DE19937537A1 - Substituierte 2-Dialkylaminoalkylbiphenyl-Derivate - Google Patents
Substituierte 2-Dialkylaminoalkylbiphenyl-DerivateInfo
- Publication number
- DE19937537A1 DE19937537A1 DE19937537A DE19937537A DE19937537A1 DE 19937537 A1 DE19937537 A1 DE 19937537A1 DE 19937537 A DE19937537 A DE 19937537A DE 19937537 A DE19937537 A DE 19937537A DE 19937537 A1 DE19937537 A1 DE 19937537A1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- dimethylamine
- ylmethyl
- corresponding hydrochloride
- hydrochloride
- 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.)
- Withdrawn
Links
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 324
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 130
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 117
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 97
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 87
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 83
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 80
- 239000000203 mixture Substances 0.000 claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 43
- 239000002253 acid Substances 0.000 claims description 42
- -1 acetamidyl Chemical group 0.000 claims description 41
- 239000003814 drug Substances 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 20
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- 238000004519 manufacturing process Methods 0.000 claims description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 14
- 150000003254 radicals Chemical class 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 12
- 208000002193 Pain Diseases 0.000 claims description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical class [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 11
- 229940079593 drug Drugs 0.000 claims description 11
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 10
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 10
- 230000036407 pain Effects 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- 238000006555 catalytic reaction Methods 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- ATBFEBMKNZQVRM-UHFFFAOYSA-N 2-[2-(3-methoxyphenyl)phenyl]-n,n-dimethylethanamine;hydrochloride Chemical compound Cl.COC1=CC=CC(C=2C(=CC=CC=2)CCN(C)C)=C1 ATBFEBMKNZQVRM-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 150000005840 aryl radicals Chemical group 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- MRRVGKUDNXCCTR-UHFFFAOYSA-N n-[4-[2-[(dimethylamino)methyl]phenyl]-2-(trifluoromethoxy)phenyl]acetamide;hydrochloride Chemical compound Cl.CN(C)CC1=CC=CC=C1C1=CC=C(NC(C)=O)C(OC(F)(F)F)=C1 MRRVGKUDNXCCTR-UHFFFAOYSA-N 0.000 claims description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
- 208000007848 Alcoholism Diseases 0.000 claims description 6
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- 206010011224 Cough Diseases 0.000 claims description 6
- 206010012735 Diarrhoea Diseases 0.000 claims description 6
- 206010013654 Drug abuse Diseases 0.000 claims description 6
- 208000007882 Gastritis Diseases 0.000 claims description 6
- 206010020751 Hypersensitivity Diseases 0.000 claims description 6
- 206010061218 Inflammation Diseases 0.000 claims description 6
- 206010046543 Urinary incontinence Diseases 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 6
- 206010001584 alcohol abuse Diseases 0.000 claims description 6
- 208000025746 alcohol use disease Diseases 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 206010015037 epilepsy Diseases 0.000 claims description 6
- 208000023504 respiratory system disease Diseases 0.000 claims description 6
- 208000011117 substance-related disease Diseases 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 claims description 6
- ZKKYKEFYUMPRRT-UHFFFAOYSA-N 2-[2-(4-chloro-3-methoxyphenyl)phenyl]-n,n-dimethylethanamine;hydrochloride Chemical compound Cl.C1=C(Cl)C(OC)=CC(C=2C(=CC=CC=2)CCN(C)C)=C1 ZKKYKEFYUMPRRT-UHFFFAOYSA-N 0.000 claims description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 235000019253 formic acid Nutrition 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 150000002430 hydrocarbons Chemical class 0.000 claims description 5
