SK286836B6 - Substituované deriváty aminometyl-fenyl-cyklohexánu, spôsob ich výroby, liečivá tieto zlúčeniny obsahujúce a ich použitie - Google Patents
Substituované deriváty aminometyl-fenyl-cyklohexánu, spôsob ich výroby, liečivá tieto zlúčeniny obsahujúce a ich použitie Download PDFInfo
- Publication number
- SK286836B6 SK286836B6 SK981-2002A SK9812002A SK286836B6 SK 286836 B6 SK286836 B6 SK 286836B6 SK 9812002 A SK9812002 A SK 9812002A SK 286836 B6 SK286836 B6 SK 286836B6
- Authority
- SK
- Slovakia
- Prior art keywords
- dimethylaminomethyl
- methoxyphenyl
- rac
- benzoic acid
- group
- Prior art date
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- ULRBJKIRTCBMRW-UHFFFAOYSA-N (1-phenylcyclohexyl)methanamine Chemical class C=1C=CC=CC=1C1(CN)CCCCC1 ULRBJKIRTCBMRW-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 239000003814 drug Substances 0.000 title claims abstract description 21
- 150000001875 compounds Chemical class 0.000 title claims description 27
- 238000004519 manufacturing process Methods 0.000 title claims description 18
- 229940079593 drug Drugs 0.000 claims abstract description 4
- 208000007848 Alcoholism Diseases 0.000 claims abstract description 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 3
- 206010011224 Cough Diseases 0.000 claims abstract description 3
- 206010013654 Drug abuse Diseases 0.000 claims abstract description 3
- 208000007882 Gastritis Diseases 0.000 claims abstract description 3
- 206010020751 Hypersensitivity Diseases 0.000 claims abstract description 3
- 206010061218 Inflammation Diseases 0.000 claims abstract description 3
- 206010001584 alcohol abuse Diseases 0.000 claims abstract description 3
- 208000025746 alcohol use disease Diseases 0.000 claims abstract description 3
- 206010015037 epilepsy Diseases 0.000 claims abstract description 3
- 230000002757 inflammatory effect Effects 0.000 claims abstract description 3
- 208000020016 psychiatric disease Diseases 0.000 claims abstract description 3
- 208000011117 substance-related disease Diseases 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 195
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 165
- -1 rac- trans-Z-3- [4-dimethylaminomethyl-3- (3-methoxyphenyl) cyclohexylidene-methyl] benzoic acid rac-trans-E-3- [4-dimethylaminomethyl-3- (3-methoxyphenyl) cyclohexylidene-methyl] benzoic acid Chemical compound 0.000 claims description 122
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 99
- 239000005711 Benzoic acid Substances 0.000 claims description 96
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 88
- 235000010233 benzoic acid Nutrition 0.000 claims description 78
- 239000002585 base Substances 0.000 claims description 70
- 239000001257 hydrogen Substances 0.000 claims description 66
- 229910052739 hydrogen Inorganic materials 0.000 claims description 66
- 125000000217 alkyl group Chemical group 0.000 claims description 62
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 60
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 57
- 125000003342 alkenyl group Chemical group 0.000 claims description 47
- 125000000304 alkynyl group Chemical group 0.000 claims description 47
- 229910052799 carbon Inorganic materials 0.000 claims description 44
- 229920006395 saturated elastomer Polymers 0.000 claims description 43
