JP2017513955A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2017513955A5 JP2017513955A5 JP2017507914A JP2017507914A JP2017513955A5 JP 2017513955 A5 JP2017513955 A5 JP 2017513955A5 JP 2017507914 A JP2017507914 A JP 2017507914A JP 2017507914 A JP2017507914 A JP 2017507914A JP 2017513955 A5 JP2017513955 A5 JP 2017513955A5
- Authority
- JP
- Japan
- Prior art keywords
- methoxy
- purin
- dihydroxytetrahydrofuran
- alkyl
- amino
- 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.)
- Granted
Links
- 125000000217 alkyl group Chemical group 0.000 claims 120
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims 96
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 94
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 40
- 125000005843 halogen group Chemical group 0.000 claims 34
- 125000001424 substituent group Chemical group 0.000 claims 33
- 125000003118 aryl group Chemical group 0.000 claims 29
- 150000003839 salts Chemical class 0.000 claims 29
- 150000001875 compounds Chemical class 0.000 claims 28
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 23
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 19
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 17
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 16
- 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims 16
- 229910052799 carbon Inorganic materials 0.000 claims 16
- 229910052739 hydrogen Inorganic materials 0.000 claims 14
- -1 (Methylsulfonyl) methyl Chemical group 0.000 claims 13
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 10
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 10
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 9
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 9
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 8
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 2
- QMCUISJHXICPLC-XNIJJKJLSA-N NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)(C(=O)O)CC1=C(C=CC=C1F)F)O)O Chemical compound NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)(C(=O)O)CC1=C(C=CC=C1F)F)O)O QMCUISJHXICPLC-XNIJJKJLSA-N 0.000 claims 2
- OGXXBFXUZNNBBS-UQAWHXBNSA-N O[C@@H]1[C@@H](COC(C(O)=O)C(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C(N[C@@H]3CCOC3)N=C(Cl)N=C12 Chemical compound O[C@@H]1[C@@H](COC(C(O)=O)C(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C(N[C@@H]3CCOC3)N=C(Cl)N=C12 OGXXBFXUZNNBBS-UQAWHXBNSA-N 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- OYYIRWXXCQBYJG-QLRVTQMJSA-N 2-[[(1R,2R,3S,4R)-4-(5-chloro-4-oxoquinazolin-3-yl)-2,3-dihydroxycyclopentyl]methoxy]-2-phosphonoacetic acid Chemical compound ClC1=C2C(N(C=NC2=CC=C1)[C@H]1[C@@H]([C@@H]([C@H](C1)COC(C(=O)O)P(=O)(O)O)O)O)=O OYYIRWXXCQBYJG-QLRVTQMJSA-N 0.000 claims 1
- NNACJYKNBNMOIB-FDGLDMCPSA-N 2-[[(2R,3S,4R,5R)-3,4-dihydroxy-5-[6-(4-hydroxypiperidin-1-yl)purin-9-yl]oxolan-2-yl]methoxy]-2-phosphonoacetic acid Chemical compound O[C@@H]1[C@H](O[C@H]([C@@H]1O)N1C2=NC=NC(=C2N=C1)N1CCC(CC1)O)COC(C(=O)O)P(=O)(O)O NNACJYKNBNMOIB-FDGLDMCPSA-N 0.000 claims 1
- KJEXWSKRPPXAMG-XNIJJKJLSA-N 2-[[(2R,3S,4R,5R)-5-(6-amino-2-chloropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy]-2-[(4-fluorophenyl)methyl]propanedioic acid Chemical compound NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)(C(=O)O)CC1=CC=C(C=C1)F)O)O KJEXWSKRPPXAMG-XNIJJKJLSA-N 0.000 claims 1
