JP2019535825A5 - - Google Patents
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- Publication number
- JP2019535825A5 JP2019535825A5 JP2019547227A JP2019547227A JP2019535825A5 JP 2019535825 A5 JP2019535825 A5 JP 2019535825A5 JP 2019547227 A JP2019547227 A JP 2019547227A JP 2019547227 A JP2019547227 A JP 2019547227A JP 2019535825 A5 JP2019535825 A5 JP 2019535825A5
- Authority
- JP
- Japan
- Prior art keywords
- decane
- ethyl
- azaspiro
- oxa
- piperazine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 piperazine-1-yl Chemical group 0.000 claims description 158
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 92
- 125000000217 alkyl group Chemical group 0.000 claims description 84
- 150000001875 compounds Chemical class 0.000 claims description 47
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 36
- 229940002612 prodrug Drugs 0.000 claims description 36
- 239000000651 prodrug Substances 0.000 claims description 36
- 150000003839 salts Chemical class 0.000 claims description 36
- 239000012453 solvate Substances 0.000 claims description 36
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 32
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 30
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 30
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 claims description 29
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- YRCGAHTZOXPQPR-UHFFFAOYSA-N 2-ethylnonanoic acid Chemical compound CCCCCCCC(CC)C(O)=O YRCGAHTZOXPQPR-UHFFFAOYSA-N 0.000 claims description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
- VFLQCKVZBDPECH-FQEVSTJZSA-N (3R)-3-[2-[4-(4-methoxyphenyl)piperazin-1-yl]ethyl]-8-methylsulfonyl-2-oxa-8-azaspiro[4.5]decan-1-one Chemical compound COC1=CC=C(C=C1)N1CCN(CC1)CC[C@@H]1OC(C2(C1)CCN(CC2)S(=O)(=O)C)=O VFLQCKVZBDPECH-FQEVSTJZSA-N 0.000 claims description 12
- VFLQCKVZBDPECH-HXUWFJFHSA-N (3S)-3-[2-[4-(4-methoxyphenyl)piperazin-1-yl]ethyl]-8-methylsulfonyl-2-oxa-8-azaspiro[4.5]decan-1-one Chemical compound COC1=CC=C(C=C1)N1CCN(CC1)CC[C@H]1OC(C2(C1)CCN(CC2)S(=O)(=O)C)=O VFLQCKVZBDPECH-HXUWFJFHSA-N 0.000 claims description 12
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 10
- 208000002193 Pain Diseases 0.000 claims description 8
