RU2259349C2 - Замещенные производные 2-диалкиламиноалкилбифенила - Google Patents
Замещенные производные 2-диалкиламиноалкилбифенила Download PDFInfo
- Publication number
- RU2259349C2 RU2259349C2 RU2002105496/04A RU2002105496A RU2259349C2 RU 2259349 C2 RU2259349 C2 RU 2259349C2 RU 2002105496/04 A RU2002105496/04 A RU 2002105496/04A RU 2002105496 A RU2002105496 A RU 2002105496A RU 2259349 C2 RU2259349 C2 RU 2259349C2
- Authority
- RU
- Russia
- Prior art keywords
- corresponding hydrochloride
- dimethylamine
- ylmethyl
- alkyl
- hydrochloride
- Prior art date
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- -1 NR6aR7a Chemical group 0.000 claims abstract description 44
- 150000001875 compounds Chemical class 0.000 claims abstract description 34
- 239000002253 acid Substances 0.000 claims abstract description 32
- 239000003814 drug Substances 0.000 claims abstract description 18
- 208000002193 Pain Diseases 0.000 claims abstract description 16
- 230000036407 pain Effects 0.000 claims abstract description 16
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 12
- 238000011282 treatment Methods 0.000 claims abstract description 12
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
- 239000000126 substance Substances 0.000 claims abstract description 10
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 208000007848 Alcoholism Diseases 0.000 claims abstract description 8
- 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 8
- 206010011224 Cough Diseases 0.000 claims abstract description 8
- 206010012735 Diarrhoea Diseases 0.000 claims abstract description 8
- 208000007882 Gastritis Diseases 0.000 claims abstract description 8
- 206010015037 epilepsy Diseases 0.000 claims abstract description 8
- 201000007930 alcohol dependence Diseases 0.000 claims abstract description 7
- 230000002757 inflammatory effect Effects 0.000 claims abstract description 6
- 150000007513 acids Chemical class 0.000 claims abstract description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 4
- 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 abstract description 3
- 201000010099 disease Diseases 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 328
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 186
- 239000000203 mixture Substances 0.000 claims description 137
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 132
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 120
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 103
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 87
- 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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 10
- 229940079593 drug Drugs 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical class [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 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 7
- 206010020751 Hypersensitivity Diseases 0.000 claims description 7
- 206010061218 Inflammation Diseases 0.000 claims description 7
- 206010046543 Urinary incontinence Diseases 0.000 claims description 7
- 239000013543 active substance Substances 0.000 claims description 7
- 238000007796 conventional method Methods 0.000 claims description 7
- 206010013663 drug dependence Diseases 0.000 claims description 7
- 208000020016 psychiatric disease Diseases 0.000 claims description 7
- 208000023504 respiratory system disease Diseases 0.000 claims description 7
- 208000011117 substance-related disease Diseases 0.000 claims description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
- PDXBFKSMNSEDCE-UHFFFAOYSA-N 1-[2-(1h-indol-5-yl)phenyl]-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC=CC=C1C1=CC=C(NC=C2)C2=C1 PDXBFKSMNSEDCE-UHFFFAOYSA-N 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- 150000002430 hydrocarbons Chemical class 0.000 claims description 6
