JP2017532364A5 - - Google Patents
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- JP2017532364A5 JP2017532364A5 JP2017523340A JP2017523340A JP2017532364A5 JP 2017532364 A5 JP2017532364 A5 JP 2017532364A5 JP 2017523340 A JP2017523340 A JP 2017523340A JP 2017523340 A JP2017523340 A JP 2017523340A JP 2017532364 A5 JP2017532364 A5 JP 2017532364A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- phenyl
- azaspiro
- sulfanyl
- propyl
- 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.)
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- -1 cyano, hydroxyl Chemical group 0.000 claims 41
- 125000000217 alkyl group Chemical group 0.000 claims 26
- 150000001875 compounds Chemical class 0.000 claims 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 21
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 21
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 14
- 125000003545 alkoxy group Chemical group 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 11
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 125000005843 halogen group Chemical group 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 7
- PUMREIFKTMLCAF-UHFFFAOYSA-N 4-methyl-1,3-oxazole Chemical compound CC1=COC=N1 PUMREIFKTMLCAF-UHFFFAOYSA-N 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 4
- ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 150000002431 hydrogen Chemical group 0.000 claims 4
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000003282 alkyl amino group Chemical group 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 3
- DOTLHOVQYVFUDB-YKSBVNFPSA-N (2R,3S)-5-[3-[[5-(2-methoxypyridin-3-yl)-4-methyl-1,2,4-triazol-3-yl]sulfanyl]propyl]-2-[4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptane Chemical compound COC1=NC=CC=C1C=1N(C(=NN=1)SCCCN1C[C@@]2(C[C@@H]2C2=CC=C(C=C2)C(F)(F)F)CC1)C DOTLHOVQYVFUDB-YKSBVNFPSA-N 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- RNOVGJWJVRESAA-UHFFFAOYSA-N 4-fluoro-2-(trifluoromethyl)phenol Chemical group OC1=CC=C(F)C=C1C(F)(F)F RNOVGJWJVRESAA-UHFFFAOYSA-N 0.000 claims 2
- 125000002527 bicyclic carbocyclic group Chemical group 0.000 claims 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims 2
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 229910052760 oxygen Chemical group 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- JGGOHKJHMHHQML-OFNKIYASSA-N (2R,3S)-2-(4-fluorophenyl)-5-[3-[(4-methyl-5-pyridin-3-yl-1,2,4-triazol-3-yl)sulfanyl]propyl]-5-azaspiro[2.4]heptane Chemical compound FC1=CC=C(C=C1)[C@H]1C[C@@]11CN(CC1)CCCSC1=NN=C(N1C)C=1C=NC=CC=1 JGGOHKJHMHHQML-OFNKIYASSA-N 0.000 claims 1
