JP2004536845A5 - - Google Patents
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- JP2004536845A5 JP2004536845A5 JP2003511806A JP2003511806A JP2004536845A5 JP 2004536845 A5 JP2004536845 A5 JP 2004536845A5 JP 2003511806 A JP2003511806 A JP 2003511806A JP 2003511806 A JP2003511806 A JP 2003511806A JP 2004536845 A5 JP2004536845 A5 JP 2004536845A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrazol
- urea
- butyl
- tert
- ethoxy
- 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 thiomorpholine sulfoxide Chemical class 0.000 claims 64
- 125000000217 alkyl group Chemical group 0.000 claims 41
- 239000004202 carbamide Substances 0.000 claims 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 17
- 125000000623 heterocyclic group Chemical group 0.000 claims 16
- 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 13
- 125000003545 alkoxy group Chemical group 0.000 claims 13
- 125000001624 naphthyl group Chemical group 0.000 claims 13
- 125000005843 halogen group Chemical group 0.000 claims 11
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 9
- 125000004043 oxo group Chemical group O=* 0.000 claims 8
- 201000010099 disease Diseases 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 7
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 claims 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 125000004076 pyridyl group Chemical group 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 5
- 239000002253 acid Substances 0.000 claims 5
- 150000001875 compounds Chemical class 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 4
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 4
- 206010019280 Heart failures Diseases 0.000 claims 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 4
- 125000002541 furyl group Chemical group 0.000 claims 4
- 125000002883 imidazolyl group Chemical group 0.000 claims 4
- 125000001786 isothiazolyl group Chemical group 0.000 claims 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims 4
- 125000002098 pyridazinyl group Chemical group 0.000 claims 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims 4
- 125000001544 thienyl group Chemical group 0.000 claims 4
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 3
- 208000024827 Alzheimer disease Diseases 0.000 claims 3
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims 3
- 208000009137 Behcet syndrome Diseases 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 201000009273 Endometriosis Diseases 0.000 claims 3
- 206010033645 Pancreatitis Diseases 0.000 claims 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 206010040047 Sepsis Diseases 0.000 claims 3
- 206010046851 Uveitis Diseases 0.000 claims 3
- 150000007513 acids Chemical class 0.000 claims 3
- 208000038016 acute inflammation Diseases 0.000 claims 3
- 230000006022 acute inflammation Effects 0.000 claims 3
- 208000037976 chronic inflammation Diseases 0.000 claims 3
- 230000006020 chronic inflammation Effects 0.000 claims 3
- 125000000753 cycloalkyl group 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
- MVCOAUNKQVWQHZ-UHFFFAOYSA-N doramapimod Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OCCN3CCOCC3)=CC=2)=CC(C(C)(C)C)=N1 MVCOAUNKQVWQHZ-UHFFFAOYSA-N 0.000 claims 3
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims 3
- 125000005647 linker group Chemical group 0.000 claims 3
- 210000004072 lung Anatomy 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 3
- 229930192474 thiophene Natural products 0.000 claims 3
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims 2
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims 2
- DYRRBMLFLLRLKB-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylpyrazol-3-yl)-3-[4-(2-morpholin-4-ylethoxy)naphthalen-1-yl]urea Chemical compound CN1N=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1OCCN1CCOCC1 DYRRBMLFLLRLKB-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
