JP2002539206A5 - - Google Patents
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- JP2002539206A5 JP2002539206A5 JP2000605581A JP2000605581A JP2002539206A5 JP 2002539206 A5 JP2002539206 A5 JP 2002539206A5 JP 2000605581 A JP2000605581 A JP 2000605581A JP 2000605581 A JP2000605581 A JP 2000605581A JP 2002539206 A5 JP2002539206 A5 JP 2002539206A5
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- Japan
- Prior art keywords
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- tert
- butyl
- naphthalen
- urea
- Prior art date
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- 150000001875 compounds Chemical class 0.000 description 25
- 125000000217 alkyl group Chemical group 0.000 description 23
- -1 thiomorpholine sulfoxide Chemical class 0.000 description 13
- 239000008194 pharmaceutical composition Substances 0.000 description 11
- 229910052736 halogen Inorganic materials 0.000 description 10
- 150000002367 halogens Chemical class 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 125000005843 halogen group Chemical group 0.000 description 8
- 125000001624 naphthyl group Chemical group 0.000 description 8
- 125000004043 oxo group Chemical group O=* 0.000 description 8
- 230000001154 acute effect Effects 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
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- 208000002193 Pain Diseases 0.000 description 4
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- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
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- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
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- 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 2
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- 125000003435 aroyl group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
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- 125000002541 furyl group Chemical group 0.000 description 2
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- 230000002757 inflammatory effect Effects 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
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- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- 125000002098 pyridazinyl group Chemical group 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
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- 208000011580 syndromic disease Diseases 0.000 description 2
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 230000008733 trauma Effects 0.000 description 2
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 description 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 1
