PT2260042E - Derivados de ciclo-hexano espirocíclicos substituídos - Google Patents

Info

Publication number

PT2260042E

PT2260042E PT09724314T PT09724314T PT2260042E PT 2260042 E PT2260042 E PT 2260042E PT 09724314 T PT09724314 T PT 09724314T PT 09724314 T PT09724314 T PT 09724314T PT 2260042 E PT2260042 E PT 2260042E

Authority

PT

Portugal

Prior art keywords

indole

cyclohexane

amine

phenyl

dimethyl

Prior art date

2008-03-27

Links

• Espacenet
• Global Dossier
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• 125000000113 cyclohexyl group Chemical class [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims description 142
• -1 N, N-dimethyl-3,4-diphenyl-4 ', 9'-dihydro-3'H-spiro [cyclohexane-1,1'-pyrano [3,4-b] indole] -4 -amide Chemical compound 0.000 claims description 62
• 125000001931 aliphatic group Chemical group 0.000 claims description 61
• 125000003118 aryl group Chemical group 0.000 claims description 51
• 239000000203 mixture Substances 0.000 claims description 49
• 229910052757 nitrogen Inorganic materials 0.000 claims description 49
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
• 125000001424 substituent group Chemical group 0.000 claims description 37
• 238000006467 substitution reaction Methods 0.000 claims description 34
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 33
• 125000001072 heteroaryl group Chemical group 0.000 claims description 28
• 150000003839 salts Chemical class 0.000 claims description 25
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 22
• 239000003814 drug Substances 0.000 claims description 22
• 229920006395 saturated elastomer Polymers 0.000 claims description 22
• 125000005842 heteroatom Chemical group 0.000 claims description 20
• RERZNCLIYCABFS-UHFFFAOYSA-N harmaline Chemical compound C1CN=C(C)C2=C1C1=CC=C(OC)C=C1N2 RERZNCLIYCABFS-UHFFFAOYSA-N 0.000 claims description 19
• KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 17
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 17
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 17
• 208000002193 Pain Diseases 0.000 claims description 16
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 12
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 11
• 125000000623 heterocyclic group Chemical group 0.000 claims description 10
• 229940005483 opioid analgesics Drugs 0.000 claims description 10
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
• 238000004519 manufacturing process Methods 0.000 claims description 8
• CGLYBEYFUQIRIS-UHFFFAOYSA-N 3'-benzyl-n,n-dimethyl-1'-phenylspiro[2,3,4,9-tetrahydropyrido[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1C(N(C)C)(C=2C=CC=CC=2)CCC2(C3=C(C4=CC=CC=C4N3)CCN2)C1CC1=CC=CC=C1 CGLYBEYFUQIRIS-UHFFFAOYSA-N 0.000 claims description 7
