JP2007535548A5 - - Google Patents
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- Publication number
- JP2007535548A5 JP2007535548A5 JP2007510941A JP2007510941A JP2007535548A5 JP 2007535548 A5 JP2007535548 A5 JP 2007535548A5 JP 2007510941 A JP2007510941 A JP 2007510941A JP 2007510941 A JP2007510941 A JP 2007510941A JP 2007535548 A5 JP2007535548 A5 JP 2007535548A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- isochroman
- piperidin
- aminomethyl
- hydroxy
- 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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- OYNWTHUVMYDYGL-OALUTQOASA-N n-[[(1r,3s)-6-methyl-3-piperidin-4-yl-5-propan-2-yloxy-3,4-dihydro-1h-isochromen-1-yl]methyl]formamide Chemical compound C1([C@H]2O[C@@H](CNC=O)C=3C=CC(C)=C(C=3C2)OC(C)C)CCNCC1 OYNWTHUVMYDYGL-OALUTQOASA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 57
- -1 phenylcarbamoyl Chemical group 0.000 claims 29
- 229910052739 hydrogen Inorganic materials 0.000 claims 20
- 239000001257 hydrogen Substances 0.000 claims 20
- 150000001875 compounds Chemical class 0.000 claims 14
- 150000002431 hydrogen Chemical class 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 235000010290 biphenyl Nutrition 0.000 claims 6
- 239000004305 biphenyl Substances 0.000 claims 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 4
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000001318 4-trifluoromethylbenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(F)(F)F 0.000 claims 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 2
- 125000006267 biphenyl group Chemical group 0.000 claims 2
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims 2
- 125000005117 dialkylcarbamoyl group Chemical group 0.000 claims 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical group C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 claims 2
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- OLAHHVRNGLPLAS-PPLCUNABSA-N (1R)-1-[[4-[(1R,3S)-1-(aminomethyl)-5-hydroxy-6-methyl-3,4-dihydro-1H-isochromen-3-yl]piperidin-1-yl]sulfonylmethyl]-7,7-dimethylbicyclo[2.2.1]heptan-2-one Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1S(=O)(=O)C[C@]1(C2(C)C)C(=O)CC2CC1 OLAHHVRNGLPLAS-PPLCUNABSA-N 0.000 claims 1
- BZWGHAQNOBMVFM-JUQRWGLSSA-N (1R,3S)-6-methyl-1-(methylaminomethyl)-3-[1-(1-phenylethyl)piperidin-4-yl]-3,4-dihydro-1H-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@H](C3=CC=C(C)C(O)=C3C2)CNC)CCN1C(C)C1=CC=CC=C1 BZWGHAQNOBMVFM-JUQRWGLSSA-N 0.000 claims 1
- JCMGZTZNYJBGOG-VXKWHMMOSA-N (1r,3s)-1-(aminomethyl)-3-(1-benzylpiperidin-4-yl)-6-methyl-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1CC1=CC=CC=C1 JCMGZTZNYJBGOG-VXKWHMMOSA-N 0.000 claims 1
- RUXMQAQPHCLAHN-VXKWHMMOSA-N (1r,3s)-1-(aminomethyl)-3-(1-benzylsulfonylpiperidin-4-yl)-6-methyl-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1S(=O)(=O)CC1=CC=CC=C1 RUXMQAQPHCLAHN-VXKWHMMOSA-N 0.000 claims 1
- LAONOWKNQSTAKL-CQBHRIGDSA-N (1r,3s)-1-(aminomethyl)-3-(1-butylpiperidin-4-yl)-6-methyl-3,4-dihydro-1h-isochromen-5-ol;(1r,3s)-1-(aminomethyl)-3-[1-(2,3-dihydro-1h-inden-2-yl)piperidin-4-yl]-6-methyl-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CN(CCCC)CCC1[C@H]1O[C@@H](CN)C2=CC=C(C)C(O)=C2C1.C1C2=CC=CC=C2CC1N(CC1)CCC1[C@H]1O[C@@H](CN)C2=CC=C(C)C(O)=C2C1 LAONOWKNQSTAKL-CQBHRIGDSA-N 0.000 claims 1
- QZOJKYSWGFYCIY-OALUTQOASA-N (1r,3s)-1-(aminomethyl)-3-(1-butylsulfonylpiperidin-4-yl)-6-methyl-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CN(S(=O)(=O)CCCC)CCC1[C@H]1O[C@@H](CN)C2=CC=C(C)C(O)=C2C1 QZOJKYSWGFYCIY-OALUTQOASA-N 0.000 claims 1
