CH679208A5 - - Google Patents
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- Publication number
- CH679208A5 CH679208A5 CH1539/90A CH153990A CH679208A5 CH 679208 A5 CH679208 A5 CH 679208A5 CH 1539/90 A CH1539/90 A CH 1539/90A CH 153990 A CH153990 A CH 153990A CH 679208 A5 CH679208 A5 CH 679208A5
- Authority
- CH
- Switzerland
- Prior art keywords
- adamantane
- sep
- amino
- hydrogen
- ethyl
- Prior art date
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- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical class C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims abstract description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 23
- 239000001257 hydrogen Substances 0.000 claims abstract description 23
- 206010008120 Cerebral ischaemia Diseases 0.000 claims abstract description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
- 230000002265 prevention Effects 0.000 claims abstract description 9
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 8
- 239000003814 drug Substances 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 201000006474 Brain Ischemia Diseases 0.000 claims description 13
- 206010008118 cerebral infarction Diseases 0.000 claims description 13
- 210000002569 neuron Anatomy 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 208000028867 ischemia Diseases 0.000 claims description 4
- 208000024827 Alzheimer disease Diseases 0.000 claims description 2
- 230000007850 degeneration Effects 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 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 1
- 229940052761 dopaminergic adamantane derivative Drugs 0.000 abstract description 8
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 150000001875 compounds Chemical class 0.000 description 38
- 238000012360 testing method Methods 0.000 description 31
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
- 238000002360 preparation method Methods 0.000 description 27
- 239000012074 organic phase Substances 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 238000001816 cooling Methods 0.000 description 14
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 14
- 235000019341 magnesium sulphate Nutrition 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 description 13
- -1 3,5-disubstituted 1-amino-adamantanes Chemical class 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 12
- NIKSPBIUZXJSKI-UHFFFAOYSA-N 3-ethyl-5-phenyladamantan-1-ol Chemical compound C1C(CC)(C2)CC(C3)CC1(O)CC32C1=CC=CC=C1 NIKSPBIUZXJSKI-UHFFFAOYSA-N 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- 239000003826 tablet Substances 0.000 description 11
- LPIWUJAIURURAQ-UHFFFAOYSA-N 1-(2-bromoethyl)-3,5-dimethyladamantane Chemical compound C1C(C2)CC3(C)CC1(C)CC2(CCBr)C3 LPIWUJAIURURAQ-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 238000009835 boiling Methods 0.000 description 10
- ZZSRHVAPYKSVGX-UHFFFAOYSA-N 1-bromo-3-ethyl-5,7-dimethyladamantane Chemical compound C1C(C2)(C)CC3(C)CC2(Br)CC1(CC)C3 ZZSRHVAPYKSVGX-UHFFFAOYSA-N 0.000 description 9
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 9
- 229910052794 bromium Inorganic materials 0.000 description 9