- 230000002757 inflammatory effect Effects 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- PSRAHCYZRYXJAE-UHFFFAOYSA-N n,n-dimethyl-2-[2-(3-propan-2-yloxyphenyl)phenyl]ethanamine;hydrochloride Chemical compound Cl.CC(C)OC1=CC=CC(C=2C(=CC=CC=2)CCN(C)C)=C1 PSRAHCYZRYXJAE-UHFFFAOYSA-N 0.000 claims description 5
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical class [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 claims description 5
- 208000020016 psychiatric disease Diseases 0.000 claims description 5
- UKSZBOKPHAQOMP-SVLSSHOZSA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 UKSZBOKPHAQOMP-SVLSSHOZSA-N 0.000 claims description 4
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 4
- LOTJKAVABSBRAJ-UHFFFAOYSA-N 1-[2-(1,3-benzodioxol-5-yl)phenyl]-n,n-dimethylmethanamine;hydrochloride Chemical compound Cl.CN(C)CC1=CC=CC=C1C1=CC=C(OCO2)C2=C1 LOTJKAVABSBRAJ-UHFFFAOYSA-N 0.000 claims description 4
- NNTSLBLAWBQHFT-UHFFFAOYSA-N 1-[2-(2,3-difluorophenyl)phenyl]-n,n-dimethylmethanamine;hydrochloride Chemical compound Cl.CN(C)CC1=CC=CC=C1C1=CC=CC(F)=C1F NNTSLBLAWBQHFT-UHFFFAOYSA-N 0.000 claims description 4
- JGTYWHKITUBWHM-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)phenyl]-n,n-dimethylmethanamine;hydrochloride Chemical compound Cl.CN(C)CC1=CC=CC=C1C1=CC=C(Cl)C=C1Cl JGTYWHKITUBWHM-UHFFFAOYSA-N 0.000 claims description 4
- YEERDUIEZIAHCJ-UHFFFAOYSA-N 1-[2-(2,5-difluorophenyl)phenyl]-n,n-dimethylmethanamine;hydrochloride Chemical compound Cl.CN(C)CC1=CC=CC=C1C1=CC(F)=CC=C1F YEERDUIEZIAHCJ-UHFFFAOYSA-N 0.000 claims description 4
- SPCRKWSUFQTLCR-UHFFFAOYSA-N 1-[2-(2-fluorophenyl)phenyl]-n,n-dimethylmethanamine;hydrochloride Chemical compound Cl.CN(C)CC1=CC=CC=C1C1=CC=CC=C1F SPCRKWSUFQTLCR-UHFFFAOYSA-N 0.000 claims description 4
- GHLKMHYJCAGBIQ-UHFFFAOYSA-N 1-[2-(2-methoxyphenyl)phenyl]-n,n-dimethylmethanamine;hydrochloride Chemical compound Cl.COC1=CC=CC=C1C1=CC=CC=C1CN(C)C GHLKMHYJCAGBIQ-UHFFFAOYSA-N 0.000 claims description 4
- CQUCXIVEMATMHA-UHFFFAOYSA-N 1-[2-(3,4-difluorophenyl)phenyl]-n,n-dimethylmethanamine;hydrochloride Chemical compound Cl.CN(C)CC1=CC=CC=C1C1=CC=C(F)C(F)=C1 CQUCXIVEMATMHA-UHFFFAOYSA-N 0.000 claims description 4
- KKBYEGMXEPPHTK-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenyl)phenyl]-n,n-dimethylmethanamine;hydrochloride Chemical compound Cl.CN(C)CC1=CC=CC=C1C1=CC(Cl)=CC(Cl)=C1 KKBYEGMXEPPHTK-UHFFFAOYSA-N 0.000 claims description 4
- BTVTXQPZZVHAPR-UHFFFAOYSA-N 1-[2-(3-chloro-4-fluorophenyl)phenyl]-n,n-dimethylmethanamine;hydrochloride Chemical compound Cl.CN(C)CC1=CC=CC=C1C1=CC=C(F)C(Cl)=C1 BTVTXQPZZVHAPR-UHFFFAOYSA-N 0.000 claims description 4
- FZWGTVDAJIKWEA-UHFFFAOYSA-N 1-[2-(3-chlorophenyl)phenyl]-n,n-dimethylmethanamine;hydrochloride Chemical compound Cl.CN(C)CC1=CC=CC=C1C1=CC=CC(Cl)=C1 FZWGTVDAJIKWEA-UHFFFAOYSA-N 0.000 claims description 4
- ZFVZFGFSMHGMGU-UHFFFAOYSA-N 1-[2-(3-fluorophenyl)phenyl]-n,n-dimethylmethanamine;hydrochloride Chemical compound Cl.CN(C)CC1=CC=CC=C1C1=CC=CC(F)=C1 ZFVZFGFSMHGMGU-UHFFFAOYSA-N 0.000 claims description 4
- CPIIAVGEOBCKCS-UHFFFAOYSA-N 1-[2-(4-chloro-3-methoxyphenyl)phenyl]-n,n-dimethylmethanamine;hydrochloride Chemical compound Cl.C1=C(Cl)C(OC)=CC(C=2C(=CC=CC=2)CN(C)C)=C1 CPIIAVGEOBCKCS-UHFFFAOYSA-N 0.000 claims description 4
- QIWYPOSWKSRTHW-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)phenyl]-n,n-dimethylmethanamine;hydrochloride Chemical compound Cl.CN(C)CC1=CC=CC=C1C1=CC=C(F)C=C1 QIWYPOSWKSRTHW-UHFFFAOYSA-N 0.000 claims description 4
- AEQHXHUXXCAHCY-UHFFFAOYSA-N 1-[3-[2-[2-(dimethylamino)ethyl]phenyl]phenyl]ethanone;hydrochloride Chemical compound Cl.CN(C)CCC1=CC=CC=C1C1=CC=CC(C(C)=O)=C1 AEQHXHUXXCAHCY-UHFFFAOYSA-N 0.000 claims description 4
- LVMYQXVDXQMYIM-UHFFFAOYSA-N 2-chloro-5-[2-[(dimethylamino)methyl]phenyl]phenol;hydrochloride Chemical compound Cl.CN(C)CC1=CC=CC=C1C1=CC=C(Cl)C(O)=C1 LVMYQXVDXQMYIM-UHFFFAOYSA-N 0.000 claims description 4
