TW201414727A - 其係[鄰雙(雜)芳基]-[2-(間雙(雜)芳基)吡咯啶-1-基]甲酮衍生物之食慾素受體拮抗劑 - Google Patents
其係[鄰雙(雜)芳基]-[2-(間雙(雜)芳基)吡咯啶-1-基]甲酮衍生物之食慾素受體拮抗劑 Download PDFInfo
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- TW201414727A TW201414727A TW102136619A TW102136619A TW201414727A TW 201414727 A TW201414727 A TW 201414727A TW 102136619 A TW102136619 A TW 102136619A TW 102136619 A TW102136619 A TW 102136619A TW 201414727 A TW201414727 A TW 201414727A
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- Prior art keywords
- phenyl
- triazol
- methanone
- pyrrolidin
- methyl
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- 125000003118 aryl group Chemical group 0.000 title claims abstract description 22
- 229940123730 Orexin receptor antagonist Drugs 0.000 title abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 457
- 150000003839 salts Chemical class 0.000 claims abstract description 33
- 239000003814 drug Substances 0.000 claims abstract description 19
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- -1 2,3-dihydro-benzoyl group Chemical group 0.000 claims description 356
- 125000001424 substituent group Chemical group 0.000 claims description 176
- 125000000217 alkyl group Chemical group 0.000 claims description 156
- 238000000034 method Methods 0.000 claims description 117
- 239000000203 mixture Substances 0.000 claims description 111
- 229910052736 halogen Inorganic materials 0.000 claims description 90
- 150000002367 halogens Chemical class 0.000 claims description 90
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 90
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 73
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 68
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 67
- 102000002512 Orexin Human genes 0.000 claims description 58
- 108060005714 orexin Proteins 0.000 claims description 58
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 56
- 125000001072 heteroaryl group Chemical group 0.000 claims description 48
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 47
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 45
- 229910052757 nitrogen Inorganic materials 0.000 claims description 43
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 39
- 125000005842 heteroatom Chemical group 0.000 claims description 37
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims description 33
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 28
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- 125000004076 pyridyl group Chemical group 0.000 claims description 25
- 208000019116 sleep disease Diseases 0.000 claims description 25
- 208000019901 Anxiety disease Diseases 0.000 claims description 24
- 229910052799 carbon Inorganic materials 0.000 claims description 21
- 238000011282 treatment Methods 0.000 claims description 21
- 206010012335 Dependence Diseases 0.000 claims description 19
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 19
- 201000010099 disease Diseases 0.000 claims description 16
- 230000004064 dysfunction Effects 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- 208000019022 Mood disease Diseases 0.000 claims description 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
- 208000010877 cognitive disease Diseases 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 125000002971 oxazolyl group Chemical group 0.000 claims description 14
- 239000001301 oxygen Substances 0.000 claims description 14
- 239000011593 sulfur Substances 0.000 claims description 14
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 13
- 229940079593 drug Drugs 0.000 claims description 13
- 125000001153 fluoro group Chemical group F* 0.000 claims description 13
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 11
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 11
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 11
- 125000001425 triazolyl group Chemical group 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000000532 dioxanyl group Chemical group 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 9
- 208000017194 Affective disease Diseases 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 8
- 125000004304 oxazol-5-yl group Chemical group O1C=NC=C1* 0.000 claims description 8
- 208000027559 Appetite disease Diseases 0.000 claims description 7
- 230000036528 appetite Effects 0.000 claims description 7
- 235000019789 appetite Nutrition 0.000 claims description 7
- 230000004630 mental health Effects 0.000 claims description 7
- 208000020685 sleep-wake disease Diseases 0.000 claims description 7
- 125000000335 thiazolyl group Chemical group 0.000 claims description 7
- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims description 6
- 230000002265 prevention Effects 0.000 claims description 6
- 125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 125000004498 isoxazol-4-yl group Chemical group O1N=CC(=C1)* 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- AQBWFIUDEKGTJW-IBGZPJMESA-N (4,5-dimethyl-2-pyrazol-1-ylphenyl)-[(2s)-2-[3-[2-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]methanone Chemical compound N=1OC([C@@H]2CCCN2C(=O)C=2C=C(C(=CC=2N2N=CC=C2)C)C)=NC=1C1=CC=CC=C1OC(F)(F)F AQBWFIUDEKGTJW-IBGZPJMESA-N 0.000 claims description 2
- KFAYFXBNCHFRIM-QFIPXVFZSA-N (5-methoxy-2-phenylphenyl)-[(2s)-2-[3-[2-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]methanone Chemical compound N1([C@@H](CCC1)C=1ON=C(N=1)C=1C(=CC=CC=1)OC(F)(F)F)C(=O)C1=CC(OC)=CC=C1C1=CC=CC=C1 KFAYFXBNCHFRIM-QFIPXVFZSA-N 0.000 claims description 2
- JJLSTITYUOAKRB-QFIPXVFZSA-N (5-methyl-2-phenylphenyl)-[(2s)-2-[3-[2-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]methanone Chemical compound N1([C@@H](CCC1)C=1ON=C(N=1)C=1C(=CC=CC=1)OC(F)(F)F)C(=O)C1=CC(C)=CC=C1C1=CC=CC=C1 JJLSTITYUOAKRB-QFIPXVFZSA-N 0.000 claims description 2
- HRQHDSAGTVVGDG-IBGZPJMESA-N (5-methyl-2-pyrazol-1-ylphenyl)-[(2s)-2-[3-[2-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]methanone Chemical compound N=1OC([C@@H]2CCCN2C(=O)C=2C(=CC=C(C=2)C)N2N=CC=C2)=NC=1C1=CC=CC=C1OC(F)(F)F HRQHDSAGTVVGDG-IBGZPJMESA-N 0.000 claims description 2
- WNOBZVLDCLHESG-QFIPXVFZSA-N C(C)OC1=C(C=CC=C1)C1=CN=C(N1)[C@H]1N(CCC1)C(=O)C1=C(C=CC(=C1)C)N1N=CC=N1 Chemical compound C(C)OC1=C(C=CC=C1)C1=CN=C(N1)[C@H]1N(CCC1)C(=O)C1=C(C=CC(=C1)C)N1N=CC=N1 WNOBZVLDCLHESG-QFIPXVFZSA-N 0.000 claims description 2
- IWZYKLXJSHEIAN-KRWDZBQOSA-N CC1=CC(=C(C=C1)C(=O)N1[C@@H](CCC1)C1=NN=C(N1)C1=C(C=CC=C1)OC(F)(F)F)N1N=CC=N1 Chemical compound CC1=CC(=C(C=C1)C(=O)N1[C@@H](CCC1)C1=NN=C(N1)C1=C(C=CC=C1)OC(F)(F)F)N1N=CC=N1 IWZYKLXJSHEIAN-KRWDZBQOSA-N 0.000 claims description 2
- NGHOTNWDFFRERR-IBGZPJMESA-N CC1=CC(=C(C=C1C)C(=O)N1[C@@H](CCC1)C1=NC(=NO1)C1=C(C=CC=C1)C(F)(F)F)N1N=CC=N1 Chemical compound CC1=CC(=C(C=C1C)C(=O)N1[C@@H](CCC1)C1=NC(=NO1)C1=C(C=CC=C1)C(F)(F)F)N1N=CC=N1 NGHOTNWDFFRERR-IBGZPJMESA-N 0.000 claims description 2
- JIXLYZFMWGQCJO-IBGZPJMESA-N CC1=CC(=C(C=C1C)C(=O)N1[C@@H](CCC1)C1=NN=C(N1)C1=C(C(=CC=C1)F)OC)N1N=CC=N1 Chemical compound CC1=CC(=C(C=C1C)C(=O)N1[C@@H](CCC1)C1=NN=C(N1)C1=C(C(=CC=C1)F)OC)N1N=CC=N1 JIXLYZFMWGQCJO-IBGZPJMESA-N 0.000 claims description 2
- OWTICHBQSWXRQS-IBGZPJMESA-N CC1=CC(=C(C=C1C)C(=O)N1[C@@H](CCC1)C1=NN=C(N1)C1=C(C=CC=C1)OC)N1N=CC=N1 Chemical compound CC1=CC(=C(C=C1C)C(=O)N1[C@@H](CCC1)C1=NN=C(N1)C1=C(C=CC=C1)OC)N1N=CC=N1 OWTICHBQSWXRQS-IBGZPJMESA-N 0.000 claims description 2
- TVSGVYBYINFSEV-IBGZPJMESA-N CC1=CC(=C(C=C1C)C(=O)N1[C@@H](CCC1)C1=NN=C(N1)C=1C(=NC=CC1)OCC)N1N=CC=N1 Chemical compound CC1=CC(=C(C=C1C)C(=O)N1[C@@H](CCC1)C1=NN=C(N1)C=1C(=NC=CC1)OCC)N1N=CC=N1 TVSGVYBYINFSEV-IBGZPJMESA-N 0.000 claims description 2
- NTNSUMPZQLAAMK-DEOSSOPVSA-N CC1=CC(=C(C=C1C)C(=O)N1[C@@](CCC1)(C1=NN=C(N1)C1=C(C=CC=C1)OC(F)(F)F)C)N1N=CC=N1 Chemical compound CC1=CC(=C(C=C1C)C(=O)N1[C@@](CCC1)(C1=NN=C(N1)C1=C(C=CC=C1)OC(F)(F)F)C)N1N=CC=N1 NTNSUMPZQLAAMK-DEOSSOPVSA-N 0.000 claims description 2
- SLBSYBMINGTPCZ-IBGZPJMESA-N CC=1C=CC(=C(C1)C(=O)N1[C@@H](CCC1)C1=NC(=NO1)C1=C(C=CC=C1)C(F)(F)F)N1N=CC=N1 Chemical compound CC=1C=CC(=C(C1)C(=O)N1[C@@H](CCC1)C1=NC(=NO1)C1=C(C=CC=C1)C(F)(F)F)N1N=CC=N1 SLBSYBMINGTPCZ-IBGZPJMESA-N 0.000 claims description 2
- PGHJKLNWJBQMBU-SFHVURJKSA-N CC=1C=CC(=C(C1)C(=O)N1[C@@H](CCC1)C1=NN=C(N1)C1=C(C=CC=C1)OC(F)(F)F)N1N=CC=N1 Chemical compound CC=1C=CC(=C(C1)C(=O)N1[C@@H](CCC1)C1=NN=C(N1)C1=C(C=CC=C1)OC(F)(F)F)N1N=CC=N1 PGHJKLNWJBQMBU-SFHVURJKSA-N 0.000 claims description 2
- SGCLCURYCKUVAD-IBGZPJMESA-N CCOc1c(F)cccc1-c1nc(no1)[C@@H]1CCCN1C(=O)c1cc(OC)c(C)cc1-n1nccn1 Chemical compound CCOc1c(F)cccc1-c1nc(no1)[C@@H]1CCCN1C(=O)c1cc(OC)c(C)cc1-n1nccn1 SGCLCURYCKUVAD-IBGZPJMESA-N 0.000 claims description 2
- LYLJJUAAANDBTD-IBGZPJMESA-N CCOc1c(F)cccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1cc(OC)c(C)cc1-n1nccn1 Chemical compound CCOc1c(F)cccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1cc(OC)c(C)cc1-n1nccn1 LYLJJUAAANDBTD-IBGZPJMESA-N 0.000 claims description 2