- HRXWPOIWJLNUHM-UHFFFAOYSA-N 1-[5-(1-hydroxy-2-methylpropan-2-yl)-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-(2-morpholin-4-ylethoxy)naphthalen-1-yl]urea Chemical compound C1=NC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OCCN3CCOCC3)=CC=2)=CC(C(C)(C)CO)=N1 HRXWPOIWJLNUHM-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
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
- 208000021063 Respiratory fume inhalation disease Diseases 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 206010048873 Traumatic arthritis Diseases 0.000 claims 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 2
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 230000033115 angiogenesis Effects 0.000 claims 2
- 125000003435 aroyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 claims 2
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 claims 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims 2
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims 2
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 125000006563 (C1-3) alkylaminocarbonyl group Chemical group 0.000 claims 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims 1
- NQPJDJVGBDHCAD-UHFFFAOYSA-N 1,3-diazinan-2-one Chemical compound OC1=NCCCN1 NQPJDJVGBDHCAD-UHFFFAOYSA-N 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims 1
- DLZPVMJTPYORIX-UHFFFAOYSA-N 1-(2-butyl-5-tert-butylpyrazol-3-yl)-3-[4-(2-morpholin-4-ylethoxy)naphthalen-1-yl]urea Chemical compound CCCCN1N=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1OCCN1CCOCC1 DLZPVMJTPYORIX-UHFFFAOYSA-N 0.000 claims 1
- YRYVQLMOTNGDOH-UHFFFAOYSA-N 1-(5-tert-butyl-2-pyridin-3-ylpyrazol-3-yl)-3-[4-(2-morpholin-4-ylethoxy)naphthalen-1-yl]urea Chemical compound C=1C=CN=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1OCCN1CCOCC1 YRYVQLMOTNGDOH-UHFFFAOYSA-N 0.000 claims 1
- BLSGQTZPQMDWPC-UHFFFAOYSA-N 1-[4-(2-morpholin-4-ylethoxy)naphthalen-1-yl]-3-(2-phenyl-5-propan-2-ylpyrazol-3-yl)urea Chemical compound C=1C=CC=CC=1N1N=C(C(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1OCCN1CCOCC1 BLSGQTZPQMDWPC-UHFFFAOYSA-N 0.000 claims 1
- GPWFFJYJAIOOMC-UHFFFAOYSA-N 1-[5-(1-hydroxy-2-methylpropan-2-yl)-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-(2-morpholin-4-ylethoxy)naphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OCCN3CCOCC3)=CC=2)=CC(C(C)(C)CO)=N1 GPWFFJYJAIOOMC-UHFFFAOYSA-N 0.000 claims 1
- NEKPZKLUEBSNGL-UHFFFAOYSA-N 1-[5-(1-hydroxy-2-methylpropan-2-yl)-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-(1-oxo-1,4-thiazinan-4-yl)ethoxy]naphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OCCN3CCS(=O)CC3)=CC=2)=CC(C(C)(C)CO)=N1 NEKPZKLUEBSNGL-UHFFFAOYSA-N 0.000 claims 1
- DYETUMUJYHNLLD-UHFFFAOYSA-N 1-[5-(1-hydroxy-2-methylpropan-2-yl)-2-methylpyrazol-3-yl]-3-[4-(2-morpholin-4-ylethoxy)naphthalen-1-yl]urea Chemical compound CN1N=C(C(C)(C)CO)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1OCCN1CCOCC1 DYETUMUJYHNLLD-UHFFFAOYSA-N 0.000 claims 1
- NGVRVKAFSKIREU-UHFFFAOYSA-N 1-[5-(2-methyl-1-oxopropan-2-yl)-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-(2-morpholin-4-ylethoxy)naphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OCCN3CCOCC3)=CC=2)=CC(C(C)(C)C=O)=N1 NGVRVKAFSKIREU-UHFFFAOYSA-N 0.000 claims 1
- FQNLSQWPAZJSAA-UHFFFAOYSA-N 1-[5-tert-butyl-2-(2-hydroxy-4-methylphenyl)pyrazol-3-yl]-3-[4-(2-morpholin-4-ylethoxy)naphthalen-1-yl]urea Chemical compound OC1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OCCN3CCOCC3)=CC=2)=CC(C(C)(C)C)=N1 FQNLSQWPAZJSAA-UHFFFAOYSA-N 0.000 claims 1
