JP2011521968A5 - - Google Patents
Download PDFInfo
- Publication number
- 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.)
- Pending
Links
- 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
- 208000003200 Adenoma Diseases 0.000 claims description 3
- 206010001233 Adenoma benign Diseases 0.000 claims description 3
- 206010005003 Bladder cancer Diseases 0.000 claims description 3
- 206010005949 Bone cancer Diseases 0.000 claims description 3
- 208000018084 Bone neoplasm Diseases 0.000 claims description 3
- 206010006187 Breast cancer Diseases 0.000 claims description 3
- 208000026310 Breast neoplasm Diseases 0.000 claims description 3
- 206010008342 Cervix carcinoma Diseases 0.000 claims description 3
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 3
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims description 3
- 208000017604 Hodgkin disease Diseases 0.000 claims description 3
- 208000010747 Hodgkins lymphoma Diseases 0.000 claims description 3
- 208000008839 Kidney Neoplasms Diseases 0.000 claims description 3
- 206010023825 Laryngeal cancer Diseases 0.000 claims description 3
- 206010062038 Lip neoplasm Diseases 0.000 claims description 3
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 3
- 206010025323 Lymphomas Diseases 0.000 claims description 3
- 208000001894 Nasopharyngeal Neoplasms Diseases 0.000 claims description 3
- 206010061306 Nasopharyngeal cancer Diseases 0.000 claims description 3
- 206010029260 Neuroblastoma Diseases 0.000 claims description 3
- 206010030155 Oesophageal carcinoma Diseases 0.000 claims description 3
- 206010033128 Ovarian cancer Diseases 0.000 claims description 3
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 3
- 208000016222 Pancreatic disease Diseases 0.000 claims description 3
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 3
- 208000009565 Pharyngeal Neoplasms Diseases 0.000 claims description 3
- 206010034811 Pharyngeal cancer Diseases 0.000 claims description 3
- 206010060862 Prostate cancer Diseases 0.000 claims description 3
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 3
- 208000015634 Rectal Neoplasms Diseases 0.000 claims description 3
- 206010038389 Renal cancer Diseases 0.000 claims description 3
- 206010039491 Sarcoma Diseases 0.000 claims description 3
- 201000010208 Seminoma Diseases 0.000 claims description 3
- 208000000453 Skin Neoplasms Diseases 0.000 claims description 3
- 208000005718 Stomach Neoplasms Diseases 0.000 claims description 3
- 208000024313 Testicular Neoplasms Diseases 0.000 claims description 3
- 206010057644 Testis cancer Diseases 0.000 claims description 3
- 208000024770 Thyroid neoplasm Diseases 0.000 claims description 3
- 206010062129 Tongue neoplasm Diseases 0.000 claims description 3
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 3
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims description 3
- 208000009956 adenocarcinoma Diseases 0.000 claims description 3
- 201000009036 biliary tract cancer Diseases 0.000 claims description 3
- 208000020790 biliary tract neoplasm Diseases 0.000 claims description 3
- 208000015322 bone marrow disease Diseases 0.000 claims description 3
- 201000000220 brain stem cancer Diseases 0.000 claims description 3
- 201000007455 central nervous system cancer Diseases 0.000 claims description 3
- 201000010881 cervical cancer Diseases 0.000 claims description 3
- 230000001886 ciliary effect Effects 0.000 claims description 3
