JP2007523208A5 - - Google Patents
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- Publication number
- JP2007523208A5 JP2007523208A5 JP2007500152A JP2007500152A JP2007523208A5 JP 2007523208 A5 JP2007523208 A5 JP 2007523208A5 JP 2007500152 A JP2007500152 A JP 2007500152A JP 2007500152 A JP2007500152 A JP 2007500152A JP 2007523208 A5 JP2007523208 A5 JP 2007523208A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- azabicyclo
- thio
- propyl
- triazol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims description 15
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims description 8
- 229960003638 dopamine Drugs 0.000 claims description 4
- -1 2-pyrrolidinonyl Chemical group 0.000 claims 50
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 36
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 31
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 23
- 150000003839 salts Chemical class 0.000 claims 22
- 125000000217 alkyl group Chemical group 0.000 claims 16
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 15
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 11
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 9
- PUMREIFKTMLCAF-UHFFFAOYSA-N 4-methyl-1,3-oxazole Chemical compound CC1=COC=N1 PUMREIFKTMLCAF-UHFFFAOYSA-N 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 125000001475 halogen functional group Chemical group 0.000 claims 8
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 7
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 6
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 6
- 208000028017 Psychotic disease Diseases 0.000 claims 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 125000004076 pyridyl group Chemical group 0.000 claims 5
- 125000000842 isoxazolyl group Chemical group 0.000 claims 4
- 201000009032 substance abuse Diseases 0.000 claims 4
- 231100000736 substance abuse Toxicity 0.000 claims 4
- 208000011117 substance-related disease Diseases 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 3
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 3
- GLSJOAMLOIMSGI-KMDAROACSA-N 4-methyl-5-[4-methyl-5-[3-[(1s,5r)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexan-3-yl]butylsulfanyl]-1,2,4-triazol-3-yl]-1,3-oxazole Chemical compound C([C@]1(C[C@H]1C1)C=2C=CC(=CC=2)C(F)(F)F)N1C(C)CCSC(N1C)=NN=C1C=1OC=NC=1C GLSJOAMLOIMSGI-KMDAROACSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 3
- 230000009286 beneficial effect Effects 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- 125000000335 thiazolyl group Chemical group 0.000 claims 3
- 125000001544 thienyl group Chemical group 0.000 claims 3
- PSAASTBVOYWQMI-CJAUYULYSA-N 1-[2-methoxy-5-[(1r,5s)-3-[3-[[4-methyl-5-(4-methyl-1,3-oxazol-5-yl)-1,2,4-triazol-3-yl]sulfanyl]propyl]-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]propan-1-one Chemical compound C1=C(OC)C(C(=O)CC)=CC([C@]23[C@H](C2)CN(CCCSC=2N(C(C4=C(N=CO4)C)=NN=2)C)C3)=C1 PSAASTBVOYWQMI-CJAUYULYSA-N 0.000 claims 2
- HMMLWDCQIVJIHP-KDYSTLNUSA-N 2-methyl-5-[4-methyl-5-[3-[(1s,5r)-1-phenyl-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-1,2,4-triazol-3-yl]quinoline Chemical compound C1([C@]23C[C@H]2CN(C3)CCCSC2=NN=C(N2C)C=2C3=CC=C(N=C3C=CC=2)C)=CC=CC=C1 HMMLWDCQIVJIHP-KDYSTLNUSA-N 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical compound C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 claims 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
- UAOBDKREOZMZJQ-HXOBKFHXSA-N 4-methyl-5-[4-methyl-5-[3-[(1r,5s)-1-(2-methyl-1,3-benzothiazol-5-yl)-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-1,2,4-triazol-3-yl]-1,3-oxazole Chemical compound C([C@H]1C[C@]1(C1)C=2C=C3N=C(SC3=CC=2)C)N1CCCSC(N1C)=NN=C1C=1OC=NC=1C UAOBDKREOZMZJQ-HXOBKFHXSA-N 0.000 claims 2
- MLHRKLZCJRKSHO-UTKZUKDTSA-N 4-methyl-5-[4-methyl-5-[3-[(1r,5s)-1-[3-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-1,2,4-triazol-3-yl]-1,3-oxazole Chemical compound N1=COC(C=2N(C(SCCCN3C[C@@]4(C[C@@H]4C3)C=3C=C(C=CC=3)C(F)(F)F)=NN=2)C)=C1C MLHRKLZCJRKSHO-UTKZUKDTSA-N 0.000 claims 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 2
- RDNMLFUSVMBDDY-FGZHOGPDSA-N 5-[5-[3-[(1r,5s)-1-(3-chlorophenyl)-5-methyl-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-4-methyl-1,2,4-triazol-3-yl]-4-methyl-1,3-oxazole Chemical compound N1=COC(C=2N(C(SCCCN3C[C@]4(C[C@]4(C)C3)C=3C=C(Cl)C=CC=3)=NN=2)C)=C1C RDNMLFUSVMBDDY-FGZHOGPDSA-N 0.000 claims 2
- VUFRFPUOFHXBBM-HRFSGMKKSA-N 5-[5-[3-[(1r,5s)-1-(4-bromophenyl)-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-4-methyl-1,2,4-triazol-3-yl]-2-methylquinoline Chemical compound C1([C@@]23C[C@@H]2CN(C3)CCCSC2=NN=C(N2C)C=2C3=CC=C(N=C3C=CC=2)C)=CC=C(Br)C=C1 VUFRFPUOFHXBBM-HRFSGMKKSA-N 0.000 claims 2
