MX2012011412A - Compuestos triciclicos e inhibidores de quinasa de union a dominio pdz (pbk) que contienen el mismo. - Google Patents
Compuestos triciclicos e inhibidores de quinasa de union a dominio pdz (pbk) que contienen el mismo.Info
- Publication number
- MX2012011412A MX2012011412A MX2012011412A MX2012011412A MX2012011412A MX 2012011412 A MX2012011412 A MX 2012011412A MX 2012011412 A MX2012011412 A MX 2012011412A MX 2012011412 A MX2012011412 A MX 2012011412A MX 2012011412 A MX2012011412 A MX 2012011412A
- Authority
- MX
- Mexico
- Prior art keywords
- quinolin
- phenyl
- hydroxy
- methoxy
- oxo
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 153
- 239000003112 inhibitor Substances 0.000 title claims abstract description 9
- 201000010099 disease Diseases 0.000 claims abstract description 33
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 33
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 22
- 201000011510 cancer Diseases 0.000 claims abstract description 19
- -1 cyano, nitro, amino Chemical group 0.000 claims description 877
- 229910052739 hydrogen Inorganic materials 0.000 claims description 310
- 239000001257 hydrogen Substances 0.000 claims description 309
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 269
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 191
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 178
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 160
- 125000000217 alkyl group Chemical group 0.000 claims description 156
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 152
- 125000001424 substituent group Chemical group 0.000 claims description 147
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 138
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 128
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 122
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 116
- 150000003839 salts Chemical class 0.000 claims description 114
- 229910052736 halogen Inorganic materials 0.000 claims description 110
- 125000005936 piperidyl group Chemical group 0.000 claims description 103
- 150000002367 halogens Chemical class 0.000 claims description 100
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 90
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 90
- 125000003545 alkoxy group Chemical group 0.000 claims description 65
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 65
- VLCMRTMCMQJSKM-UHFFFAOYSA-N phenyl-[4-phenyl-8-(trifluoromethyl)quinolin-3-yl]methanone Chemical compound C=1C=CC=CC=1C(=O)C1=CN=C2C(C(F)(F)F)=CC=CC2=C1C1=CC=CC=C1 VLCMRTMCMQJSKM-UHFFFAOYSA-N 0.000 claims description 54
- COLGMZQCAPDJEQ-UHFFFAOYSA-N 5h-thieno[2,3-c]quinolin-4-one Chemical compound O=C1NC2=CC=CC=C2C2=C1SC=C2 COLGMZQCAPDJEQ-UHFFFAOYSA-N 0.000 claims description 51
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 51
- 125000001072 heteroaryl group Chemical group 0.000 claims description 50
- 125000004193 piperazinyl group Chemical group 0.000 claims description 50
- 125000002757 morpholinyl group Chemical group 0.000 claims description 39
- 125000003118 aryl group Chemical group 0.000 claims description 35
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 34
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 34
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 33
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 33