- 201000004101 esophageal cancer Diseases 0.000 claims description 3
- 230000003325 follicular Effects 0.000 claims description 3
- 206010017758 gastric cancer Diseases 0.000 claims description 3
- 208000005017 glioblastoma Diseases 0.000 claims description 3
- 201000010982 kidney cancer Diseases 0.000 claims description 3
- 206010023841 laryngeal neoplasm Diseases 0.000 claims description 3
- 208000032839 leukemia Diseases 0.000 claims description 3
- 201000006721 lip cancer Diseases 0.000 claims description 3
- 210000004185 liver Anatomy 0.000 claims description 3
- 201000007270 liver cancer Diseases 0.000 claims description 3
- 208000014018 liver neoplasm Diseases 0.000 claims description 3
- 201000005249 lung adenocarcinoma Diseases 0.000 claims description 3
- 201000005202 lung cancer Diseases 0.000 claims description 3
- 208000020816 lung neoplasm Diseases 0.000 claims description 3
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 3
- 201000001441 melanoma Diseases 0.000 claims description 3
- 208000024691 pancreas disease Diseases 0.000 claims description 3
- 201000002528 pancreatic cancer Diseases 0.000 claims description 3
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 3
- 206010038038 rectal cancer Diseases 0.000 claims description 3
- 201000001275 rectum cancer Diseases 0.000 claims description 3
- 201000000849 skin cancer Diseases 0.000 claims description 3
- 208000000649 small cell carcinoma Diseases 0.000 claims description 3
- 201000002314 small intestine cancer Diseases 0.000 claims description 3
- 201000011549 stomach cancer Diseases 0.000 claims description 3
- 201000003120 testicular cancer Diseases 0.000 claims description 3
- 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
- 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 claims description 2
- 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 claims description 2
- 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
- XLONKHTYYXTLNL-UHFFFAOYSA-N 4-[9-methyl-8-[(4-methylsulfonylpiperazin-1-yl)methyl]-2-pyridin-3-ylpurin-6-yl]morpholine Chemical compound N=1C2=C(N3CCOCC3)N=C(C=3C=NC=CC=3)N=C2N(C)C=1CN1CCN(S(C)(=O)=O)CC1 XLONKHTYYXTLNL-UHFFFAOYSA-N 0.000 claims description 2
- 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
- NMSXNXUCMSOCQX-UHFFFAOYSA-N 5-[8-[[4-(azetidin-1-yl)piperidin-1-yl]methyl]-9-ethyl-6-morpholin-4-ylpurin-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)CCC1N1CCC1 NMSXNXUCMSOCQX-UHFFFAOYSA-N 0.000 claims description 2
- RHXUXGFENWIZLX-UHFFFAOYSA-N 5-[8-[[4-(azetidin-1-yl)piperidin-1-yl]methyl]-9-ethyl-6-morpholin-4-ylpurin-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)CCC1N1CCC1 RHXUXGFENWIZLX-UHFFFAOYSA-N 0.000 claims description 2
- QJQGJTVWYYKZAF-UHFFFAOYSA-N 5-[8-[[4-(dimethylamino)piperidin-1-yl]methyl]-9-ethyl-6-morpholin-4-ylpurin-2-yl]pyrimidin-2-amine Chemical compound N=1C2=C(N3CCOCC3)N=C(C=3C=NC(N)=NC=3)N=C2N(CC)C=1CN1CCC(N(C)C)CC1 QJQGJTVWYYKZAF-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 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 claims description 2
- 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 claims description 2
- BHQMKXSPJSCTDH-UHFFFAOYSA-N 5-[9-ethyl-6-morpholin-4-yl-8-[(4-morpholin-4-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)CCC1N1CCOCC1 BHQMKXSPJSCTDH-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 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 claims description 2