- JXYVPFJAUMEJFE-UHFFFAOYSA-N 3-ethyl-5,7-dimethyladamantan-1-amine;hydrochloride Chemical compound Cl.C1C(C2)(C)CC3(C)CC2(N)CC1(CC)C3 JXYVPFJAUMEJFE-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 230000001773 anti-convulsant effect Effects 0.000 description 8
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 5
- 230000029936 alkylation Effects 0.000 description 5
- 238000005804 alkylation reaction Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- ISDSLPMQFWIUPU-UHFFFAOYSA-N 1-propan-2-yladamantane Chemical compound C1C(C2)CC3CC2CC1(C(C)C)C3 ISDSLPMQFWIUPU-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical class C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 210000004556 brain Anatomy 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 4
- BUGYDGFZZOZRHP-UHFFFAOYSA-N memantine Chemical compound C1C(C2)CC3(C)CC1(C)CC2(N)C3 BUGYDGFZZOZRHP-UHFFFAOYSA-N 0.000 description 4
- 239000004540 pour-on Substances 0.000 description 4
- 235000010265 sodium sulphite Nutrition 0.000 description 4
- WLPZAHQYMVQLHL-UHFFFAOYSA-N 3-cyclohexyladamantan-1-amine Chemical compound C1C(N)(C2)CC(C3)CC1CC32C1CCCCC1 WLPZAHQYMVQLHL-UHFFFAOYSA-N 0.000 description 3
- OVQNSGBYKOJYBK-UHFFFAOYSA-N 3-ethyladamantan-1-amine Chemical compound C1C(C2)CC3CC2(N)CC1(CC)C3 OVQNSGBYKOJYBK-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- 102000004310 Ion Channels Human genes 0.000 description 3
- 108090000862 Ion Channels Proteins 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- 230000003042 antagnostic effect Effects 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 229940117975 chromium trioxide Drugs 0.000 description 3
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 3
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- FQPYRWAIWQNTFQ-UHFFFAOYSA-N n,3,5-trimethyladamantan-1-amine Chemical compound C1C(C2)CC3(C)CC2(C)CC1(NC)C3 FQPYRWAIWQNTFQ-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000000324 neuroprotective effect Effects 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- QUCXLVDIVQWYJR-UHFFFAOYSA-N 1-bromo-3,5-dimethyladamantane Chemical compound C1C(C2)CC3(C)CC1(C)CC2(Br)C3 QUCXLVDIVQWYJR-UHFFFAOYSA-N 0.000 description 2
- QUUCNKWMKRZRGC-UHFFFAOYSA-N 1-bromo-3-ethyladamantane Chemical compound C1C(C2)CC3CC2(Br)CC1(CC)C3 QUUCNKWMKRZRGC-UHFFFAOYSA-N 0.000 description 2
- YQMDWXLAPBTRCZ-UHFFFAOYSA-N 1-bromo-3-phenyladamantane Chemical compound C1C(Br)(C2)CC(C3)CC1CC32C1=CC=CC=C1 YQMDWXLAPBTRCZ-UHFFFAOYSA-N 0.000 description 2
- IOPVEZQBHDNEEW-UHFFFAOYSA-N 1-bromo-3-propan-2-yladamantane Chemical compound C1C(C2)CC3CC2(Br)CC1(C(C)C)C3 IOPVEZQBHDNEEW-UHFFFAOYSA-N 0.000 description 2
- FTNPDAKMYKMVKB-UHFFFAOYSA-N 1-ethyl-3,5-dimethyladamantane Chemical compound C1C(C2)CC3(C)CC2(C)CC1(CC)C3 FTNPDAKMYKMVKB-UHFFFAOYSA-N 0.000 description 2
- RTVIOLNBTCXFJS-UHFFFAOYSA-N 1-ethyl-3-phenyladamantane Chemical compound C1C(CC)(C2)CC(C3)CC1CC32C1=CC=CC=C1 RTVIOLNBTCXFJS-UHFFFAOYSA-N 0.000 description 2
- XACJBFHSZJWBBP-UHFFFAOYSA-N 1-phenyladamantane Chemical compound C1C(C2)CC(C3)CC1CC23C1=CC=CC=C1 XACJBFHSZJWBBP-UHFFFAOYSA-N 0.000 description 2