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 description 1
- NQPJDJVGBDHCAD-UHFFFAOYSA-N 1,3-diazinan-2-one Chemical compound OC1=NCCCN1 NQPJDJVGBDHCAD-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- VSIYJQNFMOOGCU-UHFFFAOYSA-N 1-(cyclohexen-1-yl)cyclohexene Chemical group C1CCCC(C=2CCCCC=2)=C1 VSIYJQNFMOOGCU-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 1
- PGWWISXRLLMODG-UHFFFAOYSA-N 5-tert-butyl-3-[[4-[2-(3,4-dimethoxyphenyl)ethoxy]naphthalen-1-yl]carbamoylamino]-n-methyl-1h-pyrrole-2-carboxamide Chemical compound N1C(C(C)(C)C)=CC(NC(=O)NC=2C3=CC=CC=C3C(OCCC=3C=C(OC)C(OC)=CC=3)=CC=2)=C1C(=O)NC PGWWISXRLLMODG-UHFFFAOYSA-N 0.000 description 1
- XALRWHKVUNCXFD-UHFFFAOYSA-N 5-tert-butyl-3-[[4-[2-(3,4-dimethoxyphenyl)ethoxy]naphthalen-1-yl]carbamoylamino]-n-methylthiophene-2-carboxamide Chemical compound S1C(C(C)(C)C)=CC(NC(=O)NC=2C3=CC=CC=C3C(OCCC=3C=C(OC)C(OC)=CC=3)=CC=2)=C1C(=O)NC XALRWHKVUNCXFD-UHFFFAOYSA-N 0.000 description 1
- DBINKLWMKFHELZ-RTBURBONSA-N 5-tert-butyl-3-[[4-[2-[(2r,6r)-2,6-dimethylmorpholin-4-yl]ethoxy]naphthalen-1-yl]carbamoylamino]-n-methylthiophene-2-carboxamide Chemical compound S1C(C(C)(C)C)=CC(NC(=O)NC=2C3=CC=CC=C3C(OCCN3C[C@@H](C)O[C@H](C)C3)=CC=2)=C1C(=O)NC DBINKLWMKFHELZ-RTBURBONSA-N 0.000 description 1
- ZFBZFJLVVHBHEP-UHFFFAOYSA-N 5-tert-butyl-3-[[4-[2-[2-[(dimethylamino)methyl]-3,3-dimethylmorpholin-4-yl]ethoxy]naphthalen-1-yl]carbamoylamino]-n-methylthiophene-2-carboxamide Chemical compound S1C(C(C)(C)C)=CC(NC(=O)NC=2C3=CC=CC=C3C(OCCN3C(C(CN(C)C)OCC3)(C)C)=CC=2)=C1C(=O)NC ZFBZFJLVVHBHEP-UHFFFAOYSA-N 0.000 description 1
- VSNYNOHBCOGJTN-UHFFFAOYSA-N 5-tert-butyl-n-methyl-3-[[4-(2-morpholin-4-ylethoxy)naphthalen-1-yl]carbamoylamino]-1h-pyrrole-2-carboxamide Chemical compound N1C(C(C)(C)C)=CC(NC(=O)NC=2C3=CC=CC=C3C(OCCN3CCOCC3)=CC=2)=C1C(=O)NC VSNYNOHBCOGJTN-UHFFFAOYSA-N 0.000 description 1
- NKIIHOYVIVWGIQ-UHFFFAOYSA-N 5-tert-butyl-n-methyl-3-[[4-(2-morpholin-4-ylethoxy)naphthalen-1-yl]carbamoylamino]thiophene-2-carboxamide Chemical compound S1C(C(C)(C)C)=CC(NC(=O)NC=2C3=CC=CC=C3C(OCCN3CCOCC3)=CC=2)=C1C(=O)NC NKIIHOYVIVWGIQ-UHFFFAOYSA-N 0.000 description 1
- YORFITFIMBVABT-UHFFFAOYSA-N 5-tert-butyl-n-methyl-3-[[4-(pyridin-4-ylmethoxy)naphthalen-1-yl]carbamoylamino]-1h-pyrrole-2-carboxamide Chemical compound N1C(C(C)(C)C)=CC(NC(=O)NC=2C3=CC=CC=C3C(OCC=3C=CN=CC=3)=CC=2)=C1C(=O)NC YORFITFIMBVABT-UHFFFAOYSA-N 0.000 description 1
- PGFKYUQJHNYVPG-UHFFFAOYSA-N 5-tert-butyl-n-methyl-3-[[4-(pyridin-4-ylmethoxy)naphthalen-1-yl]carbamoylamino]thiophene-2-carboxamide Chemical compound S1C(C(C)(C)C)=CC(NC(=O)NC=2C3=CC=CC=C3C(OCC=3C=CN=CC=3)=CC=2)=C1C(=O)NC PGFKYUQJHNYVPG-UHFFFAOYSA-N 0.000 description 1
