JP2013515710A5 - - Google Patents
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- Publication number
- JP2013515710A5 JP2013515710A5 JP2012545434A JP2012545434A JP2013515710A5 JP 2013515710 A5 JP2013515710 A5 JP 2013515710A5 JP 2012545434 A JP2012545434 A JP 2012545434A JP 2012545434 A JP2012545434 A JP 2012545434A JP 2013515710 A5 JP2013515710 A5 JP 2013515710A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- pyrido
- aminocyclobutyl
- oxazin
- oxazine
- 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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- 238000000034 method Methods 0.000 claims description 2
- -1 CO 2 H Chemical group 0.000 claims 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 25
- 150000001875 compounds Chemical class 0.000 claims 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 15
- 125000000623 heterocyclic group Chemical group 0.000 claims 9
- NWZXAAOTMBDUQY-UHFFFAOYSA-N 3,4-dihydro-1,4-oxazin-2-one Chemical compound O=C1CNC=CO1 NWZXAAOTMBDUQY-UHFFFAOYSA-N 0.000 claims 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- OELZFJUWWFRWLC-UHFFFAOYSA-N oxazine-1 Chemical compound C1=CC(N(CC)CC)=CC2=[O+]C3=CC(N(CC)CC)=CC=C3N=C21 OELZFJUWWFRWLC-UHFFFAOYSA-N 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 229910052740 iodine Inorganic materials 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- ZHELFSWAVCCBJT-UHFFFAOYSA-N 1-(4-(1-(fluoromethyl)-8-phenyl-4h-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-7-yl)phenyl)cyclobutanamine Chemical compound C=1C=C(C=2C(=CC=3N4C(CF)=NN=C4COC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 ZHELFSWAVCCBJT-UHFFFAOYSA-N 0.000 claims 2
- XSPSKUFJPJSWTA-UHFFFAOYSA-N 1-[4-[3-(1-methylimidazol-4-yl)-9-phenyl-5,6-dihydro-[1,2,4]triazolo[3,4-f][1,6]naphthyridin-8-yl]phenyl]cyclobutan-1-amine Chemical compound CN1C=NC(C=2N3CCC4=NC(=C(C=5C=CC=CC=5)C=C4C3=NN=2)C=2C=CC(=CC=2)C2(N)CCC2)=C1 XSPSKUFJPJSWTA-UHFFFAOYSA-N 0.000 claims 2
- PCBLBPATLXZIRA-UHFFFAOYSA-N 6-[4-(1-aminocyclobutyl)phenyl]-1-(2-fluoroethyl)-7-phenylpyrido[2,3-b][1,4]oxazin-2-one Chemical compound C=1C=C(C=2C(=CC=3N(CCF)C(=O)COC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 PCBLBPATLXZIRA-UHFFFAOYSA-N 0.000 claims 2
- TYPLXPVWCKUONI-UHFFFAOYSA-N 6-[4-(1-aminocyclobutyl)phenyl]-1-ethyl-7-phenylpyrido[2,3-b][1,4]oxazin-2-one Chemical compound C=1C=CC=CC=1C=1C=C2N(CC)C(=O)COC2=NC=1C(C=C1)=CC=C1C1(N)CCC1 TYPLXPVWCKUONI-UHFFFAOYSA-N 0.000 claims 2
- OPDVFILITGRNEO-UHFFFAOYSA-N 6-[4-(1-aminocyclobutyl)phenyl]-7-phenyl-1-(2,2,2-trifluoroethyl)pyrido[2,3-b][1,4]oxazin-2-one Chemical compound C=1C=C(C=2C(=CC=3N(CC(F)(F)F)C(=O)COC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 OPDVFILITGRNEO-UHFFFAOYSA-N 0.000 claims 2
- ONPCAEAHRTVIAJ-UHFFFAOYSA-N 6-[4-(1-aminocyclobutyl)phenyl]-7-phenyl-1-prop-2-ynylpyrido[2,3-b][1,4]oxazin-2-one Chemical compound C=1C=C(C=2C(=CC=3N(CC#C)C(=O)COC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 ONPCAEAHRTVIAJ-UHFFFAOYSA-N 0.000 claims 2