- IVTPNYYUYXTGHX-IRXDYDNUSA-N (1r,3s)-1-(aminomethyl)-3-(1-ethylsulfonylpiperidin-4-yl)-6-methyl-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CN(S(=O)(=O)CC)CCC1[C@H]1O[C@@H](CN)C2=CC=C(C)C(O)=C2C1 IVTPNYYUYXTGHX-IRXDYDNUSA-N 0.000 claims 1
- YZRRWCPYASKLRL-ZEQRLZLVSA-N (1r,3s)-1-(aminomethyl)-3-[1-(1-benzofuran-2-ylmethyl)piperidin-4-yl]-6-methyl-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1=CC=C2OC(CN3CCC(CC3)[C@H]3O[C@@H](CN)C4=CC=C(C(=C4C3)O)C)=CC2=C1 YZRRWCPYASKLRL-ZEQRLZLVSA-N 0.000 claims 1
- CEJVKVYLAVYIIS-GOTSBHOMSA-N (1r,3s)-1-(aminomethyl)-3-[1-(1-benzothiophen-3-ylmethyl)piperidin-4-yl]-6-methyl-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1=CC=C2C(CN3CCC(CC3)[C@H]3O[C@@H](CN)C4=CC=C(C(=C4C3)O)C)=CSC2=C1 CEJVKVYLAVYIIS-GOTSBHOMSA-N 0.000 claims 1
- WZOIZYRTPCTDBG-ZEQRLZLVSA-N (1r,3s)-1-(aminomethyl)-3-[1-(1h-indol-3-ylmethyl)piperidin-4-yl]-6-methyl-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1=CC=C2C(CN3CCC(CC3)[C@H]3O[C@@H](CN)C4=CC=C(C(=C4C3)O)C)=CNC2=C1 WZOIZYRTPCTDBG-ZEQRLZLVSA-N 0.000 claims 1
- CIILVARJBBOHLY-OALUTQOASA-N (1r,3s)-1-(aminomethyl)-3-[1-(2,2-dimethylpropyl)piperidin-4-yl]-6-methyl-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN(CC(C)(C)C)CC1 CIILVARJBBOHLY-OALUTQOASA-N 0.000 claims 1
- ISPLQTPMNBBWRZ-VMPREFPWSA-N (1r,3s)-1-(aminomethyl)-3-[1-(2,2-diphenylethyl)piperidin-4-yl]-6-methyl-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 ISPLQTPMNBBWRZ-VMPREFPWSA-N 0.000 claims 1
- GUBHHPKJGREISE-VMPREFPWSA-N (1r,3s)-1-(aminomethyl)-3-[1-(2,2-diphenylethylsulfonyl)piperidin-4-yl]-6-methyl-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1S(=O)(=O)CC(C=1C=CC=CC=1)C1=CC=CC=C1 GUBHHPKJGREISE-VMPREFPWSA-N 0.000 claims 1
- VNCSCEMQMVQUAE-PMACEKPBSA-N (1r,3s)-1-(aminomethyl)-3-[1-(2,4-dichlorophenyl)sulfonylpiperidin-4-yl]-6-methyl-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1S(=O)(=O)C1=CC=C(Cl)C=C1Cl VNCSCEMQMVQUAE-PMACEKPBSA-N 0.000 claims 1
- DGDZQJQCRDBSDN-PMACEKPBSA-N (1r,3s)-1-(aminomethyl)-3-[1-(2,5-dichlorophenyl)sulfonylpiperidin-4-yl]-6-methyl-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1S(=O)(=O)C1=CC(Cl)=CC=C1Cl DGDZQJQCRDBSDN-PMACEKPBSA-N 0.000 claims 1
- SVLJTNQPHKXTSI-IRXDYDNUSA-N (1r,3s)-1-(aminomethyl)-3-[1-(2-hydroxyethyl)piperidin-4-yl]-6-methyl-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN(CCO)CC1 SVLJTNQPHKXTSI-IRXDYDNUSA-N 0.000 claims 1
- YHODLJWMKZWBRO-SFTDATJTSA-N (1r,3s)-1-(aminomethyl)-3-[1-(3,4-dichlorophenyl)sulfonylpiperidin-4-yl]-6-methyl-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1S(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 YHODLJWMKZWBRO-SFTDATJTSA-N 0.000 claims 1
- YOQOMPMDCZYGQX-ZEQRLZLVSA-N (1r,3s)-1-(aminomethyl)-3-[1-(3,4-dihydro-1h-isoquinolin-2-ylsulfonyl)piperidin-4-yl]-6-methyl-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC2=CC=CC=C2CN1S(=O)(=O)N(CC1)CCC1[C@H]1O[C@@H](CN)C2=CC=C(C)C(O)=C2C1 YOQOMPMDCZYGQX-ZEQRLZLVSA-N 0.000 claims 1
- FOLRFDBEPLCPAT-GMAHTHKFSA-N (1r,3s)-1-(aminomethyl)-3-[1-(3,4-dimethoxyphenyl)sulfonylpiperidin-4-yl]-6-methyl-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1=C(OC)C(OC)=CC=C1S(=O)(=O)N1CCC([C@H]2O[C@@H](CN)C3=CC=C(C)C(O)=C3C2)CC1 FOLRFDBEPLCPAT-GMAHTHKFSA-N 0.000 claims 1
- AELGNNXBPYKOQB-SVBPBHIXSA-N (1r,3s)-1-(aminomethyl)-3-[1-(4-benzylpiperidin-1-yl)sulfonylpiperidin-4-yl]-6-methyl-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1S(=O)(=O)N(CC1)CCC1CC1=CC=CC=C1 AELGNNXBPYKOQB-SVBPBHIXSA-N 0.000 claims 1
- YNTBUMALJNLLQH-SFTDATJTSA-N (1r,3s)-1-(aminomethyl)-3-[1-(4-chlorophenyl)sulfonylpiperidin-4-yl]-6-methyl-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1S(=O)(=O)C1=CC=C(Cl)C=C1 YNTBUMALJNLLQH-SFTDATJTSA-N 0.000 claims 1
