JP2011509290A5 - - Google Patents
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- JP2011509290A5 JP2011509290A5 JP2010541891A JP2010541891A JP2011509290A5 JP 2011509290 A5 JP2011509290 A5 JP 2011509290A5 JP 2010541891 A JP2010541891 A JP 2010541891A JP 2010541891 A JP2010541891 A JP 2010541891A JP 2011509290 A5 JP2011509290 A5 JP 2011509290A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrazolo
- pyrimidin
- phenyl
- amine
- formula
- 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
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- -1 3,5-dimethylphenyl group Chemical class 0.000 claims 53
- 150000001875 compounds Chemical class 0.000 claims 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 15
- 239000002904 solvent Substances 0.000 claims 12
- 239000000203 mixture Substances 0.000 claims 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 9
- 238000000034 method Methods 0.000 claims 9
- 238000010992 reflux Methods 0.000 claims 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 8
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 6
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 6
- QUKPALAWEPMWOS-UHFFFAOYSA-N 1h-pyrazolo[3,4-d]pyrimidine Chemical class C1=NC=C2C=NNC2=N1 QUKPALAWEPMWOS-UHFFFAOYSA-N 0.000 claims 5
- 229910052783 alkali metal Inorganic materials 0.000 claims 5
- 239000002585 base Substances 0.000 claims 5
- 239000003586 protic polar solvent Substances 0.000 claims 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims 4
- OEICGMPRFOJHKO-UHFFFAOYSA-N 2-(ethoxymethylidene)propanedinitrile Chemical compound CCOC=C(C#N)C#N OEICGMPRFOJHKO-UHFFFAOYSA-N 0.000 claims 4
- MAKQREKUUHPPIS-UHFFFAOYSA-N 5-amino-1-phenyl-1H-pyrazole-4-carbonitrile Chemical compound NC1=C(C#N)C=NN1C1=CC=CC=C1 MAKQREKUUHPPIS-UHFFFAOYSA-N 0.000 claims 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 4
- 229910021529 ammonia Inorganic materials 0.000 claims 4
- 239000000010 aprotic solvent Substances 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 230000003463 hyperproliferative effect Effects 0.000 claims 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 4
- 239000011707 mineral Substances 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 4
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 125000003282 alkyl amino group Chemical group 0.000 claims 3
- 239000001099 ammonium carbonate Substances 0.000 claims 3
- 235000012501 ammonium carbonate Nutrition 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 3
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- BXDZOYLPNAIDOC-UHFFFAOYSA-N N-[5-[(5-tert-butyl-1,3-oxazol-2-yl)methylsulfanyl]-1,3-thiazol-2-yl]-1-[2-[2-[2-[2-[2-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]amino]ethoxy]ethoxy]ethoxy]ethylamino]-2-oxoethyl]piperidine-4-carboxamide Chemical compound CC(C)(C)c1cnc(CSc2cnc(NC(=O)C3CCN(CC(=O)NCCOCCOCCOCCNc4cccc5C(=O)N(C6CCC(=O)NC6=O)C(=O)c45)CC3)s2)o1 BXDZOYLPNAIDOC-UHFFFAOYSA-N 0.000 claims 2
- 150000007513 acids Chemical class 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 239000012736 aqueous medium Substances 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- 125000005605 benzo group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 208000014829 head and neck neoplasm Diseases 0.000 claims 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 2
