HRP20120281T1 - Derivati azabiciklo[3.1.0]heksana, korisni kao modulatori dopaminskih receptora d3 - Google Patents
Derivati azabiciklo[3.1.0]heksana, korisni kao modulatori dopaminskih receptora d3 Download PDFInfo
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- HRP20120281T1 HRP20120281T1 HR20120281T HRP20120281T HRP20120281T1 HR P20120281 T1 HRP20120281 T1 HR P20120281T1 HR 20120281 T HR20120281 T HR 20120281T HR P20120281 T HRP20120281 T HR P20120281T HR P20120281 T1 HRP20120281 T1 HR P20120281T1
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- HR
- Croatia
- Prior art keywords
- methyl
- azabicyclo
- thio
- propyl
- triazol
- Prior art date
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- QRDSDKAGXMWBID-UHFFFAOYSA-N 5-azabicyclo[3.1.0]hexane Chemical class C1CCN2CC21 QRDSDKAGXMWBID-UHFFFAOYSA-N 0.000 title claims 6
- 102000004073 Dopamine D3 Receptors Human genes 0.000 title 1
- 108090000525 Dopamine D3 Receptors Proteins 0.000 title 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 48
- 150000001875 compounds Chemical class 0.000 claims abstract 23
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 22
- -1 -CH2-N-pyrrolyl Chemical group 0.000 claims abstract 18
- 150000003839 salts Chemical class 0.000 claims abstract 17
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims abstract 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract 9
- 150000002367 halogens Chemical class 0.000 claims abstract 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 7
- 239000001257 hydrogen Substances 0.000 claims abstract 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 7
- 125000004076 pyridyl group Chemical group 0.000 claims abstract 7
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 6
- 125000001424 substituent group Chemical group 0.000 claims abstract 6
- 125000000842 isoxazolyl group Chemical group 0.000 claims abstract 5
- 125000000335 thiazolyl group Chemical group 0.000 claims abstract 4
- 125000001544 thienyl group Chemical group 0.000 claims abstract 4
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims abstract 3
- 125000002619 bicyclic group Chemical group 0.000 claims abstract 3
- 229910052801 chlorine Inorganic materials 0.000 claims abstract 3
- 239000000460 chlorine Substances 0.000 claims abstract 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract 3
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 3
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 3
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims abstract 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 26
- 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 24
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 12
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 8
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 6
- 208000028017 Psychotic disease Diseases 0.000 claims 5
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 3
- 201000009032 substance abuse Diseases 0.000 claims 3
- 231100000736 substance abuse Toxicity 0.000 claims 3
- 208000011117 substance-related disease Diseases 0.000 claims 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- BIUDHHGROGJSHN-UHFFFAOYSA-N 4-fluoro-3-(trifluoromethyl)benzaldehyde Chemical group FC1=CC=C(C=O)C=C1C(F)(F)F BIUDHHGROGJSHN-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- 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 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
- 238000000034 method Methods 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
- 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
- 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
- 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
- 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
- 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
- OWNUCKLLDLFPLN-PGRDOPGGSA-N (1s,5r)-3-[3-[[4-methyl-5-(3-methylfuran-2-yl)-1,2,4-triazol-3-yl]sulfanyl]propyl]-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane Chemical compound C1=COC(C=2N(C(SCCCN3C[C@]4(C[C@H]4C3)C=3C=CC(=CC=3)C(F)(F)F)=NN=2)C)=C1C OWNUCKLLDLFPLN-PGRDOPGGSA-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
- 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
- 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
- UHFLLBIGYQQGJT-GAJHUEQPSA-N 1-[2-hydroxy-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(O)C(C(=O)C)=CC([C@@]23[C@@H](C2)CN(CCCSC=2N(C(C4=C(N=CO4)C)=NN=2)C)C3)=C1 UHFLLBIGYQQGJT-GAJHUEQPSA-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
- 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 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
- 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
- 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
- NOIIYJIVSIMWOI-NBGIEHNGSA-N 2-methyl-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]-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(F)(F)F)C=C1 NOIIYJIVSIMWOI-NBGIEHNGSA-N 0.000 claims 1
- AWJOAMPQOUEKCN-KDYSTLNUSA-N 2-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]quinoline 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(F)(F)F)C=C1 AWJOAMPQOUEKCN-KDYSTLNUSA-N 0.000 claims 1
- FIPYQMORLUNLLH-WNCULLNHSA-N 2-methyl-6-[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]quinoline Chemical compound C1([C@]23C[C@H]2CN(C3)CCCSC2=NN=C(N2C)C2=CC3=CC=C(N=C3C=C2)C)=CC=C(C(F)(F)F)C=C1 FIPYQMORLUNLLH-WNCULLNHSA-N 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- JUGUEPMVIYWOOX-HFZDXXHNSA-N 3,5-dimethyl-4-[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]-1,2-oxazole Chemical compound N1=COC(C=2N(C(SCCCN3C[C@]4(C[C@H]4C3)C=3C=CC(=CC=3)C3=C(ON=C3C)C)=NN=2)C)=C1C JUGUEPMVIYWOOX-HFZDXXHNSA-N 0.000 claims 1
- LBUZXCGCCAXMJH-MQBBKVSDSA-N 4-[(1s)-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]phenol Chemical compound C1([C@]23CC2CN(C3)CCCSC2=NN=C(N2C)C=2C3=CC=C(N=C3C=CC=2)C)=CC=C(O)C=C1 LBUZXCGCCAXMJH-MQBBKVSDSA-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
- 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 1
- 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 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
- 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
- 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 1
- 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 1
- 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 1
- 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 1
- OTIQETSFLFLTJQ-YCRPNKLZSA-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]-4-methyl-1,3-oxazole Chemical compound N1=COC(C=2N(C(SCCCN3C[C@]4(C[C@H]4C3)C=3C=C(Cl)C(Cl)=CC=3)=NN=2)C)=C1C OTIQETSFLFLTJQ-YCRPNKLZSA-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