- SPSIQJQHKXSAKX-UHFFFAOYSA-N n-[2-[2-[(dimethylamino)methyl]phenyl]-4-(trifluoromethoxy)phenyl]acetamide Chemical compound CN(C)CC1=CC=CC=C1C1=CC(OC(F)(F)F)=CC=C1NC(C)=O SPSIQJQHKXSAKX-UHFFFAOYSA-N 0.000 claims description 6
- FDPZLVPLMIXVAX-UHFFFAOYSA-N n-[4-[2-[(dimethylamino)methyl]phenyl]-2-(trifluoromethoxy)phenyl]acetamide Chemical compound CN(C)CC1=CC=CC=C1C1=CC=C(NC(C)=O)C(OC(F)(F)F)=C1 FDPZLVPLMIXVAX-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- SUOYYQRYHPEYLQ-UHFFFAOYSA-N 1-[2-(4-chloro-3-methoxyphenyl)phenyl]-n,n-dimethylmethanamine Chemical compound C1=C(Cl)C(OC)=CC(C=2C(=CC=CC=2)CN(C)C)=C1 SUOYYQRYHPEYLQ-UHFFFAOYSA-N 0.000 claims description 5
- PFPFBJNHLYMTGR-UHFFFAOYSA-N 2-[2-(3-methoxyphenyl)phenyl]-n,n-dimethylethanamine Chemical compound COC1=CC=CC(C=2C(=CC=CC=2)CCN(C)C)=C1 PFPFBJNHLYMTGR-UHFFFAOYSA-N 0.000 claims description 5
- 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 5
- JTJQMICKNVMEDF-UHFFFAOYSA-N 1-[2-(1,3-benzodioxol-5-yl)phenyl]-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC=CC=C1C1=CC=C(OCO2)C2=C1 JTJQMICKNVMEDF-UHFFFAOYSA-N 0.000 claims description 4
- SNIFFGBBEWKUBK-UHFFFAOYSA-N 1-[2-(2,3-difluorophenyl)phenyl]-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC=CC=C1C1=CC=CC(F)=C1F SNIFFGBBEWKUBK-UHFFFAOYSA-N 0.000 claims description 4
- KJJFSSKZRIADGY-UHFFFAOYSA-N 1-[2-(2,5-difluorophenyl)phenyl]-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC=CC=C1C1=CC(F)=CC=C1F KJJFSSKZRIADGY-UHFFFAOYSA-N 0.000 claims description 4
- HDAZXBAXHBHAKY-UHFFFAOYSA-N 1-[2-(2,5-dimethoxyphenyl)phenyl]-n,n-dimethylmethanamine Chemical compound COC1=CC=C(OC)C(C=2C(=CC=CC=2)CN(C)C)=C1 HDAZXBAXHBHAKY-UHFFFAOYSA-N 0.000 claims description 4
- XHRRKQAJVXMETQ-UHFFFAOYSA-N 1-[2-(2-fluorophenyl)phenyl]-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC=CC=C1C1=CC=CC=C1F XHRRKQAJVXMETQ-UHFFFAOYSA-N 0.000 claims description 4
- NGBLJEJJDVRALS-UHFFFAOYSA-N 1-[2-(2-methoxyphenyl)phenyl]-n,n-dimethylmethanamine Chemical compound COC1=CC=CC=C1C1=CC=CC=C1CN(C)C NGBLJEJJDVRALS-UHFFFAOYSA-N 0.000 claims description 4
- OTRMKSUBIQNHCR-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenyl)phenyl]-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC=CC=C1C1=CC=C(Cl)C(Cl)=C1 OTRMKSUBIQNHCR-UHFFFAOYSA-N 0.000 claims description 4
- KTWXEUKXOLJXMB-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenyl)phenyl]-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC=CC=C1C1=CC(Cl)=CC(Cl)=C1 KTWXEUKXOLJXMB-UHFFFAOYSA-N 0.000 claims description 4
- FHVFEMXXFFTDPH-UHFFFAOYSA-N 1-[2-(3,5-difluorophenyl)phenyl]-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC=CC=C1C1=CC(F)=CC(F)=C1 FHVFEMXXFFTDPH-UHFFFAOYSA-N 0.000 claims description 4
- FAVQYIOENLBFBX-UHFFFAOYSA-N 1-[2-(3-fluorophenyl)phenyl]-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC=CC=C1C1=CC=CC(F)=C1 FAVQYIOENLBFBX-UHFFFAOYSA-N 0.000 claims description 4
- SBFNZQDDWACYDX-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)phenyl]-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC=CC=C1C1=CC=C(F)C=C1 SBFNZQDDWACYDX-UHFFFAOYSA-N 0.000 claims description 4
- OYNHUQIKBDRNEA-UHFFFAOYSA-N 1-[2-[3-(difluoromethyl)phenyl]phenyl]-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC=CC=C1C1=CC=CC(C(F)F)=C1 OYNHUQIKBDRNEA-UHFFFAOYSA-N 0.000 claims description 4
- KPHPPVMJRZLUTJ-UHFFFAOYSA-N 1-[2-[4-fluoro-3-(trifluoromethyl)phenyl]phenyl]-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC=CC=C1C1=CC=C(F)C(C(F)(F)F)=C1 KPHPPVMJRZLUTJ-UHFFFAOYSA-N 0.000 claims description 4
