HRP20100181T1 - Derivati tetralina i indana i njihove upotrebe - Google Patents
Derivati tetralina i indana i njihove upotrebe Download PDFInfo
- Publication number
- HRP20100181T1 HRP20100181T1 HR20100181T HRP20100181T HRP20100181T1 HR P20100181 T1 HRP20100181 T1 HR P20100181T1 HR 20100181 T HR20100181 T HR 20100181T HR P20100181 T HRP20100181 T HR P20100181T HR P20100181 T1 HRP20100181 T1 HR P20100181T1
- Authority
- HR
- Croatia
- Prior art keywords
- alkyl
- tetrahydro
- naphthalen
- benzenesulfonyl
- hydrogen
- Prior art date
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- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 title 3
- 125000003392 indanyl group Chemical class C1(CCC2=CC=CC=C12)* 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 93
- 239000001257 hydrogen Substances 0.000 claims abstract 93
- 125000000217 alkyl group Chemical group 0.000 claims abstract 80
- 150000002431 hydrogen Chemical group 0.000 claims abstract 43
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 41
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 38
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract 36
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 36
- 125000003884 phenylalkyl group Chemical group 0.000 claims abstract 36
- 150000001875 compounds Chemical class 0.000 claims abstract 34
- 125000004404 heteroalkyl group Chemical group 0.000 claims abstract 26
- -1 cyano, hydroxy Chemical group 0.000 claims abstract 22
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 14
- 125000004442 acylamino group Chemical group 0.000 claims abstract 12
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract 12
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract 12
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 12
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims abstract 10
- 125000003118 aryl group Chemical group 0.000 claims abstract 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract 4
- 125000004641 (C1-C12) haloalkyl group Chemical group 0.000 claims abstract 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 3
- 125000001624 naphthyl group Chemical group 0.000 claims abstract 3
- 150000003839 salts Chemical class 0.000 claims abstract 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 16
- 125000005843 halogen group Chemical group 0.000 claims 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 11
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 4
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- WHWNEIBCIIYGLO-UHFFFAOYSA-N 2-[6-(benzenesulfonyl)-1,2,3,4-tetrahydronaphthalen-1-yl]-n,n-dimethylethanamine Chemical compound C=1C=C2C(CCN(C)C)CCCC2=CC=1S(=O)(=O)C1=CC=CC=C1 WHWNEIBCIIYGLO-UHFFFAOYSA-N 0.000 claims 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 125000002636 imidazolinyl group Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- FYEXYFFIQHSUGX-MRXNPFEDSA-N (1r)-6-(benzenesulfonyl)-1,2,3,4-tetrahydronaphthalene-1-carboxamide Chemical compound C([C@H](C1=CC=2)C(=O)N)CCC1=CC=2S(=O)(=O)C1=CC=CC=C1 FYEXYFFIQHSUGX-MRXNPFEDSA-N 0.000 claims 1