- APSHRLPOALCGDX-ZEQRLZLVSA-N (1r,3s)-1-(aminomethyl)-3-[1-(4-tert-butylphenyl)sulfonylpiperidin-4-yl]-6-methyl-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1S(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 APSHRLPOALCGDX-ZEQRLZLVSA-N 0.000 claims 1
- ISZDRKXEFUPQGJ-SFTDATJTSA-N (1r,3s)-1-(aminomethyl)-3-[1-(benzenesulfonyl)piperidin-4-yl]-6-methyl-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1S(=O)(=O)C1=CC=CC=C1 ISZDRKXEFUPQGJ-SFTDATJTSA-N 0.000 claims 1
- LNLHKRLPAWEOJX-VXKWHMMOSA-N (1r,3s)-1-(aminomethyl)-3-[1-(cyclohexylmethyl)piperidin-4-yl]-6-methyl-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1CC1CCCCC1 LNLHKRLPAWEOJX-VXKWHMMOSA-N 0.000 claims 1
- KZCKECFGRRBOFO-OALUTQOASA-N (1r,3s)-1-(aminomethyl)-3-[1-(cyclopropylmethyl)piperidin-4-yl]-6-methyl-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1CC1CC1 KZCKECFGRRBOFO-OALUTQOASA-N 0.000 claims 1
- XJLVLCNUXNFUNK-PMACEKPBSA-N (1r,3s)-1-(aminomethyl)-3-[1-(furan-3-ylmethyl)piperidin-4-yl]-6-methyl-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1CC=1C=COC=1 XJLVLCNUXNFUNK-PMACEKPBSA-N 0.000 claims 1
- BKUKIADILJRFEL-CONSDPRKSA-N (1r,3s)-1-(aminomethyl)-3-[1-[(1-benzylindol-3-yl)methyl]piperidin-4-yl]-6-methyl-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1CC(C1=CC=CC=C11)=CN1CC1=CC=CC=C1 BKUKIADILJRFEL-CONSDPRKSA-N 0.000 claims 1
- DSZANASAFNZUBB-VXKWHMMOSA-N (1r,3s)-1-(aminomethyl)-3-[1-[(2,4-difluorophenyl)methyl]piperidin-4-yl]-6-methyl-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1CC1=CC=C(F)C=C1F DSZANASAFNZUBB-VXKWHMMOSA-N 0.000 claims 1
- WFMVDHNJDJZDSV-VXKWHMMOSA-N (1r,3s)-1-(aminomethyl)-3-[1-[(2-chlorophenyl)methyl]piperidin-4-yl]-6-methyl-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1CC1=CC=CC=C1Cl WFMVDHNJDJZDSV-VXKWHMMOSA-N 0.000 claims 1
- ICWRGXVYGWHJMF-VXKWHMMOSA-N (1r,3s)-1-(aminomethyl)-3-[1-[(2-fluorophenyl)methyl]piperidin-4-yl]-6-methyl-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1CC1=CC=CC=C1F ICWRGXVYGWHJMF-VXKWHMMOSA-N 0.000 claims 1
- HASIZRCMXSGWPU-GOTSBHOMSA-N (1r,3s)-1-(aminomethyl)-3-[1-[(2-methoxyphenyl)methyl]piperidin-4-yl]-6-methyl-3,4-dihydro-1h-isochromen-5-ol Chemical compound COC1=CC=CC=C1CN1CCC([C@H]2O[C@@H](CN)C3=CC=C(C)C(O)=C3C2)CC1 HASIZRCMXSGWPU-GOTSBHOMSA-N 0.000 claims 1
- OKJKOFVMFSMYQK-VXKWHMMOSA-N (1r,3s)-1-(aminomethyl)-3-[1-[(3,4-dichlorophenyl)methyl]piperidin-4-yl]-6-methyl-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1CC1=CC=C(Cl)C(Cl)=C1 OKJKOFVMFSMYQK-VXKWHMMOSA-N 0.000 claims 1
- CVKAWMSGTCXRDK-VXKWHMMOSA-N (1r,3s)-1-(aminomethyl)-3-[1-[(3,4-dichlorophenyl)methylsulfonyl]piperidin-4-yl]-6-methyl-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1S(=O)(=O)CC1=CC=C(Cl)C(Cl)=C1 CVKAWMSGTCXRDK-VXKWHMMOSA-N 0.000 claims 1
- WACIWQMIFIPFBM-VXKWHMMOSA-N (1r,3s)-1-(aminomethyl)-3-[1-[(3,4-difluorophenyl)methyl]piperidin-4-yl]-6-methyl-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1CC1=CC=C(F)C(F)=C1 WACIWQMIFIPFBM-VXKWHMMOSA-N 0.000 claims 1
- DPEVOCZNTQEATI-VXKWHMMOSA-N (1r,3s)-1-(aminomethyl)-3-[1-[(3-chlorophenyl)methyl]piperidin-4-yl]-6-methyl-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1CC1=CC=CC(Cl)=C1 DPEVOCZNTQEATI-VXKWHMMOSA-N 0.000 claims 1
- WQYNJHHSJLOYSJ-VXKWHMMOSA-N (1r,3s)-1-(aminomethyl)-3-[1-[(3-fluorophenyl)methyl]piperidin-4-yl]-6-methyl-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1CC1=CC=CC(F)=C1 WQYNJHHSJLOYSJ-VXKWHMMOSA-N 0.000 claims 1
- BAHPHSJGRDWLDW-GOTSBHOMSA-N (1r,3s)-1-(aminomethyl)-3-[1-[(3-methoxyphenyl)methyl]piperidin-4-yl]-6-methyl-3,4-dihydro-1h-isochromen-5-ol Chemical compound COC1=CC=CC(CN2CCC(CC2)[C@H]2O[C@@H](CN)C3=CC=C(C)C(O)=C3C2)=C1 BAHPHSJGRDWLDW-GOTSBHOMSA-N 0.000 claims 1
