CA2476281A1

CA2476281A1 - Pyrimidine compounds

Pyrimidine compounds Download PDF

Info

Publication number: CA2476281A1
Authority: CA; Canada
Prior art keywords: amino; phenyl; methyl; alkyl; pyrimidin
Prior art date: 2002-02-08
Legal status : Abandoned

Application number

CA002476281A

Other languages

English (en)

French (fr)

Inventor

Mui Cheung

Kristen Elizabeth Nailor

Douglas Mccord Sammond

James Marvin Veal

Current Assignee

SmithKline Beecham Corp

Original Assignee

Individual

Priority date

2002-02-08

Filing date

2003-02-07

Publication date

2003-08-14

2003-02-07 Application filed by Individual filed Critical Individual

2003-08-14 Publication of CA2476281A1 publication Critical patent/CA2476281A1/en

Status Abandoned legal-status Critical Current

Links

150000003230 pyrimidines Chemical class 0.000 title abstract description 7
238000000034 method Methods 0.000 claims abstract description 55
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 46
101000753291 Homo sapiens Angiopoietin-1 receptor Proteins 0.000 claims abstract description 36
102100022014 Angiopoietin-1 receptor Human genes 0.000 claims abstract description 35
238000011282 treatment Methods 0.000 claims abstract description 30
229940091171 VEGFR-2 tyrosine kinase inhibitor Drugs 0.000 claims abstract description 5
150000001875 compounds Chemical class 0.000 claims description 150
125000000217 alkyl group Chemical group 0.000 claims description 125
-1 aralkoxy Chemical group 0.000 claims description 124
239000001257 hydrogen Substances 0.000 claims description 121
229910052739 hydrogen Inorganic materials 0.000 claims description 121
150000002431 hydrogen Chemical group 0.000 claims description 113
125000000753 cycloalkyl group Chemical group 0.000 claims description 92
125000000623 heterocyclic group Chemical group 0.000 claims description 82
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 77
125000003118 aryl group Chemical group 0.000 claims description 75
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 74
125000003545 alkoxy group Chemical group 0.000 claims description 73
150000003839 salts Chemical class 0.000 claims description 70
125000001072 heteroaryl group Chemical group 0.000 claims description 59
239000012453 solvate Substances 0.000 claims description 57
125000004104 aryloxy group Chemical group 0.000 claims description 49
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 48
230000000694 effects Effects 0.000 claims description 38
125000001188 haloalkyl group Chemical group 0.000 claims description 37
102100033177 Vascular endothelial growth factor receptor 2 Human genes 0.000 claims description 36
229910052736 halogen Inorganic materials 0.000 claims description 36
150000002367 halogens Chemical group 0.000 claims description 35
125000003710 aryl alkyl group Chemical group 0.000 claims description 31
108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 claims description 30
125000004438 haloalkoxy group Chemical group 0.000 claims description 30
206010028980 Neoplasm Diseases 0.000 claims description 29
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 28
BJHCYTJNPVGSBZ-YXSASFKJSA-N 1-[4-[6-amino-5-[(Z)-methoxyiminomethyl]pyrimidin-4-yl]oxy-2-chlorophenyl]-3-ethylurea Chemical compound CCNC(=O)Nc1ccc(Oc2ncnc(N)c2\C=N/OC)cc1Cl BJHCYTJNPVGSBZ-YXSASFKJSA-N 0.000 claims description 26
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 26
125000003282 alkyl amino group Chemical group 0.000 claims description 26
