JP2005503400A

JP2005503400A - サイトカイン媒介病の治療方法

サイトカイン媒介病の治療方法 Download PDF

Info

Publication number: JP2005503400A
Authority: JP; Japan
Prior art keywords: phenyl; pyridin; naphthalen; alkyl; urea
Prior art date: 2001-09-13
Legal status : Pending

Application number

JP2003526402A

Other languages

English (en)

Japanese (ja)

Other versions

JP2005503400A5 (https=

Inventor

ニールモス

ジョンアールリーガン

Original Assignee

ベーリンガーインゲルハイムファーマシューティカルズインコーポレイテッド

Priority date

2001-09-13

Filing date

2002-09-09

Publication date

2005-02-03

2002-09-09 Application filed by ベーリンガーインゲルハイムファーマシューティカルズインコーポレイテッド filed Critical ベーリンガーインゲルハイムファーマシューティカルズインコーポレイテッド

2005-02-03 Publication of JP2005503400A publication Critical patent/JP2005503400A/ja

2006-01-05 Publication of JP2005503400A5 publication Critical patent/JP2005503400A5/ja

Status Pending legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 71
102000004127 Cytokines Human genes 0.000 title claims abstract description 51
108090000695 Cytokines Proteins 0.000 title claims abstract description 51
230000001404 mediated effect Effects 0.000 title claims abstract description 23
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 59
201000010099 disease Diseases 0.000 title claims description 54
206010019280 Heart failures Diseases 0.000 claims abstract description 17
206010028980 Neoplasm Diseases 0.000 claims abstract description 17
206010007559 Cardiac failure congestive Diseases 0.000 claims abstract description 16
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims abstract description 16
201000011510 cancer Diseases 0.000 claims abstract description 16
206010002556 Ankylosing Spondylitis Diseases 0.000 claims abstract description 15
208000009137 Behcet syndrome Diseases 0.000 claims abstract description 15
201000009273 Endometriosis Diseases 0.000 claims abstract description 15
206010033645 Pancreatitis Diseases 0.000 claims abstract description 15
206010040047 Sepsis 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 14
208000016604 Lyme disease Diseases 0.000 claims abstract description 13
-1 pyridinonyl Chemical group 0.000 claims description 755
125000000217 alkyl group Chemical group 0.000 claims description 265
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 214
150000002825 nitriles Chemical class 0.000 claims description 143
239000004202 carbamide Substances 0.000 claims description 128
125000004076 pyridyl group Chemical group 0.000 claims description 125
229910052736 halogen Inorganic materials 0.000 claims description 124
150000002367 halogens Chemical class 0.000 claims description 114
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 108
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 100
150000001875 compounds Chemical class 0.000 claims description 94
125000000623 heterocyclic group Chemical group 0.000 claims description 90
125000002883 imidazolyl group Chemical group 0.000 claims description 85
125000003545 alkoxy group Chemical group 0.000 claims description 80
125000003118 aryl group Chemical group 0.000 claims description 79
125000004043 oxo group Chemical group O=* 0.000 claims description 69
125000000714 pyrimidinyl group Chemical group 0.000 claims description 69
229910052717 sulfur Inorganic materials 0.000 claims description 69
125000001624 naphthyl group Chemical group 0.000 claims description 68
229910052760 oxygen Inorganic materials 0.000 claims description 66
125000003373 pyrazinyl group Chemical group 0.000 claims description 64
125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims description 63
125000001072 heteroaryl group Chemical group 0.000 claims description 63
125000004193 piperazinyl group Chemical group 0.000 claims description 52
125000003226 pyrazolyl group Chemical group 0.000 claims description 51
125000002098 pyridazinyl group Chemical group 0.000 claims description 50
125000002541 furyl group Chemical group 0.000 claims description 48
125000005843 halogen group Chemical group 0.000 claims description 47
125000000168 pyrrolyl group Chemical group 0.000 claims description 46
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 45
229910052757 nitrogen Inorganic materials 0.000 claims description 42
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 41
125000003386 piperidinyl group Chemical group 0.000 claims description 41
125000001544 thienyl group Chemical group 0.000 claims description 39
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 32
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 30
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 30
238000011282 treatment Methods 0.000 claims description 30
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 29
125000003435 aroyl group Chemical group 0.000 claims description 27
125000003831 tetrazolyl group Chemical group 0.000 claims description 26
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 25
125000000753 cycloalkyl group Chemical group 0.000 claims description 25
125000004433 nitrogen atom Chemical group N* 0.000 claims description 25
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 24
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 24
125000001786 isothiazolyl group Chemical group 0.000 claims description 24
125000000842 isoxazolyl 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
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 23
125000004432 carbon atom Chemical group C* 0.000 claims description 21
125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 20
125000001041 indolyl group Chemical group 0.000 claims description 20
125000003282 alkyl amino group Chemical group 0.000 claims description 19
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 19
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 18
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 17
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 17
125000006576 di-(C1-C3-alkyl)-aminocarbonyl group Chemical group 0.000 claims description 17
208000038016 acute inflammation Diseases 0.000 claims description 16
230000006022 acute inflammation Effects 0.000 claims description 16
125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 16
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 16
125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 16
125000005842 heteroatom Chemical group 0.000 claims description 16
210000004072 lung Anatomy 0.000 claims description 16
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 16
125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 16
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 15
208000037976 chronic inflammation Diseases 0.000 claims description 15
230000006020 chronic inflammation Effects 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
125000003342 alkenyl group Chemical group 0.000 claims description 14
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 13
125000000392 cycloalkenyl group Chemical group 0.000 claims description 13
125000005494 pyridonyl group Chemical group 0.000 claims description 13
229920006395 saturated elastomer Polymers 0.000 claims description 13
208000021063 Respiratory fume inhalation disease Diseases 0.000 claims description 12
125000000304 alkynyl group Chemical group 0.000 claims description 12
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 12
125000004599 benzpyrazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 12
125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 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
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 12
125000005553 heteroaryloxy group Chemical group 0.000 claims description 11
VSIYJQNFMOOGCU-UHFFFAOYSA-N 1-(cyclohexen-1-yl)cyclohexene Chemical group C1CCCC(C=2CCCCC=2)=C1 VSIYJQNFMOOGCU-UHFFFAOYSA-N 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
125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 claims description 10
125000005436 dihydrobenzothiophenyl group Chemical group S1C(CC2=C1C=CC=C2)* 0.000 claims description 10
QYCGBAJADAGLLK-UHFFFAOYSA-N 1-(cyclohepten-1-yl)cycloheptene Chemical group C1CCCCC=C1C1=CCCCCC1 QYCGBAJADAGLLK-UHFFFAOYSA-N 0.000 claims description 9
125000005046 dihydronaphthyl group Chemical group 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 8
FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims description 8
125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims description 8
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 8
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 8
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 8
125000005940 1,4-dioxanyl group Chemical group 0.000 claims description 7
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 7
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 7
125000003277 amino group Chemical group 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
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
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 6
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
125000005056 dihydrothiazolyl group Chemical group S1C(NC=C1)* 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
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 6
125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 6
125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims description 6
125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 6
125000000081 (C5-C8) cycloalkenyl 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
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 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
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 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
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
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 5
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 5
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 5
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 5
125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 5
230000036961 partial effect Effects 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
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 5
229910052727 yttrium Inorganic materials 0.000 claims description 5
BNBBKSUHPPUOLO-UHFFFAOYSA-N (3-tert-butylphenyl) n-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]carbamate Chemical compound CC(C)(C)C1=CC=CC(OC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 BNBBKSUHPPUOLO-UHFFFAOYSA-N 0.000 claims description 4
125000006594 (C1-C3) alkylsulfony group Chemical group 0.000 claims description 4
WQEJWTVTSDKASV-UHFFFAOYSA-N 1-(1-acetyl-3,3-dimethyl-2h-indol-5-yl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C=1C=C2N(C(=O)C)CC(C)(C)C2=CC=1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 WQEJWTVTSDKASV-UHFFFAOYSA-N 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
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
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 4
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 4
VVADCVAKMLBGPC-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-(6-pyridin-3-yloxypyridin-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=C1OC1=CC=CN=C1 VVADCVAKMLBGPC-UHFFFAOYSA-N 0.000 claims description 4
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 4
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 4
OLHILEWECVENBS-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-(hydroxymethyl)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(CO)N=C1 OLHILEWECVENBS-UHFFFAOYSA-N 0.000 claims description 4
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 4
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 4
FBHTZEIJBMNUJC-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-[(1-oxothian-4-yl)amino]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=C1NC1CCS(=O)CC1 FBHTZEIJBMNUJC-UHFFFAOYSA-N 0.000 claims description 4
OXGNMBLVMSVAPZ-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-[(2,6-dimethylpiperidin-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)CCCC1C OXGNMBLVMSVAPZ-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
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 4
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 4
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 4
GYIDFUYJHFDKSW-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-[[2-cyanoethyl(pyridin-3-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)CC1=CC=CN=C1 GYIDFUYJHFDKSW-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
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 4
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 4
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 4
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 4
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 4
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 4
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 4
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 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
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 4
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 4
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 4
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 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
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 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
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 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
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 4
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 4
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 4
PQHOEPBLRPBZKT-UHFFFAOYSA-N 1-[5-tert-butyl-3-(ethylsulfonylamino)-2-methoxyphenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CCS(=O)(=O)NC1=CC(C(C)(C)C)=CC(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1OC PQHOEPBLRPBZKT-UHFFFAOYSA-N 0.000 claims description 4
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 4
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 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
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 4
GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims description 4
KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 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
125000002618 bicyclic heterocycle group Chemical group 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
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
125000002950 monocyclic group Chemical group 0.000 claims description 4
DAIAIOBTYVJHHJ-UHFFFAOYSA-N n-[1-[[5-[4-[(5-tert-butyl-2-methoxyphenyl)carbamoylamino]naphthalen-1-yl]pyridin-2-yl]methyl]pyrrolidin-3-yl]acetamide Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CC(NC(C)=O)CC1 DAIAIOBTYVJHHJ-UHFFFAOYSA-N 0.000 claims description 4
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 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
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 4
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 4
125000001181 organosilyl group Chemical group [SiH3]* 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
125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
NAZWEBNDZAMONP-UHFFFAOYSA-N 1-(5-tert-butyl-2-imidazol-1-ylphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C=1C(C(C)(C)C)=CC=C(N2C=NC=C2)C=1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 NAZWEBNDZAMONP-UHFFFAOYSA-N 0.000 claims description 3
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 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
UPXGUSBHVAVLGH-UHFFFAOYSA-N 1-[2-tert-butyl-4-(methanesulfonamido)-5-methoxyphenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=C(NS(C)(=O)=O)C(OC)=CC(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1C(C)(C)C UPXGUSBHVAVLGH-UHFFFAOYSA-N 0.000 claims description 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 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
125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 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
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
125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 3
