ES2533788T3 - Compuestos inhibidores de PI3K de tipo purina y métodos de uso - Google Patents
Compuestos inhibidores de PI3K de tipo purina y métodos de uso Download PDFInfo
- Publication number
- ES2533788T3 ES2533788T3 ES09755767.2T ES09755767T ES2533788T3 ES 2533788 T3 ES2533788 T3 ES 2533788T3 ES 09755767 T ES09755767 T ES 09755767T ES 2533788 T3 ES2533788 T3 ES 2533788T3
- Authority
- ES
- Spain
- Prior art keywords
- morpholino
- purin
- alkylene
- methyl
- heterocyclyl
- Prior art date
- 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.)
- Active
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- 150000001875 compounds Chemical class 0.000 title abstract description 9
- 239000012828 PI3K inhibitor Substances 0.000 title 1
- 229940043441 phosphoinositide 3-kinase inhibitor Drugs 0.000 title 1
- -1 -CH2OH Chemical group 0.000 abstract description 18
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract description 3
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- 125000002947 alkylene group Chemical group 0.000 abstract description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 3
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 abstract description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 2
- 125000001072 heteroaryl group Chemical group 0.000 abstract 2
- 125000006736 (C6-C20) aryl group Chemical group 0.000 abstract 1
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 abstract 1
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004452 carbocyclyl group Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 229940095102 methyl benzoate Drugs 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- AOUUDIQPMYTKOI-UHFFFAOYSA-N 1-[2-[2-(2-aminopyrimidin-5-yl)-6-morpholin-4-ylpurin-9-yl]acetyl]-n-methylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)NC)CCN1C(=O)CN1C2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2N=C1 AOUUDIQPMYTKOI-UHFFFAOYSA-N 0.000 description 1
- WSNVDDJLJHPORH-UHFFFAOYSA-N 1-[3-[2-(2-aminopyrimidin-5-yl)-6-morpholin-4-ylpurin-9-yl]propanoyl]-n-methylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)NC)CCN1C(=O)CCN1C2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2N=C1 WSNVDDJLJHPORH-UHFFFAOYSA-N 0.000 description 1
- HKSCZWCKMLMLDU-UHFFFAOYSA-N 1-[3-[[2-(2-aminopyrimidin-5-yl)-6-morpholin-4-ylpurin-9-yl]methyl]pyrrolidin-1-yl]ethanone Chemical compound C1N(C(=O)C)CCC1CN1C2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2N=C1 HKSCZWCKMLMLDU-UHFFFAOYSA-N 0.000 description 1
- AGDHHJRWRSOCAF-UHFFFAOYSA-N 1-[4-[[2-(2-aminopyrimidin-5-yl)-6-morpholin-4-ylpurin-9-yl]methyl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1CN1C2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2N=C1 AGDHHJRWRSOCAF-UHFFFAOYSA-N 0.000 description 1
- XHVHZFXNUIYBBO-UHFFFAOYSA-N 2-[2-(1h-indazol-4-yl)-9-methyl-6-morpholin-4-ylpurin-8-yl]propan-2-ol Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2N(C)C(C(C)(C)O)=NC2=C1N1CCOCC1 XHVHZFXNUIYBBO-UHFFFAOYSA-N 0.000 description 1
- KQNBNJOVKJOMDH-UHFFFAOYSA-N 2-[2-(2-aminopyrimidin-5-yl)-6-morpholin-4-yl-9-propylpurin-8-yl]propan-2-ol Chemical compound N1=C2N(CCC)C(C(C)(C)O)=NC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 KQNBNJOVKJOMDH-UHFFFAOYSA-N 0.000 description 1
