JP2019505558A5 - - Google Patents
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- Publication number
- JP2019505558A5 JP2019505558A5 JP2018544154A JP2018544154A JP2019505558A5 JP 2019505558 A5 JP2019505558 A5 JP 2019505558A5 JP 2018544154 A JP2018544154 A JP 2018544154A JP 2018544154 A JP2018544154 A JP 2018544154A JP 2019505558 A5 JP2019505558 A5 JP 2019505558A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrazolo
- dihydro
- oxazine
- carboxamide
- 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.)
- Granted
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- 150000003839 salts Chemical class 0.000 claims description 71
- 150000001875 compounds Chemical class 0.000 claims description 55
- -1 cyano, hydroxy Chemical group 0.000 claims description 50
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 29
- 125000001072 heteroaryl group Chemical group 0.000 claims description 28
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 20
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 14
- JROPBYGZSRBHDV-UHFFFAOYSA-N oxazine-2-carboxamide Chemical compound NC(=O)N1OC=CC=C1 JROPBYGZSRBHDV-UHFFFAOYSA-N 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000002393 azetidinyl group Chemical group 0.000 claims description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 5
- MJHYQMWSWMXYQH-UHFFFAOYSA-N 3-(4-cyano-5-fluoro-2-methylphenyl)-N-cyclopropyl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxamide Chemical compound C(#N)C1=CC(=C(C=C1F)C=1C(=NN2C=1OCCC2)C(=O)NC1CC1)C MJHYQMWSWMXYQH-UHFFFAOYSA-N 0.000 claims description 4
- HXVNESZNUYSKMT-UHFFFAOYSA-N 4-[2-(azetidine-1-carbonyl)-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazin-3-yl]-2-fluoro-5-methylbenzonitrile Chemical compound Cc1cc(C#N)c(F)cc1-c1c2OCCCn2nc1C(=O)N1CCC1 HXVNESZNUYSKMT-UHFFFAOYSA-N 0.000 claims description 4
- GRFHQTKEAOBDST-NSHDSACASA-N ClC1=CC(=C(C=C1)C=1C(=NN2C=1OC[C@H](C2)F)C(=O)NC1CC1)C Chemical compound ClC1=CC(=C(C=C1)C=1C(=NN2C=1OC[C@H](C2)F)C(=O)NC1CC1)C GRFHQTKEAOBDST-NSHDSACASA-N 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 4
- 208000011117 substance-related disease Diseases 0.000 claims description 4
- NXQIEDDZYQXLGS-LLVKDONJSA-N (6R)-3-(4-chlorophenyl)-N-cyclopropyl-6-fluoro-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxamide Chemical compound F[C@H]1COc2c(c(nn2C1)C(=O)NC1CC1)-c1ccc(Cl)cc1 NXQIEDDZYQXLGS-LLVKDONJSA-N 0.000 claims description 2
- QMOPFHQOZKALTC-ZETCQYMHSA-N (6S)-3-(4-chloro-2,5-difluorophenyl)-N-cyclopropyl-6-fluoro-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxamide Chemical compound ClC1=CC(=C(C=C1F)C=1C(=NN2C=1OC[C@H](C2)F)C(=O)NC1CC1)F QMOPFHQOZKALTC-ZETCQYMHSA-N 0.000 claims description 2
- NXQIEDDZYQXLGS-NSHDSACASA-N (6S)-3-(4-chlorophenyl)-N-cyclopropyl-6-fluoro-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxamide Chemical compound F[C@@H]1COc2c(c(nn2C1)C(=O)NC1CC1)-c1ccc(Cl)cc1 NXQIEDDZYQXLGS-NSHDSACASA-N 0.000 claims description 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 claims description 2
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 2