- KWVCMUVZXMIWLA-UHFFFAOYSA-N 5-[9-methyl-8-[(4-methylsulfonylpiperazin-1-yl)methyl]-6-morpholin-4-ylpurin-2-yl]pyridin-2-amine Chemical compound N=1C2=C(N3CCOCC3)N=C(C=3C=NC(N)=CC=3)N=C2N(C)C=1CN1CCN(S(C)(=O)=O)CC1 KWVCMUVZXMIWLA-UHFFFAOYSA-N 0.000 claims description 2
- 208000019838 Blood disease Diseases 0.000 claims description 2
- OJXQQSGPFJPLCE-UHFFFAOYSA-N CC(C(=O)C1CNCCC1C(=O)NC)N2C=NC3=C2N=C(N=C3N4CCOCC4)C5=CN=C(N=C5)N Chemical compound CC(C(=O)C1CNCCC1C(=O)NC)N2C=NC3=C2N=C(N=C3N4CCOCC4)C5=CN=C(N=C5)N OJXQQSGPFJPLCE-UHFFFAOYSA-N 0.000 claims description 2
- 208000029462 Immunodeficiency disease Diseases 0.000 claims description 2
- 208000003445 Mouth Neoplasms Diseases 0.000 claims description 2
- 108010025020 Nerve Growth Factor Proteins 0.000 claims description 2
- 102000007072 Nerve Growth Factors Human genes 0.000 claims description 2
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 2
- 239000002246 antineoplastic agent Substances 0.000 claims description 2
- 239000003443 antiviral agent Substances 0.000 claims description 2
- 229940127089 cytotoxic agent Drugs 0.000 claims description 2
- 206010012601 diabetes mellitus Diseases 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 208000014951 hematologic disease Diseases 0.000 claims description 2
- 208000018706 hematopoietic system disease Diseases 0.000 claims description 2
- 239000002955 immunomodulating agent Substances 0.000 claims description 2
- 229940121354 immunomodulator Drugs 0.000 claims description 2
- 208000012987 lip and oral cavity carcinoma Diseases 0.000 claims description 2
- 208000019423 liver disease Diseases 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 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 claims description 2
- 239000003900 neurotrophic factor Substances 0.000 claims description 2
- 201000005443 oral cavity cancer Diseases 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 229940124597 therapeutic agent Drugs 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 3
- 210000000214 mouth Anatomy 0.000 claims 2
- 230000000069 prophylactic effect Effects 0.000 claims 2
- 206010041823 squamous cell carcinoma Diseases 0.000 claims 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 1
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 230000002584 immunomodulator Effects 0.000 claims 1
- 230000003780 keratinization Effects 0.000 claims 1
- 208000003849 large cell carcinoma Diseases 0.000 claims 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 claims 1
- 208000017572 squamous cell neoplasm Diseases 0.000 claims 1
- 125000004404 heteroalkyl group Chemical group 0.000 description 6
- 241000124008 Mammalia Species 0.000 description 5
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- 125000002619 bicyclic group Chemical group 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 208000035475 disorder Diseases 0.000 description 4
- 230000003463 hyperproliferative effect Effects 0.000 description 4
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 4
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 4
- 150000002475 indoles Chemical class 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 102000010400 1-phosphatidylinositol-3-kinase activity proteins Human genes 0.000 description 3
- 108091007960 PI3Ks Proteins 0.000 description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 description 2
- 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 description 2
