AU2013250726B2 - Substituted hetero-bicyclic compounds, compositions and medicinal applications thereof - Google Patents
Substituted hetero-bicyclic compounds, compositions and medicinal applications thereof Download PDFInfo
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- AU2013250726B2 AU2013250726B2 AU2013250726A AU2013250726A AU2013250726B2 AU 2013250726 B2 AU2013250726 B2 AU 2013250726B2 AU 2013250726 A AU2013250726 A AU 2013250726A AU 2013250726 A AU2013250726 A AU 2013250726A AU 2013250726 B2 AU2013250726 B2 AU 2013250726B2
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- AU
- Australia
- Prior art keywords
- phenyl
- dihydro
- pyrrolo
- benzoxazepin
- cyclopropyl
- 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.)
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- 239000000203 mixture Substances 0.000 title description 44
- 125000002618 bicyclic heterocycle group Chemical group 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 144
- 238000000034 method Methods 0.000 claims abstract description 92
- 150000003839 salts Chemical class 0.000 claims abstract description 35
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 28
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 25
- 201000010099 disease Diseases 0.000 claims abstract description 19
- 230000001404 mediated effect Effects 0.000 claims abstract description 19
- 238000002360 preparation method Methods 0.000 claims abstract description 18
- 238000011282 treatment Methods 0.000 claims abstract description 11
- 208000035475 disorder Diseases 0.000 claims abstract description 9
- 230000008569 process Effects 0.000 claims abstract description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 406
- -1 furanylene Chemical group 0.000 claims description 260
- 125000000217 alkyl group Chemical group 0.000 claims description 193
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 159
- 229910052736 halogen Inorganic materials 0.000 claims description 119
- 150000002367 halogens Chemical group 0.000 claims description 119
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 118
- 125000001188 haloalkyl group Chemical group 0.000 claims description 112
- 125000003118 aryl group Chemical group 0.000 claims description 94
- 229910052739 hydrogen Inorganic materials 0.000 claims description 92
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 90
- 239000001257 hydrogen Substances 0.000 claims description 90
- 125000001072 heteroaryl group Chemical group 0.000 claims description 88
- 125000000623 heterocyclic group Chemical group 0.000 claims description 75
- 125000001424 substituent group Chemical group 0.000 claims description 73
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 70
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 70
- 125000003342 alkenyl group Chemical group 0.000 claims description 61
- 125000000304 alkynyl group Chemical group 0.000 claims description 61
- 125000002947 alkylene group Chemical group 0.000 claims description 60
- 150000002431 hydrogen Chemical group 0.000 claims description 60
- 125000005842 heteroatom Chemical group 0.000 claims description 58
- 125000003545 alkoxy group Chemical group 0.000 claims description 53
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 48
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 48
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 46
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 41
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims description 40
- 229910052757 nitrogen Inorganic materials 0.000 claims description 37
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 36
- 125000002252 acyl group Chemical group 0.000 claims description 35
- 229910006069 SO3H Inorganic materials 0.000 claims description 33