- ZSEWWHJKGCHKPU-UHFFFAOYSA-N 1-[3-[2-[2-(dimethylamino)ethyl]phenyl]phenyl]ethanone Chemical compound CN(C)CCC1=CC=CC=C1C1=CC=CC(C(C)=O)=C1 ZSEWWHJKGCHKPU-UHFFFAOYSA-N 0.000 claims description 4
- QXVPQVPPQAGMRL-UHFFFAOYSA-N 2-[2-(4-chloro-3-methoxyphenyl)phenyl]-n,n-dimethylethanamine Chemical compound C1=C(Cl)C(OC)=CC(C=2C(=CC=CC=2)CCN(C)C)=C1 QXVPQVPPQAGMRL-UHFFFAOYSA-N 0.000 claims description 4
- VIQLLOSQHKNCDO-UHFFFAOYSA-N 2-[2-[(dimethylamino)methyl]phenyl]-4-(trifluoromethoxy)aniline Chemical compound CN(C)CC1=CC=CC=C1C1=CC(OC(F)(F)F)=CC=C1N VIQLLOSQHKNCDO-UHFFFAOYSA-N 0.000 claims description 4
- RZYZVPIOXYSUBY-UHFFFAOYSA-N 2-amino-5-[2-[(dimethylamino)methyl]phenyl]phenol Chemical compound CN(C)CC1=CC=CC=C1C1=CC=C(N)C(O)=C1 RZYZVPIOXYSUBY-UHFFFAOYSA-N 0.000 claims description 4
- YCLCBIXTKVEJJY-UHFFFAOYSA-N 2-chloro-5-[2-[(dimethylamino)methyl]phenyl]phenol Chemical compound CN(C)CC1=CC=CC=C1C1=CC=C(Cl)C(O)=C1 YCLCBIXTKVEJJY-UHFFFAOYSA-N 0.000 claims description 4
- XYQDZLIZLSPCLF-UHFFFAOYSA-N 3-[2-[(dimethylamino)methyl]phenyl]benzaldehyde Chemical compound CN(C)CC1=CC=CC=C1C1=CC=CC(C=O)=C1 XYQDZLIZLSPCLF-UHFFFAOYSA-N 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- GWBXJEYJOFJIDE-UHFFFAOYSA-N n,n-dimethyl-1-[2-(4-methylsulfonylphenyl)phenyl]methanamine Chemical compound CN(C)CC1=CC=CC=C1C1=CC=C(S(C)(=O)=O)C=C1 GWBXJEYJOFJIDE-UHFFFAOYSA-N 0.000 claims description 4
- 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 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- MJOBAQLOUXHZMY-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)phenyl]-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC=CC=C1C1=CC=C(Cl)C=C1Cl MJOBAQLOUXHZMY-UHFFFAOYSA-N 0.000 claims description 3
- RIOGUJGOLAUMTE-UHFFFAOYSA-N 1-[2-(3,4-difluorophenyl)phenyl]-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC=CC=C1C1=CC=C(F)C(F)=C1 RIOGUJGOLAUMTE-UHFFFAOYSA-N 0.000 claims description 3
- PPHDOJRHRRTMIU-UHFFFAOYSA-N 1-[2-(3-chloro-4-fluorophenyl)phenyl]-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC=CC=C1C1=CC=C(F)C(Cl)=C1 PPHDOJRHRRTMIU-UHFFFAOYSA-N 0.000 claims description 3
- GERRSWMXAXUWPR-UHFFFAOYSA-N 1-[2-(3-chlorophenyl)phenyl]-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC=CC=C1C1=CC=CC(Cl)=C1 GERRSWMXAXUWPR-UHFFFAOYSA-N 0.000 claims description 3
- HNAYTOFGCJTVGH-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)phenyl]-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC=CC=C1C1=CC=C(Cl)C=C1 HNAYTOFGCJTVGH-UHFFFAOYSA-N 0.000 claims description 3
- FAZQQEZPBSDIHS-UHFFFAOYSA-N 2,6-dichloro-4-[2-[(dimethylamino)methyl]phenyl]aniline Chemical compound CN(C)CC1=CC=CC=C1C1=CC(Cl)=C(N)C(Cl)=C1 FAZQQEZPBSDIHS-UHFFFAOYSA-N 0.000 claims description 3
- OZMWAZUMBANJDD-UHFFFAOYSA-N 2-chloro-5-[2-[2-(dimethylamino)ethyl]phenyl]phenol Chemical compound CN(C)CCC1=CC=CC=C1C1=CC=C(Cl)C(O)=C1 OZMWAZUMBANJDD-UHFFFAOYSA-N 0.000 claims description 3
- SJNQGAJHCYNNCI-UHFFFAOYSA-N 3-[2-[(dimethylamino)methyl]phenyl]phenol Chemical compound CN(C)CC1=CC=CC=C1C1=CC=CC(O)=C1 SJNQGAJHCYNNCI-UHFFFAOYSA-N 0.000 claims description 3
- VWYRCIJMCZVEJI-UHFFFAOYSA-N 3-[2-[2-(dimethylamino)ethyl]phenyl]phenol Chemical compound CN(C)CCC1=CC=CC=C1C1=CC=CC(O)=C1 VWYRCIJMCZVEJI-UHFFFAOYSA-N 0.000 claims description 3
- 238000006555 catalytic reaction Methods 0.000 claims description 3
- JTYYDDGYKKMUNY-UHFFFAOYSA-N n,n-dimethyl-2-[2-(3-propan-2-yloxyphenyl)phenyl]ethanamine Chemical compound CC(C)OC1=CC=CC(C=2C(=CC=CC=2)CCN(C)C)=C1 JTYYDDGYKKMUNY-UHFFFAOYSA-N 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical class [Pd+2] MUJIDPITZJWBSW-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
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 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