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- YDOXFHKHFBQMJI-UHFFFAOYSA-N 5-tert-butyl-n-methyl-3-[[4-[2-(1-oxo-1,4-thiazinan-4-yl)ethoxy]naphthalen-1-yl]carbamoylamino]thiophene-2-carboxamide Chemical compound S1C(C(C)(C)C)=CC(NC(=O)NC=2C3=CC=CC=C3C(OCCN3CCS(=O)CC3)=CC=2)=C1C(=O)NC YDOXFHKHFBQMJI-UHFFFAOYSA-N 0.000 description 1
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- VGZGHNQNNYORPX-UHFFFAOYSA-N 5-tert-butyl-n-methyl-3-[[4-[2-(1-oxothiolan-3-yl)ethoxy]naphthalen-1-yl]carbamoylamino]thiophene-2-carboxamide Chemical compound S1C(C(C)(C)C)=CC(NC(=O)NC=2C3=CC=CC=C3C(OCCC3CS(=O)CC3)=CC=2)=C1C(=O)NC VGZGHNQNNYORPX-UHFFFAOYSA-N 0.000 description 1
- VDLCFWXMZIWBKJ-UHFFFAOYSA-N 5-tert-butyl-n-methyl-3-[[4-[2-(oxan-4-yl)ethoxy]naphthalen-1-yl]carbamoylamino]-1h-pyrrole-2-carboxamide Chemical compound N1C(C(C)(C)C)=CC(NC(=O)NC=2C3=CC=CC=C3C(OCCC3CCOCC3)=CC=2)=C1C(=O)NC VDLCFWXMZIWBKJ-UHFFFAOYSA-N 0.000 description 1
- NXGOYFFGLZUXHT-UHFFFAOYSA-N 5-tert-butyl-n-methyl-3-[[4-[2-(oxan-4-yl)ethoxy]naphthalen-1-yl]carbamoylamino]thiophene-2-carboxamide Chemical compound S1C(C(C)(C)C)=CC(NC(=O)NC=2C3=CC=CC=C3C(OCCC3CCOCC3)=CC=2)=C1C(=O)NC NXGOYFFGLZUXHT-UHFFFAOYSA-N 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N Acetylene Chemical group C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
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- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 206010040070 Septic Shock Diseases 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
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- 125000003342 alkenyl group Chemical group 0.000 description 1
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- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
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- AFSRNVKUVDCLSW-UHFFFAOYSA-N methyl 5-tert-butyl-1-methyl-3-[[4-(2-morpholin-4-ylethoxy)naphthalen-1-yl]carbamoylamino]pyrrole-2-carboxylate Chemical compound C1=C(C(C)(C)C)N(C)C(C(=O)OC)=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1OCCN1CCOCC1 AFSRNVKUVDCLSW-UHFFFAOYSA-N 0.000 description 1
- HGLZTHSWAWGVLG-UHFFFAOYSA-N methyl 5-tert-butyl-1-methyl-3-[[4-[2-(1-oxo-1,4-thiazinan-4-yl)ethoxy]naphthalen-1-yl]carbamoylamino]pyrrole-2-carboxylate Chemical compound C1=C(C(C)(C)C)N(C)C(C(=O)OC)=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1OCCN1CCS(=O)CC1 HGLZTHSWAWGVLG-UHFFFAOYSA-N 0.000 description 1
- UBEHIWRIYATGFG-UHFFFAOYSA-N methyl 5-tert-butyl-1-methyl-3-[[4-[2-(1-oxothiolan-3-yl)ethoxy]naphthalen-1-yl]carbamoylamino]pyrrole-2-carboxylate Chemical compound C1=C(C(C)(C)C)N(C)C(C(=O)OC)=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1OCCC1CS(=O)CC1 UBEHIWRIYATGFG-UHFFFAOYSA-N 0.000 description 1
