JP2004534787A5 - - Google Patents
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- JP2004534787A5 JP2004534787A5 JP2003501992A JP2003501992A JP2004534787A5 JP 2004534787 A5 JP2004534787 A5 JP 2004534787A5 JP 2003501992 A JP2003501992 A JP 2003501992A JP 2003501992 A JP2003501992 A JP 2003501992A JP 2004534787 A5 JP2004534787 A5 JP 2004534787A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- group
- cyclopropyl
- optionally
- amino
- 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.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims 102
- -1 hydroxy, amino Chemical group 0.000 claims 71
- 125000003545 alkoxy group Chemical group 0.000 claims 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 34
- 125000001072 heteroaryl group Chemical group 0.000 claims 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 21
- 150000001875 compounds Chemical class 0.000 claims 19
- 125000000623 heterocyclic group Chemical group 0.000 claims 18
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 16
- 125000003386 piperidinyl group Chemical group 0.000 claims 16
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 16
- 125000002252 acyl group Chemical group 0.000 claims 15
- 150000002825 nitriles Chemical class 0.000 claims 15
- 125000005843 halogen group Chemical group 0.000 claims 14
- 125000004076 pyridyl group Chemical group 0.000 claims 14
- 125000004043 oxo group Chemical group O=* 0.000 claims 13
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 12
- 125000003226 pyrazolyl group Chemical group 0.000 claims 12
- 125000002757 morpholinyl group Chemical group 0.000 claims 11
- 125000002098 pyridazinyl group Chemical group 0.000 claims 11
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 11
- 125000002883 imidazolyl group Chemical group 0.000 claims 10
- 125000001624 naphthyl group Chemical group 0.000 claims 10
- 125000001544 thienyl group Chemical group 0.000 claims 10
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims 9
- 229910052736 halogen Inorganic materials 0.000 claims 9
- 125000003373 pyrazinyl group Chemical group 0.000 claims 9
- 125000003118 aryl group Chemical group 0.000 claims 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 8
- 150000002367 halogens Chemical class 0.000 claims 8
- 125000004193 piperazinyl group Chemical group 0.000 claims 8
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 8
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 8
- 125000003831 tetrazolyl group Chemical group 0.000 claims 8
- 125000000335 thiazolyl group Chemical group 0.000 claims 8
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 8
- 239000004202 carbamide Substances 0.000 claims 7
- 125000002971 oxazolyl group Chemical group 0.000 claims 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 7
- 125000000168 pyrrolyl group Chemical group 0.000 claims 7
- ZCAGUOCUDGWENZ-UHFFFAOYSA-N thiomorpholinyl sulfoxide group Chemical group N1(CCSCC1)S(=O)N1CCSCC1 ZCAGUOCUDGWENZ-UHFFFAOYSA-N 0.000 claims 7
- 125000001425 triazolyl group Chemical group 0.000 claims 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 6
- WCNFFKHKJLERFM-UHFFFAOYSA-N thiomorpholinyl sulfone group Chemical group N1(CCSCC1)S(=O)(=O)N1CCSCC1 WCNFFKHKJLERFM-UHFFFAOYSA-N 0.000 claims 6
- 125000003435 aroyl group Chemical group 0.000 claims 5
