ES2318308T3 - Compuestos fusionados que inhiben el receptor (vr1) subtipo 1 de receptores vainilloides. - Google Patents

Info

Publication number

ES2318308T3

ES2318308T3 ES04754996T ES04754996T ES2318308T3 ES 2318308 T3 ES2318308 T3 ES 2318308T3 ES 04754996 T ES04754996 T ES 04754996T ES 04754996 T ES04754996 T ES 04754996T ES 2318308 T3 ES2318308 T3 ES 2318308T3

Authority

ES

Spain

Prior art keywords

compound

formula

dihydro

inden

indazol

Prior art date

2003-06-12

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 - Lifetime

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 648
• 238000000034 method Methods 0.000 claims abstract description 127
• 150000003839 salts Chemical class 0.000 claims abstract description 55
• 241000124008 Mammalia Species 0.000 claims abstract description 23
• 230000036407 pain Effects 0.000 claims abstract description 19
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 14
• 208000004454 Hyperalgesia Diseases 0.000 claims abstract description 11
• 208000035154 Hyperesthesia Diseases 0.000 claims abstract description 9
• 206010046543 Urinary incontinence Diseases 0.000 claims abstract description 9
• 230000002757 inflammatory effect Effects 0.000 claims abstract description 9
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 372
• -1 carboxy, carboxy Chemical group 0.000 claims description 253
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 225
• 239000002253 acid Substances 0.000 claims description 119
• 239000000203 mixture Substances 0.000 claims description 117
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 109
• 125000000217 alkyl group Chemical group 0.000 claims description 103
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 99
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 98
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 90
• 229910052739 hydrogen Inorganic materials 0.000 claims description 90
• 239000001257 hydrogen Substances 0.000 claims description 90
• 239000002904 solvent Substances 0.000 claims description 73
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 62
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 50
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 50
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 45
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 32
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
• 229910052736 halogen Inorganic materials 0.000 claims description 31
• 125000003545 alkoxy group Chemical group 0.000 claims description 30
• 150000002367 halogens Chemical class 0.000 claims description 30
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 29
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 28
• 125000003118 aryl group Chemical group 0.000 claims description 26
• 238000002360 preparation method Methods 0.000 claims description 26
• 238000011282 treatment Methods 0.000 claims description 24
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 23
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 22
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 22
• 125000001188 haloalkyl group Chemical group 0.000 claims description 22
• 239000012298 atmosphere Substances 0.000 claims description 21
• 125000004966 cyanoalkyl group Chemical group 0.000 claims description 20
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 20
