JP2015503507A5 - - Google Patents
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- JP2015503507A5 JP2015503507A5 JP2014548963A JP2014548963A JP2015503507A5 JP 2015503507 A5 JP2015503507 A5 JP 2015503507A5 JP 2014548963 A JP2014548963 A JP 2014548963A JP 2014548963 A JP2014548963 A JP 2014548963A JP 2015503507 A5 JP2015503507 A5 JP 2015503507A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- dihydropyrano
- carbonitrile
- pyrazole
- methyl
- 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
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- GMDKZHJZAGRRGP-UHFFFAOYSA-N 6-amino-3-(3,4-dimethoxyphenyl)-4-(4-fluorophenyl)-1-methyl-4h-pyrano[2,3-c]pyrazole-5-carbonitrile Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C)C2=C1C(C=1C=CC(F)=CC=1)C(C#N)=C(N)O2 GMDKZHJZAGRRGP-UHFFFAOYSA-N 0.000 claims description 4
- OOCJZFSWSZJDAT-UHFFFAOYSA-N 6-amino-4-(4-methoxyphenyl)-1,3-diphenyl-4h-pyrano[2,3-c]pyrazole-5-carbonitrile Chemical compound C1=CC(OC)=CC=C1C1C(C#N)=C(N)OC2=C1C(C=1C=CC=CC=1)=NN2C1=CC=CC=C1 OOCJZFSWSZJDAT-UHFFFAOYSA-N 0.000 claims description 4
- NZVWFTPWXPMPBG-UHFFFAOYSA-N 6-amino-4-(4-methoxyphenyl)-1-methyl-3-phenyl-4h-pyrano[2,3-c]pyrazole-5-carbonitrile Chemical compound C1=CC(OC)=CC=C1C1C(C#N)=C(N)OC2=C1C(C=1C=CC=CC=1)=NN2C NZVWFTPWXPMPBG-UHFFFAOYSA-N 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- MZKALFCNIJHTJG-UHFFFAOYSA-N 2,5-diphenyl-4h-pyrazol-3-one Chemical compound O=C1CC(C=2C=CC=CC=2)=NN1C1=CC=CC=C1 MZKALFCNIJHTJG-UHFFFAOYSA-N 0.000 claims description 3
- SYIHKMOPWDYBOS-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-2-methyl-4h-pyrazol-3-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C)C(=O)C1 SYIHKMOPWDYBOS-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims 20
- 239000008194 pharmaceutical composition Substances 0.000 claims 20
- 102000006688 ral GTP-Binding Proteins Human genes 0.000 claims 7
- 108010087304 ral GTP-Binding Proteins Proteins 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 6
- 230000027455 binding Effects 0.000 claims 5
- 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 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 102000004169 proteins and genes Human genes 0.000 claims 3
- 108090000623 proteins and genes Proteins 0.000 claims 3
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims 2
- GDXRSVQMDSLVIB-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-2-phenyl-4h-pyrazol-3-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C=2C=CC=CC=2)C(=O)C1 GDXRSVQMDSLVIB-UHFFFAOYSA-N 0.000 claims 2
- NXBVNTCZEKBZTM-UHFFFAOYSA-N 5-(4-methoxyphenyl)-2-methyl-4h-pyrazol-3-one Chemical compound C1=CC(OC)=CC=C1C1=NN(C)C(=O)C1 NXBVNTCZEKBZTM-UHFFFAOYSA-N 0.000 claims 2
- JSJKAIQJGDEDOI-UHFFFAOYSA-N 5-(4-methoxyphenyl)-2-phenyl-4h-pyrazol-3-one Chemical compound C1=CC(OC)=CC=C1C1=NN(C=2C=CC=CC=2)C(=O)C1 JSJKAIQJGDEDOI-UHFFFAOYSA-N 0.000 claims 2