- WHSQFIQYHWFGJP-UHFFFAOYSA-N 8-[4-(1-aminocyclobutyl)phenyl]-9-phenyl-5,6-dihydro-2h-[1,2,4]triazolo[3,4-f][1,6]naphthyridin-3-one Chemical compound C=1C=C(C=2C(=CC=3C=4N(C(NN=4)=O)CCC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 WHSQFIQYHWFGJP-UHFFFAOYSA-N 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical group CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- LEWQODPOJTZWOQ-UHFFFAOYSA-N C=1C=CC=CC=1C=1C=C2N3C(CC)=NN=C3COC2=NC=1C(C=C1)=CC=C1C1(N)CCC1 Chemical compound C=1C=CC=CC=1C=1C=C2N3C(CC)=NN=C3COC2=NC=1C(C=C1)=CC=C1C1(N)CCC1 LEWQODPOJTZWOQ-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000002837 carbocyclic group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- UNIBOURSKRHLOY-UHFFFAOYSA-N (4-(8-phenyl-1-(pyridin-3-yl)-4h-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-7-yl)phenyl)cyclobutanamine Chemical compound C=1C=C(C=2C(=CC=3N4C(C=5C=NC=CC=5)=NN=C4COC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 UNIBOURSKRHLOY-UHFFFAOYSA-N 0.000 claims 1
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 1
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- MHDIOHFSRDIGEQ-UHFFFAOYSA-N 1-(4-(1,8-diphenyl-4h-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-7-yl)phenyl)cyclobutanamine Chemical compound C=1C=C(C=2C(=CC=3N4C(C=5C=CC=CC=5)=NN=C4COC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 MHDIOHFSRDIGEQ-UHFFFAOYSA-N 0.000 claims 1
- OHXSUVOLMXOMGJ-UHFFFAOYSA-N 1-(4-(1-(2-methoxyethyl)-8-phenyl-4h-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-7-yl)phenyl)cyclobutanamine Chemical compound C=1C=CC=CC=1C=1C=C2N3C(CCOC)=NN=C3COC2=NC=1C(C=C1)=CC=C1C1(N)CCC1 OHXSUVOLMXOMGJ-UHFFFAOYSA-N 0.000 claims 1
- RXTDIQQYHCTJQN-UHFFFAOYSA-N 1-(4-(1-(difluoromethyl)-8-phenyl-4h-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-7-yl)phenyl)cyclobutanamine Chemical compound C=1C=C(C=2C(=CC=3N4C(C(F)F)=NN=C4COC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 RXTDIQQYHCTJQN-UHFFFAOYSA-N 0.000 claims 1
- YEKDYCNXBILBRN-UHFFFAOYSA-N 1-(4-(1-cyclopropyl-8-phenyl-4h-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-7-yl)phenyl)cyclobutanamine Chemical compound C=1C=C(C=2C(=CC=3N4C(C5CC5)=NN=C4COC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 YEKDYCNXBILBRN-UHFFFAOYSA-N 0.000 claims 1
- GZXCMAUVXKMEAY-UHFFFAOYSA-N 1-(4-(1-isobutyl-8-phenyl-4h-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-7-yl)phenyl)cyclobutanamine Chemical compound C=1C=CC=CC=1C=1C=C2N3C(CC(C)C)=NN=C3COC2=NC=1C(C=C1)=CC=C1C1(N)CCC1 GZXCMAUVXKMEAY-UHFFFAOYSA-N 0.000 claims 1
- WQWMHNATXQHWFH-UHFFFAOYSA-N 1-(4-(1-isopropyl-8-phenyl-4h-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-7-yl)phenyl)cyclobutanamine Chemical compound C=1C=CC=CC=1C=1C=C2N3C(C(C)C)=NN=C3COC2=NC=1C(C=C1)=CC=C1C1(N)CCC1 WQWMHNATXQHWFH-UHFFFAOYSA-N 0.000 claims 1