- YXMCFEMTFYAHFD-OSWLWWHVSA-N C(C)(=O)NNC(C(OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)N1C2=NC(=NC(=C2N=C1)N)Cl)P(O)(O)=O)=O Chemical compound C(C)(=O)NNC(C(OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)N1C2=NC(=NC(=C2N=C1)N)Cl)P(O)(O)=O)=O YXMCFEMTFYAHFD-OSWLWWHVSA-N 0.000 claims 1
- HDMQNESUKKEGDK-HTTXCKMZSA-N C(C)(C)(C)OC(C(OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)N1C2=NC(=NC(=C2N=C1)OC)OC)P(O)(O)=O)=O Chemical compound C(C)(C)(C)OC(C(OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)N1C2=NC(=NC(=C2N=C1)OC)OC)P(O)(O)=O)=O HDMQNESUKKEGDK-HTTXCKMZSA-N 0.000 claims 1
- MMYSSOQJLSGEIO-RTAOWTGSSA-N C(C)NC(C(OC[C@@H]1[C@H]([C@H]([C@@H](C1)N1C2=NC=NC(=C2N=C1)NCC)O)O)P(O)(O)=O)=O Chemical compound C(C)NC(C(OC[C@@H]1[C@H]([C@H]([C@@H](C1)N1C2=NC=NC(=C2N=C1)NCC)O)O)P(O)(O)=O)=O MMYSSOQJLSGEIO-RTAOWTGSSA-N 0.000 claims 1
- JJTMJMCSFXBNRE-VCKWHPSQSA-N C(C1=CC=CC=C1)(=O)NC1=C2N=CN(C2=NC(=N1)I)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)P(=O)(O)O)O)O Chemical compound C(C1=CC=CC=C1)(=O)NC1=C2N=CN(C2=NC(=N1)I)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)P(=O)(O)O)O)O JJTMJMCSFXBNRE-VCKWHPSQSA-N 0.000 claims 1
- FWWPZKBZBGKNPG-PNXMHIEFSA-N CC1=NC(=C2N=CN(C2=N1)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)P(=O)(O)O)O)O)C Chemical compound CC1=NC(=C2N=CN(C2=N1)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)P(=O)(O)O)O)O)C FWWPZKBZBGKNPG-PNXMHIEFSA-N 0.000 claims 1
- DDRJOQIPWNVAIN-UQALVKDESA-N CCNC(=O)C(OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(=O)N(C)C1=O)P(O)(O)=O Chemical compound CCNC(=O)C(OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(=O)N(C)C1=O)P(O)(O)=O DDRJOQIPWNVAIN-UQALVKDESA-N 0.000 claims 1
- BFHYAOVYTYZXAQ-HEOLNDPQSA-N CCOC(=O)C(OC[C@H]1C[C@H]([C@H](O)[C@@H]1O)N1N=NC2=C1N=C(Cl)N=C2N)P(O)(O)=O Chemical compound CCOC(=O)C(OC[C@H]1C[C@H]([C@H](O)[C@@H]1O)N1N=NC2=C1N=C(Cl)N=C2N)P(O)(O)=O BFHYAOVYTYZXAQ-HEOLNDPQSA-N 0.000 claims 1
- MAWBBBBUAWAYIY-RIEBNTRSSA-N CCOC(=O)C(OC[C@H]1C[C@H]([C@H](O)[C@@H]1O)N1N=NC2=C1N=C(Cl)N=C2NC1CCCC1)P(O)(O)=O Chemical compound CCOC(=O)C(OC[C@H]1C[C@H]([C@H](O)[C@@H]1O)N1N=NC2=C1N=C(Cl)N=C2NC1CCCC1)P(O)(O)=O MAWBBBBUAWAYIY-RIEBNTRSSA-N 0.000 claims 1
- IXBOQMWWBLJCNG-YRDFTPMFSA-N CCOC(=O)C(OC[C@H]1C[C@H]([C@H](O)[C@@H]1O)N1N=NC2=C1N=C(Cl)N=C2N[C@@H]1CCOC1)P(O)(O)=O Chemical compound CCOC(=O)C(OC[C@H]1C[C@H]([C@H](O)[C@@H]1O)N1N=NC2=C1N=C(Cl)N=C2N[C@@H]1CCOC1)P(O)(O)=O IXBOQMWWBLJCNG-YRDFTPMFSA-N 0.000 claims 1
- IXBOQMWWBLJCNG-AIJVHSERSA-N CCOC(=O)C(OC[C@H]1C[C@H]([C@H](O)[C@@H]1O)N1N=NC2=C1N=C(Cl)N=C2N[C@H]1CCOC1)P(O)(O)=O Chemical compound CCOC(=O)C(OC[C@H]1C[C@H]([C@H](O)[C@@H]1O)N1N=NC2=C1N=C(Cl)N=C2N[C@H]1CCOC1)P(O)(O)=O IXBOQMWWBLJCNG-AIJVHSERSA-N 0.000 claims 1
- 229940127272 CD73 inhibitor Drugs 0.000 claims 1
- HBNCWUFGFIVBQK-QWKSCMCOSA-N CNC(=O)C(OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(=O)N(C)C1=O)P(O)(O)=O Chemical compound CNC(=O)C(OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(=O)N(C)C1=O)P(O)(O)=O HBNCWUFGFIVBQK-QWKSCMCOSA-N 0.000 claims 1
- RBLJDONPZPVMLS-QHQIBUKQSA-N COC1=NC(=C2N=CN(C2=N1)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)P(=O)(O)O)O)O)OC Chemical compound COC1=NC(=C2N=CN(C2=N1)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)P(=O)(O)O)O)O)OC RBLJDONPZPVMLS-QHQIBUKQSA-N 0.000 claims 1
