CH500983A - Verfahren zur Herstellung von 1-Amino-isochinolinen - Google Patents
Verfahren zur Herstellung von 1-Amino-isochinolinenInfo
- Publication number
- CH500983A CH500983A CH932568A CH932568A CH500983A CH 500983 A CH500983 A CH 500983A CH 932568 A CH932568 A CH 932568A CH 932568 A CH932568 A CH 932568A CH 500983 A CH500983 A CH 500983A
- Authority
- CH
- Switzerland
- Prior art keywords
- added
- formula
- chloroform
- water
- potassium
- Prior art date
Links
- OSILBMSORKFRTB-UHFFFAOYSA-N isoquinolin-1-amine Chemical compound C1=CC=C2C(N)=NC=CC2=C1 OSILBMSORKFRTB-UHFFFAOYSA-N 0.000 title claims description 7
- 230000002048 spasmolytic effect Effects 0.000 title abstract description 4
- 239000000812 cholinergic antagonist Substances 0.000 title 1
- 230000003001 depressive effect Effects 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 239000002253 acid Substances 0.000 claims abstract description 15
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 10
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 49
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 20
- 150000002825 nitriles Chemical class 0.000 claims description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 13
- 238000002844 melting Methods 0.000 claims description 13
- 230000008018 melting Effects 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- 239000011541 reaction mixture Substances 0.000 claims description 13
- 239000000243 solution Substances 0.000 claims description 12
- -1 1-amino-3- (4,5-dimethoxy-o-tolyl) -6,7-dimethoxyisoquinoline Chemical compound 0.000 claims description 11
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 11
- 229910052783 alkali metal Inorganic materials 0.000 claims description 11
- 239000002585 base Substances 0.000 claims description 11
- 229910052700 potassium Inorganic materials 0.000 claims description 11
- 239000011591 potassium Substances 0.000 claims description 11
- 150000001340 alkali metals Chemical class 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 8
- 239000012044 organic layer Substances 0.000 claims description 8
- 238000004458 analytical method Methods 0.000 claims description 7
- 239000013078 crystal Substances 0.000 claims description 7
- 239000003208 petroleum Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 239000000725 suspension Substances 0.000 claims description 7
- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000002244 precipitate Substances 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims description 5
- 235000019341 magnesium sulphate Nutrition 0.000 claims description 5
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 claims description 4
- 239000002775 capsule Substances 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 239000000839 emulsion Substances 0.000 claims description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 231100000252 nontoxic Toxicity 0.000 claims description 4
- 230000003000 nontoxic effect Effects 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000006187 pill Substances 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- 239000006188 syrup Substances 0.000 claims description 4
- 235000020357 syrup Nutrition 0.000 claims description 4
- NWPNXBQSRGKSJB-UHFFFAOYSA-N 2-methylbenzonitrile Chemical compound CC1=CC=CC=C1C#N NWPNXBQSRGKSJB-UHFFFAOYSA-N 0.000 claims description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 3
- UZDXATQPJOOHQJ-UHFFFAOYSA-N 2-ethylbenzonitrile Chemical compound CCC1=CC=CC=C1C#N UZDXATQPJOOHQJ-UHFFFAOYSA-N 0.000 claims description 2
- FMPKUGLILJSAJA-UHFFFAOYSA-N 3-(2-methylphenyl)isoquinolin-1-amine Chemical compound CC1=CC=CC=C1C1=CC2=CC=CC=C2C(N)=N1 FMPKUGLILJSAJA-UHFFFAOYSA-N 0.000 claims description 2
- FVSAUKQRVYDVMD-UHFFFAOYSA-N 4,5-dimethoxy-2-methylbenzonitrile Chemical compound COC1=CC(C)=C(C#N)C=C1OC FVSAUKQRVYDVMD-UHFFFAOYSA-N 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- 108010010803 Gelatin Proteins 0.000 claims 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 claims description 2
- 229920002472 Starch Polymers 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- BQIKRTGTPBOIMK-UHFFFAOYSA-N [O]C[O] Chemical compound [O]C[O] BQIKRTGTPBOIMK-UHFFFAOYSA-N 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
- 150000005010 aminoquinolines Chemical class 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 239000008116 calcium stearate Substances 0.000 claims description 2