239000008194 pharmaceutical composition Substances 0.000 claims description 26
241000124008 Mammalia Species 0.000 claims description 25
230000033115 angiogenesis Effects 0.000 claims description 25
201000011510 cancer Diseases 0.000 claims description 25
125000001769 aryl amino group Chemical group 0.000 claims description 23
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 19
239000003795 chemical substances by application Substances 0.000 claims description 18
125000004093 cyano group Chemical group *C#N 0.000 claims description 17
239000004202 carbamide Substances 0.000 claims description 16
239000003814 drug Substances 0.000 claims description 16
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 16
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 15
102000009465 Growth Factor Receptors Human genes 0.000 claims description 15
108010009202 Growth Factor Receptors Proteins 0.000 claims description 15
239000000460 chlorine Chemical group 0.000 claims description 15
229910052801 chlorine Inorganic materials 0.000 claims description 15
125000001691 aryl alkyl amino group Chemical group 0.000 claims description 14
238000002360 preparation method Methods 0.000 claims description 13
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 11
108091008605 VEGF receptors Proteins 0.000 claims description 10
125000001475 halogen functional group Chemical group 0.000 claims description 10
230000001404 mediated effect Effects 0.000 claims description 10
239000002246 antineoplastic agent Substances 0.000 claims description 9
125000004966 cyanoalkyl group Chemical group 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 9
229910052760 oxygen Inorganic materials 0.000 claims description 9
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 9
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
241001024304 Mino Species 0.000 claims description 7
238000011319 anticancer therapy Methods 0.000 claims description 7
229940034982 antineoplastic agent Drugs 0.000 claims description 7
102000001301 EGF receptor Human genes 0.000 claims description 6
108060006698 EGF receptor Proteins 0.000 claims description 6
101000851007 Homo sapiens Vascular endothelial growth factor receptor 2 Proteins 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
239000003085 diluting agent Substances 0.000 claims description 6
239000003937 drug carrier Substances 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
239000000546 pharmaceutical excipient Substances 0.000 claims description 6
238000002560 therapeutic procedure Methods 0.000 claims description 6
HTDWNYJVQSYOBM-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-[4-[methyl-[2-(4-sulfamoylanilino)pyrimidin-4-yl]amino]phenyl]urea Chemical compound C=1C=NC(NC=2C=CC(=CC=2)S(N)(=O)=O)=NC=1N(C)C(C=C1)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 HTDWNYJVQSYOBM-UHFFFAOYSA-N 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
SNRUTMWCDZHKKM-UHFFFAOYSA-N 1-[4-[methyl-[2-(3-sulfamoylanilino)pyrimidin-4-yl]amino]phenyl]-3-[4-(trifluoromethoxy)phenyl]urea Chemical compound C=1C=NC(NC=2C=C(C=CC=2)S(N)(=O)=O)=NC=1N(C)C(C=C1)=CC=C1NC(=O)NC1=CC=C(OC(F)(F)F)C=C1 SNRUTMWCDZHKKM-UHFFFAOYSA-N 0.000 claims description 4
DTUXNRWKSVIUOF-UHFFFAOYSA-N 1-[4-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]-3-propylurea Chemical compound C1=CC(NC(=O)NCCC)=CC=C1N(C)C1=CC=NC(NC=2C=C(CS(C)(=O)=O)C=CC=2)=N1 DTUXNRWKSVIUOF-UHFFFAOYSA-N 0.000 claims description 4