- 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
- QRXTUDGXPZADAH-NPMXOYFQSA-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]-1-methyl-3-(trifluoromethyl)thieno[2,3-c]pyrazole Chemical compound C1([C@]23C[C@H]2CN(C3)CCCSC=2N(C(=NN=2)C=2SC=3N(C)N=C(C=3C=2)C(F)(F)F)C)=CC=C(Br)C=C1 QRXTUDGXPZADAH-NPMXOYFQSA-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
- 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 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
- QLOCSQXNJJSRQH-HRAATJIYSA-N 5-[5-[3-[(1s,5r)-1-(4-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=CC(F)=CC=3)=NN=2)C)=C1C QLOCSQXNJJSRQH-HRAATJIYSA-N 0.000 claims 1
- 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 1
- 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 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
- QAVVHLXXCTZXLE-FBVQZCABSA-N 5-[5-[3-[(1s,5r)-1-[2-fluoro-3-(trifluoromethyl)phenyl]-2-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(SCCCC3N[C@]4(C[C@H]4C3)C=3C(=C(C=CC=3)C(F)(F)F)F)=NN=2)C)=C1C QAVVHLXXCTZXLE-FBVQZCABSA-N 0.000 claims 1
- LLTRSGMRUYHGQM-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-oxazole Chemical compound O1C(C)=NC(C)=C1C(N1C)=NN=C1SCCCN1C[C@@]2(C=3C(=CC(=CC=3)C(F)(F)F)F)C[C@H]2C1 LLTRSGMRUYHGQM-AOMKIAJQSA-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
- VLGWIPCXNBQWLT-BTYIYWSLSA-N 5-[5-[3-[(1s,5r)-1-[2-fluoro-5-(trifluoromethyl)phenyl]-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=C(C=3)C(F)(F)F)F)=NN=2)C)=C1C VLGWIPCXNBQWLT-BTYIYWSLSA-N 0.000 claims 1
- WKHUFILLPNZZHI-HFZDXXHNSA-N 5-[5-[3-[(1s,5r)-1-[3-(2,4-dimethyl-1,3-thiazol-5-yl)phenyl]-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-4-methyl-1,2,4-triazol-3-yl]-4-methyl-1,3-oxazole Chemical compound S1C(C)=NC(C)=C1C1=CC=CC([C@@]23[C@@H](C2)CN(CCCSC=2N(C(C4=C(N=CO4)C)=NN=2)C)C3)=C1 WKHUFILLPNZZHI-HFZDXXHNSA-N 0.000 claims 1
- ZGGNCUMBXZMKPD-HFZDXXHNSA-N 5-[5-[3-[(1s,5r)-1-[3-fluoro-4-(pyrrol-1-ylmethyl)phenyl]-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(CN4C=CC=C4)=CC=3)=NN=2)C)=C1C ZGGNCUMBXZMKPD-HFZDXXHNSA-N 0.000 claims 1
- WDDOLFDBAGPKBI-IKZMBGHXSA-N 5-[5-[3-[(1s,5r)-1-[3-fluoro-5-(trifluoromethyl)phenyl]-2-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(SCCCC3N[C@]4(C[C@H]4C3)C=3C=C(C=C(F)C=3)C(F)(F)F)=NN=2)C)=C1C WDDOLFDBAGPKBI-IKZMBGHXSA-N 0.000 claims 1
- DUOGVBWBIVGZCL-HFZDXXHNSA-N 5-[5-[3-[(1s,5r)-1-[4-(2,4-dimethyl-1,3-thiazol-5-yl)phenyl]-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-4-methyl-1,2,4-triazol-3-yl]-4-methyl-1,3-oxazole Chemical compound S1C(C)=NC(C)=C1C1=CC=C([C@@]23[C@@H](C2)CN(CCCSC=2N(C(C4=C(N=CO4)C)=NN=2)C)C3)C=C1 DUOGVBWBIVGZCL-HFZDXXHNSA-N 0.000 claims 1
- BYFBIHGWAJPFIB-YCRPNKLZSA-N 5-[5-[3-[(1s,5r)-1-[4-fluoro-3-(trifluoromethyl)phenyl]-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(C(F)=CC=3)C(F)(F)F)=NN=2)C)=C1C BYFBIHGWAJPFIB-YCRPNKLZSA-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
- SLHOJTDTIDHLRK-WXVAWEFUSA-N 6-[5-[3-[(1s,5r)-1-(4-chlorophenyl)-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)C2=CC3=CC=C(N=C3C=C2)C)=CC=C(Cl)C=C1 SLHOJTDTIDHLRK-WXVAWEFUSA-N 0.000 claims 1
- PHOYQXNYVNYDOX-UHFFFAOYSA-N C(#N)Cl(O)OC(F)(F)F Chemical group C(#N)Cl(O)OC(F)(F)F PHOYQXNYVNYDOX-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Chemical group 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- 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
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- 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
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Abstract
Spoj formule (I), ili njegova farmaceutski prihvatljiva sol, naznačen time što• G se bira iz skupine koju čine: fenil, piridil, benzotiazolil, indazolil; • p je cijeli broj, od 0 do 5; • R1 se neovisno bira iz skupine koju čine: halogen, hidroksi, cijano, C1-4-alkil, halogen-C1-4-alkil, C1-4-alkoksi, halogen-C1-4-alkoksi, C1-4-alkanoil; ili odgovara skupini R5;• R2 je vodik ili C1-4-alkil; • R3 je C1-4-alkil; • R4 je vodik, fenilna, heterociklilna, 5- ili 6-eročlana heteroaromatska skupina ili 8- do 11-eročlana biciklička skupina, od kojih svaka može biti supstituirana s 1, 2, 3 ili 4 supstituenta, koje se bira iz skupine koju čine: halogen, cijano, n-C1-4-alkil, halogen-C1-4-alkil, C1-4-alkoksi, C1-4-alkanoil; • R5 je ostatak kojeg se bira iz skupine koju čine: izoksazolil, -CH2-N-pirolil, 1,1-dioksido-2-izotiazolidinil, tienil, tiazolil, piridil, 2-pirolidinonil, gdje takva skupina može biti supstituirana s jednim ili dva supstituenta, koje se bira između: halogena, cijano, C1-4-alkila, halogen-C1-4-alkila, C1-4-alkoksi, C1-4-alkanoila; gdje kada R1 je klor, a p je 1, takav R1 se ne nalazi u orto položaju u odnosu na vezu koja ga povezuje s ostatkom molekule; te gdje kada R1 odgovara R5, p je 1. Patent sadrži još 27 patentnih zahtjeva.
Claims (28)
1. Spoj formule (I), ili njegova farmaceutski prihvatljiva sol,
[image]
naznačen time što
• G se bira iz skupine koju čine: fenil, piridil, benzotiazolil, indazolil;
• p je cijeli broj, od 0 do 5;
• R1 se neovisno bira iz skupine koju čine: halogen, hidroksi, cijano, C1-4-alkil, halogen-C1-4-alkil, C1-4-alkoksi, halogen-C1-4-alkoksi, C1-4-alkanoil; ili odgovara skupini R5;
• R2 je vodik ili C1-4-alkil;
• R3 je C1-4-alkil;
• R4 je vodik, fenilna, heterociklilna, 5- ili 6-eročlana heteroaromatska skupina ili 8- do 11-eročlana biciklička skupina, od kojih svaka može biti supstituirana s 1, 2, 3 ili 4 supstituenta, koje se bira iz skupine koju čine: halogen, cijano, n-C1-4-alkil, halogen-C1-4-alkil, C1-4-alkoksi, C1-4-alkanoil;
• R5 je ostatak kojeg se bira iz skupine koju čine: izoksazolil, -CH2-N-pirolil, 1,1-dioksido-2-izotiazolidinil, tienil, tiazolil, piridil, 2-pirolidinonil, gdje takva skupina može biti supstituirana s jednim ili dva supstituenta, koje se bira između: halogena, cijano, C1-4-alkila, halogen-C1-4-alkila, C1-4-alkoksi, C1-4-alkanoila;
gdje kada R1 je klor, a p je 1, takav R1 se ne nalazi u orto položaju u odnosu na vezu koja ga povezuje s ostatkom molekule; te gdje kada R1 odgovara R5, p je 1.
2. Spoj formule (I)', u skladu s patentnim zahtjevom 1, ili njegova farmaceutski prihvatljiva sol,
[image]
naznačen time što su G, p, R1, R2, R3, R4, te R5 definirani kao u patentnom zahtjevu 1.
3. Spoj u skladu s patentnim zahtjevom 1 ili patentnim zahtjevom 2, naznačen time što je R1 brom, fluor, trifluormetoksi, cijano, hidroksi, klor, metoksi, tert-butil, trifluormetil; a R5 je izoksazolil, 2-pirolidinonil, -CH2-N-pirolil, 1,1-dioksido-2-izotiazolidinil, 2-tienil, 2-piridil, 2-tiazolil.