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 40
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 35
- QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 35
- 229910052760 oxygen Inorganic materials 0.000 claims description 34
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 29
- 239000001301 oxygen Substances 0.000 claims description 29
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 28
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 26
- 229910052731 fluorine Inorganic materials 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 25
- 229910052801 chlorine Inorganic materials 0.000 claims description 25
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 23
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 23
- 229910052717 sulfur Inorganic materials 0.000 claims description 23
- 239000011593 sulfur Substances 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 22
- 239000011737 fluorine Substances 0.000 claims description 21
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 20
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 20
- 229910052794 bromium Inorganic materials 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- 239000000460 chlorine Substances 0.000 claims description 19
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 18
- 150000004702 methyl esters Chemical class 0.000 claims description 18
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 16
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 14
- 150000007513 acids Chemical class 0.000 claims description 13
- 150000003840 hydrochlorides Chemical class 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 208000002193 Pain Diseases 0.000 claims description 12
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 12
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 11
- 238000007239 Wittig reaction Methods 0.000 claims description 11
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- 230000036407 pain Effects 0.000 claims description 10
- YBUVQHYYHOZGGO-FDVLFSPDSA-N 3-[(e)-[(3r,4r)-4-[(dimethylamino)methyl]-3-(3-methoxyphenyl)cyclohexylidene]methyl]benzoic acid Chemical compound COC1=CC=CC([C@H]2[C@@H](CCC(/C2)=C\C=2C=C(C=CC=2)C(O)=O)CN(C)C)=C1 YBUVQHYYHOZGGO-FDVLFSPDSA-N 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- ZAOTZYDAHWQLIJ-VXKWHMMOSA-N CN(C)C[C@H]1[C@@H](CC(CC1)=C/C=1C=C(C(=O)O)C=CC1)C1=CC=CC=C1 Chemical compound CN(C)C[C@H]1[C@@H](CC(CC1)=C/C=1C=C(C(=O)O)C=CC1)C1=CC=CC=C1 ZAOTZYDAHWQLIJ-VXKWHMMOSA-N 0.000 claims description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 6
- FFSJEKPWJWWMFU-VIZOYTHASA-N 1-[(4e)-2-(3-methoxyphenyl)-4-propylidenecyclohex-2-en-1-yl]-n,n-dimethylmethanamine Chemical compound CC\C=C1/CCC(CN(C)C)C(C=2C=C(OC)C=CC=2)=C1 FFSJEKPWJWWMFU-VIZOYTHASA-N 0.000 claims description 5
- PDTFVNNHBFQIAG-LZYBPNLTSA-N 1-[(4e)-4-butylidene-2-(3-methoxyphenyl)cyclohex-2-en-1-yl]-n,n-dimethylmethanamine Chemical compound CCC\C=C1/CCC(CN(C)C)C(C=2C=C(OC)C=CC=2)=C1 PDTFVNNHBFQIAG-LZYBPNLTSA-N 0.000 claims description 5
- KEAFIFOBAFRWKR-UHFFFAOYSA-N 1-[2-(3-methoxyphenyl)-4-propan-2-ylidenecyclohex-2-en-1-yl]-n,n-dimethylmethanamine Chemical compound COC1=CC=CC(C=2C(CCC(C=2)=C(C)C)CN(C)C)=C1 KEAFIFOBAFRWKR-UHFFFAOYSA-N 0.000 claims description 5