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 5
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 5
- 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 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 5
- 125000006576 di-(C1-C3-alkyl)-aminocarbonyl group Chemical group 0.000 claims 5
- 150000002148 esters Chemical class 0.000 claims 5
- 125000002541 furyl group Chemical group 0.000 claims 5
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- QYCGBAJADAGLLK-UHFFFAOYSA-N 1-(cyclohepten-1-yl)cycloheptene Chemical group C1CCCCC=C1C1=CCCCCC1 QYCGBAJADAGLLK-UHFFFAOYSA-N 0.000 claims 4
- VSIYJQNFMOOGCU-UHFFFAOYSA-N 1-(cyclohexen-1-yl)cyclohexene Chemical group C1CCCC(C=2CCCCC=2)=C1 VSIYJQNFMOOGCU-UHFFFAOYSA-N 0.000 claims 4
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 claims 4
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 claims 4
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims 4
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims 4
- 125000005053 dihydropyrimidinyl group Chemical group N1(CN=CC=C1)* 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 4
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 4
- 125000001786 isothiazolyl group Chemical group 0.000 claims 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims 4
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims 3
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 3
- 208000011231 Crohn disease Diseases 0.000 claims 3
- 206010019280 Heart failures Diseases 0.000 claims 3
- 201000004681 Psoriasis Diseases 0.000 claims 3
- 230000001154 acute effect Effects 0.000 claims 3
- 125000003277 amino group Chemical group 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 208000014674 injury Diseases 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- MPXYAGHDKITTQX-UHFFFAOYSA-N 1-(2-cyclohexylcyclopropyl)-3-[4-[2-(pyrrolidine-1-carbonyl)pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C=1C=C(OC=2C=C(N=CC=2)C(=O)N2CCCC2)C2=CC=CC=C2C=1NC(=O)NC1CC1C1CCCCC1 MPXYAGHDKITTQX-UHFFFAOYSA-N 0.000 claims 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 2
- LQPVTFUPUUWMIV-UHFFFAOYSA-N 4-(pyridin-2-ylmethyl)morpholine Chemical compound C=1C=CC=NC=1CN1CCOCC1 LQPVTFUPUUWMIV-UHFFFAOYSA-N 0.000 claims 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- 206010009900 Colitis ulcerative Diseases 0.000 claims 2
- 102000004127 Cytokines Human genes 0.000 claims 2
- 108090000695 Cytokines Proteins 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 2
- 206010040070 Septic Shock Diseases 0.000 claims 2
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 2
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 2
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 230000033115 angiogenesis Effects 0.000 claims 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001041 indolyl group Chemical group 0.000 claims 2
- 239000012948 isocyanate Substances 0.000 claims 2
- 150000002513 isocyanates Chemical class 0.000 claims 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 201000008482 osteoarthritis Diseases 0.000 claims 2
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims 2
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 230000008733 trauma Effects 0.000 claims 2
