JP2013515710A5 - - Google Patents
Download PDFInfo
- 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
Links
- 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
- XVSPTJWQXXJYDR-UHFFFAOYSA-N 2-[6-[4-(1-aminocyclobutyl)phenyl]-7-phenyl-2,3-dihydropyrido[2,3-b][1,4]oxazin-1-yl]acetamide Chemical compound C=1C=CC=CC=1C=1C=C2N(CC(=O)N)CCOC2=NC=1C(C=C1)=CC=C1C1(N)CCC1 XVSPTJWQXXJYDR-UHFFFAOYSA-N 0.000 claims 1
- GJRMWYPJAUGGEV-UHFFFAOYSA-N 2-[6-[4-(1-aminocyclobutyl)phenyl]-7-phenyl-2,3-dihydropyrido[2,3-b][1,4]oxazin-1-yl]acetonitrile Chemical compound C=1C=C(C=2C(=CC=3N(CC#N)CCOC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 GJRMWYPJAUGGEV-UHFFFAOYSA-N 0.000 claims 1
- ZPMCFJHGCCVDSO-UHFFFAOYSA-N 2-[[7-[4-(1-aminocyclobutyl)phenyl]-8-phenyl-4,5-dihydro-1h-pyrazolo[3,4-f]quinolin-3-yl]amino]ethanol Chemical compound C=1C=C(C=2C(=CC=3C4=NNC(NCCO)=C4CCC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 ZPMCFJHGCCVDSO-UHFFFAOYSA-N 0.000 claims 1
- CBSZMUKNHGGWTB-UHFFFAOYSA-N 6-[4-(1-aminocyclobutyl)phenyl]-1,3-bis(2-fluoroethyl)-7-phenyl-4h-pyrido[3,2-d]pyrimidin-2-one Chemical compound C=1C=C(C=2C(=CC=3N(CCF)C(=O)N(CCF)CC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 CBSZMUKNHGGWTB-UHFFFAOYSA-N 0.000 claims 1
- NWHKZRUEBBMTIK-UHFFFAOYSA-N 6-[4-(1-aminocyclobutyl)phenyl]-1,3-dimethyl-7-phenyl-4h-pyrido[3,2-d]pyrimidin-2-one Chemical compound C=1C=CC=CC=1C=1C=C2N(C)C(=O)N(C)CC2=NC=1C(C=C1)=CC=C1C1(N)CCC1 NWHKZRUEBBMTIK-UHFFFAOYSA-N 0.000 claims 1
- NQFLAKUMWCFPJG-UHFFFAOYSA-N 6-[4-(1-aminocyclobutyl)phenyl]-1,3-dimethyl-7-phenylpyrido[2,3-b][1,4]oxazin-2-one Chemical compound C=1C=CC=CC=1C=1C=C2N(C)C(=O)C(C)OC2=NC=1C(C=C1)=CC=C1C1(N)CCC1 NQFLAKUMWCFPJG-UHFFFAOYSA-N 0.000 claims 1
- DZRLIUVGYKDKQL-UHFFFAOYSA-N 6-[4-(1-aminocyclobutyl)phenyl]-1-(1-methylpyrazol-4-yl)-7-phenylpyrido[2,3-b][1,4]oxazin-2-one Chemical compound C1=NN(C)C=C1N1C2=CC(C=3C=CC=CC=3)=C(C=3C=CC(=CC=3)C3(N)CCC3)N=C2OCC1=O DZRLIUVGYKDKQL-UHFFFAOYSA-N 0.000 claims 1
- IEOVEQJKRDSTQE-UHFFFAOYSA-N 6-[4-(1-aminocyclobutyl)phenyl]-1-(1h-imidazol-2-ylmethyl)-7-phenylpyrido[2,3-b][1,4]oxazin-2-one Chemical compound C=1C=C(C=2C(=CC=3N(CC=4NC=CN=4)C(=O)COC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 IEOVEQJKRDSTQE-UHFFFAOYSA-N 0.000 claims 1
- GFMVVXSPCBIUSV-UHFFFAOYSA-N 6-[4-(1-aminocyclobutyl)phenyl]-1-(1h-imidazol-5-ylmethyl)-7-phenylpyrido[2,3-b][1,4]oxazin-2-one Chemical compound C=1C=C(C=2C(=CC=3N(CC=4NC=NC=4)C(=O)COC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 GFMVVXSPCBIUSV-UHFFFAOYSA-N 0.000 claims 1
