MXPA06001759A - 2,4-pirimidinadiaminas utiles en el tratamiento de enfermedades neoplasticas, desordenes del sistema inmune e inflamatorios. - Google Patents

Info

Publication number

MXPA06001759A

MXPA06001759A MXPA06001759A MXPA06001759A MXPA06001759A MX PA06001759 A MXPA06001759 A MX PA06001759A MX PA06001759 A MXPA06001759 A MX PA06001759A MX PA06001759 A MXPA06001759 A MX PA06001759A MX PA06001759 A MXPA06001759 A MX PA06001759A

Authority

MX

Mexico

Prior art keywords

substituted

unsubstituted

methyl

alkyl

hydrogen

Prior art date

2003-08-15

Links

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• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 42
• 201000010099 disease Diseases 0.000 title claims abstract description 34
• 230000001613 neoplastic effect Effects 0.000 title claims description 10
• 208000027866 inflammatory disease Diseases 0.000 title claims description 6
• 230000002757 inflammatory effect Effects 0.000 title claims description 6
• 208000026278 immune system disease Diseases 0.000 title claims 4
• YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical class NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 title 1
• 125000003118 aryl group Chemical group 0.000 claims abstract description 40
• 230000005764 inhibitory process Effects 0.000 claims abstract description 18
• 239000003814 drug Substances 0.000 claims abstract description 14
• 238000004519 manufacturing process Methods 0.000 claims abstract description 14
• 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims abstract description 9
• 230000002265 prevention Effects 0.000 claims abstract description 8
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims abstract description 6
• -1 akoxy d-Cs Chemical group 0.000 claims description 717
• 150000001875 compounds Chemical class 0.000 claims description 160
• 229910052739 hydrogen Inorganic materials 0.000 claims description 121
• 239000001257 hydrogen Substances 0.000 claims description 118
• 125000003545 alkoxy group Chemical group 0.000 claims description 66
• 125000000217 alkyl group Chemical group 0.000 claims description 65
• 150000002431 hydrogen Chemical group 0.000 claims description 62
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 59
• 125000000623 heterocyclic group Chemical group 0.000 claims description 50
• 238000000034 method Methods 0.000 claims description 42
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 41
• 125000001424 substituent group Chemical group 0.000 claims description 41
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 41
• 229910052736 halogen Inorganic materials 0.000 claims description 40
• 150000002367 halogens Chemical class 0.000 claims description 39
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 38
• 125000001188 haloalkyl group Chemical group 0.000 claims description 38
• 150000003839 salts Chemical class 0.000 claims description 38
• 229910052717 sulfur Inorganic materials 0.000 claims description 38
• 125000001153 fluoro group Chemical group F* 0.000 claims description 34
• 125000005842 heteroatom Chemical group 0.000 claims description 34
• 229910052760 oxygen Inorganic materials 0.000 claims description 33
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 31
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 28
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 25
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 23
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 22
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 20
• 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 20
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
• 125000005843 halogen group Chemical group 0.000 claims description 19
• 239000004480 active ingredient Substances 0.000 claims description 18
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 18
• 150000003254 radicals Chemical class 0.000 claims description 18
• 239000000460 chlorine Substances 0.000 claims description 17
• 125000001072 heteroaryl group Chemical group 0.000 claims description 16
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 16
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
• 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 15
• 239000008194 pharmaceutical composition Substances 0.000 claims description 14
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 13
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 13
• 229910052801 chlorine Inorganic materials 0.000 claims description 13
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
• 230000000694 effects Effects 0.000 claims description 13
• 125000000586 2-(4-morpholinyl)ethoxy group Chemical group [H]C([H])(O*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 12
• GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 12
• 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims description 12
• 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims description 12
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 12
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 12
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
• 125000004104 aryloxy group Chemical group 0.000 claims description 11
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
• 229910052794 bromium Inorganic materials 0.000 claims description 11
• 125000004432 carbon atom Chemical group C* 0.000 claims description 11
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 11
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 11
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