- 208000035475 disorder Diseases 0.000 claims description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 7
- JATPKJKMOVOWTJ-KRWDZBQOSA-N (3R)-3-[2-(3,4-dihydro-1H-isoquinolin-2-yl)ethyl]-2-oxa-8-azaspiro[4.5]decan-1-one Chemical compound C1N(CCC2=CC=CC=C12)CC[C@@H]1OC(C2(C1)CCNCC2)=O JATPKJKMOVOWTJ-KRWDZBQOSA-N 0.000 claims description 6
- MSGHYIDKBULJMQ-SFHVURJKSA-N (3R)-3-[2-(3,4-dihydro-1H-isoquinolin-2-yl)ethyl]-8-methylsulfonyl-2-oxa-8-azaspiro[4.5]decan-1-one Chemical compound C1N(CCC2=CC=CC=C12)CC[C@@H]1OC(C2(C1)CCN(CC2)S(=O)(=O)C)=O MSGHYIDKBULJMQ-SFHVURJKSA-N 0.000 claims description 6
- LVEFDAMYUHHQHJ-SFHVURJKSA-N (3R)-3-[2-(4-phenylpiperazin-1-yl)ethyl]-2,8-dioxaspiro[4.5]decan-1-one Chemical compound C1(=CC=CC=C1)N1CCN(CC1)CC[C@@H]1OC(C2(C1)CCOCC2)=O LVEFDAMYUHHQHJ-SFHVURJKSA-N 0.000 claims description 6
- DWSVKSNIDKVXAT-SFHVURJKSA-N (3R)-3-[2-[4-(2-methyl-1H-benzimidazol-4-yl)piperazin-1-yl]ethyl]-8-methylsulfonyl-2-oxa-8-azaspiro[4.5]decan-1-one Chemical compound CC1=NC2=C(N1)C(=CC=C2)N1CCN(CC1)CC[C@@H]1OC(C2(C1)CCN(CC2)S(=O)(=O)C)=O DWSVKSNIDKVXAT-SFHVURJKSA-N 0.000 claims description 6
- DYLOBGVCXUVCDQ-IBGZPJMESA-N (3R)-3-[2-[4-(2-propan-2-ylphenyl)piperazin-1-yl]ethyl]-2-oxa-8-azaspiro[4.5]decan-1-one Chemical compound C(C)(C)C1=C(C=CC=C1)N1CCN(CC1)CC[C@@H]1OC(C2(C1)CCNCC2)=O DYLOBGVCXUVCDQ-IBGZPJMESA-N 0.000 claims description 6
- NLRPHTYPVQBVTM-IBGZPJMESA-N (3R)-3-[2-[4-(4-chlorophenyl)piperazin-1-yl]ethyl]-8-methylsulfonyl-2-oxa-8-azaspiro[4.5]decan-1-one Chemical compound ClC1=CC=C(C=C1)N1CCN(CC1)CC[C@@H]1OC(C2(C1)CCN(CC2)S(=O)(=O)C)=O NLRPHTYPVQBVTM-IBGZPJMESA-N 0.000 claims description 6
- XUOWOSJIOQXTHR-IBGZPJMESA-N (3R)-3-[2-[4-(4-fluorophenyl)piperazin-1-yl]ethyl]-8-methylsulfonyl-2-oxa-8-azaspiro[4.5]decan-1-one Chemical compound FC1=CC=C(C=C1)N1CCN(CC1)CC[C@@H]1OC(C2(C1)CCN(CC2)S(=O)(=O)C)=O XUOWOSJIOQXTHR-IBGZPJMESA-N 0.000 claims description 6
- DBNZOMHCFYYUFH-SFHVURJKSA-N (3R)-3-[2-[4-(4-hydroxyphenyl)piperazin-1-yl]ethyl]-2,8-dioxaspiro[4.5]decan-1-one Chemical compound OC1=CC=C(C=C1)N1CCN(CC1)CC[C@@H]1OC(C2(C1)CCOCC2)=O DBNZOMHCFYYUFH-SFHVURJKSA-N 0.000 claims description 6
- GYYVGYZHBSQYSA-IBGZPJMESA-N (3R)-3-[2-[4-(4-iodophenyl)piperazin-1-yl]ethyl]-8-methylsulfonyl-2-oxa-8-azaspiro[4.5]decan-1-one Chemical compound IC1=CC=C(C=C1)N1CCN(CC1)CC[C@@H]1OC(C2(C1)CCN(CC2)S(=O)(=O)C)=O GYYVGYZHBSQYSA-IBGZPJMESA-N 0.000 claims description 6