- NKHFMWKHXYOSJE-SDTWEEQHSA-N ClC1=C2C(N(C=NC2=CC=C1)[C@H]1[C@@H]([C@@H]([C@H](C1)COC(C(=O)O)C(=O)O)O)O)=O Chemical compound ClC1=C2C(N(C=NC2=CC=C1)[C@H]1[C@@H]([C@@H]([C@H](C1)COC(C(=O)O)C(=O)O)O)O)=O NKHFMWKHXYOSJE-SDTWEEQHSA-N 0.000 claims 1
- KDAUBZMRXUEEIY-IOSLPCCCSA-N ClC1=NC(=C2N=CN(C2=N1)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)(C(=O)O)C)O)O)NC Chemical compound ClC1=NC(=C2N=CN(C2=N1)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)(C(=O)O)C)O)O)NC KDAUBZMRXUEEIY-IOSLPCCCSA-N 0.000 claims 1
- PWSPRWKVAKSRBN-QTQZEZTPSA-N ClC1=NC(=C2N=CN(C2=N1)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)(C(=O)O)CC1=CC=C(C=C1)F)O)O)NC1CCCC1 Chemical compound ClC1=NC(=C2N=CN(C2=N1)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)(C(=O)O)CC1=CC=C(C=C1)F)O)O)NC1CCCC1 PWSPRWKVAKSRBN-QTQZEZTPSA-N 0.000 claims 1
- OGXXBFXUZNNBBS-XLZJSAHRSA-N ClC1=NC(=C2N=CN(C2=N1)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)C(=O)O)O)O)N[C@@H]1COCC1 Chemical compound ClC1=NC(=C2N=CN(C2=N1)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)C(=O)O)O)O)N[C@@H]1COCC1 OGXXBFXUZNNBBS-XLZJSAHRSA-N 0.000 claims 1
- XVPMURAJTFPVRM-JPJRCZBHSA-N ClC1=NC(=C2N=CN(C2=N1)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)P(=O)(O)O)O)O)Cl Chemical compound ClC1=NC(=C2N=CN(C2=N1)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)P(=O)(O)O)O)O)Cl XVPMURAJTFPVRM-JPJRCZBHSA-N 0.000 claims 1
- SSYZTARPABQFID-QHQIBUKQSA-N ClC1=NC(=C2N=CN(C2=N1)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)P(=O)(O)O)O)O)OCC Chemical compound ClC1=NC(=C2N=CN(C2=N1)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)P(=O)(O)O)O)O)OCC SSYZTARPABQFID-QHQIBUKQSA-N 0.000 claims 1
- JGTWTQBQBGKBFZ-DXXSKVHTSA-N NC1=C2N=CN(C2=NC(=N1)C#N)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)OC(C)(C)C)P(O)(O)=O)O)O Chemical compound NC1=C2N=CN(C2=NC(=N1)C#N)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)OC(C)(C)C)P(O)(O)=O)O)O JGTWTQBQBGKBFZ-DXXSKVHTSA-N 0.000 claims 1
- ZZNWMLAVCIQQLD-ZKUZGDEQSA-N NC1=C2N=CN(C2=NC(=N1)C)[C@H]1[C@@H]([C@@H]([C@H](O1)CO[C@H](C(=O)O)P(=O)(O)O)O)O Chemical compound NC1=C2N=CN(C2=NC(=N1)C)[C@H]1[C@@H]([C@@H]([C@H](O1)CO[C@H](C(=O)O)P(=O)(O)O)O)O ZZNWMLAVCIQQLD-ZKUZGDEQSA-N 0.000 claims 1
- CIVPXOCMWPFMIF-IWCJZZDYSA-N NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)(C(=O)O)CC1=C(C=CC=C1)S(=O)(=O)C)O)O Chemical compound NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)(C(=O)O)CC1=C(C=CC=C1)S(=O)(=O)C)O)O CIVPXOCMWPFMIF-IWCJZZDYSA-N 0.000 claims 1
- MYUXBGBQHXGNLZ-XNIJJKJLSA-N NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)(C(=O)O)CC1=CC(=CC(=C1)F)F)O)O Chemical compound NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)(C(=O)O)CC1=CC(=CC(=C1)F)F)O)O MYUXBGBQHXGNLZ-XNIJJKJLSA-N 0.000 claims 1
- UWPWDHNHBVJIPL-LSCFUAHRSA-N NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)(C(=O)O)CC1=CC=C(C=C1)C#N)O)O Chemical compound NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)(C(=O)O)CC1=CC=C(C=C1)C#N)O)O UWPWDHNHBVJIPL-LSCFUAHRSA-N 0.000 claims 1
- BOVGAKLPQQBCFB-XNIJJKJLSA-N NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)(C(=O)O)CC1=CC=C(C=C1)Cl)O)O Chemical compound NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)(C(=O)O)CC1=CC=C(C=C1)Cl)O)O BOVGAKLPQQBCFB-XNIJJKJLSA-N 0.000 claims 1
