SK412002A3 - 3-amino-2-benzyl-1-phenyl-propane derivatives, process for producing thereof, drugs comprising said derivatives and their use - Google Patents
3-amino-2-benzyl-1-phenyl-propane derivatives, process for producing thereof, drugs comprising said derivatives and their use Download PDFInfo
- Publication number
- SK412002A3 SK412002A3 SK41-2002A SK412002A SK412002A3 SK 412002 A3 SK412002 A3 SK 412002A3 SK 412002 A SK412002 A SK 412002A SK 412002 A3 SK412002 A3 SK 412002A3
- Authority
- SK
- Slovakia
- Prior art keywords
- phenyl
- benzyl
- corresponding hydrochloride
- dimethylamino
- represent
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 93
- OUGPXHYMXCVURU-UHFFFAOYSA-N 2-benzyl-3-phenylpropan-1-amine Chemical class C=1C=CC=CC=1CC(CN)CC1=CC=CC=C1 OUGPXHYMXCVURU-UHFFFAOYSA-N 0.000 title claims abstract description 74
- 239000003814 drug Substances 0.000 title claims abstract description 28
- 229940079593 drug Drugs 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 80
- 239000000126 substance Substances 0.000 claims abstract description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 290
- 150000003254 radicals Chemical class 0.000 claims description 136
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 112
- 239000001257 hydrogen Substances 0.000 claims description 82
- 229910052739 hydrogen Inorganic materials 0.000 claims description 82
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 80
- 125000004432 carbon atom Chemical group C* 0.000 claims description 78
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 71
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 66
- -1 OR 7 or SR 7 Chemical class 0.000 claims description 56
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 46
- 150000003839 salts Chemical class 0.000 claims description 39
- 238000003747 Grignard reaction Methods 0.000 claims description 36
- 239000002253 acid Substances 0.000 claims description 33
- 150000007513 acids Chemical class 0.000 claims description 33
- 125000002947 alkylene group Chemical group 0.000 claims description 33
- 238000006683 Mannich reaction Methods 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 31
- 229910052801 chlorine Inorganic materials 0.000 claims description 31
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 24
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 24
- 239000011777 magnesium Substances 0.000 claims description 24
- 229910052749 magnesium Inorganic materials 0.000 claims description 24
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 23
- 150000005840 aryl radicals Chemical group 0.000 claims description 22
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 22
- 229910052740 iodine Inorganic materials 0.000 claims description 22
- 238000004519 manufacturing process Methods 0.000 claims description 20
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 18
- 239000000460 chlorine Substances 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 17
- XYAYVKVKURJWKT-UHFFFAOYSA-N 2-benzyl-3-(dimethylamino)-1-(3-methoxyphenyl)propan-1-one Chemical compound COC1=CC=CC(C(=O)C(CN(C)C)CC=2C=CC=CC=2)=C1 XYAYVKVKURJWKT-UHFFFAOYSA-N 0.000 claims description 16