- 235000013539 calcium stearate Nutrition 0.000 claims description 2
- 238000004587 chromatography analysis Methods 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 230000003111 delayed effect Effects 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000003480 eluent Substances 0.000 claims description 2
- 229920000159 gelatin Polymers 0.000 claims description 2
- 239000008273 gelatin Substances 0.000 claims description 2
- 235000019322 gelatine Nutrition 0.000 claims description 2
- 235000011852 gelatine desserts Nutrition 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229940057995 liquid paraffin Drugs 0.000 claims description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 claims description 2
- 239000000314 lubricant Substances 0.000 claims description 2
- 235000019359 magnesium stearate Nutrition 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 235000008390 olive oil Nutrition 0.000 claims description 2
- 239000004006 olive oil Substances 0.000 claims description 2
- 238000007911 parenteral administration Methods 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 239000008107 starch Substances 0.000 claims description 2
- 235000019698 starch Nutrition 0.000 claims description 2
- 239000008174 sterile solution Substances 0.000 claims description 2
- 239000008223 sterile water Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 2
- 239000008158 vegetable oil Substances 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 150000001339 alkali metal compounds Chemical class 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- QSACPWSIIRFHHR-UHFFFAOYSA-N 2,6-dimethylbenzonitrile Chemical compound CC1=CC=CC(C)=C1C#N QSACPWSIIRFHHR-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- RQLKAKQYERUOJD-UHFFFAOYSA-N lithium;1,3,5-trimethylbenzene-6-ide Chemical compound [Li+].CC1=CC(C)=[C-]C(C)=C1 RQLKAKQYERUOJD-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- LKVNUNSCQWUTRM-UHFFFAOYSA-N 3-phenylisoquinolin-1-amine Chemical compound C=1C2=CC=CC=C2C(N)=NC=1C1=CC=CC=C1 LKVNUNSCQWUTRM-UHFFFAOYSA-N 0.000 description 1
- BXWSZTOFUTUGKG-UHFFFAOYSA-N 3-tert-butylisoquinolin-1-amine Chemical compound C1=CC=C2C(N)=NC(C(C)(C)C)=CC2=C1 BXWSZTOFUTUGKG-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- FHKPLLOSJHHKNU-INIZCTEOSA-N [(3S)-3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(oxan-4-yl)methanone Chemical compound C(C)N1N=CC(=C1C)C=1N(C2=NC=NC(=C2N=1)O[C@@H]1CN(CC1)C(=O)C1CCOCC1)C FHKPLLOSJHHKNU-INIZCTEOSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 230000036760 body temperature Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 150000002537 isoquinolines Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2895167A GB1173227A (en) | 1967-06-22 | 1967-06-22 | Amino-Isoquinolines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH500983A true CH500983A (de) | 1970-12-31 |
Family
ID=10283841
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH932568A CH500983A (de) | 1967-06-22 | 1968-06-21 | Verfahren zur Herstellung von 1-Amino-isochinolinen |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE716821A (forum.php) |
| CH (1) | CH500983A (forum.php) |
| DE (1) | DE1770670A1 (forum.php) |
| FR (2) | FR7723M (forum.php) |
| GB (1) | GB1173227A (forum.php) |
| NL (1) | NL6808726A (forum.php) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3991063A (en) * | 1971-09-09 | 1976-11-09 | Wijbe Thomas Nauta | Aminoisoquinolines |
| WO1999011622A1 (en) * | 1997-09-03 | 1999-03-11 | Guilford Pharmaceuticals Inc. | Amino-substituted compounds, methods, and compositions for inhibiting parp activity |
| US6197785B1 (en) | 1997-09-03 | 2001-03-06 | Guilford Pharmaceuticals Inc. | Alkoxy-substituted compounds, methods, and compositions for inhibiting PARP activity |
| US6291425B1 (en) | 1999-09-01 | 2001-09-18 | Guilford Pharmaceuticals Inc. | Compounds, methods and pharmaceutical compositions for treating cellular damage, such as neural or cardiovascular tissue damage |
| US6426415B1 (en) | 1997-09-03 | 2002-07-30 | Guilford Pharmaceuticals Inc. | Alkoxy-substituted compounds, methods and compositions for inhibiting parp activity |
| US6635642B1 (en) | 1997-09-03 | 2003-10-21 | Guilford Pharmaceuticals Inc. | PARP inhibitors, pharmaceutical compositions comprising same, and methods of using same |
| US6514983B1 (en) | 1997-09-03 | 2003-02-04 | Guilford Pharmaceuticals Inc. | Compounds, methods and pharmaceutical compositions for treating neural or cardiovascular tissue damage |
