JP2004517925A5 - - Google Patents
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- Publication number
- JP2004517925A5 JP2004517925A5 JP2002559412A JP2002559412A JP2004517925A5 JP 2004517925 A5 JP2004517925 A5 JP 2004517925A5 JP 2002559412 A JP2002559412 A JP 2002559412A JP 2002559412 A JP2002559412 A JP 2002559412A JP 2004517925 A5 JP2004517925 A5 JP 2004517925A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- amino
- indazol
- pyrimidinyl
- 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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- YIYZHARUXWKUEN-UHFFFAOYSA-N benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1.NS(=O)(=O)C1=CC=CC=C1 YIYZHARUXWKUEN-UHFFFAOYSA-N 0.000 claims 23
- 125000000217 alkyl group Chemical group 0.000 claims 19
- 229910052739 hydrogen Inorganic materials 0.000 claims 17
- 239000001257 hydrogen Substances 0.000 claims 15
- 150000002431 hydrogen Chemical class 0.000 claims 13
- -1 C (O) R 1 Chemical group 0.000 claims 11
- 229910052736 halogen Inorganic materials 0.000 claims 8
- 150000002367 halogens Chemical class 0.000 claims 8
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 7
- 150000001875 compounds Chemical class 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 239000011780 sodium chloride Substances 0.000 claims 7
- 239000012453 solvate Substances 0.000 claims 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims 4
- 125000001188 haloalkyl group Chemical group 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 4
- 239000001301 oxygen Substances 0.000 claims 4
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000001769 aryl amino group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims 2
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 230000004977 physiological function Effects 0.000 claims 2
- 230000035790 physiological processes and functions Effects 0.000 claims 2
- OVTQMMYLOJBKOP-UHFFFAOYSA-N 1-[4-[[5-fluoro-4-[methyl-(3-methyl-2H-indazol-6-yl)amino]pyrimidin-2-yl]amino]phenyl]-N-methylmethanesulfonamide Chemical compound C1=CC(CS(=O)(=O)NC)=CC=C1NC1=NC=C(F)C(N(C)C=2C=C3NN=C(C)C3=CC=2)=N1 OVTQMMYLOJBKOP-UHFFFAOYSA-N 0.000 claims 1
- BPGZHRULBGZUFP-UHFFFAOYSA-N 1-[4-methoxy-3-[[4-[(3-methyl-2H-indazol-6-yl)amino]pyrimidin-2-yl]amino]phenyl]propan-1-one Chemical compound CCC(=O)C1=CC=C(OC)C(NC=2N=C(NC=3C=C4NN=C(C)C4=CC=3)C=CN=2)=C1 BPGZHRULBGZUFP-UHFFFAOYSA-N 0.000 claims 1
- MGSXZPZPZIPVHO-UHFFFAOYSA-N 2-[(3-methyl-2H-indazol-6-yl)-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]acetonitrile Chemical compound C=1C=C2C(C)=NNC2=CC=1N(CC#N)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 MGSXZPZPZIPVHO-UHFFFAOYSA-N 0.000 claims 1
