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
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 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
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 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
- NNLBRYQGMOYARS-UHFFFAOYSA-N thiane 1-oxide Chemical compound O=S1CCCCC1 NNLBRYQGMOYARS-UHFFFAOYSA-N 0.000 description 1
- 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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Families Citing this family (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7329670B1 (en) | 1997-12-22 | 2008-02-12 | Bayer Pharmaceuticals Corporation | Inhibition of RAF kinase using aryl and heteroaryl substituted heterocyclic ureas |
| US7517880B2 (en) | 1997-12-22 | 2009-04-14 | Bayer Pharmaceuticals Corporation | Inhibition of p38 kinase using symmetrical and unsymmetrical diphenyl ureas |
| EP1158985B1 (en) | 1999-01-13 | 2011-12-28 | Bayer HealthCare LLC | OMEGA-CARBOXY ARYL SUBSTITUTED DIPHENYL UREAS AS p38 KINASE INHIBITORS |
| US8124630B2 (en) | 1999-01-13 | 2012-02-28 | Bayer Healthcare Llc | ω-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
| EP1140840B1 (en) * | 1999-01-13 | 2006-03-22 | Bayer Pharmaceuticals Corp. | -g(v)-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
| ME00275B (me) | 1999-01-13 | 2011-02-10 | Bayer Corp | ω-KARBOKSIARIL SUPSTITUISANI DIFENIL KARBAMIDI KAO INHIBITORI RAF KINAZE |
| UA73492C2 (en) * | 1999-01-19 | 2005-08-15 | Aromatic heterocyclic compounds as antiinflammatory agents | |
| CA2374737C (en) * | 1999-07-09 | 2008-02-12 | Boehringer Ingelheim Pharmaceuticals, Inc. | Novel process for synthesis of heteroaryl-substituted urea compounds |
| EP1232150B1 (en) | 1999-11-16 | 2007-10-10 | Boehringer Ingelheim Pharmaceuticals Inc. | Urea derivatives as anti-inflammatory agents |
| US7235576B1 (en) | 2001-01-12 | 2007-06-26 | Bayer Pharmaceuticals Corporation | Omega-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
| US7371763B2 (en) | 2001-04-20 | 2008-05-13 | Bayer Pharmaceuticals Corporation | Inhibition of raf kinase using quinolyl, isoquinolyl or pyridyl ureas |
| JP2004530690A (ja) | 2001-05-16 | 2004-10-07 | 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 | 抗炎症性薬剤として有用なジアリールウレア誘導体 |
| EP1395561A1 (en) | 2001-05-25 | 2004-03-10 | Boehringer Ingelheim Pharmaceuticals Inc. | Carbamate and oxamide compounds as inhibitors of cytokine production |
| EP1414810B1 (en) | 2001-06-05 | 2006-08-30 | Boehringer Ingelheim Pharmaceuticals Inc. | 1,4-disubstituted benzo-fused cycloalkyl urea compounds |
| US6881741B2 (en) * | 2001-06-11 | 2005-04-19 | Virochem Pharma Inc. | Compounds and methods for the treatment or prevention of Flavivirus infections |
| US8329924B2 (en) * | 2001-06-11 | 2012-12-11 | Vertex Pharmaceuticals (Canada) Incorporated | Compounds and methods for the treatment or prevention of Flavivirus infections |
| EP1709965A3 (en) * | 2001-07-11 | 2006-12-27 | Boehringer Ingelheim Pharmaceuticals, Inc. | Methods of treating cytokine mediate diseases |
| WO2003005999A2 (en) * | 2001-07-11 | 2003-01-23 | Boehringer Ingelheim Pharmaceuticals, Inc. | Methods of treating cytokine mediated diseases |
| WO2003029241A1 (en) * | 2001-10-04 | 2003-04-10 | Smithkline Beecham Corporation | Chk1 kinase inhibitors |
| EP1438048A1 (en) * | 2001-10-18 | 2004-07-21 | Boehringer Ingelheim Pharmaceuticals Inc. | 1,4-disubstituted benzo-fused urea compounds as cytokine inhibitors |
| WO2003068229A1 (en) | 2002-02-11 | 2003-08-21 | Bayer Pharmaceuticals Corporation | Pyridine, quinoline, and isoquinoline n-oxides as kinase inhibitors |
| US20040023961A1 (en) * | 2002-02-11 | 2004-02-05 | Bayer Corporation | Aryl ureas with raf kinase and angiogenisis inhibiting activity |
| ATE529406T1 (de) | 2002-02-11 | 2011-11-15 | Bayer Healthcare Llc | Aryl-harnstoffe als kinase inhibitoren |
| SI1478358T1 (sl) | 2002-02-11 | 2013-09-30 | Bayer Healthcare Llc | Sorafenib tozilat za zdravljenje bolezni, značilnih po abnormalni angiogenezi |
| EP1480973B1 (en) | 2002-02-25 | 2008-02-13 | Boehringer Ingelheim Pharmaceuticals Inc. | 1,4-disubstituted benzofused cycloalkyl urea compounds useful in treating cytokine mediated diseases |
| ES2278170T3 (es) | 2002-07-09 | 2007-08-01 | BOEHRINGER INGELHEIM PHARMA GMBH & CO.KG | Composiciones farmaceuticas de anticolinergicos e inhibidores de la quinasa p38 en el tratamiento de enfermedades respiratorias. |
| EP1549621A1 (en) | 2002-08-08 | 2005-07-06 | Boehringer Ingelheim Pharmaceuticals Inc. | Fluorinated phenyl-naphthalenyl-urea compounds as inhibitors of cytokines involved in inflammatory processes |
| US7232828B2 (en) | 2002-08-10 | 2007-06-19 | Bethesda Pharmaceuticals, Inc. | PPAR Ligands that do not cause fluid retention, edema or congestive heart failure |
| DK1569896T3 (da) | 2002-12-06 | 2007-12-10 | Xention Ltd | Tetrahydronaphthalenderivater |
| AU2003288200A1 (en) | 2002-12-09 | 2004-06-30 | Bayer Healthcare Ag | Tetrahydro-naphthalene derivatives as vanilloid receptor antagonists |
| KR101058696B1 (ko) * | 2002-12-10 | 2011-08-22 | 바이로켐 파마 인코포레이티드 | 후라비바이러스 감염의 치료 또는 예방을 위한 화합물과방법 |
| US7196114B2 (en) * | 2003-02-17 | 2007-03-27 | Sanofi-Aventis Deutschland Gmbh | Substituted 3-(benzoylureido) thiophene derivatives, processes for preparing them and their use |
| US7557129B2 (en) | 2003-02-28 | 2009-07-07 | Bayer Healthcare Llc | Cyanopyridine derivatives useful in the treatment of cancer and other disorders |
| US7135575B2 (en) * | 2003-03-03 | 2006-11-14 | Array Biopharma, Inc. | P38 inhibitors and methods of use thereof |
| US7521447B2 (en) * | 2003-03-03 | 2009-04-21 | Array Biopharma Inc. | P38 inhibitors and methods of use thereof |
| US7078419B2 (en) * | 2003-03-10 | 2006-07-18 | Boehringer Ingelheim Pharmaceuticals, Inc. | Cytokine inhibitors |
| GB0308511D0 (en) * | 2003-04-14 | 2003-05-21 | Astex Technology Ltd | Pharmaceutical compounds |
| US7846963B2 (en) * | 2003-05-17 | 2010-12-07 | Korea Research Institute Of Bioscience And Biotechnology | 2-oxo-heterocyclic compounds and the pharmaceutical compositions comprising the same |
| KR100594377B1 (ko) * | 2003-05-17 | 2006-06-30 | 한국생명공학연구원 | 항염증 활성을 갖는 신규 2-옥소-피페리딘 유도체(ⅰ)화합물, 이의 제조방법 및 이를 포함하는 염증 질환의치료를 위한 조성물 |
| EP1636585B2 (en) | 2003-05-20 | 2012-06-13 | Bayer HealthCare LLC | Diaryl ureas with kinase inhibiting activity |
| EP1663978B1 (en) | 2003-07-23 | 2007-11-28 | Bayer Pharmaceuticals Corporation | Fluoro substituted omega-carboxyaryl diphenyl urea for the treatment and prevention of diseases and conditions |
| SMAP200600037A (it) * | 2004-04-22 | 2006-11-22 | Procter & Gamble | Uree trisostituite come inibitori di citochina |
| EP2295426A1 (en) | 2004-04-30 | 2011-03-16 | Bayer HealthCare, LLC | Substituted pyrazolyl urea derivatives useful in the treatment of cancer |
| US20060035893A1 (en) | 2004-08-07 | 2006-02-16 | Boehringer Ingelheim International Gmbh | Pharmaceutical compositions for treatment of respiratory and gastrointestinal disorders |
| US7612200B2 (en) | 2004-12-07 | 2009-11-03 | Locus Pharmaceuticals, Inc. | Inhibitors of protein kinases |
| US7741479B2 (en) | 2004-12-07 | 2010-06-22 | Locus Pharmaceuticals, Inc. | Urea inhibitors of MAP kinases |
| PE20060777A1 (es) | 2004-12-24 | 2006-10-06 | Boehringer Ingelheim Int | Derivados de indolinona para el tratamiento o la prevencion de enfermedades fibroticas |
| US20070185098A1 (en) * | 2006-01-04 | 2007-08-09 | Locus Pharmaceuticals, Inc. | Inhibitors of protein kinases |
| RS52298B (sr) * | 2006-01-31 | 2012-12-31 | Array Biopharma Inc. | Inhibitori kinaze i postupak njihove upotrebe |
| JP5290186B2 (ja) * | 2006-11-15 | 2013-09-18 | ヴァイロケム ファーマ インコーポレイテッド | フラビウイルス感染症の治療または予防用のチオフェン類似体 |
| EP1992344A1 (en) | 2007-05-18 | 2008-11-19 | Institut Curie | P38 alpha as a therapeutic target in pathologies linked to FGFR3 mutation |
| US10065934B2 (en) | 2014-07-17 | 2018-09-04 | Sunshine Lake Pharma Co., Ltd. | Substituted urea derivatives and pharmaceutical uses thereof |
Family Cites Families (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE293352C (https=) | ||||
| US4105766A (en) | 1977-08-19 | 1978-08-08 | Sterling Drug Inc. | 4,5-Dihydro-5-oxopyrazolo[1,5-a]quinazoline-3-carboxylic acid derivatives |
| HU185294B (en) | 1980-12-29 | 1984-12-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing substituted urea derivatives |
| JPS60169469A (ja) * | 1983-12-27 | 1985-09-02 | シンテツクス（ユ−・エス・エイ）インコ−ポレイテツド | ４ｈ−１，３−ベンズオキサジン−４−オン化合物 |
| JPS61228444A (ja) | 1985-04-02 | 1986-10-11 | Fuji Photo Film Co Ltd | ハロゲン化銀カラ−写真感光材料 |
| EP0272866A1 (en) | 1986-12-23 | 1988-06-29 | Merck & Co. Inc. | 1,4-Benzodiazepines with 5-membered heterocyclic rings |
| CA1317939C (en) * | 1987-07-01 | 1993-05-18 | Janssen Pharmaceutica Naamloze Vennootschap | ¬(bicyclic heterocyclyl)methyl and -hetero| substituted hexahydro-1h-azepines and pyrrolidines |
| GB8908869D0 (en) | 1989-04-19 | 1989-06-07 | Shell Int Research | A process for the preparation of aromatic ureas |