- NKIUMOVWDJZMRB-PIKZIKFNSA-N 5-[5-[3-[(1r,5s)-1-(4-methoxyphenyl)-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-4-methyl-1,2,4-triazol-3-yl]-2-methylquinoline Chemical compound C1=CC(OC)=CC=C1[C@]1(CN(CCCSC=2N(C(C=3C4=CC=C(C)N=C4C=CC=3)=NN=2)C)C2)[C@@H]2C1 NKIUMOVWDJZMRB-PIKZIKFNSA-N 0.000 claims 2
- DRKUAUJUSZGTGW-XJFCNFDWSA-N 5-[5-[3-[(1r,5s)-1-(4-tert-butylphenyl)-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-4-methyl-1,2,4-triazol-3-yl]-2-methylquinoline Chemical compound C1([C@@]23C[C@@H]2CN(C3)CCCSC2=NN=C(N2C)C=2C3=CC=C(N=C3C=CC=2)C)=CC=C(C(C)(C)C)C=C1 DRKUAUJUSZGTGW-XJFCNFDWSA-N 0.000 claims 2
- URICTYNITRPTLS-UZTOHYMASA-N 5-[5-[3-[(1s,5r)-1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-4-methyl-1,2,4-triazol-3-yl]-2-methylquinoline Chemical compound C1([C@]23C[C@H]2CN(C3)CCCSC2=NN=C(N2C)C=2C3=CC=C(N=C3C=CC=2)C)=CC=C(Cl)C(Cl)=C1 URICTYNITRPTLS-UZTOHYMASA-N 0.000 claims 2
- VUFRFPUOFHXBBM-CCLHPLFOSA-N 5-[5-[3-[(1s,5r)-1-(4-bromophenyl)-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-4-methyl-1,2,4-triazol-3-yl]-2-methylquinoline Chemical compound C1([C@]23C[C@H]2CN(C3)CCCSC2=NN=C(N2C)C=2C3=CC=C(N=C3C=CC=2)C)=CC=C(Br)C=C1 VUFRFPUOFHXBBM-CCLHPLFOSA-N 0.000 claims 2
- NKIUMOVWDJZMRB-RBTNQOKQSA-N 5-[5-[3-[(1s,5r)-1-(4-methoxyphenyl)-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-4-methyl-1,2,4-triazol-3-yl]-2-methylquinoline Chemical compound C1=CC(OC)=CC=C1[C@@]1(CN(CCCSC=2N(C(C=3C4=CC=C(C)N=C4C=CC=3)=NN=2)C)C2)[C@H]2C1 NKIUMOVWDJZMRB-RBTNQOKQSA-N 0.000 claims 2
- DRKUAUJUSZGTGW-QXNWPYRLSA-N 5-[5-[3-[(1s,5r)-1-(4-tert-butylphenyl)-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-4-methyl-1,2,4-triazol-3-yl]-2-methylquinoline Chemical compound C1([C@]23C[C@H]2CN(C3)CCCSC2=NN=C(N2C)C=2C3=CC=C(N=C3C=CC=2)C)=CC=C(C(C)(C)C)C=C1 DRKUAUJUSZGTGW-QXNWPYRLSA-N 0.000 claims 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 230000001575 pathological effect Effects 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- GKACMWQTMKXQPT-WMZHIEFXSA-N (1s,5r)-1-(4-bromophenyl)-3-[3-[(4-ethyl-5-pyridin-3-yl-1,2,4-triazol-3-yl)sulfanyl]propyl]-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@]23C[C@H]2CN(C3)CCCSC=2N(C(=NN=2)C=2C=NC=CC=2)CC)=CC=C(Br)C=C1 GKACMWQTMKXQPT-WMZHIEFXSA-N 0.000 claims 1
- POPJUDCEQMELRU-LAUBAEHRSA-N (1s,5r)-1-(4-bromophenyl)-3-[3-[(4-methyl-5-pyridazin-4-yl-1,2,4-triazol-3-yl)sulfanyl]propyl]-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@]23C[C@H]2CN(C3)CCCSC=2N(C(=NN=2)C=2C=NN=CC=2)C)=CC=C(Br)C=C1 POPJUDCEQMELRU-LAUBAEHRSA-N 0.000 claims 1
- HTPVMIVXLCGVPI-PGRDOPGGSA-N (1s,5r)-1-(4-bromophenyl)-3-[3-[(4-methyl-5-pyridin-3-yl-1,2,4-triazol-3-yl)sulfanyl]propyl]-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@]23C[C@H]2CN(C3)CCCSC=2N(C(=NN=2)C=2C=NC=CC=2)C)=CC=C(Br)C=C1 HTPVMIVXLCGVPI-PGRDOPGGSA-N 0.000 claims 1
- ZUWBWKOPWGGXEZ-LAUBAEHRSA-N (1s,5r)-1-(4-bromophenyl)-3-[3-[(4-methyl-5-pyrimidin-5-yl-1,2,4-triazol-3-yl)sulfanyl]propyl]-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@]23C[C@H]2CN(C3)CCCSC=2N(C(=NN=2)C=2C=NC=NC=2)C)=CC=C(Br)C=C1 ZUWBWKOPWGGXEZ-LAUBAEHRSA-N 0.000 claims 1
- SZFGGKSIQQDFKO-MGPUTAFESA-N (1s,5r)-1-(4-bromophenyl)-3-[3-[[4-methyl-5-(1-methyltriazol-4-yl)-1,2,4-triazol-3-yl]sulfanyl]propyl]-3-azabicyclo[3.1.0]hexane Chemical compound N1=NN(C)C=C1C(N1C)=NN=C1SCCCN1C[C@@]2(C=3C=CC(Br)=CC=3)C[C@H]2C1 SZFGGKSIQQDFKO-MGPUTAFESA-N 0.000 claims 1
- ZOVUVPBEDQGAEY-HRAATJIYSA-N (1s,5r)-1-(4-bromophenyl)-3-[3-[[4-methyl-5-(2-methylpyrazol-3-yl)-1,2,4-triazol-3-yl]sulfanyl]propyl]-3-azabicyclo[3.1.0]hexane Chemical compound CN1N=CC=C1C(N1C)=NN=C1SCCCN1C[C@@]2(C=3C=CC(Br)=CC=3)C[C@H]2C1 ZOVUVPBEDQGAEY-HRAATJIYSA-N 0.000 claims 1
- CAFSAVHFADPFEJ-FDDCHVKYSA-N (1s,5r)-1-(4-bromophenyl)-3-[3-[[4-methyl-5-(2-methylpyridin-3-yl)-1,2,4-triazol-3-yl]sulfanyl]propyl]-3-azabicyclo[3.1.0]hexane Chemical compound CC1=NC=CC=C1C(N1C)=NN=C1SCCCN1C[C@@]2(C=3C=CC(Br)=CC=3)C[C@H]2C1 CAFSAVHFADPFEJ-FDDCHVKYSA-N 0.000 claims 1
- WCOFNBHSYDWYKP-HTAPYJJXSA-N (1s,5r)-1-(4-bromophenyl)-3-[3-[[4-methyl-5-(3-methylfuran-2-yl)-1,2,4-triazol-3-yl]sulfanyl]propyl]-3-azabicyclo[3.1.0]hexane Chemical compound C1=COC(C=2N(C(SCCCN3C[C@]4(C[C@H]4C3)C=3C=CC(Br)=CC=3)=NN=2)C)=C1C WCOFNBHSYDWYKP-HTAPYJJXSA-N 0.000 claims 1
- XPYNDTGYDNWMBS-FDDCHVKYSA-N (1s,5r)-1-(4-bromophenyl)-3-[3-[[4-methyl-5-(3-methylpyridin-2-yl)-1,2,4-triazol-3-yl]sulfanyl]propyl]-3-azabicyclo[3.1.0]hexane Chemical compound CC1=CC=CN=C1C(N1C)=NN=C1SCCCN1C[C@@]2(C=3C=CC(Br)=CC=3)C[C@H]2C1 XPYNDTGYDNWMBS-FDDCHVKYSA-N 0.000 claims 1