- GLVBVEAYUYEUFB-UHFFFAOYSA-N 6-[4-(1-aminocyclobutyl)phenyl]-1-(2,2-difluoroethyl)-7-phenylpyrido[2,3-b][1,4]oxazin-2-one Chemical compound C=1C=C(C=2C(=CC=3N(CC(F)F)C(=O)COC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 GLVBVEAYUYEUFB-UHFFFAOYSA-N 0.000 claims 1
- GOFODIWMDFMZID-UHFFFAOYSA-N 6-[4-(1-aminocyclobutyl)phenyl]-1-(2-methoxyethyl)-7-phenylpyrido[2,3-b][1,4]oxazin-2-one Chemical compound C=1C=CC=CC=1C=1C=C2N(CCOC)C(=O)COC2=NC=1C(C=C1)=CC=C1C1(N)CCC1 GOFODIWMDFMZID-UHFFFAOYSA-N 0.000 claims 1
- YPGQFEJOEFHTSD-UHFFFAOYSA-N 6-[4-(1-aminocyclobutyl)phenyl]-1-(2-methylpropyl)-7-phenylpyrido[2,3-b][1,4]oxazin-2-one Chemical compound C=1C=CC=CC=1C=1C=C2N(CC(C)C)C(=O)COC2=NC=1C(C=C1)=CC=C1C1(N)CCC1 YPGQFEJOEFHTSD-UHFFFAOYSA-N 0.000 claims 1
- DDFASEHWDBONOY-UHFFFAOYSA-N 6-[4-(1-aminocyclobutyl)phenyl]-1-(cyclopropylmethyl)-7-phenylpyrido[2,3-b][1,4]oxazin-2-one Chemical compound C=1C=C(C=2C(=CC=3N(CC4CC4)C(=O)COC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 DDFASEHWDBONOY-UHFFFAOYSA-N 0.000 claims 1
- GTCJZNRUXLASBU-UHFFFAOYSA-N 6-[4-(1-aminocyclobutyl)phenyl]-1-(methylsulfonylmethyl)-7-phenylpyrido[2,3-b][1,4]oxazin-2-one Chemical compound C=1C=CC=CC=1C=1C=C2N(CS(=O)(=O)C)C(=O)COC2=NC=1C(C=C1)=CC=C1C1(N)CCC1 GTCJZNRUXLASBU-UHFFFAOYSA-N 0.000 claims 1
- LHNRRCISPVAAHG-UHFFFAOYSA-N 6-[4-(1-aminocyclobutyl)phenyl]-1-[3-hydroxy-2-(hydroxymethyl)-2-methylpropyl]-7-phenylpyrido[2,3-b][1,4]oxazin-2-one Chemical compound C=1C=CC=CC=1C=1C=C2N(CC(CO)(CO)C)C(=O)COC2=NC=1C(C=C1)=CC=C1C1(N)CCC1 LHNRRCISPVAAHG-UHFFFAOYSA-N 0.000 claims 1
- LOFOGDPXGKXIAP-UHFFFAOYSA-N 6-[4-(1-aminocyclobutyl)phenyl]-1-cyclobutyl-7-phenylpyrido[2,3-b][1,4]oxazin-2-one Chemical compound C=1C=C(C=2C(=CC=3N(C4CCC4)C(=O)COC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 LOFOGDPXGKXIAP-UHFFFAOYSA-N 0.000 claims 1
- FGCNQTFIKCHKBG-UHFFFAOYSA-N 6-[4-(1-aminocyclobutyl)phenyl]-1-cyclopentyl-7-phenylpyrido[2,3-b][1,4]oxazin-2-one Chemical compound C=1C=C(C=2C(=CC=3N(C4CCCC4)C(=O)COC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 FGCNQTFIKCHKBG-UHFFFAOYSA-N 0.000 claims 1
- OUIAHCNJFSBJQQ-UHFFFAOYSA-N 6-[4-(1-aminocyclobutyl)phenyl]-1-methyl-7-phenylpyrido[2,3-b][1,4]oxazin-2-one Chemical compound C=1C=CC=CC=1C=1C=C2N(C)C(=O)COC2=NC=1C(C=C1)=CC=C1C1(N)CCC1 OUIAHCNJFSBJQQ-UHFFFAOYSA-N 0.000 claims 1
- NWTWFWLYUOZBPS-UHFFFAOYSA-N 6-[4-(1-aminocyclobutyl)phenyl]-1-methyl-7-pyridin-3-ylpyrido[2,3-b][1,4]oxazin-2-one Chemical compound C=1C=CN=CC=1C=1C=C2N(C)C(=O)COC2=NC=1C(C=C1)=CC=C1C1(N)CCC1 NWTWFWLYUOZBPS-UHFFFAOYSA-N 0.000 claims 1
