ES2494365T3 - Compuestos de pirazolopirimidina que inhiben PI3K y métodos de uso - Google Patents

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Publication number

ES2494365T3

ES2494365T3 ES09706948.8T ES09706948T ES2494365T3 ES 2494365 T3 ES2494365 T3 ES 2494365T3 ES 09706948 T ES09706948 T ES 09706948T ES 2494365 T3 ES2494365 T3 ES 2494365T3

Authority

ES

Spain

Prior art keywords

pyrazolo

methyl

indazol

pyrimidin

heteroaryl

Prior art date

2008-01-30

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.)

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• 238000000034 method Methods 0.000 title claims description 203
• 108091007960 PI3Ks Proteins 0.000 title claims description 15
• 102000010400 1-phosphatidylinositol-3-kinase activity proteins Human genes 0.000 title claims 2
• OGEBRHQLRGFBNV-RZDIXWSQSA-N chembl2036808 Chemical class C12=NC(NCCCC)=NC=C2C(C=2C=CC(F)=CC=2)=NN1C[C@H]1CC[C@H](N)CC1 OGEBRHQLRGFBNV-RZDIXWSQSA-N 0.000 title description 2
• -1 -CH2OH Chemical group 0.000 claims abstract description 256
• 150000001875 compounds Chemical class 0.000 claims abstract description 218
• 125000002947 alkylene group Chemical group 0.000 claims abstract description 68
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims abstract description 54
• 125000006736 (C6-C20) aryl group Chemical group 0.000 claims abstract description 39
• 150000003839 salts Chemical class 0.000 claims abstract description 36
• 125000003118 aryl group Chemical group 0.000 claims abstract description 30
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 28
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 25
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 25
• 125000004419 alkynylene group Chemical group 0.000 claims abstract description 24
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 24
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 24
• 229910052801 chlorine Inorganic materials 0.000 claims abstract description 23
• 229910052740 iodine Inorganic materials 0.000 claims abstract description 22
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 22
• 229910052794 bromium Inorganic materials 0.000 claims abstract description 21
• 229910052731 fluorine Inorganic materials 0.000 claims abstract description 21
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 21
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 19
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 15
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims abstract description 14
• 125000000304 alkynyl group Chemical group 0.000 claims abstract description 13
• 125000004452 carbocyclyl group Chemical group 0.000 claims abstract description 13
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims abstract description 12
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims abstract description 11
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 11
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 11
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 11
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 10
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 10
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 9
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 8
• 125000006413 ring segment Chemical group 0.000 claims abstract description 7
• 125000002950 monocyclic group Chemical group 0.000 claims abstract description 6
• 125000004122 cyclic group Chemical group 0.000 claims abstract description 5
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• 208000035475 disorder Diseases 0.000 claims description 31
• 201000011510 cancer Diseases 0.000 claims description 27
• 239000008194 pharmaceutical composition Substances 0.000 claims description 24
• 239000003795 chemical substances by application Substances 0.000 claims description 18
• 241000124008 Mammalia Species 0.000 claims description 16
• 239000002246 antineoplastic agent Substances 0.000 claims description 14
• 125000002619 bicyclic group Chemical group 0.000 claims description 13
• 229940127089 cytotoxic agent Drugs 0.000 claims description 13
• 230000001225 therapeutic effect Effects 0.000 claims description 13
• 230000003463 hyperproliferative effect Effects 0.000 claims description 12
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 12
• 239000003085 diluting agent Substances 0.000 claims description 11
• 238000004519 manufacturing process Methods 0.000 claims description 10
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
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• 125000004076 pyridyl group Chemical group 0.000 claims description 5
• BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical group C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 4
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• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 4
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
• 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 4
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 4
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• 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
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• 125000000335 thiazolyl group Chemical group 0.000 claims description 4
• 125000001425 triazolyl group Chemical group 0.000 claims description 4
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• DVFCXODQTMEIII-UHFFFAOYSA-N 1-[3-[[6-(1h-indazol-4-yl)-1-methylpyrazolo[3,4-d]pyrimidin-4-yl]amino]propyl]pyrrolidin-2-one Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2N(C)N=CC2=C1NCCCN1CCCC1=O DVFCXODQTMEIII-UHFFFAOYSA-N 0.000 claims description 3
• DEDPRRGCSNEHDQ-UHFFFAOYSA-N 1-ethyl-6-(1h-indazol-4-yl)-n-(3-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2N(CC)N=CC2=C1NC1=CC=CC(OC)=C1 DEDPRRGCSNEHDQ-UHFFFAOYSA-N 0.000 claims description 3
• JUXOGGBJGKFDTQ-UHFFFAOYSA-N 6-(1h-indazol-4-yl)-n-(3-methoxyphenyl)-1,3-dimethylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound COC1=CC=CC(NC=2C=3C(C)=NN(C)C=3N=C(N=2)C=2C=3C=NNC=3C=CC=2)=C1 JUXOGGBJGKFDTQ-UHFFFAOYSA-N 0.000 claims description 3
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• OGCQGFQJVQHXRO-UHFFFAOYSA-N n'-[6-(1h-indazol-4-yl)-1-methylpyrazolo[3,4-d]pyrimidin-4-yl]-n,n,n'-trimethylethane-1,2-diamine Chemical compound N=1C=2N(C)N=CC=2C(N(C)CCN(C)C)=NC=1C1=CC=CC2=C1C=NN2 OGCQGFQJVQHXRO-UHFFFAOYSA-N 0.000 claims description 3
• PUTDXFRAEQEARA-UHFFFAOYSA-N n-(1,3-benzodioxol-5-yl)-6-(1h-indazol-4-yl)-1-methylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound N1=C2N(C)N=CC2=C(NC=2C=C3OCOC3=CC=2)N=C1C1=CC=CC2=C1C=NN2 PUTDXFRAEQEARA-UHFFFAOYSA-N 0.000 claims description 3
• HRWGMCMXHYQOMA-UHFFFAOYSA-N n-(3,4-dimethoxyphenyl)-6-(1h-indazol-4-yl)-1-methylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC(C=2C=3C=NNC=3C=CC=2)=NC2=C1C=NN2C HRWGMCMXHYQOMA-UHFFFAOYSA-N 0.000 claims description 3
• KXXIEFFDVCDMCR-UHFFFAOYSA-N n-(3-methoxyphenyl)-1-methyl-6-(1h-pyrazol-4-yl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound COC1=CC=CC(NC=2C=3C=NN(C)C=3N=C(N=2)C2=CNN=C2)=C1 KXXIEFFDVCDMCR-UHFFFAOYSA-N 0.000 claims description 3
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