- TVOWXONSXDBYAG-WMZHIEFXSA-N (1s,5r)-1-(4-bromophenyl)-3-[3-[[4-methyl-5-(5-methylpyridin-3-yl)-1,2,4-triazol-3-yl]sulfanyl]propyl]-3-azabicyclo[3.1.0]hexane Chemical compound CC1=CN=CC(C=2N(C(SCCCN3C[C@]4(C[C@H]4C3)C=3C=CC(Br)=CC=3)=NN=2)C)=C1 TVOWXONSXDBYAG-WMZHIEFXSA-N 0.000 claims 1
- XWYQMRGVVCAGPL-WMZHIEFXSA-N (1s,5r)-1-(4-bromophenyl)-3-[3-[[4-methyl-5-(6-methylpyridin-3-yl)-1,2,4-triazol-3-yl]sulfanyl]propyl]-3-azabicyclo[3.1.0]hexane Chemical compound C1=NC(C)=CC=C1C(N1C)=NN=C1SCCCN1C[C@@]2(C=3C=CC(Br)=CC=3)C[C@H]2C1 XWYQMRGVVCAGPL-WMZHIEFXSA-N 0.000 claims 1
- ACTJTIJRIQDHEB-PGRDOPGGSA-N (1s,5r)-1-(4-bromophenyl)-3-[3-[[4-methyl-5-(oxan-4-yl)-1,2,4-triazol-3-yl]sulfanyl]propyl]-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@]23C[C@H]2CN(C3)CCCSC=2N(C(=NN=2)C2CCOCC2)C)=CC=C(Br)C=C1 ACTJTIJRIQDHEB-PGRDOPGGSA-N 0.000 claims 1
- GIWTTYIZASKYKT-YCRPNKLZSA-N (1s,5r)-1-(4-bromophenyl)-3-[3-[[4-methyl-5-[1-methyl-3-(trifluoromethyl)pyrazol-4-yl]-1,2,4-triazol-3-yl]sulfanyl]propyl]-3-azabicyclo[3.1.0]hexane Chemical compound FC(F)(F)C1=NN(C)C=C1C(N1C)=NN=C1SCCCN1C[C@@]2(C=3C=CC(Br)=CC=3)C[C@H]2C1 GIWTTYIZASKYKT-YCRPNKLZSA-N 0.000 claims 1
- NVNFYUKRFGJWDM-GAJHUEQPSA-N (1s,5r)-1-(4-bromophenyl)-3-[3-[[4-methyl-5-[2-methyl-6-(trifluoromethyl)pyridin-3-yl]-1,2,4-triazol-3-yl]sulfanyl]propyl]-3-azabicyclo[3.1.0]hexane Chemical compound CC1=NC(C(F)(F)F)=CC=C1C(N1C)=NN=C1SCCCN1C[C@@]2(C=3C=CC(Br)=CC=3)C[C@H]2C1 NVNFYUKRFGJWDM-GAJHUEQPSA-N 0.000 claims 1
- AIEYZNFNEQHWKO-WMZHIEFXSA-N (1s,5r)-1-(4-bromophenyl)-3-[3-[[4-methyl-5-[4-(trifluoromethyl)phenyl]-1,2,4-triazol-3-yl]sulfanyl]propyl]-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@]23C[C@H]2CN(C3)CCCSC=2N(C(=NN=2)C=2C=CC(=CC=2)C(F)(F)F)C)=CC=C(Br)C=C1 AIEYZNFNEQHWKO-WMZHIEFXSA-N 0.000 claims 1
- BUNMQAXAYZRBJI-HTAPYJJXSA-N (1s,5r)-1-(4-bromophenyl)-3-[3-[[5-(1,5-dimethylpyrazol-4-yl)-4-methyl-1,2,4-triazol-3-yl]sulfanyl]propyl]-3-azabicyclo[3.1.0]hexane Chemical compound C1=NN(C)C(C)=C1C(N1C)=NN=C1SCCCN1C[C@@]2(C=3C=CC(Br)=CC=3)C[C@H]2C1 BUNMQAXAYZRBJI-HTAPYJJXSA-N 0.000 claims 1
- DHPMGQUNTCQWHG-FDDCHVKYSA-N (1s,5r)-1-(4-bromophenyl)-3-[3-[[5-(2,5-dimethylfuran-3-yl)-4-methyl-1,2,4-triazol-3-yl]sulfanyl]propyl]-3-azabicyclo[3.1.0]hexane Chemical compound O1C(C)=CC(C=2N(C(SCCCN3C[C@]4(C[C@H]4C3)C=3C=CC(Br)=CC=3)=NN=2)C)=C1C DHPMGQUNTCQWHG-FDDCHVKYSA-N 0.000 claims 1
- BCASKIBJIZNNHQ-GAJHUEQPSA-N (1s,5r)-1-(4-bromophenyl)-3-[3-[[5-(3,4-difluorophenyl)-4-methyl-1,2,4-triazol-3-yl]sulfanyl]propyl]-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@]23C[C@H]2CN(C3)CCCSC=2N(C(=NN=2)C=2C=C(F)C(F)=CC=2)C)=CC=C(Br)C=C1 BCASKIBJIZNNHQ-GAJHUEQPSA-N 0.000 claims 1
- ICMWFZOZUUSQNF-YCRPNKLZSA-N (1s,5r)-1-(4-bromophenyl)-3-[3-[[5-(5-chloro-1-methylpyrazol-4-yl)-4-methyl-1,2,4-triazol-3-yl]sulfanyl]propyl]-3-azabicyclo[3.1.0]hexane Chemical compound CN1N=CC(C=2N(C(SCCCN3C[C@]4(C[C@H]4C3)C=3C=CC(Br)=CC=3)=NN=2)C)=C1Cl ICMWFZOZUUSQNF-YCRPNKLZSA-N 0.000 claims 1
- HRNYFPHZFKDZFM-YCRPNKLZSA-N (1s,5r)-1-(4-bromophenyl)-3-[3-[[5-(5-chlorothiophen-2-yl)-4-methyl-1,2,4-triazol-3-yl]sulfanyl]propyl]-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@]23C[C@H]2CN(C3)CCCSC=2N(C(=NN=2)C=2SC(Cl)=CC=2)C)=CC=C(Br)C=C1 HRNYFPHZFKDZFM-YCRPNKLZSA-N 0.000 claims 1
- JJASSNLYKBIBDB-KKSFZXQISA-N (1s,5r)-1-[2-fluoro-4-(trifluoromethyl)phenyl]-3-[3-[(4-methyl-5-pyridazin-4-yl-1,2,4-triazol-3-yl)sulfanyl]propyl]-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@]23C[C@H]2CN(C3)CCCSC=2N(C(=NN=2)C=2C=NN=CC=2)C)=CC=C(C(F)(F)F)C=C1F JJASSNLYKBIBDB-KKSFZXQISA-N 0.000 claims 1
- JCQGGPNAPQZIIU-KKSFZXQISA-N (1s,5r)-1-[2-fluoro-4-(trifluoromethyl)phenyl]-3-[3-[(4-methyl-5-pyrimidin-5-yl-1,2,4-triazol-3-yl)sulfanyl]propyl]-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@]23C[C@H]2CN(C3)CCCSC=2N(C(=NN=2)C=2C=NC=NC=2)C)=CC=C(C(F)(F)F)C=C1F JCQGGPNAPQZIIU-KKSFZXQISA-N 0.000 claims 1
- IIBPCCLUIAWPNP-SBUREZEXSA-N (1s,5r)-1-[2-fluoro-4-(trifluoromethyl)phenyl]-3-[3-[[4-methyl-5-(2-methylpyridin-3-yl)-1,2,4-triazol-3-yl]sulfanyl]propyl]-3-azabicyclo[3.1.0]hexane Chemical compound CC1=NC=CC=C1C(N1C)=NN=C1SCCCN1C[C@@]2(C=3C(=CC(=CC=3)C(F)(F)F)F)C[C@H]2C1 IIBPCCLUIAWPNP-SBUREZEXSA-N 0.000 claims 1
- XMDQXTSZWZHIQV-AOMKIAJQSA-N (1s,5r)-1-[2-fluoro-4-(trifluoromethyl)phenyl]-3-[3-[[4-methyl-5-(5-methylpyrazin-2-yl)-1,2,4-triazol-3-yl]sulfanyl]propyl]-3-azabicyclo[3.1.0]hexane Chemical compound C1=NC(C)=CN=C1C(N1C)=NN=C1SCCCN1C[C@@]2(C=3C(=CC(=CC=3)C(F)(F)F)F)C[C@H]2C1 XMDQXTSZWZHIQV-AOMKIAJQSA-N 0.000 claims 1
- SWSAZAYWDBMULB-MBSDFSHPSA-N (1s,5r)-1-[2-fluoro-4-(trifluoromethyl)phenyl]-3-[3-[[4-methyl-5-[4-(trifluoromethyl)phenyl]-1,2,4-triazol-3-yl]sulfanyl]propyl]-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@]23C[C@H]2CN(C3)CCCSC=2N(C(=NN=2)C=2C=CC(=CC=2)C(F)(F)F)C)=CC=C(C(F)(F)F)C=C1F SWSAZAYWDBMULB-MBSDFSHPSA-N 0.000 claims 1