- DULOJLPCJMCVLG-UHFFFAOYSA-N 6-[4-(1-aminocyclobutyl)phenyl]-1-methyl-7-thiophen-2-ylpyrido[2,3-b][1,4]oxazin-2-one Chemical compound C=1C=CSC=1C=1C=C2N(C)C(=O)COC2=NC=1C(C=C1)=CC=C1C1(N)CCC1 DULOJLPCJMCVLG-UHFFFAOYSA-N 0.000 claims 1
- WFNUGBUHLGLXNY-UHFFFAOYSA-N 6-[4-(1-aminocyclobutyl)phenyl]-1-methyl-7-thiophen-3-ylpyrido[2,3-b][1,4]oxazin-2-one Chemical compound C1=CSC=C1C=1C=C2N(C)C(=O)COC2=NC=1C(C=C1)=CC=C1C1(N)CCC1 WFNUGBUHLGLXNY-UHFFFAOYSA-N 0.000 claims 1
- DAZFUYIYXOQPKK-UHFFFAOYSA-N 6-[4-(1-aminocyclobutyl)phenyl]-3-(2-hydroxyethyl)-7-phenyl-1h-pyrido[2,3-b][1,4]oxazin-2-one Chemical compound C=1C=C(C=2C(=CC=3NC(=O)C(CCO)OC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 DAZFUYIYXOQPKK-UHFFFAOYSA-N 0.000 claims 1
- PURQUVUJKKWRPB-UHFFFAOYSA-N 6-[4-(1-aminocyclobutyl)phenyl]-3-(methoxymethyl)-1-methyl-7-phenylpyrido[2,3-b][1,4]oxazin-2-one Chemical compound C=1C=CC=CC=1C=1C=C2N(C)C(=O)C(COC)OC2=NC=1C(C=C1)=CC=C1C1(N)CCC1 PURQUVUJKKWRPB-UHFFFAOYSA-N 0.000 claims 1
- DMYJOLURQRNMJA-UHFFFAOYSA-N 6-[4-(1-aminocyclobutyl)phenyl]-3-methyl-7-phenyl-1h-pyrido[2,3-b][1,4]oxazin-2-one Chemical compound C=1C=CC=CC=1C=1C=C2NC(=O)C(C)OC2=NC=1C(C=C1)=CC=C1C1(N)CCC1 DMYJOLURQRNMJA-UHFFFAOYSA-N 0.000 claims 1
- BRMDACQOFUBGBK-UHFFFAOYSA-N 6-[4-(1-aminocyclobutyl)phenyl]-7-(4-fluorophenyl)-1-methylpyrido[2,3-b][1,4]oxazin-2-one Chemical compound C=1C=C(F)C=CC=1C=1C=C2N(C)C(=O)COC2=NC=1C(C=C1)=CC=C1C1(N)CCC1 BRMDACQOFUBGBK-UHFFFAOYSA-N 0.000 claims 1
- CJCNPBJXBPTLDE-UHFFFAOYSA-N 6-[4-(1-aminocyclobutyl)phenyl]-7-(cyclopropylmethyl)-1-methylpyrido[2,3-b][1,4]oxazin-2-one Chemical compound C1=C2N(C)C(=O)COC2=NC(C=2C=CC(=CC=2)C2(N)CCC2)=C1CC1CC1 CJCNPBJXBPTLDE-UHFFFAOYSA-N 0.000 claims 1
- BTWHCONTGPUGQC-UHFFFAOYSA-N 6-[4-(1-aminocyclobutyl)phenyl]-7-phenyl-1-(1,3-thiazol-4-ylmethyl)pyrido[2,3-b][1,4]oxazin-2-one Chemical compound C=1C=C(C=2C(=CC=3N(CC=4N=CSC=4)C(=O)COC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 BTWHCONTGPUGQC-UHFFFAOYSA-N 0.000 claims 1
- CIBUCWJPEDVMIV-UHFFFAOYSA-N 6-[4-(1-aminocyclobutyl)phenyl]-7-phenyl-1-(pyridin-2-ylmethyl)pyrido[2,3-b][1,4]oxazin-2-one Chemical compound C=1C=C(C=2C(=CC=3N(CC=4N=CC=CC=4)C(=O)COC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 CIBUCWJPEDVMIV-UHFFFAOYSA-N 0.000 claims 1
- VGBRIJALNZRVBN-UHFFFAOYSA-N 6-[4-(1-aminocyclobutyl)phenyl]-7-phenyl-1-(pyridin-3-ylmethyl)pyrido[2,3-b][1,4]oxazin-2-one Chemical compound C=1C=C(C=2C(=CC=3N(CC=4C=NC=CC=4)C(=O)COC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 VGBRIJALNZRVBN-UHFFFAOYSA-N 0.000 claims 1
