HRP20010665A2 - Compounds useful as anti-inflammatory agents - Google Patents
Compounds useful as anti-inflammatory agents Download PDFInfo
- Publication number
- HRP20010665A2 HRP20010665A2 HR20010665A HRP20010665A HRP20010665A2 HR P20010665 A2 HRP20010665 A2 HR P20010665A2 HR 20010665 A HR20010665 A HR 20010665A HR P20010665 A HRP20010665 A HR P20010665A HR P20010665 A2 HRP20010665 A2 HR P20010665A2
- Authority
- HR
- Croatia
- Prior art keywords
- alkyl
- phenyl
- amino
- pyridin
- naphthalen
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 105
- 239000002260 anti-inflammatory agent Substances 0.000 title description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 title description 2
- -1 oxapyl Chemical compound 0.000 claims description 790
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 328
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 308
- 229910052736 halogen Inorganic materials 0.000 claims description 200
- 150000002367 halogens Chemical class 0.000 claims description 200
- 229910020008 S(O) Inorganic materials 0.000 claims description 197
- 125000004076 pyridyl group Chemical group 0.000 claims description 186
- 239000004202 carbamide Substances 0.000 claims description 180
- 150000002825 nitriles Chemical class 0.000 claims description 171
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 159
- 125000000623 heterocyclic group Chemical group 0.000 claims description 149
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 144
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims description 129
- 125000000217 alkyl group Chemical group 0.000 claims description 120
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 118
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 117
- 125000002883 imidazolyl group Chemical group 0.000 claims description 117
- 125000001424 substituent group Chemical group 0.000 claims description 116
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 106
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 99
- 125000004043 oxo group Chemical group O=* 0.000 claims description 96
- 229910052760 oxygen Inorganic materials 0.000 claims description 96
- 125000001624 naphthyl group Chemical group 0.000 claims description 91
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 90
- 125000001072 heteroaryl group Chemical group 0.000 claims description 87
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 85
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 80
- 125000003118 aryl group Chemical group 0.000 claims description 76
- 125000002541 furyl group Chemical group 0.000 claims description 71
- 125000004193 piperazinyl group Chemical group 0.000 claims description 70
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 69
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 69
- 125000001544 thienyl group Chemical group 0.000 claims description 59
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 55
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 54
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 54
- 125000003386 piperidinyl group Chemical group 0.000 claims description 54
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 51
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 51
- 229910052757 nitrogen Inorganic materials 0.000 claims description 50
- 229910052717 sulfur Inorganic materials 0.000 claims description 45
- 125000006576 di-(C1-C3-alkyl)-aminocarbonyl group Chemical group 0.000 claims description 43
- 125000005843 halogen group Chemical group 0.000 claims description 43
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 42
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 42
- 125000003435 aroyl group Chemical group 0.000 claims description 40
- 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 39
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 38
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 38
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 36
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 36
- 102000004127 Cytokines Human genes 0.000 claims description 35
- 108090000695 Cytokines Proteins 0.000 claims description 35
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 35
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 35
- 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 35
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 34
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 34
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 34
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 34
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 34
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 34
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 32
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 32
- 201000010099 disease Diseases 0.000 claims description 32
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 32
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 32
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 31
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 30
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 28
- 125000001041 indolyl group Chemical group 0.000 claims description 28
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 27
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 26