| US6346536B1 (en) | 1997-09-03 | 2002-02-12 | Guilford Pharmaceuticals Inc. | Poly(ADP-ribose) polymerase inhibitors and method for treating neural or cardiovascular tissue damage using the same |
| US6395749B1 (en) | 1998-05-15 | 2002-05-28 | Guilford Pharmaceuticals Inc. | Carboxamide compounds, methods, and compositions for inhibiting PARP activity |
| US6387902B1 (en) | 1998-12-31 | 2002-05-14 | Guilford Pharmaceuticals, Inc. | Phenazine compounds, methods and pharmaceutical compositions for inhibiting PARP |
| WO2001090077A1 (en) | 2000-05-19 | 2001-11-29 | Guilford Pharmaceuticals, Inc. | Sulfonamide and carbamide derivatives of 6(5h)phenanthridinones and their uses |
| WO2001091796A2 (en) | 2000-06-01 | 2001-12-06 | Guilford Pharmaceuticals Inc. | Methods, compounds and compositions for treating gout |
-
1967
- 1967-06-22 GB GB2895167A patent/GB1173227A/en not_active Expired
- 1967-06-22 FR FR166799A patent/FR7723M/fr not_active Expired
-
1968
- 1968-06-19 BE BE716821D patent/BE716821A/xx unknown
- 1968-06-20 FR FR1579053D patent/FR1579053A/fr not_active Expired
- 1968-06-20 DE DE19681770670 patent/DE1770670A1/de active Pending
- 1968-06-21 NL NL6808726A patent/NL6808726A/xx unknown
- 1968-06-21 CH CH932568A patent/CH500983A/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GB1173227A (en) | 1969-12-03 |
| FR1579053A (forum.php) | 1969-08-22 |
| BE716821A (forum.php) | 1968-12-19 |
| NL6808726A (forum.php) | 1968-12-23 |
| DE1770670A1 (de) | 1971-11-11 |
| FR7723M (forum.php) | 1970-03-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1595915C3 (de) | Pyrrolidinderivate | |
| DE2558501C2 (forum.php) | ||
| DD141520A5 (de) | Verfahren zur herstellung neuer derivate von 4-amino-5-alkylsulfonyl-ortho-anisamiden | |
| DE2205815A1 (de) | Piperazinderivate und verfahren zu ihrer herstellung | |
| EP0110372A1 (de) | 1-Phenylisochinolinderivate und Verfahren zu ihrer Herstellung, diese Verbindung enthaltende pharmazeutische Präparate und deren Anwendung | |
| DE2901170C2 (forum.php) | ||
| DE2002840A1 (de) | 2,3,5-trisubstit,-2'-Hydroxy-6,7-benzomorphane und Verfahren zu deren Herstellung | |
| CH500983A (de) | Verfahren zur Herstellung von 1-Amino-isochinolinen | |
| DE2112026B2 (de) | 3-Phenyl-H2-[pyrroUdinyl-(l)] äthylamino)-3,4dihydroisochinolin, seiner Herstellung und die es enthaltenden medizinischen Zusammensetzungen | |
| DE2847792C2 (forum.php) | ||
| DE3149010A1 (de) | (+)-2-(1-(2,6-dichlorphenoxy)-ethyl)-1,3- diazacyclopent-2-en, dessen herstellung und seine verwendung in pharamazeutischen praeparaten | |
| DE1911464C3 (de) | 3,4-Dihydroisochinoline, Verfahren zu ihrer Herstellung und Arzneimittel | |
| DE2162011B2 (de) | 2-Phenyl-3-(4-methyl-piperazinocarbonyloxy)- 1-isoindolinon- derivate, ihre Herstellung und diese enthaltende pharmazeutische Zusammensetzungen | |
| DD298397A5 (de) | Verfahren zur herstellung von 1-(heterocyclylsulfonyl-3-/4-(2-pyrimidinyl)-1-piperazinyl/propanen | |
| DE2138528A1 (de) | Pyrazolo(3,4 b)pyndin 5 carboxamide und deren Salze, Verfahren zum Herstellen solcher Substanzen und Arzneimittel mit einem Gehalt daran | |
| DE2244265A1 (de) | Neue imidazolderivate, ihre herstellung und die medizinischen zusammensetzungen, die sie enthalten | |
| DE2833892A1 (de) | 12h-dibenzo eckige klammer auf d,g eckige klammer zu eckige klammer auf 1,3,6 eckige klammer zu dioxazocinderivate, solche enthaltende arzneimittel und verfahren zur herstellung derselben | |
| DE2836062A1 (de) | N-(4-pyrazolidinyl)benzamide und deren salze und sie enthaltende pharmazeutische zubereitungen | |
| AT249650B (de) | Verfahren zur Herstellung des Dimethylaminoäthylmonoesters der Bernsteinsäure in Form seines inneren Salzes | |
| DE2432030C3 (de) | 1-(3-Acetylaminopropyl)-4- (2,5dichlorphenyO-plperazin deren Salze, Verfahren zu deren Herstellung und pharmazeutische Mittel | |
| AT377519B (de) | Verfahren zur herstellung von neuen derivaten von (alkyl-(4-chinolyl))-piperidin oder -pyrroldin und ihren salzen | |
| AT366371B (de) | Verfahren zur herstellung von neuen n-(4pyrazolidinyl)benzamiden, deren salzen und optischaktiven formen | |
| DE1670019A1 (de) | Aeetylenische Imide und Verfahren zu deren Herstellung | |
| AT220150B (de) | Verfahren zur Herstellung von neuen, substituierten Piperidinen | |
| DE2404924A1 (de) | Ergolinderivate |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |