CA2462441A1 - 1,4-disubstituted benzo-fused urea compounds as cytokine inhibitors - Google Patents

Info

Publication number

CA2462441A1

CA2462441A1 CA002462441A CA2462441A CA2462441A1 CA 2462441 A1 CA2462441 A1 CA 2462441A1 CA 002462441 A CA002462441 A CA 002462441A CA 2462441 A CA2462441 A CA 2462441A CA 2462441 A1 CA2462441 A1 CA 2462441A1

Authority

CA

Canada

Prior art keywords

alkyl

phenyl

naphthalen

butyl

methoxy

Prior art date

2001-10-18

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 102000004127 Cytokines Human genes 0.000 title claims description 45
• 108090000695 Cytokines Proteins 0.000 title claims description 45
• 239000003112 inhibitor Substances 0.000 title description 11
• 150000003672 ureas Chemical class 0.000 title description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 106
• 238000000034 method Methods 0.000 claims abstract description 37
• 125000000217 alkyl group Chemical group 0.000 claims description 216
• -1 hydroxy, amino Chemical group 0.000 claims description 215
• 239000004202 carbamide Substances 0.000 claims description 67
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 58
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 48
• 201000010099 disease Diseases 0.000 claims description 42
• 125000000623 heterocyclic group Chemical group 0.000 claims description 41
• 125000001624 naphthyl group Chemical group 0.000 claims description 39
• 125000003545 alkoxy group Chemical group 0.000 claims description 37
• 239000002904 solvent Substances 0.000 claims description 34
• 125000002757 morpholinyl group Chemical group 0.000 claims description 33
• 125000004043 oxo group Chemical group O=* 0.000 claims description 33
• 125000004076 pyridyl group Chemical group 0.000 claims description 33
• 229910052739 hydrogen Inorganic materials 0.000 claims description 32
• 239000001257 hydrogen Substances 0.000 claims description 32
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 30
• 125000003118 aryl group Chemical group 0.000 claims description 28
• 150000002431 hydrogen Chemical class 0.000 claims description 28
• 229910020008 S(O) Inorganic materials 0.000 claims description 27
• 125000002252 acyl group Chemical group 0.000 claims description 27
• 125000004193 piperazinyl group Chemical group 0.000 claims description 25
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 24
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 23
• 229910052736 halogen Inorganic materials 0.000 claims description 23
• 150000002367 halogens Chemical class 0.000 claims description 22
• 125000001072 heteroaryl group Chemical group 0.000 claims description 22
• 229910052757 nitrogen Inorganic materials 0.000 claims description 22
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 19
• 125000002883 imidazolyl group Chemical group 0.000 claims description 19
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 19
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 19
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 19
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 19
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 19
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 19
• 229920006395 saturated elastomer Polymers 0.000 claims description 18
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 17
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
• 125000001041 indolyl group Chemical group 0.000 claims description 17
• 150000002825 nitriles Chemical class 0.000 claims description 17
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 17
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 17
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 17
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 17
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 17
• 229910052760 oxygen Inorganic materials 0.000 claims description 16
• 125000004432 carbon atom Chemical group C* 0.000 claims description 15
• 125000005843 halogen group Chemical group 0.000 claims description 15
• 208000014674 injury Diseases 0.000 claims description 14
• 230000001154 acute effect Effects 0.000 claims description 13
• 125000003435 aroyl group Chemical group 0.000 claims description 13
• 125000002971 oxazolyl group Chemical group 0.000 claims description 13