• XLEGHKKTFZALDA-UHFFFAOYSA-N 3'-fluoro-n,n-dimethyl-1'-phenylspiro[2,3,4,9-tetrahydropyrido[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1CC2(C3=C(C4=CC=CC=C4N3)CCN2)C(F)CC1(N(C)C)C1=CC=CC=C1 XLEGHKKTFZALDA-UHFFFAOYSA-N 0.000 claims description 7
• 125000004122 cyclic group Chemical group 0.000 claims description 7
• XXYDNDDLCYHHNL-UHFFFAOYSA-N n,n,3'-trimethyl-1'-phenylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1CC2(C3=C(C4=CC=CC=C4N3)CCO2)C(C)CC1(N(C)C)C1=CC=CC=C1 XXYDNDDLCYHHNL-UHFFFAOYSA-N 0.000 claims description 7
• MVXVYAKCVDQRLW-UHFFFAOYSA-N 1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CN=C2NC=CC2=C1 MVXVYAKCVDQRLW-UHFFFAOYSA-N 0.000 claims description 6
• 239000013543 active substance Substances 0.000 claims description 6
• 230000000694 effects Effects 0.000 claims description 6
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
• RGRFHXRVKJVFOG-UHFFFAOYSA-N 3',6-difluoro-n,n-dimethyl-1'-phenylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1CC2(C3=C(C4=CC(F)=CC=C4N3)CCO2)C(F)CC1(N(C)C)C1=CC=CC=C1 RGRFHXRVKJVFOG-UHFFFAOYSA-N 0.000 claims description 5
• ZRVFZCWVNBOHAP-UHFFFAOYSA-N 3'-[(3-fluorophenyl)methyl]-n,n-dimethyl-1'-phenylspiro[2,3,4,9-tetrahydropyrido[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1C(N(C)C)(C=2C=CC=CC=2)CCC2(C3=C(C4=CC=CC=C4N3)CCN2)C1CC1=CC=CC(F)=C1 ZRVFZCWVNBOHAP-UHFFFAOYSA-N 0.000 claims description 5
• 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims description 5
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
• 229940079593 drug Drugs 0.000 claims description 5
• 229910052717 sulfur Inorganic materials 0.000 claims description 5
• WYEZTUIJZFLRTP-UHFFFAOYSA-N 2',2'-difluoro-n,n-dimethyl-1'-phenylspiro[2,3,4,9-tetrahydropyrido[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1CC2(C3=C(C4=CC=CC=C4N3)CCN2)CC(F)(F)C1(N(C)C)C1=CC=CC=C1 WYEZTUIJZFLRTP-UHFFFAOYSA-N 0.000 claims description 4
• DBWJRYDBOSDJPY-UHFFFAOYSA-N 3',3',6-trifluoro-1'-(3-fluorophenyl)-n,n-dimethylspiro[2,3,4,9-tetrahydropyrido[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1CC2(C3=C(C4=CC(F)=CC=C4N3)CCN2)C(F)(F)CC1(N(C)C)C1=CC=CC(F)=C1 DBWJRYDBOSDJPY-UHFFFAOYSA-N 0.000 claims description 4
• YJTZWNKGTJGABL-UHFFFAOYSA-N 3'-benzyl-n,n-dimethyl-1'-phenylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1C(N(C)C)(C=2C=CC=CC=2)CCC2(C3=C(C4=CC=CC=C4N3)CCO2)C1CC1=CC=CC=C1 YJTZWNKGTJGABL-UHFFFAOYSA-N 0.000 claims description 4
• ILNCEOIGYRKHIT-UHFFFAOYSA-N 3'-fluoro-n,n-dimethyl-1'-phenylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1CC2(C3=C(C4=CC=CC=C4N3)CCO2)C(F)CC1(N(C)C)C1=CC=CC=C1 ILNCEOIGYRKHIT-UHFFFAOYSA-N 0.000 claims description 4
• 208000024827 Alzheimer disease Diseases 0.000 claims description 4
• 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims description 4
