NO743534L - - Google Patents
Info
- Publication number
- NO743534L NO743534L NO743534A NO743534A NO743534L NO 743534 L NO743534 L NO 743534L NO 743534 A NO743534 A NO 743534A NO 743534 A NO743534 A NO 743534A NO 743534 L NO743534 L NO 743534L
- Authority
- NO
- Norway
- Prior art keywords
- carbon atoms
- compounds
- formula
- isoquinoline
- alkyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 8
- -1 1-(2-hydroxy-3-isopropyl-aminopropoxy)-isoquinoline Chemical compound 0.000 claims description 7
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 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 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 3
- IDILZPYOXZCHSP-UHFFFAOYSA-N 5-[(7-methoxyisoquinolin-1-yl)oxymethyl]-2-phenyl-3-propan-2-yl-1,3-oxazolidine Chemical compound C12=CC(OC)=CC=C2C=CN=C1OCC(O1)CN(C(C)C)C1C1=CC=CC=C1 IDILZPYOXZCHSP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- HNOAXSVPMXZKBT-UHFFFAOYSA-N (2-phenyl-3-propan-2-yl-1,3-oxazolidin-5-yl)methanol Chemical compound CC(C)N1CC(CO)OC1C1=CC=CC=C1 HNOAXSVPMXZKBT-UHFFFAOYSA-N 0.000 description 2
- YKBZGEJJKPNRSI-UHFFFAOYSA-N 3-(propan-2-ylamino)propane-1,2-diol Chemical compound CC(C)NCC(O)CO YKBZGEJJKPNRSI-UHFFFAOYSA-N 0.000 description 2
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 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
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940039009 isoproterenol Drugs 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000002503 metabolic effect Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 229940072033 potash Drugs 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 230000007306 turnover Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- AVVWARLASXCKIH-BTJKTKAUSA-N (z)-but-2-enedioic acid;1-isoquinolin-1-yloxy-3-(propan-2-ylamino)propan-2-ol Chemical compound OC(=O)\C=C/C(O)=O.C1=CC=C2C(OCC(O)CNC(C)C)=NC=CC2=C1 AVVWARLASXCKIH-BTJKTKAUSA-N 0.000 description 1
- RKECOJQWOKZZQD-UHFFFAOYSA-N 1-(6-methoxyisoquinolin-1-yl)oxy-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)COC1=NC=CC2=CC(OC)=CC=C21 RKECOJQWOKZZQD-UHFFFAOYSA-N 0.000 description 1
- ZFABSYAPGQRBDK-UHFFFAOYSA-N 1-(7-methoxyisoquinolin-1-yl)oxy-3-(propan-2-ylamino)propan-2-ol Chemical compound C1=CN=C(OCC(O)CNC(C)C)C2=CC(OC)=CC=C21 ZFABSYAPGQRBDK-UHFFFAOYSA-N 0.000 description 1
- SSBMOLGNIQJGPF-UHFFFAOYSA-N 1-chloro-7-methoxyisoquinoline Chemical compound C1=CN=C(Cl)C2=CC(OC)=CC=C21 SSBMOLGNIQJGPF-UHFFFAOYSA-N 0.000 description 1
- MSQCQINLJMEVNJ-UHFFFAOYSA-N 1-chloroisoquinoline Chemical compound C1=CC=C2C(Cl)=NC=CC2=C1 MSQCQINLJMEVNJ-UHFFFAOYSA-N 0.000 description 1
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 description 1
- FWWOWPGPERBCNJ-UHFFFAOYSA-N 2-hydroxy-4-(2-hydroxyethoxy)-4-oxobutanoic acid Chemical compound OCCOC(=O)CC(O)C(O)=O FWWOWPGPERBCNJ-UHFFFAOYSA-N 0.000 description 1
- VUGCBIWQHSRQBZ-UHFFFAOYSA-N 2-methylbut-3-yn-2-amine Chemical compound CC(C)(N)C#C VUGCBIWQHSRQBZ-UHFFFAOYSA-N 0.000 description 1
- GROIXABKSDRPLV-UHFFFAOYSA-N 5-(isoquinolin-1-yloxymethyl)-2-phenyl-3-propan-2-yl-1,3-oxazolidine Chemical compound CC(C)N1CC(COC=2C3=CC=CC=C3C=CN=2)OC1C1=CC=CC=C1 GROIXABKSDRPLV-UHFFFAOYSA-N 0.000 description 1