4. Spoj u skladu s bilo kojim od patentnih zahtjeva 1-3, naznačen time što je p 1 ili 2.
5. Spoj u skladu s bilo kojim od patentnih zahtjeva 1-4, naznačen time što je R2 vodik.
6. Spoj u skladu s bilo kojim od patentnih zahtjeva 1-4, naznačen time što je R4 izborno supstituirani fenil, izborno supstituirani kinolinil, izborno supstituirani piranil, izborno supstituirani piridinil, izborno supstituirani pirazolil, izborno supstituirani pirimidil, izborno supstituirani piridazinil, izborno supstituirani pirazinil, izborno supstituirani furanil, izborno supstituirani tienil, izborno supstituirani oksazolil, izborno supstituirani izoksazolil, izborno supstituirani tiazolil, izborno supstituirani triazolil.
7. Spoj formule (IB), ili njegova farmaceutski prihvatljiva sol, naznačen time što su R1, p, R3 i R4 definirani kao u bilo kojem od patentnih zahtjeva 1-6.
[image]
8. Spoj formule (IC), ili njegova farmaceutski prihvatljiva sol, naznačen time što su R1, p, R3 i R4 definirani kao u bilo kojem od patentnih zahtjeva 1-6.
[image]
9. Spoj formule (ID), ili njegova farmaceutski prihvatljiva sol, naznačen time što su R1, p, R3 i R4 definirani kao u bilo kojem od patentnih zahtjeva 1-6.
[image]
10. Spoj formule (IE), ili njegova farmaceutski prihvatljiva sol, naznačen time što je G 2-piridil ili 3-piridil, a R1, p, R3 i R4 su definirani kao u bilo kojem od patentnih zahtjeva 1-6.
[image]
11. Spoj formule (IF), ili njegova farmaceutski prihvatljiva sol, naznačen time što su R1, p, R3 i R4 definirani kao u bilo kojem od patentnih zahtjeva 1-6.
[image]
12. Stereokemijski izomer, obogaćen (1S,5R) konfiguracijom formule (IA), ili njegova farmaceutski prihvatljiva sol
[image]
naznačen time što
• G se bira iz skupine koju čine: fenil, piridil, benzotiazolil, indazolil;
• p je cijeli broj, od 0 do 5;
• R1 se neovisno bira iz skupine koju čine: halogen, hidroksi, cijano, C1-4-alkil, halogen-C1-4-alkil, C1-4-alkoksi, halogen-C1-4-alkoksi, C1-4-alkanoil; ili odgovara skupini R5;
• R2 je vodik ili C1-4-alkil;
• R3 je C1-4-alkil;
• R4 je vodik, fenilna, heterociklilna, 5- ili 6-eročlana heteroaromatska skupina ili 8- do 11-eročlana biciklička skupina, od kojih svaka može biti supstituirana s 1, 2, 3 ili 4 supstituenta, koje se bira iz skupine koju čine: halogen, cijano, n-C1-4-alkil, halogen-C1-4-alkil, C1-4-alkoksi, C1-4-alkanoil;
• R5 je ostatak kojeg se bira iz skupine koju čine: izoksazolil, -CH2-N-pirolil, 1,1-dioksido-2-izotiazolidinil, tienil, tiazolil, piridil, 2-pirolidinonil, gdje takva skupina može biti supstituirana s jednim ili dva supstituenta, koje se bira između: halogena, cijano, C1-4-alkila, halogen-C1-4-alkila, C1-4-alkoksi, C1-4-alkanoila;
gdje kada R1 je klor, a p je 1, takav R1 se ne nalazi u orto položaju u odnosu na vezu koja ga povezuje s ostatkom molekule; te gdje kada R1 odgovara R5, p je 1.
13. Stereokemijski izomer, obogaćen (1S,5R) konfiguracijom formule (IB)', ili njegova farmaceutski prihvatljiva sol, naznačen time što su R1, p, R3 i R4 definirani kao u bilo kojem od patentnih zahtjeva 1-6.
[image]
14. Stereokemijski izomer, obogaćen (1S,5R) konfiguracijom formule (IC)', ili njegova farmaceutski prihvatljiva sol, naznačen time što su R1, p, R3 i R4 definirani kao u bilo kojem od patentnih zahtjeva 1-6.
[image]
15. Stereokemijski izomer, obogaćen (1S,5R) konfiguracijom formule (ID)', ili njegova farmaceutski prihvatljiva sol, naznačen time što su R1, p, R3 i R4 definirani kao u bilo kojem od patentnih zahtjeva 1-6.
[image]
16. Stereokemijski izomer, obogaćen (1S,5R) konfiguracijom ili (1R,5R) konfiguracijom formule (IE)', ili njegova farmaceutski prihvatljiva sol, naznačen time što je G 2-piridil ili 3-piridil, a R1, p, R3 i R4 su definirani kao u bilo kojem od patentnih zahtjeva 1-6.
[image]
17. Stereokemijski izomer, obogaćen (1S,5R) konfiguracijom formule (IF)', ili njegova farmaceutski prihvatljiva sol, naznačen time što su R1, p, R3 i R4 definirani kao u bilo kojem od patentnih zahtjeva 1-6.
[image]
18. Stereokemijski izomer, obogaćen (1R,5S) konfiguracijom, naznačen time što ga se bira iz skupine, u skladu s patentnim zahtjevom 1, koju čine:
• 5-[5-({3-[(1R,5S)-1-(4-metoksifenil)-3-azabiciklo[3.1.0]heks-3-il]propil}tio)-4-metil-4H-1,2,4-triazol-3-il]-2-metilkinolin, enantiomer 2;
• 5-[5-({3-[(1R,5S)-1-(4-bromfenil)-3-azabiciklo[3.1.0]heks-3-il]propil}tio)-4-metil-4H-1,2,4-triazol-3-il]-2-metilkinolin, enantiomer 1;
• 5-[5-({3-[(1R,5S)-1-(4-tert-butilfenil)-3-azabiciklo[3.1.0]heks-3-il]propil}tio)-4-metil-4H-1,2,4-triazol-3-il]-2-metilkinolin, enantiomer 1;
• (1R,5S)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-1-[3-(trifluormetil)fenil]-3-azabiciklo[3.1.0]heksan, enantiomer 2; Prim. 22
• (1R,5S)-1-(3-klorfenil)-5-metil-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan, enantiomer 2;
• 1-[5-[(1R,5S)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heks-1-il]-2-(metiloksi)fenil]-1-propanon, enantiomer 2;
• 2-metil-5-[(1R,5S)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heks-1-il]-1,3-benzotiazol, enantiomer 2; ili njihove farmaceutski prihvatljive soli.