GMIGDYDIMXGYOL-UHFFFAOYSA-N n-acetyl-n-[5-tert-butyl-2-methoxy-3-[[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]carbamoylamino]phenyl]acetamide Chemical compound C1=C(C(C)(C)C)C=C(N(C(C)=O)C(C)=O)C(OC)=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 GMIGDYDIMXGYOL-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
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[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
ULZLBCDVMYGAHV-UHFFFAOYSA-N 1-(2,2-difluoro-1,3-benzodioxol-5-yl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=C2OC(F)(F)OC2=CC=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 ULZLBCDVMYGAHV-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
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
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
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
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 2
SYEWQIACIPTFRA-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-[(2-methylsulfanylethylamino)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=C1C1=CC=C(CNCCSC)N=C1 SYEWQIACIPTFRA-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
ULVQEVVJODEZCC-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-[[3-(dimethylamino)pyrrolidin-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(N(C)C)CC1 ULVQEVVJODEZCC-UHFFFAOYSA-N 0.000 claims description 2
ZEZSFDXTRYVVAM-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylphenyl)-3-[4-[4-(morpholin-4-ylmethyl)piperidin-1-yl]naphthalen-1-yl]urea Chemical compound CC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1N1CCC(CN2CCOCC2)CC1 ZEZSFDXTRYVVAM-UHFFFAOYSA-N 0.000 claims description 2
PWENNHRVYOERJZ-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylsulfanylpyridin-3-yl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CSC1=NC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 PWENNHRVYOERJZ-UHFFFAOYSA-N 0.000 claims description 2
RFSCUKVBDSZLJK-UHFFFAOYSA-N 1-(6-tert-butyl-1,3-benzodioxol-5-yl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CC(C)(C)C1=CC=2OCOC=2C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 RFSCUKVBDSZLJK-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
PRPNFLYMCIAXMC-UHFFFAOYSA-N 1-[2-ethylsulfonyl-5-(trifluoromethyl)phenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CCS(=O)(=O)C1=CC=C(C(F)(F)F)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 PRPNFLYMCIAXMC-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
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
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
TUBMTBGAIWWEQK-UHFFFAOYSA-N 1-[5-tert-butyl-3-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-2-hydroxyphenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound OC=1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=CC(C(C)(C)C)=CC=1CC1COC(C)(C)O1 TUBMTBGAIWWEQK-UHFFFAOYSA-N 0.000 claims description 2
LJJFRDKKIIEGQB-UHFFFAOYSA-N 1-[6-chloro-4-(trifluoromethyl)pyridin-2-yl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound FC(F)(F)C1=CC(Cl)=NC(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 LJJFRDKKIIEGQB-UHFFFAOYSA-N 0.000 claims description 2
AWHKQZGPADWBLT-UHFFFAOYSA-N 1-[6-tert-butyl-4-(2-morpholin-4-ylethyl)-3-oxo-1,4-benzoxazin-8-yl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C=12OCC(=O)N(CCN3CCOCC3)C2=CC(C(C)(C)C)=CC=1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 AWHKQZGPADWBLT-UHFFFAOYSA-N 0.000 claims description 2
IDKOTTUTKZEGRW-UHFFFAOYSA-N 1-[[5-[4-[(5-tert-butyl-2-methoxyphenyl)carbamoylamino]naphthalen-1-yl]pyridin-2-yl]methyl]piperidine-4-carboxamide Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCC(C(N)=O)CC1 IDKOTTUTKZEGRW-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
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
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
RVAVFVOISHIQLI-UHFFFAOYSA-N n-[4-tert-butyl-2-[[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]carbamoylamino]phenyl]furan-2-carboxamide Chemical compound C=1C=C(C=2C=NC(CN3CCOCC3)=CC=2)C2=CC=CC=C2C=1NC(=O)NC1=CC(C(C)(C)C)=CC=C1NC(=O)C1=CC=CO1 RVAVFVOISHIQLI-UHFFFAOYSA-N 0.000 claims description 2
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 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
150000003254 radicals Chemical class 0.000 claims description 2
125000005505 thiomorpholino group Chemical group 0.000 claims description 2
125000004953 trihalomethyl group Chemical group 0.000 claims description 2
125000002252 acyl group Chemical group 0.000 claims 10
125000004442 acylamino group Chemical group 0.000 claims 6
125000002837 carbocyclic group Chemical group 0.000 claims 2
HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 2
125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 1
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
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 1
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 1
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 1
ZDCYCEGUVOQVHD-UHFFFAOYSA-N 1-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]-3-(1,3,3-trimethyl-2h-indol-5-yl)urea Chemical compound C=1C=C2N(C)CC(C)(C)C2=CC=1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 ZDCYCEGUVOQVHD-UHFFFAOYSA-N 0.000 claims 1
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
UNKPHKXVYMTNQW-UHFFFAOYSA-N COC1=C(CC(N)=O)C=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 Chemical compound COC1=C(CC(N)=O)C=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 UNKPHKXVYMTNQW-UHFFFAOYSA-N 0.000 claims 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
125000005241 heteroarylamino group Chemical group 0.000 claims 1
230000001154 acute effect Effects 0.000 abstract description 10
239000000779 smoke Substances 0.000 abstract description 4
125000006615 aromatic heterocyclic group Chemical group 0.000 abstract description 3
206010035664 Pneumonia Diseases 0.000 abstract description 2
230000001684 chronic effect Effects 0.000 abstract description 2
108060008682 Tumor Necrosis Factor Proteins 0.000 description 38
102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 38
102000000589 Interleukin-1 Human genes 0.000 description 23
108010002352 Interleukin-1 Proteins 0.000 description 23
MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 22
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 21
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 20
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 16
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
208000024827 Alzheimer disease Diseases 0.000 description 13
102000004889 Interleukin-6 Human genes 0.000 description 12
108090001005 Interleukin-6 Proteins 0.000 description 12
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 12
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 12
230000004054 inflammatory process Effects 0.000 description 11
230000000770 proinflammatory effect Effects 0.000 description 11
206010061218 Inflammation Diseases 0.000 description 10
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
210000004027 cell Anatomy 0.000 description 10
125000002757 morpholinyl group Chemical group 0.000 description 10
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
208000022559 Inflammatory bowel disease Diseases 0.000 description 9
230000006378 damage Effects 0.000 description 9
230000002757 inflammatory effect Effects 0.000 description 9
208000014674 injury Diseases 0.000 description 9
125000004457 alkyl amino carbonyl group Chemical group 0.000 description 8
239000003112 inhibitor Substances 0.000 description 8
229930192474 thiophene Natural products 0.000 description 8
FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 7
108010017213 Granulocyte-Macrophage Colony-Stimulating Factor Proteins 0.000 description 7
102100039620 Granulocyte-macrophage colony-stimulating factor Human genes 0.000 description 7
108090001007 Interleukin-8 Proteins 0.000 description 7
102000004890 Interleukin-8 Human genes 0.000 description 7
230000014509 gene expression Effects 0.000 description 7
238000004519 manufacturing process Methods 0.000 description 7
230000008569 process Effects 0.000 description 7
206010039073 rheumatoid arthritis Diseases 0.000 description 7
150000003839 salts Chemical class 0.000 description 7
239000000126 substance Substances 0.000 description 7
102100026018 Interleukin-1 receptor antagonist protein Human genes 0.000 description 6
101710144554 Interleukin-1 receptor antagonist protein Proteins 0.000 description 6
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 6
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
210000000988 bone and bone Anatomy 0.000 description 6
WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical group C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 description 6
MAWOHFOSAIXURX-UHFFFAOYSA-N cyclopentylcyclopentane Chemical group C1CCCC1C1CCCC1 MAWOHFOSAIXURX-UHFFFAOYSA-N 0.000 description 6
239000002552 dosage form Substances 0.000 description 6
239000003814 drug Substances 0.000 description 6
125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 6
208000011580 syndromic disease Diseases 0.000 description 6
206010001052 Acute respiratory distress syndrome Diseases 0.000 description 5
241000725303 Human immunodeficiency virus Species 0.000 description 5
208000013616 Respiratory Distress Syndrome Diseases 0.000 description 5
208000027418 Wounds and injury Diseases 0.000 description 5
239000002253 acid Substances 0.000 description 5
208000011341 adult acute respiratory distress syndrome Diseases 0.000 description 5
201000000028 adult respiratory distress syndrome Diseases 0.000 description 5
ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical group C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 description 5
238000011161 development Methods 0.000 description 5
230000018109 developmental process Effects 0.000 description 5
208000035475 disorder Diseases 0.000 description 5
201000006417 multiple sclerosis Diseases 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
125000004568 thiomorpholinyl group Chemical group 0.000 description 5
UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 4
LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 4
BBOPRMNMLDLRKQ-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[5-(morpholin-4-ylmethyl)pyridin-2-yl]naphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3N=CC(CN4CCOCC4)=CC=3)=CC=2)=CC(C(C)(C)C)=N1 BBOPRMNMLDLRKQ-UHFFFAOYSA-N 0.000 description 4
KAZMQKPLIPWQNO-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=CC(C(C)(C)C)=N1 KAZMQKPLIPWQNO-UHFFFAOYSA-N 0.000 description 4
208000006386 Bone Resorption Diseases 0.000 description 4
206010006895 Cachexia Diseases 0.000 description 4
206010020772 Hypertension Diseases 0.000 description 4
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
208000002193 Pain Diseases 0.000 description 4
102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 4
108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 4
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
206010040070 Septic Shock Diseases 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000002671 adjuvant Substances 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
230000024279 bone resorption Effects 0.000 description 4
125000005356 cycloalkylalkenyl group Chemical group 0.000 description 4
229940079593 drug Drugs 0.000 description 4
230000026030 halogenation Effects 0.000 description 4
238000005658 halogenation reaction Methods 0.000 description 4
230000001939 inductive effect Effects 0.000 description 4
208000015181 infectious disease Diseases 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
230000003902 lesion Effects 0.000 description 4
239000000203 mixture Substances 0.000 description 4
230000008506 pathogenesis Effects 0.000 description 4
239000000651 prodrug Substances 0.000 description 4
229940002612 prodrug Drugs 0.000 description 4
208000024891 symptom Diseases 0.000 description 4
230000008733 trauma Effects 0.000 description 4
ITBZMXUGTUHWGK-UHFFFAOYSA-N 1-(2-methyl-5-phenylphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CC1=CC=C(C=2C=CC=CC=2)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 ITBZMXUGTUHWGK-UHFFFAOYSA-N 0.000 description 3
SEHRPXLAFSFMSI-UHFFFAOYSA-N 1-(2-methyl-5-propan-2-ylphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CC(C)C1=CC=C(C)C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 SEHRPXLAFSFMSI-UHFFFAOYSA-N 0.000 description 3
OKJJYXJBKGPJLH-UHFFFAOYSA-N 1-(2-tert-butyl-5-methylpyridin-4-yl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CC1=CN=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 OKJJYXJBKGPJLH-UHFFFAOYSA-N 0.000 description 3
QCYRZCANKXBEHZ-UHFFFAOYSA-N 1-(3-tert-butylphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CC(C)(C)C1=CC=CC(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 QCYRZCANKXBEHZ-UHFFFAOYSA-N 0.000 description 3
FFBUDLJONCUVMD-UHFFFAOYSA-N 1-(5-butan-2-yl-2-methoxyphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CCC(C)C1=CC=C(OC)C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 FFBUDLJONCUVMD-UHFFFAOYSA-N 0.000 description 3
GQLCRASPHLJOAW-UHFFFAOYSA-N 1-(5-chloro-2,4-dimethoxyphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 GQLCRASPHLJOAW-UHFFFAOYSA-N 0.000 description 3
TVJZPCWJLIDBMN-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-(morpholin-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=C1CN1CCOCC1 TVJZPCWJLIDBMN-UHFFFAOYSA-N 0.000 description 3
DVBKZPSCTGHZHB-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 DVBKZPSCTGHZHB-UHFFFAOYSA-N 0.000 description 3
WUGLAQLTUHTAJZ-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylpyridin-3-yl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CC1=NC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 WUGLAQLTUHTAJZ-UHFFFAOYSA-N 0.000 description 3
UHWHXNSOZPFADL-UHFFFAOYSA-N 1-(5-tert-butyl-2-phenylphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C=1C(C(C)(C)C)=CC=C(C=2C=CC=CC=2)C=1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 UHWHXNSOZPFADL-UHFFFAOYSA-N 0.000 description 3
MOCYVOKWTBPIGE-UHFFFAOYSA-N 1-[2-methoxy-5-(2-methylbutan-2-yl)phenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CCC(C)(C)C1=CC=C(OC)C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 MOCYVOKWTBPIGE-UHFFFAOYSA-N 0.000 description 3
KBYAIWPIVQYVDZ-UHFFFAOYSA-N 1-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]-3-[4-(trifluoromethoxy)phenyl]urea Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 KBYAIWPIVQYVDZ-UHFFFAOYSA-N 0.000 description 3
YTISFTRMFXFAKS-UHFFFAOYSA-N 1-[5-tert-butyl-2-(2-methylpyrimidin-5-yl)phenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=NC(C)=NC=C1C1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 YTISFTRMFXFAKS-UHFFFAOYSA-N 0.000 description 3
FRPYEOALLMIMQH-UHFFFAOYSA-N 1-[5-tert-butyl-2-(2-methylpyrimidin-5-yl)pyrazol-3-yl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=NC(C)=NC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=CC(C(C)(C)C)=N1 FRPYEOALLMIMQH-UHFFFAOYSA-N 0.000 description 3
JTRWJPGNIGWPEL-UHFFFAOYSA-N 1-[5-tert-butyl-2-(2-methylsulfanylpyrimidin-5-yl)pyrazol-3-yl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=NC(SC)=NC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=CC(C(C)(C)C)=N1 JTRWJPGNIGWPEL-UHFFFAOYSA-N 0.000 description 3
WMRRCPFERWSFEX-UHFFFAOYSA-N 1-[5-tert-butyl-2-(3-hydroxypropyl)phenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CC(C)(C)C1=CC=C(CCCO)C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 WMRRCPFERWSFEX-UHFFFAOYSA-N 0.000 description 3
HWLKVWAXMATBJX-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[6-[(1-oxo-1,4-thiazinan-4-yl)methyl]pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCS(=O)CC4)=CC=3)=CC=2)=CC(C(C)(C)C)=N1 HWLKVWAXMATBJX-UHFFFAOYSA-N 0.000 description 3
SOZBHYOHAZVOBT-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methoxypyridin-3-yl)pyrazol-3-yl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=NC(OC)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=CC(C(C)(C)C)=N1 SOZBHYOHAZVOBT-UHFFFAOYSA-N 0.000 description 3
