JP2013508334A5 - - Google Patents
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- Publication number
- JP2013508334A5 JP2013508334A5 JP2012534671A JP2012534671A JP2013508334A5 JP 2013508334 A5 JP2013508334 A5 JP 2013508334A5 JP 2012534671 A JP2012534671 A JP 2012534671A JP 2012534671 A JP2012534671 A JP 2012534671A JP 2013508334 A5 JP2013508334 A5 JP 2013508334A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- amino
- pyrazolo
- pyrimidin
- hydroxyphenyl
- 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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- 125000000217 alkyl group Chemical group 0.000 claims 90
- -1 2-((4-amino-3- (3-hydroxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-1-yl) methyl ) -3- (2-chlorobenzyl) -4-oxo-3,4-dihydroquinazolin-5-yl Chemical group 0.000 claims 28
- 150000001875 compounds Chemical class 0.000 claims 22
- 229910052739 hydrogen Inorganic materials 0.000 claims 19
- 239000001257 hydrogen Substances 0.000 claims 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 14
- 125000003545 alkoxy group Chemical group 0.000 claims 12
- 125000003118 aryl group Chemical group 0.000 claims 11
- 125000005843 halogen group Chemical group 0.000 claims 8
- 229910052757 nitrogen Inorganic materials 0.000 claims 8
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- 125000000623 heterocyclic group Chemical group 0.000 claims 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- QMNUDYFKZYBWQX-UHFFFAOYSA-N 1H-quinazolin-4-one Chemical compound C1=CC=C2C(=O)N=CNC2=C1 QMNUDYFKZYBWQX-UHFFFAOYSA-N 0.000 claims 6
- 125000004452 carbocyclyl group Chemical group 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000001188 haloalkyl group Chemical group 0.000 claims 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 150000002431 hydrogen Chemical group 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 229920006395 saturated elastomer Polymers 0.000 claims 4
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 3
- 239000000543 intermediate Substances 0.000 claims 3
- 230000000155 isotopic effect Effects 0.000 claims 3
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 claims 2
- XWTYSIMOBUGWOL-UHFFFAOYSA-N (+-)-Terbutaline Chemical compound CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1 XWTYSIMOBUGWOL-UHFFFAOYSA-N 0.000 claims 1
- CMRGXVSRHBPJNJ-UHFFFAOYSA-N 2-[[4-amino-3-(3-fluoro-4-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-[(2-chlorophenyl)methyl]-5-ethynylquinazolin-4-one Chemical compound N1=C(C=2C=C(F)C(O)=CC=2)C=2C(N)=NC=NC=2N1CC1=NC2=CC=CC(C#C)=C2C(=O)N1CC1=CC=CC=C1Cl CMRGXVSRHBPJNJ-UHFFFAOYSA-N 0.000 claims 1