- GPDZHKOGLHALQL-GCJKJVERSA-N (2R,3S)-5-[3-[(4-methyl-5-pyrazin-2-yl-1,2,4-triazol-3-yl)sulfanyl]propyl]-2-[4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptane Chemical compound CN1C(=NN=C1C1=NC=CN=C1)SCCCN1C[C@@]2(C[C@@H]2C2=CC=C(C=C2)C(F)(F)F)CC1 GPDZHKOGLHALQL-GCJKJVERSA-N 0.000 claims 1
- ACKJXZGTUCARLB-KNQAVFIVSA-N (2R,3S)-5-[3-[(4-methyl-5-pyridazin-4-yl-1,2,4-triazol-3-yl)sulfanyl]propyl]-2-[4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptane Chemical compound CN1C(=NN=C1C1=CN=NC=C1)SCCCN1C[C@@]2(C[C@@H]2C2=CC=C(C=C2)C(F)(F)F)CC1 ACKJXZGTUCARLB-KNQAVFIVSA-N 0.000 claims 1
- CTRVTEOXKBMCKO-QPPBQGQZSA-N (2R,3S)-5-[3-[(5-cyclohexyl-4-methyl-1,2,4-triazol-3-yl)sulfanyl]propyl]-2-[4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptane Chemical compound C1(CCCCC1)C=1N(C(=NN=1)SCCCN1C[C@@]2(C[C@@H]2C2=CC=C(C=C2)C(F)(F)F)CC1)C CTRVTEOXKBMCKO-QPPBQGQZSA-N 0.000 claims 1
- KIDLIVLNXRZSJP-KNQAVFIVSA-N (2R,3S)-5-[3-[[4-methyl-5-(1-methylpyrazol-4-yl)-1,2,4-triazol-3-yl]sulfanyl]propyl]-2-[4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptane Chemical compound CN1C(=NN=C1C=1C=NN(C=1)C)SCCCN1C[C@@]2(C[C@@H]2C2=CC=C(C=C2)C(F)(F)F)CC1 KIDLIVLNXRZSJP-KNQAVFIVSA-N 0.000 claims 1
- BADZIIJBCNPURN-GCJKJVERSA-N (2R,3S)-5-[3-[[4-methyl-5-(2-methylpyrazol-3-yl)-1,2,4-triazol-3-yl]sulfanyl]propyl]-2-[4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptane Chemical compound CN1C(=NN=C1C1=CC=NN1C)SCCCN1C[C@@]2(C[C@@H]2C2=CC=C(C=C2)C(F)(F)F)CC1 BADZIIJBCNPURN-GCJKJVERSA-N 0.000 claims 1
- MJUZYNLBBPDZMI-QPPBQGQZSA-N (2R,3S)-5-[3-[[4-methyl-5-(2-methylpyridin-3-yl)-1,2,4-triazol-3-yl]sulfanyl]propyl]-2-[4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptane Chemical compound CN1C(=NN=C1C=1C(=NC=CC=1)C)SCCCN1C[C@@]2(C[C@@H]2C2=CC=C(C=C2)C(F)(F)F)CC1 MJUZYNLBBPDZMI-QPPBQGQZSA-N 0.000 claims 1
- WSVPKQPBMGHTOP-XXBNENTESA-N (2R,3S)-5-[3-[[4-methyl-5-(3-methylpyrazin-2-yl)-1,2,4-triazol-3-yl]sulfanyl]propyl]-2-[4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptane Chemical compound CN1C(=NN=C1C1=NC=CN=C1C)SCCCN1C[C@@]2(C[C@@H]2C2=CC=C(C=C2)C(F)(F)F)CC1 WSVPKQPBMGHTOP-XXBNENTESA-N 0.000 claims 1
- RBJIRQAVFUSFOC-YKSBVNFPSA-N (2R,3S)-5-[3-[[4-methyl-5-(3-methylpyridin-2-yl)-1,2,4-triazol-3-yl]sulfanyl]propyl]-2-[4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptane Chemical compound CN1C(=NN=C1C1=NC=CC=C1C)SCCCN1C[C@@]2(C[C@@H]2C2=CC=C(C=C2)C(F)(F)F)CC1 RBJIRQAVFUSFOC-YKSBVNFPSA-N 0.000 claims 1
- ZXFZECKVGJDLHN-IRPSRAIASA-N (2R,3S)-5-[3-[[4-methyl-5-(6-phenoxypyridin-3-yl)-1,2,4-triazol-3-yl]sulfanyl]propyl]-2-[4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptane Chemical compound CN1C(=NN=C1C=1C=NC(=CC=1)OC1=CC=CC=C1)SCCCN1C[C@@]2(C[C@@H]2C2=CC=C(C=C2)C(F)(F)F)CC1 ZXFZECKVGJDLHN-IRPSRAIASA-N 0.000 claims 1
