JP2003526613A5 - - Google Patents
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- JP2003526613A5 JP2003526613A5 JP2000593580A JP2000593580A JP2003526613A5 JP 2003526613 A5 JP2003526613 A5 JP 2003526613A5 JP 2000593580 A JP2000593580 A JP 2000593580A JP 2000593580 A JP2000593580 A JP 2000593580A JP 2003526613 A5 JP2003526613 A5 JP 2003526613A5
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- JP
- Japan
- Prior art keywords
- substituted
- group
- acid
- halogen
- optionally
- Prior art date
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- 125000005842 heteroatom Chemical group 0.000 description 125
- 229910052757 nitrogen Inorganic materials 0.000 description 119
- 229910052760 oxygen Inorganic materials 0.000 description 118
- 229910052717 sulfur Inorganic materials 0.000 description 111
- 229910052736 halogen Inorganic materials 0.000 description 97
- 150000002367 halogens Chemical group 0.000 description 94
- 150000001875 compounds Chemical class 0.000 description 64
- 229910052799 carbon Inorganic materials 0.000 description 61
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 57
- 125000001424 substituent group Chemical group 0.000 description 55
- 125000004432 carbon atom Chemical group C* 0.000 description 40
- 229910052739 hydrogen Inorganic materials 0.000 description 32
- 239000001257 hydrogen Substances 0.000 description 32
- 238000006467 substitution reaction Methods 0.000 description 32
- 125000003118 aryl group Chemical group 0.000 description 30
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 26
- -1 pritonyl Chemical group 0.000 description 25
- 125000003545 alkoxy group Chemical group 0.000 description 24
- 150000003839 salts Chemical class 0.000 description 23
- 125000000217 alkyl group Chemical group 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 16
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 15
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
- 125000001072 heteroaryl group Chemical group 0.000 description 14
- 125000003710 aryl alkyl group Chemical group 0.000 description 13
- 125000002947 alkylene group Chemical group 0.000 description 12
- 125000004076 pyridyl group Chemical group 0.000 description 12
- 125000000714 pyrimidinyl group Chemical group 0.000 description 12
- 229910003827 NRaRb Inorganic materials 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 10
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 10
- 150000001768 cations Chemical class 0.000 description 10
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 10
- 239000001301 oxygen Substances 0.000 description 10
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 10
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 9
- 125000000753 cycloalkyl group Chemical group 0.000 description 9
- 125000005750 substituted cyclic group Chemical group 0.000 description 9
- 239000011593 sulfur Substances 0.000 description 9
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 8
- 125000004122 cyclic group Chemical group 0.000 description 7
- 125000003341 7 membered heterocyclic group Chemical group 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 5
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 5
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 5
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 5