- CZPSDXRGZVEKMW-UHFFFAOYSA-N methyl 5-tert-butyl-2-[[4-[2-(1-oxo-1,4-thiazinan-4-yl)ethoxy]naphthalen-1-yl]carbamoylamino]thiophene-3-carboxylate Chemical compound C1=C(C(C)(C)C)SC(NC(=O)NC=2C3=CC=CC=C3C(OCCN3CCS(=O)CC3)=CC=2)=C1C(=O)OC CZPSDXRGZVEKMW-UHFFFAOYSA-N 0.000 description 1
- IDTITQIMVNKGAR-UHFFFAOYSA-N methyl 5-tert-butyl-2-[[4-[2-(oxan-4-yl)ethoxy]naphthalen-1-yl]carbamoylamino]thiophene-3-carboxylate Chemical compound C1=C(C(C)(C)C)SC(NC(=O)NC=2C3=CC=CC=C3C(OCCC3CCOCC3)=CC=2)=C1C(=O)OC IDTITQIMVNKGAR-UHFFFAOYSA-N 0.000 description 1
- AKOLQLJOAIIHPN-UHFFFAOYSA-N methyl 5-tert-butyl-3-[[4-(2-imidazol-1-ylethoxy)naphthalen-1-yl]carbamoylamino]-1h-pyrrole-2-carboxylate Chemical compound N1C(C(C)(C)C)=CC(NC(=O)NC=2C3=CC=CC=C3C(OCCN3C=NC=C3)=CC=2)=C1C(=O)OC AKOLQLJOAIIHPN-UHFFFAOYSA-N 0.000 description 1
- MSARKUQLCOSNJQ-UHFFFAOYSA-N methyl 5-tert-butyl-3-[[4-(2-imidazol-1-ylethoxy)naphthalen-1-yl]carbamoylamino]thiophene-2-carboxylate Chemical compound S1C(C(C)(C)C)=CC(NC(=O)NC=2C3=CC=CC=C3C(OCCN3C=NC=C3)=CC=2)=C1C(=O)OC MSARKUQLCOSNJQ-UHFFFAOYSA-N 0.000 description 1
- RQZHLBMETZFUMB-UHFFFAOYSA-N methyl 5-tert-butyl-3-[[4-(2-morpholin-4-ylethoxy)naphthalen-1-yl]carbamoylamino]-1h-pyrrole-2-carboxylate Chemical compound N1C(C(C)(C)C)=CC(NC(=O)NC=2C3=CC=CC=C3C(OCCN3CCOCC3)=CC=2)=C1C(=O)OC RQZHLBMETZFUMB-UHFFFAOYSA-N 0.000 description 1
- SNTFQLGVKIFINZ-UHFFFAOYSA-N methyl 5-tert-butyl-3-[[4-(2-morpholin-4-ylethoxy)naphthalen-1-yl]carbamoylamino]thiophene-2-carboxylate Chemical compound S1C(C(C)(C)C)=CC(NC(=O)NC=2C3=CC=CC=C3C(OCCN3CCOCC3)=CC=2)=C1C(=O)OC SNTFQLGVKIFINZ-UHFFFAOYSA-N 0.000 description 1
- BSZWPWXZBOUAGH-UHFFFAOYSA-N methyl 5-tert-butyl-3-[[4-(2-pyridin-4-ylethoxy)naphthalen-1-yl]carbamoylamino]-1h-pyrrole-2-carboxylate Chemical compound N1C(C(C)(C)C)=CC(NC(=O)NC=2C3=CC=CC=C3C(OCCC=3C=CN=CC=3)=CC=2)=C1C(=O)OC BSZWPWXZBOUAGH-UHFFFAOYSA-N 0.000 description 1
- JLGOWJGNJIUPET-UHFFFAOYSA-N methyl 5-tert-butyl-3-[[4-(pyridin-4-ylmethoxy)naphthalen-1-yl]carbamoylamino]-1h-pyrrole-2-carboxylate Chemical compound N1C(C(C)(C)C)=CC(NC(=O)NC=2C3=CC=CC=C3C(OCC=3C=CN=CC=3)=CC=2)=C1C(=O)OC JLGOWJGNJIUPET-UHFFFAOYSA-N 0.000 description 1
- YDKOVAGUKFXVCU-UHFFFAOYSA-N methyl 5-tert-butyl-3-[[4-(pyridin-4-ylmethoxy)naphthalen-1-yl]carbamoylamino]thiophene-2-carboxylate Chemical compound S1C(C(C)(C)C)=CC(NC(=O)NC=2C3=CC=CC=C3C(OCC=3C=CN=CC=3)=CC=2)=C1C(=O)OC YDKOVAGUKFXVCU-UHFFFAOYSA-N 0.000 description 1
- UYTZCZYZLBOCQR-UHFFFAOYSA-N methyl 5-tert-butyl-3-[[4-[2-(1-oxo-1,4-thiazinan-4-yl)ethoxy]naphthalen-1-yl]carbamoylamino]-1h-pyrrole-2-carboxylate Chemical compound N1C(C(C)(C)C)=CC(NC(=O)NC=2C3=CC=CC=C3C(OCCN3CCS(=O)CC3)=CC=2)=C1C(=O)OC UYTZCZYZLBOCQR-UHFFFAOYSA-N 0.000 description 1
