DE2243789A1 - 1-aminoisochinolinderivate, ihre salze mit saeuren und quartaeren ammoniumsalze, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel - Google Patents
1-aminoisochinolinderivate, ihre salze mit saeuren und quartaeren ammoniumsalze, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittelInfo
- Publication number
- DE2243789A1 DE2243789A1 DE2243789A DE2243789A DE2243789A1 DE 2243789 A1 DE2243789 A1 DE 2243789A1 DE 2243789 A DE2243789 A DE 2243789A DE 2243789 A DE2243789 A DE 2243789A DE 2243789 A1 DE2243789 A1 DE 2243789A1
- Authority
- DE
- Germany
- Prior art keywords
- isoquinoline
- amino
- pyridyl
- salts
- quaternary ammonium
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 150000003839 salts Chemical class 0.000 title claims description 20
- OSILBMSORKFRTB-UHFFFAOYSA-N isoquinolin-1-amine Chemical class C1=CC=C2C(N)=NC=CC2=C1 OSILBMSORKFRTB-UHFFFAOYSA-N 0.000 title claims description 14
- 150000001875 compounds Chemical class 0.000 title claims description 12
- 239000002253 acid Substances 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 10
- 150000007513 acids Chemical class 0.000 title claims description 9
- 229940126601 medicinal product Drugs 0.000 title description 2
- 150000003863 ammonium salts Chemical class 0.000 title 1
- -1 alkyl radicals Chemical class 0.000 claims description 43
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 150000001339 alkali metal compounds Chemical class 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 150000002825 nitriles Chemical class 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- IOJUKYJPPGILIH-UHFFFAOYSA-N 3-pyridin-2-yl-4-undecylisoquinolin-1-amine Chemical compound N1=C(N)C2=CC=CC=C2C(CCCCCCCCCCC)=C1C1=CC=CC=N1 IOJUKYJPPGILIH-UHFFFAOYSA-N 0.000 claims description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 150000005840 aryl radicals Chemical class 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- XAOOYSYTTGMKJX-UHFFFAOYSA-N 3-pyrrolidin-1-ylisoquinolin-1-amine Chemical compound C=1C2=CC=CC=C2C(N)=NC=1N1CCCC1 XAOOYSYTTGMKJX-UHFFFAOYSA-N 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- CJEZLXXESOYJHS-UHFFFAOYSA-N 1-pyridin-2-ylisoquinoline Chemical compound N1=CC=CC=C1C1=NC=CC2=CC=CC=C12 CJEZLXXESOYJHS-UHFFFAOYSA-N 0.000 claims 1
- AMCCFAMDPQHLQK-UHFFFAOYSA-N 3-pyridin-4-ylisoquinolin-1-amine Chemical compound C=1C2=CC=CC=C2C(N)=NC=1C1=CC=NC=C1 AMCCFAMDPQHLQK-UHFFFAOYSA-N 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 239000002585 base Substances 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- NWPNXBQSRGKSJB-UHFFFAOYSA-N 2-methylbenzonitrile Chemical compound CC1=CC=CC=C1C#N NWPNXBQSRGKSJB-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 229910052700 potassium Inorganic materials 0.000 description 5
- 239000011591 potassium Substances 0.000 description 5
- 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 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- SZYOCGSGLNKIQO-UHFFFAOYSA-N 3-pyridin-2-ylisoquinolin-1-amine Chemical compound C=1C2=CC=CC=C2C(N)=NC=1C1=CC=CC=N1 SZYOCGSGLNKIQO-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- OAGOUCJGXNLJNL-UHFFFAOYSA-N dimethylcyanamide Chemical compound CN(C)C#N OAGOUCJGXNLJNL-UHFFFAOYSA-N 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000002674 ointment Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 230000029058 respiratory gaseous exchange Effects 0.000 description 3