- WXNXGSDVKPBNGU-PGRDOPGGSA-N (1s,5r)-3-[3-[(4-methyl-5-phenyl-1,2,4-triazol-3-yl)sulfanyl]propyl]-1-[6-(trifluoromethyl)pyridin-3-yl]-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@]23C[C@H]2CN(C3)CCCSC=2N(C(=NN=2)C=2C=CC=CC=2)C)=CC=C(C(F)(F)F)N=C1 WXNXGSDVKPBNGU-PGRDOPGGSA-N 0.000 claims 1
- OTKZOEOQKWTXMD-GHTZIAJQSA-N (1s,5r)-3-[3-[(4-methyl-5-pyridazin-4-yl-1,2,4-triazol-3-yl)sulfanyl]propyl]-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@]23C[C@H]2CN(C3)CCCSC=2N(C(=NN=2)C=2C=NN=CC=2)C)=CC=C(C(F)(F)F)C=C1 OTKZOEOQKWTXMD-GHTZIAJQSA-N 0.000 claims 1
- ZUBZEOWJXKKPSY-GHTZIAJQSA-N (1s,5r)-3-[3-[(4-methyl-5-pyrimidin-5-yl-1,2,4-triazol-3-yl)sulfanyl]propyl]-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@]23C[C@H]2CN(C3)CCCSC=2N(C(=NN=2)C=2C=NC=NC=2)C)=CC=C(C(F)(F)F)C=C1 ZUBZEOWJXKKPSY-GHTZIAJQSA-N 0.000 claims 1
- WHGLFZPJAYDODK-WMZHIEFXSA-N (1s,5r)-3-[3-[[4-methyl-5-(2-methylpyridin-3-yl)-1,2,4-triazol-3-yl]sulfanyl]propyl]-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane Chemical compound CC1=NC=CC=C1C(N1C)=NN=C1SCCCN1C[C@@]2(C=3C=CC(=CC=3)C(F)(F)F)C[C@H]2C1 WHGLFZPJAYDODK-WMZHIEFXSA-N 0.000 claims 1
- VCUZSEOWZWQCDM-HTAPYJJXSA-N (1s,5r)-3-[3-[[4-methyl-5-(2-methylpyridin-3-yl)-1,2,4-triazol-3-yl]sulfanyl]propyl]-1-[6-(trifluoromethyl)pyridin-3-yl]-3-azabicyclo[3.1.0]hexane Chemical compound CC1=NC=CC=C1C(N1C)=NN=C1SCCCN1C[C@@]2(C=3C=NC(=CC=3)C(F)(F)F)C[C@H]2C1 VCUZSEOWZWQCDM-HTAPYJJXSA-N 0.000 claims 1
- AEXFOTSQBUVBKJ-PGRDOPGGSA-N (1s,5r)-3-[3-[[4-methyl-5-(5-methylpyrazin-2-yl)-1,2,4-triazol-3-yl]sulfanyl]propyl]-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane Chemical compound C1=NC(C)=CN=C1C(N1C)=NN=C1SCCCN1C[C@@]2(C=3C=CC(=CC=3)C(F)(F)F)C[C@H]2C1 AEXFOTSQBUVBKJ-PGRDOPGGSA-N 0.000 claims 1
- GXTDRNOVSQHWKB-HRAATJIYSA-N (1s,5r)-3-[3-[[4-methyl-5-(5-methylpyrazin-2-yl)-1,2,4-triazol-3-yl]sulfanyl]propyl]-1-[6-(trifluoromethyl)pyridin-3-yl]-3-azabicyclo[3.1.0]hexane Chemical compound C1=NC(C)=CN=C1C(N1C)=NN=C1SCCCN1C[C@@]2(C=3C=NC(=CC=3)C(F)(F)F)C[C@H]2C1 GXTDRNOVSQHWKB-HRAATJIYSA-N 0.000 claims 1
- CCJLDYTVWAENSM-NZQKXSOJSA-N (1s,5r)-3-[3-[[4-methyl-5-(6-methylpyridin-3-yl)-1,2,4-triazol-3-yl]sulfanyl]propyl]-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane Chemical compound C1=NC(C)=CC=C1C(N1C)=NN=C1SCCCN1C[C@@]2(C=3C=CC(=CC=3)C(F)(F)F)C[C@H]2C1 CCJLDYTVWAENSM-NZQKXSOJSA-N 0.000 claims 1
- RUIZWYILWQFWPT-PGRDOPGGSA-N (1s,5r)-3-[3-[[4-methyl-5-(6-methylpyridin-3-yl)-1,2,4-triazol-3-yl]sulfanyl]propyl]-1-[6-(trifluoromethyl)pyridin-3-yl]-3-azabicyclo[3.1.0]hexane Chemical compound C1=NC(C)=CC=C1C(N1C)=NN=C1SCCCN1C[C@@]2(C=3C=NC(=CC=3)C(F)(F)F)C[C@H]2C1 RUIZWYILWQFWPT-PGRDOPGGSA-N 0.000 claims 1
- KZBPRKVXUYDFQJ-PGRDOPGGSA-N (1s,5r)-3-[3-[[4-methyl-5-(oxan-4-yl)-1,2,4-triazol-3-yl]sulfanyl]propyl]-1-[4-(trifluoromethoxy)phenyl]-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@]23C[C@H]2CN(C3)CCCSC=2N(C(=NN=2)C2CCOCC2)C)=CC=C(OC(F)(F)F)C=C1 KZBPRKVXUYDFQJ-PGRDOPGGSA-N 0.000 claims 1
- HJAJGYFKFFRJEC-SIKLNZKXSA-N (1s,5r)-3-[3-[[4-methyl-5-(oxan-4-yl)-1,2,4-triazol-3-yl]sulfanyl]propyl]-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@]23C[C@H]2CN(C3)CCCSC=2N(C(=NN=2)C2CCOCC2)C)=CC=C(C(F)(F)F)C=C1 HJAJGYFKFFRJEC-SIKLNZKXSA-N 0.000 claims 1
- PTRHJEYSWXFORZ-PGRDOPGGSA-N (1s,5r)-3-[3-[[4-methyl-5-[4-(trifluoromethyl)phenyl]-1,2,4-triazol-3-yl]sulfanyl]propyl]-1-[6-(trifluoromethyl)pyridin-3-yl]-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@]23C[C@H]2CN(C3)CCCSC=2N(C(=NN=2)C=2C=CC(=CC=2)C(F)(F)F)C)=CC=C(C(F)(F)F)N=C1 PTRHJEYSWXFORZ-PGRDOPGGSA-N 0.000 claims 1
- SYCYUYFGTJYLJB-PGRDOPGGSA-N (1s,5r)-3-[3-[[5-(1,5-dimethylpyrazol-4-yl)-4-methyl-1,2,4-triazol-3-yl]sulfanyl]propyl]-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane Chemical compound C1=NN(C)C(C)=C1C(N1C)=NN=C1SCCCN1C[C@@]2(C=3C=CC(=CC=3)C(F)(F)F)C[C@H]2C1 SYCYUYFGTJYLJB-PGRDOPGGSA-N 0.000 claims 1
- HSORSBPOHUZXNY-KCWXNJEJSA-N 1-[2-hydroxy-5-[(1s,5r)-3-[3-[[4-methyl-5-(2-methylquinolin-5-yl)-1,2,4-triazol-3-yl]sulfanyl]propyl]-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]ethanone Chemical compound C1=C(O)C(C(=O)C)=CC([C@@]23[C@@H](C2)CN(CCCSC=2N(C(C=4C5=CC=C(C)N=C5C=CC=4)=NN=2)C)C3)=C1 HSORSBPOHUZXNY-KCWXNJEJSA-N 0.000 claims 1
- KHWKHOXPNILXFK-NBGIEHNGSA-N 1-[2-hydroxy-5-[(1s,5r)-3-[3-[[4-methyl-5-[4-(trifluoromethyl)phenyl]-1,2,4-triazol-3-yl]sulfanyl]propyl]-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]ethanone Chemical compound C1=C(O)C(C(=O)C)=CC([C@@]23[C@@H](C2)CN(CCCSC=2N(C(C=4C=CC(=CC=4)C(F)(F)F)=NN=2)C)C3)=C1 KHWKHOXPNILXFK-NBGIEHNGSA-N 0.000 claims 1
