JP2005503400A5 - - Google Patents
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- Publication number
- JP2005503400A5 JP2005503400A5 JP2003526402A JP2003526402A JP2005503400A5 JP 2005503400 A5 JP2005503400 A5 JP 2005503400A5 JP 2003526402 A JP2003526402 A JP 2003526402A JP 2003526402 A JP2003526402 A JP 2003526402A JP 2005503400 A5 JP2005503400 A5 JP 2005503400A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- pyridin
- naphthalen
- ylmethyl
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- -1 pyridinonyl Chemical group 0.000 claims 191
- 125000000217 alkyl group Chemical group 0.000 claims 130
- 125000003545 alkoxy group Chemical group 0.000 claims 47
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 45
- 150000002825 nitriles Chemical class 0.000 claims 39
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 31
- 125000004076 pyridyl group Chemical group 0.000 claims 30
- 229910052736 halogen Inorganic materials 0.000 claims 26
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 26
- 125000002883 imidazolyl group Chemical group 0.000 claims 24
- 150000002367 halogens Chemical class 0.000 claims 23
- 125000003118 aryl group Chemical group 0.000 claims 21
- 239000004202 carbamide Substances 0.000 claims 20
- 125000004043 oxo group Chemical group O=* 0.000 claims 20
- 229910052717 sulfur Inorganic materials 0.000 claims 20
- 229910052760 oxygen Inorganic materials 0.000 claims 19
- 125000001072 heteroaryl group Chemical group 0.000 claims 18
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 17
- 125000004193 piperazinyl group Chemical group 0.000 claims 16
- 125000003373 pyrazinyl group Chemical group 0.000 claims 16
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 16
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims 15
- 125000005843 halogen group Chemical group 0.000 claims 15
- 239000008194 pharmaceutical composition Substances 0.000 claims 15
- 125000001624 naphthyl group Chemical group 0.000 claims 14
- 229910052757 nitrogen Inorganic materials 0.000 claims 14
- 125000000168 pyrrolyl group Chemical group 0.000 claims 14
- 125000000623 heterocyclic group Chemical group 0.000 claims 13
- 125000002098 pyridazinyl group Chemical group 0.000 claims 12
- 125000002541 furyl group Chemical group 0.000 claims 11
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 11
- 125000003226 pyrazolyl group Chemical group 0.000 claims 11
- 125000002252 acyl group Chemical group 0.000 claims 10
- 125000003386 piperidinyl group Chemical group 0.000 claims 9
- 125000003831 tetrazolyl group Chemical group 0.000 claims 9
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 8
- 201000010099 disease Diseases 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 8
- 125000001544 thienyl group Chemical group 0.000 claims 8
- 125000004432 carbon atom Chemical group C* 0.000 claims 7
- 125000005879 dioxolanyl group Chemical group 0.000 claims 7
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 7
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 7
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 7
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 7
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 6
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 6
- 102000004127 Cytokines Human genes 0.000 claims 6
- 108090000695 Cytokines Proteins 0.000 claims 6
- 206010019280 Heart failures Diseases 0.000 claims 6
- 206010028980 Neoplasm Diseases 0.000 claims 6
- 125000004442 acylamino group Chemical group 0.000 claims 6
- 125000000304 alkynyl group Chemical group 0.000 claims 6
- 201000011510 cancer Diseases 0.000 claims 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 6
- 125000006576 di-(C1-C3-alkyl)-aminocarbonyl group Chemical group 0.000 claims 6
- 125000001041 indolyl group Chemical group 0.000 claims 6
- 230000001404 mediated effect Effects 0.000 claims 6
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 6
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 5
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims 5
- 208000009137 Behcet syndrome Diseases 0.000 claims 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 5
- 201000009273 Endometriosis Diseases 0.000 claims 5
- 208000016604 Lyme disease Diseases 0.000 claims 5
