CA2458029A1

CA2458029A1 - Methods of treating cytokine mediated diseases

Methods of treating cytokine mediated diseases Download PDF

Info

Publication number: CA2458029A1
Authority: CA; Canada
Prior art keywords: naphthalen; pyridin; phenyl; urea; ylmethyl
Prior art date: 2001-09-13
Legal status : Abandoned

Application number

CA002458029A

Other languages

English (en)

French (fr)

Inventor

Neil Moss

John R. Regan

Current Assignee

Boehringer Ingelheim Pharmaceuticals Inc

Original Assignee

Individual

Priority date

2001-09-13

Filing date

2002-09-09

Publication date

2003-03-20

2002-09-09 Application filed by Individual filed Critical Individual

2003-03-20 Publication of CA2458029A1 publication Critical patent/CA2458029A1/en

Status Abandoned legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 88
102000004127 Cytokines Human genes 0.000 title claims abstract description 53
108090000695 Cytokines Proteins 0.000 title claims abstract description 53
230000001404 mediated effect Effects 0.000 title claims abstract description 23
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 55
201000010099 disease Diseases 0.000 title claims description 51
206010019280 Heart failures Diseases 0.000 claims abstract description 17
206010028980 Neoplasm Diseases 0.000 claims abstract description 17
208000038016 acute inflammation Diseases 0.000 claims abstract description 17
230000006022 acute inflammation Effects 0.000 claims abstract description 17
210000004072 lung Anatomy 0.000 claims abstract description 17
208000009137 Behcet syndrome Diseases 0.000 claims abstract description 16
206010007559 Cardiac failure congestive Diseases 0.000 claims abstract description 16
201000011510 cancer Diseases 0.000 claims abstract description 16
208000037976 chronic inflammation Diseases 0.000 claims abstract description 16
230000006020 chronic inflammation Effects 0.000 claims abstract description 16
239000000779 smoke Substances 0.000 claims abstract description 16
206010002556 Ankylosing Spondylitis Diseases 0.000 claims abstract description 15
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims abstract description 15
201000009273 Endometriosis Diseases 0.000 claims abstract description 15
208000016604 Lyme disease Diseases 0.000 claims abstract description 15
206010040047 Sepsis Diseases 0.000 claims abstract description 15
206010046851 Uveitis Diseases 0.000 claims abstract description 15
206010048873 Traumatic arthritis Diseases 0.000 claims abstract description 14
238000007887 coronary angioplasty Methods 0.000 claims abstract description 14
208000037803 restenosis Diseases 0.000 claims abstract description 13
-1 pyridinonyl Chemical group 0.000 claims description 525
125000000217 alkyl group Chemical group 0.000 claims description 406
239000004202 carbamide Substances 0.000 claims description 246
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 227
229910020008 S(O) Inorganic materials 0.000 claims description 145
125000003545 alkoxy group Chemical group 0.000 claims description 143
229910052736 halogen Inorganic materials 0.000 claims description 130
125000004076 pyridyl group Chemical group 0.000 claims description 123
150000002367 halogens Chemical class 0.000 claims description 120
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 112
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 108
150000001875 compounds Chemical class 0.000 claims description 92
125000000623 heterocyclic group Chemical group 0.000 claims description 90
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 87
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 87
125000002883 imidazolyl group Chemical group 0.000 claims description 84
125000001624 naphthyl group Chemical group 0.000 claims description 71
125000004043 oxo group Chemical group O=* 0.000 claims description 70
229910052760 oxygen Inorganic materials 0.000 claims description 70
125000000714 pyrimidinyl group Chemical group 0.000 claims description 69
125000003373 pyrazinyl group Chemical group 0.000 claims description 63
125000001072 heteroaryl group Chemical group 0.000 claims description 61
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 53
125000004193 piperazinyl group Chemical group 0.000 claims description 52
125000003226 pyrazolyl group Chemical group 0.000 claims description 52
125000003118 aryl group Chemical group 0.000 claims description 51
125000002098 pyridazinyl group Chemical group 0.000 claims description 50
125000000168 pyrrolyl group Chemical group 0.000 claims description 50
125000002541 furyl group Chemical group 0.000 claims description 48
125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims description 42
125000005843 halogen group Chemical group 0.000 claims description 42
150000002825 nitriles Chemical class 0.000 claims description 39
125000001544 thienyl group Chemical group 0.000 claims description 39
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 36
229910052757 nitrogen Inorganic materials 0.000 claims description 36
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 33
125000000753 cycloalkyl group Chemical group 0.000 claims description 32
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 32
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 29
229910052717 sulfur Inorganic materials 0.000 claims description 28
