JP2013508334A5 - - Google Patents
Download PDFInfo
- 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
Links
- 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
- GFPPJADRSAPASM-UHFFFAOYSA-N 2-[[4-amino-3-(4-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-[(2-chlorophenyl)methyl]-5-(6-oxo-6-pyrrolidin-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)N1CCCC1 GFPPJADRSAPASM-UHFFFAOYSA-N 0.000 claims 1
- XZLPIOCVALKFBZ-UHFFFAOYSA-N 2-[[4-amino-3-(4-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=CC(O)=CC=3)=N1)=N2 XZLPIOCVALKFBZ-UHFFFAOYSA-N 0.000 claims 1
- ORTOQALNRIMPBF-UHFFFAOYSA-N 2-[[4-amino-3-(4-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=CC(O)=CC=3)=N1)=N2 ORTOQALNRIMPBF-UHFFFAOYSA-N 0.000 claims 1
- OMVAPOKEPFCGEF-UHFFFAOYSA-N 2-[[4-amino-3-(4-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-[(2-chlorophenyl)methyl]-5-[6-[4-(2-methoxyethyl)piperazin-1-yl]-6-oxohex-1-ynyl]quinazolin-4-one Chemical compound C1CN(CCOC)CCN1C(=O)CCCC#CC1=CC=CC2=C1C(=O)N(CC=1C(=CC=CC=1)Cl)C(CN1C3=NC=NC(N)=C3C(C=3C=CC(O)=CC=3)=N1)=N2 OMVAPOKEPFCGEF-UHFFFAOYSA-N 0.000 claims 1
- VNIUXACFQIIIKG-UHFFFAOYSA-N 2-[[4-amino-3-(4-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-[(2-chlorophenyl)methyl]-5-[6-[4-(dimethylamino)piperidin-1-yl]-6-oxohex-1-ynyl]quinazolin-4-one Chemical compound C1CC(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=CC(O)=CC=3)=N1)=N2 VNIUXACFQIIIKG-UHFFFAOYSA-N 0.000 claims 1
- DENSYDWNLNJEQR-UHFFFAOYSA-N 2-[[4-amino-3-(4-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-[(2-chlorophenyl)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=CC=CC=C1Cl DENSYDWNLNJEQR-UHFFFAOYSA-N 0.000 claims 1
- DQQLMDLGTUARHB-UHFFFAOYSA-N 2-[[4-amino-3-(4-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-[(2-fluoro-3-methoxyphenyl)methyl]-5-(6-morpholin-4-yl-6-oxohex-1-ynyl)quinazolin-4-one Chemical compound COC1=CC=CC(CN2C(C3=C(C#CCCCC(=O)N4CCOCC4)C=CC=C3N=C2CN2C3=NC=NC(N)=C3C(C=3C=CC(O)=CC=3)=N2)=O)=C1F DQQLMDLGTUARHB-UHFFFAOYSA-N 0.000 claims 1
- XLKAZSKSPDCMIH-UHFFFAOYSA-N 2-[[4-amino-3-(4-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-[(2-fluorophenyl)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)F)=NC1=CC=CC=2C#CCCCC(=O)N1CCOCC1 XLKAZSKSPDCMIH-UHFFFAOYSA-N 0.000 claims 1
- UVULXADMHSSQFC-UHFFFAOYSA-N 2-[[4-amino-3-(4-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-[(3,4-dichlorophenyl)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=CC=C(Cl)C(Cl)=C1 UVULXADMHSSQFC-UHFFFAOYSA-N 0.000 claims 1
- YZBJQYMFMJIIBT-UHFFFAOYSA-N 2-[[4-amino-3-(4-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-[(3-chloro-2-fluorophenyl)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=CC=CC(Cl)=C1F YZBJQYMFMJIIBT-UHFFFAOYSA-N 0.000 claims 1
- ALEMKYQPUYKWDY-UHFFFAOYSA-N 2-[[4-amino-3-(4-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-[(3-chlorophenyl)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=CC=CC(Cl)=C1 ALEMKYQPUYKWDY-UHFFFAOYSA-N 0.000 claims 1
- ANTOVNWJHMCCOO-UHFFFAOYSA-N 2-[[4-amino-3-(4-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-[(3-methoxyphenyl)methyl]-5-(3-methoxyprop-1-ynyl)quinazolin-4-one Chemical compound C=1C=CC(OC)=CC=1CN1C(=O)C=2C(C#CCOC)=CC=CC=2N=C1CN(C1=NC=NC(N)=C11)N=C1C1=CC=C(O)C=C1 ANTOVNWJHMCCOO-UHFFFAOYSA-N 0.000 claims 1
- ZMQNQPZQOPWFCX-UHFFFAOYSA-N 2-[[4-amino-3-(4-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-[(4-chloro-2-fluorophenyl)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=CC=C(Cl)C=C1F ZMQNQPZQOPWFCX-UHFFFAOYSA-N 0.000 claims 1
- XIGSLUIZTRLSRB-UHFFFAOYSA-N 2-[[4-amino-3-(4-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-[(4-chlorophenyl)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=CC=C(Cl)C=C1 XIGSLUIZTRLSRB-UHFFFAOYSA-N 0.000 claims 1
- PLFCUZPWISVLBA-UHFFFAOYSA-N 2-[[4-amino-3-(4-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-[2-(2-methoxyphenyl)ethyl]-5-(6-morpholin-4-yl-6-oxohex-1-ynyl)quinazolin-4-one Chemical compound COC1=CC=CC=C1CCN1C(=O)C2=C(C#CCCCC(=O)N3CCOCC3)C=CC=C2N=C1CN1C2=NC=NC(N)=C2C(C=2C=CC(O)=CC=2)=N1 PLFCUZPWISVLBA-UHFFFAOYSA-N 0.000 claims 1
