CZ302984B6 - Substituované deriváty 2-dialkylaminoalkylbifenylu, zpusob jejich výroby, léciva tyto látky obsahující a jejich použití - Google Patents
Substituované deriváty 2-dialkylaminoalkylbifenylu, zpusob jejich výroby, léciva tyto látky obsahující a jejich použití Download PDFInfo
- Publication number
- CZ302984B6 CZ302984B6 CZ20020492A CZ2002492A CZ302984B6 CZ 302984 B6 CZ302984 B6 CZ 302984B6 CZ 20020492 A CZ20020492 A CZ 20020492A CZ 2002492 A CZ2002492 A CZ 2002492A CZ 302984 B6 CZ302984 B6 CZ 302984B6
- Authority
- CZ
- Czechia
- Prior art keywords
- corresponding hydrochloride
- dimethylamine
- ylmethyl
- hydrochloride
- substituted
- Prior art date
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- 239000003814 drug Substances 0.000 title claims abstract description 33
- 238000000034 method Methods 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 48
- 208000002193 Pain Diseases 0.000 claims abstract description 12
- 230000036407 pain Effects 0.000 claims abstract description 10
- 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 7
- 208000007882 Gastritis Diseases 0.000 claims abstract description 7
- 206010015037 epilepsy Diseases 0.000 claims abstract description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 473
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 170
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 120
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 117
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 105
- 239000000203 mixture Substances 0.000 claims description 92
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 91
- 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 82
- -1 acetamidyl Chemical group 0.000 claims description 49
- 235000019441 ethanol Nutrition 0.000 claims description 47
- 125000004432 carbon atom Chemical group C* 0.000 claims description 38
- 229910052757 nitrogen Inorganic materials 0.000 claims description 34
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 32
- 239000002253 acid Substances 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 238000006243 chemical reaction 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
- 125000002947 alkylene group Chemical group 0.000 claims description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 12
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 11
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 238000007796 conventional method Methods 0.000 claims description 8
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 229940079593 drug Drugs 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000001424 substituent group Chemical group 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
- 206010011224 Cough Diseases 0.000 claims description 6
- 206010012735 Diarrhoea 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
- 208000020016 psychiatric disease Diseases 0.000 claims description 6
- 208000023504 respiratory system disease Diseases 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 claims description 6
- 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 5
- 208000007848 Alcoholism Diseases 0.000 claims description 5
- 206010013654 Drug abuse Diseases 0.000 claims description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 5
- 239000013543 active substance Substances 0.000 claims description 5
- 206010001584 alcohol abuse Diseases 0.000 claims description 5
- 208000025746 alcohol use disease Diseases 0.000 claims description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical group 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
- 208000011117 substance-related disease Diseases 0.000 claims description 5
- 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
- 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 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 150000005840 aryl radicals Chemical class 0.000 claims description 4
- 238000006555 catalytic reaction Methods 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
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 235000019253 formic acid Nutrition 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 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 4
- 150000002940 palladium Chemical class 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
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 4
- 229910052723 transition metal Inorganic materials 0.000 claims description 4
- 150000003624 transition metals Chemical class 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
- 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 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
- 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 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
- 150000007513 acids Chemical class 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 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
- 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
- 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 3
- 238000000746 purification Methods 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 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 2
- 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 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
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- 239000011260 aqueous acid Substances 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
- 125000005843 halogen group Chemical group 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 239000011630 iodine Chemical group 0.000 claims description 2
- 229910052740 iodine Chemical group 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 239000012279 sodium borohydride Substances 0.000 claims description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims 5
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 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 2
- 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 1
- 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 1
- 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 1
- GZNUGXLDNUTRHC-UHFFFAOYSA-N 1-chloro-2-methoxy-4-phenylbenzene Chemical group C1=C(Cl)C(OC)=CC(C=2C=CC=CC=2)=C1 GZNUGXLDNUTRHC-UHFFFAOYSA-N 0.000 claims 1
- GPWNWKWQOLEVEQ-UHFFFAOYSA-N 2,4-diaminopyrimidine-5-carbaldehyde Chemical compound NC1=NC=C(C=O)C(N)=N1 GPWNWKWQOLEVEQ-UHFFFAOYSA-N 0.000 claims 1
- VTQAISOXVCPZHW-UHFFFAOYSA-N 2-[2-(3,4-dimethoxyphenyl)phenyl]-n,n-dimethylethanamine Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC=CC=C1CCN(C)C VTQAISOXVCPZHW-UHFFFAOYSA-N 0.000 claims 1