- MQYXDHFLBFNMAM-UHFFFAOYSA-N 2-[(3-methyl-2H-indazol-6-yl)-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]acetonitrile Chemical compound C=1C=C2C(C)=NNC2=CC=1N(CC#N)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 MQYXDHFLBFNMAM-UHFFFAOYSA-N 0.000 claims 1
- YTTBOOLPGZCTSF-UHFFFAOYSA-N 3-[[4-[[2-[(3-chlorophenyl)methyl]-3-methylindazol-6-yl]-methylamino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C=1C=NC(NC=2C=C(C=CC=2)S(N)(=O)=O)=NC=1N(C)C(=CC1=N2)C=CC1=C(C)N2CC1=CC=CC(Cl)=C1 YTTBOOLPGZCTSF-UHFFFAOYSA-N 0.000 claims 1
- IBCFYVDVAYYIBT-UHFFFAOYSA-N 3-[[5-fluoro-4-[methyl-(3-methyl-2H-indazol-6-yl)amino]pyrimidin-2-yl]amino]-4-methoxy-N-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(OC)C(NC=2N=C(C(F)=CN=2)N(C)C=2C=C3NN=C(C)C3=CC=2)=C1 IBCFYVDVAYYIBT-UHFFFAOYSA-N 0.000 claims 1
- CBNFOUWNKLWLNA-UHFFFAOYSA-N 3-[[5-fluoro-4-[methyl-(3-methyl-2H-indazol-6-yl)amino]pyrimidin-2-yl]amino]-4-methoxybenzamide Chemical compound COC1=CC=C(C(N)=O)C=C1NC1=NC=C(F)C(N(C)C=2C=C3NN=C(C)C3=CC=2)=N1 CBNFOUWNKLWLNA-UHFFFAOYSA-N 0.000 claims 1
- DSWWZJMZQVRSAG-UHFFFAOYSA-N 3-[[5-fluoro-4-[methyl-(3-methyl-2H-indazol-6-yl)amino]pyrimidin-2-yl]amino]-N-propan-2-ylbenzenesulfonamide Chemical compound CC(C)NS(=O)(=O)C1=CC=CC(NC=2N=C(C(F)=CN=2)N(C)C=2C=C3NN=C(C)C3=CC=2)=C1 DSWWZJMZQVRSAG-UHFFFAOYSA-N 0.000 claims 1
- QDVXRMFTKAQZOJ-UHFFFAOYSA-N 4-N-(1,3-dimethylindazol-6-yl)-4-N-methyl-2-N-[3-(methylsulfonylmethyl)phenyl]pyrimidine-2,4-diamine Chemical compound C=1C=C2C(C)=NN(C)C2=CC=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 QDVXRMFTKAQZOJ-UHFFFAOYSA-N 0.000 claims 1
- OKMPHEGFRRVGRS-UHFFFAOYSA-N 4-N-(2,3-dimethylindazol-6-yl)-4-N-methyl-2-N-[3-(methylsulfonylmethyl)phenyl]pyrimidine-2,4-diamine Chemical compound C1=CC2=C(C)N(C)N=C2C=C1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 OKMPHEGFRRVGRS-UHFFFAOYSA-N 0.000 claims 1
- ZUKWQTLSOWOKOR-UHFFFAOYSA-N 4-[[5-fluoro-4-[methyl-(3-methyl-2H-indazol-6-yl)amino]pyrimidin-2-yl]amino]-3-methoxybenzenesulfonamide Chemical compound COC1=CC(S(N)(=O)=O)=CC=C1NC1=NC=C(F)C(N(C)C=2C=C3NN=C(C)C3=CC=2)=N1 ZUKWQTLSOWOKOR-UHFFFAOYSA-N 0.000 claims 1
- IDXNGTHGCYPLSM-UHFFFAOYSA-N 5-[[4-[(2,3-dimethylindazol-6-yl)-methylamino]-1,3,5-triazin-2-yl]amino]-2-methylbenzenesulfonamide Chemical compound C1=CC2=C(C)N(C)N=C2C=C1N(C)C(N=1)=NC=NC=1NC1=CC=C(C)C(S(N)(=O)=O)=C1 IDXNGTHGCYPLSM-UHFFFAOYSA-N 0.000 claims 1
- CCAVHDVJKVYFCH-UHFFFAOYSA-N 5-fluoro-2-N-(2-methoxy-5-propan-2-ylsulfonylphenyl)-4-N-methyl-4-N-(3-methyl-2H-indazol-6-yl)pyrimidine-2,4-diamine Chemical compound COC1=CC=C(S(=O)(=O)C(C)C)C=C1NC1=NC=C(F)C(N(C)C=2C=C3NN=C(C)C3=CC=2)=N1 CCAVHDVJKVYFCH-UHFFFAOYSA-N 0.000 claims 1