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 32
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims description 25
- 230000001419 dependent effect Effects 0.000 claims description 24
- 239000008194 pharmaceutical composition Substances 0.000 claims description 23
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 22
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 22
- 125000002393 azetidinyl group Chemical group 0.000 claims description 20
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 18
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 18
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 18
- 125000004076 pyridyl group Chemical group 0.000 claims description 18
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 16
- 125000005943 1,2,3,6-tetrahydropyridyl group Chemical group 0.000 claims description 15
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 15
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 14
- 125000002883 imidazolyl group Chemical group 0.000 claims description 14
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 13
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 12
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 12
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
- LLAPDLPYIYKTGQ-UHFFFAOYSA-N 1-aminoethyl Chemical group C[CH]N LLAPDLPYIYKTGQ-UHFFFAOYSA-N 0.000 claims description 11
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 11
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 11
- 125000002541 furyl group Chemical group 0.000 claims description 10
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 10
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
- 125000001544 thienyl group Chemical group 0.000 claims description 10
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 9
- OLYOORKNESCLTH-UHFFFAOYSA-N 7,8,9-trihydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=2C(O)=C(O)C(O)=CC=2NC(=O)C2=C1C=CS2 OLYOORKNESCLTH-UHFFFAOYSA-N 0.000 claims description 9
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 9
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 9
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 125000005999 2-bromoethyl group Chemical group 0.000 claims description 8
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 8
- 102220595571 Major vault protein_R52A_mutation Human genes 0.000 claims description 8
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 8
- 102220558655 Nuclear protein 1_R51A_mutation Human genes 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 7
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 7
- 125000003566 oxetanyl group Chemical group 0.000 claims description 7
- 125000000335 thiazolyl group Chemical group 0.000 claims description 7
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 6
- MMHDVVJAYIEIGD-UHFFFAOYSA-N 9-(4-amino-3-methoxyphenyl)-8-methoxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(N)C(OC)=C1 MMHDVVJAYIEIGD-UHFFFAOYSA-N 0.000 claims description 6
- BOLQOFVUCLAHOY-UHFFFAOYSA-N 9-[4-(2-aminoethyl)phenyl]-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(CCN)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 BOLQOFVUCLAHOY-UHFFFAOYSA-N 0.000 claims description 6
- QOZYMUQOKYGGAL-UHFFFAOYSA-N 9-[4-[1-(dimethylamino)ethyl]phenyl]-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(C(N(C)C)C)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 QOZYMUQOKYGGAL-UHFFFAOYSA-N 0.000 claims description 6