- MLUIDWFMONXGGW-UHFFFAOYSA-N 6-[4-(1-aminocyclobutyl)phenyl]-7-phenyl-1-(pyridin-4-ylmethyl)pyrido[2,3-b][1,4]oxazin-2-one Chemical compound C=1C=C(C=2C(=CC=3N(CC=4C=CN=CC=4)C(=O)COC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 MLUIDWFMONXGGW-UHFFFAOYSA-N 0.000 claims 1
- MLJZMOJWGCDMQQ-UHFFFAOYSA-N 6-[4-(1-aminocyclobutyl)phenyl]-7-phenyl-1-propan-2-ylpyrido[2,3-b][1,4]oxazin-2-one Chemical compound C=1C=CC=CC=1C=1C=C2N(C(C)C)C(=O)COC2=NC=1C(C=C1)=CC=C1C1(N)CCC1 MLJZMOJWGCDMQQ-UHFFFAOYSA-N 0.000 claims 1
- GYIHHVUIPMCEQS-UHFFFAOYSA-N 6-[4-(1-aminocyclobutyl)phenyl]-7-phenyl-1-propylpyrido[2,3-b][1,4]oxazin-2-one Chemical compound C=1C=CC=CC=1C=1C=C2N(CCC)C(=O)COC2=NC=1C(C=C1)=CC=C1C1(N)CCC1 GYIHHVUIPMCEQS-UHFFFAOYSA-N 0.000 claims 1
- SLXZMJSSMZWMKD-UHFFFAOYSA-N 6-[4-(1-aminocyclobutyl)phenyl]-7-phenyl-1-pyridin-3-ylpyrido[2,3-b][1,4]oxazin-2-one Chemical compound C=1C=C(C=2C(=CC=3N(C=4C=NC=CC=4)C(=O)COC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 SLXZMJSSMZWMKD-UHFFFAOYSA-N 0.000 claims 1
- CHAMOVIZBSWUAJ-UHFFFAOYSA-N 6-[4-(1-aminocyclobutyl)phenyl]-7-phenyl-3,4-dihydro-1h-pyrido[3,2-d]pyrimidin-2-one Chemical compound C=1C=C(C=2C(=CC=3NC(=O)NCC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 CHAMOVIZBSWUAJ-UHFFFAOYSA-N 0.000 claims 1
- QLMATKCYCZWIJV-UHFFFAOYSA-N 6-[4-(1-aminocyclobutyl)phenyl]-n-ethyl-7-phenyl-2,3-dihydropyrido[2,3-b][1,4]oxazine-1-carboxamide Chemical compound C=1C=CC=CC=1C=1C=C2N(C(=O)NCC)CCOC2=NC=1C(C=C1)=CC=C1C1(N)CCC1 QLMATKCYCZWIJV-UHFFFAOYSA-N 0.000 claims 1
- IEWFASGSTOALEY-UHFFFAOYSA-N 6-[4-(aminomethyl)phenyl]-1-methyl-7-phenylpyrido[2,3-b][1,4]oxazin-2-one Chemical compound C=1C=CC=CC=1C=1C=C2N(C)C(=O)COC2=NC=1C1=CC=C(CN)C=C1 IEWFASGSTOALEY-UHFFFAOYSA-N 0.000 claims 1
- UITGKMCRFFFYFA-UHFFFAOYSA-N 7-(4-(1-aminocyclobutyl)phenyl)-8-phenyl-2,4-dihydro-1h-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-1-one Chemical compound C=1C=C(C=2C(=CC=3N4C(=O)NN=C4COC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 UITGKMCRFFFYFA-UHFFFAOYSA-N 0.000 claims 1
- XYUREUIZTFCREF-UHFFFAOYSA-N 7-(4-(1-aminocyclobutyl)phenyl)-8-phenyl-2-(2,2,2-trifluoroethyl)-2,4-dihydro-1h-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-1-one Chemical compound C=1C=C(C=2C(=CC=3N4C(=O)N(CC(F)(F)F)N=C4COC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 XYUREUIZTFCREF-UHFFFAOYSA-N 0.000 claims 1
- LZEJUKSBIPPYJU-UHFFFAOYSA-N 7-(4-(1-aminocyclobutyl)phenyl)-8-phenyl-4h-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazine-1-carboxamide Chemical compound C=1C=CC=CC=1C=1C=C2N3C(C(=O)N)=NN=C3COC2=NC=1C(C=C1)=CC=C1C1(N)CCC1 LZEJUKSBIPPYJU-UHFFFAOYSA-N 0.000 claims 1