- ZKOKCWFNIWRXFQ-PDGQHHTCSA-N 3-[(z)-[4-[(dimethylamino)methyl]-3-(3-methoxyphenyl)cyclohex-2-en-1-ylidene]methyl]benzoic acid Chemical compound COC1=CC=CC(C=2C(CCC(/C=2)=C/C=2C=C(C=CC=2)C(O)=O)CN(C)C)=C1 ZKOKCWFNIWRXFQ-PDGQHHTCSA-N 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000004494 ethyl ester group Chemical group 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- XFEYHOSPEZRHLP-PDGQHHTCSA-N methyl 3-[(z)-[4-[(dimethylamino)methyl]-3-(3-hydroxyphenyl)cyclohex-2-en-1-ylidene]methyl]benzoate Chemical compound COC(=O)C1=CC=CC(\C=C\2C=C(C(CN(C)C)CC/2)C=2C=C(O)C=CC=2)=C1 XFEYHOSPEZRHLP-PDGQHHTCSA-N 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- XWUNRYNRMAOMLL-UDLLKNRZSA-N 1-[(1r,2r,4e)-4-benzylidene-2-(3-methoxyphenyl)cyclohexyl]-n,n-dimethylmethanamine Chemical compound COC1=CC=CC([C@H]2[C@@H](CCC(/C2)=C\C=2C=CC=CC=2)CN(C)C)=C1 XWUNRYNRMAOMLL-UDLLKNRZSA-N 0.000 claims description 4
- LRCJLISEXSAJRV-QGOAFFKASA-N 1-[(4e)-4-[(4-chlorophenyl)methylidene]-2-(3-methoxyphenyl)cyclohex-2-en-1-yl]-n,n-dimethylmethanamine Chemical compound COC1=CC=CC(C=2C(CCC(/C=2)=C\C=2C=CC(Cl)=CC=2)CN(C)C)=C1 LRCJLISEXSAJRV-QGOAFFKASA-N 0.000 claims description 4
- RGJHPUWGXMRYDT-WQRHYEAKSA-N 3-[(5z)-2-[(dimethylamino)methyl]-5-[[3-(hydroxymethyl)phenyl]methylidene]cyclohexen-1-yl]phenol Chemical compound C1CC(CN(C)C)=C(C=2C=C(O)C=CC=2)C\C1=C/C1=CC=CC(CO)=C1 RGJHPUWGXMRYDT-WQRHYEAKSA-N 0.000 claims description 4
- ZKOKCWFNIWRXFQ-LDADJPATSA-N 3-[(e)-[4-[(dimethylamino)methyl]-3-(3-methoxyphenyl)cyclohex-2-en-1-ylidene]methyl]benzoic acid Chemical compound COC1=CC=CC(C=2C(CCC(/C=2)=C\C=2C=C(C=CC=2)C(O)=O)CN(C)C)=C1 ZKOKCWFNIWRXFQ-LDADJPATSA-N 0.000 claims description 4
- AIAXBQOUKAKNQT-UNMCSNQZSA-N CN(C)C[C@H]1[C@@H](CC(CC1)=C/C=1C=C(C(=O)O)C=CC1)C1=CC(=CC=C1)C(F)(F)F Chemical compound CN(C)C[C@H]1[C@@H](CC(CC1)=C/C=1C=C(C(=O)O)C=CC1)C1=CC(=CC=C1)C(F)(F)F AIAXBQOUKAKNQT-UNMCSNQZSA-N 0.000 claims description 4
- LNFGLRFDOFQLMN-SEJIEREQSA-N COC(C1=CC(=CC=C1)/C=C1/C[C@H]([C@@H](CC1)CN(C)C)C1=CC=CC=C1)=O Chemical compound COC(C1=CC(=CC=C1)/C=C1/C[C@H]([C@@H](CC1)CN(C)C)C1=CC=CC=C1)=O LNFGLRFDOFQLMN-SEJIEREQSA-N 0.000 claims description 4
- YTFCWMRQDKIXHH-AJHLYOENSA-N COC(C1=CC(=CC=C1)/C=C1/C[C@H]([C@H](CC1)CN(C)C)C1=CC(=CC=C1)OC)=O Chemical compound COC(C1=CC(=CC=C1)/C=C1/C[C@H]([C@H](CC1)CN(C)C)C1=CC(=CC=C1)OC)=O YTFCWMRQDKIXHH-AJHLYOENSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- CKLXGNSJQIFWCX-UPVQGACJSA-N [3-[(E)-[(3R,4R)-4-[(dimethylamino)methyl]-3-(3-methoxyphenyl)cyclohexylidene]methyl]phenyl]methanol Chemical compound CN(C)C[C@H]1[C@@H](CC(CC1)=CC=1C=C(C=CC1)CO)C1=CC(=CC=C1)OC CKLXGNSJQIFWCX-UPVQGACJSA-N 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- GMXBFVANGQDTHM-XSFVSMFZSA-N methyl 3-[(e)-[4-[(dimethylamino)methyl]-3-(3-methoxyphenyl)-2-methylcyclohex-2-en-1-ylidene]methyl]benzoate Chemical compound COC(=O)C1=CC=CC(\C=C/2C(=C(C(CN(C)C)CC\2)C=2C=C(OC)C=CC=2)C)=C1 GMXBFVANGQDTHM-XSFVSMFZSA-N 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 claims description 4
- XWUNRYNRMAOMLL-APKUOOJESA-N 1-[(1r,2s,4z)-4-benzylidene-2-(3-methoxyphenyl)cyclohexyl]-n,n-dimethylmethanamine Chemical compound COC1=CC=CC([C@@H]2[C@@H](CCC(/C2)=C/C=2C=CC=CC=2)CN(C)C)=C1 XWUNRYNRMAOMLL-APKUOOJESA-N 0.000 claims description 3