- 230000002265 prevention Effects 0.000 claims description 3
- 229910052723 transition metal Inorganic materials 0.000 claims description 3
- 150000003624 transition metals Chemical class 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 6
- 230000004054 inflammatory process Effects 0.000 claims 2
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 1
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 claims 1
- 150000004985 diamines Chemical class 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 230000007704 transition Effects 0.000 claims 1
- 239000000460 chlorine Substances 0.000 abstract description 7
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 6
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 abstract 3
- 125000005843 halogen group Chemical group 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- 208000008967 Enuresis Diseases 0.000 abstract 1
- 208000026935 allergic disease Diseases 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 208000035475 disorder Diseases 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 230000007721 medicinal effect Effects 0.000 abstract 1
- 238000011321 prophylaxis Methods 0.000 abstract 1
- 230000000241 respiratory effect Effects 0.000 abstract 1
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 88
- 239000000243 solution Substances 0.000 description 84
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 81
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 75
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 67
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 54
- 239000012074 organic phase Substances 0.000 description 45
- 238000012545 processing Methods 0.000 description 45
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 43
- 238000010992 reflux Methods 0.000 description 43
- 239000012299 nitrogen atmosphere Substances 0.000 description 42
- 229910000029 sodium carbonate Inorganic materials 0.000 description 37
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 34
- 238000010828 elution Methods 0.000 description 34
- 239000000741 silica gel Substances 0.000 description 34
- 229910002027 silica gel Inorganic materials 0.000 description 34
- 239000012071 phase Substances 0.000 description 25
- VTANQTUBPZSWHY-UHFFFAOYSA-N 1-(2-dimethoxyboranylphenyl)-n,n-dimethylmethanamine Chemical compound COB(OC)C1=CC=CC=C1CN(C)C VTANQTUBPZSWHY-UHFFFAOYSA-N 0.000 description 18
- ZPZPSZZVDFMNQS-UHFFFAOYSA-N 1-(2-bromophenyl)-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC=CC=C1Br ZPZPSZZVDFMNQS-UHFFFAOYSA-N 0.000 description 17
- 239000007864 aqueous solution Substances 0.000 description 17
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 13
- 238000003756 stirring Methods 0.000 description 12
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 8
- 239000000284 extract Substances 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- CEQDOZNXFWUMTG-UHFFFAOYSA-N 2-(2-bromophenyl)-n,n-dimethylethanamine Chemical compound CN(C)CCC1=CC=CC=C1Br CEQDOZNXFWUMTG-UHFFFAOYSA-N 0.000 description 6
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Classifications
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- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
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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
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- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
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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
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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