- NWNROKSRSGRKAQ-UHFFFAOYSA-N 1-(4-(8-phenyl-1-(2,2,2-trifluoroethyl)-4h-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-7-yl)phenyl)cyclobutanamine Chemical compound C=1C=C(C=2C(=CC=3N4C(CC(F)(F)F)=NN=C4COC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 NWNROKSRSGRKAQ-UHFFFAOYSA-N 0.000 claims 1
- HMPBHPUCYHYBQF-UHFFFAOYSA-N 1-(4-(8-phenyl-1-(pyridin-2-yl)-4h-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-7-yl)phenyl)cyclobutanamine Chemical compound C=1C=C(C=2C(=CC=3N4C(C=5N=CC=CC=5)=NN=C4COC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 HMPBHPUCYHYBQF-UHFFFAOYSA-N 0.000 claims 1
- XYFOHFJFPXUJBI-UHFFFAOYSA-N 1-(4-(8-phenyl-1-(pyridin-4-yl)-4h-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-7-yl)phenyl)cyclobutanamine Chemical compound C=1C=C(C=2C(=CC=3N4C(C=5C=CN=CC=5)=NN=C4COC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 XYFOHFJFPXUJBI-UHFFFAOYSA-N 0.000 claims 1
- LVERCWIILYCPEO-UHFFFAOYSA-N 1-(4-(8-phenyl-1-(trifluoromethyl)-4h-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-7-yl)phenyl)cyclobutanamine Chemical compound C=1C=C(C=2C(=CC=3N4C(=NN=C4COC=3N=2)C(F)(F)F)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 LVERCWIILYCPEO-UHFFFAOYSA-N 0.000 claims 1
- UXXPENKPFIICLW-UHFFFAOYSA-N 1-(4-(8-phenyl-1-propyl-4h-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-7-yl)phenyl)cyclobutanamine Chemical compound C=1C=CC=CC=1C=1C=C2N3C(CCC)=NN=C3COC2=NC=1C(C=C1)=CC=C1C1(N)CCC1 UXXPENKPFIICLW-UHFFFAOYSA-N 0.000 claims 1
- VAYVHKTUAXILPZ-UHFFFAOYSA-N 1-[4-(1-methyl-7-phenyl-2,3-dihydropyrido[2,3-b][1,4]oxazin-6-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=CC=CC=1C=1C=C2N(C)CCOC2=NC=1C(C=C1)=CC=C1C1(N)CCC1 VAYVHKTUAXILPZ-UHFFFAOYSA-N 0.000 claims 1
- YQFZPYCKAXAXNW-UHFFFAOYSA-N 1-[4-(1-methylsulfonyl-7-phenyl-2,3-dihydropyrido[2,3-b][1,4]oxazin-6-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=CC=CC=1C=1C=C2N(S(=O)(=O)C)CCOC2=NC=1C(C=C1)=CC=C1C1(N)CCC1 YQFZPYCKAXAXNW-UHFFFAOYSA-N 0.000 claims 1
- VBIFMSRKSIWTPA-UHFFFAOYSA-N 1-[4-(12-phenyl-8-oxa-2,4,5,10-tetrazatricyclo[7.4.0.02,6]trideca-1(9),3,5,10,12-pentaen-11-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C=2C(=CC=3N4C=NN=C4COC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 VBIFMSRKSIWTPA-UHFFFAOYSA-N 0.000 claims 1
- GYEMFQKVWHAVNP-UHFFFAOYSA-N 1-[4-(2,2-dioxo-7-phenyl-1-pyridin-3-ylpyrido[3,2-e][1,3,4]oxathiazin-6-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C=2C(=CC=3N(C=4C=NC=CC=4)S(=O)(=O)COC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 GYEMFQKVWHAVNP-UHFFFAOYSA-N 0.000 claims 1
- BUUJVQQLJXZEPW-UHFFFAOYSA-N 1-[4-(2-methoxyimino-1-methyl-7-phenylpyrido[2,3-b][1,4]oxazin-6-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=CC=CC=1C=1C=C2N(C)C(=NOC)COC2=NC=1C(C=C1)=CC=C1C1(N)CCC1 BUUJVQQLJXZEPW-UHFFFAOYSA-N 0.000 claims 1