- XDYNHGYEFOZFNS-AQTBWJFISA-N 1-[(4z)-4-[(4-fluorophenyl)methylidene]-2-(3-methoxyphenyl)cyclohex-2-en-1-yl]-n,n-dimethylmethanamine Chemical compound COC1=CC=CC(C=2C(CCC(/C=2)=C/C=2C=CC(F)=CC=2)CN(C)C)=C1 XDYNHGYEFOZFNS-AQTBWJFISA-N 0.000 claims description 3
- WIWUZKGBRABBQO-SFQUDFHCSA-N 3-[(3e)-3-[(4-chlorophenyl)methylidene]-6-[(dimethylamino)methyl]cyclohexen-1-yl]phenol Chemical compound C1=C(C=2C=C(O)C=CC=2)C(CN(C)C)CC\C1=C/C1=CC=C(Cl)C=C1 WIWUZKGBRABBQO-SFQUDFHCSA-N 0.000 claims description 3
- IRQOWQQKJKWVFF-JWGURIENSA-N 3-[(z)-[4-[(dimethylamino)methyl]-3-(3-methoxyphenyl)cyclohex-2-en-1-ylidene]methyl]-n,n-diethylbenzamide Chemical compound CCN(CC)C(=O)C1=CC=CC(\C=C\2C=C(C(CN(C)C)CC/2)C=2C=C(OC)C=CC=2)=C1 IRQOWQQKJKWVFF-JWGURIENSA-N 0.000 claims description 3
- YBUVQHYYHOZGGO-GGAORHGYSA-N CN(C)C[C@@H]1[C@@H](CC(CC1)=C/C=1C=C(C(=O)O)C=CC1)C1=CC(=CC=C1)OC Chemical compound CN(C)C[C@@H]1[C@@H](CC(CC1)=C/C=1C=C(C(=O)O)C=CC1)C1=CC(=CC=C1)OC YBUVQHYYHOZGGO-GGAORHGYSA-N 0.000 claims description 3
- ZAOTZYDAHWQLIJ-YADHBBJMSA-N CN(C)C[C@@H]1[C@@H](CC(CC1)=CC=1C=C(C(=O)O)C=CC1)C1=CC=CC=C1 Chemical compound CN(C)C[C@@H]1[C@@H](CC(CC1)=CC=1C=C(C(=O)O)C=CC1)C1=CC=CC=C1 ZAOTZYDAHWQLIJ-YADHBBJMSA-N 0.000 claims description 3
- YBUVQHYYHOZGGO-GMAHTHKFSA-N CN(C)C[C@H]1[C@@H](CC(CC1)=C/C=1C=C(C(=O)O)C=CC1)C1=CC(=CC=C1)OC Chemical compound CN(C)C[C@H]1[C@@H](CC(CC1)=C/C=1C=C(C(=O)O)C=CC1)C1=CC(=CC=C1)OC YBUVQHYYHOZGGO-GMAHTHKFSA-N 0.000 claims description 3
- YTFCWMRQDKIXHH-GYACYKCWSA-N COC(C1=CC(=CC=C1)/C=C1/C[C@H]([C@@H](CC1)CN(C)C)C1=CC(=CC=C1)OC)=O Chemical compound COC(C1=CC(=CC=C1)/C=C1/C[C@H]([C@@H](CC1)CN(C)C)C1=CC(=CC=C1)OC)=O YTFCWMRQDKIXHH-GYACYKCWSA-N 0.000 claims description 3
- YTFCWMRQDKIXHH-UPVQGACJSA-N COC(C1=CC(=CC=C1)C=C1/C[C@H]([C@@H](CC1)CN(C)C)C1=CC(=CC=C1)OC)=O Chemical compound COC(C1=CC(=CC=C1)C=C1/C[C@H]([C@@H](CC1)CN(C)C)C1=CC(=CC=C1)OC)=O YTFCWMRQDKIXHH-UPVQGACJSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 206010012735 Diarrhoea Diseases 0.000 claims description 3
- 208000003251 Pruritus Diseases 0.000 claims description 3
- 206010046543 Urinary incontinence Diseases 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 230000007803 itching Effects 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
- XWUNRYNRMAOMLL-GMAHTHKFSA-N 1-[(1R,2R)-4-benzylidene-2-(3-methoxyphenyl)cyclohexyl]-N,N-dimethylmethanamine Chemical compound COC1=CC=CC([C@H]2[C@@H](CCC(C2)=CC=2C=CC=CC=2)CN(C)C)=C1 XWUNRYNRMAOMLL-GMAHTHKFSA-N 0.000 claims description 2
- XWUNRYNRMAOMLL-HHMCTSDTSA-N 1-[(1r,2s,4e)-4-benzylidene-2-(3-methoxyphenyl)cyclohexyl]-n,n-dimethylmethanamine Chemical compound COC1=CC=CC([C@@H]2[C@@H](CCC(/C2)=C\C=2C=CC=CC=2)CN(C)C)=C1 XWUNRYNRMAOMLL-HHMCTSDTSA-N 0.000 claims description 2
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/74—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with rings other than six-membered aromatic rings being part of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/38—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to acyclic carbon atoms and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/30—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to hydrogen atoms or to acyclic carbon atoms
-
- 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
- C07C2601/14—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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pulmonology (AREA)