- BVFQMGAICIPIGU-UHFFFAOYSA-N 5-[(6-methoxyisoquinolin-1-yl)oxymethyl]-2-phenyl-3-propan-2-yl-1,3-oxazolidine Chemical compound N=1C=CC2=CC(OC)=CC=C2C=1OCC(O1)CN(C(C)C)C1C1=CC=CC=C1 BVFQMGAICIPIGU-UHFFFAOYSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 206010058177 Hyperkinetic heart syndrome Diseases 0.000 description 1
- 235000000434 Melocanna baccifera Nutrition 0.000 description 1
- 241001497770 Melocanna baccifera Species 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 210000001789 adipocyte Anatomy 0.000 description 1
- 230000001800 adrenalinergic effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000003288 anthiarrhythmic effect Effects 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- 238000010009 beating Methods 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 201000010063 epididymitis Diseases 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 230000004116 glycogenolysis Effects 0.000 description 1
- 210000002837 heart atrium Anatomy 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229960001317 isoprenaline Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 230000004130 lipolysis Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 208000009157 neurocirculatory asthenia Diseases 0.000 description 1
- 150000002917 oxazolidines Chemical class 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 206010042431 subvalvular aortic stenosis Diseases 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D263/06—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by oxygen atoms, attached to ring carbon atoms
-
- 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
-
- 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
- C07D217/24—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1430773A CH581113A5 (da) | 1973-10-08 | 1973-10-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO743534L true NO743534L (da) | 1975-05-05 |
Family
ID=4399720
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO743534A NO743534L (da) | 1973-10-08 | 1974-09-30 |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS5082078A (da) |
| AT (1) | ATA802974A (da) |
| AU (2) | AU498889B2 (da) |
| BE (1) | BE820789A (da) |
| CA (1) | CA1021772A (da) |
| CH (1) | CH581113A5 (da) |
| DD (1) | DD114605A5 (da) |
| DE (1) | DE2447756A1 (da) |
| DK (1) | DK135766B (da) |
| ES (1) | ES430759A1 (da) |
| FI (1) | FI286374A (da) |
| FR (1) | FR2247242B1 (da) |
| GB (1) | GB1474775A (da) |
| HU (1) | HU169126B (da) |
| IL (1) | IL45797A (da) |
| NL (1) | NL7413105A (da) |
| NO (1) | NO743534L (da) |
| PH (1) | PH11611A (da) |
| SE (1) | SE7412310L (da) |
| SU (1) | SU567403A3 (da) |
| ZA (1) | ZA746409B (da) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK116976A (da) * | 1975-03-26 | 1976-09-27 | Sandoz Ag | Fremgangsmade til fremstilling af isoquinolinderivater |
| US4129565A (en) * | 1975-07-11 | 1978-12-12 | Nisshin Flour Milling Co., Ltd. | Isocarbostyril derivatives |
| SE7804318L (sv) * | 1977-05-02 | 1978-11-03 | Merck & Co Inc | Nya naftyridiner |
| EP0711804A3 (de) | 1994-11-14 | 1999-09-22 | Ciba SC Holding AG | Kryptolichtschutzmittel |
| US6426415B1 (en) | 1997-09-03 | 2002-07-30 | Guilford Pharmaceuticals Inc. | Alkoxy-substituted compounds, methods and compositions for inhibiting parp activity |