- QNYZSAKFAQDNGK-UHFFFAOYSA-N 3-phenyladamantan-1-ol Chemical compound C1C(O)(C2)CC(C3)CC1CC32C1=CC=CC=C1 QNYZSAKFAQDNGK-UHFFFAOYSA-N 0.000 description 2
- DHWQMEWSEZKXHY-UHFFFAOYSA-N 3-propan-2-yladamantan-1-amine;hydrochloride Chemical compound Cl.C1C(C2)CC3CC2(N)CC1(C(C)C)C3 DHWQMEWSEZKXHY-UHFFFAOYSA-N 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 208000007101 Muscle Cramp Diseases 0.000 description 2
- 102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000001961 anticonvulsive agent Substances 0.000 description 2
- 229960003965 antiepileptics Drugs 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 229940099112 cornstarch Drugs 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 229960003638 dopamine Drugs 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 210000001320 hippocampus Anatomy 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
- CLYOOVNORYNXMD-UHFFFAOYSA-N methyl adamantane-1-carboxylate Chemical compound C1C(C2)CC3CC2CC1(C(=O)OC)C3 CLYOOVNORYNXMD-UHFFFAOYSA-N 0.000 description 2
- 239000003703 n methyl dextro aspartic acid receptor blocking agent Substances 0.000 description 2
- 230000001991 pathophysiological effect Effects 0.000 description 2
- 229950010883 phencyclidine Drugs 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- CWNOIUTVJRWADX-UHFFFAOYSA-N 1,3-dimethyladamantane Chemical compound C1C(C2)CC3CC1(C)CC2(C)C3 CWNOIUTVJRWADX-UHFFFAOYSA-N 0.000 description 1
- LZLRNLVOPUAITP-UHFFFAOYSA-N 1-bromo-3-ethyl-5-phenyladamantane Chemical compound C1C(CC)(C2)CC(C3)CC1(Br)CC32C1=CC=CC=C1 LZLRNLVOPUAITP-UHFFFAOYSA-N 0.000 description 1
- VQHPRVYDKRESCL-UHFFFAOYSA-N 1-bromoadamantane Chemical compound C1C(C2)CC3CC2CC1(Br)C3 VQHPRVYDKRESCL-UHFFFAOYSA-N 0.000 description 1
- OZNXTQSXSHODFR-UHFFFAOYSA-N 1-chloroadamantane Chemical class C1C(C2)CC3CC2CC1(Cl)C3 OZNXTQSXSHODFR-UHFFFAOYSA-N 0.000 description 1
- LXTHCCWEYOKFSR-UHFFFAOYSA-N 1-ethyladamantane Chemical compound C1C(C2)CC3CC2CC1(CC)C3 LXTHCCWEYOKFSR-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- ITAALVOWSKQISP-UHFFFAOYSA-N 3,5-diethyl-7-methyladamantan-1-amine Chemical compound C1C(C2)(C)CC3(N)CC1(CC)CC2(CC)C3 ITAALVOWSKQISP-UHFFFAOYSA-N 0.000 description 1
- SUVNEFNZAWETBP-UHFFFAOYSA-N 3,5-diethyladamantan-1-amine Chemical compound C1C(C2)CC3(N)CC1(CC)CC2(CC)C3 SUVNEFNZAWETBP-UHFFFAOYSA-N 0.000 description 1
- XUONURYAKCELNT-UHFFFAOYSA-N 3-cyclohexyladamantan-1-amine;hydrochloride Chemical compound Cl.C1C(N)(C2)CC(C3)CC1CC32C1CCCCC1 XUONURYAKCELNT-UHFFFAOYSA-N 0.000 description 1
- QJZCXHNEPQJAPJ-UHFFFAOYSA-N 3-ethyl-5,7-dimethyladamantan-1-amine Chemical compound C1C(C2)(C)CC3(C)CC2(N)CC1(CC)C3 QJZCXHNEPQJAPJ-UHFFFAOYSA-N 0.000 description 1
- KMRHMPLKDOCESH-UHFFFAOYSA-N 3-ethyl-5-phenyladamantan-1-amine Chemical compound C1C(CC)(C2)CC(C3)CC1(N)CC32C1=CC=CC=C1 KMRHMPLKDOCESH-UHFFFAOYSA-N 0.000 description 1
- NMLWLANWDKUOBD-UHFFFAOYSA-N 3-methyl-5-phenyladamantan-1-amine Chemical compound C1C(C)(C2)CC(C3)CC1(N)CC32C1=CC=CC=C1 NMLWLANWDKUOBD-UHFFFAOYSA-N 0.000 description 1
- MWXAHLMUYMJXTG-UHFFFAOYSA-N 3-phenyladamantan-1-amine Chemical compound C1C(N)(C2)CC(C3)CC1CC32C1=CC=CC=C1 MWXAHLMUYMJXTG-UHFFFAOYSA-N 0.000 description 1
- VCZOJIYQTDUXBF-UHFFFAOYSA-N 3-phenyladamantan-1-amine;hydrochloride Chemical compound Cl.C1C(N)(C2)CC(C3)CC1CC32C1=CC=CC=C1 VCZOJIYQTDUXBF-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/34—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton
- C07C211/38—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton containing condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
- C07C2603/74—Adamantanes
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Epidemiology (AREA)
- Hospice & Palliative Care (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychiatry (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)
- Medicinal Preparation (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP89106657A EP0392059B1 (de) | 1989-04-14 | 1989-04-14 | Verwendung von Adamantan-Derivaten zur Prävention und Behandlung der cerebralen Ischämie |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH679208A5 true CH679208A5 (Direct) | 1992-01-15 |
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ID=8201228
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1539/90A CH679208A5 (Direct) | 1989-04-14 | 1990-04-10 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US5061703A (Direct) |
| EP (1) | EP0392059B1 (Direct) |
| JP (1) | JP2821233B2 (Direct) |
| AT (1) | ATE94384T1 (Direct) |
| CA (1) | CA2014453C (Direct) |
| CH (1) | CH679208A5 (Direct) |
| DD (1) | DD293493A5 (Direct) |
| DE (2) | DE58905637D1 (Direct) |
| DK (1) | DK173356B1 (Direct) |
| ES (1) | ES2059602T3 (Direct) |
| HU (1) | HU215592B (Direct) |
| IE (1) | IE63467B1 (Direct) |
| LU (1) | LU90988I2 (Direct) |
| NL (1) | NL300107I1 (Direct) |
| PT (1) | PT93763B (Direct) |
| SE (1) | SE9001329L (Direct) |
Families Citing this family (125)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5334618A (en) * | 1991-04-04 | 1994-08-02 | The Children's Medical Center Corporation | Method of preventing NMDA receptor-mediated neuronal damage |
| US5506231A (en) * | 1989-03-31 | 1996-04-09 | The Children's Medical Center Corporation | Treatment of aids dementia, myelopathy and blindness |
| US5455279A (en) * | 1991-04-19 | 1995-10-03 | The Children's Medical Center Corporation | Regimen method of mediating neuronal damage using nitroglycerine |
| WO1992017168A1 (en) * | 1991-04-04 | 1992-10-15 | The Children's Medical Center Corporation | Method of preventing nmda receptor-mediated neuronal damage |
| US5614560A (en) * | 1991-04-04 | 1997-03-25 | Children's Medical Center Corporation | Method of preventing NMDA receptor-mediated neuronal damage |
| DE4225730C2 (de) * | 1992-08-04 | 2003-04-30 | Merz Pharma Gmbh & Co Kgaa | Verfahren zur Herstellung von festen Arzneiformkörpern mit protrahierter 2-Stufen-Freisetzung |
| IL112099A (en) * | 1993-12-23 | 1999-07-14 | Ortho Pharma Corp | N-oxides of 4-arylpiperazines and 4-arylpiperidines and pharmaceutical compositions containing them |
| DE19510189A1 (de) * | 1995-03-21 | 1996-09-26 | Hartmut Dr Goebel | Verwendung von Amantadin |
| DE19528388A1 (de) * | 1995-08-02 | 1997-02-06 | Hans Peter Prof Dr Med Zenner | Verwendung von Adamantan-Derivaten zur Behandlung von Erkrankungen des Innenohrs |