- GFRPGDSXDPEGMV-UHFFFAOYSA-N 2-[2-(2-aminopyrimidin-5-yl)-6-morpholin-4-ylpurin-9-yl]-1-(4-methylsulfonylpiperazin-1-yl)ethanone Chemical compound C1CN(S(=O)(=O)C)CCN1C(=O)CN1C2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2N=C1 GFRPGDSXDPEGMV-UHFFFAOYSA-N 0.000 description 1
- QQDUFKGDCXYVHR-UHFFFAOYSA-N 2-[2-(2-aminopyrimidin-5-yl)-6-morpholin-4-ylpurin-9-yl]-1-morpholin-4-ylethanone Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(N=CN2CC(=O)N3CCOCC3)C2=N1 QQDUFKGDCXYVHR-UHFFFAOYSA-N 0.000 description 1
- AJVDFTWUNKUSJU-UHFFFAOYSA-N 2-[2-(2-aminopyrimidin-5-yl)-6-morpholin-4-ylpurin-9-yl]acetic acid Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(N=CN2CC(O)=O)C2=N1 AJVDFTWUNKUSJU-UHFFFAOYSA-N 0.000 description 1
- HDTHTJYWODPMJO-UHFFFAOYSA-N 2-[2-(2-aminopyrimidin-5-yl)-6-morpholin-4-ylpurin-9-yl]ethanol Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(N=CN2CCO)C2=N1 HDTHTJYWODPMJO-UHFFFAOYSA-N 0.000 description 1
- QJGFOGJKIDPKSZ-UHFFFAOYSA-N 2-[2-(2-aminopyrimidin-5-yl)-9-butyl-6-morpholin-4-ylpurin-8-yl]propan-2-ol Chemical compound N1=C2N(CCCC)C(C(C)(C)O)=NC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 QJGFOGJKIDPKSZ-UHFFFAOYSA-N 0.000 description 1
- YWTFMRUDEJHZGF-UHFFFAOYSA-N 2-[2-(2-aminopyrimidin-5-yl)-9-methyl-6-morpholin-4-ylpurin-8-yl]propan-2-ol Chemical compound N1=C2N(C)C(C(C)(C)O)=NC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 YWTFMRUDEJHZGF-UHFFFAOYSA-N 0.000 description 1
- LWQWJNNUZUSBMF-UHFFFAOYSA-N 2-[2-(3-hydroxyphenyl)-6-morpholin-4-ylpurin-9-yl]-n-methylacetamide Chemical compound N1=C2N(CC(=O)NC)C=NC2=C(N2CCOCC2)N=C1C1=CC=CC(O)=C1 LWQWJNNUZUSBMF-UHFFFAOYSA-N 0.000 description 1
- XCEDXQNTFRMXPP-UHFFFAOYSA-N 2-[2-(6-aminopyridin-3-yl)-9-methyl-6-morpholin-4-ylpurin-8-yl]propan-2-ol Chemical compound N1=C2N(C)C(C(C)(C)O)=NC2=C(N2CCOCC2)N=C1C1=CC=C(N)N=C1 XCEDXQNTFRMXPP-UHFFFAOYSA-N 0.000 description 1
- NMTMVOGZGOVEJE-UHFFFAOYSA-N 2-[4-[[2-(2-amino-4-methylpyrimidin-5-yl)-9-ethyl-6-morpholin-4-ylpurin-8-yl]methyl]piperazin-1-yl]-2-methylpropanamide Chemical compound N=1C2=C(N3CCOCC3)N=C(C=3C(=NC(N)=NC=3)C)N=C2N(CC)C=1CN1CCN(C(C)(C)C(N)=O)CC1 NMTMVOGZGOVEJE-UHFFFAOYSA-N 0.000 description 1
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 1
- GRGVZPAJQCAWAX-UHFFFAOYSA-N 3-(9-benzyl-6-morpholin-4-ylpurin-2-yl)phenol Chemical compound OC1=CC=CC(C=2N=C3N(CC=4C=CC=CC=4)C=NC3=C(N3CCOCC3)N=2)=C1 GRGVZPAJQCAWAX-UHFFFAOYSA-N 0.000 description 1
- NITGMBBDIUJMRW-UHFFFAOYSA-N 3-[2-(2-aminopyrimidin-5-yl)-6-morpholin-4-ylpurin-9-yl]-1-(4-methylsulfonylpiperazin-1-yl)propan-1-one Chemical compound C1CN(S(=O)(=O)C)CCN1C(=O)CCN1C2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2N=C1 NITGMBBDIUJMRW-UHFFFAOYSA-N 0.000 description 1
- NGECFAVNFYGEQO-CQSZACIVSA-N 3-[2-(2-aminopyrimidin-5-yl)-6-morpholin-4-ylpurin-9-yl]-1-[(3r)-3-hydroxypyrrolidin-1-yl]propan-1-one Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(N=CN2CCC(=O)N3C[C@H](O)CC3)C2=N1 NGECFAVNFYGEQO-CQSZACIVSA-N 0.000 description 1
- NGECFAVNFYGEQO-AWEZNQCLSA-N 3-[2-(2-aminopyrimidin-5-yl)-6-morpholin-4-ylpurin-9-yl]-1-[(3s)-3-hydroxypyrrolidin-1-yl]propan-1-one Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(N=CN2CCC(=O)N3C[C@@H](O)CC3)C2=N1 NGECFAVNFYGEQO-AWEZNQCLSA-N 0.000 description 1