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 claims description 2
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims description 2
- PHRSCPGZAINQTD-UHFFFAOYSA-N 2H-1,3-oxazine-2-carboxamide Chemical compound O1C(N=CC=C1)C(=O)N PHRSCPGZAINQTD-UHFFFAOYSA-N 0.000 claims description 2
- LGFLTCBFNXDCLY-UHFFFAOYSA-N 3-(3-chloro-4-fluorophenyl)-N-cyclopropyl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxamide Chemical compound Fc1ccc(cc1Cl)-c1c2OCCCn2nc1C(=O)NC1CC1 LGFLTCBFNXDCLY-UHFFFAOYSA-N 0.000 claims description 2
- GBWMEFKBLUNZIM-UHFFFAOYSA-N 3-(3-chlorophenyl)-N-cyclopropyl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxamide Chemical compound Clc1cccc(c1)-c1c2OCCCn2nc1C(=O)NC1CC1 GBWMEFKBLUNZIM-UHFFFAOYSA-N 0.000 claims description 2
- FGOAWTXGIORNAM-UHFFFAOYSA-N 3-(4-chloro-2,3-difluorophenyl)-N-cyclopropyl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxamide Chemical compound Fc1c(Cl)ccc(-c2c3OCCCn3nc2C(=O)NC2CC2)c1F FGOAWTXGIORNAM-UHFFFAOYSA-N 0.000 claims description 2
- WYSBJUKHVQZOHC-UHFFFAOYSA-N 3-(4-chloro-2,5-difluorophenyl)-N-cyclopropyl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxamide Chemical compound Fc1cc(-c2c3OCCCn3nc2C(=O)NC2CC2)c(F)cc1Cl WYSBJUKHVQZOHC-UHFFFAOYSA-N 0.000 claims description 2
- MYPOVEUFNMJGML-UHFFFAOYSA-N 3-(4-chloro-2,5-difluorophenyl)-N-ethyl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxamide Chemical compound CCNC(=O)c1nn2CCCOc2c1-c1cc(F)c(Cl)cc1F MYPOVEUFNMJGML-UHFFFAOYSA-N 0.000 claims description 2
- IFCNLIRUYVNPKA-UHFFFAOYSA-N 3-(4-chloro-2-fluorophenyl)-N-cyclopropyl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxamide Chemical compound Fc1cc(Cl)ccc1-c1c2OCCCn2nc1C(=O)NC1CC1 IFCNLIRUYVNPKA-UHFFFAOYSA-N 0.000 claims description 2
- RQKJDWFZSBVQSW-UHFFFAOYSA-N 3-(4-chloro-2-methylphenyl)-N-cyclopropyl-6,6-difluoro-5,7-dihydropyrazolo[5,1-b][1,3]oxazine-2-carboxamide Chemical compound Cc1cc(Cl)ccc1-c1c2OCC(F)(F)Cn2nc1C(=O)NC1CC1 RQKJDWFZSBVQSW-UHFFFAOYSA-N 0.000 claims description 2
- KXLPTRRQYABNIU-UHFFFAOYSA-N 3-(4-chloro-2-methylphenyl)-N-cyclopropyl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxamide Chemical compound Cc1cc(Cl)ccc1-c1c2OCCCn2nc1C(=O)NC1CC1 KXLPTRRQYABNIU-UHFFFAOYSA-N 0.000 claims description 2
- GRFHQTKEAOBDST-UHFFFAOYSA-N 3-(4-chloro-2-methylphenyl)-N-cyclopropyl-6-fluoro-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxamide Chemical compound Cc1cc(Cl)ccc1-c1c(nn2CC(F)COc12)C(=O)NC1CC1 GRFHQTKEAOBDST-UHFFFAOYSA-N 0.000 claims description 2
- ZDSSYIMMEPTDEO-UHFFFAOYSA-N 3-(4-chloro-3,5-difluorophenyl)-N-cyclopropyl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxamide Chemical compound Fc1cc(cc(F)c1Cl)-c1c2OCCCn2nc1C(=O)NC1CC1 ZDSSYIMMEPTDEO-UHFFFAOYSA-N 0.000 claims description 2
- TWKMZYIUVKFGDK-UHFFFAOYSA-N 3-(4-chloro-3-fluorophenyl)-N-cyclopropyl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxamide Chemical compound Fc1cc(ccc1Cl)-c1c2OCCCn2nc1C(=O)NC1CC1 TWKMZYIUVKFGDK-UHFFFAOYSA-N 0.000 claims description 2
