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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (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 (enExample) |
| EP (1) | EP2279188B1 (enExample) |
| JP (1) | JP2011521968A (enExample) |
| KR (1) | KR20110042153A (enExample) |
| CN (1) | CN102105474B (enExample) |
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| RU (1) | RU2509081C2 (enExample) |
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| ZA (1) | ZA201007524B (enExample) |
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- 2009-05-29 WO PCT/US2009/045603 patent/WO2009146406A1/en not_active Ceased
- 2009-05-29 RU RU2010154428/04A patent/RU2509081C2/ru not_active IP Right Cessation
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| WO2009146406A1 (en) | 2009-12-03 |
| US20120135988A1 (en) | 2012-05-31 |
| US8445487B2 (en) | 2013-05-21 |
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| ZA201007524B (en) | 2012-01-25 |
| RU2509081C2 (ru) | 2014-03-10 |
| MX2010012583A (es) | 2011-02-24 |
| AU2009251291B2 (en) | 2013-05-02 |
| US8158624B2 (en) | 2012-04-17 |
| RU2010154428A (ru) | 2012-07-10 |
| EP2279188B1 (en) | 2015-01-28 |
| AU2009251291A1 (en) | 2009-12-03 |
| IL208838A0 (en) | 2011-01-31 |
| CA2721851A1 (en) | 2009-12-03 |
| US20090318411A1 (en) | 2009-12-24 |
| JP2011521968A (ja) | 2011-07-28 |
| BRPI0909614A2 (pt) | 2015-09-22 |
| CN102105474B (zh) | 2014-01-08 |
| KR20110042153A (ko) | 2011-04-25 |
| EP2279188A1 (en) | 2011-02-02 |
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