19. Spoj, ili njegova farmaceutski prihvatljiva sol, u skladu s bilo kojim od patentnih zahtjeva 1-17, naznačen time što ga se bira iz skupine koju čine:
• 5-[5-({3-[(1R,5S/1S,5R)-1-(4-metoksifenil)-3-azabiciklo[3.1.0]heks-3-il]propil}tio)-4-metil-4H-1,2,4-triazol-3-il]-2-metilkinolin;
• 5-[5-({3-[(1S,5R)-1-(4-metoksifenil)-3-azabiciklo[3.1.0]heks-3-il]propil}tio)-4-metil-4H-1,2,4-triazol-3-il]-2-metilkinolin, enantiomer 1;
• 5-[5-({3-[(1R,5S/1S,5R)-1-(4-bromfenil)-3-azabiciklo[3.1.0]heks-3-il]propil}tio)-4-metil-4H-1,2,4-triazol-3-il]-2-metilkinolin;
• 5-[5-({3-[(1S,5R)-1-(4-bromfenil)-3-azabiciklo[3.1.0]heks-3-il]propil}tio)-4-metil-4H-1,2,4-triazol-3-il]-2-metilkinolin, enantiomer 2;
• 2-metil-5-[4-metil-5-({3-[(1R,5S/1S,5R)-1-fenil-3-azabiciklo[3.1.0]heks-3-il]propil}tio)-4H-1,2,4-triazol-3-il]kinolin;
• 2-metil-5-(4-metil-5-({3-[(1S,5R)-1-fenil-3-azabiciklo[3.1.0]heks-3-il]propil}tio)-4H-1,2,4-triazol-3-il]kinolin, enantiomer 2;
• 5-[5-({3-[(1R,5S/1S,5R)-1-(3,4-diklorfenil)-3-azabiciklo[3.1.0]heks-3-il]propil}tio)-4-metil-4H-1,2,4-triazol-3-il]-2-metilkinolin;
• 5-[5-({3-[(1S,5R)-1-(3,4-diklorfenil)-3-azabiciklo[3.1.0]heks-3-il]propil}tio)-4-metil-4H-1,2,4-triazol-3-il]-2-metilkinolin, enantiomer 1;
• 5-(5-({3-[(1R,5S/1S,SR)-1-(4-tert-butilfenil)-3-azabiciklo[3.1.0]heks-3-il]propil)tio)-4-metil-4H-1,2,4-triazol-3-il]-2-metilkinolin;
• 5-[5-({3-[(1S,5R)-1-(4-tert-butilfenil)-3-azabiciklo[3.1.0]heks-3-il]propil}tio)-4-metil-4H-1,2,4-triazol-3-il]-2-metilkinolin, enantiomer 2;
• 5-[5-({3-[(1R,5S)-1-(4-tert-butilfenil)-3-azabiciklo[3.1.0]heks-3-il]propil}tio)-4-metil-4H-1,2,4-triazol-3-il]-2-metilkinolin, enantiomer 1;
• 4-[(1R,5S/1S,5R)-3-(3-{[4-metil-5-(2-metilkinolin-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heks-1-il]benzonitril;
• 4-[(1R,5S/1S,5R)-3-(3-{[4-metil-5-(2-metilkinolin-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heks-1-il]fenol;
• (1R,5S/1S,5R)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-1-fenil-3-azabiciklo[3.1.0]heksan;
• (1R,5S/1S,5R)-1-(4-bromfenil)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-(4-bromfenil)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan, enantiomer 1;
• (1R,5S/1S,5R)-1-(4-tert-butilfenil)-3-(3{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1R,5S/1S,5R)-1-(3,4-diklorfenil)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-(3,4-diklorfenil)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan, enantiomer 2;
• (1R,5S/1S,5R)-1-(4-metoksifenil)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-(4-metoksifenil)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il)tio}propil)-3-azabiciklo[3.1.0]heksan, enantiomer 2;
• (1R,5S/1S,5R)-1-[4-(5-metil-3-izoksazolil)fenil]-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-1-[4-(trifluormetil)fenil]-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-3-(3-{(4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-1-[4-(trifluormetil)fenil]-3-azabiciklo[3.1.0]heksan;
• (1R,5S/1S,5R)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-1-[3-(trifluormetil)fenil]-3-azabiciklo[3.1.0]heksan);
• (1S,5R)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il}tio}propil)-1-[3-(trifluormetil)fenil]-3-azabiciklo[3.1.0]heksan, enantiomer 2;
• (1R,5S/1S,5R)-1-[4-fluor-3-(trifluormetil)fenil]-3-(3-{(4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-[4-fluor-3-(trifluormetil)fenil]-3-(3-{(4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan, enantiomer 1;
• 1-[5-[(1S,5R/1R,5S)-3-{3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heks-1-il)-2-(metiloksi)fenil]etanon;
• 1-[5-[{1S,5R)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heks-1-il)-2-(metiloksi)fenil]etanon, enantiomer 1;
• (1S,5R/1R,5S)-1-(4-klorfenil)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-(4-klorfenil)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan, enantiomer 1;
• (1S,5R/1R,5S)-1-{4-fluorfenil)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-(4-fluorfenil)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan, enantiomer 1;
• (1S,5R/1R,5S)-1-(3-klorfenil)-5-metil-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-(3-klorfenil)-5-metil-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan, enantiomer 1;
• (1S,5R/1R,5S)-1-(3-fluorfenil)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-(3-fluorfenil)-3-(3-{(4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio]propil)-3-azabiciklo[3.1.0]heksan, enantiomer 1;
• (1S,5R/1R,5S)-3-(3-{(4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-1-[3-(metiloksi)fenil]-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-1-[3-(metiloksi)fenil]-3-azabiciklo[3.1.0]heksan, enantiomer 1;
• (1S,5R)-1-(4-bromfenil)-3-(3-{[4-metil-5-(tetrahidro-2H-piran-4-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-(4-bromfenil)-3-(3-({4-metil-5-[4-(trifluormetil)fenil]-4H-1,2,4-triazol-3-il}tio}propil]-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-(4-bromfenil)-3-(3-{[4-metil-5-(3-piridinil)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-(4-bromfenil)-3-(3-{[5-(3,4-difluorfenil)-4-metil-4H-1,2,4-triazol-3-il]tiolpropil)-3-azabiciklo[3.1.0]heksan;
• 6-[5-({3-[(1S,5R/1R,5S)-1-(4-klorfenil)-3-azabiciklo[3.1.0]heks-3-il]propil}tio)-4-metil-4H-1,2,4-triazol-3-il]-2-metilkinolin;
• 6-[5-({3-[(1S,5R)-1-(4-klorfenil)-3-azabiciklo[3.1.0]heks-3-il]propil}tio)-4-metil-4H-1,2,4-triazol-3-il]-2-metilkinolin, enantiomer 1;
• (1S,5R/1R,5S)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-1-(4-[(trifluormetil)oksi]fenil}-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-1-{4-[(trifluormetil)oksi]fenil}-3-azabiciklo[3.1.0]heksan, enantiomer 1;
• (1S,5R/1R,5S)-3-(3-{(4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-1-[2-metil-4-(trifluormetil)fenil]-3-azabiciklo[3.1.0]heksan;
• (1S,5R/1R,5S)-3-(3-{[4-metil-5-(tetrahidro-2H-piran-4-il)-4H-1,2,4-triazol-3-il]tio}propil)-1-{4-[(trifluormetil)oksi]fenil}-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-3-(3-{[4-metil-5-(tetrahidro-2H-piran-4-il)-4H-1,2,4-triazol-3-il]tio}propil)-1-{4-[(trifluormetil)oksi]fenil}3-azabiciklo[3.1.0]heksan, enantiomer 2;
• (1R,5S/1S,5R)-1-(3-bromfenil)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-3-(1-metil-3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-1-[4-(trifluormetil)fenil]-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-3-(1-metil-3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-1-[4-(trifluormetil)fenil]-3-azabiciklo[3.1.0]heksan, dijastereoizomer 1;