- FGLDMQPYGIRXEJ-CAWMZFRYSA-N (2r)-n-[[6-(3-fluorophenyl)sulfonyl-1,2,3,4-tetrahydronaphthalen-1-yl]methyl]pyrrolidine-2-carboxamide Chemical compound FC1=CC=CC(S(=O)(=O)C=2C=C3CCCC(CNC(=O)[C@@H]4NCCC4)C3=CC=2)=C1 FGLDMQPYGIRXEJ-CAWMZFRYSA-N 0.000 claims 1
- SWYDSKFXSYZNJJ-FBLFFUNLSA-N (2r)-n-[[6-(benzenesulfonyl)-1,2,3,4-tetrahydronaphthalen-1-yl]methyl]pyrrolidine-2-carboxamide Chemical compound O=C([C@@H]1NCCC1)NCC(C1=CC=2)CCCC1=CC=2S(=O)(=O)C1=CC=CC=C1 SWYDSKFXSYZNJJ-FBLFFUNLSA-N 0.000 claims 1
- KBUYEZWLERBYIJ-HNNXBMFYSA-N 1-[(1r)-6-(3-methoxyphenyl)sulfonyl-1,2,3,4-tetrahydronaphthalen-1-yl]-n-methylmethanamine Chemical compound C([C@H](C1=CC=2)CNC)CCC1=CC=2S(=O)(=O)C1=CC=CC(OC)=C1 KBUYEZWLERBYIJ-HNNXBMFYSA-N 0.000 claims 1
- YUUJDPSKULOBRB-HNNXBMFYSA-N 1-[(1r)-6-(benzenesulfonyl)-1,2,3,4-tetrahydronaphthalen-1-yl]-n-methylmethanamine Chemical compound C([C@H](C1=CC=2)CNC)CCC1=CC=2S(=O)(=O)C1=CC=CC=C1 YUUJDPSKULOBRB-HNNXBMFYSA-N 0.000 claims 1
- CDRDILQTZRZELO-AWEZNQCLSA-N 1-[(1r)-6-(benzenesulfonyl)-8-fluoro-1,2,3,4-tetrahydronaphthalen-1-yl]-n-methylmethanamine Chemical compound C([C@H](C1=C(F)C=2)CNC)CCC1=CC=2S(=O)(=O)C1=CC=CC=C1 CDRDILQTZRZELO-AWEZNQCLSA-N 0.000 claims 1
- YUUJDPSKULOBRB-OAHLLOKOSA-N 1-[(1s)-6-(benzenesulfonyl)-1,2,3,4-tetrahydronaphthalen-1-yl]-n-methylmethanamine Chemical compound C([C@@H](C1=CC=2)CNC)CCC1=CC=2S(=O)(=O)C1=CC=CC=C1 YUUJDPSKULOBRB-OAHLLOKOSA-N 0.000 claims 1
- WQHJXIPHTNCZDI-UHFFFAOYSA-M 1-[2-[5-(benzenesulfonyl)-2,3-dihydro-1h-inden-1-yl]ethyl]-1-methylpyrrol-1-ium;iodide Chemical compound [I-].C1CC2=CC(S(=O)(=O)C=3C=CC=CC=3)=CC=C2C1CC[N+]1(C)C=CC=C1 WQHJXIPHTNCZDI-UHFFFAOYSA-M 0.000 claims 1
- YGCKSNXSJRECSM-UHFFFAOYSA-N 1-[2-[6-(benzenesulfonyl)-1,2,3,4-tetrahydronaphthalen-1-yl]ethyl]imidazole Chemical compound C=1C=C2C(CCN3C=NC=C3)CCCC2=CC=1S(=O)(=O)C1=CC=CC=C1 YGCKSNXSJRECSM-UHFFFAOYSA-N 0.000 claims 1
- AMSVUDARVLJWMO-UHFFFAOYSA-N 1-[2-[7-(benzenesulfonyl)-1,2,3,4-tetrahydronaphthalen-1-yl]ethyl]imidazole Chemical compound C=1C=C2CCCC(CCN3C=NC=C3)C2=CC=1S(=O)(=O)C1=CC=CC=C1 AMSVUDARVLJWMO-UHFFFAOYSA-N 0.000 claims 1
- NRYDNXHYNZSEFM-UHFFFAOYSA-N 1-[6-(3-chlorophenyl)sulfonyl-1,2,3,4-tetrahydronaphthalen-1-yl]-n-methylmethanamine Chemical compound C=1C=C2C(CNC)CCCC2=CC=1S(=O)(=O)C1=CC=CC(Cl)=C1 NRYDNXHYNZSEFM-UHFFFAOYSA-N 0.000 claims 1
- AUWNTFXZAMDCBS-UHFFFAOYSA-N 1-[6-(3-fluorophenyl)sulfonyl-1,2,3,4-tetrahydronaphthalen-1-yl]-n-methylmethanamine Chemical compound C=1C=C2C(CNC)CCCC2=CC=1S(=O)(=O)C1=CC=CC(F)=C1 AUWNTFXZAMDCBS-UHFFFAOYSA-N 0.000 claims 1
- BNWCQYXIEXHUHJ-UHFFFAOYSA-N 1-[6-(benzenesulfonyl)-1,2,3,4-tetrahydronaphthalen-1-yl]-n,n-dimethylmethanamine Chemical compound C=1C=C2C(CN(C)C)CCCC2=CC=1S(=O)(=O)C1=CC=CC=C1 BNWCQYXIEXHUHJ-UHFFFAOYSA-N 0.000 claims 1
- YUUJDPSKULOBRB-UHFFFAOYSA-N 1-[6-(benzenesulfonyl)-1,2,3,4-tetrahydronaphthalen-1-yl]-n-methylmethanamine Chemical compound C=1C=C2C(CNC)CCCC2=CC=1S(=O)(=O)C1=CC=CC=C1 YUUJDPSKULOBRB-UHFFFAOYSA-N 0.000 claims 1