- QUMNHSLYCANEIS-IBGZPJMESA-N CCOc1c(F)cccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1ccc(C)cc1-n1nccn1 Chemical compound CCOc1c(F)cccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1ccc(C)cc1-n1nccn1 QUMNHSLYCANEIS-IBGZPJMESA-N 0.000 claims description 2
- MUHYLIWIJWRUEE-NRFANRHFSA-N CCOc1ccccc1-c1cnc([nH]1)[C@@H]1CCCN1C(=O)c1ccc(C)cc1-n1nccn1 Chemical compound CCOc1ccccc1-c1cnc([nH]1)[C@@H]1CCCN1C(=O)c1ccc(C)cc1-n1nccn1 MUHYLIWIJWRUEE-NRFANRHFSA-N 0.000 claims description 2
- OLOZJJINZBPHSF-IBGZPJMESA-N CCOc1cnccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1cc(C)ccc1-n1nccn1 Chemical compound CCOc1cnccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1cc(C)ccc1-n1nccn1 OLOZJJINZBPHSF-IBGZPJMESA-N 0.000 claims description 2
- GNQFOWZBJSCIJQ-SFHVURJKSA-N CCOc1ncccc1-c1nnc([nH]1)[C@@H]1CCCN1C(=O)c1cc(Cl)c(C)cc1-n1nccn1 Chemical compound CCOc1ncccc1-c1nnc([nH]1)[C@@H]1CCCN1C(=O)c1cc(Cl)c(C)cc1-n1nccn1 GNQFOWZBJSCIJQ-SFHVURJKSA-N 0.000 claims description 2
- QCLSFIKPJILTAA-SFHVURJKSA-N CCOc1ncccc1-c1nnc([nH]1)[C@@H]1CCCN1C(=O)c1cc(OC)c(C)cc1-n1nccn1 Chemical compound CCOc1ncccc1-c1nnc([nH]1)[C@@H]1CCCN1C(=O)c1cc(OC)c(C)cc1-n1nccn1 QCLSFIKPJILTAA-SFHVURJKSA-N 0.000 claims description 2
- QPSRSPZUAGXOPN-KRWDZBQOSA-N CCOc1ncccc1-c1nnc([nH]1)[C@@H]1CCCN1C(=O)c1cc(OC)c(Cl)cc1-n1nccn1 Chemical compound CCOc1ncccc1-c1nnc([nH]1)[C@@H]1CCCN1C(=O)c1cc(OC)c(Cl)cc1-n1nccn1 QPSRSPZUAGXOPN-KRWDZBQOSA-N 0.000 claims description 2
- USGYMEPRBRHADY-SFHVURJKSA-N CCOc1ncccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1cc(Cl)c(C)cc1-n1nccn1 Chemical compound CCOc1ncccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1cc(Cl)c(C)cc1-n1nccn1 USGYMEPRBRHADY-SFHVURJKSA-N 0.000 claims description 2
- PAHRATIJXNTTMH-FQEVSTJZSA-N CCOc1ncccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1cc(OC)c(C)cc1-c1ncccn1 Chemical compound CCOc1ncccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1cc(OC)c(C)cc1-c1ncccn1 PAHRATIJXNTTMH-FQEVSTJZSA-N 0.000 claims description 2
- UJFJDIFKGXVSMY-KRWDZBQOSA-N CCOc1ncccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1cc(OC)c(Cl)cc1-n1nccn1 Chemical compound CCOc1ncccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1cc(OC)c(Cl)cc1-n1nccn1 UJFJDIFKGXVSMY-KRWDZBQOSA-N 0.000 claims description 2
- OXAADNBQTUMYTR-KRWDZBQOSA-N CCOc1ncccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1cc(OC)c(F)cc1-n1nccn1 Chemical compound CCOc1ncccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1cc(OC)c(F)cc1-n1nccn1 OXAADNBQTUMYTR-KRWDZBQOSA-N 0.000 claims description 2
- UZFYPNSAEROKQQ-IBGZPJMESA-N COC1=C(C=C(C=C1)C)C1=NC(=NO1)[C@H]1N(CCC1)C(=O)C1=C(C=C(C=C1)C)N1N=CC=N1 Chemical compound COC1=C(C=C(C=C1)C)C1=NC(=NO1)[C@H]1N(CCC1)C(=O)C1=C(C=C(C=C1)C)N1N=CC=N1 UZFYPNSAEROKQQ-IBGZPJMESA-N 0.000 claims description 2
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- MZISTCJNJATLBB-KRWDZBQOSA-N COC=1C(=CC(=C(C1)C(=O)N1[C@@H](CCC1)C1=NOC(=N1)C1=C(C=CC=C1)OC(F)(F)F)N1N=CC=N1)C Chemical compound COC=1C(=CC(=C(C1)C(=O)N1[C@@H](CCC1)C1=NOC(=N1)C1=C(C=CC=C1)OC(F)(F)F)N1N=CC=N1)C MZISTCJNJATLBB-KRWDZBQOSA-N 0.000 claims description 2
- ODORFZKNSBZADC-FQEVSTJZSA-N COC=1C=C(C=CC1)C1=NOC(=N1)[C@H]1N(CCC1)C(=O)C1=C(C=CC(=C1)C)N1N=CC=N1 Chemical compound COC=1C=C(C=CC1)C1=NOC(=N1)[C@H]1N(CCC1)C(=O)C1=C(C=CC(=C1)C)N1N=CC=N1 ODORFZKNSBZADC-FQEVSTJZSA-N 0.000 claims description 2
- MNDDUDYFBNUSMN-SFHVURJKSA-N COc1c(Cl)cccc1-c1nc(no1)[C@@H]1CCCN1C(=O)c1cc(Cl)ccc1-n1nccn1 Chemical compound COc1c(Cl)cccc1-c1nc(no1)[C@@H]1CCCN1C(=O)c1cc(Cl)ccc1-n1nccn1 MNDDUDYFBNUSMN-SFHVURJKSA-N 0.000 claims description 2
- NVXVUURIOYXZOO-NRFANRHFSA-N COc1c(F)cccc1-c1cc(on1)[C@@H]1CCCN1C(=O)c1cc(C)ccc1-n1nccn1 Chemical compound COc1c(F)cccc1-c1cc(on1)[C@@H]1CCCN1C(=O)c1cc(C)ccc1-n1nccn1 NVXVUURIOYXZOO-NRFANRHFSA-N 0.000 claims description 2
- WTMWAONOZHUUEE-KRWDZBQOSA-N COc1c(F)cccc1-c1nnc([nH]1)[C@@H]1CCCN1C(=O)c1ccc(Cl)cc1-n1nccn1 Chemical compound COc1c(F)cccc1-c1nnc([nH]1)[C@@H]1CCCN1C(=O)c1ccc(Cl)cc1-n1nccn1 WTMWAONOZHUUEE-KRWDZBQOSA-N 0.000 claims description 2
- QYHPIHQZYLRNIG-KRWDZBQOSA-N COc1c(F)cccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1ccc(Cl)cc1-n1nccn1 Chemical compound COc1c(F)cccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1ccc(Cl)cc1-n1nccn1 QYHPIHQZYLRNIG-KRWDZBQOSA-N 0.000 claims description 2
- FETULTQYTLUDQW-KRWDZBQOSA-N COc1c(F)cccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1ccc(cc1-n1nccn1)C(F)(F)F Chemical compound COc1c(F)cccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1ccc(cc1-n1nccn1)C(F)(F)F FETULTQYTLUDQW-KRWDZBQOSA-N 0.000 claims description 2
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- JJYKGAQEFYNQGC-NRFANRHFSA-N COc1cc(C(=O)N2CCC[C@H]2c2cc(on2)-c2cccc(Cl)c2C)c(cc1C)-n1nccn1 Chemical compound COc1cc(C(=O)N2CCC[C@H]2c2cc(on2)-c2cccc(Cl)c2C)c(cc1C)-n1nccn1 JJYKGAQEFYNQGC-NRFANRHFSA-N 0.000 claims description 2
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- FGJVFGAGGIQTLO-SFHVURJKSA-N COc1cc(C(=O)N2CCC[C@H]2c2nc(no2)-c2cccc(Cl)c2C)c(cc1OC)-n1nccn1 Chemical compound COc1cc(C(=O)N2CCC[C@H]2c2nc(no2)-c2cccc(Cl)c2C)c(cc1OC)-n1nccn1 FGJVFGAGGIQTLO-SFHVURJKSA-N 0.000 claims description 2
- SLPBBNNNUASMRF-IBGZPJMESA-N COc1cc(C(=O)N2CCC[C@H]2c2nc(no2)-c2cccc(F)c2C)c(cc1C)-n1nccn1 Chemical compound COc1cc(C(=O)N2CCC[C@H]2c2nc(no2)-c2cccc(F)c2C)c(cc1C)-n1nccn1 SLPBBNNNUASMRF-IBGZPJMESA-N 0.000 claims description 2
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- HAUFXBYQCBBPLG-KRWDZBQOSA-N COc1cc(C(=O)N2CCC[C@H]2c2nc(no2)-c2cccc(F)c2OC)c(cc1OC)-n1nccn1 Chemical compound COc1cc(C(=O)N2CCC[C@H]2c2nc(no2)-c2cccc(F)c2OC)c(cc1OC)-n1nccn1 HAUFXBYQCBBPLG-KRWDZBQOSA-N 0.000 claims description 2
- WDDLEGYJQLYTLS-SFHVURJKSA-N COc1cc(C(=O)N2CCC[C@H]2c2nc(no2)-c2ccccc2OC(F)(F)F)c(cc1C)-n1cccn1 Chemical compound COc1cc(C(=O)N2CCC[C@H]2c2nc(no2)-c2ccccc2OC(F)(F)F)c(cc1C)-n1cccn1 WDDLEGYJQLYTLS-SFHVURJKSA-N 0.000 claims description 2
- CJXLJKJEJSIZHV-KRWDZBQOSA-N COc1cc(C(=O)N2CCC[C@H]2c2nnc([nH]2)-c2cccc(F)c2OC)c(cc1Cl)-n1nccn1 Chemical compound COc1cc(C(=O)N2CCC[C@H]2c2nnc([nH]2)-c2cccc(F)c2OC)c(cc1Cl)-n1nccn1 CJXLJKJEJSIZHV-KRWDZBQOSA-N 0.000 claims description 2
- RSXKWQLWTISAIG-KRWDZBQOSA-N COc1cc(C(=O)N2CCC[C@H]2c2nnc([nH]2)-c2ccccc2OC)c(cc1Cl)-n1nccn1 Chemical compound COc1cc(C(=O)N2CCC[C@H]2c2nnc([nH]2)-c2ccccc2OC)c(cc1Cl)-n1nccn1 RSXKWQLWTISAIG-KRWDZBQOSA-N 0.000 claims description 2
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- SGSJJQIHTRVECV-IBGZPJMESA-N COc1cc(C(=O)N2CCC[C@H]2c2noc(n2)-c2cc(C)ccc2OC)c(cc1C)-n1nccn1 Chemical compound COc1cc(C(=O)N2CCC[C@H]2c2noc(n2)-c2cc(C)ccc2OC)c(cc1C)-n1nccn1 SGSJJQIHTRVECV-IBGZPJMESA-N 0.000 claims description 2
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- RCGXSJKXQQBROC-INIZCTEOSA-N COc1cc(C(=O)N2CCC[C@H]2c2noc(n2)-c2ccccc2OC(F)(F)F)c(cc1Cl)-n1nccn1 Chemical compound COc1cc(C(=O)N2CCC[C@H]2c2noc(n2)-c2ccccc2OC(F)(F)F)c(cc1Cl)-n1nccn1 RCGXSJKXQQBROC-INIZCTEOSA-N 0.000 claims description 2
- XZFQMZJMIJHWDC-IBGZPJMESA-N COc1ccc(C(=O)N2CCC[C@H]2c2nc(no2)-c2cccc(Cl)c2C)c(c1)-n1nccn1 Chemical compound COc1ccc(C(=O)N2CCC[C@H]2c2nc(no2)-c2cccc(Cl)c2C)c(c1)-n1nccn1 XZFQMZJMIJHWDC-IBGZPJMESA-N 0.000 claims description 2
- AGAFBABVKPULNQ-FQEVSTJZSA-N COc1ccc(C)c(c1)-c1nc(no1)[C@@H]1CCCN1C(=O)c1cc(Cl)ccc1-n1nccn1 Chemical compound COc1ccc(C)c(c1)-c1nc(no1)[C@@H]1CCCN1C(=O)c1cc(Cl)ccc1-n1nccn1 AGAFBABVKPULNQ-FQEVSTJZSA-N 0.000 claims description 2
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- WYRXYORDVZVURM-IBGZPJMESA-N COc1ccc(c(c1)C(=O)N1CCC[C@H]1c1nc(no1)-c1cccc(F)c1OC)-n1nccn1 Chemical compound COc1ccc(c(c1)C(=O)N1CCC[C@H]1c1nc(no1)-c1cccc(F)c1OC)-n1nccn1 WYRXYORDVZVURM-IBGZPJMESA-N 0.000 claims description 2
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- RNJSXDPVIKEQDS-IBGZPJMESA-N Cc1ccc(c(c1)C(=O)N1CCC[C@H]1c1nc(no1)-c1cccc(Cl)c1)-n1nccn1 Chemical compound Cc1ccc(c(c1)C(=O)N1CCC[C@H]1c1nc(no1)-c1cccc(Cl)c1)-n1nccn1 RNJSXDPVIKEQDS-IBGZPJMESA-N 0.000 claims description 2
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- JFKPHXAMVDYFHM-IBGZPJMESA-N ClC1=CC(=C(C=C1)C(=O)N1[C@@H](CCC1)C1=NOC(=N1)C1=C(C=CC(=C1)C)C)N1N=CC=N1 Chemical compound ClC1=CC(=C(C=C1)C(=O)N1[C@@H](CCC1)C1=NOC(=N1)C1=C(C=CC(=C1)C)C)N1N=CC=N1 JFKPHXAMVDYFHM-IBGZPJMESA-N 0.000 claims description 2
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- GHRXATDKOUMVDJ-KRWDZBQOSA-N N=1N(N=CC1)C1=C(C=CC=C1)C(=O)N1[C@@H](CCC1)C1=NC(=NO1)C1=C(C=CC=C1)OC(F)(F)F Chemical compound N=1N(N=CC1)C1=C(C=CC=C1)C(=O)N1[C@@H](CCC1)C1=NC(=NO1)C1=C(C=CC=C1)OC(F)(F)F GHRXATDKOUMVDJ-KRWDZBQOSA-N 0.000 claims description 2
- ZITUKKHGVQJWGU-QFIPXVFZSA-N [(2s)-2-[3-(1-methylindol-3-yl)-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound N1([C@@H](CCC1)C=1ON=C(N=1)C=1C2=CC=CC=C2N(C)C=1)C(=O)C1=CC(C)=CC=C1N1N=CC=N1 ZITUKKHGVQJWGU-QFIPXVFZSA-N 0.000 claims description 2