- ZTFKDFSMPRZEIS-UHFFFAOYSA-N 2-[[4-amino-3-(4-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-benzyl-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=CC=CC=C1 ZTFKDFSMPRZEIS-UHFFFAOYSA-N 0.000 claims 1
- ZLSDYPZEGQPHCJ-UHFFFAOYSA-N 2-[[4-amino-3-(4-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-5-[5-[bis(2-methoxyethyl)amino]pent-1-ynyl]-3-[(2-chlorophenyl)methyl]quinazolin-4-one Chemical compound C=1C=CC=C(Cl)C=1CN1C(=O)C=2C(C#CCCCN(CCOC)CCOC)=CC=CC=2N=C1CN(C1=NC=NC(N)=C11)N=C1C1=CC=C(O)C=C1 ZLSDYPZEGQPHCJ-UHFFFAOYSA-N 0.000 claims 1
- XBXWIWWWJFNCCA-UHFFFAOYSA-N 2-[[4-amino-3-(4-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-5-ethynyl-3-[(2-fluoro-4-methoxyphenyl)methyl]quinazolin-4-one Chemical compound FC1=CC(OC)=CC=C1CN1C(=O)C2=C(C#C)C=CC=C2N=C1CN1C2=NC=NC(N)=C2C(C=2C=CC(O)=CC=2)=N1 XBXWIWWWJFNCCA-UHFFFAOYSA-N 0.000 claims 1
- PNUHFWYRJGONAZ-UHFFFAOYSA-N 2-[[4-amino-3-(4-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-5-ethynyl-3-[(2-fluoro-5-methoxyphenyl)methyl]quinazolin-4-one Chemical compound COC1=CC=C(F)C(CN2C(C3=C(C#C)C=CC=C3N=C2CN2C3=NC=NC(N)=C3C(C=3C=CC(O)=CC=3)=N2)=O)=C1 PNUHFWYRJGONAZ-UHFFFAOYSA-N 0.000 claims 1
- JZGHEKRTCCGWQA-UHFFFAOYSA-N 2-[[4-amino-3-(4-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-5-ethynyl-3-[(2-fluorophenyl)methyl]quinazolin-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=CC=CC=C1F JZGHEKRTCCGWQA-UHFFFAOYSA-N 0.000 claims 1
- POQBZRJCKHPFHP-UHFFFAOYSA-N 2-[[4-amino-3-(4-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=CC(O)=CC=3)=N2)=O)=C1 POQBZRJCKHPFHP-UHFFFAOYSA-N 0.000 claims 1
- HIWBXNVIXWHNRQ-UHFFFAOYSA-N 2-[[4-amino-3-(4-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-5-ethynyl-3-[(4-fluorophenyl)methyl]quinazolin-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=CC=C(F)C=C1 HIWBXNVIXWHNRQ-UHFFFAOYSA-N 0.000 claims 1
- SLSFBDKQYOLPNC-UHFFFAOYSA-N 2-[[4-amino-3-(4-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-5-ethynyl-3-[(4-methoxyphenyl)methyl]quinazolin-4-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)C2=C(C#C)C=CC=C2N=C1CN1C2=NC=NC(N)=C2C(C=2C=CC(O)=CC=2)=N1 SLSFBDKQYOLPNC-UHFFFAOYSA-N 0.000 claims 1
- CVJWUNOFWLMXGY-UHFFFAOYSA-N 2-[[4-amino-3-(4-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=CC(O)=CC=2)=N1 CVJWUNOFWLMXGY-UHFFFAOYSA-N 0.000 claims 1
- YLJFVCGZFNADBT-UHFFFAOYSA-N 2-[[4-amino-3-(4-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=CC(O)=CC=3)=N2)=O)=N1 YLJFVCGZFNADBT-UHFFFAOYSA-N 0.000 claims 1
- TXEDXUBVQBSOMA-UHFFFAOYSA-N 2-[[4-amino-3-(4-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-5-ethynyl-3-[[2-(trifluoromethyl)phenyl]methyl]quinazolin-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=CC=CC=C1C(F)(F)F TXEDXUBVQBSOMA-UHFFFAOYSA-N 0.000 claims 1
- WKSBDNHHEHXNMM-UHFFFAOYSA-N 2-[[4-amino-3-(4-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=CC(O)=CC=2)C=2C(N)=NC=NC=2N1CC1=NC2=CC=CC(C#C)=C2C(=O)N1CC1=CC=CC(C(F)(F)F)=C1 WKSBDNHHEHXNMM-UHFFFAOYSA-N 0.000 claims 1
- MSOXMABFRIRTIK-UHFFFAOYSA-N 2-[[4-amino-3-(4-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=CC(O)=CC=2)C=2C(N)=NC=NC=2N1CC1=NC2=CC=CC(C#C)=C2C(=O)N1CC1=CC=C(C(F)(F)F)C=C1 MSOXMABFRIRTIK-UHFFFAOYSA-N 0.000 claims 1
- HESROJVDPXQZDW-UHFFFAOYSA-N 3-[2-[[4-amino-3-(4-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-[(2-chlorophenyl)methyl]-4-oxoquinazolin-5-yl]prop-2-ynylurea Chemical compound C=1C=CC=C(Cl)C=1CN1C(=O)C=2C(C#CCNC(=O)N)=CC=CC=2N=C1CN(C1=NC=NC(N)=C11)N=C1C1=CC=C(O)C=C1 HESROJVDPXQZDW-UHFFFAOYSA-N 0.000 claims 1
- INEFQSAZKFSDNE-UHFFFAOYSA-N 3-[[2-[[4-amino-3-(3-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-5-ethynyl-4-oxoquinazolin-3-yl]methyl]benzonitrile 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#N)=C1 INEFQSAZKFSDNE-UHFFFAOYSA-N 0.000 claims 1
