AU2007205114B2 - Cycloalkylamines as monoamine reuptake inhibitors - Google Patents
Cycloalkylamines as monoamine reuptake inhibitors Download PDFInfo
- Publication number
- AU2007205114B2 AU2007205114B2 AU2007205114A AU2007205114A AU2007205114B2 AU 2007205114 B2 AU2007205114 B2 AU 2007205114B2 AU 2007205114 A AU2007205114 A AU 2007205114A AU 2007205114 A AU2007205114 A AU 2007205114A AU 2007205114 B2 AU2007205114 B2 AU 2007205114B2
- Authority
- AU
- Australia
- Prior art keywords
- dichlorophenyl
- methyl
- cyclohexyl
- cyclohexanol
- cis
- 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.)
- Ceased
Links
- 239000003112 inhibitor Substances 0.000 title description 7
- 230000000407 monoamine reuptake Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 326
- 238000000034 method Methods 0.000 claims abstract description 251
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 24
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 23
- 208000019116 sleep disease Diseases 0.000 claims abstract description 11
- 208000019901 Anxiety disease Diseases 0.000 claims abstract description 10
- 230000036506 anxiety Effects 0.000 claims abstract description 9
- 201000000980 schizophrenia Diseases 0.000 claims abstract description 9
- 208000020685 sleep-wake disease Diseases 0.000 claims abstract description 9
- 210000003169 central nervous system Anatomy 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims description 170
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 75
- 150000003839 salts Chemical class 0.000 claims description 74
- 125000000217 alkyl group Chemical group 0.000 claims description 56
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 39
- 239000003814 drug Substances 0.000 claims description 30
- 238000002360 preparation method Methods 0.000 claims description 29
- 229910052736 halogen Inorganic materials 0.000 claims description 28
- 150000002367 halogens Chemical class 0.000 claims description 27
- 208000015114 central nervous system disease Diseases 0.000 claims description 26
- 208000002193 Pain Diseases 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 25
- 208000012902 Nervous system disease Diseases 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 16
- 125000004429 atom Chemical group 0.000 claims description 16
- XAXLSVQFDZVYNG-UHFFFAOYSA-N 1-[1-(3,4-dichlorophenyl)cyclohexyl]ethanamine Chemical compound C=1C=C(Cl)C(Cl)=CC=1C1(C(N)C)CCCCC1 XAXLSVQFDZVYNG-UHFFFAOYSA-N 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 208000035475 disorder Diseases 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 13
