ES2426023T3 - Compuestos bicíclicos para la reducción de producción de beta amiloide - Google Patents

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Publication number

ES2426023T3

ES2426023T3 ES10700643T ES10700643T ES2426023T3 ES 2426023 T3 ES2426023 T3 ES 2426023T3 ES 10700643 T ES10700643 T ES 10700643T ES 10700643 T ES10700643 T ES 10700643T ES 2426023 T3 ES2426023 T3 ES 2426023T3

Authority

ES

Spain

Prior art keywords

triazolo

phenyl

tetrahydro

azepin

chloro

Prior art date

2009-01-16

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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• 238000004519 manufacturing process Methods 0.000 title claims description 16
• 230000009467 reduction Effects 0.000 title claims description 9
• 125000002619 bicyclic group Chemical group 0.000 title description 5
• 108010090849 Amyloid beta-Peptides Proteins 0.000 title description 3
• 102000013455 Amyloid beta-Peptides Human genes 0.000 title description 3
• -1 hydroxy, amino Chemical group 0.000 claims abstract description 408
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 180
• 150000001875 compounds Chemical class 0.000 claims abstract description 151
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 87
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 66
• 125000005843 halogen group Chemical group 0.000 claims abstract description 59
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 39
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 38
• 125000004076 pyridyl group Chemical group 0.000 claims abstract description 36
• 239000001257 hydrogen Substances 0.000 claims abstract description 35
• 125000001424 substituent group Chemical group 0.000 claims abstract description 32
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 31
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 29
• 150000003839 salts Chemical class 0.000 claims abstract description 29
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 27
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 26
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 19
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims abstract description 18
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract description 17
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 17
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 15
• 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 14
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 13
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 12
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims abstract description 11
• 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 10
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims abstract description 7
• 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims abstract description 7
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 6
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
• 239000001301 oxygen Substances 0.000 claims abstract description 5
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
• 239000011593 sulfur Substances 0.000 claims abstract description 5
• 238000000034 method Methods 0.000 claims description 143
• GJPUTKWVQJEZPE-UHFFFAOYSA-N 1h-azepin-2-amine Chemical compound NC1=CC=CC=CN1 GJPUTKWVQJEZPE-UHFFFAOYSA-N 0.000 claims description 128
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 115
• 238000011282 treatment Methods 0.000 claims description 35
