HRP20100076T1 - Heterociklički supstituirani fenil metanoni kao inhibitori glicin transportera 1 - Google Patents
Heterociklički supstituirani fenil metanoni kao inhibitori glicin transportera 1 Download PDFInfo
- Publication number
- HRP20100076T1 HRP20100076T1 HR20100076T HRP20100076T HRP20100076T1 HR P20100076 T1 HRP20100076 T1 HR P20100076T1 HR 20100076 T HR20100076 T HR 20100076T HR P20100076 T HRP20100076 T HR P20100076T HR P20100076 T1 HRP20100076 T1 HR P20100076T1
- Authority
- HR
- Croatia
- Prior art keywords
- alkyl
- phenyl
- methanone
- methanesulfonyl
- dihydro
- Prior art date
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- 102000010726 Glycine Plasma Membrane Transport Proteins Human genes 0.000 title 1
- 108010063380 Glycine Plasma Membrane Transport Proteins Proteins 0.000 title 1
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical class O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 title 1
- 125000000623 heterocyclic group Chemical group 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 151
- 229910052736 halogen Inorganic materials 0.000 claims abstract 68
- 150000002367 halogens Chemical class 0.000 claims abstract 68
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 40
- 150000001875 compounds Chemical class 0.000 claims abstract 38
- 125000003118 aryl group Chemical group 0.000 claims abstract 34
- 150000003950 cyclic amides Chemical class 0.000 claims abstract 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 30
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract 30
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 30
- -1 aromatic bicyclic amine Chemical class 0.000 claims abstract 29
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 27
- 239000001257 hydrogen Substances 0.000 claims abstract 27
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 25
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 22
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 20
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 20
- 125000005842 heteroatom Chemical group 0.000 claims abstract 20
- 150000002431 hydrogen Chemical class 0.000 claims abstract 20
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 20
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 20
- 239000001301 oxygen Substances 0.000 claims abstract 20
- 239000011593 sulfur Substances 0.000 claims abstract 20
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 11
- 150000003839 salts Chemical class 0.000 claims abstract 11
- 125000001424 substituent group Chemical group 0.000 claims abstract 11
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims abstract 10
- 239000002253 acid Substances 0.000 claims abstract 10
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims abstract 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 7
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- JRGDSXFYQDPYOM-UHFFFAOYSA-N (2-hydroxy-5-nitrophenyl)-(6-nitroindazol-1-yl)methanone Chemical compound OC1=CC=C([N+]([O-])=O)C=C1C(=O)N1C2=CC([N+]([O-])=O)=CC=C2C=N1 JRGDSXFYQDPYOM-UHFFFAOYSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 206010012289 Dementia Diseases 0.000 claims 2
- 208000028017 Psychotic disease Diseases 0.000 claims 2
- 230000019771 cognition Effects 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 230000004064 dysfunction Effects 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- ODWSKYWNNDKJDY-JTQLQIEISA-N (2-methyl-5,7-dihydropyrrolo[3,4-d]pyrimidin-6-yl)-[5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=NC(C)=NC=C2C1 ODWSKYWNNDKJDY-JTQLQIEISA-N 0.000 claims 1
- GZVWYSKFTMYPSO-NSHDSACASA-N (4-bromo-2,3-dihydroindol-1-yl)-[5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1C(C=CC=C2Br)=C2CC1 GZVWYSKFTMYPSO-NSHDSACASA-N 0.000 claims 1
- PXYSIEMCUMYDQC-UHFFFAOYSA-N (4-bromoindol-1-yl)-[5-methylsulfonyl-2-(1,1,1-trifluoropropan-2-yloxy)phenyl]methanone Chemical compound FC(F)(F)C(C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1C2=CC=CC(Br)=C2C=C1 PXYSIEMCUMYDQC-UHFFFAOYSA-N 0.000 claims 1
- PMHTXHPTXUWQKO-UHFFFAOYSA-N (5,6-dichloro-1,3-dihydroisoindol-2-yl)-(5-methylsulfonyl-2-propan-2-yloxyphenyl)methanone Chemical compound CC(C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(Cl)=C(Cl)C=C2C1 PMHTXHPTXUWQKO-UHFFFAOYSA-N 0.000 claims 1
- YDGHLWRHPWUQEO-UHFFFAOYSA-N (5,6-dichloro-1,3-dihydroisoindol-2-yl)-[5-methylsulfonyl-2-(1,1,1-trifluoropropan-2-yloxy)phenyl]methanone Chemical compound FC(F)(F)C(C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(Cl)=C(Cl)C=C2C1 YDGHLWRHPWUQEO-UHFFFAOYSA-N 0.000 claims 1
- OFTSLWXWKWLBNM-ZDUSSCGKSA-N (5,6-dimethylbenzimidazol-1-yl)-[5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1C2=CC(C)=C(C)C=C2N=C1 OFTSLWXWKWLBNM-ZDUSSCGKSA-N 0.000 claims 1
- RVNLVSDKEGGKPP-VIFPVBQESA-N (5,7-dichloroindazol-1-yl)-[5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1C2=C(Cl)C=C(Cl)C=C2C=N1 RVNLVSDKEGGKPP-VIFPVBQESA-N 0.000 claims 1
- INTMQCVFGHNJDQ-NSHDSACASA-N (5-bromoindol-1-yl)-[5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1C2=CC=C(Br)C=C2C=C1 INTMQCVFGHNJDQ-NSHDSACASA-N 0.000 claims 1
- MJSKLOMAAVPWGI-GFCCVEGCSA-N (5-chloro-6-ethylsulfanyl-1,3-dihydroisoindol-2-yl)-[5-methylsulfonyl-2-[(2r)-1,1,1-trifluoropropan-2-yl]oxyphenyl]methanone Chemical compound C1C=2C=C(Cl)C(SCC)=CC=2CN1C(=O)C1=CC(S(C)(=O)=O)=CC=C1O[C@H](C)C(F)(F)F MJSKLOMAAVPWGI-GFCCVEGCSA-N 0.000 claims 1
- RFHABOWIQCVCCR-UHFFFAOYSA-N (5-chloro-6-methoxy-1,3-dihydroisoindol-2-yl)-[2-(2-methylpropoxy)-5-methylsulfonylphenyl]methanone Chemical compound C1C=2C=C(Cl)C(OC)=CC=2CN1C(=O)C1=CC(S(C)(=O)=O)=CC=C1OCC(C)C RFHABOWIQCVCCR-UHFFFAOYSA-N 0.000 claims 1