- OOUUSTJOZYKIFZ-MHECFPHRSA-N 1-[2-methoxy-4-[(1s,5r)-3-[3-[[4-methyl-5-(4-methyl-1,3-oxazol-5-yl)-1,2,4-triazol-3-yl]sulfanyl]propyl]-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]ethanone Chemical compound C1=C(C(C)=O)C(OC)=CC([C@@]23[C@@H](C2)CN(CCCSC=2N(C(C4=C(N=CO4)C)=NN=2)C)C3)=C1 OOUUSTJOZYKIFZ-MHECFPHRSA-N 0.000 claims 1
- GHYALLPUTLGENT-AVRWGWEMSA-N 1-[2-methoxy-4-[(1s,5r)-3-[3-[[4-methyl-5-(4-methyl-1,3-oxazol-5-yl)-1,2,4-triazol-3-yl]sulfanyl]propyl]-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]propan-1-one Chemical compound C1=C(OC)C(C(=O)CC)=CC=C1[C@@]1(CN(CCCSC=2N(C(C3=C(N=CO3)C)=NN=2)C)C2)[C@H]2C1 GHYALLPUTLGENT-AVRWGWEMSA-N 0.000 claims 1
- WUXMBXJSTUXONL-NBGIEHNGSA-N 1-[2-methoxy-5-[(1s,5r)-3-[3-[(4-methyl-5-pyridin-3-yl-1,2,4-triazol-3-yl)sulfanyl]propyl]-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]ethanone Chemical compound C1=C(C(C)=O)C(OC)=CC=C1[C@@]1(CN(CCCSC=2N(C(C=3C=NC=CC=3)=NN=2)C)C2)[C@H]2C1 WUXMBXJSTUXONL-NBGIEHNGSA-N 0.000 claims 1
- WWMANSPKRWDTJQ-SMSORMJASA-N 1-[2-methoxy-5-[(1s,5r)-3-[3-[[4-methyl-5-(2-methylquinolin-5-yl)-1,2,4-triazol-3-yl]sulfanyl]propyl]-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]ethanone Chemical compound C1=C(C(C)=O)C(OC)=CC=C1[C@@]1(CN(CCCSC=2N(C(C=3C4=CC=C(C)N=C4C=CC=3)=NN=2)C)C2)[C@H]2C1 WWMANSPKRWDTJQ-SMSORMJASA-N 0.000 claims 1
- YQNWPSNHRUBNBO-MHECFPHRSA-N 1-[2-methoxy-5-[(1s,5r)-3-[3-[[4-methyl-5-(4-methyl-1,3-oxazol-5-yl)-1,2,4-triazol-3-yl]sulfanyl]propyl]-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]ethanone Chemical compound C1=C(C(C)=O)C(OC)=CC=C1[C@@]1(CN(CCCSC=2N(C(C3=C(N=CO3)C)=NN=2)C)C2)[C@H]2C1 YQNWPSNHRUBNBO-MHECFPHRSA-N 0.000 claims 1
- PSAASTBVOYWQMI-AVRWGWEMSA-N 1-[2-methoxy-5-[(1s,5r)-3-[3-[[4-methyl-5-(4-methyl-1,3-oxazol-5-yl)-1,2,4-triazol-3-yl]sulfanyl]propyl]-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]propan-1-one Chemical compound C1=C(OC)C(C(=O)CC)=CC([C@@]23[C@@H](C2)CN(CCCSC=2N(C(C4=C(N=CO4)C)=NN=2)C)C3)=C1 PSAASTBVOYWQMI-AVRWGWEMSA-N 0.000 claims 1
- SIWHEXWKLXJQML-NBGIEHNGSA-N 1-[2-methoxy-5-[(1s,5r)-3-[3-[[4-methyl-5-(oxan-4-yl)-1,2,4-triazol-3-yl]sulfanyl]propyl]-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]ethanone Chemical compound C1=C(C(C)=O)C(OC)=CC=C1[C@@]1(CN(CCCSC=2N(C(C3CCOCC3)=NN=2)C)C2)[C@H]2C1 SIWHEXWKLXJQML-NBGIEHNGSA-N 0.000 claims 1
- XHXOKGKTIICKOZ-HFZDXXHNSA-N 1-[2-methoxy-5-[(1s,5r)-3-[3-[[4-methyl-5-[4-(trifluoromethyl)phenyl]-1,2,4-triazol-3-yl]sulfanyl]propyl]-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]ethanone Chemical compound C1=C(C(C)=O)C(OC)=CC=C1[C@@]1(CN(CCCSC=2N(C(C=3C=CC(=CC=3)C(F)(F)F)=NN=2)C)C2)[C@H]2C1 XHXOKGKTIICKOZ-HFZDXXHNSA-N 0.000 claims 1
- CDTMYUYGZNHOPV-GTYOFVGBSA-N 1-[4-[(1s,5r)-3-[3-[[4-methyl-5-(2-methylquinolin-5-yl)-1,2,4-triazol-3-yl]sulfanyl]propyl]-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]pyrrolidin-2-one Chemical compound C1=CC([C@]23C[C@H]2CN(C3)CCCSC2=NN=C(N2C)C=2C3=CC=C(N=C3C=CC=2)C)=CC=C1N1CCCC1=O CDTMYUYGZNHOPV-GTYOFVGBSA-N 0.000 claims 1
- ZKGLMIMJGUYTID-AVRWGWEMSA-N 1-[5-[(1s,5r)-3-[3-[[5-(3,4-difluorophenyl)-4-methyl-1,2,4-triazol-3-yl]sulfanyl]propyl]-3-azabicyclo[3.1.0]hexan-1-yl]-2-hydroxyphenyl]ethanone Chemical compound C1=C(O)C(C(=O)C)=CC([C@@]23[C@@H](C2)CN(CCCSC=2N(C(C=4C=C(F)C(F)=CC=4)=NN=2)C)C3)=C1 ZKGLMIMJGUYTID-AVRWGWEMSA-N 0.000 claims 1
- DBHVXGHVYLHGTG-AFMDSPMNSA-N 1-[5-[(1s,5r)-3-[3-[[5-(3,4-difluorophenyl)-4-methyl-1,2,4-triazol-3-yl]sulfanyl]propyl]-3-azabicyclo[3.1.0]hexan-1-yl]-2-methoxyphenyl]ethanone Chemical compound C1=C(C(C)=O)C(OC)=CC=C1[C@@]1(CN(CCCSC=2N(C(C=3C=C(F)C(F)=CC=3)=NN=2)C)C2)[C@H]2C1 DBHVXGHVYLHGTG-AFMDSPMNSA-N 0.000 claims 1
- WGSXKYXKAARAKD-UHFFFAOYSA-N 1-fluoro-3-isocyanato-5-(trifluoromethyl)benzene Chemical group FC1=CC(N=C=O)=CC(C(F)(F)F)=C1 WGSXKYXKAARAKD-UHFFFAOYSA-N 0.000 claims 1
- ODIJMXCJWMOZFJ-PGRDOPGGSA-N 2,4-dimethyl-5-[4-methyl-5-[3-[(1s,5r)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-1,2,4-triazol-3-yl]-1,3-thiazole Chemical compound S1C(C)=NC(C)=C1C(N1C)=NN=C1SCCCN1C[C@@]2(C=3C=CC(=CC=3)C(F)(F)F)C[C@H]2C1 ODIJMXCJWMOZFJ-PGRDOPGGSA-N 0.000 claims 1
- QGHRENZJUREQGK-HRAATJIYSA-N 2,4-dimethyl-5-[4-methyl-5-[3-[(1s,5r)-1-[6-(trifluoromethyl)pyridin-3-yl]-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-1,2,4-triazol-3-yl]-1,3-thiazole Chemical compound S1C(C)=NC(C)=C1C(N1C)=NN=C1SCCCN1C[C@@]2(C=3C=NC(=CC=3)C(F)(F)F)C[C@H]2C1 QGHRENZJUREQGK-HRAATJIYSA-N 0.000 claims 1
- PNKRTTBCLUZVBM-NBGIEHNGSA-N 2-methyl-5-[(1s,5r)-3-[3-[(4-methyl-5-phenyl-1,2,4-triazol-3-yl)sulfanyl]propyl]-3-azabicyclo[3.1.0]hexan-1-yl]-1,3-benzothiazole Chemical compound C([C@@H]1C[C@@]1(C1)C=2C=C3N=C(SC3=CC=2)C)N1CCCSC(N1C)=NN=C1C1=CC=CC=C1 PNKRTTBCLUZVBM-NBGIEHNGSA-N 0.000 claims 1