- 239000012047 saturated solution Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- LYQVICCMZKLQRR-UHFFFAOYSA-N 3-pyridin-4-ylisoquinoline Chemical compound N1=CC2=CC=CC=C2C=C1C1=CC=NC=C1 LYQVICCMZKLQRR-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 241000204031 Mycoplasma Species 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- 206010035664 Pneumonia Diseases 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000005018 casein Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(3+);trinitrate Chemical compound [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-UHFFFAOYSA-N 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000012907 medicinal substance Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- 239000004006 olive oil Substances 0.000 description 2
- 235000008390 olive oil Nutrition 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
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- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920001592 potato starch Polymers 0.000 description 2
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- 150000003254 radicals Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- QHZLMUACJMDIAE-SFHVURJKSA-N 1-hexadecanoyl-sn-glycerol Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)CO QHZLMUACJMDIAE-SFHVURJKSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 description 1
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- AZAUUQDHXPRWCL-UHFFFAOYSA-N 3-pyridin-3-ylisoquinolin-1-amine;dihydrochloride Chemical compound Cl.Cl.C=1C2=CC=CC=C2C(N)=NC=1C1=CC=CN=C1 AZAUUQDHXPRWCL-UHFFFAOYSA-N 0.000 description 1
- DYEKLSGRKXAKMB-UHFFFAOYSA-N 3-pyridin-4-ylisoquinolin-1-amine;dihydrochloride Chemical compound Cl.Cl.C=1C2=CC=CC=C2C(N)=NC=1C1=CC=NC=C1 DYEKLSGRKXAKMB-UHFFFAOYSA-N 0.000 description 1
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- SDZFKVMWEHVERV-UHFFFAOYSA-N 5-chloro-3-pyridin-2-ylisoquinolin-1-amine Chemical compound C=1C2=C(Cl)C=CC=C2C(N)=NC=1C1=CC=CC=N1 SDZFKVMWEHVERV-UHFFFAOYSA-N 0.000 description 1
- MVIBRSRSKGBEJE-UHFFFAOYSA-N 6,7-dimethoxy-3-n,3-n-dimethylisoquinoline-1,3-diamine Chemical compound CN(C)C1=NC(N)=C2C=C(OC)C(OC)=CC2=C1 MVIBRSRSKGBEJE-UHFFFAOYSA-N 0.000 description 1
- UNQLRETWAQYHAR-UHFFFAOYSA-N 6,7-dimethoxy-3-pyridin-2-ylisoquinolin-1-amine Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=CC=1C1=CC=CC=N1 UNQLRETWAQYHAR-UHFFFAOYSA-N 0.000 description 1
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- ZJTKEALCVYKULN-UHFFFAOYSA-N 7-methyl-3-pyridin-2-ylisoquinolin-1-amine Chemical compound N1=C(N)C2=CC(C)=CC=C2C=C1C1=CC=CC=N1 ZJTKEALCVYKULN-UHFFFAOYSA-N 0.000 description 1
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- YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 1
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- XUSVYILHSCLJTD-UHFFFAOYSA-N iodomethane;3-pyridin-2-ylisoquinolin-1-amine Chemical compound IC.C=1C2=CC=CC=C2C(N)=NC=1C1=CC=CC=N1 XUSVYILHSCLJTD-UHFFFAOYSA-N 0.000 description 1
- GJXWZWIUXACAFN-UHFFFAOYSA-N iodomethane;3-pyridin-4-ylisoquinolin-1-amine Chemical compound IC.C=1C2=CC=CC=C2C(N)=NC=1C1=CC=NC=C1 GJXWZWIUXACAFN-UHFFFAOYSA-N 0.000 description 1
- 150000002537 isoquinolines Chemical class 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
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- 235000019388 lanolin Nutrition 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- GZUXJHMPEANEGY-UHFFFAOYSA-N methyl bromide Substances BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000003883 ointment base Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 229940051027 pasteurella multocida Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229940068965 polysorbates Drugs 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- GPHQHTOMRSGBNZ-UHFFFAOYSA-N pyridine-4-carbonitrile Chemical compound N#CC1=CC=NC=C1 GPHQHTOMRSGBNZ-UHFFFAOYSA-N 0.000 description 1
- QJRYYOWARFCJQZ-UHFFFAOYSA-N pyrrolidine-1-carbonitrile Chemical compound N#CN1CCCC1 QJRYYOWARFCJQZ-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001119 rodenticidal effect Effects 0.000 description 1
