PT1749001E - 3-piperidinilisocroman-5-oles como agonistas da dopamina - Google Patents

Info

Publication number

PT1749001E

PT1749001E PT05740005T PT05740005T PT1749001E PT 1749001 E PT1749001 E PT 1749001E PT 05740005 T PT05740005 T PT 05740005T PT 05740005 T PT05740005 T PT 05740005T PT 1749001 E PT1749001 E PT 1749001E

Authority

PT

Portugal

Prior art keywords

aminomethyl

piperidin

methylisochroman

methyl

benzyl

Prior art date

2004-04-29

Links

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• 239000003136 dopamine receptor stimulating agent Substances 0.000 title description 17
• 229940052760 dopamine agonists Drugs 0.000 title description 7
• PEUXHIGWBHZERT-UHFFFAOYSA-N 3-piperidin-1-yl-3,4-dihydro-1h-isochromen-5-ol Chemical class C1C=2C(O)=CC=CC=2COC1N1CCCCC1 PEUXHIGWBHZERT-UHFFFAOYSA-N 0.000 title 1
• -1 phenylcarbamoyl Chemical group 0.000 claims description 204
• 150000001875 compounds Chemical class 0.000 claims description 152
• 125000000217 alkyl group Chemical group 0.000 claims description 108
• VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims description 75
• 229910052739 hydrogen Inorganic materials 0.000 claims description 51
• 239000001257 hydrogen Substances 0.000 claims description 49
• 229960003638 dopamine Drugs 0.000 claims description 37
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 30
• 150000003839 salts Chemical class 0.000 claims description 27
• 238000011282 treatment Methods 0.000 claims description 27
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 25
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 24
• 239000003814 drug Substances 0.000 claims description 24
• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 23
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 22
• ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 22
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
• 230000000694 effects Effects 0.000 claims description 21
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 18
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
• 229910052736 halogen Inorganic materials 0.000 claims description 18
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 17
• 150000002367 halogens Chemical class 0.000 claims description 17
• BYJXGCRAXIIOLC-UHFFFAOYSA-N 3,4-dihydro-1h-isochromen-5-ol Chemical compound C1OCCC2=C1C=CC=C2O BYJXGCRAXIIOLC-UHFFFAOYSA-N 0.000 claims description 15
• 208000035475 disorder Diseases 0.000 claims description 15
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 14
• BDWGHVFBRSMPDD-GJZGRUSLSA-N 4-[(1r,3s)-1-(aminomethyl)-5-hydroxy-6-methyl-3,4-dihydro-1h-isochromen-3-yl]piperidine-1-carboxylic acid Chemical compound C1([C@H]2O[C@@H](CN)C3=CC=C(C(=C3C2)O)C)CCN(C(O)=O)CC1 BDWGHVFBRSMPDD-GJZGRUSLSA-N 0.000 claims description 11
• 208000018737 Parkinson disease Diseases 0.000 claims description 11
• 125000004432 carbon atom Chemical group C* 0.000 claims description 11
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
• 238000002360 preparation method Methods 0.000 claims description 11
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 10
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 9
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 9
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 9
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 7
• 208000012902 Nervous system disease Diseases 0.000 claims description 7
• 239000003937 drug carrier Substances 0.000 claims description 7
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
• 230000003935 attention Effects 0.000 claims description 6
• 230000006399 behavior Effects 0.000 claims description 6
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 6
• 125000001072 heteroaryl group Chemical group 0.000 claims description 6
• 239000008194 pharmaceutical composition Substances 0.000 claims description 6
• 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 6
• 125000001424 substituent group Chemical group 0.000 claims description 6
• OLKAFFLKIMAYMJ-SQJZIBIZSA-N (1R,3S)-3-[1-(3-aminobutyl)piperidin-4-yl]-1-(aminomethyl)-6-methyl-3,4-dihydro-1H-isochromen-5-ol Chemical compound C1CN(CCC(N)C)CCC1[C@H]1O[C@@H](CN)C2=CC=C(C)C(O)=C2C1 OLKAFFLKIMAYMJ-SQJZIBIZSA-N 0.000 claims description 5
• 125000003890 2-phenylbutyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 5
• 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 description 5
• 208000025966 Neurological disease Diseases 0.000 claims description 5
• 230000001149 cognitive effect Effects 0.000 claims description 5
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 5
• 208000011117 substance-related disease Diseases 0.000 claims description 5
• DNUTZBZXLPWRJG-UHFFFAOYSA-N 1-Piperidine carboxylic acid Chemical compound OC(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-N 0.000 claims description 4
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
• 125000003342 alkenyl group Chemical group 0.000 claims description 4