• (1S,5R)-3-(1-metil-3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-1-[4-(trifluormetil)fenil]-3-azabiciklo[3.1.0]heksan, dijastereoizomer 2;
• (1R,5S/1S,5R)-1-[2-fluor-5-(trifluormetil)fenil]-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-[2-fluor-5-(trifluormetil)fenil]-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan, enantiomer 2;
• 1-[4-[(1R,5S/1S,5R)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heks-1-il]-2-(metiloksi)fenil]etanon;
• 1-[4-[(1R,5S/1S,5R)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heks-1-il]-2-(metiloksi)fenil]-1-propanon;
• (1R,5S/1S,5R)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-1-[2-(trifluormetil)fenil]-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-3-(3-{[4-metil-5-(2-metil-3-piridinil)-4H-1.2,4-triazol-3-il]tio}propil)-1-[4-(trifluormetil)fenil]-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-3-(3-{[5-(1,5-dimetil-1H-pirazol-4-il)-4-metil-4H-1,2,4-triazol-3-il]tio}propil)-1-[4-(trifluormetil)fenil]-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-3-(3-{[4-metil-5-(5-pirimidinil)-4H-1,2,4-triazol-3-il]tio}propil)-1-[4-(trifluormetil)fenil]-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-3-(3-{[4-metil-5-(3-metil-2-furanil)-4H-1,2,4-triazol-3-il]tio}propil)-1-[4-(trifluormetil)fenil]-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-3-(3-{[4-metil-5-(6-metil-3-piridinil)-4H-1,2,4-triazol-3-il]tio}propil)-1-[4-(trifluormetil)fenil]-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-3-(3-{[5-(2,4-dimetil-1,3-tiazol-5-il)-4-metil-4H-1,2,4-triazol-3-il]tio}propil)-1-[4-(trifluormetil)fenil]-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-3-(3-([4-metil-5-(5-metil-2-pirazinil)-4H-1,2,4-triazol-3-il]tio)propil)-1-[4-(trifluormetil)fenil]-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-3-(3-{[4-metil-5-(tetrahidro-2H-piran-4-il)-4H-1,2,4-triazol-3-il]tio}propil)-1-[4-(trifluormetil)fenil]-3-azabiciklo[3.1.0]heksan;
• 2-metil-6-{4-metil-5-[(3-{(1S,5R)-1-[4-(trifluormetil)fenil]-3-azabiciklo[3.1.0]heks-3-il}propil)tio]-4H-1,2,4-triazol-3-il}kinolin;
• 8-fluor-2-metil-5-{4-metil-5-[(3-{(1S,SR)-1-[4-(trifluormetil)fenil]-3-azabiciklo[3.1.0]heks-3-il}propil)tio]-4H-1,2,4-triazol-3-il}kinolin;
• 2-metil-5-{4-metil-5-[(3-{(1S,5R)-1-[4-(trifluormetil)fenil]-3-azabiciklo[3.1.0]heks-3-il}propil)tio]-4H-1,2,4-triazol-3-il}kinolin;
• (1S,5R)-1-[2-fluor-4-(trifluormetil)fenil]-3-(3-{[4-metil-5-(2-metil-3-piridinil)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-[2-fluor-4-(trifluormetil)fenil]-3-(3{[4-metil-5-(4-piridazinil)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-[2-fluor-4-(trifluormetil)fenil]-3-(3-{[4-metil-5-(5-pirimidinil)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-3-(3-{[5-(2,4-dimetil-1,3-tiazol-5-il)-4-metil-4H-1,2,4-triazol-3-il]tio}propil)-1-[2-fluor-4-(trifluormetil)fenil]-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-[2-fluor-4-(trifluormetil)fenil]-3-(3-{[4-metil-5-(5-metil-2-pirazinil)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-[2-fluor-4-(trifluormetil)fenil]-3-[3-((4-metil-5-[4-(trifluormetil)fenil]-4H-1,2,4-triazol-3-il}tio)propil]-3-azabiciklo[3.1.0]heksan;
• 1-{4-[(1R,5S/1S,5R)-3-(3-{[4-metil-5-(2-metil-5-kinolinil)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heks-1-il]fenil}-2-pirolidinon;
• 5-{5-[(3-{(1R,5S/1S,5R)-1-[4-(1,1-dioksido-2-izotiazolidinil)fenil]-3-azabiciklo[3.1.0]heks-3-il}propil)tio]-4-metil-4H-1,2,4-triazol-3-il}-2-metilkinolin;
• (1R,5S/1S,5R)-1-[3-fluor-4-(trifluormetil)fenil]-5-metil-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• 1-(2-(metiloksi)-5-{(1R,5S/1S,5R)-3-[3-({4-metil-5-[4-(trifluormetil)fenil]-4H-1,2,4-triazol-3-il}tio)propil]-3-azabiciklo[3.1.0]heks-1-il}fenil)etanon;
• 1-[5-[(1R,5S/1S,5R)-3-(3-{[5-(3,4-difluorfenil)-4-metil-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heks-1-il]-2-(metiloksi)fenil]etanon;
• 1-{2-(metiloksi)-5-[(1R,5S/1S,5R)-3-(3-{[4-metil-5-(3-piridinil)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heks-1-il]fenil}etanon;
• 1-[5-[(1R,5S/1S,5R)-3-(3-{[4-metil-5-(2-metil-5-kinolinil)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heks-1-il]-2-(metiloksi)fenil]etanon;
• 1-{2-(metiloksi)-5-[(1R,5S/1S,5R)-3-(3-{[4-metil-5-(tetrahidro-2H-piran-4-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heks-1-il]fenil}etanon;
• 1-(2-hidroksi-5-{(1R,5S/1S,5R)-3-[3-({4-metil-5-[4-(trifluormetil)fenil]-4H-1,2,4-triazol-3-il}tio)propil]-3-azabiciklo[3.1.0]heks-1-il}fenil)etanon;
• 1-{5-[(1R,5S/1S,5R)-3-(3-{[5-(3,4-difluorfenil)-4-metil-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heks-1-il]-2-hidroksifenil}etanon;
• 1-{2-hidroksi-5-[(1R,5S/1S,5R)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heks-1-il]fenil}etanon;
• 1-{2-hidroksi-5-[(1R,5S/1S,5R)-3-(3-{[4-metil-5-(2-metil-5-kinolinil)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heks-1-il]fenil}etanon;
• 1-[5-[(1R,5S/1S,5R)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heks-1-il]-2-(metiloksi)fenil]-1-propanon;
• 1-[5-[(1S,5R)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heks-1-il]-2-(metiloksi)fenil]-1-propanon, enantiomer 1;
• 2-metil-5-[(1R,5S/1S,5R)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heks-1-il]-1,3-benzotiazol;
• 2-metil-5-[(1S,5R)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heks-1-il]-1,3-benzotiazol, enantiomer 1;
• 2-metil-6-[(1R,5S/1S,5R)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heks-1-il]-1,3-benzotiazol;
• 1-metil-5-[(1R,5S/1S,5R)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2.4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heks-1-il]-1H-indazol;
• 1-metil-5-[(1S,5R)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heks-1-il]-1H-indazol, enantiomer 1;
• (1R,5S/1S,5R)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-1-[6-(trifluormetil)-3-piridinil]-3-azabiciklo[3.1.0]heksan;