IRJNKEVLQRRUSA-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=NC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=CC(C(C)(C)C)=N1 IRJNKEVLQRRUSA-UHFFFAOYSA-N 0.000 description 3
BOAGBUKUGQYVKM-UHFFFAOYSA-N 1-[5-tert-butyl-2-(methoxymethyl)phenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COCC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 BOAGBUKUGQYVKM-UHFFFAOYSA-N 0.000 description 3
XZMNYZSIMZGMEY-UHFFFAOYSA-N 1-[5-tert-butyl-2-(morpholine-4-carbonyl)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(=O)N1CCOCC1 XZMNYZSIMZGMEY-UHFFFAOYSA-N 0.000 description 3
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 3
208000030507 AIDS Diseases 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
208000011231 Crohn disease Diseases 0.000 description 3
206010012289 Dementia Diseases 0.000 description 3
208000031886 HIV Infections Diseases 0.000 description 3
208000037357 HIV infectious disease Diseases 0.000 description 3
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
210000001744 T-lymphocyte Anatomy 0.000 description 3
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 3
206010067584 Type 1 diabetes mellitus Diseases 0.000 description 3
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 3
239000005557 antagonist Substances 0.000 description 3
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 3
210000003169 central nervous system Anatomy 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
125000004122 cyclic group Chemical group 0.000 description 3
230000016396 cytokine production Effects 0.000 description 3
206010012601 diabetes mellitus Diseases 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000002158 endotoxin Substances 0.000 description 3
125000005844 heterocyclyloxy group Chemical group 0.000 description 3
208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 3
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 3
210000000265 leukocyte Anatomy 0.000 description 3
229920006008 lipopolysaccharide Polymers 0.000 description 3
208000010125 myocardial infarction Diseases 0.000 description 3
230000007302 negative regulation of cytokine production Effects 0.000 description 3
210000000440 neutrophil Anatomy 0.000 description 3
201000008482 osteoarthritis Diseases 0.000 description 3
210000005259 peripheral blood Anatomy 0.000 description 3
239000011886 peripheral blood Substances 0.000 description 3
239000008194 pharmaceutical composition Substances 0.000 description 3
108090000623 proteins and genes Proteins 0.000 description 3
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 3
108020003175 receptors Proteins 0.000 description 3
102000005962 receptors Human genes 0.000 description 3
230000004044 response Effects 0.000 description 3
150000003335 secondary amines Chemical class 0.000 description 3
210000003491 skin Anatomy 0.000 description 3
150000003512 tertiary amines Chemical class 0.000 description 3
238000012360 testing method Methods 0.000 description 3
150000003536 tetrazoles Chemical class 0.000 description 3
DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 3
230000006433 tumor necrosis factor production Effects 0.000 description 3
125000006527 (C1-C5) alkyl group Chemical group 0.000 description 2
125000006619 (C1-C6) dialkylamino group Chemical group 0.000 description 2
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 2
125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 description 2
KZSAABCCRZPRJK-UHFFFAOYSA-N 1-(3-tert-butylphenyl)-3-[4-[4-(morpholin-4-ylmethyl)phenyl]naphthalen-1-yl]urea Chemical compound CC(C)(C)C1=CC=CC(NC(=O)NC=2C3=CC=CC=C3C(C=3C=CC(CN4CCOCC4)=CC=3)=CC=2)=C1 KZSAABCCRZPRJK-UHFFFAOYSA-N 0.000 description 2
CAQYVODRHABUJH-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxy-3-propylphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CCCC1=CC(C(C)(C)C)=CC(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1OC CAQYVODRHABUJH-UHFFFAOYSA-N 0.000 description 2
MIBYPKINMBREPE-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[2-(morpholin-4-ylmethyl)phenyl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C1=CC=CC=C1CN1CCOCC1 MIBYPKINMBREPE-UHFFFAOYSA-N 0.000 description 2
RDBWUJDARKEUNS-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[4-(oxan-4-ylamino)phenyl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=C1)=CC=C1NC1CCOCC1 RDBWUJDARKEUNS-UHFFFAOYSA-N 0.000 description 2
SYGFXFLLYOMQKH-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[4-(thiomorpholin-4-ylmethyl)phenyl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=C1)=CC=C1CN1CCSCC1 SYGFXFLLYOMQKH-UHFFFAOYSA-N 0.000 description 2
HZMQYZHTBFZUTB-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylphenyl)-3-[4-[4-(morpholin-4-ylmethyl)imidazol-1-yl]naphthalen-1-yl]urea Chemical compound CC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1N1C=C(CN2CCOCC2)N=C1 HZMQYZHTBFZUTB-UHFFFAOYSA-N 0.000 description 2
NMJPRGQFIVOUJR-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylphenyl)-3-[4-[4-(morpholin-4-ylmethyl)phenyl]naphthalen-1-yl]urea Chemical compound CC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=C1)=CC=C1CN1CCOCC1 NMJPRGQFIVOUJR-UHFFFAOYSA-N 0.000 description 2
ULCWMQOJQGXRRU-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylphenyl)-3-[4-[6-(3-methoxypropylamino)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=NC(NCCCOC)=CC=C1C(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=CC=C1C ULCWMQOJQGXRRU-UHFFFAOYSA-N 0.000 description 2
YNOBSNNZZPAJLM-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylphenyl)-3-[4-[6-[3-methoxypropyl(methyl)amino]pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=NC(N(C)CCCOC)=CC=C1C(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=CC=C1C YNOBSNNZZPAJLM-UHFFFAOYSA-N 0.000 description 2
HTEMUDPCVAMLEB-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylpyrazol-3-yl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CN1N=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 HTEMUDPCVAMLEB-UHFFFAOYSA-N 0.000 description 2
VKTLDTPBPJGRIJ-UHFFFAOYSA-N 1-(5-tert-butyl-2-morpholin-4-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=C1N1CCOCC1 VKTLDTPBPJGRIJ-UHFFFAOYSA-N 0.000 description 2
URDGGACDWSWQMA-UHFFFAOYSA-N 1-[2-(2-aminopyrimidin-5-yl)-5-tert-butylpyrazol-3-yl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C=1N=C(N)N=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 URDGGACDWSWQMA-UHFFFAOYSA-N 0.000 description 2
QHNXXXAKKWZQOY-UHFFFAOYSA-N 1-[2-(6-aminopyridin-3-yl)-5-tert-butylpyrazol-3-yl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C=1C=C(N)N=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 QHNXXXAKKWZQOY-UHFFFAOYSA-N 0.000 description 2
HXTMKULUSANYTM-UHFFFAOYSA-N 1-[2-methoxy-5-(1-methylcyclopropyl)phenyl]-3-[4-[2-(morpholin-4-ylmethyl)pyrimidin-5-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C2(C)CC2)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CN=C1CN1CCOCC1 HXTMKULUSANYTM-UHFFFAOYSA-N 0.000 description 2
DIPZYLWYNOYUJR-UHFFFAOYSA-N 1-[2-methoxy-5-(2-methylbutan-2-yl)phenyl]-3-[4-[4-(thiomorpholin-4-ylmethyl)phenyl]naphthalen-1-yl]urea Chemical compound CCC(C)(C)C1=CC=C(OC)C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=CC(CN4CCSCC4)=CC=3)=CC=2)=C1 DIPZYLWYNOYUJR-UHFFFAOYSA-N 0.000 description 2
SVGQPGDMEXQRQN-UHFFFAOYSA-N 1-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 SVGQPGDMEXQRQN-UHFFFAOYSA-N 0.000 description 2
ZNYNPFIRXYNDQU-UHFFFAOYSA-N 1-[5-tert-butyl-2-(2-cyanoethyl)pyrazol-3-yl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound N#CCCN1N=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 ZNYNPFIRXYNDQU-UHFFFAOYSA-N 0.000 description 2
DXBVYGQYSUEISI-UHFFFAOYSA-N 1-[5-tert-butyl-2-(2-methoxypyrimidin-5-yl)pyrazol-3-yl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=NC(OC)=NC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=CC(C(C)(C)C)=N1 DXBVYGQYSUEISI-UHFFFAOYSA-N 0.000 description 2
FHLQPCUMQVYGNX-UHFFFAOYSA-N 1-[5-tert-butyl-2-(2-methylpyrimidin-5-yl)pyrazol-3-yl]-3-[4-[6-(oxan-4-ylamino)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=NC(C)=NC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(NC4CCOCC4)=CC=3)=CC=2)=CC(C(C)(C)C)=N1 FHLQPCUMQVYGNX-UHFFFAOYSA-N 0.000 description 2
MCKFAVIMAYCFIH-UHFFFAOYSA-N 1-[5-tert-butyl-2-(2-methylpyrimidin-5-yl)pyrazol-3-yl]-3-[4-[6-[(1-oxo-1,4-thiazinan-4-yl)methyl]pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=NC(C)=NC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCS(=O)CC4)=CC=3)=CC=2)=CC(C(C)(C)C)=N1 MCKFAVIMAYCFIH-UHFFFAOYSA-N 0.000 description 2
XDGJCAJXCUILEZ-UHFFFAOYSA-N 1-[5-tert-butyl-2-(3-morpholin-4-yl-3-oxopropyl)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=C1CCC(=O)N1CCOCC1 XDGJCAJXCUILEZ-UHFFFAOYSA-N 0.000 description 2
ASJFQKWXDUOSDG-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-(3-morpholin-4-ylcyclohepten-1-yl)naphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3CCCCC(C=3)N3CCOCC3)=CC=2)=CC(C(C)(C)C)=N1 ASJFQKWXDUOSDG-UHFFFAOYSA-N 0.000 description 2
WXBMMVPWYARDGV-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-(morpholin-4-ylmethyl)pyrimidin-5-yl]naphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=NC=3)=CC=2)=CC(C(C)(C)C)=N1 WXBMMVPWYARDGV-UHFFFAOYSA-N 0.000 description 2
USGPKPYWOURZEK-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-(morpholine-4-carbonyl)pyrimidin-5-yl]naphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(=NC=3)C(=O)N3CCOCC3)=CC=2)=CC(C(C)(C)C)=N1 USGPKPYWOURZEK-UHFFFAOYSA-N 0.000 description 2
BMXNQGASYHVGST-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[3-(morpholin-4-ylmethyl)phenyl]naphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=C(CN4CCOCC4)C=CC=3)=CC=2)=CC(C(C)(C)C)=N1 BMXNQGASYHVGST-UHFFFAOYSA-N 0.000 description 2
JHCPOCAZTCPCQQ-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[4-(morpholin-4-ylmethyl)phenyl]naphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=CC(CN4CCOCC4)=CC=3)=CC=2)=CC(C(C)(C)C)=N1 JHCPOCAZTCPCQQ-UHFFFAOYSA-N 0.000 description 2
DDSUPZFRUFSRID-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[4-[methylamino(pyridin-3-yl)methyl]phenyl]naphthalen-1-yl]urea Chemical compound C=1C=CN=CC=1C(NC)C(C=C1)=CC=C1C(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=NN1C1=CC=C(C)C=C1 DDSUPZFRUFSRID-UHFFFAOYSA-N 0.000 description 2
IKJJFZMMHAIPNB-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[5-(morpholin-4-ylmethyl)furan-2-yl]naphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3OC(CN4CCOCC4)=CC=3)=CC=2)=CC(C(C)(C)C)=N1 IKJJFZMMHAIPNB-UHFFFAOYSA-N 0.000 description 2
HWPPZXCPZJQDSK-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[6-(thiomorpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCSCC4)=CC=3)=CC=2)=CC(C(C)(C)C)=N1 HWPPZXCPZJQDSK-UHFFFAOYSA-N 0.000 description 2
HZOOQEANFBKRIM-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[6-[(1-oxothian-4-yl)amino]pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(NC4CCS(=O)CC4)=CC=3)=CC=2)=CC(C(C)(C)C)=N1 HZOOQEANFBKRIM-UHFFFAOYSA-N 0.000 description 2
SIOKWKLHLCPFPN-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[3-(morpholin-4-ylmethyl)cyclohexen-1-yl]naphthalen-1-yl]urea Chemical compound C1=NC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3CCCC(CN4CCOCC4)C=3)=CC=2)=CC(C(C)(C)C)=N1 SIOKWKLHLCPFPN-UHFFFAOYSA-N 0.000 description 2
KNAHYEJUOBRJIC-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[3-hydroxy-4-(oxolan-3-ylmethyl)phenyl]naphthalen-1-yl]urea Chemical compound C1=NC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=C(O)C(CC4COCC4)=CC=3)=CC=2)=CC(C(C)(C)C)=N1 KNAHYEJUOBRJIC-UHFFFAOYSA-N 0.000 description 2
XFJUDEHDAGOXMR-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[4-(furan-2-ylmethyl)-3-hydroxyphenyl]naphthalen-1-yl]urea Chemical compound C1=NC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=C(O)C(CC=4OC=CC=4)=CC=3)=CC=2)=CC(C(C)(C)C)=N1 XFJUDEHDAGOXMR-UHFFFAOYSA-N 0.000 description 2
OVPDTMKGYGGJNU-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[4-(morpholin-4-ylmethyl)phenyl]naphthalen-1-yl]urea Chemical compound C1=NC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=CC(CN4CCOCC4)=CC=3)=CC=2)=CC(C(C)(C)C)=N1 OVPDTMKGYGGJNU-UHFFFAOYSA-N 0.000 description 2
AITNULMUNMWYTC-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[4-[[2-cyanoethyl(oxolan-2-ylmethyl)amino]methyl]phenyl]naphthalen-1-yl]urea Chemical compound C1=NC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=CC(CN(CCC#N)CC4OCCC4)=CC=3)=CC=2)=CC(C(C)(C)C)=N1 AITNULMUNMWYTC-UHFFFAOYSA-N 0.000 description 2
OCYIIPQUEFWVOX-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[4-[[2-cyanoethyl(pyridin-3-ylmethyl)amino]methyl]phenyl]naphthalen-1-yl]urea Chemical compound C1=NC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=CC(CN(CCC#N)CC=4C=NC=CC=4)=CC=3)=CC=2)=CC(C(C)(C)C)=N1 OCYIIPQUEFWVOX-UHFFFAOYSA-N 0.000 description 2
GUFFIMDDQASHSZ-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[4-methoxy-6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound N=1C=C(C=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=NC(C)=CC=3)=CC=2)C(OC)=CC=1CN1CCOCC1 GUFFIMDDQASHSZ-UHFFFAOYSA-N 0.000 description 2
MKQIWKMKTHHOCV-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[6-(1-morpholin-4-ylpropyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C=1C=C(C=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=NC(C)=CC=3)=CC=2)C=NC=1C(CC)N1CCOCC1 MKQIWKMKTHHOCV-UHFFFAOYSA-N 0.000 description 2
MXEDNULIXVIKDP-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[6-(2-oxa-5-azabicyclo[2.2.1]heptan-5-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=NC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4C5CC(OC5)C4)=CC=3)=CC=2)=CC(C(C)(C)C)=N1 MXEDNULIXVIKDP-UHFFFAOYSA-N 0.000 description 2
DVJVCKCZQZCEDE-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[6-(3-cyanopropoxy)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=NC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(OCCCC#N)=CC=3)=CC=2)=CC(C(C)(C)C)=N1 DVJVCKCZQZCEDE-UHFFFAOYSA-N 0.000 description 2
KXRIDVAKSBVUNI-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[6-(4-hydroxybutoxy)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=NC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(OCCCCO)=CC=3)=CC=2)=CC(C(C)(C)C)=N1 KXRIDVAKSBVUNI-UHFFFAOYSA-N 0.000 description 2
CLADYCSYECLIBL-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[6-(4-hydroxybutylamino)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=NC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(NCCCCO)=CC=3)=CC=2)=CC(C(C)(C)C)=N1 CLADYCSYECLIBL-UHFFFAOYSA-N 0.000 description 2
WLOIMSRPDWSQAE-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[6-(oxan-4-ylamino)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=NC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(NC4CCOCC4)=CC=3)=CC=2)=CC(C(C)(C)C)=N1 WLOIMSRPDWSQAE-UHFFFAOYSA-N 0.000 description 2
VNJBNRJGLBZRMN-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[6-(pyridin-3-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=NC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CC=4C=NC=CC=4)=CC=3)=CC=2)=CC(C(C)(C)C)=N1 VNJBNRJGLBZRMN-UHFFFAOYSA-N 0.000 description 2
YEBURKNDXZVPML-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[6-[(2,6-dimethylmorpholin-4-yl)methyl]pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1C(C)OC(C)CN1CC1=CC=C(C=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=NC(C)=CC=3)=CC=2)C=N1 YEBURKNDXZVPML-UHFFFAOYSA-N 0.000 description 2
DYHSPTUMGZFPAR-UHFFFAOYSA-N 2-[4-tert-butyl-2-[[4-[6-[(2,6-dimethylmorpholin-4-yl)methyl]pyridin-3-yl]naphthalen-1-yl]carbamoylamino]phenoxy]acetamide Chemical compound C1C(C)OC(C)CN1CC1=CC=C(C=2C3=CC=CC=C3C(NC(=O)NC=3C(=CC=C(C=3)C(C)(C)C)OCC(N)=O)=CC=2)C=N1 DYHSPTUMGZFPAR-UHFFFAOYSA-N 0.000 description 2
SYPCACMBAYWOGV-UHFFFAOYSA-N 3-[4-[(5-tert-butyl-2-methoxyphenyl)carbamoylamino]naphthalen-1-yl]benzamide Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C1=CC=CC(C(N)=O)=C1 SYPCACMBAYWOGV-UHFFFAOYSA-N 0.000 description 2
ZGXFVYOWURGVSM-UHFFFAOYSA-N 4-[4-(2-morpholin-4-yl-2-thiomorpholin-4-ylthiomorpholin-4-yl)sulfinyl-2-thiomorpholin-4-ylthiomorpholin-2-yl]morpholine Chemical compound C1CSC(N2CCSCC2)(N2CCOCC2)CN1S(=O)N(C1)CCSC1(N1CCSCC1)N1CCOCC1 ZGXFVYOWURGVSM-UHFFFAOYSA-N 0.000 description 2