• 125000003386 piperidinyl group Chemical group 0.000 claims description 13
• 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 13
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 13
• 125000000335 thiazolyl group Chemical group 0.000 claims description 13
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 12
• 125000003282 alkyl amino group Chemical group 0.000 claims description 12
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 12
• 230000006378 damage Effects 0.000 claims description 12
• 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 12
• 230000002757 inflammatory effect Effects 0.000 claims description 12
• 238000011282 treatment Methods 0.000 claims description 12
• IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 11
• 125000003342 alkenyl group Chemical group 0.000 claims description 11
• 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 11
• 125000004122 cyclic group Chemical group 0.000 claims description 11
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 11
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 11
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 10
• 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 10
• 125000005872 benzooxazolyl group Chemical group 0.000 claims description 10
• 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 claims description 10
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 10
• 125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 claims description 10
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 10
• 230000001404 mediated effect Effects 0.000 claims description 10
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 9
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
• 125000000304 alkynyl group Chemical group 0.000 claims description 9
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 9
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
• 125000002541 furyl group Chemical group 0.000 claims description 9
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 9
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 9
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 9
• 150000003839 salts Chemical class 0.000 claims description 9
• 125000001544 thienyl group Chemical group 0.000 claims description 9
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
• 208000002193 Pain Diseases 0.000 claims description 8
• 150000004982 aromatic amines Chemical class 0.000 claims description 8
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
• 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 8
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 8
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
• 230000008569 process Effects 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• 208000011580 syndromic disease Diseases 0.000 claims description 8
• 230000008733 trauma Effects 0.000 claims description 8
• 125000006594 (C1-C3) alkylsulfony group Chemical group 0.000 claims description 7
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 7
• 206010040070 Septic Shock Diseases 0.000 claims description 7
• 208000027418 Wounds and injury Diseases 0.000 claims description 7
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 7
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 7
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
• 125000001425 triazolyl group Chemical group 0.000 claims description 7
• 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 6
• 208000024827 Alzheimer disease Diseases 0.000 claims description 6
• 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 6
• 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 6
• 125000001246 bromo group Chemical group Br* 0.000 claims description 6
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
• 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 6
• 150000002148 esters Chemical class 0.000 claims description 6
• 125000001153 fluoro group Chemical group F* 0.000 claims description 6
• 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 claims description 6
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 6
• 201000006417 multiple sclerosis Diseases 0.000 claims description 6
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 6
• 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 6