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 26
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 26
125000003831 tetrazolyl group Chemical group 0.000 claims description 26
125000004433 nitrogen atom Chemical group N* 0.000 claims description 25
125000003386 piperidinyl group Chemical group 0.000 claims description 24
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 24
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 23
125000000304 alkynyl group Chemical group 0.000 claims description 23
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 23
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 23
125000001786 isothiazolyl group Chemical group 0.000 claims description 23
125000000842 isoxazolyl group Chemical group 0.000 claims description 23
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 23
125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 23
125000004432 carbon atom Chemical group C* 0.000 claims description 22
125000000392 cycloalkenyl group Chemical group 0.000 claims description 22
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 22
125000001041 indolyl group Chemical group 0.000 claims description 22
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 21
125000003282 alkyl amino group Chemical group 0.000 claims description 20
125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 20
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 19
125000006576 di-(C1-C3-alkyl)-aminocarbonyl group Chemical group 0.000 claims description 18
238000011282 treatment Methods 0.000 claims description 18
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 17
125000003342 alkenyl group Chemical group 0.000 claims description 16
125000003435 aroyl group Chemical group 0.000 claims description 16
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 16
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 16
125000005842 heteroatom Chemical group 0.000 claims description 16
125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 16
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 15
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 15
125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 15
125000005879 dioxolanyl group Chemical group 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 15
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 15
208000024827 Alzheimer disease Diseases 0.000 claims description 14
206010033645 Pancreatitis Diseases 0.000 claims description 14
125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 14
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 13
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 13
125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 claims description 13
125000005494 pyridonyl group Chemical group 0.000 claims description 13
229920006395 saturated elastomer Polymers 0.000 claims description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
125000004599 benzpyrazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 12
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 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
QYCGBAJADAGLLK-UHFFFAOYSA-N 1-(cyclohepten-1-yl)cycloheptene Chemical group C1CCCCC=C1C1=CCCCCC1 QYCGBAJADAGLLK-UHFFFAOYSA-N 0.000 claims description 10
VSIYJQNFMOOGCU-UHFFFAOYSA-N 1-(cyclohexen-1-yl)cyclohexene Chemical group C1CCCC(C=2CCCCC=2)=C1 VSIYJQNFMOOGCU-UHFFFAOYSA-N 0.000 claims description 10
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
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 10
125000005436 dihydrobenzothiophenyl group Chemical group S1C(CC2=C1C=CC=C2)* 0.000 claims description 10
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 10
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 9
125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 claims description 9
125000005046 dihydronaphthyl group Chemical group 0.000 claims description 9
125000005056 dihydrothiazolyl group Chemical group S1C(NC=C1)* 0.000 claims description 9
125000005553 heteroaryloxy group Chemical group 0.000 claims description 9
125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 9
FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims description 8
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 8
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 8
125000005940 1,4-dioxanyl group Chemical group 0.000 claims description 7
GFGAVPLNMQVFHP-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-[(2,6-dimethylmorpholin-4-yl)methyl]pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CC(C)OC(C)C1 GFGAVPLNMQVFHP-UHFFFAOYSA-N 0.000 claims description 7
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 7
229910052799 carbon Inorganic materials 0.000 claims description 7
125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 claims description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 7
102220104380 rs199933920 Human genes 0.000 claims description 7
238000002560 therapeutic procedure Methods 0.000 claims description 7
125000001425 triazolyl group Chemical group 0.000 claims description 7
HYSJPAQMILEQFY-UHFFFAOYSA-N 1-(3-methylnaphthalen-2-yl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CC1=CC2=CC=CC=C2C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 HYSJPAQMILEQFY-UHFFFAOYSA-N 0.000 claims description 6
125000003277 amino group Chemical group 0.000 claims description 6