- MWAQMPLOXKXEKU-UHFFFAOYSA-N 1-[4-(3-bromo-12-phenyl-8-oxa-2,4,5,10-tetrazatricyclo[7.4.0.02,6]trideca-1(9),3,5,10,12-pentaen-11-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C=2C(=CC=3N4C(Br)=NN=C4COC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 MWAQMPLOXKXEKU-UHFFFAOYSA-N 0.000 claims 1
- YKNLEDGFGQBMPO-UHFFFAOYSA-N 1-[4-(3-methylsulfanyl-8-phenyl-4,5-dihydro-1h-pyrazolo[3,4-f]quinolin-7-yl)phenyl]cyclobutan-1-amine Chemical compound CSC=1NN=C(C2=CC=3C=4C=CC=CC=4)C=1CCC2=NC=3C(C=C1)=CC=C1C1(N)CCC1 YKNLEDGFGQBMPO-UHFFFAOYSA-N 0.000 claims 1
- JVVCSSJSQMDTGQ-UHFFFAOYSA-N 1-[4-(3-methylsulfonyl-8-phenyl-4,5-dihydro-2h-pyrazolo[3,4-f]quinolin-7-yl)phenyl]cyclobutan-1-amine Chemical compound CS(=O)(=O)C=1NN=C(C2=CC=3C=4C=CC=CC=4)C=1CCC2=NC=3C(C=C1)=CC=C1C1(N)CCC1 JVVCSSJSQMDTGQ-UHFFFAOYSA-N 0.000 claims 1
- LPEYFAZQXCYZMG-UHFFFAOYSA-N 1-[4-(3-morpholin-4-yl-8-phenyl-4,5-dihydro-1h-pyrazolo[3,4-f]quinolin-7-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C=2C(=CC=3C=4C(=C(NN=4)N4CCOCC4)CCC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 LPEYFAZQXCYZMG-UHFFFAOYSA-N 0.000 claims 1
- LZXPRSFNFBZMEH-UHFFFAOYSA-N 1-[4-(7-phenyl-2,3-dihydro-1h-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C=2C(=CC=3NCCOC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 LZXPRSFNFBZMEH-UHFFFAOYSA-N 0.000 claims 1
- LYXMLLYMPIPKHT-UHFFFAOYSA-N 1-[4-(9-phenyl-1,4,5,6-tetrahydropyrazolo[3,4]cyclohepta[1,3-d]pyridin-8-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C=2C(=CC=3C4=NNC=C4CCCC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 LYXMLLYMPIPKHT-UHFFFAOYSA-N 0.000 claims 1
- SBAMQONAOGRMKA-UHFFFAOYSA-N 1-[6-[4-(1-aminocyclobutyl)phenyl]-7-phenyl-2,3-dihydropyrido[2,3-b][1,4]oxazin-1-yl]ethanone Chemical compound C=1C=CC=CC=1C=1C=C2N(C(=O)C)CCOC2=NC=1C(C=C1)=CC=C1C1(N)CCC1 SBAMQONAOGRMKA-UHFFFAOYSA-N 0.000 claims 1
- UCQAPQHUBARVNY-UHFFFAOYSA-N 11-[4-(1-aminocyclobutyl)phenyl]-12-phenyl-8-oxa-2,4,5,10-tetrazatricyclo[7.4.0.02,6]trideca-1(9),3,5,10,12-pentaen-3-amine Chemical compound C=1C=CC=CC=1C=1C=C2N3C(N)=NN=C3COC2=NC=1C(C=C1)=CC=C1C1(N)CCC1 UCQAPQHUBARVNY-UHFFFAOYSA-N 0.000 claims 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- OPPWGZOXGYILPO-UHFFFAOYSA-N 2-(7-(4-(1-aminocyclobutyl)phenyl)-1-oxo-8-phenyl-1h-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-2(4h)-yl)acetonitrile Chemical compound C=1C=C(C=2C(=CC=3N4C(=O)N(CC#N)N=C4COC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 OPPWGZOXGYILPO-UHFFFAOYSA-N 0.000 claims 1
- AJCQGNODDLIOPK-QGZVFWFLSA-N 2-[(3r)-6-[4-(1-aminocyclobutyl)phenyl]-3-methyl-2-oxo-7-phenylpyrido[2,3-b][1,4]oxazin-1-yl]acetonitrile Chemical compound O([C@@H](C(N(CC#N)C1=CC=2C=3C=CC=CC=3)=O)C)C1=NC=2C(C=C1)=CC=C1C1(N)CCC1 AJCQGNODDLIOPK-QGZVFWFLSA-N 0.000 claims 1