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 26
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 25
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 24
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 24
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 claims description 24
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 22
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 22
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 20
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 20
- 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 20
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 20
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 20
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 19
- 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 18
- 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 18
- 125000002757 morpholinyl group Chemical group 0.000 claims description 18
- 229920006395 saturated elastomer Polymers 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 16
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 claims description 16
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 16
- 125000005494 pyridonyl group Chemical group 0.000 claims description 16
- 102220104380 rs199933920 Human genes 0.000 claims description 16
- 229930192474 thiophene Natural products 0.000 claims description 16
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 15
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 14
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 14
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 14
- 238000011282 treatment Methods 0.000 claims description 14
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims description 13
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 13
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 12
- QYCGBAJADAGLLK-UHFFFAOYSA-N 1-(cyclohepten-1-yl)cycloheptene Chemical group C1CCCCC=C1C1=CCCCCC1 QYCGBAJADAGLLK-UHFFFAOYSA-N 0.000 claims description 12
- VSIYJQNFMOOGCU-UHFFFAOYSA-N 1-(cyclohexen-1-yl)cyclohexene Chemical group C1CCCC(C=2CCCCC=2)=C1 VSIYJQNFMOOGCU-UHFFFAOYSA-N 0.000 claims description 12
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 12
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 12
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 12
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 12
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical group C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 claims description 12
- MAWOHFOSAIXURX-UHFFFAOYSA-N cyclopentylcyclopentane Chemical group C1CCCC1C1CCCC1 MAWOHFOSAIXURX-UHFFFAOYSA-N 0.000 claims description 12
- 125000005436 dihydrobenzothiophenyl group Chemical group S1C(CC2=C1C=CC=C2)* 0.000 claims description 12
- 125000005046 dihydronaphthyl group Chemical group 0.000 claims description 12
- 125000005879 dioxolanyl group Chemical group 0.000 claims description 12
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 12
- 102220084927 rs778740017 Human genes 0.000 claims description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 10
- 125000005940 1,4-dioxanyl group Chemical group 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- 125000004599 benzpyrazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical group C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 claims description 10
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 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 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
- 125000001425 triazolyl group Chemical group 0.000 claims description 10
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims description 8
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 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
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 8
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 8
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 8
- 230000001154 acute effect Effects 0.000 claims description 8
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000005056 dihydrothiazolyl group Chemical group S1C(NC=C1)* 0.000 claims description 8
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 8
- 230000002757 inflammatory effect Effects 0.000 claims description 8
- 208000014674 injury Diseases 0.000 claims description 8
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 8
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 8
- 125000005505 thiomorpholino group Chemical group 0.000 claims description 8
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 8
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 7
- 230000006378 damage Effects 0.000 claims description 7
- 230000001404 mediated effect Effects 0.000 claims description 7
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 7
- 125000006563 (C1-3) alkylaminocarbonyl group Chemical group 0.000 claims description 6
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 6
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 6
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 125000002243 cyclohexanonyl group Chemical group *C1(*)C(=O)C(*)(*)C(*)(*)C(*)(*)C1(*)* 0.000 claims description 6
- 150000003335 secondary amines Chemical class 0.000 claims description 6
- 150000003512 tertiary amines Chemical class 0.000 claims description 6