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 19
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 19
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 18
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 18
• 238000004519 manufacturing process Methods 0.000 claims description 18
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 17
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 17
• 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 16
• 239000003814 drug Substances 0.000 claims description 16
• 125000000623 heterocyclic group Chemical group 0.000 claims description 16
• 238000003756 stirring Methods 0.000 claims description 16
• 125000005243 carbonyl alkyl group Chemical group 0.000 claims description 15
• 125000003342 alkenyl group Chemical group 0.000 claims description 14
• 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 14
• 125000004414 alkyl thio group Chemical group 0.000 claims description 14
• 125000000304 alkynyl group Chemical group 0.000 claims description 14
• 239000004202 carbamide Substances 0.000 claims description 14
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
• 108010062740 TRPV Cation Channels Proteins 0.000 claims description 13
• 102000011040 TRPV Cation Channels Human genes 0.000 claims description 13
• 125000005093 alkyl carbonyl alkyl group Chemical group 0.000 claims description 13
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
• 208000035475 disorder Diseases 0.000 claims description 13
• 125000004995 haloalkylthio group Chemical group 0.000 claims description 13
• 125000005358 mercaptoalkyl group Chemical group 0.000 claims description 13
• QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 13
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
• 229940079593 drug Drugs 0.000 claims description 12
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
• 229910052757 nitrogen Inorganic materials 0.000 claims description 12
• VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 11
• 125000004967 formylalkyl group Chemical group 0.000 claims description 11
• 229910052763 palladium Inorganic materials 0.000 claims description 11
• 235000010288 sodium nitrite Nutrition 0.000 claims description 10
• YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 claims description 10
• 210000003932 urinary bladder Anatomy 0.000 claims description 10
• 229910052799 carbon Inorganic materials 0.000 claims description 9
• 238000010438 heat treatment Methods 0.000 claims description 8
• XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 claims description 8
• 239000012279 sodium borohydride Substances 0.000 claims description 8
• 229910000033 sodium borohydride Inorganic materials 0.000 claims description 8
• VPSCJCQPUGKRNC-UHFFFAOYSA-N 1-(5-tert-butyl-2,3-dihydro-1h-inden-1-yl)-3-isoquinolin-5-ylurea Chemical compound N1=CC=C2C(NC(=O)NC3C4=CC=C(C=C4CC3)C(C)(C)C)=CC=CC2=C1 VPSCJCQPUGKRNC-UHFFFAOYSA-N 0.000 claims description 7
• TYOYXJNGINZFET-GOSISDBHSA-N 1-[(1r)-5-tert-butyl-2,3-dihydro-1h-inden-1-yl]-3-(1h-indazol-4-yl)urea Chemical compound N([C@H]1C2=CC=C(C=C2CC1)C(C)(C)C)C(=O)NC1=CC=CC2=C1C=NN2 TYOYXJNGINZFET-GOSISDBHSA-N 0.000 claims description 7
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 7
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