- 102220541603 Centrin-1_R22A_mutation Human genes 0.000 claims description 6
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- CQVWOXVVCUGWCR-UHFFFAOYSA-N 9-[4-[2-(dimethylamino)ethyl]phenyl]-8-methoxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(CCN(C)C)C=C1 CQVWOXVVCUGWCR-UHFFFAOYSA-N 0.000 claims description 5
- 102220595577 Major vault protein_R24A_mutation Human genes 0.000 claims description 5
- 102220587413 N-acetylserotonin O-methyltransferase-like protein_R23A_mutation Human genes 0.000 claims description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 5
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 5
- 125000003725 azepanyl group Chemical group 0.000 claims description 5
- 125000004069 aziridinyl group Chemical group 0.000 claims description 5
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 5
- RJCAGQWAPIQFON-UHFFFAOYSA-N 3-[4-(8-methoxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]-3-oxopropanenitrile Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(C(=O)CC#N)C=C1 RJCAGQWAPIQFON-UHFFFAOYSA-N 0.000 claims description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- UDLWPNDDGXJCSJ-UHFFFAOYSA-N 7,9-dimethoxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound O=C1NC2=CC(OC)=CC(OC)=C2C2=C1SC=C2 UDLWPNDDGXJCSJ-UHFFFAOYSA-N 0.000 claims description 4
- UUFOMVOYZDQBCL-UHFFFAOYSA-N 8-hydroxy-1-piperazin-1-yl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=2C3=CC(O)=CC=C3NC(=O)C=2SC=C1N1CCNCC1 UUFOMVOYZDQBCL-UHFFFAOYSA-N 0.000 claims description 4
- IUOPTDPZGPEDCM-UHFFFAOYSA-N 8-hydroxy-3-(hydroxymethyl)-5h-pyrrolo[2,3-c]quinolin-4-one Chemical compound O=C1NC2=CC=C(O)C=C2C2=C1N(CO)C=C2 IUOPTDPZGPEDCM-UHFFFAOYSA-N 0.000 claims description 4
- WFMSDZQYKMADIC-UHFFFAOYSA-N 8-hydroxy-5-methylthieno[2,3-c]quinolin-4-one Chemical compound O=C1N(C)C2=CC=C(O)C=C2C2=C1SC=C2 WFMSDZQYKMADIC-UHFFFAOYSA-N 0.000 claims description 4
- VNZHYDZSNHVQQS-UHFFFAOYSA-N 8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C12=CC(O)=CC=C2NC(=O)C2=C1C=CS2 VNZHYDZSNHVQQS-UHFFFAOYSA-N 0.000 claims description 4
- CHYRZPZOSVMSHU-UHFFFAOYSA-N 8-hydroxy-9-(3-hydroxyphenyl)-5h-thieno[2,3-c]quinolin-4-one Chemical compound OC1=CC=CC(C=2C=3C=4C=CSC=4C(=O)NC=3C=CC=2O)=C1 CHYRZPZOSVMSHU-UHFFFAOYSA-N 0.000 claims description 4
- NHZZDHMAWQRUFV-UHFFFAOYSA-N 8-hydroxy-9-(4-hydroxyphenyl)-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(O)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 NHZZDHMAWQRUFV-UHFFFAOYSA-N 0.000 claims description 4
- BZEIRDSCZXTXMX-OWOJBTEDSA-N 8-hydroxy-9-[(e)-3-(3-hydroxypyrrolidin-1-yl)prop-1-enyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1C(O)CCN1C\C=C\C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 BZEIRDSCZXTXMX-OWOJBTEDSA-N 0.000 claims description 4
- ZTMOUJUDDNQUIH-UHFFFAOYSA-N 8-hydroxy-9-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1CN(C)CCN1CC1=CC=C(C=2C=3C=4C=CSC=4C(=O)NC=3C=CC=2O)C=C1 ZTMOUJUDDNQUIH-UHFFFAOYSA-N 0.000 claims description 4
- GRFNKXDTGNQDOH-UHFFFAOYSA-N 8-methoxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C12=CC(OC)=CC=C2NC(=O)C2=C1C=CS2 GRFNKXDTGNQDOH-UHFFFAOYSA-N 0.000 claims description 4