• (1R,5S/1S,5R)-1-(4-bromfenil)-3-(3-{[4-metil-5-(2-metil-3-piridinil)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1R,5S/1S,5R)-1-(4-bromfenil)-3-(3-{[4-metil-5-(4-piridazinil)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1R,5S/1S,5R)-1-(4-bromfenil)-3-(3-{[5-(5-klor-1-metil-1H-pirazol-4-il)-4-metil-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1R,5S/1S,5R)-1-(4-bromfenil)-3-(3-{[4-metil-5-(1-metil-1H-1,2,3-triazo)-4-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1R,5S/1S,5R)-1-(4-bromfenil)-3-(3{[5-(1,5-dimetil-H-pirazol-4-il)-4-metil-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1R,5S/1S,5R)-1-(4-bromfenil)-3-(3-{[4-metil-5-(5-pirimidinil)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1R,5S/1S,5R}-1-(4-bromfenil}-3-[3-({4-metil-5-[1-metil-3-(trifluormetil)-1H-pirazol-4-il]-4H-1,2,4-triazol-3-il}tio)propil]-3-azabiciklo[3.1.0]heksan;
• (1R,5S/1S,5R)-1-(4-bromfenil)-3-(3-{[4-metil-5-(3-metil-2-furanil)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1R,5S/1S,5R)-1-(4-bromfenil)-3-(3-{[4-metil-5-(3-metil-5-izoksazolil)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1R,5S/1S,5R)-1-(4-bromfenil)-3-(3-{[4-metil-5-(6-metil-3-piridinil)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1R,5S/1S,5R)-1-(4-bromfenil}-3-(3-{[4-metil-5-(1-metil-1H-pirazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1R,5S/1S,5R)-1-(4-bromfenil)-3-(3-{[4-metil-5-(5-metil-3-piridinil)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1R,5S/1S,5R)-1-(4-bromfenil)-3-[3-({4-metil-5-[2-metil-5-(trifluormetil)-1,3-oksazol-4-il]-4H-1,2,4-triazol-3-il}tio)propil]-3-azabiciklo[3.1.0]heksan;
• (1R,5S/1S,5R)-1-(4-bromfenil)-3-(3{[4-metil-5-(3-metil-2-piridinil)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1R,5S/1S,5R)-1-(4-bromfenil)-3-(3-{[5-(2,4-dimetil-1,3-tiazol-5-il)-4-metil-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1R,5S/1S,5R)-1-(4-bromfenil)-3-(3-{[5-(2,5-dimetil-3-furanil)-4-metil-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1R,5S/1S,5R)-1-(4-bromfenil)-3-(3-{-[5-(5-klor-2-tienil)-4-metil-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0.]heksan;
• (1R,5S/1S,5R)-1-(4-bromfenil)-3-(3-{[4-etil-5-(3-piridinil)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1R,5S/1S,5R)-1-(4-bromfenil)-3-[3-({4-metil-5-[2-metil-6-(trifluormetil)-3-piridinil]-4H-1,2,4-triazol-3-il}tio)propil]-3-azabiciklo[3.1.0]heksan;
• 5-[5-({3-[(1R,5S/1S,5R)-1-(4-bromfenil)-3-azabiciklo[3.1.0]heks-3-il]propil}tio)-4-metil-4H-1,2,4-triazol-3-il]-1-metil-3-(trifluormetil)-1H-tieno[2,3-c]pirazol;
• 3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-(1R,5R/1S,5S)-1-[5-(trifluormetil)-2-piridinil]-3-azabiciklo[3.1.0]heksan;
• 3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-(1R,5R)-1-[5-(trifluormetil)-2-piridinil]-3-azabiciklo[3.1.0]heksan, enantiomer 2;
• 3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-(1R,5R/1S,5S)-1-[6-(trifluormetil)-2-piridinil]-3-azabiciklo[3.1.0]heksan;
• (1R,5S/1S,5R)-1-[3-fluor-4-(1H-pirol-1-ilmetil)fenil]-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1S,5R/1R,5S)-3-(3-{[4-metil-5-(5-metil-2-pirazinil)-4H-1,2,4-triazol-3-il]tio}propil)-1-[6-(trifluormetil)-3-piridinil]-3-azabiciklo[3.1.0]heksan;
• (1S,5R/1R,5S)-3-(3-([4-metil-5-(6-metil-3-piridinil)-4H-1,2,4-triazol-3-il]tio}propil)-1-[6-(trifluormetil)-3-piridinil]-3-azabiciklo[3.1.0]heksan;
• (1S,5R/1R,5S)-3-(3-{[4-metil-5-(2-metil-3-piridinil)-4H-1,2,4-triazol-3-il]tio}propil)-1-[6-(trifluormetil)-3-piridinil]-3-azabiciklo[3.1.0]heksan;
• (1S,5R/1R,5S)-3-(3-[(4-metil-5-fenil-4H-1,2,4-triazol-3-il)tio]propil)-1-[6-(trifluormetil)-3-piridinil]-3-azabiciklo[3.1.0]heksan;
• (1S,SR/1R,5S)-3-(3-{[5-(2,4-dimetil-1,3-tiazol-5-il)-4-metil-4H-1,2,4-triazol-3-il]tio}propil)-1-[6-(trifluormetil)-3-piridinil]-3-azabiciklo[3.1.0]heksan;
• (1S,SR/1R,5S)-3-[3-({4-metil-5-[4-(trifluormetil)fenil]-4H-1,2,4-triazol-3-il}tio)propil]-1-[6-(trifluormetil)-3-piridinil]-3-azabiciklo[3.1.0]heksan;
• (1S,5R/1R,SS)-2-metil-5-[3-(3-{[4-metil-5-(5-metil-2-pirazinil)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heks-1-il]-1,3-benzotiazol;
• (1S,5R/1R,5S)-2-metil-5-[3-(3-{[4-metil-5-(6-metil-3-piridinil)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heks-1-il]-1,3-benzotiazol;
• (1S,5R/1R,5S)-2-metil-5-(3-{3-[(4-metil-5-fenil-4H-1,2,4-triazol-3-il)tio]propil}-3-azabiciklo[3.1.0]heks-1-il)-1,3-benzotiazol;
• (1S,5R/1R,5S)-5-[3-(3-{[5-(2,4-dimetil-1,3-tiazol-5-il)-4-metil-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heks-1-il]-2-metil-1,3-benzotiazol;
• (1S,5R/1R,5S)-2-metil-5-{3-[3-({4-metil-5-[4-(trifluormetil)fenil]-4H-1,2,4-triazol-3-il}tio)propil]-3-azabiciklo[3.1.0]heks-1-il}-1,3-benzotiazol;
• (1S,5R)-2-metil-5-{3-[3-({4-metil-5-[4-(trifluormetil)fenil]-4H-1,2,4-triazol-3-il}tio)propil]-3-azabiciklo[3.1.0]heks-1-il)-1,3-benzotiazol, enantiomer 1;
• (1R.5S/1S,5R)-1-[3-fluor-5-(trifluormetil)fenil]-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)azabiciklo[3.1.0]heksan;
• (1S,5R)-1-[3-fluor-5-(trifluormetil)fenil]-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)azabiciklo[3.1.0]heksan, enantiomer 2;
• (1R,5S/1S,5R)-1-[2-fluor-3-(trifluormetil)fenil]-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)azabiciklo[3.1.0]heksan;
• (1S,5R)-1-[2-fluor-3-(trifluormetil)fenil]-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)azabiciklo[3.1.0]heksan, enantiomer 2;
• (1R,5S/1S,5R)-1-[4-(metiloksi)-5-(trifluormetil)fenil]-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)azabiciklo[3.1.0]heksan;
• (1R,5S/1S,5R)-1-[4-(4-klor-2-fluorfenil]-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)azabiciklo[3.1.0]heksan;
• (1R,5S/1S,5R)-1-[3-(2-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-1-(3-[(trifluormetil)oksi]fenil}-3-azabiciklo[3.1.0]heksan;
• (1R,5S/1S,5R)-1-(2-fluor-4-metilfenil)-3-(2-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1R,5S/1S,5R)-1-[3-klor-4-(metiloksi)fenil]-3-(2-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1R,5S/1S,5R)-1-[4-(2,4-dimetil-1,3-tiazol-5-il)fenil]-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1R,5S/1S,5R)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-1-{4-[6-(trifluormetil)-2-piridinil]fenil}-3-azabiciklo[3.1.0]heksan;
• (1R,5S/1S,5R)-1-[3-(2,4-dimetil-1,3-tiazol-5-il)fenil]-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1R,5S/1S,5R)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-1-[3-(5-metil-2-tienil)fenil]-3-azabiciklo[3.1.0]heksan;
• (1R,5S/1S,5R)-1-[4-(3,5-dimetil-4-izoksazolil)fenil]-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-3-(3-{[5-(2,4-dimetil-1,3-oksazol-5-il)-4-metil-4H-1,2,4-triazol-3-il]tio}propil)-1-[2-fluor-4-(trifluormetil)fenil]-3-azabiciklo[3.1.0]heksan.