- IBTFIJSOSVWYBH-UHFFFAOYSA-N 1-[6-(benzenesulfonyl)-7-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl]-n-methylmethanamine Chemical compound COC=1C=C2C(CNC)CCCC2=CC=1S(=O)(=O)C1=CC=CC=C1 IBTFIJSOSVWYBH-UHFFFAOYSA-N 0.000 claims 1
- RAMYSUYACXEDTH-AWEZNQCLSA-N 1-[[(1r)-6-(3-fluorophenyl)sulfonyl-1,2,3,4-tetrahydronaphthalen-1-yl]methyl]-1-methylurea Chemical compound C([C@H](C1=CC=2)CN(C)C(N)=O)CCC1=CC=2S(=O)(=O)C1=CC=CC(F)=C1 RAMYSUYACXEDTH-AWEZNQCLSA-N 0.000 claims 1
- MVDUOOINMKHGMU-AWEZNQCLSA-N 1-[[(1r)-6-(3-fluorophenyl)sulfonyl-1,2,3,4-tetrahydronaphthalen-1-yl]methyl]-3-methylurea Chemical compound C([C@H](C1=CC=2)CNC(=O)NC)CCC1=CC=2S(=O)(=O)C1=CC=CC(F)=C1 MVDUOOINMKHGMU-AWEZNQCLSA-N 0.000 claims 1
- FOVVMXIMXXDBHY-UHFFFAOYSA-N 1-[[7-(benzenesulfonyl)-1,2,3,4-tetrahydronaphthalen-1-yl]methyl]-2-methyl-3-phenylguanidine Chemical compound C=1C=CC=CC=1N=C(NC)NCC(C1=C2)CCCC1=CC=C2S(=O)(=O)C1=CC=CC=C1 FOVVMXIMXXDBHY-UHFFFAOYSA-N 0.000 claims 1
- FUFJBZCOEVVFIS-AWEZNQCLSA-N 1-cyano-2-[[(1r)-6-(2-fluorophenyl)sulfonyl-1,2,3,4-tetrahydronaphthalen-1-yl]methyl]guanidine Chemical compound FC1=CC=CC=C1S(=O)(=O)C1=CC=C([C@H](CNC(=N)NC#N)CCC2)C2=C1 FUFJBZCOEVVFIS-AWEZNQCLSA-N 0.000 claims 1
- HGAWOQUMCZNLBM-INIZCTEOSA-N 2-(dimethylamino)-n-[[(1r)-6-(3-fluorophenyl)sulfonyl-1,2,3,4-tetrahydronaphthalen-1-yl]methyl]acetamide Chemical compound C([C@H](C1=CC=2)CNC(=O)CN(C)C)CCC1=CC=2S(=O)(=O)C1=CC=CC(F)=C1 HGAWOQUMCZNLBM-INIZCTEOSA-N 0.000 claims 1
- TWZOMKQMAROWLV-CQSZACIVSA-N 2-[(1r)-6-(benzenesulfonyl)-1,2,3,4-tetrahydronaphthalen-1-yl]acetamide Chemical compound C([C@@H](C1=CC=2)CC(=O)N)CCC1=CC=2S(=O)(=O)C1=CC=CC=C1 TWZOMKQMAROWLV-CQSZACIVSA-N 0.000 claims 1
- ZGMDYQDWHQCXJN-UHFFFAOYSA-N 2-[2-[7-(benzenesulfonyl)-1,2,3,4-tetrahydronaphthalen-1-yl]ethyl]guanidine Chemical compound C1=C2C(CCNC(=N)N)CCCC2=CC=C1S(=O)(=O)C1=CC=CC=C1 ZGMDYQDWHQCXJN-UHFFFAOYSA-N 0.000 claims 1
- GIYMIIHLGYHFMY-UHFFFAOYSA-N 2-[5-(benzenesulfonyl)-2,3-dihydro-1h-inden-1-yl]-n-methylethanamine Chemical compound C=1C=C2C(CCNC)CCC2=CC=1S(=O)(=O)C1=CC=CC=C1 GIYMIIHLGYHFMY-UHFFFAOYSA-N 0.000 claims 1
- DVWCIWXZXNOOCY-UHFFFAOYSA-N 2-[5-(benzenesulfonyl)-2,3-dihydro-1h-inden-1-yl]ethanamine Chemical compound C=1C=C2C(CCN)CCC2=CC=1S(=O)(=O)C1=CC=CC=C1 DVWCIWXZXNOOCY-UHFFFAOYSA-N 0.000 claims 1
- CLQOXVAQDAZCNX-UHFFFAOYSA-N 2-[6-(2-fluorophenyl)sulfonyl-1,2,3,4-tetrahydronaphthalen-1-yl]ethanamine Chemical compound C=1C=C2C(CCN)CCCC2=CC=1S(=O)(=O)C1=CC=CC=C1F CLQOXVAQDAZCNX-UHFFFAOYSA-N 0.000 claims 1
- RXWXPYGBFCWMJM-UHFFFAOYSA-N 2-[6-(benzenesulfonyl)-1,2,3,4-tetrahydronaphthalen-1-yl]-n-(diaminomethylidene)acetamide Chemical compound C=1C=C2C(CC(=O)NC(=N)N)CCCC2=CC=1S(=O)(=O)C1=CC=CC=C1 RXWXPYGBFCWMJM-UHFFFAOYSA-N 0.000 claims 1
- LITMVMQZVLEKEX-UHFFFAOYSA-N 2-[6-(benzenesulfonyl)-1,2,3,4-tetrahydronaphthalen-1-yl]ethanamine Chemical compound C=1C=C2C(CCN)CCCC2=CC=1S(=O)(=O)C1=CC=CC=C1 LITMVMQZVLEKEX-UHFFFAOYSA-N 0.000 claims 1