- SYCVVGUTFUBQMP-UHFFFAOYSA-N 6-amino-1,3,4-triphenyl-4h-pyrano[2,3-c]pyrazole-5-carbonitrile Chemical compound O1C(N)=C(C#N)C(C=2C=CC=CC=2)C2=C1N(C=1C=CC=CC=1)N=C2C1=CC=CC=C1 SYCVVGUTFUBQMP-UHFFFAOYSA-N 0.000 claims 2
- XKIUDYBVYGLWGY-UHFFFAOYSA-N 6-amino-1,3-dimethyl-4-phenyl-4h-pyrano[2,3-c]pyrazole-5-carbonitrile Chemical compound C1=2C(C)=NN(C)C=2OC(N)=C(C#N)C1C1=CC=CC=C1 XKIUDYBVYGLWGY-UHFFFAOYSA-N 0.000 claims 2
- ODYQQEGFOATJHL-UHFFFAOYSA-N 6-amino-1-methyl-3,4-diphenyl-4h-pyrano[2,3-c]pyrazole-5-carbonitrile Chemical compound N#CC1=C(N)OC=2N(C)N=C(C=3C=CC=CC=3)C=2C1C1=CC=CC=C1 ODYQQEGFOATJHL-UHFFFAOYSA-N 0.000 claims 2
- ZTPKVVZQRNAVOM-UHFFFAOYSA-N 6-amino-3,4-bis(4-methoxyphenyl)-1-methyl-4h-pyrano[2,3-c]pyrazole-5-carbonitrile Chemical compound C1=CC(OC)=CC=C1C1C(C#N)=C(N)OC2=C1C(C=1C=CC(OC)=CC=1)=NN2C ZTPKVVZQRNAVOM-UHFFFAOYSA-N 0.000 claims 2
- AZBZPRFEFCPULP-UHFFFAOYSA-N 6-amino-3,4-bis(4-methoxyphenyl)-1-phenyl-4h-pyrano[2,3-c]pyrazole-5-carbonitrile Chemical compound C1=CC(OC)=CC=C1C1C(C#N)=C(N)OC2=C1C(C=1C=CC(OC)=CC=1)=NN2C1=CC=CC=C1 AZBZPRFEFCPULP-UHFFFAOYSA-N 0.000 claims 2
- JRPYVPUCLKTUEM-UHFFFAOYSA-N 6-amino-3-(3,4-dimethoxyphenyl)-1-methyl-4-phenyl-4h-pyrano[2,3-c]pyrazole-5-carbonitrile Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C)C2=C1C(C=1C=CC=CC=1)C(C#N)=C(N)O2 JRPYVPUCLKTUEM-UHFFFAOYSA-N 0.000 claims 2
- UONYAMWNGJIPBM-UHFFFAOYSA-N 6-amino-3-(3,4-dimethoxyphenyl)-4-(4-fluorophenyl)-1-phenyl-4h-pyrano[2,3-c]pyrazole-5-carbonitrile Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(C=2C=CC=CC=2)C2=C1C(C=1C=CC(F)=CC=1)C(C#N)=C(N)O2 UONYAMWNGJIPBM-UHFFFAOYSA-N 0.000 claims 2
- APGMIYQSKPWOIM-UHFFFAOYSA-N 6-amino-3-(4-methoxyphenyl)-1,4-diphenyl-4h-pyrano[2,3-c]pyrazole-5-carbonitrile Chemical compound C1=CC(OC)=CC=C1C1=NN(C=2C=CC=CC=2)C2=C1C(C=1C=CC=CC=1)C(C#N)=C(N)O2 APGMIYQSKPWOIM-UHFFFAOYSA-N 0.000 claims 2
- AFZCVZDIMNSNTG-UHFFFAOYSA-N 6-amino-3-(4-methoxyphenyl)-1-methyl-4-phenyl-4h-pyrano[2,3-c]pyrazole-5-carbonitrile Chemical compound C1=CC(OC)=CC=C1C1=NN(C)C2=C1C(C=1C=CC=CC=1)C(C#N)=C(N)O2 AFZCVZDIMNSNTG-UHFFFAOYSA-N 0.000 claims 2
- PRYBIJAJECYWEP-UHFFFAOYSA-N 6-amino-3-methyl-1,4-diphenyl-4h-pyrano[2,3-c]pyrazole-5-carbonitrile Chemical compound C1=2C(C)=NN(C=3C=CC=CC=3)C=2OC(N)=C(C#N)C1C1=CC=CC=C1 PRYBIJAJECYWEP-UHFFFAOYSA-N 0.000 claims 2
- GHGGSZZQRQFCAA-UHFFFAOYSA-N 6-amino-4-(4-fluorophenyl)-1,3-dimethyl-4h-pyrano[2,3-c]pyrazole-5-carbonitrile Chemical compound C1=2C(C)=NN(C)C=2OC(N)=C(C#N)C1C1=CC=C(F)C=C1 GHGGSZZQRQFCAA-UHFFFAOYSA-N 0.000 claims 2
- PWCFOCGCELAIIU-UHFFFAOYSA-N 6-amino-4-(4-fluorophenyl)-1,3-diphenyl-4h-pyrano[2,3-c]pyrazole-5-carbonitrile Chemical compound O1C(N)=C(C#N)C(C=2C=CC(F)=CC=2)C2=C1N(C=1C=CC=CC=1)N=C2C1=CC=CC=C1 PWCFOCGCELAIIU-UHFFFAOYSA-N 0.000 claims 2