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 33
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 33
- 239000003814 drug Substances 0.000 claims description 29
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 28
- 229910052717 sulfur Inorganic materials 0.000 claims description 25
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 24
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 claims description 23
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 125000004442 acylamino group Chemical group 0.000 claims description 20
- 125000004423 acyloxy group Chemical group 0.000 claims description 20
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 19
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 19
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 19
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 19
- 125000004043 oxo group Chemical group O=* 0.000 claims description 19
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 18
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims description 18
- 125000000468 ketone group Chemical group 0.000 claims description 17
- 229930194542 Keto Natural products 0.000 claims description 16
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 16
- 229910052705 radium Inorganic materials 0.000 claims description 16
- 229910052701 rubidium Inorganic materials 0.000 claims description 16
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical group C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 14
- 125000004414 alkyl thio group Chemical group 0.000 claims description 13
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 13
- 125000005157 alkyl carboxy group Chemical group 0.000 claims description 12
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 12
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 12
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 10
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 10
- GPAAEZIXSQCCES-UHFFFAOYSA-N 1-methoxy-2-(2-methoxyethoxymethoxymethoxy)ethane Chemical compound COCCOCOCOCCOC GPAAEZIXSQCCES-UHFFFAOYSA-N 0.000 claims description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Chemical group C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 8
- 125000004976 cyclobutylene group Chemical group 0.000 claims description 8
- 125000004956 cyclohexylene group Chemical group 0.000 claims description 8
- 125000004980 cyclopropylene group Chemical group 0.000 claims description 8
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 8
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 7
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 7
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 7
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 7
- 125000002757 morpholinyl group Chemical group 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- 125000003386 piperidinyl group Chemical group 0.000 claims description 7
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 7
- 150000003852 triazoles Chemical class 0.000 claims description 7
- UNTNRNUQVKDIPV-UHFFFAOYSA-N 3h-dithiazole Chemical compound N1SSC=C1 UNTNRNUQVKDIPV-UHFFFAOYSA-N 0.000 claims description 6
- 125000002393 azetidinyl group Chemical group 0.000 claims description 6
- 125000005047 dihydroimidazolyl group Chemical group N1(CNC=C1)* 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000002883 imidazolyl group Chemical group 0.000 claims description 6
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
- 125000005564 oxazolylene group Chemical group 0.000 claims description 6
- 125000003566 oxetanyl group Chemical group 0.000 claims description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 6
- ZGNXATVKGIJQGC-UHFFFAOYSA-N piperidine-3-carbonitrile Chemical compound N#CC1CCCNC1 ZGNXATVKGIJQGC-UHFFFAOYSA-N 0.000 claims description 6
