JP2004517855A5 - - Google Patents
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- Publication number
- JP2004517855A5 JP2004517855A5 JP2002554676A JP2002554676A JP2004517855A5 JP 2004517855 A5 JP2004517855 A5 JP 2004517855A5 JP 2002554676 A JP2002554676 A JP 2002554676A JP 2002554676 A JP2002554676 A JP 2002554676A JP 2004517855 A5 JP2004517855 A5 JP 2004517855A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrimidin
- yloxy
- amide
- ethoxy
- phenyl
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 description 30
- 125000000217 alkyl group Chemical group 0.000 description 24
- -1 mono-substituted phenyl Chemical group 0.000 description 15
- 201000010099 disease Diseases 0.000 description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 11
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 10
- 125000003545 alkoxy group Chemical group 0.000 description 10
- 102000002045 Endothelin Human genes 0.000 description 9
- 108050009340 Endothelin Proteins 0.000 description 9
- ZUBDGKVDJUIMQQ-UBFCDGJISA-N endothelin-1 Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(O)=O)NC(=O)[C@H]1NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@@H](CC=2C=CC(O)=CC=2)NC(=O)[C@H](C(C)C)NC(=O)[C@H]2CSSC[C@@H](C(N[C@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N2)=O)NC(=O)[C@@H](CO)NC(=O)[C@H](N)CSSC1)C1=CNC=N1 ZUBDGKVDJUIMQQ-UBFCDGJISA-N 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 125000003282 alkyl amino group Chemical group 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- 125000001072 heteroaryl group Chemical group 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 239000008194 pharmaceutical composition Substances 0.000 description 6
- 0 **c1c(NS(N(*)*)(=O)=O)nc(*)nc1O* Chemical compound **c1c(NS(N(*)*)(=O)=O)nc(*)nc1O* 0.000 description 5
- 125000004414 alkyl thio group Chemical group 0.000 description 5
- SVEKJHBWJWHXKV-UHFFFAOYSA-N benzylsulfamic acid Chemical compound OS(=O)(=O)NCC1=CC=CC=C1 SVEKJHBWJWHXKV-UHFFFAOYSA-N 0.000 description 5
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- XOJVVFBFDXDTEG-UHFFFAOYSA-N pristane Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 description 4
- 206010002383 Angina Pectoris Diseases 0.000 description 3
- 208000024172 Cardiovascular disease Diseases 0.000 description 3
- 208000031226 Hyperlipidaemia Diseases 0.000 description 3
- 206010020772 Hypertension Diseases 0.000 description 3
- 208000019695 Migraine disease Diseases 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- 206010047163 Vasospasm Diseases 0.000 description 3
- 201000011510 cancer Diseases 0.000 description 3