- AEWXJAHRKNGRAE-UHFFFAOYSA-N 7-[4-(1-aminocyclobutyl)phenyl]-1-(2-fluoroethyl)-8-phenyl-4,5-dihydro-3h-pyrido[2,3-b][1,4]diazepin-2-one Chemical compound C=1C=C(C=2C(=CC=3N(CCF)C(=O)CCNC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 AEWXJAHRKNGRAE-UHFFFAOYSA-N 0.000 claims 1
- XODGOUPFHYCPDZ-UHFFFAOYSA-N 7-[4-(1-aminocyclobutyl)phenyl]-3a-methyl-8-phenyl-4,5-dihydro-2h-pyrazolo[3,4-f]quinolin-3-one Chemical compound C=1C=CC=CC=1C=1C=C2C(=NNC3=O)C3(C)CCC2=NC=1C(C=C1)=CC=C1C1(N)CCC1 XODGOUPFHYCPDZ-UHFFFAOYSA-N 0.000 claims 1
- NITOMDUSIVJEBT-UHFFFAOYSA-N 7-[4-(1-aminocyclobutyl)phenyl]-8-phenyl-1,2,4,5-tetrahydropyrazolo[3,4-f]quinolin-3-one Chemical compound C=1C=C(C=2C(=CC=3C4=NNC(O)=C4CCC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 NITOMDUSIVJEBT-UHFFFAOYSA-N 0.000 claims 1
- KMUTXERCNQZBPA-UHFFFAOYSA-N 7-[4-(1-aminocyclobutyl)phenyl]-8-phenyl-1,3,4,5-tetrahydropyrido[2,3-b][1,4]diazepin-2-one Chemical compound C=1C=C(C=2C(=CC=3NC(=O)CCNC=3N=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 KMUTXERCNQZBPA-UHFFFAOYSA-N 0.000 claims 1
- QDKUJSJXDPWWRL-UHFFFAOYSA-N 7-[4-(1-aminocyclobutyl)phenyl]-n-methyl-8-phenyl-4,5-dihydro-1h-pyrazolo[3,4-f]quinolin-3-amine Chemical compound CNC=1NN=C(C2=CC=3C=4C=CC=CC=4)C=1CCC2=NC=3C(C=C1)=CC=C1C1(N)CCC1 QDKUJSJXDPWWRL-UHFFFAOYSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- KELVIOAJFZDRRC-UHFFFAOYSA-N C1(=CC=CC=C1)C1=CC2=C(CCC=3C=NC=NC23)N=C1C1=CC=C(C=C1)C1(CCC1)N.NC1(CCC1)C1=CC=C(C=C1)C1=NC=2CCC=3C(C2C=C1C1=CC=CC=C1)=NNC3NCCO Chemical compound C1(=CC=CC=C1)C1=CC2=C(CCC=3C=NC=NC23)N=C1C1=CC=C(C=C1)C1(CCC1)N.NC1(CCC1)C1=CC=C(C=C1)C1=NC=2CCC=3C(C2C=C1C1=CC=CC=C1)=NNC3NCCO KELVIOAJFZDRRC-UHFFFAOYSA-N 0.000 claims 1
- HDQLNGUIEWEXOC-UHFFFAOYSA-N C1(=CC=CC=C1)C=1C(=NC=2CCC=3C(C2C1)=NNC3)C3=CC=C(C=C3)C3(CCC3)N.CON=C3C=1C=C(C(=NC1CCC3)C3=CC=C(C=C3)C3(CCC3)N)C3=CC=CC=C3 Chemical compound C1(=CC=CC=C1)C=1C(=NC=2CCC=3C(C2C1)=NNC3)C3=CC=C(C=C3)C3(CCC3)N.CON=C3C=1C=C(C(=NC1CCC3)C3=CC=C(C=C3)C3(CCC3)N)C3=CC=CC=C3 HDQLNGUIEWEXOC-UHFFFAOYSA-N 0.000 claims 1
- VBUACCGBMFBILV-UHFFFAOYSA-N C1(=CC=CC=C1)C=1C(=NC=2CCN3C(C2C1)=NN=C3)C3=CC=C(C=C3)C3(CCC3)N.C(C)N3CC=1C=C(C(=NC1CC3)C3=CC=C(C=C3)C3(CCC3)N)C3=CC=CC=C3 Chemical compound C1(=CC=CC=C1)C=1C(=NC=2CCN3C(C2C1)=NN=C3)C3=CC=C(C=C3)C3(CCC3)N.C(C)N3CC=1C=C(C(=NC1CC3)C3=CC=C(C=C3)C3(CCC3)N)C3=CC=CC=C3 VBUACCGBMFBILV-UHFFFAOYSA-N 0.000 claims 1
- WFWFLSFDCGGSPQ-UHFFFAOYSA-N C=1C=CC=CC=1C=1C=C2N3C(N(C)C)=NN=C3COC2=NC=1C(C=C1)=CC=C1C1(N)CCC1 Chemical compound C=1C=CC=CC=1C=1C=C2N3C(N(C)C)=NN=C3COC2=NC=1C(C=C1)=CC=C1C1(N)CCC1 WFWFLSFDCGGSPQ-UHFFFAOYSA-N 0.000 claims 1