• ZQOHBQZZPJFTBS-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-(4-piperidin-1-yl-2,3-dihydro-1h-inden-1-yl)urea Chemical compound C=1C=CC=2NN=CC=2C=1NC(=O)NC1CCC2=C1C=CC=C2N1CCCCC1 ZQOHBQZZPJFTBS-UHFFFAOYSA-N 0.000 claims description 6
• FGZOWQBNDORKQL-UHFFFAOYSA-N 1-[5-(2-cyanopropan-2-yl)-2,3-dihydro-1h-inden-1-yl]-3-(1h-indazol-4-yl)urea Chemical compound C1CC2=CC(C(C)(C#N)C)=CC=C2C1NC(=O)NC1=CC=CC2=C1C=NN2 FGZOWQBNDORKQL-UHFFFAOYSA-N 0.000 claims description 6
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 6
• 238000000605 extraction Methods 0.000 claims description 6
• 125000001072 heteroaryl group Chemical group 0.000 claims description 6
• PCUDEEPQUVIGBR-UHFFFAOYSA-N 1-(4,5-dimethoxy-2,3-dihydro-1h-inden-1-yl)-3-(1h-indazol-4-yl)urea Chemical compound C1CC2=C(OC)C(OC)=CC=C2C1NC(=O)NC1=CC=CC2=C1C=NN2 PCUDEEPQUVIGBR-UHFFFAOYSA-N 0.000 claims description 5
• UJHPWLQNPUIFJU-UHFFFAOYSA-N 1-(5-tert-butyl-2,3-dihydro-1h-inden-1-yl)-3-(3-methylisoquinolin-5-yl)urea Chemical compound C1CC2=CC(C(C)(C)C)=CC=C2C1NC(=O)NC1=C2C=C(C)N=CC2=CC=C1 UJHPWLQNPUIFJU-UHFFFAOYSA-N 0.000 claims description 5
• 125000002757 morpholinyl group Chemical group 0.000 claims description 5
• 125000004193 piperazinyl group Chemical group 0.000 claims description 5
• 125000003386 piperidinyl group Chemical group 0.000 claims description 5
• 125000004076 pyridyl group Chemical group 0.000 claims description 5
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
• ZBISBOUCIVCJOF-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-(5-methoxy-2,3-dihydro-1h-inden-1-yl)urea Chemical compound C1CC2=CC(OC)=CC=C2C1NC(=O)NC1=CC=CC2=C1C=NN2 ZBISBOUCIVCJOF-UHFFFAOYSA-N 0.000 claims description 4
• SVYGRCSOIPQXGO-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-(5-piperidin-1-yl-2,3-dihydro-1h-inden-1-yl)urea Chemical compound C=1C=CC=2NN=CC=2C=1NC(=O)NC(C1=CC=2)CCC1=CC=2N1CCCCC1 SVYGRCSOIPQXGO-UHFFFAOYSA-N 0.000 claims description 4
• XBOINVGXFLCYNR-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-[4-(4-methylpiperidin-1-yl)-2,3-dihydro-1h-inden-1-yl]urea Chemical compound C1CC(C)CCN1C1=CC=CC2=C1CCC2NC(=O)NC1=CC=CC2=C1C=NN2 XBOINVGXFLCYNR-UHFFFAOYSA-N 0.000 claims description 4
• YCAAQLHPLMLUQY-UHFFFAOYSA-N 1-(5,6-dimethoxy-2,3-dihydro-1h-inden-1-yl)-3-(1h-indazol-4-yl)urea Chemical compound C1=2C=C(OC)C(OC)=CC=2CCC1NC(=O)NC1=CC=CC2=C1C=NN2 YCAAQLHPLMLUQY-UHFFFAOYSA-N 0.000 claims description 4
• 125000004429 atom Chemical group 0.000 claims description 4
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 4
• UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 4
• 125000005961 oxazepanyl group Chemical group 0.000 claims description 4
• PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 4
• ASHXOMOCDINDTE-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-(4-morpholin-4-yl-2,3-dihydro-1h-inden-1-yl)urea Chemical compound C=1C=CC=2NN=CC=2C=1NC(=O)NC1CCC2=C1C=CC=C2N1CCOCC1 ASHXOMOCDINDTE-UHFFFAOYSA-N 0.000 claims description 3
• PKVCREBZFWTVRQ-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-(4-pyridin-2-yl-2,3-dihydro-1h-inden-1-yl)urea Chemical compound C=1C=CC=2NN=CC=2C=1NC(=O)NC1CCC2=C1C=CC=C2C1=CC=CC=N1 PKVCREBZFWTVRQ-UHFFFAOYSA-N 0.000 claims description 3
• UIIWXLYPGXOGTO-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-(4-pyridin-3-yl-2,3-dihydro-1h-inden-1-yl)urea Chemical compound C=1C=CC=2NN=CC=2C=1NC(=O)NC1CCC2=C1C=CC=C2C1=CC=CN=C1 UIIWXLYPGXOGTO-UHFFFAOYSA-N 0.000 claims description 3