- 230000007062 hydrolysis Effects 0.000 claims 2
- 238000006460 hydrolysis reaction Methods 0.000 claims 2
- 150000004679 hydroxides Chemical class 0.000 claims 2
- 238000011065 in-situ storage Methods 0.000 claims 2
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 claims 2
- SJBHYUWNPFYYNI-UHFFFAOYSA-N n-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-1-(3,5-dimethylphenyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound CC1=CC(C)=CC(N2C3=NC=NC(NCC=4C=C5OCCOC5=CC=4)=C3C=N2)=C1 SJBHYUWNPFYYNI-UHFFFAOYSA-N 0.000 claims 2
- 230000003472 neutralizing effect Effects 0.000 claims 2
- 125000002560 nitrile group Chemical group 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 229940067157 phenylhydrazine Drugs 0.000 claims 2
- 150000004031 phenylhydrazines Chemical class 0.000 claims 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims 2
- OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 claims 2
- 235000010288 sodium nitrite Nutrition 0.000 claims 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000005296 thioaryloxy group Chemical group 0.000 claims 2
- 125000005404 thioheteroaryloxy group Chemical group 0.000 claims 2
- 125000005270 trialkylamine group Chemical group 0.000 claims 2
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims 1
- HPARLNRMYDSBNO-UHFFFAOYSA-N 1,4-benzodioxine Chemical compound C1=CC=C2OC=COC2=C1 HPARLNRMYDSBNO-UHFFFAOYSA-N 0.000 claims 1
- YSWUDFATSBPVFL-UHFFFAOYSA-N 1-(3,5-dimethylphenyl)-n-[(3,4,5-trimethoxyphenyl)methyl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound COC1=C(OC)C(OC)=CC(CNC=2C=3C=NN(C=3N=CN=2)C=2C=C(C)C=C(C)C=2)=C1 YSWUDFATSBPVFL-UHFFFAOYSA-N 0.000 claims 1
- SQAKOPVOUSLGRS-UHFFFAOYSA-N 1-(3,5-dimethylphenyl)-n-[2-(2-methoxyethoxy)ethyl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound N1=CC=2C(NCCOCCOC)=NC=NC=2N1C1=CC(C)=CC(C)=C1 SQAKOPVOUSLGRS-UHFFFAOYSA-N 0.000 claims 1
- STYVEAOALAEULT-UHFFFAOYSA-N 1-(3-iodophenyl)pyrazolo[3,4-d]pyrimidine Chemical class IC1=CC=CC(N2C3=NC=NC=C3C=N2)=C1 STYVEAOALAEULT-UHFFFAOYSA-N 0.000 claims 1
- GETXGBDZZACJPV-UHFFFAOYSA-N 1-(3-methylphenyl)-n-[(3,4,5-trimethoxyphenyl)methyl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound COC1=C(OC)C(OC)=CC(CNC=2C=3C=NN(C=3N=CN=2)C=2C=C(C)C=CC=2)=C1 GETXGBDZZACJPV-UHFFFAOYSA-N 0.000 claims 1
- VLVZKHQSYVUBEA-UHFFFAOYSA-N 1-(3-methylphenyl)-n-[[4-(3-morpholin-4-ylpropoxy)phenyl]methyl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound CC1=CC=CC(N2C3=NC=NC(NCC=4C=CC(OCCCN5CCOCC5)=CC=4)=C3C=N2)=C1 VLVZKHQSYVUBEA-UHFFFAOYSA-N 0.000 claims 1
- GSILHXSZYLRDCW-UHFFFAOYSA-N 1-(3-methylphenyl)pyrazolo[3,4-d]pyrimidine Chemical class CC1=CC=CC(N2C3=NC=NC=C3C=N2)=C1 GSILHXSZYLRDCW-UHFFFAOYSA-N 0.000 claims 1
- ROEFWOWUWFIFHP-UHFFFAOYSA-N 2-[[1-(3,5-dimethylphenyl)pyrazolo[3,4-d]pyrimidin-4-yl]amino]acetic acid Chemical compound CC1=CC(C)=CC(N2C3=NC=NC(NCC(O)=O)=C3C=N2)=C1 ROEFWOWUWFIFHP-UHFFFAOYSA-N 0.000 claims 1