- MKFKTQOJJMIDOC-UHFFFAOYSA-N 3-(4-chloro-3-fluorophenyl)-N-cyclopropyl-6-fluoro-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxamide Chemical compound FC1COc2c(c(nn2C1)C(=O)NC1CC1)-c1ccc(Cl)c(F)c1 MKFKTQOJJMIDOC-UHFFFAOYSA-N 0.000 claims description 2
- KPTCNORYAGZPTM-UHFFFAOYSA-N 3-(4-chloro-3-fluorophenyl)-N-methyl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxamide Chemical compound CNC(=O)c1nn2CCCOc2c1-c1ccc(Cl)c(F)c1 KPTCNORYAGZPTM-UHFFFAOYSA-N 0.000 claims description 2
- SPFPGSNCBFECSG-UHFFFAOYSA-N 3-(4-chloro-3-fluorophenyl)-N-propan-2-yl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxamide Chemical compound CC(C)NC(=O)c1nn2CCCOc2c1-c1ccc(Cl)c(F)c1 SPFPGSNCBFECSG-UHFFFAOYSA-N 0.000 claims description 2
- AIIYPFJZLRJGEL-UHFFFAOYSA-N 3-(4-chloro-5-fluoro-2-methylphenyl)-N-cyclopropyl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxamide Chemical compound Cc1cc(Cl)c(F)cc1-c1c2OCCCn2nc1C(=O)NC1CC1 AIIYPFJZLRJGEL-UHFFFAOYSA-N 0.000 claims description 2
- WYVVCFNADZMHEN-UHFFFAOYSA-N 3-(4-chloro-5-fluoro-2-methylphenyl)-N-ethyl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxamide Chemical compound CCNC(=O)c1nn2CCCOc2c1-c1cc(F)c(Cl)cc1C WYVVCFNADZMHEN-UHFFFAOYSA-N 0.000 claims description 2
- XWLDNGLNMIBYMP-UHFFFAOYSA-N 3-(4-chloro-5-fluoro-2-methylphenyl)-N-methyl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxamide Chemical compound CNC(=O)c1nn2CCCOc2c1-c1cc(F)c(Cl)cc1C XWLDNGLNMIBYMP-UHFFFAOYSA-N 0.000 claims description 2
- GYVJFOZZFFIUSZ-UHFFFAOYSA-N 3-(4-chlorophenyl)-N-cyclopropyl-5-methyl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxamide Chemical compound CC1CCn2nc(C(=O)NC3CC3)c(c2O1)-c1ccc(Cl)cc1 GYVJFOZZFFIUSZ-UHFFFAOYSA-N 0.000 claims description 2
- NHVPCMGYIPONNR-UHFFFAOYSA-N 3-(4-chlorophenyl)-N-cyclopropyl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxamide Chemical compound Clc1ccc(cc1)-c1c2OCCCn2nc1C(=O)NC1CC1 NHVPCMGYIPONNR-UHFFFAOYSA-N 0.000 claims description 2
- NXQIEDDZYQXLGS-UHFFFAOYSA-N 3-(4-chlorophenyl)-N-cyclopropyl-6-fluoro-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxamide Chemical compound FC1COc2c(c(nn2C1)C(=O)NC1CC1)-c1ccc(Cl)cc1 NXQIEDDZYQXLGS-UHFFFAOYSA-N 0.000 claims description 2
- ZTEOJNWIHZBBMB-UHFFFAOYSA-N 3-(4-chlorophenyl)-N-cyclopropyl-7-methyl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxamide Chemical compound CC1CCOc2c(c(nn12)C(=O)NC1CC1)-c1ccc(Cl)cc1 ZTEOJNWIHZBBMB-UHFFFAOYSA-N 0.000 claims description 2
- KEZOJFATBPGWGR-UHFFFAOYSA-N 3-(4-cyano-2,5-difluorophenyl)-N-cyclopropyl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxamide Chemical compound Fc1cc(-c2c3OCCCn3nc2C(=O)NC2CC2)c(F)cc1C#N KEZOJFATBPGWGR-UHFFFAOYSA-N 0.000 claims description 2
- MGICYBWWARAATG-UHFFFAOYSA-N 3-(4-cyano-2-methylphenyl)-N-cyclopropyl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxamide Chemical compound Cc1cc(ccc1-c1c2OCCCn2nc1C(=O)NC1CC1)C#N MGICYBWWARAATG-UHFFFAOYSA-N 0.000 claims description 2
- RQCIGHZUMYJCCJ-UHFFFAOYSA-N 3-(4-cyano-3-fluorophenyl)-N-cyclopropyl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxamide Chemical compound C(#N)C1=C(C=C(C=C1)C=1C(=NN2C=1OCCC2)C(=O)NC1CC1)F RQCIGHZUMYJCCJ-UHFFFAOYSA-N 0.000 claims description 2