- ZFZKPWFNIIBZJD-XNIJJKJLSA-N NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)(C(=O)O)CC1=CC=CC=C1)O)O Chemical compound NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)(C(=O)O)CC1=CC=CC=C1)O)O ZFZKPWFNIIBZJD-XNIJJKJLSA-N 0.000 claims 1
- AKQLZWWBBFMBMO-SDBHATRESA-N NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)(C(=O)O)CC1=NC=CC=C1)O)O Chemical compound NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)(C(=O)O)CC1=NC=CC=C1)O)O AKQLZWWBBFMBMO-SDBHATRESA-N 0.000 claims 1
- GZBUYOTUXSRKEE-QYVSTXNMSA-N NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)(C(=O)O)CC1CC1)O)O Chemical compound NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)(C(=O)O)CC1CC1)O)O GZBUYOTUXSRKEE-QYVSTXNMSA-N 0.000 claims 1
- FGAFHLCJLQFWAP-ZRFIDHNTSA-N NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)(C(=O)O)CC=1SC=CN1)O)O Chemical compound NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)(C(=O)O)CC=1SC=CN1)O)O FGAFHLCJLQFWAP-ZRFIDHNTSA-N 0.000 claims 1
- GAXFSNUKRJNBBJ-IOSLPCCCSA-N NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)(C(=O)O)COC)O)O Chemical compound NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)(C(=O)O)COC)O)O GAXFSNUKRJNBBJ-IOSLPCCCSA-N 0.000 claims 1
- QVERRRVPLJPAII-LSCFUAHRSA-N NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)(C(=O)O)COCC1=CC=CC=C1)O)O Chemical compound NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)(C(=O)O)COCC1=CC=CC=C1)O)O QVERRRVPLJPAII-LSCFUAHRSA-N 0.000 claims 1
- VNDRHKSOWDUKOB-BHBWVORQSA-N NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)C(=O)O)O)O Chemical compound NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)C(=O)O)O)O VNDRHKSOWDUKOB-BHBWVORQSA-N 0.000 claims 1
- LBYMBTPZPDLDBZ-CFGMHQHXSA-N NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1[C@@H]([C@@H]([C@H](O1)CO[C@@H](C(=O)O)P(=O)(O)O)O)O Chemical compound NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1[C@@H]([C@@H]([C@H](O1)CO[C@@H](C(=O)O)P(=O)(O)O)O)O LBYMBTPZPDLDBZ-CFGMHQHXSA-N 0.000 claims 1
- LBYMBTPZPDLDBZ-KXSYMAMXSA-N NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1[C@@H]([C@@H]([C@H](O1)CO[C@H](C(=O)O)P(=O)(O)O)O)O Chemical compound NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1[C@@H]([C@@H]([C@H](O1)CO[C@H](C(=O)O)P(=O)(O)O)O)O LBYMBTPZPDLDBZ-KXSYMAMXSA-N 0.000 claims 1
- XYAVCQTXWJKTHK-QHQIBUKQSA-N NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1[C@@H]([C@@H]([C@H](O1)CSC(C(=O)OCC)P(O)(O)=O)O)O Chemical compound NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1[C@@H]([C@@H]([C@H](O1)CSC(C(=O)OCC)P(O)(O)=O)O)O XYAVCQTXWJKTHK-QHQIBUKQSA-N 0.000 claims 1
- VJIZTMICECSZHQ-PTPKGGSUSA-N NC1=C2N=CN(C2=NC(=N1)F)[C@H]1[C@@H]([C@@H]([C@H](O1)CO[C@@](CC(=O)O)(C(=O)OCC)P(=O)(O)O)O)O Chemical compound NC1=C2N=CN(C2=NC(=N1)F)[C@H]1[C@@H]([C@@H]([C@H](O1)CO[C@@](CC(=O)O)(C(=O)OCC)P(=O)(O)O)O)O VJIZTMICECSZHQ-PTPKGGSUSA-N 0.000 claims 1
- SGCANUARCJWKQX-KXSYMAMXSA-N NC1=C2N=CN(C2=NC(=N1)F)[C@H]1[C@@H]([C@@H]([C@H](O1)CO[C@H](C(=O)O)P(=O)(O)O)O)O Chemical compound NC1=C2N=CN(C2=NC(=N1)F)[C@H]1[C@@H]([C@@H]([C@H](O1)CO[C@H](C(=O)O)P(=O)(O)O)O)O SGCANUARCJWKQX-KXSYMAMXSA-N 0.000 claims 1
- VJIZTMICECSZHQ-BFDBYCNMSA-N NC1=C2N=CN(C2=NC(=N1)F)[C@H]1[C@@H]([C@@H]([C@H](O1)CO[C@](CC(=O)O)(C(=O)OCC)P(=O)(O)O)O)O Chemical compound NC1=C2N=CN(C2=NC(=N1)F)[C@H]1[C@@H]([C@@H]([C@H](O1)CO[C@](CC(=O)O)(C(=O)OCC)P(=O)(O)O)O)O VJIZTMICECSZHQ-BFDBYCNMSA-N 0.000 claims 1