- 206010033645 Pancreatitis Diseases 0.000 claims 5
- 206010040047 Sepsis Diseases 0.000 claims 5
- 125000003342 alkenyl group Chemical group 0.000 claims 5
- 125000003435 aroyl group Chemical group 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 5
- 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims 5
- 125000005842 heteroatom Chemical group 0.000 claims 5
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims 5
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 5
- 125000001786 isothiazolyl group Chemical group 0.000 claims 5
- 125000000842 isoxazolyl group Chemical group 0.000 claims 5
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 5
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims 4
- 208000024827 Alzheimer disease Diseases 0.000 claims 4
- 206010048873 Traumatic arthritis Diseases 0.000 claims 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 4
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 4
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 4
- 238000007887 coronary angioplasty Methods 0.000 claims 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000005494 pyridonyl group Chemical group 0.000 claims 4
- 208000037803 restenosis Diseases 0.000 claims 4
- 239000000779 smoke Substances 0.000 claims 4
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 4
- 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 3
- 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 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 class C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 KLPFPTSVYVEKOL-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 206010035664 Pneumonia Diseases 0.000 claims 3
- 230000001154 acute effect Effects 0.000 claims 3
- 125000004599 benzpyrazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 3
- 230000001684 chronic effect Effects 0.000 claims 3
- 125000005436 dihydrobenzothiophenyl group Chemical group S1C(CC2=C1C=CC=C2)* 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 3
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- 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 2
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 2
- 125000006594 (C1-C3) alkylsulfony group Chemical group 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 125000005940 1,4-dioxanyl group Chemical group 0.000 claims 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- QYCGBAJADAGLLK-UHFFFAOYSA-N 1-(cyclohepten-1-yl)cycloheptene Chemical group C1CCCCC=C1C1=CCCCCC1 QYCGBAJADAGLLK-UHFFFAOYSA-N 0.000 claims 2
- VSIYJQNFMOOGCU-UHFFFAOYSA-N 1-(cyclohexen-1-yl)cyclohexene Chemical group C1CCCC(C=2CCCCC=2)=C1 VSIYJQNFMOOGCU-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- ZCPTVULXWYSYNL-UHFFFAOYSA-N 1-[5-tert-butyl-2-(dimethylamino)phenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CN(C)C1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 ZCPTVULXWYSYNL-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- 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 2
- MRRTWVXKQWEBCG-UHFFFAOYSA-N 1-[5-tert-butyl-3-(2,3-dihydroxypropyl)-2-methoxyphenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COC1=C(CC(O)CO)C=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 MRRTWVXKQWEBCG-UHFFFAOYSA-N 0.000 claims 2
- 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 2
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- 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 2
- 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 2
- 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 2
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- 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 2
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- 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 1
- 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 1
- 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 1
- 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 1
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- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims 1
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- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
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- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims 1