• 239000002671 adjuvant Substances 0.000 claims description 4
• 230000003444 anaesthetic effect Effects 0.000 claims description 4
• 125000002950 monocyclic group Chemical group 0.000 claims description 4
• NNHQQQAFJCVHTJ-UHFFFAOYSA-N n,n-dimethyl-1'-phenyl-3'-phenylsulfanylspiro[2,3,4,9-tetrahydropyrido[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1C(N(C)C)(C=2C=CC=CC=2)CCC2(C3=C(C4=CC=CC=C4N3)CCN2)C1SC1=CC=CC=C1 NNHQQQAFJCVHTJ-UHFFFAOYSA-N 0.000 claims description 4
• LYLYGYZNYSHTPY-UHFFFAOYSA-N n,n-dimethyl-1'-phenyl-3'-phenylsulfanylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1C(N(C)C)(C=2C=CC=CC=2)CCC2(C3=C(C4=CC=CC=C4N3)CCO2)C1SC1=CC=CC=C1 LYLYGYZNYSHTPY-UHFFFAOYSA-N 0.000 claims description 4
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
• 229910052760 oxygen Inorganic materials 0.000 claims description 4
• XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 4
• RJLKEYGXHXIEMB-UHFFFAOYSA-N 2-[5'-(dimethylamino)-5'-phenylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,2'-cyclohexane]-1'-yl]acetonitrile Chemical compound C1CC2(C3=C(C4=CC=CC=C4N3)CCO2)C(CC#N)CC1(N(C)C)C1=CC=CC=C1 RJLKEYGXHXIEMB-UHFFFAOYSA-N 0.000 claims description 3
• MHEHAGBCOANASI-UHFFFAOYSA-N 2-[5'-(dimethylamino)-5'-phenylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,2'-cyclohexane]-1'-yl]ethanol Chemical compound C1CC2(C3=C(C4=CC=CC=C4N3)CCO2)C(CCO)CC1(N(C)C)C1=CC=CC=C1 MHEHAGBCOANASI-UHFFFAOYSA-N 0.000 claims description 3
• YZTKCOYZTZVEIJ-UHFFFAOYSA-N 3',3'-difluoro-1'-(3-fluorophenyl)-n,n-dimethylspiro[2,3,4,9-tetrahydropyrido[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1CC2(C3=C(C4=CC=CC=C4N3)CCN2)C(F)(F)CC1(N(C)C)C1=CC=CC(F)=C1 YZTKCOYZTZVEIJ-UHFFFAOYSA-N 0.000 claims description 3
• KJRIQDNHVYBMSO-UHFFFAOYSA-N 3',5',6-trifluoro-1'-(3-fluorophenyl)-n,n-dimethylspiro[2,3,4,9-tetrahydropyrido[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1C(F)C2(C3=C(C4=CC(F)=CC=C4N3)CCN2)C(F)CC1(N(C)C)C1=CC=CC(F)=C1 KJRIQDNHVYBMSO-UHFFFAOYSA-N 0.000 claims description 3
• KRZPNWSAXBSKRL-UHFFFAOYSA-N 3',5'-difluoro-1'-(3-fluorophenyl)-n,n-dimethylspiro[2,3,4,9-tetrahydropyrido[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1C(F)C2(C3=C(C4=CC=CC=C4N3)CCN2)C(F)CC1(N(C)C)C1=CC=CC(F)=C1 KRZPNWSAXBSKRL-UHFFFAOYSA-N 0.000 claims description 3
• MPELBLISKJKROZ-UHFFFAOYSA-N 3',6-difluoro-1'-(3-fluorophenyl)-n,n-dimethylspiro[2,3,4,9-tetrahydropyrido[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1CC2(C3=C(C4=CC(F)=CC=C4N3)CCN2)C(F)CC1(N(C)C)C1=CC=CC(F)=C1 MPELBLISKJKROZ-UHFFFAOYSA-N 0.000 claims description 3
• LEZGTFHHHFCMIE-UHFFFAOYSA-N 3'-[(3-fluorophenyl)methyl]-n,n-dimethyl-1'-phenylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1C(N(C)C)(C=2C=CC=CC=2)CCC2(C3=C(C4=CC=CC=C4N3)CCO2)C1CC1=CC=CC(F)=C1 LEZGTFHHHFCMIE-UHFFFAOYSA-N 0.000 claims description 3
