BRPI0706621A2 - composto, composição farmacêutica, métodos para tratar um distúrbio mediado por quinase em um mamìfero e para tratar um distúrbio relacionado com a proliferação em um mamìfero, e , uso do composto - Google Patents

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Publication number

BRPI0706621A2

BRPI0706621A2 BRPI0706621-0A BRPI0706621A BRPI0706621A2 BR PI0706621 A2 BRPI0706621 A2 BR PI0706621A2 BR PI0706621 A BRPI0706621 A BR PI0706621A BR PI0706621 A2 BRPI0706621 A2 BR PI0706621A2

Authority

BR

Brazil

Prior art keywords

formula

amino

thiazol

alkyl

phenyl

Prior art date

2006-01-18

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 283
• 238000000034 method Methods 0.000 title claims abstract description 98
• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 39
• 230000001404 mediated effect Effects 0.000 title claims abstract description 30
• 108091000080 Phosphotransferase Proteins 0.000 title claims abstract description 24
• 102000020233 phosphotransferase Human genes 0.000 title claims abstract description 24
• 241000124008 Mammalia Species 0.000 title claims description 24
• 230000035755 proliferation Effects 0.000 title claims description 8
• 239000000203 mixture Substances 0.000 claims abstract description 164
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 96
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 65
• 201000011510 cancer Diseases 0.000 claims abstract description 52
• 208000035475 disorder Diseases 0.000 claims abstract description 49
• 201000010099 disease Diseases 0.000 claims abstract description 47
• 230000010261 cell growth Effects 0.000 claims abstract description 15
• 230000002159 abnormal effect Effects 0.000 claims abstract description 14
• 206010061218 Inflammation Diseases 0.000 claims abstract description 12
• 230000004054 inflammatory process Effects 0.000 claims abstract description 12
• 208000030159 metabolic disease Diseases 0.000 claims abstract description 11
• -1 C 1 -C 6 alkoxy Chemical group 0.000 claims description 582
• 125000003118 aryl group Chemical group 0.000 claims description 127
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 95
• 125000001072 heteroaryl group Chemical group 0.000 claims description 84
• 125000000623 heterocyclic group Chemical group 0.000 claims description 73
• 102100033810 RAC-alpha serine/threonine-protein kinase Human genes 0.000 claims description 57
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 49
• 125000000217 alkyl group Chemical group 0.000 claims description 45
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 44
• 239000003814 drug Substances 0.000 claims description 41
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
• 150000003839 salts Chemical class 0.000 claims description 34
• 125000005843 halogen group Chemical group 0.000 claims description 32
• 238000009739 binding Methods 0.000 claims description 31
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 29
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 27
• 125000005842 heteroatom Chemical group 0.000 claims description 27
• 230000027455 binding Effects 0.000 claims description 24
• 125000001424 substituent group Chemical group 0.000 claims description 24
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 23
• 125000004432 carbon atom Chemical group C* 0.000 claims description 23
• 125000004076 pyridyl group Chemical group 0.000 claims description 23
• 229940124597 therapeutic agent Drugs 0.000 claims description 22
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 21
• 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims description 19
• 229910052799 carbon Inorganic materials 0.000 claims description 18
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
• JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims description 18
• 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims description 16
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 16
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
• 229910052757 nitrogen Inorganic materials 0.000 claims description 16
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 15
• 125000002837 carbocyclic group Chemical group 0.000 claims description 14
• 229910052739 hydrogen Inorganic materials 0.000 claims description 14