- 125000006594 (C1-C3) alkylsulfony group Chemical group 0.000 claims 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000005940 1,4-dioxanyl group Chemical group 0.000 claims 1
- SQYOEJNTQRWGLO-UHFFFAOYSA-N 1-(2-benzylcyclopropyl)-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)NC1CC1CC1=CC=CC=C1 SQYOEJNTQRWGLO-UHFFFAOYSA-N 0.000 claims 1
- BPVFNCBBULZSEP-UHFFFAOYSA-N 1-(2-butan-2-ylcyclopropyl)-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CCC(C)C1CC1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1CCOCC1 BPVFNCBBULZSEP-UHFFFAOYSA-N 0.000 claims 1
- USWZBIQWDUXAIZ-UHFFFAOYSA-N 1-(2-cyclohexylcyclopropyl)-3-[4-(2,6-dimethylpyrimidin-4-yl)oxynaphthalen-1-yl]urea Chemical compound CC1=NC(C)=CC(OC=2C3=CC=CC=C3C(NC(=O)NC3C(C3)C3CCCCC3)=CC=2)=N1 USWZBIQWDUXAIZ-UHFFFAOYSA-N 0.000 claims 1
- WJVNQMVASKNSHR-UHFFFAOYSA-N 1-(2-cyclohexylcyclopropyl)-3-[4-(2-methoxypyrimidin-4-yl)oxynaphthalen-1-yl]urea Chemical compound COC1=NC=CC(OC=2C3=CC=CC=C3C(NC(=O)NC3C(C3)C3CCCCC3)=CC=2)=N1 WJVNQMVASKNSHR-UHFFFAOYSA-N 0.000 claims 1
- DFPBFNWQWQOZBV-UHFFFAOYSA-N 1-(2-cyclohexylcyclopropyl)-3-[4-(2-morpholin-4-ylethoxy)naphthalen-1-yl]urea Chemical compound C=1C=C(OCCN2CCOCC2)C2=CC=CC=C2C=1NC(=O)NC1CC1C1CCCCC1 DFPBFNWQWQOZBV-UHFFFAOYSA-N 0.000 claims 1
- UEOSIGXXAOPSGI-UHFFFAOYSA-N 1-(2-cyclohexylcyclopropyl)-3-[4-(2-oxopyran-4-yl)oxynaphthalen-1-yl]urea Chemical compound C=1C=C(OC2=CC(=O)OC=C2)C2=CC=CC=C2C=1NC(=O)NC1CC1C1CCCCC1 UEOSIGXXAOPSGI-UHFFFAOYSA-N 0.000 claims 1
- ZACYIDDNAATDHR-UHFFFAOYSA-N 1-(2-cyclohexylcyclopropyl)-3-[4-(6-methyl-2-propan-2-ylpyrimidin-4-yl)oxynaphthalen-1-yl]urea Chemical compound CC(C)C1=NC(C)=CC(OC=2C3=CC=CC=C3C(NC(=O)NC3C(C3)C3CCCCC3)=CC=2)=N1 ZACYIDDNAATDHR-UHFFFAOYSA-N 0.000 claims 1
- WTPGYKKIXGTHIA-UHFFFAOYSA-N 1-(2-cyclohexylcyclopropyl)-3-[4-[(2-oxo-1h-pyrimidin-6-yl)oxy]naphthalen-1-yl]urea Chemical compound C=1C=C(OC=2NC(=O)N=CC=2)C2=CC=CC=C2C=1NC(=O)NC1CC1C1CCCCC1 WTPGYKKIXGTHIA-UHFFFAOYSA-N 0.000 claims 1
- BWIVUHDZFXKVGY-UHFFFAOYSA-N 1-(2-cyclohexylcyclopropyl)-3-[4-[1-(oxan-4-ylmethyl)-2-oxopyridin-4-yl]naphthalen-1-yl]urea Chemical compound C=1C=C(C2=CC(=O)N(CC3CCOCC3)C=C2)C2=CC=CC=C2C=1NC(=O)NC1CC1C1CCCCC1 BWIVUHDZFXKVGY-UHFFFAOYSA-N 0.000 claims 1
- AYZQQZWXENCOII-UHFFFAOYSA-N 1-(2-cyclohexylcyclopropyl)-3-[4-[2-(1-phenylethylamino)pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C=1C=CC=CC=1C(C)NC(N=1)=NC=CC=1OC(C1=CC=CC=C11)=CC=C1NC(=O)NC1CC1C1CCCCC1 AYZQQZWXENCOII-UHFFFAOYSA-N 0.000 claims 1
- BJLVRYGACIYWDD-UHFFFAOYSA-N 1-(2-cyclohexylcyclopropyl)-3-[4-[2-(cyclopropylmethylamino)-6-methylpyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound N=1C(NCC2CC2)=NC(C)=CC=1OC(C1=CC=CC=C11)=CC=C1NC(=O)NC1CC1C1CCCCC1 BJLVRYGACIYWDD-UHFFFAOYSA-N 0.000 claims 1
- QJKOEAGVNHGHCL-UHFFFAOYSA-N 1-(2-cyclohexylcyclopropyl)-3-[4-[2-(cyclopropylmethylamino)pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C=1C=C(OC=2N=C(NCC3CC3)N=CC=2)C2=CC=CC=C2C=1NC(=O)NC1CC1C1CCCCC1 QJKOEAGVNHGHCL-UHFFFAOYSA-N 0.000 claims 1
- JKRMTAKRPGNSKI-UHFFFAOYSA-N 1-(2-cyclohexylcyclopropyl)-3-[4-[2-(pyrrolidin-1-ylmethyl)pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C=1C=C(OC=2C=C(CN3CCCC3)N=CC=2)C2=CC=CC=C2C=1NC(=O)NC1CC1C1CCCCC1 JKRMTAKRPGNSKI-UHFFFAOYSA-N 0.000 claims 1