- CHDOQLWVULWYAZ-LLVKDONJSA-N (5-chloro-6-methoxy-1,3-dihydroisoindol-2-yl)-[5-methylsulfonyl-2-[(2r)-1,1,1-trifluoropropan-2-yl]oxyphenyl]methanone Chemical compound C1C=2C=C(Cl)C(OC)=CC=2CN1C(=O)C1=CC(S(C)(=O)=O)=CC=C1O[C@H](C)C(F)(F)F CHDOQLWVULWYAZ-LLVKDONJSA-N 0.000 claims 1
- CHDOQLWVULWYAZ-NSHDSACASA-N (5-chloro-6-methoxy-1,3-dihydroisoindol-2-yl)-[5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]methanone Chemical compound C1C=2C=C(Cl)C(OC)=CC=2CN1C(=O)C1=CC(S(C)(=O)=O)=CC=C1O[C@@H](C)C(F)(F)F CHDOQLWVULWYAZ-NSHDSACASA-N 0.000 claims 1
- LITVJQNBFOTFAL-UHFFFAOYSA-N (5-chloro-6-methyl-1,3-dihydroisoindol-2-yl)-[2-(2-methylpropoxy)-5-methylsulfonylphenyl]methanone Chemical compound CC(C)COC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(Cl)=C(C)C=C2C1 LITVJQNBFOTFAL-UHFFFAOYSA-N 0.000 claims 1
- MGFZADNLHFPSOZ-GFCCVEGCSA-N (5-chloro-6-methyl-1,3-dihydroisoindol-2-yl)-[5-methylsulfonyl-2-[(2r)-1,1,1-trifluoropropan-2-yl]oxyphenyl]methanone Chemical compound FC(F)(F)[C@@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(Cl)=C(C)C=C2C1 MGFZADNLHFPSOZ-GFCCVEGCSA-N 0.000 claims 1
- MGFZADNLHFPSOZ-LBPRGKRZSA-N (5-chloro-6-methyl-1,3-dihydroisoindol-2-yl)-[5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(Cl)=C(C)C=C2C1 MGFZADNLHFPSOZ-LBPRGKRZSA-N 0.000 claims 1
- GDHJGONKLCGKNS-UHFFFAOYSA-N (5-chloro-6-morpholin-4-yl-1,3-dihydroisoindol-2-yl)-(5-methylsulfonyl-2-phenylphenyl)methanone Chemical compound C1C2=CC(Cl)=C(N3CCOCC3)C=C2CN1C(=O)C1=CC(S(=O)(=O)C)=CC=C1C1=CC=CC=C1 GDHJGONKLCGKNS-UHFFFAOYSA-N 0.000 claims 1
- DNUBDUGYBRTHPP-UHFFFAOYSA-N (5-chloro-6-morpholin-4-yl-1,3-dihydroisoindol-2-yl)-[2-(2-methylpropoxy)-5-methylsulfonylphenyl]methanone Chemical compound CC(C)COC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(N3CCOCC3)=C(Cl)C=C2C1 DNUBDUGYBRTHPP-UHFFFAOYSA-N 0.000 claims 1
- DPBHPWPUONMPSM-UHFFFAOYSA-N (5-chloro-6-morpholin-4-yl-1,3-dihydroisoindol-2-yl)-[2-(3-fluorophenyl)-5-methylsulfonylphenyl]methanone Chemical compound C1C2=CC(Cl)=C(N3CCOCC3)C=C2CN1C(=O)C1=CC(S(=O)(=O)C)=CC=C1C1=CC=CC(F)=C1 DPBHPWPUONMPSM-UHFFFAOYSA-N 0.000 claims 1
- MPKKJSPIPSRXIG-UHFFFAOYSA-N (5-chloro-6-morpholin-4-yl-1,3-dihydroisoindol-2-yl)-[2-(4-fluorophenyl)-5-methylsulfonylphenyl]methanone Chemical compound C1C2=CC(Cl)=C(N3CCOCC3)C=C2CN1C(=O)C1=CC(S(=O)(=O)C)=CC=C1C1=CC=C(F)C=C1 MPKKJSPIPSRXIG-UHFFFAOYSA-N 0.000 claims 1
- VZAYXTTZMDEICL-UHFFFAOYSA-N (5-chloro-6-morpholin-4-yl-1,3-dihydroisoindol-2-yl)-[2-(cyclobutylmethoxy)-5-methylsulfonylphenyl]methanone Chemical compound C1C2=CC(Cl)=C(N3CCOCC3)C=C2CN1C(=O)C1=CC(S(=O)(=O)C)=CC=C1OCC1CCC1 VZAYXTTZMDEICL-UHFFFAOYSA-N 0.000 claims 1
- VYVCXXVUPXNSTR-JTQLQIEISA-N (5-chloroindazol-1-yl)-[5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1C2=CC=C(Cl)C=C2C=N1 VYVCXXVUPXNSTR-JTQLQIEISA-N 0.000 claims 1
- CLQVMZDHOLVTOZ-ZDUSSCGKSA-N (5-ethylsulfanyl-1,3-dihydroisoindol-2-yl)-[5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]methanone Chemical compound C1C2=CC(SCC)=CC=C2CN1C(=O)C1=CC(S(C)(=O)=O)=CC=C1O[C@@H](C)C(F)(F)F CLQVMZDHOLVTOZ-ZDUSSCGKSA-N 0.000 claims 1
- DAIZMHOOIYCBFR-UHFFFAOYSA-N (5-fluoro-6-morpholin-4-yl-1,3-dihydroisoindol-2-yl)-[5-methylsulfonyl-2-(2,2,3,3,3-pentafluoropropoxy)phenyl]methanone Chemical compound CS(=O)(=O)C1=CC=C(OCC(F)(F)C(F)(F)F)C(C(=O)N2CC3=CC(=C(F)C=C3C2)N2CCOCC2)=C1 DAIZMHOOIYCBFR-UHFFFAOYSA-N 0.000 claims 1
- XBSGAMYFNRAPRR-AWEZNQCLSA-N (5-fluoro-6-morpholin-4-yl-1,3-dihydroisoindol-2-yl)-[5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(N3CCOCC3)=C(F)C=C2C1 XBSGAMYFNRAPRR-AWEZNQCLSA-N 0.000 claims 1
- FOYVORAJILCOFQ-UHFFFAOYSA-N (5-methoxy-1,3-dihydroisoindol-2-yl)-(5-methylsulfonyl-2-propan-2-yloxyphenyl)methanone Chemical compound C1C2=CC(OC)=CC=C2CN1C(=O)C1=CC(S(C)(=O)=O)=CC=C1OC(C)C FOYVORAJILCOFQ-UHFFFAOYSA-N 0.000 claims 1
- WMEPBRFDCMCRTQ-UHFFFAOYSA-N (5-methylsulfonyl-2-propan-2-yloxyphenyl)-[2-(trifluoromethyl)-5,7-dihydropyrrolo[3,4-d]pyrimidin-6-yl]methanone Chemical compound CC(C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=NC(C(F)(F)F)=NC=C2C1 WMEPBRFDCMCRTQ-UHFFFAOYSA-N 0.000 claims 1
- COUMNQLBHDURFU-UHFFFAOYSA-N (5-methylsulfonyl-2-propan-2-yloxyphenyl)-[5-(oxan-3-yl)-1,3-dihydroisoindol-2-yl]methanone Chemical compound CC(C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(C3COCCC3)=CC=C2C1 COUMNQLBHDURFU-UHFFFAOYSA-N 0.000 claims 1
- SPASPLFBANPFIF-UHFFFAOYSA-N (5-methylsulfonyl-2-propan-2-yloxyphenyl)-[5-(oxan-4-yl)-1,3-dihydroisoindol-2-yl]methanone Chemical compound CC(C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(C3CCOCC3)=CC=C2C1 SPASPLFBANPFIF-UHFFFAOYSA-N 0.000 claims 1
- QYEUILPVHPNJMA-UHFFFAOYSA-N (5-methylsulfonyl-2-propan-2-yloxyphenyl)-[5-(oxan-4-yloxy)-1,3-dihydroisoindol-2-yl]methanone Chemical compound CC(C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(OC3CCOCC3)=CC=C2C1 QYEUILPVHPNJMA-UHFFFAOYSA-N 0.000 claims 1
- BITVFAUEXCHPJT-UHFFFAOYSA-N (5-methylsulfonyl-2-propan-2-yloxyphenyl)-[5-(oxolan-3-yl)-1,3-dihydroisoindol-2-yl]methanone Chemical compound CC(C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(C3COCC3)=CC=C2C1 BITVFAUEXCHPJT-UHFFFAOYSA-N 0.000 claims 1
- HJYJHHFVZMJARO-NSHDSACASA-N (6-chloroindol-1-yl)-[5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1C2=CC(Cl)=CC=C2C=C1 HJYJHHFVZMJARO-NSHDSACASA-N 0.000 claims 1
- LHSREBCKTALJMP-UHFFFAOYSA-N 1-(5-methylsulfonyl-2-phenylbenzoyl)-2,3-dihydroindole-4-carbonitrile Chemical compound C1CC(C(=CC=C2)C#N)=C2N1C(=O)C1=CC(S(=O)(=O)C)=CC=C1C1=CC=CC=C1 LHSREBCKTALJMP-UHFFFAOYSA-N 0.000 claims 1
- XOQVAUAXSIMFCO-LBPRGKRZSA-N 1-[5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxybenzoyl]indole-6-carbonitrile Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1C2=CC(C#N)=CC=C2C=C1 XOQVAUAXSIMFCO-LBPRGKRZSA-N 0.000 claims 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 1
- 239000012317 TBTU Substances 0.000 claims 1
- FZUQHSIURYGGQE-UHFFFAOYSA-N [2-(2,2-dimethylpropoxy)-5-methylsulfonylphenyl]-[5-(oxan-4-yl)-1,3-dihydroisoindol-2-yl]methanone Chemical compound CC(C)(C)COC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(C3CCOCC3)=CC=C2C1 FZUQHSIURYGGQE-UHFFFAOYSA-N 0.000 claims 1
- KKVWTQYWUKZMBL-UHFFFAOYSA-N [2-(2-methylpropoxy)-5-methylsulfonylphenyl]-[3-(trifluoromethyl)-5,7-dihydropyrrolo[3,4-b]pyridin-6-yl]methanone Chemical compound CC(C)COC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=NC=C(C(F)(F)F)C=C2C1 KKVWTQYWUKZMBL-UHFFFAOYSA-N 0.000 claims 1
- RXUFITNVTSMEHU-UHFFFAOYSA-N [2-(2-methylpropoxy)-5-methylsulfonylphenyl]-[5-(oxan-4-yl)-1,3-dihydroisoindol-2-yl]methanone Chemical compound CC(C)COC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(C3CCOCC3)=CC=C2C1 RXUFITNVTSMEHU-UHFFFAOYSA-N 0.000 claims 1
- ZIYXEFUIAMUALD-UHFFFAOYSA-N [2-(2-methylpropoxy)-5-methylsulfonylphenyl]-[5-(trifluoromethyl)-1,3-dihydroisoindol-2-yl]methanone Chemical compound CC(C)COC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(C(F)(F)F)=CC=C2C1 ZIYXEFUIAMUALD-UHFFFAOYSA-N 0.000 claims 1
- HXKDSNZJKHAINQ-UHFFFAOYSA-N [2-(3,4-difluorophenyl)-5-methylsulfonylphenyl]-[3-(trifluoromethyl)-5,7-dihydropyrrolo[3,4-b]pyridin-6-yl]methanone Chemical compound C1C2=CC(C(F)(F)F)=CN=C2CN1C(=O)C1=CC(S(=O)(=O)C)=CC=C1C1=CC=C(F)C(F)=C1 HXKDSNZJKHAINQ-UHFFFAOYSA-N 0.000 claims 1
- BKVZSBFREBVDRU-UHFFFAOYSA-N [2-(3,4-difluorophenyl)-5-methylsulfonylphenyl]-[6-(trifluoromethyl)-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]methanone Chemical compound C1C2=CN=C(C(F)(F)F)C=C2CN1C(=O)C1=CC(S(=O)(=O)C)=CC=C1C1=CC=C(F)C(F)=C1 BKVZSBFREBVDRU-UHFFFAOYSA-N 0.000 claims 1
- ONGSUIXZRWIZCU-AWEZNQCLSA-N [2-(4-fluorophenyl)-5,7-dihydropyrrolo[3,4-b]pyridin-6-yl]-[5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=NC(C=3C=CC(F)=CC=3)=CC=C2C1 ONGSUIXZRWIZCU-AWEZNQCLSA-N 0.000 claims 1
- XUXCCYATCIEXOP-UHFFFAOYSA-N [2-(4-fluorophenyl)-5-methylsulfonylphenyl]-[3-(trifluoromethyl)-5,7-dihydropyrrolo[3,4-b]pyridin-6-yl]methanone Chemical compound C1C2=CC(C(F)(F)F)=CN=C2CN1C(=O)C1=CC(S(=O)(=O)C)=CC=C1C1=CC=C(F)C=C1 XUXCCYATCIEXOP-UHFFFAOYSA-N 0.000 claims 1
- QMVMTEKLTFRTEL-UHFFFAOYSA-N [2-(4-fluorophenyl)-5-methylsulfonylphenyl]-[5-(oxan-4-yl)-1,3-dihydroisoindol-2-yl]methanone Chemical compound C1C2=CC=C(C3CCOCC3)C=C2CN1C(=O)C1=CC(S(=O)(=O)C)=CC=C1C1=CC=C(F)C=C1 QMVMTEKLTFRTEL-UHFFFAOYSA-N 0.000 claims 1
- CBVPGMMOGFHFNL-UHFFFAOYSA-N [2-(4-fluorophenyl)-5-methylsulfonylphenyl]-[6-(trifluoromethyl)-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]methanone Chemical compound C1C2=CN=C(C(F)(F)F)C=C2CN1C(=O)C1=CC(S(=O)(=O)C)=CC=C1C1=CC=C(F)C=C1 CBVPGMMOGFHFNL-UHFFFAOYSA-N 0.000 claims 1
- ZEKREXWPKRIBMN-UHFFFAOYSA-N [2-(cyclobutylmethoxy)-5-methylsulfonylphenyl]-[3-(trifluoromethyl)-5,7-dihydropyrrolo[3,4-b]pyridin-6-yl]methanone Chemical compound C1C2=CC(C(F)(F)F)=CN=C2CN1C(=O)C1=CC(S(=O)(=O)C)=CC=C1OCC1CCC1 ZEKREXWPKRIBMN-UHFFFAOYSA-N 0.000 claims 1
- POLQRULFUMOWNU-UHFFFAOYSA-N [2-(cyclobutylmethoxy)-5-methylsulfonylphenyl]-[6-(trifluoromethyl)-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]methanone Chemical compound C1C2=CN=C(C(F)(F)F)C=C2CN1C(=O)C1=CC(S(=O)(=O)C)=CC=C1OCC1CCC1 POLQRULFUMOWNU-UHFFFAOYSA-N 0.000 claims 1
- HYVOJOYGCNRIEG-UHFFFAOYSA-N [2-(cyclopropylmethoxy)-5-methylsulfonylphenyl]-[5-(oxan-4-yl)-1,3-dihydroisoindol-2-yl]methanone Chemical compound C1C2=CC=C(C3CCOCC3)C=C2CN1C(=O)C1=CC(S(=O)(=O)C)=CC=C1OCC1CC1 HYVOJOYGCNRIEG-UHFFFAOYSA-N 0.000 claims 1
- PMZIPRVTVJXHQD-AWEZNQCLSA-N [3-(4-fluorophenyl)-5,7-dihydropyrrolo[3,4-b]pyridin-6-yl]-[5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=NC=C(C=3C=CC(F)=CC=3)C=C2C1 PMZIPRVTVJXHQD-AWEZNQCLSA-N 0.000 claims 1
- HPOWVUGMTBBXPJ-UHFFFAOYSA-N [5-(2-chlorophenyl)-1,3-dihydroisoindol-2-yl]-[5-methylsulfonyl-2-(1,1,1-trifluoropropan-2-yloxy)phenyl]methanone Chemical compound FC(F)(F)C(C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(C=3C(=CC=CC=3)Cl)=CC=C2C1 HPOWVUGMTBBXPJ-UHFFFAOYSA-N 0.000 claims 1
- DXLOGJMASBWQIY-UHFFFAOYSA-N [5-(2-fluorophenyl)-1,3-dihydroisoindol-2-yl]-[5-methylsulfonyl-2-(1,1,1-trifluoropropan-2-yloxy)phenyl]methanone Chemical compound FC(F)(F)C(C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(C=3C(=CC=CC=3)F)=CC=C2C1 DXLOGJMASBWQIY-UHFFFAOYSA-N 0.000 claims 1
- UHDIWSKEEGYAKE-INIZCTEOSA-N [5-(2-methylpyridin-4-yl)-1,3-dihydroisoindol-2-yl]-[5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(C=3C=C(C)N=CC=3)=CC=C2C1 UHDIWSKEEGYAKE-INIZCTEOSA-N 0.000 claims 1
- OKUFFZIBLVGPAJ-HNNXBMFYSA-N [5-(3,3-difluoropiperidin-1-yl)-1,3-dihydroisoindol-2-yl]-[5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(N3CC(F)(F)CCC3)=CC=C2C1 OKUFFZIBLVGPAJ-HNNXBMFYSA-N 0.000 claims 1
- DDWBKOXMLRCFMR-UHFFFAOYSA-N [5-(3,5-difluorophenyl)-1,3-dihydroisoindol-2-yl]-[5-methylsulfonyl-2-(1,1,1-trifluoropropan-2-yloxy)phenyl]methanone Chemical compound FC(F)(F)C(C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(C=3C=C(F)C=C(F)C=3)=CC=C2C1 DDWBKOXMLRCFMR-UHFFFAOYSA-N 0.000 claims 1
- CXZOILZPGPBGBA-ZDUSSCGKSA-N [5-(3-fluorooxetan-3-yl)-1,3-dihydroisoindol-2-yl]-[5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(C3(F)COC3)=CC=C2C1 CXZOILZPGPBGBA-ZDUSSCGKSA-N 0.000 claims 1