- FAPNBNUTFBHNBO-UHFFFAOYSA-N 2-[[4-amino-3-(3-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-(1-benzofuran-5-ylmethyl)-5-(6-morpholin-4-yl-6-oxohex-1-ynyl)quinazolin-4-one Chemical compound N1=C(C=2C=C(O)C=CC=2)C=2C(N)=NC=NC=2N1CC(N(C(=O)C1=2)CC=3C=C4C=COC4=CC=3)=NC1=CC=CC=2C#CCCCC(=O)N1CCOCC1 FAPNBNUTFBHNBO-UHFFFAOYSA-N 0.000 claims 1
- CKCITHXJZULXIJ-UHFFFAOYSA-N 2-[[4-amino-3-(3-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-[(2-chlorophenyl)methyl]-5-(5-morpholin-4-yl-5-oxopent-1-ynyl)quinazolin-4-one Chemical compound N1=C(C=2C=C(O)C=CC=2)C=2C(N)=NC=NC=2N1CC(N(C(=O)C1=2)CC=3C(=CC=CC=3)Cl)=NC1=CC=CC=2C#CCCC(=O)N1CCOCC1 CKCITHXJZULXIJ-UHFFFAOYSA-N 0.000 claims 1
- DNUSLLSECCYLAU-UHFFFAOYSA-N 2-[[4-amino-3-(3-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-[(2-chlorophenyl)methyl]-5-(6-morpholin-4-yl-6-oxohex-1-ynyl)quinazolin-4-one Chemical compound N1=C(C=2C=C(O)C=CC=2)C=2C(N)=NC=NC=2N1CC(N(C(=O)C1=2)CC=3C(=CC=CC=3)Cl)=NC1=CC=CC=2C#CCCCC(=O)N1CCOCC1 DNUSLLSECCYLAU-UHFFFAOYSA-N 0.000 claims 1
- AONITTJLFLDVOT-UHFFFAOYSA-N 2-[[4-amino-3-(3-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-[(2-chlorophenyl)methyl]-5-[3-(2-methoxyethoxy)prop-1-ynyl]quinazolin-4-one Chemical compound C=1C=CC=C(Cl)C=1CN1C(=O)C=2C(C#CCOCCOC)=CC=CC=2N=C1CN(C1=NC=NC(N)=C11)N=C1C1=CC=CC(O)=C1 AONITTJLFLDVOT-UHFFFAOYSA-N 0.000 claims 1
- IPGQKTUMRGDJGJ-UHFFFAOYSA-N 2-[[4-amino-3-(3-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-[(2-chlorophenyl)methyl]-5-[3-(2-morpholin-4-ylethoxy)prop-1-ynyl]quinazolin-4-one Chemical compound N1=C(C=2C=C(O)C=CC=2)C=2C(N)=NC=NC=2N1CC(N(C(=O)C1=2)CC=3C(=CC=CC=3)Cl)=NC1=CC=CC=2C#CCOCCN1CCOCC1 IPGQKTUMRGDJGJ-UHFFFAOYSA-N 0.000 claims 1
- JPHWBLBSAYTMQE-UHFFFAOYSA-N 2-[[4-amino-3-(3-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-[(2-chlorophenyl)methyl]-5-[6-(4-methyl-1,4-diazepan-1-yl)-6-oxohex-1-ynyl]quinazolin-4-one Chemical compound C1CN(C)CCCN1C(=O)CCCC#CC1=CC=CC2=C1C(=O)N(CC=1C(=CC=CC=1)Cl)C(CN1C3=NC=NC(N)=C3C(C=3C=C(O)C=CC=3)=N1)=N2 JPHWBLBSAYTMQE-UHFFFAOYSA-N 0.000 claims 1
- ATTXPHLOHVVXMX-UHFFFAOYSA-N 2-[[4-amino-3-(3-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-[(2-chlorophenyl)methyl]-5-[6-(4-methylpiperazin-1-yl)-6-oxohex-1-ynyl]quinazolin-4-one Chemical compound C1CN(C)CCN1C(=O)CCCC#CC1=CC=CC2=C1C(=O)N(CC=1C(=CC=CC=1)Cl)C(CN1C3=NC=NC(N)=C3C(C=3C=C(O)C=CC=3)=N1)=N2 ATTXPHLOHVVXMX-UHFFFAOYSA-N 0.000 claims 1
- RYGLVCKHXMFBSY-UHFFFAOYSA-N 2-[[4-amino-3-(3-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-[(2-chlorophenyl)methyl]-5-[6-(4-morpholin-4-ylpiperidin-1-yl)-6-oxohex-1-ynyl]quinazolin-4-one Chemical compound N1=C(C=2C=C(O)C=CC=2)C=2C(N)=NC=NC=2N1CC(N(C(=O)C1=2)CC=3C(=CC=CC=3)Cl)=NC1=CC=CC=2C#CCCCC(=O)N(CC1)CCC1N1CCOCC1 RYGLVCKHXMFBSY-UHFFFAOYSA-N 0.000 claims 1