- IZVRIZOELUPIKP-UHFFFAOYSA-N CC1(C=2C(C=3C=C(C(=NC3C1)C1=CC=C(C=C1)C1(CCC1)N)C1=CC=CC=C1)=NNC2)C.NC2(CCC2)C2=CC=C(C=C2)C2=NC=1CC(CC(C1C=C2C2=CC=CC=C2)=O)(C)C Chemical compound CC1(C=2C(C=3C=C(C(=NC3C1)C1=CC=C(C=C1)C1(CCC1)N)C1=CC=CC=C1)=NNC2)C.NC2(CCC2)C2=CC=C(C=C2)C2=NC=1CC(CC(C1C=C2C2=CC=CC=C2)=O)(C)C IZVRIZOELUPIKP-UHFFFAOYSA-N 0.000 claims 1
- 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
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims 1
- STQTYJLNNSUSBK-UHFFFAOYSA-N NC1(CCC1)C1=CC=C(C=C1)C1=NC=2CCC=3C(C2C=C1C1=CC=CC=C1)=NNC3O.C3(=CC=CC=C3)C=3C(=NC=1CCC=2C(C1C3)=NNC2)C2=CC=C(C=C2)C2(CCC2)N Chemical compound NC1(CCC1)C1=CC=C(C=C1)C1=NC=2CCC=3C(C2C=C1C1=CC=CC=C1)=NNC3O.C3(=CC=CC=C3)C=3C(=NC=1CCC=2C(C1C3)=NNC2)C2=CC=C(C=C2)C2(CCC2)N STQTYJLNNSUSBK-UHFFFAOYSA-N 0.000 claims 1
- 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
- 230000002265 prevention Effects 0.000 claims 1
- 238000001959 radiotherapy Methods 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- BYUAYHGIDFCNDB-UHFFFAOYSA-N 8-[4-(1-aminocyclobutyl)phenyl]-9-phenyl-5,6-dihydropyrido[2,3-h]quinazolin-2-amine Chemical compound C=1C=CC=CC=1C=1C=C2C3=NC(N)=NC=C3CCC2=NC=1C(C=C1)=CC=C1C1(N)CCC1 BYUAYHGIDFCNDB-UHFFFAOYSA-N 0.000 description 2
- 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
- 239000000047 product Substances 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 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
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0922589.7A GB0922589D0 (en) | 2009-12-23 | 2009-12-23 | Pharmaceutical compounds |
| GB0922589.7 | 2009-12-23 | ||
| PCT/GB2010/002329 WO2011077098A1 (en) | 2009-12-23 | 2010-12-23 | Inhibitors of akt activity |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013515710A JP2013515710A (ja) | 2013-05-09 |
| JP2013515710A5 true JP2013515710A5 (https=) | 2013-10-31 |
| JP5923043B2 JP5923043B2 (ja) | 2016-05-24 |
Family
ID=41716932
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012545434A Active JP5923043B2 (ja) | 2009-12-23 | 2010-12-23 | Ａｋｔ活性の阻害剤 |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US9221838B2 (https=) |
| EP (1) | EP2516435B8 (https=) |
| JP (1) | JP5923043B2 (https=) |
| KR (1) | KR20140015157A (https=) |
| CN (1) | CN102791708B (https=) |
| AU (1) | AU2010334591C1 (https=) |
| BR (1) | BR112012015677A2 (https=) |
| CA (1) | CA2783340C (https=) |
| CY (1) | CY1115686T1 (https=) |
| DK (1) | DK2516435T3 (https=) |
| ES (1) | ES2503794T3 (https=) |
| GB (1) | GB0922589D0 (https=) |