- DVUOLXOWKHDIAV-XXBNENTESA-N (2R,3S)-5-[3-[[4-methyl-5-[2-(trifluoromethyl)pyridin-3-yl]-1,2,4-triazol-3-yl]sulfanyl]propyl]-2-[4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptane Chemical compound CN1C(=NN=C1C=1C(=NC=CC=1)C(F)(F)F)SCCCN1C[C@@]2(C[C@@H]2C2=CC=C(C=C2)C(F)(F)F)CC1 DVUOLXOWKHDIAV-XXBNENTESA-N 0.000 claims 1
- YGYAGUWNTSRVJU-BVAGGSTKSA-N (2R,3S)-5-[3-[[4-methyl-5-[4-(1,2,4-triazol-4-yl)phenyl]-1,2,4-triazol-3-yl]sulfanyl]propyl]-2-[4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptane Chemical compound CN1C(=NN=C1C1=CC=C(C=C1)N1C=NN=C1)SCCCN1C[C@@]2(C[C@@H]2C2=CC=C(C=C2)C(F)(F)F)CC1 YGYAGUWNTSRVJU-BVAGGSTKSA-N 0.000 claims 1
- IWCSEKQLVZIHPU-BWKNWUBXSA-N (2R,3S)-5-[3-[[4-methyl-5-[4-(2H-tetrazol-5-yl)phenyl]-1,2,4-triazol-3-yl]sulfanyl]propyl]-2-[4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptane Chemical compound CN1C(=NN=C1C1=CC=C(C=C1)C1=NN=NN1)SCCCN1C[C@@]2(C[C@@H]2C2=CC=C(C=C2)C(F)(F)F)CC1 IWCSEKQLVZIHPU-BWKNWUBXSA-N 0.000 claims 1
- MRFLPGUUAPCTFB-RDGATRHJSA-N (2R,3S)-5-[3-[[5-(2,6-dimethylpyridin-3-yl)-4-methyl-1,2,4-triazol-3-yl]sulfanyl]propyl]-2-[4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptane Chemical compound CC1=NC(=CC=C1C=1N(C(=NN=1)SCCCN1C[C@@]2(C[C@@H]2C2=CC=C(C=C2)C(F)(F)F)CC1)C)C MRFLPGUUAPCTFB-RDGATRHJSA-N 0.000 claims 1
- IKSPSLCLHNNQFS-XXBNENTESA-N (2S,3S)-2-(2,4-difluorophenyl)-5-[3-[(4-methyl-5-pyridin-3-yl-1,2,4-triazol-3-yl)sulfanyl]propyl]-5-azaspiro[2.4]heptane Chemical compound FC1=C(C=CC(=C1)F)[C@H]1C[C@@]11CN(CC1)CCCSC1=NN=C(N1C)C=1C=NC=CC=1 IKSPSLCLHNNQFS-XXBNENTESA-N 0.000 claims 1
- JZCCFPRFOOIKRY-XXBNENTESA-N (2S,3S)-2-[2-fluoro-4-(trifluoromethyl)phenyl]-5-[3-[(4-methyl-5-pyridin-3-yl-1,2,4-triazol-3-yl)sulfanyl]propyl]-5-azaspiro[2.4]heptane Chemical compound FC1=C(C=CC(=C1)C(F)(F)F)[C@H]1C[C@@]11CN(CC1)CCCSC1=NN=C(N1C)C=1C=NC=CC=1 JZCCFPRFOOIKRY-XXBNENTESA-N 0.000 claims 1
- GXOYNBTVJDTLKB-YKSBVNFPSA-N (2S,3S)-2-[2-fluoro-4-(trifluoromethyl)phenyl]-5-[4-[4-methyl-5-(oxan-4-yl)-1,2,4-triazol-3-yl]butyl]-5-azaspiro[2.4]heptane Chemical compound FC1=C(C=CC(=C1)C(F)(F)F)[C@H]1C[C@@]11CN(CC1)CCCCC1=NN=C(N1C)C1CCOCC1 GXOYNBTVJDTLKB-YKSBVNFPSA-N 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- HMTJKRFRBLRBNL-BVAGGSTKSA-N 1-[4-[4-methyl-5-[3-[(2R,3S)-2-[4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptan-5-yl]propylsulfanyl]-1,2,4-triazol-3-yl]phenyl]ethanone Chemical compound CN1C(=NN=C1SCCCN1C[C@@]2(C[C@@H]2C2=CC=C(C=C2)C(F)(F)F)CC1)C1=CC=C(C=C1)C(C)=O HMTJKRFRBLRBNL-BVAGGSTKSA-N 0.000 claims 1
- BKKDXLNOKQPSKN-RDGATRHJSA-N 1-[4-[4-methyl-5-[3-[(2R,3S)-2-[4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptan-5-yl]propylsulfanyl]-1,2,4-triazol-3-yl]piperidin-1-yl]ethanone Chemical compound CN1C(=NN=C1SCCCN1C[C@@]2(C[C@@H]2C2=CC=C(C=C2)C(F)(F)F)CC1)C1CCN(CC1)C(C)=O BKKDXLNOKQPSKN-RDGATRHJSA-N 0.000 claims 1