125000005872 benzooxazolyl group Chemical group 0.000 claims description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 claims description 6
125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 6
125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 6
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 5
ZMQPIXAVYIDIBG-UHFFFAOYSA-N 1-(2,3-dimethyl-1h-indol-5-yl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=C2C(C)=C(C)NC2=CC=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 ZMQPIXAVYIDIBG-UHFFFAOYSA-N 0.000 claims description 5
PZXHLFLLNPJDJD-UHFFFAOYSA-N 1-(3-amino-5-tert-butyl-2-methoxyphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COC1=C(N)C=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 PZXHLFLLNPJDJD-UHFFFAOYSA-N 0.000 claims description 5
SYRCZMWWOSOYQG-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-(thiomorpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCSCC1 SYRCZMWWOSOYQG-UHFFFAOYSA-N 0.000 claims description 5
BCYXSXJASCDAPJ-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-[(4-methylpiperazin-1-yl)methyl]pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCN(C)CC1 BCYXSXJASCDAPJ-UHFFFAOYSA-N 0.000 claims description 5
QAMPLFFTYHFJJP-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxypyridin-3-yl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COC1=NC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 QAMPLFFTYHFJJP-UHFFFAOYSA-N 0.000 claims description 5
KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 5
125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 5
125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 5
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 5
CGONTLDBLAAPSU-UHFFFAOYSA-N n-[5-tert-butyl-2-methoxy-3-[[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]carbamoylamino]phenyl]acetamide Chemical compound COC1=C(NC(C)=O)C=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 CGONTLDBLAAPSU-UHFFFAOYSA-N 0.000 claims description 5
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 5
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 5
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 5
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 5
125000005505 thiomorpholino group Chemical group 0.000 claims description 5
125000006594 (C1-C3) alkylsulfony group Chemical group 0.000 claims description 4
JWVPCJKQLGUCRA-UHFFFAOYSA-N 1-(3,3-dimethyl-2-oxo-1h-indol-5-yl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=C2C(C)(C)C(=O)NC2=CC=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 JWVPCJKQLGUCRA-UHFFFAOYSA-N 0.000 claims description 4
XMJCSEMZSSHAPU-UHFFFAOYSA-N 1-(3-amino-5-tert-butyl-2-methoxyphenyl)-3-[4-(6-methylpyridin-3-yl)naphthalen-1-yl]urea Chemical compound COC1=C(N)C=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C1=CC=C(C)N=C1 XMJCSEMZSSHAPU-UHFFFAOYSA-N 0.000 claims description 4
HPQQHGUMMVKGPO-UHFFFAOYSA-N 1-(5-cyclohexyl-2-methoxyphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C2CCCCC2)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 HPQQHGUMMVKGPO-UHFFFAOYSA-N 0.000 claims description 4
ZHEMIWZWBVZODY-UHFFFAOYSA-N 1-(5-tert-butyl-2-ethoxyphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CCOC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 ZHEMIWZWBVZODY-UHFFFAOYSA-N 0.000 claims description 4
FBPMUUXVDWZTBK-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[2-(morpholin-4-ylmethyl)pyrimidin-5-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CN=C1CN1CCOCC1 FBPMUUXVDWZTBK-UHFFFAOYSA-N 0.000 claims description 4
YFMSNBUWORKEJK-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-[(3-oxopiperazin-1-yl)methyl]pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CC(=O)NCC1 YFMSNBUWORKEJK-UHFFFAOYSA-N 0.000 claims description 4
SXWHJWVLUMVFGS-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-[[4-(3-methoxyphenyl)piperazin-1-yl]methyl]pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=CC(N2CCN(CC=3N=CC(=CC=3)C=3C4=CC=CC=C4C(NC(=O)NC=4C(=CC=C(C=4)C(C)(C)C)OC)=CC=3)CC2)=C1 SXWHJWVLUMVFGS-UHFFFAOYSA-N 0.000 claims description 4
HOULHNIBVCNAGC-UHFFFAOYSA-N 1-[2,4-dimethoxy-5-(trifluoromethyl)phenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COC1=CC(OC)=C(C(F)(F)F)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 HOULHNIBVCNAGC-UHFFFAOYSA-N 0.000 claims description 4
FBVHTEUZJDFLTA-UHFFFAOYSA-N 1-[2-methoxy-5-(trifluoromethyl)phenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(F)(F)F)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 FBVHTEUZJDFLTA-UHFFFAOYSA-N 0.000 claims description 4
BUNHUXDJKLVIBC-UHFFFAOYSA-N 1-[2-methoxy-5-[(2-methylpropan-2-yl)oxy]phenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(OC(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 BUNHUXDJKLVIBC-UHFFFAOYSA-N 0.000 claims description 4
ICGUENJRUODDDI-UHFFFAOYSA-N 1-[4-[6-[[bis(2-cyanoethyl)amino]methyl]pyridin-3-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=CC=C(CN(CCC#N)CCC#N)N=C1 ICGUENJRUODDDI-UHFFFAOYSA-N 0.000 claims description 4
KVOJMIMBKVGVQO-UHFFFAOYSA-N 1-[4-[6-[[bis(2-methoxyethyl)amino]methyl]pyridin-3-yl]naphthalen-1-yl]-3-(5-tert-butyl-2-methoxyphenyl)urea Chemical compound C1=NC(CN(CCOC)CCOC)=CC=C1C(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=CC=C1OC KVOJMIMBKVGVQO-UHFFFAOYSA-N 0.000 claims description 4