| 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 |
| 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 |
| US6514983B1 (en) | 1997-09-03 | 2003-02-04 | Guilford Pharmaceuticals Inc. | Compounds, methods and pharmaceutical compositions for treating neural or cardiovascular tissue damage |
| US6197785B1 (en) * | 1997-09-03 | 2001-03-06 | 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 |
| 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 |
| AU2001264595A1 (en) | 2000-05-19 | 2001-12-03 | Guilford Pharmaceuticals Inc. | Sulfonamide and carbamide derivatives of 6(5h)phenanthridinones and their uses |
| US6348475B1 (en) | 2000-06-01 | 2002-02-19 | Guilford Pharmaceuticals Inc. | Methods, compounds and compositions for treating gout |
-
1973
- 1973-10-08 CH CH1430773A patent/CH581113A5/xx not_active IP Right Cessation
-
1974
- 1974-09-30 NO NO743534A patent/NO743534L/no unknown
- 1974-09-30 DK DK514874AA patent/DK135766B/da unknown
- 1974-09-30 SE SE7412310A patent/SE7412310L/xx unknown
- 1974-10-01 FI FI2863/74A patent/FI286374A/fi unknown
- 1974-10-03 GB GB4290974A patent/GB1474775A/en not_active Expired
- 1974-10-04 NL NL7413105A patent/NL7413105A/xx not_active Application Discontinuation
- 1974-10-04 DD DD181520A patent/DD114605A5/xx unknown
- 1974-10-07 BE BE149290A patent/BE820789A/xx unknown
- 1974-10-07 IL IL45797A patent/IL45797A/xx unknown
- 1974-10-07 JP JP49114815A patent/JPS5082078A/ja active Pending
- 1974-10-07 CA CA210,857A patent/CA1021772A/en not_active Expired
- 1974-10-07 DE DE19742447756 patent/DE2447756A1/de not_active Withdrawn
- 1974-10-07 ES ES430759A patent/ES430759A1/es not_active Expired
- 1974-10-07 PH PH16382A patent/PH11611A/en unknown
- 1974-10-07 AT AT802974A patent/ATA802974A/de not_active Application Discontinuation
- 1974-10-08 FR FR7433761A patent/FR2247242B1/fr not_active Expired
- 1974-10-08 HU HUSA2697A patent/HU169126B/hu unknown
- 1974-10-08 SU SU7402066522A patent/SU567403A3/ru active
- 1974-10-08 AU AU74090/74A patent/AU498889B2/en not_active Expired
- 1974-10-08 ZA ZA00746409A patent/ZA746409B/xx unknown
- 1974-10-09 AU AU74130/74A patent/AU7413074A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IL45797A0 (en) | 1974-12-31 |
| AU7409074A (en) | 1976-04-15 |
| AU7413074A (en) | 1976-04-15 |
| NL7413105A (nl) | 1975-04-10 |
| CA1021772A (en) | 1977-11-29 |
| SU567403A3 (ru) | 1977-07-30 |
| CH581113A5 (da) | 1976-10-29 |
| HU169126B (da) | 1976-09-28 |
| FR2247242B1 (da) | 1978-07-21 |
| DD114605A5 (da) | 1975-08-12 |
| AU7408974A (en) | 1976-04-15 |
| DE2447756A1 (de) | 1975-04-10 |
| BE820789A (fr) | 1975-04-07 |
| FR2247242A1 (da) | 1975-05-09 |
| AU498889B2 (en) | 1979-03-29 |
| FI286374A (da) | 1975-04-09 |
| IL45797A (en) | 1978-04-30 |
| DK514874A (da) | 1975-06-09 |
| ES430759A1 (es) | 1977-04-16 |
| ATA802974A (de) | 1979-07-15 |
| DK135766B (da) | 1977-06-20 |
| SE7412310L (da) | 1975-04-09 |
| JPS5082078A (da) | 1975-07-03 |
| ZA746409B (en) | 1976-05-26 |
| DK135766C (da) | 1977-11-21 |
| PH11611A (en) | 1978-04-12 |
| GB1474775A (en) | 1977-05-25 |
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