- GEROZKBIIKZJQD-IBGZPJMESA-N (3R)-3-[2-[4-(4-methylphenyl)piperazin-1-yl]ethyl]-1-oxo-2-oxa-8-azaspiro[4.5]decane-8-carboxylic acid Chemical compound CC1=CC=C(C=C1)N2CCN(CC2)CC[C@H]3CC4(CCN(CC4)C(=O)O)C(=O)O3 GEROZKBIIKZJQD-IBGZPJMESA-N 0.000 claims description 6
- AOQMTPLAFACCAA-IBGZPJMESA-N (3R)-3-[2-[4-(4-methylphenyl)piperazin-1-yl]ethyl]-2-oxa-8-azaspiro[4.5]decan-1-one Chemical compound C1(=CC=C(C=C1)N1CCN(CC1)CC[C@@H]1OC(C2(C1)CCNCC2)=O)C AOQMTPLAFACCAA-IBGZPJMESA-N 0.000 claims description 6
- VJBPXHGLMVAHSC-QFIPXVFZSA-N (3R)-3-[2-[4-(4-methylphenyl)piperazin-1-yl]ethyl]-8-(1-methylpyrazol-4-yl)sulfonyl-2-oxa-8-azaspiro[4.5]decan-1-one Chemical compound CN1N=CC(=C1)S(=O)(=O)N1CCC2(C[C@@H](OC2=O)CCN2CCN(CC2)C2=CC=C(C=C2)C)CC1 VJBPXHGLMVAHSC-QFIPXVFZSA-N 0.000 claims description 6
- RFVGDDCWNZROBF-QHCPKHFHSA-N (3R)-3-[2-[4-(4-methylphenyl)piperazin-1-yl]ethyl]-8-(2-methylpropylsulfonyl)-2-oxa-8-azaspiro[4.5]decan-1-one Chemical compound C(C(C)C)S(=O)(=O)N1CCC2(C[C@@H](OC2=O)CCN2CCN(CC2)C2=CC=C(C=C2)C)CC1 RFVGDDCWNZROBF-QHCPKHFHSA-N 0.000 claims description 6
- PPYWCSCCCMLOJK-NRFANRHFSA-N (3R)-3-[2-[4-(4-methylphenyl)piperazin-1-yl]ethyl]-8-(3,3,3-trifluoropropylsulfonyl)-2-oxa-8-azaspiro[4.5]decan-1-one Chemical compound C1(=CC=C(C=C1)N1CCN(CC1)CC[C@@H]1OC(C2(C1)CCN(CC2)S(=O)(=O)CCC(F)(F)F)=O)C PPYWCSCCCMLOJK-NRFANRHFSA-N 0.000 claims description 6
- IBCZAESGPAEFDR-NRFANRHFSA-N (3R)-3-[2-[4-(4-methylphenyl)piperazin-1-yl]ethyl]-8-(methylsulfonylmethylsulfonyl)-2-oxa-8-azaspiro[4.5]decan-1-one Chemical compound CS(=O)(=O)CS(=O)(=O)N1CCC2(C[C@@H](OC2=O)CCN2CCN(CC2)C2=CC=C(C=C2)C)CC1 IBCZAESGPAEFDR-NRFANRHFSA-N 0.000 claims description 6
- HAABJSKHNYVPIS-FQEVSTJZSA-N (3R)-3-[2-[4-(4-methylphenyl)piperazin-1-yl]ethyl]-8-methylsulfonyl-2-oxa-8-azaspiro[4.5]decan-1-one Chemical compound CS(=O)(=O)N1CCC2(C[C@@H](OC2=O)CCN2CCN(CC2)C2=CC=C(C=C2)C)CC1 HAABJSKHNYVPIS-FQEVSTJZSA-N 0.000 claims description 6
- XRAXHGOJXJICHV-QFIPXVFZSA-N (3R)-3-[2-[4-(4-methylphenyl)piperazin-1-yl]ethyl]-8-propan-2-ylsulfonyl-2-oxa-8-azaspiro[4.5]decan-1-one Chemical compound C(C)(C)S(=O)(=O)N1CCC2(C[C@@H](OC2=O)CCN2CCN(CC2)C2=CC=C(C=C2)C)CC1 XRAXHGOJXJICHV-QFIPXVFZSA-N 0.000 claims description 6