FQAMJOYQZKEDGX-UHFFFAOYSA-N 1-[5-(2,2-dimethylpropanoyl)-2-methylphenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CC1=CC=C(C(=O)C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 FQAMJOYQZKEDGX-UHFFFAOYSA-N 0.000 claims description 4
CCBYJKVGOSVVLE-UHFFFAOYSA-N 1-[5-tert-butyl-2-(3-hydroxyprop-1-ynyl)phenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CC(C)(C)C1=CC=C(C#CCO)C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 CCBYJKVGOSVVLE-UHFFFAOYSA-N 0.000 claims description 4
YNPXZZMQKNKUHC-UHFFFAOYSA-N 1-[5-tert-butyl-2-methoxy-3-(2,2,2-trifluoroethylsulfonylamino)phenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=C(C(C)(C)C)C=C(NS(=O)(=O)CC(F)(F)F)C(OC)=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 YNPXZZMQKNKUHC-UHFFFAOYSA-N 0.000 claims description 4
IGBDEMKWRDVXMC-UHFFFAOYSA-N 1-[5-tert-butyl-2-methyl-3-[3-(oxan-2-yloxy)prop-1-ynyl]phenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=C(C(C)(C)C)C=C(C#CCOC2OCCCC2)C(C)=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 IGBDEMKWRDVXMC-UHFFFAOYSA-N 0.000 claims description 4
KSHWQBSJRNVYMU-UHFFFAOYSA-N 1-[5-tert-butyl-3-(2,3-dihydroxypropyl)-2-hydroxyphenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CC(C)(C)C1=CC(CC(O)CO)=C(O)C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 KSHWQBSJRNVYMU-UHFFFAOYSA-N 0.000 claims description 4
IUIBRMQDNNSMAC-UHFFFAOYSA-N 1-[[5-[4-[(5-tert-butyl-2-methoxyphenyl)carbamoylamino]naphthalen-1-yl]pyridin-2-yl]methyl]piperidine-3-carboxamide Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CC(C(N)=O)CCC1 IUIBRMQDNNSMAC-UHFFFAOYSA-N 0.000 claims description 4
TWTPPEZVNRJSQU-UHFFFAOYSA-N 2-[4-tert-butyl-2-[[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]carbamoylamino]phenoxy]acetamide Chemical compound CC(C)(C)C1=CC=C(OCC(N)=O)C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 TWTPPEZVNRJSQU-UHFFFAOYSA-N 0.000 claims description 4
GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims description 4
125000004442 acylamino group Chemical group 0.000 claims description 4
150000001408 amides Chemical class 0.000 claims description 4
125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 4
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
125000002243 cyclohexanonyl group Chemical group *C1(*)C(=O)C(*)(*)C(*)(*)C(*)(*)C1(*)* 0.000 claims description 4
125000004652 decahydroisoquinolinyl group Chemical group C1(NCCC2CCCCC12)* 0.000 claims description 4
125000004856 decahydroquinolinyl group Chemical group N1(CCCC2CCCCC12)* 0.000 claims description 4
125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 claims description 4
125000005044 dihydroquinolinyl group Chemical group N1(CC=CC2=CC=CC=C12)* 0.000 claims description 4
125000000532 dioxanyl group Chemical group 0.000 claims description 4
125000005883 dithianyl group Chemical group 0.000 claims description 4
125000002636 imidazolinyl group Chemical group 0.000 claims description 4
125000002950 monocyclic group Chemical group 0.000 claims description 4
VZTPVFAWGLVYSE-UHFFFAOYSA-N n-[5-tert-butyl-2-methoxy-3-[[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]carbamoylamino]phenyl]-2,2,2-trifluoroacetamide Chemical compound C1=C(C(C)(C)C)C=C(NC(=O)C(F)(F)F)C(OC)=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 VZTPVFAWGLVYSE-UHFFFAOYSA-N 0.000 claims description 4
CBBNEQNYUJVZPQ-UHFFFAOYSA-N n-[5-tert-butyl-2-methoxy-3-[[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]carbamoylamino]phenyl]-2-methylpropanamide Chemical compound C1=C(C(C)(C)C)C=C(NC(=O)C(C)C)C(OC)=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 CBBNEQNYUJVZPQ-UHFFFAOYSA-N 0.000 claims description 4
125000005968 oxazolinyl group Chemical group 0.000 claims description 4
125000003566 oxetanyl group Chemical group 0.000 claims description 4
125000005545 phthalimidyl group Chemical group 0.000 claims description 4
125000001422 pyrrolinyl group Chemical group 0.000 claims description 4
125000003507 tetrahydrothiofenyl group Chemical group 0.000 claims description 4
125000001984 thiazolidinyl group Chemical group 0.000 claims description 4
125000002769 thiazolinyl group Chemical group 0.000 claims description 4
125000005503 thioxanyl group Chemical group 0.000 claims description 4
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
CDGVKVKZQCDYCD-UHFFFAOYSA-N 1-(5-tert-butyl-1,3-benzoxazol-7-yl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C=12OC=NC2=CC(C(C)(C)C)=CC=1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 CDGVKVKZQCDYCD-UHFFFAOYSA-N 0.000 claims description 3
UVDHLVZENVKMSJ-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxy-3-nitrophenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=C(C(C)(C)C)C=C([N+]([O-])=O)C(OC)=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 UVDHLVZENVKMSJ-UHFFFAOYSA-N 0.000 claims description 3
JNWZPGHDLVFOHU-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[5-(morpholin-4-ylmethyl)pyrazin-2-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(N=C1)=CN=C1CN1CCOCC1 JNWZPGHDLVFOHU-UHFFFAOYSA-N 0.000 claims description 3
NNXDLNQHNUKICX-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-(1,3-dioxolan-2-yl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C1=CC=C(C2OCCO2)N=C1 NNXDLNQHNUKICX-UHFFFAOYSA-N 0.000 claims description 3