| WO1991004027A1 (en) | 1989-09-15 | 1991-04-04 | Pfizer Inc. | New n-aryl and n-heteroarylamide and urea derivatives as inhibitors of acyl coenzyme a: cholesterol acyl transferase (acat) |
| IE913204A1 (en) * | 1990-09-13 | 1992-02-25 | Beecham Group Plc | Novel compounds |
| US5162360A (en) * | 1991-06-24 | 1992-11-10 | Warner-Lambert Company | 2-heteroatom containing urea and thiourea ACAT inhibitors |
| MX9300141A (es) | 1992-01-13 | 1994-07-29 | Smithkline Beecham Corp | Compuestos de imidazol novedosos, procedimiento para su preparacion y composiciones farmaceuticas que lo contienen. |
| AU4028393A (en) | 1992-05-28 | 1993-12-30 | Pfizer Inc. | New (N)-aryl and (N)-heteroarylurea derivatives as inhibitors of acyl coenzyme a:cholesterol acyl transferase (ACAT) |
| US5342942A (en) | 1992-06-09 | 1994-08-30 | Warner-Lambert Company | Pyrazoloquinazolone derivatives as neurotrophic agents |
| GB9302275D0 (en) | 1993-02-05 | 1993-03-24 | Smithkline Beecham Plc | Novel compounds |
| EP0692483A1 (en) | 1993-03-30 | 1996-01-17 | Yoshitomi Pharmaceutical Industries, Ltd. | Cell adhesion inhibitor and thienotriazolodiazepine compound |
| CN1048731C (zh) | 1993-09-17 | 2000-01-26 | 史密丝克莱恩比彻姆公司 | 编码细胞因子抑制性抗炎药物结合蛋白质的多核苷酸 |
| US5783664A (en) | 1993-09-17 | 1998-07-21 | Smithkline Beecham Corporation | Cytokine suppressive anit-inflammatory drug binding proteins |
| US5869043A (en) | 1993-09-17 | 1999-02-09 | Smithkline Beecham Corporation | Drug binding protein |
| US6306840B1 (en) * | 1995-01-23 | 2001-10-23 | Biogen, Inc. | Cell adhesion inhibitors |
| JPH11503110A (ja) * | 1995-02-17 | 1999-03-23 | スミスクライン・ビーチャム・コーポレイション | Ｉｌ−８受容体拮抗剤 |
| US5739143A (en) | 1995-06-07 | 1998-04-14 | Smithkline Beecham Corporation | Imidazole compounds and compositions |
| IL118544A (en) | 1995-06-07 | 2001-08-08 | Smithkline Beecham Corp | History of imidazole, the process for their preparation and the pharmaceutical preparations containing them |
| AU702887B2 (en) | 1995-10-31 | 1999-03-11 | Merck & Co., Inc. | Substituted pyridyl pyrroles, compositions containing such compounds and methods of use |
| US6074862A (en) | 1995-12-20 | 2000-06-13 | Signal Pharmaceuticals Inc. | Mitogen-activated protein kinase kinase MEK6 and variants thereof |
| US6096748A (en) | 1996-03-13 | 2000-08-01 | Smithkline Beecham Corporation | Pyrimidine compounds useful in treating cytokine mediated diseases |
| EP0889887A4 (en) | 1996-03-25 | 2003-06-11 | Smithkline Beecham Corp | TREATMENT OF CENTRAL NERVOUS SYSTEM INJURIES |
| EP0889888A4 (en) | 1996-03-25 | 2003-01-08 | Smithkline Beecham Corp | NEW TREATMENT OF LESIONS IN THE CENTRAL NERVOUS SYSTEM |
| US5948885A (en) | 1996-05-20 | 1999-09-07 | Signal Pharmaceuticals, Inc. | Mitogen-activated protein kinase p38-2 and methods of use therefor |
| JP2002515744A (ja) | 1996-05-20 | 2002-05-28 | シグナル ファーマシュウティカルズ，インコーポレイテッド | マイトジェン活性化プロテインキナーゼｐ３８―２およびその使用方法 |
