEOLLLDS-UHFFFAOYSA-N 0.000 claims 1
- GMGYJBTXGBSQGB-UHFFFAOYSA-N 1-(6-fluoro-2-methyl-3,4-dihydro-2h-chromen-4-yl)-3-(1h-indazol-4-yl)urea Chemical compound C12=CC(F)=CC=C2OC(C)CC1NC(=O)NC1=CC=CC2=C1C=NN2 GMGYJBTXGBSQGB-UHFFFAOYSA-N 0.000 claims 1
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| NZ (1) | NZ555318A (enExample) |
| TW (1) | TW200633712A (enExample) |
| WO (1) | WO2006065484A2 (enExample) |
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| WO2008110863A1 (en) * | 2007-03-15 | 2008-09-18 | Glenmark Pharmaceuticals S.A. | Indazole derivatives and their use as vanilloid receptor ligands |
| JP5562865B2 (ja) | 2007-12-17 | 2014-07-30 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | Ｔｒｐｖ１のイミダゾロ−、オキサゾロ−、及びチアゾロピリミジン・モジュレーター |
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| EP2310918B1 (en) * | 2008-06-17 | 2014-10-08 | Rosemount, Inc. | Rf adapter for field device with variable voltage drop |
| US8929948B2 (en) | 2008-06-17 | 2015-01-06 | Rosemount Inc. | Wireless communication adapter for field devices |
| US8694060B2 (en) | 2008-06-17 | 2014-04-08 | Rosemount Inc. | Form factor and electromagnetic interference protection for process device wireless adapters |
| WO2010023512A1 (en) * | 2008-08-28 | 2010-03-04 | Matrix Laboratories Ltd. | Novel vanilloid receptor modulators, process for their preparation and pharmaceutical compositions containing them |
| UY32180A (es) * | 2008-10-17 | 2010-05-31 | Abbott Lab | Antagonistas del receptor transitorio potencial de vanilloides 1 (trpv1) |
| US8609692B2 (en) * | 2008-10-17 | 2013-12-17 | Abbvie Inc. | TRPV1 antagonists |
| US8349852B2 (en) | 2009-01-13 | 2013-01-08 | Novartis Ag | Quinazolinone derivatives useful as vanilloid antagonists |
| CN101654435B (zh) * | 2009-06-09 | 2014-01-29 | 沈阳药科大学 | N-苯甲基喹啉羧酸类化合物、组合物及其制备方法 |
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| US9674976B2 (en) | 2009-06-16 | 2017-06-06 | Rosemount Inc. | Wireless process communication adapter with improved encapsulation |
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| US8598156B2 (en) | 2010-03-25 | 2013-12-03 | Glaxosmithkline Llc | Chemical compounds |
| US10761524B2 (en) | 2010-08-12 | 2020-09-01 | Rosemount Inc. | Wireless adapter with process diagnostics |
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| US9310794B2 (en) | 2011-10-27 | 2016-04-12 | Rosemount Inc. | Power supply for industrial process field device |
| US8969325B2 (en) | 2011-12-19 | 2015-03-03 | Abbvie Inc. | TRPV1 antagonists |
| US8859584B2 (en) | 2011-12-19 | 2014-10-14 | Abbvie, Inc. | TRPV1 antagonists |
| US8796328B2 (en) | 2012-06-20 | 2014-08-05 | Abbvie Inc. | TRPV1 antagonists |
| CN103739547B (zh) * | 2014-01-03 | 2015-09-02 | 沈阳药科大学 | 2-[6-甲氧基-3-(2,3-二氯苯基)甲基-4-氧代-1,4-二氢-1(4h)-喹啉基]乙酸的合成方法 |
| US9783527B2 (en) * | 2014-09-16 | 2017-10-10 | Abbvie Inc. | Indazole ureas and method of use |