- BNNMDMGPZUOOOE-UHFFFAOYSA-N 4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.CC1=CC=C(S(O)(=O)=O)C=C1 BNNMDMGPZUOOOE-UHFFFAOYSA-N 0.000 description 5
- 239000005711 Benzoic acid Substances 0.000 description 5
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 5
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 5
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 125000002877 alkyl aryl group Chemical group 0.000 description 5
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 5
- 229940092714 benzenesulfonic acid Drugs 0.000 description 5
- 235000010233 benzoic acid Nutrition 0.000 description 5
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 5
- 235000015165 citric acid Nutrition 0.000 description 5
- 239000001530 fumaric acid Substances 0.000 description 5
- 235000011087 fumaric acid Nutrition 0.000 description 5
- 150000007529 inorganic bases Chemical class 0.000 description 5
- 239000004310 lactic acid Substances 0.000 description 5
- 235000014655 lactic acid Nutrition 0.000 description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 5
- 239000011976 maleic acid Substances 0.000 description 5
- 239000001630 malic acid Substances 0.000 description 5
- 235000011090 malic acid Nutrition 0.000 description 5
- 229960002510 mandelic acid Drugs 0.000 description 5
- 229940098779 methanesulfonic acid Drugs 0.000 description 5
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 5
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 5
- 150000007524 organic acids Chemical class 0.000 description 5
- 235000005985 organic acids Nutrition 0.000 description 5
- 150000007530 organic bases Chemical class 0.000 description 5
- 235000006408 oxalic acid Nutrition 0.000 description 5
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 5
- 239000008194 pharmaceutical composition Substances 0.000 description 5
- 229960004889 salicylic acid Drugs 0.000 description 5
- 235000002906 tartaric acid Nutrition 0.000 description 5
- 239000011975 tartaric acid Substances 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- 125000005213 alkyl heteroaryl group Chemical group 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 125000003107 substituted aryl group Chemical group 0.000 description 3
- WZXCMMDJRYMKQT-UHFFFAOYSA-N 4-[3-[[4-bromo-3-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC(OC=2C=C(NC(=O)NC=3C=C(C(Br)=CC=3)C(F)(F)F)C=CC=2)=C1 WZXCMMDJRYMKQT-UHFFFAOYSA-N 0.000 description 2
- 125000006164 6-membered heteroaryl group Chemical group 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- RIUDVVSYVXYAOP-UHFFFAOYSA-N (3-tert-butylphenyl)urea Chemical compound CC(C)(C)C1=CC=CC(NC(N)=O)=C1 RIUDVVSYVXYAOP-UHFFFAOYSA-N 0.000 description 1
- BXBLUKHRPWBUJU-UHFFFAOYSA-N (5-tert-butyl-2-methoxyphenyl)urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(N)=O BXBLUKHRPWBUJU-UHFFFAOYSA-N 0.000 description 1
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 description 1
- KUJYWIMYUCLJRI-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-(1,3-dioxoisoindol-5-yl)oxyphenyl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=C(C(=O)NC2=O)C2=C1 KUJYWIMYUCLJRI-UHFFFAOYSA-N 0.000 description 1
- PZCQMBMLJHRIRJ-UHFFFAOYSA-N 4-[2-chloro-4-[[2-methoxy-5-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC(OC=2C(=CC(NC(=O)NC=3C(=CC=C(C=3)C(F)(F)F)OC)=CC=2)Cl)=C1 PZCQMBMLJHRIRJ-UHFFFAOYSA-N 0.000 description 1