- ANCNAKDZYQJJFB-UHFFFAOYSA-N 5-fluoro-4-N-methyl-4-N-(3-methyl-2H-indazol-6-yl)-2-N-(4-methylsulfonylphenyl)pyrimidine-2,4-diamine Chemical compound C=1C=C2C(C)=NNC2=CC=1N(C)C(C(=CN=1)F)=NC=1NC1=CC=C(S(C)(=O)=O)C=C1 ANCNAKDZYQJJFB-UHFFFAOYSA-N 0.000 claims 1
- IJIKZGCUKZGSHO-UHFFFAOYSA-N 5-fluoro-4-N-methyl-4-N-(3-methyl-2H-indazol-6-yl)-2-N-[3-(methylsulfonylmethyl)phenyl]pyrimidine-2,4-diamine Chemical compound C=1C=C2C(C)=NNC2=CC=1N(C)C(C(=CN=1)F)=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 IJIKZGCUKZGSHO-UHFFFAOYSA-N 0.000 claims 1
- AQRABUUXKQANHS-UHFFFAOYSA-N 5-fluoro-4-N-methyl-4-N-(3-methyl-2H-indazol-6-yl)-2-N-[3-(propan-2-ylsulfonylmethyl)phenyl]pyrimidine-2,4-diamine Chemical compound CC(C)S(=O)(=O)CC1=CC=CC(NC=2N=C(C(F)=CN=2)N(C)C=2C=C3NN=C(C)C3=CC=2)=C1 AQRABUUXKQANHS-UHFFFAOYSA-N 0.000 claims 1
- JRMPYMHBRVUPFL-UHFFFAOYSA-N C(#C)C1(NC(=NC=C1)NC1=CC(=CC=C1)CS(=O)(=O)C)NC1=CC=C2C(=NNC2=C1)C Chemical compound C(#C)C1(NC(=NC=C1)NC1=CC(=CC=C1)CS(=O)(=O)C)NC1=CC=C2C(=NNC2=C1)C JRMPYMHBRVUPFL-UHFFFAOYSA-N 0.000 claims 1
- SYURXPQNHWWIQV-UHFFFAOYSA-N C(C)(C)S(=O)(=O)C=1C=CC(=C(C=1)C1(NC=CC(=N1)N(C1=CC=C2C(=NNC2=C1)C)C)N)OC Chemical compound C(C)(C)S(=O)(=O)C=1C=CC(=C(C=1)C1(NC=CC(=N1)N(C1=CC=C2C(=NNC2=C1)C)C)N)OC SYURXPQNHWWIQV-UHFFFAOYSA-N 0.000 claims 1
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- SOFVXWOEBIPQLP-UHFFFAOYSA-N C(C)(C)S(=O)(=O)CC=1C=C(C=CC=1)C1(NC=CC(=N1)N(C1=CC=C2C(=NNC2=C1)C)C)N Chemical compound C(C)(C)S(=O)(=O)CC=1C=C(C=CC=1)C1(NC=CC(=N1)N(C1=CC=C2C(=NNC2=C1)C)C)N SOFVXWOEBIPQLP-UHFFFAOYSA-N 0.000 claims 1
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- WIQJFZRIFRHEAI-UHFFFAOYSA-N C(C)C1(NC(=NC=C1F)NC1=C(C=CC(=C1)S(=O)(=O)C)OC)NC1=CC=C2C(=NNC2=C1)C Chemical compound C(C)C1(NC(=NC=C1F)NC1=C(C=CC(=C1)S(=O)(=O)C)OC)NC1=CC=C2C(=NNC2=C1)C WIQJFZRIFRHEAI-UHFFFAOYSA-N 0.000 claims 1
- MKQLDHOHEOAOHJ-UHFFFAOYSA-N C(C)C1=NNC2=CC(=CC=C12)C1(NC(=NC=C1F)NC1=CC(=CC=C1)CS(=O)(=O)C)NC Chemical compound C(C)C1=NNC2=CC(=CC=C12)C1(NC(=NC=C1F)NC1=CC(=CC=C1)CS(=O)(=O)C)NC MKQLDHOHEOAOHJ-UHFFFAOYSA-N 0.000 claims 1
- YCSRKCLLXHHELU-UHFFFAOYSA-N C(C)S(=O)(=O)C1=CC=C(C=C1)C1(NC=CC(=N1)N(C1=CC=C2C(=NNC2=C1)C)C)N Chemical compound C(C)S(=O)(=O)C1=CC=C(C=C1)C1(NC=CC(=N1)N(C1=CC=C2C(=NNC2=C1)C)C)N YCSRKCLLXHHELU-UHFFFAOYSA-N 0.000 claims 1
- IDELGVLOWFHGCY-UHFFFAOYSA-N C(C)S(=O)(=O)C=1C=CC(=C(C1)C1(NC=CC(=N1)N(C1=CC=C2C(=NNC2=C1)C)C)N)OC Chemical compound C(C)S(=O)(=O)C=1C=CC(=C(C1)C1(NC=CC(=N1)N(C1=CC=C2C(=NNC2=C1)C)C)N)OC IDELGVLOWFHGCY-UHFFFAOYSA-N 0.000 claims 1
- XJJKEJHOYVBADS-UHFFFAOYSA-N C(C)S(=O)(=O)C=1C=CC(=C(C=1)C1(NC=C(C(=N1)N(C1=CC=C2C(=NNC2=C1)C)C)F)N)OC Chemical compound C(C)S(=O)(=O)C=1C=CC(=C(C=1)C1(NC=C(C(=N1)N(C1=CC=C2C(=NNC2=C1)C)C)F)N)OC XJJKEJHOYVBADS-UHFFFAOYSA-N 0.000 claims 1