RZBFJKANZHTGNJ-UHFFFAOYSA-N 4-tert-butyl-2-[[4-[2-chloro-4-(morpholin-4-ylmethyl)phenyl]naphthalen-1-yl]carbamoylamino]benzamide Chemical compound CC(C)(C)C1=CC=C(C(N)=O)C(NC(=O)NC=2C3=CC=CC=C3C(C=3C(=CC(CN4CCOCC4)=CC=3)Cl)=CC=2)=C1 RZBFJKANZHTGNJ-UHFFFAOYSA-N 0.000 description 2
BUXDDVRTTIYFHI-UHFFFAOYSA-N 5-[3-tert-butyl-5-[[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]carbamoylamino]pyrazol-1-yl]-2-methylbenzamide Chemical compound C1=C(C(N)=O)C(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=CC(C(C)(C)C)=N1 BUXDDVRTTIYFHI-UHFFFAOYSA-N 0.000 description 2
208000031261 Acute myeloid leukaemia Diseases 0.000 description 2
201000001320 Atherosclerosis Diseases 0.000 description 2
208000023275 Autoimmune disease Diseases 0.000 description 2
208000020084 Bone disease Diseases 0.000 description 2
208000014644 Brain disease Diseases 0.000 description 2
208000000094 Chronic Pain Diseases 0.000 description 2
235000008733 Citrus aurantifolia Nutrition 0.000 description 2
206010009900 Colitis ulcerative Diseases 0.000 description 2
208000035473 Communicable disease Diseases 0.000 description 2
206010012438 Dermatitis atopic Diseases 0.000 description 2
206010059866 Drug resistance Diseases 0.000 description 2
238000008157 ELISA kit Methods 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
206010018366 Glomerulonephritis acute Diseases 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
208000009329 Graft vs Host Disease Diseases 0.000 description 2
241000700721 Hepatitis B virus Species 0.000 description 2
101000611183 Homo sapiens Tumor necrosis factor Proteins 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
206010021143 Hypoxia Diseases 0.000 description 2
108010002350 Interleukin-2 Proteins 0.000 description 2
102000000588 Interleukin-2 Human genes 0.000 description 2
ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 2
229930182816 L-glutamine Natural products 0.000 description 2
102000055008 Matrilin Proteins Human genes 0.000 description 2
108010072582 Matrilin Proteins Proteins 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
208000034578 Multiple myelomas Diseases 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
208000033776 Myeloid Acute Leukemia Diseases 0.000 description 2
206010051606 Necrotising colitis Diseases 0.000 description 2
208000003076 Osteolysis Diseases 0.000 description 2
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
206010035226 Plasma cell myeloma Diseases 0.000 description 2
201000004681 Psoriasis Diseases 0.000 description 2
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
206010037660 Pyrexia Diseases 0.000 description 2
239000012980 RPMI-1640 medium Substances 0.000 description 2
208000006011 Stroke Diseases 0.000 description 2
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
235000011941 Tilia x europaea Nutrition 0.000 description 2
206010044248 Toxic shock syndrome Diseases 0.000 description 2
231100000650 Toxic shock syndrome Toxicity 0.000 description 2
201000006704 Ulcerative Colitis Diseases 0.000 description 2
206010046851 Uveitis Diseases 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
231100000851 acute glomerulonephritis Toxicity 0.000 description 2
208000005298 acute pain Diseases 0.000 description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
230000000172 allergic effect Effects 0.000 description 2
238000010171 animal model Methods 0.000 description 2
230000003092 anti-cytokine Effects 0.000 description 2
238000013459 approach Methods 0.000 description 2
206010003246 arthritis Diseases 0.000 description 2
208000006673 asthma Diseases 0.000 description 2
230000003143 atherosclerotic effect Effects 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
201000008937 atopic dermatitis Diseases 0.000 description 2
208000010668 atopic eczema Diseases 0.000 description 2
239000002585 base Substances 0.000 description 2
230000008901 benefit Effects 0.000 description 2
125000005605 benzo group Chemical group 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
230000000903 blocking effect Effects 0.000 description 2
230000000747 cardiac effect Effects 0.000 description 2
230000001413 cellular effect Effects 0.000 description 2
208000015114 central nervous system disease Diseases 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
230000001276 controlling effect Effects 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
230000001419 dependent effect Effects 0.000 description 2
206010013663 drug dependence Diseases 0.000 description 2
230000004064 dysfunction Effects 0.000 description 2
239000012091 fetal bovine serum Substances 0.000 description 2
208000024908 graft versus host disease Diseases 0.000 description 2
210000003714 granulocyte Anatomy 0.000 description 2
238000001631 haemodialysis Methods 0.000 description 2
208000019622 heart disease Diseases 0.000 description 2
230000000322 hemodialysis Effects 0.000 description 2
102000057041 human TNF Human genes 0.000 description 2
238000011534 incubation Methods 0.000 description 2
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
230000006698 induction Effects 0.000 description 2
230000028709 inflammatory response Effects 0.000 description 2
208000030603 inherited susceptibility to asthma Diseases 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
210000003734 kidney Anatomy 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
239000004571 lime Substances 0.000 description 2
208000029791 lytic metastatic bone lesion Diseases 0.000 description 2
210000002540 macrophage Anatomy 0.000 description 2
239000002609 medium Substances 0.000 description 2
239000002207 metabolite Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
125000000896 monocarboxylic acid group Chemical group 0.000 description 2
TVBZKMHBLROHSN-UHFFFAOYSA-N n-[5-[4-[[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]pyridin-2-yl]acetamide Chemical compound C1=NC(NC(=O)C)=CC=C1C(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=NN1C1=CC=C(C)N=C1 TVBZKMHBLROHSN-UHFFFAOYSA-N 0.000 description 2
208000004995 necrotizing enterocolitis Diseases 0.000 description 2
229910017604 nitric acid Inorganic materials 0.000 description 2
125000006574 non-aromatic ring group Chemical group 0.000 description 2
210000000963 osteoblast Anatomy 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 description 2
108010068338 p38 Mitogen-Activated Protein Kinases Proteins 0.000 description 2
230000007918 pathogenicity Effects 0.000 description 2
230000007310 pathophysiology Effects 0.000 description 2
230000037361 pathway Effects 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
201000006195 perinatal necrotizing enterocolitis Diseases 0.000 description 2
208000028169 periodontal disease Diseases 0.000 description 2
239000002464 receptor antagonist Substances 0.000 description 2
229940044551 receptor antagonist Drugs 0.000 description 2
230000009467 reduction Effects 0.000 description 2
238000006722 reduction reaction Methods 0.000 description 2
230000002829 reductive effect Effects 0.000 description 2
230000001105 regulatory effect Effects 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
230000036303 septic shock Effects 0.000 description 2
210000002966 serum Anatomy 0.000 description 2
208000017520 skin disease Diseases 0.000 description 2
UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
208000011117 substance-related disease Diseases 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
201000000596 systemic lupus erythematosus Diseases 0.000 description 2
RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
150000003573 thiols Chemical class 0.000 description 2
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 2
230000002537 thrombolytic effect Effects 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
238000002054 transplantation Methods 0.000 description 2
230000000472 traumatic effect Effects 0.000 description 2
150000003672 ureas Chemical class 0.000 description 2
MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 description 1
NQPJDJVGBDHCAD-UHFFFAOYSA-N 1,3-diazinan-2-one Chemical compound OC1=NCCCN1 NQPJDJVGBDHCAD-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
REERFUMNYQUJQG-UHFFFAOYSA-N 1-(1,3-benzothiazol-6-yl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C=1C=C2N=CSC2=CC=1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 REERFUMNYQUJQG-UHFFFAOYSA-N 0.000 description 1
GVSWVZOVDXUIFL-UHFFFAOYSA-N 1-(2,3-dichlorophenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound ClC1=CC=CC(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1Cl GVSWVZOVDXUIFL-UHFFFAOYSA-N 0.000 description 1
SUAXLPQBMQNTSP-UHFFFAOYSA-N 1-(2,3-dimethylphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CC1=CC=CC(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1C SUAXLPQBMQNTSP-UHFFFAOYSA-N 0.000 description 1
WUQGLNIDHPPBNI-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound ClC1=CC(Cl)=CC=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 WUQGLNIDHPPBNI-UHFFFAOYSA-N 0.000 description 1
SYBGVADGOHETFE-UHFFFAOYSA-N 1-(2,4-dimethoxyphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COC1=CC(OC)=CC=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 SYBGVADGOHETFE-UHFFFAOYSA-N 0.000 description 1
RXDWJZREJOZEGL-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CC1=CC(C)=CC=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 RXDWJZREJOZEGL-UHFFFAOYSA-N 0.000 description 1
SFPBHNAFVHSBPU-UHFFFAOYSA-N 1-(2,5-dichlorophenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound ClC1=CC=C(Cl)C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 SFPBHNAFVHSBPU-UHFFFAOYSA-N 0.000 description 1
CYCLXMSCCANVDK-UHFFFAOYSA-N 1-(2,5-diethoxyphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CCOC1=CC=C(OCC)C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 CYCLXMSCCANVDK-UHFFFAOYSA-N 0.000 description 1
AWEJMFLMIIIWQH-UHFFFAOYSA-N 1-(2,5-difluorophenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound FC1=CC=C(F)C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 AWEJMFLMIIIWQH-UHFFFAOYSA-N 0.000 description 1
FAZWSMQUSZIVSV-UHFFFAOYSA-N 1-(2,5-dimethoxyphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(OC)C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 FAZWSMQUSZIVSV-UHFFFAOYSA-N 0.000 description 1
WUXVANAGFKJIES-UHFFFAOYSA-N 1-(2,6-dibromo-4-propan-2-ylphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound BrC1=CC(C(C)C)=CC(Br)=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 WUXVANAGFKJIES-UHFFFAOYSA-N 0.000 description 1
CRTPUTWKRSDIKT-UHFFFAOYSA-N 1-(2-chloro-6-methylphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CC1=CC=CC(Cl)=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 CRTPUTWKRSDIKT-UHFFFAOYSA-N 0.000 description 1
MCESVWQYJXZHOH-UHFFFAOYSA-N 1-(2-ethoxyphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CCOC1=CC=CC=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 MCESVWQYJXZHOH-UHFFFAOYSA-N 0.000 description 1
VQDANEUSMXVNGY-UHFFFAOYSA-N 1-(2-fluoro-5-nitrophenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound [O-][N+](=O)C1=CC=C(F)C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 VQDANEUSMXVNGY-UHFFFAOYSA-N 0.000 description 1
BKVJLRPQHGWDNH-UHFFFAOYSA-N 1-(2-methoxy-4-nitrophenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COC1=CC([N+]([O-])=O)=CC=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 BKVJLRPQHGWDNH-UHFFFAOYSA-N 0.000 description 1
YRWFTPPPNBPMNF-UHFFFAOYSA-N 1-(2-methoxy-5-methylphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 YRWFTPPPNBPMNF-UHFFFAOYSA-N 0.000 description 1
NVRRPPBQBVYFJF-UHFFFAOYSA-N 1-(2-methoxy-5-nitrophenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C([N+]([O-])=O)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 NVRRPPBQBVYFJF-UHFFFAOYSA-N 0.000 description 1
NTGITDUWLJNPCG-UHFFFAOYSA-N 1-(2-methoxy-5-phenylphenyl)-3-[4-[4-(oxan-4-ylmethyl)imidazol-1-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C=2C=CC=CC=2)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1N(C=1)C=NC=1CC1CCOCC1 NTGITDUWLJNPCG-UHFFFAOYSA-N 0.000 description 1
DTMGDZVXFBDPCJ-UHFFFAOYSA-N 1-(2-methoxy-5-trimethylsilylphenyl)-3-[4-[4-(oxan-4-ylamino)phenyl]naphthalen-1-yl]urea Chemical compound COC1=CC=C([Si](C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=C1)=CC=C1NC1CCOCC1 DTMGDZVXFBDPCJ-UHFFFAOYSA-N 0.000 description 1
IZUDERUUDIJAIC-UHFFFAOYSA-N 1-(2-methoxyphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=CC=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 IZUDERUUDIJAIC-UHFFFAOYSA-N 0.000 description 1
WZCAGFROEGNXOQ-UHFFFAOYSA-N 1-(2-methyl-1,3-dioxoisoindol-5-yl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=C2C(=O)N(C)C(=O)C2=CC=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 WZCAGFROEGNXOQ-UHFFFAOYSA-N 0.000 description 1
SLCLHNJCNWDURK-UHFFFAOYSA-N 1-(2-methyl-3-nitrophenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=CC=C([N+]([O-])=O)C(C)=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 SLCLHNJCNWDURK-UHFFFAOYSA-N 0.000 description 1
DNIOFXKFGFGVAV-UHFFFAOYSA-N 1-(2-methyl-4-nitrophenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CC1=CC([N+]([O-])=O)=CC=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 DNIOFXKFGFGVAV-UHFFFAOYSA-N 0.000 description 1
XBWMGYBQDGAPLE-UHFFFAOYSA-N 1-(2-methyl-5-phenylphenyl)-3-[4-[4-(2-pyridin-4-ylethyl)piperazin-1-yl]naphthalen-1-yl]urea Chemical compound CC1=CC=C(C=2C=CC=CC=2)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1N(CC1)CCN1CCC1=CC=NC=C1 XBWMGYBQDGAPLE-UHFFFAOYSA-N 0.000 description 1
VTOFXBYEZWMSIR-UHFFFAOYSA-N 1-(2-methyl-6-propan-2-ylphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CC(C)C1=CC=CC(C)=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 VTOFXBYEZWMSIR-UHFFFAOYSA-N 0.000 description 1
ISWYJMDOFPGKKL-UHFFFAOYSA-N 1-(2-methylsulfanylphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CSC1=CC=CC=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 ISWYJMDOFPGKKL-UHFFFAOYSA-N 0.000 description 1
MYUPRBWNKVNHHN-UHFFFAOYSA-N 1-(3,4-dimethylphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=C(C)C(C)=CC=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 MYUPRBWNKVNHHN-UHFFFAOYSA-N 0.000 description 1
UCVHVJOQGPMCSJ-UHFFFAOYSA-N 1-(3,5-dimethoxyphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COC1=CC(OC)=CC(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 UCVHVJOQGPMCSJ-UHFFFAOYSA-N 0.000 description 1
DELSLEWHRQVXEV-UHFFFAOYSA-N 1-(3-chloro-2-methoxyphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COC1=C(Cl)C=CC=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 DELSLEWHRQVXEV-UHFFFAOYSA-N 0.000 description 1
NVYYWTXAJCTIRC-UHFFFAOYSA-N 1-(3-chloro-4-methylphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=C(Cl)C(C)=CC=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 NVYYWTXAJCTIRC-UHFFFAOYSA-N 0.000 description 1
SKGOFDWOHKOHPM-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound ClC1=CC=CC(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 SKGOFDWOHKOHPM-UHFFFAOYSA-N 0.000 description 1
GTNFKGBUXGFUIS-UHFFFAOYSA-N 1-(3-cyanophenyl)-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=CC(C#N)=C1 GTNFKGBUXGFUIS-UHFFFAOYSA-N 0.000 description 1
GCEWIOVJYXKEEO-UHFFFAOYSA-N 1-(3-cyclopentyloxy-4-methoxyphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=C(OC2CCCC2)C(OC)=CC=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 GCEWIOVJYXKEEO-UHFFFAOYSA-N 0.000 description 1
GMCBUMYNOUFINM-UHFFFAOYSA-N 1-(3-ethylphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CCC1=CC=CC(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 GMCBUMYNOUFINM-UHFFFAOYSA-N 0.000 description 1
RMRDSOFRYIUFBR-UHFFFAOYSA-N 1-(3-fluorophenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound FC1=CC=CC(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 RMRDSOFRYIUFBR-UHFFFAOYSA-N 0.000 description 1
OSHNTNCCRAGCQP-UHFFFAOYSA-N 1-(3-iodophenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound IC1=CC=CC(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 OSHNTNCCRAGCQP-UHFFFAOYSA-N 0.000 description 1
KGVLJKGUKCFSDO-UHFFFAOYSA-N 1-(3-methoxynaphthalen-2-yl)-3-[4-[4-(morpholin-4-ylmethyl)piperidin-1-yl]naphthalen-1-yl]urea Chemical compound COC1=CC2=CC=CC=C2C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1N(CC1)CCC1CN1CCOCC1 KGVLJKGUKCFSDO-UHFFFAOYSA-N 0.000 description 1