- 208000024714 major depressive disease Diseases 0.000 claims description 13
- 230000004770 neurodegeneration Effects 0.000 claims description 13
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 13
- ZJNJPYFFMXVAGY-UHFFFAOYSA-N 1-[1-(3,4-dichlorophenyl)cyclohexyl]-n-methylethanamine Chemical compound C=1C=C(Cl)C(Cl)=CC=1C1(C(C)NC)CCCCC1 ZJNJPYFFMXVAGY-UHFFFAOYSA-N 0.000 claims description 12
- 239000012453 solvate Substances 0.000 claims description 12
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 11
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 10
- 208000012672 seasonal affective disease Diseases 0.000 claims description 10
- 208000001640 Fibromyalgia Diseases 0.000 claims description 9
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
- OMVGECAOWGXULY-UHFFFAOYSA-N [1-[4-(trifluoromethoxy)phenyl]cyclohexyl]methanamine Chemical compound C=1C=C(OC(F)(F)F)C=CC=1C1(CN)CCCCC1 OMVGECAOWGXULY-UHFFFAOYSA-N 0.000 claims description 8
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 7
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 7
- 150000002431 hydrogen Chemical group 0.000 claims description 7
- DIOWQSMFSBKMCS-UHFFFAOYSA-N n,n-dimethyl-1-(1-naphthalen-2-ylcyclohexyl)ethanamine Chemical compound C=1C=C2C=CC=CC2=CC=1C1(C(N(C)C)C)CCCCC1 DIOWQSMFSBKMCS-UHFFFAOYSA-N 0.000 claims description 7
- 208000004296 neuralgia Diseases 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 208000028173 post-traumatic stress disease Diseases 0.000 claims description 7
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 6
- 206010013954 Dysphoria Diseases 0.000 claims description 6
- 208000018737 Parkinson disease Diseases 0.000 claims description 6
- 208000005793 Restless legs syndrome Diseases 0.000 claims description 6
- AWFDYLNQFMKXDE-UHFFFAOYSA-N [1-(3,4-difluorophenyl)cyclohexyl]methanamine;hydrochloride Chemical compound Cl.C=1C=C(F)C(F)=CC=1C1(CN)CCCCC1 AWFDYLNQFMKXDE-UHFFFAOYSA-N 0.000 claims description 6
- 230000007278 cognition impairment Effects 0.000 claims description 6
- 208000024732 dysthymic disease Diseases 0.000 claims description 6
- OMEZNRIAKKKRHT-UHFFFAOYSA-N n-methyl-1-[1-[4-(trifluoromethyl)phenyl]cyclohexyl]methanamine Chemical compound C=1C=C(C(F)(F)F)C=CC=1C1(CNC)CCCCC1 OMEZNRIAKKKRHT-UHFFFAOYSA-N 0.000 claims description 6
- 208000021722 neuropathic pain Diseases 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- RZJVBWDUILULEO-UHFFFAOYSA-N 1-[1-(3,4-dichlorophenyl)cyclohexyl]-n-methylpropan-1-amine Chemical compound C=1C=C(Cl)C(Cl)=CC=1C1(C(NC)CC)CCCCC1 RZJVBWDUILULEO-UHFFFAOYSA-N 0.000 claims description 5