VRQBVALNRMCCRQ-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-(morpholine-4-carbonyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C1=CC=C(C(=O)N2CCOCC2)N=C1 VRQBVALNRMCCRQ-UHFFFAOYSA-N 0.000 claims description 3
USPQVAWOBXKNOF-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-(oxan-4-ylamino)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1NC1CCOCC1 USPQVAWOBXKNOF-UHFFFAOYSA-N 0.000 claims description 3
BYPZLIPMLRPGCS-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-[(2-methyl-3-oxopiperazin-1-yl)methyl]pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1C(C)C(=O)NCC1 BYPZLIPMLRPGCS-UHFFFAOYSA-N 0.000 claims description 3
LNMOYKCXUACLIC-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-[(oxolan-3-ylamino)methyl]pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CNC1COCC1 LNMOYKCXUACLIC-UHFFFAOYSA-N 0.000 claims description 3
LFMQDEIBFGMGHX-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-[[2-(methoxymethyl)morpholin-4-yl]methyl]pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1COC(COC)CN1CC1=CC=C(C=2C3=CC=CC=C3C(NC(=O)NC=3C(=CC=C(C=3)C(C)(C)C)OC)=CC=2)C=N1 LFMQDEIBFGMGHX-UHFFFAOYSA-N 0.000 claims description 3
FPQDJMDZVOJUJL-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-[[2-cyanoethyl(oxolan-2-ylmethyl)amino]methyl]pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN(CCC#N)CC1OCCC1 FPQDJMDZVOJUJL-UHFFFAOYSA-N 0.000 claims description 3
RSRIISDWBQWUPX-UHFFFAOYSA-N 1-(5-tert-butyl-2-methyl-1,3-benzoxazol-7-yl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C=12OC(C)=NC2=CC(C(C)(C)C)=CC=1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 RSRIISDWBQWUPX-UHFFFAOYSA-N 0.000 claims description 3
KFXVPIJOIPYPSH-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylphenyl)-3-[4-[5-(methanesulfonamido)pyrazin-2-yl]naphthalen-1-yl]urea Chemical compound CC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C1=CN=C(NS(C)(=O)=O)C=N1 KFXVPIJOIPYPSH-UHFFFAOYSA-N 0.000 claims description 3
BFMKWXXXLFBTMH-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylsulfanylphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CSC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 BFMKWXXXLFBTMH-UHFFFAOYSA-N 0.000 claims description 3
BRZWHPXAPTYZID-UHFFFAOYSA-N 1-(5-tert-butyl-2-oxo-3h-1,3-benzoxazol-7-yl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C=12OC(=O)NC2=CC(C(C)(C)C)=CC=1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 BRZWHPXAPTYZID-UHFFFAOYSA-N 0.000 claims description 3
TYBHUHOIYNNGQO-UHFFFAOYSA-N 1-(5-tert-butyl-2-propan-2-yloxyphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CC(C)OC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 TYBHUHOIYNNGQO-UHFFFAOYSA-N 0.000 claims description 3
LPLXKSPOWLXYGG-UHFFFAOYSA-N 1-(5-tert-butyl-2-propoxyphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CCCOC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 LPLXKSPOWLXYGG-UHFFFAOYSA-N 0.000 claims description 3
GZRSLWDGXYUDLG-UHFFFAOYSA-N 1-(5-tert-butyl-2-pyrrolidin-1-ylphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C=1C=C(C=2C=NC(CN3CCOCC3)=CC=2)C2=CC=CC=C2C=1NC(=O)NC1=CC(C(C)(C)C)=CC=C1N1CCCC1 GZRSLWDGXYUDLG-UHFFFAOYSA-N 0.000 claims description 3
USGJETFWAMMMLN-UHFFFAOYSA-N 1-(5-tert-butyl-3-cyano-2-methoxyphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=C(C(C)(C)C)C=C(C#N)C(OC)=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 USGJETFWAMMMLN-UHFFFAOYSA-N 0.000 claims description 3
AHZOPOQRANAHAY-UHFFFAOYSA-N 1-(6-tert-butyl-3-oxo-4h-1,4-benzoxazin-8-yl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C=12OCC(=O)NC2=CC(C(C)(C)C)=CC=1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 AHZOPOQRANAHAY-UHFFFAOYSA-N 0.000 claims description 3
GZOFCRDWNOPBEB-UHFFFAOYSA-N 1-(6-tert-butyl-4-methyl-3-oxo-1,4-benzoxazin-8-yl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=C(C(C)(C)C)C=C2N(C)C(=O)COC2=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 GZOFCRDWNOPBEB-UHFFFAOYSA-N 0.000 claims description 3
MUQPJRRMNAGMKL-UHFFFAOYSA-N 1-[2-methylsulfinyl-5-(trifluoromethyl)phenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CS(=O)C1=CC=C(C(F)(F)F)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 MUQPJRRMNAGMKL-UHFFFAOYSA-N 0.000 claims description 3
LHRSCHWQXZSVDM-UHFFFAOYSA-N 1-[3-(benzenesulfonamido)-5-tert-butyl-2-methoxyphenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=C(C(C)(C)C)C=C(NS(=O)(=O)C=2C=CC=CC=2)C(OC)=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 LHRSCHWQXZSVDM-UHFFFAOYSA-N 0.000 claims description 3
MUNNAQCVMSTQDD-UHFFFAOYSA-N 1-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]-3-[3-(trifluoromethylsulfonyl)phenyl]urea Chemical compound FC(F)(F)S(=O)(=O)C1=CC=CC(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 MUNNAQCVMSTQDD-UHFFFAOYSA-N 0.000 claims description 3
HPNQMSKRZIBEMH-UHFFFAOYSA-N 1-[5-(1-cyanocyclopropyl)-2-methoxyphenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C2(CC2)C#N)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 HPNQMSKRZIBEMH-UHFFFAOYSA-N 0.000 claims description 3
LLVFXQIIDJSAES-UHFFFAOYSA-N 1-[5-tert-butyl-2-(1-methylpyrazol-4-yl)phenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=NN(C)C=C1C1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 LLVFXQIIDJSAES-UHFFFAOYSA-N 0.000 claims description 3
OXSRFMNERVPWMR-UHFFFAOYSA-N 1-[5-tert-butyl-3-(3-hydroxyprop-1-ynyl)-2-methylphenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=C(C(C)(C)C)C=C(C#CCO)C(C)=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 OXSRFMNERVPWMR-UHFFFAOYSA-N 0.000 claims description 3