- FQKXMSNIIBZBSZ-NRFANRHFSA-N (3R)-8-(1H-imidazol-5-ylsulfonyl)-3-[2-[4-(4-methylphenyl)piperazin-1-yl]ethyl]-2-oxa-8-azaspiro[4.5]decan-1-one Chemical compound N1C=NC(=C1)S(=O)(=O)N1CCC2(C[C@@H](OC2=O)CCN2CCN(CC2)C2=CC=C(C=C2)C)CC1 FQKXMSNIIBZBSZ-NRFANRHFSA-N 0.000 claims description 6
- SVLHYKSKWDHJTK-DEOSSOPVSA-N (3R)-8-(benzenesulfonyl)-3-[2-[4-(4-methylphenyl)piperazin-1-yl]ethyl]-2-oxa-8-azaspiro[4.5]decan-1-one Chemical compound C1(=CC=CC=C1)S(=O)(=O)N1CCC2(C[C@@H](OC2=O)CCN2CCN(CC2)C2=CC=C(C=C2)C)CC1 SVLHYKSKWDHJTK-DEOSSOPVSA-N 0.000 claims description 6
- HCALZOPJVCEXCO-NRFANRHFSA-N (3R)-8-acetyl-3-[2-[4-(4-methylphenyl)piperazin-1-yl]ethyl]-2-oxa-8-azaspiro[4.5]decan-1-one Chemical compound C(C)(=O)N1CCC2(C[C@@H](OC2=O)CCN2CCN(CC2)C2=CC=C(C=C2)C)CC1 HCALZOPJVCEXCO-NRFANRHFSA-N 0.000 claims description 6
- QWTRNVUDPLLEAB-SANMLTNESA-N (3R)-8-benzyl-3-[2-[4-(4-methylphenyl)piperazin-1-yl]ethyl]-2-oxa-8-azaspiro[4.5]decan-1-one Chemical compound C(C1=CC=CC=C1)N1CCC2(C[C@@H](OC2=O)CCN2CCN(CC2)C2=CC=C(C=C2)C)CC1 QWTRNVUDPLLEAB-SANMLTNESA-N 0.000 claims description 6
- KDOXPDDODOMYHZ-DEOSSOPVSA-N (3R)-8-cyclohexylsulfonyl-3-[2-[4-(4-methylphenyl)piperazin-1-yl]ethyl]-2-oxa-8-azaspiro[4.5]decan-1-one Chemical compound C1(CCCCC1)S(=O)(=O)N1CCC2(C[C@@H](OC2=O)CCN2CCN(CC2)C2=CC=C(C=C2)C)CC1 KDOXPDDODOMYHZ-DEOSSOPVSA-N 0.000 claims description 6
- FEBDLPMJOFFKLE-QHCPKHFHSA-N (3R)-8-cyclopentylsulfonyl-3-[2-[4-(4-methylphenyl)piperazin-1-yl]ethyl]-2-oxa-8-azaspiro[4.5]decan-1-one Chemical compound C1(CCCC1)S(=O)(=O)N1CCC2(C[C@@H](OC2=O)CCN2CCN(CC2)C2=CC=C(C=C2)C)CC1 FEBDLPMJOFFKLE-QHCPKHFHSA-N 0.000 claims description 6
- JJEZISOSFDGULR-NRFANRHFSA-N (3R)-8-cyclopropylsulfonyl-3-[2-[4-(4-methylphenyl)piperazin-1-yl]ethyl]-2-oxa-8-azaspiro[4.5]decan-1-one Chemical compound C1(CC1)S(=O)(=O)N1CCC2(C[C@@H](OC2=O)CCN2CCN(CC2)C2=CC=C(C=C2)C)CC1 JJEZISOSFDGULR-NRFANRHFSA-N 0.000 claims description 6
- LTLWVHRDJYSFHE-NRFANRHFSA-N (3R)-8-ethylsulfonyl-3-[2-[4-(4-methylphenyl)piperazin-1-yl]ethyl]-2-oxa-8-azaspiro[4.5]decan-1-one Chemical compound C(C)S(=O)(=O)N1CCC2(C[C@@H](OC2=O)CCN2CCN(CC2)C2=CC=C(C=C2)C)CC1 LTLWVHRDJYSFHE-NRFANRHFSA-N 0.000 claims description 6