- LGDUEGBBOZVQQA-UHFFFAOYSA-N 6-amino-4-(4-fluorophenyl)-1-methyl-3-phenyl-4h-pyrano[2,3-c]pyrazole-5-carbonitrile Chemical compound N#CC1=C(N)OC=2N(C)N=C(C=3C=CC=CC=3)C=2C1C1=CC=C(F)C=C1 LGDUEGBBOZVQQA-UHFFFAOYSA-N 0.000 claims 2
- NEYQQEJZTHZMMT-UHFFFAOYSA-N 6-amino-4-(4-fluorophenyl)-3-(4-methoxyphenyl)-1-methyl-4h-pyrano[2,3-c]pyrazole-5-carbonitrile Chemical compound C1=CC(OC)=CC=C1C1=NN(C)C2=C1C(C=1C=CC(F)=CC=1)C(C#N)=C(N)O2 NEYQQEJZTHZMMT-UHFFFAOYSA-N 0.000 claims 2
- RCVFMHJNRULPOD-UHFFFAOYSA-N 6-amino-4-(4-fluorophenyl)-3-(4-methoxyphenyl)-1-phenyl-4h-pyrano[2,3-c]pyrazole-5-carbonitrile Chemical compound C1=CC(OC)=CC=C1C1=NN(C=2C=CC=CC=2)C2=C1C(C=1C=CC(F)=CC=1)C(C#N)=C(N)O2 RCVFMHJNRULPOD-UHFFFAOYSA-N 0.000 claims 2
- SDHROKOVSZAYNC-UHFFFAOYSA-N 6-amino-4-(4-fluorophenyl)-3-methyl-1-phenyl-4h-pyrano[2,3-c]pyrazole-5-carbonitrile Chemical compound C1=2C(C)=NN(C=3C=CC=CC=3)C=2OC(N)=C(C#N)C1C1=CC=C(F)C=C1 SDHROKOVSZAYNC-UHFFFAOYSA-N 0.000 claims 2
- PKILIQNZXIGJQU-UHFFFAOYSA-N 6-amino-4-(4-methoxyphenyl)-1,3-dimethyl-4h-pyrano[2,3-c]pyrazole-5-carbonitrile Chemical compound C1=CC(OC)=CC=C1C1C(C#N)=C(N)OC2=C1C(C)=NN2C PKILIQNZXIGJQU-UHFFFAOYSA-N 0.000 claims 2
- VDANGQOCOBTKTG-UHFFFAOYSA-N 6-amino-4-(4-methoxyphenyl)-3-methyl-1-phenyl-4h-pyrano[2,3-c]pyrazole-5-carbonitrile Chemical compound C1=CC(OC)=CC=C1C1C(C#N)=C(N)OC2=C1C(C)=NN2C1=CC=CC=C1 VDANGQOCOBTKTG-UHFFFAOYSA-N 0.000 claims 2
- 101100172879 Caenorhabditis elegans sec-5 gene Proteins 0.000 claims 2
- 101150046010 EXO84 gene Proteins 0.000 claims 2
- 102000013366 Filamin Human genes 0.000 claims 2
- 108060002900 Filamin Proteins 0.000 claims 2
- 102100021223 Glucosidase 2 subunit beta Human genes 0.000 claims 2
- 101001040875 Homo sapiens Glucosidase 2 subunit beta Proteins 0.000 claims 2
- 101000730665 Homo sapiens Phospholipase D1 Proteins 0.000 claims 2
- 101000823782 Homo sapiens Y-box-binding protein 3 Proteins 0.000 claims 2
- 101000964266 Loxosceles laeta Dermonecrotic toxin Proteins 0.000 claims 2
- 150000001204 N-oxides Chemical class 0.000 claims 2
- 102100038914 RalA-binding protein 1 Human genes 0.000 claims 2
- 101710200757 RalA-binding protein 1 Proteins 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 102100022221 Y-box-binding protein 3 Human genes 0.000 claims 2
- 125000004423 acyloxy group Chemical group 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- NDELSWXIAJLWOU-UHFFFAOYSA-N 2,5-dimethyl-4h-pyrazol-3-one Chemical compound CN1N=C(C)CC1=O NDELSWXIAJLWOU-UHFFFAOYSA-N 0.000 claims 1
- NWXCKWDMRABXRQ-UHFFFAOYSA-N 2-[2-(2-methoxyphenyl)-4-(4-methoxyphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol Chemical compound C1=CC(OC)=CC=C1C1=NC(C=2C(=CC=CC=2)OC)NC(C=2C(=CC=CC=2)O)C1 NWXCKWDMRABXRQ-UHFFFAOYSA-N 0.000 claims 1