| ES2239357T3 (es) | 1996-06-10 | 2005-09-16 | MERCK & CO., INC. | Imidazoles sustituidos que tienen actividad inhibidora de citoquinas. |
| JP4373497B2 (ja) | 1996-06-19 | 2009-11-25 | ローン−プーラン・ロレ・リミテツド | 置換されたアザビシクロ化合物、ならびにｔｎｆおよびサイクリックａｍｐホスホジエステラーゼ産生の阻害剤としてのそれらの使用 |
| WO1998007425A1 (en) | 1996-08-21 | 1998-02-26 | Smithkline Beecham Corporation | Imidazole compounds, compositions and use |
| CA2267656A1 (en) | 1996-10-09 | 1998-04-16 | Medical Research Council | Map kinases: polypeptides, polynucleotides and uses thereof |
| 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 |
| DE69826695T2 (de) * | 1997-05-23 | 2006-02-02 | Bayer Pharmaceuticals Corp., West Haven | Arylharnstoffderivate zur behandlung von inflammatorischen oder immunomodulatorischen erkrankungen |
| DK0986382T3 (da) | 1997-05-23 | 2008-10-20 | Bayer Pharmaceuticals Corp | RAF-kinasehæmmere |
| 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 |
| PT1056725E (pt) | 1997-12-22 | 2006-09-29 | Bayer Pharmaceuticals Corp | Inibicao da raf-quinase usando ureias heterociclicas substituidas com arilo e heteroarilo |
| ATE529109T1 (de) * | 1997-12-22 | 2011-11-15 | Bayer Healthcare Llc | Hemmung der p38 kinase aktivität durch substituierte heterocyclische harnstoffe |
| DE69831013T2 (de) * | 1997-12-22 | 2006-04-20 | Bayer Pharmaceuticals Corp., West Haven | Inhibierung der raf-kinase durch substituierte heterocyclische harnstoffverbindungen |
| WO1999032463A1 (en) * | 1997-12-22 | 1999-07-01 | Bayer Corporation | INHIBITION OF p38 KINASE USING SYMMETRICAL AND UNSYMMETRICAL DIPHENYL UREAS |
| IL136768A0 (en) * | 1997-12-22 | 2001-06-14 | Bayer Ag | INHIBITION OF p38 KINASE ACTIVITY USING ARYL AND HETEROARYL SUBSTITUTED HETEROCYCLIC UREAS |
| WO1999046244A1 (en) | 1998-03-12 | 1999-09-16 | Novo Nordisk A/S | Modulators of protein tyrosine phosphatases (ptpases) |
| GB9823873D0 (en) * | 1998-10-30 | 1998-12-30 | Pharmacia & Upjohn Spa | 2-ureido-thiazole derivatives,process for their preparation,and their use as antitumour agents |
| SK7692001A3 (en) * | 1998-12-09 | 2002-09-10 | Wyeth Corp | Thiourea inhibitors of herpes viruses |
| AU2055500A (en) * | 1998-12-23 | 2000-07-31 | Eli Lilly And Company | Aromatic amides |
| UA73492C2 (en) * | 1999-01-19 | 2005-08-15 | Aromatic heterocyclic compounds as antiinflammatory agents |
-
2000
- 2000-01-31 JP JP2000605581A patent/JP2002539206A/ja active Pending
- 2000-01-31 ES ES00909993T patent/ES2251360T3/es not_active Expired - Lifetime
- 2000-01-31 MX MXPA01009077A patent/MXPA01009077A/es not_active IP Right Cessation
- 2000-01-31 AT AT00909993T patent/ATE309237T1/de active
- 2000-01-31 WO PCT/US2000/002008 patent/WO2000055152A1/en not_active Ceased
- 2000-01-31 EP EP00909993A patent/EP1163236B1/en not_active Expired - Lifetime
- 2000-01-31 DE DE60023853T patent/DE60023853T2/de not_active Expired - Lifetime
- 2000-01-31 CA CA002361998A patent/CA2361998C/en not_active Expired - Fee Related
- 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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