- AJCUHKYNVWGAMK-CFGMHQHXSA-N NC1=C2N=CN(C2=NC(=N1)I)[C@H]1[C@@H]([C@@H]([C@H](O1)CO[C@@H](C(=O)O)P(=O)(O)O)O)O Chemical compound NC1=C2N=CN(C2=NC(=N1)I)[C@H]1[C@@H]([C@@H]([C@H](O1)CO[C@@H](C(=O)O)P(=O)(O)O)O)O AJCUHKYNVWGAMK-CFGMHQHXSA-N 0.000 claims 1
- AJCUHKYNVWGAMK-KXSYMAMXSA-N NC1=C2N=CN(C2=NC(=N1)I)[C@H]1[C@@H]([C@@H]([C@H](O1)CO[C@H](C(=O)O)P(=O)(O)O)O)O Chemical compound NC1=C2N=CN(C2=NC(=N1)I)[C@H]1[C@@H]([C@@H]([C@H](O1)CO[C@H](C(=O)O)P(=O)(O)O)O)O AJCUHKYNVWGAMK-KXSYMAMXSA-N 0.000 claims 1
- IIOWKKLLJJXIDK-OAPDWXTOSA-N NC1=C2N=CN(C2=NC(=N1)SC)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)OCC)P(O)(O)=O)O)O Chemical compound NC1=C2N=CN(C2=NC(=N1)SC)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)OCC)P(O)(O)=O)O)O IIOWKKLLJJXIDK-OAPDWXTOSA-N 0.000 claims 1
- DYFWYSSWTRWBDC-DZUKYTIJSA-N NC1=C2N=CN(C2=NC=N1)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)NO)P(O)(O)=O)O)O Chemical compound NC1=C2N=CN(C2=NC=N1)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)NO)P(O)(O)=O)O)O DYFWYSSWTRWBDC-DZUKYTIJSA-N 0.000 claims 1
- LTQZCPJUUPDELT-RPKMEZRRSA-N NC1=C2N=CN(C2=NC=N1)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)C(=O)O)O)O Chemical compound NC1=C2N=CN(C2=NC=N1)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)C(=O)O)O)O LTQZCPJUUPDELT-RPKMEZRRSA-N 0.000 claims 1
- JDSZIPBOWSSAOP-QHQIBUKQSA-N NC1=C2N=CN(C2=NC=N1)[C@H]1[C@@H]([C@@H]([C@H](O1)CSC(C(=O)OC)P(O)(O)=O)O)O Chemical compound NC1=C2N=CN(C2=NC=N1)[C@H]1[C@@H]([C@@H]([C@H](O1)CSC(C(=O)OC)P(O)(O)=O)O)O JDSZIPBOWSSAOP-QHQIBUKQSA-N 0.000 claims 1
- AFFILDHYLOSONF-HEOLNDPQSA-N NC=1C2=C(N=C(N1)Br)N(N=N2)[C@H]2[C@@H]([C@@H]([C@H](C2)COC(C(=O)OCC)P(O)(O)=O)O)O Chemical compound NC=1C2=C(N=C(N1)Br)N(N=N2)[C@H]2[C@@H]([C@@H]([C@H](C2)COC(C(=O)OCC)P(O)(O)=O)O)O AFFILDHYLOSONF-HEOLNDPQSA-N 0.000 claims 1
- OFRRTZLVHRSMMO-DCEZOGAWSA-N O[C@@H]1[C@H](O[C@H]([C@@H]1O)N1C(N(C(C=C1)=O)C)=O)CO[C@@H](C(=O)O)P(=O)(O)O Chemical compound O[C@@H]1[C@H](O[C@H]([C@@H]1O)N1C(N(C(C=C1)=O)C)=O)CO[C@@H](C(=O)O)P(=O)(O)O OFRRTZLVHRSMMO-DCEZOGAWSA-N 0.000 claims 1
- OFRRTZLVHRSMMO-NAHXDTDZSA-N O[C@@H]1[C@H](O[C@H]([C@@H]1O)N1C(N(C(C=C1)=O)C)=O)CO[C@H](C(=O)O)P(=O)(O)O Chemical compound O[C@@H]1[C@H](O[C@H]([C@@H]1O)N1C(N(C(C=C1)=O)C)=O)CO[C@H](C(=O)O)P(=O)(O)O OFRRTZLVHRSMMO-NAHXDTDZSA-N 0.000 claims 1
- XOTGQOBBWXNESB-JPJRCZBHSA-N O[C@@H]1[C@H](O[C@H]([C@@H]1O)N1C2=NC(=NC(=C2N=C1)NO)I)COC(C(=O)O)P(=O)(O)O Chemical compound O[C@@H]1[C@H](O[C@H]([C@@H]1O)N1C2=NC(=NC(=C2N=C1)NO)I)COC(C(=O)O)P(=O)(O)O XOTGQOBBWXNESB-JPJRCZBHSA-N 0.000 claims 1
- ABNPHTLAJHVJGX-JTPBVDGGSA-N O[C@@H]1[C@H](O[C@H]([C@@H]1O)N1C2=NC=NC(=C2N=C1)NC(C)C)COC(C(=O)O)P(=O)(O)O Chemical compound O[C@@H]1[C@H](O[C@H]([C@@H]1O)N1C2=NC=NC(=C2N=C1)NC(C)C)COC(C(=O)O)P(=O)(O)O ABNPHTLAJHVJGX-JTPBVDGGSA-N 0.000 claims 1
- FMSLMPQVLVZWID-QHQIBUKQSA-N O[C@@H]1[C@H](O[C@H]([C@@H]1O)N1C2=NC=NC(=C2N=C1)NC)COC(C(=O)O)P(=O)(O)O Chemical compound O[C@@H]1[C@H](O[C@H]([C@@H]1O)N1C2=NC=NC(=C2N=C1)NC)COC(C(=O)O)P(=O)(O)O FMSLMPQVLVZWID-QHQIBUKQSA-N 0.000 claims 1
- BMLJLDZEZRMGAF-CMAHQRSQSA-N O[C@@H]1[C@H](O[C@H]([C@@H]1O)N1C2=NC=NC(=C2N=C1)NC1=CC=CC=C1)COC(C(=O)O)P(=O)(O)O Chemical compound O[C@@H]1[C@H](O[C@H]([C@@H]1O)N1C2=NC=NC(=C2N=C1)NC1=CC=CC=C1)COC(C(=O)O)P(=O)(O)O BMLJLDZEZRMGAF-CMAHQRSQSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 0 CN(CC(*C1*)C(*)C1O*)CC(*)(*)* Chemical compound CN(CC(*C1*)C(*)C1O*)CC(*)(*)* 0.000 description 7