QDPZFULULDYXQB-UHFFFAOYSA-N 1-(3-methoxyphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=CC(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 QDPZFULULDYXQB-UHFFFAOYSA-N 0.000 description 1
XZFXEARDACDSNZ-UHFFFAOYSA-N 1-(3-methylnaphthalen-2-yl)-3-[4-[4-(morpholin-4-ylmethyl)phenyl]naphthalen-1-yl]urea Chemical compound CC1=CC2=CC=CC=C2C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=C1)=CC=C1CN1CCOCC1 XZFXEARDACDSNZ-UHFFFAOYSA-N 0.000 description 1
OVHYJLACXNXRRN-UHFFFAOYSA-N 1-(3-methylphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CC1=CC=CC(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 OVHYJLACXNXRRN-UHFFFAOYSA-N 0.000 description 1
RTKWZFFSSWSSOK-UHFFFAOYSA-N 1-(3-methylsulfanylphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CSC1=CC=CC(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 RTKWZFFSSWSSOK-UHFFFAOYSA-N 0.000 description 1
MIDPIMMHFWHYPR-UHFFFAOYSA-N 1-(3-tert-butyl-5-methylsulfinylphenyl)-3-[4-[6-[(1-methylpiperidin-4-yl)methyl]pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1CN(C)CCC1CC1=CC=C(C=2C3=CC=CC=C3C(NC(=O)NC=3C=C(C=C(C=3)S(C)=O)C(C)(C)C)=CC=2)C=N1 MIDPIMMHFWHYPR-UHFFFAOYSA-N 0.000 description 1
GGENDVBBYGMGAB-UHFFFAOYSA-N 1-(3-tert-butylphenyl)-3-[4-(3-pyridin-3-ylpropoxy)naphthalen-1-yl]urea Chemical compound CC(C)(C)C1=CC=CC(NC(=O)NC=2C3=CC=CC=C3C(OCCCC=3C=NC=CC=3)=CC=2)=C1 GGENDVBBYGMGAB-UHFFFAOYSA-N 0.000 description 1
YSQIRQHMWBJMDD-UHFFFAOYSA-N 1-(4,5-dimethyl-2-nitrophenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=C(C)C(C)=CC(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1[N+]([O-])=O YSQIRQHMWBJMDD-UHFFFAOYSA-N 0.000 description 1
WOWFGNLVWKITNL-UHFFFAOYSA-N 1-(4-butoxyphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=CC(OCCCC)=CC=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 WOWFGNLVWKITNL-UHFFFAOYSA-N 0.000 description 1
UJQAWNVZBADKJV-UHFFFAOYSA-N 1-(4-butyl-2-methylphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CC1=CC(CCCC)=CC=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 UJQAWNVZBADKJV-UHFFFAOYSA-N 0.000 description 1
MTKUHPDTFAQCFX-UHFFFAOYSA-N 1-(4-chloro-2-nitrophenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 MTKUHPDTFAQCFX-UHFFFAOYSA-N 0.000 description 1
OAOJFUBUJNSPAI-UHFFFAOYSA-N 1-(4-chloro-3-nitrophenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 OAOJFUBUJNSPAI-UHFFFAOYSA-N 0.000 description 1
BOKYQOSMBRSLII-UHFFFAOYSA-N 1-(4-cyanophenyl)-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#N)C=C1 BOKYQOSMBRSLII-UHFFFAOYSA-N 0.000 description 1
SJIPXUFJHFYJLW-UHFFFAOYSA-N 1-(4-ethoxyphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=CC(OCC)=CC=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 SJIPXUFJHFYJLW-UHFFFAOYSA-N 0.000 description 1
DRWRBWVNLUABQH-UHFFFAOYSA-N 1-(4-methoxy-2-methylphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CC1=CC(OC)=CC=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 DRWRBWVNLUABQH-UHFFFAOYSA-N 0.000 description 1
FJKDPIXCLCCJAW-UHFFFAOYSA-N 1-(4-methoxyphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=CC(OC)=CC=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 FJKDPIXCLCCJAW-UHFFFAOYSA-N 0.000 description 1
CMADJBMFLMNTPD-UHFFFAOYSA-N 1-(4-methyl-2-nitrophenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound [O-][N+](=O)C1=CC(C)=CC=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 CMADJBMFLMNTPD-UHFFFAOYSA-N 0.000 description 1
HLZMRNBZAURXQE-UHFFFAOYSA-N 1-(4-methyl-3-nitrophenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=C([N+]([O-])=O)C(C)=CC=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 HLZMRNBZAURXQE-UHFFFAOYSA-N 0.000 description 1
MEEUJAATDOYEJC-UHFFFAOYSA-N 1-(4-methylsulfanylphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=CC(SC)=CC=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 MEEUJAATDOYEJC-UHFFFAOYSA-N 0.000 description 1
GFMFIGFHLIFYCS-UHFFFAOYSA-N 1-(5-chloro-2-methoxyphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(Cl)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 GFMFIGFHLIFYCS-UHFFFAOYSA-N 0.000 description 1
NCOSCXYSLWUWPO-UHFFFAOYSA-N 1-(5-chloro-2-methylphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CC1=CC=C(Cl)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 NCOSCXYSLWUWPO-UHFFFAOYSA-N 0.000 description 1
FEMSKAZXWCRQRB-UHFFFAOYSA-N 1-(5-ethylsulfonyl-2-methoxyphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 FEMSKAZXWCRQRB-UHFFFAOYSA-N 0.000 description 1
PNRCNWGZYUYWER-UHFFFAOYSA-N 1-(5-tert-butyl-2-cyclopentyloxyphenyl)-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=C1OC1CCCC1 PNRCNWGZYUYWER-UHFFFAOYSA-N 0.000 description 1
LJPDYRPCIMUGJC-UHFFFAOYSA-N 1-(5-tert-butyl-2-hydroxyphenyl)-3-[4-[5-(morpholin-4-ylmethyl)pyrazin-2-yl]naphthalen-1-yl]urea Chemical compound CC(C)(C)C1=CC=C(O)C(NC(=O)NC=2C3=CC=CC=C3C(C=3N=CC(CN4CCOCC4)=NC=3)=CC=2)=C1 LJPDYRPCIMUGJC-UHFFFAOYSA-N 0.000 description 1
OOZAZFBOXVEMTO-UHFFFAOYSA-N 1-(5-tert-butyl-2-hydroxyphenyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CC(C)(C)C1=CC=C(O)C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 OOZAZFBOXVEMTO-UHFFFAOYSA-N 0.000 description 1
QNKAOKYOALTOPO-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxy-3-propylphenyl)-3-[4-[4-(pyrrolidine-1-carbonyl)phenyl]naphthalen-1-yl]urea Chemical compound CCCC1=CC(C(C)(C)C)=CC(NC(=O)NC=2C3=CC=CC=C3C(C=3C=CC(=CC=3)C(=O)N3CCCC3)=CC=2)=C1OC QNKAOKYOALTOPO-UHFFFAOYSA-N 0.000 description 1
LPMUPSRIFUGLPK-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[4-[(2-methyl-3-oxopiperazin-1-yl)methyl]phenyl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=C1)=CC=C1CN1C(C)C(=O)NCC1 LPMUPSRIFUGLPK-UHFFFAOYSA-N 0.000 description 1
FXFWXNAYTVAMNY-UHFFFAOYSA-N 1-(5-tert-butyl-2-phenoxyphenyl)-3-[4-[6-(oxan-4-yloxy)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C=1C=C(C=2C=NC(OC3CCOCC3)=CC=2)C2=CC=CC=C2C=1NC(=O)NC1=CC(C(C)(C)C)=CC=C1OC1=CC=CC=C1 FXFWXNAYTVAMNY-UHFFFAOYSA-N 0.000 description 1
VUDBDCWAXPFING-UHFFFAOYSA-N 1-(5-tert-butyl-2-phenylphenyl)-3-[4-(pyridin-4-ylmethoxy)naphthalen-1-yl]urea Chemical compound C=1C(C(C)(C)C)=CC=C(C=2C=CC=CC=2)C=1NC(=O)NC(C1=CC=CC=C11)=CC=C1OCC1=CC=NC=C1 VUDBDCWAXPFING-UHFFFAOYSA-N 0.000 description 1
PFHCERCJWUXQSI-UHFFFAOYSA-N 1-(5-tert-butyl-2-phenylpyrazol-3-yl)-3-[4-[4-(piperidin-1-ylmethyl)phenyl]naphthalen-1-yl]urea Chemical compound C=1C=CC=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=C1)=CC=C1CN1CCCCC1 PFHCERCJWUXQSI-UHFFFAOYSA-N 0.000 description 1
PJOXIJLFHGXSBL-UHFFFAOYSA-N 1-(5-tert-butyl-2-phenylpyrazol-3-yl)-3-[4-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]naphthalen-1-yl]urea Chemical compound C1CN(C)CCN1CC1=CC=C(C=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC=CC=3)=CC=2)C=C1 PJOXIJLFHGXSBL-UHFFFAOYSA-N 0.000 description 1
ORJSKGLMRJXJBK-UHFFFAOYSA-N 1-(5-tert-butyl-3-cyano-2-methoxyphenyl)-3-[4-[2-[(2,6-dimethylmorpholin-4-yl)methyl]pyrimidin-5-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)=CN=C1CN1CC(C)OC(C)C1 ORJSKGLMRJXJBK-UHFFFAOYSA-N 0.000 description 1
UBVPVRCZHPIPGW-UHFFFAOYSA-N 1-(6-methoxy-3,3-dimethyl-1,2-dihydroinden-5-yl)-3-[4-[4-(morpholine-4-carbonyl)phenyl]naphthalen-1-yl]urea Chemical compound COC1=CC=2CCC(C)(C)C=2C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=C1)=CC=C1C(=O)N1CCOCC1 UBVPVRCZHPIPGW-UHFFFAOYSA-N 0.000 description 1
XTASSHAKXLGJIB-UHFFFAOYSA-N 1-(7-methoxy-1,4,4-trimethyl-2,3-dihydroquinolin-6-yl)-3-[4-[6-(oxan-4-yloxy)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=2N(C)CCC(C)(C)C=2C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1OC1CCOCC1 XTASSHAKXLGJIB-UHFFFAOYSA-N 0.000 description 1
MZGLGJINJPQUKP-UHFFFAOYSA-N 1-(7-tert-butyl-2,4-dimethyl-1,3-benzoxazol-5-yl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C=1C(C(C)(C)C)=C2OC(C)=NC2=C(C)C=1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 MZGLGJINJPQUKP-UHFFFAOYSA-N 0.000 description 1
DXUSBDZJVDGKLG-UHFFFAOYSA-N 1-[2-(difluoromethoxy)phenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound FC(F)OC1=CC=CC=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 DXUSBDZJVDGKLG-UHFFFAOYSA-N 0.000 description 1
MHRIZTNZAKDVOM-UHFFFAOYSA-N 1-[2-(hydroxymethyl)-4-phenylcyclohexyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound OCC1CC(C=2C=CC=CC=2)CCC1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 MHRIZTNZAKDVOM-UHFFFAOYSA-N 0.000 description 1
NABBWDSOZIZSSI-UHFFFAOYSA-N 1-[2-[3-[(dimethylamino)methyl]phenyl]-5-(1-methylcyclohexyl)pyrazol-3-yl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CN(C)CC1=CC=CC(N2C(=CC(=N2)C2(C)CCCCC2)NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 NABBWDSOZIZSSI-UHFFFAOYSA-N 0.000 description 1
QVSLQEKXVVLVLF-UHFFFAOYSA-N 1-[2-chloro-5-(trifluoromethyl)phenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound FC(F)(F)C1=CC=C(Cl)C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 QVSLQEKXVVLVLF-UHFFFAOYSA-N 0.000 description 1
FXELSCIRQCPZSX-UHFFFAOYSA-N 1-[2-fluoro-3-(trifluoromethyl)phenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=CC=C(C(F)(F)F)C(F)=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 FXELSCIRQCPZSX-UHFFFAOYSA-N 0.000 description 1
QZSMGFLWRPYBMA-UHFFFAOYSA-N 1-[2-fluoro-5-(trifluoromethyl)phenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound FC1=CC=C(C(F)(F)F)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 QZSMGFLWRPYBMA-UHFFFAOYSA-N 0.000 description 1
XIQRXBRRDXIGRH-UHFFFAOYSA-N 1-[2-fluoro-6-(trifluoromethyl)phenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound FC1=CC=CC(C(F)(F)F)=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 XIQRXBRRDXIGRH-UHFFFAOYSA-N 0.000 description 1
SDDFXDGQQJJYFY-UHFFFAOYSA-N 1-[2-methoxy-5-(1,1,2,2,2-pentafluoroethyl)phenyl]-3-[4-[4-(morpholin-4-ylmethyl)piperidin-1-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(F)(F)C(F)(F)F)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1N1CCC(CN2CCOCC2)CC1 SDDFXDGQQJJYFY-UHFFFAOYSA-N 0.000 description 1
IZENUBLIMNLUPI-UHFFFAOYSA-N 1-[2-methoxy-5-(1-methylcyclohexyl)phenyl]-3-[4-[4-(1-methylpiperidin-4-yl)sulfanylphenyl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C2(C)CCCCC2)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=C1)=CC=C1SC1CCN(C)CC1 IZENUBLIMNLUPI-UHFFFAOYSA-N 0.000 description 1
HOTFUBVPHPRIFG-UHFFFAOYSA-N 1-[2-methoxy-5-(2-phenylpropan-2-yl)phenyl]-3-[4-[6-(2-pyridin-4-ylethyl)pyridazin-3-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C=2C=CC=CC=2)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(N=N1)=CC=C1CCC1=CC=NC=C1 HOTFUBVPHPRIFG-UHFFFAOYSA-N 0.000 description 1
FGYPTHNWLKARTL-UHFFFAOYSA-N 1-[2-methoxy-5-[3-(trifluoromethyl)-1-bicyclo[1.1.1]pentanyl]phenyl]-3-[4-[4-(morpholin-4-ylmethyl)phenyl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C23CC(C2)(C3)C(F)(F)F)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=C1)=CC=C1CN1CCOCC1 FGYPTHNWLKARTL-UHFFFAOYSA-N 0.000 description 1
YWSQDZYHPYLOFB-UHFFFAOYSA-N 1-[2-methylsulfanyl-5-(trifluoromethyl)phenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CSC1=CC=C(C(F)(F)F)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 YWSQDZYHPYLOFB-UHFFFAOYSA-N 0.000 description 1
SBOIKWPUEBZGJT-UHFFFAOYSA-N 1-[3,5-bis(trifluoromethyl)phenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 SBOIKWPUEBZGJT-UHFFFAOYSA-N 0.000 description 1
FPUUGIBFPPUPNA-UHFFFAOYSA-N 1-[3-methoxy-5-(trifluoromethyl)phenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound FC(F)(F)C1=CC(OC)=CC(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 FPUUGIBFPPUPNA-UHFFFAOYSA-N 0.000 description 1
GQYLQHFCYCXCAS-UHFFFAOYSA-N 1-[3-tert-butyl-5-(1-methylimidazol-4-yl)phenyl]-3-[4-[5-(morpholin-4-ylmethyl)pyridin-2-yl]naphthalen-1-yl]urea Chemical compound CN1C=NC(C=2C=C(C=C(NC(=O)NC=3C4=CC=CC=C4C(C=4N=CC(CN5CCOCC5)=CC=4)=CC=3)C=2)C(C)(C)C)=C1 GQYLQHFCYCXCAS-UHFFFAOYSA-N 0.000 description 1
YWTHBRKLKCHYBH-UHFFFAOYSA-N 1-[3-tert-butyl-5-(3-pyrrolidin-1-ylprop-1-ynyl)phenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C=1C(C#CCN2CCCC2)=CC(C(C)(C)C)=CC=1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 YWTHBRKLKCHYBH-UHFFFAOYSA-N 0.000 description 1
GKBQVCYHOMWCQT-UHFFFAOYSA-N 1-[3-tert-butyl-5-[4-(dimethylamino)phenyl]phenyl]-3-[4-[2-(morpholin-4-ylmethyl)pyrimidin-5-yl]naphthalen-1-yl]urea Chemical compound C1=CC(N(C)C)=CC=C1C1=CC(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=NC=3)=CC=2)=CC(C(C)(C)C)=C1 GKBQVCYHOMWCQT-UHFFFAOYSA-N 0.000 description 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 description 1
NUDHSTZFJXZRRH-UHFFFAOYSA-N 1-[4-[4-[[bis(2-cyanoethyl)amino]methyl]phenyl]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)C=C1 NUDHSTZFJXZRRH-UHFFFAOYSA-N 0.000 description 1
IUIIKMAXKVASOZ-UHFFFAOYSA-N 1-[4-[6-(imidazol-1-ylmethyl)pyridin-3-yl]naphthalen-1-yl]-3-[2-methoxy-5-(1-phenylcyclopropyl)phenyl]urea Chemical compound COC1=CC=C(C2(CC2)C=2C=CC=CC=2)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1C=CN=C1 IUIIKMAXKVASOZ-UHFFFAOYSA-N 0.000 description 1
DZTYZESAZHRWEL-UHFFFAOYSA-N 1-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]-3-(2,4,6-trichlorophenyl)urea Chemical compound ClC1=CC(Cl)=CC(Cl)=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 DZTYZESAZHRWEL-UHFFFAOYSA-N 0.000 description 1
OKTQQECLESQZMT-UHFFFAOYSA-N 1-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]-3-(2-pentoxy-5-phenylphenyl)urea Chemical compound CCCCCOC1=CC=C(C=2C=CC=CC=2)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 OKTQQECLESQZMT-UHFFFAOYSA-N 0.000 description 1
QOVMEGLQDPRYJR-UHFFFAOYSA-N 1-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]-3-(2-phenoxyphenyl)urea Chemical compound C=1C=C(C=2C=NC(CN3CCOCC3)=CC=2)C2=CC=CC=C2C=1NC(=O)NC1=CC=CC=C1OC1=CC=CC=C1 QOVMEGLQDPRYJR-UHFFFAOYSA-N 0.000 description 1
JZQIYUOWHSFMHD-UHFFFAOYSA-N 1-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]-3-(3,4,5-trimethoxyphenyl)urea Chemical compound COC1=C(OC)C(OC)=CC(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 JZQIYUOWHSFMHD-UHFFFAOYSA-N 0.000 description 1
RVNIHSVMRBJWGV-UHFFFAOYSA-N 1-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]-3-(3-phenoxyphenyl)urea Chemical compound C=1C=C(C=2C=NC(CN3CCOCC3)=CC=2)C2=CC=CC=C2C=1NC(=O)NC(C=1)=CC=CC=1OC1=CC=CC=C1 RVNIHSVMRBJWGV-UHFFFAOYSA-N 0.000 description 1
VGYHEUSLDXFJCX-UHFFFAOYSA-N 1-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]-3-(4-phenylmethoxyphenyl)urea Chemical compound C=1C=C(C=2C=NC(CN3CCOCC3)=CC=2)C2=CC=CC=C2C=1NC(=O)NC(C=C1)=CC=C1OCC1=CC=CC=C1 VGYHEUSLDXFJCX-UHFFFAOYSA-N 0.000 description 1
XTRFOLYPDHICQA-UHFFFAOYSA-N 1-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]-3-(4-phenylphenyl)urea Chemical compound C=1C=C(C=2C=NC(CN3CCOCC3)=CC=2)C2=CC=CC=C2C=1NC(=O)NC(C=C1)=CC=C1C1=CC=CC=C1 XTRFOLYPDHICQA-UHFFFAOYSA-N 0.000 description 1
XUSKDFHOLIZMPZ-UHFFFAOYSA-N 1-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]-3-(4-propan-2-ylphenyl)urea Chemical compound C1=CC(C(C)C)=CC=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 XUSKDFHOLIZMPZ-UHFFFAOYSA-N 0.000 description 1
HPGCGTTYJWYWKO-UHFFFAOYSA-N 1-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]-3-[3-(1,3-oxazol-5-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=CN=CO1 HPGCGTTYJWYWKO-UHFFFAOYSA-N 0.000 description 1
HCSXXHQZLIWWCF-UHFFFAOYSA-N 1-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]-3-[3-(trifluoromethylsulfanyl)phenyl]urea Chemical compound FC(F)(F)SC1=CC=CC(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 HCSXXHQZLIWWCF-UHFFFAOYSA-N 0.000 description 1
MSYXLPKGQJTTIR-UHFFFAOYSA-N 1-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound C1=CC(C(F)(F)F)=CC=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 MSYXLPKGQJTTIR-UHFFFAOYSA-N 0.000 description 1
LEEKRWMUGPKUQK-UHFFFAOYSA-N 1-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]-3-[4-(trifluoromethylsulfanyl)phenyl]urea Chemical compound C1=CC(SC(F)(F)F)=CC=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 LEEKRWMUGPKUQK-UHFFFAOYSA-N 0.000 description 1