- IUPUCLUJXIGKDX-UHFFFAOYSA-N 3-[2-[(dimethylamino)methyl]phenyl]benzaldehyde;hydrochloride Chemical compound Cl.CN(C)CC1=CC=CC=C1C1=CC=CC(C=O)=C1 IUPUCLUJXIGKDX-UHFFFAOYSA-N 0.000 claims description 4
- DVTZTGNOJXKDDR-UHFFFAOYSA-N 3-[2-[2-(dimethylamino)ethyl]phenyl]phenol;hydrochloride Chemical compound Cl.CN(C)CCC1=CC=CC=C1C1=CC=CC(O)=C1 DVTZTGNOJXKDDR-UHFFFAOYSA-N 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 239000003638 chemical reducing agent Substances 0.000 claims description 4
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims description 4
- 230000007704 transition Effects 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- JSAKNBAXRRCREQ-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)phenyl]-n,n-dimethylmethanamine;hydrochloride Chemical compound Cl.CN(C)CC1=CC=CC=C1C1=CC=C(Cl)C=C1 JSAKNBAXRRCREQ-UHFFFAOYSA-N 0.000 claims description 3
- IGYIRFURJSFNKH-UHFFFAOYSA-N 1-[2-[4-fluoro-3-(trifluoromethyl)phenyl]phenyl]-n,n-dimethylmethanamine;hydrochloride Chemical compound Cl.CN(C)CC1=CC=CC=C1C1=CC=C(F)C(C(F)(F)F)=C1 IGYIRFURJSFNKH-UHFFFAOYSA-N 0.000 claims description 3
- GCHJSUGGDVKKGZ-UHFFFAOYSA-N 2-chloro-5-[2-[2-(dimethylamino)ethyl]phenyl]phenol;hydrochloride Chemical compound Cl.CN(C)CCC1=CC=CC=C1C1=CC=C(Cl)C(O)=C1 GCHJSUGGDVKKGZ-UHFFFAOYSA-N 0.000 claims description 3
- ZTBMPURAQYWVAH-UHFFFAOYSA-N 3-[2-[(dimethylamino)methyl]phenyl]phenol;hydrochloride Chemical compound Cl.CN(C)CC1=CC=CC=C1C1=CC=CC(O)=C1 ZTBMPURAQYWVAH-UHFFFAOYSA-N 0.000 claims description 3
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- 239000004327 boric acid Substances 0.000 claims description 3
- 238000007796 conventional method Methods 0.000 claims description 3
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- JTGKZJUNMVUTCB-UHFFFAOYSA-N n,n-dimethyl-1-[2-(3-propan-2-yloxyphenyl)phenyl]methanamine;hydrochloride Chemical compound Cl.CC(C)OC1=CC=CC(C=2C(=CC=CC=2)CN(C)C)=C1 JTGKZJUNMVUTCB-UHFFFAOYSA-N 0.000 claims description 3
- ZDRZVIAOOISSGB-UHFFFAOYSA-N n,n-dimethyl-1-[2-(4-methylsulfonylphenyl)phenyl]methanamine;hydrochloride Chemical compound Cl.CN(C)CC1=CC=CC=C1C1=CC=C(S(C)(=O)=O)C=C1 ZDRZVIAOOISSGB-UHFFFAOYSA-N 0.000 claims description 3
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 claims description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 3
- 238000010561 standard procedure Methods 0.000 claims description 3
- QESBJURPUBEZJE-UHFFFAOYSA-N 1-[2-(2,3-dimethoxyphenyl)phenyl]-n,n-dimethylmethanamine Chemical compound COC1=CC=CC(C=2C(=CC=CC=2)CN(C)C)=C1OC QESBJURPUBEZJE-UHFFFAOYSA-N 0.000 claims description 2
- RBLPHFRSGBIGTA-UHFFFAOYSA-N 1-[2-(3-methoxyphenyl)phenyl]-n,n-dimethylmethanamine Chemical compound COC1=CC=CC(C=2C(=CC=CC=2)CN(C)C)=C1 RBLPHFRSGBIGTA-UHFFFAOYSA-N 0.000 claims description 2
- XGLRGTYNFHFDKR-UHFFFAOYSA-N 2-[2-[(dimethylamino)methyl]phenyl]benzaldehyde Chemical compound CN(C)CC1=CC=CC=C1C1=CC=CC=C1C=O XGLRGTYNFHFDKR-UHFFFAOYSA-N 0.000 claims description 2
- UKANVZGMQAYFOX-UHFFFAOYSA-N 2-[2-[(dimethylamino)methyl]phenyl]phenol Chemical compound CN(C)CC1=CC=CC=C1C1=CC=CC=C1O UKANVZGMQAYFOX-UHFFFAOYSA-N 0.000 claims description 2
- JZCULWLYQSXRCK-UHFFFAOYSA-N 2-amino-5-[2-[(dimethylamino)methyl]phenyl]phenol hydrochloride Chemical compound NC1=C(C=C(C=C1)C1=C(C=CC=C1)CN(C)C)O.Cl JZCULWLYQSXRCK-UHFFFAOYSA-N 0.000 claims description 2
- AYKPSESUHIAKAR-UHFFFAOYSA-N 3-[2-[(dimethylamino)methyl]phenyl]benzene-1,2-diol Chemical compound CN(C)CC1=CC=CC=C1C1=CC=CC(O)=C1O AYKPSESUHIAKAR-UHFFFAOYSA-N 0.000 claims description 2
- DBACJLCLFSETSR-UHFFFAOYSA-N 5-chloro-2-[2-[(dimethylamino)methyl]phenyl]benzonitrile Chemical compound CN(C)CC1=CC=CC=C1C1=CC=C(Cl)C=C1C#N DBACJLCLFSETSR-UHFFFAOYSA-N 0.000 claims description 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 2
- FSTSRDCRWBKMHI-UHFFFAOYSA-N CN(C)CC1=C(C=CC=C1)C1=C(C=CC(=C1)OC(F)(F)F)N.Cl Chemical compound CN(C)CC1=C(C=CC=C1)C1=C(C=CC(=C1)OC(F)(F)F)N.Cl FSTSRDCRWBKMHI-UHFFFAOYSA-N 0.000 claims description 2