- 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 1
- 125000003113 cycloheptyloxy group Chemical group C1(CCCCCC1)O* 0.000 claims 1
- 125000002243 cyclohexanonyl group Chemical group *C1(*)C(=O)C(*)(*)C(*)(*)C(*)(*)C1(*)* 0.000 claims 1
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- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000004652 decahydroisoquinolinyl group Chemical group C1(NCCC2CCCCC12)* 0.000 claims 1
- 125000004856 decahydroquinolinyl group Chemical group N1(CCCC2CCCCC12)* 0.000 claims 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004582 dihydrobenzothienyl group Chemical group S1C(CC2=C1C=CC=C2)* 0.000 claims 1
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- 125000005044 dihydroquinolinyl group Chemical group N1(CC=CC2=CC=CC=C12)* 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
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- 125000001153 fluoro group Chemical group F* 0.000 claims 1
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- 230000001738 genotoxic effect Effects 0.000 claims 1
- 125000005241 heteroarylamino group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 125000002636 imidazolinyl group Chemical group 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 1
- 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 claims 1
- 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 1
- 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 1
- 125000005968 oxazolinyl group Chemical group 0.000 claims 1
- 125000003566 oxetanyl group Chemical group 0.000 claims 1
- 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 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims 1
- 125000005545 phthalimidyl group Chemical group 0.000 claims 1
- 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 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims 1
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- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000001984 thiazolidinyl group Chemical group 0.000 claims 1
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| US31895801P | 2001-09-13 | 2001-09-13 | |
| PCT/US2002/028615 WO2003022273A1 (en) | 2001-09-13 | 2002-09-09 | Methods of treating cytokine mediated diseases |
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| US20030220336A1 (en) * | 2002-04-05 | 2003-11-27 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Method of treating mucus hypersecretion |
| US7521480B2 (en) | 2002-11-21 | 2009-04-21 | Neurosearch | Aryl ureido benzoic acid derivatives and their use |
| US7202257B2 (en) * | 2003-12-24 | 2007-04-10 | Deciphera Pharmaceuticals, Llc | Anti-inflammatory medicaments |
| US7144911B2 (en) | 2002-12-31 | 2006-12-05 | Deciphera Pharmaceuticals Llc | Anti-inflammatory medicaments |
| US8338120B2 (en) | 2003-05-05 | 2012-12-25 | Probiodrug Ag | Method of treating inflammation with glutaminyl cyclase inhibitors |
| CN1838958A (zh) * | 2003-08-22 | 2006-09-27 | 贝林格尔·英格海姆药物公司 | 治疗慢性阻塞性肺病和肺动脉高血压的方法 |
| SG146624A1 (en) | 2003-09-11 | 2008-10-30 | Kemia Inc | Cytokine inhibitors |
| AU2005267185A1 (en) * | 2004-06-25 | 2006-02-02 | Icos Corporation | Bisarylurea derivatives useful for inhibiting CHK1 |
| CA2592118C (en) | 2004-12-23 | 2015-11-17 | Deciphera Pharmaceuticals, Llc | Urea derivatives as enzyme modulators |
| TWI370130B (en) | 2005-11-24 | 2012-08-11 | Eisai R&D Man Co Ltd | Two cyclic cinnamide compound |
| TWI378091B (en) | 2006-03-09 | 2012-12-01 | Eisai R&D Man Co Ltd | Multi-cyclic cinnamide derivatives |
| US20080064717A1 (en) * | 2006-05-19 | 2008-03-13 | Rajesh Iyengar | Inhibitors of diacylglycerol O-acyltransferase type 1 enzyme |
| US20080015227A1 (en) * | 2006-05-19 | 2008-01-17 | Kym Philip R | Inhibitors of diacylglycerol O-acyltransferase type 1 enzyme |
| EP2019093A4 (en) * | 2006-05-19 | 2011-02-23 | Eisai R&D Man Co Ltd | CINEMA ACID AMID DERIVATIVE FROM THE UREA TYPE |
| US8188113B2 (en) | 2006-09-14 | 2012-05-29 | Deciphera Pharmaceuticals, Inc. | Dihydropyridopyrimidinyl, dihydronaphthyidinyl and related compounds useful as kinase inhibitors for the treatment of proliferative diseases |
| EP2066642A1 (en) * | 2006-09-25 | 2009-06-10 | Arete Therapeutics, INC. | Soluble epoxide hydrolase inhibitors |