| IL (1) | IL220153A (https=) |
| MX (1) | MX2012007274A (https=) |
| NZ (1) | NZ600453A (https=) |
| PL (1) | PL2516435T3 (https=) |
| PT (1) | PT2516435E (https=) |
| RU (1) | RU2579513C2 (https=) |
| SG (1) | SG181517A1 (https=) |
| SI (1) | SI2516435T1 (https=) |
| WO (1) | WO2011077098A1 (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201205164D0 (en) | 2012-03-23 | 2012-05-09 | Almac Discovery Ltd | Pharmaceutical compounds |
| CA2971763A1 (en) * | 2014-12-23 | 2016-06-30 | Bergenbio Asa | Inhibitors of akt kinase |
| CN111943962A (zh) * | 2015-02-27 | 2020-11-17 | 大鹏药品工业株式会社 | 咪唑并噁嗪晶体、含有所述晶体的药物组合物和制备所述晶体的方法 |
| GB201603779D0 (en) | 2016-03-04 | 2016-04-20 | Mission Therapeutics Ltd | Novel compounds |
| US11208478B2 (en) | 2016-08-07 | 2021-12-28 | The Wistar Institute Of Anatomy And Biology | Methods of detecting and treating a tumor expressing pT346 PDK1 |
| PE20200696A1 (es) * | 2017-06-22 | 2020-06-16 | Curadev Pharma Ltd | Moduladores de moleculas pequenas de sting humana |
| KR102917509B1 (ko) | 2017-09-07 | 2026-01-26 | 오거스타 유니버시티 리서치 인스티튜트, 인크. | 특이적 akt3 활성제 및 이의 용도 |
| 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 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUT76853A (en) * | 1994-11-14 | 1997-12-29 | Warner Lambert Co | 6-aryl pyrido[2,3-d]pyrimidines and naphthyridines for inhibiting protein tyrosine kinase mediated cellular proliferation and pharmaceutical compositions containing the same |
| 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 |
| US8008317B2 (en) * | 2005-06-10 | 2011-08-30 | Merck Sharp & Dohme Corp. | Inhibitors of akt activtiy |
| CA2656507C (en) * | 2006-07-17 | 2012-03-20 | 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 |
| CA2726317A1 (en) | 2008-06-03 | 2009-12-10 | Merck Sharp & Dohme Corp. | Inhibitors of akt activity |
| EP2299825B1 (en) | 2008-06-03 | 2013-07-31 | Merck Sharp & Dohme Corp. | Inhibitors of akt activity |
-
2009
- 2009-12-23 GB GBGB0922589.7A patent/GB0922589D0/en not_active Ceased
-
2010
- 2010-12-23 ES ES10800980.4T patent/ES2503794T3/es active Active
- 2010-12-23 SG SG2012041232A patent/SG181517A1/en unknown
- 2010-12-23 RU RU2012131115/04A patent/RU2579513C2/ru not_active IP Right Cessation
- 2010-12-23 EP EP10800980.4A patent/EP2516435B8/en active Active
- 2010-12-23 SI SI201030774T patent/SI2516435T1/sl unknown
- 2010-12-23 DK DK10800980.4T patent/DK2516435T3/da active
- 2010-12-23 AU AU2010334591A patent/AU2010334591C1/en not_active Ceased
- 2010-12-23 BR BRBR112012015677-2A patent/BR112012015677A2/pt not_active Application Discontinuation