- HVJFNWREPXKNTP-VXKWHMMOSA-N (1r,3s)-1-(aminomethyl)-3-[1-[(4-chlorophenyl)methyl]piperidin-4-yl]-6-methyl-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1CC1=CC=C(Cl)C=C1 HVJFNWREPXKNTP-VXKWHMMOSA-N 0.000 claims 1
- RGNDYJCYQSQOJH-VXKWHMMOSA-N (1r,3s)-1-(aminomethyl)-3-[1-[(4-fluorophenyl)methyl]piperidin-4-yl]-6-methyl-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1CC1=CC=C(F)C=C1 RGNDYJCYQSQOJH-VXKWHMMOSA-N 0.000 claims 1
- OZVOFCNULPJLIC-VXKWHMMOSA-N (1r,3s)-1-(aminomethyl)-3-[1-[(4-hydroxyphenyl)methyl]piperidin-4-yl]-6-methyl-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1CC1=CC=C(O)C=C1 OZVOFCNULPJLIC-VXKWHMMOSA-N 0.000 claims 1
- DZXZXIDJMYENCB-GOTSBHOMSA-N (1r,3s)-1-(aminomethyl)-3-[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]-6-methyl-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1=CC(OC)=CC=C1CN1CCC([C@H]2O[C@@H](CN)C3=CC=C(C)C(O)=C3C2)CC1 DZXZXIDJMYENCB-GOTSBHOMSA-N 0.000 claims 1
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- CLLNIZRGMNIZEW-NSOVKSMOSA-N (1r,3s)-1-(aminomethyl)-6-methyl-3-[1-[(4-phenoxyphenyl)methyl]piperidin-4-yl]-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1CC(C=C1)=CC=C1OC1=CC=CC=C1 CLLNIZRGMNIZEW-NSOVKSMOSA-N 0.000 claims 1
- HUHHWGPOQMXEBM-NSOVKSMOSA-N (1r,3s)-1-(aminomethyl)-6-methyl-3-[1-[(4-phenylphenyl)methyl]piperidin-4-yl]-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1CC(C=C1)=CC=C1C1=CC=CC=C1 HUHHWGPOQMXEBM-NSOVKSMOSA-N 0.000 claims 1
- ZMYGQIOWLKIFBO-DQEYMECFSA-N (1r,3s)-1-(aminomethyl)-6-methyl-3-[1-[(4-propan-2-ylphenyl)methyl]piperidin-4-yl]-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1=CC(C(C)C)=CC=C1CN1CCC([C@H]2O[C@@H](CN)C3=CC=C(C)C(O)=C3C2)CC1 ZMYGQIOWLKIFBO-DQEYMECFSA-N 0.000 claims 1
- JTXBKECSTHRGKL-PMACEKPBSA-N (1r,3s)-1-(aminomethyl)-6-methyl-3-[1-[2-(trifluoromethyl)phenyl]sulfonylpiperidin-4-yl]-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1S(=O)(=O)C1=CC=CC=C1C(F)(F)F JTXBKECSTHRGKL-PMACEKPBSA-N 0.000 claims 1
- AQBFDRGNZFPVLW-VXKWHMMOSA-N (1r,3s)-1-(aminomethyl)-6-methyl-3-[1-[[2-(trifluoromethyl)phenyl]methyl]piperidin-4-yl]-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1CC1=CC=CC=C1C(F)(F)F AQBFDRGNZFPVLW-VXKWHMMOSA-N 0.000 claims 1
- BVIGEHJQWMSXJX-VXKWHMMOSA-N (1r,3s)-1-(aminomethyl)-6-methyl-3-[1-[[3-(trifluoromethyl)phenyl]methyl]piperidin-4-yl]-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1CC1=CC=CC(C(F)(F)F)=C1 BVIGEHJQWMSXJX-VXKWHMMOSA-N 0.000 claims 1
- DSHIBJZTINSGRG-VXKWHMMOSA-N (1r,3s)-1-(aminomethyl)-6-methyl-3-[1-[[4-(trifluoromethyl)phenyl]methyl]piperidin-4-yl]-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1CC1=CC=C(C(F)(F)F)C=C1 DSHIBJZTINSGRG-VXKWHMMOSA-N 0.000 claims 1
- AEFIJVQTTVJTTJ-ZEQRLZLVSA-N (1r,3s)-1-(ethylaminomethyl)-6-methyl-3-[1-[[4-(trifluoromethyl)phenyl]methyl]piperidin-4-yl]-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@H](C3=CC=C(C)C(O)=C3C2)CNCC)CCN1CC1=CC=C(C(F)(F)F)C=C1 AEFIJVQTTVJTTJ-ZEQRLZLVSA-N 0.000 claims 1
- JDSFRKFCLIOIID-ZEQRLZLVSA-N (1r,3s)-1-[(dimethylamino)methyl]-6-methyl-3-[1-[[4-(trifluoromethyl)phenyl]methyl]piperidin-4-yl]-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@H](C3=CC=C(C)C(O)=C3C2)CN(C)C)CCN1CC1=CC=C(C(F)(F)F)C=C1 JDSFRKFCLIOIID-ZEQRLZLVSA-N 0.000 claims 1
- OJGFVNGKSLRIBZ-UIOOFZCWSA-N (1r,3s)-3-(1-benzylpiperidin-4-yl)-1-(diethylaminomethyl)-6-methyl-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@H](C3=CC=C(C)C(O)=C3C2)CN(CC)CC)CCN1CC1=CC=CC=C1 OJGFVNGKSLRIBZ-UIOOFZCWSA-N 0.000 claims 1
- ZQHIZUHWKITBPZ-ZEQRLZLVSA-N (1r,3s)-3-(1-benzylpiperidin-4-yl)-1-(ethylaminomethyl)-6-methyl-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@H](C3=CC=C(C)C(O)=C3C2)CNCC)CCN1CC1=CC=CC=C1 ZQHIZUHWKITBPZ-ZEQRLZLVSA-N 0.000 claims 1