• JOZPEVMCAKXSEY-UHFFFAOYSA-N pyrimido[5,4-d]pyrimidine Chemical compound N1=CN=CC2=NC=NC=C21 JOZPEVMCAKXSEY-UHFFFAOYSA-N 0.000 claims description 6
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
• 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 5
• 208000011231 Crohn disease Diseases 0.000 claims description 5
• 201000009906 Meningitis Diseases 0.000 claims description 5
• 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 5
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
• 208000037976 chronic inflammation Diseases 0.000 claims description 5
• 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 claims description 5
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 5
• 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 5
• 125000005046 dihydronaphthyl group Chemical group 0.000 claims description 5
• 201000008482 osteoarthritis Diseases 0.000 claims description 5
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 5
• 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 claims description 5
• QYCGBAJADAGLLK-UHFFFAOYSA-N 1-(cyclohepten-1-yl)cycloheptene Chemical group C1CCCCC=C1C1=CCCCCC1 QYCGBAJADAGLLK-UHFFFAOYSA-N 0.000 claims description 4
• VSIYJQNFMOOGCU-UHFFFAOYSA-N 1-(cyclohexen-1-yl)cyclohexene Chemical group C1CCCC(C=2CCCCC=2)=C1 VSIYJQNFMOOGCU-UHFFFAOYSA-N 0.000 claims description 4
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
• 208000009137 Behcet syndrome Diseases 0.000 claims description 4
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 4
• 206010007559 Cardiac failure congestive Diseases 0.000 claims description 4
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 4
• 208000000094 Chronic Pain Diseases 0.000 claims description 4
• 206010009900 Colitis ulcerative Diseases 0.000 claims description 4
• 206010019280 Heart failures Diseases 0.000 claims description 4
• 201000004681 Psoriasis Diseases 0.000 claims description 4
• 208000006011 Stroke Diseases 0.000 claims description 4
• 206010044248 Toxic shock syndrome Diseases 0.000 claims description 4
• 231100000650 Toxic shock syndrome Toxicity 0.000 claims description 4
• 201000006704 Ulcerative Colitis Diseases 0.000 claims description 4
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
• 208000038016 acute inflammation Diseases 0.000 claims description 4
• 230000006022 acute inflammation Effects 0.000 claims description 4
• 208000005298 acute pain Diseases 0.000 claims description 4
• 208000006673 asthma Diseases 0.000 claims description 4
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
• 125000002837 carbocyclic group Chemical group 0.000 claims description 4
• 238000007887 coronary angioplasty Methods 0.000 claims description 4
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
• 125000003113 cycloheptyloxy group Chemical group C1(CCCCCC1)O* 0.000 claims description 4
• 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 claims description 4
• 206010012601 diabetes mellitus Diseases 0.000 claims description 4
• 210000003714 granulocyte Anatomy 0.000 claims description 4
• 238000001631 haemodialysis Methods 0.000 claims description 4
• 230000000322 hemodialysis Effects 0.000 claims description 4
• 210000004072 lung Anatomy 0.000 claims description 4
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
• 208000037890 multiple organ injury Diseases 0.000 claims description 4
• 208000010125 myocardial infarction Diseases 0.000 claims description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
• 239000008194 pharmaceutical composition Substances 0.000 claims description 4
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
• 208000037803 restenosis Diseases 0.000 claims description 4
• 208000017520 skin disease Diseases 0.000 claims description 4
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
• 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 4
• 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims description 3
• 201000001320 Atherosclerosis Diseases 0.000 claims description 3
• 206010012442 Dermatitis contact Diseases 0.000 claims description 3
• 208000009329 Graft vs Host Disease Diseases 0.000 claims description 3
• 206010051606 Necrotising colitis Diseases 0.000 claims description 3
• 206010063837 Reperfusion injury Diseases 0.000 claims description 3
• 206010040047 Sepsis Diseases 0.000 claims description 3