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
• BXLHOSHUHPPGDV-UHFFFAOYSA-N 1h-azepin-2-ol Chemical compound OC1=CC=CC=CN1 BXLHOSHUHPPGDV-UHFFFAOYSA-N 0.000 claims description 27
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 27
• 208000024827 Alzheimer disease Diseases 0.000 claims description 25
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 20
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
• 239000008194 pharmaceutical composition Substances 0.000 claims description 18
• JZFSLMDLIPKTAO-UHFFFAOYSA-N 1,3-dihydroazepin-2-one Chemical compound O=C1CC=CC=CN1 JZFSLMDLIPKTAO-UHFFFAOYSA-N 0.000 claims description 15
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 15
• 125000002883 imidazolyl group Chemical group 0.000 claims description 14
• 125000001425 triazolyl group Chemical group 0.000 claims description 14
• 208000035475 disorder Diseases 0.000 claims description 12
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 7
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 7
• 201000010374 Down Syndrome Diseases 0.000 claims description 7
• DZHSAHHDTRWUTF-SIQRNXPUSA-N amyloid-beta polypeptide 42 Chemical compound C([C@@H](C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@H](C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)NCC(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(O)=O)[C@@H](C)CC)C(C)C)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC(O)=O)C(C)C)C(C)C)C1=CC=CC=C1 DZHSAHHDTRWUTF-SIQRNXPUSA-N 0.000 claims description 7
• 239000003085 diluting agent Substances 0.000 claims description 7
• 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 6
• 208000002780 macular degeneration Diseases 0.000 claims description 6
• VTHAWVAAIFRQTO-UHFFFAOYSA-N n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-9-(4-fluorophenyl)-8,9-dihydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C=1C=C(N2C=C(Cl)N=C2)C(OC)=CC=1NC(=NN1CC=CC2)N=C1C2C1=CC=C(F)C=C1 VTHAWVAAIFRQTO-UHFFFAOYSA-N 0.000 claims description 6
• APOKHFRRRWYFQT-UHFFFAOYSA-N 1H-azepine-2,3-diol Chemical compound N1C(=C(C=CC=C1)O)O APOKHFRRRWYFQT-UHFFFAOYSA-N 0.000 claims description 5
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 5
• ZQKKUACPEQGYGK-UHFFFAOYSA-N 9-(4-fluorophenyl)-n-[3-methoxy-4-(3-methyl-1,2,4-triazol-1-yl)phenyl]-8,9-dihydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C=1C=C(N2N=C(C)N=C2)C(OC)=CC=1NC(=NN1CC=CC2)N=C1C2C1=CC=C(F)C=C1 ZQKKUACPEQGYGK-UHFFFAOYSA-N 0.000 claims description 5
• 208000005145 Cerebral amyloid angiopathy Diseases 0.000 claims description 5
• 206010064930 age-related macular degeneration Diseases 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• OIZXNQQCBZBLPI-UHFFFAOYSA-N n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-9-(3,4,5-trifluorophenyl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C=1C=C(N2C=C(Cl)N=C2)C(OC)=CC=1NC(=NN1CCCC2)N=C1C2C1=CC(F)=C(F)C(F)=C1 OIZXNQQCBZBLPI-UHFFFAOYSA-N 0.000 claims description 5
• IECYPDLRLARBTB-UHFFFAOYSA-N n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-9-(4-fluorophenyl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C=1C=C(N2C=C(Cl)N=C2)C(OC)=CC=1NC(=NN1CCCC2)N=C1C2C1=CC=C(F)C=C1 IECYPDLRLARBTB-UHFFFAOYSA-N 0.000 claims description 5
• 230000002829 reductive effect Effects 0.000 claims description 5
• WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 4
• 241000124008 Mammalia Species 0.000 claims description 4
• 201000002481 Myositis Diseases 0.000 claims description 4