- LWAZWWUDDCHEOC-UHFFFAOYSA-N [5-(3-fluorophenyl)-1,3-dihydroisoindol-2-yl]-[5-methylsulfonyl-2-(1,1,1-trifluoropropan-2-yloxy)phenyl]methanone Chemical compound FC(F)(F)C(C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(C=3C=C(F)C=CC=3)=CC=C2C1 LWAZWWUDDCHEOC-UHFFFAOYSA-N 0.000 claims 1
- TVFXKPCFFGXQCQ-UHFFFAOYSA-N [5-(3-methoxyphenyl)-1,3-dihydroisoindol-2-yl]-[5-methylsulfonyl-2-(1,1,1-trifluoropropan-2-yloxy)phenyl]methanone Chemical compound COC1=CC=CC(C=2C=C3CN(CC3=CC=2)C(=O)C=2C(=CC=C(C=2)S(C)(=O)=O)OC(C)C(F)(F)F)=C1 TVFXKPCFFGXQCQ-UHFFFAOYSA-N 0.000 claims 1
- IKBJCLSOPBDEIG-UHFFFAOYSA-N [5-(4-fluorophenyl)-1,3-dihydroisoindol-2-yl]-[5-methylsulfonyl-2-(1,1,1-trifluoropropan-2-yloxy)phenyl]methanone Chemical compound FC(F)(F)C(C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(C=3C=CC(F)=CC=3)=CC=C2C1 IKBJCLSOPBDEIG-UHFFFAOYSA-N 0.000 claims 1
- GYIITRHKVCMECI-UHFFFAOYSA-N [5-chloro-6-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-1,3-dihydroisoindol-2-yl]-[5-methylsulfonyl-2-(2,2,3,3,3-pentafluoropropoxy)phenyl]methanone Chemical compound CS(=O)(=O)C1=CC=C(OCC(F)(F)C(F)(F)F)C(C(=O)N2CC3=CC(=C(Cl)C=C3C2)N2C3CCC2COC3)=C1 GYIITRHKVCMECI-UHFFFAOYSA-N 0.000 claims 1
- AAQPNPFTHGDKRX-AWEZNQCLSA-N [5-chloro-6-(oxan-4-yl)-1,3-dihydroisoindol-2-yl]-[5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(C3CCOCC3)=C(Cl)C=C2C1 AAQPNPFTHGDKRX-AWEZNQCLSA-N 0.000 claims 1
- YFHIJEAPFFHRQA-UHFFFAOYSA-N [5-chloro-6-(oxan-4-yloxy)-1,3-dihydroisoindol-2-yl]-(5-methylsulfonyl-2-propan-2-yloxyphenyl)methanone Chemical compound CC(C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(OC3CCOCC3)=C(Cl)C=C2C1 YFHIJEAPFFHRQA-UHFFFAOYSA-N 0.000 claims 1
- WLJUKBDZQGXESS-UHFFFAOYSA-N [5-chloro-6-(oxan-4-yloxy)-1,3-dihydroisoindol-2-yl]-[5-methylsulfonyl-2-(2,2,3,3,3-pentafluoropropoxy)phenyl]methanone Chemical compound CS(=O)(=O)C1=CC=C(OCC(F)(F)C(F)(F)F)C(C(=O)N2CC3=CC(OC4CCOCC4)=C(Cl)C=C3C2)=C1 WLJUKBDZQGXESS-UHFFFAOYSA-N 0.000 claims 1
- LPYNHSXWOYDDBY-AWEZNQCLSA-N [5-chloro-6-(oxan-4-yloxy)-1,3-dihydroisoindol-2-yl]-[5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(OC3CCOCC3)=C(Cl)C=C2C1 LPYNHSXWOYDDBY-AWEZNQCLSA-N 0.000 claims 1
- CNOKOGIBXFCMGY-LSLKUGRBSA-N [5-chloro-6-(oxolan-3-yl)-1,3-dihydroisoindol-2-yl]-[5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(C3COCC3)=C(Cl)C=C2C1 CNOKOGIBXFCMGY-LSLKUGRBSA-N 0.000 claims 1
- XFJQHUOKMYOHES-UHFFFAOYSA-N [5-ethoxy-6-(trifluoromethyl)-1,3-dihydroisoindol-2-yl]-(5-methylsulfonyl-2-propan-2-yloxyphenyl)methanone Chemical compound C1C=2C=C(C(F)(F)F)C(OCC)=CC=2CN1C(=O)C1=CC(S(C)(=O)=O)=CC=C1OC(C)C XFJQHUOKMYOHES-UHFFFAOYSA-N 0.000 claims 1
- PFLDGVGZHBVBSK-LBPRGKRZSA-N [5-ethylsulfanyl-6-(trifluoromethyl)-1,3-dihydroisoindol-2-yl]-[5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]methanone Chemical compound C1C=2C=C(C(F)(F)F)C(SCC)=CC=2CN1C(=O)C1=CC(S(C)(=O)=O)=CC=C1O[C@@H](C)C(F)(F)F PFLDGVGZHBVBSK-LBPRGKRZSA-N 0.000 claims 1
- FOXTUKCLKYTYRT-AWEZNQCLSA-N [5-fluoro-6-(oxan-4-yl)-1,3-dihydroisoindol-2-yl]-[5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(C3CCOCC3)=C(F)C=C2C1 FOXTUKCLKYTYRT-AWEZNQCLSA-N 0.000 claims 1
- FIWXVNBIMNXFCW-UHFFFAOYSA-N [5-fluoro-6-(oxan-4-yloxy)-1,3-dihydroisoindol-2-yl]-(5-methylsulfonyl-2-propan-2-yloxyphenyl)methanone Chemical compound CC(C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(OC3CCOCC3)=C(F)C=C2C1 FIWXVNBIMNXFCW-UHFFFAOYSA-N 0.000 claims 1
- FARKUFWPLXRSDR-UHFFFAOYSA-N [5-fluoro-6-(oxan-4-yloxy)-1,3-dihydroisoindol-2-yl]-[5-methylsulfonyl-2-(2,2,3,3,3-pentafluoropropoxy)phenyl]methanone Chemical compound CS(=O)(=O)C1=CC=C(OCC(F)(F)C(F)(F)F)C(C(=O)N2CC3=CC(OC4CCOCC4)=C(F)C=C3C2)=C1 FARKUFWPLXRSDR-UHFFFAOYSA-N 0.000 claims 1
- MQTVAEYPCMNZBU-AWEZNQCLSA-N [5-fluoro-6-(oxan-4-yloxy)-1,3-dihydroisoindol-2-yl]-[5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(OC3CCOCC3)=C(F)C=C2C1 MQTVAEYPCMNZBU-AWEZNQCLSA-N 0.000 claims 1
- YBRXGVZGAMVUAN-JTQLQIEISA-N [5-fluoro-6-(trifluoromethyl)-1,3-dihydroisoindol-2-yl]-[5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(C(F)(F)F)=C(F)C=C2C1 YBRXGVZGAMVUAN-JTQLQIEISA-N 0.000 claims 1
- RNCOFDWLLFETFF-NSHDSACASA-N [5-methoxy-6-(trifluoromethyl)-1,3-dihydroisoindol-2-yl]-[5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]methanone Chemical compound C1C=2C=C(C(F)(F)F)C(OC)=CC=2CN1C(=O)C1=CC(S(C)(=O)=O)=CC=C1O[C@@H](C)C(F)(F)F RNCOFDWLLFETFF-NSHDSACASA-N 0.000 claims 1
- UNUBOUXVYLYZQL-INIZCTEOSA-N [5-methyl-6-(oxan-4-yl)-1,3-dihydroisoindol-2-yl]-[5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(C3CCOCC3)=C(C)C=C2C1 UNUBOUXVYLYZQL-INIZCTEOSA-N 0.000 claims 1
- ZMPQHZOEHWFNEX-UHFFFAOYSA-N [5-methylsulfonyl-2-(1,1,1-trifluoropropan-2-yloxy)phenyl]-(5-thiophen-3-yl-1,3-dihydroisoindol-2-yl)methanone Chemical compound FC(F)(F)C(C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(C3=CSC=C3)=CC=C2C1 ZMPQHZOEHWFNEX-UHFFFAOYSA-N 0.000 claims 1
- LLBKNKWIAIDCSJ-UHFFFAOYSA-N [5-methylsulfonyl-2-(1,1,1-trifluoropropan-2-yloxy)phenyl]-[5-(3-methylthiophen-2-yl)-1,3-dihydroisoindol-2-yl]methanone Chemical compound FC(F)(F)C(C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(C3=C(C=CS3)C)=CC=C2C1 LLBKNKWIAIDCSJ-UHFFFAOYSA-N 0.000 claims 1
- WWZHXNNTQKWOFV-UHFFFAOYSA-N [5-methylsulfonyl-2-(1,1,1-trifluoropropan-2-yloxy)phenyl]-[5-(4-methylthiophen-2-yl)-1,3-dihydroisoindol-2-yl]methanone Chemical compound FC(F)(F)C(C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(C=3SC=C(C)C=3)=CC=C2C1 WWZHXNNTQKWOFV-UHFFFAOYSA-N 0.000 claims 1
- XTUXOLKZWFQPCF-UHFFFAOYSA-N [5-methylsulfonyl-2-(2,2,3,3,3-pentafluoropropoxy)phenyl]-[3-(trifluoromethyl)-5,7-dihydropyrrolo[3,4-b]pyridin-6-yl]methanone Chemical compound CS(=O)(=O)C1=CC=C(OCC(F)(F)C(F)(F)F)C(C(=O)N2CC3=NC=C(C=C3C2)C(F)(F)F)=C1 XTUXOLKZWFQPCF-UHFFFAOYSA-N 0.000 claims 1