- SGXVQHQYAMRXNE-UHFFFAOYSA-N 2-[4-(4-ethylphenyl)-2-(4-methylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol Chemical compound C1=CC(CC)=CC=C1C1=NC(C=2C=CC(C)=CC=2)NC(C=2C(=CC=CC=2)O)C1 SGXVQHQYAMRXNE-UHFFFAOYSA-N 0.000 claims 1
- PWNPNWGMUVGBAZ-UHFFFAOYSA-N 2-benzyl-5-phenyl-4h-pyrazol-3-one Chemical compound O=C1CC(C=2C=CC=CC=2)=NN1CC1=CC=CC=C1 PWNPNWGMUVGBAZ-UHFFFAOYSA-N 0.000 claims 1
- NIXIJMXBXHWPEK-UHFFFAOYSA-N 2-methyl-5-phenyl-4h-pyrazol-3-one Chemical compound C1C(=O)N(C)N=C1C1=CC=CC=C1 NIXIJMXBXHWPEK-UHFFFAOYSA-N 0.000 claims 1
- XERBEDAMDXRGFD-UHFFFAOYSA-N 6-(2-chlorophenyl)-5-pentanoyl-8,9,10,11-tetrahydro-6h-benzo[b][1,4]benzodiazepin-7-one Chemical compound C1CCC(=O)C2=C1NC1=CC=CC=C1N(C(=O)CCCC)C2C1=CC=CC=C1Cl XERBEDAMDXRGFD-UHFFFAOYSA-N 0.000 claims 1
- CLMQBVUFKIKYLU-UHFFFAOYSA-N 6-amino-4-(2,5-dimethoxyphenyl)-3-naphthalen-2-yl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile Chemical compound COC1=CC=C(OC)C(C2C(=C(N)OC=3C2=C(NN=3)C=2C=C3C=CC=CC3=CC=2)C#N)=C1 CLMQBVUFKIKYLU-UHFFFAOYSA-N 0.000 claims 1
- NFPWWZIRTMIQKT-UHFFFAOYSA-N 6-amino-4-(3,5-dichloro-2-hydroxyphenyl)-3-propyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile Chemical compound C12=C(CCC)NN=C2OC(N)=C(C#N)C1C1=CC(Cl)=CC(Cl)=C1O NFPWWZIRTMIQKT-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 206010027476 Metastases Diseases 0.000 claims 1
- 101150093978 RALB gene Proteins 0.000 claims 1
- 101150033538 Rala gene Proteins 0.000 claims 1
- 125000005236 alkanoylamino group Chemical group 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 238000002512 chemotherapy Methods 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 claims 1
- 108010050749 geranylgeranyltransferase type-I Proteins 0.000 claims 1
- 238000009169 immunotherapy Methods 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 230000009401 metastasis Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 238000001959 radiotherapy Methods 0.000 claims 1
- 238000001356 surgical procedure Methods 0.000 claims 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 4
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000004885 tandem mass spectrometry Methods 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 2
- UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161578869P | 2011-12-21 | 2011-12-21 | |
| US61/578,869 | 2011-12-21 | ||
| PCT/US2012/071341 WO2013096820A1 (en) | 2011-12-21 | 2012-12-21 | Anti-cancer compounds targeting ral gtpases and methods of using the same |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015503507A JP2015503507A (ja) | 2015-02-02 |
| JP2015503507A5 true JP2015503507A5 (https=) | 2016-02-25 |
| JP6473330B2 JP6473330B2 (ja) | 2019-02-20 |
Family
ID=48669550
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014548963A Expired - Fee Related JP6473330B2 (ja) | 2011-12-21 | 2012-12-21 | ＲａｌＧＴＰアーゼを標的とする抗がん化合物及びその使用方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (3) | US9353121B2 (https=) |