- 239000003128 rodenticide Substances 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 201000004595 synovitis Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 238000005303 weighing Methods 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
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
- A23K20/132—Heterocyclic compounds containing only one nitrogen as hetero atom
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
- A23K20/137—Heterocyclic compounds containing two hetero atoms, of which at least one is nitrogen
Landscapes
- Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Food Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Animal Husbandry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4214371 | 1971-09-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2243789A1 true DE2243789A1 (de) | 1973-03-15 |
Family
ID=10423051
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2243789A Ceased DE2243789A1 (de) | 1971-09-09 | 1972-09-06 | 1-aminoisochinolinderivate, ihre salze mit saeuren und quartaeren ammoniumsalze, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS4834887A (enExample) |
| BE (1) | BE788608A (enExample) |
| CA (1) | CA985686A (enExample) |
| DE (1) | DE2243789A1 (enExample) |
| FR (1) | FR2154484A1 (enExample) |
| GB (1) | GB1353508A (enExample) |
| NL (1) | NL7212206A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008063548A3 (en) * | 2006-11-17 | 2009-01-08 | Rexahn Pharmaceuticals Inc | 5, 6, or 7-substituted-s- (hetero)arylisoquinolinamine derivatives as antitumor agents |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5272806A (en) * | 1975-12-16 | 1977-06-17 | Niyuu Mekanitsukusu Yuugen | Apparatus for arranging veneers |
| DE2826526A1 (de) * | 1977-06-17 | 1979-01-04 | Gist Brocades Nv | Kupferkomplexe von phenanthrolin-, isochinolin- und chinazolinderivaten, verfahren zu ihrer herstellung und ihre verwendung bei der bekaempfung von mykoplasmainfektionen |
| JPS5731043Y2 (enExample) * | 1979-02-27 | 1982-07-08 | ||
| HU178522B (en) * | 1979-04-11 | 1982-05-28 | Egyt Gyogyszervegyeszeti Gyar | Process for producing amino-isoquinoline derivatives |
| AU572585B2 (en) * | 1983-09-29 | 1988-05-12 | Akzo N.V. | Quinazoline and isoquinoline derivatives |
-
0
- BE BE788608D patent/BE788608A/xx unknown
-
1971
- 1971-09-09 GB GB4214371A patent/GB1353508A/en not_active Expired
-
1972
- 1972-09-06 DE DE2243789A patent/DE2243789A1/de not_active Ceased
- 1972-09-08 NL NL7212206A patent/NL7212206A/xx not_active Application Discontinuation
- 1972-09-08 CA CA151,259A patent/CA985686A/en not_active Expired
- 1972-09-08 FR FR7231992A patent/FR2154484A1/fr not_active Withdrawn
- 1972-09-09 JP JP47090876A patent/JPS4834887A/ja active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008063548A3 (en) * | 2006-11-17 | 2009-01-08 | Rexahn Pharmaceuticals Inc | 5, 6, or 7-substituted-s- (hetero)arylisoquinolinamine derivatives as antitumor agents |
| US8034829B2 (en) | 2006-11-17 | 2011-10-11 | Rexahn Pharmaceuticals, Inc. | 5, 6, or 7-substituted-3-(hetero)arylisoquinolinamine derivatives and therapeutic use thereof |
| US8314123B2 (en) | 2006-11-17 | 2012-11-20 | Rexahn Pharmaceuticals, Inc. | 5, 6, or 7-substituted -3-(hetero) arylisoquinolinamine derivatives and therapeutic use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2154484A1 (enExample) | 1973-05-11 |
| NL7212206A (enExample) | 1973-03-13 |
| BE788608A (fr) | 1973-03-08 |
| GB1353508A (en) | 1974-05-22 |
| JPS4834887A (enExample) | 1973-05-22 |
| CA985686A (en) | 1976-03-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8131 | Rejection |