- IONUVCVGGHEYJY-IBGZPJMESA-N (3R)-8-methylsulfonyl-3-[2-[4-(4-nitrophenyl)piperazin-1-yl]ethyl]-2-oxa-8-azaspiro[4.5]decan-1-one Chemical compound CS(=O)(=O)N1CCC2(C[C@@H](OC2=O)CCN2CCN(CC2)C2=CC=C(C=C2)[N+](=O)[O-])CC1 IONUVCVGGHEYJY-IBGZPJMESA-N 0.000 claims description 6
- JATPKJKMOVOWTJ-QGZVFWFLSA-N (3S)-3-[2-(3,4-dihydro-1H-isoquinolin-2-yl)ethyl]-2-oxa-8-azaspiro[4.5]decan-1-one Chemical compound C1N(CCC2=CC=CC=C12)CC[C@H]1OC(C2(C1)CCNCC2)=O JATPKJKMOVOWTJ-QGZVFWFLSA-N 0.000 claims description 6
- MSGHYIDKBULJMQ-GOSISDBHSA-N (3S)-3-[2-(3,4-dihydro-1H-isoquinolin-2-yl)ethyl]-8-methylsulfonyl-2-oxa-8-azaspiro[4.5]decan-1-one Chemical compound C1N(CCC2=CC=CC=C12)CC[C@H]1OC(C2(C1)CCN(CC2)S(=O)(=O)C)=O MSGHYIDKBULJMQ-GOSISDBHSA-N 0.000 claims description 6
- LVEFDAMYUHHQHJ-GOSISDBHSA-N (3S)-3-[2-(4-phenylpiperazin-1-yl)ethyl]-2,8-dioxaspiro[4.5]decan-1-one Chemical compound C1(=CC=CC=C1)N1CCN(CC1)CC[C@H]1OC(C2(C1)CCOCC2)=O LVEFDAMYUHHQHJ-GOSISDBHSA-N 0.000 claims description 6
- DWSVKSNIDKVXAT-GOSISDBHSA-N (3S)-3-[2-[4-(2-methyl-1H-benzimidazol-4-yl)piperazin-1-yl]ethyl]-8-methylsulfonyl-2-oxa-8-azaspiro[4.5]decan-1-one Chemical compound CC1=NC2=C(N1)C(=CC=C2)N1CCN(CC1)CC[C@H]1OC(C2(C1)CCN(CC2)S(=O)(=O)C)=O DWSVKSNIDKVXAT-GOSISDBHSA-N 0.000 claims description 6
- DYLOBGVCXUVCDQ-LJQANCHMSA-N (3S)-3-[2-[4-(2-propan-2-ylphenyl)piperazin-1-yl]ethyl]-2-oxa-8-azaspiro[4.5]decan-1-one Chemical compound C(C)(C)C1=C(C=CC=C1)N1CCN(CC1)CC[C@H]1OC(C2(C1)CCNCC2)=O DYLOBGVCXUVCDQ-LJQANCHMSA-N 0.000 claims description 6
- NLRPHTYPVQBVTM-LJQANCHMSA-N (3S)-3-[2-[4-(4-chlorophenyl)piperazin-1-yl]ethyl]-8-methylsulfonyl-2-oxa-8-azaspiro[4.5]decan-1-one Chemical compound ClC1=CC=C(C=C1)N1CCN(CC1)CC[C@H]1OC(C2(C1)CCN(CC2)S(=O)(=O)C)=O NLRPHTYPVQBVTM-LJQANCHMSA-N 0.000 claims description 6
- XUOWOSJIOQXTHR-LJQANCHMSA-N (3S)-3-[2-[4-(4-fluorophenyl)piperazin-1-yl]ethyl]-8-methylsulfonyl-2-oxa-8-azaspiro[4.5]decan-1-one Chemical compound FC1=CC=C(C=C1)N1CCN(CC1)CC[C@H]1OC(C2(C1)CCN(CC2)S(=O)(=O)C)=O XUOWOSJIOQXTHR-LJQANCHMSA-N 0.000 claims description 6
- DBNZOMHCFYYUFH-GOSISDBHSA-N (3S)-3-[2-[4-(4-hydroxyphenyl)piperazin-1-yl]ethyl]-2,8-dioxaspiro[4.5]decan-1-one Chemical compound OC1=CC=C(C=C1)N1CCN(CC1)CC[C@H]1OC(C2(C1)CCOCC2)=O DBNZOMHCFYYUFH-GOSISDBHSA-N 0.000 claims description 6
