MXPA03003580A - Inhibidores de la familia src con base de tienopirimidina. - Google Patents

Info

Publication number

MXPA03003580A

MXPA03003580A MXPA03003580A MXPA03003580A MXPA03003580A MX PA03003580 A MXPA03003580 A MX PA03003580A MX PA03003580 A MXPA03003580 A MX PA03003580A MX PA03003580 A MXPA03003580 A MX PA03003580A MX PA03003580 A MXPA03003580 A MX PA03003580A

Authority

MX

Mexico

Prior art keywords

hydrazone

pyrimidin

phenyl

methylthieno

hydroxy

Prior art date

2000-10-23

Links

• Espacenet
• Global Dossier
• Discuss

• RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical compound C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 title abstract description 57
• 239000003112 inhibitor Substances 0.000 title description 43
• 150000001875 compounds Chemical class 0.000 claims abstract description 137
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 62
• 201000010099 disease Diseases 0.000 claims abstract description 58
• 238000011282 treatment Methods 0.000 claims abstract description 53
• 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims abstract description 40
• 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims abstract description 40
• 208000026935 allergic disease Diseases 0.000 claims abstract description 19
• 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 18
• 230000000172 allergic effect Effects 0.000 claims abstract description 15
• 208000012902 Nervous system disease Diseases 0.000 claims abstract description 14
• 208000025966 Neurological disease Diseases 0.000 claims abstract description 14
• 230000003463 hyperproliferative effect Effects 0.000 claims abstract description 14
• 208000036142 Viral infection Diseases 0.000 claims abstract description 13
• 230000009385 viral infection Effects 0.000 claims abstract description 13
• 208000001132 Osteoporosis Diseases 0.000 claims abstract description 12
• 208000026278 immune system disease Diseases 0.000 claims abstract description 12
• 150000007857 hydrazones Chemical class 0.000 claims description 235
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 191
• -1 4-pyridinyl Chemical group 0.000 claims description 111
• GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 claims description 106
• 229910052739 hydrogen Inorganic materials 0.000 claims description 93
• 239000001257 hydrogen Substances 0.000 claims description 92
• JVTZFYYHCGSXJV-UHFFFAOYSA-N isovanillin Chemical compound COC1=CC=C(C=O)C=C1O JVTZFYYHCGSXJV-UHFFFAOYSA-N 0.000 claims description 86
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 79
• 125000000217 alkyl group Chemical group 0.000 claims description 76
• 210000004027 cell Anatomy 0.000 claims description 76
• QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 claims description 72
• 206010028980 Neoplasm Diseases 0.000 claims description 68
• 125000003118 aryl group Chemical group 0.000 claims description 58
• 229910052736 halogen Inorganic materials 0.000 claims description 46
• 150000002367 halogens Chemical group 0.000 claims description 46
• 239000003814 drug Substances 0.000 claims description 43
• CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 claims description 43
• 125000006574 non-aromatic ring group Chemical group 0.000 claims description 41
• 238000000034 method Methods 0.000 claims description 35
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 32
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 31
• 201000011510 cancer Diseases 0.000 claims description 23
• 150000003839 salts Chemical class 0.000 claims description 22
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
• 238000010992 reflux Methods 0.000 claims description 21
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 14
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 12
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 12
• 230000002401 inhibitory effect Effects 0.000 claims description 12
• 230000012010 growth Effects 0.000 claims description 10
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 10
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 8
• 239000003937 drug carrier Substances 0.000 claims description 8
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 7
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 7
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• 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 5
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 5
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• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 5
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• BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 claims description 5
• ADZUEEUKBYCSEY-UHFFFAOYSA-N 1h-indole-5-carbaldehyde Chemical compound O=CC1=CC=C2NC=CC2=C1 ADZUEEUKBYCSEY-UHFFFAOYSA-N 0.000 claims description 4
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
• IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 claims description 4
• WMPDAIZRQDCGFH-UHFFFAOYSA-N 3-methoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1 WMPDAIZRQDCGFH-UHFFFAOYSA-N 0.000 claims description 4
• UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 claims description 4
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 4
• 206010002198 Anaphylactic reaction Diseases 0.000 claims description 4
• 208000006386 Bone Resorption Diseases 0.000 claims description 4
• 241000124008 Mammalia Species 0.000 claims description 4
• NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 4
• 150000001299 aldehydes Chemical class 0.000 claims description 4
• 230000036783 anaphylactic response Effects 0.000 claims description 4
• 208000003455 anaphylaxis Diseases 0.000 claims description 4
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• 206010015037 epilepsy Diseases 0.000 claims description 4
• HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims description 4
• ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 claims description 4
• HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 claims description 4
• DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 claims description 4
• 101001004391 Drosophila melanogaster Protein jim lovell Proteins 0.000 claims description 3
• 230000022131 cell cycle Effects 0.000 claims description 3
• 230000004069 differentiation Effects 0.000 claims description 3
• 150000002431 hydrogen Chemical class 0.000 claims description 3
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
• 230000035755 proliferation Effects 0.000 claims description 3
• 230000002194 synthesizing effect Effects 0.000 claims description 3
• ZGTFNNUASMWGTM-UHFFFAOYSA-N 1,3-thiazole-2-carbaldehyde Chemical compound O=CC1=NC=CS1 ZGTFNNUASMWGTM-UHFFFAOYSA-N 0.000 claims description 2
• 125000006017 1-propenyl group Chemical group 0.000 claims description 2
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• UHDNUPHSDMOGCR-UHFFFAOYSA-N 3-Formylbenzoic acid Chemical compound OC(=O)C1=CC=CC(C=O)=C1 UHDNUPHSDMOGCR-UHFFFAOYSA-N 0.000 claims description 2
• SUISZCALMBHJQX-UHFFFAOYSA-N 3-bromobenzaldehyde Chemical compound BrC1=CC=CC(C=O)=C1 SUISZCALMBHJQX-UHFFFAOYSA-N 0.000 claims description 2
• 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 2
• VGSOCYWCRMXQAB-UHFFFAOYSA-N 3-chloro-4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1Cl VGSOCYWCRMXQAB-UHFFFAOYSA-N 0.000 claims description 2
• QZMGMXBYJZVAJN-UHFFFAOYSA-N 3-ethoxybenzaldehyde Chemical compound CCOC1=CC=CC(C=O)=C1 QZMGMXBYJZVAJN-UHFFFAOYSA-N 0.000 claims description 2
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