• OYQRPDVQQSMHBP-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-(4-pyridin-4-yl-2,3-dihydro-1h-inden-1-yl)urea Chemical compound C=1C=CC=2NN=CC=2C=1NC(=O)NC1CCC2=C1C=CC=C2C1=CC=NC=C1 OYQRPDVQQSMHBP-UHFFFAOYSA-N 0.000 claims description 3
• UOHCGMBECWOBEU-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-(4-pyrrolidin-1-yl-2,3-dihydro-1h-inden-1-yl)urea Chemical compound C=1C=CC=2NN=CC=2C=1NC(=O)NC1CCC2=C1C=CC=C2N1CCCC1 UOHCGMBECWOBEU-UHFFFAOYSA-N 0.000 claims description 3
• YPTLZNNIGSSJPU-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-(5-methyl-2,3-dihydro-1h-inden-1-yl)urea Chemical compound C1CC2=CC(C)=CC=C2C1NC(=O)NC1=CC=CC2=C1C=NN2 YPTLZNNIGSSJPU-UHFFFAOYSA-N 0.000 claims description 3
• VEHLEPIVJNKFAH-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-(5-propan-2-yl-2,3-dihydro-1h-inden-1-yl)urea Chemical compound C1CC2=CC(C(C)C)=CC=C2C1NC(=O)NC1=CC=CC2=C1C=NN2 VEHLEPIVJNKFAH-UHFFFAOYSA-N 0.000 claims description 3
• HESYILDXDKYKKC-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-(6-methoxy-2,3-dihydro-1h-inden-1-yl)urea Chemical compound C12=CC(OC)=CC=C2CCC1NC(=O)NC1=CC=CC2=C1C=NN2 HESYILDXDKYKKC-UHFFFAOYSA-N 0.000 claims description 3
• ICPVUQZAKSTNQF-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-(6-methyl-2,3-dihydro-1h-inden-1-yl)urea Chemical compound C12=CC(C)=CC=C2CCC1NC(=O)NC1=CC=CC2=C1C=NN2 ICPVUQZAKSTNQF-UHFFFAOYSA-N 0.000 claims description 3
• QDWZACMXOZMDBC-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-(7-methyl-2,3-dihydro-1h-inden-1-yl)urea Chemical compound C1=2C(C)=CC=CC=2CCC1NC(=O)NC1=CC=CC2=C1C=NN2 QDWZACMXOZMDBC-UHFFFAOYSA-N 0.000 claims description 3
• JCWHPUARHCLHRE-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-[4-(2-methylpyrrolidin-1-yl)-2,3-dihydro-1h-inden-1-yl]urea Chemical compound CC1CCCN1C1=CC=CC2=C1CCC2NC(=O)NC1=CC=CC2=C1C=NN2 JCWHPUARHCLHRE-UHFFFAOYSA-N 0.000 claims description 3
• PLURPZUDSOIBDO-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-[4-(4-methylpiperazin-1-yl)-2,3-dihydro-1h-inden-1-yl]urea Chemical compound C1CN(C)CCN1C1=CC=CC2=C1CCC2NC(=O)NC1=CC=CC2=C1C=NN2 PLURPZUDSOIBDO-UHFFFAOYSA-N 0.000 claims description 3
• SQKBVJVKOIQJGQ-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-[4-(trifluoromethoxy)-2,3-dihydro-1h-inden-1-yl]urea Chemical compound C1CC=2C(OC(F)(F)F)=CC=CC=2C1NC(=O)NC1=CC=CC2=C1C=NN2 SQKBVJVKOIQJGQ-UHFFFAOYSA-N 0.000 claims description 3
• KJRJYJCHGDZPPX-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-[5-(1-methoxy-2-methylpropan-2-yl)-2,3-dihydro-1h-inden-1-yl]urea Chemical compound C1CC2=CC(C(C)(C)COC)=CC=C2C1NC(=O)NC1=CC=CC2=C1C=NN2 KJRJYJCHGDZPPX-UHFFFAOYSA-N 0.000 claims description 3
• NBBJYIVJMJCFCE-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-[5-(2-methylpiperidin-1-yl)-2,3-dihydro-1h-inden-1-yl]urea Chemical compound CC1CCCCN1C1=CC=C(C(CC2)NC(=O)NC=3C=4C=NNC=4C=CC=3)C2=C1 NBBJYIVJMJCFCE-UHFFFAOYSA-N 0.000 claims description 3
• PNBWVYYXZCLQRU-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-[5-(3-methylpiperidin-1-yl)-2,3-dihydro-1h-inden-1-yl]urea Chemical compound C1C(C)CCCN1C1=CC=C(C(CC2)NC(=O)NC=3C=4C=NNC=4C=CC=3)C2=C1 PNBWVYYXZCLQRU-UHFFFAOYSA-N 0.000 claims description 3