- QMGNUCWTUCYBBS-UHFFFAOYSA-N [5-methylsulfonyl-2-(2,2,3,3,3-pentafluoropropoxy)phenyl]-[5-(oxan-3-yl)-1,3-dihydroisoindol-2-yl]methanone Chemical compound CS(=O)(=O)C1=CC=C(OCC(F)(F)C(F)(F)F)C(C(=O)N2CC3=CC(=CC=C3C2)C2COCCC2)=C1 QMGNUCWTUCYBBS-UHFFFAOYSA-N 0.000 claims 1
- CHDGAZUFGXPSOD-UHFFFAOYSA-N [5-methylsulfonyl-2-(2,2,3,3,3-pentafluoropropoxy)phenyl]-[5-(oxan-4-yloxy)-1,3-dihydroisoindol-2-yl]methanone Chemical compound CS(=O)(=O)C1=CC=C(OCC(F)(F)C(F)(F)F)C(C(=O)N2CC3=CC(OC4CCOCC4)=CC=C3C2)=C1 CHDGAZUFGXPSOD-UHFFFAOYSA-N 0.000 claims 1
- ITNOIEAXUCFUJP-UHFFFAOYSA-N [5-methylsulfonyl-2-(2,2,3,3,3-pentafluoropropoxy)phenyl]-[5-(oxolan-3-yl)-1,3-dihydroisoindol-2-yl]methanone Chemical compound CS(=O)(=O)C1=CC=C(OCC(F)(F)C(F)(F)F)C(C(=O)N2CC3=CC(=CC=C3C2)C2COCC2)=C1 ITNOIEAXUCFUJP-UHFFFAOYSA-N 0.000 claims 1
- QYVINWIAZNTJHX-UHFFFAOYSA-N [5-methylsulfonyl-2-(2,2,3,3,3-pentafluoropropoxy)phenyl]-[6-(trifluoromethyl)-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]methanone Chemical compound CS(=O)(=O)C1=CC=C(OCC(F)(F)C(F)(F)F)C(C(=O)N2CC3=CC(=NC=C3C2)C(F)(F)F)=C1 QYVINWIAZNTJHX-UHFFFAOYSA-N 0.000 claims 1
- RVVFXDPJPAKDHH-UHFFFAOYSA-N [5-methylsulfonyl-2-(2,2,3,3-tetrafluoropropoxy)phenyl]-[3-(trifluoromethyl)-5,7-dihydropyrrolo[3,4-b]pyridin-6-yl]methanone Chemical compound CS(=O)(=O)C1=CC=C(OCC(F)(F)C(F)F)C(C(=O)N2CC3=NC=C(C=C3C2)C(F)(F)F)=C1 RVVFXDPJPAKDHH-UHFFFAOYSA-N 0.000 claims 1
- RWMDJKQARMFVDS-UHFFFAOYSA-N [5-methylsulfonyl-2-(2,2,3,3-tetrafluoropropoxy)phenyl]-[6-(trifluoromethyl)-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]methanone Chemical compound CS(=O)(=O)C1=CC=C(OCC(F)(F)C(F)F)C(C(=O)N2CC3=CC(=NC=C3C2)C(F)(F)F)=C1 RWMDJKQARMFVDS-UHFFFAOYSA-N 0.000 claims 1
- DSFRGIKAQFSVOE-SNVBAGLBSA-N [5-methylsulfonyl-2-[(2r)-1,1,1-trifluoropropan-2-yl]oxyphenyl]-[3-(trifluoromethyl)-5,7-dihydropyrrolo[3,4-b]pyridin-6-yl]methanone Chemical compound FC(F)(F)[C@@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=NC=C(C(F)(F)F)C=C2C1 DSFRGIKAQFSVOE-SNVBAGLBSA-N 0.000 claims 1
- ZJTJVQCPJFQLHB-LLVKDONJSA-N [5-methylsulfonyl-2-[(2r)-1,1,1-trifluoropropan-2-yl]oxyphenyl]-[5-(trifluoromethyl)-1,3-dihydroisoindol-2-yl]methanone Chemical compound FC(F)(F)[C@@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(C(F)(F)F)=CC=C2C1 ZJTJVQCPJFQLHB-LLVKDONJSA-N 0.000 claims 1
- FIXWHAZRUQGPAS-JTQLQIEISA-N [5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]-(5-nitroindazol-1-yl)methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1C2=CC=C([N+]([O-])=O)C=C2C=N1 FIXWHAZRUQGPAS-JTQLQIEISA-N 0.000 claims 1
- JOLOIRNKELNRQF-INIZCTEOSA-N [5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]-(5-phenyl-1,3-dihydroisoindol-2-yl)methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(C=3C=CC=CC=3)=CC=C2C1 JOLOIRNKELNRQF-INIZCTEOSA-N 0.000 claims 1
- FWMYBTUOMODPKL-AWEZNQCLSA-N [5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]-(5-pyrazol-1-yl-1,3-dihydroisoindol-2-yl)methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(N3N=CC=C3)=CC=C2C1 FWMYBTUOMODPKL-AWEZNQCLSA-N 0.000 claims 1
- QEPSWXGVJNMPAJ-HNNXBMFYSA-N [5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]-(5-pyridin-3-yl-1,3-dihydroisoindol-2-yl)methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(C=3C=NC=CC=3)=CC=C2C1 QEPSWXGVJNMPAJ-HNNXBMFYSA-N 0.000 claims 1
- XICAQVBMJIEJFN-HNNXBMFYSA-N [5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]-(5-pyridin-4-yl-1,3-dihydroisoindol-2-yl)methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(C=3C=CN=CC=3)=CC=C2C1 XICAQVBMJIEJFN-HNNXBMFYSA-N 0.000 claims 1
- WHLLOKUPJGBJKA-AWEZNQCLSA-N [5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]-(5-thiophen-2-yl-1,3-dihydroisoindol-2-yl)methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(C=3SC=CC=3)=CC=C2C1 WHLLOKUPJGBJKA-AWEZNQCLSA-N 0.000 claims 1
- APINBDQEXUILFS-AWEZNQCLSA-N [5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]-(6-morpholin-4-yl-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl)methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(N3CCOCC3)=NC=C2C1 APINBDQEXUILFS-AWEZNQCLSA-N 0.000 claims 1
- UFIZIVMFKPXYEK-VIFPVBQESA-N [5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]-[2-(trifluoromethyl)-5,7-dihydropyrrolo[3,4-d]pyrimidin-6-yl]methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=NC(C(F)(F)F)=NC=C2C1 UFIZIVMFKPXYEK-VIFPVBQESA-N 0.000 claims 1
- VQVMGCWLHGRHNB-NSHDSACASA-N [5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]-[2-methyl-3-(trifluoromethyl)-5,7-dihydropyrrolo[3,4-b]pyridin-6-yl]methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=NC(C)=C(C(F)(F)F)C=C2C1 VQVMGCWLHGRHNB-NSHDSACASA-N 0.000 claims 1
- DSFRGIKAQFSVOE-JTQLQIEISA-N [5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]-[3-(trifluoromethyl)-5,7-dihydropyrrolo[3,4-b]pyridin-6-yl]methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=NC=C(C(F)(F)F)C=C2C1 DSFRGIKAQFSVOE-JTQLQIEISA-N 0.000 claims 1
- SSPGEPJBIIXYAV-ZDUSSCGKSA-N [5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]-[5-(1,3-thiazol-2-yl)-1,3-dihydroisoindol-2-yl]methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(C=3SC=CN=3)=CC=C2C1 SSPGEPJBIIXYAV-ZDUSSCGKSA-N 0.000 claims 1
- CPVPHNHEUNPGLG-LBPRGKRZSA-N [5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]-[5-(2,2,2-trifluoroethoxy)-1,3-dihydroisoindol-2-yl]methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(OCC(F)(F)F)=CC=C2C1 CPVPHNHEUNPGLG-LBPRGKRZSA-N 0.000 claims 1