- GYYVGYZHBSQYSA-LJQANCHMSA-N (3S)-3-[2-[4-(4-iodophenyl)piperazin-1-yl]ethyl]-8-methylsulfonyl-2-oxa-8-azaspiro[4.5]decan-1-one Chemical compound IC1=CC=C(C=C1)N1CCN(CC1)CC[C@H]1OC(C2(C1)CCN(CC2)S(=O)(=O)C)=O GYYVGYZHBSQYSA-LJQANCHMSA-N 0.000 claims description 6
- GEROZKBIIKZJQD-LJQANCHMSA-N (3S)-3-[2-[4-(4-methylphenyl)piperazin-1-yl]ethyl]-1-oxo-2-oxa-8-azaspiro[4.5]decane-8-carboxylic acid Chemical compound CC1=CC=C(C=C1)N2CCN(CC2)CC[C@@H]3CC4(CCN(CC4)C(=O)O)C(=O)O3 GEROZKBIIKZJQD-LJQANCHMSA-N 0.000 claims description 6
- AOQMTPLAFACCAA-LJQANCHMSA-N (3S)-3-[2-[4-(4-methylphenyl)piperazin-1-yl]ethyl]-2-oxa-8-azaspiro[4.5]decan-1-one Chemical compound C1(=CC=C(C=C1)N1CCN(CC1)CC[C@H]1OC(C2(C1)CCNCC2)=O)C AOQMTPLAFACCAA-LJQANCHMSA-N 0.000 claims description 6
- RFVGDDCWNZROBF-HSZRJFAPSA-N (3S)-3-[2-[4-(4-methylphenyl)piperazin-1-yl]ethyl]-8-(2-methylpropylsulfonyl)-2-oxa-8-azaspiro[4.5]decan-1-one Chemical compound CC(C)CS(=O)(=O)N1CCC2(C[C@@H](CCN3CCN(CC3)c3ccc(C)cc3)OC2=O)CC1 RFVGDDCWNZROBF-HSZRJFAPSA-N 0.000 claims description 6
- PPYWCSCCCMLOJK-OAQYLSRUSA-N (3S)-3-[2-[4-(4-methylphenyl)piperazin-1-yl]ethyl]-8-(3,3,3-trifluoropropylsulfonyl)-2-oxa-8-azaspiro[4.5]decan-1-one Chemical compound C1(=CC=C(C=C1)N1CCN(CC1)CC[C@H]1OC(C2(C1)CCN(CC2)S(=O)(=O)CCC(F)(F)F)=O)C PPYWCSCCCMLOJK-OAQYLSRUSA-N 0.000 claims description 6
- IBCZAESGPAEFDR-OAQYLSRUSA-N (3S)-3-[2-[4-(4-methylphenyl)piperazin-1-yl]ethyl]-8-(methylsulfonylmethylsulfonyl)-2-oxa-8-azaspiro[4.5]decan-1-one Chemical compound CS(=O)(=O)CS(=O)(=O)N1CCC2(C[C@H](OC2=O)CCN2CCN(CC2)C2=CC=C(C=C2)C)CC1 IBCZAESGPAEFDR-OAQYLSRUSA-N 0.000 claims description 6
- RJOLIGKCRQYQOL-HSZRJFAPSA-N (3S)-3-[2-[4-(4-methylphenyl)piperazin-1-yl]ethyl]-8-(oxan-4-ylsulfonyl)-2-oxa-8-azaspiro[4.5]decan-1-one Chemical compound O1CCC(CC1)S(=O)(=O)N1CCC2(C[C@H](OC2=O)CCN2CCN(CC2)C2=CC=C(C=C2)C)CC1 RJOLIGKCRQYQOL-HSZRJFAPSA-N 0.000 claims description 6
- COMNXBZKDGZNBB-LJQANCHMSA-N (3S)-3-[2-[4-(4-methylphenyl)piperazin-1-yl]ethyl]-8-(trifluoromethylsulfonyl)-2-oxa-8-azaspiro[4.5]decan-1-one Chemical compound Cc1ccc(cc1)N1CCN(CC[C@@H]2CC3(CCN(CC3)S(=O)(=O)C(F)(F)F)C(=O)O2)CC1 COMNXBZKDGZNBB-LJQANCHMSA-N 0.000 claims description 6