ITLMWHYFKHLGOI-UHFFFAOYSA-N 1-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]-3-naphthalen-2-ylurea Chemical compound C=1C=C2C=CC=CC2=CC=1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 ITLMWHYFKHLGOI-UHFFFAOYSA-N 0.000 description 1
ZDXNVBXXPNTCDV-UHFFFAOYSA-N 1-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]-3-phenylurea Chemical compound C=1C=C(C=2C=NC(CN3CCOCC3)=CC=2)C2=CC=CC=C2C=1NC(=O)NC1=CC=CC=C1 ZDXNVBXXPNTCDV-UHFFFAOYSA-N 0.000 description 1
VMIXRXULLUDLCC-UHFFFAOYSA-N 1-[4-chloro-2-(trifluoromethyl)phenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound FC(F)(F)C1=CC(Cl)=CC=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 VMIXRXULLUDLCC-UHFFFAOYSA-N 0.000 description 1
LUMDRDSNLWYIAJ-UHFFFAOYSA-N 1-[4-chloro-3-(trifluoromethyl)phenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 LUMDRDSNLWYIAJ-UHFFFAOYSA-N 0.000 description 1
BDCNTBMKZQYZPK-UHFFFAOYSA-N 1-[4-fluoro-3-(trifluoromethyl)phenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=C(C(F)(F)F)C(F)=CC=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 BDCNTBMKZQYZPK-UHFFFAOYSA-N 0.000 description 1
XYCOYKZYTVPXSZ-UHFFFAOYSA-N 1-[5-(1-cyanocyclopropyl)-2-methoxyphenyl]-3-[4-[2-(morpholin-4-ylmethyl)pyrimidin-5-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)=CN=C1CN1CCOCC1 XYCOYKZYTVPXSZ-UHFFFAOYSA-N 0.000 description 1
VAZOYARPRLVOKK-UHFFFAOYSA-N 1-[5-(butylsulfamoyl)-2-methoxyphenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CCCCNS(=O)(=O)C1=CC=C(OC)C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 VAZOYARPRLVOKK-UHFFFAOYSA-N 0.000 description 1
FYRMGVWDFQZNGA-UHFFFAOYSA-N 1-[5-[1-(hydroxymethyl)cyclopropyl]-2-methoxyphenyl]-3-[4-[4-(morpholin-4-ylmethyl)phenyl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C2(CO)CC2)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=C1)=CC=C1CN1CCOCC1 FYRMGVWDFQZNGA-UHFFFAOYSA-N 0.000 description 1
NSAQAZKZZFADBN-UHFFFAOYSA-N 1-[5-tert-butyl-1-[2-(diethylamino)ethyl]-2-oxopyridin-3-yl]-3-[4-[6-(1-methylpiperidin-4-yl)oxypyridin-3-yl]naphthalen-1-yl]urea Chemical compound O=C1N(CCN(CC)CC)C=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1OC1CCN(C)CC1 NSAQAZKZZFADBN-UHFFFAOYSA-N 0.000 description 1
HXNARSOBTYIVTI-UHFFFAOYSA-N 1-[5-tert-butyl-2-(1h-pyrazol-4-yl)phenyl]-3-[4-(2-morpholin-4-ylethoxy)naphthalen-1-yl]urea Chemical compound C=1C=C(OCCN2CCOCC2)C2=CC=CC=C2C=1NC(=O)NC1=CC(C(C)(C)C)=CC=C1C=1C=NNC=1 HXNARSOBTYIVTI-UHFFFAOYSA-N 0.000 description 1
MOJPDKUUTRIKNP-UHFFFAOYSA-N 1-[5-tert-butyl-2-(2-cyclopropylpyrimidin-5-yl)pyrazol-3-yl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C=1N=C(C2CC2)N=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 MOJPDKUUTRIKNP-UHFFFAOYSA-N 0.000 description 1
WWSGPSTYXUUGKA-UHFFFAOYSA-N 1-[5-tert-butyl-2-(2-methylpyrimidin-5-yl)pyrazol-3-yl]-3-[4-[2-(morpholin-4-ylmethyl)pyrimidin-5-yl]naphthalen-1-yl]urea Chemical compound C1=NC(C)=NC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=NC=3)=CC=2)=CC(C(C)(C)C)=N1 WWSGPSTYXUUGKA-UHFFFAOYSA-N 0.000 description 1
MVUKHCMSUFRDNK-UHFFFAOYSA-N 1-[5-tert-butyl-2-(2-methylpyrimidin-5-yl)pyrazol-3-yl]-3-[4-[4-(morpholin-4-ylmethyl)phenyl]naphthalen-1-yl]urea Chemical compound C1=NC(C)=NC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=CC(CN4CCOCC4)=CC=3)=CC=2)=CC(C(C)(C)C)=N1 MVUKHCMSUFRDNK-UHFFFAOYSA-N 0.000 description 1
OVBWFOWXZMICRG-UHFFFAOYSA-N 1-[5-tert-butyl-2-(2-methylpyrimidin-5-yl)pyrazol-3-yl]-3-[4-[5-(morpholin-4-ylmethyl)pyrazin-2-yl]naphthalen-1-yl]urea Chemical compound C1=NC(C)=NC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3N=CC(CN4CCOCC4)=NC=3)=CC=2)=CC(C(C)(C)C)=N1 OVBWFOWXZMICRG-UHFFFAOYSA-N 0.000 description 1
ZVTAQYKESHSLHQ-UHFFFAOYSA-N 1-[5-tert-butyl-2-(2-methylpyrimidin-5-yl)pyrazol-3-yl]-3-[4-[6-(morpholine-4-carbonyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=NC(C)=NC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(=CC=3)C(=O)N3CCOCC3)=CC=2)=CC(C(C)(C)C)=N1 ZVTAQYKESHSLHQ-UHFFFAOYSA-N 0.000 description 1
UVKLKCLMBHRNBS-UHFFFAOYSA-N 1-[5-tert-butyl-2-(2-morpholin-4-yl-2-oxoethoxy)phenyl]-3-[4-[6-(2-pyridin-4-ylethyl)pyridazin-3-yl]naphthalen-1-yl]urea Chemical compound C=1C=C(C=2N=NC(CCC=3C=CN=CC=3)=CC=2)C2=CC=CC=C2C=1NC(=O)NC1=CC(C(C)(C)C)=CC=C1OCC(=O)N1CCOCC1 UVKLKCLMBHRNBS-UHFFFAOYSA-N 0.000 description 1
UEQRWQVJAQYPAI-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[3-(2-methyl-4-morpholin-4-ylphenyl)naphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C=C(C=2)C=2C(=CC(=CC=2)N2CCOCC2)C)=CC(C(C)(C)C)=N1 UEQRWQVJAQYPAI-UHFFFAOYSA-N 0.000 description 1
IHQYQTOVSWVUSK-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-(2-methyl-4-morpholin-4-ylphenyl)naphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C(=CC(=CC=3)N3CCOCC3)C)=CC=2)=CC(C(C)(C)C)=N1 IHQYQTOVSWVUSK-UHFFFAOYSA-N 0.000 description 1
ALGANHBCSBPFLJ-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-(3-methylsulfinylphenyl)naphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=C(C=CC=3)S(C)=O)=CC=2)=CC(C(C)(C)C)=N1 ALGANHBCSBPFLJ-UHFFFAOYSA-N 0.000 description 1
JKLFIEZXJIVSJZ-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-(3-methylsulfonylphenyl)naphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=C(C=CC=3)S(C)(=O)=O)=CC=2)=CC(C(C)(C)C)=N1 JKLFIEZXJIVSJZ-UHFFFAOYSA-N 0.000 description 1
HZCMATDIMJCKIP-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-(3-morpholin-4-ylcyclohexen-1-yl)naphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3CCCC(C=3)N3CCOCC3)=CC=2)=CC(C(C)(C)C)=N1 HZCMATDIMJCKIP-UHFFFAOYSA-N 0.000 description 1
SKTLTPXXGDRZGT-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-(3-morpholin-4-ylphenyl)naphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=C(C=CC=3)N3CCOCC3)=CC=2)=CC(C(C)(C)C)=N1 SKTLTPXXGDRZGT-UHFFFAOYSA-N 0.000 description 1
VGXFLFBXAFHANE-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-(4-morpholin-4-ylphenyl)naphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=CC(=CC=3)N3CCOCC3)=CC=2)=CC(C(C)(C)C)=N1 VGXFLFBXAFHANE-UHFFFAOYSA-N 0.000 description 1
CARWVQWRYKBXLE-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-(6-oxo-1-pyridin-4-yl-2,3-dihydropyridin-4-yl)naphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3CCN(C(=O)C=3)C=3C=CN=CC=3)=CC=2)=CC(C(C)(C)C)=N1 CARWVQWRYKBXLE-UHFFFAOYSA-N 0.000 description 1
JIIKGDUUABJJLU-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-(6-pyridin-3-yloxypyridin-3-yl)naphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(OC=4C=NC=CC=4)=CC=3)=CC=2)=CC(C(C)(C)C)=N1 JIIKGDUUABJJLU-UHFFFAOYSA-N 0.000 description 1
NAQVMJURUKMKMV-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[3-(2-morpholin-4-ylethylamino)cyclohexen-1-yl]naphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3CCCC(C=3)NCCN3CCOCC3)=CC=2)=CC(C(C)(C)C)=N1 NAQVMJURUKMKMV-UHFFFAOYSA-N 0.000 description 1
PEYFPLYHYJCFLS-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[3-(morpholine-4-carbonyl)phenyl]naphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=C(C=CC=3)C(=O)N3CCOCC3)=CC=2)=CC(C(C)(C)C)=N1 PEYFPLYHYJCFLS-UHFFFAOYSA-N 0.000 description 1
YMTLTNAESUCGOE-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[3-oxo-4-[(1-oxo-1,4-thiazinan-4-yl)methyl]cyclohexen-1-yl]naphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3CCC(CN4CCS(=O)CC4)C(=O)C=3)=CC=2)=CC(C(C)(C)C)=N1 YMTLTNAESUCGOE-UHFFFAOYSA-N 0.000 description 1
VVULTIQZIBDJBN-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[3-oxo-4-[(1-oxothiolan-3-yl)methyl]cyclohexen-1-yl]naphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3CCC(CC4CS(=O)CC4)C(=O)C=3)=CC=2)=CC(C(C)(C)C)=N1 VVULTIQZIBDJBN-UHFFFAOYSA-N 0.000 description 1
CECNUIGWRRXUBK-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[4-(dimethylamino)phenyl]naphthalen-1-yl]urea Chemical compound C1=CC(N(C)C)=CC=C1C(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=NN1C1=CC=C(C)C=C1 CECNUIGWRRXUBK-UHFFFAOYSA-N 0.000 description 1
KUQLITRTIJXKBL-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[4-(morpholin-4-ylmethyl)-3-oxocyclohexen-1-yl]naphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3CCC(CN4CCOCC4)C(=O)C=3)=CC=2)=CC(C(C)(C)C)=N1 KUQLITRTIJXKBL-UHFFFAOYSA-N 0.000 description 1
SXEMQWFLKYPVSF-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[4-(morpholin-4-ylmethyl)imidazol-1-yl]naphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(N3C=C(CN4CCOCC4)N=C3)=CC=2)=CC(C(C)(C)C)=N1 SXEMQWFLKYPVSF-UHFFFAOYSA-N 0.000 description 1
UBFIQFLZFCCWTQ-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[4-[(2-pyridin-4-ylethylamino)methyl]phenyl]naphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=CC(CNCCC=4C=CN=CC=4)=CC=3)=CC=2)=CC(C(C)(C)C)=N1 UBFIQFLZFCCWTQ-UHFFFAOYSA-N 0.000 description 1
BSQWOONHGXKYPN-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[4-[(dimethylamino)methyl]phenyl]naphthalen-1-yl]urea Chemical compound C1=CC(CN(C)C)=CC=C1C(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=NN1C1=CC=C(C)C=C1 BSQWOONHGXKYPN-UHFFFAOYSA-N 0.000 description 1
HZMRKDCJYRCOBI-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[6-[hydroxy(pyridin-3-yl)methyl]pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(=CC=3)C(O)C=3C=NC=CC=3)=CC=2)=CC(C(C)(C)C)=N1 HZMRKDCJYRCOBI-UHFFFAOYSA-N 0.000 description 1
BCRSNFJKYNVRJZ-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-(6-oxo-1-pyridin-4-yl-2,3-dihydropyridin-4-yl)naphthalen-1-yl]urea Chemical compound C1=NC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3CCN(C(=O)C=3)C=3C=CN=CC=3)=CC=2)=CC(C(C)(C)C)=N1 BCRSNFJKYNVRJZ-UHFFFAOYSA-N 0.000 description 1
WIAANKLDUHBKIL-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[1-(oxan-4-ylmethyl)-6-oxo-2,3-dihydropyridin-4-yl]naphthalen-1-yl]urea Chemical compound C1=NC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3CCN(CC4CCOCC4)C(=O)C=3)=CC=2)=CC(C(C)(C)C)=N1 WIAANKLDUHBKIL-UHFFFAOYSA-N 0.000 description 1
HEZQFXSUBYYSAA-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[2-oxo-1-(pyridin-4-ylmethyl)piperidin-4-yl]naphthalen-1-yl]urea Chemical compound C1=NC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C3CC(=O)N(CC=4C=CN=CC=4)CC3)=CC=2)=CC(C(C)(C)C)=N1 HEZQFXSUBYYSAA-UHFFFAOYSA-N 0.000 description 1
PHJNXMRZUNXTNX-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[3-(2-morpholin-4-ylethoxy)phenyl]naphthalen-1-yl]urea Chemical compound C1=NC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=C(OCCN4CCOCC4)C=CC=3)=CC=2)=CC(C(C)(C)C)=N1 PHJNXMRZUNXTNX-UHFFFAOYSA-N 0.000 description 1
HSFLKMGQEKZVJB-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[3-(2-phenylethylamino)cyclohexen-1-yl]naphthalen-1-yl]urea Chemical compound C1=NC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3CCCC(C=3)NCCC=3C=CC=CC=3)=CC=2)=CC(C(C)(C)C)=N1 HSFLKMGQEKZVJB-UHFFFAOYSA-N 0.000 description 1
BZACDDLNKGCJIT-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[3-(n-methylanilino)cyclohexen-1-yl]naphthalen-1-yl]urea Chemical compound C=1C=CC=CC=1N(C)C(C=1)CCCC=1C(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=NN1C1=CC=C(C)N=C1 BZACDDLNKGCJIT-UHFFFAOYSA-N 0.000 description 1
QHNFIMMYAMKZGG-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[3-[2-(4-methoxyphenyl)ethylamino]cyclohexen-1-yl]naphthalen-1-yl]urea Chemical compound C1=CC(OC)=CC=C1CCNC1C=C(C=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=NC(C)=CC=3)=CC=2)CCC1 QHNFIMMYAMKZGG-UHFFFAOYSA-N 0.000 description 1
CCXAOUGARNDNOE-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[3-[2-(dimethylamino)ethylamino]cyclohexen-1-yl]naphthalen-1-yl]urea Chemical compound CN(C)CCNC1CCCC(C=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=NC(C)=CC=3)=CC=2)=C1 CCXAOUGARNDNOE-UHFFFAOYSA-N 0.000 description 1
NQSMYWBOMXTRMP-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[3-[furan-2-yl(methyl)amino]cyclohexen-1-yl]naphthalen-1-yl]urea Chemical compound C=1C=COC=1N(C)C(C=1)CCCC=1C(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=NN1C1=CC=C(C)N=C1 NQSMYWBOMXTRMP-UHFFFAOYSA-N 0.000 description 1
YQLZMQZEURCIBM-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[3-[methyl(pyridin-2-yl)amino]cyclohexen-1-yl]naphthalen-1-yl]urea Chemical compound C=1C=CC=NC=1N(C)C(C=1)CCCC=1C(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=NN1C1=CC=C(C)N=C1 YQLZMQZEURCIBM-UHFFFAOYSA-N 0.000 description 1
YEHSVFFUGWPDHS-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[3-[methyl(pyridin-3-yl)amino]cyclohexen-1-yl]naphthalen-1-yl]urea Chemical compound C=1C=CN=CC=1N(C)C(C=1)CCCC=1C(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=NN1C1=CC=C(C)N=C1 YEHSVFFUGWPDHS-UHFFFAOYSA-N 0.000 description 1
JCQJTMOQWQNIRR-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[3-[methyl(pyridin-4-yl)amino]cyclohexen-1-yl]naphthalen-1-yl]urea Chemical compound C=1C=NC=CC=1N(C)C(C=1)CCCC=1C(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=NN1C1=CC=C(C)N=C1 JCQJTMOQWQNIRR-UHFFFAOYSA-N 0.000 description 1
FIUPTBDERXQHNT-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[3-hydroxy-4-(1h-imidazol-2-ylmethyl)phenyl]naphthalen-1-yl]urea Chemical compound C1=NC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=C(O)C(CC=4NC=CN=4)=CC=3)=CC=2)=CC(C(C)(C)C)=N1 FIUPTBDERXQHNT-UHFFFAOYSA-N 0.000 description 1
GIAVPYIFVUYJDJ-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[3-hydroxy-4-(pyridin-3-ylmethyl)phenyl]naphthalen-1-yl]urea Chemical compound C1=NC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=C(O)C(CC=4C=NC=CC=4)=CC=3)=CC=2)=CC(C(C)(C)C)=N1 GIAVPYIFVUYJDJ-UHFFFAOYSA-N 0.000 description 1
JAYHQWUBYOMJDE-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[3-methoxy-5-(2-morpholin-4-ylethoxy)phenyl]naphthalen-1-yl]urea Chemical compound C=1C(C=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=NC(C)=CC=3)=CC=2)=CC(OC)=CC=1OCCN1CCOCC1 JAYHQWUBYOMJDE-UHFFFAOYSA-N 0.000 description 1
LYXKKQJAFLTMSN-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[4-(furan-2-ylmethyl)-3-methoxyphenyl]naphthalen-1-yl]urea Chemical compound COC1=CC(C=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=NC(C)=CC=3)=CC=2)=CC=C1CC1=CC=CO1 LYXKKQJAFLTMSN-UHFFFAOYSA-N 0.000 description 1
SGUUMAQWHXLAAC-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[4-(furan-3-ylmethyl)-3-hydroxyphenyl]naphthalen-1-yl]urea Chemical compound C1=NC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=C(O)C(CC4=COC=C4)=CC=3)=CC=2)=CC(C(C)(C)C)=N1 SGUUMAQWHXLAAC-UHFFFAOYSA-N 0.000 description 1
IXTITMXEHYGGCM-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[4-(morpholin-4-ylmethyl)imidazol-1-yl]naphthalen-1-yl]urea Chemical compound C1=NC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(N3C=C(CN4CCOCC4)N=C3)=CC=2)=CC(C(C)(C)C)=N1 IXTITMXEHYGGCM-UHFFFAOYSA-N 0.000 description 1
ICQKLSHONDDLAY-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[4-[(3,4-dimethoxyphenyl)methyl]-3-hydroxyphenyl]naphthalen-1-yl]urea Chemical compound C1=C(OC)C(OC)=CC=C1CC1=CC=C(C=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=NC(C)=CC=3)=CC=2)C=C1O ICQKLSHONDDLAY-UHFFFAOYSA-N 0.000 description 1
FPPJHMYVKAPSSO-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[4-[(3-hydroxypiperidin-1-yl)methyl]phenyl]naphthalen-1-yl]urea Chemical compound C1=NC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=CC(CN4CC(O)CCC4)=CC=3)=CC=2)=CC(C(C)(C)C)=N1 FPPJHMYVKAPSSO-UHFFFAOYSA-N 0.000 description 1
XQYVRZQMNKTDKE-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[4-[[2-cyanoethyl(pyridin-2-ylmethyl)amino]methyl]phenyl]naphthalen-1-yl]urea Chemical compound C1=NC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=CC(CN(CCC#N)CC=4N=CC=CC=4)=CC=3)=CC=2)=CC(C(C)(C)C)=N1 XQYVRZQMNKTDKE-UHFFFAOYSA-N 0.000 description 1
NWLHMDNQIGBRLZ-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[4-[[2-methoxyethyl(methyl)amino]methyl]phenyl]naphthalen-1-yl]urea Chemical compound C1=CC(CN(C)CCOC)=CC=C1C(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=NN1C1=CC=C(C)N=C1 NWLHMDNQIGBRLZ-UHFFFAOYSA-N 0.000 description 1
WUXJTRGACDOALB-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[5-(morpholin-4-ylmethyl)pyrazin-2-yl]naphthalen-1-yl]urea Chemical compound C1=NC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3N=CC(CN4CCOCC4)=NC=3)=CC=2)=CC(C(C)(C)C)=N1 WUXJTRGACDOALB-UHFFFAOYSA-N 0.000 description 1