20. Spoj, ili njegova farmaceutski prihvatljiva sol, u skladu s bilo kojim od patentnih zahtjeva 1-17, naznačen time što ga se bira iz skupine koju čine:
• 4-[(1S,5R)-3-(3-{[4-metil-5-(2-metilkinolin-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heks1-il]benzonitril;
• 4-[(1S,SR)-3-(3-{[4-metil-5-(2-metilkinolin-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heks-1-il]fenol;
• (1S,5R)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-1-fenil-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-(4-tert-butilfenil)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-[4-(5-metil-3-izoksazolil)fenil]-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil]-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-1-[3-(trifluormetil)fenil]-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-[4-fluor-3-(trifluormetil)fenil]-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-1-[2-metil-4-(trifluormetil)fenil]-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-(3-bromfenil)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• 1-[4-[(1S,5R)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heks-1-il]-2-(metiloksi)fenil]etanon;
• 1-[4-[(1S,5R)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heks-1-il]-2-(metiloksi)fenil]-1-propanon;
• (1S,5R)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-1-[2-(trifluormetil)fenil]-3-azabiciklo[3.1.0]heksan;
• 1-{4-[(1S,5R)-3-(3-{[4-metil-5-(2-metil-5-kinolinil)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heks-1-il]fenil}-2-pirolidinon;
• 5-{5-[(3-{(1S,5R)-1-[4-(1,1-dioksido-2-izotiazolidinil)fenil]-3-azabicikle[3.1.0]heks-3-il}propil)tio]-4-metil-4H-1,2,4-triazol-3-il}-2-metilkinolin;
• 1-(2-(metiloksi)-5-{(1S,5R)-3-[3-({4-metil-5-[4-(trifluormetil)fenil]-4H-1,2,4-triazol-3-il}tio)propil]-3-azabiciklo[3.1.0]heks-1-il}fenil)etanon;
• 1-[5-[(1S,5R)-3-(3-{[5-(3,4-difluorfenil)-4-metil-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heks-1-il]-2-(metiloksi)fenil]etanon;
• 1-{2-(metiloksi)-5-[(1S,5R)-3-(3-{[4-metil-5-(3-piridinil)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heks-1-il]fenil}etanon;
• 1-[5-[(1S,5R)-3-(3-{[4-metil-5-(2-metil-5-kinolinil)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heks-1-il]-2-(metiloksi)fenil]etanon;
• 1-{2-(metiloksi)-5-[(1S,5R)-3-(3-{[4-metil-5-(tetrahidro-2H-piran-4-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heks-1-il]fenil}etanon;
• 1-(2-hidroksi-5-{(1S,5R)-3-[3-({4-metil-5-[4-(trifluormetil)fenil]-4H-1,2,4-triazol-3-il}tio)propil]-3-azabiciklo[3.1.0]heks-1-il}fenil)etanon;
• 1-{5-[(1S,5R)-3-(3-{[5-(3,4-difluorfenil)-4-metil-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heks-1-il]-2-hidroksifenil}etanon;
• 1-{2-hidroksi-5-[(1S,5R)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heks-1-il]fenil}etanon;
• 1-{2-hidroksi-5-[(1S,5R)-3-(3-{[4-metil-5-(2-metil-5-kinolinil)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heks-1-il]fenil}etanon;
• 2-metil-6-[(1S,5R)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heks-1-il]-1,3-benzotiazol;
• (1S,5R)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-1-[6-(trifluormetil)-3-piridinil]-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-(4-bromfenil)-3-(3-{[4-metil-5-(2-metil-3-piridinil)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-(4-bromfenil)-3-(3-{[4-metil-5-(4-piridazinil)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-(4-bromfenil)-3-(3-{[5-(5-klor-1-metil-1H-pirazol-4-il)-4-metil-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-(4-bromfenil)-3-(3-{[4-metil-5-(1-metil-1H-1,2,3-triazol-4-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-(4-bromfenil)-3-(3-{[5-(1,5-dimetil-1H-pirazol-4-il)-4-metil-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-(4-bromfenil)-3-(3-{[4-metil-5-(5-pirimidinil)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-(4-bromfenil)-3-[3-({4-metil-5-[1-metil-3-(trifluormetil)-1H-pirazol-4-il]-4H-1,2,4-triazol-3-il}tio)propil]-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-(4-bromfenil)-3-(3-{[4-metil-5-(3-metil-2-furanil)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-(4-bromfenil)-3-(3-{[4-metil-5-(3-metil-5-izoksazolil)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-(4-bromfenil)-3-(3-{[4-metil-5-(6-metil-3-piridinil)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-(4-bromfenil)-3-(3-{[4-metil-5-(1-metil-1H-pirazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-(4-bromfenil)-3-(3-{[4-metil-5-(5-metil-3-piridinil)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-(4-bromfenil)-3-[3-({4-metil-5-[2-metil-5-(trifluormetil)-1,3-oksazol-4-il]-4H-1,2,4-triazol-3-il}tio)propil]-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-(4-bromfenil)-3-(3-{[4-metil-5-(3-metil-2-piridinil)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-(4-bromfenil)-3-(3-{[5-(2,4-dimetil-1,3-tiazol-5-il)-4-metil-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-(4-bromfenil)-3-(3-{[5-(2,5-dimetil-3-furanil)-4-metil-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-(4-bromfenil)-3-(3-{-[5-(5-klor-2-tienil)-4-metil-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-(4-bromfenil)-3-(3-{[4-etil-5-(3-piridinil)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-(4-bromfenil)-3-[3-({4-metil-5-[2-metil-6-(trifluormetil)-3-piridinil]-4H-1,2,4-triazol-3-il}tio)propil]-3-azabiciklo[3.1.0]heksan;
• 5-[5-({3-[(1S,5R)-1-(4-bromfenil)-3-azabiciklo[3.1.0]heks-3-il]propil}tio)-4-metil-4H-1,2,4-triazol-3-il]-1-metil-3-(triftuorometil)-1H-tieno[2,3-c]pirazol;