- XHGAULXLKKZIQP-UHFFFAOYSA-N 3-[2-(2-aminopyrimidin-5-yl)-6-morpholin-4-ylpurin-9-yl]propan-1-ol Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(N=CN2CCCO)C2=N1 XHGAULXLKKZIQP-UHFFFAOYSA-N 0.000 description 1
- CODFKSZBVMZBRH-UHFFFAOYSA-N 3-[2-(2-aminopyrimidin-5-yl)-6-morpholin-4-ylpurin-9-yl]propanoic acid Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(N=CN2CCC(O)=O)C2=N1 CODFKSZBVMZBRH-UHFFFAOYSA-N 0.000 description 1
- ZENYQCKYSXLZEH-UHFFFAOYSA-N 3-[6-morpholin-4-yl-9-(pyridin-4-ylmethyl)purin-2-yl]phenol Chemical compound OC1=CC=CC(C=2N=C3N(CC=4C=CN=CC=4)C=NC3=C(N3CCOCC3)N=2)=C1 ZENYQCKYSXLZEH-UHFFFAOYSA-N 0.000 description 1
- DGAMBEREUILCPV-UHFFFAOYSA-N 3-[9-(2-hydroxyethyl)-6-morpholin-4-ylpurin-2-yl]phenol Chemical compound N1=C2N(CCO)C=NC2=C(N2CCOCC2)N=C1C1=CC=CC(O)=C1 DGAMBEREUILCPV-UHFFFAOYSA-N 0.000 description 1
- NDUUVXXLPJLSJB-UHFFFAOYSA-N 3-[9-(2-methylpropyl)-6-morpholin-4-ylpurin-2-yl]phenol Chemical compound N1=C2N(CC(C)C)C=NC2=C(N2CCOCC2)N=C1C1=CC=CC(O)=C1 NDUUVXXLPJLSJB-UHFFFAOYSA-N 0.000 description 1
- BITPBCRAXMHMRI-UHFFFAOYSA-N 3-[9-[(4-fluorophenyl)methyl]-6-morpholin-4-ylpurin-2-yl]phenol Chemical compound OC1=CC=CC(C=2N=C3N(CC=4C=CC(F)=CC=4)C=NC3=C(N3CCOCC3)N=2)=C1 BITPBCRAXMHMRI-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- FXEDTOMEAAGWRT-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-9-(2-methoxyethyl)-8-[(4-methylsulfonylpiperazin-1-yl)methyl]purin-6-yl]morpholine Chemical compound N=1C2=C(N3CCOCC3)N=C(C=3C=4C=NNC=4C=CC=3)N=C2N(CCOC)C=1CN1CCN(S(C)(=O)=O)CC1 FXEDTOMEAAGWRT-UHFFFAOYSA-N 0.000 description 1
- AGEYEBVSRFUXAM-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-9-methyl-8-[(4-methylsulfonylpiperazin-1-yl)methyl]purin-6-yl]morpholine Chemical compound N=1C2=C(N3CCOCC3)N=C(C=3C=4C=NNC=4C=CC=3)N=C2N(C)C=1CN1CCN(S(C)(=O)=O)CC1 AGEYEBVSRFUXAM-UHFFFAOYSA-N 0.000 description 1
- BSKPTSSXGDEZDB-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-9-methylpurin-6-yl]morpholine Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2N(C)C=NC2=C1N1CCOCC1 BSKPTSSXGDEZDB-UHFFFAOYSA-N 0.000 description 1
- MAXIMYAATWVVQK-UHFFFAOYSA-N 4-[2-(2-methoxypyrimidin-5-yl)-9-methyl-8-[(4-methylsulfonylpiperazin-1-yl)methyl]purin-6-yl]morpholine Chemical compound C1=NC(OC)=NC=C1C1=NC(N2CCOCC2)=C(N=C(CN2CCN(CC2)S(C)(=O)=O)N2C)C2=N1 MAXIMYAATWVVQK-UHFFFAOYSA-N 0.000 description 1
- COJBUQKMQKJJBX-UHFFFAOYSA-N 4-[2-[2-(3-hydroxyphenyl)-6-morpholin-4-ylpurin-9-yl]acetyl]piperazin-2-one Chemical compound OC1=CC=CC(C=2N=C3N(CC(=O)N4CC(=O)NCC4)C=NC3=C(N3CCOCC3)N=2)=C1 COJBUQKMQKJJBX-UHFFFAOYSA-N 0.000 description 1
- MELXZZULKDAPHV-UHFFFAOYSA-N 5-(9-methyl-6-morpholin-4-ylpurin-2-yl)pyridin-2-amine Chemical compound N1=C2N(C)C=NC2=C(N2CCOCC2)N=C1C1=CC=C(N)N=C1 MELXZZULKDAPHV-UHFFFAOYSA-N 0.000 description 1
- OGLQNIWTBCUNNG-UHFFFAOYSA-N 5-(9-methyl-6-morpholin-4-ylpurin-2-yl)pyrimidin-2-amine Chemical compound N1=C2N(C)C=NC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 OGLQNIWTBCUNNG-UHFFFAOYSA-N 0.000 description 1
- RDSWHFASXQEXJX-UHFFFAOYSA-N 5-[6-morpholin-4-yl-9-(2-morpholin-4-ylethyl)purin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(N=CN2CCN3CCOCC3)C2=N1 RDSWHFASXQEXJX-UHFFFAOYSA-N 0.000 description 1