• QQSNYWRELALBNA-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-[5-(4-methylpiperidin-1-yl)-2,3-dihydro-1h-inden-1-yl]urea Chemical compound C1CC(C)CCN1C1=CC=C(C(CC2)NC(=O)NC=3C=4C=NNC=4C=CC=3)C2=C1 QQSNYWRELALBNA-UHFFFAOYSA-N 0.000 claims description 3
• UKSFKXHTHRJUIA-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-[5-(4-phenylpiperazin-1-yl)-2,3-dihydro-1h-inden-1-yl]urea Chemical compound C=1C=CC=2NN=CC=2C=1NC(=O)NC(C1=CC=2)CCC1=CC=2N(CC1)CCN1C1=CC=CC=C1 UKSFKXHTHRJUIA-UHFFFAOYSA-N 0.000 claims description 3
• GHAQCPBCRKBIGN-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-[5-(4-phenylpiperidin-1-yl)-2,3-dihydro-1h-inden-1-yl]urea Chemical compound C=1C=CC=2NN=CC=2C=1NC(=O)NC(C1=CC=2)CCC1=CC=2N(CC1)CCC1C1=CC=CC=C1 GHAQCPBCRKBIGN-UHFFFAOYSA-N 0.000 claims description 3
• RZFOJZILWOUWLX-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-[5-(4-piperidin-1-ylpiperidin-1-yl)-2,3-dihydro-1h-inden-1-yl]urea Chemical compound C=1C=CC=2NN=CC=2C=1NC(=O)NC(C1=CC=2)CCC1=CC=2N(CC1)CCC1N1CCCCC1 RZFOJZILWOUWLX-UHFFFAOYSA-N 0.000 claims description 3
• WFTZESZPFIQNRC-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-[5-[4-(trifluoromethyl)piperidin-1-yl]-2,3-dihydro-1h-inden-1-yl]urea Chemical compound C1CC(C(F)(F)F)CCN1C1=CC=C(C(CC2)NC(=O)NC=3C=4C=NNC=4C=CC=3)C2=C1 WFTZESZPFIQNRC-UHFFFAOYSA-N 0.000 claims description 3
• OUIHQJINQZAAFC-UHFFFAOYSA-N 1-(4-bromo-2,3-dihydro-1h-inden-1-yl)-3-(1h-indazol-4-yl)urea Chemical compound C1CC=2C(Br)=CC=CC=2C1NC(=O)NC1=CC=CC2=C1C=NN2 OUIHQJINQZAAFC-UHFFFAOYSA-N 0.000 claims description 3
• FCINXFUMHCCMJT-UHFFFAOYSA-N 1-(4-chloro-2,3-dihydro-1h-inden-1-yl)-3-(1h-indazol-4-yl)urea Chemical compound C1CC=2C(Cl)=CC=CC=2C1NC(=O)NC1=CC=CC2=C1C=NN2 FCINXFUMHCCMJT-UHFFFAOYSA-N 0.000 claims description 3
• DEHOJLUMBBKMOD-UHFFFAOYSA-N 1-(5-bromo-2,3-dihydro-1h-inden-1-yl)-3-isoquinolin-5-ylurea Chemical compound N1=CC=C2C(NC(=O)NC3C4=CC=C(C=C4CC3)Br)=CC=CC2=C1 DEHOJLUMBBKMOD-UHFFFAOYSA-N 0.000 claims description 3
• BGZQKFANVOPJDS-UHFFFAOYSA-N 1-(5-tert-butyl-2,2-difluoro-1,3-dihydroinden-1-yl)-3-(1h-indazol-4-yl)urea Chemical compound FC1(F)CC2=CC(C(C)(C)C)=CC=C2C1NC(=O)NC1=CC=CC2=C1C=NN2 BGZQKFANVOPJDS-UHFFFAOYSA-N 0.000 claims description 3
• TYOYXJNGINZFET-UHFFFAOYSA-N 1-(5-tert-butyl-2,3-dihydro-1h-inden-1-yl)-3-(1h-indazol-4-yl)urea Chemical compound C1CC2=CC(C(C)(C)C)=CC=C2C1NC(=O)NC1=CC=CC2=C1C=NN2 TYOYXJNGINZFET-UHFFFAOYSA-N 0.000 claims description 3
• JMWSQSYRBYDBND-UHFFFAOYSA-N 1-(5-tert-butyl-2,3-dihydro-1h-inden-2-yl)-3-(1h-indazol-4-yl)urea Chemical compound C1C2=CC(C(C)(C)C)=CC=C2CC1NC(=O)NC1=CC=CC2=C1C=NN2 JMWSQSYRBYDBND-UHFFFAOYSA-N 0.000 claims description 3
• GNRVWTIJRDMIID-UHFFFAOYSA-N 1-(5-tert-butyl-2-fluoro-2,3-dihydro-1h-inden-1-yl)-3-(1h-indazol-4-yl)urea Chemical compound FC1CC2=CC(C(C)(C)C)=CC=C2C1NC(=O)NC1=CC=CC2=C1C=NN2 GNRVWTIJRDMIID-UHFFFAOYSA-N 0.000 claims description 3
• NHEQTPFLJJJJKT-UHFFFAOYSA-N 1-(6-fluoro-2,3-dihydro-1h-inden-1-yl)-3-(1h-indazol-4-yl)urea Chemical compound C12=CC(F)=CC=C2CCC1NC(=O)NC1=CC=CC2=C1C=NN2 NHEQTPFLJJJJKT-UHFFFAOYSA-N 0.000 claims description 3
• NHZJKQDNRCCOFK-UHFFFAOYSA-N 1-(6-fluoro-5-piperidin-1-yl-2,3-dihydro-1h-inden-1-yl)-3-(1h-indazol-4-yl)urea Chemical compound FC1=CC=2C(NC(=O)NC=3C=4C=NNC=4C=CC=3)CCC=2C=C1N1CCCCC1 NHZJKQDNRCCOFK-UHFFFAOYSA-N 0.000 claims description 3
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