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 238000007796 conventional method Methods 0.000 claims description 13
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- 208000002193 Pain Diseases 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 12
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 12
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims description 10
- 229930182817 methionine Natural products 0.000 claims description 10
- 230000036407 pain Effects 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 238000005882 aldol condensation 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
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 150000003840 hydrochlorides Chemical class 0.000 claims description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 claims description 6
- DLWXDAOTAJIQMA-UHFFFAOYSA-N 2-benzyl-3-(dimethylamino)-1-(3-phenylmethoxyphenyl)propan-1-one Chemical compound C=1C=CC(OCC=2C=CC=CC=2)=CC=1C(=O)C(CN(C)C)CC1=CC=CC=C1 DLWXDAOTAJIQMA-UHFFFAOYSA-N 0.000 claims description 5
- 150000001299 aldehydes Chemical class 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 5
- YMBYCDJJYGZUFJ-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)-3-(3-methylphenyl)propan-1-one Chemical compound COC1=CC=CC(C(=O)C(CN(C)C)CC=2C=C(C)C=CC=2)=C1 YMBYCDJJYGZUFJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- 150000001336 alkenes Chemical class 0.000 claims description 4
- 238000011065 in-situ storage Methods 0.000 claims description 4
- 229910052744 lithium Inorganic materials 0.000 claims description 4
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000011701 zinc Chemical group 0.000 claims description 4
- 229910052725 zinc Chemical group 0.000 claims description 4
- UQGHIGZYYSTGFO-UHFFFAOYSA-N 2-benzyl-3-(dimethylamino)-1-(3-hydroxyphenyl)propan-1-one Chemical compound C=1C=CC(O)=CC=1C(=O)C(CN(C)C)CC1=CC=CC=C1 UQGHIGZYYSTGFO-UHFFFAOYSA-N 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 206010046543 Urinary incontinence Diseases 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 150000002902 organometallic compounds Chemical class 0.000 claims description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- UQGHIGZYYSTGFO-MRXNPFEDSA-N (2r)-2-benzyl-3-(dimethylamino)-1-(3-hydroxyphenyl)propan-1-one Chemical compound C([C@H](CN(C)C)C(=O)C=1C=C(O)C=CC=1)C1=CC=CC=C1 UQGHIGZYYSTGFO-MRXNPFEDSA-N 0.000 claims description 2
- XYAYVKVKURJWKT-QGZVFWFLSA-N (2r)-2-benzyl-3-(dimethylamino)-1-(3-methoxyphenyl)propan-1-one Chemical compound COC1=CC=CC(C(=O)[C@@H](CN(C)C)CC=2C=CC=CC=2)=C1 XYAYVKVKURJWKT-QGZVFWFLSA-N 0.000 claims description 2
- BPODRCVWCQXHKK-INIZCTEOSA-N (2s)-2-[(dimethylamino)methyl]-3-(3-fluorophenyl)-1-(3-methoxyphenyl)propan-1-one Chemical compound COC1=CC=CC(C(=O)[C@H](CN(C)C)CC=2C=C(F)C=CC=2)=C1 BPODRCVWCQXHKK-INIZCTEOSA-N 0.000 claims description 2
- UQGHIGZYYSTGFO-INIZCTEOSA-N (2s)-2-benzyl-3-(dimethylamino)-1-(3-hydroxyphenyl)propan-1-one Chemical compound C([C@@H](CN(C)C)C(=O)C=1C=C(O)C=CC=1)C1=CC=CC=C1 UQGHIGZYYSTGFO-INIZCTEOSA-N 0.000 claims description 2