- DOMDPAWFXGRPIZ-UHFFFAOYSA-N 1-[5-tert-butyl-2-(3-hydroxy-4-methylphenyl)pyrazol-3-yl]-3-[4-(2-morpholin-4-ylethoxy)naphthalen-1-yl]urea Chemical compound C1=C(O)C(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OCCN3CCOCC3)=CC=2)=CC(C(C)(C)C)=N1 DOMDPAWFXGRPIZ-UHFFFAOYSA-N 0.000 claims 1
- VAHMFBZVPBYUSH-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-chlorophenyl)pyrazol-3-yl]-3-[4-(2-morpholin-4-ylethoxy)naphthalen-1-yl]urea Chemical compound C=1C=C(Cl)C=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1OCCN1CCOCC1 VAHMFBZVPBYUSH-UHFFFAOYSA-N 0.000 claims 1
- JTAHPJDVRUYIDX-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-(2-morpholin-4-yl-2-oxoethoxy)naphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OCC(=O)N3CCOCC3)=CC=2)=CC(C(C)(C)C)=N1 JTAHPJDVRUYIDX-UHFFFAOYSA-N 0.000 claims 1
- RCOGIBMVENMBNJ-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-(2-pyridin-4-ylethoxy)naphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OCCC=3C=CN=CC=3)=CC=2)=CC(C(C)(C)C)=N1 RCOGIBMVENMBNJ-UHFFFAOYSA-N 0.000 claims 1
- OVJUKFHZHSSCFX-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-(2-pyridin-4-ylethyl)naphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(CCC=3C=CN=CC=3)=CC=2)=CC(C(C)(C)C)=N1 OVJUKFHZHSSCFX-UHFFFAOYSA-N 0.000 claims 1
- IWLBEANDLWYRTM-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-(2-thiomorpholin-4-ylethoxy)naphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OCCN3CCSCC3)=CC=2)=CC(C(C)(C)C)=N1 IWLBEANDLWYRTM-UHFFFAOYSA-N 0.000 claims 1
- VPELAYYSGMYZKW-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-(3-morpholin-4-ylpropyl)naphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(CCCN3CCOCC3)=CC=2)=CC(C(C)(C)C)=N1 VPELAYYSGMYZKW-UHFFFAOYSA-N 0.000 claims 1
- YYAWSVKLYLGEPL-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-(morpholin-4-ylmethyl)naphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(CN3CCOCC3)=CC=2)=CC(C(C)(C)C)=N1 YYAWSVKLYLGEPL-UHFFFAOYSA-N 0.000 claims 1
- YJNDCPGAAFQGMR-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-(pyridin-4-ylmethoxy)naphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OCC=3C=CN=CC=3)=CC=2)=CC(C(C)(C)C)=N1 YJNDCPGAAFQGMR-UHFFFAOYSA-N 0.000 claims 1
- FSRAFIIZCVNXAC-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-(1,3-dioxo-1,4-thiazinan-4-yl)ethoxy]naphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OCCN3C(CS(=O)CC3)=O)=CC=2)=CC(C(C)(C)C)=N1 FSRAFIIZCVNXAC-UHFFFAOYSA-N 0.000 claims 1
- NCSDBBSAVVCWFT-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-(3,4-dimethoxyphenyl)ethoxy]naphthalen-1-yl]urea Chemical compound C1=C(OC)C(OC)=CC=C1CCOC(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=NN1C1=CC=C(C)C=C1 NCSDBBSAVVCWFT-UHFFFAOYSA-N 0.000 claims 1
- SNWXRPUJJGRSBN-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[3-(oxan-2-yloxy)but-1-ynyl]naphthalen-1-yl]urea Chemical compound C=1C=C(NC(=O)NC=2N(N=C(C=2)C(C)(C)C)C=2C=CC(C)=CC=2)C2=CC=CC=C2C=1C#CC(C)OC1CCCCO1 SNWXRPUJJGRSBN-UHFFFAOYSA-N 0.000 claims 1
- GAFMKNVIISYECB-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[3-(oxan-2-yloxy)prop-1-ynyl]naphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(C#CCOC3OCCCC3)=CC=2)=CC(C(C)(C)C)=N1 GAFMKNVIISYECB-UHFFFAOYSA-N 0.000 claims 1
- OBWCIXSXYKHZQK-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methoxypyridin-3-yl)pyrazol-3-yl]-3-[4-(2-morpholin-4-ylethoxy)naphthalen-1-yl]urea Chemical compound C1=NC(OC)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OCCN3CCOCC3)=CC=2)=CC(C(C)(C)C)=N1 OBWCIXSXYKHZQK-UHFFFAOYSA-N 0.000 claims 1
- YLBUMXMJUWDTFN-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-(2-hydroxy-2-pyridin-4-ylethoxy)naphthalen-1-yl]urea Chemical compound C1=NC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OCC(O)C=3C=CN=CC=3)=CC=2)=CC(C(C)(C)C)=N1 YLBUMXMJUWDTFN-UHFFFAOYSA-N 0.000 claims 1