• 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 14
• 238000002360 preparation method Methods 0.000 claims description 14
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 13
• 125000002619 bicyclic group Chemical group 0.000 claims description 13
• 230000005764 inhibitory process Effects 0.000 claims description 12
• 101710113459 RAC-alpha serine/threonine-protein kinase Proteins 0.000 claims description 11
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 11
• 125000002541 furyl group Chemical group 0.000 claims description 11
• 229910052760 oxygen Inorganic materials 0.000 claims description 11
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 10
• 125000001041 indolyl group Chemical group 0.000 claims description 10
• 125000001624 naphthyl group Chemical group 0.000 claims description 10
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 9
• 125000002950 monocyclic group Chemical group 0.000 claims description 9
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 9
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 8
• 125000003545 alkoxy group Chemical group 0.000 claims description 8
• 206010012601 diabetes mellitus Diseases 0.000 claims description 8
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 8
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• 125000001544 thienyl group Chemical group 0.000 claims description 8
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 7
• RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims description 7
• 102000008130 Cyclic AMP-Dependent Protein Kinases Human genes 0.000 claims description 7
• 101100481408 Danio rerio tie2 gene Proteins 0.000 claims description 7
• 125000004429 atom Chemical group 0.000 claims description 7
• 125000001246 bromo group Chemical group Br* 0.000 claims description 7
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
• 125000006308 propyl amino group Chemical group 0.000 claims description 7
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 6
• 125000006345 2,2,2-trifluoroethoxymethyl group Chemical group [H]C([H])(*)OC([H])([H])C(F)(F)F 0.000 claims description 6
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 6
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 6
• 101100481410 Mus musculus Tek gene Proteins 0.000 claims description 6
• 208000016097 disease of metabolism Diseases 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 claims description 6
• 108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 claims description 6
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
• YOHYSYJDKVYCJI-UHFFFAOYSA-N n-[3-[[6-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]phenyl]cyclopropanecarboxamide Chemical compound FC(F)(F)C1=CC=CC(NC=2N=CN=C(NC=3C=C(NC(=O)C4CC4)C=CC=3)C=2)=C1 YOHYSYJDKVYCJI-UHFFFAOYSA-N 0.000 claims description 6
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
• 102000001267 GSK3 Human genes 0.000 claims description 5
• 108060006662 GSK3 Proteins 0.000 claims description 5
• 101000669921 Homo sapiens Rho-associated protein kinase 2 Proteins 0.000 claims description 5
• 101001001648 Homo sapiens Serine/threonine-protein kinase pim-2 Proteins 0.000 claims description 5
• 102000003923 Protein Kinase C Human genes 0.000 claims description 5
• 102100039314 Rho-associated protein kinase 2 Human genes 0.000 claims description 5
• 102100036120 Serine/threonine-protein kinase pim-2 Human genes 0.000 claims description 5
• NFVJNJQRWPQVOA-UHFFFAOYSA-N n-[2-chloro-5-(trifluoromethyl)phenyl]-2-[3-(4-ethyl-5-ethylsulfanyl-1,2,4-triazol-3-yl)piperidin-1-yl]acetamide Chemical compound CCN1C(SCC)=NN=C1C1CN(CC(=O)NC=2C(=CC=C(C=2)C(F)(F)F)Cl)CCC1 NFVJNJQRWPQVOA-UHFFFAOYSA-N 0.000 claims description 5
• PRXJKVDDVOWRHR-SFHVURJKSA-N (2s)-1-n-(5-phthalazin-6-yl-1,3-thiazol-2-yl)-3-[4-(trifluoromethyl)phenyl]propane-1,2-diamine Chemical compound C([C@@H](CNC=1SC(=CN=1)C=1C=C2C=NN=CC2=CC=1)N)C1=CC=C(C(F)(F)F)C=C1 PRXJKVDDVOWRHR-SFHVURJKSA-N 0.000 claims description 4
• KMDQAOCMEQUOAQ-INIZCTEOSA-N (2s)-1-n-[5-(1,6-naphthyridin-2-yl)-1,3-thiazol-2-yl]-3-[4-(trifluoromethyl)phenyl]propane-1,2-diamine Chemical compound C([C@@H](CNC=1SC(=CN=1)C=1N=C2C=CN=CC2=CC=1)N)C1=CC=C(C(F)(F)F)C=C1 KMDQAOCMEQUOAQ-INIZCTEOSA-N 0.000 claims description 4
