NO122482B - - Google Patents
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- Publication number
- NO122482B NO122482B NO16994967A NO16994967A NO122482B NO 122482 B NO122482 B NO 122482B NO 16994967 A NO16994967 A NO 16994967A NO 16994967 A NO16994967 A NO 16994967A NO 122482 B NO122482 B NO 122482B
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- hydrogen
- methyl
- general formula
- tetraazaphenalene
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- -1 hydroxy- Chemical class 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- DNPVEBBFVJUASY-UHFFFAOYSA-N ctk0i2885 Chemical class N1N=CC2=CC=CC3=CN=NC1=C32 DNPVEBBFVJUASY-UHFFFAOYSA-N 0.000 claims description 5
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 5
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 20
- 239000000203 mixture Substances 0.000 description 19
- 239000000706 filtrate Substances 0.000 description 18
- 239000002244 precipitate Substances 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- 238000010992 reflux Methods 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 10
- SJTCSECMUIVKNU-UHFFFAOYSA-N 12-methyl-2,3,11,12-tetrazatricyclo[7.3.1.05,13]trideca-1(13),2,4,6,8,10-hexaene Chemical compound CN1N=CC2=CC=CC3=CN=NC1=C32 SJTCSECMUIVKNU-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 6
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 5
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 5
- DBRDGLWIILLOHI-UHFFFAOYSA-N 4-chloro-12-methyl-2,3,11,12-tetrazatricyclo[7.3.1.05,13]trideca-1,3,5,7,9(13),10-hexaene Chemical compound ClC=1N=NC=2N(N=CC3=CC=CC1C23)C DBRDGLWIILLOHI-UHFFFAOYSA-N 0.000 description 5
- KXDQRXKKTYUWTO-UHFFFAOYSA-N 4-oxo-1-phenyl-3H-phthalazine-5-carboxylic acid Chemical class C1(=CC=CC=C1)C1=NNC(C2=C(C=CC=C12)C(=O)O)=O KXDQRXKKTYUWTO-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 5
- 229940071870 hydroiodic acid Drugs 0.000 description 5
- 238000004809 thin layer chromatography Methods 0.000 description 5
- BWJAOVUPAKDWMQ-UHFFFAOYSA-N 4-chloro-12-phenyl-2,3,11,12-tetrazatricyclo[7.3.1.05,13]trideca-1,3,5,7,9(13),10-hexaene Chemical compound ClC=1N=NC=2N(N=CC3=CC=CC1C23)C2=CC=CC=C2 BWJAOVUPAKDWMQ-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000007717 exclusion Effects 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- AWGBNOQONQAYBG-UHFFFAOYSA-N 12-methyl-2,3,11,12-tetrazatricyclo[7.3.1.05,13]trideca-1,5,7,9(13),10-pentaene-4-thione Chemical compound S=C1NN=C2N(N=CC=3C=CC=C1C23)C AWGBNOQONQAYBG-UHFFFAOYSA-N 0.000 description 3
- OZEXQKPZNWAGQZ-UHFFFAOYSA-N 12-phenyl-2,3,11,12-tetrazatricyclo[7.3.1.05,13]trideca-1(13),2,4,6,8,10-hexaene Chemical compound C1(=CC=CC=C1)N1N=CC2=CC=CC3=CN=NC1=C32 OZEXQKPZNWAGQZ-UHFFFAOYSA-N 0.000 description 3
- GBXYCEXJPRKVTQ-UHFFFAOYSA-N 2,3,11,12-tetrazatricyclo[7.3.1.05,13]trideca-1,5,7,9(13),10-pentaen-4-one Chemical compound O=C1NNC=2N=NC=C3C=CC=C1C23 GBXYCEXJPRKVTQ-UHFFFAOYSA-N 0.000 description 3