- BACQHWSKKKMEGV-BWKNWUBXSA-N 1-[4-[5-[3-[(2S,3S)-2-[2-fluoro-4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptan-5-yl]propylsulfanyl]-4-methyl-1,2,4-triazol-3-yl]piperidin-1-yl]ethanone Chemical compound FC1=C(C=CC(=C1)C(F)(F)F)[C@H]1C[C@@]11CN(CC1)CCCSC=1N(C(=NN=1)C1CCN(CC1)C(C)=O)C BACQHWSKKKMEGV-BWKNWUBXSA-N 0.000 claims 1
- JVGDBVAGMMZAGB-YKSBVNFPSA-N 1-methyl-4-[4-methyl-5-[3-[(2R,3S)-2-[4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptan-5-yl]propylsulfanyl]-1,2,4-triazol-3-yl]pyridin-2-one Chemical compound CN1C(C=C(C=C1)C1=NN=C(N1C)SCCCN1C[C@@]2(C[C@@H]2C2=CC=C(C=C2)C(F)(F)F)CC1)=O JVGDBVAGMMZAGB-YKSBVNFPSA-N 0.000 claims 1
- DRMNJQDZXRGJRN-YKSBVNFPSA-N 1-methyl-5-[4-methyl-5-[3-[(2R,3S)-2-[4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptan-5-yl]propylsulfanyl]-1,2,4-triazol-3-yl]pyridin-2-one Chemical compound CN1C(C=CC(=C1)C1=NN=C(N1C)SCCCN1C[C@@]2(C[C@@H]2C2=CC=C(C=C2)C(F)(F)F)CC1)=O DRMNJQDZXRGJRN-YKSBVNFPSA-N 0.000 claims 1
- NMEPMLDUQJFQOK-KCWPFWIISA-N 2-[3-[4-methyl-5-[3-[(2R,3S)-2-[4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptan-5-yl]propylsulfanyl]-1,2,4-triazol-3-yl]phenyl]-1,3-oxazole Chemical compound CN1C(=NN=C1C1=CC(=CC=C1)C=1OC=CN=1)SCCCN1C[C@@]2(C[C@@H]2C2=CC=C(C=C2)C(F)(F)F)CC1 NMEPMLDUQJFQOK-KCWPFWIISA-N 0.000 claims 1
- GVNGVHIMGMRLJR-GJZUVCINSA-N 2-[4-[4-methyl-5-[3-[(2R,3S)-2-[4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptan-5-yl]propylsulfanyl]-1,2,4-triazol-3-yl]phenyl]-1,3,4-oxadiazole Chemical compound CN1C(=NN=C1C1=CC=C(C=C1)C=1OC=NN=1)SCCCN1C[C@@]2(C[C@@H]2C2=CC=C(C=C2)C(F)(F)F)CC1 GVNGVHIMGMRLJR-GJZUVCINSA-N 0.000 claims 1
- VUGZGZOSCLESTN-BVAGGSTKSA-N 2-[4-[4-methyl-5-[3-[(2R,3S)-2-[4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptan-5-yl]propylsulfanyl]-1,2,4-triazol-3-yl]phenyl]acetonitrile Chemical compound CN1C(=NN=C1SCCCN1C[C@@]2(C[C@@H]2C2=CC=C(C=C2)C(F)(F)F)CC1)C1=CC=C(C=C1)CC#N VUGZGZOSCLESTN-BVAGGSTKSA-N 0.000 claims 1
- YMMKVLDFUKHZTJ-UTKZUKDTSA-N 2-[4-methyl-5-[3-[(2R,3S)-2-[4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptan-5-yl]propylsulfanyl]-1,2,4-triazol-3-yl]-1,3-thiazole Chemical compound CN1C(=NN=C1C=1SC=CN=1)SCCCN1C[C@@]2(C[C@@H]2C2=CC=C(C=C2)C(F)(F)F)CC1 YMMKVLDFUKHZTJ-UTKZUKDTSA-N 0.000 claims 1
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 claims 1
- IHJPCMRDCZSJMC-KCWPFWIISA-N 3-methoxy-1-[4-[4-methyl-5-[3-[(2R,3S)-2-[4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptan-5-yl]propylsulfanyl]-1,2,4-triazol-3-yl]piperidin-1-yl]propan-1-one Chemical compound COCCC(=O)N1CCC(CC1)C1=NN=C(N1C)SCCCN1C[C@@]2(C[C@@H]2C2=CC=C(C=C2)C(F)(F)F)CC1 IHJPCMRDCZSJMC-KCWPFWIISA-N 0.000 claims 1