• PHTMVIAGTMTVSK-UHFFFAOYSA-N [1,2,4]triazolo[1,5-a]pyridin-2-amine Chemical compound C1=CC=CN2N=C(N)N=C21 PHTMVIAGTMTVSK-UHFFFAOYSA-N 0.000 claims description 4
• 208000010877 cognitive disease Diseases 0.000 claims description 4
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 4
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
• 230000008569 process Effects 0.000 claims description 4
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
• PETFLWQZSWIXIC-LJQANCHMSA-N (9r)-n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-9-(4-fluorophenyl)-7-methylidene-5,6,8,9-tetrahydro-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C1([C@@H]2C3=NC(=NN3CCC(=C)C2)NC=2C=C(C(=CC=2)N2C=C(Cl)N=C2)OC)=CC=C(F)C=C1 PETFLWQZSWIXIC-LJQANCHMSA-N 0.000 claims description 3
• NQZLDYNWFMODIM-UHFFFAOYSA-N 1h-azepin-3-ol Chemical compound OC1=CNC=CC=C1 NQZLDYNWFMODIM-UHFFFAOYSA-N 0.000 claims description 3
• ATMGMCKLGOHVRT-UHFFFAOYSA-N 9-(4-fluorophenyl)-n-[3-methoxy-4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C=1C=C(C=2ON=C(C)N=2)C(OC)=CC=1NC(=NN1CCCC2)N=C1C2C1=CC=C(F)C=C1 ATMGMCKLGOHVRT-UHFFFAOYSA-N 0.000 claims description 3
• 206010067889 Dementia with Lewy bodies Diseases 0.000 claims description 3
• 201000002832 Lewy body dementia Diseases 0.000 claims description 3
• 206010028980 Neoplasm Diseases 0.000 claims description 3
• 201000011510 cancer Diseases 0.000 claims description 3
• 210000003000 inclusion body Anatomy 0.000 claims description 3
• 208000027061 mild cognitive impairment Diseases 0.000 claims description 3
• MZOJBYNMNGPCME-UHFFFAOYSA-N n-[2-fluoro-5-methoxy-4-(3-methyl-1,2,4-triazol-1-yl)phenyl]-9-[4-(2,2,2-trifluoroethoxy)phenyl]-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound FC=1C=C(N2N=C(C)N=C2)C(OC)=CC=1NC(=NN1CCCC2)N=C1C2C1=CC=C(OCC(F)(F)F)C=C1 MZOJBYNMNGPCME-UHFFFAOYSA-N 0.000 claims description 3
• ZGEIPGMPHOCQIY-UHFFFAOYSA-N n-[3-fluoro-4-(3-methyl-1,2,4-triazol-1-yl)phenyl]-9-[4-(2,2,2-trifluoroethoxy)phenyl]-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound N1=C(C)N=CN1C(C(=C1)F)=CC=C1NC1=NN2CCCCC(C=3C=CC(OCC(F)(F)F)=CC=3)C2=N1 ZGEIPGMPHOCQIY-UHFFFAOYSA-N 0.000 claims description 3
• GXUIBEGWVDCQHE-UHFFFAOYSA-N n-[3-fluoro-4-(5-methyl-1,2,4-triazol-1-yl)phenyl]-8-(4-fluorophenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-amine Chemical compound CC1=NC=NN1C(C(=C1)F)=CC=C1NC1=NN2CCCC(C=3C=CC(F)=CC=3)C2=N1 GXUIBEGWVDCQHE-UHFFFAOYSA-N 0.000 claims description 3
• KNHITGRUZFMVLF-UHFFFAOYSA-N n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-9-(2,4-dichlorophenyl)-8,9-dihydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C=1C=C(N2C=C(Cl)N=C2)C(OC)=CC=1NC(=NN1CC=CC2)N=C1C2C1=CC=C(Cl)C=C1Cl KNHITGRUZFMVLF-UHFFFAOYSA-N 0.000 claims description 3
• UPLRVCGMDNCGNC-UHFFFAOYSA-N n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-9-(2-fluorophenyl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C=1C=C(N2C=C(Cl)N=C2)C(OC)=CC=1NC(=NN1CCCC2)N=C1C2C1=CC=CC=C1F UPLRVCGMDNCGNC-UHFFFAOYSA-N 0.000 claims description 3
• XRRCVLNYATYOLT-UHFFFAOYSA-N n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-9-(3-fluorophenyl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C=1C=C(N2C=C(Cl)N=C2)C(OC)=CC=1NC(=NN1CCCC2)N=C1C2C1=CC=CC(F)=C1 XRRCVLNYATYOLT-UHFFFAOYSA-N 0.000 claims description 3
• ZQKKUACPEQGYGK-LJQANCHMSA-N (9r)-9-(4-fluorophenyl)-n-[3-methoxy-4-(3-methyl-1,2,4-triazol-1-yl)phenyl]-8,9-dihydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C1([C@@H]2C3=NC(=NN3CC=CC2)NC=2C=C(C(=CC=2)N2N=C(C)N=C2)OC)=CC=C(F)C=C1 ZQKKUACPEQGYGK-LJQANCHMSA-N 0.000 claims description 2