- XYAYVKVKURJWKT-KRWDZBQOSA-N (2s)-2-benzyl-3-(dimethylamino)-1-(3-methoxyphenyl)propan-1-one Chemical compound COC1=CC=CC(C(=O)[C@H](CN(C)C)CC=2C=CC=CC=2)=C1 XYAYVKVKURJWKT-KRWDZBQOSA-N 0.000 claims description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 2
- HNXAIDPRVNGKAG-SQFVCTCFSA-N (e)-2-benzyl-3-(3-methoxyphenyl)-n,n-dimethylpent-3-en-1-amine Chemical compound COC1=CC=CC(C(=C\C)\C(CN(C)C)CC=2C=CC=CC=2)=C1 HNXAIDPRVNGKAG-SQFVCTCFSA-N 0.000 claims description 2
- KWJMWNUSSAICTB-UHFFFAOYSA-N 1-(3-methoxyphenyl)-2-(methylaminomethyl)-3-(3-methylphenyl)propan-1-one Chemical compound C=1C=CC(OC)=CC=1C(=O)C(CNC)CC1=CC=CC(C)=C1 KWJMWNUSSAICTB-UHFFFAOYSA-N 0.000 claims description 2
- AKKTVUYEFOMFHP-UHFFFAOYSA-N 2-(dimethylamino)-3-(3-fluorophenyl)-1-(3-hydroxyphenyl)-2-methylpropan-1-one Chemical compound C=1C=CC(O)=CC=1C(=O)C(C)(N(C)C)CC1=CC=CC(F)=C1 AKKTVUYEFOMFHP-UHFFFAOYSA-N 0.000 claims description 2
- UJQWVLWXAWPVGQ-UHFFFAOYSA-N 2-[(3-chlorophenyl)methyl]-3-(dimethylamino)-1-(3-hydroxyphenyl)propan-1-one Chemical compound C=1C=CC(O)=CC=1C(=O)C(CN(C)C)CC1=CC=CC(Cl)=C1 UJQWVLWXAWPVGQ-UHFFFAOYSA-N 0.000 claims description 2
- YVNINYUFTHVSHJ-UHFFFAOYSA-N 2-[(3-chlorophenyl)methyl]-3-(dimethylamino)-1-(3-methoxyphenyl)propan-1-one Chemical compound COC1=CC=CC(C(=O)C(CN(C)C)CC=2C=C(Cl)C=CC=2)=C1 YVNINYUFTHVSHJ-UHFFFAOYSA-N 0.000 claims description 2
- UFQDFVKTMNKXDJ-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-1,3,6-triphenylhexan-1-one Chemical compound C=1C=CC=CC=1C(=O)C(CN(C)C)C(C=1C=CC=CC=1)CCCC1=CC=CC=C1 UFQDFVKTMNKXDJ-UHFFFAOYSA-N 0.000 claims description 2
- XJUCTUHNBZDEKE-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-1,3-bis(3-methoxyphenyl)-3-phenylpropan-1-one Chemical compound COC1=CC=CC(C(C(CN(C)C)C(=O)C=2C=C(OC)C=CC=2)C=2C=CC=CC=2)=C1 XJUCTUHNBZDEKE-UHFFFAOYSA-N 0.000 claims description 2
- GJNGUVXJRYGDDQ-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-1,3-bis(3-methoxyphenyl)propan-1-one Chemical compound COC1=CC=CC(CC(CN(C)C)C(=O)C=2C=C(OC)C=CC=2)=C1 GJNGUVXJRYGDDQ-UHFFFAOYSA-N 0.000 claims description 2
- SPAJWQDRXDRCTL-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-1-(3-hydroxyphenyl)-3-(3-methylphenyl)propan-1-one Chemical compound C=1C=CC(O)=CC=1C(=O)C(CN(C)C)CC1=CC=CC(C)=C1 SPAJWQDRXDRCTL-UHFFFAOYSA-N 0.000 claims description 2
- YRUIFXZZCDMATG-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-1-(3-hydroxyphenyl)-3-[3-(trifluoromethyl)phenyl]propan-1-one Chemical compound C=1C=CC(O)=CC=1C(=O)C(CN(C)C)CC1=CC=CC(C(F)(F)F)=C1 YRUIFXZZCDMATG-UHFFFAOYSA-N 0.000 claims description 2
- CGKLENWFXVNKDM-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)-3-(4-methoxyphenyl)propan-1-one Chemical compound C1=CC(OC)=CC=C1CC(CN(C)C)C(=O)C1=CC=CC(OC)=C1 CGKLENWFXVNKDM-UHFFFAOYSA-N 0.000 claims description 2
- KPNXDMUUSBDNLT-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)-3-[3-(trifluoromethyl)phenyl]propan-1-one Chemical compound COC1=CC=CC(C(=O)C(CN(C)C)CC=2C=C(C=CC=2)C(F)(F)F)=C1 KPNXDMUUSBDNLT-UHFFFAOYSA-N 0.000 claims description 2