| CN109574972A (zh) * | 2018-07-13 | 2019-04-05 | 郑州大学 | 一种3-烷基取代-4-色满酮类化合物及其制备方法 |
| AR123656A1 (es) * | 2020-09-30 | 2022-12-28 | Univ Leuven Kath | Derivados de 1,2,3,4-tetrahidroquinolina |
| CN120398870A (zh) * | 2024-01-31 | 2025-08-01 | 深圳晶蛋生物医药科技有限公司 | 一种苯并吗啉类化合物及其应用 |
| WO2026134866A1 (ko) * | 2024-12-20 | 2026-06-25 | 고려대학교 산학협력단 | 신규한 크로멘-벤즈이미다졸 유도체 또는 이의 약학적으로 허용가능한 염 및 이의 용도 |
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| NL8900565A (nl) | 1989-03-08 | 1990-10-01 | Philips Nv | Methode voor de verwerking van een radio data signaal, alsmede ontvanger voor de uitvoering van deze methode. |
| IL93610A0 (en) * | 1989-03-08 | 1990-12-23 | Merck Sharp & Dohme | Tetrahydroquinoline derivatives,their preparation and pharmaceutical compositions containing them |
| US5374643A (en) | 1992-09-11 | 1994-12-20 | E. R. Squibb & Sons, Inc. | Aryl urea (thiourea) and cyanoguanidine derivatives |
| JP2000516958A (ja) * | 1996-08-26 | 2000-12-19 | ジェネティックス・インスチチュート・インコーポレーテッド | ホスホリパーゼ酵素の阻害剤 |
| ES2292488T3 (es) * | 1999-11-16 | 2008-03-16 | Boehringer Ingelheim Pharmaceuticals Inc. | Derivados de la urea, como agentes antiinflamatorios. |
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| CN102161653A (zh) * | 2004-11-24 | 2011-08-24 | 雅培制药有限公司 | 抑制香草素受体亚型1(vr1)受体的苯并二氢吡喃基脲化合物及其用途 |
| AU2006306146A1 (en) * | 2005-10-28 | 2007-05-03 | Abbott Laboratories | Indazole derivatives that inhibit TRPV1 receptor |
-
2005
- 2005-11-22 CN CN2011100508496A patent/CN102161653A/zh active Pending
- 2005-11-22 NZ NZ555318A patent/NZ555318A/en not_active IP Right Cessation
- 2005-11-22 CA CA002588909A patent/CA2588909A1/en not_active Abandoned
- 2005-11-22 CN CNA2005800467732A patent/CN101443327A/zh active Pending
- 2005-11-22 KR KR1020077014371A patent/KR101250824B1/ko not_active Expired - Fee Related
- 2005-11-22 EP EP05825417A patent/EP1844038A2/en not_active Withdrawn
- 2005-11-22 WO PCT/US2005/042545 patent/WO2006065484A2/en not_active Ceased
- 2005-11-22 US US11/285,448 patent/US7812019B2/en not_active Expired - Fee Related
- 2005-11-22 MX MX2007006205A patent/MX2007006205A/es active IP Right Grant
- 2005-11-22 JP JP2007543471A patent/JP4932730B2/ja not_active Expired - Fee Related
- 2005-11-22 BR BRPI0518581-5A patent/BRPI0518581A2/pt not_active IP Right Cessation
- 2005-11-22 KR KR1020127028557A patent/KR20120137420A/ko not_active Withdrawn
- 2005-11-22 AU AU2005316972A patent/AU2005316972B2/en not_active Ceased
- 2005-11-22 EP EP12181173A patent/EP2527339A1/en not_active Withdrawn
- 2005-11-24 TW TW094141323A patent/TW200633712A/zh unknown
-
2007
- 2007-05-20 IL IL183321A patent/IL183321A0/en unknown
-
2010
- 2010-09-03 US US12/875,839 patent/US8440691B2/en not_active Expired - Fee Related
-
2012
- 2012-01-11 JP JP2012003232A patent/JP2012111766A/ja active Pending
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