- YVTHIABVFFJHMP-FQEVSTJZSA-N [(2s)-2-[3-(1-methylpyrrolo[2,3-b]pyridin-3-yl)-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound N1([C@@H](CCC1)C=1ON=C(N=1)C=1C2=CC=CN=C2N(C)C=1)C(=O)C1=CC(C)=CC=C1N1N=CC=N1 YVTHIABVFFJHMP-FQEVSTJZSA-N 0.000 claims description 2
- YPFANHJCIUGNFX-IBGZPJMESA-N [(2s)-2-[3-(2,3-dihydro-1,4-benzodioxin-5-yl)-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound N1([C@@H](CCC1)C=1ON=C(N=1)C=1C=2OCCOC=2C=CC=1)C(=O)C1=CC(C)=CC=C1N1N=CC=N1 YPFANHJCIUGNFX-IBGZPJMESA-N 0.000 claims description 2
- KLYDQFHKQVGPQO-QFIPXVFZSA-N [(2s)-2-[3-(2-cyclopropylphenyl)-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound N=1OC([C@@H]2CCCN2C(=O)C=2C(=CC=C(C=2)C)N2N=CC=N2)=NC=1C1=CC=CC=C1C1CC1 KLYDQFHKQVGPQO-QFIPXVFZSA-N 0.000 claims description 2
- OVALEAYBEXPOBZ-IBGZPJMESA-N [(2s)-2-[3-(2-ethoxyphenyl)-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]-[4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound CCOC1=CC=CC=C1C1=NOC([C@H]2N(CCC2)C(=O)C=2C(=CC(C)=CC=2)N2N=CC=N2)=N1 OVALEAYBEXPOBZ-IBGZPJMESA-N 0.000 claims description 2
- MOOJFCAHSQXGTF-FQEVSTJZSA-N [(2s)-2-[3-(2-ethoxyphenyl)-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound CCOC1=CC=CC=C1C1=NOC([C@H]2N(CCC2)C(=O)C=2C(=CC=C(C)C=2)N2N=CC=N2)=N1 MOOJFCAHSQXGTF-FQEVSTJZSA-N 0.000 claims description 2
- OICXNPWYVQDQDJ-SFHVURJKSA-N [(2s)-2-[3-(2-ethoxypyridin-3-yl)-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]-[5-methoxy-4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound CCOC1=NC=CC=C1C1=NOC([C@H]2N(CCC2)C(=O)C=2C(=CC(C)=C(OC)C=2)N2N=CC=N2)=N1 OICXNPWYVQDQDJ-SFHVURJKSA-N 0.000 claims description 2
- XDTWUYIFUWJHJO-IBGZPJMESA-N [(2s)-2-[3-(2-ethoxypyridin-3-yl)-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]-[5-methyl-2-(1,3-oxazol-2-yl)phenyl]methanone Chemical compound CCOC1=NC=CC=C1C1=NOC([C@H]2N(CCC2)C(=O)C=2C(=CC=C(C)C=2)C=2OC=CN=2)=N1 XDTWUYIFUWJHJO-IBGZPJMESA-N 0.000 claims description 2
- HNDFUSHHJCZIBK-IBGZPJMESA-N [(2s)-2-[3-(2-ethoxypyridin-3-yl)-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound CCOC1=NC=CC=C1C1=NOC([C@H]2N(CCC2)C(=O)C=2C(=CC=C(C)C=2)N2N=CC=N2)=N1 HNDFUSHHJCZIBK-IBGZPJMESA-N 0.000 claims description 2
- JOJYKUAAFKCDAP-NRFANRHFSA-N [(2s)-2-[3-(2-ethylphenyl)-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound CCC1=CC=CC=C1C1=NOC([C@H]2N(CCC2)C(=O)C=2C(=CC=C(C)C=2)N2N=CC=N2)=N1 JOJYKUAAFKCDAP-NRFANRHFSA-N 0.000 claims description 2
- DYOCRWOKDQEUMZ-DEOSSOPVSA-N [(2s)-2-[3-(3-chloro-2-methylphenyl)-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]-(5-methoxy-2-phenylphenyl)methanone Chemical compound N1([C@@H](CCC1)C=1ON=C(N=1)C=1C(=C(Cl)C=CC=1)C)C(=O)C1=CC(OC)=CC=C1C1=CC=CC=C1 DYOCRWOKDQEUMZ-DEOSSOPVSA-N 0.000 claims description 2
- AOTBDTKVDOOBKK-DEOSSOPVSA-N [(2s)-2-[3-(3-chloro-2-methylphenyl)-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]-(5-methyl-2-phenylphenyl)methanone Chemical compound N1([C@@H](CCC1)C=1ON=C(N=1)C=1C(=C(Cl)C=CC=1)C)C(=O)C1=CC(C)=CC=C1C1=CC=CC=C1 AOTBDTKVDOOBKK-DEOSSOPVSA-N 0.000 claims description 2
- OQKNBRCSHWHRMT-IBGZPJMESA-N [(2s)-2-[3-(3-chloro-2-methylphenyl)-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]-[5-methoxy-4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound N=1OC([C@@H]2CCCN2C(=O)C=2C=C(C(=CC=2N2N=CC=N2)C)OC)=NC=1C1=CC=CC(Cl)=C1C OQKNBRCSHWHRMT-IBGZPJMESA-N 0.000 claims description 2
- RGPJTJSFVNOMPE-FQEVSTJZSA-N [(2s)-2-[3-(3-chloro-2-methylphenyl)-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]-[5-methyl-2-(1,3-oxazol-2-yl)phenyl]methanone Chemical compound N1([C@@H](CCC1)C=1ON=C(N=1)C=1C(=C(Cl)C=CC=1)C)C(=O)C1=CC(C)=CC=C1C1=NC=CO1 RGPJTJSFVNOMPE-FQEVSTJZSA-N 0.000 claims description 2
- LIQZDMACERNNNO-SFHVURJKSA-N [(2s)-2-[3-(3-fluoro-2-methoxyphenyl)-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]-[5-methoxy-4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound N=1OC([C@@H]2CCCN2C(=O)C=2C=C(C(=CC=2N2N=CC=N2)C)OC)=NC=1C1=CC=CC(F)=C1OC LIQZDMACERNNNO-SFHVURJKSA-N 0.000 claims description 2
- PHECLAFBTXLENM-IBGZPJMESA-N [(2s)-2-[3-(3-fluoro-2-methoxyphenyl)-1h-1,2,4-triazol-5-yl]pyrrolidin-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound COC1=C(F)C=CC=C1C1=NNC([C@H]2N(CCC2)C(=O)C=2C(=CC=C(C)C=2)N2N=CC=N2)=N1 PHECLAFBTXLENM-IBGZPJMESA-N 0.000 claims description 2
- FHKLCVQERNPNFB-SFHVURJKSA-N [(2s)-2-[3-[2-(difluoromethoxy)phenyl]-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]-[4,5-dimethyl-2-(triazol-2-yl)phenyl]methanone Chemical compound N=1OC([C@@H]2CCCN2C(=O)C=2C=C(C(=CC=2N2N=CC=N2)C)C)=NC=1C1=CC=CC=C1OC(F)F FHKLCVQERNPNFB-SFHVURJKSA-N 0.000 claims description 2
- UOSSAVXHFVDLHG-FQEVSTJZSA-N [(2s)-2-[5-(2,3-dimethylphenyl)-1,2,4-oxadiazol-3-yl]pyrrolidin-1-yl]-[5-methoxy-4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound N=1C([C@@H]2CCCN2C(=O)C=2C=C(C(=CC=2N2N=CC=N2)C)OC)=NOC=1C1=CC=CC(C)=C1C UOSSAVXHFVDLHG-FQEVSTJZSA-N 0.000 claims description 2
- WAEXOHCHFPXJKG-IBGZPJMESA-N [(2s)-2-[5-(2-ethoxy-3-fluorophenyl)-1,2,4-oxadiazol-3-yl]pyrrolidin-1-yl]-[4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound CCOC1=C(F)C=CC=C1C1=NC([C@H]2N(CCC2)C(=O)C=2C(=CC(C)=CC=2)N2N=CC=N2)=NO1 WAEXOHCHFPXJKG-IBGZPJMESA-N 0.000 claims description 2
- PTYRUMWEJWQKEX-FQEVSTJZSA-N [(2s)-2-[5-(2-ethylphenyl)-1,2,4-oxadiazol-3-yl]pyrrolidin-1-yl]-[4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound CCC1=CC=CC=C1C1=NC([C@H]2N(CCC2)C(=O)C=2C(=CC(C)=CC=2)N2N=CC=N2)=NO1 PTYRUMWEJWQKEX-FQEVSTJZSA-N 0.000 claims description 2
- KYTNZCGPNOLKFR-SFHVURJKSA-N [(2s)-2-[5-(3-chloro-2-methoxyphenyl)-1,2,4-oxadiazol-3-yl]pyrrolidin-1-yl]-[4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound COC1=C(Cl)C=CC=C1C1=NC([C@H]2N(CCC2)C(=O)C=2C(=CC(C)=CC=2)N2N=CC=N2)=NO1 KYTNZCGPNOLKFR-SFHVURJKSA-N 0.000 claims description 2
- YGMFAGAXNKHGHK-SFHVURJKSA-N [(2s)-2-[5-(3-fluoro-2-methoxyphenyl)-1,2,4-oxadiazol-3-yl]pyrrolidin-1-yl]-[4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound COC1=C(F)C=CC=C1C1=NC([C@H]2N(CCC2)C(=O)C=2C(=CC(C)=CC=2)N2N=CC=N2)=NO1 YGMFAGAXNKHGHK-SFHVURJKSA-N 0.000 claims description 2
- BXNCXMMOWAUHNN-FQEVSTJZSA-N [4,5-dimethyl-2-(triazol-2-yl)phenyl]-[(2s)-2-[3-(2-ethoxyphenyl)-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]methanone Chemical compound CCOC1=CC=CC=C1C1=NOC([C@H]2N(CCC2)C(=O)C=2C(=CC(C)=C(C)C=2)N2N=CC=N2)=N1 BXNCXMMOWAUHNN-FQEVSTJZSA-N 0.000 claims description 2
- ATARZXBFRHLHQO-IBGZPJMESA-N [4,5-dimethyl-2-(triazol-2-yl)phenyl]-[(2s)-2-[3-(3-fluoro-2-methoxyphenyl)-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]methanone Chemical compound COC1=C(F)C=CC=C1C1=NOC([C@H]2N(CCC2)C(=O)C=2C(=CC(C)=C(C)C=2)N2N=CC=N2)=N1 ATARZXBFRHLHQO-IBGZPJMESA-N 0.000 claims description 2
- XFRQAEZGKBUEPA-FQEVSTJZSA-N [4,5-dimethyl-2-(triazol-2-yl)phenyl]-[(2s)-2-[3-(3-fluoro-2-methylphenyl)-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]methanone Chemical compound N=1OC([C@@H]2CCCN2C(=O)C=2C=C(C(=CC=2N2N=CC=N2)C)C)=NC=1C1=CC=CC(F)=C1C XFRQAEZGKBUEPA-FQEVSTJZSA-N 0.000 claims description 2
- ALLRFJYWSLYPOG-FQEVSTJZSA-N [4,5-dimethyl-2-(triazol-2-yl)phenyl]-[(2s)-2-[5-(2-ethoxy-3-fluorophenyl)-1,2,4-oxadiazol-3-yl]pyrrolidin-1-yl]methanone Chemical compound CCOC1=C(F)C=CC=C1C1=NC([C@H]2N(CCC2)C(=O)C=2C(=CC(C)=C(C)C=2)N2N=CC=N2)=NO1 ALLRFJYWSLYPOG-FQEVSTJZSA-N 0.000 claims description 2
- WFKJFMTZYPXCJR-NRFANRHFSA-N [4,5-dimethyl-2-(triazol-2-yl)phenyl]-[(2s)-2-[5-(2-ethylphenyl)-1,2,4-oxadiazol-3-yl]pyrrolidin-1-yl]methanone Chemical compound CCC1=CC=CC=C1C1=NC([C@H]2N(CCC2)C(=O)C=2C(=CC(C)=C(C)C=2)N2N=CC=N2)=NO1 WFKJFMTZYPXCJR-NRFANRHFSA-N 0.000 claims description 2
- UEQIXEFMENPZOI-NRFANRHFSA-N [4,5-dimethyl-2-(triazol-2-yl)phenyl]-[(2s)-2-[5-(5-methoxy-2-methylphenyl)-1,2,4-oxadiazol-3-yl]pyrrolidin-1-yl]methanone Chemical compound COC1=CC=C(C)C(C=2ON=C(N=2)[C@H]2N(CCC2)C(=O)C=2C(=CC(C)=C(C)C=2)N2N=CC=N2)=C1 UEQIXEFMENPZOI-NRFANRHFSA-N 0.000 claims description 2
- VKQDVMGJZIQRCE-KRWDZBQOSA-N [4-chloro-2-(triazol-2-yl)phenyl]-[(2s)-2-[5-(3-fluoro-2-methoxyphenyl)-1,2,4-oxadiazol-3-yl]pyrrolidin-1-yl]methanone Chemical compound COC1=C(F)C=CC=C1C1=NC([C@H]2N(CCC2)C(=O)C=2C(=CC(Cl)=CC=2)N2N=CC=N2)=NO1 VKQDVMGJZIQRCE-KRWDZBQOSA-N 0.000 claims description 2
- FRYUNBZKBYREKE-INIZCTEOSA-N [4-chloro-2-(triazol-2-yl)phenyl]-[(2s)-2-[5-[2-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-3-yl]pyrrolidin-1-yl]methanone Chemical compound FC(F)(F)OC1=CC=CC=C1C1=NC([C@H]2N(CCC2)C(=O)C=2C(=CC(Cl)=CC=2)N2N=CC=N2)=NO1 FRYUNBZKBYREKE-INIZCTEOSA-N 0.000 claims description 2
- UPCSQQLORDJECH-IBGZPJMESA-N [4-chloro-5-methoxy-2-(triazol-2-yl)phenyl]-[(2s)-2-[5-(2,3-dimethylphenyl)-1,2,4-oxadiazol-3-yl]pyrrolidin-1-yl]methanone Chemical compound N=1C([C@@H]2CCCN2C(=O)C=2C=C(C(=CC=2N2N=CC=N2)Cl)OC)=NOC=1C1=CC=CC(C)=C1C UPCSQQLORDJECH-IBGZPJMESA-N 0.000 claims description 2