- XATOQOXZNMLDIC-UHFFFAOYSA-N 2-[[4-amino-3-(3-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-[(2-chlorophenyl)methyl]-5-[6-[3-(dimethylamino)pyrrolidin-1-yl]-6-oxohex-1-ynyl]quinazolin-4-one Chemical compound C1C(N(C)C)CCN1C(=O)CCCC#CC1=CC=CC2=C1C(=O)N(CC=1C(=CC=CC=1)Cl)C(CN1C3=NC=NC(N)=C3C(C=3C=C(O)C=CC=3)=N1)=N2 XATOQOXZNMLDIC-UHFFFAOYSA-N 0.000 claims 1
- GUOMZPPHSZMFRS-UHFFFAOYSA-N 2-[[4-amino-3-(3-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-[(2-chlorophenyl)methyl]-5-ethynylquinazolin-4-one Chemical compound N1=C(C=2C=C(O)C=CC=2)C=2C(N)=NC=NC=2N1CC1=NC2=CC=CC(C#C)=C2C(=O)N1CC1=CC=CC=C1Cl GUOMZPPHSZMFRS-UHFFFAOYSA-N 0.000 claims 1
- KKFFLLPTNWZVPK-UHFFFAOYSA-N 2-[[4-amino-3-(3-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-[(2-fluorophenyl)methyl]-5-[3-[2-(2-methoxyethoxy)ethoxy]prop-1-ynyl]quinazolin-4-one Chemical compound C=1C=CC=C(F)C=1CN1C(=O)C=2C(C#CCOCCOCCOC)=CC=CC=2N=C1CN(C1=NC=NC(N)=C11)N=C1C1=CC=CC(O)=C1 KKFFLLPTNWZVPK-UHFFFAOYSA-N 0.000 claims 1
- CWQXXYJTVPJDGB-UHFFFAOYSA-N 2-[[4-amino-3-(3-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-[(2-methyl-1,3-thiazol-4-yl)methyl]-5-(6-morpholin-4-yl-6-oxohex-1-ynyl)quinazolin-4-one Chemical compound S1C(C)=NC(CN2C(C3=C(C#CCCCC(=O)N4CCOCC4)C=CC=C3N=C2CN2C3=NC=NC(N)=C3C(C=3C=C(O)C=CC=3)=N2)=O)=C1 CWQXXYJTVPJDGB-UHFFFAOYSA-N 0.000 claims 1
- ODGUATJPXSLVMA-UHFFFAOYSA-N 2-[[4-amino-3-(3-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-[(3-chlorophenyl)methyl]-5-ethynylquinazolin-4-one Chemical compound N1=C(C=2C=C(O)C=CC=2)C=2C(N)=NC=NC=2N1CC1=NC2=CC=CC(C#C)=C2C(=O)N1CC1=CC=CC(Cl)=C1 ODGUATJPXSLVMA-UHFFFAOYSA-N 0.000 claims 1
- IUWJCOTVUGFZTA-UHFFFAOYSA-N 2-[[4-amino-3-(3-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-[(4-chlorophenyl)methyl]-5-(3-methoxyprop-1-ynyl)quinazolin-4-one Chemical compound C=1C=C(Cl)C=CC=1CN1C(=O)C=2C(C#CCOC)=CC=CC=2N=C1CN(C1=NC=NC(N)=C11)N=C1C1=CC=CC(O)=C1 IUWJCOTVUGFZTA-UHFFFAOYSA-N 0.000 claims 1
- ZTVJMMUPVCALPD-UHFFFAOYSA-N 2-[[4-amino-3-(3-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-[(4-chlorophenyl)methyl]-5-ethynylquinazolin-4-one Chemical compound N1=C(C=2C=C(O)C=CC=2)C=2C(N)=NC=NC=2N1CC1=NC2=CC=CC(C#C)=C2C(=O)N1CC1=CC=C(Cl)C=C1 ZTVJMMUPVCALPD-UHFFFAOYSA-N 0.000 claims 1
- WPAIGOKKTHBTOQ-UHFFFAOYSA-N 2-[[4-amino-3-(3-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-[(5-methylpyrazin-2-yl)methyl]-5-(6-morpholin-4-yl-6-oxohex-1-ynyl)quinazolin-4-one Chemical compound C1=NC(C)=CN=C1CN1C(=O)C2=C(C#CCCCC(=O)N3CCOCC3)C=CC=C2N=C1CN1C2=NC=NC(N)=C2C(C=2C=C(O)C=CC=2)=N1 WPAIGOKKTHBTOQ-UHFFFAOYSA-N 0.000 claims 1
- WZVLLCCQFGLPMC-UHFFFAOYSA-N 2-[[4-amino-3-(3-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-5-(3-methoxyprop-1-ynyl)-3-[[3-(trifluoromethyl)phenyl]methyl]quinazolin-4-one Chemical compound C=1C=CC(C(F)(F)F)=CC=1CN1C(=O)C=2C(C#CCOC)=CC=CC=2N=C1CN(C1=NC=NC(N)=C11)N=C1C1=CC=CC(O)=C1 WZVLLCCQFGLPMC-UHFFFAOYSA-N 0.000 claims 1