| EP (1) | EP2793881B1 (https=) |
| JP (1) | JP6473330B2 (https=) |
| KR (1) | KR102097343B1 (https=) |
| CN (1) | CN104271132B (https=) |
| AU (1) | AU2012358317B2 (https=) |
| CA (1) | CA2859985C (https=) |
| WO (1) | WO2013096820A1 (https=) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2859985C (en) | 2011-12-21 | 2020-11-03 | The Regents Of The University Of Colorado | Anti-cancer compounds targeting ral gtpases and methods of using the same |
| EP3166609B1 (en) | 2014-07-10 | 2020-03-11 | The Regents of The University of Colorado, A Body Corporate | 6-amino-1,3-dimethyl-4-(4-(trifluoromethyl)phenyl)-1,4-dihydropyrano [2,3-c]pyrazole-5-carbonitrile and related compounds as ral gtpase inhibitors for treating cancer metastasis |
| EP3194383B1 (en) | 2014-09-19 | 2019-11-06 | Forma Therapeutics, Inc. | Quinolinone pyrimidines compositions as mutant-isocitrate dehydrogenase inhibitors |
| MA53352A (fr) | 2014-09-19 | 2021-09-15 | Forma Therapeutics Inc | Dérivés de pyridin-2-(1h)-one-quinolinone en tant qu'inhibiteurs d'isocitrate déshydrogénase |
| US10934291B2 (en) | 2014-09-25 | 2021-03-02 | Duke University | Kinase inhibitors and related methods of use |
| US10646475B2 (en) | 2015-03-10 | 2020-05-12 | The Trustees Of Princeton University | SHMT inhibitors |
| WO2016205460A1 (en) * | 2015-06-16 | 2016-12-22 | Nantbioscience, Inc. | Polycyclic derivatives targeting ral gtpases and their therapeutical applications |
| BR112018003417B1 (pt) | 2016-06-22 | 2023-10-24 | Vanderbilt University | Composto modulador alostérico positivo do receptor muscarínico de acetilcolina m4 e composição farmacêutica que o compreende |
| US10077273B2 (en) | 2016-09-14 | 2018-09-18 | The Trustees Of Princeton University | SHMT inhibitors |
| US10947241B2 (en) | 2016-10-28 | 2021-03-16 | Seoul National University Hospital | Phenyl phthalazine derivative, method for the preparation thereof, and pharmaceutical composition comprising the same |
| EP3544961B1 (en) | 2016-11-07 | 2021-08-18 | Vanderbilt University | Positive allosteric modulators of the muscarinic acetylcholine receptor m4 |
| WO2018085803A1 (en) | 2016-11-07 | 2018-05-11 | Vanderbilt University | Positive allosteric modulators of the muscarinic acetylcholine receptor m4 |
| US10961253B2 (en) | 2016-11-07 | 2021-03-30 | Vanderbilt University | Positive allosteric modulators of the muscarinic acetylcholine receptor M4 |
| CN110024421B (zh) | 2016-11-23 | 2020-12-25 | 瑞典爱立信有限公司 | 用于自适应控制去相关滤波器的方法和装置 |
| US11376254B2 (en) | 2017-12-05 | 2022-07-05 | Vanderbilt University | Positive allosteric modulators of the muscarinic acetylcholine receptor M4 |
| TW201930311A (zh) | 2017-12-05 | 2019-08-01 | 泛德比爾特大學 | 蕈毒鹼型乙醯膽鹼受體m4之正向別構調節劑 |
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