- QGFBZOQSENQYGF-UHFFFAOYSA-N methyl 5-tert-butyl-3-[[4-[2-(1-oxo-1,4-thiazinan-4-yl)ethoxy]naphthalen-1-yl]carbamoylamino]thiophene-2-carboxylate Chemical compound S1C(C(C)(C)C)=CC(NC(=O)NC=2C3=CC=CC=C3C(OCCN3CCS(=O)CC3)=CC=2)=C1C(=O)OC QGFBZOQSENQYGF-UHFFFAOYSA-N 0.000 description 1
- WQMSTOXLUWLOBN-UHFFFAOYSA-N methyl 5-tert-butyl-3-[[4-[2-(1-oxothiolan-3-yl)ethoxy]naphthalen-1-yl]carbamoylamino]-1h-pyrrole-2-carboxylate Chemical compound N1C(C(C)(C)C)=CC(NC(=O)NC=2C3=CC=CC=C3C(OCCC3CS(=O)CC3)=CC=2)=C1C(=O)OC WQMSTOXLUWLOBN-UHFFFAOYSA-N 0.000 description 1
- YEGBDXBXHLNPFL-UHFFFAOYSA-N methyl 5-tert-butyl-3-[[4-[2-(1-oxothiolan-3-yl)ethoxy]naphthalen-1-yl]carbamoylamino]thiophene-2-carboxylate Chemical compound S1C(C(C)(C)C)=CC(NC(=O)NC=2C3=CC=CC=C3C(OCCC3CS(=O)CC3)=CC=2)=C1C(=O)OC YEGBDXBXHLNPFL-UHFFFAOYSA-N 0.000 description 1
- XUNILHAEIFZHSW-UHFFFAOYSA-N methyl 5-tert-butyl-3-[[4-[2-(3,4-dimethoxyphenyl)ethoxy]naphthalen-1-yl]carbamoylamino]-1h-pyrrole-2-carboxylate Chemical compound N1C(C(C)(C)C)=CC(NC(=O)NC=2C3=CC=CC=C3C(OCCC=3C=C(OC)C(OC)=CC=3)=CC=2)=C1C(=O)OC XUNILHAEIFZHSW-UHFFFAOYSA-N 0.000 description 1
- BRHHYAOYOSUZAT-UHFFFAOYSA-N methyl 5-tert-butyl-3-[[4-[2-(3,4-dimethoxyphenyl)ethoxy]naphthalen-1-yl]carbamoylamino]thiophene-2-carboxylate Chemical compound S1C(C(C)(C)C)=CC(NC(=O)NC=2C3=CC=CC=C3C(OCCC=3C=C(OC)C(OC)=CC=3)=CC=2)=C1C(=O)OC BRHHYAOYOSUZAT-UHFFFAOYSA-N 0.000 description 1
- GOGYNLIFHQOMGV-UHFFFAOYSA-N methyl 5-tert-butyl-3-[[4-[2-(oxan-4-yl)ethoxy]naphthalen-1-yl]carbamoylamino]-1h-pyrrole-2-carboxylate Chemical compound N1C(C(C)(C)C)=CC(NC(=O)NC=2C3=CC=CC=C3C(OCCC3CCOCC3)=CC=2)=C1C(=O)OC GOGYNLIFHQOMGV-UHFFFAOYSA-N 0.000 description 1
- QHRWPZMVOPDARN-UHFFFAOYSA-N methyl 5-tert-butyl-3-[[4-[2-(oxan-4-yl)ethoxy]naphthalen-1-yl]carbamoylamino]thiophene-2-carboxylate Chemical compound S1C(C(C)(C)C)=CC(NC(=O)NC=2C3=CC=CC=C3C(OCCC3CCOCC3)=CC=2)=C1C(=O)OC QHRWPZMVOPDARN-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
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- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
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- 239000002904 solvent Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical compound O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 description 1
- BUGOPWGPQGYYGR-UHFFFAOYSA-N thiane 1,1-dioxide Chemical compound O=S1(=O)CCCCC1 BUGOPWGPQGYYGR-UHFFFAOYSA-N 0.000 description 1
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- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- YFHICDDUDORKJB-UHFFFAOYSA-N trimethylene carbonate Chemical compound O=C1OCCCO1 YFHICDDUDORKJB-UHFFFAOYSA-N 0.000 description 1