- NPVZLKPHHQORRB-DUXPYHPUSA-N 9-[(e)-3-(3-aminopiperidin-1-yl)prop-1-enyl]-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1C(N)CCCN1C\C=C\C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 NPVZLKPHHQORRB-DUXPYHPUSA-N 0.000 claims description 4
- GIBDONKBIIVTDJ-ONEGZZNKSA-N 9-[(e)-3-[3-(dimethylamino)pyrrolidin-1-yl]prop-1-enyl]-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1C(N(C)C)CCN1C\C=C\C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 GIBDONKBIIVTDJ-ONEGZZNKSA-N 0.000 claims description 4
- YLOILQKJJQZBAK-UHFFFAOYSA-N 9-[4-(aminomethyl)phenyl]-8-hydroxy-2-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound S1C(C)=CC(C=23)=C1C(=O)NC3=CC=C(O)C=2C1=CC=C(CN)C=C1 YLOILQKJJQZBAK-UHFFFAOYSA-N 0.000 claims description 4
- 102220540772 E3 ubiquitin-protein ligase CHIP_R72A_mutation Human genes 0.000 claims description 4
- 102220483127 Gasdermin-A_R73A_mutation Human genes 0.000 claims description 4
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- 102220521661 Ribosome biogenesis protein NSA2 homolog_R71A_mutation Human genes 0.000 claims description 4
- 102220545880 Vacuolar protein sorting-associated protein 41 homolog_R75A_mutation Human genes 0.000 claims description 4
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 4
- AUQDITHEDVOTCU-UHFFFAOYSA-N cyclopropyl cyanide Chemical compound N#CC1CC1 AUQDITHEDVOTCU-UHFFFAOYSA-N 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- ZCRZCMUDOWDGOB-UHFFFAOYSA-N ethanesulfonimidic acid Chemical compound CCS(N)(=O)=O ZCRZCMUDOWDGOB-UHFFFAOYSA-N 0.000 claims description 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
- DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims description 4
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 4
- PXMYGNBQBZWICC-UHFFFAOYSA-N 1,8-dihydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C12=CC(O)=CC=C2NC(=O)C2=C1C(O)=CS2 PXMYGNBQBZWICC-UHFFFAOYSA-N 0.000 claims description 3
- PSBBIANZFFGOJW-UHFFFAOYSA-N 1-(3-aminopiperidin-1-yl)-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1C(N)CCCN1C1=CSC2=C1C1=CC(O)=CC=C1NC2=O PSBBIANZFFGOJW-UHFFFAOYSA-N 0.000 claims description 3
- BYIQVAUNWASMFP-UHFFFAOYSA-N 1-(4-hydroxyphenyl)-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(O)=CC=C1C1=CSC2=C1C1=CC=CC=C1NC2=O BYIQVAUNWASMFP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 3
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims description 3
- HMSHDQWZLJEWGN-UHFFFAOYSA-N 2-[4-(8-methoxy-6-methyl-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)anilino]acetonitrile Chemical compound COC1=CC(C)=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(NCC#N)C=C1 HMSHDQWZLJEWGN-UHFFFAOYSA-N 0.000 claims description 3
- LUQIJWBJLLLVCZ-UHFFFAOYSA-N 2-fluoro-n-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)benzenesulfonamide Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(S(=O)(=O)NCCO)C(F)=C1 LUQIJWBJLLLVCZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- LZSXYVQDQFUTRV-UHFFFAOYSA-N 3,5-dihydropyrrolo[2,3-c]quinolin-4-one Chemical compound O=C1NC2=CC=CC=C2C2=C1NC=C2 LZSXYVQDQFUTRV-UHFFFAOYSA-N 0.000 claims description 3
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 3
- CMRJVQPBTWNUIT-UHFFFAOYSA-N 4-(8-hydroxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)-n-(3-methylbutyl)benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NCCC(C)C)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 CMRJVQPBTWNUIT-UHFFFAOYSA-N 0.000 claims description 3