JWSABMNLFXDLGN-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[5-(morpholine-4-carbonyl)pyrazin-2-yl]naphthalen-1-yl]urea Chemical compound C1=NC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3N=CC(=NC=3)C(=O)N3CCOCC3)=CC=2)=CC(C(C)(C)C)=N1 JWSABMNLFXDLGN-UHFFFAOYSA-N 0.000 description 1
WZOBNENWIXYHIE-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[6-(3-methoxypropylamino)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=NC(NCCCOC)=CC=C1C(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=NN1C1=CC=C(C)N=C1 WZOBNENWIXYHIE-UHFFFAOYSA-N 0.000 description 1
QIPOFOVHSNDLFR-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[6-(imidazol-1-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=NC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4C=NC=C4)=CC=3)=CC=2)=CC(C(C)(C)C)=N1 QIPOFOVHSNDLFR-UHFFFAOYSA-N 0.000 description 1
VGAXCJBQWVVJCD-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[6-(oxan-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=NC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CC4CCOCC4)=CC=3)=CC=2)=CC(C(C)(C)C)=N1 VGAXCJBQWVVJCD-UHFFFAOYSA-N 0.000 description 1
BHMXRCWXMHPUGV-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[6-(pyridin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=NC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CC=4C=CN=CC=4)=CC=3)=CC=2)=CC(C(C)(C)C)=N1 BHMXRCWXMHPUGV-UHFFFAOYSA-N 0.000 description 1
WBRPYBZVNDGOPW-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[6-[(1-methylpiperidin-4-yl)amino]pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1CN(C)CCC1NC1=CC=C(C=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=NC(C)=CC=3)=CC=2)C=N1 WBRPYBZVNDGOPW-UHFFFAOYSA-N 0.000 description 1
QBSZKIFIVMHWAA-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[6-[(1-oxo-1,4-thiazinan-4-yl)methyl]pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=NC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCS(=O)CC4)=CC=3)=CC=2)=CC(C(C)(C)C)=N1 QBSZKIFIVMHWAA-UHFFFAOYSA-N 0.000 description 1
RZGGQVGHFLXQDL-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[6-[(1-oxothian-4-yl)amino]pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=NC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(NC4CCS(=O)CC4)=CC=3)=CC=2)=CC(C(C)(C)C)=N1 RZGGQVGHFLXQDL-UHFFFAOYSA-N 0.000 description 1
QQWQPWRNNKDCIT-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[6-[(1-oxothiolan-3-yl)methyl]pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=NC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CC4CS(=O)CC4)=CC=3)=CC=2)=CC(C(C)(C)C)=N1 QQWQPWRNNKDCIT-UHFFFAOYSA-N 0.000 description 1
ILSAXKWINSZDNL-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[6-[3-methoxypropyl(methyl)amino]pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=NC(N(C)CCCOC)=CC=C1C(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=NN1C1=CC=C(C)N=C1 ILSAXKWINSZDNL-UHFFFAOYSA-N 0.000 description 1
YFZUZDQLWRZHGS-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-oxo-1h-pyridin-3-yl)pyrazol-3-yl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=CC(=O)NC=C1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 YFZUZDQLWRZHGS-UHFFFAOYSA-N 0.000 description 1
BJVKHYJDQWVCMI-UHFFFAOYSA-N 1-[6-tert-butyl-4-[2-(dimethylamino)ethyl]-3-oxo-1,4-benzoxazin-8-yl]-3-[4-[6-(thiomorpholin-4-ylamino)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound C1=C(C(C)(C)C)C=C2N(CCN(C)C)C(=O)COC2=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1NN1CCSCC1 BJVKHYJDQWVCMI-UHFFFAOYSA-N 0.000 description 1
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
XLXANWGTOZKKAZ-UHFFFAOYSA-N 2-(pyrrolidin-1-ylmethyl)pyridine Chemical compound C=1C=CC=NC=1CN1CCCC1 XLXANWGTOZKKAZ-UHFFFAOYSA-N 0.000 description 1
HKNYPYATWZNINL-UHFFFAOYSA-N 2-[4-tert-butyl-2-[[4-[5-(pyrrolidin-1-ylmethyl)pyridin-2-yl]naphthalen-1-yl]carbamoylamino]phenoxy]-n-methylacetamide Chemical compound CNC(=O)COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(N=C1)=CC=C1CN1CCCC1 HKNYPYATWZNINL-UHFFFAOYSA-N 0.000 description 1
NEOQJMIGRQDLOB-UHFFFAOYSA-N 2-amino-4-[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]benzamide Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=C(N)C(C(N)=O)=CC=3)=CC=2)=CC(C(C)(C)C)=N1 NEOQJMIGRQDLOB-UHFFFAOYSA-N 0.000 description 1
125000000872 2-diethylaminoethoxy group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 description 1
VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical group C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 description 1
MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
HLSAQRWCIRURAK-UHFFFAOYSA-N 3-[5-tert-butyl-2-methoxy-3-[[4-[6-(pyrrolidin-1-ylmethyl)pyridin-3-yl]naphthalen-1-yl]carbamoylamino]phenyl]prop-2-enamide Chemical compound C1=C(C(C)(C)C)C=C(C=CC(N)=O)C(OC)=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCCC1 HLSAQRWCIRURAK-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical compound OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 description 1
VIUDNHJNUDJCMW-UHFFFAOYSA-N 5-[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]pyridine-3-carboxamide Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=C(C=NC=3)C(N)=O)=CC=2)=CC(C(C)(C)C)=N1 VIUDNHJNUDJCMW-UHFFFAOYSA-N 0.000 description 1
AYQWJGOJDRFTDG-UHFFFAOYSA-N 5-tert-butyl-n,1-dimethyl-3-[[4-(3-morpholin-4-ylcyclohexen-1-yl)naphthalen-1-yl]carbamoylamino]pyrrole-2-carboxamide Chemical compound C1=C(C(C)(C)C)N(C)C(C(=O)NC)=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C1=CC(N2CCOCC2)CCC1 AYQWJGOJDRFTDG-UHFFFAOYSA-N 0.000 description 1
DGTAPLGGJIUJGF-UHFFFAOYSA-N 5-tert-butyl-n,1-dimethyl-3-[[4-(6-oxo-1-pyridin-4-yl-2,3-dihydropyridin-4-yl)naphthalen-1-yl]carbamoylamino]pyrrole-2-carboxamide Chemical compound C1=C(C(C)(C)C)N(C)C(C(=O)NC)=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C1=CC(=O)N(C=2C=CN=CC=2)CC1 DGTAPLGGJIUJGF-UHFFFAOYSA-N 0.000 description 1
WAIRRLYHTBPAQI-UHFFFAOYSA-N 5-tert-butyl-n-methyl-3-[[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]carbamoylamino]thiophene-2-carboxamide Chemical compound S1C(C(C)(C)C)=CC(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1C(=O)NC WAIRRLYHTBPAQI-UHFFFAOYSA-N 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
206010048998 Acute phase reaction Diseases 0.000 description 1
206010001939 Aminoaciduria Diseases 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
102000013455 Amyloid beta-Peptides Human genes 0.000 description 1
108010090849 Amyloid beta-Peptides Proteins 0.000 description 1
206010002198 Anaphylactic reaction Diseases 0.000 description 1
206010002650 Anorexia nervosa and bulimia Diseases 0.000 description 1
208000019901 Anxiety disease Diseases 0.000 description 1
200000000007 Arterial disease Diseases 0.000 description 1
208000012657 Atopic disease Diseases 0.000 description 1
206010003645 Atopy Diseases 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
102000004506 Blood Proteins Human genes 0.000 description 1
108010017384 Blood Proteins Proteins 0.000 description 1
241000589969 Borreliella burgdorferi Species 0.000 description 1
108091003079 Bovine Serum Albumin Proteins 0.000 description 1
201000006474 Brain Ischemia Diseases 0.000 description 1
229940124638 COX inhibitor Drugs 0.000 description 1
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
208000024172 Cardiovascular disease Diseases 0.000 description 1
206010008027 Cerebellar atrophy Diseases 0.000 description 1
206010008120 Cerebral ischaemia Diseases 0.000 description 1
206010063094 Cerebral malaria Diseases 0.000 description 1
102000008186 Collagen Human genes 0.000 description 1
108010035532 Collagen Proteins 0.000 description 1
206010010904 Convulsion Diseases 0.000 description 1
102000010907 Cyclooxygenase 2 Human genes 0.000 description 1
108010037462 Cyclooxygenase 2 Proteins 0.000 description 1
208000016192 Demyelinating disease Diseases 0.000 description 1
206010012442 Dermatitis contact Diseases 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
208000032131 Diabetic Neuropathies Diseases 0.000 description 1
206010013975 Dyspnoeas Diseases 0.000 description 1
208000032274 Encephalopathy Diseases 0.000 description 1
241000709661 Enterovirus Species 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
108010008165 Etanercept Proteins 0.000 description 1
KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
206010016654 Fibrosis Diseases 0.000 description 1
201000004311 Gilles de la Tourette syndrome Diseases 0.000 description 1
208000010412 Glaucoma Diseases 0.000 description 1
206010018364 Glomerulonephritis Diseases 0.000 description 1
208000035895 Guillain-Barré syndrome Diseases 0.000 description 1
206010019233 Headaches Diseases 0.000 description 1
208000032087 Hereditary Leber Optic Atrophy Diseases 0.000 description 1
206010020365 Homocystinuria Diseases 0.000 description 1
208000023105 Huntington disease Diseases 0.000 description 1
206010049645 Hypercatabolism Diseases 0.000 description 1
208000035150 Hypercholesterolemia Diseases 0.000 description 1
206010020751 Hypersensitivity Diseases 0.000 description 1
208000013016 Hypoglycemia Diseases 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
102000008070 Interferon-gamma Human genes 0.000 description 1
108010074328 Interferon-gamma Proteins 0.000 description 1
102000019223 Interleukin-1 receptor Human genes 0.000 description 1
108050006617 Interleukin-1 receptor Proteins 0.000 description 1
102000051628 Interleukin-1 receptor antagonist Human genes 0.000 description 1
108700021006 Interleukin-1 receptor antagonist Proteins 0.000 description 1
102000010781 Interleukin-6 Receptors Human genes 0.000 description 1
108010038501 Interleukin-6 Receptors Proteins 0.000 description 1
208000021342 Isolated sulfite oxidase deficiency Diseases 0.000 description 1
201000003533 Leber congenital amaurosis Diseases 0.000 description 1
102000003960 Ligases Human genes 0.000 description 1
108090000364 Ligases Proteins 0.000 description 1
206010025323 Lymphomas Diseases 0.000 description 1
102000043136 MAP kinase family Human genes 0.000 description 1
108091054455 MAP kinase family Proteins 0.000 description 1
208000009564 MELAS Syndrome Diseases 0.000 description 1
201000009035 MERRF syndrome Diseases 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
208000005903 Manganese Poisoning Diseases 0.000 description 1
201000009906 Meningitis Diseases 0.000 description 1
206010027202 Meningitis bacterial Diseases 0.000 description 1
206010027260 Meningitis viral Diseases 0.000 description 1
206010027439 Metal poisoning Diseases 0.000 description 1
PGBFYLVIMDQYMS-UHFFFAOYSA-N Methyl thiophene-2-carboxylate Chemical compound COC(=O)C1=CC=CS1 PGBFYLVIMDQYMS-UHFFFAOYSA-N 0.000 description 1
206010049567 Miller Fisher syndrome Diseases 0.000 description 1
206010028116 Mucosal inflammation Diseases 0.000 description 1
201000010927 Mucositis Diseases 0.000 description 1
208000034486 Multi-organ failure Diseases 0.000 description 1
208000010718 Multiple Organ Failure Diseases 0.000 description 1
241000699660 Mus musculus Species 0.000 description 1
208000000112 Myalgia Diseases 0.000 description 1
206010069825 Myoclonic epilepsy and ragged-red fibres Diseases 0.000 description 1
201000002481 Myositis Diseases 0.000 description 1
229910003844 NSO2 Inorganic materials 0.000 description 1
208000012902 Nervous system disease Diseases 0.000 description 1
208000025966 Neurological disease Diseases 0.000 description 1
244000061176 Nicotiana tabacum Species 0.000 description 1
235000002637 Nicotiana tabacum Nutrition 0.000 description 1
102000008299 Nitric Oxide Synthase Human genes 0.000 description 1
108010021487 Nitric Oxide Synthase Proteins 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
208000008589 Obesity Diseases 0.000 description 1
240000007817 Olea europaea Species 0.000 description 1
208000003435 Optic Neuritis Diseases 0.000 description 1
206010061323 Optic neuropathy Diseases 0.000 description 1
208000010191 Osteitis Deformans Diseases 0.000 description 1
208000001132 Osteoporosis Diseases 0.000 description 1
239000012826 P38 inhibitor Substances 0.000 description 1
208000027868 Paget disease Diseases 0.000 description 1
208000018737 Parkinson disease Diseases 0.000 description 1
229930182555 Penicillin Natural products 0.000 description 1
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
108091005804 Peptidases Proteins 0.000 description 1
208000037581 Persistent Infection Diseases 0.000 description 1
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
BELBBZDIHDAJOR-UHFFFAOYSA-N Phenolsulfonephthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2S(=O)(=O)O1 BELBBZDIHDAJOR-UHFFFAOYSA-N 0.000 description 1
208000021161 Plasma cell disease Diseases 0.000 description 1
208000005374 Poisoning Diseases 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
239000004365 Protease Substances 0.000 description 1
102000001708 Protein Isoforms Human genes 0.000 description 1
108010029485 Protein Isoforms Proteins 0.000 description 1
201000001177 Pyomyositis Diseases 0.000 description 1
241000700159 Rattus Species 0.000 description 1
206010063837 Reperfusion injury Diseases 0.000 description 1
208000017442 Retinal disease Diseases 0.000 description 1
208000006289 Rett Syndrome Diseases 0.000 description 1
102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 1
241000219061 Rheum Species 0.000 description 1
208000025747 Rheumatic disease Diseases 0.000 description 1
206010070835 Skin sensitisation Diseases 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
108700036932 Sulfite oxidase deficiency Proteins 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
208000033809 Suppuration Diseases 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 description 1
208000000323 Tourette Syndrome Diseases 0.000 description 1
208000016620 Tourette disease Diseases 0.000 description 1
241000256838 Vespula Species 0.000 description 1
241000700605 Viruses Species 0.000 description 1
AEJGVAMKSAPCJU-UHFFFAOYSA-N [4-[2-(morpholin-4-ylmethyl)pyrimidin-5-yl]naphthalen-1-yl]urea Chemical compound N1(CCOCC1)CC1=NC=C(C=N1)C1=CC=C(C2=CC=CC=C12)NC(=O)N AEJGVAMKSAPCJU-UHFFFAOYSA-N 0.000 description 1
OWIHJQAJFPSPPR-UHFFFAOYSA-N [4-[6-[3-methoxypropyl(methyl)amino]pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COCCCN(C)c1ccc(cn1)-c1ccc(NC(N)=O)c2ccccc12 OWIHJQAJFPSPPR-UHFFFAOYSA-N 0.000 description 1
230000002159 abnormal effect Effects 0.000 description 1
230000005856 abnormality Effects 0.000 description 1
238000009825 accumulation Methods 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
208000012871 acute dyspnea Diseases 0.000 description 1
206010069351 acute lung injury Diseases 0.000 description 1
230000004658 acute-phase response Effects 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
230000032683 aging Effects 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000004183 alkoxy alkyl group Chemical group 0.000 description 1
239000013566 allergen Substances 0.000 description 1
208000002029 allergic contact dermatitis Diseases 0.000 description 1
208000026935 allergic disease Diseases 0.000 description 1
230000007815 allergy Effects 0.000 description 1
VREFGVBLTWBCJP-UHFFFAOYSA-N alprazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1 VREFGVBLTWBCJP-UHFFFAOYSA-N 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
229940063655 aluminum stearate Drugs 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 1
230000036783 anaphylactic response Effects 0.000 description 1
208000003455 anaphylaxis Diseases 0.000 description 1
208000022531 anorexia Diseases 0.000 description 1
229940121363 anti-inflammatory agent Drugs 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
230000036506 anxiety Effects 0.000 description 1
238000003782 apoptosis assay Methods 0.000 description 1
230000006907 apoptotic process Effects 0.000 description 1
210000001367 artery Anatomy 0.000 description 1
210000001188 articular cartilage Anatomy 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
201000009904 bacterial meningitis Diseases 0.000 description 1
210000000227 basophil cell of anterior lobe of hypophysis Anatomy 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
238000004820 blood count Methods 0.000 description 1
230000010072 bone remodeling Effects 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