• 206010048873 Traumatic arthritis Diseases 0.000 claims description 3
• 230000006020 chronic inflammation Effects 0.000 claims description 3
• VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims description 3
• 208000024908 graft versus host disease Diseases 0.000 claims description 3
• 208000004995 necrotizing enterocolitis Diseases 0.000 claims description 3
• 201000006195 perinatal necrotizing enterocolitis Diseases 0.000 claims description 3
• 230000036303 septic shock Effects 0.000 claims description 3
• 239000000779 smoke Substances 0.000 claims description 3
• 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 3
• GFXRDJDHGXRRLM-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-(4-purin-9-ylnaphthalen-1-yl)urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1N1C2=NC=NC=C2N=C1 GFXRDJDHGXRRLM-UHFFFAOYSA-N 0.000 claims description 2
• LGKYJRSKTYUTQH-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-(4-pyrrolo[3,2-c]pyridin-1-ylnaphthalen-1-yl)urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1N1C2=CC=NC=C2C=C1 LGKYJRSKTYUTQH-UHFFFAOYSA-N 0.000 claims description 2
• BDNZGSDHXKKWCP-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-(2-oxo-1h-pyrido[2,3-b][1,4]oxazin-7-yl)naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C1=CN=C(OCC(=O)N2)C2=C1 BDNZGSDHXKKWCP-UHFFFAOYSA-N 0.000 claims description 2
• RGIRAMBPYYWIFF-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-(2-oxo-3,4-dihydro-1h-pyrido[2,3-b]pyrazin-7-yl)naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C1=CN=C(NCC(=O)N2)C2=C1 RGIRAMBPYYWIFF-UHFFFAOYSA-N 0.000 claims description 2
• BRVFPNRCSFKJJL-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-(6-morpholin-4-ylpurin-9-yl)naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1N1C2=NC=NC(N3CCOCC3)=C2N=C1 BRVFPNRCSFKJJL-UHFFFAOYSA-N 0.000 claims description 2
• SMJMNVALWCFSQR-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-(1-morpholin-4-yl-2,3-dihydro-1h-inden-5-yl)naphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=C4CCC(C4=CC=3)N3CCOCC3)=CC=2)=CC(C(C)(C)C)=N1 SMJMNVALWCFSQR-UHFFFAOYSA-N 0.000 claims description 2
• SACWWEGFEOSUBD-UHFFFAOYSA-N 1-[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]-3-(4-pyrrolo[3,2-c]pyridin-1-ylnaphthalen-1-yl)urea Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1N1C2=CC=NC=C2C=C1 SACWWEGFEOSUBD-UHFFFAOYSA-N 0.000 claims description 2
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 2
• 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 2
• 201000009273 Endometriosis Diseases 0.000 claims description 2
• 206010018364 Glomerulonephritis Diseases 0.000 claims description 2
• 208000035895 Guillain-Barré syndrome Diseases 0.000 claims description 2
• 208000016604 Lyme disease Diseases 0.000 claims description 2
• 206010049567 Miller Fisher syndrome Diseases 0.000 claims description 2
• 208000001132 Osteoporosis Diseases 0.000 claims description 2
• 206010033645 Pancreatitis Diseases 0.000 claims description 2
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• 229960003966 nicotinamide Drugs 0.000 claims description 2
• 239000011570 nicotinamide Substances 0.000 claims description 2
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 8
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 8
• 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 6
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 6
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
• 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 1
• YRJJMMBZLAUPTQ-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-(4-isoquinolin-5-ylnaphthalen-1-yl)urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C1=CC=CC2=CN=CC=C12 YRJJMMBZLAUPTQ-UHFFFAOYSA-N 0.000 claims 1
• FQJARBQAKUWBOY-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-(4-purin-7-ylnaphthalen-1-yl)urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1N1C2=CN=CN=C2N=C1 FQJARBQAKUWBOY-UHFFFAOYSA-N 0.000 claims 1
• GPVASNCSSAILMO-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-(4-pyrazolo[3,4-d]pyrimidin-1-ylnaphthalen-1-yl)urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1N1C2=NC=NC=C2C=N1 GPVASNCSSAILMO-UHFFFAOYSA-N 0.000 claims 1
• IGLDXFIDXMXHJS-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-(1-methyl-2-oxopyrido[2,3-b][1,4]oxazin-7-yl)naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C1=CN=C(OCC(=O)N2C)C2=C1 IGLDXFIDXMXHJS-UHFFFAOYSA-N 0.000 claims 1
