SK287353B6 - Substituované deriváty 2-dialkylaminoalkylbifenylu, spôsob ich výroby, lieky tieto látky obsahujúce a ich použitie - Google Patents
Substituované deriváty 2-dialkylaminoalkylbifenylu, spôsob ich výroby, lieky tieto látky obsahujúce a ich použitie Download PDFInfo
- Publication number
- SK287353B6 SK287353B6 SK203-2002A SK2032002A SK287353B6 SK 287353 B6 SK287353 B6 SK 287353B6 SK 2032002 A SK2032002 A SK 2032002A SK 287353 B6 SK287353 B6 SK 287353B6
- Authority
- SK
- Slovakia
- Prior art keywords
- diethyl ether
- mmol
- hydrochloride
- carbon atoms
- dimethylamine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 239000003814 drug Substances 0.000 title description 14
- 229940079593 drug Drugs 0.000 title description 6
- -1 acetamidyl Chemical group 0.000 claims abstract description 41
- 150000001875 compounds Chemical class 0.000 claims abstract description 23
- 125000003118 aryl group Chemical group 0.000 claims abstract description 22
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims abstract description 7
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 239000002253 acid Substances 0.000 claims abstract description 6
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 5
- 150000007513 acids Chemical class 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 131
- 229910052757 nitrogen Inorganic materials 0.000 claims description 39
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000002947 alkylene group Chemical group 0.000 claims description 13
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]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
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 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 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 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
- 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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-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 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 150000005840 aryl radicals Chemical class 0.000 claims description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 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 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
- 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 2
- 150000003254 radicals Chemical class 0.000 claims 5
- IVTBYGAHXYCWQD-UHFFFAOYSA-N 2-[4-[(dimethylamino)methyl]phenyl]benzonitrile Chemical compound C1=CC(CN(C)C)=CC=C1C1=CC=CC=C1C#N IVTBYGAHXYCWQD-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 abstract description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 abstract 2
- 125000006237 oxymethylenoxy group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 463
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 111
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 98
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 97
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 88
- 239000000203 mixture Substances 0.000 description 83
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 81
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 74
- 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 description 73
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 72
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 70
- 239000012074 organic phase Substances 0.000 description 49
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 46
- 235000019341 magnesium sulphate Nutrition 0.000 description 46
- 239000000243 solution Substances 0.000 description 46
- 238000010992 reflux Methods 0.000 description 44
- 235000019441 ethanol Nutrition 0.000 description 42
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 41
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 41
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 36
- 239000011541 reaction mixture Substances 0.000 description 36
- 229910000029 sodium carbonate Inorganic materials 0.000 description 35
- 238000010828 elution Methods 0.000 description 34
- 239000000741 silica gel Substances 0.000 description 34
- 229910002027 silica gel Inorganic materials 0.000 description 34
- AZFVLHQDIIJLJG-UHFFFAOYSA-N chloromethylsilane Chemical compound [SiH3]CCl AZFVLHQDIIJLJG-UHFFFAOYSA-N 0.000 description 33
- 239000012071 phase Substances 0.000 description 30
- 230000002378 acidificating effect Effects 0.000 description 24
- ZPZPSZZVDFMNQS-UHFFFAOYSA-N 1-(2-bromophenyl)-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC=CC=C1Br ZPZPSZZVDFMNQS-UHFFFAOYSA-N 0.000 description 18
- 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 17
- 239000007864 aqueous solution Substances 0.000 description 17
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 16
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 238000003756 stirring Methods 0.000 description 13
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 12
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000000284 extract Substances 0.000 description 10
- 208000002193 Pain Diseases 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- CEQDOZNXFWUMTG-UHFFFAOYSA-N 2-(2-bromophenyl)-n,n-dimethylethanamine Chemical compound CN(C)CCC1=CC=CC=C1Br CEQDOZNXFWUMTG-UHFFFAOYSA-N 0.000 description 6
- 238000007796 conventional method Methods 0.000 description 6
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 5
- NLLGFYPSWCMUIV-UHFFFAOYSA-N (3-methoxyphenyl)boronic acid Chemical compound COC1=CC=CC(B(O)O)=C1 NLLGFYPSWCMUIV-UHFFFAOYSA-N 0.000 description 4
- SSIDIGWIEQDEDG-UHFFFAOYSA-N 1-[2-(3-methoxyphenyl)phenyl]-n,n-dimethylmethanamine;hydrochloride Chemical compound Cl.COC1=CC=CC(C=2C(=CC=CC=2)CN(C)C)=C1 SSIDIGWIEQDEDG-UHFFFAOYSA-N 0.000 description 4
- KPDPMYBMPREJGJ-UHFFFAOYSA-N 2-(2-dimethoxyboranylphenyl)-n,n-dimethylethanamine Chemical compound COB(OC)C1=CC=CC=C1CCN(C)C KPDPMYBMPREJGJ-UHFFFAOYSA-N 0.000 description 4
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 4
- 208000007848 Alcoholism Diseases 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 208000024172 Cardiovascular disease Diseases 0.000 description 4
- 206010011224 Cough Diseases 0.000 description 4
- 206010012735 Diarrhoea Diseases 0.000 description 4
- 206010013654 Drug abuse Diseases 0.000 description 4
- 208000007882 Gastritis Diseases 0.000 description 4
- 206010020751 Hypersensitivity Diseases 0.000 description 4
- 206010061218 Inflammation Diseases 0.000 description 4
- 241000699666 Mus <mouse, genus> Species 0.000 description 4
- 206010046543 Urinary incontinence Diseases 0.000 description 4
- VUDCTLOJEPCNRS-UHFFFAOYSA-N [2-[(dimethylamino)methyl]phenyl]boronic acid Chemical compound CN(C)CC1=CC=CC=C1B(O)O VUDCTLOJEPCNRS-UHFFFAOYSA-N 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 206010001584 alcohol abuse Diseases 0.000 description 4
- 208000025746 alcohol use disease Diseases 0.000 description 4
- 235000011089 carbon dioxide Nutrition 0.000 description 4
- 206010015037 epilepsy Diseases 0.000 description 4
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 4