108091008606 PDGF receptors Proteins 0.000 claims description 4
102000011653 Platelet-Derived Growth Factor Receptors Human genes 0.000 claims description 4
102000009484 Vascular Endothelial Growth Factor Receptors Human genes 0.000 claims description 4
102100033178 Vascular endothelial growth factor receptor 1 Human genes 0.000 claims description 4
102100033179 Vascular endothelial growth factor receptor 3 Human genes 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
WQAKQQBRJGAFLY-UHFFFAOYSA-N 1-(3-fluorophenyl)-3-[4-[methyl-[2-(3-sulfamoylanilino)pyrimidin-4-yl]amino]phenyl]urea Chemical compound C=1C=NC(NC=2C=C(C=CC=2)S(N)(=O)=O)=NC=1N(C)C(C=C1)=CC=C1NC(=O)NC1=CC=CC(F)=C1 WQAKQQBRJGAFLY-UHFFFAOYSA-N 0.000 claims description 3
ISIGZINVBPDMCU-UHFFFAOYSA-N 1-(3-fluorophenyl)-3-[4-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]urea;hydrochloride Chemical compound Cl.C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1)=CC=C1NC(=O)NC1=CC=CC(F)=C1 ISIGZINVBPDMCU-UHFFFAOYSA-N 0.000 claims description 3
XLMYZJFXAGIZQZ-UHFFFAOYSA-N 1-[2-fluoro-5-(trifluoromethyl)phenyl]-3-[3-[methyl-[2-(3-sulfamoylanilino)pyrimidin-4-yl]amino]phenyl]urea Chemical compound C=1C=NC(NC=2C=C(C=CC=2)S(N)(=O)=O)=NC=1N(C)C(C=1)=CC=CC=1NC(=O)NC1=CC(C(F)(F)F)=CC=C1F XLMYZJFXAGIZQZ-UHFFFAOYSA-N 0.000 claims description 3
YBLPVRFSDNONDP-UHFFFAOYSA-N 1-[4-[[2-(5-ethylsulfonyl-2-methoxyanilino)pyrimidin-4-yl]-methylamino]phenyl]-3-(3-fluorophenyl)urea Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2N=C(C=CN=2)N(C)C=2C=CC(NC(=O)NC=3C=C(F)C=CC=3)=CC=2)=C1 YBLPVRFSDNONDP-UHFFFAOYSA-N 0.000 claims description 3
WWOTVVREYCGACQ-UHFFFAOYSA-N 1-[4-[methyl-[2-(3-sulfamoylanilino)pyrimidin-4-yl]amino]phenyl]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound C=1C=NC(NC=2C=C(C=CC=2)S(N)(=O)=O)=NC=1N(C)C(C=C1)=CC=C1NC(=O)NC1=CC=C(C(F)(F)F)C=C1 WWOTVVREYCGACQ-UHFFFAOYSA-N 0.000 claims description 3
HJEZSTRTPQMQRB-UHFFFAOYSA-N 1-[4-[methyl-[2-(3-sulfamoylanilino)pyrimidin-4-yl]amino]phenyl]-3-phenylurea Chemical compound C=1C=NC(NC=2C=C(C=CC=2)S(N)(=O)=O)=NC=1N(C)C(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1 HJEZSTRTPQMQRB-UHFFFAOYSA-N 0.000 claims description 3
RJINUSFBYKYLTQ-UHFFFAOYSA-N 1-[4-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]-3-phenylthiourea Chemical compound C=1C=NC(NC=2C=C(CS(C)(=O)=O)C=CC=2)=NC=1N(C)C(C=C1)=CC=C1NC(=S)NC1=CC=CC=C1 RJINUSFBYKYLTQ-UHFFFAOYSA-N 0.000 claims description 3
RZBKPAOZLPAYEX-UHFFFAOYSA-N 1-methyl-1-[4-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]-3-phenylurea Chemical compound C=1C=C(N(C)C=2N=C(NC=3C=C(CS(C)(=O)=O)C=CC=3)N=CC=2)C=CC=1N(C)C(=O)NC1=CC=CC=C1 RZBKPAOZLPAYEX-UHFFFAOYSA-N 0.000 claims description 3
101000851018 Homo sapiens Vascular endothelial growth factor receptor 1 Proteins 0.000 claims description 3
101000851030 Homo sapiens Vascular endothelial growth factor receptor 3 Proteins 0.000 claims description 3
VYWQTJWGWLKBQA-UHFFFAOYSA-N [amino(hydroxy)methylidene]azanium;chloride Chemical compound Cl.NC(N)=O VYWQTJWGWLKBQA-UHFFFAOYSA-N 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 3
JLHIIIXVHUQRSA-UHFFFAOYSA-N phenyl n-[4-[methyl-[2-(4-methyl-3-sulfamoylanilino)pyrimidin-4-yl]amino]phenyl]carbamate Chemical compound C=1C=NC(NC=2C=C(C(C)=CC=2)S(N)(=O)=O)=NC=1N(C)C(C=C1)=CC=C1NC(=O)OC1=CC=CC=C1 JLHIIIXVHUQRSA-UHFFFAOYSA-N 0.000 claims description 3