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- 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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- 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
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- 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
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- 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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- C07C317/32—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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- Neurosurgery (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Pulmonology (AREA)
- Psychiatry (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Hematology (AREA)
- Heart & Thoracic Surgery (AREA)
- Immunology (AREA)
- Addiction (AREA)
- Rheumatology (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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Furan Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19937537.2 | 1999-08-09 | ||
| DE19937537A DE19937537A1 (de) | 1999-08-09 | 1999-08-09 | Substituierte 2-Dialkylaminoalkylbiphenyl-Derivate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2002105496A RU2002105496A (ru) | 2003-12-20 |
| RU2259349C2 true RU2259349C2 (ru) | 2005-08-27 |
Family
ID=7917726
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2002105496/04A RU2259349C2 (ru) | 1999-08-09 | 2000-07-25 | Замещенные производные 2-диалкиламиноалкилбифенила |
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|---|---|
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| EP (1) | EP1202953B1 (enExample) |
| JP (1) | JP5042422B2 (enExample) |
| KR (1) | KR100723816B1 (enExample) |
| CN (2) | CN1245376C (enExample) |
| AR (1) | AR025052A1 (enExample) |
| AT (1) | ATE338021T1 (enExample) |
| AU (1) | AU778596B2 (enExample) |
| BR (1) | BR0013316A (enExample) |
| CA (1) | CA2380857C (enExample) |
| CO (1) | CO5200790A1 (enExample) |
| CY (1) | CY1105387T1 (enExample) |
| CZ (1) | CZ302984B6 (enExample) |
| DE (2) | DE19937537A1 (enExample) |
| DK (1) | DK1202953T3 (enExample) |
| ES (1) | ES2270861T3 (enExample) |
| HK (1) | HK1046400B (enExample) |
| HU (1) | HUP0202075A3 (enExample) |
| IL (2) | IL148058A0 (enExample) |
| MX (1) | MXPA02001372A (enExample) |
| NO (1) | NO327670B1 (enExample) |
| NZ (1) | NZ517364A (enExample) |
| PE (1) | PE20010384A1 (enExample) |
| PL (1) | PL199880B1 (enExample) |
| PT (1) | PT1202953E (enExample) |
| RU (1) | RU2259349C2 (enExample) |
| SI (1) | SI1202953T1 (enExample) |
| SK (1) | SK287353B6 (enExample) |
| WO (1) | WO2001010816A2 (enExample) |
| ZA (1) | ZA200201917B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2814636C1 (ru) * | 2020-09-11 | 2024-03-04 | Бейджинг Хунхуэй Медитек Ко., Лтд | Способ получения водорастворимых производных магнолола и производных хонокиола и их интермедиатов, и родственных моногидрокси-защищенных интермедиатов |
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| 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 |
| JP5491416B2 (ja) | 2008-02-01 | 2014-05-14 | パンミラ ファーマシューティカルズ,エルエルシー. | プロスタグランジンd2受容体のn,n−2置換アミノアルキルビフェニルアンタゴニスト |
| EP2245002A4 (en) * | 2008-02-01 | 2011-08-17 | Amira Pharmaceuticals Inc | AMINOALKYLBIPHENYL ANTAGONISTS N, N 'DISUBSTITUTED FROM D2 RECEPTORS OF PROSTAGLANDIN |
| US8242145B2 (en) * | 2008-02-14 | 2012-08-14 | Panmira Pharmaceuticals, Llc | Cyclic diaryl ether compounds as antagonists of prostaglandin D2 receptors |
| EP2245022A4 (en) * | 2008-02-25 | 2012-02-22 | Panmira Pharmaceuticals Llc | ANTAGONISTS OF PROSTAGLANDIN D2 RECEPTORS |
| EP2268611A2 (en) * | 2008-04-02 | 2011-01-05 | Amira Pharmaceuticals, Inc. | Aminoalkylphenyl antagonists of prostaglandin d2 receptors |