| US7790756B2 (en) | 2006-10-11 | 2010-09-07 | Deciphera Pharmaceuticals, Llc | Kinase inhibitors useful for the treatment of myleoproliferative diseases and other proliferative diseases |
| TW200848054A (en) | 2007-02-28 | 2008-12-16 | Eisai R&D Man Co Ltd | Two cyclic oxomorpholine derivatives |
| JP5930573B2 (ja) * | 2007-03-01 | 2016-06-15 | プロビオドルグ エージー | グルタミニルシクラーゼ阻害剤の新規使用 |
| WO2008140895A1 (en) * | 2007-04-20 | 2008-11-20 | Deciphera Pharmaceuticals, Llc | Kinase inhibitors useful for the treatment of myleoproliferative diseases and other proliferative diseases |
| US20110189167A1 (en) * | 2007-04-20 | 2011-08-04 | Flynn Daniel L | Methods and Compositions for the Treatment of Myeloproliferative Diseases and other Proliferative Diseases |
| US7935815B2 (en) | 2007-08-31 | 2011-05-03 | Eisai R&D Management Co., Ltd. | Imidazoyl pyridine compounds and salts thereof |
| AR068121A1 (es) | 2007-08-31 | 2009-11-04 | Eisai R&D Man Co Ltd | Compuestos multiciclicos para tratar enfermedades neurodegenerativas |
| CA2742007C (en) | 2008-10-29 | 2014-07-08 | Deciphera Pharmaceuticals, Llc | Cyclopropane amides and analogs exhibiting anti-cancer and anti-proliferative activities |
| KR20120059558A (ko) * | 2009-08-19 | 2012-06-08 | 암비트 바이오사이언시즈 코포레이션 | 바이아릴 화합물 및 이의 사용 방법 |
| JP6130383B2 (ja) | 2011-09-30 | 2017-05-17 | エンドゥ ファーマシューティカルズ，インコーポレイティド | ピリジン誘導体 |
| JP6105594B2 (ja) | 2011-09-30 | 2017-03-29 | エンドゥ ファーマシューティカルズ，インコーポレイティド | 癌処置用ｃｙｐ１７阻害剤としてのイミダゾール誘導体 |
| US8461179B1 (en) | 2012-06-07 | 2013-06-11 | Deciphera Pharmaceuticals, Llc | Dihydronaphthyridines and related compounds useful as kinase inhibitors for the treatment of proliferative diseases |
| WO2019126731A1 (en) | 2017-12-22 | 2019-06-27 | Petra Pharma Corporation | Aminopyridine derivatives as phosphatidylinositol phosphate kinase inhibitors |
| CN118903436A (zh) | 2018-01-31 | 2024-11-08 | 德西费拉制药有限责任公司 | 治疗肥大细胞增多症的组合疗法 |
| KR102708177B1 (ko) | 2018-01-31 | 2024-09-23 | 데시페라 파마슈티칼스, 엘엘씨. | 위장관 기질 종양의 치료를 위한 병용 요법 |
| IL330104A (en) | 2019-03-11 | 2026-08-01 | Deciphera Pharmaceuticals Llc | Crystalline forms of rifatinib |
| TW202112767A (zh) | 2019-06-17 | 2021-04-01 | 美商佩特拉製藥公司 | 作為磷脂酸肌醇磷酸激酶抑制劑之胺基吡啶衍生物 |
| US12691108B2 (en) | 2019-08-12 | 2026-07-28 | Deciphera Pharmaceuticals, Llc | Methods for treating vascular malformations |
| HRP20260411T1 (hr) | 2019-08-12 | 2026-05-08 | Deciphera Pharmaceuticals, Llc | Ripretinib za liječenje gastrointestinalnih stromalnih tumora |
| FI4084779T3 (fi) | 2019-12-30 | 2024-12-16 | Deciphera Pharmaceuticals Llc | 1-(4-bromi-5-(1-etyyli-7-(metyyliamino)-2-okso-1,2-dihydro-1,6-naftyridin-3-yyli)-2-fluorifenyyli)-3-fenyyliurean koostumuksia |
| US11779572B1 (en) | 2022-09-02 | 2023-10-10 | Deciphera Pharmaceuticals, Llc | Methods of treating gastrointestinal stromal tumors |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU1367599A (en) | 1997-11-03 | 1999-05-24 | Boehringer Ingelheim Pharmaceuticals, Inc. | Aromatic heterocyclic compounds as anti-inflammatory agents |
| EP2298311B1 (en) * | 1999-01-13 | 2012-05-09 | Bayer HealthCare LLC | w-Carboxy aryl substituted diphenyl ureas as p38 kinase inhibitors |
| UA73492C2 (en) * | 1999-01-19 | 2005-08-15 | Aromatic heterocyclic compounds as antiinflammatory agents | |
| TR200102817T2 (tr) | 1999-03-12 | 2002-05-21 | Boehringer Ingelheim Pharmaceuticals, Inc. | Antiinflamatuar ajanlar olarak faydalı bileşikler |
| US6608052B2 (en) * | 2000-02-16 | 2003-08-19 | Boehringer Ingelheim Pharmaceuticals, Inc. | Compounds useful as anti-inflammatory agents |
| ATE338035T1 (de) * | 2001-06-05 | 2006-09-15 | Boehringer Ingelheim Pharma | 1,4-disubstituierte benzokondensierte cycloalkyl harnstoffverbindungen |
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2002
- 2002-09-09 WO PCT/US2002/028615 patent/WO2003022273A1/en not_active Ceased
- 2002-09-09 US US10/237,306 patent/US7211575B2/en not_active Expired - Lifetime
- 2002-09-09 CA CA002458029A patent/CA2458029A1/en not_active Abandoned
- 2002-09-09 JP JP2003526402A patent/JP2005503400A/ja active Pending
- 2002-09-09 EP EP02797884A patent/EP1427412A1/en not_active Withdrawn
-
2007
- 2007-03-09 US US11/684,173 patent/US20070155724A1/en not_active Abandoned
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