HEYFWBNHOLNEAS-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-[3-[methyl-[2-(3-sulfamoylanilino)pyrimidin-4-yl]amino]phenyl]urea Chemical compound C=1C=NC(NC=2C=C(C=CC=2)S(N)(=O)=O)=NC=1N(C)C(C=1)=CC=CC=1NC(=O)NC1=CC=CC(Cl)=C1 HEYFWBNHOLNEAS-UHFFFAOYSA-N 0.000 claims description 2
USCPNRWCYGQBGN-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-[4-[[2-(5-ethylsulfonyl-2-methoxyanilino)pyrimidin-4-yl]-methylamino]phenyl]urea Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2N=C(C=CN=2)N(C)C=2C=CC(NC(=O)NC=3C=C(Cl)C=CC=3)=CC=2)=C1 USCPNRWCYGQBGN-UHFFFAOYSA-N 0.000 claims description 2
FBJSJFFPULLXSB-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-[4-[methyl-[2-(3-sulfamoylanilino)pyrimidin-4-yl]amino]phenyl]urea Chemical compound C=1C=NC(NC=2C=C(C=CC=2)S(N)(=O)=O)=NC=1N(C)C(C=C1)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 FBJSJFFPULLXSB-UHFFFAOYSA-N 0.000 claims description 2
WEFUYPPGCWFHOF-UHFFFAOYSA-N 1-(3-ethylphenyl)-3-[4-[methyl-[2-(4-sulfamoylanilino)pyrimidin-4-yl]amino]phenyl]urea Chemical compound CCC1=CC=CC(NC(=O)NC=2C=CC(=CC=2)N(C)C=2N=C(NC=3C=CC(=CC=3)S(N)(=O)=O)N=CC=2)=C1 WEFUYPPGCWFHOF-UHFFFAOYSA-N 0.000 claims description 2
AQUAEPAQYKSAME-UHFFFAOYSA-N 1-(3-fluorophenyl)-3-[3-[methyl-[2-(3-sulfamoylanilino)pyrimidin-4-yl]amino]phenyl]urea Chemical compound C=1C=NC(NC=2C=C(C=CC=2)S(N)(=O)=O)=NC=1N(C)C(C=1)=CC=CC=1NC(=O)NC1=CC=CC(F)=C1 AQUAEPAQYKSAME-UHFFFAOYSA-N 0.000 claims description 2
COHPSKLOBDZSLF-UHFFFAOYSA-N 1-(3-fluorophenyl)-3-[4-[methyl-[2-(4-sulfamoylanilino)pyrimidin-4-yl]amino]phenyl]urea Chemical compound C=1C=NC(NC=2C=CC(=CC=2)S(N)(=O)=O)=NC=1N(C)C(C=C1)=CC=C1NC(=O)NC1=CC=CC(F)=C1 COHPSKLOBDZSLF-UHFFFAOYSA-N 0.000 claims description 2
UIIXIQWTXSGBOP-UHFFFAOYSA-N 1-(4-fluorophenyl)-3-[4-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]urea Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1)=CC=C1NC(=O)NC1=CC=C(F)C=C1 UIIXIQWTXSGBOP-UHFFFAOYSA-N 0.000 claims description 2
RREMTKSPGOIRHQ-UHFFFAOYSA-N 1-[2-(dimethylamino)ethyl]-3-[4-[methyl-[2-[3-(2-methylsulfonylethyl)anilino]pyrimidin-4-yl]amino]phenyl]urea Chemical compound C1=CC(NC(=O)NCCN(C)C)=CC=C1N(C)C1=CC=NC(NC=2C=C(CCS(C)(=O)=O)C=CC=2)=N1 RREMTKSPGOIRHQ-UHFFFAOYSA-N 0.000 claims description 2
PPTQWMQTXBVAHT-UHFFFAOYSA-N 1-[2-fluoro-5-(trifluoromethyl)phenyl]-3-[4-[methyl-[2-(3-sulfamoylanilino)pyrimidin-4-yl]amino]phenyl]urea Chemical compound C=1C=NC(NC=2C=C(C=CC=2)S(N)(=O)=O)=NC=1N(C)C(C=C1)=CC=C1NC(=O)NC1=CC(C(F)(F)F)=CC=C1F PPTQWMQTXBVAHT-UHFFFAOYSA-N 0.000 claims description 2
YJFKREHADGLMHG-UHFFFAOYSA-N 1-[2-fluoro-5-(trifluoromethyl)phenyl]-3-[4-[methyl-[2-(4-sulfamoylanilino)pyrimidin-4-yl]amino]phenyl]urea Chemical compound C=1C=NC(NC=2C=CC(=CC=2)S(N)(=O)=O)=NC=1N(C)C(C=C1)=CC=C1NC(=O)NC1=CC(C(F)(F)F)=CC=C1F YJFKREHADGLMHG-UHFFFAOYSA-N 0.000 claims description 2
RYIZQWVKFLSVHM-UHFFFAOYSA-N 1-[4-[[2-(5-ethylsulfonyl-2-methoxyanilino)pyrimidin-4-yl]-methylamino]phenyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2N=C(C=CN=2)N(C)C=2C=CC(NC(=O)NC=3C(=CC=C(C=3)C(F)(F)F)F)=CC=2)=C1 RYIZQWVKFLSVHM-UHFFFAOYSA-N 0.000 claims description 2
GPYWESCRKLXARA-UHFFFAOYSA-N 1-[4-[methyl-[2-(4-sulfamoylanilino)pyrimidin-4-yl]amino]phenyl]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound C=1C=NC(NC=2C=CC(=CC=2)S(N)(=O)=O)=NC=1N(C)C(C=C1)=CC=C1NC(=O)NC1=CC=C(C(F)(F)F)C=C1 GPYWESCRKLXARA-UHFFFAOYSA-N 0.000 claims description 2
DQXBQPHEQRETIN-UHFFFAOYSA-N 1-[4-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]-3-(2-phenylethyl)urea Chemical compound C=1C=NC(NC=2C=C(CS(C)(=O)=O)C=CC=2)=NC=1N(C)C(C=C1)=CC=C1NC(=O)NCCC1=CC=CC=C1 DQXBQPHEQRETIN-UHFFFAOYSA-N 0.000 claims description 2