- 108091000080 Phosphotransferase Proteins 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 102000020233 phosphotransferase Human genes 0.000 description 2
- 150000003212 purines Chemical class 0.000 description 2
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- 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
- 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
- QUVMETYUBXOTMG-UHFFFAOYSA-N 2-[9-(2-hydroxyethyl)-2-(1h-indol-4-yl)-6-morpholin-4-ylpurin-8-yl]propan-2-ol Chemical compound N1=C(C=2C=3C=CNC=3C=CC=2)N=C2N(CCO)C(C(C)(O)C)=NC2=C1N1CCOCC1 QUVMETYUBXOTMG-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
- 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
- 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
- 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
- XDQBBPSIOSPKHU-UHFFFAOYSA-N 5-[8-[[4-(dimethylamino)piperidin-1-yl]methyl]-9-ethyl-6-morpholin-4-ylpurin-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=1CN1CCC(N(C)C)CC1 XDQBBPSIOSPKHU-UHFFFAOYSA-N 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 230000035772 mutation Effects 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
- 230000002018 overexpression Effects 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5755908P | 2008-05-30 | 2008-05-30 | |
| US61/057,559 | 2008-05-30 | ||
| PCT/US2009/045603 WO2009146406A1 (en) | 2008-05-30 | 2009-05-29 | Purine pi3k inhibitor compounds and methods of use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011521968A JP2011521968A (ja) | 2011-07-28 |
| JP2011521968A5 true JP2011521968A5 (en:Method) | 2012-07-12 |
Family
ID=41017038
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011511842A Pending JP2011521968A (ja) | 2008-05-30 | 2009-05-29 | プリンｐｉ３ｋ阻害剤化合物および使用方法 |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US8158624B2 (en:Method) |
| EP (1) | EP2279188B1 (en:Method) |
| JP (1) | JP2011521968A (en:Method) |
| KR (1) | KR20110042153A (en:Method) |
| CN (1) | CN102105474B (en:Method) |
| AU (1) | AU2009251291B2 (en:Method) |
| BR (1) | BRPI0909614A2 (en:Method) |
| CA (1) | CA2721851A1 (en:Method) |
| ES (1) | ES2533788T3 (en:Method) |
| IL (1) | IL208838A0 (en:Method) |
| MX (1) | MX2010012583A (en:Method) |
| RU (1) | RU2509081C2 (en:Method) |
| WO (1) | WO2009146406A1 (en:Method) |
| ZA (1) | ZA201007524B (en:Method) |
Families Citing this family (63)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2681081C2 (ru) * | 2007-10-05 | 2019-03-04 | Верастэм, Инк. | Пиримидинзамещенные производные пурина, фармацевтическая композиция на их основе, способ ингибирования протеинкиназ, способ лечения или профилактики заболеваний, чувствительных к ингибированию протеинкиназ, и способ лечения пролиферативных заболеваний |
| CN101909631B (zh) * | 2007-10-25 | 2012-09-12 | 健泰科生物技术公司 | 制备噻吩并嘧啶化合物的方法 |
| GB0721095D0 (en) * | 2007-10-26 | 2007-12-05 | Piramed Ltd | Pharmaceutical compounds |
| CN101835779B (zh) * | 2007-10-26 | 2014-01-29 | 霍夫曼-拉罗奇有限公司 | 作为pi3激酶抑制剂的嘌呤衍生物 |
| US8193182B2 (en) | 2008-01-04 | 2012-06-05 | Intellikine, Inc. | Substituted isoquinolin-1(2H)-ones, and methods of use thereof |
| MX2010007419A (es) | 2008-01-04 | 2010-11-12 | Intellikine Inc | Ciertas entidades quimicas, composiciones y metodos. |
| JP5731978B2 (ja) | 2008-09-26 | 2015-06-10 | インテリカイン， エルエルシー | 複素環キナーゼ阻害剤 |
| US20100233733A1 (en) * | 2009-02-10 | 2010-09-16 | Nodality, Inc., A Delaware Corporation | Multiple mechanisms for modulation of the pi3 kinase pathway |