- TXEGIIUTZDNUKA-GCJKJVERSA-N 3-methyl-5-[4-methyl-5-[3-[(2R,3S)-2-[4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptan-5-yl]propylsulfanyl]-1,2,4-triazol-3-yl]-1,2-oxazole Chemical compound CN1C(=NN=C1C1=CC(=NO1)C)SCCCN1C[C@@]2(C[C@@H]2C2=CC=C(C=C2)C(F)(F)F)CC1 TXEGIIUTZDNUKA-GCJKJVERSA-N 0.000 claims 1
- OLSWHYGQZCEOFP-BWKNWUBXSA-N 3-methyl-6-[4-methyl-5-[3-[(2R,3S)-2-[4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptan-5-yl]propylsulfanyl]-1,2,4-triazol-3-yl]-[1,2,4]triazolo[4,3-a]pyridine Chemical compound CN1C(=NN=C1C=1C=CC=2N(C=1)C(=NN=2)C)SCCCN1C[C@@]2(C[C@@H]2C2=CC=C(C=C2)C(F)(F)F)CC1 OLSWHYGQZCEOFP-BWKNWUBXSA-N 0.000 claims 1
- ITIATPRLDJMYTO-RDGATRHJSA-N 4-[4-methyl-5-[3-[(2R,3S)-2-[4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptan-5-yl]propylsulfanyl]-1,2,4-triazol-3-yl]benzonitrile Chemical compound CN1C(=NN=C1SCCCN1C[C@@]2(C[C@@H]2C2=CC=C(C=C2)C(F)(F)F)CC1)C1=CC=C(C#N)C=C1 ITIATPRLDJMYTO-RDGATRHJSA-N 0.000 claims 1
- XNMSLJNWIPSTJD-KNQAVFIVSA-N 4-[4-methyl-5-[3-[(2R,3S)-2-[4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptan-5-yl]propylsulfanyl]-1,2,4-triazol-3-yl]morpholine Chemical compound CN1C(=NN=C1N1CCOCC1)SCCCN1C[C@@]2(C[C@@H]2C2=CC=C(C=C2)C(F)(F)F)CC1 XNMSLJNWIPSTJD-KNQAVFIVSA-N 0.000 claims 1
- ARSLLTCMIOZESX-PNYWAOBFSA-N 4-[4-methyl-5-[3-[(2R,3S)-2-[4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptan-5-yl]propylsulfanyl]-1,2,4-triazol-3-yl]piperidin-2-one Chemical compound CN1C(=NN=C1SCCCN1C[C@@]2(C[C@@H]2C2=CC=C(C=C2)C(F)(F)F)CC1)C1CC(NCC1)=O ARSLLTCMIOZESX-PNYWAOBFSA-N 0.000 claims 1
- LGSHURNTQKZWCE-QPPBQGQZSA-N 4-[4-methyl-5-[3-[(2R,3S)-2-[4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptan-5-yl]propylsulfanyl]-1,2,4-triazol-3-yl]pyridine-2-carbonitrile Chemical compound CN1C(=NN=C1SCCCN1C[C@@]2(C[C@@H]2C2=CC=C(C=C2)C(F)(F)F)CC1)C1=CC(=NC=C1)C#N LGSHURNTQKZWCE-QPPBQGQZSA-N 0.000 claims 1
- KDMBMLINAPXLCW-UZLBHIALSA-N 4-[4-methyl-5-[3-[(2R,3S)-2-[4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptan-5-yl]propylsulfanyl]-1,2,4-triazol-3-yl]thiadiazole Chemical compound CN1C(=NN=C1C=1N=NSC=1)SCCCN1C[C@@]2(C[C@@H]2C2=CC=C(C=C2)C(F)(F)F)CC1 KDMBMLINAPXLCW-UZLBHIALSA-N 0.000 claims 1
- BMDSVLIJPPCGHQ-DVECYGJZSA-N 4-[5-[3-[(2S,3S)-2-[2-fluoro-4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptan-5-yl]propylsulfanyl]-4-methyl-1,2,4-triazol-3-yl]-1-methylpyridin-2-one Chemical compound FC1=C(C=CC(=C1)C(F)(F)F)[C@H]1C[C@@]11CN(CC1)CCCSC=1N(C(=NN=1)C1=CC(N(C=C1)C)=O)C BMDSVLIJPPCGHQ-DVECYGJZSA-N 0.000 claims 1
- NFIANDWIUXYLJZ-GCJKJVERSA-N 4-methyl-5-[4-methyl-5-[3-[(2R,3S)-2-[4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptan-5-yl]propylsulfanyl]-1,2,4-triazol-3-yl]-1,3-thiazole Chemical compound CN1C(=NN=C1C1=C(N=CS1)C)SCCCN1C[C@@]2(C[C@@H]2C2=CC=C(C=C2)C(F)(F)F)CC1 NFIANDWIUXYLJZ-GCJKJVERSA-N 0.000 claims 1