- LWQUSLJKUPOEQI-UHFFFAOYSA-N 3-[[2-[[4-amino-3-(4-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-5-ethynyl-4-oxoquinazolin-3-yl]methyl]benzonitrile Chemical compound N1=C(C=2C=CC(O)=CC=2)C=2C(N)=NC=NC=2N1CC1=NC2=CC=CC(C#C)=C2C(=O)N1CC1=CC=CC(C#N)=C1 LWQUSLJKUPOEQI-UHFFFAOYSA-N 0.000 claims 1
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- FAEKTNGTNFHFRB-UHFFFAOYSA-N 4-[[2-[[4-amino-3-(4-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-5-ethynyl-4-oxoquinazolin-3-yl]methyl]benzonitrile Chemical compound N1=C(C=2C=CC(O)=CC=2)C=2C(N)=NC=NC=2N1CC1=NC2=CC=CC(C#C)=C2C(=O)N1CC1=CC=C(C#N)C=C1 FAEKTNGTNFHFRB-UHFFFAOYSA-N 0.000 claims 1
- NLAFCFUVNPEKMI-UHFFFAOYSA-N 6-[2-[[4-amino-3-(4-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-[(2-chlorophenyl)methyl]-4-oxoquinazolin-5-yl]hex-5-ynoic acid Chemical compound N1=C(C=2C=CC(O)=CC=2)C=2C(N)=NC=NC=2N1CC1=NC2=CC=CC(C#CCCCC(O)=O)=C2C(=O)N1CC1=CC=CC=C1Cl NLAFCFUVNPEKMI-UHFFFAOYSA-N 0.000 claims 1
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 claims 1
- KUVIULQEHSCUHY-XYWKZLDCSA-N Beclometasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COC(=O)CC)(OC(=O)CC)[C@@]1(C)C[C@@H]2O KUVIULQEHSCUHY-XYWKZLDCSA-N 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 206010006458 Bronchitis chronic Diseases 0.000 claims 1
- VOVIALXJUBGFJZ-KWVAZRHASA-N Budesonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O VOVIALXJUBGFJZ-KWVAZRHASA-N 0.000 claims 1
- RZTUGPPWTDSNQK-UHFFFAOYSA-N CS(=O)(=O)C=1C=C(CC2=NC3=CC=CC=C3C(N2)=O)C=CC=1 Chemical compound CS(=O)(=O)C=1C=C(CC2=NC3=CC=CC=C3C(N2)=O)C=CC=1 RZTUGPPWTDSNQK-UHFFFAOYSA-N 0.000 claims 1
- 206010006895 Cachexia Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 1
- 206010010741 Conjunctivitis Diseases 0.000 claims 1
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims 1
- 201000003883 Cystic fibrosis Diseases 0.000 claims 1
- 206010012434 Dermatitis allergic Diseases 0.000 claims 1
- 206010012442 Dermatitis contact Diseases 0.000 claims 1
- 206010014561 Emphysema Diseases 0.000 claims 1
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims 1
- 102000014150 Interferons Human genes 0.000 claims 1
- 108010050904 Interferons Proteins 0.000 claims 1
- 229940122696 MAP kinase inhibitor Drugs 0.000 claims 1
- 206010027476 Metastases Diseases 0.000 claims 1
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 claims 1
- 206010033645 Pancreatitis Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 206010039085 Rhinitis allergic Diseases 0.000 claims 1
- GIIZNNXWQWCKIB-UHFFFAOYSA-N Serevent Chemical compound C1=C(O)C(CO)=CC(C(O)CNCCCCCCOCCCCC=2C=CC=CC=2)=C1 GIIZNNXWQWCKIB-UHFFFAOYSA-N 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 229960004150 aciclovir Drugs 0.000 claims 1
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 claims 1
- 208000002205 allergic conjunctivitis Diseases 0.000 claims 1
- 201000010105 allergic rhinitis Diseases 0.000 claims 1
- 239000003443 antiviral agent Substances 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 208000024998 atopic conjunctivitis Diseases 0.000 claims 1
- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- 208000010668 atopic eczema Diseases 0.000 claims 1
- 229950000210 beclometasone dipropionate Drugs 0.000 claims 1
- 229940125388 beta agonist Drugs 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 206010006451 bronchitis Diseases 0.000 claims 1
- 229960004436 budesonide Drugs 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 208000029771 childhood onset asthma Diseases 0.000 claims 1
- 208000007451 chronic bronchitis Diseases 0.000 claims 1
- 208000010247 contact dermatitis Diseases 0.000 claims 1
- 208000035250 cutaneous malignant susceptibility to 1 melanoma Diseases 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229960001469 fluticasone furoate Drugs 0.000 claims 1
- XTULMSXFIHGYFS-VLSRWLAYSA-N fluticasone furoate Chemical compound O([C@]1([C@@]2(C)C[C@H](O)[C@]3(F)[C@@]4(C)C=CC(=O)C=C4[C@@H](F)C[C@H]3[C@@H]2C[C@H]1C)C(=O)SCF)C(=O)C1=CC=CO1 XTULMSXFIHGYFS-VLSRWLAYSA-N 0.000 claims 1
- 229960000289 fluticasone propionate Drugs 0.000 claims 1