- 208000028867 ischemia Diseases 0.000 description 3
- 206010027599 migraine Diseases 0.000 description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 230000002062 proliferating effect Effects 0.000 description 3
- AIOGYCKREZXJJZ-UHFFFAOYSA-N 4-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-5-(4-chlorophenyl)-6-[[methyl(pyridin-2-yl)sulfamoyl]amino]pyrimidine Chemical compound N=1C=NC(OCCOC=2N=CC(Br)=CN=2)=C(C=2C=CC(Cl)=CC=2)C=1NS(=O)(=O)N(C)C1=CC=CC=N1 AIOGYCKREZXJJZ-UHFFFAOYSA-N 0.000 description 2
- PIJUSICWAKBTEZ-UHFFFAOYSA-N 5-(4-bromophenyl)-6-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-n-(ethylsulfamoyl)pyrimidin-4-amine Chemical compound C=1C=C(Br)C=CC=1C=1C(NS(=O)(=O)NCC)=NC=NC=1OCCOC1=NC=C(Br)C=N1 PIJUSICWAKBTEZ-UHFFFAOYSA-N 0.000 description 2
- GADXZXTXFHEOKH-UHFFFAOYSA-N 5-(4-bromophenyl)-n-(ethylsulfamoyl)-6-[2-(5-methylsulfanylpyrimidin-2-yl)oxyethoxy]pyrimidin-4-amine Chemical compound C=1C=C(Br)C=CC=1C=1C(NS(=O)(=O)NCC)=NC=NC=1OCCOC1=NC=C(SC)C=N1 GADXZXTXFHEOKH-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- 208000027866 inflammatory disease Diseases 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- OUCYWJAACMAXQD-UHFFFAOYSA-N pyridin-2-ylcarbamic acid Chemical compound OC(=O)NC1=CC=CC=N1 OUCYWJAACMAXQD-UHFFFAOYSA-N 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- CDYRIYSNNRFTJE-UHFFFAOYSA-N 4-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-5-(4-chlorophenyl)-6-[[furan-2-yl(methyl)sulfamoyl]amino]pyrimidine Chemical compound N=1C=NC(OCCOC=2N=CC(Br)=CN=2)=C(C=2C=CC(Cl)=CC=2)C=1NS(=O)(=O)N(C)C1=CC=CO1 CDYRIYSNNRFTJE-UHFFFAOYSA-N 0.000 description 1
- WDQPEDYBKDHJLW-UHFFFAOYSA-N 4-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-5-(4-chlorophenyl)-6-[[methyl(pyridin-3-yl)sulfamoyl]amino]pyrimidine Chemical compound N=1C=NC(OCCOC=2N=CC(Br)=CN=2)=C(C=2C=CC(Cl)=CC=2)C=1NS(=O)(=O)N(C)C1=CC=CN=C1 WDQPEDYBKDHJLW-UHFFFAOYSA-N 0.000 description 1
- UDJIQNVFLWLRET-UHFFFAOYSA-N 4-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-5-(4-chlorophenyl)-6-[[methyl(pyridin-4-yl)sulfamoyl]amino]pyrimidine Chemical compound N=1C=NC(OCCOC=2N=CC(Br)=CN=2)=C(C=2C=CC(Cl)=CC=2)C=1NS(=O)(=O)N(C)C1=CC=NC=C1 UDJIQNVFLWLRET-UHFFFAOYSA-N 0.000 description 1
- DCNYMZHJYGMUAP-UHFFFAOYSA-N 4-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-5-(4-chlorophenyl)-6-[[methyl(thiophen-2-yl)sulfamoyl]amino]pyrimidine Chemical compound N=1C=NC(OCCOC=2N=CC(Br)=CN=2)=C(C=2C=CC(Cl)=CC=2)C=1NS(=O)(=O)N(C)C1=CC=CS1 DCNYMZHJYGMUAP-UHFFFAOYSA-N 0.000 description 1