• 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 claims description 10
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 10
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
• 208000035475 disorder Diseases 0.000 claims description 8
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 8
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 8
• 125000003386 piperidinyl group Chemical group 0.000 claims description 8
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 7
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 7
• 125000000172 C5-C10 aryl group Chemical group 0.000 claims description 7
• 125000002947 alkylene group Chemical group 0.000 claims description 7
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 7
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 7
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 6
• 206010025323 Lymphomas Diseases 0.000 claims description 6
• 210000001744 T-lymphocyte Anatomy 0.000 claims description 6
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 6
• 229940088679 drug related substance Drugs 0.000 claims description 6
• 230000001404 mediated effect Effects 0.000 claims description 6
• 125000004193 piperazinyl group Chemical group 0.000 claims description 6
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
• UYJNQQDJUOUFQJ-UHFFFAOYSA-N 2-[[5-chloro-2-[2-methoxy-4-(4-morpholinyl)anilino]-4-pyrimidinyl]amino]-N-methylbenzamide Chemical compound CNC(=O)C1=CC=CC=C1NC1=NC(NC=2C(=CC(=CC=2)N2CCOCC2)OC)=NC=C1Cl UYJNQQDJUOUFQJ-UHFFFAOYSA-N 0.000 claims description 5
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 5
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 5
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
• 210000000987 immune system Anatomy 0.000 claims description 5
• 230000002062 proliferating effect Effects 0.000 claims description 5
• 239000005977 Ethylene Substances 0.000 claims description 4
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
• 125000003282 alkyl amino group Chemical group 0.000 claims description 4
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
• 150000002825 nitriles Chemical class 0.000 claims description 4
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 3
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 3
• 208000026310 Breast neoplasm Diseases 0.000 claims description 3
• 239000008186 active pharmaceutical agent Substances 0.000 claims description 3
• 125000002431 aminoalkoxy group Chemical group 0.000 claims description 3
• 125000001246 bromo group Chemical group Br* 0.000 claims description 3
• 229910052792 caesium Inorganic materials 0.000 claims description 3
• 125000002837 carbocyclic group Chemical group 0.000 claims description 3
• 208000037765 diseases and disorders Diseases 0.000 claims description 3
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 3
• 150000004677 hydrates Chemical class 0.000 claims description 3
• 201000001441 melanoma Diseases 0.000 claims description 3
• 230000002611 ovarian Effects 0.000 claims description 3
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
• 125000004076 pyridyl group Chemical group 0.000 claims description 3
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
• 239000012453 solvate Substances 0.000 claims description 3
• 210000001685 thyroid gland Anatomy 0.000 claims description 3
• UWMGQQWDXJETSN-UHFFFAOYSA-N 2-[[5-bromo-2-(2-methoxy-5-morpholin-4-ylanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC=C1NC1=NC(NC=2C(=CC=C(C=2)N2CCOCC2)OC)=NC=C1Br UWMGQQWDXJETSN-UHFFFAOYSA-N 0.000 claims description 2
• UIURJGHFUQVQKB-UHFFFAOYSA-N 2-[[5-chloro-2-[2-methoxy-4-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]amino]-n-propan-2-ylbenzenesulfonamide Chemical compound COC1=CC(N2CCN(C)CC2)=CC=C1NC(N=1)=NC=C(Cl)C=1NC1=CC=CC=C1S(=O)(=O)NC(C)C UIURJGHFUQVQKB-UHFFFAOYSA-N 0.000 claims description 2
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
• 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 2
• 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 2
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 2
• 208000002699 Digestive System Neoplasms Diseases 0.000 claims description 2
• 125000004414 alkyl thio group Chemical group 0.000 claims description 2
• 210000003719 b-lymphocyte Anatomy 0.000 claims description 2
• 210000003979 eosinophil Anatomy 0.000 claims description 2
• 210000004602 germ cell Anatomy 0.000 claims description 2
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 2
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 2
• 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 2
• 230000001537 neural effect Effects 0.000 claims description 2
• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 201000008968 osteosarcoma Diseases 0.000 claims description 2
• 229940002612 prodrug Drugs 0.000 claims description 2
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• 208000025421 tumor of uterus Diseases 0.000 claims description 2
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• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
• 206010020751 Hypersensitivity Diseases 0.000 claims 1
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• 108010046882 ZAP-70 Protein-Tyrosine Kinase Proteins 0.000 abstract description 16
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• 239000000243 solution Substances 0.000 description 63
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• 239000000203 mixture Substances 0.000 description 60
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