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- LITBTKAXHNNSMV-UHFFFAOYSA-N CN1N=C2C=C(C=CC2=C1C)C1(NC(=NC=C1)NC1=C(C=CC(=C1)S(=O)(=O)CC)OC)NC Chemical compound CN1N=C2C=C(C=CC2=C1C)C1(NC(=NC=C1)NC1=C(C=CC(=C1)S(=O)(=O)CC)OC)NC LITBTKAXHNNSMV-UHFFFAOYSA-N 0.000 claims 1
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- 102100013180 KDR Human genes 0.000 claims 1
- 101710030888 KDR Proteins 0.000 claims 1
- FHCXJZSNEBTJKE-UHFFFAOYSA-N N-[2-methyl-5-[[4-[methyl-(3-methyl-2H-indazol-6-yl)amino]-1,3,5-triazin-2-yl]amino]phenyl]methanesulfonamide Chemical compound C=1C=C2C(C)=NNC2=CC=1N(C)C(N=1)=NC=NC=1NC1=CC=C(C)C(NS(C)(=O)=O)=C1 FHCXJZSNEBTJKE-UHFFFAOYSA-N 0.000 claims 1
- YDHRSWAPJJCSGX-UHFFFAOYSA-N N-[3-[[4-[ethyl-(3-methyl-2H-indazol-6-yl)amino]pyrimidin-2-yl]amino]phenyl]acetamide Chemical compound C=1C=C2C(C)=NNC2=CC=1N(CC)C(N=1)=CC=NC=1NC1=CC=CC(NC(C)=O)=C1 YDHRSWAPJJCSGX-UHFFFAOYSA-N 0.000 claims 1
- AXBKRLMNVZOBIH-UHFFFAOYSA-N N-[3-[[4-[methyl-(3-methyl-2H-indazol-6-yl)amino]pyrimidin-2-yl]amino]phenyl]acetamide Chemical compound C=1C=C2C(C)=NNC2=CC=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(NC(C)=O)=C1 AXBKRLMNVZOBIH-UHFFFAOYSA-N 0.000 claims 1
- RBENAORRCGKTLF-UHFFFAOYSA-N N-[3-[[4-[methyl-(3-methyl-2H-indazol-6-yl)amino]pyrimidin-2-yl]amino]phenyl]methanesulfonamide Chemical compound C=1C=C2C(C)=NNC2=CC=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(NS(C)(=O)=O)=C1 RBENAORRCGKTLF-UHFFFAOYSA-N 0.000 claims 1
- AYHVTCLZDJHJSE-UHFFFAOYSA-N N-[4-[[4-[methyl-(3-methyl-2H-indazol-6-yl)amino]-1,3,5-triazin-2-yl]amino]phenyl]acetamide Chemical compound C=1C=C2C(C)=NNC2=CC=1N(C)C(N=1)=NC=NC=1NC1=CC=C(NC(C)=O)C=C1 AYHVTCLZDJHJSE-UHFFFAOYSA-N 0.000 claims 1
- ARZWRWBLDKOLFV-UHFFFAOYSA-N N-[5-[[5-fluoro-4-[methyl-(3-methyl-2H-indazol-6-yl)amino]pyrimidin-2-yl]amino]-2-methylphenyl]methanesulfonamide Chemical compound C=1C=C2C(C)=NNC2=CC=1N(C)C(C(=CN=1)F)=NC=1NC1=CC=C(C)C(NS(C)(=O)=O)=C1 ARZWRWBLDKOLFV-UHFFFAOYSA-N 0.000 claims 1
- CCDZAMNZEXREEV-UHFFFAOYSA-N N-[[3-[[4-[methyl-(3-methyl-2H-indazol-6-yl)amino]pyrimidin-2-yl]amino]phenyl]methyl]methanesulfonamide Chemical compound C=1C=C2C(C)=NNC2=CC=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CNS(C)(=O)=O)=C1 CCDZAMNZEXREEV-UHFFFAOYSA-N 0.000 claims 1
- WSOASQNARKHWJC-UHFFFAOYSA-N N-[[4-[[4-[methyl-(3-methyl-2H-indazol-6-yl)amino]pyrimidin-2-yl]amino]phenyl]methyl]ethanesulfonamide Chemical compound C1=CC(CNS(=O)(=O)CC)=CC=C1NC1=NC=CC(N(C)C=2C=C3NN=C(C)C3=CC=2)=N1 WSOASQNARKHWJC-UHFFFAOYSA-N 0.000 claims 1
- RPRKQNOHZFUQTF-UHFFFAOYSA-N N1N=CC2=CC=C(C=C12)C1(NC(=NC=C1)NC1=CC(=CC=C1)CS(=O)(=O)C)NC Chemical compound N1N=CC2=CC=C(C=C12)C1(NC(=NC=C1)NC1=CC(=CC=C1)CS(=O)(=O)C)NC RPRKQNOHZFUQTF-UHFFFAOYSA-N 0.000 claims 1