- DTUURQKCKMPNGR-UHFFFAOYSA-N 5-[9-[(3-methoxyphenyl)methyl]-6-morpholin-4-ylpurin-2-yl]pyrimidin-2-amine Chemical compound COC1=CC=CC(CN2C3=NC(=NC(=C3N=C2)N2CCOCC2)C=2C=NC(N)=NC=2)=C1 DTUURQKCKMPNGR-UHFFFAOYSA-N 0.000 description 1
- KAPWFCMMNVOORR-UHFFFAOYSA-N 5-[9-[(4-methylsulfonylphenyl)methyl]-6-morpholin-4-ylpurin-2-yl]pyrimidin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1CN1C2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2N=C1 KAPWFCMMNVOORR-UHFFFAOYSA-N 0.000 description 1
- TUCAPDBFAOJHOT-UHFFFAOYSA-N 5-[9-ethyl-6-morpholin-4-yl-8-[(4-morpholin-4-ylpiperidin-1-yl)methyl]purin-2-yl]-4-methylpyrimidin-2-amine Chemical compound N=1C2=C(N3CCOCC3)N=C(C=3C(=NC(N)=NC=3)C)N=C2N(CC)C=1CN(CC1)CCC1N1CCOCC1 TUCAPDBFAOJHOT-UHFFFAOYSA-N 0.000 description 1
- FPQFBQMNHUKFDS-UHFFFAOYSA-N 5-[9-ethyl-6-morpholin-4-yl-8-[(4-piperidin-1-ylpiperidin-1-yl)methyl]purin-2-yl]-4-methylpyrimidin-2-amine Chemical compound N=1C2=C(N3CCOCC3)N=C(C=3C(=NC(N)=NC=3)C)N=C2N(CC)C=1CN(CC1)CCC1N1CCCCC1 FPQFBQMNHUKFDS-UHFFFAOYSA-N 0.000 description 1
- VTAHIFPHJDMNQT-UHFFFAOYSA-N 5-[9-ethyl-6-morpholin-4-yl-8-[(4-piperidin-1-ylpiperidin-1-yl)methyl]purin-2-yl]pyrimidin-2-amine Chemical compound N=1C2=C(N3CCOCC3)N=C(C=3C=NC(N)=NC=3)N=C2N(CC)C=1CN(CC1)CCC1N1CCCCC1 VTAHIFPHJDMNQT-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000001506 immunosuppresive effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000001361 intraarterial administration Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000007913 intrathecal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- WHRNQECLXDEWAY-UHFFFAOYSA-N n-[1-[[2-(2-amino-4-methylpyrimidin-5-yl)-9-ethyl-6-morpholin-4-ylpurin-8-yl]methyl]piperidin-4-yl]-n-methylmethanesulfonamide Chemical compound N=1C2=C(N3CCOCC3)N=C(C=3C(=NC(N)=NC=3)C)N=C2N(CC)C=1CN1CCC(N(C)S(C)(=O)=O)CC1 WHRNQECLXDEWAY-UHFFFAOYSA-N 0.000 description 1
- KSQHFCOCMGKFHC-UHFFFAOYSA-N n-[1-[[2-(2-aminopyrimidin-5-yl)-9-ethyl-6-morpholin-4-ylpurin-8-yl]methyl]piperidin-4-yl]-n-methylmethanesulfonamide Chemical compound N=1C2=C(N3CCOCC3)N=C(C=3C=NC(N)=NC=3)N=C2N(CC)C=1CN1CCC(N(C)S(C)(=O)=O)CC1 KSQHFCOCMGKFHC-UHFFFAOYSA-N 0.000 description 1
- BMEOUALTYJSZAF-UHFFFAOYSA-N n-[4-[9-methyl-8-[(4-methylsulfonylpiperazin-1-yl)methyl]-6-morpholin-4-ylpurin-2-yl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=NC(N2CCOCC2)=C(N=C(CN2CCN(CC2)S(C)(=O)=O)N2C)C2=N1 BMEOUALTYJSZAF-UHFFFAOYSA-N 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US57559 | 1987-06-03 | ||
| US5755908P | 2008-05-30 | 2008-05-30 | |
| PCT/US2009/045603 WO2009146406A1 (en) | 2008-05-30 | 2009-05-29 | Purine pi3k inhibitor compounds and methods of use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2533788T3 true ES2533788T3 (es) | 2015-04-14 |
Family
ID=41017038
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES09755767.2T Active ES2533788T3 (es) | 2008-05-30 | 2009-05-29 | Compuestos inhibidores de PI3K de tipo purina y métodos de uso |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US8158624B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2279188B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP2011521968A (cg-RX-API-DMAC7.html) |