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
• 208000009205 Tinnitus Diseases 0.000 claims description 3
• 239000000654 additive Substances 0.000 claims description 3
• 125000002723 alicyclic group Chemical group 0.000 claims description 3
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
• 125000002619 bicyclic group Chemical group 0.000 claims description 3
• 208000035475 disorder Diseases 0.000 claims description 3
• 239000001301 oxygen Substances 0.000 claims description 3
• 125000003367 polycyclic group Chemical group 0.000 claims description 3
• 239000011593 sulfur Substances 0.000 claims description 3
• 231100000886 tinnitus Toxicity 0.000 claims description 3
• ZWAFHWCKPOMXPK-UHFFFAOYSA-N 1'-butyl-2',2',6-trifluoro-n,n-dimethylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1C(F)(F)C(CCCC)(N(C)C)CCC21C(NC=1C3=CC(F)=CC=1)=C3CCO2 ZWAFHWCKPOMXPK-UHFFFAOYSA-N 0.000 claims description 2
• NDBLPZORFSBNFP-UHFFFAOYSA-N 1'-butyl-2',6-difluoro-n,n-dimethylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1C(F)C(CCCC)(N(C)C)CCC21C(NC=1C3=CC(F)=CC=1)=C3CCO2 NDBLPZORFSBNFP-UHFFFAOYSA-N 0.000 claims description 2
• XWZRWYMJXBMBEJ-UHFFFAOYSA-N 1'-butyl-3',3',6-trifluoro-n,n-dimethylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound FC1(F)CC(CCCC)(N(C)C)CCC11C(NC=2C3=CC(F)=CC=2)=C3CCO1 XWZRWYMJXBMBEJ-UHFFFAOYSA-N 0.000 claims description 2
• JLSORPCRDLLDLD-UHFFFAOYSA-N 1'-butyl-3',6-difluoro-n,n-dimethylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound FC1CC(CCCC)(N(C)C)CCC11C(NC=2C3=CC(F)=CC=2)=C3CCO1 JLSORPCRDLLDLD-UHFFFAOYSA-N 0.000 claims description 2
• QERFEDFJCNNUNU-UHFFFAOYSA-N 2',2',6-trifluoro-1'-(3-fluorophenyl)-n,n-dimethylspiro[2,3,4,9-tetrahydropyrido[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1CC2(C3=C(C4=CC(F)=CC=C4N3)CCN2)CC(F)(F)C1(N(C)C)C1=CC=CC(F)=C1 QERFEDFJCNNUNU-UHFFFAOYSA-N 0.000 claims description 2
• LZFDDVHXABBJPX-UHFFFAOYSA-N 2',2',6-trifluoro-n,n-dimethyl-1'-phenylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1CC2(C3=C(C4=CC(F)=CC=C4N3)CCO2)CC(F)(F)C1(N(C)C)C1=CC=CC=C1 LZFDDVHXABBJPX-UHFFFAOYSA-N 0.000 claims description 2
• KROQWYPFFGMGID-UHFFFAOYSA-N 2',2',6-trifluoro-n,n-dimethyl-1'-thiophen-2-ylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1CC2(C3=C(C4=CC(F)=CC=C4N3)CCO2)CC(F)(F)C1(N(C)C)C1=CC=CS1 KROQWYPFFGMGID-UHFFFAOYSA-N 0.000 claims description 2
• PRYJGPVLQGEIHP-UHFFFAOYSA-N 2',6-difluoro-1'-(3-fluorophenyl)-n,n-dimethylspiro[2,3,4,9-tetrahydropyrido[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1CC2(C3=C(C4=CC(F)=CC=C4N3)CCN2)CC(F)C1(N(C)C)C1=CC=CC(F)=C1 PRYJGPVLQGEIHP-UHFFFAOYSA-N 0.000 claims description 2