- GXOJEQYMTYZUDE-UHFFFAOYSA-N Cl.Cl.CN(C)Cc1ccccc1-c1cc(OC(F)(F)F)ccc1NC(C)=O Chemical compound Cl.Cl.CN(C)Cc1ccccc1-c1cc(OC(F)(F)F)ccc1NC(C)=O GXOJEQYMTYZUDE-UHFFFAOYSA-N 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- QPUUXDZYYMLHSF-UHFFFAOYSA-N N1C=CC2=CC(=CC=C12)C1=C(CN(C)C)C=CC=C1.Cl Chemical compound N1C=CC2=CC(=CC=C12)C1=C(CN(C)C)C=CC=C1.Cl QPUUXDZYYMLHSF-UHFFFAOYSA-N 0.000 claims description 2
- ZRBPLHLFULGGTN-UHFFFAOYSA-N [2-[2-[(dimethylamino)methyl]phenyl]phenyl]methanol Chemical compound CN(C)CC1=CC=CC=C1C1=CC=CC=C1CO ZRBPLHLFULGGTN-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 239000011260 aqueous acid Substances 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 claims description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- YKLQQSCKXGGJHJ-UHFFFAOYSA-N n,n-dimethyl-1-(2-phenylphenyl)methanamine Chemical compound CN(C)CC1=CC=CC=C1C1=CC=CC=C1 YKLQQSCKXGGJHJ-UHFFFAOYSA-N 0.000 claims description 2
- YCAAJYWHKCBJQE-UHFFFAOYSA-N n,n-dimethyl-1-[2-(2-methylphenyl)phenyl]methanamine Chemical compound CN(C)CC1=CC=CC=C1C1=CC=CC=C1C YCAAJYWHKCBJQE-UHFFFAOYSA-N 0.000 claims description 2
- QGOOAEPVHQYWJX-UHFFFAOYSA-N n,n-dimethyl-1-[2-(4-methylphenyl)phenyl]methanamine Chemical compound CN(C)CC1=CC=CC=C1C1=CC=C(C)C=C1 QGOOAEPVHQYWJX-UHFFFAOYSA-N 0.000 claims description 2
- IJSVXEHKKUEEJL-UHFFFAOYSA-N n,n-dimethyl-2-(2-phenylphenyl)ethanamine Chemical compound CN(C)CCC1=CC=CC=C1C1=CC=CC=C1 IJSVXEHKKUEEJL-UHFFFAOYSA-N 0.000 claims description 2
- 239000012279 sodium borohydride Substances 0.000 claims description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 2
- AXQMVEUTZFEOKL-UHFFFAOYSA-N 1-[2-(3,5-difluorophenyl)phenyl]-N,N-dimethylmethanamine dihydrochloride Chemical compound FC=1C=C(C=C(C1)F)C1=C(C=CC=C1)CN(C)C.Cl.Cl AXQMVEUTZFEOKL-UHFFFAOYSA-N 0.000 claims 1
- DCODZSCRDJNPGK-UHFFFAOYSA-N ClC=1C=C(C=CC1Cl)C1=C(C=CC=C1)CN(C)C.Cl.C1(=C(C=CC=C1)CN(C)C)C1=CC=CC=C1.Cl Chemical compound ClC=1C=C(C=CC1Cl)C1=C(C=CC=C1)CN(C)C.Cl.C1(=C(C=CC=C1)CN(C)C)C1=CC=CC=C1.Cl DCODZSCRDJNPGK-UHFFFAOYSA-N 0.000 claims 1
- 208000020401 Depressive disease Diseases 0.000 claims 1
- XDIKPIDIPALTFU-UHFFFAOYSA-N FC(C=1C=C(C=CC1)C1=C(C=CC=C1)CN(C)C)F.Cl.CN(C)CC1=C(C=CC=C1)C=1C(=CC=CC1)C=O.Cl Chemical compound FC(C=1C=C(C=CC1)C1=C(C=CC=C1)CN(C)C)F.Cl.CN(C)CC1=C(C=CC=C1)C=1C(=CC=CC1)C=O.Cl XDIKPIDIPALTFU-UHFFFAOYSA-N 0.000 claims 1
- 239000008186 active pharmaceutical agent Substances 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 229910052723 transition metal Inorganic materials 0.000 claims 1
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- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
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- SHHWWZMWTUTJPY-UHFFFAOYSA-N n-[4-bromo-2-(trifluoromethoxy)phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(Br)C=C1OC(F)(F)F SHHWWZMWTUTJPY-UHFFFAOYSA-N 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 230000001737 promoting effect Effects 0.000 description 1
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- 238000000611 regression analysis Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 239000011780 sodium chloride Substances 0.000 description 1
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- 239000003826 tablet Substances 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
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- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/29—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having 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
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- C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having 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
- C07C215/48—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having 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 amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups
- C07C215/50—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having 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 amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups with amino groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
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- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having 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
- C07C215/48—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having 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 amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups
- C07C215/52—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having 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 amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups linked by carbon chains having two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
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- 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
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- 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
- C07C217/56—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 amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
- C07C217/58—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 amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms with amino groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
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- C07C217/56—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 amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
- C07C217/60—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 amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms linked by carbon chains having two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
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- C07C223/00—Compounds containing amino and —CHO groups bound to the same carbon skeleton
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- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/02—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton
- C07C225/14—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated
- C07C225/16—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/42—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
- C07C233/43—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of a saturated carbon skeleton
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- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/58—Radicals substituted by nitrogen atoms
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Neurosurgery (AREA)
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- Pain & Pain Management (AREA)
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- Hematology (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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Priority Applications (33)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19937537A DE19937537A1 (de) | 1999-08-09 | 1999-08-09 | Substituierte 2-Dialkylaminoalkylbiphenyl-Derivate |
| ES00951440T ES2270861T3 (es) | 1999-08-09 | 2000-07-25 | Derivados de 2-aminoalquilbifenilo. |
| PT00951440T PT1202953E (pt) | 1999-08-09 | 2000-07-25 | Derivados substituídos de 2-dialquilaminoalquibifenilo |
| EP00951440A EP1202953B1 (de) | 1999-08-09 | 2000-07-25 | Substituierte 2-dialkylaminoalkylbiphenyl-derivate |
| SI200030909T SI1202953T1 (sl) | 1999-08-09 | 2000-07-25 | Substituirani 2-dialkilaminoalkilbifenilni derivati |
| AU64374/00A AU778596B2 (en) | 1999-08-09 | 2000-07-25 | Substituted 2-dialkylaminoalkylbiphenyl derivatives |
| RU2002105496/04A RU2259349C2 (ru) | 1999-08-09 | 2000-07-25 | Замещенные производные 2-диалкиламиноалкилбифенила |
| MXPA02001372A MXPA02001372A (es) | 1999-08-09 | 2000-07-25 | Derivados sustituidos de 2-dialquilaminoalquilbifenilo. |
| CNB00813734XA CN1245376C (zh) | 1999-08-09 | 2000-07-25 | 取代的2-二烷基氨基烷基联苯衍生物 |
| BR0013316-7A BR0013316A (pt) | 1999-08-09 | 2000-07-25 | Derivados substituìdos de 2-dialquilaminoalquilbifenila, seu processo de fabricação e seu uso. |