• VNJJNEUHBAJYST-QGZVFWFLSA-N (9r)-n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-9-(2,4-difluorophenyl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C1([C@@H]2C3=NC(=NN3CCCC2)NC=2C=C(C(=CC=2)N2C=C(Cl)N=C2)OC)=CC=C(F)C=C1F VNJJNEUHBAJYST-QGZVFWFLSA-N 0.000 claims description 2
• UPLRVCGMDNCGNC-QGZVFWFLSA-N (9r)-n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-9-(2-fluorophenyl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C1([C@@H]2C3=NC(=NN3CCCC2)NC=2C=C(C(=CC=2)N2C=C(Cl)N=C2)OC)=CC=CC=C1F UPLRVCGMDNCGNC-QGZVFWFLSA-N 0.000 claims description 2
• OIZXNQQCBZBLPI-OAHLLOKOSA-N (9r)-n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-9-(3,4,5-trifluorophenyl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C1([C@@H]2C3=NC(=NN3CCCC2)NC=2C=C(C(=CC=2)N2C=C(Cl)N=C2)OC)=CC(F)=C(F)C(F)=C1 OIZXNQQCBZBLPI-OAHLLOKOSA-N 0.000 claims description 2
• IECYPDLRLARBTB-GOSISDBHSA-N (9r)-n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-9-(4-fluorophenyl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C1([C@@H]2C3=NC(=NN3CCCC2)NC=2C=C(C(=CC=2)N2C=C(Cl)N=C2)OC)=CC=C(F)C=C1 IECYPDLRLARBTB-GOSISDBHSA-N 0.000 claims description 2
• VTHAWVAAIFRQTO-GOSISDBHSA-N (9r)-n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-9-(4-fluorophenyl)-8,9-dihydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C1([C@@H]2C3=NC(=NN3CC=CC2)NC=2C=C(C(=CC=2)N2C=C(Cl)N=C2)OC)=CC=C(F)C=C1 VTHAWVAAIFRQTO-GOSISDBHSA-N 0.000 claims description 2
• CTDJIZCCHAQGEI-UHFFFAOYSA-N 2-[4-(4-chloroimidazol-1-yl)-3-methoxyanilino]-7-ethyl-9-(4-fluorophenyl)-5,6,8,9-tetrahydro-[1,2,4]triazolo[1,5-a]azepin-7-ol Chemical compound N1=C2C(C=3C=CC(F)=CC=3)CC(CC)(O)CCN2N=C1NC(C=C1OC)=CC=C1N1C=NC(Cl)=C1 CTDJIZCCHAQGEI-UHFFFAOYSA-N 0.000 claims description 2
• NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 2
• GDTOJGYZPQAPBA-UHFFFAOYSA-N 7-(azetidin-1-yl)-n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-9-(4-fluorophenyl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C=1C=C(N2C=C(Cl)N=C2)C(OC)=CC=1NC(=NN1CC2)N=C1C(C=1C=CC(F)=CC=1)CC2N1CCC1 GDTOJGYZPQAPBA-UHFFFAOYSA-N 0.000 claims description 2
• STCJZEUXGBWJQB-UHFFFAOYSA-N 9-(4-fluorophenyl)-n-[3-methoxy-4-(3-methyl-1,2-oxazol-5-yl)phenyl]-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C=1C=C(C=2ON=C(C)C=2)C(OC)=CC=1NC(=NN1CCCC2)N=C1C2C1=CC=C(F)C=C1 STCJZEUXGBWJQB-UHFFFAOYSA-N 0.000 claims description 2
• XYQTVJRDVVTBMA-UHFFFAOYSA-N 9-(4-fluorophenyl)-n-[3-methoxy-4-(6-methylpyridazin-4-yl)phenyl]-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C=1C=C(C=2C=C(C)N=NC=2)C(OC)=CC=1NC(=NN1CCCC2)N=C1C2C1=CC=C(F)C=C1 XYQTVJRDVVTBMA-UHFFFAOYSA-N 0.000 claims description 2
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
• HGYRHOIVRTUKEJ-UHFFFAOYSA-N n-[3-fluoro-4-(3-methyl-1,2,4-triazol-1-yl)phenyl]-9-(4-fluorophenyl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound N1=C(C)N=CN1C(C(=C1)F)=CC=C1NC1=NN2CCCCC(C=3C=CC(F)=CC=3)C2=N1 HGYRHOIVRTUKEJ-UHFFFAOYSA-N 0.000 claims description 2
• YVPHOYSDZMKDTF-UHFFFAOYSA-N n-[3-fluoro-4-(3-methyl-1,2,4-triazol-1-yl)phenyl]-9-[4-(trifluoromethoxy)phenyl]-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound N1=C(C)N=CN1C(C(=C1)F)=CC=C1NC1=NN2CCCCC(C=3C=CC(OC(F)(F)F)=CC=3)C2=N1 YVPHOYSDZMKDTF-UHFFFAOYSA-N 0.000 claims description 2
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