- SCYWJISGNIGZNZ-DHIUTWEWSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[2-[(2r,6r)-2,6-dimethylmorpholin-4-yl]ethoxy]naphthalen-1-yl]urea Chemical compound C1[C@@H](C)O[C@H](C)CN1CCOC(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=NN1C1=CC=C(C)N=C1 SCYWJISGNIGZNZ-DHIUTWEWSA-N 0.000 claims 1
- ODYQQLBOZJWPOI-UHFFFAOYSA-N 1-[5-tert-butyl-2-[3-[(dimethylamino)methyl]-4-methylphenyl]pyrazol-3-yl]-3-[4-(2-morpholin-4-ylethoxy)naphthalen-1-yl]urea Chemical compound C1=C(C)C(CN(C)C)=CC(N2C(=CC(=N2)C(C)(C)C)NC(=O)NC=2C3=CC=CC=C3C(OCCN3CCOCC3)=CC=2)=C1 ODYQQLBOZJWPOI-UHFFFAOYSA-N 0.000 claims 1
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| EP1041982B1 (en) | 1997-12-22 | 2011-10-19 | Bayer HealthCare LLC | INHIBITION OF p38 KINASE ACTIVITY USING SUBSTITUTED HETEROCYCLIC UREAS |
| EP1042305B1 (en) | 1997-12-22 | 2005-06-08 | Bayer Pharmaceuticals Corp. | INHIBITION OF p38 KINASE USING SYMMETRICAL AND UNSYMMETRICAL DIPHENYL UREAS |
| UA73492C2 (en) * | 1999-01-19 | 2005-08-15 | Aromatic heterocyclic compounds as antiinflammatory agents | |
| EE04799B1 (et) | 1999-03-12 | 2007-04-16 | Boehringer Ingelheim Pharmaceuticals, Inc. | Ühendid, mis on kasulikud põletikuvastaste vahenditena, nende ühendite valmistamise meetodid ja neid sisaldavad farmatseutilised kompositsioonid |
| EP1163236B1 (en) | 1999-03-12 | 2005-11-09 | Boehringer Ingelheim Pharmaceuticals Inc. | Aromatic heterocyclic compounds as anti-inflammatory agents |
| EP1232150B1 (en) | 1999-11-16 | 2007-10-10 | Boehringer Ingelheim Pharmaceuticals Inc. | Urea derivatives as anti-inflammatory agents |
| US6492529B1 (en) * | 2000-01-18 | 2002-12-10 | Boehringer Ingelheim Pharmaceuticals, Inc. | Bis pyrazole-1H-pyrazole intermediates and their synthesis |
| US6525046B1 (en) * | 2000-01-18 | 2003-02-25 | Boehringer Ingelheim Pharmaceuticals, Inc. | Aromatic heterocyclic compounds as antiinflammatory agents |
| KR20020091170A (ko) * | 2000-03-31 | 2002-12-05 | 아이덱 파마슈티칼즈 코포레이션 | Ｂ 세포 림프종의 치료를 위한 항-사이토카인 항체 또는길항제 및 항-ｃｄ２０의 조합된 사용 |
| US20020028826A1 (en) | 2000-06-15 | 2002-03-07 | Robl Jeffrey A. | HMG-CoA reductase inhibitors and method |
| US6620821B2 (en) | 2000-06-15 | 2003-09-16 | Bristol-Myers Squibb Company | HMG-CoA reductase inhibitors and method |
| DE60117046T2 (de) | 2000-10-26 | 2006-09-28 | Fournier Laboratories Ireland Ltd. | Kombination von fenofibrat und von coenzym q10 für die behandlung der endothelial- missfunktion |
| EP1408950B1 (en) * | 2001-07-11 | 2007-04-25 | Boehringer Ingelheim Pharmaceuticals Inc. | Methods of treating cytokine mediated diseases |
| EP1438048A1 (en) * | 2001-10-18 | 2004-07-21 | Boehringer Ingelheim Pharmaceuticals Inc. | 1,4-disubstituted benzo-fused urea compounds as cytokine inhibitors |
| AU2003209116A1 (en) * | 2002-02-11 | 2003-09-04 | Bayer Pharmaceuticals Corporation | Aryl ureas with angiogenesis inhibiting activity |
-
2002
- 2002-07-01 EP EP02746764A patent/EP1408950B1/en not_active Expired - Lifetime
- 2002-07-01 US US10/187,942 patent/US6916814B2/en not_active Expired - Lifetime
- 2002-07-01 JP JP2003511806A patent/JP2004536845A/ja active Pending
- 2002-07-01 AU AU2002316459A patent/AU2002316459A1/en not_active Abandoned
- 2002-07-01 DE DE60219793T patent/DE60219793T2/de not_active Expired - Fee Related
- 2002-07-01 ES ES02746764T patent/ES2284887T3/es not_active Expired - Lifetime
- 2002-07-01 CA CA002453147A patent/CA2453147A1/en not_active Abandoned
- 2002-07-01 AT AT02746764T patent/ATE360417T1/de not_active IP Right Cessation
- 2002-07-01 WO PCT/US2002/020649 patent/WO2003005999A2/en not_active Ceased
-
2004
- 2004-01-20 US US10/761,913 patent/US20040152725A1/en not_active Abandoned
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