- WMOAAZSEJDNDRZ-UHFFFAOYSA-N 4-[2-chloro-4-[[4-chloro-2-methoxy-5-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC(OC=2C(=CC(NC(=O)NC=3C(=CC(Cl)=C(C=3)C(F)(F)F)OC)=CC=2)Cl)=C1 WMOAAZSEJDNDRZ-UHFFFAOYSA-N 0.000 description 1
- JQRCJEFLYSNDOH-UHFFFAOYSA-N 4-[3-[[2-methoxy-5-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC(OC=2C=C(NC(=O)NC=3C(=CC=C(C=3)C(F)(F)F)OC)C=CC=2)=C1 JQRCJEFLYSNDOH-UHFFFAOYSA-N 0.000 description 1
- NMRPWERDAUJWLD-UHFFFAOYSA-N 4-[3-[[2-methoxy-5-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]pyridine-2-carboxamide Chemical compound COC1=CC=C(C(F)(F)F)C=C1NC(=O)NC1=CC=CC(OC=2C=C(N=CC=2)C(N)=O)=C1 NMRPWERDAUJWLD-UHFFFAOYSA-N 0.000 description 1
- KERKECQWQMFQPX-UHFFFAOYSA-N 4-[3-[[4-chloro-2-methoxy-5-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC(OC=2C=C(NC(=O)NC=3C(=CC(Cl)=C(C=3)C(F)(F)F)OC)C=CC=2)=C1 KERKECQWQMFQPX-UHFFFAOYSA-N 0.000 description 1
- RSDXTEAFHPMIAZ-UHFFFAOYSA-N 4-[3-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC(OC=2C=C(NC(=O)NC=3C=C(C(Cl)=CC=3)C(F)(F)F)C=CC=2)=C1 RSDXTEAFHPMIAZ-UHFFFAOYSA-N 0.000 description 1
- HRLTXHASHFPQAJ-UHFFFAOYSA-N 4-[3-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]pyridine-2-carboxamide Chemical compound C1=NC(C(=O)N)=CC(OC=2C=C(NC(=O)NC=3C=C(C(Cl)=CC=3)C(F)(F)F)C=CC=2)=C1 HRLTXHASHFPQAJ-UHFFFAOYSA-N 0.000 description 1
- GOAGFZRGKHLHRT-UHFFFAOYSA-N 4-[3-chloro-4-[[2-methoxy-5-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC(OC=2C=C(Cl)C(NC(=O)NC=3C(=CC=C(C=3)C(F)(F)F)OC)=CC=2)=C1 GOAGFZRGKHLHRT-UHFFFAOYSA-N 0.000 description 1
- SITFWSXSQYZWRX-UHFFFAOYSA-N 4-[3-chloro-4-[[4-chloro-2-methoxy-5-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC(OC=2C=C(Cl)C(NC(=O)NC=3C(=CC(Cl)=C(C=3)C(F)(F)F)OC)=CC=2)=C1 SITFWSXSQYZWRX-UHFFFAOYSA-N 0.000 description 1
- JNWMCRIBVQCVQU-UHFFFAOYSA-N 4-[4-[[2-methoxy-5-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC(OC=2C=CC(NC(=O)NC=3C(=CC=C(C=3)C(F)(F)F)OC)=CC=2)=C1 JNWMCRIBVQCVQU-UHFFFAOYSA-N 0.000 description 1
- QQZNUVIRTSPCLZ-UHFFFAOYSA-N 4-[4-[[2-methoxy-5-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]pyridine-2-carboxamide Chemical compound COC1=CC=C(C(F)(F)F)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC(C(N)=O)=C1 QQZNUVIRTSPCLZ-UHFFFAOYSA-N 0.000 description 1
- AMKGGWUQNQADDG-UHFFFAOYSA-N 4-[4-[[2-methoxy-5-(trifluoromethyl)phenyl]carbamoylamino]phenyl]sulfanyl-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC(SC=2C=CC(NC(=O)NC=3C(=CC=C(C=3)C(F)(F)F)OC)=CC=2)=C1 AMKGGWUQNQADDG-UHFFFAOYSA-N 0.000 description 1
- WWQRKFRUJIHXLV-UHFFFAOYSA-N 4-[4-[[4-bromo-3-(trifluoromethyl)phenyl]carbamoylamino]-2-chlorophenoxy]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC(OC=2C(=CC(NC(=O)NC=3C=C(C(Br)=CC=3)C(F)(F)F)=CC=2)Cl)=C1 WWQRKFRUJIHXLV-UHFFFAOYSA-N 0.000 description 1
- DHMDTRVWYXIDFX-UHFFFAOYSA-N 4-[4-[[4-bromo-3-(trifluoromethyl)phenyl]carbamoylamino]-3-chlorophenoxy]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC(OC=2C=C(Cl)C(NC(=O)NC=3C=C(C(Br)=CC=3)C(F)(F)F)=CC=2)=C1 DHMDTRVWYXIDFX-UHFFFAOYSA-N 0.000 description 1
- WINHEDROZCCEOE-UHFFFAOYSA-N 4-[4-[[4-bromo-3-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC(OC=2C=CC(NC(=O)NC=3C=C(C(Br)=CC=3)C(F)(F)F)=CC=2)=C1 WINHEDROZCCEOE-UHFFFAOYSA-N 0.000 description 1