- JWQODELKRKCFSL-UHFFFAOYSA-N 2-[2-[4-(1-aminocyclobutyl)phenyl]-5-oxo-3-phenyl-7,8-dihydro-1,6-naphthyridin-6-yl]acetonitrile Chemical compound C=1C=C(C=2C(=CC=3C(=O)N(CC#N)CCC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 JWQODELKRKCFSL-UHFFFAOYSA-N 0.000 claims 1
- LXSQJDOLOHDLAG-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-3-phenyl-6,7,8,9-tetrahydrocyclohepta[b]pyridin-5-one Chemical compound C=1C=C(C=2C(=CC=3C(=O)CCCCC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 LXSQJDOLOHDLAG-UHFFFAOYSA-N 0.000 claims 1
- RXUGULUVCUDDPG-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-3-phenyl-7,8-dihydro-6h-1,6-naphthyridin-5-one Chemical compound C=1C=C(C=2C(=CC=3C(=O)NCCC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 RXUGULUVCUDDPG-UHFFFAOYSA-N 0.000 claims 1
- ZOMDGORASNQGTF-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-3-phenyl-8h-pyrano[3,4-b]pyridin-5-one Chemical compound C=1C=C(C=2C(=CC=3C(=O)COCC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 ZOMDGORASNQGTF-UHFFFAOYSA-N 0.000 claims 1
- PRELDKIOBPTFCG-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-6-methyl-3-phenyl-7,8-dihydro-1,6-naphthyridin-5-one 2-[4-(1-aminocyclobutyl)phenyl]-3-phenyl-7,8-dihydro-6H-1,6-naphthyridin-5-one Chemical compound NC1(CCC1)c1ccc(cc1)-c1nc2CCNC(=O)c2cc1-c1ccccc1.CN1CCc2nc(-c3ccc(cc3)C3(N)CCC3)c(cc2C1=O)-c1ccccc1 PRELDKIOBPTFCG-UHFFFAOYSA-N 0.000 claims 1
- GTNIQZFAEZKKKH-UHFFFAOYSA-N 2-[6-[4-(1-aminocyclobutyl)phenyl]-3-(2-hydroxyethyl)-2-oxo-7-phenylpyrido[2,3-b][1,4]oxazin-1-yl]acetonitrile Chemical compound C=1C=C(C=2C(=CC=3N(CC#N)C(=O)C(CCO)OC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 GTNIQZFAEZKKKH-UHFFFAOYSA-N 0.000 claims 1
- ORJUJQFUGVDYRS-UHFFFAOYSA-N 2-[6-[4-(1-aminocyclobutyl)phenyl]-3-(methoxymethyl)-2-oxo-7-phenylpyrido[2,3-b][1,4]oxazin-1-yl]acetonitrile Chemical compound C=1C=CC=CC=1C=1C=C2N(CC#N)C(=O)C(COC)OC2=NC=1C(C=C1)=CC=C1C1(N)CCC1 ORJUJQFUGVDYRS-UHFFFAOYSA-N 0.000 claims 1
- AJCQGNODDLIOPK-UHFFFAOYSA-N 2-[6-[4-(1-aminocyclobutyl)phenyl]-3-methyl-2-oxo-7-phenylpyrido[2,3-b][1,4]oxazin-1-yl]acetonitrile Chemical compound C=1C=CC=CC=1C=1C=C2N(CC#N)C(=O)C(C)OC2=NC=1C(C=C1)=CC=C1C1(N)CCC1 AJCQGNODDLIOPK-UHFFFAOYSA-N 0.000 claims 1
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- RJMOOKQFEZAOSO-UHFFFAOYSA-N CN1N=CC2=C1C=1C=C(C(=NC1CC2)C2=CC=C(C=C2)C2(CCC2)N)C2=CC=CC=C2.CN2N=C1C=3C=C(C(=NC3CCC1=C2)C2=CC=C(C=C2)C2(CCC2)N)C2=CC=CC=C2 Chemical compound CN1N=CC2=C1C=1C=C(C(=NC1CC2)C2=CC=C(C=C2)C2(CCC2)N)C2=CC=CC=C2.CN2N=C1C=3C=C(C(=NC3CCC1=C2)C2=CC=C(C=C2)C2(CCC2)N)C2=CC=CC=C2 RJMOOKQFEZAOSO-UHFFFAOYSA-N 0.000 claims 1
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- BYGDVJVULHWEMY-UHFFFAOYSA-N NC1(CCC1)C1=CC=C(C=C1)C1=NC=2CCCC(C2C=C1C1=CC=CC=C1)=NO.NC1(CCC1)C1=CC=C(C=C1)C1=NC=2CCCC(C2C=C1C1=CC=CC=C1)=O Chemical compound NC1(CCC1)C1=CC=C(C=C1)C1=NC=2CCCC(C2C=C1C1=CC=CC=C1)=NO.NC1(CCC1)C1=CC=C(C=C1)C1=NC=2CCCC(C2C=C1C1=CC=CC=C1)=O BYGDVJVULHWEMY-UHFFFAOYSA-N 0.000 claims 1