- DTTHGYPBDBANKG-UHFFFAOYSA-N 2-[[1-(3-cyanophenyl)pyrazolo[3,4-d]pyrimidin-4-yl]amino]acetic acid Chemical compound N1=CC=2C(NCC(=O)O)=NC=NC=2N1C1=CC=CC(C#N)=C1 DTTHGYPBDBANKG-UHFFFAOYSA-N 0.000 claims 1
- KDMNJOUCLAIXDH-UHFFFAOYSA-N 2-[[1-(3-methylphenyl)pyrazolo[3,4-d]pyrimidin-4-yl]amino]acetic acid Chemical compound CC1=CC=CC(N2C3=NC=NC(NCC(O)=O)=C3C=N2)=C1 KDMNJOUCLAIXDH-UHFFFAOYSA-N 0.000 claims 1
- ZVNYYNAAEVZNDW-UHFFFAOYSA-N 2-phenylpyrazol-3-amine Chemical compound NC1=CC=NN1C1=CC=CC=C1 ZVNYYNAAEVZNDW-UHFFFAOYSA-N 0.000 claims 1
- PNAQLBVTHVBJOU-UHFFFAOYSA-N 3,5-dimethylpyrazolo[3,4-d]pyrimidine Chemical class N1=CN(C)C=C2C(C)=NN=C21 PNAQLBVTHVBJOU-UHFFFAOYSA-N 0.000 claims 1
- PNSVHQUIJWZNRG-UHFFFAOYSA-N 3-[4-[(3,4,5-trimethoxyphenyl)methylamino]pyrazolo[3,4-d]pyrimidin-1-yl]benzonitrile Chemical compound COC1=C(OC)C(OC)=CC(CNC=2C=3C=NN(C=3N=CN=2)C=2C=C(C=CC=2)C#N)=C1 PNSVHQUIJWZNRG-UHFFFAOYSA-N 0.000 claims 1
- BWEHNFAHJYUHNO-UHFFFAOYSA-N 3-[4-[(4-methoxyphenyl)methylamino]pyrazolo[3,4-d]pyrimidin-1-yl]benzonitrile Chemical compound C1=CC(OC)=CC=C1CNC1=NC=NC2=C1C=NN2C1=CC=CC(C#N)=C1 BWEHNFAHJYUHNO-UHFFFAOYSA-N 0.000 claims 1
- OXZQINWSJIVXFQ-UHFFFAOYSA-N 3-[4-[[3,4-bis(2-methoxyethoxy)phenyl]methylamino]pyrazolo[3,4-d]pyrimidin-1-yl]benzonitrile Chemical compound C1=C(OCCOC)C(OCCOC)=CC=C1CNC1=NC=NC2=C1C=NN2C1=CC=CC(C#N)=C1 OXZQINWSJIVXFQ-UHFFFAOYSA-N 0.000 claims 1
- DWRMZQCPYGFIGS-UHFFFAOYSA-N 3-[4-[[4-(3-morpholin-4-ylpropoxy)phenyl]methylamino]pyrazolo[3,4-d]pyrimidin-1-yl]benzonitrile Chemical compound N#CC1=CC=CC(N2C3=NC=NC(NCC=4C=CC(OCCCN5CCOCC5)=CC=4)=C3C=N2)=C1 DWRMZQCPYGFIGS-UHFFFAOYSA-N 0.000 claims 1
- OYZFRHPWEVEJQH-UHFFFAOYSA-N 3-[4-[[4-methoxy-3-(3-morpholin-4-ylpropoxy)phenyl]methylamino]pyrazolo[3,4-d]pyrimidin-1-yl]benzonitrile Chemical compound C1=C(OCCCN2CCOCC2)C(OC)=CC=C1CNC(C=1C=N2)=NC=NC=1N2C1=CC=CC(C#N)=C1 OYZFRHPWEVEJQH-UHFFFAOYSA-N 0.000 claims 1
- 125000006305 3-iodophenyl group Chemical group [H]C1=C([H])C(I)=C([H])C(*)=C1[H] 0.000 claims 1
- WJHAGGMBBWXXCU-UHFFFAOYSA-N 3-pyrazolo[3,4-d]pyrimidin-1-ylbenzonitrile Chemical class N#CC1=CC=CC(N2C3=NC=NC=C3C=N2)=C1 WJHAGGMBBWXXCU-UHFFFAOYSA-N 0.000 claims 1
- YMXQUFUYCADCFL-UHFFFAOYSA-N 4-chloro-1h-pyrazolo[3,4-d]pyrimidine Chemical class ClC1=NC=NC2=C1C=NN2 YMXQUFUYCADCFL-UHFFFAOYSA-N 0.000 claims 1
- ZUCMUUMUEOALJU-UHFFFAOYSA-N 4-chloro-3-phenyl-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=2C(Cl)=NC=NC=2NN=C1C1=CC=CC=C1 ZUCMUUMUEOALJU-UHFFFAOYSA-N 0.000 claims 1
- UBKSUPKIDNXMMC-UHFFFAOYSA-N 5-amino-1-phenylpyrazole-4-carboxamide Chemical compound NC1=C(C(=O)N)C=NN1C1=CC=CC=C1 UBKSUPKIDNXMMC-UHFFFAOYSA-N 0.000 claims 1
- 206010005003 Bladder cancer Diseases 0.000 claims 1
- 208000003174 Brain Neoplasms Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims 1
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 206010030155 Oesophageal carcinoma Diseases 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 208000024770 Thyroid neoplasm Diseases 0.000 claims 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 1
