BRPI0720635A2 - Compostos orgânicos e seus usos - Google Patents

Info

Publication number

BRPI0720635A2

BRPI0720635A2 BRPI0720635-6A BRPI0720635A BRPI0720635A2 BR PI0720635 A2 BRPI0720635 A2 BR PI0720635A2 BR PI0720635 A BRPI0720635 A BR PI0720635A BR PI0720635 A2 BRPI0720635 A2 BR PI0720635A2

Authority

BR

Brazil

Prior art keywords

substituted

unsubstituted

alkyl

group

compound

Prior art date

2006-12-22

Links

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• 150000002894 organic compounds Chemical class 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims description 335
• -1 nitro, hydroxy Chemical group 0.000 claims description 217
• 125000000217 alkyl group Chemical group 0.000 claims description 125
• 229910052739 hydrogen Inorganic materials 0.000 claims description 125
• 239000001257 hydrogen Substances 0.000 claims description 94
• 102000001253 Protein Kinase Human genes 0.000 claims description 91
• 108060006633 protein kinase Proteins 0.000 claims description 91
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 89
• 229910052736 halogen Inorganic materials 0.000 claims description 82
• 150000002367 halogens Chemical class 0.000 claims description 78
• 125000003118 aryl group Chemical group 0.000 claims description 73
• 238000000034 method Methods 0.000 claims description 72
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 59
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 55
• 208000035475 disorder Diseases 0.000 claims description 51
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 47
• 206010028980 Neoplasm Diseases 0.000 claims description 45
• 125000000623 heterocyclic group Chemical group 0.000 claims description 45
• 125000003545 alkoxy group Chemical group 0.000 claims description 43
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 38
• 102100024457 Cyclin-dependent kinase 9 Human genes 0.000 claims description 38
• 101000980930 Homo sapiens Cyclin-dependent kinase 9 Proteins 0.000 claims description 38
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 34
• 150000003839 salts Chemical class 0.000 claims description 34
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 33
• 201000011510 cancer Diseases 0.000 claims description 31
• 238000006243 chemical reaction Methods 0.000 claims description 28
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 28
• 238000011282 treatment Methods 0.000 claims description 28
• 229910052799 carbon Inorganic materials 0.000 claims description 27
• IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 26
• 230000000694 effects Effects 0.000 claims description 25
• 229910052757 nitrogen Inorganic materials 0.000 claims description 25
• 206010061218 Inflammation Diseases 0.000 claims description 24
• 230000004054 inflammatory process Effects 0.000 claims description 24
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 23
• 150000002148 esters Chemical class 0.000 claims description 23
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 22
• 208000036142 Viral infection Diseases 0.000 claims description 20
• 239000003795 chemical substances by application Substances 0.000 claims description 20
• 239000003814 drug Substances 0.000 claims description 20
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 20
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• 108010025464 Cyclin-Dependent Kinase 4 Proteins 0.000 claims description 19
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• 150000001408 amides Chemical class 0.000 claims description 19
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• 102100026810 Cyclin-dependent kinase 7 Human genes 0.000 claims description 18
• 101000911952 Homo sapiens Cyclin-dependent kinase 7 Proteins 0.000 claims description 18
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
• 239000000460 chlorine Chemical group 0.000 claims description 18
• 150000002825 nitriles Chemical class 0.000 claims description 16
• 229910052760 oxygen Inorganic materials 0.000 claims description 16
• 206010007572 Cardiac hypertrophy Diseases 0.000 claims description 15
• 208000006029 Cardiomegaly Diseases 0.000 claims description 15
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 15
• BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 14
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 14
• 108010025454 Cyclin-Dependent Kinase 5 Proteins 0.000 claims description 14
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• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 14
• 150000001412 amines Chemical class 0.000 claims description 14
• 229940079593 drug Drugs 0.000 claims description 14
• BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 13
• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 13
• 239000003112 inhibitor Substances 0.000 claims description 13
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 12
• 125000003277 amino group Chemical group 0.000 claims description 12
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
• 108010025468 Cyclin-Dependent Kinase 6 Proteins 0.000 claims description 11
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• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 11
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 11
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• 241000124008 Mammalia Species 0.000 claims description 10
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
• 229910052731 fluorine Inorganic materials 0.000 claims description 10
• 230000002496 gastric effect Effects 0.000 claims description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 9
• 208000037976 chronic inflammation Diseases 0.000 claims description 9
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 9
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
• 150000003852 triazoles Chemical class 0.000 claims description 9
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• 101000715946 Homo sapiens Cyclin-dependent kinase 3 Proteins 0.000 claims description 8
• 101000980937 Homo sapiens Cyclin-dependent kinase 8 Proteins 0.000 claims description 8
• 241000725303 Human immunodeficiency virus Species 0.000 claims description 8
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 8
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 8
• 230000004663 cell proliferation Effects 0.000 claims description 8
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• 210000001072 colon Anatomy 0.000 claims description 8
• 231100000433 cytotoxic Toxicity 0.000 claims description 8
• 230000001472 cytotoxic effect Effects 0.000 claims description 8
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 8
• 210000000056 organ Anatomy 0.000 claims description 8
• 150000003457 sulfones Chemical class 0.000 claims description 8
• NAROVGXVMKGQLH-UHFFFAOYSA-N 4-(1h-imidazol-2-yl)morpholine Chemical compound C1COCCN1C1=NC=CN1 NAROVGXVMKGQLH-UHFFFAOYSA-N 0.000 claims description 7
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 7
• JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 claims description 7
• 239000011737 fluorine Substances 0.000 claims description 7
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• NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 claims description 6
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
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• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
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• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
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• FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 claims description 5
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• 229910052794 bromium Inorganic materials 0.000 claims description 5
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
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• 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 4
• NQVIIUBWMBHLOZ-UHFFFAOYSA-N 2-[2-hydroxyethyl-[6-[(4-methoxyphenyl)methylamino]-9-propan-2-ylpurin-2-yl]amino]ethanol Chemical compound C1=CC(OC)=CC=C1CNC1=NC(N(CCO)CCO)=NC2=C1N=CN2C(C)C NQVIIUBWMBHLOZ-UHFFFAOYSA-N 0.000 claims description 4
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• OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 claims description 4
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