- HAABJSKHNYVPIS-HXUWFJFHSA-N (3S)-3-[2-[4-(4-methylphenyl)piperazin-1-yl]ethyl]-8-methylsulfonyl-2-oxa-8-azaspiro[4.5]decan-1-one Chemical compound CS(=O)(=O)N1CCC2(C[C@H](OC2=O)CCN2CCN(CC2)C2=CC=C(C=C2)C)CC1 HAABJSKHNYVPIS-HXUWFJFHSA-N 0.000 claims description 6
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| EP2341912B1 (en) | 2008-09-05 | 2014-01-22 | Supernus Pharmaceuticals, Inc. | Method of treatment of attention deficit/hyperactivity disorder (adhd) |
| WO2010069390A1 (en) | 2008-12-19 | 2010-06-24 | Nokia Siemens Networks Oy | Method and device for data processing in an udwdm network and communication system comprising such device |
| US8637263B1 (en) * | 2010-10-14 | 2014-01-28 | Epiomed Therapeutics, Inc. | Assay for determination of compounds having anti-emetic activity |
| CA2816551A1 (en) | 2010-11-03 | 2012-05-10 | Mcmaster University | Method of treating mucosal inflammation |
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| US9464062B2 (en) * | 2012-11-28 | 2016-10-11 | Temple University—Of the Commonwealth System of Higher Education | Disubstituted oxazolidin-2-ones 5-hydroxytryptamine receptor 2B activity modulators |
| WO2014164756A1 (en) * | 2013-03-11 | 2014-10-09 | Temple University Of The Commonwealth System Of Higher Education | Novel 5-hydroxytryptamine receptor 7 activity modulators and their method of use |
| EP3200589B1 (en) | 2014-09-10 | 2026-03-11 | Temple University Of The Commonwealth System Of Higher Education | Novel 5-hydroxytryptamine receptor 7 activity modulators and their method of use |
| US20180221365A1 (en) | 2015-05-12 | 2018-08-09 | Temple University-Of The Commonwealth System Of Higher Education | Novel sigma-2 receptor binders and their method of use |
| EP3541790B1 (en) | 2016-11-15 | 2025-09-03 | Temple University - Of The Commonwealth System of Higher Education | 3-(2-(4-phenylpiperazin-1-yl)ethyl)-2-oxa-8-azaspiro[4.5]decan-1-one derivatives and related compounds as 5-hydroxytryptamine receptor 7 (5-ht7) modulators for treating e.g. inflammatory bowel disease, circadian rhythm disorder or depression |
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| JP7365238B2 (ja) | 2017-03-21 | 2023-10-19 | テンプル・ユニバーシティ－オブ・ザ・コモンウェルス・システム・オブ・ハイアー・エデュケイション | ５－ヒドロキシトリプタミン受容体７調節物質および治療剤としてのその使用 |
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