- PARWGYPSBMSXSC-UHFFFAOYSA-N [4-(2-methoxyethoxy)phenyl]methanamine Chemical compound COCCOC1=CC=C(CN)C=C1 PARWGYPSBMSXSC-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000005236 alkanoylamino group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 150000003973 alkyl amines Chemical class 0.000 claims 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 claims 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 201000004101 esophageal cancer Diseases 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000002346 iodo group Chemical group I* 0.000 claims 1
- 201000010982 kidney cancer Diseases 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- 208000026037 malignant tumor of neck Diseases 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- XERHTFBEABJMAL-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-1-(3,5-dimethylphenyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound CC1=CC(C)=CC(N2C3=NC=NC(NCC=4C=C5OCOC5=CC=4)=C3C=N2)=C1 XERHTFBEABJMAL-UHFFFAOYSA-N 0.000 claims 1
- IIBPUCIUZPGZFD-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-1-(3-ethynylphenyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C#CC1=CC=CC(N2C3=NC=NC(NCC=4C=C5OCOC5=CC=4)=C3C=N2)=C1 IIBPUCIUZPGZFD-UHFFFAOYSA-N 0.000 claims 1
- KEZHXUVPGGBABO-UHFFFAOYSA-N n-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-1-(3-methylphenyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound CC1=CC=CC(N2C3=NC=NC(NCC=4C=C5OCCOC5=CC=4)=C3C=N2)=C1 KEZHXUVPGGBABO-UHFFFAOYSA-N 0.000 claims 1
- JUIGKLFOQNJFIC-UHFFFAOYSA-N n-[(3,4-dimethoxyphenyl)methyl]-1-(3,5-dimethylphenyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1=C(OC)C(OC)=CC=C1CNC1=NC=NC2=C1C=NN2C1=CC(C)=CC(C)=C1 JUIGKLFOQNJFIC-UHFFFAOYSA-N 0.000 claims 1
- XYFNVSNOCNUOOR-UHFFFAOYSA-N n-[(3,4-dimethoxyphenyl)methyl]-1-(3-methylphenyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1=C(OC)C(OC)=CC=C1CNC1=NC=NC2=C1C=NN2C1=CC=CC(C)=C1 XYFNVSNOCNUOOR-UHFFFAOYSA-N 0.000 claims 1
- KSESLOVJGZDCDV-UHFFFAOYSA-N n-[(4-methoxyphenyl)methyl]-1-(3-methylphenyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1CNC1=NC=NC2=C1C=NN2C1=CC=CC(C)=C1 KSESLOVJGZDCDV-UHFFFAOYSA-N 0.000 claims 1
- UXLQRQRZMYFOJQ-UHFFFAOYSA-N n-[2-(2-methoxyethoxy)ethyl]-1-(3-methylphenyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound N1=CC=2C(NCCOCCOC)=NC=NC=2N1C1=CC=CC(C)=C1 UXLQRQRZMYFOJQ-UHFFFAOYSA-N 0.000 claims 1
- QYFVWAXNXLJXPI-UHFFFAOYSA-N n-[[3,4-bis(2-methoxyethoxy)phenyl]methyl]-1-(3,5-dimethylphenyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1=C(OCCOC)C(OCCOC)=CC=C1CNC1=NC=NC2=C1C=NN2C1=CC(C)=CC(C)=C1 QYFVWAXNXLJXPI-UHFFFAOYSA-N 0.000 claims 1
- DVQNZXMUTFGQDI-UHFFFAOYSA-N n-[[3,4-bis(2-methoxyethoxy)phenyl]methyl]-1-(3-methylphenyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1=C(OCCOC)C(OCCOC)=CC=C1CNC1=NC=NC2=C1C=NN2C1=CC=CC(C)=C1 DVQNZXMUTFGQDI-UHFFFAOYSA-N 0.000 claims 1
- UYWJCYDXLYIFMY-UHFFFAOYSA-N n-[[4-(2-methoxyethoxy)phenyl]methyl]-1-(3-methylphenyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1=CC(OCCOC)=CC=C1CNC1=NC=NC2=C1C=NN2C1=CC=CC(C)=C1 UYWJCYDXLYIFMY-UHFFFAOYSA-N 0.000 claims 1
- IJTBHPAXFRYDQY-UHFFFAOYSA-N n-[[4-methoxy-3-(3-morpholin-4-ylpropoxy)phenyl]methyl]-1-(3-methylphenyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1=C(OCCCN2CCOCC2)C(OC)=CC=C1CNC(C=1C=N2)=NC=NC=1N2C1=CC=CC(C)=C1 IJTBHPAXFRYDQY-UHFFFAOYSA-N 0.000 claims 1