- LGFUPYWNJPMKKF-UHFFFAOYSA-N 5-(4-bromophenyl)-4-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-6-[[furan-2-yl(methyl)sulfamoyl]amino]pyrimidine Chemical compound N=1C=NC(OCCOC=2N=CC(Br)=CN=2)=C(C=2C=CC(Br)=CC=2)C=1NS(=O)(=O)N(C)C1=CC=CO1 LGFUPYWNJPMKKF-UHFFFAOYSA-N 0.000 description 1
- HQTCWMOCUPICJI-UHFFFAOYSA-N 5-(4-bromophenyl)-4-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-6-[[methyl(pyridin-2-yl)sulfamoyl]amino]pyrimidine Chemical compound N=1C=NC(OCCOC=2N=CC(Br)=CN=2)=C(C=2C=CC(Br)=CC=2)C=1NS(=O)(=O)N(C)C1=CC=CC=N1 HQTCWMOCUPICJI-UHFFFAOYSA-N 0.000 description 1
- ISJQPCOMTBDAMT-UHFFFAOYSA-N 5-(4-bromophenyl)-4-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-6-[[methyl(pyridin-3-yl)sulfamoyl]amino]pyrimidine Chemical compound N=1C=NC(OCCOC=2N=CC(Br)=CN=2)=C(C=2C=CC(Br)=CC=2)C=1NS(=O)(=O)N(C)C1=CC=CN=C1 ISJQPCOMTBDAMT-UHFFFAOYSA-N 0.000 description 1
- OHDJBKMKVMFQIY-UHFFFAOYSA-N 5-(4-bromophenyl)-4-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-6-[[methyl(pyridin-4-yl)sulfamoyl]amino]pyrimidine Chemical compound N=1C=NC(OCCOC=2N=CC(Br)=CN=2)=C(C=2C=CC(Br)=CC=2)C=1NS(=O)(=O)N(C)C1=CC=NC=C1 OHDJBKMKVMFQIY-UHFFFAOYSA-N 0.000 description 1
- ZLDJCOJFGRLYDN-UHFFFAOYSA-N 5-(4-bromophenyl)-4-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-6-[[methyl(thiophen-2-yl)sulfamoyl]amino]pyrimidine Chemical compound N=1C=NC(OCCOC=2N=CC(Br)=CN=2)=C(C=2C=CC(Br)=CC=2)C=1NS(=O)(=O)N(C)C1=CC=CS1 ZLDJCOJFGRLYDN-UHFFFAOYSA-N 0.000 description 1
- GWOUVHUMXSOJQE-UHFFFAOYSA-N 5-(4-bromophenyl)-4-[2-(5-methoxypyrimidin-2-yl)oxyethoxy]-6-[[methyl(pyridin-2-yl)sulfamoyl]amino]pyrimidine Chemical compound N1=CC(OC)=CN=C1OCCOC1=NC=NC(NS(=O)(=O)N(C)C=2N=CC=CC=2)=C1C1=CC=C(Br)C=C1 GWOUVHUMXSOJQE-UHFFFAOYSA-N 0.000 description 1
- GRMNNBBUDDGUJW-UHFFFAOYSA-N 5-(4-bromophenyl)-4-[2-(5-methoxypyrimidin-2-yl)oxyethoxy]-6-[[methyl(thiophen-2-yl)sulfamoyl]amino]pyrimidine Chemical compound N1=CC(OC)=CN=C1OCCOC1=NC=NC(NS(=O)(=O)N(C)C=2SC=CC=2)=C1C1=CC=C(Br)C=C1 GRMNNBBUDDGUJW-UHFFFAOYSA-N 0.000 description 1
- SCCMBDIZRNGJIJ-UHFFFAOYSA-N 5-(4-bromophenyl)-4-[[furan-2-yl(methyl)sulfamoyl]amino]-6-[2-(5-methoxypyrimidin-2-yl)oxyethoxy]pyrimidine Chemical compound N1=CC(OC)=CN=C1OCCOC1=NC=NC(NS(=O)(=O)N(C)C=2OC=CC=2)=C1C1=CC=C(Br)C=C1 SCCMBDIZRNGJIJ-UHFFFAOYSA-N 0.000 description 1
- XYCFQJYVDREZPE-UHFFFAOYSA-N 5-(4-bromophenyl)-4-[[furan-2-yl(methyl)sulfamoyl]amino]-6-[2-(5-methylsulfanylpyrimidin-2-yl)oxyethoxy]pyrimidine Chemical compound N1=CC(SC)=CN=C1OCCOC1=NC=NC(NS(=O)(=O)N(C)C=2OC=CC=2)=C1C1=CC=C(Br)C=C1 XYCFQJYVDREZPE-UHFFFAOYSA-N 0.000 description 1