- CICKNGAWODWCEX-UHFFFAOYSA-N 3-(4-cyano-5-fluoro-2-methylphenyl)-N-cyclopropyl-6-fluoro-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxamide Chemical compound Cc1cc(C#N)c(F)cc1-c1c(nn2CC(F)COc12)C(=O)NC1CC1 CICKNGAWODWCEX-UHFFFAOYSA-N 0.000 claims description 2
- GWWNXYAZKUJVBF-UHFFFAOYSA-N 3-(4-cyano-5-fluoro-2-methylphenyl)-N-ethyl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxamide Chemical compound CCNC(=O)c1nn2CCCOc2c1-c1cc(F)c(cc1C)C#N GWWNXYAZKUJVBF-UHFFFAOYSA-N 0.000 claims description 2
- QQMQNXMQOPTOHL-UHFFFAOYSA-N 3-(5-cyano-2-fluorophenyl)-N-cyclopropyl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxamide Chemical compound Fc1ccc(cc1-c1c2OCCCn2nc1C(=O)NC1CC1)C#N QQMQNXMQOPTOHL-UHFFFAOYSA-N 0.000 claims description 2
- WAMLUDBFCUDTPT-UHFFFAOYSA-N 3-(6-cyanopyridin-3-yl)-N-cyclopropyl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxamide Chemical compound O=C(NC1CC1)c1nn2CCCOc2c1-c1ccc(nc1)C#N WAMLUDBFCUDTPT-UHFFFAOYSA-N 0.000 claims description 2
- HIZORNOKOHJTBO-UHFFFAOYSA-N 4-[2-(azetidine-1-carbonyl)-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazin-3-yl]-2,5-difluorobenzonitrile Chemical compound Fc1cc(-c2c3OCCCn3nc2C(=O)N2CCC2)c(F)cc1C#N HIZORNOKOHJTBO-UHFFFAOYSA-N 0.000 claims description 2
- JVQZYDGQUZXTDQ-UHFFFAOYSA-N 4-[2-(azetidine-1-carbonyl)-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazin-3-yl]-2,6-difluorobenzonitrile Chemical compound Fc1cc(cc(F)c1C#N)-c1c2OCCCn2nc1C(=O)N1CCC1 JVQZYDGQUZXTDQ-UHFFFAOYSA-N 0.000 claims description 2
- 208000024827 Alzheimer disease Diseases 0.000 claims description 2
- 208000019901 Anxiety disease Diseases 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 2
- TUHZURBDZPBKQB-UHFFFAOYSA-N ClC1=CC=C(C=C1)C=1C(=NN2C=1OCC(C2)(F)F)C(=O)NC1CC1 Chemical compound ClC1=CC=C(C=C1)C=1C(=NN2C=1OCC(C2)(F)F)C(=O)NC1CC1 TUHZURBDZPBKQB-UHFFFAOYSA-N 0.000 claims description 2
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims description 2
- 101001098805 Homo sapiens cAMP-specific 3',5'-cyclic phosphodiesterase 4A Proteins 0.000 claims description 2
- 101000988424 Homo sapiens cAMP-specific 3',5'-cyclic phosphodiesterase 4B Proteins 0.000 claims description 2
- 101000988423 Homo sapiens cAMP-specific 3',5'-cyclic phosphodiesterase 4C Proteins 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
- 206010061218 Inflammation Diseases 0.000 claims description 2
- XMTOCICLPIPODV-UHFFFAOYSA-N N-cyclopropyl-3-(3,4-dichlorophenyl)-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxamide Chemical compound Clc1ccc(cc1Cl)-c1c2OCCCn2nc1C(=O)NC1CC1 XMTOCICLPIPODV-UHFFFAOYSA-N 0.000 claims description 2
- MYBATSJXBUMOOH-UHFFFAOYSA-N N-cyclopropyl-3-[2-(difluoromethoxy)pyridin-4-yl]-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxamide Chemical compound FC(F)Oc1cc(ccn1)-c1c(nn2CCCOc12)C(=O)NC1CC1 MYBATSJXBUMOOH-UHFFFAOYSA-N 0.000 claims description 2
- ONZFTFUFKHZXEF-UHFFFAOYSA-N N-cyclopropyl-3-pyrazolo[1,5-a]pyridin-6-yl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxamide Chemical compound O=C(NC1CC1)c1nn2CCCOc2c1-c1ccc2ccnn2c1 ONZFTFUFKHZXEF-UHFFFAOYSA-N 0.000 claims description 2