- BLBBORNCXNYNND-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-3-(2-fluorophenyl)-1-(3-methoxyphenyl)propan-1-one Chemical compound COC1=CC=CC(C(=O)C(CN(C)C)CC=2C(=CC=CC=2)F)=C1 BLBBORNCXNYNND-UHFFFAOYSA-N 0.000 claims description 2
- BPODRCVWCQXHKK-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-3-(3-fluorophenyl)-1-(3-methoxyphenyl)propan-1-one Chemical compound COC1=CC=CC(C(=O)C(CN(C)C)CC=2C=C(F)C=CC=2)=C1 BPODRCVWCQXHKK-UHFFFAOYSA-N 0.000 claims description 2
- PPXXMOWEQXWOPF-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-3-(4-fluorophenyl)-1-(3-hydroxyphenyl)propan-1-one Chemical compound C=1C=CC(O)=CC=1C(=O)C(CN(C)C)CC1=CC=C(F)C=C1 PPXXMOWEQXWOPF-UHFFFAOYSA-N 0.000 claims description 2
- JOLDPXSQOUUSMV-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-3-(4-fluorophenyl)-1-(3-methoxyphenyl)propan-1-one Chemical compound COC1=CC=CC(C(=O)C(CN(C)C)CC=2C=CC(F)=CC=2)=C1 JOLDPXSQOUUSMV-UHFFFAOYSA-N 0.000 claims description 2
- RGICCULPCWNRAB-UHFFFAOYSA-N 2-[2-(2-hexoxyethoxy)ethoxy]ethanol Chemical group CCCCCCOCCOCCOCCO RGICCULPCWNRAB-UHFFFAOYSA-N 0.000 claims description 2
- HMDPCNRYOPOJAO-UHFFFAOYSA-N 2-benzyl-1-(2,3-dichlorophenyl)-3-(dimethylamino)propan-1-one Chemical compound C=1C=CC(Cl)=C(Cl)C=1C(=O)C(CN(C)C)CC1=CC=CC=C1 HMDPCNRYOPOJAO-UHFFFAOYSA-N 0.000 claims description 2
- RMLRCSZWPMEARA-UHFFFAOYSA-N 2-benzyl-1-(2,5-dichlorophenyl)-3-(dimethylamino)propan-1-one Chemical compound C=1C(Cl)=CC=C(Cl)C=1C(=O)C(CN(C)C)CC1=CC=CC=C1 RMLRCSZWPMEARA-UHFFFAOYSA-N 0.000 claims description 2
- YKWWJVZYSJBOHO-UHFFFAOYSA-N 2-benzyl-1-(2-chloro-4-fluorophenyl)-3-(dimethylamino)propan-1-one Chemical compound C=1C=C(F)C=C(Cl)C=1C(=O)C(CN(C)C)CC1=CC=CC=C1 YKWWJVZYSJBOHO-UHFFFAOYSA-N 0.000 claims description 2
- JCRJFMMROVBZEC-UHFFFAOYSA-N 2-benzyl-1-(3,5-dimethoxyphenyl)-3-(dimethylamino)propan-1-one Chemical compound COC1=CC(OC)=CC(C(=O)C(CN(C)C)CC=2C=CC=CC=2)=C1 JCRJFMMROVBZEC-UHFFFAOYSA-N 0.000 claims description 2
- GCTQWYYAKZHTIQ-UHFFFAOYSA-N 2-benzyl-1-(3-methoxyphenyl)-n,n-dimethylpropane-1,3-diamine Chemical compound COC1=CC=CC(C(C(CN)CC=2C=CC=CC=2)N(C)C)=C1 GCTQWYYAKZHTIQ-UHFFFAOYSA-N 0.000 claims description 2
- GWSRWJKXNOQSKA-UHFFFAOYSA-N 2-benzyl-3-(dimethylamino)-1-(2,3,4-trimethoxyphenyl)propan-1-one Chemical compound COC1=C(OC)C(OC)=CC=C1C(=O)C(CN(C)C)CC1=CC=CC=C1 GWSRWJKXNOQSKA-UHFFFAOYSA-N 0.000 claims description 2
- SVHZZSSWPXFHHE-UHFFFAOYSA-N 2-benzyl-3-(dimethylamino)-1-(2-fluorophenyl)propan-1-one Chemical compound C=1C=CC=C(F)C=1C(=O)C(CN(C)C)CC1=CC=CC=C1 SVHZZSSWPXFHHE-UHFFFAOYSA-N 0.000 claims description 2
- KBLBGJMLNNRNPI-UHFFFAOYSA-N 2-benzyl-3-(dimethylamino)-1-(2-hydroxy-5-methoxyphenyl)propan-1-one Chemical compound COC1=CC=C(O)C(C(=O)C(CN(C)C)CC=2C=CC=CC=2)=C1 KBLBGJMLNNRNPI-UHFFFAOYSA-N 0.000 claims description 2
- XFUZUEYXSZIHFU-UHFFFAOYSA-N 2-benzyl-3-(dimethylamino)-1-(2-hydroxyphenyl)propan-1-one Chemical compound C=1C=CC=C(O)C=1C(=O)C(CN(C)C)CC1=CC=CC=C1 XFUZUEYXSZIHFU-UHFFFAOYSA-N 0.000 claims description 2
- OJTJWOBDQMRDAU-UHFFFAOYSA-N 2-benzyl-3-(dimethylamino)-1-(2-methoxyphenyl)propan-1-one Chemical compound COC1=CC=CC=C1C(=O)C(CN(C)C)CC1=CC=CC=C1 OJTJWOBDQMRDAU-UHFFFAOYSA-N 0.000 claims description 2