- HVSRHDAIPVEISZ-UHFFFAOYSA-N 5-(4-bromophenyl)-4-[[methyl(pyridin-2-yl)sulfamoyl]amino]-6-[2-(5-methylsulfanylpyrimidin-2-yl)oxyethoxy]pyrimidine Chemical compound N1=CC(SC)=CN=C1OCCOC1=NC=NC(NS(=O)(=O)N(C)C=2N=CC=CC=2)=C1C1=CC=C(Br)C=C1 HVSRHDAIPVEISZ-UHFFFAOYSA-N 0.000 description 1
- WTEIMXRBTNAONF-UHFFFAOYSA-N 5-(4-bromophenyl)-4-[[methyl(pyridin-3-yl)sulfamoyl]amino]-6-[2-(5-methylsulfanylpyrimidin-2-yl)oxyethoxy]pyrimidine Chemical compound N1=CC(SC)=CN=C1OCCOC1=NC=NC(NS(=O)(=O)N(C)C=2C=NC=CC=2)=C1C1=CC=C(Br)C=C1 WTEIMXRBTNAONF-UHFFFAOYSA-N 0.000 description 1
- FAYAMAAFPRXGJT-UHFFFAOYSA-N 5-(4-bromophenyl)-6-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-n-(butylsulfamoyl)pyrimidin-4-amine Chemical compound C=1C=C(Br)C=CC=1C=1C(NS(=O)(=O)NCCCC)=NC=NC=1OCCOC1=NC=C(Br)C=N1 FAYAMAAFPRXGJT-UHFFFAOYSA-N 0.000 description 1
- FWDCVKXLJHFYKJ-UHFFFAOYSA-N 5-(4-bromophenyl)-6-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-n-(cyclopentylsulfamoyl)pyrimidin-4-amine Chemical compound C1=CC(Br)=CC=C1C(C(=NC=N1)OCCOC=2N=CC(Br)=CN=2)=C1NS(=O)(=O)NC1CCCC1 FWDCVKXLJHFYKJ-UHFFFAOYSA-N 0.000 description 1
- LKOLDYBWXOYQMQ-UHFFFAOYSA-N 5-(4-bromophenyl)-6-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-n-(cyclopropylsulfamoyl)pyrimidin-4-amine Chemical compound C1=CC(Br)=CC=C1C(C(=NC=N1)OCCOC=2N=CC(Br)=CN=2)=C1NS(=O)(=O)NC1CC1 LKOLDYBWXOYQMQ-UHFFFAOYSA-N 0.000 description 1
- BRSITRUZDCGGKH-UHFFFAOYSA-N 5-(4-bromophenyl)-6-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-n-(methylsulfamoyl)pyrimidin-4-amine Chemical compound C=1C=C(Br)C=CC=1C=1C(NS(=O)(=O)NC)=NC=NC=1OCCOC1=NC=C(Br)C=N1 BRSITRUZDCGGKH-UHFFFAOYSA-N 0.000 description 1
- TYCTWXNHVWBKAM-UHFFFAOYSA-N 5-(4-bromophenyl)-6-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-n-[(4-fluorophenyl)methylsulfamoyl]pyrimidin-4-amine Chemical compound C1=CC(F)=CC=C1CNS(=O)(=O)NC1=NC=NC(OCCOC=2N=CC(Br)=CN=2)=C1C1=CC=C(Br)C=C1 TYCTWXNHVWBKAM-UHFFFAOYSA-N 0.000 description 1
- JBMDWSYCKXKSIX-UHFFFAOYSA-N 5-(4-bromophenyl)-6-[2-(5-methoxypyrimidin-2-yl)oxyethoxy]-n-(methylsulfamoyl)pyrimidin-4-amine Chemical compound C=1C=C(Br)C=CC=1C=1C(NS(=O)(=O)NC)=NC=NC=1OCCOC1=NC=C(OC)C=N1 JBMDWSYCKXKSIX-UHFFFAOYSA-N 0.000 description 1
- IDRSXRPOEONBKT-UHFFFAOYSA-N 5-(4-bromophenyl)-6-[2-(5-methoxypyrimidin-2-yl)oxyethoxy]-n-(propylsulfamoyl)pyrimidin-4-amine Chemical compound C=1C=C(Br)C=CC=1C=1C(NS(=O)(=O)NCCC)=NC=NC=1OCCOC1=NC=C(OC)C=N1 IDRSXRPOEONBKT-UHFFFAOYSA-N 0.000 description 1
- LDYLIYKANSSERK-UHFFFAOYSA-N 5-(4-bromophenyl)-6-[2-(5-methylsulfanylpyrimidin-2-yl)oxyethoxy]-n-(propylsulfamoyl)pyrimidin-4-amine Chemical compound C=1C=C(Br)C=CC=1C=1C(NS(=O)(=O)NCCC)=NC=NC=1OCCOC1=NC=C(SC)C=N1 LDYLIYKANSSERK-UHFFFAOYSA-N 0.000 description 1