- ARMBTBRZUSBEGS-UIOOFZCWSA-N (1r,3s)-3-(1-benzylpiperidin-4-yl)-1-[(cyclobutylamino)methyl]-6-methyl-3,4-dihydro-1h-isochromen-5-ol Chemical compound C([C@H]1C2=CC=C(C(=C2C[C@H](O1)C1CCN(CC=2C=CC=CC=2)CC1)O)C)NC1CCC1 ARMBTBRZUSBEGS-UIOOFZCWSA-N 0.000 claims 1
- ROUWUDWWWUOBOZ-ZEQRLZLVSA-N (1r,3s)-3-(1-benzylpiperidin-4-yl)-1-[(dimethylamino)methyl]-6-methyl-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@H](C3=CC=C(C)C(O)=C3C2)CN(C)C)CCN1CC1=CC=CC=C1 ROUWUDWWWUOBOZ-ZEQRLZLVSA-N 0.000 claims 1
- QOQNMLXBGPDAKG-DQEYMECFSA-N (1r,3s)-3-(1-benzylpiperidin-4-yl)-1-[[ethyl(methyl)amino]methyl]-6-methyl-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@H](C3=CC=C(C)C(O)=C3C2)CN(C)CC)CCN1CC1=CC=CC=C1 QOQNMLXBGPDAKG-DQEYMECFSA-N 0.000 claims 1
- NCYZQXDFUDUZJP-GOTSBHOMSA-N (1r,3s)-3-(1-benzylpiperidin-4-yl)-6-methyl-1-(methylaminomethyl)-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@H](C3=CC=C(C)C(O)=C3C2)CNC)CCN1CC1=CC=CC=C1 NCYZQXDFUDUZJP-GOTSBHOMSA-N 0.000 claims 1
- RVGKITHRHMXVPD-DQEYMECFSA-N (1r,3s)-3-(1-benzylpiperidin-4-yl)-6-methyl-1-(propylaminomethyl)-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@H](C3=CC=C(C)C(O)=C3C2)CNCCC)CCN1CC1=CC=CC=C1 RVGKITHRHMXVPD-DQEYMECFSA-N 0.000 claims 1
- RMJZFVIGUQUPAT-UIOOFZCWSA-N (1r,3s)-3-(1-benzylpiperidin-4-yl)-6-methyl-1-(pyrrolidin-1-ylmethyl)-3,4-dihydro-1h-isochromen-5-ol Chemical compound C([C@H]1C2=CC=C(C(=C2C[C@H](O1)C1CCN(CC=2C=CC=CC=2)CC1)O)C)N1CCCC1 RMJZFVIGUQUPAT-UIOOFZCWSA-N 0.000 claims 1
- CFYYWPYMSFBKGA-UIOOFZCWSA-N (1r,3s)-3-(1-benzylpiperidin-4-yl)-6-methyl-1-[[methyl(propyl)amino]methyl]-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@H](C3=CC=C(C)C(O)=C3C2)CN(C)CCC)CCN1CC1=CC=CC=C1 CFYYWPYMSFBKGA-UIOOFZCWSA-N 0.000 claims 1
- UZIYVHWKAPTLIM-GOTSBHOMSA-N (1r,3s)-3-[1-(cyclohexylmethyl)piperidin-4-yl]-6-methyl-1-(methylaminomethyl)-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@H](C3=CC=C(C)C(O)=C3C2)CNC)CCN1CC1CCCCC1 UZIYVHWKAPTLIM-GOTSBHOMSA-N 0.000 claims 1
- QKOIEBXTHJUZTJ-GOTSBHOMSA-N (1r,3s)-3-[1-[(3,4-difluorophenyl)methyl]piperidin-4-yl]-6-methyl-1-(methylaminomethyl)-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@H](C3=CC=C(C)C(O)=C3C2)CNC)CCN1CC1=CC=C(F)C(F)=C1 QKOIEBXTHJUZTJ-GOTSBHOMSA-N 0.000 claims 1
- FNIYMCLMIFKUEQ-GOTSBHOMSA-N (1r,3s)-3-[1-[(4-fluorophenyl)methyl]piperidin-4-yl]-6-methyl-1-(methylaminomethyl)-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@H](C3=CC=C(C)C(O)=C3C2)CNC)CCN1CC1=CC=C(F)C=C1 FNIYMCLMIFKUEQ-GOTSBHOMSA-N 0.000 claims 1
- DMPUCMGWNGRQJO-ZEQRLZLVSA-N (1r,3s)-3-[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]-6-methyl-1-(methylaminomethyl)-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@H](C3=CC=C(C)C(O)=C3C2)CNC)CCN1CC1=CC=C(OC)C=C1 DMPUCMGWNGRQJO-ZEQRLZLVSA-N 0.000 claims 1
- MBWROEPUMJSIIK-IRXDYDNUSA-N (1r,3s)-6-methyl-1-(methylaminomethyl)-3-(1-methylpiperidin-4-yl)-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1([C@H]2O[C@H](C3=CC=C(C)C(O)=C3C2)CNC)CCN(C)CC1 MBWROEPUMJSIIK-IRXDYDNUSA-N 0.000 claims 1
- PUJWGCPTXQMICM-RBCOLISLSA-N (1r,3s)-6-methyl-1-(methylaminomethyl)-3-[1-(2-phenylbutyl)piperidin-4-yl]-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@@H](CNC)C3=CC=C(C)C(O)=C3C2)CCN1CC(CC)C1=CC=CC=C1 PUJWGCPTXQMICM-RBCOLISLSA-N 0.000 claims 1
- HQBATKZCCGLDHC-ZEQRLZLVSA-N (1r,3s)-6-methyl-1-(methylaminomethyl)-3-[1-[(4-methylphenyl)methyl]piperidin-4-yl]-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@H](C3=CC=C(C)C(O)=C3C2)CNC)CCN1CC1=CC=C(C)C=C1 HQBATKZCCGLDHC-ZEQRLZLVSA-N 0.000 claims 1
- CSLNIYHOVWNBFK-VMPREFPWSA-N (1r,3s)-6-methyl-1-(methylaminomethyl)-3-[1-[(4-phenylphenyl)methyl]piperidin-4-yl]-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@H](C3=CC=C(C)C(O)=C3C2)CNC)CCN1CC(C=C1)=CC=C1C1=CC=CC=C1 CSLNIYHOVWNBFK-VMPREFPWSA-N 0.000 claims 1