- KCFYWMBKFIZTLB-UHFFFAOYSA-N 4-(8-hydroxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)benzonitrile Chemical compound OC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(C#N)C=C1 KCFYWMBKFIZTLB-UHFFFAOYSA-N 0.000 claims description 3
- OYOXGRMMUWXDQR-UHFFFAOYSA-N 4-(8-methoxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)benzonitrile Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(C#N)C=C1 OYOXGRMMUWXDQR-UHFFFAOYSA-N 0.000 claims description 3
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- VGLHOZOMRLVVBW-SNVBAGLBSA-N 6-bromo-8-hydroxy-9-[4-[(1r)-1-(methylamino)ethyl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC([C@@H](C)NC)=CC=C1C1=C(O)C=C(Br)C2=C1C(C=CS1)=C1C(=O)N2 VGLHOZOMRLVVBW-SNVBAGLBSA-N 0.000 claims description 3
- FEJNENOPRDTEIM-UHFFFAOYSA-N 6-bromo-9-[3-fluoro-4-[2-(methylamino)ethyl]phenyl]-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=C(F)C(CCNC)=CC=C1C1=C(O)C=C(Br)C2=C1C(C=CS1)=C1C(=O)N2 FEJNENOPRDTEIM-UHFFFAOYSA-N 0.000 claims description 3
- FSWSJPMIDVZHAO-UHFFFAOYSA-N 6-fluoro-8-methoxy-9-(1,2,3,6-tetrahydropyridin-4-yl)-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC(F)=C2NC(=O)C=3SC=CC=3C2=C1C1=CCNCC1 FSWSJPMIDVZHAO-UHFFFAOYSA-N 0.000 claims description 3
- YKLBSLRCVXWLCU-UHFFFAOYSA-N 7,8,9-trimethoxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=2C(OC)=C(OC)C(OC)=CC=2NC(=O)C2=C1C=CS2 YKLBSLRCVXWLCU-UHFFFAOYSA-N 0.000 claims description 3
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- LDUCTRARFMXGAS-UHFFFAOYSA-N tert-butyl n-[2-[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-3-methylbutyl]carbamate Chemical compound C1=C(F)C(C(CNC(=O)OC(C)(C)C)C(C)C)=CC=C1B1OC(C)(C)C(C)(C)O1 LDUCTRARFMXGAS-UHFFFAOYSA-N 0.000 description 1
- OYBJFEDZLYPTGH-UHFFFAOYSA-N tert-butyl n-[2-[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propyl]-n-methylcarbamate Chemical compound C1=C(F)C(C(CN(C)C(=O)OC(C)(C)C)C)=CC=C1B1OC(C)(C)C(C)(C)O1 OYBJFEDZLYPTGH-UHFFFAOYSA-N 0.000 description 1
- YSWGHDMGGXFIDV-UHFFFAOYSA-N tert-butyl n-[2-[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propyl]carbamate Chemical compound C1=C(F)C(C(CNC(=O)OC(C)(C)C)C)=CC=C1B1OC(C)(C)C(C)(C)O1 YSWGHDMGGXFIDV-UHFFFAOYSA-N 0.000 description 1
- ZEVUECAHTUAWBP-UHFFFAOYSA-N tert-butyl n-[2-[2-fluoro-4-(8-methoxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]ethyl]carbamate Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(CCNC(=O)OC(C)(C)C)C(F)=C1 ZEVUECAHTUAWBP-UHFFFAOYSA-N 0.000 description 1
- VOLRCGKQEIHPQR-UHFFFAOYSA-N tert-butyl n-[2-[2-fluoro-4-(8-methoxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]propyl]carbamate Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(C(C)CNC(=O)OC(C)(C)C)C(F)=C1 VOLRCGKQEIHPQR-UHFFFAOYSA-N 0.000 description 1
- APLMGABQZZNQOE-UHFFFAOYSA-N tert-butyl n-[2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]butyl]carbamate Chemical compound C1=CC(C(CNC(=O)OC(C)(C)C)CC)=CC=C1B1OC(C)(C)C(C)(C)O1 APLMGABQZZNQOE-UHFFFAOYSA-N 0.000 description 1
- KFTWYIAAHLUIBS-UHFFFAOYSA-N tert-butyl n-[2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propyl]carbamate Chemical compound C1=CC(C(CNC(=O)OC(C)(C)C)C)=CC=C1B1OC(C)(C)C(C)(C)O1 KFTWYIAAHLUIBS-UHFFFAOYSA-N 0.000 description 1
- KSCFWYPOKVCWIQ-UHFFFAOYSA-N tert-butyl n-[2-[4-(6-chloro-8-methoxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]propyl]carbamate Chemical compound COC1=CC(Cl)=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(C(C)CNC(=O)OC(C)(C)C)C=C1 KSCFWYPOKVCWIQ-UHFFFAOYSA-N 0.000 description 1