- CKQJENKLIZUINM-MHECFPHRSA-N 2-methyl-5-[(1s,5r)-3-[3-[[4-methyl-5-(5-methylpyrazin-2-yl)-1,2,4-triazol-3-yl]sulfanyl]propyl]-3-azabicyclo[3.1.0]hexan-1-yl]-1,3-benzothiazole Chemical compound C([C@@H]1C[C@@]1(C1)C=2C=C3N=C(SC3=CC=2)C)N1CCCSC(N1C)=NN=C1C1=CN=C(C)C=N1 CKQJENKLIZUINM-MHECFPHRSA-N 0.000 claims 1
- DRBBHLNQSPVHLL-NBGIEHNGSA-N 2-methyl-5-[(1s,5r)-3-[3-[[4-methyl-5-(6-methylpyridin-3-yl)-1,2,4-triazol-3-yl]sulfanyl]propyl]-3-azabicyclo[3.1.0]hexan-1-yl]-1,3-benzothiazole Chemical compound C([C@@H]1C[C@@]1(C1)C=2C=C3N=C(SC3=CC=2)C)N1CCCSC(N1C)=NN=C1C1=CC=C(C)N=C1 DRBBHLNQSPVHLL-NBGIEHNGSA-N 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- CLLQEXUCEWAACY-RBISFHTESA-N 4-[(1s,5r)-3-[3-[[4-methyl-5-(2-methylquinolin-5-yl)-1,2,4-triazol-3-yl]sulfanyl]propyl]-3-azabicyclo[3.1.0]hexan-1-yl]benzonitrile Chemical compound C1([C@]23C[C@H]2CN(C3)CCCSC2=NN=C(N2C)C=2C3=CC=C(N=C3C=CC=2)C)=CC=C(C#N)C=C1 CLLQEXUCEWAACY-RBISFHTESA-N 0.000 claims 1
- SQHSACZAZLANKD-YCRPNKLZSA-N 4-[5-[3-[(1s,5r)-1-(4-bromophenyl)-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-4-methyl-1,2,4-triazol-3-yl]-2-methyl-5-(trifluoromethyl)-1,3-oxazole Chemical compound O1C(C)=NC(C=2N(C(SCCCN3C[C@]4(C[C@H]4C3)C=3C=CC(Br)=CC=3)=NN=2)C)=C1C(F)(F)F SQHSACZAZLANKD-YCRPNKLZSA-N 0.000 claims 1
- FPFPTUKYJWTWPY-YWZLYKJASA-N 4-methyl-5-[4-methyl-5-[3-[(1r,5r)-1-[5-(trifluoromethyl)pyridin-2-yl]-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-1,2,4-triazol-3-yl]-1,3-oxazole Chemical compound N1=COC(C=2N(C(SCCCN3C[C@]4(C[C@H]4C3)C=3N=CC(=CC=3)C(F)(F)F)=NN=2)C)=C1C FPFPTUKYJWTWPY-YWZLYKJASA-N 0.000 claims 1
- JWUUYXCKKOYVDZ-XOBRGWDASA-N 4-methyl-5-[4-methyl-5-[3-[(1r,5r)-1-[6-(trifluoromethyl)pyridin-2-yl]-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-1,2,4-triazol-3-yl]-1,3-oxazole Chemical compound N1=COC(C=2N(C(SCCCN3C[C@]4(C[C@H]4C3)C=3N=C(C=CC=3)C(F)(F)F)=NN=2)C)=C1C JWUUYXCKKOYVDZ-XOBRGWDASA-N 0.000 claims 1
- LEUDJRMEBMLZBI-FDDCHVKYSA-N 4-methyl-5-[4-methyl-5-[3-[(1s,5r)-1-(1-methylindazol-5-yl)-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-1,2,4-triazol-3-yl]-1,3-oxazole Chemical compound N1=COC(C=2N(C(SCCCN3C[C@]4(C[C@H]4C3)C=3C=C4C=NN(C)C4=CC=3)=NN=2)C)=C1C LEUDJRMEBMLZBI-FDDCHVKYSA-N 0.000 claims 1
- UAOBDKREOZMZJQ-GAJHUEQPSA-N 4-methyl-5-[4-methyl-5-[3-[(1s,5r)-1-(2-methyl-1,3-benzothiazol-5-yl)-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-1,2,4-triazol-3-yl]-1,3-oxazole Chemical compound C([C@@H]1C[C@@]1(C1)C=2C=C3N=C(SC3=CC=2)C)N1CCCSC(N1C)=NN=C1C=1OC=NC=1C UAOBDKREOZMZJQ-GAJHUEQPSA-N 0.000 claims 1
- OIERNJOFVGMUEF-GAJHUEQPSA-N 4-methyl-5-[4-methyl-5-[3-[(1s,5r)-1-(2-methyl-1,3-benzothiazol-6-yl)-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-1,2,4-triazol-3-yl]-1,3-oxazole Chemical compound C([C@@H]1C[C@@]1(C1)C2=CC=C3N=C(SC3=C2)C)N1CCCSC(N1C)=NN=C1C=1OC=NC=1C OIERNJOFVGMUEF-GAJHUEQPSA-N 0.000 claims 1
- KYPWROFHQUYOCS-BTYIYWSLSA-N 4-methyl-5-[4-methyl-5-[3-[(1s,5r)-1-[2-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-1,2,4-triazol-3-yl]-1,3-oxazole Chemical compound N1=COC(C=2N(C(SCCCN3C[C@]4(C[C@H]4C3)C=3C(=CC=CC=3)C(F)(F)F)=NN=2)C)=C1C KYPWROFHQUYOCS-BTYIYWSLSA-N 0.000 claims 1
- KFCVKULFYARZLT-JTSKRJEESA-N 4-methyl-5-[4-methyl-5-[3-[(1s,5r)-1-[2-methyl-4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-1,2,4-triazol-3-yl]-1,3-oxazole Chemical compound N1=COC(C=2N(C(SCCCN3C[C@]4(C[C@H]4C3)C=3C(=CC(=CC=3)C(F)(F)F)C)=NN=2)C)=C1C KFCVKULFYARZLT-JTSKRJEESA-N 0.000 claims 1
- FKRBBYMVCAJBHR-HFZDXXHNSA-N 4-methyl-5-[4-methyl-5-[3-[(1s,5r)-1-[3-(5-methylthiophen-2-yl)phenyl]-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-1,2,4-triazol-3-yl]-1,3-oxazole Chemical compound S1C(C)=CC=C1C1=CC=CC([C@@]23[C@@H](C2)CN(CCCSC=2N(C(C4=C(N=CO4)C)=NN=2)C)C3)=C1 FKRBBYMVCAJBHR-HFZDXXHNSA-N 0.000 claims 1
- MLHRKLZCJRKSHO-LAUBAEHRSA-N 4-methyl-5-[4-methyl-5-[3-[(1s,5r)-1-[3-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-1,2,4-triazol-3-yl]-1,3-oxazole Chemical compound N1=COC(C=2N(C(SCCCN3C[C@]4(C[C@H]4C3)C=3C=C(C=CC=3)C(F)(F)F)=NN=2)C)=C1C MLHRKLZCJRKSHO-LAUBAEHRSA-N 0.000 claims 1
- SRVOWVHRVJSZKO-HRAATJIYSA-N 4-methyl-5-[4-methyl-5-[3-[(1s,5r)-1-[4-(trifluoromethoxy)phenyl]-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-1,2,4-triazol-3-yl]-1,3-oxazole Chemical compound N1=COC(C=2N(C(SCCCN3C[C@]4(C[C@H]4C3)C=3C=CC(OC(F)(F)F)=CC=3)=NN=2)C)=C1C SRVOWVHRVJSZKO-HRAATJIYSA-N 0.000 claims 1
- HIRZFMOIKMLUHF-LAUBAEHRSA-N 4-methyl-5-[4-methyl-5-[3-[(1s,5r)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-1,2,4-triazol-3-yl]-1,3-oxazole Chemical compound N1=COC(C=2N(C(SCCCN3C[C@]4(C[C@H]4C3)C=3C=CC(=CC=3)C(F)(F)F)=NN=2)C)=C1C HIRZFMOIKMLUHF-LAUBAEHRSA-N 0.000 claims 1