| WO2010114484A1 (en) | 2009-04-03 | 2010-10-07 | S*Bio Pte Ltd | Pyrimidine substituted purine compounds as kinase (s) inhibitors |
| CA2760791C (en) | 2009-05-07 | 2017-06-20 | Intellikine, Inc. | Heterocyclic compounds and uses thereof |
| US8158625B2 (en) * | 2009-05-27 | 2012-04-17 | Genentech, Inc. | Bicyclic indole-pyrimidine PI3K inhibitor compounds selective for P110 delta, and methods of use |
| SG175708A1 (en) | 2009-05-27 | 2011-12-29 | Genentech Inc | Bicyclic pyrimidine pi3k inhibitor compounds selective for p110 delta, and methods of use |
| JP5572715B2 (ja) * | 2009-11-12 | 2014-08-13 | エフ・ホフマン−ラ・ロシュ・アクチェンゲゼルシャフト | Ｎ−７置換プリン及びピラゾロピリミジン化合物、組成物及び使用方法 |
| ES2596654T3 (es) * | 2009-11-12 | 2017-01-11 | F. Hoffmann-La Roche Ag | Compuestos de purina N-9-sustituida, composiciones y métodos de uso |
| CN103002738A (zh) | 2010-05-21 | 2013-03-27 | 英特利凯恩有限责任公司 | 用于激酶调节的化学化合物、组合物和方法 |
| 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 |
| EP2616469B1 (en) | 2010-09-14 | 2016-10-26 | Exelixis, Inc. | 9h-purine compounds as pi3k-delta inhibitors and methods for their manufacture |
| JP2013545749A (ja) | 2010-11-10 | 2013-12-26 | インフィニティー ファーマシューティカルズ， インコーポレイテッド | 複素環化合物及びその使用 |
| NZ609448A (en) * | 2010-12-16 | 2015-07-31 | Hoffmann La Roche | Tricyclic pi3k inhibitor compounds and methods of use |
| US8809349B2 (en) | 2011-01-10 | 2014-08-19 | Infinity Pharmaceuticals, Inc. | Processes for preparing isoquinolinones and solid forms of isoquinolinones |
| WO2012156379A1 (en) | 2011-05-13 | 2012-11-22 | Universität Zürich | PIK3/P110α INHIBITORS FOR PREVENTION OF RESTENOSIS BY APPLICATION AS AN IMPLANT COATING |
| TWI565709B (zh) | 2011-07-19 | 2017-01-11 | 英菲尼提製藥股份有限公司 | 雜環化合物及其用途 |
| US8969363B2 (en) | 2011-07-19 | 2015-03-03 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| CA2843222A1 (en) * | 2011-07-28 | 2013-01-31 | Genentech, Inc. | Pik3ca h1047r knock-in non-human animal breast cancer model |
| SG11201400310WA (en) | 2011-08-29 | 2014-06-27 | Infinity Pharmaceuticals Inc | Heterocyclic compounds and uses thereof |
| KR20140090218A (ko) * | 2011-10-28 | 2014-07-16 | 노파르티스 아게 | 신규 퓨린 유도체 및 질환의 치료에서의 그의 용도 |
| US20150011569A1 (en) * | 2011-12-15 | 2015-01-08 | Philadelphia Health & Education Corporation D/B/A Drexel University College Of Medicine | NOVEL P13K p110 INHIBITORS AND METHODS OF USE THEREOF |
| US8940742B2 (en) | 2012-04-10 | 2015-01-27 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| KR20160027219A (ko) | 2012-05-23 | 2016-03-09 | 에프. 호프만-라 로슈 아게 | 내배엽 및 간세포를 수득하고 사용하는 조성물 및 방법 |
| 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) |
| MX386085B (es) | 2012-11-01 | 2025-03-18 | Infinity Pharmaceuticals Inc | Tratamiento de canceres utilizando moduladores de las isoformas de pi3 cinasa |
| 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 |
| HRP20181141T1 (hr) * | 2013-05-02 | 2018-09-21 | F. Hoffmann - La Roche Ag | Derivati purina kao agonisti cb2 receptora |
| 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 |
| WO2015051241A1 (en) | 2013-10-04 | 2015-04-09 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| CN105793255B (zh) | 2013-10-04 | 2018-11-16 | 无限药品股份有限公司 | 杂环化合物及其用途 |
| MX381304B (es) * | 2013-10-16 | 2025-03-12 | Shanghai Yingli Pharm Co Ltd | Compuesto heterocíclico fusionado, método de preparación del mismo, composición farmacéutica, y usos del mismo. |
| 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 |
| MX382033B (es) | 2014-03-19 | 2025-03-13 | Infinity Pharmaceuticals Inc | Compuestos heterocíclicos para utilizarlos en el tratamiento de trastornos mediados por pi3k-gamma. |