- JOXDYCMJCFLLKT-UHFFFAOYSA-N 2-[6-(benzenesulfonyl)-7-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl]-n-methylethanamine Chemical compound COC=1C=C2C(CCNC)CCCC2=CC=1S(=O)(=O)C1=CC=CC=C1 JOXDYCMJCFLLKT-UHFFFAOYSA-N 0.000 claims 1
- ORUASUBYHJIEIH-UHFFFAOYSA-N 2-[6-(benzenesulfonyl)-7-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl]ethanamine Chemical compound COC1=CC=2C(CCN)CCCC=2C=C1S(=O)(=O)C1=CC=CC=C1 ORUASUBYHJIEIH-UHFFFAOYSA-N 0.000 claims 1
- TYOOZUGUCZLUBH-UHFFFAOYSA-N 2-[7-(benzenesulfonyl)-1,2,3,4-tetrahydronaphthalen-1-yl]ethanamine Chemical compound C1=C2C(CCN)CCCC2=CC=C1S(=O)(=O)C1=CC=CC=C1 TYOOZUGUCZLUBH-UHFFFAOYSA-N 0.000 claims 1
- PDEREELDEZAWRB-UHFFFAOYSA-N 2-[7-(benzenesulfonyl)-1,2,3,4-tetrahydronaphthalen-1-yl]ethanimidamide Chemical compound C1=C2C(CC(=N)N)CCCC2=CC=C1S(=O)(=O)C1=CC=CC=C1 PDEREELDEZAWRB-UHFFFAOYSA-N 0.000 claims 1
- XZULINOKXSMSLT-HNNXBMFYSA-N 2-[[(1r)-6-(3-fluorophenyl)sulfonyl-1,2,3,4-tetrahydronaphthalen-1-yl]methyl-methylamino]acetamide Chemical compound C([C@H](C1=CC=2)CN(C)CC(N)=O)CCC1=CC=2S(=O)(=O)C1=CC=CC(F)=C1 XZULINOKXSMSLT-HNNXBMFYSA-N 0.000 claims 1
- YZCZIRLLUMPZNG-AWEZNQCLSA-N 2-[[(1r)-6-(3-fluorophenyl)sulfonyl-1,2,3,4-tetrahydronaphthalen-1-yl]methylamino]-1,4-dihydroimidazol-5-one Chemical compound FC1=CC=CC(S(=O)(=O)C=2C=C3CCC[C@@H](CNC=4NC(=O)CN=4)C3=CC=2)=C1 YZCZIRLLUMPZNG-AWEZNQCLSA-N 0.000 claims 1
- BFTGZENXFFDRLJ-HNNXBMFYSA-N 2-[[(1r)-6-(3-fluorophenyl)sulfonyl-1,2,3,4-tetrahydronaphthalen-1-yl]methylamino]-n-methylacetamide Chemical compound C([C@H](C1=CC=2)CNCC(=O)NC)CCC1=CC=2S(=O)(=O)C1=CC=CC(F)=C1 BFTGZENXFFDRLJ-HNNXBMFYSA-N 0.000 claims 1
- ORYIDMJUFFUMMP-AWEZNQCLSA-N 2-[[(1r)-6-(3-fluorophenyl)sulfonyl-1,2,3,4-tetrahydronaphthalen-1-yl]methylamino]acetamide Chemical compound C([C@H](C1=CC=2)CNCC(=O)N)CCC1=CC=2S(=O)(=O)C1=CC=CC(F)=C1 ORYIDMJUFFUMMP-AWEZNQCLSA-N 0.000 claims 1
- OSRIONOQBURAGV-HNNXBMFYSA-N 2-[[(1r)-6-(3-fluorophenyl)sulfonyl-1,2,3,4-tetrahydronaphthalen-1-yl]methylamino]ethanol Chemical compound C([C@H](C1=CC=2)CNCCO)CCC1=CC=2S(=O)(=O)C1=CC=CC(F)=C1 OSRIONOQBURAGV-HNNXBMFYSA-N 0.000 claims 1
- AKHFOAQLUXPFBJ-UHFFFAOYSA-N 2-[[6-(benzenesulfonyl)-1,2,3,4-tetrahydronaphthalen-1-yl]methyl]guanidine Chemical compound C=1C=C2C(CNC(=N)N)CCCC2=CC=1S(=O)(=O)C1=CC=CC=C1 AKHFOAQLUXPFBJ-UHFFFAOYSA-N 0.000 claims 1
- JNJDOCZPYLMVEL-UHFFFAOYSA-N 2-[[7-(benzenesulfonyl)-1,2,3,4-tetrahydronaphthalen-1-yl]methyl]guanidine Chemical compound C1=C2C(CNC(=N)N)CCCC2=CC=C1S(=O)(=O)C1=CC=CC=C1 JNJDOCZPYLMVEL-UHFFFAOYSA-N 0.000 claims 1
- YCNMWVYNBBMOHG-AWEZNQCLSA-N 2-amino-n-[[(1r)-6-(3-fluorophenyl)sulfonyl-1,2,3,4-tetrahydronaphthalen-1-yl]methyl]acetamide Chemical compound C([C@H](C1=CC=2)CNC(=O)CN)CCC1=CC=2S(=O)(=O)C1=CC=CC(F)=C1 YCNMWVYNBBMOHG-AWEZNQCLSA-N 0.000 claims 1
- KSPFKMBOSOZVJS-UHFFFAOYSA-N 3-[5-(benzenesulfonyl)-2,3-dihydro-1h-inden-1-yl]propan-1-amine Chemical compound C=1C=C2C(CCCN)CCC2=CC=1S(=O)(=O)C1=CC=CC=C1 KSPFKMBOSOZVJS-UHFFFAOYSA-N 0.000 claims 1