• LWXBCDQNUNGQQD-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-(1h-imidazo[4,5-b]pyridin-6-yl)naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C1=CN=C(NC=N2)C2=C1 LWXBCDQNUNGQQD-UHFFFAOYSA-N 0.000 claims 1
• RNCMAOCPXYKQJL-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-(2,3-dioxo-1,4-dihydropyrido[2,3-b]pyrazin-7-yl)naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C1=CN=C(NC(=O)C(=O)N2)C2=C1 RNCMAOCPXYKQJL-UHFFFAOYSA-N 0.000 claims 1
• WYQKCQFUPDWHCC-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-(2,6-dioxo-3h-purin-7-yl)naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1N1C(C(=O)NC(=O)N2)=C2N=C1 WYQKCQFUPDWHCC-UHFFFAOYSA-N 0.000 claims 1
• KXUVCEDBYKZYRR-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-(2,6-dioxo-3h-purin-9-yl)naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1N1C(NC(=O)NC2=O)=C2N=C1 KXUVCEDBYKZYRR-UHFFFAOYSA-N 0.000 claims 1
• RAMUKMWOTXRIBZ-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-(2-oxo-1,3-dihydroimidazo[4,5-b]pyridin-6-yl)naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C1=CN=C(NC(=O)N2)C2=C1 RAMUKMWOTXRIBZ-UHFFFAOYSA-N 0.000 claims 1
• FIHPLXYJKLRSEG-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-(2-oxo-1h-pyrido[2,3-b][1,4]thiazin-7-yl)naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C1=CN=C(SCC(=O)N2)C2=C1 FIHPLXYJKLRSEG-UHFFFAOYSA-N 0.000 claims 1
• ZEYQCADOVROZAI-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-(3-methyl-2-oxo-1h-pyrido[2,3-b][1,4]oxazin-7-yl)naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C1=CN=C(OC(C)C(=O)N2)C2=C1 ZEYQCADOVROZAI-UHFFFAOYSA-N 0.000 claims 1
• FNUCGIUYJLQGTE-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-(3-methylsulfonylimidazo[4,5-b]pyridin-6-yl)naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C1=CN=C(N(C=N2)S(C)(=O)=O)C2=C1 FNUCGIUYJLQGTE-UHFFFAOYSA-N 0.000 claims 1
• OBNVHKPLGYVJQF-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-(6-pyrrolidin-1-ylpurin-9-yl)naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1N1C2=NC=NC(N3CCCC3)=C2N=C1 OBNVHKPLGYVJQF-UHFFFAOYSA-N 0.000 claims 1
• RBQDFLPJMCDTKL-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[2-(diethylaminomethyl)-1h-imidazo[4,5-b]pyridin-6-yl]naphthalen-1-yl]urea Chemical compound C=1N=C2NC(CN(CC)CC)=NC2=CC=1C(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=CC=C1OC RBQDFLPJMCDTKL-UHFFFAOYSA-N 0.000 claims 1
• HFGRIYIRFNSLEL-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[2-(methanesulfonamido)-1h-imidazo[4,5-b]pyridin-6-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C1=CN=C(NC(NS(C)(=O)=O)=N2)C2=C1 HFGRIYIRFNSLEL-UHFFFAOYSA-N 0.000 claims 1
• UWSGRULLVOUDKW-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[2-(morpholin-4-ylmethyl)-1h-imidazo[4,5-b]pyridin-6-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C1=CN=C(NC(CN2CCOCC2)=N2)C2=C1 UWSGRULLVOUDKW-UHFFFAOYSA-N 0.000 claims 1
• RUHDQLHHQYFCNP-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[2-(pyrrolidin-1-ylmethyl)-1h-imidazo[4,5-b]pyridin-6-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C1=CN=C(NC(CN2CCCC2)=N2)C2=C1 RUHDQLHHQYFCNP-UHFFFAOYSA-N 0.000 claims 1
• DPNUIQBGLKWCQO-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[2-[(4-methylpiperazin-1-yl)methyl]-1h-imidazo[4,5-b]pyridin-6-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C1=CN=C(NC(CN2CCN(C)CC2)=N2)C2=C1 DPNUIQBGLKWCQO-UHFFFAOYSA-N 0.000 claims 1
• CHSWPBWRDOIDMS-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[2-methyl-6-(2-morpholin-4-ylethylamino)purin-9-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1N1C2=NC(C)=NC(NCCN3CCOCC3)=C2N=C1 CHSWPBWRDOIDMS-UHFFFAOYSA-N 0.000 claims 1
• YAICRUMJCXODKK-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[2-oxo-3-(pyridin-2-ylmethyl)-1h-pyrido[2,3-b][1,4]oxazin-7-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C1=CN=C(OC(CC=2N=CC=CC=2)C(=O)N2)C2=C1 YAICRUMJCXODKK-UHFFFAOYSA-N 0.000 claims 1
• VOASWDZRPLPJSC-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[3-(2-morpholin-4-ylethyl)imidazo[4,5-b]pyridin-6-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C1=CN=C(N(CCN2CCOCC2)C=N2)C2=C1 VOASWDZRPLPJSC-UHFFFAOYSA-N 0.000 claims 1