- Addiction (AREA)
- Psychiatry (AREA)
- Urology & Nephrology (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Rheumatology (AREA)
- Anesthesiology (AREA)
- Otolaryngology (AREA)
- Heart & Thoracic Surgery (AREA)
- Immunology (AREA)
- Dermatology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10000312A DE10000312A1 (de) | 2000-01-05 | 2000-01-05 | Substituierte Aminomethyl-Phenyl-Cyclohexanderivate |
| PCT/EP2000/013281 WO2001049654A2 (de) | 2000-01-05 | 2000-12-27 | Substituierte aminomethyl-phenyl-cyclohexanderivate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK9812002A3 SK9812002A3 (en) | 2003-02-04 |
| SK286836B6 true SK286836B6 (sk) | 2009-06-05 |
Family
ID=7626853
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK981-2002A SK286836B6 (sk) | 2000-01-05 | 2000-12-27 | Substituované deriváty aminometyl-fenyl-cyklohexánu, spôsob ich výroby, liečivá tieto zlúčeniny obsahujúce a ich použitie |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US6673794B2 (cs) |
| EP (1) | EP1246793B1 (cs) |
| JP (1) | JP2003519210A (cs) |
| KR (1) | KR20020063294A (cs) |
| CN (1) | CN100379719C (cs) |
| AR (1) | AR033506A1 (cs) |
| AT (1) | ATE282021T1 (cs) |
| AU (1) | AU780547B2 (cs) |
| BR (1) | BR0016942A (cs) |
| CA (1) | CA2396304A1 (cs) |
| CO (1) | CO5251382A1 (cs) |
| CZ (1) | CZ20022337A3 (cs) |
| DE (2) | DE10000312A1 (cs) |
| ES (1) | ES2231312T3 (cs) |
| HU (1) | HU225102B1 (cs) |
| IL (2) | IL150557A0 (cs) |
| MX (1) | MXPA02006700A (cs) |
| NO (1) | NO20022985L (cs) |
| NZ (1) | NZ520467A (cs) |
| PE (1) | PE20011044A1 (cs) |
| PL (1) | PL364873A1 (cs) |
| PT (1) | PT1246793E (cs) |
| RU (1) | RU2002120905A (cs) |
| SK (1) | SK286836B6 (cs) |
| WO (1) | WO2001049654A2 (cs) |
| ZA (1) | ZA200206151B (cs) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10049483A1 (de) * | 2000-09-29 | 2002-05-02 | Gruenenthal Gmbh | Substituierte 1-Aminobutan-3-ol-Derivate |
| DE10112198A1 (de) * | 2001-03-14 | 2002-09-19 | Gruenenthal Gmbh | Substituierte Dimethyl-[1-(1-phenyl-cyclohexyl)-piperidin-3-ylmethyl]-amine |
| DE10224107A1 (de) * | 2002-05-29 | 2003-12-11 | Gruenenthal Gmbh | Kombination ausgewählter Opioide mit anderen Wirkstoffen zur Therapie der Harninkontinenz |
| EP1562567B1 (de) | 2002-11-22 | 2017-06-14 | Grünenthal GmbH | Kombination ausgewählter analgetika mit cox ii-inhibitoren |
| US20040248979A1 (en) * | 2003-06-03 | 2004-12-09 | Dynogen Pharmaceuticals, Inc. | Method of treating lower urinary tract disorders |
| DE102005034973A1 (de) * | 2005-07-22 | 2007-02-15 | Grünenthal GmbH | Salz von Dimethylaminomethyl-phenyl-cyclohexan und dessen kristalline Formen |
| KR100684436B1 (ko) * | 2005-09-08 | 2007-02-16 | 주식회사 다원 | 항산화, 지질과산화 억제에 따른 항노화, 항염증 및 거담 활성을 갖는 단풍마 및 가시오가피 혼합추출물을 함유하는 조성물 |
| DE102005061428A1 (de) * | 2005-12-22 | 2007-08-16 | Grünenthal GmbH | Substituierte Cyclohexylmethyl-Derivate |
| DE102005061427A1 (de) * | 2005-12-22 | 2007-06-28 | Grünenthal GmbH | Substituierte Oxadiazol-Derivate |
| DE102005061430A1 (de) * | 2005-12-22 | 2007-07-05 | Grünenthal GmbH | Substituierte Imidazolin-Derivate |
| KR101581289B1 (ko) * | 2007-05-31 | 2015-12-31 | 세프라코 아이엔시. | 모노아민 재흡수 억제제로서 페닐 치환된 시클로알킬아민 |
| CN113197935B (zh) * | 2021-04-13 | 2022-06-24 | 开平健之源保健食品有限公司 | 一种厚朴提取物的提取方法 |