- DHCDPTKCANZVJQ-UHFFFAOYSA-N NC1(CCC1)C1=CC=C(C=C1)C=1C(=CC2=C(OCC(N2C)=O)N1)C1=CC=CC=C1.NC1(CCC1)C1=CC=C(C=C1)C=1C(=CC2=C(OCC(N2)=O)N1)C1=CC=CC=C1 Chemical compound NC1(CCC1)C1=CC=C(C=C1)C=1C(=CC2=C(OCC(N2C)=O)N1)C1=CC=CC=C1.NC1(CCC1)C1=CC=C(C=C1)C=1C(=CC2=C(OCC(N2)=O)N1)C1=CC=CC=C1 DHCDPTKCANZVJQ-UHFFFAOYSA-N 0.000 claims 1
- RFFFKMOABOFIDF-UHFFFAOYSA-N Pentanenitrile Chemical compound CCCCC#N RFFFKMOABOFIDF-UHFFFAOYSA-N 0.000 claims 1
- NURSLEUFEUWLGL-UHFFFAOYSA-N [4-(3-ethyl-12-phenyl-8-oxa-2,4,5,10-tetrazatricyclo[7.4.0.02,6]trideca-1(9),3,5,10,12-pentaen-11-yl)phenyl]methanamine Chemical compound C=1C=CC=CC=1C=1C=C2N3C(CC)=NN=C3COC2=NC=1C1=CC=C(CN)C=C1 NURSLEUFEUWLGL-UHFFFAOYSA-N 0.000 claims 1
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 1
- 125000002527 bicyclic carbocyclic group Chemical group 0.000 claims 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 150000002829 nitrogen Chemical class 0.000 claims 1
- 150000002923 oximes Chemical class 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
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- 238000001959 radiotherapy Methods 0.000 claims 1
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
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- 239000013557 residual solvent Substances 0.000 description 1
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- 239000002904 solvent Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- YVMMQBXXZDTISI-UHFFFAOYSA-N tert-butyl n-[1-[4-(2-amino-9-phenyl-5,6-dihydropyrido[2,3-h]quinazolin-8-yl)phenyl]cyclobutyl]carbamate Chemical compound C=1C=C(C=2C(=CC=3C4=NC(N)=NC=C4CCC=3N=2)C=2C=CC=CC=2)C=CC=1C1(NC(=O)OC(C)(C)C)CCC1 YVMMQBXXZDTISI-UHFFFAOYSA-N 0.000 description 1
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| GB0922589.7 | 2009-12-23 | ||
| PCT/GB2010/002329 WO2011077098A1 (en) | 2009-12-23 | 2010-12-23 | Inhibitors of akt activity |
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| JP2013515710A JP2013515710A (ja) | 2013-05-09 |
| JP2013515710A5 true JP2013515710A5 (https=) | 2013-10-31 |
| JP5923043B2 JP5923043B2 (ja) | 2016-05-24 |
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| EP (1) | EP2516435B8 (https=) |
| JP (1) | JP5923043B2 (https=) |
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| GB (1) | GB0922589D0 (https=) |
| IL (1) | IL220153A (https=) |
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| NZ (1) | NZ600453A (https=) |
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| SI (1) | SI2516435T1 (https=) |
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| GB201205164D0 (en) * | 2012-03-23 | 2012-05-09 | Almac Discovery Ltd | Pharmaceutical compounds |
| JP6787899B2 (ja) * | 2014-12-23 | 2020-11-18 | ベルゲンビオ アーエスアー | 医薬的活性化合物 |
| US10323044B2 (en) * | 2015-02-27 | 2019-06-18 | Taiho Pharmaceutical Co., Ltd. | Crystal of imidazo-oxazine, pharmaceutical composition containing said crystal, and method for producing said crystal |