- UJZIDGHMYHHWQD-UHFFFAOYSA-N 1-(2-cyclohexylcyclopropyl)-3-[4-[2-[(3-hydroxypyrrolidin-1-yl)methyl]pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C1C(O)CCN1CC1=CC(OC=2C3=CC=CC=C3C(NC(=O)NC3C(C3)C3CCCCC3)=CC=2)=CC=N1 UJZIDGHMYHHWQD-UHFFFAOYSA-N 0.000 claims 1
- HKUYFTNLJYVTLF-UHFFFAOYSA-N 1-(2-cyclohexylcyclopropyl)-3-[4-[2-[(4-hydroxypiperidin-1-yl)methyl]pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C1CC(O)CCN1CC1=CC(OC=2C3=CC=CC=C3C(NC(=O)NC3C(C3)C3CCCCC3)=CC=2)=CC=N1 HKUYFTNLJYVTLF-UHFFFAOYSA-N 0.000 claims 1
- WTYGFERUUPJRKE-UHFFFAOYSA-N 1-(2-cyclohexylcyclopropyl)-3-[4-[2-[(4-methylpiperazin-1-yl)methyl]pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C1CN(C)CCN1CC1=CC(OC=2C3=CC=CC=C3C(NC(=O)NC3C(C3)C3CCCCC3)=CC=2)=CC=N1 WTYGFERUUPJRKE-UHFFFAOYSA-N 0.000 claims 1
- PXCFXNNMZXODJI-UHFFFAOYSA-N 1-(2-cyclohexylcyclopropyl)-3-[4-[2-[(dimethylamino)methyl]pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C1=NC(CN(C)C)=CC(OC=2C3=CC=CC=C3C(NC(=O)NC3C(C3)C3CCCCC3)=CC=2)=C1 PXCFXNNMZXODJI-UHFFFAOYSA-N 0.000 claims 1
- GGBIBLMYRDWIGH-UHFFFAOYSA-N 1-(2-cyclohexylcyclopropyl)-3-[4-[2-[2-(dimethylamino)ethylamino]-6-methylpyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound CN(C)CCNC1=NC(C)=CC(OC=2C3=CC=CC=C3C(NC(=O)NC3C(C3)C3CCCCC3)=CC=2)=N1 GGBIBLMYRDWIGH-UHFFFAOYSA-N 0.000 claims 1
- UYBMSZYMFRQKRS-UHFFFAOYSA-N 1-(2-cyclohexylcyclopropyl)-3-[4-[2-[2-(dimethylamino)ethylamino]pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound CN(C)CCNC1=NC=CC(OC=2C3=CC=CC=C3C(NC(=O)NC3C(C3)C3CCCCC3)=CC=2)=N1 UYBMSZYMFRQKRS-UHFFFAOYSA-N 0.000 claims 1
- MMWUKRPBBCTSAP-UHFFFAOYSA-N 1-(2-cyclohexylcyclopropyl)-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)NC1CC1C1CCCCC1 MMWUKRPBBCTSAP-UHFFFAOYSA-N 0.000 claims 1
- CRDSINQVTJXRER-UHFFFAOYSA-N 1-(2-cyclohexylcyclopropyl)-3-[4-[6-methyl-2-(methylamino)pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound CNC1=NC(C)=CC(OC=2C3=CC=CC=C3C(NC(=O)NC3C(C3)C3CCCCC3)=CC=2)=N1 CRDSINQVTJXRER-UHFFFAOYSA-N 0.000 claims 1
- HMRYXKHDGKQONM-UHFFFAOYSA-N 1-(2-cyclohexylcyclopropyl)-3-[4-[6-methyl-2-(morpholin-4-ylmethyl)pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound N=1C(CN2CCOCC2)=NC(C)=CC=1OC(C1=CC=CC=C11)=CC=C1NC(=O)NC1CC1C1CCCCC1 HMRYXKHDGKQONM-UHFFFAOYSA-N 0.000 claims 1
- UWQWZVZBDWJLFE-UHFFFAOYSA-N 1-(2-cyclohexylcyclopropyl)-3-[4-[[4-(dimethylamino)-6-methoxy-1,3,5-triazin-2-yl]oxy]naphthalen-1-yl]urea Chemical compound CN(C)C1=NC(OC)=NC(OC=2C3=CC=CC=C3C(NC(=O)NC3C(C3)C3CCCCC3)=CC=2)=N1 UWQWZVZBDWJLFE-UHFFFAOYSA-N 0.000 claims 1
- AJHAAXDFDFUONW-UHFFFAOYSA-N 1-(2-cyclohexylcyclopropyl)-3-[4-[[4-methoxy-6-(methylamino)-1,3,5-triazin-2-yl]oxy]naphthalen-1-yl]urea Chemical compound CNC1=NC(OC)=NC(OC=2C3=CC=CC=C3C(NC(=O)NC3C(C3)C3CCCCC3)=CC=2)=N1 AJHAAXDFDFUONW-UHFFFAOYSA-N 0.000 claims 1
- XVCHGUFWDBYNHE-UHFFFAOYSA-N 1-[2-(1-acetylpyrrol-2-yl)cyclopropyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CC(=O)N1C=CC=C1C1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)C1 XVCHGUFWDBYNHE-UHFFFAOYSA-N 0.000 claims 1
- CEVZHNKVGCWVQW-UHFFFAOYSA-N 1-[2-(1-acetylpyrrolidin-2-yl)cyclopropyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CC(=O)N1CCCC1C1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)C1 CEVZHNKVGCWVQW-UHFFFAOYSA-N 0.000 claims 1