- ZROHQKHHRGZGNC-UHFFFAOYSA-N 3-[6-(3-fluorophenyl)sulfonyl-1,2,3,4-tetrahydronaphthalen-1-yl]propan-1-amine Chemical compound C=1C=C2C(CCCN)CCCC2=CC=1S(=O)(=O)C1=CC=CC(F)=C1 ZROHQKHHRGZGNC-UHFFFAOYSA-N 0.000 claims 1
- NPHSNVUGSBUBCU-UHFFFAOYSA-N 3-[6-(benzenesulfonyl)-1,2,3,4-tetrahydronaphthalen-1-yl]propanimidamide Chemical compound C=1C=C2C(CCC(=N)N)CCCC2=CC=1S(=O)(=O)C1=CC=CC=C1 NPHSNVUGSBUBCU-UHFFFAOYSA-N 0.000 claims 1
- UALCDYCEOQSUDI-HNNXBMFYSA-N 3-[[(1r)-6-(3-fluorophenyl)sulfonyl-1,2,3,4-tetrahydronaphthalen-1-yl]methyl]-1,1-dimethylurea Chemical compound C([C@H](C1=CC=2)CNC(=O)N(C)C)CCC1=CC=2S(=O)(=O)C1=CC=CC(F)=C1 UALCDYCEOQSUDI-HNNXBMFYSA-N 0.000 claims 1
- MJFXTASINWICHJ-HNNXBMFYSA-N 3-[[(5r)-5-(aminomethyl)-5,6,7,8-tetrahydronaphthalen-2-yl]sulfonyl]benzonitrile Chemical compound C([C@H](C1=CC=2)CN)CCC1=CC=2S(=O)(=O)C1=CC=CC(C#N)=C1 MJFXTASINWICHJ-HNNXBMFYSA-N 0.000 claims 1
- ZEYRKYDLUSGEGJ-ZDUSSCGKSA-N 3-[[(5r)-5-(aminomethyl)-5,6,7,8-tetrahydronaphthalen-2-yl]sulfonyl]phenol Chemical compound C([C@H](C1=CC=2)CN)CCC1=CC=2S(=O)(=O)C1=CC=CC(O)=C1 ZEYRKYDLUSGEGJ-ZDUSSCGKSA-N 0.000 claims 1
- FYEXYFFIQHSUGX-UHFFFAOYSA-N 6-(benzenesulfonyl)-1,2,3,4-tetrahydronaphthalene-1-carboxamide Chemical compound C=1C=C2C(C(=O)N)CCCC2=CC=1S(=O)(=O)C1=CC=CC=C1 FYEXYFFIQHSUGX-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- 208000030814 Eating disease Diseases 0.000 claims 1
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 1
- 208000023105 Huntington disease Diseases 0.000 claims 1
- 208000026139 Memory disease Diseases 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 208000025966 Neurological disease Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 208000028017 Psychotic disease Diseases 0.000 claims 1
- IOLMIJPTSIFVSF-LBPRGKRZSA-N [(1r)-6-(1-methylimidazol-2-yl)sulfonyl-1,2,3,4-tetrahydronaphthalen-1-yl]methanamine Chemical compound CN1C=CN=C1S(=O)(=O)C1=CC=C([C@H](CN)CCC2)C2=C1 IOLMIJPTSIFVSF-LBPRGKRZSA-N 0.000 claims 1
- PAQUVAIORCYZFB-AWEZNQCLSA-N [(1r)-6-(1h-indol-3-ylsulfonyl)-1,2,3,4-tetrahydronaphthalen-1-yl]methanamine Chemical compound C1=CC=C2C(S(=O)(=O)C=3C=C4CCC[C@H](C4=CC=3)CN)=CNC2=C1 PAQUVAIORCYZFB-AWEZNQCLSA-N 0.000 claims 1
- QUNVWLZIMPVCFO-NSHDSACASA-N [(1r)-6-(1h-pyrazol-4-ylsulfonyl)-1,2,3,4-tetrahydronaphthalen-1-yl]methanamine Chemical compound C([C@H](C1=CC=2)CN)CCC1=CC=2S(=O)(=O)C=1C=NNC=1 QUNVWLZIMPVCFO-NSHDSACASA-N 0.000 claims 1
- LKMQZMYQTGQFSV-LBPRGKRZSA-N [(1r)-6-(1h-pyrrol-3-ylsulfonyl)-1,2,3,4-tetrahydronaphthalen-1-yl]methanamine Chemical compound C([C@H](C1=CC=2)CN)CCC1=CC=2S(=O)(=O)C=1C=CNC=1 LKMQZMYQTGQFSV-LBPRGKRZSA-N 0.000 claims 1
- RJCGVXCLLBQVMP-ZDUSSCGKSA-N [(1r)-6-(3-fluorophenyl)sulfonyl-1,2,3,4-tetrahydronaphthalen-1-yl]methanamine Chemical compound C([C@H](C1=CC=2)CN)CCC1=CC=2S(=O)(=O)C1=CC=CC(F)=C1 RJCGVXCLLBQVMP-ZDUSSCGKSA-N 0.000 claims 1
- MTTHRRVVGMPYQG-ZDUSSCGKSA-N [(1r)-6-(3-fluorophenyl)sulfonyl-1,2,3,4-tetrahydronaphthalen-1-yl]methylurea Chemical compound C([C@H](C1=CC=2)CNC(=O)N)CCC1=CC=2S(=O)(=O)C1=CC=CC(F)=C1 MTTHRRVVGMPYQG-ZDUSSCGKSA-N 0.000 claims 1