- 230000033115 angiogenesis Effects 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims 1
- CUIHSIWYWATEQL-UHFFFAOYSA-N pazopanib Chemical compound C1=CC2=C(C)N(C)N=C2C=C1N(C)C(N=1)=CC=NC=1NC1=CC=C(C)C(S(N)(=O)=O)=C1 CUIHSIWYWATEQL-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
Claims (7)
- 下記式(I)の化合物もしくはその塩、溶媒和物、または生理学的に機能する誘導体:
Dは:
X1は水素、C1-C4アルキル、C1-C4ハロアルキル、またはC1-C4ヒドロキシアルキルである;
X2は水素、C1-C4アルキル、C1-C4ハロアルキル、C(O)R1、またはアラルキルである;
X3は水素またはハロゲンである;
X4は水素、C1-C4アルキル、C1-C4ハロアルキル、ヘテロアラルキル、シアノアルキル、-(CH2)pC=CH(CH2)tH、-(CH2)pC≡C(CH2)tH、またはC3-C7シクロアルキルである;
pは1、2、または3である;
tは0または1である;
WはNまたはC-R[式中Rは水素、ハロゲン、またはシアノである]である;
Q1は水素、ハロゲン、C1-C2ハロアルキル、C1-C2アルキル、C1-C2アルコキシ、またはC1-C2ハロアルコキシである;
Q2はA1またはA2である;
Q3はQ2がA2である場合はA1であり、Q2がA1である場合はA2である;
ここで、
A1は水素、ハロゲン、C1-C3アルキル、C1-C3ハロアルキル、-OR1である、
A2は-(Z)m-(Z1)-(Z2)で定義される基であり、この式中
ZはCH2であり、mは0、1、2、または3であるか、あるいは
ZはNR2であり、mは0または1であるか、あるいは
Zは酸素であり、mは0または1であるか、あるいは
ZはCH2NR2であり、mは0または1である;
Z1はS(O)2、S(O)、またはC(O)である;
Z2はC1-C4アルキル、NR3R4、アリール、アリールアミノ、アラルキル、アラルコキシ、またはヘテロアリールである、
R1はC1-C4アルキルである;
R2、R3、およびR4はそれぞれ独立に水素、C1-C4アルキル、C3-C7シクロアルキル、-S(O)2R5、および-C(O)R5から選択される;
R5はC1-C4アルキル、またはC3-C7シクロアルキルである;そして
Zが酸素である場合Z1はS(O)2であり、Dが:
- 下記式(III)の化合物もしくはその塩、溶媒和物、または生理学的に機能する誘導体:
X1は水素、C1-C4アルキル、C1-C4ハロアルキル、またはC1-C4ヒドロキシアルキルである;
X2はC1-C4アルキル、C1-C4ハロアルキル、またはC(O)R1である;
X3は水素またはハロゲンである;
X4は水素、C1-C4アルキル、C1-C4ハロアルキル、ヘテロアラルキル、シアノアルキル、-(CH2)pC=CH(CH2)tH、-(CH2)pC≡C(CH2)tH、またはC3-C7シクロアルキルである;
pは1、2、または3である;
tは0または1である;
WはNまたはC-R[式中Rは水素、ハロゲン、またはシアノである]である;
Q1は水素、ハロゲン、C1-C2ハロアルキル、C1-C2アルキル、C1-C2アルコキシ、またはC1-C2ハロアルコキシである;
Q2はA1またはA2である;
Q3はQ2がA2である場合はA1であり、Q2がA1である場合はA2である;
ここで、
A1は水素、ハロゲン、C1-C3アルキル、C1-C3ハロアルキル、-OR1である、
A2は-(Z)m-(Z1)-(Z2)で定義される基であり、この式中
ZはCH2であり、mは0、1、2、または3であるか、あるいは
ZはNR2であり、mは0または1であるか、あるいは
Zは酸素であり、mは0または1であるか、あるいは
ZはCH2NR2であり、mは0または1である;
Z1はS(O)2、S(O)、またはC(O)である;
Z2はC1-C4アルキル、NR3R4、アリール、アリールアミノ、アラルキル、アラルコキシ、またはヘテロアリールである、
R1はC1-C4アルキルである;
R2、R3、およびR4はそれぞれ独立に水素、C1-C4アルキル、C3-C7シクロアルキル、-S(O)2R5、および-C(O)R5から選択される;
R5はC1-C4アルキル、またはC3-C7シクロアルキルである;そして
Zが酸素である場合Z1はS(O)2である]。 - N2-[5-(エチルスルホニル)-2-メトキシフェニル]-5-フルオロ-N4-メチル-N4-(3-メチル-1H-インダゾール-6-イル)-2,4-ピリミジンジアミン;
3-({5-フルオロ-4-[メチル(3-メチル-1H-インダゾール-6-イル)アミノ]-2-ピリミジニル}アミノ)-4-メトキシ-N-メチルベンゼンスルホンアミド;
5-フルオロ-N4-メチル-N4-(3-メチル-1H-インダゾール-6-イル)-N2-{3-[(メチルスルホニル)メチル]フェニル}-2,4-ピリミジンジアミン;
3-({5-フルオロ-4-[メチル(3-メチル-1H-インダゾール-6-イル)アミノ]-2-ピリミジニル}アミノ)-N-イソプロピルベンゼンスルホンアミド;
5-フルオロ-N2-[5-(イソプロピルスルホニル)-2-メトキシフェニル]-N4-メチル-N4-(3-メチル-1H-インダゾール-6-イル)-2,4-ピリミジンジアミン;
N-[5-({5-フルオロ-4-[メチル(3-メチル-1H-インダゾール-6-イル)アミノ]-2-ピリミジニル}アミノ)-2-メチルフェニル]メタンスルホンアミド;
5-フルオロ-N4-メチル-N4-(3-メチル-1H-インダゾール-6-イル)-N2-[4-(メチルスルホニル)フェニル]-2,4-ピリミジンジアミン;
N4-(3-エチル-1H-インダゾール-6-イル)-5-フルオロ-N4-メチル-N2-{3-[(メチルスルホニル)メチル]フェニル}-2,4-ピリミジンジアミン;