- WMWTYOKRWGGJOA-CENSZEJFSA-N fluticasone propionate Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)SCF)(OC(=O)CC)[C@@]2(C)C[C@@H]1O WMWTYOKRWGGJOA-CENSZEJFSA-N 0.000 claims 1
- 229960002848 formoterol Drugs 0.000 claims 1
- BPZSYCZIITTYBL-UHFFFAOYSA-N formoterol Chemical compound C1=CC(OC)=CC=C1CC(C)NCC(O)C1=CC=C(O)C(NC=O)=C1 BPZSYCZIITTYBL-UHFFFAOYSA-N 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 229960004078 indacaterol Drugs 0.000 claims 1
- QZZUEBNBZAPZLX-QFIPXVFZSA-N indacaterol Chemical compound N1C(=O)C=CC2=C1C(O)=CC=C2[C@@H](O)CNC1CC(C=C(C(=C2)CC)CC)=C2C1 QZZUEBNBZAPZLX-QFIPXVFZSA-N 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 229940079322 interferon Drugs 0.000 claims 1
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims 1
- OEXHQOGQTVQTAT-JRNQLAHRSA-N ipratropium Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)[N@@+]2(C)C(C)C)C(=O)C(CO)C1=CC=CC=C1 OEXHQOGQTVQTAT-JRNQLAHRSA-N 0.000 claims 1
- 229960001888 ipratropium Drugs 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 230000009401 metastasis Effects 0.000 claims 1
- 229940095102 methyl benzoate Drugs 0.000 claims 1
- 239000002829 mitogen activated protein kinase inhibitor Substances 0.000 claims 1
- 229960002744 mometasone furoate Drugs 0.000 claims 1
- WOFMFGQZHJDGCX-ZULDAHANSA-N mometasone furoate Chemical compound O([C@]1([C@@]2(C)C[C@H](O)[C@]3(Cl)[C@@]4(C)C=CC(=O)C=C4CC[C@H]3[C@@H]2C[C@H]1C)C(=O)CCl)C(=O)C1=CC=CO1 WOFMFGQZHJDGCX-ZULDAHANSA-N 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 239000003149 muscarinic antagonist Substances 0.000 claims 1
- NRHJQBIYQBAJBZ-UHFFFAOYSA-N n-[4-[2-[[4-amino-3-(3-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-[(2-chlorophenyl)methyl]-4-oxoquinazolin-5-yl]but-3-ynyl]morpholine-4-carboxamide 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#CCCNC(=O)N1CCOCC1 NRHJQBIYQBAJBZ-UHFFFAOYSA-N 0.000 claims 1
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 1
- PGZUMBJQJWIWGJ-ONAKXNSWSA-N oseltamivir phosphate Chemical compound OP(O)(O)=O.CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C1 PGZUMBJQJWIWGJ-ONAKXNSWSA-N 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 claims 1
- 108010068338 p38 Mitogen-Activated Protein Kinases Proteins 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 229940061374 relenza Drugs 0.000 claims 1
- 208000023504 respiratory system disease Diseases 0.000 claims 1
- 206010039083 rhinitis Diseases 0.000 claims 1
- 229960002052 salbutamol Drugs 0.000 claims 1
- 229960004017 salmeterol Drugs 0.000 claims 1
- 201000000306 sarcoidosis Diseases 0.000 claims 1
- 201000009890 sinusitis Diseases 0.000 claims 1
- 150000003431 steroids Chemical class 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 230000001629 suppression Effects 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- 229940065721 systemic for obstructive airway disease xanthines Drugs 0.000 claims 1
- 229940061367 tamiflu Drugs 0.000 claims 1
- 229960000195 terbutaline Drugs 0.000 claims 1
- 229960000278 theophylline Drugs 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 230000004614 tumor growth Effects 0.000 claims 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 1
- ARAIBEBZBOPLMB-UFGQHTETSA-N zanamivir Chemical compound CC(=O)N[C@@H]1[C@@H](N=C(N)N)C=C(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO ARAIBEBZBOPLMB-UFGQHTETSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0918249.4A GB0918249D0 (en) | 2009-10-19 | 2009-10-19 | Compounds |
| GB0918249.4 | 2009-10-19 | ||
| PCT/EP2010/065746 WO2011048111A1 (en) | 2009-10-19 | 2010-10-19 | Compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013508334A JP2013508334A (ja) | 2013-03-07 |
| JP2013508334A5 true JP2013508334A5 (OSRAM) | 2013-12-05 |
| JP5889792B2 JP5889792B2 (ja) | 2016-03-22 |
Family
ID=41462531
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012534671A Expired - Fee Related JP5889792B2 (ja) | 2009-10-19 | 2010-10-19 | 化合物 |
Country Status (35)
| Country | Link |
|---|---|
| US (4) | US8741909B2 (OSRAM) |