• YWFSYTUYNDXVIJ-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[3-(pyridin-2-ylmethyl)imidazo[4,5-b]pyridin-6-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C1=CN=C(N(CC=2N=CC=CC=2)C=N2)C2=C1 YWFSYTUYNDXVIJ-UHFFFAOYSA-N 0.000 claims 1
• RUNYVZLSLHZJPN-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[3-[(3,4-dimethoxyphenyl)methyl]-2-oxo-1h-pyrido[2,3-b][1,4]oxazin-7-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C1=CN=C(OC(CC=2C=C(OC)C(OC)=CC=2)C(=O)N2)C2=C1 RUNYVZLSLHZJPN-UHFFFAOYSA-N 0.000 claims 1
• HTRLABBITBZKCZ-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[3-[2-(dimethylamino)ethyl]-2-oxo-1h-pyrido[2,3-b][1,4]oxazin-7-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C1=CN=C(OC(CCN(C)C)C(=O)N2)C2=C1 HTRLABBITBZKCZ-UHFFFAOYSA-N 0.000 claims 1
• JORCFHWIBCLMLA-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[3-[2-(dimethylamino)ethyl]imidazo[4,5-b]pyridin-6-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C1=CN=C(N(CCN(C)C)C=N2)C2=C1 JORCFHWIBCLMLA-UHFFFAOYSA-N 0.000 claims 1
• MFNVSFHWWDQXFD-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-(1-methoxypropan-2-ylamino)purin-9-yl]naphthalen-1-yl]urea Chemical compound C1=NC=2C(NC(C)COC)=NC=NC=2N1C(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=CC=C1OC MFNVSFHWWDQXFD-UHFFFAOYSA-N 0.000 claims 1
• XRCPKMBWTVIZAQ-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-(1-phenylethylamino)purin-9-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1N1C2=NC=NC(NC(C)C=3C=CC=CC=3)=C2N=C1 XRCPKMBWTVIZAQ-UHFFFAOYSA-N 0.000 claims 1
• WDGOEGHJRTXTBF-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-(2-methoxyethylamino)purin-9-yl]naphthalen-1-yl]urea Chemical compound C1=NC=2C(NCCOC)=NC=NC=2N1C(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=CC=C1OC WDGOEGHJRTXTBF-UHFFFAOYSA-N 0.000 claims 1
• SHPFSQVYQZPMSL-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-(2-morpholin-4-ylethylamino)purin-9-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1N1C2=NC=NC(NCCN3CCOCC3)=C2N=C1 SHPFSQVYQZPMSL-UHFFFAOYSA-N 0.000 claims 1
• BQZCUGNIMAJJKA-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-(4-methylpiperazin-1-yl)purin-9-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1N1C2=NC=NC(N3CCN(C)CC3)=C2N=C1 BQZCUGNIMAJJKA-UHFFFAOYSA-N 0.000 claims 1
• XGSBSBCEXMWWBA-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-(cyclohexylamino)purin-9-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1N1C2=NC=NC(NC3CCCCC3)=C2N=C1 XGSBSBCEXMWWBA-UHFFFAOYSA-N 0.000 claims 1
• HITXXXNPUVTGAO-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-(cyclopentylamino)purin-9-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1N1C2=NC=NC(NC3CCCC3)=C2N=C1 HITXXXNPUVTGAO-UHFFFAOYSA-N 0.000 claims 1
• NOCLETXPYUISBZ-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-(cyclopropylamino)-2-methylpurin-9-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1N1C2=NC(C)=NC(NC3CC3)=C2N=C1 NOCLETXPYUISBZ-UHFFFAOYSA-N 0.000 claims 1
• TZZJDHNYMADGQV-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-(cyclopropylamino)purin-9-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1N1C2=NC=NC(NC3CC3)=C2N=C1 TZZJDHNYMADGQV-UHFFFAOYSA-N 0.000 claims 1
• AZGCHACUSMJIER-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-(cyclopropylmethylamino)purin-9-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1N1C2=NC=NC(NCC3CC3)=C2N=C1 AZGCHACUSMJIER-UHFFFAOYSA-N 0.000 claims 1
• IDYXYTUIVTVJFX-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-(dimethylamino)purin-9-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1N1C2=NC=NC(N(C)C)=C2N=C1 IDYXYTUIVTVJFX-UHFFFAOYSA-N 0.000 claims 1
• VFNOTBKNTFUDEQ-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-(ethylamino)-2-methylpurin-9-yl]naphthalen-1-yl]urea Chemical compound C1=NC=2C(NCC)=NC(C)=NC=2N1C(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=CC=C1OC VFNOTBKNTFUDEQ-UHFFFAOYSA-N 0.000 claims 1
• ACVGALLCMNWGHN-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-(methylamino)purin-9-yl]naphthalen-1-yl]urea Chemical compound C1=NC=2C(NC)=NC=NC=2N1C(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=CC=C1OC ACVGALLCMNWGHN-UHFFFAOYSA-N 0.000 claims 1
• RTHSSZZEWFLZCY-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-(oxan-4-ylamino)purin-9-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1N1C2=NC=NC(NC3CCOCC3)=C2N=C1 RTHSSZZEWFLZCY-UHFFFAOYSA-N 0.000 claims 1