| IL14805800A IL148058A0 (en) | 1999-08-09 | 2000-07-25 | Substituted 2-dialkylaminoalkylbiphenyl derivatives |
| PCT/EP2000/007095 WO2001010816A2 (de) | 1999-08-09 | 2000-07-25 | Substituierte 2-dialkylaminoalkylbiphenyl-derivate |
| NZ517364A NZ517364A (en) | 1999-08-09 | 2000-07-25 | Substituted 2-dialkylaminoalkylbiphenyl derivatives having analgesic effect suitable for treatment of pain |
| PL353876A PL199880B1 (pl) | 1999-08-09 | 2000-07-25 | Podstawione pochodne 2-aminoalkilobifenylu, sposób ich wytwarzania, środek leczniczy oraz zastosowanie |
| CZ20020492A CZ302984B6 (cs) | 1999-08-09 | 2000-07-25 | Substituované deriváty 2-dialkylaminoalkylbifenylu, zpusob jejich výroby, léciva tyto látky obsahující a jejich použití |
| DK00951440T DK1202953T3 (da) | 1999-08-09 | 2000-07-25 | Substituerede 2-dialkylaminoalkylbiphenylderivater |
| JP2001515283A JP5042422B2 (ja) | 1999-08-09 | 2000-07-25 | 置換された2−ジアルキルアミノアルキルビフェニル誘導体 |
| SK203-2002A SK287353B6 (sk) | 1999-08-09 | 2000-07-25 | Substituované deriváty 2-dialkylaminoalkylbifenylu, spôsob ich výroby, lieky tieto látky obsahujúce a ich použitie |
| CA2380857A CA2380857C (en) | 1999-08-09 | 2000-07-25 | Substituted 2-dialkylaminoalkylbiphenyl derivatives |
| DE50013404T DE50013404D1 (de) | 1999-08-09 | 2000-07-25 | Substituierte 2-dialkylaminoalkylbiphenyl-derivate |
| CN200610004917A CN100575334C (zh) | 1999-08-09 | 2000-07-25 | 取代的2-二烷基氨基烷基联苯衍生物 |
| HK02107800.3A HK1046400B (zh) | 1999-08-09 | 2000-07-25 | 取代的2-二烷基氨基烷基联苯衍生物 |
| HU0202075A HUP0202075A3 (en) | 1999-08-09 | 2000-07-25 | Substituted 2-dialkylaminoalkylbiphenyl derivatives, process for their preparation, pharmaceutical compositions containing them and their use |
| AT00951440T ATE338021T1 (de) | 1999-08-09 | 2000-07-25 | Substituierte 2-dialkylaminoalkylbiphenyl- derivate |
| KR1020027001825A KR100723816B1 (ko) | 1999-08-09 | 2000-07-25 | 치환된 2-아미노알킬비페닐 유도체 |
| PE2000000759A PE20010384A1 (es) | 1999-08-09 | 2000-08-01 | Derivados de 2-aminoalquilbifenilo sustituidos y procedimiento para su preparacion |
| CO00058414A CO5200790A1 (es) | 1999-08-09 | 2000-08-03 | Derivados de 2-dialquilaminoalquilbifenil sustituidos, procedimiento para su preparacion y medicamentos que contienen estos compuestos |
| ARP000104054A AR025052A1 (es) | 1999-08-09 | 2000-08-04 | Derivados de 2-dialquilaminoalquilbifenilo sustituidos, procedimiento para su preparacion, medicamentos que contienen estos compuestos y el uso de estoscompuestos para la preparacion de medicamentos. |
| IL148058A IL148058A (en) | 1999-08-09 | 2002-02-06 | Transformed history of 2-dialkylaminoalkylbiphenyl |
| NO20020610A NO327670B1 (no) | 1999-08-09 | 2002-02-07 | Substituerte 2-dialkylaminoalkylbifenylderivater, fremgangsmate for fremstilling, legemidler omfattende disse samt deres anvendelse |
| US10/071,229 US6710080B2 (en) | 1999-08-09 | 2002-02-11 | Substituted 2-dialkylaminoalkylbiphenyl derivatives |
| ZA200201917A ZA200201917B (en) | 1999-08-09 | 2002-03-07 | Substituted 2-dialkylaminoalkylbiphenyl derivatives. |
| CY20061101399T CY1105387T1 (el) | 1999-08-09 | 2006-09-27 | Υποκατεστημενα παραγωγα 2-διαλκυλαμινοαλκυλοδιφαινθλιου |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19937537A DE19937537A1 (de) | 1999-08-09 | 1999-08-09 | Substituierte 2-Dialkylaminoalkylbiphenyl-Derivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19937537A1 true DE19937537A1 (de) | 2001-03-08 |
Family
ID=7917726
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19937537A Withdrawn DE19937537A1 (de) | 1999-08-09 | 1999-08-09 | Substituierte 2-Dialkylaminoalkylbiphenyl-Derivate |
| DE50013404T Expired - Lifetime DE50013404D1 (de) | 1999-08-09 | 2000-07-25 | Substituierte 2-dialkylaminoalkylbiphenyl-derivate |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE50013404T Expired - Lifetime DE50013404D1 (de) | 1999-08-09 | 2000-07-25 | Substituierte 2-dialkylaminoalkylbiphenyl-derivate |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US6710080B2 (https=) |