- CQMNENXLLSABNA-UIOOFZCWSA-N (1r,3s)-6-methyl-1-(methylaminomethyl)-3-[1-[(4-propan-2-ylphenyl)methyl]piperidin-4-yl]-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@H](C3=CC=C(C)C(O)=C3C2)CNC)CCN1CC1=CC=C(C(C)C)C=C1 CQMNENXLLSABNA-UIOOFZCWSA-N 0.000 claims 1
- QCDCUTGCURHFGT-GOTSBHOMSA-N (1r,3s)-6-methyl-1-(methylaminomethyl)-3-[1-[[4-(trifluoromethyl)phenyl]methyl]piperidin-4-yl]-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CC([C@H]2O[C@H](C3=CC=C(C)C(O)=C3C2)CNC)CCN1CC1=CC=C(C(F)(F)F)C=C1 QCDCUTGCURHFGT-GOTSBHOMSA-N 0.000 claims 1
- SPJKISXDHRUHEO-SFTDATJTSA-N (2-chlorophenyl) 4-[(1r,3s)-1-(aminomethyl)-5-hydroxy-6-methyl-3,4-dihydro-1h-isochromen-3-yl]piperidine-1-carboxylate Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1C(=O)OC1=CC=CC=C1Cl SPJKISXDHRUHEO-SFTDATJTSA-N 0.000 claims 1
- GLNGOKSBSUHCMT-SFTDATJTSA-N (2-hydroxyphenyl) 4-[(1r,3s)-1-(aminomethyl)-5-hydroxy-6-methyl-3,4-dihydro-1h-isochromen-3-yl]piperidine-1-carboxylate Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1C(=O)OC1=CC=CC=C1O GLNGOKSBSUHCMT-SFTDATJTSA-N 0.000 claims 1
- FHFQGBILDBKPRE-SFTDATJTSA-N (4-bromophenyl) 4-[(1r,3s)-1-(aminomethyl)-5-hydroxy-6-methyl-3,4-dihydro-1h-isochromen-3-yl]piperidine-1-carboxylate Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1C(=O)OC1=CC=C(Br)C=C1 FHFQGBILDBKPRE-SFTDATJTSA-N 0.000 claims 1
- SZENZJVYXDZRPU-SFTDATJTSA-N (4-chlorophenyl) 4-[(1r,3s)-1-(aminomethyl)-5-hydroxy-6-methyl-3,4-dihydro-1h-isochromen-3-yl]piperidine-1-carboxylate Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1C(=O)OC1=CC=C(Cl)C=C1 SZENZJVYXDZRPU-SFTDATJTSA-N 0.000 claims 1
- WZLLJDRVGFKYJD-SFTDATJTSA-N (4-fluorophenyl) 4-[(1r,3s)-1-(aminomethyl)-5-hydroxy-6-methyl-3,4-dihydro-1h-isochromen-3-yl]piperidine-1-carboxylate Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1C(=O)OC1=CC=C(F)C=C1 WZLLJDRVGFKYJD-SFTDATJTSA-N 0.000 claims 1
- MGTJZIPOLCIFDC-VXKWHMMOSA-N (4-methoxyphenyl) 4-[(1r,3s)-1-(aminomethyl)-5-hydroxy-6-methyl-3,4-dihydro-1h-isochromen-3-yl]piperidine-1-carboxylate Chemical compound C1=CC(OC)=CC=C1OC(=O)N1CCC([C@H]2O[C@@H](CN)C3=CC=C(C)C(O)=C3C2)CC1 MGTJZIPOLCIFDC-VXKWHMMOSA-N 0.000 claims 1
- OIZLMGWETJTHSO-VXKWHMMOSA-N (4-methylphenyl) 4-[(1r,3s)-1-(aminomethyl)-5-hydroxy-6-methyl-3,4-dihydro-1h-isochromen-3-yl]piperidine-1-carboxylate Chemical compound C1=CC(C)=CC=C1OC(=O)N1CCC([C@H]2O[C@@H](CN)C3=CC=C(C)C(O)=C3C2)CC1 OIZLMGWETJTHSO-VXKWHMMOSA-N 0.000 claims 1
- OLAHHVRNGLPLAS-CWKMGFASSA-N (4s)-4-[[4-[(1r,3s)-1-(aminomethyl)-5-hydroxy-6-methyl-3,4-dihydro-1h-isochromen-3-yl]piperidin-1-yl]sulfonylmethyl]-7,7-dimethylbicyclo[2.2.1]heptan-3-one Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1S(=O)(=O)C[C@@]1(C2(C)C)C(=O)CC2CC1 OLAHHVRNGLPLAS-CWKMGFASSA-N 0.000 claims 1
- MPXDWMFKYLXSCA-GOTSBHOMSA-N 1-[2-[4-[(1r,3s)-1-(aminomethyl)-5-hydroxy-6-methyl-3,4-dihydro-1h-isochromen-3-yl]piperidin-1-yl]ethyl]-3-(4-fluorophenyl)urea Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1CCNC(=O)NC1=CC=C(F)C=C1 MPXDWMFKYLXSCA-GOTSBHOMSA-N 0.000 claims 1
- NJSYHLKGARRBGS-GOTSBHOMSA-N 1-[2-[4-[(1r,3s)-1-(aminomethyl)-5-hydroxy-6-methyl-3,4-dihydro-1h-isochromen-3-yl]piperidin-1-yl]ethyl]-3-phenylurea Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1CCNC(=O)NC1=CC=CC=C1 NJSYHLKGARRBGS-GOTSBHOMSA-N 0.000 claims 1
- SRWXAAISFUFMBO-VXKWHMMOSA-N 1-[4-[(1r,3s)-1-(aminomethyl)-5-hydroxy-6-methyl-3,4-dihydro-1h-isochromen-3-yl]piperidin-1-yl]-2-phenylethanone Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1C(=O)CC1=CC=CC=C1 SRWXAAISFUFMBO-VXKWHMMOSA-N 0.000 claims 1