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- YLVJKGOPOMYBOW-ZDUSSCGKSA-N [(1r)-6-[(5-fluoro-1h-indol-3-yl)sulfonyl]-1,2,3,4-tetrahydronaphthalen-1-yl]methanamine Chemical compound C1=C(F)C=C2C(S(=O)(=O)C=3C=C4CCC[C@H](C4=CC=3)CN)=CNC2=C1 YLVJKGOPOMYBOW-ZDUSSCGKSA-N 0.000 claims 1
- GEGRUTUYLJXAAU-LBPRGKRZSA-N [(1r)-6-[(6-fluoro-1h-benzimidazol-4-yl)sulfonyl]-1,2,3,4-tetrahydronaphthalen-1-yl]methanamine Chemical compound C([C@H](C1=CC=2)CN)CCC1=CC=2S(=O)(=O)C1=CC(F)=CC2=C1NC=N2 GEGRUTUYLJXAAU-LBPRGKRZSA-N 0.000 claims 1
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- JXOPYIMVAYRSFM-UHFFFAOYSA-N [6-(benzenesulfonyl)-1,2,3,4-tetrahydronaphthalen-1-yl]methanamine Chemical compound C=1C=C2C(CN)CCCC2=CC=1S(=O)(=O)C1=CC=CC=C1 JXOPYIMVAYRSFM-UHFFFAOYSA-N 0.000 claims 1
- GAHMIXAUEZAMRF-UHFFFAOYSA-N [6-(benzenesulfonyl)-1,2,3,4-tetrahydronaphthalen-1-yl]methylurea Chemical compound C=1C=C2C(CNC(=O)N)CCCC2=CC=1S(=O)(=O)C1=CC=CC=C1 GAHMIXAUEZAMRF-UHFFFAOYSA-N 0.000 claims 1
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- UGNVDFVTKCKDRU-CYBMUJFWSA-N n-(diaminomethylidene)-2-[(1r)-6-(3-fluorophenyl)sulfonyl-1,2,3,4-tetrahydronaphthalen-1-yl]acetamide Chemical compound C([C@@H](C1=CC=2)CC(=O)NC(=N)N)CCC1=CC=2S(=O)(=O)C1=CC=CC(F)=C1 UGNVDFVTKCKDRU-CYBMUJFWSA-N 0.000 claims 1
- RLBLLJTVMSEORL-UHFFFAOYSA-N n-[2-[5-(benzenesulfonyl)-2,3-dihydro-1h-inden-1-yl]ethyl]-4,5-dihydro-1h-imidazol-2-amine Chemical compound C=1C=C2C(CCNC=3NCCN=3)CCC2=CC=1S(=O)(=O)C1=CC=CC=C1 RLBLLJTVMSEORL-UHFFFAOYSA-N 0.000 claims 1
- CVRJOWVPDJEUTB-UHFFFAOYSA-N n-[2-[7-(benzenesulfonyl)-1,2,3,4-tetrahydronaphthalen-1-yl]ethyl]pyrimidin-2-amine Chemical compound C=1C=C2CCCC(CCNC=3N=CC=CN=3)C2=CC=1S(=O)(=O)C1=CC=CC=C1 CVRJOWVPDJEUTB-UHFFFAOYSA-N 0.000 claims 1
- BIFDMBXNADJSHB-INIZCTEOSA-N n-[[(1r)-6-(1h-indol-3-ylsulfonyl)-1,2,3,4-tetrahydronaphthalen-1-yl]methyl]acetamide Chemical compound C1=CC=C2C(S(=O)(=O)C=3C=C4CCC[C@H](C4=CC=3)CNC(=O)C)=CNC2=C1 BIFDMBXNADJSHB-INIZCTEOSA-N 0.000 claims 1
- VAEJKIVMXXKIFX-HNNXBMFYSA-N n-[[(1r)-6-(3-fluorophenyl)sulfonyl-1,2,3,4-tetrahydronaphthalen-1-yl]methyl]-1h-imidazole-2-carboxamide Chemical compound FC1=CC=CC(S(=O)(=O)C=2C=C3CCC[C@@H](CNC(=O)C=4NC=CN=4)C3=CC=2)=C1 VAEJKIVMXXKIFX-HNNXBMFYSA-N 0.000 claims 1
- URBDMKKVFOMBMB-INIZCTEOSA-N n-[[(1r)-6-(3-fluorophenyl)sulfonyl-1,2,3,4-tetrahydronaphthalen-1-yl]methyl]-1h-pyrrole-2-carboxamide Chemical compound FC1=CC=CC(S(=O)(=O)C=2C=C3CCC[C@@H](CNC(=O)C=4NC=CC=4)C3=CC=2)=C1 URBDMKKVFOMBMB-INIZCTEOSA-N 0.000 claims 1
- DZSWVOUBCXRCEE-HNNXBMFYSA-N n-[[(1r)-6-(3-fluorophenyl)sulfonyl-1,2,3,4-tetrahydronaphthalen-1-yl]methyl]-2-(methylamino)acetamide Chemical compound C([C@H](C1=CC=2)CNC(=O)CNC)CCC1=CC=2S(=O)(=O)C1=CC=CC(F)=C1 DZSWVOUBCXRCEE-HNNXBMFYSA-N 0.000 claims 1