- PFIIOMYDQZYTJG-UHFFFAOYSA-N n-methyl-2,3-dihydro-1,4-benzodioxin-6-amine Chemical compound O1CCOC2=CC(NC)=CC=C21 PFIIOMYDQZYTJG-UHFFFAOYSA-N 0.000 claims 1
- 150000002829 nitrogen Chemical group 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- JOVOSQBPPZZESK-UHFFFAOYSA-N phenylhydrazine hydrochloride Chemical class Cl.NNC1=CC=CC=C1 JOVOSQBPPZZESK-UHFFFAOYSA-N 0.000 claims 1
- 229940038531 phenylhydrazine hydrochloride Drugs 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 206010041823 squamous cell carcinoma Diseases 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims 1
- 201000002510 thyroid cancer Diseases 0.000 claims 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 claims 1
- 201000005112 urinary bladder cancer Diseases 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
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| IN109CH2008 | 2008-01-11 | ||
| PCT/IN2009/000037 WO2009098715A2 (en) | 2008-01-11 | 2009-01-12 | Novel pyrazolo [3, 4 -d] pyrimidine derivatives as anti -cancer agents |
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| JP2011509290A JP2011509290A (ja) | 2011-03-24 |
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| JP (1) | JP2011509290A (https=) |
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| KR101763656B1 (ko) | 2009-06-29 | 2017-08-01 | 인사이트 홀딩스 코포레이션 | Ｐｉ3ｋ 저해물질로서의 피리미디논 |
| US8759359B2 (en) * | 2009-12-18 | 2014-06-24 | Incyte Corporation | Substituted heteroaryl fused derivatives as PI3K inhibitors |
| TW201130842A (en) * | 2009-12-18 | 2011-09-16 | Incyte Corp | Substituted fused aryl and heteroaryl derivatives as PI3K inhibitors |
| EP2558463A1 (en) | 2010-04-14 | 2013-02-20 | Incyte Corporation | Fused derivatives as i3 inhibitors |
| WO2011163195A1 (en) | 2010-06-21 | 2011-12-29 | Incyte Corporation | Fused pyrrole derivatives as pi3k inhibitors |
| EP3660016A1 (en) | 2010-12-20 | 2020-06-03 | Incyte Holdings Corporation | N-(1-(substituted-phenyl)ethyl)-9h-purin-6-amines as pi3k inhibitors |
| US9108984B2 (en) | 2011-03-14 | 2015-08-18 | Incyte Corporation | Substituted diamino-pyrimidine and diamino-pyridine derivatives as PI3K inhibitors |
| WO2012135009A1 (en) | 2011-03-25 | 2012-10-04 | Incyte Corporation | Pyrimidine-4,6-diamine derivatives as pi3k inhibitors |
| PT3513793T (pt) | 2011-09-02 | 2021-05-10 | Incyte Holdings Corp | Heterociclilaminas como inibidores de pi3k |
| AR090548A1 (es) | 2012-04-02 | 2014-11-19 | Incyte Corp | Azaheterociclobencilaminas biciclicas como inhibidores de pi3k |
| CN102746307B (zh) * | 2012-07-09 | 2013-07-31 | 四川大学 | 1-n-苄基别嘌醇衍生物及其制备方法和用途 |
| CN102746309B (zh) * | 2012-07-09 | 2013-06-05 | 四川大学 | 1-N-乙基-4-N-2′-取代酰基肼-1H-吡唑[3,4-d]嘧啶类衍生物及其制备方法和用途 |
| CN103965202B (zh) * | 2014-05-21 | 2016-01-20 | 邹宏丽 | 二环稠合杂环化合物、其制备方法及用途 |
| WO2015191677A1 (en) | 2014-06-11 | 2015-12-17 | Incyte Corporation | Bicyclic heteroarylaminoalkyl phenyl derivatives as pi3k inhibitors |
| SG10201907576SA (en) | 2015-02-27 | 2019-09-27 | Incyte Corp | Salts of pi3k inhibitor and processes for their preparation |
| US9732097B2 (en) | 2015-05-11 | 2017-08-15 | Incyte Corporation | Process for the synthesis of a phosphoinositide 3-kinase inhibitor |