- 2010-12-23 WO PCT/GB2010/002329 patent/WO2011077098A1/en not_active Ceased
- 2010-12-23 KR KR1020127019033A patent/KR20140015157A/ko not_active Ceased
- 2010-12-23 CA CA2783340A patent/CA2783340C/en not_active Expired - Fee Related
- 2010-12-23 MX MX2012007274A patent/MX2012007274A/es active IP Right Grant
- 2010-12-23 PT PT108009804T patent/PT2516435E/pt unknown
- 2010-12-23 US US13/517,219 patent/US9221838B2/en active Active
- 2010-12-23 JP JP2012545434A patent/JP5923043B2/ja active Active
- 2010-12-23 PL PL10800980T patent/PL2516435T3/pl unknown
- 2010-12-23 NZ NZ600453A patent/NZ600453A/xx not_active IP Right Cessation
- 2010-12-23 CN CN201080059321.9A patent/CN102791708B/zh active Active
-
2012
- 2012-06-04 IL IL220153A patent/IL220153A/en not_active IP Right Cessation
-
2014
- 2014-10-31 CY CY20141100899T patent/CY1115686T1/el unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2013515710A5 (https=) | ||
| RU2012131115A (ru) | Ингибиторы активности акт | |
| JP7654071B2 (ja) | 複素環スピロ化合物及び使用方法 | |
| CN111484480A (zh) | 一种多环类衍生物抑制剂、其制备方法和应用 | |
| AU2011278279B2 (en) | IP receptor agonist heterocyclic compounds | |
| Litvinov | Chemistry and biological activities of 1, 8-naphthyridines | |
| JP2020527174A5 (https=) | ||
| JP2012515205A5 (https=) | ||
| JP2016500671A5 (https=) | ||
| CN102399233A (zh) | PI3K和mTOR双重抑制剂类化合物 | |
| WO2012167600A1 (zh) | 一种杂环并吡啶酮类化合物，其中间体、制备方法和用途 | |
| IL275489B2 (en) | Chromenopyridine derivatives as phosphatidylinositol phosphate kinase inhibitors | |
| ME02635B (me) | Novi derivati pirola, postupak njihove priprave i farmaceutski pripravci koji ih sadrže | |
| KR20180030199A (ko) | 콜로니 자극 인자-1 수용체(csf-1r) 저해제 | |
| CA3085460A1 (en) | Aryl-bipyridine amine derivatives as phosphatidylinositol phosphate kinase inhibitors | |
| RU2009123930A (ru) | Химические соединения 637: пиридопиримидиндионы в качестве ингибиторов pde4 | |
| BR112021005896A2 (pt) | moduladores da monoacilglicerol lipase | |
| AU2020332462B2 (en) | Azaheteroaryl compound and application thereof | |
| JP2015510881A5 (https=) | ||
| US20250136592A1 (en) | C-linked inhibitors of enl/af9 yeats | |
| CA2819955A1 (en) | Substituted imidazoquinoline derivatives | |
| CA2474823A1 (en) | Heteroaryl substituted 2-pyridinyl and 2-pyrimidinyl-6,7,8,9-tetrahydropyrimido[1,2-a] pyrimidin-4-one derivatives | |
| WO2021043245A1 (en) | Hydantoin derivative | |
| RU2019126033A (ru) | Бициклические амины в качестве новых ингибиторов jak-киназы | |
| BR112021005936A2 (pt) | moduladores de monoacilglicerol lipase |