- XESGTQXHHPZNJK-AWEZNQCLSA-N n-[[(1r)-6-(3-fluorophenyl)sulfonyl-1,2,3,4-tetrahydronaphthalen-1-yl]methyl]-2-hydroxyacetamide Chemical compound C([C@H](C1=CC=2)CNC(=O)CO)CCC1=CC=2S(=O)(=O)C1=CC=CC(F)=C1 XESGTQXHHPZNJK-AWEZNQCLSA-N 0.000 claims 1
- YQBHAOBHMAGPDP-INIZCTEOSA-N n-[[(1r)-6-(3-fluorophenyl)sulfonyl-1,2,3,4-tetrahydronaphthalen-1-yl]methyl]-n-methylacetamide Chemical compound C([C@H](C1=CC=2)CN(C)C(C)=O)CCC1=CC=2S(=O)(=O)C1=CC=CC(F)=C1 YQBHAOBHMAGPDP-INIZCTEOSA-N 0.000 claims 1
- AVJDSQQZGDSHKX-HNNXBMFYSA-N n-[[(1r)-6-(3-fluorophenyl)sulfonyl-1,2,3,4-tetrahydronaphthalen-1-yl]methyl]acetamide Chemical compound C([C@H](C1=CC=2)CNC(=O)C)CCC1=CC=2S(=O)(=O)C1=CC=CC(F)=C1 AVJDSQQZGDSHKX-HNNXBMFYSA-N 0.000 claims 1
- QVHNGLRPAQDRMO-AWEZNQCLSA-N n-[[(1r)-6-(3-fluorophenyl)sulfonyl-1,2,3,4-tetrahydronaphthalen-1-yl]methyl]methanesulfonamide Chemical compound C([C@H](C1=CC=2)CNS(=O)(=O)C)CCC1=CC=2S(=O)(=O)C1=CC=CC(F)=C1 QVHNGLRPAQDRMO-AWEZNQCLSA-N 0.000 claims 1
- VDBMDXVKPMDOPB-HNNXBMFYSA-N n-[[(1r)-6-(benzenesulfonyl)-8-fluoro-1,2,3,4-tetrahydronaphthalen-1-yl]methyl]acetamide Chemical compound C([C@H](C1=C(F)C=2)CNC(=O)C)CCC1=CC=2S(=O)(=O)C1=CC=CC=C1 VDBMDXVKPMDOPB-HNNXBMFYSA-N 0.000 claims 1
- PFVHIMNVYLPCPM-UHFFFAOYSA-N n-[[6-(3-fluorophenyl)sulfonyl-1,2,3,4-tetrahydronaphthalen-1-yl]methyl]ethanamine Chemical compound C=1C=C2C(CNCC)CCCC2=CC=1S(=O)(=O)C1=CC=CC(F)=C1 PFVHIMNVYLPCPM-UHFFFAOYSA-N 0.000 claims 1
- OXXNGFOEILUFTQ-UHFFFAOYSA-N n-[[6-(benzenesulfonyl)-1,2,3,4-tetrahydronaphthalen-1-yl]methyl]-4,5-dihydro-1h-imidazol-2-amine Chemical compound C=1C=C2C(CNC=3NCCN=3)CCCC2=CC=1S(=O)(=O)C1=CC=CC=C1 OXXNGFOEILUFTQ-UHFFFAOYSA-N 0.000 claims 1
- CMDKVJLGJQXJNY-UHFFFAOYSA-N n-[[6-(benzenesulfonyl)-1,2,3,4-tetrahydronaphthalen-1-yl]methyl]pyrimidin-2-amine Chemical compound C=1C=C2C(CNC=3N=CC=CN=3)CCCC2=CC=1S(=O)(=O)C1=CC=CC=C1 CMDKVJLGJQXJNY-UHFFFAOYSA-N 0.000 claims 1
- USEIBHVWUBIONJ-UHFFFAOYSA-N n-[[7-(benzenesulfonyl)-1,2,3,4-tetrahydronaphthalen-1-yl]methyl]-5,5-dimethyl-4,6-dihydro-1h-pyrimidin-2-amine Chemical compound C1C(C)(C)CNC(NCC2C3=CC(=CC=C3CCC2)S(=O)(=O)C=2C=CC=CC=2)=N1 USEIBHVWUBIONJ-UHFFFAOYSA-N 0.000 claims 1
- DGYWYRINPHBYNZ-AWEZNQCLSA-N n-methyl-1-[(1r)-6-(1-methylpyrrol-3-yl)sulfonyl-1,2,3,4-tetrahydronaphthalen-1-yl]methanamine Chemical compound C([C@H](C1=CC=2)CNC)CCC1=CC=2S(=O)(=O)C=1C=CN(C)C=1 DGYWYRINPHBYNZ-AWEZNQCLSA-N 0.000 claims 1
- FATVWPGDOJVMQE-ZDUSSCGKSA-N n-methyl-1-[(1r)-6-(1h-pyrrol-3-ylsulfonyl)-1,2,3,4-tetrahydronaphthalen-1-yl]methanamine Chemical compound C([C@H](C1=CC=2)CNC)CCC1=CC=2S(=O)(=O)C=1C=CNC=1 FATVWPGDOJVMQE-ZDUSSCGKSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
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Classifications
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- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
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- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
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- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
