PT2311825E - Piramidinaminas como moduladores da angiogénese - Google Patents

Info

Publication number

PT2311825E

PT2311825E PT91591388T PT01159138T PT2311825E PT 2311825 E PT2311825 E PT 2311825E PT 91591388 T PT91591388 T PT 91591388T PT 01159138 T PT01159138 T PT 01159138T PT 2311825 E PT2311825 E PT 2311825E

Authority

PT

Portugal

Prior art keywords

methyl

amino

indazol

pyrimidinyl

hydrogen

Prior art date

2000-12-21

Links

• Espacenet
• Global Dossier
• Discuss

• 239000000587 angiogenesis modulating agent Substances 0.000 title 1
• 229940076002 angiogenesis modulator Drugs 0.000 title 1
• LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical class NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 title 1
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 38
• 238000011282 treatment Methods 0.000 claims abstract description 28
• -1 cyanomethyl Chemical group 0.000 claims description 169
• 229910052739 hydrogen Inorganic materials 0.000 claims description 153
• 150000001875 compounds Chemical class 0.000 claims description 149
• 239000001257 hydrogen Substances 0.000 claims description 138
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 92
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 82
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 60
• 150000003839 salts Chemical class 0.000 claims description 58
• 125000000217 alkyl group Chemical group 0.000 claims description 52
• 229910052736 halogen Chemical group 0.000 claims description 48
• 150000002367 halogens Chemical group 0.000 claims description 48
• 239000012453 solvate Substances 0.000 claims description 47
• 102100033177 Vascular endothelial growth factor receptor 2 Human genes 0.000 claims description 37
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 36
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 36
• 238000002360 preparation method Methods 0.000 claims description 35
• 101000851007 Homo sapiens Vascular endothelial growth factor receptor 2 Proteins 0.000 claims description 34
• 230000000694 effects Effects 0.000 claims description 31
• 239000008194 pharmaceutical composition Substances 0.000 claims description 24
• 239000000460 chlorine Substances 0.000 claims description 21
• 230000033115 angiogenesis Effects 0.000 claims description 19
• 229910052801 chlorine Inorganic materials 0.000 claims description 17
• 239000003814 drug Substances 0.000 claims description 17
• 125000001188 haloalkyl group Chemical group 0.000 claims description 17
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 12
• 125000004966 cyanoalkyl group Chemical group 0.000 claims description 12
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
• 230000001404 mediated effect Effects 0.000 claims description 9
• AJJWFOBQWWYSKG-UHFFFAOYSA-N 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(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 AJJWFOBQWWYSKG-UHFFFAOYSA-N 0.000 claims description 7
• 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 7
• 238000002560 therapeutic procedure Methods 0.000 claims description 7
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
• 239000003085 diluting agent Substances 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• 229910052799 carbon Inorganic materials 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
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• 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 description 3
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• VTXJRGSOKKDRGH-UHFFFAOYSA-N 2-n-(5-ethylsulfonyl-2-methoxyphenyl)-4-n-methyl-4-n-(3-methyl-2h-indazol-6-yl)pyrimidine-2,4-diamine Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2N=C(C=CN=2)N(C)C2=CC3=NNC(C)=C3C=C2)=C1 VTXJRGSOKKDRGH-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• CMYGIORLGUFXRP-UHFFFAOYSA-N 4-n-(2,3-dimethylindazol-6-yl)-2-n-(5-ethylsulfonyl-2-methoxyphenyl)-4-n-methylpyrimidine-2,4-diamine Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2N=C(C=CN=2)N(C)C2=CC3=NN(C)C(C)=C3C=C2)=C1 CMYGIORLGUFXRP-UHFFFAOYSA-N 0.000 claims description 2
• BOKJLELAASHRDE-UHFFFAOYSA-N 4-n-ethyl-2-n-(5-ethylsulfonyl-2-methoxyphenyl)-4-n-(3-methyl-2h-indazol-6-yl)pyrimidine-2,4-diamine Chemical compound C=1C=C2C(C)=NNC2=CC=1N(CC)C(N=1)=CC=NC=1NC1=CC(S(=O)(=O)CC)=CC=C1OC BOKJLELAASHRDE-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 150000002431 hydrogen Chemical class 0.000 claims 10
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