| CN120081750A (zh) * | 2025-05-06 | 2025-06-03 | 山东新华制药股份有限公司 | 3-[3-(二甲基氨基)甲基-1-环己烯-2-基]苯酚盐酸盐及其同分异构体的制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5223541A (en) * | 1991-09-13 | 1993-06-29 | Mcneilab, Inc. | Tramadol n-oxide material, enantiomers and compositions thereof, and their use |
| IL112569A (en) * | 1994-02-10 | 1999-12-22 | Wyeth John & Brother Ltd | Pharmaceutical compositions comprising cyclohexylamine derivatives certain such novel compounds and their preparation |
| DE4426245A1 (de) * | 1994-07-23 | 1996-02-22 | Gruenenthal Gmbh | 1-Phenyl-3-dimethylamino-propanverbindungen mit pharmakologischer Wirkung |
| DE19525137C2 (de) * | 1995-07-11 | 2003-02-27 | Gruenenthal Gmbh | 6-Dimethylaminomethyl-1-phenyl-cyclohexanverbin -dungen als Zwischenprodukte zur Herstellung pharmazeutischer Wirkstoffe |
| DE19547766A1 (de) * | 1995-12-20 | 1997-06-26 | Gruenenthal Gmbh | 1-Phenyl-2-dimethylaminomethyl-cyclohexan-1-ol-verbindungen als pharmazeutische Wirkstoffe |
| DE19857475A1 (de) * | 1998-12-14 | 2000-06-15 | Gruenenthal Gmbh | Substituierte Cycloheptene, deren Herstellung und Verwendung |
-
2000
- 2000-01-05 DE DE10000312A patent/DE10000312A1/de not_active Withdrawn
- 2000-12-27 DE DE50008626T patent/DE50008626D1/de not_active Expired - Lifetime
- 2000-12-27 PT PT00993710T patent/PT1246793E/pt unknown
- 2000-12-27 NZ NZ520467A patent/NZ520467A/en unknown
- 2000-12-27 CA CA002396304A patent/CA2396304A1/en not_active Abandoned
- 2000-12-27 RU RU2002120905/04A patent/RU2002120905A/ru not_active Application Discontinuation
- 2000-12-27 IL IL15055700A patent/IL150557A0/xx active IP Right Grant
- 2000-12-27 KR KR1020027008700A patent/KR20020063294A/ko not_active Withdrawn
- 2000-12-27 JP JP2001550194A patent/JP2003519210A/ja active Pending
- 2000-12-27 ES ES00993710T patent/ES2231312T3/es not_active Expired - Lifetime
- 2000-12-27 EP EP00993710A patent/EP1246793B1/de not_active Expired - Lifetime
- 2000-12-27 CN CNB008192650A patent/CN100379719C/zh not_active Expired - Fee Related
- 2000-12-27 SK SK981-2002A patent/SK286836B6/sk not_active IP Right Cessation
- 2000-12-27 AT AT00993710T patent/ATE282021T1/de active
- 2000-12-27 WO PCT/EP2000/013281 patent/WO2001049654A2/de active IP Right Grant
- 2000-12-27 HU HU0204001A patent/HU225102B1/hu not_active IP Right Cessation
- 2000-12-27 MX MXPA02006700A patent/MXPA02006700A/es active IP Right Grant
- 2000-12-27 PL PL00364873A patent/PL364873A1/xx not_active IP Right Cessation
- 2000-12-27 CZ CZ20022337A patent/CZ20022337A3/cs unknown
- 2000-12-27 AU AU28438/01A patent/AU780547B2/en not_active Ceased
- 2000-12-27 BR BR0016942-0A patent/BR0016942A/pt not_active Application Discontinuation
-
2001
- 2001-01-02 AR ARP010100009A patent/AR033506A1/es unknown
- 2001-01-04 CO CO01000528A patent/CO5251382A1/es not_active Application Discontinuation
- 2001-01-04 PE PE2001000010A patent/PE20011044A1/es not_active Application Discontinuation
-
2002
- 2002-06-20 NO NO20022985A patent/NO20022985L/no unknown
- 2002-07-03 IL IL150557A patent/IL150557A/en not_active IP Right Cessation
- 2002-07-05 US US10/189,190 patent/US6673794B2/en not_active Expired - Fee Related
- 2002-08-01 ZA ZA200206151A patent/ZA200206151B/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed due to non-payment of maintenance fees |
Effective date: 20091227 |