4-({5-フルオロ-4-[メチル(3-メチル-1H-インダゾール-6-イル)アミノ]-2-ピリミジニル}アミノ)ベンゼンスルホンアミド;
N4-エチル-5-フルオロ-N2-[2-メトキシ-5-(メチルスルホニル)フェニル]-N4-(3-メチル-1H-インダゾール-6-イル)-2,4-ピリミジンジアミン;
[4-({5-フルオロ-4-[メチル(3-メチル-1H-インダゾール-6-イル)アミノ]-2-ピリミジニル}アミノ)フェニル]-N-メチルメタンスルホンアミド;
5-フルオロ-N2-{3-[(イソプロピルスルホニル)メチル]フェニル}-N4-メチル-N4-(3-メチル-1H-インダゾール-6-イル)-2,4-ピリミジンジアミン;
3-({5-フルオロ-4-[メチル(3-メチル-1H-インダゾール-6-イル)アミノ]-2-ピリミジニル}アミノ)-4-メトキシベンズアミド;
4-({5-フルオロ-4-[メチル(3-メチル-1H-インダゾール-6-イル)アミノ]-2-ピリミジニル}アミノ)-3-メトキシベンゼンスルホンアミド;
N2-(3-メチル-1H-インダゾール-6-イル)-N4-{3-[(メチルスルホニル)メチル]フェニル}-1,3,5-トリアジン-2,4-ジアミントリフルオロ酢酸;
N2-メチル-N2-(3-メチル-1H-インダゾール-6-イル)-N4-{3-[(メチルスルホニル)メチル]フェニル}-1,3,5-トリアジン-2,4-ジアミン;
N2-[5-(エチルスルホニル)-2-メトキシフェニル]-N4-メチル-N4-(3-メチル-1H-インダゾール-6-イル)-1,3,5-トリアジン-2,4-ジアミン;
N-[2-メチル-5-({4-[メチル(3-メチル-1H-インダゾール-6-イル)アミノ]-1,3,5-トリアジン-2-イル}アミノ)フェニル]メタンスルホンアミド;
N2-メチル-N2-(3-メチル-1H-インダゾール-6-イル)-N4-[3-(メチルスルホニル)フェニル]-1,3,5-トリアジン-2,4-ジアミン;
N-[4-({4-[メチル(3-メチル-1H-インダゾール-6-イル)アミノ]-1,3,5-トリアジン-2-イル}アミノ)フェニル]アセトアミド;
3-({4-[メチル(3-メチル-1H-インダゾール-6-イル)アミノ]-2-ピリミジニル}アミノ)ベンゼンスルホンアミド;
N2-[5-(エチルスルホニル)-2-メトキシフェニル]-N4-メチル-N4-(3-メチル-1H-インダゾール-6-イル)-2,4-ピリミジンジアミン;
N4-メチル-N4-(3-メチル-1H-インダゾール-6-イル)-N2-{3-[(メチルスルホニル)メチル]フェニル}-2,4-ピリミジンジアミン;
N-イソプロピル-3-({4-[メチル(3-メチル-1H-インダゾール-6-イル)アミノ]-2-ピリミジニル}アミノ)ベンゼンスルホンアミド;
N-シクロプロピル-3-({4-[メチル(3-メチル-1H-インダゾール-6-イル)アミノ]-2-ピリミジニル}アミノ)ベンゼンスルホンアミド;
N4-エチル-N2-[5-(エチルスルホニル)-2-メトキシフェニル]-N4-(3-メチル-1H-インダゾール-6-イル)-2,4-ピリミジンジアミン;
N-[3-({4-[メチル(3-メチル-1H-インダゾール-6-イル)アミノ]-2-ピリミジニル}アミノ)フェニル]メタンスルホンアミド;
N2-{3-[(イソプロピルスルホニル)メチル]フェニル}-N4-メチル-N4-(3-メチル-1H-インダゾール-6-イル)-2,4-ピリミジンジアミン;
N2-{4-[(イソプロピルスルホニル)メチル]フェニル}-N4-メチル-N4-(3-メチル-1H-インダゾール-6-イル)-2,4-ピリミジンジアミン;
N2-[5-(イソブチルスルホニル)-2-メトキシフェニル]-N4-(3-メチル-1H-インダゾール-6-イル)-2,4-ピリミジンジアミン;
N-[3-({4-[メチル(3-メチル-1H-インダゾール-6-イル)アミノ]-2-ピリミジニル}アミノ)フェニル]アセトアミド;
N-[3-({4-[エチル(3-メチル-1H-インダゾール-6-イル)アミノ]-2-ピリミジニル}アミノ)フェニル]アセトアミド;
N2-(2-メトキシ-5-{[(5-メチル-3-イソオキサゾリル)メチル]スルホニル}フェニル)-N4-(3-メチル-1H-インダゾール-6-イル)-2,4-ピリミジンジアミン;
4-メトキシ-3-({4-[(3-メチル-1H-インダゾール-6-イル)アミノ]-2-ピリミジニル}アミノ)ベンゼンスルホンアミド;
N2-[5-(イソプロピルスルホニル)-2-メトキシフェニル]-N4-メチル-N4-(3-メチル-1H-インダゾール-6-イル)-2,4-ピリミジンジアミン;
N2-[5-(エチルスルホニル)-2-メトキシフェニル]-N4-イソプロピル-N4-(3-メチル-1H-インダゾール-6-イル)-2,4-ピリミジンジアミン;
N4-(1H-インダゾール-6-イル)-N4-メチル-N2-{3-[(メチルスルホニル)メチル]フェニル}-2,4-ピリミジンジアミン;
N4-(1,3-ジメチル-1H-インダゾール-6-イル)-N4-メチル-N2-{3-[(メチルスルホニル)メチル]フェニル}-2,4-ピリミジンジアミン;
N4-(2,3-ジメチル-2H-インダゾール-6-イル)-N4-メチル-N2-{3-[(メチルスルホニル)メチル]フェニル}-2,4-ピリミジンジアミン;
N4-(2,3-ジメチル-2H-インダゾール-6-イル)-N2-[5-(エチルスルホニル)-2-メトキシフェニル]-N4-メチル-2,4-ピリミジンジアミン;
1-[4-メトキシ-3-({4-[(3-メチル-1H-インダゾール-6-イル)アミノ]-2-ピリミジニル}アミノ)フェニル]-1-プロパノン;
4-メトキシ-N-[3-({4-[メチル(3-メチル-1H-インダゾール-6-イル)アミノ]-2-ピリミジニル}アミノ)フェニル]ベンゼンスルホンアミド;
4-メトキシ-N-メチル-3-({4-[(3-メチル-1H-インダゾール-6-イル)アミノ]-2-ピリミジニル}アミノ)ベンゼンスルホンアミド;