- IVQHYUPLQLTXGR-UHFFFAOYSA-N tert-butyl n-[2-[4-(8-methoxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]-2-methylpropyl]carbamate Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(C(C)(C)CNC(=O)OC(C)(C)C)C=C1 IVQHYUPLQLTXGR-UHFFFAOYSA-N 0.000 description 1
- FSDRBIKAQRWBGZ-UHFFFAOYSA-N tert-butyl n-[2-[4-(8-methoxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]-3-methylbutyl]carbamate Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(C(CNC(=O)OC(C)(C)C)C(C)C)C=C1 FSDRBIKAQRWBGZ-UHFFFAOYSA-N 0.000 description 1
- HOHABEUYPZVONR-UHFFFAOYSA-N tert-butyl n-[2-[4-(8-methoxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]ethyl]-n-methylcarbamate Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(CCN(C)C(=O)OC(C)(C)C)C=C1 HOHABEUYPZVONR-UHFFFAOYSA-N 0.000 description 1
- LVEISNPADCGBDA-UHFFFAOYSA-N tert-butyl n-[2-[4-(8-methoxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]propan-2-yl]carbamate Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(C(C)(C)NC(=O)OC(C)(C)C)C=C1 LVEISNPADCGBDA-UHFFFAOYSA-N 0.000 description 1
- WOPPNXTWWYUSFX-UHFFFAOYSA-N tert-butyl n-[2-[4-(8-methoxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]propyl]carbamate Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(C(C)CNC(=O)OC(C)(C)C)C=C1 WOPPNXTWWYUSFX-UHFFFAOYSA-N 0.000 description 1
- QBLBAUGTVCKBKF-UHFFFAOYSA-N tert-butyl n-[2-methyl-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propyl]carbamate Chemical compound C1=CC(C(C)(C)CNC(=O)OC(C)(C)C)=CC=C1B1OC(C)(C)C(C)(C)O1 QBLBAUGTVCKBKF-UHFFFAOYSA-N 0.000 description 1
- LUCVSPFSLFHHLD-UHFFFAOYSA-N tert-butyl n-[[1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclopropyl]methyl]carbamate Chemical compound C=1C=C(B2OC(C)(C)C(C)(C)O2)C=CC=1C1(CNC(=O)OC(C)(C)C)CC1 LUCVSPFSLFHHLD-UHFFFAOYSA-N 0.000 description 1
- HOFZVSNQDUGHPA-UHFFFAOYSA-N tert-butyl n-[[4-(6-fluoro-8-methoxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]methyl]carbamate Chemical compound COC1=CC(F)=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(CNC(=O)OC(C)(C)C)C=C1 HOFZVSNQDUGHPA-UHFFFAOYSA-N 0.000 description 1
- VZRIRNYLDPITDV-UHFFFAOYSA-N tert-butyl n-[[4-(8-methoxy-6-methyl-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]methyl]carbamate Chemical compound COC1=CC(C)=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(CNC(=O)OC(C)(C)C)C=C1 VZRIRNYLDPITDV-UHFFFAOYSA-N 0.000 description 1
- YRSBMLYBZHELAV-UHFFFAOYSA-N tert-butyl n-ethyl-n-[1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl]carbamate Chemical compound C1=CC(C(C)N(CC)C(=O)OC(C)(C)C)=CC=C1B1OC(C)(C)C(C)(C)O1 YRSBMLYBZHELAV-UHFFFAOYSA-N 0.000 description 1
- ZCTAYVAYISRTIV-CQSZACIVSA-N tert-butyl n-methyl-n-[(1r)-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl]carbamate Chemical compound C1=CC([C@H](N(C)C(=O)OC(C)(C)C)C)=CC=C1B1OC(C)(C)C(C)(C)O1 ZCTAYVAYISRTIV-CQSZACIVSA-N 0.000 description 1
- DPCJGNAOBDBZTM-UHFFFAOYSA-N tert-butyl n-methyl-n-[3-methyl-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]butyl]carbamate Chemical compound C1=CC(C(CN(C)C(=O)OC(C)(C)C)C(C)C)=CC=C1B1OC(C)(C)C(C)(C)O1 DPCJGNAOBDBZTM-UHFFFAOYSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 230000002381 testicular Effects 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- ARYHTUPFQTUBBG-UHFFFAOYSA-N thiophen-2-ylboronic acid Chemical compound OB(O)C1=CC=CS1 ARYHTUPFQTUBBG-UHFFFAOYSA-N 0.000 description 1