208000029028 brain injury Diseases 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
238000004364 calculation method Methods 0.000 description 1
239000007894 caplet Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910002091 carbon monoxide Inorganic materials 0.000 description 1
239000000969 carrier Substances 0.000 description 1
210000000845 cartilage Anatomy 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
230000024245 cell differentiation Effects 0.000 description 1
230000004663 cell proliferation Effects 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
230000002490 cerebral effect Effects 0.000 description 1
206010008118 cerebral infarction Diseases 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
230000001713 cholinergic effect Effects 0.000 description 1
210000001612 chondrocyte Anatomy 0.000 description 1
208000021735 chronic enteritis Diseases 0.000 description 1
230000007882 cirrhosis Effects 0.000 description 1
208000019425 cirrhosis of liver Diseases 0.000 description 1
229920001436 collagen Polymers 0.000 description 1
238000002648 combination therapy Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
230000002596 correlated effect Effects 0.000 description 1
208000029039 cyanide poisoning Diseases 0.000 description 1
YSCUSPWOQQCNHQ-UHFFFAOYSA-N cyclohexanone hexan-1-ol Chemical compound C1(CCCCC1)=O.C(CCCCC)O YSCUSPWOQQCNHQ-UHFFFAOYSA-N 0.000 description 1
239000000824 cytostatic agent Substances 0.000 description 1
230000001085 cytostatic effect Effects 0.000 description 1
206010061428 decreased appetite Diseases 0.000 description 1
230000007123 defense Effects 0.000 description 1
230000002950 deficient Effects 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
230000008021 deposition Effects 0.000 description 1
238000001514 detection method Methods 0.000 description 1
KZNICNPSHKQLFF-UHFFFAOYSA-N dihydromaleimide Natural products O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
KCSIVKUACGHGPH-UHFFFAOYSA-N dimethyl 5-[[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]carbamoylamino]benzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC(C(=O)OC)=CC(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 KCSIVKUACGHGPH-UHFFFAOYSA-N 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
VZFRNCSOCOPNDB-AJKFJWDBSA-N domoic acid Chemical compound OC(=O)[C@@H](C)\C=C\C=C(/C)[C@H]1CN[C@H](C(O)=O)[C@H]1CC(O)=O VZFRNCSOCOPNDB-AJKFJWDBSA-N 0.000 description 1
VZFRNCSOCOPNDB-UHFFFAOYSA-N domoic acid Natural products OC(=O)C(C)C=CC=C(C)C1CNC(C(O)=O)C1CC(O)=O VZFRNCSOCOPNDB-UHFFFAOYSA-N 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
238000012377 drug delivery Methods 0.000 description 1
239000012636 effector Substances 0.000 description 1
239000003792 electrolyte Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
229940073621 enbrel Drugs 0.000 description 1
230000002124 endocrine Effects 0.000 description 1
206010015037 epilepsy Diseases 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
GNHWYXRSHRJMDP-UHFFFAOYSA-N ethyl 3-[[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]carbamoylamino]benzoate Chemical compound CCOC(=O)C1=CC=CC(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 GNHWYXRSHRJMDP-UHFFFAOYSA-N 0.000 description 1
JGENQXRHGVLQOK-UHFFFAOYSA-N ethyl 4-[[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 JGENQXRHGVLQOK-UHFFFAOYSA-N 0.000 description 1
210000003527 eukaryotic cell Anatomy 0.000 description 1
230000001605 fetal effect Effects 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
230000006870 function Effects 0.000 description 1
239000008187 granular material Substances 0.000 description 1
230000012010 growth Effects 0.000 description 1
239000003102 growth factor Substances 0.000 description 1
231100000869 headache Toxicity 0.000 description 1
230000036541 health Effects 0.000 description 1
208000007386 hepatic encephalopathy Diseases 0.000 description 1
206010073071 hepatocellular carcinoma Diseases 0.000 description 1
231100000844 hepatocellular carcinoma Toxicity 0.000 description 1
125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
230000000971 hippocampal effect Effects 0.000 description 1
230000013632 homeostatic process Effects 0.000 description 1
125000001183 hydrocarbyl group Chemical group 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000033444 hydroxylation Effects 0.000 description 1
238000005805 hydroxylation reaction Methods 0.000 description 1
208000023399 hyperprolinemia Diseases 0.000 description 1
230000002218 hypoglycaemic effect Effects 0.000 description 1
230000001146 hypoxic effect Effects 0.000 description 1
210000002865 immune cell Anatomy 0.000 description 1
239000012642 immune effector Substances 0.000 description 1
230000036737 immune function Effects 0.000 description 1
230000008073 immune recognition Effects 0.000 description 1
229940121354 immunomodulator Drugs 0.000 description 1
229910052738 indium Inorganic materials 0.000 description 1
239000012678 infectious agent Substances 0.000 description 1
210000004969 inflammatory cell Anatomy 0.000 description 1
208000027866 inflammatory disease Diseases 0.000 description 1
229960000598 infliximab Drugs 0.000 description 1
206010022000 influenza Diseases 0.000 description 1
230000004941 influx Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
229960003130 interferon gamma Drugs 0.000 description 1
239000003407 interleukin 1 receptor blocking agent Substances 0.000 description 1
230000021995 interleukin-8 production Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000007919 intrasynovial administration Methods 0.000 description 1
230000009545 invasion Effects 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000002085 irritant Substances 0.000 description 1
231100000021 irritant Toxicity 0.000 description 1
208000001875 irritant dermatitis Diseases 0.000 description 1
208000028867 ischemia Diseases 0.000 description 1
210000004153 islets of langerhan Anatomy 0.000 description 1
VZFRNCSOCOPNDB-OXYNIABMSA-N isodomoic acid D Natural products CC(C=C/C=C(/C)C1CNC(C1CC(=O)O)C(=O)O)C(=O)O VZFRNCSOCOPNDB-OXYNIABMSA-N 0.000 description 1
238000011813 knockout mouse model Methods 0.000 description 1
238000012332 laboratory investigation Methods 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
229940067606 lecithin Drugs 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
208000032839 leukemia Diseases 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
238000012417 linear regression Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
210000004698 lymphocyte Anatomy 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
206010025482 malaise Diseases 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
208000027202 mammary Paget disease Diseases 0.000 description 1
229910052748 manganese Inorganic materials 0.000 description 1
239000011572 manganese Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
210000004379 membrane Anatomy 0.000 description 1
239000012528 membrane Substances 0.000 description 1
108020004999 messenger RNA Proteins 0.000 description 1
208000030159 metabolic disease Diseases 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
NXAHPYBSEXEXPT-UHFFFAOYSA-N methyl 4-methoxy-3-[[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]carbamoylamino]benzoate Chemical compound COC(=O)C1=CC=C(OC)C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 NXAHPYBSEXEXPT-UHFFFAOYSA-N 0.000 description 1
XRRWPONERREOCZ-UHFFFAOYSA-N methyl 5-tert-butyl-1-methyl-3-[[4-(3-morpholin-4-ylcyclohexen-1-yl)naphthalen-1-yl]carbamoylamino]pyrrole-2-carboxylate Chemical compound C1=C(C(C)(C)C)N(C)C(C(=O)OC)=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C1=CC(N2CCOCC2)CCC1 XRRWPONERREOCZ-UHFFFAOYSA-N 0.000 description 1
VAJGUMSBKIWZPH-UHFFFAOYSA-N methyl 5-tert-butyl-1-methyl-3-[[4-(6-oxo-1-pyridin-4-yl-2,3-dihydropyridin-4-yl)naphthalen-1-yl]carbamoylamino]pyrrole-2-carboxylate Chemical compound C1=C(C(C)(C)C)N(C)C(C(=O)OC)=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C1=CC(=O)N(C=2C=CN=CC=2)CC1 VAJGUMSBKIWZPH-UHFFFAOYSA-N 0.000 description 1
ARUDGTVSHPBRDS-UHFFFAOYSA-N methyl 5-tert-butyl-3-[[4-(3-morpholin-4-ylcyclohexen-1-yl)naphthalen-1-yl]carbamoylamino]thiophene-2-carboxylate Chemical compound S1C(C(C)(C)C)=CC(NC(=O)NC=2C3=CC=CC=C3C(C=3CCCC(C=3)N3CCOCC3)=CC=2)=C1C(=O)OC ARUDGTVSHPBRDS-UHFFFAOYSA-N 0.000 description 1
UWYKWAAIAXCYMM-UHFFFAOYSA-N methyl 5-tert-butyl-3-[[4-(6-oxo-1-pyridin-4-yl-2,3-dihydropyridin-4-yl)naphthalen-1-yl]carbamoylamino]thiophene-2-carboxylate Chemical compound S1C(C(C)(C)C)=CC(NC(=O)NC=2C3=CC=CC=C3C(C=3CCN(C(=O)C=3)C=3C=CN=CC=3)=CC=2)=C1C(=O)OC UWYKWAAIAXCYMM-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
ZAHQPTJLOCWVPG-UHFFFAOYSA-N mitoxantrone dihydrochloride Chemical compound Cl.Cl.O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO ZAHQPTJLOCWVPG-UHFFFAOYSA-N 0.000 description 1
210000003003 monocyte-macrophage precursor cell Anatomy 0.000 description 1
238000010172 mouse model Methods 0.000 description 1
208000029744 multiple organ dysfunction syndrome Diseases 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
208000013465 muscle pain Diseases 0.000 description 1
208000031225 myocardial ischemia Diseases 0.000 description 1
HIJNVNMNKCAXFS-UHFFFAOYSA-N n-[3-tert-butyl-5-[[4-[5-(oxan-4-ylamino)pyridin-2-yl]naphthalen-1-yl]carbamoylamino]phenyl]-2-morpholin-4-ylacetamide Chemical compound C=1C(NC(=O)NC=2C3=CC=CC=C3C(C=3N=CC(NC4CCOCC4)=CC=3)=CC=2)=CC(C(C)(C)C)=CC=1NC(=O)CN1CCOCC1 HIJNVNMNKCAXFS-UHFFFAOYSA-N 0.000 description 1
AFASVBQWMUSSDY-UHFFFAOYSA-N n-[4-tert-butyl-2-[[4-(6-oxo-1h-pyridin-3-yl)naphthalen-1-yl]carbamoylamino]phenyl]-2-morpholin-4-ylacetamide Chemical compound C=1C=C(C2=CNC(=O)C=C2)C2=CC=CC=C2C=1NC(=O)NC1=CC(C(C)(C)C)=CC=C1NC(=O)CN1CCOCC1 AFASVBQWMUSSDY-UHFFFAOYSA-N 0.000 description 1
XRDBSOVLPQXHKU-UHFFFAOYSA-N n-[4-tert-butyl-2-[[4-[4-(1-methylpiperidin-4-yl)oxyphenyl]naphthalen-1-yl]carbamoylamino]phenyl]acetamide Chemical compound C1CN(C)CCC1OC1=CC=C(C=2C3=CC=CC=C3C(NC(=O)NC=3C(=CC=C(C=3)C(C)(C)C)NC(C)=O)=CC=2)C=C1 XRDBSOVLPQXHKU-UHFFFAOYSA-N 0.000 description 1
125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
201000009240 nasopharyngitis Diseases 0.000 description 1
230000002956 necrotizing effect Effects 0.000 description 1
210000000653 nervous system Anatomy 0.000 description 1
208000004296 neuralgia Diseases 0.000 description 1
210000002682 neurofibrillary tangle Anatomy 0.000 description 1
208000021722 neuropathic pain Diseases 0.000 description 1
201000001119 neuropathy Diseases 0.000 description 1
230000007823 neuropathy Effects 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
235000020824 obesity Nutrition 0.000 description 1
230000000771 oncological effect Effects 0.000 description 1
208000020911 optic nerve disease Diseases 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
230000003349 osteoarthritic effect Effects 0.000 description 1
210000002997 osteoclast Anatomy 0.000 description 1
230000002018 overexpression Effects 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
229940094443 oxytocics prostaglandins Drugs 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
244000045947 parasite Species 0.000 description 1
244000052769 pathogen Species 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
230000001991 pathophysiological effect Effects 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
208000033808 peripheral neuropathy Diseases 0.000 description 1
230000002085 persistent effect Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229960003531 phenolsulfonphthalein Drugs 0.000 description 1
XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
231100000572 poisoning Toxicity 0.000 description 1
230000000607 poisoning effect Effects 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
208000001685 postmenopausal osteoporosis Diseases 0.000 description 1
230000001124 posttranscriptional effect Effects 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000011533 pre-incubation Methods 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000005522 programmed cell death Effects 0.000 description 1
208000037821 progressive disease Diseases 0.000 description 1
230000002062 proliferating effect Effects 0.000 description 1
230000035755 proliferation Effects 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
150000003180 prostaglandins Chemical class 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
125000006513 pyridinyl methyl group Chemical group 0.000 description 1
238000003127 radioimmunoassay Methods 0.000 description 1
238000001959 radiotherapy Methods 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000026749 regulation of bone remodeling Effects 0.000 description 1
230000010410 reperfusion Effects 0.000 description 1
230000010076 replication Effects 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
208000032253 retinal ischemia Diseases 0.000 description 1
230000000552 rheumatic effect Effects 0.000 description 1
206010039083 rhinitis Diseases 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
201000000980 schizophrenia Diseases 0.000 description 1
230000035939 shock Effects 0.000 description 1
238000009097 single-agent therapy Methods 0.000 description 1
231100000370 skin sensitisation Toxicity 0.000 description 1
150000003384 small molecules Chemical class 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000000243 solution Substances 0.000 description 1
241000894007 species Species 0.000 description 1
210000000278 spinal cord Anatomy 0.000 description 1
238000011699 spontaneously hypertensive rat Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
210000000130 stem cell Anatomy 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
239000011593 sulfur Chemical group 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000005062 synaptic transmission Effects 0.000 description 1
210000001179 synovial fluid Anatomy 0.000 description 1
210000001258 synovial membrane Anatomy 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
125000006223 tetrahydrofuranylmethyl group Chemical group 0.000 description 1
ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical compound O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 description 1
BUGOPWGPQGYYGR-UHFFFAOYSA-N thiane 1,1-dioxide Chemical compound O=S1(=O)CCCCC1 BUGOPWGPQGYYGR-UHFFFAOYSA-N 0.000 description 1
NNLBRYQGMOYARS-UHFFFAOYSA-N thiane 1-oxide Chemical compound O=S1CCCCC1 NNLBRYQGMOYARS-UHFFFAOYSA-N 0.000 description 1
150000003595 thromboxanes Chemical class 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
230000000451 tissue damage Effects 0.000 description 1
231100000827 tissue damage Toxicity 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
QQJLHRRUATVHED-UHFFFAOYSA-N tramazoline Chemical compound N1CCN=C1NC1=CC=CC2=C1CCCC2 QQJLHRRUATVHED-UHFFFAOYSA-N 0.000 description 1
229960001262 tramazoline Drugs 0.000 description 1
238000011830 transgenic mouse model Methods 0.000 description 1
238000011269 treatment regimen Methods 0.000 description 1
YFHICDDUDORKJB-UHFFFAOYSA-N trimethylene carbonate Chemical compound O=C1OCCCO1 YFHICDDUDORKJB-UHFFFAOYSA-N 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1
230000005951 type IV hypersensitivity Effects 0.000 description 1
210000004509 vascular smooth muscle cell Anatomy 0.000 description 1
229940124549 vasodilator Drugs 0.000 description 1
239000003071 vasodilator agent Substances 0.000 description 1
239000002435 venom Substances 0.000 description 1
210000001048 venom Anatomy 0.000 description 1
231100000611 venom Toxicity 0.000 description 1
230000006648 viral gene expression Effects 0.000 description 1
230000029812 viral genome replication Effects 0.000 description 1
201000010044 viral meningitis Diseases 0.000 description 1
230000003612 virological effect Effects 0.000 description 1
230000009278 visceral effect Effects 0.000 description 1
208000029257 vision disease Diseases 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
208000016261 weight loss Diseases 0.000 description 1
230000004580 weight loss Effects 0.000 description 1
230000029663 wound healing Effects 0.000 description 1