JJHSDQDGIZUPON-UHFFFAOYSA-N 1-[5-tert-butyl-3-(ethylamino)-2-methoxyphenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CCNC1=CC(C(C)(C)C)=CC(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1OC JJHSDQDGIZUPON-UHFFFAOYSA-N 0.000 claims description 3
ZKKCYGKTHPYSLR-UHFFFAOYSA-N 1-[5-tert-butyl-3-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-2-methoxyphenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=C(C(C)(C)C)C=C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)C(OC)=C1CC1COC(C)(C)O1 ZKKCYGKTHPYSLR-UHFFFAOYSA-N 0.000 claims description 3
VUJVQDMCLKCGNP-UHFFFAOYSA-N 1-[5-tert-butyl-3-[2-(diethylamino)ethyl]-2-methoxyphenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CCN(CC)CCC1=CC(C(C)(C)C)=CC(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1OC VUJVQDMCLKCGNP-UHFFFAOYSA-N 0.000 claims description 3
POKPQQXNRDFJKE-UHFFFAOYSA-N 2-(5-tert-butyl-2-methoxyphenyl)-n-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]acetamide Chemical compound COC1=CC=C(C(C)(C)C)C=C1CC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 POKPQQXNRDFJKE-UHFFFAOYSA-N 0.000 claims description 3
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
125000002619 bicyclic group Chemical group 0.000 claims description 3
125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
125000003113 cycloheptyloxy group Chemical group C1(CCCCCC1)O* 0.000 claims description 3
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
125000004582 dihydrobenzothienyl group Chemical group S1C(CC2=C1C=CC=C2)* 0.000 claims description 3
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 3
125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 3
KGJOEOIQYVJQFZ-UHFFFAOYSA-N n-[5-[4-[(5-tert-butyl-2-methoxyphenyl)carbamoylamino]naphthalen-1-yl]pyridin-2-yl]acetamide Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C1=CC=C(NC(C)=O)N=C1 KGJOEOIQYVJQFZ-UHFFFAOYSA-N 0.000 claims description 3
ASKMNBKOUIHYNF-UHFFFAOYSA-N n-[5-tert-butyl-2-methoxy-3-[[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]carbamoylamino]phenyl]-n-methylacetamide Chemical compound C1=C(C(C)(C)C)C=C(N(C)C(C)=O)C(OC)=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 ASKMNBKOUIHYNF-UHFFFAOYSA-N 0.000 claims description 3
XZOIAOHMOBBSMM-UHFFFAOYSA-N n-[5-tert-butyl-2-methoxy-3-[[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]carbamoylamino]phenyl]propanamide Chemical compound CCC(=O)NC1=CC(C(C)(C)C)=CC(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1OC XZOIAOHMOBBSMM-UHFFFAOYSA-N 0.000 claims description 3
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
125000000335 thiazolyl group Chemical group 0.000 claims description 3
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
RGDYCIHVZRSMAR-UHFFFAOYSA-N 1,3-bis[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C=1C=C(C=2C=NC(CN3CCOCC3)=CC=2)C2=CC=CC=C2C=1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 RGDYCIHVZRSMAR-UHFFFAOYSA-N 0.000 claims description 2
CBEQVMLALWOOQZ-UHFFFAOYSA-N 1-(1-acetyl-2,3-dihydroindol-5-yl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C=1C=C2N(C(=O)C)CCC2=CC=1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 CBEQVMLALWOOQZ-UHFFFAOYSA-N 0.000 claims description 2
YNCLMYJXNRLKIU-UHFFFAOYSA-N 1-(2,5-ditert-butylphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CC(C)(C)C1=CC=C(C(C)(C)C)C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 YNCLMYJXNRLKIU-UHFFFAOYSA-N 0.000 claims description 2
NZLMNKKHXFTHNB-UHFFFAOYSA-N 1-(2-methoxy-5-phenoxyphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)C(OC)=CC=C1OC1=CC=CC=C1 NZLMNKKHXFTHNB-UHFFFAOYSA-N 0.000 claims description 2
JBQZUUIMGVSOBI-UHFFFAOYSA-N 1-(2-methoxydibenzofuran-3-yl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COC1=CC(C2=CC=CC=C2O2)=C2C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 JBQZUUIMGVSOBI-UHFFFAOYSA-N 0.000 claims description 2
DUKOBXKBDNMPMC-UHFFFAOYSA-N 1-(3,3-dimethyl-2-oxo-1h-indol-7-yl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CC1(C)C(=O)NC2=C1C=CC=C2NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 DUKOBXKBDNMPMC-UHFFFAOYSA-N 0.000 claims description 2
TZQUDCVXRIQQNV-UHFFFAOYSA-N 1-(3-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound OC1=CC=2CCCCC=2C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 TZQUDCVXRIQQNV-UHFFFAOYSA-N 0.000 claims description 2
YOTMDOZVZLPFOE-UHFFFAOYSA-N 1-(3-hydroxynaphthalen-2-yl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound OC1=CC2=CC=CC=C2C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 YOTMDOZVZLPFOE-UHFFFAOYSA-N 0.000 claims description 2
QWXGKJCBIRHWBX-UHFFFAOYSA-N 1-(4-amino-3,5-dibromophenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=C(Br)C(N)=C(Br)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 QWXGKJCBIRHWBX-UHFFFAOYSA-N 0.000 claims description 2
ITPDMJOSPFQMSH-UHFFFAOYSA-N 1-(4-anilino-2-methoxyphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C=1C=C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)C(OC)=CC=1NC1=CC=CC=C1 ITPDMJOSPFQMSH-UHFFFAOYSA-N 0.000 claims description 2
ZRJLFXTYVMVNFT-UHFFFAOYSA-N 1-(4-tert-butylphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=CC(C(C)(C)C)=CC=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 ZRJLFXTYVMVNFT-UHFFFAOYSA-N 0.000 claims description 2