- IDVJAKOPKJBANF-IBGZPJMESA-N [4-chloro-5-methoxy-2-(triazol-2-yl)phenyl]-[(2s)-2-[5-(2,5-dimethylphenyl)-1,2,4-oxadiazol-3-yl]pyrrolidin-1-yl]methanone Chemical compound N=1C([C@@H]2CCCN2C(=O)C=2C=C(C(=CC=2N2N=CC=N2)Cl)OC)=NOC=1C1=CC(C)=CC=C1C IDVJAKOPKJBANF-IBGZPJMESA-N 0.000 claims description 2
- OODNYHMRLDGQLL-SFHVURJKSA-N [4-chloro-5-methoxy-2-(triazol-2-yl)phenyl]-[(2s)-2-[5-(2-methoxy-5-methylphenyl)-1,2,4-oxadiazol-3-yl]pyrrolidin-1-yl]methanone Chemical compound N=1C([C@@H]2CCCN2C(=O)C=2C=C(C(=CC=2N2N=CC=N2)Cl)OC)=NOC=1C1=CC(C)=CC=C1OC OODNYHMRLDGQLL-SFHVURJKSA-N 0.000 claims description 2
- IPMQEASFHAYFRE-IBGZPJMESA-N [4-chloro-5-methoxy-2-(triazol-2-yl)phenyl]-[(2s)-2-[5-(3-methoxy-5-methylphenyl)-1,2,4-oxadiazol-3-yl]pyrrolidin-1-yl]methanone Chemical compound COC1=CC(C)=CC(C=2ON=C(N=2)[C@H]2N(CCC2)C(=O)C=2C(=CC(Cl)=C(OC)C=2)N2N=CC=N2)=C1 IPMQEASFHAYFRE-IBGZPJMESA-N 0.000 claims description 2
- CHNRUHKJLUIOKH-IBGZPJMESA-N [5-chloro-2-(triazol-2-yl)phenyl]-[(2s)-2-[3-(2-ethoxyphenyl)-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]methanone Chemical compound CCOC1=CC=CC=C1C1=NOC([C@H]2N(CCC2)C(=O)C=2C(=CC=C(Cl)C=2)N2N=CC=N2)=N1 CHNRUHKJLUIOKH-IBGZPJMESA-N 0.000 claims description 2
- GHVMBSHTEQHUHQ-SFHVURJKSA-N [5-chloro-2-(triazol-2-yl)phenyl]-[(2s)-2-[5-(2-ethoxypyridin-3-yl)-1,2,4-oxadiazol-3-yl]pyrrolidin-1-yl]methanone Chemical compound CCOC1=NC=CC=C1C1=NC([C@H]2N(CCC2)C(=O)C=2C(=CC=C(Cl)C=2)N2N=CC=N2)=NO1 GHVMBSHTEQHUHQ-SFHVURJKSA-N 0.000 claims description 2
- RKKXHCSZASMNJB-FQEVSTJZSA-N [5-chloro-2-(triazol-2-yl)phenyl]-[(2s)-2-[5-(2-ethylphenyl)-1,2,4-oxadiazol-3-yl]pyrrolidin-1-yl]methanone Chemical compound CCC1=CC=CC=C1C1=NC([C@H]2N(CCC2)C(=O)C=2C(=CC=C(Cl)C=2)N2N=CC=N2)=NO1 RKKXHCSZASMNJB-FQEVSTJZSA-N 0.000 claims description 2
- OKUWLYOXCJVLDR-KRWDZBQOSA-N [5-methoxy-4-methyl-2-(triazol-2-yl)phenyl]-[(2s)-2-[3-[2-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]methanone Chemical compound N=1OC([C@@H]2CCCN2C(=O)C=2C=C(C(=CC=2N2N=CC=N2)C)OC)=NC=1C1=CC=CC=C1OC(F)(F)F OKUWLYOXCJVLDR-KRWDZBQOSA-N 0.000 claims description 2
- DUMKORAJXQRADB-SFHVURJKSA-N [5-methyl-2-(1,3-oxazol-2-yl)phenyl]-[(2s)-2-[3-[2-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]methanone Chemical compound N1([C@@H](CCC1)C=1ON=C(N=1)C=1C(=CC=CC=1)OC(F)(F)F)C(=O)C1=CC(C)=CC=C1C1=NC=CO1 DUMKORAJXQRADB-SFHVURJKSA-N 0.000 claims description 2
- GKOVSCFLLBBOMY-FQEVSTJZSA-N [5-methyl-2-(triazol-2-yl)phenyl]-[(2s)-2-[3-(2-propan-2-yloxypyridin-3-yl)-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]methanone Chemical compound CC(C)OC1=NC=CC=C1C1=NOC([C@H]2N(CCC2)C(=O)C=2C(=CC=C(C)C=2)N2N=CC=N2)=N1 GKOVSCFLLBBOMY-FQEVSTJZSA-N 0.000 claims description 2
- MISGPPIHLOOXSD-SFHVURJKSA-N [5-methyl-2-(triazol-2-yl)phenyl]-[(2s)-2-[3-[2-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]methanone Chemical compound N=1OC([C@@H]2CCCN2C(=O)C=2C(=CC=C(C=2)C)N2N=CC=N2)=NC=1C1=CC=CC=C1OC(F)(F)F MISGPPIHLOOXSD-SFHVURJKSA-N 0.000 claims description 2
- WTIYRLUBVOWDQN-SFHVURJKSA-N [5-methyl-2-(triazol-2-yl)phenyl]-[(2s)-2-[5-[2-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-3-yl]pyrrolidin-1-yl]methanone Chemical compound N=1C([C@@H]2CCCN2C(=O)C=2C(=CC=C(C=2)C)N2N=CC=N2)=NOC=1C1=CC=CC=C1OC(F)(F)F WTIYRLUBVOWDQN-SFHVURJKSA-N 0.000 claims description 2
- 239000000470 constituent Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- SFMKLYCXWKPTSF-NRFANRHFSA-N (5-methyl-2-pyridin-2-ylphenyl)-[(2s)-2-[3-[2-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]methanone Chemical compound N1([C@@H](CCC1)C=1ON=C(N=1)C=1C(=CC=CC=1)OC(F)(F)F)C(=O)C1=CC(C)=CC=C1C1=CC=CC=N1 SFMKLYCXWKPTSF-NRFANRHFSA-N 0.000 claims 1
- KMDUTBGEZNBOMG-UHFFFAOYSA-N 2-(3-chlorophenyl)triazole Chemical compound ClC1=CC(=CC=C1)N1N=CC=N1 KMDUTBGEZNBOMG-UHFFFAOYSA-N 0.000 claims 1
- RDBXBVVGBXXYNE-UHFFFAOYSA-N 5-methyl-2-(triazol-2-yl)benzaldehyde Chemical compound O=CC1=CC(C)=CC=C1N1N=CC=N1 RDBXBVVGBXXYNE-UHFFFAOYSA-N 0.000 claims 1
- RNKHDMIFBGJSRQ-SFHVURJKSA-N C(C)OC1=NC=CC=C1C1=NOC(=N1)[C@H]1N(CCC1)C(=O)C1=C(C=C(C=C1)C)N1N=CC=N1 Chemical compound C(C)OC1=NC=CC=C1C1=NOC(=N1)[C@H]1N(CCC1)C(=O)C1=C(C=C(C=C1)C)N1N=CC=N1 RNKHDMIFBGJSRQ-SFHVURJKSA-N 0.000 claims 1
- GRTBTKHDHJBIBE-IBGZPJMESA-N C(C)OC1=NC=CC=C1C=1NC(=NN1)[C@H]1N(CCC1)C(=O)C1=C(C=CC(=C1)C)N1N=CC=N1 Chemical compound C(C)OC1=NC=CC=C1C=1NC(=NN1)[C@H]1N(CCC1)C(=O)C1=C(C=CC(=C1)C)N1N=CC=N1 GRTBTKHDHJBIBE-IBGZPJMESA-N 0.000 claims 1
- BRUXZKWUDDEDNK-IBGZPJMESA-N CC1=CC(=C(C=C1C)C(=O)N1[C@@H](CCC1)C1=NOC(=N1)C1=C(C(=CC=C1)F)OC)N1N=CC=N1 Chemical compound CC1=CC(=C(C=C1C)C(=O)N1[C@@H](CCC1)C1=NOC(=N1)C1=C(C(=CC=C1)F)OC)N1N=CC=N1 BRUXZKWUDDEDNK-IBGZPJMESA-N 0.000 claims 1
- QBOJPAJALJSCPZ-FQEVSTJZSA-N CC1=CC(=C(C=C1C)C(=O)N1[C@@H](CCC1)C1=NOC(=N1)C1=C(C(=CC=C1)OC)C)N1N=CC=N1 Chemical compound CC1=CC(=C(C=C1C)C(=O)N1[C@@H](CCC1)C1=NOC(=N1)C1=C(C(=CC=C1)OC)C)N1N=CC=N1 QBOJPAJALJSCPZ-FQEVSTJZSA-N 0.000 claims 1
- ZFAOCDJDWJPATF-FQEVSTJZSA-N CC1=CC(=C(C=C1C)C(=O)N1[C@@H](CCC1)C1=NOC(=N1)C1=C(C=CC(=C1)C)OC)N1N=CC=N1 Chemical compound CC1=CC(=C(C=C1C)C(=O)N1[C@@H](CCC1)C1=NOC(=N1)C1=C(C=CC(=C1)C)OC)N1N=CC=N1 ZFAOCDJDWJPATF-FQEVSTJZSA-N 0.000 claims 1
- QNLNRUKDTPQCQF-IBGZPJMESA-N CC=1C=CC(=C(C1)C(=O)N1[C@@H](CCC1)C1=NC(=NO1)C1=CC(=CC=C1)OC(F)(F)F)N1N=CC=N1 Chemical compound CC=1C=CC(=C(C1)C(=O)N1[C@@H](CCC1)C1=NC(=NO1)C1=CC(=CC=C1)OC(F)(F)F)N1N=CC=N1 QNLNRUKDTPQCQF-IBGZPJMESA-N 0.000 claims 1
- YSALRRJZLXWJIR-FQEVSTJZSA-N CC=1C=CC(=C(C1)C(=O)N1[C@@H](CCC1)C1=NC(=NO1)C=1C=C(C=CC1)C)N1N=CC=N1 Chemical compound CC=1C=CC(=C(C1)C(=O)N1[C@@H](CCC1)C1=NC(=NO1)C=1C=C(C=CC1)C)N1N=CC=N1 YSALRRJZLXWJIR-FQEVSTJZSA-N 0.000 claims 1
- MYWPKJICHKTMDN-SFHVURJKSA-N CCOc1c(F)cccc1-c1nc(no1)[C@@H]1CCCN1C(=O)c1cc(OC)c(Cl)cc1-n1nccn1 Chemical compound CCOc1c(F)cccc1-c1nc(no1)[C@@H]1CCCN1C(=O)c1cc(OC)c(Cl)cc1-n1nccn1 MYWPKJICHKTMDN-SFHVURJKSA-N 0.000 claims 1
- WGOKCSOLQVLCKP-FQEVSTJZSA-N CCOc1c(F)cccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1cc(C)c(C)cc1-n1nccn1 Chemical compound CCOc1c(F)cccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1cc(C)c(C)cc1-n1nccn1 WGOKCSOLQVLCKP-FQEVSTJZSA-N 0.000 claims 1
- XPAFAIBIIHHQBR-SFHVURJKSA-N CCOc1c(F)cccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1cc(OC)c(Cl)cc1-n1nccn1 Chemical compound CCOc1c(F)cccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1cc(OC)c(Cl)cc1-n1nccn1 XPAFAIBIIHHQBR-SFHVURJKSA-N 0.000 claims 1
- SZPPVOKLJAHBNZ-IBGZPJMESA-N CCOc1ccccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1cccc(F)c1-c1ccn[nH]1 Chemical compound CCOc1ccccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1cccc(F)c1-c1ccn[nH]1 SZPPVOKLJAHBNZ-IBGZPJMESA-N 0.000 claims 1
- NLURUCYGOQWQKJ-NRFANRHFSA-N CCOc1ncccc1-c1cc(on1)[C@@H]1CCCN1C(=O)c1cc(C)ccc1-n1nccn1 Chemical compound CCOc1ncccc1-c1cc(on1)[C@@H]1CCCN1C(=O)c1cc(C)ccc1-n1nccn1 NLURUCYGOQWQKJ-NRFANRHFSA-N 0.000 claims 1
- LOYJVOHUKOEBNR-IBGZPJMESA-N CCOc1ncccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1cc(C)cc(C)c1-n1nccn1 Chemical compound CCOc1ncccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1cc(C)cc(C)c1-n1nccn1 LOYJVOHUKOEBNR-IBGZPJMESA-N 0.000 claims 1
- LJLAUJLSTXXHLU-SFHVURJKSA-N CCOc1ncccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1cccc(F)c1-c1ccn[nH]1 Chemical compound CCOc1ncccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1cccc(F)c1-c1ccn[nH]1 LJLAUJLSTXXHLU-SFHVURJKSA-N 0.000 claims 1
- NQEPTESAYGYEQQ-IBGZPJMESA-N COC1=C(C=CC=C1)C1=NOC(=N1)[C@H]1N(CCC1)C(=O)C1=C(C=CC(=C1)C)N1N=CC=N1 Chemical compound COC1=C(C=CC=C1)C1=NOC(=N1)[C@H]1N(CCC1)C(=O)C1=C(C=CC(=C1)C)N1N=CC=N1 NQEPTESAYGYEQQ-IBGZPJMESA-N 0.000 claims 1
- UETJNGPHNQZUIC-FQEVSTJZSA-N COC=1C=CC(=C(C1)C1=NC(=NO1)[C@H]1N(CCC1)C(=O)C1=C(C=C(C=C1)C)N1N=CC=N1)C Chemical compound COC=1C=CC(=C(C1)C1=NC(=NO1)[C@H]1N(CCC1)C(=O)C1=C(C=C(C=C1)C)N1N=CC=N1)C UETJNGPHNQZUIC-FQEVSTJZSA-N 0.000 claims 1
- YRVOVIRWOCPRBZ-NRFANRHFSA-N COCc1ccccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1cc(C)ccc1-n1nccn1 Chemical compound COCc1ccccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1cc(C)ccc1-n1nccn1 YRVOVIRWOCPRBZ-NRFANRHFSA-N 0.000 claims 1
- ZOJKXWFXEAGBLO-SFHVURJKSA-N COc1c(F)cccc1-c1nnc([nH]1)[C@@H]1CCCN1C(=O)c1cc(Cl)c(C)cc1-n1nccn1 Chemical compound COc1c(F)cccc1-c1nnc([nH]1)[C@@H]1CCCN1C(=O)c1cc(Cl)c(C)cc1-n1nccn1 ZOJKXWFXEAGBLO-SFHVURJKSA-N 0.000 claims 1
- DXEUYBMFYQTSPN-IBGZPJMESA-N COc1c(F)cccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1cc(C)cc(C)c1-n1nccn1 Chemical compound COc1c(F)cccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1cc(C)cc(C)c1-n1nccn1 DXEUYBMFYQTSPN-IBGZPJMESA-N 0.000 claims 1
- AMUMNFNRAZYSFH-QFIPXVFZSA-N COc1c(F)cccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1cc(C)ccc1-c1ccccn1 Chemical compound COc1c(F)cccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1cc(C)ccc1-c1ccccn1 AMUMNFNRAZYSFH-QFIPXVFZSA-N 0.000 claims 1