• 229910052799 carbon Inorganic materials 0.000 claims description 4
• 230000002526 effect on cardiovascular system Effects 0.000 claims description 4
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 4
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
• 201000009032 substance abuse Diseases 0.000 claims description 4
• 231100000736 substance abuse Toxicity 0.000 claims description 4
• CZLZPANEELQSMK-DQEYMECFSA-N (1r,3s)-1-[[ethyl(methyl)amino]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)CC)CCN1CC1=CC=C(C(F)(F)F)C=C1 CZLZPANEELQSMK-DQEYMECFSA-N 0.000 claims description 3
• JUEANUAHZGBLJD-UIOOFZCWSA-N (1r,3s)-6-methyl-1-[[methyl(propyl)amino]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)CCC)CCN1CC1=CC=C(C(F)(F)F)C=C1 JUEANUAHZGBLJD-UIOOFZCWSA-N 0.000 claims description 3
• 125000003545 alkoxy group Chemical group 0.000 claims description 3
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
• 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
• 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
• KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical group C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 claims description 3
• 125000002541 furyl group Chemical group 0.000 claims description 3
• 125000002883 imidazolyl group Chemical group 0.000 claims description 3
• 125000001041 indolyl group Chemical group 0.000 claims description 3
• 125000005956 isoquinolyl group Chemical group 0.000 claims description 3
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
• 230000000926 neurological effect Effects 0.000 claims description 3
• 125000004076 pyridyl group Chemical group 0.000 claims description 3
• 125000005493 quinolyl group Chemical group 0.000 claims description 3
• 125000001544 thienyl group Chemical group 0.000 claims description 3
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• GANOWGKKRFHIEC-SFTDATJTSA-N (1r,3s)-1-(aminomethyl)-3-[1-[[2-fluoro-3-(trifluoromethyl)phenyl]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(C(F)(F)F)=C1F GANOWGKKRFHIEC-SFTDATJTSA-N 0.000 claims description 2
• QJEKQCVLLXLLHO-VXKWHMMOSA-N (1r,3s)-1-(aminomethyl)-3-[1-[[3,5-bis(trifluoromethyl)phenyl]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)(F)F)=CC(C(F)(F)F)=C1 QJEKQCVLLXLLHO-VXKWHMMOSA-N 0.000 claims description 2
• BIPLNIWXALOOIX-VXKWHMMOSA-N (1r,3s)-1-(aminomethyl)-3-[1-[[4-chloro-3-(trifluoromethyl)phenyl]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(C(F)(F)F)=C1 BIPLNIWXALOOIX-VXKWHMMOSA-N 0.000 claims description 2
• XEYSFZRGOKEOHD-OALUTQOASA-N (1r,3s)-1-(aminomethyl)-6-methyl-3-[1-(2-methylpropyl)piperidin-4-yl]-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1CN(CC(C)C)CCC1[C@H]1O[C@@H](CN)C2=CC=C(C)C(O)=C2C1 XEYSFZRGOKEOHD-OALUTQOASA-N 0.000 claims description 2
• WQBWPBGCFBCYRC-SVBPBHIXSA-N (1r,3s)-1-(aminomethyl)-6-methyl-3-[1-(4-phenylphenyl)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)C(C=C1)=CC=C1C1=CC=CC=C1 WQBWPBGCFBCYRC-SVBPBHIXSA-N 0.000 claims description 2
• JEFBHAFJWAKVSV-ZEQRLZLVSA-N (1r,3s)-1-(aminomethyl)-6-methyl-3-[1-(4-propan-2-ylphenyl)sulfonylpiperidin-4-yl]-3,4-dihydro-1h-isochromen-5-ol Chemical compound C1=CC(C(C)C)=CC=C1S(=O)(=O)N1CCC([C@H]2O[C@@H](CN)C3=CC=C(C)C(O)=C3C2)CC1 JEFBHAFJWAKVSV-ZEQRLZLVSA-N 0.000 claims description 2
• CUMQNWFEVBNNCW-UIOOFZCWSA-N (1r,3s)-1-(aminomethyl)-6-methyl-3-[1-(naphthalen-1-ylmethyl)piperidin-4-yl]-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)=CC=CC2=C1 CUMQNWFEVBNNCW-UIOOFZCWSA-N 0.000 claims description 2
• OVOGMLVELXBCCP-PMACEKPBSA-N (1r,3s)-1-(aminomethyl)-6-methyl-3-[1-(thiophen-3-ylmethyl)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=1C=CSC=1 OVOGMLVELXBCCP-PMACEKPBSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 2
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
• 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 description 2
• 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
• UOBYKYZJUGYBDK-UHFFFAOYSA-N 2-naphthoic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC=C21 UOBYKYZJUGYBDK-UHFFFAOYSA-N 0.000 claims description 2
• 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 2
• 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 2
• 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims description 2
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
• 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 description 2
• 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 2
• 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 2
• ZRSNZINYAWTAHE-UHFFFAOYSA-N Anisaldehyde Natural products COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 claims description 2
• 206010012335 Dependence Diseases 0.000 claims description 2
• CATSNJVOTSVZJV-UHFFFAOYSA-N Heptan-2-one Natural products CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 claims description 2
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