GGRJYGKEBOTNHP-UHFFFAOYSA-N 1-(5-methoxy-2-methylphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C)C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 GGRJYGKEBOTNHP-UHFFFAOYSA-N 0.000 claims description 2
BKRYIJDAFCTFOD-UHFFFAOYSA-N 1-(5-tert-butyl-2-chloropyridin-3-yl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CC(C)(C)C1=CN=C(Cl)C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 BKRYIJDAFCTFOD-UHFFFAOYSA-N 0.000 claims description 2
QNLNFLUVBSWVIG-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[4-(morpholin-4-ylmethyl)piperidin-1-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1N1CCC(CN2CCOCC2)CC1 QNLNFLUVBSWVIG-UHFFFAOYSA-N 0.000 claims description 2
OOCWXPQLMUBOTM-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-(pyridin-3-ylamino)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1NC1=CC=CN=C1 OOCWXPQLMUBOTM-UHFFFAOYSA-N 0.000 claims description 2
ICSFCDJDIQYEBI-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-[(2-morpholin-4-ylethylamino)methyl]pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CNCCN1CCOCC1 ICSFCDJDIQYEBI-UHFFFAOYSA-N 0.000 claims description 2
DBMDOWNTQPAXHX-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-[(2-piperazin-1-ylethylamino)methyl]pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CNCCN1CCNCC1 DBMDOWNTQPAXHX-UHFFFAOYSA-N 0.000 claims description 2
BIZAXCQMFGBSDV-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-[(2-pyridin-3-ylethylamino)methyl]pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CNCCC1=CC=CN=C1 BIZAXCQMFGBSDV-UHFFFAOYSA-N 0.000 claims description 2
HGUYGZUWDGTFPX-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-[(3-pyridin-3-ylpyrrolidin-1-yl)methyl]pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CC(C=2C=NC=CC=2)CC1 HGUYGZUWDGTFPX-UHFFFAOYSA-N 0.000 claims description 2
RNQGADDUAZCRFR-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-[(4-pyridin-2-ylpiperazin-1-yl)methyl]pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCN(C=2N=CC=CC=2)CC1 RNQGADDUAZCRFR-UHFFFAOYSA-N 0.000 claims description 2
SLJBHZRSDHQULA-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-[(4-pyrimidin-2-ylpiperazin-1-yl)methyl]pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCN(C=2N=CC=CN=2)CC1 SLJBHZRSDHQULA-UHFFFAOYSA-N 0.000 claims description 2
YIBZEBREYBDTGG-UHFFFAOYSA-N 1-(6-tert-butyl-3-oxo-4h-1,4-benzoxazin-7-yl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CC(C)(C)C1=CC=2NC(=O)COC=2C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 YIBZEBREYBDTGG-UHFFFAOYSA-N 0.000 claims description 2
JRUKMXCPKKAGES-UHFFFAOYSA-N 1-[2-(2-methoxyphenoxy)-5-(trifluoromethyl)phenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=CC=C1OC1=CC=C(C(F)(F)F)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 JRUKMXCPKKAGES-UHFFFAOYSA-N 0.000 claims description 2
GPGIZCCQTKUMAX-UHFFFAOYSA-N 1-[2-(4-methylphenoxy)-5-(trifluoromethyl)phenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1OC1=CC=C(C(F)(F)F)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 GPGIZCCQTKUMAX-UHFFFAOYSA-N 0.000 claims description 2
JXNJLIQCKVEDAP-UHFFFAOYSA-N 1-[3-(4-bromo-1-methylpyrazol-3-yl)phenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CN1C=C(Br)C(C=2C=C(NC(=O)NC=3C4=CC=CC=C4C(C=4C=NC(CN5CCOCC5)=CC=4)=CC=3)C=CC=2)=N1 JXNJLIQCKVEDAP-UHFFFAOYSA-N 0.000 claims description 2
UUAXUBVBEGLBSR-UHFFFAOYSA-N 1-[4-(difluoromethoxy)phenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=CC(OC(F)F)=CC=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 UUAXUBVBEGLBSR-UHFFFAOYSA-N 0.000 claims description 2
DDHYJZZWEHJDGZ-UHFFFAOYSA-N 1-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]-3-[3-(1,3,4-oxadiazol-2-yl)phenyl]urea Chemical compound C=1C=C(C=2C=NC(CN3CCOCC3)=CC=2)C2=CC=CC=C2C=1NC(=O)NC(C=1)=CC=CC=1C1=NN=CO1 DDHYJZZWEHJDGZ-UHFFFAOYSA-N 0.000 claims description 2
MEGAZNOEWHRNPW-UHFFFAOYSA-N 1-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]-3-naphthalen-1-ylurea Chemical compound C=1C=CC2=CC=CC=C2C=1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 MEGAZNOEWHRNPW-UHFFFAOYSA-N 0.000 claims description 2
UMURFXAIRXJCDG-UHFFFAOYSA-N 1-[4-[6-[(4-acetylpiperazin-1-yl)methyl]pyridin-3-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=C1C(C=N1)=CC=C1CN1CCN(C(C)=O)CC1 UMURFXAIRXJCDG-UHFFFAOYSA-N 0.000 claims description 2
JCRCYQYGUOZTJN-UHFFFAOYSA-N 1-[5-(2-methylbutan-2-yl)-2-phenoxyphenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C=1C=C(C=2C=NC(CN3CCOCC3)=CC=2)C2=CC=CC=C2C=1NC(=O)NC1=CC(C(C)(C)CC)=CC=C1OC1=CC=CC=C1 JCRCYQYGUOZTJN-UHFFFAOYSA-N 0.000 claims description 2
LMXXQARHVCAHKT-UHFFFAOYSA-N 1-[5-(diethylsulfamoyl)-2-methoxyphenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CCN(CC)S(=O)(=O)C1=CC=C(OC)C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 LMXXQARHVCAHKT-UHFFFAOYSA-N 0.000 claims description 2
PFEMRUFOORUDMI-UHFFFAOYSA-N 1-[5-(hydroxymethyl)-2-methylphenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CC1=CC=C(CO)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 PFEMRUFOORUDMI-UHFFFAOYSA-N 0.000 claims description 2
LKCURQCMUIKKBG-UHFFFAOYSA-N 1-[5-tert-butyl-1-(methanesulfonamido)-2-oxopyridin-3-yl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound O=C1N(NS(C)(=O)=O)C=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 LKCURQCMUIKKBG-UHFFFAOYSA-N 0.000 claims description 2