- PLMYPKXVXMFNHI-FQEVSTJZSA-N COc1cc(C(=O)N2CCC[C@H]2c2cc(on2)-c2ccccc2)c(cc1C)-n1nccn1 Chemical compound COc1cc(C(=O)N2CCC[C@H]2c2cc(on2)-c2ccccc2)c(cc1C)-n1nccn1 PLMYPKXVXMFNHI-FQEVSTJZSA-N 0.000 claims 1
- LCFMWSWABLJLMB-FQEVSTJZSA-N COc1cc(C(=O)N2CCC[C@H]2c2nc(no2)-c2cccc(Cl)c2C)c(cc1C)-n1cccn1 Chemical compound COc1cc(C(=O)N2CCC[C@H]2c2nc(no2)-c2cccc(Cl)c2C)c(cc1C)-n1cccn1 LCFMWSWABLJLMB-FQEVSTJZSA-N 0.000 claims 1
- GOSHEXFXRFZAPB-SFHVURJKSA-N COc1cc(C(=O)N2CCC[C@H]2c2nc(no2)-c2cccc(Cl)c2C)c(cc1F)-n1nccn1 Chemical compound COc1cc(C(=O)N2CCC[C@H]2c2nc(no2)-c2cccc(Cl)c2C)c(cc1F)-n1nccn1 GOSHEXFXRFZAPB-SFHVURJKSA-N 0.000 claims 1
- DEUNGEPMJAXTRL-SFHVURJKSA-N COc1cc(C(=O)N2CCC[C@H]2c2nc(no2)-c2cccc(F)c2C)c(cc1Cl)-n1nccn1 Chemical compound COc1cc(C(=O)N2CCC[C@H]2c2nc(no2)-c2cccc(F)c2C)c(cc1Cl)-n1nccn1 DEUNGEPMJAXTRL-SFHVURJKSA-N 0.000 claims 1
- KLCQUHRBSBBNPE-KRWDZBQOSA-N COc1cc(C(=O)N2CCC[C@H]2c2nc(no2)-c2cccc(F)c2OC)c(cc1F)-n1nccn1 Chemical compound COc1cc(C(=O)N2CCC[C@H]2c2nc(no2)-c2cccc(F)c2OC)c(cc1F)-n1nccn1 KLCQUHRBSBBNPE-KRWDZBQOSA-N 0.000 claims 1
- MMYJITCJETUVAA-SFHVURJKSA-N COc1cc(C(=O)N2CCC[C@H]2c2nc(no2)-c2ccccc2C(F)(F)F)c(cc1C)-n1nccn1 Chemical compound COc1cc(C(=O)N2CCC[C@H]2c2nc(no2)-c2ccccc2C(F)(F)F)c(cc1C)-n1nccn1 MMYJITCJETUVAA-SFHVURJKSA-N 0.000 claims 1
- XNOXJRMDPXDIPI-SFHVURJKSA-N COc1cc(C(=O)N2CCC[C@H]2c2nc(no2)-c2ccccc2Cl)c(cc1C)-n1nccn1 Chemical compound COc1cc(C(=O)N2CCC[C@H]2c2nc(no2)-c2ccccc2Cl)c(cc1C)-n1nccn1 XNOXJRMDPXDIPI-SFHVURJKSA-N 0.000 claims 1
- PUJXIDCJYRYWTP-SFHVURJKSA-N COc1cc(C(=O)N2CCC[C@H]2c2nc(no2)-c2ccccc2OC)c(cc1C)-n1nccn1 Chemical compound COc1cc(C(=O)N2CCC[C@H]2c2nc(no2)-c2ccccc2OC)c(cc1C)-n1nccn1 PUJXIDCJYRYWTP-SFHVURJKSA-N 0.000 claims 1
- PEKATTSYWBWHSV-SFHVURJKSA-N COc1cc(C(=O)N2CCC[C@H]2c2nnc([nH]2)-c2cccc(Cl)c2OC)c(cc1C)-n1nccn1 Chemical compound COc1cc(C(=O)N2CCC[C@H]2c2nnc([nH]2)-c2cccc(Cl)c2OC)c(cc1C)-n1nccn1 PEKATTSYWBWHSV-SFHVURJKSA-N 0.000 claims 1
- QUQQYPYIPBBWEY-KRWDZBQOSA-N COc1cc(C(=O)N2CCC[C@H]2c2nnc([nH]2)-c2cccc(Cl)c2OC)c(cc1Cl)-n1nccn1 Chemical compound COc1cc(C(=O)N2CCC[C@H]2c2nnc([nH]2)-c2cccc(Cl)c2OC)c(cc1Cl)-n1nccn1 QUQQYPYIPBBWEY-KRWDZBQOSA-N 0.000 claims 1
- JOZFZVGLUUAMKM-KRWDZBQOSA-N COc1cc(C(=O)N2CCC[C@H]2c2nnc([nH]2)-c2ccccc2OC(F)(F)F)c(cc1C)-n1nccn1 Chemical compound COc1cc(C(=O)N2CCC[C@H]2c2nnc([nH]2)-c2ccccc2OC(F)(F)F)c(cc1C)-n1nccn1 JOZFZVGLUUAMKM-KRWDZBQOSA-N 0.000 claims 1
- ITWIBXFRJRYAIY-INIZCTEOSA-N COc1cc(C(=O)N2CCC[C@H]2c2nnc([nH]2)-c2ccccc2OC(F)(F)F)c(cc1Cl)-n1nccn1 Chemical compound COc1cc(C(=O)N2CCC[C@H]2c2nnc([nH]2)-c2ccccc2OC(F)(F)F)c(cc1Cl)-n1nccn1 ITWIBXFRJRYAIY-INIZCTEOSA-N 0.000 claims 1
- YACRFROESHCZFU-SFHVURJKSA-N COc1cc(C(=O)N2CCC[C@H]2c2nnc([nH]2)-c2ccccc2OC)c(cc1C)-n1nccn1 Chemical compound COc1cc(C(=O)N2CCC[C@H]2c2nnc([nH]2)-c2ccccc2OC)c(cc1C)-n1nccn1 YACRFROESHCZFU-SFHVURJKSA-N 0.000 claims 1
- HYRKSIIFYOQSTD-SFHVURJKSA-N COc1cc(C(=O)N2CCC[C@H]2c2nnc(o2)-c2cccc(Cl)c2C)c(cc1Cl)-n1nccn1 Chemical compound COc1cc(C(=O)N2CCC[C@H]2c2nnc(o2)-c2cccc(Cl)c2C)c(cc1Cl)-n1nccn1 HYRKSIIFYOQSTD-SFHVURJKSA-N 0.000 claims 1
- GNFWZOLSZWTYRR-IBGZPJMESA-N COc1cc(C(=O)N2CCC[C@H]2c2noc(n2)-c2cccc(Cl)c2C)c(cc1C)-n1nccn1 Chemical compound COc1cc(C(=O)N2CCC[C@H]2c2noc(n2)-c2cccc(Cl)c2C)c(cc1C)-n1nccn1 GNFWZOLSZWTYRR-IBGZPJMESA-N 0.000 claims 1
- CKQSGZJWVRFHLL-SFHVURJKSA-N COc1cc(C(=O)N2CCC[C@H]2c2noc(n2)-c2cccc(Cl)c2C)c(cc1Cl)-n1nccn1 Chemical compound COc1cc(C(=O)N2CCC[C@H]2c2noc(n2)-c2cccc(Cl)c2C)c(cc1Cl)-n1nccn1 CKQSGZJWVRFHLL-SFHVURJKSA-N 0.000 claims 1
- RRGQDAPENZQDHE-SFHVURJKSA-N COc1cc(C(=O)N2CCC[C@H]2c2noc(n2)-c2cccc(F)c2OC)c(cc1C)-n1nccn1 Chemical compound COc1cc(C(=O)N2CCC[C@H]2c2noc(n2)-c2cccc(F)c2OC)c(cc1C)-n1nccn1 RRGQDAPENZQDHE-SFHVURJKSA-N 0.000 claims 1
- WAKHHOMDKVZUIA-IBGZPJMESA-N COc1cc(C(=O)N2CCC[C@H]2c2noc(n2)-c2cccc(OC)c2C)c(cc1C)-n1nccn1 Chemical compound COc1cc(C(=O)N2CCC[C@H]2c2noc(n2)-c2cccc(OC)c2C)c(cc1C)-n1nccn1 WAKHHOMDKVZUIA-IBGZPJMESA-N 0.000 claims 1
- BJPSPFZAURHPMP-SFHVURJKSA-N COc1cc(C(=O)N2CCC[C@H]2c2noc(n2)-c2cccc(OC)c2C)c(cc1Cl)-n1nccn1 Chemical compound COc1cc(C(=O)N2CCC[C@H]2c2noc(n2)-c2cccc(OC)c2C)c(cc1Cl)-n1nccn1 BJPSPFZAURHPMP-SFHVURJKSA-N 0.000 claims 1
- RVRXQRGZGPRNHO-FQEVSTJZSA-N COc1ccc(C)c(c1)-c1nc(no1)[C@@H]1CCCN1C(=O)c1cc(OC)c(C)cc1-n1nccn1 Chemical compound COc1ccc(C)c(c1)-c1nc(no1)[C@@H]1CCCN1C(=O)c1cc(OC)c(C)cc1-n1nccn1 RVRXQRGZGPRNHO-FQEVSTJZSA-N 0.000 claims 1
- YGPNEYKKDUXPFQ-IBGZPJMESA-N COc1ccc(C)c(c1)-c1nc(no1)[C@@H]1CCCN1C(=O)c1cc(OC)c(Cl)cc1-n1nccn1 Chemical compound COc1ccc(C)c(c1)-c1nc(no1)[C@@H]1CCCN1C(=O)c1cc(OC)c(Cl)cc1-n1nccn1 YGPNEYKKDUXPFQ-IBGZPJMESA-N 0.000 claims 1
- NJUZPIMKSDPESQ-HNNXBMFYSA-N COc1ccc(c(C(=O)N2CCC[C@H]2c2nc(no2)-c2ccccc2OC(F)(F)F)c1F)-n1nccn1 Chemical compound COc1ccc(c(C(=O)N2CCC[C@H]2c2nc(no2)-c2ccccc2OC(F)(F)F)c1F)-n1nccn1 NJUZPIMKSDPESQ-HNNXBMFYSA-N 0.000 claims 1
- MZYVEKPEYBFDIX-FQEVSTJZSA-N COc1ccc(c(c1)C(=O)N1CCC[C@H]1c1nc(no1)-c1cccc(Cl)c1C)-n1nccn1 Chemical compound COc1ccc(c(c1)C(=O)N1CCC[C@H]1c1nc(no1)-c1cccc(Cl)c1C)-n1nccn1 MZYVEKPEYBFDIX-FQEVSTJZSA-N 0.000 claims 1
- PTCUMGQXAABERF-FQEVSTJZSA-N COc1ccc(c(c1)C(=O)N1CCC[C@H]1c1nc(no1)-c1cccc(F)c1C)-n1nccn1 Chemical compound COc1ccc(c(c1)C(=O)N1CCC[C@H]1c1nc(no1)-c1cccc(F)c1C)-n1nccn1 PTCUMGQXAABERF-FQEVSTJZSA-N 0.000 claims 1
- WFRSYFPLJNYJBR-IBGZPJMESA-N COc1cccc(-c2noc(n2)[C@@H]2CCCN2C(=O)c2cc(C)ccc2-n2nccn2)c1OC Chemical compound COc1cccc(-c2noc(n2)[C@@H]2CCCN2C(=O)c2cc(C)ccc2-n2nccn2)c1OC WFRSYFPLJNYJBR-IBGZPJMESA-N 0.000 claims 1
- IRCNQCYCHFKASB-KRWDZBQOSA-N COc1ccccc1-c1nnc([nH]1)[C@@H]1CCCN1C(=O)c1ccc(Cl)cc1-n1nccn1 Chemical compound COc1ccccc1-c1nnc([nH]1)[C@@H]1CCCN1C(=O)c1ccc(Cl)cc1-n1nccn1 IRCNQCYCHFKASB-KRWDZBQOSA-N 0.000 claims 1
- DXUJRFSLVWXJAM-IBGZPJMESA-N Cc1c(Cl)cccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1ccccc1-c1ncco1 Chemical compound Cc1c(Cl)cccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1ccccc1-c1ncco1 DXUJRFSLVWXJAM-IBGZPJMESA-N 0.000 claims 1
- NWIQYFNGCHIJSD-IBGZPJMESA-N Cc1c(F)cccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1cc(F)ccc1-n1nccn1 Chemical compound Cc1c(F)cccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1cc(F)ccc1-n1nccn1 NWIQYFNGCHIJSD-IBGZPJMESA-N 0.000 claims 1
- UZAWEHKKXGQPBY-SFHVURJKSA-N Cc1c(F)cccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1ccc(Cl)cc1-n1nccn1 Chemical compound Cc1c(F)cccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1ccc(Cl)cc1-n1nccn1 UZAWEHKKXGQPBY-SFHVURJKSA-N 0.000 claims 1
- AXVKMHHQSPETDL-IBGZPJMESA-N Cc1c(F)cccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1cccc(F)c1-c1ccn[nH]1 Chemical compound Cc1c(F)cccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1cccc(F)c1-c1ccn[nH]1 AXVKMHHQSPETDL-IBGZPJMESA-N 0.000 claims 1
- AKMDANQXWMVNEY-FQEVSTJZSA-N Cc1cc(C(=O)N2CCC[C@H]2c2noc(n2)-c2cccc(F)c2C)c(cc1C)-n1nccn1 Chemical compound Cc1cc(C(=O)N2CCC[C@H]2c2noc(n2)-c2cccc(F)c2C)c(cc1C)-n1nccn1 AKMDANQXWMVNEY-FQEVSTJZSA-N 0.000 claims 1
- BAJYHTHIBJYXEG-FQEVSTJZSA-N Cc1cc(C)c(c(c1)C(=O)N1CCC[C@H]1c1nc(no1)-c1cccc(Cl)c1C)-n1nccn1 Chemical compound Cc1cc(C)c(c(c1)C(=O)N1CCC[C@H]1c1nc(no1)-c1cccc(Cl)c1C)-n1nccn1 BAJYHTHIBJYXEG-FQEVSTJZSA-N 0.000 claims 1
- XMRRXJMXOZZRAE-QHCPKHFHSA-N Cc1ccc(-c2ccccn2)c(c1)C(=O)N1CCC[C@H]1c1nc(no1)-c1cccc(Cl)c1C Chemical compound Cc1ccc(-c2ccccn2)c(c1)C(=O)N1CCC[C@H]1c1nc(no1)-c1cccc(Cl)c1C XMRRXJMXOZZRAE-QHCPKHFHSA-N 0.000 claims 1
- YFGHKUFHITWOKA-NRFANRHFSA-N Cc1ccc(-c2ccccn2)c(c1)C(=O)N1CCC[C@H]1c1nc(no1)-c1ccccc1OC(F)F Chemical compound Cc1ccc(-c2ccccn2)c(c1)C(=O)N1CCC[C@H]1c1nc(no1)-c1ccccc1OC(F)F YFGHKUFHITWOKA-NRFANRHFSA-N 0.000 claims 1
- OIWYQRRPKCUGOL-FQEVSTJZSA-N Cc1ccc(C(=O)N2CCC[C@H]2c2noc(n2)-c2cccc(C)c2C)c(c1)-n1nccn1 Chemical compound Cc1ccc(C(=O)N2CCC[C@H]2c2noc(n2)-c2cccc(C)c2C)c(c1)-n1nccn1 OIWYQRRPKCUGOL-FQEVSTJZSA-N 0.000 claims 1
- KINPBHSOFYDWIG-SFHVURJKSA-N Cc1ccc(c(C(=O)N2CCC[C@H]2c2nc(no2)-c2cccc(Cl)c2C)c1F)-n1nccn1 Chemical compound Cc1ccc(c(C(=O)N2CCC[C@H]2c2nc(no2)-c2cccc(Cl)c2C)c1F)-n1nccn1 KINPBHSOFYDWIG-SFHVURJKSA-N 0.000 claims 1
- ARHATBKAZZLECO-QHCPKHFHSA-N Cc1ccc(c(c1)C(=O)N1CCC[C@@]1(C)c1nnc([nH]1)-c1ccccc1OC(F)(F)F)-n1nccn1 Chemical compound Cc1ccc(c(c1)C(=O)N1CCC[C@@]1(C)c1nnc([nH]1)-c1ccccc1OC(F)(F)F)-n1nccn1 ARHATBKAZZLECO-QHCPKHFHSA-N 0.000 claims 1
- LXBCMXPABDHUIZ-QHCPKHFHSA-N Cc1ccc(c(c1)C(=O)N1CCC[C@H]1c1cc(no1)-c1cccc(C)c1C)-n1nccn1 Chemical compound Cc1ccc(c(c1)C(=O)N1CCC[C@H]1c1cc(no1)-c1cccc(C)c1C)-n1nccn1 LXBCMXPABDHUIZ-QHCPKHFHSA-N 0.000 claims 1
- WHFQIPFBRFYCKU-NRFANRHFSA-N Cc1ccc(c(c1)C(=O)N1CCC[C@H]1c1cc(on1)-c1ccccc1)-n1nccn1 Chemical compound Cc1ccc(c(c1)C(=O)N1CCC[C@H]1c1cc(on1)-c1ccccc1)-n1nccn1 WHFQIPFBRFYCKU-NRFANRHFSA-N 0.000 claims 1
- HORXSENWOLHVDG-IBGZPJMESA-N Cc1ccc(c(c1)C(=O)N1CCC[C@H]1c1nc(no1)-c1c(C)cccc1F)-n1nccn1 Chemical compound Cc1ccc(c(c1)C(=O)N1CCC[C@H]1c1nc(no1)-c1c(C)cccc1F)-n1nccn1 HORXSENWOLHVDG-IBGZPJMESA-N 0.000 claims 1
