MX2015004638A - Antagonistas de receptores de orexina los cuales son derivados de [orto bi-(hetero-) aril]-[2-meta bi-(hetero-) aril)-pirrolidin-1-il]-metanona. - Google Patents
Antagonistas de receptores de orexina los cuales son derivados de [orto bi-(hetero-) aril]-[2-meta bi-(hetero-) aril)-pirrolidin-1-il]-metanona.Info
- Publication number
- MX2015004638A MX2015004638A MX2015004638A MX2015004638A MX2015004638A MX 2015004638 A MX2015004638 A MX 2015004638A MX 2015004638 A MX2015004638 A MX 2015004638A MX 2015004638 A MX2015004638 A MX 2015004638A MX 2015004638 A MX2015004638 A MX 2015004638A
- Authority
- MX
- Mexico
- Prior art keywords
- phenyl
- pyrrolidin
- oxadiazol
- methyl
- triazol
- Prior art date
Links
- 125000003118 aryl group Chemical group 0.000 title claims abstract description 16
- 125000005842 heteroatom Chemical group 0.000 title claims description 26
- 229940123730 Orexin receptor antagonist Drugs 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 522
- 150000003839 salts Chemical class 0.000 claims abstract description 31
- 239000003814 drug Substances 0.000 claims abstract description 18
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- -1 2,3-dihydro-benzo [1,4] dioxinyl group Chemical group 0.000 claims description 326
- 125000001424 substituent group Chemical group 0.000 claims description 150
- 238000000034 method Methods 0.000 claims description 111
- 125000001072 heteroaryl group Chemical group 0.000 claims description 102
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 96
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 77
- 208000035475 disorder Diseases 0.000 claims description 75
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 50
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 125000005549 heteroarylene group Chemical group 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 230000004064 dysfunction Effects 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 208000019901 Anxiety disease Diseases 0.000 claims description 21
- 102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 claims description 21
- 101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 claims description 21
- 208000019116 sleep disease Diseases 0.000 claims description 21
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 19
- 150000002367 halogens Chemical class 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 201000010099 disease Diseases 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 15
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 15
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 239000011593 sulfur Substances 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 208000019022 Mood disease Diseases 0.000 claims description 11
- 206010012335 Dependence Diseases 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 8
- 125000001425 triazolyl group Chemical group 0.000 claims description 8
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 7
- 230000004630 mental health Effects 0.000 claims description 7
- 230000000446 orexinergic effect Effects 0.000 claims description 7
- 230000002265 prevention Effects 0.000 claims description 7
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
- 208000010877 cognitive disease Diseases 0.000 claims description 5
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 4
- 208000027559 Appetite disease Diseases 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 4
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 125000006085 pyrrolopyridyl group Chemical group 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 235000001484 Trigonella foenum graecum Nutrition 0.000 claims 9
- 244000250129 Trigonella foenum graecum Species 0.000 claims 9
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 6
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 2
- LISKAOIANGDBTB-UHFFFAOYSA-N 2-ethoxypyridine Chemical compound CCOC1=CC=CC=N1 LISKAOIANGDBTB-UHFFFAOYSA-N 0.000 claims 2