- KXTXIKMQFXXVEO-UHFFFAOYSA-N 2-[[4-amino-3-(3-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-5-ethynyl-3-[(2-fluorophenyl)methyl]quinazolin-4-one Chemical compound N1=C(C=2C=C(O)C=CC=2)C=2C(N)=NC=NC=2N1CC1=NC2=CC=CC(C#C)=C2C(=O)N1CC1=CC=CC=C1F KXTXIKMQFXXVEO-UHFFFAOYSA-N 0.000 claims 1
- YSQFSEVNOOJNRC-UHFFFAOYSA-N 2-[[4-amino-3-(3-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-5-ethynyl-3-[(3-methoxyphenyl)methyl]quinazolin-4-one Chemical compound COC1=CC=CC(CN2C(C3=C(C#C)C=CC=C3N=C2CN2C3=NC=NC(N)=C3C(C=3C=C(O)C=CC=3)=N2)=O)=C1 YSQFSEVNOOJNRC-UHFFFAOYSA-N 0.000 claims 1
- OTCDLPGOEYPRQV-UHFFFAOYSA-N 2-[[4-amino-3-(3-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-5-ethynyl-3-[(4-methylsulfonylphenyl)methyl]quinazolin-4-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1CN1C(=O)C2=C(C#C)C=CC=C2N=C1CN1C2=NC=NC(N)=C2C(C=2C=C(O)C=CC=2)=N1 OTCDLPGOEYPRQV-UHFFFAOYSA-N 0.000 claims 1
- LQKMEMKXODEOBY-UHFFFAOYSA-N 2-[[4-amino-3-(3-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-5-ethynyl-3-[(5-methyl-1,2-oxazol-3-yl)methyl]quinazolin-4-one Chemical compound O1C(C)=CC(CN2C(C3=C(C#C)C=CC=C3N=C2CN2C3=NC=NC(N)=C3C(C=3C=C(O)C=CC=3)=N2)=O)=N1 LQKMEMKXODEOBY-UHFFFAOYSA-N 0.000 claims 1
- MVSVRQJROSZUBJ-UHFFFAOYSA-N 2-[[4-amino-3-(3-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-5-ethynyl-3-[[3-(trifluoromethyl)phenyl]methyl]quinazolin-4-one Chemical compound N1=C(C=2C=C(O)C=CC=2)C=2C(N)=NC=NC=2N1CC1=NC2=CC=CC(C#C)=C2C(=O)N1CC1=CC=CC(C(F)(F)F)=C1 MVSVRQJROSZUBJ-UHFFFAOYSA-N 0.000 claims 1
- XJGAJHPRETZYHH-UHFFFAOYSA-N 2-[[4-amino-3-(3-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-5-ethynyl-3-[[4-(trifluoromethyl)phenyl]methyl]quinazolin-4-one Chemical compound N1=C(C=2C=C(O)C=CC=2)C=2C(N)=NC=NC=2N1CC1=NC2=CC=CC(C#C)=C2C(=O)N1CC1=CC=C(C(F)(F)F)C=C1 XJGAJHPRETZYHH-UHFFFAOYSA-N 0.000 claims 1
- RTLSICZZXIACFX-UHFFFAOYSA-N 2-[[4-amino-3-(4-fluoro-3-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-[(2-chlorophenyl)methyl]-5-ethynylquinazolin-4-one Chemical compound N1=C(C=2C=C(O)C(F)=CC=2)C=2C(N)=NC=NC=2N1CC1=NC2=CC=CC(C#C)=C2C(=O)N1CC1=CC=CC=C1Cl RTLSICZZXIACFX-UHFFFAOYSA-N 0.000 claims 1
- PTTGIRJMNMETGF-UHFFFAOYSA-N 2-[[4-amino-3-(4-hydroxy-3-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-[(2-chlorophenyl)methyl]-5-(6-morpholin-4-yl-6-oxohex-1-ynyl)quinazolin-4-one Chemical compound C1=C(O)C(OC)=CC(C=2C3=C(N)N=CN=C3N(CC=3N(C(=O)C4=C(C#CCCCC(=O)N5CCOCC5)C=CC=C4N=3)CC=3C(=CC=CC=3)Cl)N=2)=C1 PTTGIRJMNMETGF-UHFFFAOYSA-N 0.000 claims 1
- JEFQAQQSXUCVCQ-UHFFFAOYSA-N 2-[[4-amino-3-(4-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-(1-benzothiophen-2-ylmethyl)-5-(6-morpholin-4-yl-6-oxohex-1-ynyl)quinazolin-4-one Chemical compound N1=C(C=2C=CC(O)=CC=2)C=2C(N)=NC=NC=2N1CC(N(C(=O)C1=2)CC=3SC4=CC=CC=C4C=3)=NC1=CC=CC=2C#CCCCC(=O)N1CCOCC1 JEFQAQQSXUCVCQ-UHFFFAOYSA-N 0.000 claims 1