| TWI403319B (zh) * | 2008-07-03 | 2013-08-01 | Panmira Pharmaceuticals Llc | 前列腺素d2受體之雜烷基拮抗劑 |
| 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 |
| SG178252A1 (en) | 2009-08-05 | 2012-03-29 | Panmira Pharmaceuticals Llc | Dp2 antagonist and uses thereof |
| PH12012501349A1 (en) | 2010-01-06 | 2013-01-14 | 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 |
|---|---|---|---|---|
| US3443943A (en) * | 1967-07-24 | 1969-05-13 | Polaroid Corp | Photographic products and processes employing ring - closing 2 - equivalent silver halide developing agents |
| US4473709A (en) * | 1980-07-14 | 1984-09-25 | Fmc Corporation | Pyrethroid intermediates and process |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| EP0946499B1 (en) * | 1996-11-22 | 2005-06-01 | Elan Pharmaceuticals, Inc. | N-(aryl/heteroaryl/alkylacetyl) amino acid amides, pharmaceutical compositions comprising same, and methods for inhibiting beta-amyloid peptide release and/or its synthesis by use of such compounds |
| ZA985247B (en) * | 1997-06-19 | 1999-12-17 | Du Pont Merck Pharma | Guanidine mimics as factor Xa inhibitors. |
-
1999
- 1999-08-09 DE DE19937537A patent/DE19937537A1/de not_active Withdrawn
-
2000
- 2000-07-25 ES ES00951440T patent/ES2270861T3/es not_active Expired - Lifetime
- 2000-07-25 MX MXPA02001372A patent/MXPA02001372A/es active IP Right Grant
- 2000-07-25 AU AU64374/00A patent/AU778596B2/en not_active Ceased
- 2000-07-25 BR BR0013316-7A patent/BR0013316A/pt not_active IP Right Cessation
- 2000-07-25 KR KR1020027001825A patent/KR100723816B1/ko not_active Expired - Fee Related
- 2000-07-25 AT AT00951440T patent/ATE338021T1/de active
- 2000-07-25 PL PL353876A patent/PL199880B1/pl not_active IP Right Cessation
- 2000-07-25 NZ NZ517364A patent/NZ517364A/en not_active IP Right Cessation
- 2000-07-25 WO PCT/EP2000/007095 patent/WO2001010816A2/de not_active Ceased
- 2000-07-25 DK DK00951440T patent/DK1202953T3/da active
- 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 HK HK02107800.3A patent/HK1046400B/zh not_active IP Right Cessation
- 2000-07-25 SK SK203-2002A patent/SK287353B6/sk not_active IP Right Cessation
- 2000-07-25 DE DE50013404T patent/DE50013404D1/de not_active Expired - Lifetime
- 2000-07-25 HU HU0202075A patent/HUP0202075A3/hu unknown
- 2000-07-25 PT PT00951440T patent/PT1202953E/pt unknown
- 2000-07-25 CN CN200610004917A patent/CN100575334C/zh not_active Expired - Fee Related
- 2000-07-25 SI SI200030909T patent/SI1202953T1/sl unknown
- 2000-07-25 IL IL14805800A patent/IL148058A0/xx active IP Right Grant
- 2000-07-25 RU RU2002105496/04A patent/RU2259349C2/ru not_active IP Right Cessation
- 2000-07-25 CA CA2380857A patent/CA2380857C/en not_active Expired - Fee Related
- 2000-07-25 EP EP00951440A patent/EP1202953B1/de not_active Expired - Lifetime
- 2000-07-25 CZ CZ20020492A patent/CZ302984B6/cs not_active IP Right Cessation
- 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 |
|---|---|---|---|---|
| US3443943A (en) * | 1967-07-24 | 1969-05-13 | Polaroid Corp | Photographic products and processes employing ring - closing 2 - equivalent silver halide developing agents |
| US4473709A (en) * | 1980-07-14 | 1984-09-25 | Fmc Corporation | Pyrethroid intermediates and process |
Non-Patent Citations (1)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2814636C1 (ru) * | 2020-09-11 | 2024-03-04 | Бейджинг Хунхуэй Медитек Ко., Лтд | Способ получения водорастворимых производных магнолола и производных хонокиола и их интермедиатов, и родственных моногидрокси-защищенных интермедиатов |
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| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20130726 |