- FHXJRPKCODIORW-OALUTQOASA-N 1-[4-[(1r,3s)-1-(aminomethyl)-5-hydroxy-6-methyl-3,4-dihydro-1h-isochromen-3-yl]piperidin-1-yl]-3-methylbutan-1-one Chemical compound C1CN(C(=O)CC(C)C)CCC1[C@H]1O[C@@H](CN)C2=CC=C(C)C(O)=C2C1 FHXJRPKCODIORW-OALUTQOASA-N 0.000 claims 1
- OJXCFRRNVYLJNM-GOTSBHOMSA-N 1-[4-[(1r,3s)-1-(aminomethyl)-5-hydroxy-6-methyl-3,4-dihydro-1h-isochromen-3-yl]piperidin-1-yl]-3-phenylpropan-1-one Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1C(=O)CCC1=CC=CC=C1 OJXCFRRNVYLJNM-GOTSBHOMSA-N 0.000 claims 1
- CTOKPZPVKRHVEP-ROUUACIJSA-N 1-[4-[(1r,3s)-1-(aminomethyl)-5-hydroxy-6-methyl-3,4-dihydro-1h-isochromen-3-yl]piperidin-1-yl]butan-1-one Chemical compound C1CN(C(=O)CCC)CCC1[C@H]1O[C@@H](CN)C2=CC=C(C)C(O)=C2C1 CTOKPZPVKRHVEP-ROUUACIJSA-N 0.000 claims 1
- MZUQSFJVCKMDSM-IRXDYDNUSA-N 1-[4-[(1r,3s)-1-(aminomethyl)-5-hydroxy-6-methyl-3,4-dihydro-1h-isochromen-3-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1[C@H]1O[C@@H](CN)C2=CC=C(C)C(O)=C2C1 MZUQSFJVCKMDSM-IRXDYDNUSA-N 0.000 claims 1
- XBLDUOXNGORQLX-LGTSYYJHSA-N 2-[4-[(1r,3s)-1-(aminomethyl)-5-hydroxy-6-methyl-3,4-dihydro-1h-isochromen-3-yl]piperidin-1-yl]-2-phenylacetic acid Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1C(C(O)=O)C1=CC=CC=C1 XBLDUOXNGORQLX-LGTSYYJHSA-N 0.000 claims 1
- GYHILXUHOQKEMR-DQEYMECFSA-N 2-[4-[(1r,3s)-1-(ethylaminomethyl)-5-hydroxy-6-methyl-3,4-dihydro-1h-isochromen-3-yl]piperidin-1-yl]-1-phenylethanone Chemical compound C1CC([C@H]2O[C@H](C3=CC=C(C)C(O)=C3C2)CNCC)CCN1CC(=O)C1=CC=CC=C1 GYHILXUHOQKEMR-DQEYMECFSA-N 0.000 claims 1
- DBEYLWKFCXFTDT-SFTDATJTSA-N 4-[(1r,3s)-1-(aminomethyl)-5-hydroxy-6-methyl-3,4-dihydro-1h-isochromen-3-yl]-n,n-di(propan-2-yl)piperidine-1-carboxamide Chemical compound C1CN(C(=O)N(C(C)C)C(C)C)CCC1[C@H]1O[C@@H](CN)C2=CC=C(C)C(O)=C2C1 DBEYLWKFCXFTDT-SFTDATJTSA-N 0.000 claims 1
- ZITRFPVIHYXAHG-OALUTQOASA-N 4-[(1r,3s)-1-(aminomethyl)-5-hydroxy-6-methyl-3,4-dihydro-1h-isochromen-3-yl]-n,n-diethylpiperidine-1-carboxamide Chemical compound C1CN(C(=O)N(CC)CC)CCC1[C@H]1O[C@@H](CN)C2=CC=C(C)C(O)=C2C1 ZITRFPVIHYXAHG-OALUTQOASA-N 0.000 claims 1
- MOYUDENLEICFRW-IRXDYDNUSA-N 4-[(1r,3s)-1-(aminomethyl)-5-hydroxy-6-methyl-3,4-dihydro-1h-isochromen-3-yl]-n,n-dimethylpiperidine-1-carboxamide Chemical compound C1CN(C(=O)N(C)C)CCC1[C@H]1O[C@@H](CN)C2=CC=C(C)C(O)=C2C1 MOYUDENLEICFRW-IRXDYDNUSA-N 0.000 claims 1
- GRIFOUCGJCZMSD-IRXDYDNUSA-N 4-[(1r,3s)-1-(aminomethyl)-5-hydroxy-6-methyl-3,4-dihydro-1h-isochromen-3-yl]-n,n-dimethylpiperidine-1-sulfonamide Chemical compound C1CN(S(=O)(=O)N(C)C)CCC1[C@H]1O[C@@H](CN)C2=CC=C(C)C(O)=C2C1 GRIFOUCGJCZMSD-IRXDYDNUSA-N 0.000 claims 1
- NOYSAHGYOLZNFD-SVBPBHIXSA-N 4-[(1r,3s)-1-(aminomethyl)-5-hydroxy-6-methyl-3,4-dihydro-1h-isochromen-3-yl]-n,n-diphenylpiperidine-1-carboxamide Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1C(=O)N(C=1C=CC=CC=1)C1=CC=CC=C1 NOYSAHGYOLZNFD-SVBPBHIXSA-N 0.000 claims 1
- JQMTXNGSVAASLK-SFTDATJTSA-N 4-[(1r,3s)-1-(aminomethyl)-5-hydroxy-6-methyl-3,4-dihydro-1h-isochromen-3-yl]-n-(2-fluorophenyl)piperidine-1-carboxamide Chemical compound C1CC([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN1C(=O)NC1=CC=CC=C1F JQMTXNGSVAASLK-SFTDATJTSA-N 0.000 claims 1
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- UXTRSEZMEXKCQO-INIZCTEOSA-N (1s)-2-(3-methyl-2-propan-2-yloxyphenyl)-1-piperidin-4-ylethanol Chemical compound CC(C)OC1=C(C)C=CC=C1C[C@H](O)C1CCNCC1 UXTRSEZMEXKCQO-INIZCTEOSA-N 0.000 description 1
- IJFAUIBWMSPSIV-UHFFFAOYSA-N 2-(3-methyl-2-propan-2-yloxyphenyl)-1-pyridin-4-ylethanone Chemical compound CC(C)OC1=C(C)C=CC=C1CC(=O)C1=CC=NC=C1 IJFAUIBWMSPSIV-UHFFFAOYSA-N 0.000 description 1
- 239000012223 aqueous fraction Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- HHRBHXDVRRCGQY-UHFFFAOYSA-N n-(2,2-dimethoxyethyl)formamide Chemical compound COC(OC)CNC=O HHRBHXDVRRCGQY-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56655704P | 2004-04-29 | 2004-04-29 | |