| EP (1) | EP2491037B1 (OSRAM) |
| JP (1) | JP5889792B2 (OSRAM) |
| KR (1) | KR101770616B1 (OSRAM) |
| CN (1) | CN102712645B (OSRAM) |
| AR (1) | AR078674A1 (OSRAM) |
| AU (1) | AU2010309832B2 (OSRAM) |
| BR (1) | BR112012009214A2 (OSRAM) |
| CA (1) | CA2777902C (OSRAM) |
| CL (1) | CL2012000981A1 (OSRAM) |
| CR (1) | CR20120264A (OSRAM) |
| CY (1) | CY1116057T1 (OSRAM) |
| DK (1) | DK2491037T3 (OSRAM) |
| EA (1) | EA020330B3 (OSRAM) |
| EC (1) | ECSP12011805A (OSRAM) |
| ES (1) | ES2477270T3 (OSRAM) |
| GB (1) | GB0918249D0 (OSRAM) |
| HR (1) | HRP20140599T1 (OSRAM) |
| IL (1) | IL219248A (OSRAM) |
| ME (1) | ME02064B (OSRAM) |
| MX (1) | MX2012004525A (OSRAM) |
| MY (1) | MY164731A (OSRAM) |
| NI (2) | NI201200061A (OSRAM) |
| NZ (2) | NZ599162A (OSRAM) |
| PE (1) | PE20121390A1 (OSRAM) |
| PH (1) | PH12012500620A1 (OSRAM) |
| PL (1) | PL2491037T3 (OSRAM) |
| PT (1) | PT2491037E (OSRAM) |
| RS (1) | RS53385B (OSRAM) |
| SI (1) | SI2491037T1 (OSRAM) |
| SM (1) | SMT201400086B (OSRAM) |
| TW (1) | TWI478923B (OSRAM) |
| UA (1) | UA108743C2 (OSRAM) |
| WO (1) | WO2011048111A1 (OSRAM) |
| ZA (1) | ZA201203662B (OSRAM) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101945869B (zh) | 2007-12-19 | 2014-06-18 | 癌症研究技术有限公司 | 吡啶并[2,3-b]吡嗪-8-取代化合物及其用途 |
| GB0918249D0 (en) | 2009-10-19 | 2009-12-02 | Respivert Ltd | Compounds |
| US8815896B2 (en) | 2010-02-01 | 2014-08-26 | The Institute Of Cancer Research: Royal Cancer Hospital | 1-(5-tert-butyl-2-phenyl-2H-pyrazol-3-yl)-3-[2-fluoro-4-(1-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-B]pyridin-7-yloxy)-phenyl]-urea and related compounds and their use in therapy |
| UY33337A (es) * | 2010-10-18 | 2011-10-31 | Respivert Ltd | DERIVADOS SUSTITUIDOS DE 1H-PIRAZOL[ 3,4-d]PIRIMIDINA COMO INHIBIDORES DE LAS FOSFOINOSITIDA 3-QUINASAS |
| ES2661510T3 (es) | 2011-12-15 | 2018-04-02 | Novartis Ag | Uso de inhibidores de la actividad o función de PI3K |
| SG11201404522VA (en) * | 2012-03-13 | 2014-10-30 | Respivert Ltd | Crystalline pi3 kinase inhibitors |
| US8940742B2 (en) | 2012-04-10 | 2015-01-27 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| KR20150079745A (ko) | 2012-11-08 | 2015-07-08 | 리젠 파마슈티컬스 소시에떼 아노님 | Pde4 억제제 및 pi3 델타 또는 이중 pi3 델타-감마 키나아제 억제제를 함유하는 약제학적 조성물 |
| AR095353A1 (es) | 2013-03-15 | 2015-10-07 | Respivert Ltd | Compuesto |
| JO3279B1 (ar) * | 2013-03-15 | 2018-09-16 | Respivert Ltd | مشتقات 2-((4- امينو -3- (3- فلورو-5- هيدروكسي فينيل)-h1- بيرازولو [d-3,4] بيرمدين-1-يل )ميثيل )- 3- (2- تراي فلورو ميثيل ) بينزيل ) كوينازولين -4 (h3)- واحد واستخدامها كمثبطات فوسفواينوسيتايد 3- كاينيز |
| BR112015030881A2 (pt) | 2013-06-14 | 2017-10-24 | Psioxus Theraupeutics Ltd | regime de dosagem e formulações para adenovírus de tipo b |
| SG10201902074UA (en) | 2013-10-04 | 2019-04-29 | Infinity Pharmaceuticals Inc | Heterocyclic compounds and uses thereof |
| WO2015051241A1 (en) | 2013-10-04 | 2015-04-09 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| GB201320732D0 (en) | 2013-11-25 | 2014-01-08 | Cancer Rec Tech Ltd | Methods of chemical synthesis |
| GB201320729D0 (en) | 2013-11-25 | 2014-01-08 | Cancer Rec Tech Ltd | Therapeutic compounds and their use |
| CN113616656B (zh) | 2014-03-19 | 2023-02-17 | 无限药品股份有限公司 | 用于治疗PI3K-γ介导的障碍的杂环化合物 |
| GB201510197D0 (en) | 2014-06-12 | 2015-07-29 | Psioxus Therapeutics Ltd | Method of treating ovarian cancer |
| MX2017000208A (es) | 2014-07-04 | 2017-05-01 | Lupin Ltd | Derivados de quinolizinona como inhibidores de pi3k. |
| WO2016054491A1 (en) | 2014-10-03 | 2016-04-07 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| AU2016322552B2 (en) | 2015-09-14 | 2021-03-25 | Infinity Pharmaceuticals, Inc. | Solid forms of isoquinolinone derivatives, process of making, compositions comprising, and methods of using the same |
| WO2017161116A1 (en) | 2016-03-17 | 2017-09-21 | Infinity Pharmaceuticals, Inc. | Isotopologues of isoquinolinone and quinazolinone compounds and uses thereof as pi3k kinase inhibitors |