- UDPJTBIABMKTGQ-LBPRGKRZSA-N [5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]-[5-(2,2,2-trifluoroethyl)-1,3-dihydroisoindol-2-yl]methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(CC(F)(F)F)=CC=C2C1 UDPJTBIABMKTGQ-LBPRGKRZSA-N 0.000 claims 1
- YCYRPSBGKISYCO-ZDUSSCGKSA-N [5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]-[5-(3,3,3-trifluoropropoxy)-1,3-dihydroisoindol-2-yl]methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(OCCC(F)(F)F)=CC=C2C1 YCYRPSBGKISYCO-ZDUSSCGKSA-N 0.000 claims 1
- VDSQHEJXUHRGBS-AWEZNQCLSA-N [5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]-[5-(4-methyl-1,3-thiazol-2-yl)-1,3-dihydroisoindol-2-yl]methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(C=3SC=C(C)N=3)=CC=C2C1 VDSQHEJXUHRGBS-AWEZNQCLSA-N 0.000 claims 1
- KBZROKHEGUCKHW-HNNXBMFYSA-N [5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]-[5-(4-methylthiophen-3-yl)-1,3-dihydroisoindol-2-yl]methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(C=3C(=CSC=3)C)=CC=C2C1 KBZROKHEGUCKHW-HNNXBMFYSA-N 0.000 claims 1
- YLZLPESXVIEYLR-HNNXBMFYSA-N [5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]-[5-(5-methylthiophen-3-yl)-1,3-dihydroisoindol-2-yl]methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(C=3C=C(C)SC=3)=CC=C2C1 YLZLPESXVIEYLR-HNNXBMFYSA-N 0.000 claims 1
- HMIFIPICRKBVFJ-BUSXIPJBSA-N [5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]-[5-(oxan-3-yl)-1,3-dihydroisoindol-2-yl]methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(C3COCCC3)=CC=C2C1 HMIFIPICRKBVFJ-BUSXIPJBSA-N 0.000 claims 1
- IHLMQHFPWQMCHB-HNNXBMFYSA-N [5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]-[5-(oxan-4-yl)-1,3-dihydroisoindol-2-yl]methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(C3CCOCC3)=CC=C2C1 IHLMQHFPWQMCHB-HNNXBMFYSA-N 0.000 claims 1
- PTNOOYFZDZKVHK-HNNXBMFYSA-N [5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]-[5-(oxan-4-yloxy)-1,3-dihydroisoindol-2-yl]methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(OC3CCOCC3)=CC=C2C1 PTNOOYFZDZKVHK-HNNXBMFYSA-N 0.000 claims 1
- GUCLULHJCYXBTN-MBIQTGHCSA-N [5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]-[5-(oxolan-3-yl)-1,3-dihydroisoindol-2-yl]methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(C3COCC3)=CC=C2C1 GUCLULHJCYXBTN-MBIQTGHCSA-N 0.000 claims 1
- RLFTXHDBMLYLFQ-NSHDSACASA-N [5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]-[5-(trifluoromethoxy)-1,3-dihydroisoindol-2-yl]methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(OC(F)(F)F)=CC=C2C1 RLFTXHDBMLYLFQ-NSHDSACASA-N 0.000 claims 1
- ZJTJVQCPJFQLHB-NSHDSACASA-N [5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]-[5-(trifluoromethyl)-1,3-dihydroisoindol-2-yl]methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(C(F)(F)F)=CC=C2C1 ZJTJVQCPJFQLHB-NSHDSACASA-N 0.000 claims 1
- BHZQLVSRXZTNDY-RYGJVYDSSA-N [5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]-[5-[(1s,5r)-3-oxa-8-azabicyclo[3.2.1]octan-8-yl]-1,3-dihydroisoindol-2-yl]methanone Chemical compound N1([C@]2([H])CC[C@]1(COC2)[H])C(C=C1C2)=CC=C1CN2C(=O)C1=CC(S(C)(=O)=O)=CC=C1O[C@@H](C)C(F)(F)F BHZQLVSRXZTNDY-RYGJVYDSSA-N 0.000 claims 1
- DSIPQOKHFVFCBT-AWEZNQCLSA-N [6-(4-fluorophenyl)-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]-[5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxyphenyl]methanone Chemical compound FC(F)(F)[C@H](C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CC2=CC(C=3C=CC(F)=CC=3)=NC=C2C1 DSIPQOKHFVFCBT-AWEZNQCLSA-N 0.000 claims 1
- CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 claims 1
- 230000003213 activating effect Effects 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 230000006735 deficit Effects 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 230000001771 impaired effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- BZEXNVDZEVPEDU-UHFFFAOYSA-N methyl 1-(5-methylsulfonyl-2-propan-2-yloxybenzoyl)-2,3-dihydroindole-4-carboxylate Chemical compound C1CC=2C(C(=O)OC)=CC=CC=2N1C(=O)C1=CC(S(C)(=O)=O)=CC=C1OC(C)C BZEXNVDZEVPEDU-UHFFFAOYSA-N 0.000 claims 1
- VRUMVTFCOLOERS-LBPRGKRZSA-N methyl 1-[5-methylsulfonyl-2-[(2s)-1,1,1-trifluoropropan-2-yl]oxybenzoyl]-2,3-dihydroindole-4-carboxylate Chemical compound C1CC=2C(C(=O)OC)=CC=CC=2N1C(=O)C1=CC(S(C)(=O)=O)=CC=C1O[C@@H](C)C(F)(F)F VRUMVTFCOLOERS-LBPRGKRZSA-N 0.000 claims 1
- PAINOKAKFPGOPI-UHFFFAOYSA-N n-methyl-4-propan-2-yloxy-3-[5-(trifluoromethyl)-1,3-dihydroisoindole-2-carbonyl]benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(OC(C)C)C(C(=O)N2CC3=CC(=CC=C3C2)C(F)(F)F)=C1 PAINOKAKFPGOPI-UHFFFAOYSA-N 0.000 claims 1
- 230000000626 neurodegenerative effect Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229910000104 sodium hydride Inorganic materials 0.000 claims 1
- 239000012312 sodium hydride Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract 3
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/4035—Isoindoles, e.g. phthalimide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/46—Iso-indoles; Hydrogenated iso-indoles with an oxygen atom in position 1
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
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- 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
- C07D401/02—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 two hetero rings
- C07D401/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—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
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/08—Bridged systems
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EP05100813 | 2005-02-07 | ||
PCT/EP2006/000761 WO2006082001A1 (en) | 2005-02-07 | 2006-01-30 | Heterocyclic substituted phenyl methanones as inhibitors of the glycine transporter 1 |