| PCT/US2005/014487 WO2005111025A1 (en) | 2004-04-29 | 2005-04-27 | 3-piperidinylisochroman-5-ols as dopamine agonists |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007535548A JP2007535548A (ja) | 2007-12-06 |
| JP2007535548A5 true JP2007535548A5 (https=) | 2008-03-27 |
| JP4685861B2 JP4685861B2 (ja) | 2011-05-18 |
Family
ID=34967397
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007510941A Expired - Fee Related JP4685861B2 (ja) | 2004-04-29 | 2005-04-27 | ドーパミンアゴニストとしての３−ピペリジニルイソクロマン−５−オール |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7919508B2 (https=) |
| EP (1) | EP1749001B1 (https=) |
| JP (1) | JP4685861B2 (https=) |
| AR (1) | AR050245A1 (https=) |
| AT (1) | ATE459618T1 (https=) |
| DE (1) | DE602005019719D1 (https=) |
| DK (1) | DK1749001T3 (https=) |
| ES (1) | ES2342083T3 (https=) |
| PT (1) | PT1749001E (https=) |
| TW (1) | TW200607802A (https=) |
| WO (1) | WO2005111025A1 (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI3060551T1 (sl) * | 2013-10-22 | 2019-11-29 | Chiesi Farm Spa | Postopek za pripravo inhibitorja PDE4 |
| EP3137469B1 (en) * | 2014-04-28 | 2019-10-09 | Pfizer Inc | Heterocyclic compounds and their use as dopamine d1 ligands |
| US10105359B2 (en) * | 2014-10-08 | 2018-10-23 | Ucb Biopharma Sprl | Tetrahydroisoquinoline derivatives |
| UA125519C2 (uk) | 2016-07-29 | 2022-04-13 | Суновіон Фармасьютікалз Інк. | Сполуки і композиції і їх застосування |
| CA3032141A1 (en) | 2016-07-29 | 2018-02-01 | Vadim ALEXANDROV | Compounds and compositions and uses thereof |
| AU2017311691B2 (en) | 2016-08-18 | 2021-12-02 | Vidac Pharma Ltd. | Piperazine derivatives, pharmaceutical compositions and methods of use thereof |
| BR112020001433A2 (pt) | 2017-08-02 | 2020-07-28 | Sunovion Pharmaceuticals Inc. | compostos de isocromano e usos dos mesmos |
| CN111196781B (zh) * | 2018-11-16 | 2023-07-28 | 湖南中南制药有限责任公司 | 一种改进的制备五氟利多的方法 |
| MX2021010880A (es) | 2019-03-14 | 2022-01-18 | Sunovion Pharmaceuticals Inc | Sales de un compuesto de isocromanilo y formas cristalinas, procesos de preparacion, usos terapeuticos y composiciones farmaceuticas de las mismas. |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4994486A (en) * | 1989-05-31 | 1991-02-19 | Abbott Laboratories | Dopaminergic compounds |
| US4963568A (en) * | 1989-05-31 | 1990-10-16 | Abbott Laboratories | Dopamine agonists |
| ES2194303T3 (es) * | 1997-02-07 | 2003-11-16 | Aventis Pharma Inc | Derivados de (4-piperidinil)-1h-2-benzopirano utiles como agentes antipsicoticos. |
| US6004982A (en) * | 1997-09-15 | 1999-12-21 | Hoechst Marion Roussel, Inc. | 4-piperidinyl) H-2-benzopyran derivatives useful as antipsychotic agents |
-
2005
- 2005-04-27 AT AT05740005T patent/ATE459618T1/de active
- 2005-04-27 DK DK05740005.3T patent/DK1749001T3/da active
- 2005-04-27 PT PT05740005T patent/PT1749001E/pt unknown
- 2005-04-27 WO PCT/US2005/014487 patent/WO2005111025A1/en not_active Ceased
- 2005-04-27 JP JP2007510941A patent/JP4685861B2/ja not_active Expired - Fee Related
- 2005-04-27 EP EP05740005A patent/EP1749001B1/en not_active Expired - Lifetime
- 2005-04-27 ES ES05740005T patent/ES2342083T3/es not_active Expired - Lifetime
- 2005-04-27 DE DE602005019719T patent/DE602005019719D1/de not_active Expired - Lifetime
- 2005-04-28 AR ARP050101668A patent/AR050245A1/es not_active Application Discontinuation
- 2005-04-29 TW TW094113776A patent/TW200607802A/zh unknown
-
2006
- 2006-10-24 US US11/552,169 patent/US7919508B2/en not_active Expired - Fee Related
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