- UQRNZVVUDBXWRU-UHFFFAOYSA-N 2-benzyl-3-(dimethylamino)-1-(2-phenylphenyl)propan-1-one Chemical compound C=1C=CC=C(C=2C=CC=CC=2)C=1C(=O)C(CN(C)C)CC1=CC=CC=C1 UQRNZVVUDBXWRU-UHFFFAOYSA-N 0.000 claims description 2
- KLINQZNFNVZDRS-UHFFFAOYSA-N 2-benzyl-3-(dimethylamino)-1-(3,4,5-trimethoxyphenyl)propan-1-one Chemical compound COC1=C(OC)C(OC)=CC(C(=O)C(CN(C)C)CC=2C=CC=CC=2)=C1 KLINQZNFNVZDRS-UHFFFAOYSA-N 0.000 claims description 2
- WIIKSACKGWLIBQ-UHFFFAOYSA-N 2-benzyl-3-(dimethylamino)-1-(3-methylsulfanylphenyl)propan-1-one Chemical compound CSC1=CC=CC(C(=O)C(CN(C)C)CC=2C=CC=CC=2)=C1 WIIKSACKGWLIBQ-UHFFFAOYSA-N 0.000 claims description 2
- RWKUXZILGVFKAP-UHFFFAOYSA-N 2-benzyl-3-(dimethylamino)-1-(3-phenylphenyl)propan-1-one Chemical compound C=1C=CC(C=2C=CC=CC=2)=CC=1C(=O)C(CN(C)C)CC1=CC=CC=C1 RWKUXZILGVFKAP-UHFFFAOYSA-N 0.000 claims description 2
- SRRZOGHANAHAQV-UHFFFAOYSA-N 2-benzyl-3-(dimethylamino)-1-(6-hydroxynaphthalen-2-yl)propan-1-one Chemical compound C=1C=C2C=C(O)C=CC2=CC=1C(=O)C(CN(C)C)CC1=CC=CC=C1 SRRZOGHANAHAQV-UHFFFAOYSA-N 0.000 claims description 2
- UFJBXLVIZHQXTD-UHFFFAOYSA-N 2-benzyl-3-(dimethylamino)-1-[3-(trifluoromethyl)phenyl]propan-1-one Chemical compound C=1C=CC(C(F)(F)F)=CC=1C(=O)C(CN(C)C)CC1=CC=CC=C1 UFJBXLVIZHQXTD-UHFFFAOYSA-N 0.000 claims description 2
- NGIRHLFRGWPZMH-UHFFFAOYSA-N 2-benzyl-3-(dimethylamino)-1-naphthalen-2-ylpropan-1-one Chemical compound C=1C=C2C=CC=CC2=CC=1C(=O)C(CN(C)C)CC1=CC=CC=C1 NGIRHLFRGWPZMH-UHFFFAOYSA-N 0.000 claims description 2
- PQAIZQKEDKXBNI-UHFFFAOYSA-N 3-[2-benzyl-3-(dimethylamino)propanoyl]benzonitrile Chemical compound C=1C=CC(C#N)=CC=1C(=O)C(CN(C)C)CC1=CC=CC=C1 PQAIZQKEDKXBNI-UHFFFAOYSA-N 0.000 claims description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical class CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 2
- 208000007848 Alcoholism Diseases 0.000 claims description 2
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 2
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims description 2
- 206010011224 Cough Diseases 0.000 claims description 2
- 206010012735 Diarrhoea Diseases 0.000 claims description 2
- 206010013654 Drug abuse Diseases 0.000 claims description 2
- 208000007882 Gastritis Diseases 0.000 claims description 2
- 206010020751 Hypersensitivity Diseases 0.000 claims description 2
- 206010061218 Inflammation Diseases 0.000 claims description 2
- 239000005708 Sodium hypochlorite Substances 0.000 claims description 2
- 206010001584 alcohol abuse Diseases 0.000 claims description 2
- 208000025746 alcohol use disease Diseases 0.000 claims description 2
- 230000007815 allergy Effects 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 150000003935 benzaldehydes Chemical class 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/31—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/32—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to an acyclic carbon atom of the carbon skeleton
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- A—HUMAN NECESSITIES
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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