• TYCJPDLIEVIZMC-INIZCTEOSA-N (2s)-1-n-[5-(3-methyl-2h-indazol-5-yl)-1,3-thiazol-2-yl]-3-phenylpropane-1,2-diamine Chemical group C([C@H](N)CNC1=NC=C(S1)C1=CC=C2NN=C(C2=C1)C)C1=CC=CC=C1 TYCJPDLIEVIZMC-INIZCTEOSA-N 0.000 claims description 4
• VGPQUILKMXOHDS-IBGZPJMESA-N (2s)-3-(3-chlorophenyl)-1-n-(5-isoquinolin-6-yl-1,3-thiazol-2-yl)propane-1,2-diamine Chemical compound C([C@@H](CNC=1SC(=CN=1)C=1C=C2C=CN=CC2=CC=1)N)C1=CC=CC(Cl)=C1 VGPQUILKMXOHDS-IBGZPJMESA-N 0.000 claims description 4
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
• 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 4
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
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• 101000877727 Homo sapiens Forkhead box protein O1 Proteins 0.000 claims description 4
• 101000595531 Homo sapiens Serine/threonine-protein kinase pim-1 Proteins 0.000 claims description 4
• 108010001127 Insulin Receptor Proteins 0.000 claims description 4
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• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• RUQPVADMLMMXDR-IBGZPJMESA-N (2s)-1-n-(5-isoquinolin-6-yl-1,3-thiazol-2-yl)-3-[4-(trifluoromethyl)phenyl]propane-1,2-diamine Chemical compound C([C@@H](CNC=1SC(=CN=1)C=1C=C2C=CN=CC2=CC=1)N)C1=CC=C(C(F)(F)F)C=C1 RUQPVADMLMMXDR-IBGZPJMESA-N 0.000 claims description 3
• ONHHLCOLUPUJHO-DEOSSOPVSA-N (2s)-1-n-(5-isoquinolin-6-yl-4-phenyl-1,3-thiazol-2-yl)-3-[4-(trifluoromethyl)phenyl]propane-1,2-diamine Chemical compound C([C@@H](N)CC=1C=CC(=CC=1)C(F)(F)F)NC(SC=1C=2C=C3C=CN=CC3=CC=2)=NC=1C1=CC=CC=C1 ONHHLCOLUPUJHO-DEOSSOPVSA-N 0.000 claims description 3
• VGRYHOBWAAWMSO-NRFANRHFSA-N (2s)-1-n-[4-(furan-2-yl)-5-isoquinolin-6-yl-1,3-thiazol-2-yl]-3-[4-(trifluoromethyl)phenyl]propane-1,2-diamine Chemical compound C([C@@H](N)CC=1C=CC(=CC=1)C(F)(F)F)NC(SC=1C=2C=C3C=CN=CC3=CC=2)=NC=1C1=CC=CO1 VGRYHOBWAAWMSO-NRFANRHFSA-N 0.000 claims description 3
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• XJADBOIGESUADD-INIZCTEOSA-N (2s)-3-(4-chlorophenyl)-1-n-[5-(3-methyl-2h-indazol-5-yl)-1,3-thiazol-2-yl]propane-1,2-diamine Chemical compound C([C@H](N)CNC1=NC=C(S1)C1=CC=C2NN=C(C2=C1)C)C1=CC=C(Cl)C=C1 XJADBOIGESUADD-INIZCTEOSA-N 0.000 claims description 3
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• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 3
• 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 3
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 3
• BHMIRPVVPZIEGW-INIZCTEOSA-N 4-[2-[[(2s)-2-amino-3-[4-(trifluoromethyl)phenyl]propyl]amino]-1,3-thiazol-5-yl]benzamide Chemical compound C([C@@H](N)CC=1C=CC(=CC=1)C(F)(F)F)NC(S1)=NC=C1C1=CC=C(C(N)=O)C=C1 BHMIRPVVPZIEGW-INIZCTEOSA-N 0.000 claims description 3
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• XGNAWINLKHSMKO-INIZCTEOSA-N 5-[2-[[(2s)-2-amino-3-[3-(trifluoromethyl)phenyl]propyl]amino]-1,3-thiazol-5-yl]-1,3-dihydroindol-2-one Chemical compound C([C@@H](CNC=1SC(=CN=1)C=1C=C2CC(=O)NC2=CC=1)N)C1=CC=CC(C(F)(F)F)=C1 XGNAWINLKHSMKO-INIZCTEOSA-N 0.000 claims description 3
• FNQWGQWNXGGAFV-AWEZNQCLSA-N 6-[2-[[(2s)-2-amino-3-(4-methoxyphenyl)propyl]amino]-1,3-thiazol-5-yl]-3h-1,3-benzoxazol-2-one Chemical compound C1=CC(OC)=CC=C1C[C@H](N)CNC1=NC=C(C=2C=C3OC(=O)NC3=CC=2)S1 FNQWGQWNXGGAFV-AWEZNQCLSA-N 0.000 claims description 3
• JDMVDVWEHDEPEM-KRWDZBQOSA-N 6-[2-[[(2s)-2-amino-3-[4-(trifluoromethyl)phenyl]propyl]amino]-1,3-thiazol-5-yl]-3,4-dihydro-1h-quinolin-2-one Chemical compound C([C@@H](CNC=1SC(=CN=1)C=1C=C2CCC(=O)NC2=CC=1)N)C1=CC=C(C(F)(F)F)C=C1 JDMVDVWEHDEPEM-KRWDZBQOSA-N 0.000 claims description 3
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• UVFXPMPINVJLQC-INIZCTEOSA-N [2-[[(2s)-2-amino-3-[4-(trifluoromethyl)phenyl]propyl]amino]-5-(1h-indazol-5-yl)-1,3-thiazol-4-yl]methanol Chemical compound C([C@@H](CNC=1SC(=C(CO)N=1)C=1C=C2C=NNC2=CC=1)N)C1=CC=C(C(F)(F)F)C=C1 UVFXPMPINVJLQC-INIZCTEOSA-N 0.000 claims description 3
• QDYCTALEGOKETB-IBGZPJMESA-N [2-[[(2s)-2-amino-3-[4-(trifluoromethyl)phenyl]propyl]amino]-5-isoquinolin-6-yl-1,3-thiazol-4-yl]methanol Chemical compound C([C@@H](CNC=1SC(=C(CO)N=1)C=1C=C2C=CN=CC2=CC=1)N)C1=CC=C(C(F)(F)F)C=C1 QDYCTALEGOKETB-IBGZPJMESA-N 0.000 claims description 3
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