- VTEVWDZJGRFWAY-NRFANRHFSA-N Cc1ccc(c(c1)C(=O)N1CCC[C@H]1c1nc(no1)-c1cccc(C)c1C)-n1nccn1 Chemical compound Cc1ccc(c(c1)C(=O)N1CCC[C@H]1c1nc(no1)-c1cccc(C)c1C)-n1nccn1 VTEVWDZJGRFWAY-NRFANRHFSA-N 0.000 claims 1
- COTMFCFRNPCBHW-NRFANRHFSA-N Cc1ccc(c(c1)C(=O)N1CCC[C@H]1c1nc(no1)-c1cccc(Cl)c1C)-n1cccn1 Chemical compound Cc1ccc(c(c1)C(=O)N1CCC[C@H]1c1nc(no1)-c1cccc(Cl)c1C)-n1cccn1 COTMFCFRNPCBHW-NRFANRHFSA-N 0.000 claims 1
- BLLZVYPTQBWRNA-SFHVURJKSA-N Cc1ccc(c(c1)C(=O)N1CCC[C@H]1c1nc(no1)-c1cccc2OCOc12)-n1nccn1 Chemical compound Cc1ccc(c(c1)C(=O)N1CCC[C@H]1c1nc(no1)-c1cccc2OCOc12)-n1nccn1 BLLZVYPTQBWRNA-SFHVURJKSA-N 0.000 claims 1
- GUTYDJGKTMGHRF-QFIPXVFZSA-N Cc1ccc(c(c1)C(=O)N1CCC[C@H]1c1nc(no1)-c1cccc2n(C)ccc12)-n1nccn1 Chemical compound Cc1ccc(c(c1)C(=O)N1CCC[C@H]1c1nc(no1)-c1cccc2n(C)ccc12)-n1nccn1 GUTYDJGKTMGHRF-QFIPXVFZSA-N 0.000 claims 1
- JLEZJDNALDAHLQ-FQEVSTJZSA-N Cc1ccc(c(c1)C(=O)N1CCC[C@H]1c1nc(no1)-c1ccccc1C)-n1nccn1 Chemical compound Cc1ccc(c(c1)C(=O)N1CCC[C@H]1c1nc(no1)-c1ccccc1C)-n1nccn1 JLEZJDNALDAHLQ-FQEVSTJZSA-N 0.000 claims 1
- AMECXQVHMZKCLX-IBGZPJMESA-N Cc1ccc(c(c1)C(=O)N1CCC[C@H]1c1nc(no1)-c1ccccc1Cl)-n1nccn1 Chemical compound Cc1ccc(c(c1)C(=O)N1CCC[C@H]1c1nc(no1)-c1ccccc1Cl)-n1nccn1 AMECXQVHMZKCLX-IBGZPJMESA-N 0.000 claims 1
- NZXVXTQNTGPZSS-SFHVURJKSA-N Cc1ccc(c(c1)C(=O)N1CCC[C@H]1c1nc(no1)-c1ccccc1OC(F)F)-n1nccn1 Chemical compound Cc1ccc(c(c1)C(=O)N1CCC[C@H]1c1nc(no1)-c1ccccc1OC(F)F)-n1nccn1 NZXVXTQNTGPZSS-SFHVURJKSA-N 0.000 claims 1
- VJYJPTZOKUNTGS-KRWDZBQOSA-N Cc1ccc(c(c1)C(=O)N1CCC[C@H]1c1nc(no1)-c1cccnc1Cl)-n1nccn1 Chemical compound Cc1ccc(c(c1)C(=O)N1CCC[C@H]1c1nc(no1)-c1cccnc1Cl)-n1nccn1 VJYJPTZOKUNTGS-KRWDZBQOSA-N 0.000 claims 1
- PDVSZNGWSRAFQD-NRFANRHFSA-N Cc1ccc(c(c1)C(=O)N1CCC[C@H]1c1nc(no1)-c1cccnc1OC1CCC1)-n1nccn1 Chemical compound Cc1ccc(c(c1)C(=O)N1CCC[C@H]1c1nc(no1)-c1cccnc1OC1CCC1)-n1nccn1 PDVSZNGWSRAFQD-NRFANRHFSA-N 0.000 claims 1
- DPJNNAKPGUYLIP-FQEVSTJZSA-N Cc1ccc(c(c1)C(=O)N1CCC[C@H]1c1ncn(n1)-c1ccccc1)-n1nccn1 Chemical compound Cc1ccc(c(c1)C(=O)N1CCC[C@H]1c1ncn(n1)-c1ccccc1)-n1nccn1 DPJNNAKPGUYLIP-FQEVSTJZSA-N 0.000 claims 1
- QEGCRQMUQILSSB-KRWDZBQOSA-N Cc1cccc(c1)-c1ocnc1C(=O)N1CCC[C@H]1c1nc(no1)-c1ccccc1OC(F)(F)F Chemical compound Cc1cccc(c1)-c1ocnc1C(=O)N1CCC[C@H]1c1nc(no1)-c1ccccc1OC(F)(F)F QEGCRQMUQILSSB-KRWDZBQOSA-N 0.000 claims 1
- CQXDHNQICUYCME-KRWDZBQOSA-N Cc1nc(C(=O)N2CCC[C@H]2c2nnc(o2)-c2ccccc2OC(F)(F)F)c(s1)-c1cccc(F)c1 Chemical compound Cc1nc(C(=O)N2CCC[C@H]2c2nnc(o2)-c2ccccc2OC(F)(F)F)c(s1)-c1cccc(F)c1 CQXDHNQICUYCME-KRWDZBQOSA-N 0.000 claims 1
- MLVMGAOQNWHRLW-IBGZPJMESA-N ClC1=C(C=CC=C1)C1=NOC(=N1)[C@H]1N(CCC1)C(=O)C1=C(C=C(C(=C1)C)C)N1N=CC=N1 Chemical compound ClC1=C(C=CC=C1)C1=NOC(=N1)[C@H]1N(CCC1)C(=O)C1=C(C=C(C(=C1)C)C)N1N=CC=N1 MLVMGAOQNWHRLW-IBGZPJMESA-N 0.000 claims 1
- CIXFDKCSGHGGNM-KRWDZBQOSA-N ClC1=CC(=C(C=C1)C(=O)N1[C@@H](CCC1)C1=NC(=NO1)C=1C(=NC=CC1)OCC)N1N=CC=N1 Chemical compound ClC1=CC(=C(C=C1)C(=O)N1[C@@H](CCC1)C1=NC(=NO1)C=1C(=NC=CC1)OCC)N1N=CC=N1 CIXFDKCSGHGGNM-KRWDZBQOSA-N 0.000 claims 1
- XEWMCRKQHIEWNY-KRWDZBQOSA-N ClC1=CC(=C(C=C1)C(=O)N1[C@@H](CCC1)C1=NN=C(N1)C=1C(=NC=CC1)OCC)N1N=CC=N1 Chemical compound ClC1=CC(=C(C=C1)C(=O)N1[C@@H](CCC1)C1=NN=C(N1)C=1C(=NC=CC1)OCC)N1N=CC=N1 XEWMCRKQHIEWNY-KRWDZBQOSA-N 0.000 claims 1
- RMSUYCUIZRSRCK-IBGZPJMESA-N ClC1=CC(=C(C=C1)C(=O)N1[C@@H](CCC1)C1=NOC(=N1)C1=C(C(=CC=C1)C)C)N1N=CC=N1 Chemical compound ClC1=CC(=C(C=C1)C(=O)N1[C@@H](CCC1)C1=NOC(=N1)C1=C(C(=CC=C1)C)C)N1N=CC=N1 RMSUYCUIZRSRCK-IBGZPJMESA-N 0.000 claims 1
- KOAIPQZPHNCZCQ-IBGZPJMESA-N ClC1=CC(=C(C=C1)C(=O)N1[C@@H](CCC1)C1=NOC(=N1)C1=C(C=CC(=C1)OC)C)N1N=CC=N1 Chemical compound ClC1=CC(=C(C=C1)C(=O)N1[C@@H](CCC1)C1=NOC(=N1)C1=C(C=CC(=C1)OC)C)N1N=CC=N1 KOAIPQZPHNCZCQ-IBGZPJMESA-N 0.000 claims 1
- WLBCPTKNCBIYOL-KRWDZBQOSA-N ClC1=CC(=C(C=C1OC)C(=O)N1[C@@H](CCC1)C1=NOC(=N1)C=1C(=NC=CC1)OCC)N1N=CC=N1 Chemical compound ClC1=CC(=C(C=C1OC)C(=O)N1[C@@H](CCC1)C1=NOC(=N1)C=1C(=NC=CC1)OCC)N1N=CC=N1 WLBCPTKNCBIYOL-KRWDZBQOSA-N 0.000 claims 1
- SIFXMAVPETUVES-QFIPXVFZSA-N ClC=1C(=C(C=CC1)C1=CC(=NO1)[C@H]1N(CCC1)C(=O)C1=C(C=CC(=C1)C)N1N=CC=N1)C Chemical compound ClC=1C(=C(C=CC1)C1=CC(=NO1)[C@H]1N(CCC1)C(=O)C1=C(C=CC(=C1)C)N1N=CC=N1)C SIFXMAVPETUVES-QFIPXVFZSA-N 0.000 claims 1
- VWZLKTHNERNQKO-FQEVSTJZSA-N ClC=1C(=C(C=CC1)C1=NN=C(O1)[C@H]1N(CCC1)C(=O)C1=C(C=CC(=C1)C)N1N=CC=N1)C Chemical compound ClC=1C(=C(C=CC1)C1=NN=C(O1)[C@H]1N(CCC1)C(=O)C1=C(C=CC(=C1)C)N1N=CC=N1)C VWZLKTHNERNQKO-FQEVSTJZSA-N 0.000 claims 1
- BTEPZYPEINXPCH-IBGZPJMESA-N ClC=1C(=C(C=CC1)C1=NOC(=N1)[C@H]1N(CCC1)C(=O)C1=C(C=CC(=C1)F)N1N=CC=N1)C Chemical compound ClC=1C(=C(C=CC1)C1=NOC(=N1)[C@H]1N(CCC1)C(=O)C1=C(C=CC(=C1)F)N1N=CC=N1)C BTEPZYPEINXPCH-IBGZPJMESA-N 0.000 claims 1
- WGNVKGARGFBADT-IBGZPJMESA-N ClC=1C(=C(C=CC1)C1=NOC(=N1)[C@H]1N(CCC1)C(=O)C1=C(C=CC=C1)N1N=CC=N1)C Chemical compound ClC=1C(=C(C=CC1)C1=NOC(=N1)[C@H]1N(CCC1)C(=O)C1=C(C=CC=C1)N1N=CC=N1)C WGNVKGARGFBADT-IBGZPJMESA-N 0.000 claims 1
- FHDNZNJPFZFVSL-SFHVURJKSA-N ClC=1C(=C(C=CC1)C=1NC(=NN1)[C@H]1N(CCC1)C(=O)C1=C(C=C(C=C1)C)N1N=CC=N1)OC Chemical compound ClC=1C(=C(C=CC1)C=1NC(=NN1)[C@H]1N(CCC1)C(=O)C1=C(C=C(C=C1)C)N1N=CC=N1)OC FHDNZNJPFZFVSL-SFHVURJKSA-N 0.000 claims 1
- QRFOYOCARWBVAU-FQEVSTJZSA-N ClC=1C(=C(C=CC1)C=1NC(=NN1)[C@H]1N(CCC1)C(=O)C1=C(C=CC(=C1)C)N1N=CC=N1)C Chemical compound ClC=1C(=C(C=CC1)C=1NC(=NN1)[C@H]1N(CCC1)C(=O)C1=C(C=CC(=C1)C)N1N=CC=N1)C QRFOYOCARWBVAU-FQEVSTJZSA-N 0.000 claims 1
- ZJXBFVDZTOERAK-IBGZPJMESA-N ClC=1C(=C(C=CC1)C=1NC(=NN1)[C@H]1N(CCC1)C(=O)C1=C(C=CC(=C1)C)N1N=CC=N1)OC Chemical compound ClC=1C(=C(C=CC1)C=1NC(=NN1)[C@H]1N(CCC1)C(=O)C1=C(C=CC(=C1)C)N1N=CC=N1)OC ZJXBFVDZTOERAK-IBGZPJMESA-N 0.000 claims 1
- OQEBFZOMRKUDRP-DEOSSOPVSA-N ClC=1C(=C(C=CC1)C=1NC(=NN1)[C@]1(N(CCC1)C(=O)C1=C(C=C(C=C1)C)N1N=CC=N1)C)C Chemical compound ClC=1C(=C(C=CC1)C=1NC(=NN1)[C@]1(N(CCC1)C(=O)C1=C(C=C(C=C1)C)N1N=CC=N1)C)C OQEBFZOMRKUDRP-DEOSSOPVSA-N 0.000 claims 1
- DTXKFFFJIWLWGK-QHCPKHFHSA-N ClC=1C(=C(C=CC1)C=1NC(=NN1)[C@]1(N(CCC1)C(=O)C1=C(C=CC(=C1)Cl)N1N=CC=N1)C)C Chemical compound ClC=1C(=C(C=CC1)C=1NC(=NN1)[C@]1(N(CCC1)C(=O)C1=C(C=CC(=C1)Cl)N1N=CC=N1)C)C DTXKFFFJIWLWGK-QHCPKHFHSA-N 0.000 claims 1
- GEIMLFITDFJBMZ-SFHVURJKSA-N ClC=1C=CC(=C(C1)C(=O)N1[C@@H](CCC1)C1=NC(=NO1)C1=C(C(=CC=C1)F)OC)N1N=CC=N1 Chemical compound ClC=1C=CC(=C(C1)C(=O)N1[C@@H](CCC1)C1=NC(=NO1)C1=C(C(=CC=C1)F)OC)N1N=CC=N1 GEIMLFITDFJBMZ-SFHVURJKSA-N 0.000 claims 1
- QVUZFDZDFJVVPU-KRWDZBQOSA-N ClC=1C=CC(=C(C1)C(=O)N1[C@@H](CCC1)C1=NC(=NO1)C1=C(C=CC=C1)OC(F)F)N1N=CC=N1 Chemical compound ClC=1C=CC(=C(C1)C(=O)N1[C@@H](CCC1)C1=NC(=NO1)C1=C(C=CC=C1)OC(F)F)N1N=CC=N1 QVUZFDZDFJVVPU-KRWDZBQOSA-N 0.000 claims 1
- VIBREFRUWLQYNL-FQEVSTJZSA-N ClC=1C=CC(=C(C1)C(=O)N1[C@@H](CCC1)C1=NOC(=N1)C1=C(C(=CC=C1)C)C)N1N=CC=N1 Chemical compound ClC=1C=CC(=C(C1)C(=O)N1[C@@H](CCC1)C1=NOC(=N1)C1=C(C(=CC=C1)C)C)N1N=CC=N1 VIBREFRUWLQYNL-FQEVSTJZSA-N 0.000 claims 1
- VGHPMZQELSMPTA-IBGZPJMESA-N ClC=1C=CC(=C(C1)C(=O)N1[C@@H](CCC1)C1=NOC(=N1)C1=C(C(=CC=C1)F)C)N1N=CC=N1 Chemical compound ClC=1C=CC(=C(C1)C(=O)N1[C@@H](CCC1)C1=NOC(=N1)C1=C(C(=CC=C1)F)C)N1N=CC=N1 VGHPMZQELSMPTA-IBGZPJMESA-N 0.000 claims 1
- CEBUUBARAHDERG-SFHVURJKSA-N ClC=1C=CC(=C(C1)C(=O)N1[C@@H](CCC1)C1=NOC(=N1)C1=C(C(=CC=C1)F)OC)N1N=CC=N1 Chemical compound ClC=1C=CC(=C(C1)C(=O)N1[C@@H](CCC1)C1=NOC(=N1)C1=C(C(=CC=C1)F)OC)N1N=CC=N1 CEBUUBARAHDERG-SFHVURJKSA-N 0.000 claims 1
- OFAQXGAHPUYGDC-FQEVSTJZSA-N ClC=1C=CC(=C(C1)C(=O)N1[C@@H](CCC1)C1=NOC(=N1)C1=C(C=CC(=C1)C)C)N1N=CC=N1 Chemical compound ClC=1C=CC(=C(C1)C(=O)N1[C@@H](CCC1)C1=NOC(=N1)C1=C(C=CC(=C1)C)C)N1N=CC=N1 OFAQXGAHPUYGDC-FQEVSTJZSA-N 0.000 claims 1
- AIKROLIVVRRROF-IBGZPJMESA-N ClC=1C=CC(=C(C1)C(=O)N1[C@@H](CCC1)C1=NOC(=N1)C1=C(C=CC(=C1)C)OC)N1N=CC=N1 Chemical compound ClC=1C=CC(=C(C1)C(=O)N1[C@@H](CCC1)C1=NOC(=N1)C1=C(C=CC(=C1)C)OC)N1N=CC=N1 AIKROLIVVRRROF-IBGZPJMESA-N 0.000 claims 1
- LZOSVPFTHSIXES-KRWDZBQOSA-N FC(F)(F)Oc1ccccc1-c1nnc([nH]1)[C@@H]1CCCN1C(=O)c1ccccc1-n1nccn1 Chemical compound FC(F)(F)Oc1ccccc1-c1nnc([nH]1)[C@@H]1CCCN1C(=O)c1ccccc1-n1nccn1 LZOSVPFTHSIXES-KRWDZBQOSA-N 0.000 claims 1
- QEGHNHNBBCPCOI-INIZCTEOSA-N FC(F)(F)Oc1ccccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1ccc(Cl)cc1-n1nccn1 Chemical compound FC(F)(F)Oc1ccccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1ccc(Cl)cc1-n1nccn1 QEGHNHNBBCPCOI-INIZCTEOSA-N 0.000 claims 1
- IBQDXPWHNMCKKW-KRWDZBQOSA-N FC(F)(F)Oc1ccccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1ccccc1-c1ncco1 Chemical compound FC(F)(F)Oc1ccccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1ccccc1-c1ncco1 IBQDXPWHNMCKKW-KRWDZBQOSA-N 0.000 claims 1
- CPHLMMQYMYEFGL-KRWDZBQOSA-N FC(OC1=C(C=CC=C1)C1=NOC(=N1)[C@H]1N(CCC1)C(=O)C1=C(C=C(C=C1)C)N1N=CC=N1)F Chemical compound FC(OC1=C(C=CC=C1)C1=NOC(=N1)[C@H]1N(CCC1)C(=O)C1=C(C=C(C=C1)C)N1N=CC=N1)F CPHLMMQYMYEFGL-KRWDZBQOSA-N 0.000 claims 1