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- 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
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
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PCT/EP2005/013487 WO2006066790A1 (en) | 2004-12-21 | 2005-12-15 | Tetralin and indane derivatives and uses thereof |
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US7713954B2 (en) * | 2004-09-30 | 2010-05-11 | Roche Palo Alto Llc | Compositions and methods for treating cognitive disorders |
ES2359725T3 (es) * | 2004-09-30 | 2011-05-26 | F. Hoffmann-La Roche Ag | Composiciones y métodos para el tratamiento de trastornos cognitivos. |
KR100889185B1 (ko) * | 2004-12-21 | 2009-03-16 | 에프. 호프만-라 로슈 아게 | 테트랄린 및 인단 유도체 및 5-ht 길항제로서의 이의용도 |
SI1831159T1 (sl) * | 2004-12-21 | 2010-04-30 | Hoffmann La Roche | Derivati tetralina in indana ter njune uporabe |
GB0500029D0 (en) | 2005-01-04 | 2005-02-09 | Univ Belfast | Basic ionic liquids |
RU2008115032A (ru) * | 2005-11-03 | 2009-12-10 | Ф. Хоффманн-Ля Рош Аг (Ch) | Арилсульфонилхроманы в качестве ингибиторов 5-нт6 |
ES2274725B1 (es) * | 2005-11-08 | 2008-04-01 | Laboratorios Del Dr. Esteve, S.A. | Indeno derivados, su preparacion y su uso como medicamentos. |
BRPI0713736A2 (pt) * | 2006-06-20 | 2014-11-18 | Hoffmann La Roche | Derivados de tetralina e indano e emprego destes |
JP2009541249A (ja) * | 2006-06-20 | 2009-11-26 | エフ.ホフマン−ラ ロシュ アーゲー | アリールスルホニルナフタレン誘導体およびその使用 |
CN101472883A (zh) * | 2006-06-20 | 2009-07-01 | 弗·哈夫曼-拉罗切有限公司 | 芳基磺酰氨基四氢萘衍生物以及其应用 |
FR2913886B1 (fr) | 2007-03-22 | 2012-03-02 | Guerbet Sa | Utilisation de nanoparticules metalliques dans le diagnostique de la maladie d'alzheimer |
TWI498115B (zh) | 2007-12-27 | 2015-09-01 | Daiichi Sankyo Co Ltd | 咪唑羰基化合物 |
WO2010069778A1 (en) | 2008-12-18 | 2010-06-24 | F. Hoffmann-La Roche Ag | Process for synthesis of amino-methyl tetraline derivatives |
GB201406172D0 (en) * | 2014-04-04 | 2014-05-21 | Univ Nottingham | Therapy and pharmaceutical composition |
JP2019529502A (ja) * | 2016-09-30 | 2019-10-17 | バイオティー セラピーズ インコーポレイテッド | アルツハイマー病及びパーキンソン病を処置するための組成物及び方法 |
WO2023033180A1 (ja) * | 2021-09-06 | 2023-03-09 | 株式会社クレハ | アゾール誘導体のr-エナンチオマー、農園芸用薬剤および工業用材料保護剤 |
KR20230113933A (ko) | 2022-01-24 | 2023-08-01 | 삼성에스디에스 주식회사 | 프로그램 기능점수 측정 서버 및 시스템 |
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US7713954B2 (en) * | 2004-09-30 | 2010-05-11 | Roche Palo Alto Llc | Compositions and methods for treating cognitive disorders |
SI1831159T1 (sl) * | 2004-12-21 | 2010-04-30 | Hoffmann La Roche | Derivati tetralina in indana ter njune uporabe |
BRPI0713736A2 (pt) * | 2006-06-20 | 2014-11-18 | Hoffmann La Roche | Derivados de tetralina e indano e emprego destes |
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2005
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- 2005-12-15 DE DE602005019098T patent/DE602005019098D1/de active Active
- 2005-12-15 WO PCT/EP2005/013487 patent/WO2006066790A1/en active Application Filing
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