- YEXWXZVNQKZBGQ-UTKZUKDTSA-N 4-methyl-5-[4-methyl-5-[3-[(2R,3S)-2-[4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptan-5-yl]propylsulfanyl]-1,2,4-triazol-3-yl]thiadiazole Chemical compound CN1C(=NN=C1C1=C(N=NS1)C)SCCCN1C[C@@]2(C[C@@H]2C2=CC=C(C=C2)C(F)(F)F)CC1 YEXWXZVNQKZBGQ-UTKZUKDTSA-N 0.000 claims 1
- MYWIEDWDJCLOLH-XXBNENTESA-N 4-methyl-5-[4-methyl-5-[4-[(2R,3S)-2-[4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptan-5-yl]butyl]-1,2,4-triazol-3-yl]-1,3-oxazole Chemical compound CN1C(=NN=C1C1=C(N=CO1)C)CCCCN1C[C@@]2(C[C@@H]2C2=CC=C(C=C2)C(F)(F)F)CC1 MYWIEDWDJCLOLH-XXBNENTESA-N 0.000 claims 1
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- KIDLIVLNXRZSJP-UHFFFAOYSA-N 5-[3-[[4-methyl-5-(1-methylpyrazol-4-yl)-1,2,4-triazol-3-yl]sulfanyl]propyl]-2-[4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptane Chemical compound CN1C(=NN=C1C=1C=NN(C=1)C)SCCCN1CC2(CC2C2=CC=C(C=C2)C(F)(F)F)CC1 KIDLIVLNXRZSJP-UHFFFAOYSA-N 0.000 claims 1
- KMLVPTIJPYAULP-KOSHJBKYSA-N 5-[4-methyl-5-[3-[(2R,3S)-2-[4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptan-5-yl]propylsulfanyl]-1,2,4-triazol-3-yl]-1H-imidazo[4,5-b]pyridine Chemical compound N1C=NC2=NC(=CC=C21)C=1N(C(=NN=1)SCCCN1C[C@@]2(C[C@@H]2C2=CC=C(C=C2)C(F)(F)F)CC1)C KMLVPTIJPYAULP-KOSHJBKYSA-N 0.000 claims 1
- YYUNOOUJRWVVBW-XXBNENTESA-N 5-[4-methyl-5-[3-[(2R,3S)-2-[4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptan-5-yl]propylsulfanyl]-1,2,4-triazol-3-yl]-1H-pyridin-2-one Chemical compound CN1C(=NN=C1SCCCN1C[C@@]2(C[C@@H]2C2=CC=C(C=C2)C(F)(F)F)CC1)C=1C=CC(NC=1)=O YYUNOOUJRWVVBW-XXBNENTESA-N 0.000 claims 1
- IDNOJRMZJBFBHO-RLWLMLJZSA-N 5-[4-methyl-5-[3-[(2R,3S)-2-[4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptan-5-yl]propylsulfanyl]-1,2,4-triazol-3-yl]-2-pyridin-3-yl-1,3-oxazole Chemical compound CN1C(=NN=C1C1=CN=C(O1)C=1C=NC=CC=1)SCCCN1C[C@@]2(C[C@@H]2C2=CC=C(C=C2)C(F)(F)F)CC1 IDNOJRMZJBFBHO-RLWLMLJZSA-N 0.000 claims 1
- HRCUUSWFFWLUTD-PNYWAOBFSA-N 5-[4-methyl-5-[3-[(2R,3S)-2-[4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptan-5-yl]propylsulfanyl]-1,2,4-triazol-3-yl]piperidin-2-one Chemical compound CN1C(=NN=C1SCCCN1C[C@@]2(C[C@@H]2C2=CC=C(C=C2)C(F)(F)F)CC1)C1CCC(NC1)=O HRCUUSWFFWLUTD-PNYWAOBFSA-N 0.000 claims 1
- CCKIRENVCMGNMA-KCWPFWIISA-N 5-methyl-3-[4-[4-methyl-5-[3-[(2R,3S)-2-[4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptan-5-yl]propylsulfanyl]-1,2,4-triazol-3-yl]phenyl]-1,2,4-oxadiazole Chemical compound CN1C(=NN=C1C1=CC=C(C=C1)C1=NOC(=N1)C)SCCCN1C[C@@]2(C[C@@H]2C2=CC=C(C=C2)C(F)(F)F)CC1 CCKIRENVCMGNMA-KCWPFWIISA-N 0.000 claims 1