- LEMDRCLHSAJISI-SFHVURJKSA-N FC1=CC(=C(C=C1OC)C(=O)N1[C@@H](CCC1)C1=NOC(=N1)C1=C(C(=CC=C1)F)C)N1N=CC=N1 Chemical compound FC1=CC(=C(C=C1OC)C(=O)N1[C@@H](CCC1)C1=NOC(=N1)C1=C(C(=CC=C1)F)C)N1N=CC=N1 LEMDRCLHSAJISI-SFHVURJKSA-N 0.000 claims 1
- XTBHBVCTQWTHNF-SFHVURJKSA-N FC=1C(=C(C=CC1)C1=NOC(=N1)[C@H]1N(CCC1)C(=O)C1=C(C(=CC=C1)F)C=1NN=CC1)OC Chemical compound FC=1C(=C(C=CC1)C1=NOC(=N1)[C@H]1N(CCC1)C(=O)C1=C(C(=CC=C1)F)C=1NN=CC1)OC XTBHBVCTQWTHNF-SFHVURJKSA-N 0.000 claims 1
- SQFGECSWPJDNIB-SFHVURJKSA-N FC=1C(=C(C=CC1)C1=NOC(=N1)[C@H]1N(CCC1)C(=O)C1=C(C=CC(=C1)F)N1N=CC=N1)OC Chemical compound FC=1C(=C(C=CC1)C1=NOC(=N1)[C@H]1N(CCC1)C(=O)C1=C(C=CC(=C1)F)N1N=CC=N1)OC SQFGECSWPJDNIB-SFHVURJKSA-N 0.000 claims 1
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 claims 1
- ALBXNFSZYZOJKH-FQEVSTJZSA-N [(2s)-2-[3-(2-ethoxy-3-fluorophenyl)-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound CCOC1=C(F)C=CC=C1C1=NOC([C@H]2N(CCC2)C(=O)C=2C(=CC=C(C)C=2)N2N=CC=N2)=N1 ALBXNFSZYZOJKH-FQEVSTJZSA-N 0.000 claims 1
- AEQCSYKEJXBYLJ-FQEVSTJZSA-N [(2s)-2-[3-(2-ethoxyphenyl)-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]-[5-methoxy-2-(triazol-2-yl)phenyl]methanone Chemical compound CCOC1=CC=CC=C1C1=NOC([C@H]2N(CCC2)C(=O)C=2C(=CC=C(OC)C=2)N2N=CC=N2)=N1 AEQCSYKEJXBYLJ-FQEVSTJZSA-N 0.000 claims 1
- LDRMAURZTZUDBO-IBGZPJMESA-N [(2s)-2-[3-(2-ethoxyphenyl)-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]-[5-methoxy-4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound CCOC1=CC=CC=C1C1=NOC([C@H]2N(CCC2)C(=O)C=2C(=CC(C)=C(OC)C=2)N2N=CC=N2)=N1 LDRMAURZTZUDBO-IBGZPJMESA-N 0.000 claims 1
- KIQOCRUHKZKGSM-FQEVSTJZSA-N [(2s)-2-[3-(2-ethoxyphenyl)-1h-1,2,4-triazol-5-yl]pyrrolidin-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound CCOC1=CC=CC=C1C1=NNC([C@H]2N(CCC2)C(=O)C=2C(=CC=C(C)C=2)N2N=CC=N2)=N1 KIQOCRUHKZKGSM-FQEVSTJZSA-N 0.000 claims 1
- MWMQFJWXGDHJEA-QFIPXVFZSA-N [(2s)-2-[3-(2-ethoxypyridin-3-yl)-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]-(5-methyl-2-pyridin-2-ylphenyl)methanone Chemical compound CCOC1=NC=CC=C1C1=NOC([C@H]2N(CCC2)C(=O)C=2C(=CC=C(C)C=2)C=2N=CC=CC=2)=N1 MWMQFJWXGDHJEA-QFIPXVFZSA-N 0.000 claims 1
- BYRMZJPZYRHYMU-FQEVSTJZSA-N [(2s)-2-[3-(3-chloro-2-methylphenyl)-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]-[4,5-dimethyl-2-(triazol-2-yl)phenyl]methanone Chemical compound N=1OC([C@@H]2CCCN2C(=O)C=2C=C(C(=CC=2N2N=CC=N2)C)C)=NC=1C1=CC=CC(Cl)=C1C BYRMZJPZYRHYMU-FQEVSTJZSA-N 0.000 claims 1
- NGQAYYCFKZGBNI-FQEVSTJZSA-N [(2s)-2-[3-(3-chloro-2-methylphenyl)-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound N=1OC([C@@H]2CCCN2C(=O)C=2C(=CC=C(C=2)C)N2N=CC=N2)=NC=1C1=CC=CC(Cl)=C1C NGQAYYCFKZGBNI-FQEVSTJZSA-N 0.000 claims 1
- GHZBHHGLXHLLGK-IBGZPJMESA-N [(2s)-2-[3-(3-fluoro-2-methoxyphenyl)-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound COC1=C(F)C=CC=C1C1=NOC([C@H]2N(CCC2)C(=O)C=2C(=CC=C(C)C=2)N2N=CC=N2)=N1 GHZBHHGLXHLLGK-IBGZPJMESA-N 0.000 claims 1
- DXCJSSMKWSUPJG-KRWDZBQOSA-N [(2s)-2-[3-[2-(difluoromethoxy)phenyl]-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]-[5-methoxy-4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound N=1OC([C@@H]2CCCN2C(=O)C=2C=C(C(=CC=2N2N=CC=N2)C)OC)=NC=1C1=CC=CC=C1OC(F)F DXCJSSMKWSUPJG-KRWDZBQOSA-N 0.000 claims 1
- ZFLFJAHHMRXRRR-NRFANRHFSA-N [(2s)-2-[5-(2,3-dimethylphenyl)-1,2,4-oxadiazol-3-yl]pyrrolidin-1-yl]-[4,5-dimethyl-2-(triazol-2-yl)phenyl]methanone Chemical compound CC1=CC=CC(C=2ON=C(N=2)[C@H]2N(CCC2)C(=O)C=2C(=CC(C)=C(C)C=2)N2N=CC=N2)=C1C ZFLFJAHHMRXRRR-NRFANRHFSA-N 0.000 claims 1
- FCJMMEVNQNVXGE-FQEVSTJZSA-N [(2s)-2-[5-(2-ethoxy-3-fluorophenyl)-1,2,4-oxadiazol-3-yl]pyrrolidin-1-yl]-[5-methoxy-2-(triazol-2-yl)phenyl]methanone Chemical compound CCOC1=C(F)C=CC=C1C1=NC([C@H]2N(CCC2)C(=O)C=2C(=CC=C(OC)C=2)N2N=CC=N2)=NO1 FCJMMEVNQNVXGE-FQEVSTJZSA-N 0.000 claims 1
- NCMHZVAFPWWMGJ-IBGZPJMESA-N [(2s)-2-[5-(2-ethoxyphenyl)-1,2,4-oxadiazol-3-yl]pyrrolidin-1-yl]-[5-methoxy-4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound CCOC1=CC=CC=C1C1=NC([C@H]2N(CCC2)C(=O)C=2C(=CC(C)=C(OC)C=2)N2N=CC=N2)=NO1 NCMHZVAFPWWMGJ-IBGZPJMESA-N 0.000 claims 1
- HCOCPXCAVLDJOP-SFHVURJKSA-N [(2s)-2-[5-(2-ethoxypyridin-3-yl)-1,2,4-oxadiazol-3-yl]pyrrolidin-1-yl]-[4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound CCOC1=NC=CC=C1C1=NC([C@H]2N(CCC2)C(=O)C=2C(=CC(C)=CC=2)N2N=CC=N2)=NO1 HCOCPXCAVLDJOP-SFHVURJKSA-N 0.000 claims 1
- QZJBWKPFJDTYKJ-SFHVURJKSA-N [(2s)-2-[5-(2-ethoxypyridin-3-yl)-1,2,4-oxadiazol-3-yl]pyrrolidin-1-yl]-[5-methoxy-4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound CCOC1=NC=CC=C1C1=NC([C@H]2N(CCC2)C(=O)C=2C(=CC(C)=C(OC)C=2)N2N=CC=N2)=NO1 QZJBWKPFJDTYKJ-SFHVURJKSA-N 0.000 claims 1
- RHUPJZFHSQTXAK-IBGZPJMESA-N [(2s)-2-[5-(3-chloro-2-methoxyphenyl)-1,2,4-oxadiazol-3-yl]pyrrolidin-1-yl]-[4,5-dimethyl-2-(triazol-2-yl)phenyl]methanone Chemical compound COC1=C(Cl)C=CC=C1C1=NC([C@H]2N(CCC2)C(=O)C=2C(=CC(C)=C(C)C=2)N2N=CC=N2)=NO1 RHUPJZFHSQTXAK-IBGZPJMESA-N 0.000 claims 1
- CGZZINUKGZISIW-KRWDZBQOSA-N [(2s)-2-[5-(3-chloro-2-methoxyphenyl)-1,2,4-oxadiazol-3-yl]pyrrolidin-1-yl]-[4-chloro-2-(triazol-2-yl)phenyl]methanone Chemical compound COC1=C(Cl)C=CC=C1C1=NC([C@H]2N(CCC2)C(=O)C=2C(=CC(Cl)=CC=2)N2N=CC=N2)=NO1 CGZZINUKGZISIW-KRWDZBQOSA-N 0.000 claims 1
- ITUQWEVHCQGQNX-FQEVSTJZSA-N [(2s)-2-[5-(3-methoxy-5-methylphenyl)-1,2,4-oxadiazol-3-yl]pyrrolidin-1-yl]-[5-methoxy-4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound COC1=CC(C)=CC(C=2ON=C(N=2)[C@H]2N(CCC2)C(=O)C=2C(=CC(C)=C(OC)C=2)N2N=CC=N2)=C1 ITUQWEVHCQGQNX-FQEVSTJZSA-N 0.000 claims 1
- AEVKXGFMSDEVKH-INIZCTEOSA-N [2-fluoro-3-methyl-6-(triazol-2-yl)phenyl]-[(2s)-2-[3-[2-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]methanone Chemical compound N=1OC([C@@H]2CCCN2C(=O)C=2C(=CC=C(C=2F)C)N2N=CC=N2)=NC=1C1=CC=CC=C1OC(F)(F)F AEVKXGFMSDEVKH-INIZCTEOSA-N 0.000 claims 1
- VDDCPARAGTYUEF-KRWDZBQOSA-N [3-fluoro-2-(1h-pyrazol-5-yl)phenyl]-[(2s)-2-[3-[2-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]methanone Chemical compound N=1OC([C@@H]2CCCN2C(=O)C=2C=CC=C(C=2C=2NN=CC=2)F)=NC=1C1=CC=CC=C1OC(F)(F)F VDDCPARAGTYUEF-KRWDZBQOSA-N 0.000 claims 1
- AOZWQYYEGGLQBY-IBGZPJMESA-N [4,5-dimethyl-2-(triazol-2-yl)phenyl]-[(2s)-2-[3-(2-methoxyphenyl)-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]methanone Chemical compound COC1=CC=CC=C1C1=NOC([C@H]2N(CCC2)C(=O)C=2C(=CC(C)=C(C)C=2)N2N=CC=N2)=N1 AOZWQYYEGGLQBY-IBGZPJMESA-N 0.000 claims 1
- PFWMTAVODQARFU-SFHVURJKSA-N [4,5-dimethyl-2-(triazol-2-yl)phenyl]-[(2s)-2-[3-[2-(trifluoromethoxy)phenyl]-1h-1,2,4-triazol-5-yl]pyrrolidin-1-yl]methanone Chemical compound N=1NC([C@@H]2CCCN2C(=O)C=2C=C(C(=CC=2N2N=CC=N2)C)C)=NC=1C1=CC=CC=C1OC(F)(F)F PFWMTAVODQARFU-SFHVURJKSA-N 0.000 claims 1
- SXDFZCLHFGCOFB-IBGZPJMESA-N [4,5-dimethyl-2-(triazol-2-yl)phenyl]-[(2s)-2-[5-(2-ethoxypyridin-3-yl)-1,2,4-oxadiazol-3-yl]pyrrolidin-1-yl]methanone Chemical compound CCOC1=NC=CC=C1C1=NC([C@H]2N(CCC2)C(=O)C=2C(=CC(C)=C(C)C=2)N2N=CC=N2)=NO1 SXDFZCLHFGCOFB-IBGZPJMESA-N 0.000 claims 1
- JWAFZGHEIPYAAF-NRFANRHFSA-N [4,5-dimethyl-2-(triazol-2-yl)phenyl]-[(2s)-2-[5-(3-methoxy-5-methylphenyl)-1,2,4-oxadiazol-3-yl]pyrrolidin-1-yl]methanone Chemical compound COC1=CC(C)=CC(C=2ON=C(N=2)[C@H]2N(CCC2)C(=O)C=2C(=CC(C)=C(C)C=2)N2N=CC=N2)=C1 JWAFZGHEIPYAAF-NRFANRHFSA-N 0.000 claims 1
- OESAAULEOZNLQH-SFHVURJKSA-N [4,5-dimethyl-2-(triazol-2-yl)phenyl]-[(2s)-2-[5-[2-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-3-yl]pyrrolidin-1-yl]methanone Chemical compound N=1C([C@@H]2CCCN2C(=O)C=2C=C(C(=CC=2N2N=CC=N2)C)C)=NOC=1C1=CC=CC=C1OC(F)(F)F OESAAULEOZNLQH-SFHVURJKSA-N 0.000 claims 1
- KNKZHYJZNLJPTJ-IBGZPJMESA-N [4-chloro-2-(triazol-2-yl)phenyl]-[(2s)-2-[5-(2-ethylphenyl)-1,2,4-oxadiazol-3-yl]pyrrolidin-1-yl]methanone Chemical compound CCC1=CC=CC=C1C1=NC([C@H]2N(CCC2)C(=O)C=2C(=CC(Cl)=CC=2)N2N=CC=N2)=NO1 KNKZHYJZNLJPTJ-IBGZPJMESA-N 0.000 claims 1
- FEQYQBGREABPNL-IBGZPJMESA-N [4-chloro-5-methoxy-2-(triazol-2-yl)phenyl]-[(2s)-2-[5-(2-ethylphenyl)-1,2,4-oxadiazol-3-yl]pyrrolidin-1-yl]methanone Chemical compound CCC1=CC=CC=C1C1=NC([C@H]2N(CCC2)C(=O)C=2C(=CC(Cl)=C(OC)C=2)N2N=CC=N2)=NO1 FEQYQBGREABPNL-IBGZPJMESA-N 0.000 claims 1
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- KVMBKSBJKAKGHZ-HNNXBMFYSA-N tert-butyl (2s)-2-(1-phenyltriazol-4-yl)pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@H]1C1=CN(C=2C=CC=CC=2)N=N1 KVMBKSBJKAKGHZ-HNNXBMFYSA-N 0.000 description 1
- CFLBQJNMTRKAAI-HNNXBMFYSA-N tert-butyl (2s)-2-(3-phenyl-1,2-oxazol-5-yl)pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@H]1C1=CC(C=2C=CC=CC=2)=NO1 CFLBQJNMTRKAAI-HNNXBMFYSA-N 0.000 description 1
- BJGCVXTYUFBDFS-ZDUSSCGKSA-N tert-butyl (2s)-2-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@H]1C1=NN=C(C=2C=CC=CC=2)O1 BJGCVXTYUFBDFS-ZDUSSCGKSA-N 0.000 description 1