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Families Citing this family (63)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BRPI0817503B8 (pt) | 2007-10-05 | 2021-05-25 | Sstarbio Pte Ltd | derivados de purina substituídos por pirimidina, composição farmacêutica compreendendo ditos compostos e uso dos mesmos para a prevenção ou tratamento de uma condição proliferativa |
| WO2009055730A1 (en) * | 2007-10-25 | 2009-04-30 | Genentech, Inc. | Process for making thienopyrimidine compounds |
| GB0721095D0 (en) * | 2007-10-26 | 2007-12-05 | Piramed Ltd | Pharmaceutical compounds |
| JP5638955B2 (ja) * | 2007-10-26 | 2014-12-10 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | Ｐｉ３キナーゼ阻害剤として有用なプリン誘導体 |
| CN104926815B (zh) | 2008-01-04 | 2017-11-03 | 英特利凯恩有限责任公司 | 某些化学实体、组合物和方法 |
| US8193182B2 (en) | 2008-01-04 | 2012-06-05 | Intellikine, Inc. | Substituted isoquinolin-1(2H)-ones, and methods of use thereof |
| EP2346508B1 (en) | 2008-09-26 | 2016-08-24 | Intellikine, LLC | Heterocyclic kinase inhibitors |
| US20100233733A1 (en) * | 2009-02-10 | 2010-09-16 | Nodality, Inc., A Delaware Corporation | Multiple mechanisms for modulation of the pi3 kinase pathway |
| RU2506264C2 (ru) | 2009-04-03 | 2014-02-10 | Вэрастэм, Инк. | Пиримидин-замещенные пуриновые соединения в качестве ингибиторов киназы (или киназ) |
| JP5789252B2 (ja) | 2009-05-07 | 2015-10-07 | インテリカイン， エルエルシー | 複素環式化合物およびその使用 |
| MX2011012520A (es) * | 2009-05-27 | 2011-12-12 | Hoffmann La Roche | Compuestos inhibidores de pi3k de pirimidina biciclicos selectivos para p110 delta y metodos de uso de los mismos. |
| EP2451811A1 (en) * | 2009-05-27 | 2012-05-16 | F. Hoffmann-La Roche AG | Bicyclic indole-pyrimidine pi3k inhibitor compounds selective for p110 delta, and methods of use |
| EP2499143B1 (en) * | 2009-11-12 | 2016-03-16 | F.Hoffmann-La Roche Ag | N7-substituted purine and pyrazolopyrimidine compounds, compositions and methods of use |
| JP5579864B2 (ja) * | 2009-11-12 | 2014-08-27 | エフ・ホフマン−ラ・ロシュ・アクチェンゲゼルシャフト | Ｎ−９−置換プリン化合物、組成物及び使用の方法 |
| WO2011146882A1 (en) | 2010-05-21 | 2011-11-24 | Intellikine, Inc. | Chemical compounds, compositions and methods for kinase modulation |
| JP5555378B2 (ja) * | 2010-07-14 | 2014-07-23 | エフ．ホフマン−ラ ロシュ アーゲー | Ｐｉ３ｋｐ１１０デルタに選択的なプリン化合物とその使用の方法 |
| CA2812091C (en) * | 2010-09-14 | 2020-03-24 | Exelixis, Inc. | Inhibitors of pi3k-delta and methods of their use and manufacture |
| CN103298474B (zh) | 2010-11-10 | 2016-06-29 | 无限药品股份有限公司 | 杂环化合物及其用途 |
| JP5775171B2 (ja) * | 2010-12-16 | 2015-09-09 | エフ・ホフマン−ラ・ロシュ・アクチェンゲゼルシャフト | 三環系ｐｉ３ｋ阻害剤化合物及びその使用方法 |
| AR084824A1 (es) | 2011-01-10 | 2013-06-26 | Intellikine Inc | Procesos para preparar isoquinolinonas y formas solidas de isoquinolinonas |
| WO2012156379A1 (en) | 2011-05-13 | 2012-11-22 | Universität Zürich | PIK3/P110α INHIBITORS FOR PREVENTION OF RESTENOSIS BY APPLICATION AS AN IMPLANT COATING |
| CA2842190A1 (en) | 2011-07-19 | 2013-01-24 | Infinity Pharmaceuticals Inc. | Heterocyclic compounds and uses thereof |
| WO2013012915A1 (en) | 2011-07-19 | 2013-01-24 | Infinity Pharmaceuticals Inc. | Heterocyclic compounds and uses thereof |
| US20140298493A1 (en) * | 2011-07-28 | 2014-10-02 | Somasekar Seshagiri | PIK3CA H1047R Knock-In Non-Human Animal Breast Cancer Model |