- DUGOZIWVEXMGBE-UHFFFAOYSA-N Methylphenidate Chemical compound C=1C=CC=CC=1C(C(=O)OC)C1CCCCN1 DUGOZIWVEXMGBE-UHFFFAOYSA-N 0.000 claims 2
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 claims 1
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims 1
- PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical compound C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 claims 1
- 125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- CKUCAJXBWZNSLS-UHFFFAOYSA-N 2-ethoxy-3-fluorophenol Chemical compound CCOC1=C(O)C=CC=C1F CKUCAJXBWZNSLS-UHFFFAOYSA-N 0.000 claims 1
- NSPMIYGKQJPBQR-QDNHWIQGSA-N 3,5-dideuterio-1h-1,2,4-triazole Chemical compound [2H]C1=NNC([2H])=N1 NSPMIYGKQJPBQR-QDNHWIQGSA-N 0.000 claims 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- HWQKEDNHWREBQJ-UHFFFAOYSA-N 4-methyl-2-(triazol-2-yl)phenol Chemical compound CC1=CC=C(O)C(N2N=CC=N2)=C1 HWQKEDNHWREBQJ-UHFFFAOYSA-N 0.000 claims 1
- PNICOKLUBCGUPE-UHFFFAOYSA-N 5-hydroxy-1,2-oxazol-3-one Chemical compound OC=1C=C(O)ON=1 PNICOKLUBCGUPE-UHFFFAOYSA-N 0.000 claims 1
- QWZSHPBGQHXOLQ-UHFFFAOYSA-N 5-hydroxy-3h-1,3-oxazol-2-one Chemical compound OC1=CN=C(O)O1 QWZSHPBGQHXOLQ-UHFFFAOYSA-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
- GTKBGYVEQYPMTQ-IBGZPJMESA-N CCOc1ncccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1cc(OC)ccc1-n1nccn1 Chemical compound CCOc1ncccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1cc(OC)ccc1-n1nccn1 GTKBGYVEQYPMTQ-IBGZPJMESA-N 0.000 claims 1
- HYNROYDTRQQKQI-FQEVSTJZSA-N COC=1C(=C(C=CC1)C1=NC(=NO1)[C@H]1N(CCC1)C(=O)C1=C(C=CC(=C1)C)N1N=CC=N1)C Chemical compound COC=1C(=C(C=CC1)C1=NC(=NO1)[C@H]1N(CCC1)C(=O)C1=C(C=CC(=C1)C)N1N=CC=N1)C HYNROYDTRQQKQI-FQEVSTJZSA-N 0.000 claims 1
- ZREZAWDRVGUTGE-NRFANRHFSA-N COC=1C=C(C=C(C1)C)C1=NC(=NO1)[C@H]1N(CCC1)C(=O)C1=C(C=CC(=C1)C)N1N=CC=N1 Chemical compound COC=1C=C(C=C(C1)C)C1=NC(=NO1)[C@H]1N(CCC1)C(=O)C1=C(C=CC(=C1)C)N1N=CC=N1 ZREZAWDRVGUTGE-NRFANRHFSA-N 0.000 claims 1
- UBKDBBIBRAMTQD-QFIPXVFZSA-N COC=1C=C(C=CC1)C1=CN=C(N1)[C@H]1N(CCC1)C(=O)C1=C(C=CC(=C1)C)N1N=CC=N1 Chemical compound COC=1C=C(C=CC1)C1=CN=C(N1)[C@H]1N(CCC1)C(=O)C1=C(C=CC(=C1)C)N1N=CC=N1 UBKDBBIBRAMTQD-QFIPXVFZSA-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
- 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 1
- RLTWWZBLCRMJMS-SFHVURJKSA-N COc1c(F)cccc1-c1nc(no1)[C@@H]1CCCN1C(=O)c1ccccc1-n1nccn1 Chemical compound COc1c(F)cccc1-c1nc(no1)[C@@H]1CCCN1C(=O)c1ccccc1-n1nccn1 RLTWWZBLCRMJMS-SFHVURJKSA-N 0.000 claims 1
- 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 1
- XPCGYJYMBRVUIM-SFHVURJKSA-N COc1c(F)cccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1ccccc1-n1nccn1 Chemical compound COc1c(F)cccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1ccccc1-n1nccn1 XPCGYJYMBRVUIM-SFHVURJKSA-N 0.000 claims 1
- 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 1
- RTGIDLKDGHUJGH-FQEVSTJZSA-N COc1cc(C(=O)N2CCC[C@H]2c2nc(no2)-c2cccc(F)c2OC)c(cc1C)-c1ncccn1 Chemical compound COc1cc(C(=O)N2CCC[C@H]2c2nc(no2)-c2cccc(F)c2OC)c(cc1C)-c1ncccn1 RTGIDLKDGHUJGH-FQEVSTJZSA-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
- 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
- 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 1
- OPODZHORDYECHR-IBGZPJMESA-N COc1ccccc1-c1nnc([nH]1)[C@@H]1CCCN1C(=O)c1cc(C)ccc1-n1nccn1 Chemical compound COc1ccccc1-c1nnc([nH]1)[C@@H]1CCCN1C(=O)c1cc(C)ccc1-n1nccn1 OPODZHORDYECHR-IBGZPJMESA-N 0.000 claims 1
- OOYPUYSPYKAJTA-SFHVURJKSA-N Cc1c(Cl)cccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1ccc(Cl)cc1-n1nccn1 Chemical compound Cc1c(Cl)cccc1-c1noc(n1)[C@@H]1CCCN1C(=O)c1ccc(Cl)cc1-n1nccn1 OOYPUYSPYKAJTA-SFHVURJKSA-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
- 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
- CXZXWKINGRPWER-IBGZPJMESA-N Cc1ccc(C(=O)N2CCC[C@H]2c2noc(n2)-c2cccc(F)c2C)c(c1)-n1nccn1 Chemical compound Cc1ccc(C(=O)N2CCC[C@H]2c2noc(n2)-c2cccc(F)c2C)c(c1)-n1nccn1 CXZXWKINGRPWER-IBGZPJMESA-N 0.000 claims 1