- FLAQOJMPRHHQFA-UHFFFAOYSA-N 1-[1-(3-chloro-4-fluorophenyl)cyclohexyl]-n-methylmethanamine Chemical compound C=1C=C(F)C(Cl)=CC=1C1(CNC)CCCCC1 FLAQOJMPRHHQFA-UHFFFAOYSA-N 0.000 claims description 5
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 5
- PXJDTWINCCFEMX-UHFFFAOYSA-N 3-(aminomethyl)-3-(3,4-dichlorophenyl)cyclohexan-1-ol Chemical compound C=1C=C(Cl)C(Cl)=CC=1C1(CN)CCCC(O)C1 PXJDTWINCCFEMX-UHFFFAOYSA-N 0.000 claims description 5
- 208000020925 Bipolar disease Diseases 0.000 claims description 5
- PGGTUNCWXAFOIJ-UHFFFAOYSA-N [1-[4-(trifluoromethyl)phenyl]cyclohexyl]methanamine Chemical compound C=1C=C(C(F)(F)F)C=CC=1C1(CN)CCCCC1 PGGTUNCWXAFOIJ-UHFFFAOYSA-N 0.000 claims description 5
- WISXSHNMYCUZHH-UHFFFAOYSA-N n-methyl-1-(1-naphthalen-2-ylcyclohexyl)ethanamine Chemical compound C=1C=C2C=CC=CC2=CC=1C1(C(C)NC)CCCCC1 WISXSHNMYCUZHH-UHFFFAOYSA-N 0.000 claims description 5
- YNJHBZUBKJKAEC-UHFFFAOYSA-N n-methyl-1-[1-[3-(trifluoromethyl)phenyl]cyclohexyl]methanamine Chemical compound C=1C=CC(C(F)(F)F)=CC=1C1(CNC)CCCCC1 YNJHBZUBKJKAEC-UHFFFAOYSA-N 0.000 claims description 5
- ZZZAXWVNEPCNQE-UHFFFAOYSA-N n-methyl-1-[1-[4-(trifluoromethoxy)phenyl]cyclohexyl]ethanamine Chemical compound C=1C=C(OC(F)(F)F)C=CC=1C1(C(C)NC)CCCCC1 ZZZAXWVNEPCNQE-UHFFFAOYSA-N 0.000 claims description 5
- SAARGPSTPXUSIL-UHFFFAOYSA-N (1-naphthalen-2-ylcyclohexyl)methanamine Chemical compound C=1C=C2C=CC=CC2=CC=1C1(CN)CCCCC1 SAARGPSTPXUSIL-UHFFFAOYSA-N 0.000 claims description 4
- GXDMUUDAPHURSU-UHFFFAOYSA-N 1-(1-naphthalen-2-ylcyclohexyl)ethanamine Chemical compound C=1C=C2C=CC=CC2=CC=1C1(C(N)C)CCCCC1 GXDMUUDAPHURSU-UHFFFAOYSA-N 0.000 claims description 4
- JLKOYRAHLGKMSS-UHFFFAOYSA-N 1-[1-(3,4-dichlorophenyl)-3,3-difluorocyclohexyl]-n,n-dimethylmethanamine Chemical compound C=1C=C(Cl)C(Cl)=CC=1C1(CN(C)C)CCCC(F)(F)C1 JLKOYRAHLGKMSS-UHFFFAOYSA-N 0.000 claims description 4
- WCZIJHPZMNUQAK-UHFFFAOYSA-N 1-[1-(3,4-dichlorophenyl)-3,3-difluorocyclohexyl]-n-methylmethanamine Chemical compound C=1C=C(Cl)C(Cl)=CC=1C1(CNC)CCCC(F)(F)C1 WCZIJHPZMNUQAK-UHFFFAOYSA-N 0.000 claims description 4
- POKCWLLPLOIIOW-UHFFFAOYSA-N 1-[1-(3,4-dichlorophenyl)cyclohexyl]-n,3-dimethylbutan-1-amine Chemical compound C=1C=C(Cl)C(Cl)=CC=1C1(C(CC(C)C)NC)CCCCC1 POKCWLLPLOIIOW-UHFFFAOYSA-N 0.000 claims description 4
- PKNHHRUELROULR-UHFFFAOYSA-N 1-[1-(3,4-dichlorophenyl)cyclohexyl]-n,n,3-trimethylbutan-1-amine Chemical compound C=1C=C(Cl)C(Cl)=CC=1C1(C(N(C)C)CC(C)C)CCCCC1 PKNHHRUELROULR-UHFFFAOYSA-N 0.000 claims description 4
