CA2462441A1

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

1,4-disubstituted benzo-fused urea compounds as cytokine inhibitors Download PDF

Info

Publication number: CA2462441A1
Authority: CA; Canada
Prior art keywords: alkyl; phenyl; naphthalen; butyl; methoxy
Prior art date: 2001-10-18
Legal status : Abandoned

Application number

CA002462441A

Other languages

English (en)

French (fr)

Inventor

Pier F. Cirillo

Abdelhakim Hammach

John R. Regan

Current Assignee

Boehringer Ingelheim Pharmaceuticals Inc

Original Assignee

Individual

Priority date

2001-10-18

Filing date

2002-10-11

Publication date

2003-04-24

2002-10-11 Application filed by Individual filed Critical Individual

2003-04-24 Publication of CA2462441A1 publication Critical patent/CA2462441A1/en

Status Abandoned legal-status Critical Current

Links

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
208000019664 bone resorption disease Diseases 0.000 claims description 2
208000010247 contact dermatitis Diseases 0.000 claims description 2
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
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