- FSDNTQSJGHSJBG-UHFFFAOYSA-N piperidine-4-carbonitrile Chemical compound N#CC1CCNCC1 FSDNTQSJGHSJBG-UHFFFAOYSA-N 0.000 claims description 6
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 6
- 125000005550 pyrazinylene group Chemical group 0.000 claims description 6
- 125000005551 pyridylene group Chemical group 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 6
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims description 6
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- 125000005557 thiazolylene group Chemical group 0.000 claims description 6
- 125000005556 thienylene group Chemical group 0.000 claims description 6
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 6
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 6
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- OFCKZIWIVDDEOH-UHFFFAOYSA-N 4-[2-(hydroxymethyl)-3-[2-[5-(4-hydroxy-4-methylpiperidine-1-carbonyl)pyridin-2-yl]-1h-pyrrolo[2,3-b]pyridin-4-yl]phenyl]-8-(2-hydroxypropan-2-yl)-2,3-dihydro-1,4-benzoxazepin-5-one Chemical compound C=1C(C(C)(O)C)=CC=C(C2=O)C=1OCCN2C(C=1CO)=CC=CC=1C(C=1C=2)=CC=NC=1NC=2C(N=C1)=CC=C1C(=O)N1CCC(C)(O)CC1 OFCKZIWIVDDEOH-UHFFFAOYSA-N 0.000 claims description 2
- XFNUMRNWBRPEED-UHFFFAOYSA-N 7-cyclopropyl-2-methyl-3-[2-methyl-3-[6-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]phenyl]quinazolin-4-one Chemical compound C1CN(C)CCN1CC1=CC=C(C=2NC3=NC=NC(=C3C=2)C=2C(=C(C=CC=2)N2C(C3=CC=C(C=C3N=C2C)C2CC2)=O)C)C=C1 XFNUMRNWBRPEED-UHFFFAOYSA-N 0.000 claims description 2
- OMINANNSBHUJEO-UHFFFAOYSA-N 8-cyclopropyl-4-[2-(hydroxymethyl)-3-[6-[4-[(4-hydroxy-4-methylpiperidin-1-yl)methyl]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]phenyl]-2,3-dihydro-1,4-benzoxazepin-5-one Chemical compound C1CC(C)(O)CCN1CC1=CC=C(C=2NC3=NC=NC(=C3C=2)C=2C(=C(N3C(C4=CC=C(C=C4OCC3)C3CC3)=O)C=CC=2)CO)C=C1 OMINANNSBHUJEO-UHFFFAOYSA-N 0.000 claims description 2
- AZTAPUAAQAEGNK-UHFFFAOYSA-N 8-cyclopropyl-4-[3-[2-[5-[(2,4-dimethylpiperazin-1-yl)methyl]pyridin-2-yl]-1h-pyrrolo[2,3-b]pyridin-4-yl]-5-fluoro-2-(hydroxymethyl)phenyl]-6-fluoro-2,3-dihydro-1,4-benzoxazepin-5-one Chemical compound CC1CN(C)CCN1CC1=CC=C(C=2NC3=NC=CC(=C3C=2)C=2C(=C(N3C(C4=C(F)C=C(C=C4OCC3)C3CC3)=O)C=C(F)C=2)CO)N=C1 AZTAPUAAQAEGNK-UHFFFAOYSA-N 0.000 claims description 2
- OTGXLQMJILBWHE-UHFFFAOYSA-N CN(C)C(=O)N1CCC(=CC1)c1cc2c(ccnc2[nH]1)-c1cccc(N2CCOc3cc(ccc3C2=O)C(C)(C)O)c1CO Chemical compound CN(C)C(=O)N1CCC(=CC1)c1cc2c(ccnc2[nH]1)-c1cccc(N2CCOc3cc(ccc3C2=O)C(C)(C)O)c1CO OTGXLQMJILBWHE-UHFFFAOYSA-N 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 235000001968 nicotinic acid Nutrition 0.000 claims description 2
- 239000011664 nicotinic acid Substances 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 4
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 3
- XGWLVPCSDMWYMW-UHFFFAOYSA-N 4-[3-[2-[1-(azetidine-1-carbonyl)-3,6-dihydro-2h-pyridin-4-yl]-1h-pyrrolo[2,3-b]pyridin-4-yl]-2-(hydroxymethyl)phenyl]-8-cyclopropyl-6-fluoro-2,3-dihydro-1,4-benzoxazepin-5-one Chemical compound OCC1=C(N2C(C3=C(F)C=C(C=C3OCC2)C2CC2)=O)C=CC=C1C(C=1C=2)=CC=NC=1NC=2C(CC1)=CCN1C(=O)N1CCC1 XGWLVPCSDMWYMW-UHFFFAOYSA-N 0.000 claims 2
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 2
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Chemical compound OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims 2
- 125000006717 (C3-C10) cycloalkenyl group Chemical group 0.000 claims 1
- XJLSEXAGTJCILF-RXMQYKEDSA-N (R)-nipecotic acid zwitterion Chemical compound OC(=O)[C@@H]1CCCNC1 XJLSEXAGTJCILF-RXMQYKEDSA-N 0.000 claims 1
- RTKKMZSKPQGHJC-UHFFFAOYSA-N 1-[[4-[4-[3-(7-cyclopropyl-2-methyl-4-oxoquinazolin-3-yl)-2-methylphenyl]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]methyl]piperidine-3-carbonitrile Chemical compound CC1=NC2=CC(C3CC3)=CC=C2C(=O)N1C(C=1C)=CC=CC=1C(C=1C=2)=NC=NC=1NC=2C(C=C1)=CC=C1CN1CCCC(C#N)C1 RTKKMZSKPQGHJC-UHFFFAOYSA-N 0.000 claims 1