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CN (1) | CN101119968B (da) |
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CY (1) | CY1109829T1 (da) |
DE (1) | DE602006010665D1 (da) |
DK (1) | DK1848694T3 (da) |
ES (1) | ES2334578T3 (da) |
HK (1) | HK1117507A1 (da) |
HR (1) | HRP20100076T1 (da) |
IL (1) | IL184557A (da) |
MA (1) | MA29245B1 (da) |
MX (1) | MX2007009342A (da) |
MY (1) | MY140012A (da) |
NO (1) | NO340731B1 (da) |
NZ (1) | NZ556434A (da) |
PL (1) | PL1848694T3 (da) |
PT (1) | PT1848694E (da) |
RS (1) | RS51204B (da) |
RU (1) | RU2405771C2 (da) |
SI (1) | SI1848694T1 (da) |
TW (1) | TWI347944B (da) |
UA (1) | UA91536C2 (da) |
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Families Citing this family (57)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2332909B1 (en) | 2005-04-13 | 2014-10-15 | Astex Therapeutics Limited | Hydroxybenzamide derivatives and their use as inhibitors of hsp90 |
US7754725B2 (en) | 2006-03-01 | 2010-07-13 | Astex Therapeutics Ltd. | Dihydroxyphenyl isoindolymethanones |
US8883790B2 (en) | 2006-10-12 | 2014-11-11 | Astex Therapeutics Limited | Pharmaceutical combinations |
EP2073802A1 (en) * | 2006-10-12 | 2009-07-01 | Astex Therapeutics Limited | Pharmaceutical combinations |
EP2073804B1 (en) * | 2006-10-12 | 2017-09-13 | Astex Therapeutics Limited | Hydroxy-substituted benzoic acid amide compounds for use in the treatment of pain |
WO2008044027A2 (en) * | 2006-10-12 | 2008-04-17 | Astex Therapeutics Limited | Pharmaceutical compounds having hsp90 inhibitory or modulating activity |
US8916552B2 (en) | 2006-10-12 | 2014-12-23 | Astex Therapeutics Limited | Pharmaceutical combinations |
GB0620259D0 (en) | 2006-10-12 | 2006-11-22 | Astex Therapeutics Ltd | Pharmaceutical compounds |
US8093246B2 (en) * | 2006-12-14 | 2012-01-10 | Lexicon Pharmaceuticals, Inc. | O-linked pyrimidin-4-amine-based compounds, compositions comprising them, and methods of their use to treat cancer |
CA2705950A1 (en) * | 2007-11-29 | 2009-06-04 | F. Hoffmann-La Roche Ag | Preparation of dihydropyrrol derivatives as intermediates |
MX2010010773A (es) | 2008-04-01 | 2011-04-11 | Abbott Gmbh & Co Kg | Tetrahidroisoquinolinas, composiciones farmaceuticas que las contienen y su uso en terapia. |
GB0806527D0 (en) * | 2008-04-11 | 2008-05-14 | Astex Therapeutics Ltd | Pharmaceutical compounds |
BRPI0921795B8 (pt) * | 2008-11-04 | 2021-07-27 | Hoffmann La Roche | inibidores radiomarcados do transportador de glicina 1 e seu uso |
KR20110120885A (ko) | 2009-02-06 | 2011-11-04 | 바스프 에스이 | 개선된 내후성을 갖는 스티렌 공중합체 및 폴리아미드 기재 열가소성 성형 조성물 |
AR075442A1 (es) | 2009-02-16 | 2011-03-30 | Abbott Gmbh & Co Kg | Derivados de aminotetralina, composiciones farmaceuticas que las contienen y sus usos en terapia |
TW201038569A (en) * | 2009-02-16 | 2010-11-01 | Abbott Gmbh & Co Kg | Heterocyclic compounds, pharmaceutical compositions containing them, and their use in therapy |
US8846743B2 (en) | 2010-08-13 | 2014-09-30 | Abbott Laboratories | Aminoindane derivatives, pharmaceutical compositions containing them, and their use in therapy |
US9051280B2 (en) | 2010-08-13 | 2015-06-09 | AbbVie Deutschland GmbH & Co. KG | Tetraline and indane derivatives, pharmaceutical compositions containing them, and their use in therapy |
US8883839B2 (en) | 2010-08-13 | 2014-11-11 | Abbott Laboratories | Tetraline and indane derivatives, pharmaceutical compositions containing them, and their use in therapy |
US9045459B2 (en) * | 2010-08-13 | 2015-06-02 | AbbVie Deutschland GmbH & Co. KG | Phenalkylamine derivatives, pharmaceutical compositions containing them, and their use in therapy |
US8877794B2 (en) | 2010-08-13 | 2014-11-04 | Abbott Laboratories | Phenalkylamine derivatives, pharmaceutical compositions containing them, and their use in therapy |
US9309200B2 (en) | 2011-05-12 | 2016-04-12 | AbbVie Deutschland GmbH & Co. KG | Benzazepine derivatives, pharmaceutical compositions containing them, and their use in therapy |
US9012489B2 (en) * | 2011-08-03 | 2015-04-21 | Boehringer Ingelheim International Gmbh | Phenyl-3-aza-bicyclo[3.1.0]hex-3-yl-methanones and the use thereof as medicament |
MX2014001457A (es) | 2011-08-05 | 2014-08-21 | Abbvie Deutschland | Derivados de aminocromano, de aminotiocromano y de amino-1,2,3,4-tetrahidroquinolina composiciones farmaceuticas que los contienen, y su uso en terapia. |
JP2014533675A (ja) | 2011-11-18 | 2014-12-15 | アッヴィ・ドイチュラント・ゲー・エム・ベー・ハー・ウント・コー・カー・ゲー | N置換アミノベンゾシクロヘプテン、アミノテトラリン、アミノインダンおよびフェナルキルアミン誘導体、これらを含有する医薬組成物、および治療におけるこれらの使用 |
US9365512B2 (en) | 2012-02-13 | 2016-06-14 | AbbVie Deutschland GmbH & Co. KG | Isoindoline derivatives, pharmaceutical compositions containing them, and their use in therapy |
CN102911109B (zh) * | 2012-10-29 | 2014-01-15 | 山西医科大学 | 一种6-氨基-5-氟-1-异吲哚啉酮的制备方法 |
US9650334B2 (en) | 2013-03-15 | 2017-05-16 | Abbvie Inc. | Pyrrolidine derivatives, pharmaceutical compositions containing them, and their use in therapy |
US9656955B2 (en) | 2013-03-15 | 2017-05-23 | Abbvie Inc. | Pyrrolidine derivatives, pharmaceutical compositions containing them, and their use in therapy |
MX2016004934A (es) | 2013-10-17 | 2016-12-20 | Abbvie Deutschland | Derivados de aminotetralina y aminoindano, composiciones farmaceuticas que los contienen, y su uso en terapia. |
CN105992764A (zh) | 2013-10-17 | 2016-10-05 | 艾伯维德国有限责任两合公司 | 氨基色满、氨基硫代色满及氨基-1,2,3,4-四氢喹啉衍生物,包含其的药物组合物及其在治疗中的用途 |
EP3527569B1 (en) | 2014-02-03 | 2021-08-25 | Vitae Pharmaceuticals, LLC | Dihydropyrrolopyridine inhibitors of ror-gamma for use in treating drye eye |