- MZLUXGQUEIZOFQ-YKSBVNFPSA-N 6-[4-methyl-5-[3-[(2R,3S)-2-[4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptan-5-yl]propylsulfanyl]-1,2,4-triazol-3-yl]-[1,2,4]triazolo[4,3-a]pyridine Chemical compound CN1C(=NN=C1C=1C=CC=2N(C=1)C=NN=2)SCCCN1C[C@@]2(C[C@@H]2C2=CC=C(C=C2)C(F)(F)F)CC1 MZLUXGQUEIZOFQ-YKSBVNFPSA-N 0.000 claims 1
- YFBVTSTUGAZQFG-YKSBVNFPSA-N 7-[4-methyl-5-[3-[(2R,3S)-2-[4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptan-5-yl]propylsulfanyl]-1,2,4-triazol-3-yl]-[1,2,4]triazolo[4,3-a]pyridine Chemical compound CN1C(=NN=C1C1=CC=2N(C=C1)C=NN=2)SCCCN1C[C@@]2(C[C@@H]2C2=CC=C(C=C2)C(F)(F)F)CC1 YFBVTSTUGAZQFG-YKSBVNFPSA-N 0.000 claims 1
- MYBFGSHZAXDGJK-DVECYGJZSA-N 7-[5-[3-[(2S,3S)-2-[2-fluoro-4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptan-5-yl]propylsulfanyl]-4-methyl-1,2,4-triazol-3-yl]-[1,2,4]triazolo[4,3-a]pyridine Chemical compound FC1=C(C=CC(=C1)C(F)(F)F)[C@H]1C[C@@]11CN(CC1)CCCSC1=NN=C(N1C)C1=CC=2N(C=C1)C=NN=2 MYBFGSHZAXDGJK-DVECYGJZSA-N 0.000 claims 1
- QDBPUGDJXGIOJW-HFYIJGDASA-N N-[4-[4-methyl-5-[3-[(2R,3S)-2-[4-(trifluoromethyl)phenyl]-5-azaspiro[2.4]heptan-5-yl]propylsulfanyl]-1,2,4-triazol-3-yl]cyclohexyl]acetamide Chemical compound CN1C(=NN=C1SCCCN1C[C@@]2(C[C@@H]2C2=CC=C(C=C2)C(F)(F)F)CC1)C1CCC(CC1)NC(C)=O QDBPUGDJXGIOJW-HFYIJGDASA-N 0.000 claims 1
- 208000026251 Opioid-Related disease Diseases 0.000 claims 1
- 208000028017 Psychotic disease Diseases 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 230000009286 beneficial effect Effects 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
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- 239000003814 drug Substances 0.000 claims 1
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- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
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- 239000008194 pharmaceutical composition Substances 0.000 claims 1
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| CN106883192B (zh) * | 2017-03-30 | 2019-05-14 | 苏州汉德创宏生化科技有限公司 | 含氮类杂环抗肿瘤药物活性物恶唑基修饰的苯甲酸类化合物的合成方法 |
| US11447484B2 (en) | 2018-01-26 | 2022-09-20 | Shionogi & Co., Ltd. | Cyclic compound having dopamine D3 receptor antagonistic effect |
| TWI767148B (zh) * | 2018-10-10 | 2022-06-11 | 美商弗瑪治療公司 | 抑制脂肪酸合成酶(fasn) |
| MX2022002877A (es) * | 2019-09-13 | 2022-08-08 | Nimbus Saturn Inc | Antagonistas de cinasa progenitora hematopoyetica 1 (hpk1) y sus usos. |
| WO2021070090A1 (en) | 2019-10-09 | 2021-04-15 | Novartis Ag | 2-azaspiro[3.4]octane derivatives as m4 agonists |
| CN119390705A (zh) | 2019-10-09 | 2025-02-07 | 诺华股份有限公司 | 作为m4激动剂的5-氧杂-2-氮杂螺[3.4]辛烷衍生物 |
| CN110981795B (zh) * | 2019-12-18 | 2021-02-12 | 武汉世纪久海检测技术有限公司 | 一种利用2-氰基异烟酸甲酯制备2-氨酰基异烟酸的方法 |