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- 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 1
- 208000020401 Depressive disease Diseases 0.000 claims 1
- 125000005025 alkynylaryl group Chemical group 0.000 claims 1
- QYRFJLLXPINATB-UHFFFAOYSA-N hydron;2,4,5,6-tetrafluorobenzene-1,3-diamine;dichloride Chemical compound Cl.Cl.NC1=C(F)C(N)=C(F)C(F)=C1F QYRFJLLXPINATB-UHFFFAOYSA-N 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 88
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Classifications
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- 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
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- C—CHEMISTRY; METALLURGY
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- 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
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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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- C07C215/52—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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- 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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- C07C217/54—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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- C07C223/00—Compounds containing amino and —CHO groups bound to the same carbon skeleton
- C07C223/02—Compounds containing amino and —CHO groups bound to the same carbon skeleton having amino groups bound to acyclic carbon atoms of the carbon skeleton
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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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- C07C225/14—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
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- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Pulmonology (AREA)
- Diabetes (AREA)
- Rheumatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Immunology (AREA)
- Hematology (AREA)
- Addiction (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)
- Furan Compounds (AREA)
- Indole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
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 (2)
| Publication Number | Publication Date |
|---|---|
| CZ2002492A3 CZ2002492A3 (cs) | 2002-05-15 |
| CZ302984B6 true CZ302984B6 (cs) | 2012-02-01 |
Family
ID=7917726
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ20020492A CZ302984B6 (cs) | 1999-08-09 | 2000-07-25 | Substituované deriváty 2-dialkylaminoalkylbifenylu, zpusob jejich výroby, léciva tyto látky obsahující a jejich použití |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US6710080B2 (enExample) |
| 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) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6946559B2 (en) | 2000-02-02 | 2005-09-20 | 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 |
| UA98839C2 (en) * | 2008-02-01 | 2012-06-25 | Панмира Фармасьютикалз, Ллк. | N,n-disubstituted aminoalkylbiphenyl antagonists of prostaglandin d2 receptors |
| EP2257524B1 (en) * | 2008-02-01 | 2016-01-06 | Brickell Biotech, Inc. | N,n-disubstituted aminoalkylbiphenyl antagonists of prostaglandin d2 receptors |
| JP2011512359A (ja) * | 2008-02-14 | 2011-04-21 | 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受容体のアンタゴニストとしての環式ジアリールエーテル化合物 |
| US8497381B2 (en) * | 2008-02-25 | 2013-07-30 | Panmira Pharmaceuticals, Llc | Antagonists of prostaglandin D2 receptors |
| JP2011518130A (ja) * | 2008-04-02 | 2011-06-23 | 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受容体のアミノアルキルフェニルアンタゴニスト |
| WO2010003120A2 (en) * | 2008-07-03 | 2010-01-07 | Amira Pharmaceuticals, Inc. | 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 |
| WO2010042652A2 (en) | 2008-10-08 | 2010-04-15 | Amira Pharmaceuticals, Inc. | 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 |
| EP2461809A4 (en) | 2009-07-31 | 2013-06-19 | Panmira Pharmaceuticals Llc | OPHTHALMIC PHARMACEUTICAL COMPOSITIONS OF DP2 RECEPTOR ANTAGONSITES |
| CA2768587A1 (en) | 2009-08-05 | 2011-02-10 | Panmira Pharmaceuticals, Llc | Dp2 antagonist and uses thereof |
| 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 |
|---|---|---|---|---|
| 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 |
| ATE296797T1 (de) * | 1996-11-22 | 2005-06-15 | Elan Pharm Inc | N-(aryl/heteroaryl/alkylacetyl) amino saüre amide,pharmazeutische zusammensetzungen damit, und methodenzur inhibierung beta-amyloid peptid freisetzung oder synthese |
| 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 DK DK00951440T patent/DK1202953T3/da active
- 2000-07-25 EP EP00951440A patent/EP1202953B1/de not_active Expired - Lifetime
- 2000-07-25 HU HU0202075A patent/HUP0202075A3/hu unknown
- 2000-07-25 PL PL353876A patent/PL199880B1/pl 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 CN CN200610004917A patent/CN100575334C/zh not_active Expired - Fee Related
- 2000-07-25 AU AU64374/00A patent/AU778596B2/en not_active Ceased
- 2000-07-25 KR KR1020027001825A patent/KR100723816B1/ko not_active Expired - Fee Related
- 2000-07-25 MX MXPA02001372A patent/MXPA02001372A/es active IP Right Grant
- 2000-07-25 AT AT00951440T patent/ATE338021T1/de active
- 2000-07-25 BR BR0013316-7A patent/BR0013316A/pt not_active IP Right Cessation
- 2000-07-25 JP JP2001515283A patent/JP5042422B2/ja not_active Expired - Fee Related
- 2000-07-25 SI SI200030909T patent/SI1202953T1/sl unknown
- 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 DE DE50013404T patent/DE50013404D1/de not_active Expired - Lifetime
- 2000-07-25 CA CA2380857A patent/CA2380857C/en not_active Expired - Fee Related
- 2000-07-25 RU RU2002105496/04A patent/RU2259349C2/ru not_active IP Right Cessation
- 2000-07-25 CZ CZ20020492A patent/CZ302984B6/cs not_active IP Right Cessation
- 2000-07-25 PT PT00951440T patent/PT1202953E/pt unknown
- 2000-07-25 ES ES00951440T patent/ES2270861T3/es not_active Expired - Lifetime
- 2000-07-25 IL IL14805800A patent/IL148058A0/xx active IP Right Grant
- 2000-07-25 SK SK203-2002A patent/SK287353B6/sk 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
-
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 |
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Legal Events
| Date | Code | Title | Description |
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| MM4A | Patent lapsed due to non-payment of fee |
Effective date: 20130725 |