| US20150320755A1 (en) | 2014-04-16 | 2015-11-12 | 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 |
| WO2016054491A1 (en) | 2014-10-03 | 2016-04-07 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| SG11201703826TA (en) * | 2014-12-17 | 2017-07-28 | Pfizer | Formulations of a pi3k/mtor-inhibitor for intravenous administration |
| MX2017012390A (es) | 2015-03-30 | 2018-01-26 | Daiichi Sankyo Co Ltd | Derivados de 6-morfolinil-2-pirazolil-9h-purina y su uso como inhibidores de fosfoinositol-3-cinasa (pi3k). |
| 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 |
| JP6518833B2 (ja) * | 2015-04-21 | 2019-05-22 | ▲貴▼州百▲霊▼企▲業▼集▲団▼制▲薬▼股▲分▼有限公司Ｇｕｉｚｈｏｕ Ｂａｉｌｉｎｇ Ｇｒｏｕｐ Ｐｈａｒｍａｃｅｕｔｉｃａｌ Ｃｏ．，Ｌｔｄ． | プリニル−ｎ−ヒドロキシルピリミジンホルムアミド誘導体、並びにその調製方法および使用 |
| WO2016205334A1 (en) | 2015-06-16 | 2016-12-22 | Vascular Strategies Llc | Drug delivery and imaging chemical conjugate, formulations and methods of use thereof |
| US10160761B2 (en) | 2015-09-14 | 2018-12-25 | Infinity Pharmaceuticals, Inc. | Solid forms of isoquinolinones, and process of making, composition comprising, and methods of using the same |
| US10759806B2 (en) | 2016-03-17 | 2020-09-01 | Infinity Pharmaceuticals, Inc. | Isotopologues of isoquinolinone and quinazolinone compounds and uses thereof as PI3K kinase inhibitors |
| US10919914B2 (en) | 2016-06-08 | 2021-02-16 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| RU2754507C2 (ru) | 2016-06-24 | 2021-09-02 | Инфинити Фармасьютикалз, Инк. | Комбинированная терапия |
| 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 |
| 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 |
| TW201817731A (zh) * | 2016-09-29 | 2018-05-16 | 日商第一三共股份有限公司 | ［２－（１－甲基－１ｈ－吡唑－４－基）－６－（ 啉－４－基）－９ｈ－嘌呤－８－基］［４－（ 啉－４－基）哌啶－１－基］甲酮及其製藥上容許鹽之結晶 |
| CN110036109A (zh) | 2016-12-02 | 2019-07-19 | 第一三共株式会社 | 新颖的内-β-N-乙酰基氨基葡糖苷酶 |
| 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 |
| AR120173A1 (es) * | 2019-10-09 | 2022-02-02 | 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 |
| US5866702A (en) * | 1996-08-02 | 1999-02-02 | Cv Therapeutics, Incorporation | Purine inhibitors of cyclin dependent kinase 2 |
| US6790958B2 (en) * | 1996-08-02 | 2004-09-14 | Robert T. Lum | Purine inhibitors of cyclin dependent kinase 2 & IKBA |
| 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 |
| CN1186324C (zh) | 2000-04-27 | 2005-01-26 | 山之内制药株式会社 | 稠合杂芳基衍生物 |
| AU2002323475B2 (en) | 2001-09-13 | 2006-09-28 | Synta Pharmaceuticals Corp | 2-aroylimidazole compounds for treating cancer |
| US6949644B2 (en) | 2001-10-12 | 2005-09-27 | Irm Llc | Methods for the synthesis of substituted purines |
| JP2005512972A (ja) * | 2001-10-12 | 2005-05-12 | アイアールエム エルエルシー | キナーゼ阻害剤足場およびそれらの調製方法 |
| ATE355291T1 (de) * | 2001-12-18 | 2006-03-15 | Cv Therapeutics Inc | A2a adenosinrezeptorantagonisten |
| US20030139427A1 (en) | 2002-08-23 | 2003-07-24 | Osi Pharmaceuticals Inc. | Bicyclic pyrimidinyl derivatives and methods of use thereof |
| WO2004021979A2 (en) * | 2002-09-06 | 2004-03-18 | Smithkline Beecham Corporation | PYRROLO[2, 3-d]PYRIMIDINE-4-YL AND PURIN-6-YL UREA COMPOUNDS |
| US7122665B2 (en) | 2002-10-15 | 2006-10-17 | Synta Pharmaceuticals Corp. | Heterocyclic compounds |
| JP2007500241A (ja) | 2003-05-29 | 2007-01-11 | シンタ ファーマシューティカルズ コーポレーション | 過度の骨量減少に関連する疾患の予防及び治療用の複素環化合物 |
| 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 |