- IYYXUAMBMQMWBL-UHFFFAOYSA-N 5-(4-bromophenyl)-6-[2-(5-methylsulfanylpyrimidin-2-yl)oxyethoxy]pyrimidin-4-amine Chemical compound N1=CC(SC)=CN=C1OCCOC1=NC=NC(N)=C1C1=CC=C(Br)C=C1 IYYXUAMBMQMWBL-UHFFFAOYSA-N 0.000 description 1
- ZWTAXWXITAZUQP-UHFFFAOYSA-N 5-(4-bromophenyl)-n-(butylsulfamoyl)-6-[2-(5-methoxypyrimidin-2-yl)oxyethoxy]pyrimidin-4-amine Chemical compound C=1C=C(Br)C=CC=1C=1C(NS(=O)(=O)NCCCC)=NC=NC=1OCCOC1=NC=C(OC)C=N1 ZWTAXWXITAZUQP-UHFFFAOYSA-N 0.000 description 1
- XYKNJZNFEGDDIP-UHFFFAOYSA-N 5-(4-bromophenyl)-n-(butylsulfamoyl)-6-[2-(5-methylsulfanylpyrimidin-2-yl)oxyethoxy]pyrimidin-4-amine Chemical compound C=1C=C(Br)C=CC=1C=1C(NS(=O)(=O)NCCCC)=NC=NC=1OCCOC1=NC=C(SC)C=N1 XYKNJZNFEGDDIP-UHFFFAOYSA-N 0.000 description 1
- ASLHUBXUHZDUMZ-UHFFFAOYSA-N 5-(4-bromophenyl)-n-(cyclopentylsulfamoyl)-6-[2-(5-methoxypyrimidin-2-yl)oxyethoxy]pyrimidin-4-amine Chemical compound N1=CC(OC)=CN=C1OCCOC1=NC=NC(NS(=O)(=O)NC2CCCC2)=C1C1=CC=C(Br)C=C1 ASLHUBXUHZDUMZ-UHFFFAOYSA-N 0.000 description 1
- PZGKTNMDYCZDGX-UHFFFAOYSA-N 5-(4-bromophenyl)-n-(cyclopropylsulfamoyl)-6-[2-(5-methoxypyrimidin-2-yl)oxyethoxy]pyrimidin-4-amine Chemical compound N1=CC(OC)=CN=C1OCCOC1=NC=NC(NS(=O)(=O)NC2CC2)=C1C1=CC=C(Br)C=C1 PZGKTNMDYCZDGX-UHFFFAOYSA-N 0.000 description 1
- HLAWSLTYQNVRNY-UHFFFAOYSA-N 5-(4-bromophenyl)-n-(ethylsulfamoyl)-6-[2-(5-methoxypyrimidin-2-yl)oxyethoxy]pyrimidin-4-amine Chemical compound C=1C=C(Br)C=CC=1C=1C(NS(=O)(=O)NCC)=NC=NC=1OCCOC1=NC=C(OC)C=N1 HLAWSLTYQNVRNY-UHFFFAOYSA-N 0.000 description 1
- KSGHGYRWLMKYNA-UHFFFAOYSA-N 5-(4-bromophenyl)-n-(methylsulfamoyl)-6-[2-(5-methylsulfanylpyrimidin-2-yl)oxyethoxy]pyrimidin-4-amine Chemical compound C=1C=C(Br)C=CC=1C=1C(NS(=O)(=O)NC)=NC=NC=1OCCOC1=NC=C(SC)C=N1 KSGHGYRWLMKYNA-UHFFFAOYSA-N 0.000 description 1
- XEAZERSGWNZAOI-UHFFFAOYSA-N 5-(4-bromophenyl)-n-[(4-fluorophenyl)methylsulfamoyl]-6-[2-(5-methoxypyrimidin-2-yl)oxyethoxy]pyrimidin-4-amine Chemical compound N1=CC(OC)=CN=C1OCCOC1=NC=NC(NS(=O)(=O)NCC=2C=CC(F)=CC=2)=C1C1=CC=C(Br)C=C1 XEAZERSGWNZAOI-UHFFFAOYSA-N 0.000 description 1
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- XZUKUAMPTAUGHG-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-[2-(5-methoxypyrimidin-2-yl)oxyethoxy]-6-[[methyl(pyridin-2-yl)sulfamoyl]amino]pyrimidine Chemical compound N1=CC(OC)=CN=C1OCCOC1=NC=NC(NS(=O)(=O)N(C)C=2N=CC=CC=2)=C1C1=CC=C(Cl)C=C1 XZUKUAMPTAUGHG-UHFFFAOYSA-N 0.000 description 1
