ES2317201T3 - Nuevas 5-acil-indolinonas que contienen arilo, obtencion de las mismas y su utilizacion como medicamentos. - Google Patents

Info

Publication number

ES2317201T3

ES2317201T3 ES05715810T ES05715810T ES2317201T3 ES 2317201 T3 ES2317201 T3 ES 2317201T3 ES 05715810 T ES05715810 T ES 05715810T ES 05715810 T ES05715810 T ES 05715810T ES 2317201 T3 ES2317201 T3 ES 2317201T3

Authority

ES

Spain

Prior art keywords

alkyl

group

amino

substituted

alkoxy

Prior art date

2004-03-12

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Lifetime

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• 239000003814 drug Substances 0.000 title claims description 8
• 229940079593 drug Drugs 0.000 title claims description 6
• 239000000203 mixture Substances 0.000 claims abstract description 30
• 150000003839 salts Chemical class 0.000 claims abstract description 27
• 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 abstract description 18
• 125000003118 aryl group Chemical group 0.000 claims abstract description 8
• 125000000217 alkyl group Chemical group 0.000 claims description 130
• 150000001875 compounds Chemical class 0.000 claims description 71
• 125000003545 alkoxy group Chemical group 0.000 claims description 54
• -1 nitro, cyano, amino Chemical group 0.000 claims description 48
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 40
• 229910052757 nitrogen Inorganic materials 0.000 claims description 28
• 125000001424 substituent group Chemical group 0.000 claims description 24
• 239000000460 chlorine Substances 0.000 claims description 21
• 239000000126 substance Substances 0.000 claims description 21
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 20
• 229910052801 chlorine Inorganic materials 0.000 claims description 19
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 15
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 14
• 238000006243 chemical reaction Methods 0.000 claims description 14
• 229910052731 fluorine Inorganic materials 0.000 claims description 14
• 239000011737 fluorine Substances 0.000 claims description 14
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 12
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
• 125000001072 heteroaryl group Chemical group 0.000 claims description 12
• 229910052740 iodine Inorganic materials 0.000 claims description 12
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 11
• 125000004432 carbon atom Chemical group C* 0.000 claims description 11
• 238000004519 manufacturing process Methods 0.000 claims description 11
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 10
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 10
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
• 229910052794 bromium Inorganic materials 0.000 claims description 10
• 125000006842 cycloalkyleneimino group Chemical group 0.000 claims description 10
• 125000004429 atom Chemical group 0.000 claims description 9
• 238000000034 method Methods 0.000 claims description 9
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
• 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims description 8
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
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• 125000005842 heteroatom Chemical group 0.000 claims description 8
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
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• 229910052717 sulfur Inorganic materials 0.000 claims description 4
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• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
• QNFNCWDZCWGVHH-UHFFFAOYSA-N 5-acetyl-3-[(3,5-dimethoxyphenyl)-[4-[(dimethylamino)methyl]anilino]methylidene]-1h-indol-2-one Chemical compound COC1=CC(OC)=CC(C(NC=2C=CC(CN(C)C)=CC=2)=C2C3=CC(=CC=C3NC2=O)C(C)=O)=C1 QNFNCWDZCWGVHH-UHFFFAOYSA-N 0.000 claims description 2
• RKTSCIZXPPGSJB-UHFFFAOYSA-N 5-acetyl-3-[2,3-dihydro-1,4-benzodioxin-6-yl-[4-[(dimethylamino)methyl]anilino]methylidene]-1h-indol-2-one Chemical compound C1=CC(CN(C)C)=CC=C1NC(C=1C=C2OCCOC2=CC=1)=C1C2=CC(C(C)=O)=CC=C2NC1=O RKTSCIZXPPGSJB-UHFFFAOYSA-N 0.000 claims description 2
• PXKZNTZKSOMKQE-UHFFFAOYSA-N 5-acetyl-3-[[4-(diethylaminomethyl)anilino]-phenylmethylidene]-1h-indol-2-one Chemical compound C1=CC(CN(CC)CC)=CC=C1NC(C=1C=CC=CC=1)=C1C2=CC(C(C)=O)=CC=C2NC1=O PXKZNTZKSOMKQE-UHFFFAOYSA-N 0.000 claims description 2
• PBKNRZLAHOHFJY-UHFFFAOYSA-N 5-acetyl-3-[[4-[(dimethylamino)methyl]anilino]-(3-methoxyphenyl)methylidene]-1h-indol-2-one Chemical compound COC1=CC=CC(C(NC=2C=CC(CN(C)C)=CC=2)=C2C3=CC(=CC=C3NC2=O)C(C)=O)=C1 PBKNRZLAHOHFJY-UHFFFAOYSA-N 0.000 claims description 2
• 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 2
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
• 125000001246 bromo group Chemical group Br* 0.000 claims description 2
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
• 125000005111 carboxyalkoxy group Chemical group 0.000 claims description 2
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
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• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
• 230000003902 lesion Effects 0.000 claims description 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
• 150000007524 organic acids Chemical class 0.000 claims description 2
• 235000005985 organic acids Nutrition 0.000 claims description 2
• 229910052760 oxygen Inorganic materials 0.000 claims description 2
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
• 125000005544 phthalimido group Chemical group 0.000 claims description 2
• 239000003085 diluting agent Substances 0.000 claims 2
• 239000000969 carrier Substances 0.000 claims 1
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• 238000001819 mass spectrum Methods 0.000 description 82
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