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
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- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19933421A DE19933421A1 (de) | 1999-07-16 | 1999-07-16 | 2-Benzyl-3-dimethylamino-1-phenyl-propanderi- vate |
PCT/EP2000/005820 WO2001005743A1 (fr) | 1999-07-16 | 2000-06-23 | Derives de 3-amino-2-benzyl-1-phenyl-propane |
Publications (1)
Publication Number | Publication Date |
---|---|
SK412002A3 true SK412002A3 (en) | 2002-06-04 |
Family
ID=7915037
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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SK41-2002A SK412002A3 (en) | 1999-07-16 | 2000-06-23 | 3-amino-2-benzyl-1-phenyl-propane derivatives, process for producing thereof, drugs comprising said derivatives and their use |
Country Status (23)
Country | Link |
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US (1) | US6653508B2 (fr) |
EP (1) | EP1196373A1 (fr) |
JP (1) | JP2003505358A (fr) |
KR (1) | KR20020038690A (fr) |
CN (1) | CN1174955C (fr) |
AR (1) | AR043090A1 (fr) |
AU (1) | AU778632B2 (fr) |
BR (1) | BR0012622A (fr) |
CA (1) | CA2378723A1 (fr) |
CO (1) | CO5261540A1 (fr) |
CZ (1) | CZ2002185A3 (fr) |
DE (1) | DE19933421A1 (fr) |
HK (1) | HK1045987A1 (fr) |
HU (1) | HUP0201797A3 (fr) |
IL (2) | IL147636A0 (fr) |
MX (1) | MXPA02000577A (fr) |
NO (1) | NO20020212L (fr) |
NZ (1) | NZ517164A (fr) |
PE (1) | PE20010348A1 (fr) |
PL (1) | PL353647A1 (fr) |
SK (1) | SK412002A3 (fr) |
WO (1) | WO2001005743A1 (fr) |
ZA (1) | ZA200201276B (fr) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10059412A1 (de) * | 2000-11-30 | 2002-06-13 | Gruenenthal Gmbh | Verwendung von 1-Phenyl-3-dimethylamino-propanverbindungen zur Therapie der Harninkontinenz |
DE10161644A1 (de) * | 2001-12-14 | 2003-06-26 | Gruenenthal Gmbh | N,N'-disubstituierte Piperazin-Verbindungen |
DE10326097A1 (de) | 2003-06-06 | 2005-01-05 | Grünenthal GmbH | Verfahren zur Herstellung von Dimethyl-(3-aryl-butyl)-aminverbindungen |
DE10328316A1 (de) * | 2003-06-23 | 2005-01-20 | Grünenthal GmbH | Verfahren zur Herstellung von Dimethyl-(3-aryl-buthyl)-aminverbindungen als pharmazeutische Wirkstoffe |
US7435229B2 (en) * | 2004-02-25 | 2008-10-14 | Wolf Erich W | System for transcutaneous monitoring of intracranial pressure (ICP) using near infrared (NIR) telemetry |
FR2902789A1 (fr) * | 2006-06-21 | 2007-12-28 | Genfit Sa | Derives de 1,3-diphenylpropane substitues, preparations et utilisations |
CN101528674B (zh) * | 2006-10-25 | 2015-04-29 | 汉高知识产权及控股有限公司 | 亚胺*盐和使用该新的亚胺*盐制备缺电子烯烃的方法 |
WO2015075678A1 (fr) | 2013-11-21 | 2015-05-28 | Unimark Remedies Ltd. | Nouveau procédé pour la préparation de dérivés de 1-phényl-3-aminopropane |
WO2018136792A1 (fr) | 2017-01-20 | 2018-07-26 | The Regents Of The University Of California | Inhibiteurs du domaine n-terminal du récepteur d'androgène |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
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DE938732C (de) * | 1938-09-21 | 1956-02-09 | Siemens Ag | Elektrisch beheizter Kammer-Gluehofen mit Schutzgasfuellung |