| US9988401B2 (en) | 2015-05-11 | 2018-06-05 | Incyte Corporation | Crystalline forms of a PI3K inhibitor |
| CN106008527B (zh) * | 2016-06-29 | 2018-05-15 | 四川大学华西医院 | 吡唑并[3,4-d]嘧啶衍生物 |
| CN107698596A (zh) * | 2017-11-15 | 2018-02-16 | 双鹤药业（商丘）有限责任公司 | 一种别嘌醇的合成方法 |
| SG11202011680YA (en) | 2018-06-01 | 2020-12-30 | Incyte Corp | Dosing regimen for the treatment of pi3k related disorders |
| US20230121698A1 (en) * | 2019-12-23 | 2023-04-20 | Sanford Burnham Prebys Medical Discovery Institute | Ectonucleotide pyrophosphatase/phosphodiesterase 1 (enpp1) modulators and uses thereof |
| CN115304607B (zh) * | 2022-07-06 | 2023-06-27 | 华南农业大学 | 吡唑并嘧啶衍生物的制备方法 |
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| US5958930A (en) | 1991-04-08 | 1999-09-28 | Duquesne University Of The Holy Ghost | Pyrrolo pyrimidine and furo pyrimidine derivatives |
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| AU1441497A (en) | 1996-01-23 | 1997-08-20 | Novartis Ag | Pyrrolopyrimidines and processes for their preparation |
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| US6537999B2 (en) | 1996-06-06 | 2003-03-25 | Duquesne University Of The Holy Ghost | Pyrimidine derivatives and methods of making and using these derivatives |
| WO1998007726A1 (en) | 1996-08-23 | 1998-02-26 | Novartis Ag | Substituted pyrrolopyrimidines and processes for their preparation |
| DE19709488A1 (de) | 1997-03-07 | 1998-09-10 | Basf Ag | Verfahren zur N-Alkylierung von Aminen |
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| ITMI992711A1 (it) | 1999-12-27 | 2001-06-27 | Novartis Ag | Composti organici |
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| TWI238824B (en) | 2001-05-14 | 2005-09-01 | Novartis Ag | 4-amino-5-phenyl-7-cyclobutyl-pyrrolo[2,3-d]pyrimidine derivatives |
| WO2003000187A2 (en) | 2001-06-21 | 2003-01-03 | Ariad Pharmaceuticals, Inc. | Novel pyrazolo-and pyrrolo-pyrimidines and uses thereof |
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- 2009-01-12 KR KR1020107017777A patent/KR20100116607A/ko not_active Withdrawn
- 2009-01-12 GE GEAP200911914A patent/GEP20135780B/en unknown
- 2009-01-12 NZ NZ586642A patent/NZ586642A/en not_active IP Right Cessation
- 2009-01-12 JP JP2010541891A patent/JP2011509290A/ja active Pending
- 2009-01-12 AU AU2009211004A patent/AU2009211004C1/en not_active Ceased
- 2009-01-12 US US12/812,405 patent/US8349847B2/en not_active Expired - Fee Related
- 2009-01-12 AP AP2010005347A patent/AP2010005347A0/en unknown
- 2009-01-12 CN CN2009801083051A patent/CN101965350A/zh active Pending
- 2009-01-12 BR BRPI0906475-3A patent/BRPI0906475A2/pt not_active IP Right Cessation
- 2009-01-12 MX MX2010007523A patent/MX2010007523A/es not_active Application Discontinuation
- 2009-01-12 EA EA201070841A patent/EA201070841A1/ru unknown
- 2009-01-12 WO PCT/IN2009/000037 patent/WO2009098715A2/en not_active Ceased
- 2009-01-12 CA CA2711777A patent/CA2711777A1/en not_active Abandoned
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2010
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- 2010-08-11 CO CO10098749A patent/CO6382174A2/es not_active Application Discontinuation
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