| EP2132208A1 (en) | 2007-03-28 | 2009-12-16 | NeuroSearch AS | Purinyl derivatives and their use as potassium channel modulators |
| US20120004246A1 (en) * | 2007-03-28 | 2012-01-05 | Neurosearch A/S | Purinyl derivatives and their use as potassium channel modulators |
| CN101835779B (zh) * | 2007-10-26 | 2014-01-29 | 霍夫曼-拉罗奇有限公司 | 作为pi3激酶抑制剂的嘌呤衍生物 |
| 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 |
| WO2010114484A1 (en) * | 2009-04-03 | 2010-10-07 | S*Bio Pte Ltd | Pyrimidine substituted purine compounds as kinase (s) inhibitors |
| SG175708A1 (en) * | 2009-05-27 | 2011-12-29 | Genentech Inc | Bicyclic pyrimidine pi3k inhibitor compounds selective for p110 delta, and methods of use |
| US8158625B2 (en) * | 2009-05-27 | 2012-04-17 | Genentech, Inc. | Bicyclic indole-pyrimidine PI3K inhibitor compounds selective for P110 delta, and methods of use |
| ES2596654T3 (es) * | 2009-11-12 | 2017-01-11 | F. Hoffmann-La Roche Ag | Compuestos de purina N-9-sustituida, composiciones y métodos de uso |
| 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 |
-
2009
- 2009-05-29 AU AU2009251291A patent/AU2009251291B2/en not_active Ceased
- 2009-05-29 RU RU2010154428/04A patent/RU2509081C2/ru not_active IP Right Cessation
- 2009-05-29 EP EP09755767.2A patent/EP2279188B1/en active Active
- 2009-05-29 JP JP2011511842A patent/JP2011521968A/ja active Pending
- 2009-05-29 BR BRPI0909614A patent/BRPI0909614A2/pt not_active Application Discontinuation
- 2009-05-29 WO PCT/US2009/045603 patent/WO2009146406A1/en not_active Ceased
- 2009-05-29 CA CA2721851A patent/CA2721851A1/en not_active Abandoned
- 2009-05-29 ES ES09755767.2T patent/ES2533788T3/es active Active
- 2009-05-29 KR KR1020107026673A patent/KR20110042153A/ko not_active Ceased
- 2009-05-29 MX MX2010012583A patent/MX2010012583A/es active IP Right Grant
- 2009-05-29 CN CN200980129148.2A patent/CN102105474B/zh active Active
- 2009-05-29 US US12/474,613 patent/US8158624B2/en active Active
-
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
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2011521968A5 (en:Method) | ||
| JP7447002B2 (ja) | ＳＨＰ２のオクタヒドロシクロペンタ［ｃ］ピロールのアロステリック阻害剤 | |
| US10287266B2 (en) | Compounds and compositions for inhibiting the activity of SHP2 | |
| RU2010154428A (ru) | Пуриновые соединения, ингибирующие рi3к и способы применения | |
| US9815820B2 (en) | Rho kinase inhibitors | |
| JP4667537B2 (ja) | アシルチオウレア化合物又はその塩、及びその用途 | |
| KR101760651B1 (ko) | 피롤일 치환된 다이하이드로인돌 2 온 유도체, 그의 제조 방법 및 용도 | |
| JP2011510995A5 (en:Method) | ||
| CA2730271A1 (en) | Pi3k isoform selective inhibitors | |
| JP6896701B2 (ja) | イミダゾリルアミド誘導体 | |
| JP2009535390A5 (en:Method) | ||
| WO2014151871A9 (en) | Jak2 and alk2 inhibitors and methods for their use | |
| JP6581180B2 (ja) | ピリジン置換の２−アミノピリジン類タンパク質キナーゼ阻害剤 | |
| EP3181554B1 (en) | Quinazoline derivative | |
| CN107827875B (zh) | 一种苯并咪唑类衍生物作为周期蛋白依赖性激酶4/6抑制剂的应用 | |
| JP2004525139A (ja) | Ｆｌｔ−１リガンド、および血管形成により調節可能な疾患の治療におけるそれらの使用 | |
| JPWO2008139894A1 (ja) | 含窒素芳香族６員環誘導体並びにそれらを含む医薬 | |
| CN103476769B (zh) | 抗癌剂 | |
| US20130131112A1 (en) | Salts of 3-(4-amino-1-oxo-1,3-dihydro-isoindol-2-yl)piperidine-2,6-dione and derivatives thereof, or polymorphs of salts, process for preparing same and use thereof | |
| US7888380B2 (en) | 1,2,4-Triazolylaminoaryl (heteroaryl) sulfonamide derivatives | |
| CN115716850B (zh) | 芳基磷氧化合物的晶型、制备方法及用途 | |
| CN114790177B (zh) | 新型Hedgehog信号通路抑制剂 | |
| EP2426130B1 (en) | Purine derivative and antitumor agent using same |