| WO2017214269A1 (en) | 2016-06-08 | 2017-12-14 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| US10751339B2 (en) | 2018-01-20 | 2020-08-25 | Sunshine Lake Pharma Co., Ltd. | Substituted aminopyrimidine compounds and methods of use |
| CN108516976B (zh) * | 2018-04-27 | 2020-07-03 | 四川大学华西医院 | 一种7-脱氮嘌呤衍生物及其四元环超分子结构 |
| JP2022500422A (ja) * | 2018-09-18 | 2022-01-04 | ソシエテ・デ・プロデュイ・ネスレ・エス・アー | 骨格筋調節のためのｓｒｃ阻害剤化合物、それらの方法及び使用 |
| WO2022017371A1 (zh) * | 2020-07-21 | 2022-01-27 | 中国医药研究开发中心有限公司 | 具有磷脂酰肌醇3-激酶δ和γ的双重抑制剂活性的杂环化合物及其医药用途 |
Family Cites Families (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1204826B (it) | 1986-03-04 | 1989-03-10 | Chiesi Farma Spa | Composizioni farmaceutiche per inalazione |
| GB9501841D0 (en) | 1995-01-31 | 1995-03-22 | Co Ordinated Drug Dev | Improvements in and relating to carrier particles for use in dry powder inhalers |
| HU226164B1 (en) | 1998-11-13 | 2008-05-28 | Jagotec Ag | Use of magnesium stearate in dry powder compositions suitable for inhalation and compositions suitable for inhalation |
| CA2369895C (en) | 1999-01-11 | 2010-12-21 | Princeton University | High affinity inhibitors for target validation and uses thereof |
| PT1158958E (pt) | 1999-03-05 | 2007-08-13 | Chiesi Farma Spa | ''composições farmacêuticas em pó, melhoradas, para inalação'' |
| PE20011227A1 (es) | 2000-04-17 | 2002-01-07 | Chiesi Farma Spa | Formulaciones farmaceuticas para inhaladores de polvo seco en la forma de aglomerados duros |
| US6667300B2 (en) * | 2000-04-25 | 2003-12-23 | Icos Corporation | Inhibitors of human phosphatidylinositol 3-kinase delta |
| KR100785363B1 (ko) | 2000-04-25 | 2007-12-18 | 이코스 코포레이션 | 인간 포스파티딜-이노시톨 3-키나제 델타의 억제제 |
| KR100774855B1 (ko) | 2000-04-27 | 2007-11-08 | 아스텔라스세이야쿠 가부시키가이샤 | 축합 헤테로아릴 유도체 |
| US6608053B2 (en) | 2000-04-27 | 2003-08-19 | Yamanouchi Pharmaceutical Co., Ltd. | Fused heteroaryl derivatives |
| EP1217000A1 (en) | 2000-12-23 | 2002-06-26 | Aventis Pharma Deutschland GmbH | Inhibitors of factor Xa and factor VIIa |
| WO2003006628A2 (en) | 2001-07-13 | 2003-01-23 | Virtual Drug Development, Inc. | Nad synthetase inhibitors and uses thereof |
| AU2002317377A1 (en) | 2001-07-20 | 2003-03-03 | Cancer Research Technology Limited | Biphenyl apurinic/apyrimidinic site endonuclease inhibitors to treat cancer |
| AU2003301662A1 (en) | 2002-10-21 | 2004-05-13 | Bristol-Myers Squibb Company | Quinazolinones and derivatives thereof as factor xa inhibitors |
| JP4736043B2 (ja) | 2003-03-14 | 2011-07-27 | 小野薬品工業株式会社 | 含窒素複素環誘導体およびそれらを有効成分とする薬剤 |
| US7122557B2 (en) | 2003-03-18 | 2006-10-17 | Bristol-Myers Squibb Company | Sulfonyl-amidino-containing and tetrahydropyrimidino-containing compounds as factor Xa inhibitors |
| EP1625165A2 (en) | 2003-04-03 | 2006-02-15 | Protein Design Labs, Inc. | Inhibitors of integrin alpha5beta1 and their use for the control of tissue granulation |
| US7429596B2 (en) | 2003-06-20 | 2008-09-30 | The Regents Of The University Of California | 1H-pyrrolo [2,3-D] pyrimidine derivatives and methods of use thereof |
| GB0316341D0 (en) | 2003-07-11 | 2003-08-13 | Glaxo Group Ltd | Pharmaceutical formulations |
| US20100267778A1 (en) | 2003-08-04 | 2010-10-21 | Shinya Kusuda | Diphenyl ether compound, process for producing the same, and use |
| US20050043239A1 (en) | 2003-08-14 | 2005-02-24 | Jason Douangpanya | Methods of inhibiting immune responses stimulated by an endogenous factor |
| WO2005016349A1 (en) | 2003-08-14 | 2005-02-24 | Icos Corporation | Methods of inhibiting leukocyte accumulation |
| GB0326632D0 (en) | 2003-11-14 | 2003-12-17 | Jagotec Ag | Dry powder formulations |
| US20050239809A1 (en) | 2004-01-08 | 2005-10-27 | Watts Stephanie W | Methods for treating and preventing hypertension and hypertension-related disorders |
| ES2873875T3 (es) | 2004-05-13 | 2021-11-04 | Icos Corp | Quinazolinonas como inhibidores de fosfatidilinositol 3-quinasa delta humano |
| CA2730540A1 (en) | 2004-05-13 | 2005-12-01 | Vanderbilt University | Phosphoinositide 3-kinase delta selective inhibitors for inhibiting angiogenesis |