- 230000002757 inflammatory effect Effects 0.000 description 4
- 208000020016 psychiatric disease Diseases 0.000 description 4
- 208000023504 respiratory system disease Diseases 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 208000011117 substance-related disease Diseases 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 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 description 3
- DLTQWUXSLRELFD-UHFFFAOYSA-N 2,6-dichloro-4-[2-[(dimethylamino)methyl]phenyl]aniline;hydrochloride Chemical compound Cl.CN(C)CC1=CC=CC=C1C1=CC(Cl)=C(N)C(Cl)=C1 DLTQWUXSLRELFD-UHFFFAOYSA-N 0.000 description 3
- ITRNQMJXZUWZQL-UHFFFAOYSA-N 2-(2-bromophenyl)ethanamine Chemical compound NCCC1=CC=CC=C1Br ITRNQMJXZUWZQL-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 230000000202 analgesic effect Effects 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 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 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- YZYDOFGGDSDUPX-UHFFFAOYSA-M sodium;carbonic acid;chloride Chemical compound [Na+].[Cl-].OC(O)=O YZYDOFGGDSDUPX-UHFFFAOYSA-M 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- FFOZJZDPBHHBHK-UHFFFAOYSA-N 1-[2-(3,5-difluorophenyl)phenyl]-n,n-dimethylmethanamine;hydrochloride Chemical compound Cl.CN(C)CC1=CC=CC=C1C1=CC(F)=CC(F)=C1 FFOZJZDPBHHBHK-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- YYIIPTAPEQLXKT-UHFFFAOYSA-N 1-[2-[3-(difluoromethyl)phenyl]phenyl]-n,n-dimethylmethanamine;hydrochloride Chemical compound Cl.CN(C)CC1=CC=CC=C1C1=CC=CC(C(F)F)=C1 YYIIPTAPEQLXKT-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- JYWJZIQSPRFCDB-UHFFFAOYSA-N 1-bromo-3-propan-2-yloxybenzene Chemical compound CC(C)OC1=CC=CC(Br)=C1 JYWJZIQSPRFCDB-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- DTQHYIZPVGWYQV-UHFFFAOYSA-N 2-[2-[(dimethylamino)methyl]phenyl]-4-(trifluoromethoxy)aniline;dihydrochloride Chemical compound Cl.Cl.CN(C)CC1=CC=CC=C1C1=CC(OC(F)(F)F)=CC=C1N DTQHYIZPVGWYQV-UHFFFAOYSA-N 0.000 description 2
- GLQGKRDYDYKALF-UHFFFAOYSA-N 2-[2-[(dimethylamino)methyl]phenyl]benzaldehyde;hydrochloride Chemical compound Cl.CN(C)CC1=CC=CC=C1C1=CC=CC=C1C=O GLQGKRDYDYKALF-UHFFFAOYSA-N 0.000 description 2
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- 238000003556 assay Methods 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
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- 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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- 208000015181 infectious disease Diseases 0.000 description 1
- 239000011630 iodine Chemical group 0.000 description 1
- 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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- 239000011777 magnesium Substances 0.000 description 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- 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 description 1
- RZSDQDMYAIKVCF-UHFFFAOYSA-N n,n-dimethyl-1-[2-(3-propan-2-yloxyphenyl)phenyl]methanamine Chemical compound CC(C)OC1=CC=CC(C=2C(=CC=CC=2)CN(C)C)=C1 RZSDQDMYAIKVCF-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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
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- 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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- 239000000014 opioid analgesic Substances 0.000 description 1
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000611 regression analysis Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 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
- 230000036280 sedation Effects 0.000 description 1
- 230000020341 sensory perception of pain Effects 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 238000005303 weighing Methods 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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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- C07—ORGANIC CHEMISTRY
- 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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- 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
- 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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- 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
- 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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- C—CHEMISTRY; METALLURGY
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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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/56—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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- C07C217/00—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
- C07C217/60—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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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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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- C07—ORGANIC CHEMISTRY
- 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
- 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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- C—CHEMISTRY; METALLURGY
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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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- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
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- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
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- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Immunology (AREA)
- Hematology (AREA)
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- 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)
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19937537A DE19937537A1 (de) | 1999-08-09 | 1999-08-09 | Substituierte 2-Dialkylaminoalkylbiphenyl-Derivate |
| PCT/EP2000/007095 WO2001010816A2 (de) | 1999-08-09 | 2000-07-25 | Substituierte 2-dialkylaminoalkylbiphenyl-derivate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK2032002A3 SK2032002A3 (en) | 2002-06-04 |
| SK287353B6 true SK287353B6 (sk) | 2010-08-09 |
Family
ID=7917726
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK203-2002A SK287353B6 (sk) | 1999-08-09 | 2000-07-25 | Substituované deriváty 2-dialkylaminoalkylbifenylu, spôsob ich výroby, lieky tieto látky obsahujúce a ich použitie |
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) |
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| 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 |
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| 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 |
| US4473709A (en) * | 1980-07-14 | 1984-09-25 | Fmc Corporation | Pyrethroid intermediates and process |
| 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. |
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1999
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed due to non-payment of maintenance fees |
Effective date: 20130725 |