- TWJMQKQVQPFYPD-UHFFFAOYSA-N 1-[1-(3,4-dichlorophenyl)cyclohexyl]pentan-1-amine Chemical compound C=1C=C(Cl)C(Cl)=CC=1C1(C(N)CCCC)CCCCC1 TWJMQKQVQPFYPD-UHFFFAOYSA-N 0.000 claims description 4
- JKRXUDRMEIXFBV-UHFFFAOYSA-N 1-[1-(3,4-dichlorophenyl)cyclohexyl]propan-1-amine Chemical compound C=1C=C(Cl)C(Cl)=CC=1C1(C(N)CC)CCCCC1 JKRXUDRMEIXFBV-UHFFFAOYSA-N 0.000 claims description 4
- FGMVBSZPVPCFKQ-UHFFFAOYSA-N 1-[1-(3-chloro-4-fluorophenyl)cyclohexyl]-n,n-dimethylmethanamine Chemical compound C=1C=C(F)C(Cl)=CC=1C1(CN(C)C)CCCCC1 FGMVBSZPVPCFKQ-UHFFFAOYSA-N 0.000 claims description 4
- SDFJAHVREUGWBK-UHFFFAOYSA-N 1-[1-(4-chloro-3-fluorophenyl)cyclohexyl]-n-methylmethanamine Chemical compound C=1C=C(Cl)C(F)=CC=1C1(CNC)CCCCC1 SDFJAHVREUGWBK-UHFFFAOYSA-N 0.000 claims description 4
- ZQWDWCAENNSUNH-UHFFFAOYSA-N 1-[1-(6-fluoronaphthalen-2-yl)cyclohexyl]-n,n-dimethylmethanamine Chemical compound C=1C=C2C=C(F)C=CC2=CC=1C1(CN(C)C)CCCCC1 ZQWDWCAENNSUNH-UHFFFAOYSA-N 0.000 claims description 4
- UGQDLLYCIMKVNZ-UHFFFAOYSA-N 1-[1-(6-fluoronaphthalen-2-yl)cyclohexyl]-n-methylmethanamine Chemical compound C=1C=C2C=C(F)C=CC2=CC=1C1(CNC)CCCCC1 UGQDLLYCIMKVNZ-UHFFFAOYSA-N 0.000 claims description 4
- VRVDHYBVMARMIQ-UHFFFAOYSA-N 1-[1-[4-(trifluoromethoxy)phenyl]cyclohexyl]ethanamine Chemical compound C=1C=C(OC(F)(F)F)C=CC=1C1(C(N)C)CCCCC1 VRVDHYBVMARMIQ-UHFFFAOYSA-N 0.000 claims description 4
- NYMYBTSHTBHJMY-UHFFFAOYSA-N 1-[[1-(3,4-dichlorophenyl)cyclohexyl]methyl]-2-methylpyrrolidine Chemical compound CC1CCCN1CC1(C=2C=C(Cl)C(Cl)=CC=2)CCCCC1 NYMYBTSHTBHJMY-UHFFFAOYSA-N 0.000 claims description 4
- MIXZVBKGNPUNLK-UHFFFAOYSA-N 1-[[1-(3,4-dichlorophenyl)cyclohexyl]methyl]-3-methylpiperidine Chemical compound C1C(C)CCCN1CC1(C=2C=C(Cl)C(Cl)=CC=2)CCCCC1 MIXZVBKGNPUNLK-UHFFFAOYSA-N 0.000 claims description 4
- FSYUMFOIUHBSHI-UHFFFAOYSA-N 1-[[1-(3,4-dichlorophenyl)cyclohexyl]methyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1CC1(C=2C=C(Cl)C(Cl)=CC=2)CCCCC1 FSYUMFOIUHBSHI-UHFFFAOYSA-N 0.000 claims description 4
- QQKNLGCYRCQFQP-UHFFFAOYSA-N 1-[[1-(3,4-dichlorophenyl)cyclohexyl]methyl]piperidine Chemical compound C1=C(Cl)C(Cl)=CC=C1C1(CN2CCCCC2)CCCCC1 QQKNLGCYRCQFQP-UHFFFAOYSA-N 0.000 claims description 4
- YWOVEHIRDVATGZ-UHFFFAOYSA-N 1-[[1-(3,4-dichlorophenyl)cyclohexyl]methyl]pyrrolidine Chemical compound C1=C(Cl)C(Cl)=CC=C1C1(CN2CCCC2)CCCCC1 YWOVEHIRDVATGZ-UHFFFAOYSA-N 0.000 claims description 4
- NAENGEZVKXADGC-UHFFFAOYSA-N 3-(aminomethyl)-3-(3,4-dichlorophenyl)-1-methylcyclohexan-1-ol Chemical compound C1C(C)(O)CCCC1(CN)C1=CC=C(Cl)C(Cl)=C1 NAENGEZVKXADGC-UHFFFAOYSA-N 0.000 claims description 4