• XFSOQNHPVMAMKE-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-(oxolan-3-ylamino)purin-9-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1N1C2=NC=NC(NC3COCC3)=C2N=C1 XFSOQNHPVMAMKE-UHFFFAOYSA-N 0.000 claims 1
• OUEHQQHYYOOQAP-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-(propan-2-ylamino)purin-9-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1N1C2=NC=NC(NC(C)C)=C2N=C1 OUEHQQHYYOOQAP-UHFFFAOYSA-N 0.000 claims 1
• SKGZXXQLPVVWAR-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-(pyridin-2-ylmethylamino)purin-9-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1N1C2=NC=NC(NCC=3N=CC=CC=3)=C2N=C1 SKGZXXQLPVVWAR-UHFFFAOYSA-N 0.000 claims 1
• ZZNCFVXWTWQUIK-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-[2-(dimethylamino)ethyl-methylamino]purin-9-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1N1C2=NC=NC(N(C)CCN(C)C)=C2N=C1 ZZNCFVXWTWQUIK-UHFFFAOYSA-N 0.000 claims 1
• BVSCEEBXXJNZHO-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-[2-(dimethylamino)ethylamino]purin-9-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1N1C2=NC=NC(NCCN(C)C)=C2N=C1 BVSCEEBXXJNZHO-UHFFFAOYSA-N 0.000 claims 1
• GIBGYMMEMDBGQN-UHFFFAOYSA-N 1-[4-(2-amino-1h-imidazo[4,5-b]pyridin-6-yl)naphthalen-1-yl]-3-(5-tert-butyl-2-methoxyphenyl)urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C1=CN=C(NC(N)=N2)C2=C1 GIBGYMMEMDBGQN-UHFFFAOYSA-N 0.000 claims 1
• RVWOTMWQXJTPST-UHFFFAOYSA-N 1-[4-(3-benzyl-2-oxo-1h-pyrido[2,3-b][1,4]oxazin-7-yl)naphthalen-1-yl]-3-[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]urea Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C1=CN=C(OC(CC=2C=CC=CC=2)C(=O)N2)C2=C1 RVWOTMWQXJTPST-UHFFFAOYSA-N 0.000 claims 1
• PZTDOGVERGXERN-UHFFFAOYSA-N 1-[4-(3-benzylimidazo[4,5-b]pyridin-6-yl)naphthalen-1-yl]-3-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=C4N=CN(CC=5C=CC=CC=5)C4=NC=3)=CC=2)=CC(C(C)(C)C)=N1 PZTDOGVERGXERN-UHFFFAOYSA-N 0.000 claims 1
• XQSLORWSCCJGFS-UHFFFAOYSA-N 1-[4-(6-aminopurin-9-yl)naphthalen-1-yl]-3-(5-tert-butyl-2-methoxyphenyl)urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1N1C2=NC=NC(N)=C2N=C1 XQSLORWSCCJGFS-UHFFFAOYSA-N 0.000 claims 1
• UJMWDFABTSOGLR-UHFFFAOYSA-N 1-[4-[6-(benzylamino)purin-9-yl]naphthalen-1-yl]-3-(5-tert-butyl-2-methoxyphenyl)urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1N1C2=NC=NC(NCC=3C=CC=CC=3)=C2N=C1 UJMWDFABTSOGLR-UHFFFAOYSA-N 0.000 claims 1
• UVRAJRCUBXYNOP-UHFFFAOYSA-N 1-[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]-3-(4-imidazo[4,5-c]pyridin-1-ylnaphthalen-1-yl)urea Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1N1C2=CC=NC=C2N=C1 UVRAJRCUBXYNOP-UHFFFAOYSA-N 0.000 claims 1
• FSTUCHYRCRCZAW-UHFFFAOYSA-N 1-[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]-3-(4-imidazo[4,5-c]pyridin-3-ylnaphthalen-1-yl)urea Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1N1C2=CN=CC=C2N=C1 FSTUCHYRCRCZAW-UHFFFAOYSA-N 0.000 claims 1
• WQBLWSRFXLKGSR-UHFFFAOYSA-N 1-[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]-3-[4-(2-oxo-1h-pyrido[2,3-b][1,4]oxazin-7-yl)naphthalen-1-yl]urea Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C1=CN=C(OCC(=O)N2)C2=C1 WQBLWSRFXLKGSR-UHFFFAOYSA-N 0.000 claims 1
• MRIOVAXKRIDRPD-UHFFFAOYSA-N 1-[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]-3-[4-(3-methyl-2-oxo-1h-pyrido[2,3-b][1,4]oxazin-7-yl)naphthalen-1-yl]urea Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C1=CN=C(OC(C)C(=O)N2)C2=C1 MRIOVAXKRIDRPD-UHFFFAOYSA-N 0.000 claims 1
• HBYZOJIEJJYVFM-UHFFFAOYSA-N n-[6-[4-[(5-tert-butyl-2-methoxyphenyl)carbamoylamino]naphthalen-1-yl]-1h-imidazo[4,5-b]pyridin-2-yl]acetamide Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C1=CN=C(NC(NC(C)=O)=N2)C2=C1 HBYZOJIEJJYVFM-UHFFFAOYSA-N 0.000 claims 1
• KCAZXXUMRWHVQI-UHFFFAOYSA-N n-[6-[4-[(5-tert-butyl-2-methoxyphenyl)carbamoylamino]naphthalen-1-yl]-1h-imidazo[4,5-b]pyridin-2-yl]benzamide Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C1=CN=C(NC(NC(=O)C=2C=CC=CC=2)=N2)C2=C1 KCAZXXUMRWHVQI-UHFFFAOYSA-N 0.000 claims 1
• 239000002260 anti-inflammatory agent Substances 0.000 abstract description 2
• 229940121363 anti-inflammatory agent Drugs 0.000 abstract description 2
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 76
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