[(3-メチル-1H-インダゾール-6-イル)(2-{4-[(メチルスルホニル)メチル]アニリノ}-4-ピリミジニル)アミノ]アセトニトリル;
[{2-[5-(エチルスルホニル)-2-メトキシアニリノ]-4-ピリミジニル}(3-メチル-1H-インダゾール-6-イル)アミノ]アセトニトリル;
[(3-メチル-1H-インダゾール-6-イル)(2-{3-[(メチルスルホニル)メチル]アニリノ}-4-ピリミジニル)アミノ]アセトニトリル;
4-メトキシ-N-メチル-3-({4-[メチル(3-メチル-1H-インダゾール-6-イル)アミノ]-2-ピリミジニル}アミノ)ベンゼンスルホンアミド;
4-({4-[メチル(3-メチル-1H-インダゾール-6-イル)アミノ]-2-ピリミジニル}アミノ)ベンズアミド;
3-メトキシ-4-({4-[メチル(3-メチル-1H-インダゾール-6-イル)アミノ]-2-ピリミジニル}アミノ)ベンゼンスルホンアミド;
N4-エチニル-N4-(3-メチル-1H-インダゾール-6-イル)-N2-{3-[(メチルスルホニル)メチル]フェニル}-2,4-ピリミジンジアミン;
3-({4-[(3-メチル-1H-インダゾール-6-イル)(2-プロピニル)アミノ]-2-ピリミジニル}アミノ)ベンゼンスルホンアミド;
4-({4-[メチル(3-メチル-1H-インダゾール-6-イル)アミノ]-2-ピリミジニル}アミノ)ベンゼンスルホンアミド;
N4-メチル-N4-(3-メチル-1H-インダゾール-6-イル)-N2-[3-(メチルスルホニル)フェニル]-2,4-ピリミジンジアミン;
4-メトキシ-3-({4-[メチル(3-メチル-1H-インダゾール-6-イル)アミノ]-2-ピリミジニル}アミノ)ベンゼンスルホンアミド;
N2-[5-(エチルスルホニル)-2-メトキシフェニル]-N4-(3-メチル-1H-インダゾール-6-イル)-2,4-ピリミジンジアミン;
3-({4-[メチル(3-メチル-1H-インダゾール-6-イル)アミノ]-2-ピリミジニル}アミノ)ベンズアミド;
N2-[4-(エチルスルホニル)フェニル]-N4-メチル-N4-(3-メチル-1H-インダゾール-6-イル)-2,4-ピリミジンジアミン;
N-[4-({4-[メチル(3-メチル-1H-インダゾール-6-イル)アミノ]-2-ピリミジニル}アミノ)ベンジル]エタンスルホンアミド;
N-[3-({4-[メチル(3-メチル-1H-インダゾール-6-イル)アミノ]-2-ピリミジニル}アミノ)ベンジル]メタンスルホンアミド;
2-クロロ-5-({4-[メチル(3-メチル-1H-インダゾール-6-イル)アミノ]-2-ピリミジニル}アミノ)ベンゼンスルホンアミド;
2-クロロ-4-({4-[メチル(3-メチル-1H-インダゾール-6-イル)アミノ]-2-ピリミジニル}アミノ)ベンゼンスルホンアミド;
4-クロロ-3-({4-[メチル(3-メチル-1H-インダゾール-6-イル)アミノ]-2-ピリミジニル}アミノ)ベンゼンスルホンアミド;
3-メチル-4-({4-[メチル(3-メチル-1H-インダゾール-6-イル)アミノ]-2-ピリミジニル}アミノ)ベンゼンスルホンアミド;
2-メチル-5-({4-[メチル(3-メチル-1H-インダゾール-6-イル)アミノ]-2-ピリミジニル}アミノ)ベンゼンスルホンアミド;
4-メチル-3-({4-[メチル(3-メチル-1H-インダゾール-6-イル)アミノ]-2-ピリミジニル}アミノ)ベンゼンスルホンアミド;
N4-メチル-N4-(3-メチル-1H-インダゾール-6-イル)-N2-[3-(メチルスルフィニル)フェニル]-2,4-ピリミジンジアミン;
N2-[2-フルオロ-5-(メチルスルホニル)フェニル]-N4-メチル-N4-(3-メチル-1H-インダゾール-6-イル)-2,4-ピリミジンジアミン;
N2-[2-メトキシ-5-(メチルスルホニル)フェニル]-N4-メチル-N4-(3-メチル-1H-インダゾール-6-イル)-2,4-ピリミジンジアミン;
5-({4-[(2,3-ジメチル-2H-インダゾール-6-イル)(メチル)アミノ]ピリミジン-2-イル}アミノ)-2-メチルベンゼンスルホンアミド;
3-({4-[(2,3-ジメチル-2H-インダゾール-6-イル)(メチル)アミノ]ピリミジン-2-イル}アミノ)ベンゼンスルホンアミド;
2-[4-({4-[(2,3-ジメチル-2H-インダゾール-6-イル)(メチル)アミノ]ピリミジン-2-イル}アミノ)フェニル]エタンスルホンアミド;
N4-(2,3-ジメチル-2H-インダゾール-6-イル)-N4-メチル-N2-{4-[(メチルスルホニル)メチル]フェニル}ピリミジン-2,4-ジアミン;
3-({4-[[3-(ヒドロキシメチル)-2-メチル-2H-インダゾール-6-イル](メチル)アミノ]ピリミジン-2-イル}アミノ)ベンゼンスルホンアミド;
3-({4-[(1,2-ジメチル-1H-ベンズイミダゾール-5-イル)(メチル)アミノ]ピリミジン-2-イル}アミノ)ベンゼンスルホンアミド;
3-({4-[(2-ベンジル-1-メチル-1H-ベンズイミダゾール-5-イル)(メチル)アミノ]ピリミジン-2-イル}アミノ)ベンゼンスルホンアミド;
3-({4-[(2-エチル-3-メチル-2H-インダゾール-6-イル)(メチル)アミノ]ピリミジン-2-イル}アミノ)ベンゼンスルホンアミド;
3-({4-[[2-(3-クロロベンジル)-3-メチル-2H-インダゾール-6-イル](メチル)アミノ]ピリミジン-2-イル}アミノ)ベンゼンスルホンアミド;
3-({4-[(2,3-ジメチル-2H-インダゾール-6-イル)(メチル)アミノ]-1,3,5-トリアジン-2-イル}アミノ)ベンゼンスルホンアミド;および
5-({4-[(2,3-ジメチル-2H-インダゾール-6-イル)(メチル)アミノ]-1,3,5-トリアジン-2-イル}アミノ)-2-メチルベンゼンスルホンアミド;
からなる群から選択される、請求項1に記載の化合物もしくはその塩、溶媒和物、または生理学的に機能する誘導体。 - 請求項1〜3のいずれか1項に記載の化合物、もしくはその塩、溶媒和物、または生理学的に機能する誘導体の治療的に有効な量、ならびに医薬的に許容される担体、希釈剤および賦形剤の1つ以上、を含む医薬組成物。