| CN103998442B (zh) | 2011-08-29 | 2016-09-14 | 无限药品股份有限公司 | 杂环化合物及其用途 |
| WO2013061305A1 (en) | 2011-10-28 | 2013-05-02 | Novartis Ag | Novel purine derivatives and their use in the treatment of disease |
| WO2013090725A1 (en) * | 2011-12-15 | 2013-06-20 | Philadelphia Health & Education Corporation | NOVEL PI3K p110 INHIBITORS AND METHODS OF USE THEREOF |
| US8940742B2 (en) | 2012-04-10 | 2015-01-27 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| WO2013174794A1 (en) | 2012-05-23 | 2013-11-28 | F. Hoffmann-La Roche Ag | Compositions and methods of obtaining and using endoderm and hepatocyte cells |
| US8828998B2 (en) | 2012-06-25 | 2014-09-09 | Infinity Pharmaceuticals, Inc. | Treatment of lupus, fibrotic conditions, and inflammatory myopathies and other disorders using PI3 kinase inhibitors |
| WO2014068070A1 (en) | 2012-10-31 | 2014-05-08 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for preventing antiphospholipid syndrome (aps) |
| HRP20181367T4 (hr) | 2012-11-01 | 2021-11-26 | Infinity Pharmaceuticals, Inc. | Liječenje raka korištenjem modulatora izoforme pi3 kinaze |
| CN103936742B (zh) * | 2013-01-17 | 2017-05-03 | 程鹏 | 含嘌呤基的新型pi3k抑制剂及其制备方法和应用 |
| US9481667B2 (en) | 2013-03-15 | 2016-11-01 | Infinity Pharmaceuticals, Inc. | Salts and solid forms of isoquinolinones and composition comprising and methods of using the same |
| PT2991987T (pt) * | 2013-05-02 | 2018-07-13 | Hoffmann La Roche | Derivados de purina como agonistas do recetor cb2 |
| TW201520215A (zh) * | 2013-05-13 | 2015-06-01 | Daiichi Sankyo Co Ltd | Ｎ－□啉基嘌呤衍生物之製造方法 |
| US9751888B2 (en) | 2013-10-04 | 2017-09-05 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| MX389256B (es) | 2013-10-04 | 2025-03-20 | Infinity Pharmaceuticals Inc | Compuestos heterociclicos y usos de los mismos. |
| WO2015055071A1 (zh) * | 2013-10-16 | 2015-04-23 | 上海璎黎药业有限公司 | 稠合杂环化合物、其制备方法、药物组合物和用途 |
| CN103804380B (zh) * | 2014-01-24 | 2016-05-18 | 温州医科大学 | 以IKK-β为靶点的2-氨基-8-取代鸟嘌呤衍生物、应用及其制备方法 |
| CN113616656B (zh) | 2014-03-19 | 2023-02-17 | 无限药品股份有限公司 | 用于治疗PI3K-γ介导的障碍的杂环化合物 |
| WO2015160975A2 (en) | 2014-04-16 | 2015-10-22 | Infinity Pharmaceuticals, Inc. | Combination therapies |
| WO2015188369A1 (en) * | 2014-06-13 | 2015-12-17 | Merck Sharp & Dohme Corp. | Purine inhibitors of human phosphatidylinositol 3-kinase delta |
| US9708348B2 (en) | 2014-10-03 | 2017-07-18 | Infinity Pharmaceuticals, Inc. | Trisubstituted bicyclic heterocyclic compounds with kinase activities and uses thereof |
| RU2672875C1 (ru) * | 2014-12-17 | 2018-11-20 | Пфайзер Инк. | Композиции PI3K/MTOR-ингибитора для внутривенного введения |
| MY185268A (en) | 2015-03-30 | 2021-04-30 | Daiichi Sankyo Co Ltd | Pyrazole derivative useful as pi3k inhibitor |
| PL236355B1 (pl) * | 2015-04-02 | 2021-01-11 | Celon Pharma Spolka Akcyjna | Pochodne 7-(morfolin-4-ylo)pirazolo[1,5-α]pirymidyny jako inhibitory kinazy PI3 |
| KR102015826B1 (ko) * | 2015-04-21 | 2019-08-29 | 구이저우 바이링 그룹 파마슈티컬 컴퍼니 리미티드 | 퓨리닐-n-하이드록실 피리미딘 포름아미드 유도체, 이의 제조 방법 및 용도 |
| JP6871919B2 (ja) | 2015-06-16 | 2021-05-19 | ナノファギックス エルエルシー | 薬物送達及びイメージング化学コンジュゲート、製剤及びその使用方法 |
| CN114230571B (zh) | 2015-09-14 | 2025-07-08 | 无限药品股份有限公司 | 异喹啉酮的固体形式、其制备方法、包含其的组合物及其使用方法 |