- NBJDSMIOWPVWRW-UHFFFAOYSA-N 2h-oxazepin-5-one Chemical compound O=C1C=CNOC=C1 NBJDSMIOWPVWRW-UHFFFAOYSA-N 0.000 claims 1
- SUTHKAABAMUNSC-UHFFFAOYSA-N 4-[3-(8-cyclopropyl-5-oxo-2,3-dihydro-1,4-benzoxazepin-4-yl)phenyl]-2-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]-1h-pyrrolo[2,3-b]pyridine-5-carbonitrile Chemical compound C1CN(C)CCN1CC1=CC=C(C=2NC3=NC=C(C(C=4C=C(C=CC=4)N4C(C5=CC=C(C=C5OCC4)C4CC4)=O)=C3C=2)C#N)C=C1 SUTHKAABAMUNSC-UHFFFAOYSA-N 0.000 claims 1
- ZWLAXWQOLPQLCN-UHFFFAOYSA-N 4-[3-[2-[1-(azetidine-1-carbonyl)-3,6-dihydro-2h-pyridin-4-yl]-1h-pyrrolo[2,3-b]pyridin-4-yl]-5-fluoro-2-(hydroxymethyl)phenyl]-8-cyclopropyl-6-fluoro-2,3-dihydro-1,4-benzoxazepin-5-one Chemical compound OCC1=C(N2C(C3=C(F)C=C(C=C3OCC2)C2CC2)=O)C=C(F)C=C1C(C=1C=2)=CC=NC=1NC=2C(CC1)=CCN1C(=O)N1CCC1 ZWLAXWQOLPQLCN-UHFFFAOYSA-N 0.000 claims 1
- GOTAKOCZVHHKTK-UHFFFAOYSA-N 4-[4-[2-[1-(azetidine-1-carbonyl)-3,6-dihydro-2h-pyridin-4-yl]-1h-pyrrolo[2,3-b]pyridin-4-yl]-3-(hydroxymethyl)pyridin-2-yl]-8-cyclopropyl-6-fluoro-2,3-dihydro-1,4-benzoxazepin-5-one Chemical compound OCC1=C(N2C(C3=C(F)C=C(C=C3OCC2)C2CC2)=O)N=CC=C1C(C=1C=2)=CC=NC=1NC=2C(CC1)=CCN1C(=O)N1CCC1 GOTAKOCZVHHKTK-UHFFFAOYSA-N 0.000 claims 1
- RFNYBKIBJAGPMW-UHFFFAOYSA-N 4-[4-[3-[8-(1-hydroxycyclopropyl)-5-oxo-2,3-dihydro-1,4-benzoxazepin-4-yl]-2-(hydroxymethyl)phenyl]-1h-pyrrolo[2,3-b]pyridin-2-yl]-n,n-dimethyl-3,6-dihydro-2h-pyridine-1-carboxamide Chemical compound C1N(C(=O)N(C)C)CCC(C=2NC3=NC=CC(=C3C=2)C=2C(=C(N3C(C4=CC=C(C=C4OCC3)C3(O)CC3)=O)C=CC=2)CO)=C1 RFNYBKIBJAGPMW-UHFFFAOYSA-N 0.000 claims 1
- PQJNPLNGKXNJCP-UHFFFAOYSA-N 6-fluoro-4-[2-(hydroxymethyl)-3-[2-(1-methylsulfonyl-3,6-dihydro-2h-pyridin-4-yl)-1h-pyrrolo[2,3-b]pyridin-4-yl]phenyl]-8-(2-hydroxypropan-2-yl)-2,3-dihydro-1,4-benzoxazepin-5-one Chemical compound C=1C(C(C)(O)C)=CC(F)=C(C2=O)C=1OCCN2C(C=1CO)=CC=CC=1C(C=1C=2)=CC=NC=1NC=2C1=CCN(S(C)(=O)=O)CC1 PQJNPLNGKXNJCP-UHFFFAOYSA-N 0.000 claims 1
- BZLRSFSIRVBWMC-UHFFFAOYSA-N 6-fluoro-4-[2-(hydroxymethyl)-3-[2-[5-(4-methylpiperazin-1-yl)pyridin-2-yl]-1h-pyrrolo[2,3-b]pyridin-4-yl]phenyl]-8-(2-hydroxypropan-2-yl)-2,3-dihydro-1,4-benzoxazepin-5-one Chemical compound C1CN(C)CCN1C1=CC=C(C=2NC3=NC=CC(=C3C=2)C=2C(=C(N3C(C4=C(F)C=C(C=C4OCC3)C(C)(C)O)=O)C=CC=2)CO)N=C1 BZLRSFSIRVBWMC-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
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- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
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- A61K31/553—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one oxygen as ring hetero atoms, e.g. loxapine, staurosporine
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2013
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- 2013-04-18 JP JP2015506355A patent/JP6182593B2/ja active Active
- 2013-04-18 CA CA2869954A patent/CA2869954C/en active Active
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|---|---|---|---|---|
| WO2013008095A1 (en) * | 2011-07-08 | 2013-01-17 | Novartis Ag | Novel pyrrolo pyrimidine derivatives |
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| US20150064196A1 (en) | 2015-03-05 |
| IL235146A (en) | 2017-07-31 |
| IN2012CH01573A (OSRAM) | 2015-07-10 |
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| JP6182593B2 (ja) | 2017-08-16 |
| ZA201407341B (en) | 2015-06-24 |
| EP2838898B1 (en) | 2017-01-18 |
| JP2015514749A (ja) | 2015-05-21 |
| US9233983B2 (en) | 2016-01-12 |
| EP2838898A1 (en) | 2015-02-25 |
| AU2013250726A1 (en) | 2014-10-09 |
| CN104662018A (zh) | 2015-05-27 |
| CA2869954C (en) | 2023-01-03 |
| CN104662018B (zh) | 2017-10-24 |
| CA2869954A1 (en) | 2013-10-24 |
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