- BWHDROKFUHTORW-UHFFFAOYSA-N tri-tert-butylphosphine Substances CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/16—Ring systems of three rings containing carbocyclic rings other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C07D519/02—Ergot alkaloids of the cyclic peptide type
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31860610P | 2010-03-29 | 2010-03-29 | |
| PCT/US2011/030278 WO2011123419A1 (en) | 2010-03-29 | 2011-03-29 | Trycyclic compounds and pbk inhibitors containing the same |
Publications (1)
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|---|---|
| MX2012011412A true MX2012011412A (es) | 2013-02-07 |
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| MX2012011412A MX2012011412A (es) | 2010-03-29 | 2011-03-29 | Compuestos triciclicos e inhibidores de quinasa de union a dominio pdz (pbk) que contienen el mismo. |
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| Country | Link |
|---|---|
| US (2) | US8962648B2 (enExample) |
| EP (1) | EP2552206B1 (enExample) |
| JP (1) | JP5849302B2 (enExample) |
| KR (1) | KR101757502B1 (enExample) |
| CN (1) | CN102917590B (enExample) |
| AU (1) | AU2011235319B2 (enExample) |
| BR (1) | BR112012023836B1 (enExample) |
| CA (1) | CA2792941C (enExample) |
| DK (1) | DK2552206T3 (enExample) |
| ES (1) | ES2547571T3 (enExample) |
| IL (1) | IL222080B (enExample) |
| MX (1) | MX2012011412A (enExample) |
| SG (1) | SG184376A1 (enExample) |
| TW (1) | TWI503323B (enExample) |
| WO (1) | WO2011123419A1 (enExample) |
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| EA201990240A1 (ru) * | 2013-12-24 | 2019-06-28 | Бристол-Маерс Сквибб Компани | Новые трициклические соединения в качестве противораковых средств |
| TWI557011B (zh) | 2015-05-25 | 2016-11-11 | 可影像處理的自行車錶裝置 | |
| EP3307725A1 (en) | 2015-06-11 | 2018-04-18 | Basilea Pharmaceutica International AG | Efflux-pump inhibitors and therapeutic uses thereof |
| GB201617758D0 (en) | 2016-10-20 | 2016-12-07 | Almac Discovery Limited | Pharmaceutical compounds |
| CN108341774B (zh) * | 2017-01-25 | 2022-07-19 | 首药控股(北京)股份有限公司 | 取代的喹啉酮类抑制剂 |
| BR112019021136A2 (pt) | 2017-04-10 | 2020-07-21 | Bayer Aktiengesellschaft | n-ariletil-2-arilquinolina-4-carboxamidas substituídas e uso das mesmas |
| US12024715B2 (en) | 2017-11-07 | 2024-07-02 | Temple University-Of The Commonwealth System Of Higher Education | Compositions and methods for improved T cells |
| CN111099941B (zh) * | 2018-10-26 | 2022-10-18 | 中国科学院上海有机化学研究所 | 一种烷基腈类化合物的制备方法 |
| TW202300150A (zh) * | 2021-03-18 | 2023-01-01 | 美商薛定諤公司 | 環狀化合物及其使用方法 |
| CN117362304A (zh) * | 2022-07-07 | 2024-01-09 | 深圳微芯生物科技股份有限公司 | 一种甲酰胺取代的杂三环类衍生物、其制备方法及其应用 |
| WO2024097228A1 (en) * | 2022-10-31 | 2024-05-10 | Meliora Therapeutics, Inc. | Compounds targeting cdk11 and methods of using the same |
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| JPS5377096A (en) * | 1976-12-17 | 1978-07-08 | Teijin Ltd | Preparation of thieno 2,3-c quinolin-4(5h)-one-7-acetic acids |
| FR2636063B1 (fr) * | 1988-09-05 | 1993-04-30 | Centre Nat Rech Scient | Composes phenylpyrroliques utiles en tant que medicaments, leur preparation et leur application |