| EP (1) | EP1202953B1 (https=) |
| JP (1) | JP5042422B2 (https=) |
| KR (1) | KR100723816B1 (https=) |
| CN (2) | CN1245376C (https=) |
| AR (1) | AR025052A1 (https=) |
| AT (1) | ATE338021T1 (https=) |
| AU (1) | AU778596B2 (https=) |
| BR (1) | BR0013316A (https=) |
| CA (1) | CA2380857C (https=) |
| CO (1) | CO5200790A1 (https=) |
| CY (1) | CY1105387T1 (https=) |
| CZ (1) | CZ302984B6 (https=) |
| DE (2) | DE19937537A1 (https=) |
| DK (1) | DK1202953T3 (https=) |
| ES (1) | ES2270861T3 (https=) |
| HK (1) | HK1046400B (https=) |
| HU (1) | HUP0202075A3 (https=) |
| IL (2) | IL148058A0 (https=) |
| MX (1) | MXPA02001372A (https=) |
| NO (1) | NO327670B1 (https=) |
| NZ (1) | NZ517364A (https=) |
| PE (1) | PE20010384A1 (https=) |
| PL (1) | PL199880B1 (https=) |
| PT (1) | PT1202953E (https=) |
| RU (1) | RU2259349C2 (https=) |
| SI (1) | SI1202953T1 (https=) |
| SK (1) | SK287353B6 (https=) |
| WO (1) | WO2001010816A2 (https=) |
| ZA (1) | ZA200201917B (https=) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001057046A1 (en) | 2000-02-02 | 2001-08-09 | Banyu Pharmaceutical Co., Ltd. | Method of converting functional group through halogen-metal exchange reaction |
| US7506197B2 (en) * | 2005-02-07 | 2009-03-17 | International Business Machines Corporation | Multi-directional fault detection system |
| CN100364966C (zh) * | 2005-04-14 | 2008-01-30 | 上海雅本化学有限公司 | 1-[2-氨基-1-(对甲氧苯基)乙基]环己醇甲酸盐的合成方法 |
| TW200823204A (en) * | 2006-10-17 | 2008-06-01 | Arena Pharm Inc | Biphenyl sulfonyl and phenyl-heteroaryl sulfonyl modulators of the histamine H3-receptor useful for the treatment of disorders related thereto |
| EP1997493A1 (en) * | 2007-05-28 | 2008-12-03 | Laboratorios del Dr. Esteve S.A. | Combination of a 5-HT7 receptor ligand and an opioid receptor ligand |
| CN101952244B (zh) * | 2008-02-01 | 2014-11-05 | 潘米拉制药公司 | 前列腺素d2受体的n,n-二取代氨基烷基联苯拮抗剂 |
| UA98839C2 (en) * | 2008-02-01 | 2012-06-25 | Панмира Фармасьютикалз, Ллк. | N,n-disubstituted aminoalkylbiphenyl antagonists of prostaglandin d2 receptors |
| EP2257536A4 (en) * | 2008-02-14 | 2011-03-23 | Amira Pharmaceuticals Inc | CYCLIC DIARYL ETHERS AS ANTAGONISTS OF PROSTAGLANDIN D2 RECEPTORS |
| JP2011513242A (ja) * | 2008-02-25 | 2011-04-28 | アミラ ファーマシューティカルズ,インク. | プロスタグランジンd2受容体アンタゴニスト |
| WO2009145989A2 (en) * | 2008-04-02 | 2009-12-03 | Amira Pharmaceuticals, Inc. | Aminoalkylphenyl antagonists of prostaglandin d2 receptors |
| EP2307362A4 (en) * | 2008-07-03 | 2012-05-09 | Panmira Pharmaceuticals Llc | ANTAGONISTS OF PROSTAGLANDIN D2 RECEPTORS |
| GB2463788B (en) * | 2008-09-29 | 2010-12-15 | Amira Pharmaceuticals Inc | Heteroaryl antagonists of prostaglandin D2 receptors |
| WO2010039977A2 (en) * | 2008-10-01 | 2010-04-08 | Amira Pharmaceuticals, Inc. | Heteroaryl antagonists of prostaglandin d2 receptors |
| US8524748B2 (en) | 2008-10-08 | 2013-09-03 | Panmira Pharmaceuticals, Llc | Heteroalkyl biphenyl antagonists of prostaglandin D2 receptors |
| US8383654B2 (en) | 2008-11-17 | 2013-02-26 | Panmira Pharmaceuticals, Llc | Heterocyclic antagonists of prostaglandin D2 receptors |
| US20100173313A1 (en) * | 2009-01-08 | 2010-07-08 | Amira Pharmaceuticals, Inc. | Biomarkers of inflammation |
| KR20120038544A (ko) | 2009-07-31 | 2012-04-23 | 판미라 파마슈티칼스, 엘엘씨 | Dp2 수용체 길항제의 안과용 약학 조성물 |
| CN102596902A (zh) * | 2009-08-05 | 2012-07-18 | 潘米拉制药公司 | Dp2拮抗剂及其用途 |
| CA2782085A1 (en) | 2010-01-06 | 2011-07-14 | Panmira Pharmaceuticals, Llc | Dp2 antagonist and uses thereof |
| DE102010055322A1 (de) | 2010-12-21 | 2012-06-21 | Christian-Albrechts-Universität Zu Kiel | Antibakteriell und antimykotisch wirkende Substanzen |
| US20120309796A1 (en) | 2011-06-06 | 2012-12-06 | Fariborz Firooznia | Benzocycloheptene acetic acids |
| CN103864624A (zh) * | 2014-03-05 | 2014-06-18 | 湖北大学 | 一种简单碱催化的n-烷基化高效制备仲胺的方法 |
| CN115636775B (zh) * | 2021-07-20 | 2024-02-06 | 晶美晟光电材料(南京)有限公司 | 一种含硫的联苯类液晶化合物的制备方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4473709A (en) * | 1980-07-14 | 1984-09-25 | Fmc Corporation | Pyrethroid intermediates and process |