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201461984659P | 2014-04-25 | 2014-04-25 | |
| US61/984,659 | 2014-04-25 | ||
| US201462051529P | 2014-09-17 | 2014-09-17 | |
| US62/051,529 | 2014-09-17 | ||
| PCT/US2015/027235 WO2015164573A1 (en) | 2014-04-25 | 2015-04-23 | Purine derivatives as cd73 inhibitors for the treatment of cancer |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017513955A JP2017513955A (ja) | 2017-06-01 |
| JP2017513955A5 true JP2017513955A5 (OSRAM) | 2018-06-07 |
| JP6657182B2 JP6657182B2 (ja) | 2020-03-04 |
Family
ID=53175630
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017507914A Active JP6657182B2 (ja) | 2014-04-25 | 2015-04-23 | 癌治療用のｃｄ７３阻害剤としてのプリン誘導体 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US10654884B2 (OSRAM) |
| EP (1) | EP3134411B1 (OSRAM) |
| JP (1) | JP6657182B2 (OSRAM) |
| MA (1) | MA39986A (OSRAM) |
| WO (1) | WO2015164573A1 (OSRAM) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10167302B2 (en) * | 2014-05-23 | 2019-01-01 | University College Cork | Phosphonate nucleosides useful in the treatment of viral diseases |
| DK3221363T3 (da) | 2014-11-21 | 2020-08-10 | Bristol Myers Squibb Co | Antistoffer mod cd73 og anvendelser deraf |
| HRP20201756T8 (hr) | 2014-11-21 | 2021-08-20 | Bristol-Myers Squibb Company | Antitijela koja sadrže modificirane regije teškog lanca |
| CA3151595A1 (en) * | 2016-01-08 | 2017-07-13 | Arcus Biosciences, Inc. | Modulators of 5'-nucleotidase, ecto and the use thereof |
| RU2019108464A (ru) * | 2016-08-26 | 2020-09-28 | Мицубиси Танабе Фарма Корпорейшн | Бициклическое азотсодержащее гетероциклическое соединение |
| JP7125144B2 (ja) * | 2016-09-09 | 2022-08-24 | キャリセラ バイオサイエンシーズ， インコーポレイテッド | エクトヌクレオチダーゼ阻害剤およびその使用方法 |
| US11058704B2 (en) | 2016-10-03 | 2021-07-13 | Arcus Biosciences, Inc. | Inhibitors of adenosine 5′-nucleotidase |
| US11267845B2 (en) | 2016-11-18 | 2022-03-08 | Arcus Biosciences, Inc. | Inhibitors of CD73-mediated immunosuppression |
| CA3047988A1 (en) * | 2016-12-22 | 2018-06-28 | Calithera Biosciences, Inc. | Ectonucleotidase inhibitors and methods of use thereof |
| IL269150B2 (en) | 2017-03-16 | 2025-04-01 | Innate Pharma | Cancer treatment preparations and methods |
| JP2020515559A (ja) * | 2017-03-31 | 2020-05-28 | ぺロトン セラピューティクス，インク． | Ｃｄ７３阻害剤とその使用 |
| KR101841604B1 (ko) | 2017-04-26 | 2018-03-26 | 순천대학교 산학협력단 | 퍼푸린을 유효성분으로 포함하는 우울증 및 불안증의 예방 또는 치료용 조성물 |
| US11129841B2 (en) | 2017-05-10 | 2021-09-28 | Oric Pharmaceuticals, Inc. | CD73 inhibitors |
| EA039042B1 (ru) * | 2017-09-08 | 2021-11-25 | Калитера Байосайенсиз, Инк. | Ингибиторы эктонуклеотидазы и способы их применения |
| JP7274469B2 (ja) | 2017-10-06 | 2023-05-16 | イナート・ファルマ・ソシエテ・アノニム | Ｃｄ３９／ｃｄ７３軸によるｔ細胞活性の回復 |
| WO2019090111A1 (en) * | 2017-11-03 | 2019-05-09 | Oric Pharmaceuticals, Inc. | Cd73 inhibitors |
| KR102804816B1 (ko) | 2018-03-09 | 2025-05-09 | 페인스 테라퓨틱스 인코포레이티드 | 항-cd73 항체 및 이의 용도 |
| EP3761993A4 (en) * | 2018-03-09 | 2022-03-09 | Arcus Biosciences, Inc. | PARENTERALLY ADMINISTRATED IMMUNE-ENHANCERING DRUGS |
| IL304348B2 (en) * | 2018-04-30 | 2024-08-01 | Oric Pharmaceuticals Inc | CD73 inhibitors |
