JP2011521968A5 - - Google Patents
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- JP2011521968A5 JP2011521968A5 JP2011511842A JP2011511842A JP2011521968A5 JP 2011521968 A5 JP2011521968 A5 JP 2011521968A5 JP 2011511842 A JP2011511842 A JP 2011511842A JP 2011511842 A JP2011511842 A JP 2011511842A JP 2011521968 A5 JP2011521968 A5 JP 2011521968A5
- Authority
- JP
- Japan
- Prior art keywords
- cancer
- purin
- morpholino
- methyl
- aminopyrimidin
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims description 53
- 125000000623 heterocyclic group Chemical group 0.000 claims description 46
- 206010028980 Neoplasm Diseases 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 201000011510 cancer Diseases 0.000 claims description 34
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 125000002947 alkylene group Chemical group 0.000 claims description 22
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 21
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 125000000304 alkynyl group Chemical group 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 10
- 206010009944 Colon cancer Diseases 0.000 claims description 9
- -1 4- (methylsulfonyl) piperazin-1-yl Chemical group 0.000 claims description 8
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 8
- 229940079593 drug Drugs 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 208000029742 colonic neoplasm Diseases 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 6
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 6
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 229940095102 methyl benzoate Drugs 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 208000010507 Adenocarcinoma of Lung Diseases 0.000 claims description 3
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- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 3
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- 208000001894 Nasopharyngeal Neoplasms Diseases 0.000 claims description 3
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- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 3
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- 206010034811 Pharyngeal cancer Diseases 0.000 claims description 3
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- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 3
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- 201000010208 Seminoma Diseases 0.000 claims description 3
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- 206010062129 Tongue neoplasm Diseases 0.000 claims description 3
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 3
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- 208000014018 liver neoplasm Diseases 0.000 claims description 3
- 201000005249 lung adenocarcinoma Diseases 0.000 claims description 3
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- 201000000849 skin cancer Diseases 0.000 claims description 3
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- 201000002314 small intestine cancer Diseases 0.000 claims description 3
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- 230000001225 therapeutic effect Effects 0.000 claims description 3
- 201000002510 thyroid cancer Diseases 0.000 claims description 3
- 201000006134 tongue cancer Diseases 0.000 claims description 3
- 201000005112 urinary bladder cancer Diseases 0.000 claims description 3
- 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 claims description 2
- 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 claims description 2
- 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 claims description 2
- MJKNDQVAWMECBQ-UHFFFAOYSA-N 2-[2-(2-amino-4-methylpyrimidin-5-yl)-9-(2-hydroxyethyl)-6-morpholin-4-ylpurin-8-yl]propan-2-ol Chemical compound CC1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(N=C(N2CCO)C(C)(C)O)C2=N1 MJKNDQVAWMECBQ-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 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 claims description 2
- 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 claims description 2
- 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 claims description 2
- 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 claims description 2
- FDDKQQRYIKXUCV-UHFFFAOYSA-N 2-[2-(2-aminopyrimidin-5-yl)-9-(2-hydroxyethyl)-6-morpholin-4-ylpurin-8-yl]propan-2-ol Chemical compound N1=C2N(CCO)C(C(C)(O)C)=NC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 FDDKQQRYIKXUCV-UHFFFAOYSA-N 0.000 claims description 2
- KPLJRUFOHIXWBX-UHFFFAOYSA-N 2-[2-(2-aminopyrimidin-5-yl)-9-(3-hydroxypropyl)-6-morpholin-4-ylpurin-8-yl]propan-2-ol Chemical compound N1=C2N(CCCO)C(C(C)(O)C)=NC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 KPLJRUFOHIXWBX-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 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 claims description 2
- 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 claims description 2
- 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 claims description 2
- 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 claims description 2
- 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 claims description 2
- 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 claims description 2
- KPZTWHKISNKFTP-UHFFFAOYSA-N 3-[2-(2-aminopyrimidin-5-yl)-6-morpholin-4-ylpurin-9-yl]-1-morpholin-4-ylpropan-1-one Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(N=CN2CCC(=O)N3CCOCC3)C2=N1 KPZTWHKISNKFTP-UHFFFAOYSA-N 0.000 claims description 2
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- 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 claims description 2
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- 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 claims description 2
- 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 claims description 2
- 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 claims description 2
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| US6949644B2 (en) | 2001-10-12 | 2005-09-27 | Irm Llc | Methods for the synthesis of substituted purines |
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| US20080233127A1 (en) * | 2007-03-21 | 2008-09-25 | Wyeth | Imidazolopyrimidine analogs and their use as pi3 kinase and mtor inhibitors |
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| CN103003279B (zh) * | 2010-07-14 | 2015-09-23 | 弗·哈夫曼-拉罗切有限公司 | 对PI3K P110δ具有选择性的嘌呤化合物及其使用方法 |
-
2009
- 2009-05-29 US US12/474,613 patent/US8158624B2/en active Active
- 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
- 2009-05-29 AU AU2009251291A patent/AU2009251291B2/en not_active Ceased
- 2009-05-29 MX MX2010012583A patent/MX2010012583A/es active IP Right Grant
- 2009-05-29 EP EP09755767.2A patent/EP2279188B1/en active Active
- 2009-05-29 ES ES09755767.2T patent/ES2533788T3/es active Active
- 2009-05-29 BR BRPI0909614A patent/BRPI0909614A2/pt not_active Application Discontinuation
- 2009-05-29 CN CN200980129148.2A patent/CN102105474B/zh active Active
- 2009-05-29 CA CA2721851A patent/CA2721851A1/en not_active Abandoned
- 2009-05-29 JP JP2011511842A patent/JP2011521968A/ja active Pending
- 2009-05-29 KR KR1020107026673A patent/KR20110042153A/ko not_active Ceased
-
2010
- 2010-10-20 IL IL208838A patent/IL208838A0/en unknown
- 2010-10-21 ZA ZA2010/07524A patent/ZA201007524B/en unknown
-
2012
- 2012-02-09 US US13/369,941 patent/US8445487B2/en active Active
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