| DE19806348A1 (de) * | 1998-02-12 | 1999-08-19 | Schering Ag | 3,4-Dihydrochinolin-Derivate und ihre Verwendung in Arzneimitteln |
| US6506769B2 (en) | 1999-10-06 | 2003-01-14 | Boehringer Ingelheim Pharmaceuticals, Inc. | Heterocyclic compounds useful as inhibitors of tyrosine kinases |
| US6638929B2 (en) * | 1999-12-29 | 2003-10-28 | Wyeth | Tricyclic protein kinase inhibitors |
| ATE353320T1 (de) * | 1999-12-29 | 2007-02-15 | Wyeth Corp | Tricyclische proteinkinasehemmer |
| DE10242106A1 (de) | 2002-09-11 | 2004-04-15 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Phosphorgruppenhaltige Carbonsäurederivate mit organisch polymerisierbaren Gruppen |
| KR20050057404A (ko) | 2002-09-17 | 2005-06-16 | 워너-램버트 캄파니 엘엘씨 | 정신분열증 치료용 헤테로환 치환된 피페라진 |
| WO2004035577A2 (en) * | 2002-10-16 | 2004-04-29 | Gilead Sciences, Inc. | Pre-organized tricyclic integrase inhibitor compounds |
| GB0501999D0 (en) * | 2005-02-01 | 2005-03-09 | Sentinel Oncology Ltd | Pharmaceutical compounds |
| PT2061765E (pt) * | 2006-09-01 | 2015-02-06 | Senhwa Biosciences Inc | Moduladores de serina-treonina-proteína-quinase e de parp |
| WO2009010804A1 (en) * | 2007-07-19 | 2009-01-22 | Istituto Di Ricerche Di Biologia Molecolare P. Angeletti S.P.A. | Macrocyclic compounds as antiviral agents |
| AU2009219154A1 (en) * | 2008-02-29 | 2009-09-03 | Cylene Pharmaceuticals, Inc. | Protein kinase modulators |
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2011
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- 2011-03-29 DK DK11763307.3T patent/DK2552206T3/en active
- 2011-03-29 US US13/202,544 patent/US8962648B2/en active Active
- 2011-03-29 CA CA2792941A patent/CA2792941C/en active Active
- 2011-03-29 KR KR1020127027125A patent/KR101757502B1/ko not_active Expired - Fee Related
- 2011-03-29 WO PCT/US2011/030278 patent/WO2011123419A1/en not_active Ceased
- 2011-03-29 BR BR112012023836-1A patent/BR112012023836B1/pt not_active IP Right Cessation
- 2011-03-29 AU AU2011235319A patent/AU2011235319B2/en not_active Ceased
- 2011-03-29 SG SG2012072807A patent/SG184376A1/en unknown
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2012
- 2012-09-23 IL IL222080A patent/IL222080B/en active IP Right Grant
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2014
- 2014-12-09 US US14/565,047 patent/US9453025B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CA2792941A1 (en) | 2011-10-06 |
| TWI503323B (zh) | 2015-10-11 |
| JP5849302B2 (ja) | 2016-01-27 |
| BR112012023836B1 (pt) | 2022-02-01 |
| AU2011235319A1 (en) | 2012-10-11 |
| JP2013523749A (ja) | 2013-06-17 |
| TW201136939A (en) | 2011-11-01 |
| US20130178459A1 (en) | 2013-07-11 |
| RU2012145855A (ru) | 2014-05-10 |
| EP2552206A4 (en) | 2013-08-14 |
| HK1179114A1 (en) | 2013-09-27 |
| SG184376A1 (en) | 2012-11-29 |
| CA2792941C (en) | 2017-09-12 |
| WO2011123419A1 (en) | 2011-10-06 |
| US8962648B2 (en) | 2015-02-24 |
| US20150183799A1 (en) | 2015-07-02 |
| DK2552206T3 (en) | 2015-09-28 |
| IL222080B (en) | 2018-05-31 |
| KR101757502B1 (ko) | 2017-07-12 |
| ES2547571T3 (es) | 2015-10-07 |
| BR112012023836A2 (pt) | 2015-09-22 |
| CN102917590B (zh) | 2016-02-17 |
| EP2552206A1 (en) | 2013-02-06 |
| US9453025B2 (en) | 2016-09-27 |
| EP2552206B1 (en) | 2015-07-22 |
| CN102917590A (zh) | 2013-02-06 |
| KR20130020666A (ko) | 2013-02-27 |
| AU2011235319B2 (en) | 2016-07-14 |
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