- YOVGBLUPSNTJCU-UHFFFAOYSA-N 4-[[1-(3,4-dichlorophenyl)cyclohexyl]methyl]morpholine Chemical compound C1=C(Cl)C(Cl)=CC=C1C1(CN2CCOCC2)CCCCC1 YOVGBLUPSNTJCU-UHFFFAOYSA-N 0.000 claims description 4
- 208000020401 Depressive disease Diseases 0.000 claims description 4
- SVGMBLIFYWKNDC-UHFFFAOYSA-N [1-(3,4-dichlorophenyl)-3,3-difluorocyclohexyl]methanamine Chemical compound C=1C=C(Cl)C(Cl)=CC=1C1(CN)CCCC(F)(F)C1 SVGMBLIFYWKNDC-UHFFFAOYSA-N 0.000 claims description 4
- NOIYKRBEALMMGJ-UHFFFAOYSA-N [1-(3,4-dichlorophenyl)cyclohexyl]methanamine;hydrochloride Chemical compound Cl.C=1C=C(Cl)C(Cl)=CC=1C1(CN)CCCCC1 NOIYKRBEALMMGJ-UHFFFAOYSA-N 0.000 claims description 4
- KPLAPMIQSJDNJP-UHFFFAOYSA-N [1-(3-chloro-4-fluorophenyl)cyclohexyl]methanamine Chemical compound C=1C=C(F)C(Cl)=CC=1C1(CN)CCCCC1 KPLAPMIQSJDNJP-UHFFFAOYSA-N 0.000 claims description 4
- GYNBJBPUCVZGTH-UHFFFAOYSA-N [1-(4-chloro-3-fluorophenyl)cyclohexyl]methanamine Chemical compound C=1C=C(Cl)C(F)=CC=1C1(CN)CCCCC1 GYNBJBPUCVZGTH-UHFFFAOYSA-N 0.000 claims description 4
- XZUTVZVXEKNHHN-UHFFFAOYSA-N [1-(6-fluoronaphthalen-2-yl)cyclohexyl]methanamine Chemical compound C=1C=C2C=C(F)C=CC2=CC=1C1(CN)CCCCC1 XZUTVZVXEKNHHN-UHFFFAOYSA-N 0.000 claims description 4
- MILNRKCCACSUTQ-UHFFFAOYSA-N [2-(3,4-dichlorophenyl)-2-(ethylaminomethyl)cyclohexyl]methanol Chemical compound C=1C=C(Cl)C(Cl)=CC=1C1(CNCC)CCCCC1CO MILNRKCCACSUTQ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- SWBCLQGKCJMOJJ-UHFFFAOYSA-N n,n-dimethyl-1-(1-naphthalen-2-ylcyclohexyl)methanamine Chemical compound C=1C=C2C=CC=CC2=CC=1C1(CN(C)C)CCCCC1 SWBCLQGKCJMOJJ-UHFFFAOYSA-N 0.000 claims description 4
- SYDXJSKTVHXBGQ-UHFFFAOYSA-N n,n-dimethyl-1-[1-[3-(trifluoromethyl)phenyl]cyclohexyl]methanamine Chemical compound C=1C=CC(C(F)(F)F)=CC=1C1(CN(C)C)CCCCC1 SYDXJSKTVHXBGQ-UHFFFAOYSA-N 0.000 claims description 4
- OUELOCGOICYILN-UHFFFAOYSA-N n,n-dimethyl-1-[1-[4-(trifluoromethoxy)phenyl]cyclohexyl]ethanamine Chemical compound C=1C=C(OC(F)(F)F)C=CC=1C1(C(N(C)C)C)CCCCC1 OUELOCGOICYILN-UHFFFAOYSA-N 0.000 claims description 4
- TVDNUGUVGACHFB-UHFFFAOYSA-N n-methyl-1-(1-naphthalen-2-ylcyclohexyl)methanamine Chemical compound C=1C=C2C=CC=CC2=CC=1C1(CNC)CCCCC1 TVDNUGUVGACHFB-UHFFFAOYSA-N 0.000 claims description 4
- 201000002859 sleep apnea Diseases 0.000 claims description 4
- MSRLFKAAHSYYJT-UHFFFAOYSA-N 1-[1-(3,4-dichlorophenyl)cyclohexyl]-n,n-dimethylmethanamine Chemical compound C=1C=C(Cl)C(Cl)=CC=1C1(CN(C)C)CCCCC1 MSRLFKAAHSYYJT-UHFFFAOYSA-N 0.000 claims description 3