| US10759806B2 (en) | 2016-03-17 | 2020-09-01 | Infinity Pharmaceuticals, Inc. | Isotopologues of isoquinolinone and quinazolinone compounds and uses thereof as PI3K kinase inhibitors |
| WO2017214269A1 (en) | 2016-06-08 | 2017-12-14 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| CA3028718A1 (en) | 2016-06-24 | 2017-12-28 | Infinity Pharmaceuticals, Inc. | Combination therapies |
| TW201813963A (zh) | 2016-09-23 | 2018-04-16 | 美商基利科學股份有限公司 | 磷脂醯肌醇3-激酶抑制劑 |
| TW201825465A (zh) | 2016-09-23 | 2018-07-16 | 美商基利科學股份有限公司 | 磷脂醯肌醇3-激酶抑制劑 |
| TW201815787A (zh) | 2016-09-23 | 2018-05-01 | 美商基利科學股份有限公司 | 磷脂醯肌醇3-激酶抑制劑 |
| JPWO2018062382A1 (ja) * | 2016-09-29 | 2019-07-11 | 第一三共株式会社 | ［２−（１−メチル−１ｈ−ピラゾール−４−イル）−６−（モルホリン−４−イル）−９ｈ−プリン−８−イル］［４−（モルホリン−４−イル）ピペリジン−１−イル］メタノン及びその製薬上許容される塩の結晶 |
| KR102399639B1 (ko) | 2016-12-02 | 2022-05-18 | 다이이찌 산쿄 가부시키가이샤 | 신규 엔도-β-N-아세틸글루코사미니다아제 |
| SG11202103118PA (en) * | 2018-09-27 | 2021-04-29 | Shanghai Yingli Pharmaceutical Co Ltd | Crystal form of morpholino quinazoline compound, preparation method therefor and use thereof |
| UY38912A (es) * | 2019-10-09 | 2021-05-31 | Biocryst Pharm Inc | Inhibidores del factor d del complemento para administración oral |
| CN111875606B (zh) * | 2020-07-20 | 2023-04-07 | 武汉工程大学 | 一种基于虚拟对接获得的嘌呤类化合物及其制备方法和应用 |
| US11351149B2 (en) | 2020-09-03 | 2022-06-07 | Pfizer Inc. | Nitrile-containing antiviral compounds |
| CN117777134B (zh) * | 2022-12-19 | 2025-02-25 | 艾立康药业股份有限公司 | 作为mat2a抑制剂的多环类化合物 |
Family Cites Families (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3016378A (en) | 1959-07-01 | 1962-01-09 | Thomae Gmbh Dr K | Amino-substituted purine derivatives |
| JPS60260579A (ja) | 1984-01-13 | 1985-12-23 | Yoshitomi Pharmaceut Ind Ltd | プリン誘導体 |
| DE3406533A1 (de) | 1984-02-23 | 1985-08-29 | Boehringer Mannheim Gmbh, 6800 Mannheim | Verwendung von adenosin-derivaten als antiallergica und arzneimittel, die diese enthalten |
| US5332744A (en) | 1989-05-30 | 1994-07-26 | Merck & Co., Inc. | Substituted imidazo-fused 6-membered heterocycles as angiotensin II antagonists |
| US6790958B2 (en) * | 1996-08-02 | 2004-09-14 | Robert T. Lum | Purine inhibitors of cyclin dependent kinase 2 & IKBA |
| US5866702A (en) * | 1996-08-02 | 1999-02-02 | Cv Therapeutics, Incorporation | Purine inhibitors of cyclin dependent kinase 2 |
| GB9817623D0 (en) * | 1998-08-13 | 1998-10-07 | Glaxo Group Ltd | Pharmaceutical compounds |
| JP2003146987A (ja) * | 1999-05-31 | 2003-05-21 | Dainippon Pharmaceut Co Ltd | ２−アリールプリン−９−アセトアミド誘導体 |
| EP1277738B1 (en) * | 2000-04-27 | 2011-03-30 | Astellas Pharma Inc. | Condensed heteroaryl derivatives |
| JP2005504789A (ja) | 2001-09-13 | 2005-02-17 | シンタ ファーマスーティカルズ コーポレイション | 癌治療のための２−アロイルイミダゾール化合物 |
| CA2463563A1 (en) | 2001-10-12 | 2003-04-17 | Irm Llc | Kinase inhibitor scaffolds and methods for their preparation |
| US6949644B2 (en) | 2001-10-12 | 2005-09-27 | Irm Llc | Methods for the synthesis of substituted purines |
| US7189730B2 (en) * | 2001-12-18 | 2007-03-13 | Cv Therapeutics, Inc. | A2A adenosine receptor antagonists |
| US20030139427A1 (en) | 2002-08-23 | 2003-07-24 | Osi Pharmaceuticals Inc. | Bicyclic pyrimidinyl derivatives and methods of use thereof |