- STMFIEJAIJCUPM-RXFWQSSRSA-N 4-methyl-5-[4-methyl-5-[3-[(1s,5r)-1-[4-[6-(trifluoromethyl)pyridin-2-yl]phenyl]-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-1,2,4-triazol-3-yl]-1,3-oxazole Chemical compound N1=COC(C=2N(C(SCCCN3C[C@]4(C[C@H]4C3)C=3C=CC(=CC=3)C=3N=C(C=CC=3)C(F)(F)F)=NN=2)C)=C1C STMFIEJAIJCUPM-RXFWQSSRSA-N 0.000 claims 1
- QWTAGVPLIGQGIW-MGPUTAFESA-N 4-methyl-5-[4-methyl-5-[3-[(1s,5r)-1-[6-(trifluoromethyl)pyridin-3-yl]-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-1,2,4-triazol-3-yl]-1,3-oxazole Chemical compound N1=COC(C=2N(C(SCCCN3C[C@]4(C[C@H]4C3)C=3C=NC(=CC=3)C(F)(F)F)=NN=2)C)=C1C QWTAGVPLIGQGIW-MGPUTAFESA-N 0.000 claims 1
- YYLVZNFHPHPLKB-LAUBAEHRSA-N 4-methyl-5-[4-methyl-5-[3-[(1s,5r)-1-phenyl-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-1,2,4-triazol-3-yl]-1,3-oxazole Chemical compound N1=COC(C=2N(C(SCCCN3C[C@]4(C[C@H]4C3)C=3C=CC=CC=3)=NN=2)C)=C1C YYLVZNFHPHPLKB-LAUBAEHRSA-N 0.000 claims 1
- UXBIDSXSMDZFKR-MHECFPHRSA-N 5-[(1s,5r)-3-[3-[[5-(2,4-dimethyl-1,3-thiazol-5-yl)-4-methyl-1,2,4-triazol-3-yl]sulfanyl]propyl]-3-azabicyclo[3.1.0]hexan-1-yl]-2-methyl-1,3-benzothiazole Chemical compound S1C(C)=NC(C)=C1C(N1C)=NN=C1SCCCN1C[C@@]2(C=3C=C4N=C(C)SC4=CC=3)C[C@H]2C1 UXBIDSXSMDZFKR-MHECFPHRSA-N 0.000 claims 1
- MHDWNZWHPYKUAY-UJPJHGMFSA-N 5-[5-[1-[(1s,5r)-1-(2-chloro-4-methylphenyl)-3-azabicyclo[3.1.0]hexan-3-yl]propan-2-ylsulfanyl]-4-methyl-1,2,4-triazol-3-yl]-4-methyl-1,3-oxazole Chemical compound C1([C@]23C[C@H]2CN(C3)CC(C)SC=2N(C(C3=C(N=CO3)C)=NN=2)C)=CC=C(C)C=C1Cl MHDWNZWHPYKUAY-UJPJHGMFSA-N 0.000 claims 1
- NRBWMTGEADXYFF-VQBJLOOESA-N 5-[5-[1-[(1s,5r)-1-(3-chloro-4-methoxyphenyl)-3-azabicyclo[3.1.0]hexan-3-yl]propan-2-ylsulfanyl]-4-methyl-1,2,4-triazol-3-yl]-4-methyl-1,3-oxazole Chemical compound C1=C(Cl)C(OC)=CC=C1[C@@]1(CN(CC(C)SC=2N(C(C3=C(N=CO3)C)=NN=2)C)C2)[C@H]2C1 NRBWMTGEADXYFF-VQBJLOOESA-N 0.000 claims 1
- YFAACACUMCZFCU-HRAATJIYSA-N 5-[5-[3-[(1s,5r)-1-(3-bromophenyl)-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-4-methyl-1,2,4-triazol-3-yl]-4-methyl-1,3-oxazole Chemical compound N1=COC(C=2N(C(SCCCN3C[C@]4(C[C@H]4C3)C=3C=C(Br)C=CC=3)=NN=2)C)=C1C YFAACACUMCZFCU-HRAATJIYSA-N 0.000 claims 1
- RDNMLFUSVMBDDY-VXKWHMMOSA-N 5-[5-[3-[(1s,5r)-1-(3-chlorophenyl)-5-methyl-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-4-methyl-1,2,4-triazol-3-yl]-4-methyl-1,3-oxazole Chemical compound N1=COC(C=2N(C(SCCCN3C[C@@]4(C[C@@]4(C)C3)C=3C=C(Cl)C=CC=3)=NN=2)C)=C1C RDNMLFUSVMBDDY-VXKWHMMOSA-N 0.000 claims 1
- JEBLLBOUXXZBPR-HRAATJIYSA-N 5-[5-[3-[(1s,5r)-1-(3-fluorophenyl)-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-4-methyl-1,2,4-triazol-3-yl]-4-methyl-1,3-oxazole Chemical compound N1=COC(C=2N(C(SCCCN3C[C@]4(C[C@H]4C3)C=3C=C(F)C=CC=3)=NN=2)C)=C1C JEBLLBOUXXZBPR-HRAATJIYSA-N 0.000 claims 1
- VSHFJDFDEHUHMG-HTAPYJJXSA-N 5-[5-[3-[(1s,5r)-1-(3-methoxyphenyl)-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-4-methyl-1,2,4-triazol-3-yl]-4-methyl-1,3-oxazole Chemical compound COC1=CC=CC([C@@]23[C@@H](C2)CN(CCCSC=2N(C(C4=C(N=CO4)C)=NN=2)C)C3)=C1 VSHFJDFDEHUHMG-HTAPYJJXSA-N 0.000 claims 1
- QYIGIFAPYBZLOA-HTAPYJJXSA-N 5-[5-[3-[(1s,5r)-1-(4-bromophenyl)-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-4-methyl-1,2,4-triazol-3-yl]-2,4-dimethyl-1,3-thiazole Chemical compound S1C(C)=NC(C)=C1C(N1C)=NN=C1SCCCN1C[C@@]2(C=3C=CC(Br)=CC=3)C[C@H]2C1 QYIGIFAPYBZLOA-HTAPYJJXSA-N 0.000 claims 1
- RWAAUSOBGQKJNX-HRAATJIYSA-N 5-[5-[3-[(1s,5r)-1-(4-bromophenyl)-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-4-methyl-1,2,4-triazol-3-yl]-3-methyl-1,2-oxazole Chemical compound O1N=C(C)C=C1C(N1C)=NN=C1SCCCN1C[C@@]2(C=3C=CC(Br)=CC=3)C[C@H]2C1 RWAAUSOBGQKJNX-HRAATJIYSA-N 0.000 claims 1
- TXPWWEBUZHUGQI-HRAATJIYSA-N 5-[5-[3-[(1s,5r)-1-(4-bromophenyl)-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-4-methyl-1,2,4-triazol-3-yl]-4-methyl-1,3-oxazole Chemical compound N1=COC(C=2N(C(SCCCN3C[C@]4(C[C@H]4C3)C=3C=CC(Br)=CC=3)=NN=2)C)=C1C TXPWWEBUZHUGQI-HRAATJIYSA-N 0.000 claims 1
- JASDXILVHIDXCQ-HRAATJIYSA-N 5-[5-[3-[(1s,5r)-1-(4-chlorophenyl)-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-4-methyl-1,2,4-triazol-3-yl]-4-methyl-1,3-oxazole Chemical compound N1=COC(C=2N(C(SCCCN3C[C@]4(C[C@H]4C3)C=3C=CC(Cl)=CC=3)=NN=2)C)=C1C JASDXILVHIDXCQ-HRAATJIYSA-N 0.000 claims 1
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- AVTONHYDPSFOLQ-HTAPYJJXSA-N 5-[5-[3-[(1s,5r)-1-(4-methoxyphenyl)-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-4-methyl-1,2,4-triazol-3-yl]-4-methyl-1,3-oxazole Chemical compound C1=CC(OC)=CC=C1[C@@]1(CN(CCCSC=2N(C(C3=C(N=CO3)C)=NN=2)C)C2)[C@H]2C1 AVTONHYDPSFOLQ-HTAPYJJXSA-N 0.000 claims 1