- ZJAQALVESRZXBW-UHFFFAOYSA-N 1-[1-(3,4-dichlorophenyl)cyclohexyl]-n,n-dimethylpropan-1-amine Chemical compound C=1C=C(Cl)C(Cl)=CC=1C1(C(N(C)C)CC)CCCCC1 ZJAQALVESRZXBW-UHFFFAOYSA-N 0.000 claims description 3
- NDMODESSMWGHBK-UHFFFAOYSA-N 1-[1-(3,4-dichlorophenyl)cyclohexyl]-n-methylmethanamine Chemical compound C=1C=C(Cl)C(Cl)=CC=1C1(CNC)CCCCC1 NDMODESSMWGHBK-UHFFFAOYSA-N 0.000 claims description 3
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 3
- 201000003104 endogenous depression Diseases 0.000 claims description 3
- QIYANFXIRPCCFR-UHFFFAOYSA-N n,n-dimethyl-1-[1-[4-(trifluoromethyl)phenyl]cyclohexyl]methanamine Chemical compound C=1C=C(C(F)(F)F)C=CC=1C1(CN(C)C)CCCCC1 QIYANFXIRPCCFR-UHFFFAOYSA-N 0.000 claims description 3
- ZXAIYPYVRUXIRT-UHFFFAOYSA-N n-[[1-(3,4-dichlorophenyl)cyclohexyl]methyl]-n-ethylethanamine Chemical compound C=1C=C(Cl)C(Cl)=CC=1C1(CN(CC)CC)CCCCC1 ZXAIYPYVRUXIRT-UHFFFAOYSA-N 0.000 claims description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- HMFJEFLRHYKEQB-UHFFFAOYSA-N (4-fluoro-1-naphthalen-2-ylcyclohexyl)methanamine Chemical compound C=1C=C2C=CC=CC2=CC=1C1(CN)CCC(F)CC1 HMFJEFLRHYKEQB-UHFFFAOYSA-N 0.000 claims 4
- ZZUJFHUPDOBMOH-UHFFFAOYSA-N 1-(4-fluoro-1-naphthalen-2-ylcyclohexyl)-n,n-dimethylmethanamine Chemical compound C=1C=C2C=CC=CC2=CC=1C1(CN(C)C)CCC(F)CC1 ZZUJFHUPDOBMOH-UHFFFAOYSA-N 0.000 claims 4
- KAQUOFCNEYORCQ-UHFFFAOYSA-N 1-(4-fluoro-1-naphthalen-2-ylcyclohexyl)-n-methylmethanamine Chemical compound C=1C=C2C=CC=CC2=CC=1C1(CNC)CCC(F)CC1 KAQUOFCNEYORCQ-UHFFFAOYSA-N 0.000 claims 4
- FNPNFDUAOLYGJY-UHFFFAOYSA-N 1-[1-(3,4-dichlorophenyl)-4-methoxycyclohexyl]-n,n-dimethylmethanamine Chemical compound C1CC(OC)CCC1(CN(C)C)C1=CC=C(Cl)C(Cl)=C1 FNPNFDUAOLYGJY-UHFFFAOYSA-N 0.000 claims 4
- DQKBPLZDDANEEL-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-1-ethyl-4-(methylaminomethyl)cyclohexan-1-ol Chemical compound C1CC(CC)(O)CCC1(CNC)C1=CC=C(Cl)C(Cl)=C1 DQKBPLZDDANEEL-UHFFFAOYSA-N 0.000 claims 4
- IEEXXKGDHWBIJX-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-1-methyl-4-(methylaminomethyl)cyclohexan-1-ol Chemical compound C=1C=C(Cl)C(Cl)=CC=1C1(CNC)CCC(C)(O)CC1 IEEXXKGDHWBIJX-UHFFFAOYSA-N 0.000 claims 4
- SJTJLLXHBQCTJD-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-4-[(dimethylamino)methyl]-1-ethylcyclohexan-1-ol Chemical compound C1CC(CC)(O)CCC1(CN(C)C)C1=CC=C(Cl)C(Cl)=C1 SJTJLLXHBQCTJD-UHFFFAOYSA-N 0.000 claims 4
- BLESHHZNRPCXQQ-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-4-[(dimethylamino)methyl]-1-methylcyclohexan-1-ol Chemical compound C=1C=C(Cl)C(Cl)=CC=1C1(CN(C)C)CCC(C)(O)CC1 BLESHHZNRPCXQQ-UHFFFAOYSA-N 0.000 claims 4