| JP2006503826A (ja) | 2002-09-06 | 2006-02-02 | スミスクライン・ビーチャム・コーポレイション | ピロロ［２，３−ｄ］ピリミジン−４−イルおよびプリン−６−イル尿素化合物 |
| EP1556140A4 (en) | 2002-10-15 | 2006-04-19 | Synta Pharmaceuticals Corp | NEW COMPOUNDS |
| TW200510394A (en) | 2003-05-29 | 2005-03-16 | Synta Pharmaceuticals Corp | Heterocyclic compounds for preventing and treating disorders associated with excessive bone loss |
| GB0423653D0 (en) | 2004-10-25 | 2004-11-24 | Piramed Ltd | Pharmaceutical compounds |
| GB2431156A (en) * | 2005-10-11 | 2007-04-18 | Piramed Ltd | 1-cyclyl-3-substituted- -benzenes and -azines as inhibitors of phosphatidylinositol 3-kinase |
| EP2046799B1 (en) | 2006-04-26 | 2017-07-19 | Genentech, Inc. | Phosphoinositide 3-kinase inhibitor compounds and pharmaceutical compositions containing them |
| WO2008043031A1 (en) | 2006-10-04 | 2008-04-10 | Pharmacopeia, Inc. | 6-substituted 2-(benzimidazolyl)purine and purinone derivatives for immunosuppression |
| US20080233127A1 (en) * | 2007-03-21 | 2008-09-25 | Wyeth | Imidazolopyrimidine analogs and their use as pi3 kinase and mtor inhibitors |
| KR101564233B1 (ko) * | 2007-03-28 | 2015-10-29 | 뉴로서치 에이/에스 | 푸리닐 유도체 및 칼륨 채널 조절제로서의 이의 용도 |
| WO2008116909A1 (en) * | 2007-03-28 | 2008-10-02 | Neurosearch A/S | Purinyl derivatives and their use as potassium channel modulators |
| JP5638955B2 (ja) * | 2007-10-26 | 2014-12-10 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | Ｐｉ３キナーゼ阻害剤として有用なプリン誘導体 |
| TWI378933B (en) * | 2008-10-14 | 2012-12-11 | Daiichi Sankyo Co Ltd | Morpholinopurine derivatives |
| PE20100362A1 (es) * | 2008-10-30 | 2010-05-27 | Irm Llc | Derivados de purina que expanden las celulas madre hematopoyeticas |
| RU2506264C2 (ru) * | 2009-04-03 | 2014-02-10 | Вэрастэм, Инк. | Пиримидин-замещенные пуриновые соединения в качестве ингибиторов киназы (или киназ) |
| MX2011012520A (es) * | 2009-05-27 | 2011-12-12 | Hoffmann La Roche | Compuestos inhibidores de pi3k de pirimidina biciclicos selectivos para p110 delta y metodos de uso de los mismos. |
| EP2451811A1 (en) * | 2009-05-27 | 2012-05-16 | F. Hoffmann-La Roche AG | Bicyclic indole-pyrimidine pi3k inhibitor compounds selective for p110 delta, and methods of use |
| JP5579864B2 (ja) * | 2009-11-12 | 2014-08-27 | エフ・ホフマン−ラ・ロシュ・アクチェンゲゼルシャフト | Ｎ−９−置換プリン化合物、組成物及び使用の方法 |
| JP5555378B2 (ja) * | 2010-07-14 | 2014-07-23 | エフ．ホフマン−ラ ロシュ アーゲー | Ｐｉ３ｋｐ１１０デルタに選択的なプリン化合物とその使用の方法 |
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| CN102105474A (zh) | 2011-06-22 |
| ZA201007524B (en) | 2012-01-25 |
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| EP2279188A1 (en) | 2011-02-02 |
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| EP2279188B1 (en) | 2015-01-28 |
| CA2721851A1 (en) | 2009-12-03 |
| CN102105474B (zh) | 2014-01-08 |
| RU2010154428A (ru) | 2012-07-10 |
| KR20110042153A (ko) | 2011-04-25 |
| IL208838A0 (en) | 2011-01-31 |
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| JP2011521968A (ja) | 2011-07-28 |
| AU2009251291A1 (en) | 2009-12-03 |
| WO2009146406A1 (en) | 2009-12-03 |
| US20120135988A1 (en) | 2012-05-31 |
| US8158624B2 (en) | 2012-04-17 |
| US20090318411A1 (en) | 2009-12-24 |
| US8445487B2 (en) | 2013-05-21 |
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