BTOUXFPGALDZMQ-UHFFFAOYSA-N 1-[5-tert-butyl-2-(1-methylpyrazol-4-yl)phenyl]-3-[4-[4-(morpholin-4-ylmethyl)piperidin-1-yl]naphthalen-1-yl]urea Chemical compound C1=NN(C)C=C1C1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1N1CCC(CN2CCOCC2)CC1 BTOUXFPGALDZMQ-UHFFFAOYSA-N 0.000 claims description 2
GNURXJLCVXAFJJ-UHFFFAOYSA-N 1-[5-tert-butyl-2-(2-pyrrolidin-1-ylethoxy)phenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C=1C=C(C=2C=NC(CN3CCOCC3)=CC=2)C2=CC=CC=C2C=1NC(=O)NC1=CC(C(C)(C)C)=CC=C1OCCN1CCCC1 GNURXJLCVXAFJJ-UHFFFAOYSA-N 0.000 claims description 2
ZCPTVULXWYSYNL-UHFFFAOYSA-N 1-[5-tert-butyl-2-(dimethylamino)phenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CN(C)C1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 ZCPTVULXWYSYNL-UHFFFAOYSA-N 0.000 claims description 2
APHGTPBXJDMWPL-UHFFFAOYSA-N 1-[5-tert-butyl-2-(methylamino)pyridin-3-yl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CNC1=NC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 APHGTPBXJDMWPL-UHFFFAOYSA-N 0.000 claims description 2
UHGVMCQHFZBODE-UHFFFAOYSA-N 1-[5-tert-butyl-2-[3-(oxan-2-yloxy)prop-1-ynyl]phenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C=1C=C(C=2C=NC(CN3CCOCC3)=CC=2)C2=CC=CC=C2C=1NC(=O)NC1=CC(C(C)(C)C)=CC=C1C#CCOC1CCCCO1 UHGVMCQHFZBODE-UHFFFAOYSA-N 0.000 claims description 2
MRRTWVXKQWEBCG-UHFFFAOYSA-N 1-[5-tert-butyl-3-(2,3-dihydroxypropyl)-2-methoxyphenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COC1=C(CC(O)CO)C=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 MRRTWVXKQWEBCG-UHFFFAOYSA-N 0.000 claims description 2
MFSCEESLLCMMGE-UHFFFAOYSA-N 1-[6-tert-butyl-3-cyano-2-(methoxymethoxy)pyridin-4-yl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COCOC1=NC(C(C)(C)C)=CC(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1C#N MFSCEESLLCMMGE-UHFFFAOYSA-N 0.000 claims description 2
BIZOAYKLGAULJD-UHFFFAOYSA-N 2-[5-tert-butyl-7-[[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]carbamoylamino]-1,3-benzoxazol-2-yl]acetamide Chemical compound C=12OC(CC(N)=O)=NC2=CC(C(C)(C)C)=CC=1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 BIZOAYKLGAULJD-UHFFFAOYSA-N 0.000 claims description 2
UQZPGHOJMQTOHB-UHFFFAOYSA-N 2-chloro-n-(2-chloroethyl)-n-ethylethanamine Chemical compound ClCCN(CC)CCCl UQZPGHOJMQTOHB-UHFFFAOYSA-N 0.000 claims description 2
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 2
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
WOJATDXXHKRDIF-UHFFFAOYSA-N 3-[4-(2-methoxyphenyl)piperazin-1-yl]-1-(4-morpholin-4-ylphenyl)propan-1-one;dihydrochloride Chemical group Cl.Cl.COC1=CC=CC=C1N1CCN(CCC(=O)C=2C=CC(=CC=2)N2CCOCC2)CC1 WOJATDXXHKRDIF-UHFFFAOYSA-N 0.000 claims description 2
NXNOYGXRCAUQKA-UHFFFAOYSA-N 3-[[5-[4-[(5-tert-butyl-2-methylphenyl)carbamoylamino]naphthalen-1-yl]pyridin-2-yl]amino]propyl n-(5-tert-butyl-2-methylphenyl)carbamate Chemical compound CC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1NCCCOC(=O)NC1=CC(C(C)(C)C)=CC=C1C NXNOYGXRCAUQKA-UHFFFAOYSA-N 0.000 claims description 2
AYMFLFCMARIIJF-UHFFFAOYSA-N 5-tert-butyl-2-methoxy-3-[[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]carbamoylamino]benzamide Chemical compound C1=C(C(C)(C)C)C=C(C(N)=O)C(OC)=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 AYMFLFCMARIIJF-UHFFFAOYSA-N 0.000 claims description 2
IPQXTPZITPPENO-UHFFFAOYSA-N 5-tert-butyl-7-[[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]carbamoylamino]-1,3-benzoxazole-2-carboxamide Chemical compound C=12OC(C(N)=O)=NC2=CC(C(C)(C)C)=CC=1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 IPQXTPZITPPENO-UHFFFAOYSA-N 0.000 claims description 2
125000005605 benzo group Chemical group 0.000 claims description 2
125000001246 bromo group Chemical group Br* 0.000 claims description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
SIBKXTHADZRLHY-UHFFFAOYSA-N ethyl 4-[[5-[4-[(5-tert-butyl-2-methoxyphenyl)carbamoylamino]naphthalen-1-yl]pyridin-2-yl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1CC1=CC=C(C=2C3=CC=CC=C3C(NC(=O)NC=3C(=CC=C(C=3)C(C)(C)C)OC)=CC=2)C=N1 SIBKXTHADZRLHY-UHFFFAOYSA-N 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
231100000024 genotoxic Toxicity 0.000 claims description 2
230000001738 genotoxic effect Effects 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
BJPLHTBTHCPUJG-UHFFFAOYSA-N propan-2-yl 2-chloro-5-[[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]carbamoylamino]benzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 BJPLHTBTHCPUJG-UHFFFAOYSA-N 0.000 claims description 2
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
125000004953 trihalomethyl group Chemical group 0.000 claims description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 19
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 15
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 9
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 7
125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 5
125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 4
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 3
KLPFPTSVYVEKOL-UHFFFAOYSA-N 1-[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-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=C1C(C=N1)=CC=C1CN1CCOCC1 KLPFPTSVYVEKOL-UHFFFAOYSA-N 0.000 claims 3
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