- 150000003536 tetrazoles Chemical class 0.000 claims description 6
- 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 5
- 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 claims description 5
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 5
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 5
- 125000006594 (C1-C3) alkylsulfony group Chemical group 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims 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 claims description 4
- 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 claims description 4
- 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 claims description 4
- FBPMUUXVDWZTBK-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[2-(morpholin-4-ylmethyl)pyrimidin-5-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CN=C1CN1CCOCC1 FBPMUUXVDWZTBK-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- 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 4
- BYPZLIPMLRPGCS-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-[6-[(2-methyl-3-oxopiperazin-1-yl)methyl]pyridin-3-yl]naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C(C=N1)=CC=C1CN1C(C)C(=O)NCC1 BYPZLIPMLRPGCS-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
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HU228769B1 (en) * | 1996-07-24 | 2013-05-28 | Celgene Corp | Substituted 2(2,6-dioxopiperidin-3-yl)phthalimides and -1-oxoisoindolines and their use for production of pharmaceutical compositions for mammals to reduce the level of tnf-alpha |
US7517880B2 (en) * | 1997-12-22 | 2009-04-14 | Bayer Pharmaceuticals Corporation | Inhibition of p38 kinase using symmetrical and unsymmetrical diphenyl ureas |
EP1140840B1 (en) * | 1999-01-13 | 2006-03-22 | Bayer Pharmaceuticals Corp. | -g(v)-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
EP2298311B1 (en) * | 1999-01-13 | 2012-05-09 | Bayer HealthCare LLC | w-Carboxy aryl substituted diphenyl ureas as p38 kinase inhibitors |
US7351834B1 (en) * | 1999-01-13 | 2008-04-01 | Bayer Pharmaceuticals Corporation | ω-Carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
US8124630B2 (en) | 1999-01-13 | 2012-02-28 | Bayer Healthcare Llc | ω-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
EP1165516B1 (en) * | 1999-03-12 | 2004-10-06 | Boehringer Ingelheim Pharmaceuticals Inc. | Heterocyclic urea and related compounds useful as anti-inflammatory agents |
EP1466906A1 (en) * | 1999-03-12 | 2004-10-13 | Boehringer Ingelheim Pharmaceuticals Inc. | Heterocyclic urea and related compounds useful as anti-inflammatory agents |
US7629360B2 (en) | 1999-05-07 | 2009-12-08 | Celgene Corporation | Methods for the treatment of cachexia and graft v. host disease |
ATE312823T1 (de) * | 1999-07-09 | 2005-12-15 | Boehringer Ingelheim Pharma | Verfahren zur herstellung heteroarylsubstituierter ureaverbindungen |
CA2389360C (en) * | 1999-11-16 | 2008-06-03 | Steffen Breitfelder | Urea derivatives as anti-inflammatory agents |
US6822093B2 (en) | 2000-05-23 | 2004-11-23 | Boehringer Ingelheim Pharmaceuticals, Inc. | Synthesis of heteroarylamine intermediate compounds |
US6635767B2 (en) | 2000-05-23 | 2003-10-21 | Boehringer Ingelheim Pharmaceuticals, Inc. | Synthesis of heteroarylamine intermediate compounds |
MXPA03006749A (es) | 2001-02-15 | 2004-05-31 | Boehringer Ingelheim Pharma | Proceso para la sintesis de compuestos de urea sustituidos con heteroarilo, utiles como agentes antiinflamatorios. |
JP4071636B2 (ja) | 2001-04-03 | 2008-04-02 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | シクロオクタノン誘導体およびシクロデカノン誘導体、およびその用途 |
EP1381594A1 (en) * | 2001-04-13 | 2004-01-21 | Boehringer Ingelheim Pharmaceuticals Inc. | Urea compounds useful as anti-inflammatory agents |
US7371763B2 (en) * | 2001-04-20 | 2008-05-13 | Bayer Pharmaceuticals Corporation | Inhibition of raf kinase using quinolyl, isoquinolyl or pyridyl ureas |
CA2445003A1 (en) | 2001-05-16 | 2002-11-21 | Boehringer Ingelheim Pharmaceuticals, Inc. | Diarylurea derivatives useful as anti-inflammatory agents |
EP1935885A3 (en) * | 2001-05-22 | 2008-10-15 | Neurogen Corporation | Melanin concentrating hormone receptor ligands : substituted 1-benzyl-4-aryl piperazine analogues. |
US6953801B2 (en) | 2001-05-22 | 2005-10-11 | Neurogen Corporation | Melanin concentrating hormone receptor ligands: substituted 1-benzyl-4-aryl piperazine analogues |
CA2448626A1 (en) | 2001-05-25 | 2002-12-05 | Boehringer Ingelheim Pharmaceuticals, Inc. | Carbamate and oxamide compounds as inhibitors of cytokine production |
JP4424983B2 (ja) | 2001-06-05 | 2010-03-03 | 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 | 1,4−ジ置換ベンゾ−縮合シクロアルキルウレア化合物 |
CN100509797C (zh) * | 2001-06-11 | 2009-07-08 | 病毒化学医药公司 | 用作黄病毒感染抗病毒剂的噻吩衍生物 |
US8329924B2 (en) * | 2001-06-11 | 2012-12-11 | Vertex Pharmaceuticals (Canada) Incorporated | Compounds and methods for the treatment or prevention of Flavivirus infections |
US7700610B2 (en) | 2001-06-29 | 2010-04-20 | Ab Science | Use of tyrosine kinase inhibitors for treating allergic diseases |
EP1434991B1 (en) | 2001-06-29 | 2007-10-17 | AB Science | New potent, selective and non toxic c-kit inhibitors |
US20040266771A1 (en) * | 2001-06-29 | 2004-12-30 | Alain Moussy | Use of tyrosine kinase inhibitors for treating bone loss |
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