| WO2005117889A1 (en) | 2004-05-25 | 2005-12-15 | Icos Corporation | Methods for treating and/or preventing aberrant proliferation of hematopoietic |
| EP1750715A1 (en) | 2004-06-04 | 2007-02-14 | Icos Corporation | Methods for treating mast cell disorders |
| AU2005283326B2 (en) | 2004-09-13 | 2011-07-21 | Ono Pharmaceutical Co., Ltd. | Nitrogenous heterocyclic derivative and medicine containing the same as an active ingredient |
| GB0425758D0 (en) | 2004-11-23 | 2004-12-22 | Vectura Ltd | Preparation of pharmaceutical compositions |
| US20080287469A1 (en) | 2005-02-17 | 2008-11-20 | Diacovo Thomas G | Phosphoinositide 3-Kinase Inhibitors for Inhibiting Leukocyte Accumulation |
| GB0525254D0 (en) | 2005-12-12 | 2006-01-18 | Jagotec Ag | Powder compositions for inhalation |
| SI2004654T1 (sl) * | 2006-04-04 | 2013-11-29 | The Regents Of The University Of California | Pirazolopirimidinski derivati za uporabo kot kinazni antagonisti |
| KR20090017498A (ko) | 2006-04-04 | 2009-02-18 | 더 리젠트스 오브 더 유니이버시티 오브 캘리포니아 | Ｐｉ３ 키나제 길항물질 |
| CA2652886A1 (en) | 2006-05-24 | 2007-11-29 | Bayer Schering Pharma Aktiengesellschaft | High affinity human and humanized anti-.alpha.5.beta.1 integrin function blocking antibodies with reduced immunogenicity |
| MX2009000107A (es) | 2006-06-29 | 2009-01-23 | Schering Corp | Antagonistas del receptor de trombina biciclicos y triciclicos sustituidos. |
| GB0622818D0 (en) | 2006-11-15 | 2006-12-27 | Jagotec Ag | Improvements in or relating to organic compounds |
| EP2081892A4 (en) | 2006-11-17 | 2014-03-05 | Donald F Weaver | COMPOUNDS AND METHOD FOR THE TREATMENT OF PROTEIN DISAPPEARANCE |
| WO2008067219A2 (en) | 2006-11-29 | 2008-06-05 | Kalypsys, Inc. | Quinazolinone modulators of tgr5 |
| US8338437B2 (en) | 2007-02-28 | 2012-12-25 | Methylgene Inc. | Amines as small molecule inhibitors |
| US20100305113A1 (en) * | 2007-05-09 | 2010-12-02 | Hans-Georg Capraro | Substituted Imidazopyridazines as Lipid Kinase Inhibitors |
| WO2008140750A1 (en) | 2007-05-10 | 2008-11-20 | Hydra Biosciences Inc. | Compounds for modulating trpv3 function |
| WO2009088990A1 (en) * | 2008-01-04 | 2009-07-16 | Intellikine, Inc. | Certain chemical entities, compositions and methods |
| CA2738429C (en) | 2008-09-26 | 2016-10-25 | Intellikine, Inc. | Heterocyclic kinase inhibitors |
| US20110269779A1 (en) | 2008-11-18 | 2011-11-03 | Intellikine, Inc. | Methods and compositions for treatment of ophthalmic conditions |
| AU2009322187B2 (en) | 2008-12-04 | 2015-02-19 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Phosphatidylinositol-3-kinase p110 delta-targeted drugs in the treatment of CNS disorders |
| US8658648B2 (en) | 2008-12-05 | 2014-02-25 | Designmedix, Inc. | Modified chloroquines with single ring moiety or fused ring moiety |
| US20110135655A1 (en) * | 2009-01-13 | 2011-06-09 | PHILADELPHIA HEALTH AND EDUCATION CORPORATION d/b/a Drexel University College of Medicine; | Role of PI3K p110 delta Signaling in Retroviral Infection and Replication |
| MX2011009955A (es) | 2009-03-24 | 2011-11-18 | Gilead Calistoga Llc | Atropisomeros de derivados de 2-purinil-3-tolil-quinazolinona y metodos de uso. |
| BR112012002331A2 (pt) | 2009-08-05 | 2019-09-24 | Versitech Ltd | composição antiviral, composição farmacêutica e uso de quantidade efetiva de composição farmacêutica |
| GB0918249D0 (en) | 2009-10-19 | 2009-12-02 | Respivert Ltd | Compounds |
| RU2580890C2 (ru) | 2010-09-30 | 2016-04-10 | КЬЕЗИ ФАРМАЧЕУТИЧИ С.п.А. | Применение стеарата магния в составах сухого порошка для ингаляции |
| UY33337A (es) * | 2010-10-18 | 2011-10-31 | Respivert Ltd | DERIVADOS SUSTITUIDOS DE 1H-PIRAZOL[ 3,4-d]PIRIMIDINA COMO INHIBIDORES DE LAS FOSFOINOSITIDA 3-QUINASAS |
| SG11201404522VA (en) | 2012-03-13 | 2014-10-30 | Respivert Ltd | Crystalline pi3 kinase inhibitors |
-
2009
- 2009-10-19 GB GBGB0918249.4A patent/GB0918249D0/en not_active Ceased
-
2010