| WO2021127333A1 (en) * | 2019-12-19 | 2021-06-24 | Casma Therapeutics, Inc. | Trpml modulators |
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| CN116082192B (zh) * | 2021-06-11 | 2024-09-13 | 重庆医药高等专科学校 | 一种反式4-(叔丁氧羰氨基)环己烷羧酸的制备方法 |
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| US3654305A (en) | 1970-01-26 | 1972-04-04 | Robins Co Inc A H | 5-azaspiro(2.4)heptanes |
| CA2071897A1 (en) | 1989-12-28 | 1991-06-29 | Richard A. Glennon | Sigma receptor ligands and the use thereof |
| AU676993B2 (en) | 1991-06-27 | 1997-04-10 | Virginia Commonwealth University | Sigma receptor ligands and the use thereof |
| US6528529B1 (en) | 1998-03-31 | 2003-03-04 | Acadia Pharmaceuticals Inc. | Compounds with activity on muscarinic receptors |
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| US20020025967A1 (en) | 1999-12-16 | 2002-02-28 | Smith Miles P. | N-alkylpiperdine analogs and uses thereof in treating addictions |
| MY145722A (en) | 2000-04-27 | 2012-03-30 | Abbott Lab | Diazabicyclic central nervous system active agents |
| CN1649845A (zh) * | 2002-04-26 | 2005-08-03 | 先灵公司 | 蝇蕈碱拮抗剂 |
| CN101044134A (zh) | 2004-09-20 | 2007-09-26 | 塔加西普特公司 | 具有烟碱性胆碱能受体活性的氮杂螺烯和氮杂螺烷化合物 |
| GB0502509D0 (en) | 2005-02-07 | 2005-03-16 | Pfizer Ltd | Novel salt form of a dopamine agonist |
| US7977346B2 (en) | 2006-01-17 | 2011-07-12 | Guoqing Paul Chen | Spiro compounds and methods of use |
| JP2009528315A (ja) | 2006-03-01 | 2009-08-06 | ラボラトリオス・デル・ドクトル・エステベ・ソシエダッド・アノニマ | シグマ受容体阻害剤としてのピラゾール誘導体 |
| US20080247964A1 (en) | 2006-05-08 | 2008-10-09 | Yuelian Xu | Substituted azaspiro derivatives |
| TW200813051A (en) * | 2006-05-08 | 2008-03-16 | Neurogen Corp | Substituted azaspiro derivatives |
| GB0700786D0 (en) | 2007-01-15 | 2007-02-21 | Pfizer Ltd | Morpholine dopamine agonists for the treatment of pain |
| GB201004200D0 (en) | 2010-03-15 | 2010-04-28 | Univ Basel | Spirocyclic compounds and their use as therapeutic agents and diagnostic probes |
| WO2012128582A2 (en) | 2011-03-23 | 2012-09-27 | Hyundai Pharm Co., Ltd. | A COMPOUND FOR INHIBITING HUMAN 11-β-HYDROXY STEROID DEHYDROGENASE TYPE 1, AND A PHARMACEUTICAL COMPOSITION COMPRISING THE SAME |
| US8809552B2 (en) | 2011-11-01 | 2014-08-19 | Hoffmann-La Roche Inc. | Azetidine compounds, compositions and methods of use |
| AR092289A1 (es) | 2011-11-14 | 2015-04-15 | Sunshine Lake Pharma Co Ltd | Derivados de aminoquinazolina y sus sales y metodos de uso |
| ITMI20112329A1 (it) * | 2011-12-21 | 2013-06-22 | Rottapharm Spa | Nuovi derivati spiro amminici |
| RU2017118562A (ru) * | 2014-10-31 | 2018-11-30 | Индивиор ЮКей Лимитед | Соединения-антагонисты дофаминового d3-рецептора |
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