• WALZLZQINUMROW-UHFFFAOYSA-N 2',6-difluoro-n,n-dimethyl-1'-phenylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1CC2(C3=C(C4=CC(F)=CC=C4N3)CCO2)CC(F)C1(N(C)C)C1=CC=CC=C1 WALZLZQINUMROW-UHFFFAOYSA-N 0.000 claims description 2
• KRSPNUVHHWJPBX-UHFFFAOYSA-N 2'-[(dimethylamino)methyl]-n,n-dimethyl-1'-phenylspiro[2,3,4,9-tetrahydropyrido[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound CN(C)CC1CC2(C3=C(C4=CC=CC=C4N3)CCN2)CCC1(N(C)C)C1=CC=CC=C1 KRSPNUVHHWJPBX-UHFFFAOYSA-N 0.000 claims description 2
• ZTOKBWFOPCUIQE-UHFFFAOYSA-N 2'-[(dimethylamino)methyl]-n,n-dimethyl-1'-phenylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound CN(C)CC1CC2(C3=C(C4=CC=CC=C4N3)CCO2)CCC1(N(C)C)C1=CC=CC=C1 ZTOKBWFOPCUIQE-UHFFFAOYSA-N 0.000 claims description 2
• VMWCVNRWKYXQMS-UHFFFAOYSA-N 2'-fluoro-1'-(3-fluorophenyl)-n,n-dimethylspiro[2,3,4,9-tetrahydropyrido[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1CC2(C3=C(C4=CC=CC=C4N3)CCN2)CC(F)C1(N(C)C)C1=CC=CC(F)=C1 VMWCVNRWKYXQMS-UHFFFAOYSA-N 0.000 claims description 2
• JBGGXKNSLOKVFU-UHFFFAOYSA-N 2'-fluoro-n,n-dimethyl-1'-phenylspiro[2,3,4,9-tetrahydropyrido[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1CC2(C3=C(C4=CC=CC=C4N3)CCN2)CC(F)C1(N(C)C)C1=CC=CC=C1 JBGGXKNSLOKVFU-UHFFFAOYSA-N 0.000 claims description 2
• GCNWPMUGPBWWBO-UHFFFAOYSA-N 2'-fluoro-n,n-dimethyl-1'-phenylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1CC2(C3=C(C4=CC=CC=C4N3)CCO2)CC(F)C1(N(C)C)C1=CC=CC=C1 GCNWPMUGPBWWBO-UHFFFAOYSA-N 0.000 claims description 2
• YTPXABNEHGWOPC-UHFFFAOYSA-N 3',3',6-trifluoro-n-methyl-1'-phenylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1CC2(C3=C(C4=CC(F)=CC=C4N3)CCO2)C(F)(F)CC1(NC)C1=CC=CC=C1 YTPXABNEHGWOPC-UHFFFAOYSA-N 0.000 claims description 2
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• MECBATGCGBSPMO-UHFFFAOYSA-N 3',6-difluoro-n-methyl-1'-phenylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1CC2(C3=C(C4=CC(F)=CC=C4N3)CCO2)C(F)CC1(NC)C1=CC=CC=C1 MECBATGCGBSPMO-UHFFFAOYSA-N 0.000 claims description 2
• PFTQUJMDHFHCOT-UHFFFAOYSA-N 3'-(4-fluorophenyl)-n,n-dimethyl-1'-phenylspiro[2,3,4,9-tetrahydropyrido[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1C(N(C)C)(C=2C=CC=CC=2)CCC2(C3=C(C4=CC=CC=C4N3)CCN2)C1C1=CC=C(F)C=C1 PFTQUJMDHFHCOT-UHFFFAOYSA-N 0.000 claims description 2
• AUDCNKWQWXLRMW-UHFFFAOYSA-N 3'-[(4-fluorophenyl)methyl]-n,n-dimethyl-1'-phenylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1C(N(C)C)(C=2C=CC=CC=2)CCC2(C3=C(C4=CC=CC=C4N3)CCO2)C1CC1=CC=C(F)C=C1 AUDCNKWQWXLRMW-UHFFFAOYSA-N 0.000 claims description 2
• HNRGFZLGEXVUCB-UHFFFAOYSA-N 3'-fluoro-1'-(3-fluorophenyl)-n,n-dimethylspiro[2,3,4,9-tetrahydropyrido[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1CC2(C3=C(C4=CC=CC=C4N3)CCN2)C(F)CC1(N(C)C)C1=CC=CC(F)=C1 HNRGFZLGEXVUCB-UHFFFAOYSA-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
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