- 2010-10-18 TW TW099135360A patent/TWI478923B/zh not_active IP Right Cessation
- 2010-10-19 PL PL10771416T patent/PL2491037T3/pl unknown
- 2010-10-19 WO PCT/EP2010/065746 patent/WO2011048111A1/en not_active Ceased
- 2010-10-19 KR KR1020127012826A patent/KR101770616B1/ko not_active Expired - Fee Related
- 2010-10-19 HR HRP20140599AT patent/HRP20140599T1/hr unknown
- 2010-10-19 CN CN201080047955.2A patent/CN102712645B/zh not_active Expired - Fee Related
- 2010-10-19 RS RS20140344A patent/RS53385B/sr unknown
- 2010-10-19 EP EP10771416.4A patent/EP2491037B1/en active Active
- 2010-10-19 SI SI201030660T patent/SI2491037T1/sl unknown
- 2010-10-19 PE PE2012000506A patent/PE20121390A1/es not_active Application Discontinuation
- 2010-10-19 CA CA2777902A patent/CA2777902C/en not_active Expired - Fee Related
- 2010-10-19 US US13/502,465 patent/US8741909B2/en not_active Expired - Fee Related
- 2010-10-19 NZ NZ599162A patent/NZ599162A/xx not_active IP Right Cessation
- 2010-10-19 BR BR112012009214A patent/BR112012009214A2/pt not_active IP Right Cessation
- 2010-10-19 MX MX2012004525A patent/MX2012004525A/es active IP Right Grant
- 2010-10-19 EA EA201270575A patent/EA020330B3/ru not_active IP Right Cessation
- 2010-10-19 DK DK10771416.4T patent/DK2491037T3/da active
- 2010-10-19 JP JP2012534671A patent/JP5889792B2/ja not_active Expired - Fee Related
- 2010-10-19 UA UAA201203872A patent/UA108743C2/ru unknown
- 2010-10-19 PT PT107714164T patent/PT2491037E/pt unknown
- 2010-10-19 AR ARP100103812A patent/AR078674A1/es unknown
- 2010-10-19 PH PH1/2012/500620A patent/PH12012500620A1/en unknown
- 2010-10-19 AU AU2010309832A patent/AU2010309832B2/en not_active Ceased
- 2010-10-19 ES ES10771416.4T patent/ES2477270T3/es active Active
-
2011
- 2011-10-18 MY MYPI2013700611A patent/MY164731A/en unknown
- 2011-10-18 NZ NZ609147A patent/NZ609147A/en not_active IP Right Cessation
- 2011-10-18 ME MEP-2015-43A patent/ME02064B/me unknown
-
2012
- 2012-04-17 EC ECSP12011805 patent/ECSP12011805A/es unknown
- 2012-04-18 IL IL219248A patent/IL219248A/en not_active IP Right Cessation
- 2012-04-18 CL CL2012000981A patent/CL2012000981A1/es unknown
- 2012-04-18 NI NI201200061A patent/NI201200061A/es unknown
- 2012-05-18 ZA ZA2012/03662A patent/ZA201203662B/en unknown
- 2012-05-21 CR CR20120264A patent/CR20120264A/es unknown
-
2013
- 2013-04-16 NI NI201300035A patent/NI201300035A/es unknown
-
2014
- 2014-03-20 US US14/220,650 patent/US9321773B2/en not_active Expired - Fee Related
- 2014-06-30 SM SM201400086T patent/SMT201400086B/xx unknown
- 2014-07-29 CY CY20141100570T patent/CY1116057T1/el unknown
-
2016
- 2016-03-31 US US15/086,120 patent/US9834560B2/en not_active Expired - Fee Related
-
2017
- 2017-11-08 US US15/806,742 patent/US20180118754A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2013508334A5 (OSRAM) | ||
| HRP20140599T1 (hr) | Derivati kiinazolin-4(3h)-ona koji se koriste kao inhibitori pi3 kinaze | |
| ES2706651T3 (es) | Nuevos agentes antiinflamatorios | |
| ES2564422T3 (es) | Compuestos heterocíclicos que contienen N | |
| DK2630149T3 (en) | Quinazolin-4 (3H) -one derivatives, USED AS PI 3-kinase inhibitors | |
| EP2010185B1 (de) | Dihydrothienopyrimidine zur behandlung von entzündlichen erkrankungen | |
| TW200806665A (en) | Organic compounds | |
| JP2012502067A5 (OSRAM) | ||
| JP6427506B2 (ja) | 置換二環式ジヒドロピリミジノン及び好中球エラスターゼ活性の阻害薬としてのそれらの使用 | |
| JP2012524794A5 (OSRAM) | ||
| EP2813509B1 (en) | 3,4,4a,10b-tetrahydro-1h-thiopyrano-[4,3-c]isoquinoline derivatives | |
| JP2012519678A5 (OSRAM) | ||
| JP2005536485A (ja) | 置換イミダゾトリアジン類 | |
| ES2426251T3 (es) | Compuesto de pirimidopiridina usado como un modulador de CSBP/RK/p38 | |
| JP2011519845A5 (OSRAM) | ||
| JP2008535822A (ja) | 新規化合物 | |
| JP4721452B2 (ja) | Ｐｄｅ７阻害作用を有するピリジニルピラゾロピリミジノン誘導体 | |
| EP2721036B1 (en) | Novel 3,4,4a,10b-tetrahydro-1h-thiopyrano[4,3-c]isoquinoline compounds | |
| JPWO2020167990A5 (OSRAM) | ||
| HK1229722B (zh) | 作为蛋白质脱乙酰酶抑制剂和蛋白质脱乙酰酶-蛋白质激酶双重抑制剂的杂环异羟肟酸及其使用方法 | |
| JP2008501617A (ja) | Ｐｄｅ７阻害作用を有するイミダゾトリアジノン誘導体 |