| TW202017569A (zh) * | 2018-05-31 | 2020-05-16 | 美商佩樂敦治療公司 | 用於抑制cd73之組合物及方法 |
| BR112020024412A8 (pt) | 2018-06-18 | 2023-03-21 | Innate Pharma | Anticorpos, composição farmacêutica, kit, ácido nucleico, célula hospedeira, métodos de tratamento ou prevenção de câncer, de redução da atividade, de aumento da atividade e de aumento da ativação |
| CN112888696B (zh) * | 2018-06-21 | 2024-04-16 | 德琪医疗有限公司 | 外核苷酸酶抑制剂及其使用方法 |
| WO2020046813A1 (en) | 2018-08-27 | 2020-03-05 | Arcus Biosciences, Inc. | Cd73 inhibitors |
| EP3843742A4 (en) | 2018-08-28 | 2022-04-20 | Jiangsu Hengrui Medicine Co., Ltd. | CD73 INHIBITORS AND THEIR THERAPEUTIC USES |
| US11530234B2 (en) | 2018-09-11 | 2022-12-20 | Risen (Suzhou) Pharma Tech Co., Ltd. | CD73 inhibitors and pharmaceutical uses thereof |
| US10881681B2 (en) | 2018-09-11 | 2021-01-05 | Risen (Suzhou) Pharma Tech Co., Ltd. | CD73 inhibitors and pharmaceutical uses thereof |
| CN111184698A (zh) * | 2018-11-15 | 2020-05-22 | 和记黄埔医药（上海）有限公司 | 呋喹替尼制剂及其应用 |
| US11819512B2 (en) | 2018-12-13 | 2023-11-21 | Arcus Biosciences, Inc. | Solid forms of a CD73 inhibitor and the use thereof |
| CA3126735A1 (en) | 2019-01-11 | 2020-07-16 | Omeros Corporation | Methods and compositions for treating cancer |
| CN112955444B (zh) * | 2019-01-22 | 2023-12-12 | 江苏恒瑞医药股份有限公司 | 一种新型的小分子cd73抑制剂、其制备方法及其在医药上的应用 |
| AU2020239048B2 (en) | 2019-03-12 | 2025-10-16 | Arcus Biosciences, Inc. | Treatment of oncogene-driven cancers |
| WO2020190073A1 (ko) * | 2019-03-20 | 2020-09-24 | 한국화학연구원 | 신규한 아졸로피리미딘 헤테로고리 화합물을 유효 성분으로 함유하는 약제학적 조성물 |
| WO2020205538A1 (en) * | 2019-03-29 | 2020-10-08 | Eternity Bioscience Inc. | Cd73 inhibitors and therapeutic uses thereof |
| KR20210144821A (ko) | 2019-03-29 | 2021-11-30 | 아르커스 바이오사이언시즈 인코포레이티드 | 규명된 아데노신 지문을 이용한 암의 치료방법 |
| WO2020210938A1 (en) * | 2019-04-15 | 2020-10-22 | Bioardis Llc | Quinazoline derivatives as cd73 inhibitors |
| CA3143496A1 (en) * | 2019-06-20 | 2020-12-24 | Calithera Biosciences, Inc. | Ectonucleotidase inhibitors and methods of use thereof |
| US20220331343A1 (en) * | 2019-07-16 | 2022-10-20 | Oric Pharmaceuticals, Inc. | Cd73 inhibitors |
| KR20220081359A (ko) | 2019-10-09 | 2022-06-15 | 바이엘 악티엔게젤샤프트 | 살충제로서의 신규 헤테로아릴-트리아졸 화합물 |
| CA3159248C (en) * | 2019-10-30 | 2024-05-28 | Oric Pharmaceuticals, Inc. | Cd73 inhibitors |
| US11633416B1 (en) | 2020-03-06 | 2023-04-25 | Arcus Biosciences, Inc. | Oral formulations of CD73 compounds |
| WO2021247188A1 (en) | 2020-06-05 | 2021-12-09 | Bristol-Myers Squibb Company | Cd73 antagonist potency assay and methods of use thereof |
| CA3179320A1 (en) | 2020-06-17 | 2021-12-23 | Arcus Biosciences, Inc. | Crystalline forms of a cd73 inhibitor and uses thereof |
| CN118576601A (zh) * | 2020-10-23 | 2024-09-03 | 和记黄埔医药（上海）有限公司 | 一种药物组合产品在制备用于治疗结肠癌的药物中的用途 |
| CN113549076B (zh) * | 2021-07-23 | 2022-12-06 | 中国药科大学 | 一种多取代嘌呤类化合物及其制备方法和应用 |
| AU2023252914A1 (en) | 2022-04-13 | 2024-10-17 | Arcus Biosciences, Inc. | Combination therapy for treating trop-2 expressing cancers |
| WO2025137640A1 (en) | 2023-12-22 | 2025-06-26 | Gilead Sciences, Inc. | Azaspiro wrn inhibitors |