- PAFWNASGEYHRSQ-UHFFFAOYSA-N 4-[4-[[4-chloro-2-methoxy-5-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC(OC=2C=CC(NC(=O)NC=3C(=CC(Cl)=C(C=3)C(F)(F)F)OC)=CC=2)=C1 PAFWNASGEYHRSQ-UHFFFAOYSA-N 0.000 description 1
- UAEWBZYTKIMYRQ-UHFFFAOYSA-N 4-[4-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]pyridine-2-carboxamide Chemical compound C1=NC(C(=O)N)=CC(OC=2C=CC(NC(=O)NC=3C=C(C(Cl)=CC=3)C(F)(F)F)=CC=2)=C1 UAEWBZYTKIMYRQ-UHFFFAOYSA-N 0.000 description 1
- MUMRZKBJQJIUDN-UHFFFAOYSA-N 5-[4-[(5-tert-butyl-2-methoxyphenyl)carbamoylamino]phenoxy]-2-methoxy-n-methylbenzamide Chemical compound C1=C(OC)C(C(=O)NC)=CC(OC=2C=CC(NC(=O)NC=3C(=CC=C(C=3)C(C)(C)C)OC)=CC=2)=C1 MUMRZKBJQJIUDN-UHFFFAOYSA-N 0.000 description 1
- MLDQJTXFUGDVEO-UHFFFAOYSA-N BAY-43-9006 Chemical compound C1=NC(C(=O)NC)=CC(OC=2C=CC(NC(=O)NC=3C=C(C(Cl)=CC=3)C(F)(F)F)=CC=2)=C1 MLDQJTXFUGDVEO-UHFFFAOYSA-N 0.000 description 1
- KGXSGWWPDAUETG-UHFFFAOYSA-N [2-methoxy-5-(trifluoromethyl)phenyl]urea Chemical compound COC1=CC=C(C(F)(F)F)C=C1NC(N)=O KGXSGWWPDAUETG-UHFFFAOYSA-N 0.000 description 1
- ZOQDVAHCMDZLSL-UHFFFAOYSA-N [4-bromo-3-(trifluoromethyl)phenyl]urea Chemical compound NC(=O)NC1=CC=C(Br)C(C(F)(F)F)=C1 ZOQDVAHCMDZLSL-UHFFFAOYSA-N 0.000 description 1
- LZKVIXJDSBJKDT-UHFFFAOYSA-N [4-chloro-2-methoxy-5-(trifluoromethyl)phenyl]urea Chemical compound COC1=CC(Cl)=C(C(F)(F)F)C=C1NC(N)=O LZKVIXJDSBJKDT-UHFFFAOYSA-N 0.000 description 1
- LJSGLEVVMDHAGH-UHFFFAOYSA-N [4-chloro-3-(trifluoromethyl)phenyl]urea Chemical compound NC(=O)NC1=CC=C(Cl)C(C(F)(F)F)=C1 LJSGLEVVMDHAGH-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11587799P | 1999-01-13 | 1999-01-13 | |
| US60/115,877 | 1999-01-13 | ||
| US25726699A | 1999-02-25 | 1999-02-25 | |
| US09/257,266 | 1999-02-25 | ||
| US42522899A | 1999-10-22 | 1999-10-22 | |
| US09/425,228 | 1999-10-22 | ||
| PCT/US2000/000648 WO2000042012A1 (en) | 1999-01-13 | 2000-01-12 | φ-CARBOXYARYL SUBSTITUTED DIPHENYL UREAS AS RAF KINASE INHIBITORS |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006190034A Division JP4472669B2 (ja) | 1999-01-13 | 2006-07-11 | Ｒａｆキナーゼ阻害剤としてジフェニル尿素誘導体 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003526613A JP2003526613A (ja) | 2003-09-09 |
| JP2003526613A5 true JP2003526613A5 (enExample) | 2006-01-05 |
| JP3845792B2 JP3845792B2 (ja) | 2006-11-15 |
Family
ID=27381740
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000593580A Expired - Lifetime JP3845792B2 (ja) | 1999-01-13 | 2000-01-12 | ＲＡＦキナーゼ阻害剤としてのω−カルボキシアリール置換ジフェニル尿素 |
| JP2006190034A Expired - Lifetime JP4472669B2 (ja) | 1999-01-13 | 2006-07-11 | Ｒａｆキナーゼ阻害剤としてジフェニル尿素誘導体 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006190034A Expired - Lifetime JP4472669B2 (ja) | 1999-01-13 | 2006-07-11 | Ｒａｆキナーゼ阻害剤としてジフェニル尿素誘導体 |
Country Status (40)
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8110587B2 (en) | 2002-02-11 | 2012-02-07 | Bayer Healthcare Llc | Aryl ureas as kinase inhibitors |
| PE20040522A1 (es) * | 2002-05-29 | 2004-09-28 | Novartis Ag | Derivados de diarilurea dependientes de la cinasa de proteina |
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| DE1049664T1 (de) * | 1997-12-22 | 2001-05-03 | Bayer Corp., Pittsburgh | Hemmung der raf-kinase unter verwendung von symmetrisch und unsymmetrisch substituierten harnstoffen |
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