- 208000018737 Parkinson disease Diseases 0.000 claims description 2
- 102000001708 Protein Isoforms Human genes 0.000 claims description 2
- 108010029485 Protein Isoforms Proteins 0.000 claims description 2
- 208000006011 Stroke Diseases 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 208000002205 allergic conjunctivitis Diseases 0.000 claims description 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 2
- 230000036506 anxiety Effects 0.000 claims description 2
- 208000006673 asthma Diseases 0.000 claims description 2
- 208000024998 atopic conjunctivitis Diseases 0.000 claims description 2
- OEWWVAVGPPIPRO-UHFFFAOYSA-N azetidin-1-yl-[3-(3,4-dichlorophenyl)-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazin-2-yl]methanone Chemical compound Clc1ccc(cc1Cl)-c1c(nn2CCCOc12)C(=O)N1CCC1 OEWWVAVGPPIPRO-UHFFFAOYSA-N 0.000 claims description 2
- ARADJHAPDWYDIE-UHFFFAOYSA-N azetidin-1-yl-[3-(3,5-difluoro-4-methoxyphenyl)-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazin-2-yl]methanone Chemical compound COc1c(F)cc(cc1F)-c1c2OCCCn2nc1C(=O)N1CCC1 ARADJHAPDWYDIE-UHFFFAOYSA-N 0.000 claims description 2
- HGOQXTQGKPHGEY-UHFFFAOYSA-N azetidin-1-yl-[3-(4-chloro-2,3-difluorophenyl)-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazin-2-yl]methanone Chemical compound N1(CCC1)C(=O)C1=NN2C(OCCC2)=C1C1=C(C(=C(C=C1)Cl)F)F HGOQXTQGKPHGEY-UHFFFAOYSA-N 0.000 claims description 2
- LTQPXIUEDFTWNR-UHFFFAOYSA-N azetidin-1-yl-[3-(4-chloro-2,5-difluorophenyl)-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazin-2-yl]methanone Chemical compound N1(CCC1)C(=O)C1=NN2C(OCCC2)=C1C1=C(C=C(C(=C1)F)Cl)F LTQPXIUEDFTWNR-UHFFFAOYSA-N 0.000 claims description 2
- AYWBPURWDSSBNA-UHFFFAOYSA-N azetidin-1-yl-[3-(4-chloro-2-fluorophenyl)-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazin-2-yl]methanone Chemical compound Fc1cc(Cl)ccc1-c1c2OCCCn2nc1C(=O)N1CCC1 AYWBPURWDSSBNA-UHFFFAOYSA-N 0.000 claims description 2
- BLUWLSQGJDRYLP-UHFFFAOYSA-N azetidin-1-yl-[3-(4-chloro-2-methylphenyl)-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazin-2-yl]methanone Chemical compound Cc1cc(Cl)ccc1-c1c2OCCCn2nc1C(=O)N1CCC1 BLUWLSQGJDRYLP-UHFFFAOYSA-N 0.000 claims description 2
- XUMPDYRHXWOEDT-UHFFFAOYSA-N azetidin-1-yl-[3-(4-chloro-3,5-difluorophenyl)-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazin-2-yl]methanone Chemical compound Fc1cc(cc(F)c1Cl)-c1c2OCCCn2nc1C(=O)N1CCC1 XUMPDYRHXWOEDT-UHFFFAOYSA-N 0.000 claims description 2
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| EP3824906A1 (en) | 2016-12-21 | 2021-05-26 | Amgen Inc. | Anti-tnf alpha antibody formulations |
| CA3092579A1 (en) | 2018-03-01 | 2019-09-06 | Board Of Regents, The University Of Texas System | Ethanediamine-heterocycle derivatives as inhibitors of protein arginine methyltransferases |
| BR112021001608A2 (pt) * | 2018-09-10 | 2021-04-27 | Kaken Pharmaceutical Co., Ltd. | derivado de amida heteroaromático inovador e medicamento contendo o mesmo |
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