WO2015159905A1 (ja) * | 2014-04-17 | 2015-10-22 | 住友化学株式会社 | ニトロ化合物の製造方法 |
MA39927B1 (fr) * | 2014-04-30 | 2018-09-28 | Hoffmann La Roche | Inhibiteurs de glyt1 pour le traitement de troubles hématologiques |
WO2016024350A1 (ja) | 2014-08-13 | 2016-02-18 | 株式会社エス・ディー・エス バイオテック | 縮合11員環化合物及びそれらを含有する農園芸用殺菌剤 |
PT3207043T (pt) | 2014-10-14 | 2019-03-25 | Vitae Pharmaceuticals Llc | Inibidores de di-hidropirrolopiridina de ror-gama |
US9845308B2 (en) | 2014-11-05 | 2017-12-19 | Vitae Pharmaceuticals, Inc. | Isoindoline inhibitors of ROR-gamma |
US9663515B2 (en) | 2014-11-05 | 2017-05-30 | Vitae Pharmaceuticals, Inc. | Dihydropyrrolopyridine inhibitors of ROR-gamma |
EP3331876B1 (en) | 2015-08-05 | 2020-10-07 | Vitae Pharmaceuticals, LLC | Modulators of ror-gamma |
EP3364976A4 (en) | 2015-10-19 | 2019-06-05 | Board of Regents, The University of Texas System | PIPERAZINYL-NORBENZOMORPHAN COMPOUNDS AND METHOD FOR USE THEREOF |
CN108463458B (zh) | 2015-11-20 | 2022-02-01 | 生命医药有限责任公司 | ROR-γ的调节剂 |
TW202220968A (zh) | 2016-01-29 | 2022-06-01 | 美商維它藥物有限責任公司 | ROR-γ調節劑 |
CN108602765B (zh) | 2016-02-08 | 2022-05-03 | 高文有限公司 | 1,2-苯二甲醇化合物的制造方法 |
JP6649967B2 (ja) | 2016-02-08 | 2020-02-19 | 株式会社エス・ディー・エス バイオテック | 殺菌性組成物 |
CN108713016B (zh) | 2016-02-18 | 2021-10-08 | 先正达参股股份有限公司 | 杀有害生物活性吡唑衍生物 |
EP3448520A4 (en) * | 2016-04-29 | 2020-07-29 | Board Of Regents, The University Of Texas System | SIGMA RECEIVER BINDERS |
US9481674B1 (en) | 2016-06-10 | 2016-11-01 | Vitae Pharmaceuticals, Inc. | Dihydropyrrolopyridine inhibitors of ROR-gamma |
CN109415367B (zh) | 2016-06-29 | 2021-04-16 | 豪夫迈·罗氏有限公司 | 用于治疗和预防乙型肝炎病毒感染的新的二氢吡咯并嘧啶类化合物 |
DK3642202T3 (da) * | 2017-06-22 | 2023-01-30 | Pfizer | Dihydro-pyrrolo-pyridin-derivater |
UA126583C2 (uk) | 2017-07-24 | 2022-11-02 | Вітае Фармасьютікалс, Ллс | ІНГІБІТОРИ ROR<font face="Symbol">g</font> |
WO2019018975A1 (en) | 2017-07-24 | 2019-01-31 | Vitae Pharmaceuticals, Inc. | INHIBITORS OF ROR GAMMA |
IL302529A (en) | 2018-03-08 | 2023-07-01 | Incyte Corp | Aminopyrizine diol compounds as PI3K–y inhibitors |
US11046658B2 (en) | 2018-07-02 | 2021-06-29 | Incyte Corporation | Aminopyrazine derivatives as PI3K-γ inhibitors |
WO2021115560A1 (en) | 2019-12-09 | 2021-06-17 | Rottapharm Biotech S.R.L. | New fyn and vegfr2 kinase inhibitors |
US11813257B2 (en) | 2020-01-09 | 2023-11-14 | Disc Medicine, Inc. | Methods of treating erythropoietic protoporphyria, X-linked protoporphyria, or congenital erythropoietic porphyria with glycine transport inhibitors |
TW202216700A (zh) | 2020-07-02 | 2022-05-01 | 印度商皮埃企業有限公司 | 異惡唑啉化合物及其作為害蟲防治劑的用途 |
AR126996A1 (es) | 2021-09-08 | 2023-12-06 | Pi Industries Ltd | Compuestos de isoxazolina y su uso como agentes de control de plagas |
Family Cites Families (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2767191A (en) * | 1953-12-31 | 1956-10-16 | American Cyanamid Co | Dihydropyrrolo-pyridines |
DE2423847A1 (de) * | 1973-05-28 | 1975-01-02 | Ciba Geigy Ag | Neue sulfamoylbenzoesaeureamide |
DE2611705A1 (de) * | 1976-03-18 | 1977-09-22 | Josef Dipl Chem Dr Rer N Klosa | N-5-(nitrofurfuryliden-)-1-amino- hydantoin enthaltende kristalloesungsmittel |
IT1176613B (it) | 1984-08-14 | 1987-08-18 | Ravizza Spa | Derivati piperazinici farmacologicamente attivi e processo per la loro preparazione |
ES2110965T3 (es) * | 1989-07-25 | 1998-03-01 | Taiho Pharmaceutical Co Ltd | Derivado de oxoindol. |
RU2124511C1 (ru) | 1993-05-14 | 1999-01-10 | Фармасьютикал Ко., Лтд | Производные пиперазина |
US6001854A (en) * | 1996-05-31 | 1999-12-14 | Allelix Neuroscience Inc. | Pharmaceutical for treating of neurological and neuropsychiatric disorders |
SK13092000A3 (sk) | 1998-03-06 | 2001-03-12 | Janssen Pharmaceutica N. V. | Inhibítory prenosu glycínu, spôsob ich prípravy, farmaceutický prostriedok s ich obsahom a ich použitie |
CA2322164A1 (en) * | 1998-03-06 | 1999-09-10 | Ludo Edmond Josephine Kennis | Glycine transport inhibitors |
EP1218358B1 (en) | 1999-09-23 | 2006-09-13 | AstraZeneca AB | Therapeutic quinazoline compounds |
EP1296950A2 (en) | 2000-04-20 | 2003-04-02 | NPS Allelix Corp. | Aminopiperidines for use as glyt-1 inhibitors |
DOP2001000189A (es) | 2000-06-30 | 2002-03-30 | Pfizer Prod Inc | Benzofenonas y sulfonas como inhibidores de la captación de glicina |
GB0021419D0 (en) | 2000-08-31 | 2000-10-18 | Oxford Glycosciences Uk Ltd | Compounds |
CA2436133A1 (en) * | 2001-01-29 | 2002-08-08 | University Of Connecticut | Receptor selective cannabimimetic aminoalkylindoles |
GB0106661D0 (en) | 2001-03-16 | 2001-05-09 | Pfizer Ltd | Pharmaceutically active compounds |
EP1421071B1 (en) | 2001-07-02 | 2009-11-18 | High Point Pharmaceuticals, LLC | Substituted piperazine and diazepane derivaives as histamine h3 receptor modulators |
WO2003035602A1 (fr) | 2001-10-25 | 2003-05-01 | Sankyo Company, Limited | Modulateurs lipidiques |
EP1554260A1 (en) * | 2002-10-22 | 2005-07-20 | Glaxo Group Limited | Aryloxyalkylamine derivatives as h3 receptor ligands |
EP1656361B1 (en) * | 2003-08-11 | 2008-01-02 | F. Hoffmann-La Roche Ag | Piperazine with or-substituted phenyl group and their use as glyt1 inhibitors |
SI1703909T1 (sl) * | 2003-09-09 | 2009-08-31 | Hoffmann La Roche | Derivati 1-benzoil-piperazina kot inhibitorji vnosa glicina za zdravljenje psihoz |
DK1663232T3 (da) * | 2003-09-09 | 2008-02-04 | Hoffmann La Roche | Benzimidazolderivater som human chymase-inhibitorer |
GB0329362D0 (en) | 2003-12-18 | 2004-01-21 | Glaxo Group Ltd | Compounds |
CN1946685A (zh) | 2004-04-29 | 2007-04-11 | 默克公司 | 氮杂环丁烷甘氨酸转运蛋白抑制剂 |
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