- PJCHJVRTUKAXQL-ZDUSSCGKSA-N Cc1ccc(C)c(c1)-c1nc(no1)[C@@H]1CCCN1C=O Chemical compound Cc1ccc(C)c(c1)-c1nc(no1)[C@@H]1CCCN1C=O PJCHJVRTUKAXQL-ZDUSSCGKSA-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
- 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
- HMSHNWRVNFMPDS-IBGZPJMESA-N Cc1ccc(c(c1)C(=O)N1CCC[C@H]1c1nc(no1)-c1cccc(C)c1Cl)-n1nccn1 Chemical compound Cc1ccc(c(c1)C(=O)N1CCC[C@H]1c1nc(no1)-c1cccc(C)c1Cl)-n1nccn1 HMSHNWRVNFMPDS-IBGZPJMESA-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
- BYYZAURIVFCTLA-IBGZPJMESA-N Cc1ccc(c(c1)C(=O)N1CCC[C@H]1c1nc(no1)-c1cccc(OC(F)F)c1)-n1nccn1 Chemical compound Cc1ccc(c(c1)C(=O)N1CCC[C@H]1c1nc(no1)-c1cccc(OC(F)F)c1)-n1nccn1 BYYZAURIVFCTLA-IBGZPJMESA-N 0.000 claims 1
- KTQDXFVMBAMYRT-FQEVSTJZSA-N Cc1ccc(c(c1)C(=O)N1CCC[C@H]1c1noc(n1)-c1cccc(F)c1C)-n1nccn1 Chemical compound Cc1ccc(c(c1)C(=O)N1CCC[C@H]1c1noc(n1)-c1cccc(F)c1C)-n1nccn1 KTQDXFVMBAMYRT-FQEVSTJZSA-N 0.000 claims 1
- NOBGCNIGBCJHOC-UHFFFAOYSA-N ClC1=CC(=C(C=C1)O)N1N=CC=N1 Chemical compound ClC1=CC(=C(C=C1)O)N1N=CC=N1 NOBGCNIGBCJHOC-UHFFFAOYSA-N 0.000 claims 1
- BKDDWRDQKMRANE-SFHVURJKSA-N ClC1=CC(=NC(=C1)OC)C1=NC(=NO1)[C@H]1N(CCC1)C(=O)C1=C(C=CC(=C1)C)N1N=CC=N1 Chemical compound ClC1=CC(=NC(=C1)OC)C1=NC(=NO1)[C@H]1N(CCC1)C(=O)C1=C(C=CC(=C1)C)N1N=CC=N1 BKDDWRDQKMRANE-SFHVURJKSA-N 0.000 claims 1
- ODDWFVQXCLKZAD-SFHVURJKSA-N ClC=1C(=C(C=CC1)C1=NC(=NO1)[C@H]1N(CCC1)C(=O)C1=C(C=C(C(=C1)OC)F)N1N=CC=N1)C Chemical compound ClC=1C(=C(C=CC1)C1=NC(=NO1)[C@H]1N(CCC1)C(=O)C1=C(C=C(C(=C1)OC)F)N1N=CC=N1)C ODDWFVQXCLKZAD-SFHVURJKSA-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
- NZOOYKJWSORDBO-IBGZPJMESA-N ClC=1C(=C(C=CC1)C=1NC(=NN1)[C@H]1N(CCC1)C(=O)C1=C(C=C(C(=C1)C)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)C)N1N=CC=N1)OC NZOOYKJWSORDBO-IBGZPJMESA-N 0.000 claims 1
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- NZYOAGBNMCVQIV-UHFFFAOYSA-N sodium;chloro-(4-methylphenyl)sulfonylazanide;trihydrate Chemical compound O.O.O.[Na+].CC1=CC=C(S(=O)(=O)[N-]Cl)C=C1 NZYOAGBNMCVQIV-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
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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
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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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
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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
- A61P25/28—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
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- A—HUMAN NECESSITIES
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- 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)
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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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| EP12188019 | 2012-10-10 | ||
| EP13157809 | 2013-03-05 | ||
| PCT/IB2013/059233 WO2014057435A1 (en) | 2012-10-10 | 2013-10-09 | Orexin receptor antagonists which are [ortho bi (hetero )aryl]-[2-(meta bi (hetero )aryl)-pyrrolidin-1-yl]-methanone derivatives |
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| MX2015004638A true MX2015004638A (es) | 2015-07-14 |
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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 |
| EP3619199B1 (en) * | 2017-05-03 | 2021-07-07 | Idorsia Pharmaceuticals Ltd | Preparation of 2-([1,2,3]triazol-2-yl)-benzoic acid derivatives |
| 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 |
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| 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
- 2013-10-09 JP JP2015536264A patent/JP6244365B2/ja not_active Expired - Fee Related
- 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
- 2015-03-31 IL IL238052A patent/IL238052A0/en unknown
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 |
| TW201414727A (zh) | 2014-04-16 |
| 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 |
| BR112015007516A2 (pt) | 2017-07-04 |
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