- NRGFFUHOMXFFMU-UHFFFAOYSA-N 1-[2-(1-benzylpiperidin-2-yl)cyclopropyl]-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)NC1CC1C1CCCCN1CC1=CC=CC=C1 NRGFFUHOMXFFMU-UHFFFAOYSA-N 0.000 claims 1
- KXJFWGUXCARDRE-UHFFFAOYSA-N 1-[2-(2,2-dimethylpropyl)cyclopropyl]-3-[4-(2-morpholin-4-ylethoxy)naphthalen-1-yl]urea Chemical compound CC(C)(C)CC1CC1NC(=O)NC(C1=CC=CC=C11)=CC=C1OCCN1CCOCC1 KXJFWGUXCARDRE-UHFFFAOYSA-N 0.000 claims 1
- HGHCFQFNAFNHDN-UHFFFAOYSA-N 1-[2-(2-aminophenyl)cyclopropyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound NC1=CC=CC=C1C1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)C1 HGHCFQFNAFNHDN-UHFFFAOYSA-N 0.000 claims 1
- TYIKQWBTNCDNDM-UHFFFAOYSA-N 1-[2-(2-chlorophenyl)cyclopropyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound ClC1=CC=CC=C1C1C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)C1 TYIKQWBTNCDNDM-UHFFFAOYSA-N 0.000 claims 1
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| JP4736043B2 (ja) | 2003-03-14 | 2011-07-27 | 小野薬品工業株式会社 | 含窒素複素環誘導体およびそれらを有効成分とする薬剤 |
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| TW200845978A (en) | 2007-03-07 | 2008-12-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-tetrahydropyran-phenyl)-pyridin-2-one derivatives |
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| MX2011002042A (es) | 2008-09-02 | 2011-06-20 | Ortho Mcneil Janssen Pharm | Derivados de 3-azabiciclo[3.1.o]hexilo como moduladores de los receptores del glutamato metabotropico. |
| CN102232074B (zh) | 2008-11-28 | 2014-12-03 | 奥梅-杨森制药有限公司 | 作为代谢性谷氨酸盐受体调节剂的吲哚和苯并噁嗪衍生物 |
| EA020672B1 (ru) | 2009-05-12 | 2014-12-30 | Янссен Фармасьютикалс, Инк. | Производные 1,2,4-триазоло[4,3-a]пиридина и их применение для лечения или предупреждения неврологических и психиатрических расстройств |
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| EP2432776B1 (en) | 2009-05-21 | 2019-09-11 | Universite Laval | Methyl sulfanyl pyrimidines useful as antiinflammatories, analgesics, and antiepileptics |
| BR112012027901A2 (pt) | 2010-04-30 | 2015-09-08 | Univ Indiana Res & Tech Corp | processos para preparar linezolida |
| GB201009731D0 (en) * | 2010-06-10 | 2010-07-21 | Pulmagen Therapeutics Inflamma | Kinase inhibitors |
| ES2552455T3 (es) | 2010-11-08 | 2015-11-30 | Janssen Pharmaceuticals, Inc. | Derivados de 1,2,4-triazolo[4,3-a]piridina y su uso como moduladores alostéricos positivos de receptores mGluR2 |
| CA2815002C (en) | 2010-11-08 | 2019-10-22 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
| US9012448B2 (en) | 2010-11-08 | 2015-04-21 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of MGLUR2 receptors |
| WO2013186229A1 (en) | 2012-06-11 | 2013-12-19 | Ucb Pharma S.A. | Tnf -alpha modulating benzimidazoles |
| JO3368B1 (ar) | 2013-06-04 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 6، 7- ثاني هيدرو بيرازولو [5،1-a] بيرازين- 4 (5 يد)- اون واستخدامها بصفة منظمات تفارغية سلبية لمستقبلات ميجلور 2 |
| JO3367B1 (ar) | 2013-09-06 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 2،1، 4- ثلاثي زولو [3،4-a] بيريدين واستخدامها بصفة منظمات تفارغية موجبة لمستقبلات ميجلور 2 |
| UA121965C2 (uk) | 2014-01-21 | 2020-08-25 | Янссен Фармацевтика Нв | Комбінації, які містять позитивні алостеричні модулятори або ортостеричні агоністи метаботропного глутаматергічного рецептора 2 підтипу, та їх застосування |