- PJAURNROAJAHTL-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-[2-(5-methoxypyrimidin-2-yl)oxyethoxy]-6-[[methyl(pyridin-3-yl)sulfamoyl]amino]pyrimidine Chemical compound N1=CC(OC)=CN=C1OCCOC1=NC=NC(NS(=O)(=O)N(C)C=2C=NC=CC=2)=C1C1=CC=C(Cl)C=C1 PJAURNROAJAHTL-UHFFFAOYSA-N 0.000 description 1
- OJXQHXIZRWTCPD-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-[2-(5-methoxypyrimidin-2-yl)oxyethoxy]-6-[[methyl(pyridin-4-yl)sulfamoyl]amino]pyrimidine Chemical compound N1=CC(OC)=CN=C1OCCOC1=NC=NC(NS(=O)(=O)N(C)C=2C=CN=CC=2)=C1C1=CC=C(Cl)C=C1 OJXQHXIZRWTCPD-UHFFFAOYSA-N 0.000 description 1
- XRXGMFHYOVYOAC-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-[2-(5-methylsulfanylpyrimidin-2-yl)oxyethoxy]-6-[[methyl(thiophen-2-yl)sulfamoyl]amino]pyrimidine Chemical compound N1=CC(SC)=CN=C1OCCOC1=NC=NC(NS(=O)(=O)N(C)C=2SC=CC=2)=C1C1=CC=C(Cl)C=C1 XRXGMFHYOVYOAC-UHFFFAOYSA-N 0.000 description 1
- LUXYTYCSCLVIRP-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-[[furan-2-yl(methyl)sulfamoyl]amino]-6-[2-(5-methylsulfanylpyrimidin-2-yl)oxyethoxy]pyrimidine Chemical compound N1=CC(SC)=CN=C1OCCOC1=NC=NC(NS(=O)(=O)N(C)C=2OC=CC=2)=C1C1=CC=C(Cl)C=C1 LUXYTYCSCLVIRP-UHFFFAOYSA-N 0.000 description 1
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| ATE466581T1 (de) | 2001-12-07 | 2010-05-15 | Vertex Pharma | Verbindungen auf pyrimidin-basis als gsk-3-hemmer |
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| JP5230416B2 (ja) | 2005-07-29 | 2013-07-10 | テイボテク・フアーマシユーチカルズ | Ｃ型肝炎ウイルスの大員環状阻害剤 |
| ES2373685T3 (es) | 2005-07-29 | 2012-02-07 | Tibotec Pharmaceuticals | Inhibidores macrocíclicos del virus de la hepatitis c. |
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| MX2008002731A (es) | 2005-09-01 | 2008-03-26 | Hoffmann La Roche | Diaminopirimidinas como moduladores de p2x3 y p3x2/3. |
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| AR062501A1 (es) * | 2006-08-29 | 2008-11-12 | Actelion Pharmaceuticals Ltd | Composiciones terapeuticas |
| US7983024B2 (en) | 2007-04-24 | 2011-07-19 | Littelfuse, Inc. | Fuse card system for automotive circuit protection |
| MX2010001837A (es) | 2007-08-17 | 2010-03-10 | Actelion Pharmaceuticals Ltd | Derivados de 4-pirimidinasulfamida. |
| US20100222347A1 (en) | 2007-09-27 | 2010-09-02 | Kowa Company, Ltd. | Prophylactic and/or therapeutic agent for anemia, comprising tetrahydroquinoline compound as active ingredient |
| PL2254570T3 (pl) * | 2008-02-20 | 2014-05-30 | Actelion Pharmaceuticals Ltd | Połączenie zawierające paklitaksel do leczenia raka jajnika |
| JP5465720B2 (ja) * | 2008-07-08 | 2014-04-09 | インサイト・コーポレイション | インドールアミン２，３−ジオキシゲナーゼの阻害剤としての１，２，５−オキサジアゾール |
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