ZMDSDIMLVJXMJA-UHFFFAOYSA-N 1-[4-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]-3-[4-(trifluoromethoxy)phenyl]urea Chemical compound C=1C=NC(NC=2C=C(CS(C)(=O)=O)C=CC=2)=NC=1N(C)C(C=C1)=CC=C1NC(=O)NC1=CC=C(OC(F)(F)F)C=C1 ZMDSDIMLVJXMJA-UHFFFAOYSA-N 0.000 claims description 2
GDFXLACGLHMCTE-UHFFFAOYSA-N 1-[4-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]-3-propan-2-ylurea Chemical compound C1=CC(NC(=O)NC(C)C)=CC=C1N(C)C1=CC=NC(NC=2C=C(CS(C)(=O)=O)C=CC=2)=N1 GDFXLACGLHMCTE-UHFFFAOYSA-N 0.000 claims description 2
LVGQTXJDZKXBOC-UHFFFAOYSA-N 1-[4-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]-3-(4-phenylmethoxyphenyl)urea Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1)=CC=C1NC(=O)NC(C=C1)=CC=C1OCC1=CC=CC=C1 LVGQTXJDZKXBOC-UHFFFAOYSA-N 0.000 claims description 2
WUUXQSKAAWHECK-UHFFFAOYSA-N 1-[4-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]-3-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]urea Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1)=CC=C1NC(=O)NC(C=C1)=CC=C1CN1CCN(C)CC1 WUUXQSKAAWHECK-UHFFFAOYSA-N 0.000 claims description 2
HQILAAKXJCORFA-UHFFFAOYSA-N 1-cyclohexyl-3-[4-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]urea Chemical compound C=1C=NC(NC=2C=C(CS(C)(=O)=O)C=CC=2)=NC=1N(C)C(C=C1)=CC=C1NC(=O)NC1CCCCC1 HQILAAKXJCORFA-UHFFFAOYSA-N 0.000 claims description 2
QCXCNKJISLRDOZ-UHFFFAOYSA-N 1-ethyl-3-[4-[methyl-[2-[4-[2-(methylsulfamoyl)ethyl]anilino]pyrimidin-4-yl]amino]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1N(C)C1=CC=NC(NC=2C=CC(CCS(=O)(=O)NC)=CC=2)=N1 QCXCNKJISLRDOZ-UHFFFAOYSA-N 0.000 claims description 2
WTTQMMJLQSHYGL-UHFFFAOYSA-N 2-[4-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]-1-phenylguanidine Chemical compound C=1C=NC(NC=2C=C(CS(C)(=O)=O)C=CC=2)=NC=1N(C)C(C=C1)=CC=C1N=C(N)NC1=CC=CC=C1 WTTQMMJLQSHYGL-UHFFFAOYSA-N 0.000 claims description 2
ROIHUUVUCIGOLZ-UHFFFAOYSA-N n-[4-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]-1-phenylmethanesulfonamide Chemical compound C=1C=NC(NC=2C=C(CS(C)(=O)=O)C=CC=2)=NC=1N(C)C(C=C1)=CC=C1NS(=O)(=O)CC1=CC=CC=C1 ROIHUUVUCIGOLZ-UHFFFAOYSA-N 0.000 claims description 2
XGJGNIZVSIGIJT-UHFFFAOYSA-N n-[4-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]-2-phenylacetamide Chemical compound C=1C=NC(NC=2C=C(CS(C)(=O)=O)C=CC=2)=NC=1N(C)C(C=C1)=CC=C1NC(=O)CC1=CC=CC=C1 XGJGNIZVSIGIJT-UHFFFAOYSA-N 0.000 claims description 2
FWZSNFIKXFSEMO-UHFFFAOYSA-N phenyl n-[4-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]carbamate Chemical compound C=1C=NC(NC=2C=C(CS(C)(=O)=O)C=CC=2)=NC=1N(C)C(C=C1)=CC=C1NC(=O)OC1=CC=CC=C1 FWZSNFIKXFSEMO-UHFFFAOYSA-N 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 25
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 13
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 11
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 5
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 2
108010090091 TIE-2 Receptor Proteins 0.000 claims 2
102000012753 TIE-2 Receptor Human genes 0.000 claims 2
LZWJEODSCLZMOY-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-5-yl)-3-[4-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]urea Chemical compound C=1C=C(NC(=O)NC=2C=C3CCCC3=CC=2)C=CC=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 LZWJEODSCLZMOY-UHFFFAOYSA-N 0.000 claims 1
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