| KR102502485B1 (ko) | 2014-01-21 | 2023-02-21 | 얀센 파마슈티카 엔.브이. | 대사 조절형 글루탐산 작동성 수용체 제2아형의 양성 알로스테릭 조절제 또는 오르토스테릭 작동제를 포함하는 조합 및 그 용도 |
| GB201510758D0 (en) | 2015-06-18 | 2015-08-05 | Ucb Biopharma Sprl | Novel TNFa structure for use in therapy |
| GB201621907D0 (en) | 2016-12-21 | 2017-02-01 | Ucb Biopharma Sprl And Sanofi | Antibody epitope |
| HUE067314T2 (hu) | 2017-09-22 | 2024-10-28 | Jubilant Epipad LLC | Heterociklusos vegyületek mint PAD gátlók |
| KR102782563B1 (ko) | 2017-10-18 | 2025-03-14 | 주빌런트 에피파드 엘엘씨 | Pad 억제제로서의 이미다조-피리딘 화합물 |
| KR20200085836A (ko) | 2017-11-06 | 2020-07-15 | 주빌런트 프로델 엘엘씨 | Pd1/pd-l1 활성화 억제제로서의 피리미딘 유도체 |
| BR112020010322A2 (pt) | 2017-11-24 | 2020-11-17 | Jubilant Episcribe Llc | composto da fórmula i; composto da fórmula ia; composto da fórmula ib; processo de preparação de compostos da fórmula i; composição farmacêutica; método para o tratamento e/ou prevenção de várias doenças; uso dos compostos; método para o tratamento de câncer; e método para o tratamento e/ou prevenção de uma afecção mediada por prmt5 ou um distúrbio proliferativo ou câncer |
| SG11202008950PA (en) | 2018-03-13 | 2020-10-29 | Jubilant Prodel LLC | Bicyclic compounds as inhibitors of pd1/pd-l1 interaction/activation |
| CN116354891B (zh) * | 2022-11-07 | 2025-01-07 | 河南省锐达医药科技有限公司 | 一种萘基苯醚类化合物、其制备方法及应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK1043995T3 (da) | 1997-12-22 | 2007-03-05 | Bayer Pharmaceuticals Corp | Inhibering af p38 kinaseaktivitet ved anvendelse af aryl- og heteroaryl-substituerede, heterocykliske urinstoffer |
| MXPA00006233A (es) | 1997-12-22 | 2002-09-18 | Bayer Ag | Inhibicion de la actividad de la cinasa p38 utilizando ureas heterociclicas sustituidas. |
| DE69830513T2 (de) | 1997-12-22 | 2006-03-16 | Bayer Pharmaceuticals Corp., West Haven | HEMMUNG DER p38 KINASE UNTER VERWENDUNG VON SYMMETRISCHEN UND ASYMMETRISCHEN DIPHENYLHARNSTOFFEN |
| UA73492C2 (en) | 1999-01-19 | 2005-08-15 | Aromatic heterocyclic compounds as antiinflammatory agents | |
| DE60023853T2 (de) | 1999-03-12 | 2006-05-24 | Boehringer Ingelheim Pharmaceuticals, Inc., Ridgefield | Aromatische heterozyklische verbindungen als antientzündungwirkstoffe |
| HUP0202248A3 (en) | 1999-03-12 | 2006-06-28 | Boehringer Ingelheim Pharma | Compounds useful as anti-inflammatory agents |
| CA2389360C (en) | 1999-11-16 | 2008-06-03 | Steffen Breitfelder | Urea derivatives as anti-inflammatory agents |
-
2002
- 2002-05-24 WO PCT/US2002/016720 patent/WO2002098869A2/en not_active Ceased
- 2002-05-24 AT AT02737211T patent/ATE338035T1/de active
- 2002-05-24 MX MXPA03011006A patent/MXPA03011006A/es active IP Right Grant
- 2002-05-24 US US10/154,535 patent/US6720321B2/en not_active Expired - Lifetime
- 2002-05-24 DE DE60214392T patent/DE60214392T2/de not_active Expired - Lifetime
- 2002-05-24 JP JP2003501992A patent/JP4424983B2/ja not_active Expired - Lifetime
- 2002-05-24 CA CA2446193A patent/CA2446193C/en not_active Expired - Lifetime
- 2002-05-24 EP EP02737211A patent/EP1414810B1/en not_active Expired - Lifetime
- 2002-05-24 AU AU2002310156A patent/AU2002310156A1/en not_active Abandoned
- 2002-05-24 ES ES02737211T patent/ES2269709T3/es not_active Expired - Lifetime
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