RU2719599C2 - Соединения 6, 7-дигидро-5H-пиразоло[5,1-b][1,3]оксазин-2-карбоксамида - Google Patents

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Publication number

RU2719599C2

RU2719599C2 RU2018128781A RU2018128781A RU2719599C2 RU 2719599 C2 RU2719599 C2 RU 2719599C2 RU 2018128781 A RU2018128781 A RU 2018128781A RU 2018128781 A RU2018128781 A RU 2018128781A RU 2719599 C2 RU2719599 C2 RU 2719599C2

Authority

RU

Russia

Prior art keywords

pyrazolo

dihydro

oxazine

carboxamide

cyclopropyl

Prior art date

2016-02-23

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 246
• VYMFHYCOVQSQTL-UHFFFAOYSA-N 6,7-dihydro-5h-pyrazolo[5,1-b][1,3]oxazine-2-carboxamide Chemical compound O1CCCN2N=C(C(=O)N)C=C21 VYMFHYCOVQSQTL-UHFFFAOYSA-N 0.000 title 1
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 67
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 60
• 150000003839 salts Chemical class 0.000 claims abstract description 60
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 50
• 238000000034 method Methods 0.000 claims abstract description 46
• 125000001424 substituent group Chemical group 0.000 claims abstract description 43
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 38
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 36
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 27
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 27
• 239000001257 hydrogen Substances 0.000 claims abstract description 27
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 25
• 150000002367 halogens Chemical class 0.000 claims abstract description 23
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 19
• 125000004076 pyridyl group Chemical group 0.000 claims abstract description 17
• 201000010099 disease Diseases 0.000 claims abstract description 16
• 125000005843 halogen group Chemical group 0.000 claims abstract description 15
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract description 14
• 125000002393 azetidinyl group Chemical group 0.000 claims abstract description 12
• 101100296720 Dictyostelium discoideum Pde4 gene Proteins 0.000 claims abstract description 11
• 108010044467 Isoenzymes Proteins 0.000 claims abstract description 11
• 101100082610 Plasmodium falciparum (isolate 3D7) PDEdelta gene Proteins 0.000 claims abstract description 11
• 239000008194 pharmaceutical composition Substances 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 abstract description 9
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 8
• 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 7
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 7
• 201000000980 schizophrenia Diseases 0.000 claims abstract description 7
• 208000018737 Parkinson disease Diseases 0.000 claims abstract description 6
• 125000003386 piperidinyl group Chemical group 0.000 claims abstract description 6
• 208000019901 Anxiety disease Diseases 0.000 claims abstract description 5
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims abstract description 5
• 208000006011 Stroke Diseases 0.000 claims abstract description 5
• 201000006417 multiple sclerosis Diseases 0.000 claims abstract description 5
• 206010061218 Inflammation Diseases 0.000 claims abstract description 4
• 201000010105 allergic rhinitis Diseases 0.000 claims abstract description 4
• 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims abstract description 4
• 208000006673 asthma Diseases 0.000 claims abstract description 4
• 230000004054 inflammatory process Effects 0.000 claims abstract description 4
• 206010039085 Rhinitis allergic Diseases 0.000 claims abstract description 3
• 230000036506 anxiety Effects 0.000 claims abstract 2
• -1 triazolopyridinyl Chemical group 0.000 claims description 152
• 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 57
• 108010029485 Protein Isoforms Proteins 0.000 claims description 55
• 102000001708 Protein Isoforms Human genes 0.000 claims description 55
• 102100029168 cAMP-specific 3',5'-cyclic phosphodiesterase 4B Human genes 0.000 claims description 42
• 238000011282 treatment Methods 0.000 claims description 39
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
• 125000000217 alkyl group Chemical class 0.000 claims description 13
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
• 125000001153 fluoro group Chemical group F* 0.000 claims description 11
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
• 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 8
• 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 8
• 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 8
• 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 6
• 101001098805 Homo sapiens cAMP-specific 3',5'-cyclic phosphodiesterase 4A Proteins 0.000 claims description 6
• 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 6
• 102100037092 cAMP-specific 3',5'-cyclic phosphodiesterase 4A Human genes 0.000 claims description 6
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 6
• 101000988423 Homo sapiens cAMP-specific 3',5'-cyclic phosphodiesterase 4C Proteins 0.000 claims description 5
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
• 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 4
• 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 4
• 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 4
• 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 4
• 230000001404 mediated effect Effects 0.000 claims description 4
• 125000003545 alkoxy group Chemical class 0.000 claims description 3
• 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 claims description 3
• 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
• 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
• CICKNGAWODWCEX-NSHDSACASA-N (6S)-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(nn2C[C@H](F)COc12)C(=O)NC1CC1 CICKNGAWODWCEX-NSHDSACASA-N 0.000 claims 2
• 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 2
• DJQNRDCGWWXDHA-SECBINFHSA-N (6R)-3-(4-chloro-5-fluoro-2-methylphenyl)-N-cyclopropyl-6-fluoro-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxamide Chemical compound Cc1cc(Cl)c(F)cc1-c1c(nn2C[C@@H](F)COc12)C(=O)NC1CC1 DJQNRDCGWWXDHA-SECBINFHSA-N 0.000 claims 1
• 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 1
• CICKNGAWODWCEX-LLVKDONJSA-N (6R)-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(nn2C[C@@H](F)COc12)C(=O)NC1CC1 CICKNGAWODWCEX-LLVKDONJSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 1
• 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 1
• WSISMBBKFDPNKB-UHFFFAOYSA-N 3-(4-chloro-2,5-difluorophenyl)-N-cyclopropyl-6,6-difluoro-5,7-dihydropyrazolo[5,1-b][1,3]oxazine-2-carboxamide Chemical compound Fc1cc(-c2c3OCC(F)(F)Cn3nc2C(=O)NC2CC2)c(F)cc1Cl WSISMBBKFDPNKB-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• KKPVIUOWNKMGHX-UHFFFAOYSA-N 3-(4-cyano-2-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(cc1F)C#N KKPVIUOWNKMGHX-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 1
• 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 1
• ZVWGRJASDAIIGJ-UHFFFAOYSA-N 3-(5-cyano-2-methylphenyl)-N-cyclopropyl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxamide Chemical compound Cc1ccc(cc1-c1c2OCCCn2nc1C(=O)NC1CC1)C#N ZVWGRJASDAIIGJ-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• AJJQMMGWFICENJ-UHFFFAOYSA-N 3-[6-(difluoromethoxy)pyridin-3-yl]-N-methyl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxamide Chemical compound CNC(=O)c1nn2CCCOc2c1-c1ccc(OC(F)F)nc1 AJJQMMGWFICENJ-UHFFFAOYSA-N 0.000 claims 1
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