| WO1998057951A1 (en) * | 1997-06-19 | 1998-12-23 | Du Pont Pharmaceuticals Company | NOVEL GUANIDINE MIMICS AS FACTOR Xa INHIBITORS |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3443943A (en) * | 1967-07-24 | 1969-05-13 | Polaroid Corp | Photographic products and processes employing ring - closing 2 - equivalent silver halide developing agents |
| US4315926A (en) | 1979-12-26 | 1982-02-16 | Ciba-Geigy Corporation | Dibenz[c,e]azepines |
| US5283241A (en) * | 1992-08-28 | 1994-02-01 | Merck & Co., Inc. | Benzo-fused lactams promote release of growth hormone |
| KR20000069075A (ko) * | 1996-11-22 | 2000-11-25 | 진 엠. 듀발 | N-(아릴/헤테로아릴/알킬아세틸)아미노산 아미드, 이들을 함유하는 제약 조성물, 및 이들 화합물을 사용하여 베타-아밀로이드 펩티드의 방출 및(또는) 합성의 억제 방법 |
-
1999
- 1999-08-09 DE DE19937537A patent/DE19937537A1/de not_active Withdrawn
-
2000
- 2000-07-25 BR BR0013316-7A patent/BR0013316A/pt not_active IP Right Cessation
- 2000-07-25 PT PT00951440T patent/PT1202953E/pt unknown
- 2000-07-25 CA CA2380857A patent/CA2380857C/en not_active Expired - Fee Related
- 2000-07-25 WO PCT/EP2000/007095 patent/WO2001010816A2/de not_active Ceased
- 2000-07-25 SI SI200030909T patent/SI1202953T1/sl unknown
- 2000-07-25 AT AT00951440T patent/ATE338021T1/de active
- 2000-07-25 DE DE50013404T patent/DE50013404D1/de not_active Expired - Lifetime
- 2000-07-25 DK DK00951440T patent/DK1202953T3/da active
- 2000-07-25 SK SK203-2002A patent/SK287353B6/sk not_active IP Right Cessation
- 2000-07-25 HK HK02107800.3A patent/HK1046400B/zh not_active IP Right Cessation
- 2000-07-25 CN CNB00813734XA patent/CN1245376C/zh not_active Expired - Fee Related
- 2000-07-25 JP JP2001515283A patent/JP5042422B2/ja not_active Expired - Fee Related
- 2000-07-25 MX MXPA02001372A patent/MXPA02001372A/es active IP Right Grant
- 2000-07-25 RU RU2002105496/04A patent/RU2259349C2/ru not_active IP Right Cessation
- 2000-07-25 ES ES00951440T patent/ES2270861T3/es not_active Expired - Lifetime
- 2000-07-25 AU AU64374/00A patent/AU778596B2/en not_active Ceased
- 2000-07-25 EP EP00951440A patent/EP1202953B1/de not_active Expired - Lifetime
- 2000-07-25 PL PL353876A patent/PL199880B1/pl not_active IP Right Cessation
- 2000-07-25 CZ CZ20020492A patent/CZ302984B6/cs not_active IP Right Cessation
- 2000-07-25 HU HU0202075A patent/HUP0202075A3/hu unknown
- 2000-07-25 NZ NZ517364A patent/NZ517364A/en not_active IP Right Cessation
- 2000-07-25 IL IL14805800A patent/IL148058A0/xx active IP Right Grant
- 2000-07-25 KR KR1020027001825A patent/KR100723816B1/ko not_active Expired - Fee Related
- 2000-07-25 CN CN200610004917A patent/CN100575334C/zh not_active Expired - Fee Related
- 2000-08-01 PE PE2000000759A patent/PE20010384A1/es not_active Application Discontinuation
- 2000-08-03 CO CO00058414A patent/CO5200790A1/es not_active Application Discontinuation
- 2000-08-04 AR ARP000104054A patent/AR025052A1/es active IP Right Grant
-
2002
- 2002-02-06 IL IL148058A patent/IL148058A/en not_active IP Right Cessation
- 2002-02-07 NO NO20020610A patent/NO327670B1/no not_active IP Right Cessation
- 2002-02-11 US US10/071,229 patent/US6710080B2/en not_active Expired - Fee Related
- 2002-03-07 ZA ZA200201917A patent/ZA200201917B/en unknown
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2006
- 2006-09-27 CY CY20061101399T patent/CY1105387T1/el unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4473709A (en) * | 1980-07-14 | 1984-09-25 | Fmc Corporation | Pyrethroid intermediates and process |
| WO1998057951A1 (en) * | 1997-06-19 | 1998-12-23 | Du Pont Pharmaceuticals Company | NOVEL GUANIDINE MIMICS AS FACTOR Xa INHIBITORS |
Non-Patent Citations (4)
| Title |
|---|
| Acta Pharm. Suec. 14, 105-112 (1977) * |
| Dokl. Akad. Nauk. Arm. SSR 1975, 61 (1), S. 40-43,referiert in Chem. Abstr. 84:5880t, 1976 * |
| Journal of Computer-Aided Molecular Design, 1 (1987) 143-152 * |
| Receuil 67 (1948), S. 489-511 * |
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