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| DE69731964T2 (de) | 1996-10-09 | 2005-12-08 | Medical Research Council | Map-kinase: polypeptide, polynukleotide und ihre verwendung |
| CA2273102A1 (en) | 1996-12-03 | 1998-06-11 | Banyu Pharmaceutical Co., Ltd. | Urea derivatives |
| US6147080A (en) | 1996-12-18 | 2000-11-14 | Vertex Pharmaceuticals Incorporated | Inhibitors of p38 |
| US6376214B1 (en) | 1997-02-18 | 2002-04-23 | Smithkline Beecham Corporation | DNA encoding a novel homolog of CSBP/p38 MAP kinase |
| ATE399007T1 (de) | 1997-05-23 | 2008-07-15 | Bayer Pharmaceuticals Corp | Raf kinase hemmer |
| WO1998052558A1 (en) * | 1997-05-23 | 1998-11-26 | Bayer Corporation | INHIBITION OF p38 KINASE ACTIVITY BY ARYL UREAS |
| US6093742A (en) | 1997-06-27 | 2000-07-25 | Vertex Pharmaceuticals, Inc. | Inhibitors of p38 |
| US5851812A (en) | 1997-07-01 | 1998-12-22 | Tularik Inc. | IKK-β proteins, nucleic acids and methods |
| AUPP003197A0 (en) * | 1997-09-03 | 1997-11-20 | Fujisawa Pharmaceutical Co., Ltd. | New heterocyclic compounds |
| CA2223075A1 (en) | 1997-12-02 | 1999-06-02 | Smithkline Beecham Corporation | Drug binding protein |
| SK286213B6 (sk) * | 1997-12-22 | 2008-05-06 | Bayer Corporation | Substituované heterocyklické močoviny, farmaceutický prípravok ich obsahujúci a ich použitie |
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| MXPA00006233A (es) * | 1997-12-22 | 2002-09-18 | Bayer Ag | Inhibicion de la actividad de la cinasa p38 utilizando ureas heterociclicas sustituidas. |
| DE69836563T2 (de) * | 1997-12-22 | 2007-05-16 | Bayer Pharmaceuticals Corp., West Haven | INHIBIERUNG DER p38 KINASE-AKTIVITÄT DURCH DIE VERWENDUNG VON ARYL- UND HETEROARYL-SUBSTITUIERTEN HARNSTOFFEN |
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-
2000
- 2000-01-31 WO PCT/US2000/002008 patent/WO2000055152A1/en not_active Ceased
- 2000-01-31 MX MXPA01009077A patent/MXPA01009077A/es not_active IP Right Cessation
- 2000-01-31 CA CA002361998A patent/CA2361998C/en not_active Expired - Fee Related
- 2000-01-31 DE DE60023853T patent/DE60023853T2/de not_active Expired - Lifetime
- 2000-01-31 EP EP00909993A patent/EP1163236B1/en not_active Expired - Lifetime
- 2000-01-31 JP JP2000605581A patent/JP2002539206A/ja active Pending
- 2000-01-31 AT AT00909993T patent/ATE309237T1/de active
- 2000-01-31 ES ES00909993T patent/ES2251360T3/es not_active Expired - Lifetime
- 2000-02-14 US US09/503,385 patent/US6297381B1/en not_active Expired - Lifetime
- 2000-11-20 US US09/716,351 patent/US6476023B1/en not_active Expired - Lifetime
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