- HWFTXTHMZXBTKL-HNNXBMFYSA-N tert-butyl (2s)-2-(5-phenyl-1h-imidazol-2-yl)pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@H]1C1=NC=C(C=2C=CC=CC=2)N1 HWFTXTHMZXBTKL-HNNXBMFYSA-N 0.000 description 1
- KTQQDWACAUDUJC-NSHDSACASA-N tert-butyl (2s)-2-(aminomethyl)-2-methylpyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@@]1(C)CN KTQQDWACAUDUJC-NSHDSACASA-N 0.000 description 1
- NUMIITGLIZNJIC-ZETCQYMHSA-N tert-butyl (2s)-2-(n'-hydroxycarbamimidoyl)pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@H]1\C(N)=N\O NUMIITGLIZNJIC-ZETCQYMHSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical compound C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 1
- 230000035922 thirst Effects 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 231100000886 tinnitus Toxicity 0.000 description 1
- 208000004371 toothache Diseases 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000723 toxicological property Toxicity 0.000 description 1
- 230000002103 transcriptional effect Effects 0.000 description 1
- 238000011830 transgenic mouse model Methods 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 230000008736 traumatic injury Effects 0.000 description 1
- YOWGRWHKDCHINP-UHFFFAOYSA-N tributyl(1,3-oxazol-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=NC=CO1 YOWGRWHKDCHINP-UHFFFAOYSA-N 0.000 description 1
- GYUURHMITDQTRU-UHFFFAOYSA-N tributyl(pyridin-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CC=N1 GYUURHMITDQTRU-UHFFFAOYSA-N 0.000 description 1
- WTFFOOAJSDVASL-UHFFFAOYSA-N tributyl(pyrimidin-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=NC=CC=N1 WTFFOOAJSDVASL-UHFFFAOYSA-N 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- PRXNKYBFWAWBNZ-UHFFFAOYSA-N trimethylphenylammonium tribromide Chemical compound Br[Br-]Br.C[N+](C)(C)C1=CC=CC=C1 PRXNKYBFWAWBNZ-UHFFFAOYSA-N 0.000 description 1
- IFOIAHYDBXLNJX-UHFFFAOYSA-N trioxazole Chemical compound O1OC=NO1 IFOIAHYDBXLNJX-UHFFFAOYSA-N 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 208000009935 visceral pain Diseases 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 230000003936 working memory Effects 0.000 description 1
- BPICBUSOMSTKRF-UHFFFAOYSA-N xylazine Chemical compound CC1=CC=CC(C)=C1NC1=NCCCS1 BPICBUSOMSTKRF-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—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
Landscapes
- Chemical & Material Sciences (AREA)
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- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- Biomedical Technology (AREA)
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- Anesthesiology (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Epidemiology (AREA)
- Pyrrole Compounds (AREA)
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| TWI756418B (zh) * | 2017-05-03 | 2022-03-01 | 瑞士商愛杜西亞製藥有限公司 | 2-([1,2,3]三唑-2-基)-苯甲酸衍生物之製備 |
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| LT2855453T (lt) | 2012-06-04 | 2017-02-27 | Actelion Pharmaceuticals Ltd. | Benzimidazolo prolino dariniai |
| EP2970241A1 (en) | 2013-03-12 | 2016-01-20 | Actelion Pharmaceuticals Ltd. | Azetidine amide derivatives as orexin receptor antagonists |
| PT3077389T (pt) | 2013-12-03 | 2017-12-15 | Idorsia Pharmaceuticals Ltd | Forma cristalina de (s)-(2-(6-cloro-7-metil-1hbenzo[d]imidazol-2-il)-2-metilpirrolidin-1-il)(5-metoxi-2-(2h-1,2,3-triazol-2-il)fenil)metanona e a sua utilização como como antagonistas do receptor de orexina |
| UA119151C2 (uk) | 2013-12-03 | 2019-05-10 | Ідорсія Фармасьютікалз Лтд | КРИСТАЛІЧНА СОЛЬОВА ФОРМА (S)-(2-(6-ХЛОР-7-МЕТИЛ-1H-БЕНЗО[d]ІМІДАЗОЛ-2-ІЛ)-2-МЕТИЛПІРОЛІДИН-1-ІЛ)(5-МЕТОКСИ-2-(2H-1,2,3-ТРИАЗОЛ-2-ІЛ)ФЕНІЛ)МЕТАНОНУ ЯК АНТАГОНІСТ ОРЕКСИНОВОГО РЕЦЕПТОРА |
| SI3077391T1 (sl) | 2013-12-04 | 2018-11-30 | Idorsia Pharmaceuticals Ltd | Uporaba benzimidazol-prolinskih derivatov |
| JP2017024990A (ja) * | 2013-12-13 | 2017-02-02 | 大正製薬株式会社 | オキサゾリジン及びオキサジナン誘導体 |
| US9938276B2 (en) | 2014-12-19 | 2018-04-10 | Merck Sharp & Dohme Corp. | 6,5-bicyclic octahydropyrrolopyridine orexin receptor antagonists |
| WO2017012502A1 (en) | 2015-07-17 | 2017-01-26 | Sunshine Lake Pharma Co., Ltd. | Substituted quinazoline compounds and preparation and uses thereof |
| WO2017088759A1 (en) | 2015-11-23 | 2017-06-01 | Sunshine Lake Pharma Co., Ltd. | OCTAHYDROPYRROLO [3, 4-c] PYRROLE DERIVATIVES AND USES THEREOF |
| CN106986859B (zh) * | 2016-01-20 | 2020-02-11 | 广东东阳光药业有限公司 | 吲哚衍生物及其用途 |
| MA46589A (fr) | 2016-10-24 | 2019-08-28 | Yumanity Therapeutics Inc | Composés et utilisations de ces derniers |
| KR20190108118A (ko) | 2017-01-06 | 2019-09-23 | 유마니티 테라퓨틱스, 인크. | 신경계 장애의 치료를 위한 방법 |
| JP7012703B2 (ja) * | 2017-03-08 | 2022-02-14 | 武田薬品工業株式会社 | 置換ピロリジン化合物およびその用途 |
| CN108794454B (zh) * | 2017-04-27 | 2023-08-15 | 广东东阳光药业股份有限公司 | 一种咪唑环化合物的制备方法 |
| WO2019018795A1 (en) * | 2017-07-20 | 2019-01-24 | Yumanity Therapeutics | COMPOUNDS AND USES THEREOF |
| US11873298B2 (en) | 2017-10-24 | 2024-01-16 | Janssen Pharmaceutica Nv | Compounds and uses thereof |
| JP7025542B2 (ja) * | 2017-10-26 | 2022-02-24 | サウザーン リサーチ インスチチュート | Tgf-ベータ阻害剤としてのオキサジアゾール及びチアジアゾール |
| MX2020009942A (es) | 2018-03-23 | 2021-01-08 | Yumanity Therapeutics Inc | Compuestos y usos de los mismos. |
| EP3784234A1 (en) | 2018-04-25 | 2021-03-03 | Yumanity Therapeutics, Inc. | Compounds and uses thereof |
| KR20220007845A (ko) | 2019-01-24 | 2022-01-19 | 유마니티 테라퓨틱스, 인크. | 화합물 및 이의 용도 |
| EP3917616B1 (en) | 2019-01-31 | 2025-06-11 | Takeda Pharmaceutical Company Limited | Heterocyclic compounds and use thereof |
| EA202192047A1 (ru) | 2019-11-13 | 2021-12-08 | Юманити Терапьютикс, Инк. | Соединения и их применение |
| JP7681113B2 (ja) * | 2021-02-02 | 2025-05-21 | メッドシャイン ディスカバリー インコーポレイテッド | テトラヒドロピロロ環化合物及びその使用 |
| TW202400149A (zh) | 2022-05-13 | 2024-01-01 | 瑞士商愛杜西亞製藥有限公司 | 經噻唑并芳基-甲基取代之環狀肼-n-甲醯胺衍生物 |
| US11919872B1 (en) | 2023-10-11 | 2024-03-05 | King Faisal University | N′-(2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetoxy)benzimidamide as an antimicrobial compound |
| US11897850B1 (en) | 2023-10-11 | 2024-02-13 | King Faisal University | N′-(2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetoxy)-4-methoxybenzimidamide as an antimicrobial compound |
| US11912675B1 (en) | 2023-10-11 | 2024-02-27 | King Faisal University | N'-(2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetoxy)-3,4-dimethoxybenzimidamide as an antimicrobial compound |
| US11891366B1 (en) | 2023-10-12 | 2024-02-06 | King Faisal University | 4-methoxy-n′-(2-(5-phenyl-1,3,4-oxadiazol-2-ylthio)acetoxy)benzimidamide as an antimicrobial compound |
| CN119613393A (zh) * | 2024-11-13 | 2025-03-14 | 深圳华津生物科技有限公司 | Trpc5抑制剂及其制备方法和应用 |
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-
2013
- 2013-10-09 US US14/434,997 patent/US9493446B2/en not_active Expired - Fee Related
- 2013-10-09 AU AU2013328301A patent/AU2013328301A1/en not_active Abandoned
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- 2013-10-09 CA CA2885180A patent/CA2885180C/en active Active
- 2013-10-09 KR KR1020157012089A patent/KR102151288B1/ko not_active Expired - Fee Related
- 2013-10-09 MX MX2015004638A patent/MX2015004638A/es unknown
- 2013-10-09 AR ARP130103661A patent/AR092955A1/es unknown
- 2013-10-09 CN CN201380051391.3A patent/CN104703980B/zh not_active Expired - Fee Related
- 2013-10-09 TW TW102136619A patent/TW201414727A/zh unknown
- 2013-10-09 BR BR112015007516A patent/BR112015007516A2/pt not_active IP Right Cessation
- 2013-10-09 SG SG11201502493XA patent/SG11201502493XA/en unknown
- 2013-10-09 WO PCT/IB2013/059233 patent/WO2014057435A1/en not_active Ceased
- 2013-10-09 EA EA201500399A patent/EA201500399A1/ru unknown
- 2013-10-09 EP EP13805561.1A patent/EP2906553B1/en active Active
-
2015
- 2015-03-20 PH PH12015500627A patent/PH12015500627A1/en unknown
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI756418B (zh) * | 2017-05-03 | 2022-03-01 | 瑞士商愛杜西亞製藥有限公司 | 2-([1,2,3]三唑-2-基)-苯甲酸衍生物之製備 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2885180C (en) | 2021-03-02 |
| KR20150064753A (ko) | 2015-06-11 |
| EA201500399A1 (ru) | 2015-09-30 |
| CN104703980B (zh) | 2017-09-22 |
| CN104703980A (zh) | 2015-06-10 |
| EP2906553B1 (en) | 2019-06-26 |
| JP2015533157A (ja) | 2015-11-19 |
| PH12015500627A1 (en) | 2015-05-11 |
| AU2013328301A1 (en) | 2015-05-28 |
| US9493446B2 (en) | 2016-11-15 |
| WO2014057435A1 (en) | 2014-04-17 |
| AR092955A1 (es) | 2015-05-06 |
| SG11201502493XA (en) | 2015-04-29 |
| IL238052A0 (en) | 2015-05-31 |
| EP2906553A1 (en) | 2015-08-19 |
| JP6244365B2 (ja) | 2017-12-06 |
| KR102151288B1 (ko) | 2020-09-03 |
| CA2885180A1 (en) | 2014-04-17 |
| US20150252032A1 (en) | 2015-09-10 |
| AU2013328301A8 (en) | 2015-06-11 |
| MX2015004638A (es) | 2015-07-14 |
| BR112015007516A2 (pt) | 2017-07-04 |
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