| WO2025233264A1 (en) | 2024-05-07 | 2025-11-13 | Innate Pharma | Use of cd73 blocking agents in combination with anti-cd20 x cd3 t cell engagers |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2336361C (en) | 1998-07-01 | 2011-09-06 | The Trustees Of The University Of Pennsylvania | Cavity induced allosteric modification of intermolecular interactions and methods of identifying compounds that effect the same |
| US20040043959A1 (en) * | 2002-03-04 | 2004-03-04 | Bloom Laura A. | Combination therapies for treating methylthioadenosine phosphorylase deficient cells |
| US7247621B2 (en) | 2002-04-30 | 2007-07-24 | Valeant Research & Development | Antiviral phosphonate compounds and methods therefor |
| WO2006130217A2 (en) * | 2005-04-01 | 2006-12-07 | The Regents Of The University Of California | Substituted phosphate esters of nucleoside phosphonates |
| EP1860113A1 (en) * | 2006-05-24 | 2007-11-28 | Rheinische Friedrich-Wilhelms-Universität Bonn | Ectonucleotidase inhibitors |
| US8956824B2 (en) | 2006-12-04 | 2015-02-17 | British Columbia Cancer Agency Branch | Methods for identifying allosteric modulators of ship polypeptides |
| US8828944B2 (en) | 2010-04-22 | 2014-09-09 | Institut Gustave Roussy | Compounds and uses thereof to induce an immunogenic cancer cell death in a subject |
| US8865653B2 (en) | 2010-04-22 | 2014-10-21 | Institut Gustave Roussy | Method of treatment for immunogenic treatment resistant cancer |
| WO2012031320A1 (en) | 2010-09-06 | 2012-03-15 | Peter Maccallum Cancer Institute | Cancer diagnostic |
| WO2014153424A1 (en) | 2013-03-19 | 2014-09-25 | La Jolla Institute For Allergy And Immunology | Reducing diabetes in patients receiving hmg-coa reductase inhibitors (statins) |
-
2015
- 2015-04-23 EP EP15722317.3A patent/EP3134411B1/en active Active
- 2015-04-23 MA MA039986A patent/MA39986A/fr unknown
- 2015-04-23 WO PCT/US2015/027235 patent/WO2015164573A1/en not_active Ceased
- 2015-04-23 JP JP2017507914A patent/JP6657182B2/ja active Active
- 2015-04-23 US US15/306,197 patent/US10654884B2/en active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2017513955A5 (OSRAM) | ||
| AU2016377364A1 (en) | 4-amino-2-(1H-pyrazolo[3,4-b]pyridin-3-yl)-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine derivatives and the respective (1H-indazol-3-yl) derivatives as cGMP modulators for treating cardiovascular diseases | |
| JP2010504346A5 (OSRAM) | ||
| AU2009282478A1 (en) | Flavin derivatives | |
| JP2016536288A5 (OSRAM) | ||
| JP2011500758A5 (OSRAM) | ||
| JP2013532652A5 (OSRAM) | ||
| JP2015519401A5 (OSRAM) | ||
| JP2007512370A5 (OSRAM) | ||
| JP2022508953A (ja) | Ｈｂｖの処置のための５員のヘテロアリールカルボキサミド化合物 | |
| JP2010138190A5 (OSRAM) | ||
| NZ600881A (en) | Pyrazole derivatives as jak inhibitors | |
| RU2015106787A (ru) | Замещенные пирролы, активные в качестве ингибиторов киназ | |
| EA200970510A1 (ru) | Гетеромоноциклическое соединение и его применение | |
| JP2009511504A5 (OSRAM) | ||
| JP2011526917A5 (OSRAM) | ||
| JP2009542716A5 (OSRAM) | ||
| NZ604074A (en) | Piperidinone derivatives as mdm2 inhibitors for the treatment of cancer | |
| JP2009504764A5 (OSRAM) | ||
| PE20141075A1 (es) | 4-aril-n-fenil-1,3,5-triazin-2-aminas que contienen un grupo sulfoximina | |
| RU2014115476A (ru) | Производные пиразоло[4, 3-с]птридина в качестве ингибиторов киназ | |
| JP2018514544A5 (OSRAM) | ||
| JP2017516826A5 (OSRAM) | ||
| RU2015101102A (ru) | Гетероароматическое метильное производное циклического амина | |
| JP2018530582A5 (OSRAM) |