| GB201603779D0 (en) | 2016-03-04 | 2016-04-20 | Mission Therapeutics Ltd | Novel compounds |
| MA45865A (fr) * | 2016-08-07 | 2021-04-14 | Wistar Inst | Procédés de détection et de traitement d'une tumeur exprimant pt346 pdk1 |
| UA125730C2 (uk) * | 2017-06-22 | 2022-05-25 | Курадев Фарма Лімітед | Низькомолекулярні модулятори sting людини |
| MX2020002611A (es) | 2017-09-07 | 2020-07-13 | Univ Res Inst Inc Augusta | Activador especifico de akt3 y usos del mismo. |
| GB2600384A (en) * | 2020-09-30 | 2022-05-04 | Vaderis Therapeutics Ag | Allosteric AKT inhibitors for use in the treatment of hereditary hemorrhagic telangiectasia |
| WO2025250545A1 (en) * | 2024-05-28 | 2025-12-04 | Alterome Therapeutics, Inc. | Akt1 modulators |
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| PL181893B1 (pl) * | 1994-11-14 | 2001-10-31 | Warner Lambert Co | Zwiazki bedace pochodnymi pirymidyny i naftyrydyny oraz preparat farmaceutyczny zawierajacy je PL PL PL |
| TWI301760B (en) * | 2004-02-27 | 2008-10-11 | Merz Pharma Gmbh & Co Kgaa | Tetrahydroquinolinones and their use as antagonists of metabotropic glutamate receptors |
| US7910561B2 (en) * | 2004-12-15 | 2011-03-22 | Merck Sharp & Dohme Corp. | Inhibitors of Akt activity |
| EP1898903B8 (en) * | 2005-06-10 | 2013-05-15 | Merck Sharp & Dohme Corp. | Inhibitors of akt activity |
| WO2008011032A1 (en) * | 2006-07-17 | 2008-01-24 | Amgen Inc. | Quinazoline and pyridopyrimidine derivatives as p38 kinase inhibitors |
| JP2010512312A (ja) | 2006-12-06 | 2010-04-22 | メルク エンド カムパニー インコーポレーテッド | Ａｋｔ活性の阻害剤 |
| AR064010A1 (es) | 2006-12-06 | 2009-03-04 | Merck & Co Inc | Inhibidores de la actividad de la akt |
| US7999107B2 (en) * | 2007-01-31 | 2011-08-16 | Merck Sharp & Dohme Corp. | Substituted pyrano[2,3-B]pyridine derivatives as cannabinoid-1 receptor modulators |
| JP2011522048A (ja) * | 2008-06-03 | 2011-07-28 | メルク・シャープ・エンド・ドーム・コーポレイション | Ａｋｔ活性の阻害剤 |
| US8536193B2 (en) | 2008-06-03 | 2013-09-17 | Merck Sharp & Dohme Corp. | Inhibitors of AKT activity |
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2010
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- 2010-12-23 US US13/517,219 patent/US9221838B2/en active Active
- 2010-12-23 CA CA2783340A patent/CA2783340C/en not_active Expired - Fee Related
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- 2010-12-23 PT PT108009804T patent/PT2516435E/pt unknown
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- 2010-12-23 SI SI201030774T patent/SI2516435T1/sl unknown
- 2010-12-23 WO PCT/GB2010/002329 patent/WO2011077098A1/en not_active Ceased
- 2010-12-23 KR KR1020127019033A patent/KR20140015157A/ko not_active Ceased
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2012
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2014
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