- FXSIBECSKQPADN-UHFFFAOYSA-N 4-(aminomethyl)-1-(fluoromethyl)-4-naphthalen-2-ylcyclohexan-1-ol Chemical compound C=1C=C2C=CC=CC2=CC=1C1(CN)CCC(O)(CF)CC1 FXSIBECSKQPADN-UHFFFAOYSA-N 0.000 claims 4
- LZGLGBOOTDKOQF-UHFFFAOYSA-N 4-(aminomethyl)-4-(3,4-dichlorophenyl)-1-ethylcyclohexan-1-ol Chemical compound C1CC(CC)(O)CCC1(CN)C1=CC=C(Cl)C(Cl)=C1 LZGLGBOOTDKOQF-UHFFFAOYSA-N 0.000 claims 4
- AGRAHYYFJIILCF-UHFFFAOYSA-N 4-(aminomethyl)-4-(3,4-dichlorophenyl)-1-methylcyclohexan-1-ol Chemical compound C1CC(C)(O)CCC1(CN)C1=CC=C(Cl)C(Cl)=C1 AGRAHYYFJIILCF-UHFFFAOYSA-N 0.000 claims 4
- HASNBQPSUGYJNL-UHFFFAOYSA-N 4-(aminomethyl)-4-naphthalen-2-ylcyclohexan-1-ol Chemical compound C=1C=C2C=CC=CC2=CC=1C1(CN)CCC(O)CC1 HASNBQPSUGYJNL-UHFFFAOYSA-N 0.000 claims 4
- AQVVHKDUJBMBFP-UHFFFAOYSA-N 4-(methylaminomethyl)-4-naphthalen-2-ylcyclohexan-1-ol Chemical compound C=1C=C2C=CC=CC2=CC=1C1(CNC)CCC(O)CC1 AQVVHKDUJBMBFP-UHFFFAOYSA-N 0.000 claims 4
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
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- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
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- 2007-01-05 ES ES07716419.2T patent/ES2594156T3/es active Active
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- 2007-01-05 RU RU2008132320A patent/RU2430913C2/ru active
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| RU2430913C2 (ru) | 2011-10-10 |
| US20150126511A1 (en) | 2015-05-07 |
| AU2007205114A1 (en) | 2007-07-19 |
| CA2636324A1 (en) | 2007-07-19 |
| RU2008132320A (ru) | 2010-02-20 |
| EP1976513B1 (en) | 2016-08-24 |
| JP5432526B2 (ja) | 2014-03-05 |
| JP2009531277A (ja) | 2009-09-03 |
| ZA200806145B (en) | 2010-02-24 |
| NZ569630A (en) | 2011-09-30 |
| US9868718B2 (en) | 2018-01-16 |
| RU2011119990A (ru) | 2012-11-27 |
| KR20080083201A (ko) | 2008-09-16 |
| KR101294014B1 (ko) | 2013-08-09 |
| US20180230120A1 (en) | 2018-08-16 |
| WO2007081857A2 (en) | 2007-07-19 |
| CN101394847B (zh) | 2017-05-24 |
| EP1976513A4 (en) | 2012-04-18 |
| ES2594156T3 (es) | 2016-12-16 |
| IL192613A (en) | 2015-11-30 |
| US10562878B2 (en) | 2020-02-18 |
| CN101394847A (zh) | 2009-03-25 |
| EP1976513A2 (en) | 2008-10-08 |
| BRPI0706365A2 (pt) | 2011-03-22 |
| WO2007081857A3 (en) | 2007-11-08 |
| US8877975B2 (en) | 2014-11-04 |
| US20070203111A1 (en) | 2007-08-30 |
| US20100190861A1 (en) | 2010-07-29 |
| JP2013209390A (ja) | 2013-10-10 |
| IL192613A0 (en) | 2009-09-22 |
| CA2636324C (en) | 2012-03-20 |
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