- SUUZMEMRUDWAMK-UHFFFAOYSA-N 2-[[4-amino-3-(4-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-[(2,6-difluorophenyl)methyl]-5-ethynylquinazolin-4-one Chemical compound N1=C(C=2C=CC(O)=CC=2)C=2C(N)=NC=NC=2N1CC1=NC2=CC=CC(C#C)=C2C(=O)N1CC1=C(F)C=CC=C1F SUUZMEMRUDWAMK-UHFFFAOYSA-N 0.000 claims 1
- FDUASEWUQUUQIV-UHFFFAOYSA-N 2-[[4-amino-3-(4-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-[(2-chlorophenyl)methyl]-5-(3-cyclopentylprop-1-ynyl)quinazolin-4-one Chemical compound N1=C(C=2C=CC(O)=CC=2)C=2C(N)=NC=NC=2N1CC(N(C(=O)C1=2)CC=3C(=CC=CC=3)Cl)=NC1=CC=CC=2C#CCC1CCCC1 FDUASEWUQUUQIV-UHFFFAOYSA-N 0.000 claims 1
- OCKOIOGJVSPUQB-UHFFFAOYSA-N 2-[[4-amino-3-(4-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-[(2-chlorophenyl)methyl]-5-(3-methoxyprop-1-ynyl)quinazolin-4-one Chemical compound C=1C=CC=C(Cl)C=1CN1C(=O)C=2C(C#CCOC)=CC=CC=2N=C1CN(C1=NC=NC(N)=C11)N=C1C1=CC=C(O)C=C1 OCKOIOGJVSPUQB-UHFFFAOYSA-N 0.000 claims 1
- QPYLRHVOWJEPMN-UHFFFAOYSA-N 2-[[4-amino-3-(4-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-[(2-chlorophenyl)methyl]-5-(3-phenoxyprop-1-ynyl)quinazolin-4-one Chemical compound N1=C(C=2C=CC(O)=CC=2)C=2C(N)=NC=NC=2N1CC(N(C(=O)C1=2)CC=3C(=CC=CC=3)Cl)=NC1=CC=CC=2C#CCOC1=CC=CC=C1 QPYLRHVOWJEPMN-UHFFFAOYSA-N 0.000 claims 1
- FGBHYFQNMHHQLS-UHFFFAOYSA-N 2-[[4-amino-3-(4-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-[(2-chlorophenyl)methyl]-5-(3-phenylmethoxyprop-1-ynyl)quinazolin-4-one Chemical compound N1=C(C=2C=CC(O)=CC=2)C=2C(N)=NC=NC=2N1CC(N(C(=O)C1=2)CC=3C(=CC=CC=3)Cl)=NC1=CC=CC=2C#CCOCC1=CC=CC=C1 FGBHYFQNMHHQLS-UHFFFAOYSA-N 0.000 claims 1
- DFYDLTALGVPURS-UHFFFAOYSA-N 2-[[4-amino-3-(4-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-[(2-chlorophenyl)methyl]-5-(5-hydroxypent-1-ynyl)quinazolin-4-one Chemical compound N1=C(C=2C=CC(O)=CC=2)C=2C(N)=NC=NC=2N1CC1=NC2=CC=CC(C#CCCCO)=C2C(=O)N1CC1=CC=CC=C1Cl DFYDLTALGVPURS-UHFFFAOYSA-N 0.000 claims 1
- LZLZWYUFFAROFC-UHFFFAOYSA-N 2-[[4-amino-3-(4-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-[(2-chlorophenyl)methyl]-5-(6-morpholin-4-yl-6-oxohex-1-ynyl)quinazolin-4-one Chemical compound N1=C(C=2C=CC(O)=CC=2)C=2C(N)=NC=NC=2N1CC(N(C(=O)C1=2)CC=3C(=CC=CC=3)Cl)=NC1=CC=CC=2C#CCCCC(=O)N1CCOCC1 LZLZWYUFFAROFC-UHFFFAOYSA-N 0.000 claims 1
- CNJZCZBGSDJQCJ-UHFFFAOYSA-N 2-[[4-amino-3-(4-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-[(2-chlorophenyl)methyl]-5-(6-oxo-6-piperidin-1-ylhex-1-ynyl)quinazolin-4-one Chemical compound N1=C(C=2C=CC(O)=CC=2)C=2C(N)=NC=NC=2N1CC(N(C(=O)C1=2)CC=3C(=CC=CC=3)Cl)=NC1=CC=CC=2C#CCCCC(=O)N1CCCCC1 CNJZCZBGSDJQCJ-UHFFFAOYSA-N 0.000 claims 1
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