- 治療に使用される請求項1〜3のいずれか1項に記載の化合物、もしくはその塩、溶媒和物、または生理学的に機能する誘導体。
- 不適切なVEGFR2活性が介在して起こる疾患の治療に使用される医薬の製造における、請求項1〜3のいずれか1項に記載の化合物、もしくはその塩、溶媒和物、または生理学的に機能する誘導体の使用。
- 不適切な血管新生により特徴づけられる疾患の治療に使用される医薬の製造における、請求項1〜3のいずれか1項に記載の化合物、もしくはその塩、溶媒和物、または生理学的に機能する誘導体の使用。
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PCT/US2001/049367 WO2002059110A1 (en) | 2000-12-21 | 2001-12-19 | Pyrimidineamines as angiogenesis modulators |
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PT2311825E (pt) * | 2000-12-21 | 2016-01-22 | Novartis Ag | Piramidinaminas como moduladores da angiogénese |
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2001
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- 2001-12-19 WO PCT/US2001/049367 patent/WO2002059110A1/en active IP Right Grant
- 2001-12-19 AU AU2002246723A patent/AU2002246723B2/en active Active
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- 2001-12-19 DE DE122010000038C patent/DE122010000038I1/de active Pending
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- 2001-12-19 BR BR0116452-0A patent/BR0116452A/pt active Search and Examination
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- 2001-12-19 KR KR1020037008349A patent/KR100847169B1/ko active IP Right Review Request
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2003
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2004
- 2004-02-24 HK HK04101322.3A patent/HK1059926A1/xx not_active IP Right Cessation
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2006
- 2006-05-15 US US11/383,229 patent/US7262203B2/en not_active Expired - Lifetime
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2007
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2009
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- 2009-10-30 US US12/609,398 patent/US20100105712A1/en not_active Abandoned
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2010
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- 2010-07-29 CY CY2010014C patent/CY2010014I2/el unknown
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- 2010-11-10 NO NO2010020C patent/NO2010020I1/no not_active IP Right Cessation
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2011
- 2011-04-26 HK HK11104135.5A patent/HK1149930A1/xx not_active IP Right Cessation
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2012
- 2012-07-10 US US13/545,029 patent/US20120277258A1/en not_active Abandoned
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2017
- 2017-01-11 HU HUS1700003C patent/HUS1700003I1/hu unknown
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2022
- 2022-01-06 NO NO2022001C patent/NO2022001I1/no unknown
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