DE901438C (de) * | 1939-02-15 | 1954-01-11 | Siemens Ag | Einrichtung zum Erzielen gleichbleibender Stueckstaerken von aus koernigem oder pulverigem Stoff gepressten Erzeugnissen, insbesondere von Briketts aus Kohle |
GB901438A (en) * | 1959-04-29 | 1962-07-18 | Merck & Co Inc | Maleamic acid derivatives |
DE1110171B (de) * | 1959-11-27 | 1961-07-06 | Hoechst Ag | Verfahren zur Herstellung substituierter Amine |
US3277165A (en) * | 1962-02-08 | 1966-10-04 | Merck & Co Inc | Fumaramic acid derivatives |
US3342829A (en) * | 1963-06-15 | 1967-09-19 | Hoechst Ag | Bis-quaternary salts of triamines and process for preparing them |
DE4426245A1 (de) | 1994-07-23 | 1996-02-22 | Gruenenthal Gmbh | 1-Phenyl-3-dimethylamino-propanverbindungen mit pharmakologischer Wirkung |
WO1998056752A1 (fr) * | 1997-06-11 | 1998-12-17 | Nps Pharmaceuticals, Inc. | Composes actifs sur un nouveau site des canaux calciques actives par les recepteurs servant au tratitement des troubles et des maladies neurologiques |
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1999
- 1999-07-16 DE DE19933421A patent/DE19933421A1/de not_active Ceased
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2000
- 2000-06-23 PL PL00353647A patent/PL353647A1/xx not_active Application Discontinuation
- 2000-06-23 CA CA002378723A patent/CA2378723A1/fr not_active Abandoned
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- 2000-06-23 SK SK41-2002A patent/SK412002A3/sk not_active Application Discontinuation
- 2000-06-23 JP JP2001511404A patent/JP2003505358A/ja not_active Withdrawn
- 2000-06-23 EP EP00943873A patent/EP1196373A1/fr not_active Withdrawn
- 2000-06-23 WO PCT/EP2000/005820 patent/WO2001005743A1/fr not_active Application Discontinuation
- 2000-06-23 KR KR1020027000542A patent/KR20020038690A/ko not_active Application Discontinuation
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- 2000-06-23 HU HU0201797A patent/HUP0201797A3/hu unknown
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- 2002-10-10 HK HK02107391.8A patent/HK1045987A1/zh unknown
Also Published As
Publication number | Publication date |
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NO20020212D0 (no) | 2002-01-15 |
AU778632B2 (en) | 2004-12-16 |
ZA200201276B (en) | 2003-07-30 |
KR20020038690A (ko) | 2002-05-23 |
PE20010348A1 (es) | 2001-05-05 |
WO2001005743A1 (fr) | 2001-01-25 |
CN1373745A (zh) | 2002-10-09 |
HUP0201797A3 (en) | 2003-03-28 |
NO20020212L (no) | 2002-01-15 |
JP2003505358A (ja) | 2003-02-12 |
NZ517164A (en) | 2004-02-27 |
CZ2002185A3 (cs) | 2002-05-15 |
US20020161262A1 (en) | 2002-10-31 |
PL353647A1 (en) | 2003-12-01 |
AR043090A1 (es) | 2005-07-20 |
HK1045987A1 (zh) | 2002-12-20 |
US6653508B2 (en) | 2003-11-25 |
IL147636A (en) | 2006-08-20 |
EP1196373A1 (fr) | 2002-04-17 |
HUP0201797A2 (hu) | 2002-12-28 |
CO5261540A1 (es) | 2003-03-31 |
MXPA02000577A (es) | 2003-02-27 |
AU5818900A (en) | 2001-02-05 |
CN1174955C (zh) | 2004-11-10 |
IL147636A0 (en) | 2002-08-14 |
DE19933421A1 (de) | 2001-01-25 |
CA2378723A1 (fr) | 2001-01-25 |
BR0012622A (pt) | 2002-06-11 |
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