• 3-(3-{(4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-(1R,5R)-1-[6-(trifluormetil)-2-piridinil]-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-[3-fluor-4-(1H-pirol-1-ilmetil)fenil]-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-3-(3-{[4-metil-5-(5-metil-2-pirazinil)-4H-1,2,4-triazol-3-il]tio}propil)-1-[6-(trifluormetil)-3-piridinil]-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-3-(3-{[4-metil-5-(6-metil-3-piridinil)-4H-1,2,4-triazol-3-il]tio}propil)-1-[6-(trifluormetil)-3-piridinil]-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-3-(3-{[4-metil-5-(2-metil-3-piridinil)-4H-1,2,4-triazol-3-il]tio}propil)-1-[6-(trifluormetil)-3-piridinil]-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-3-(3-[(4-metil-5-fenil-4H-1,2,4-triazol-3-il)tio]propil}-1-[6-(trifluormetil)-3-piridinil]-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-3-(3-{[5-(2,4-dimetil-1,3-tiazol-5-il)-4-metil-4H-1.2.4-triazol-3-il]tio}propil)-1-[6-(trifluormetil)-3-piridinil]-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-3-[3-({4-metil-5-[4-(trifluormetil)fenil]-4H-1,2,4-triazol-3-il}tio)propil]-1-[6-(trifluormetil)-3-piridinil]-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-2-metil-5-[3-(3-{[4-metil-5-(5-metil-2-pirazinil)-4H-1,2,4-triazol-3-il]tiolpropil)-3-azabiciklo[3.1.0]heks-1-il]-1,3-benzotiazol;
• (1S,5R)-2-metil-5-[3-(3-([4-metil-5-(6-metil-3-piridinil)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heks-1-il)-1,3-benzotiazol;
• (1S,5R)-2-metil-5-(3-{3-[(4-metil-5-fenil-4H-1,2,4-triazol-3-il)tio]propil}-3-azabiciklo[3.1.0]heks-1-il)-1,3-benzotiazol;
• (1S,5R)-5-[3-(3-{[5-(2,4-dimetil-1,3-tiazol-5-il)-4-metil-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heks-1-il]-2-metil-1,3-benzotiazol;
• (1S,5R/1R,5S)-2-metil-5-{3-[3-({4-metil-5-[4-(trifluormetil)fenil]-4H-1,2,4-triazol-3-il}tio)propil]-3-azabiciklo[3.1.0]heks-1-il}-1,3-benzotiazol;
• (1S,5R)-1-[4-(4-klor-2-fluorfenil]-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)azabiciklo[3.1.0]heksan);
• (1S,5R)-1-[3-(2-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-1-{3-[(trifluormetil)oksi]fenil}-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-(2-klor-4-metilfenil)-3-(2-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-[3-klor-4-(metiloksi)fenil]-3-(2-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-[4-(2,4-dimetil-1,3-tiazol-5-il)fenil]-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il)]tio}propil)-1-{4-[6-(trifluormetil)-2-piridinil]fenil}-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-[3-(2,4-dimetil-1,3-tiazol-5-il)fenil]-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-1-[3-(5-metil-2-tienil)fenil]-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-1-[4-(3,5-dimetil-4-izoksazolil)fenil]-3-(3-{[4-metil-5-(4-metil-1,3-oksazol-5-il)-4H-1,2,4-triazol-3-il]tio}propil)-3-azabiciklo[3.1.0]heksan;
• (1S,5R)-3-(3-{[5-(2,4-dimetil-1,3-oksazol-5-il)-4-metil-4H-1,2,4-triazol-3-il]tio}propil)-1-[2-fluor-4-(trifluormetil)fenil]-3-azabiciklo[3.1.0].
21. Postupak dobivanja spoja u skladu s patentnim zahtjevom 1, naznačen time što se navedeni postupak sastoji u koracima reakcije spoja formule (XIV):
[image]
gdje su R1, R2, G i p definirani kao u patentnom zahtjevu 1, a X je izlazna skupina, sa spojem formule (V):
[image]
gdje su R3 i R4 definirani kao u patentnom zahtjevu 1.
22. Upotreba spoja u skladu s bilo kojim od patentnih zahtjeva 1-20, naznačena time što je navedeni spoj namijenjen proizvodnji medikamenta za liječenje psihoze ili psihotičnog stanja, ili zloupotrebe tvari.
23. Upotreba u skladu s patentnim zahtjevom 22, naznačena time što je stanje zloupotreba tvari.
24. Upotreba u skladu s patentnim zahtjevom 22, naznačena time što je psihotično stanje shizofrenija.
25. Spoj u skladu s bilo kojim od patentnih zahtjeva 1-20, naznačen time što je namijenjen upotrebi u terapiji.
26. Spoj u skladu s bilo kojim od patentnih zahtjeva 1-20, naznačen time što je namijenjen upotrebi liječenju psihoze ili psihotičnog stanja, ili liječenju zloupotrebe tvari.
27. Spoj u skladu s bilo kojim od patentnih zahtjeva 1-20, naznačen time što je namijenjen upotrebi liječenju shizofrenije.
28. Farmaceutski pripravak, naznačen time što sadrži spoj u skladu s bilo kojim od patentnih zahtjeva 1-20 i farmaceutski prihvatljivu podlogu.
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GB0403990A GB0403990D0 (en) | 2004-02-23 | 2004-02-23 | Compounds |
GB0404083A GB0404083D0 (en) | 2004-02-24 | 2004-02-24 | Compounds |
GB0417120A GB0417120D0 (en) | 2004-07-30 | 2004-07-30 | Compounds |
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HRP20120281T1 true HRP20120281T1 (hr) | 2012-04-30 |
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HR20100114T HRP20100114T1 (hr) | 2004-02-23 | 2010-03-02 | Derivati azabiciklo[3.1.0]heksana korisni kao modulatori dopaminskih receptora d3 |
HR20110781T HRP20110781T1 (hr) | 2004-02-23 | 2011-10-26 | Derivati azabiciklo[3.1.0]heksana, korisni kao modulatori dopaminskih receptora d3 |
HR20120281T HRP20120281T1 (hr) | 2004-02-23 | 2012-03-29 | Derivati azabiciklo[3.1.0]heksana, korisni kao modulatori dopaminskih receptora d3 |
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HR20110781T HRP20110781T1 (hr) | 2004-02-23 | 2011-10-26 | Derivati azabiciklo[3.1.0]heksana, korisni kao modulatori dopaminskih receptora d3 |
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US (3) | US7855298B2 (hr) |
EP (3) | EP2060570B1 (hr) |
JP (1) | JP4960217B2 (hr) |
KR (1) | KR101143718B1 (hr) |
CN (1) | CN1946714B (hr) |
AR (1) | AR047890A1 (hr) |
AT (3) | ATE542816T1 (hr) |
AU (2) | AU2005215918C1 (hr) |
BR (1) | BRPI0507945A (hr) |
CA (1) | CA2557115C (hr) |
CY (3) | CY1109854T1 (hr) |
DE (1) | DE602005018190D1 (hr) |
DK (3) | DK2060570T3 (hr) |
ES (2) | ES2380990T3 (hr) |
HK (1) | HK1103016A1 (hr) |
HR (3) | HRP20100114T1 (hr) |
IL (1) | IL177184A0 (hr) |
MA (1) | MA28438B1 (hr) |
NO (1) | NO20064309L (hr) |
PE (1) | PE20051173A1 (hr) |
PL (3) | PL2060570T3 (hr) |
PT (3) | PT2060570E (hr) |
RU (1) | RU2434011C2 (hr) |
SI (3) | SI1745040T1 (hr) |
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JP5237807B2 (ja) * | 2005-08-22 | 2013-07-17 | グラクソ グループ リミテッド | ドーパミンd3受容体の調節因子としてのトリアゾール誘導体 |
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- 2005-02-21 AT AT08169935T patent/ATE542816T1/de active
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