- KBYDKOYJEQUBOE-NBGIEHNGSA-N 5-[5-[3-[(1s,5r)-1-(4-tert-butylphenyl)-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-4-methyl-1,2,4-triazol-3-yl]-4-methyl-1,3-oxazole Chemical compound N1=COC(C=2N(C(SCCCN3C[C@]4(C[C@H]4C3)C=3C=CC(=CC=3)C(C)(C)C)=NN=2)C)=C1C KBYDKOYJEQUBOE-NBGIEHNGSA-N 0.000 claims 1
- CRZBMVVRCINCBG-AOMKIAJQSA-N 5-[5-[3-[(1s,5r)-1-[2-fluoro-4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-4-methyl-1,2,4-triazol-3-yl]-2,4-dimethyl-1,3-thiazole Chemical compound S1C(C)=NC(C)=C1C(N1C)=NN=C1SCCCN1C[C@@]2(C=3C(=CC(=CC=3)C(F)(F)F)F)C[C@H]2C1 CRZBMVVRCINCBG-AOMKIAJQSA-N 0.000 claims 1
- JASDXILVHIDXCQ-UHFFFAOYSA-N 5-[5-[3-[1-(4-chlorophenyl)-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-4-methyl-1,2,4-triazol-3-yl]-4-methyl-1,3-oxazole Chemical compound N1=COC(C=2N(C(SCCCN3CC4(CC4C3)C=3C=CC(Cl)=CC=3)=NN=2)C)=C1C JASDXILVHIDXCQ-UHFFFAOYSA-N 0.000 claims 1
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| US8138377B2 (en) | 2006-11-07 | 2012-03-20 | Dov Pharmaceutical, Inc. | Arylbicyclo[3.1.0]hexylamines and methods and compositions for their preparation and use |
| US9133159B2 (en) | 2007-06-06 | 2015-09-15 | Neurovance, Inc. | 1-heteroaryl-3-azabicyclo[3.1.0]hexanes, methods for their preparation and their use as medicaments |
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| AU2009271325A1 (en) | 2008-06-24 | 2010-01-21 | Merck Sharp & Dohme Corp. | Biocatalytic processes for the preparation of substantially stereomerically pure fused bicyclic proline compounds |
| AP3272A (en) | 2008-09-22 | 2015-05-31 | Cayman Chem Co | Multiheteroaryl compounds as inhibitors of H-PGDS and their use for treating prosaglandin D2 mediated diseases |
| CA2765692A1 (en) | 2009-06-26 | 2010-12-29 | Panacea Biotec Ltd. | Novel azabicyclohexanes |
| US20140206740A1 (en) | 2011-07-30 | 2014-07-24 | Neurovance, Inc. | Use Of (1R,5S)-(+)-(Napthalen-2-yl)-3-Azabicyclo[3.1.0]Hexane In The Treatment Of Conditions Affected By Monoamine Neurotransmitters |
| US20160279098A1 (en) * | 2013-11-11 | 2016-09-29 | Euthymics Bioscience, Inc. | Novel methods |
| CA2992820C (en) * | 2015-08-05 | 2022-08-16 | Indivior Uk Limited | Dopamine d3 receptor antagonists having a bicyclo moiety |
| JP7250405B2 (ja) | 2018-01-26 | 2023-04-03 | 塩野義製薬株式会社 | ドーパミンｄ３受容体拮抗作用を有する環式化合物 |
| US11787780B2 (en) | 2020-06-22 | 2023-10-17 | Corcept Therapeutics Incorporated | Quaternary indazole glucocorticoid receptor antagonists |
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| AR022230A1 (es) * | 1999-01-12 | 2002-09-04 | Abbott Gmbh & Co Kg | Compuestos de triazol, composicion farmaceutica que los comprende y uso de los mismos para preparar dicha composicion |
| GB0015562D0 (en) * | 2000-06-23 | 2000-08-16 | Pfizer Ltd | Heterocycles |
| US7429579B2 (en) * | 2000-11-14 | 2008-09-30 | Smithkline Beecham, Plc | Tetrahydrobenzazepine derivatives useful as modulators of dopamine D3 receptors (antipsychotic agents) |
| US6569887B2 (en) * | 2001-08-24 | 2003-05-27 | Dov Pharmaceuticals Inc. | (−)-1-(3,4-Dichlorophenyl)-3-azabicyclo[3.1.0]hexane, compositions thereof, and uses as a dopamine-reuptake |
| PL368919A1 (en) | 2001-10-22 | 2005-04-04 | Pfizer Products Inc. | 3-azabicyclo (3.1.0) hexane derivatives as opioid receptor antagonists |
| KR20050033070A (ko) * | 2002-08-09 | 2005-04-08 | 아스트라제네카 에이비이 | 메타보트로픽 글루타메이트 수용체-5의 조절제로서[1,2,4]옥사디아졸 |
| TW200538113A (en) * | 2004-02-23 | 2005-12-01 | Glaxo Group Ltd | Compounds |
| GB0507602D0 (en) * | 2005-04-14 | 2005-05-18 | Glaxo Group Ltd | Compounds |
| GB0507601D0 (en) * | 2005-04-14 | 2005-05-18 | Glaxo Group Ltd | Compounds |
| GB0507680D0 (en) * | 2005-04-15 | 2005-05-25 | Glaxo Group Ltd | Compounds |
| WO2006133945A1 (en) * | 2005-06-14 | 2006-12-21 | Glaxo Group Limited | Novel compounds |
| GB0517191D0 (en) * | 2005-08-22 | 2005-09-28 | Glaxo Group Ltd | Compounds |
| GB0517175D0 (en) * | 2005-08-22 | 2005-09-28 | Glaxo Group Ltd | Compounds |
| DE602006018152D1 (de) * | 2005-08-22 | 2010-12-23 | Glaxo Group Ltd | Triazolderivate als modulatoren von dopamin-d3-rezeptoren |
| GB0517193D0 (en) * | 2005-08-22 | 2005-09-28 | Glaxo Group Ltd | Novel use |
| GB0517187D0 (en) * | 2005-08-22 | 2005-09-28 | Glaxo Group Ltd | Compounds |
| AR060237A1 (es) * | 2006-04-03 | 2008-06-04 | Glaxo Group Ltd | Compuesto de 3-azabiciclo[3.1.0]hexano como moduladores del receptor de dopamina d3, su uso para la preparacion de un medicamento para el tratamiento de afecciones psicoticas y composicion farmaceutica que lo comprende. |
| GB0616574D0 (en) * | 2006-08-21 | 2006-09-27 | Glaxo Group Ltd | Compounds |
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