| US5866585A (en) * | 1997-05-22 | 1999-02-02 | Synchroneuron, Llc | Methods of treating tardive dyskinesia using NMDA receptor antagonists |
| US6057373A (en) * | 1997-05-22 | 2000-05-02 | Synchroneuron, Llc | Methods of treating tardive dyskinesia and other movement disorders using NMDA receptor antagonists |
| US6294583B1 (en) * | 1998-01-13 | 2001-09-25 | Synchroneuron, Llc | Methods of treating tardive dyskinesia and other movement disorders |
| US5952389A (en) * | 1998-01-13 | 1999-09-14 | Synchroneuron | Methods of treating tardive dyskinesia and other movement disorders |
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| US3450761A (en) * | 1967-03-30 | 1969-06-17 | Sun Oil Co | 1-aminoethyldimethyladamantane |
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-
1989
- 1989-04-14 EP EP89106657A patent/EP0392059B1/de not_active Expired - Lifetime
- 1989-04-14 ES ES89106657T patent/ES2059602T3/es not_active Expired - Lifetime
- 1989-04-14 AT AT89106657T patent/ATE94384T1/de active
- 1989-04-14 DE DE89106657T patent/DE58905637D1/de not_active Expired - Lifetime
- 1989-04-14 DE DE2002199048 patent/DE10299048I2/de active Active
-
1990
- 1990-03-16 IE IE99690A patent/IE63467B1/en not_active IP Right Cessation
- 1990-04-10 CH CH1539/90A patent/CH679208A5/de not_active IP Right Cessation
- 1990-04-11 US US07/508,109 patent/US5061703A/en not_active Expired - Lifetime
- 1990-04-11 SE SE9001329A patent/SE9001329L/xx not_active Application Discontinuation
- 1990-04-11 DK DK199000916A patent/DK173356B1/da not_active IP Right Cessation
- 1990-04-11 CA CA002014453A patent/CA2014453C/en not_active Expired - Lifetime
- 1990-04-12 PT PT93763A patent/PT93763B/pt not_active IP Right Cessation
- 1990-04-12 DD DD90339741A patent/DD293493A5/de not_active IP Right Cessation
- 1990-04-13 JP JP2099117A patent/JP2821233B2/ja not_active Expired - Lifetime
- 1990-04-13 HU HU902434A patent/HU215592B/hu unknown
-
2002
- 2002-11-13 LU LU90988C patent/LU90988I2/fr unknown
- 2002-11-14 NL NL300107C patent/NL300107I1/nl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES2059602T3 (es) | 1994-11-16 |
| US5061703A (en) | 1991-10-29 |
| HU215592B (hu) | 1999-01-28 |
| HUT58200A (en) | 1992-02-28 |
| DE10299048I1 (de) | 2003-03-27 |
| DD293493A5 (de) | 1991-09-05 |
| EP0392059B1 (de) | 1993-09-15 |
| DE10299048I2 (de) | 2006-07-13 |
| PT93763A (pt) | 1990-11-20 |
| IE900996L (en) | 1990-10-14 |
| LU90988I2 (fr) | 2003-01-13 |
| DK91690D0 (da) | 1990-04-11 |
| CA2014453A1 (en) | 1990-10-14 |
| NL300107I2 (nl) | 2003-02-03 |
| JP2821233B2 (ja) | 1998-11-05 |
| DK173356B1 (da) | 2000-08-07 |
| ATE94384T1 (de) | 1993-10-15 |
| SE9001329L (sv) | 1990-10-15 |
| CA2014453C (en) | 2000-03-28 |
| JPH02292214A (ja) | 1990-12-03 |
| EP0392059A1 (de) | 1990-10-17 |
| NL300107I1 (nl) | 2003-02-03 |
| IE63467B1 (en) | 1995-04-19 |
| HU902434D0 (en) | 1990-08-28 |
| SE9001329D0 (sv) | 1990-04-11 |
| DE58905637D1 (de) | 1993-10-21 |
| DK91690A (da) | 1990-10-15 |
| PT93763B (pt) | 1996-04-30 |
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| PL | Patent ceased |