- IUNYUMHIMGYUJO-UHFFFAOYSA-N 4-chloro-10-phenyl-2,3,11,12-tetrazatricyclo[7.3.1.05,13]trideca-1,3,5(13),6,8,10-hexaene Chemical compound ClC1=NNC=2N=NC(=C3C=CC=C1C23)C2=CC=CC=C2 IUNYUMHIMGYUJO-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 239000007868 Raney catalyst Substances 0.000 description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- 239000002168 alkylating agent Substances 0.000 description 3
- 229940100198 alkylating agent Drugs 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 150000001879 copper Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- MMRDHJMULHIHFP-UHFFFAOYSA-N 2,3,11,12-tetrazatricyclo[7.3.1.05,13]trideca-1,3,5,7,9(13),10-hexaen-4-ylhydrazine dihydrochloride Chemical compound Cl.Cl.N(N)C1=NNC=2N=NC=C3C=CC=C1C23 MMRDHJMULHIHFP-UHFFFAOYSA-N 0.000 description 2
- KTFJPMPXSYUEIP-UHFFFAOYSA-N 3-benzoylphthalic acid Chemical compound OC(=O)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1C(O)=O KTFJPMPXSYUEIP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
- 238000005695 dehalogenation reaction Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 2
- 229940067157 phenylhydrazine Drugs 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- OGFAWKRXZLGJSK-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenyl)ethanone Chemical compound OC1=CC(O)=CC=C1C(=O)CC1=CC=C([N+]([O-])=O)C=C1 OGFAWKRXZLGJSK-UHFFFAOYSA-N 0.000 description 1
- JDOLHKIOQHFKFC-UHFFFAOYSA-N 1-hydroxy-3-oxo-1h-2-benzofuran-4-carboxylic acid Chemical class C1=CC=C(C(O)=O)C2=C1C(O)OC2=O JDOLHKIOQHFKFC-UHFFFAOYSA-N 0.000 description 1
- UETOSPQPDSSVOC-UHFFFAOYSA-N 12-methyl-2,3,11,12-tetrazatricyclo[7.3.1.05,13]trideca-1,5,7,9(13),10-pentaen-4-one Chemical compound O=C1NN=C2N(N=CC=3C=CC=C1C23)C UETOSPQPDSSVOC-UHFFFAOYSA-N 0.000 description 1
- QKSHXBOMIBCYNC-UHFFFAOYSA-N 12-phenyl-2,3,11,12-tetrazatricyclo[7.3.1.05,13]trideca-1,5,7,9(13),10-pentaen-4-one Chemical compound O=C1NN=C2N(N=CC=3C=CC=C1C23)C2=CC=CC=C2 QKSHXBOMIBCYNC-UHFFFAOYSA-N 0.000 description 1
- AFBBKYQYNPNMAT-UHFFFAOYSA-N 1h-1,2,4-triazol-1-ium-3-thiolate Chemical compound SC=1N=CNN=1 AFBBKYQYNPNMAT-UHFFFAOYSA-N 0.000 description 1
- SOMQAIAICJTERE-UHFFFAOYSA-N 2,3,11,12-tetrazatricyclo[7.3.1.05,13]trideca-1,5,7,9(13),10-pentaene-4-thione Chemical compound SC1=NNC=2N=NC=C3C=CC=C1C23 SOMQAIAICJTERE-UHFFFAOYSA-N 0.000 description 1
- BSPCSKHALVHRSR-UHFFFAOYSA-N 2-chlorobutane Chemical compound CCC(C)Cl BSPCSKHALVHRSR-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
- BWLOFOWYSHIPOD-UHFFFAOYSA-N 4-bromo-12-methyl-2,3,11,12-tetrazatricyclo[7.3.1.05,13]trideca-1,3,5,7,9(13),10-hexaene Chemical compound BrC=1N=NC=2N(N=CC3=CC=CC1C23)C BWLOFOWYSHIPOD-UHFFFAOYSA-N 0.000 description 1
- VCZMGKACHRYLTQ-UHFFFAOYSA-N 4-chloro-2,3,11,12-tetrazatricyclo[7.3.1.05,13]trideca-1,3,5,7,9(13),10-hexaene Chemical compound ClC1=NNC=2N=NC=C3C=CC=C1C23 VCZMGKACHRYLTQ-UHFFFAOYSA-N 0.000 description 1
- TWWAWPHAOPTQEU-UHFFFAOYSA-N 4-methyl-2-benzofuran-1,3-dione Chemical compound CC1=CC=CC2=C1C(=O)OC2=O TWWAWPHAOPTQEU-UHFFFAOYSA-N 0.000 description 1
- RDCXJIAWTVQLHJ-UHFFFAOYSA-N 4-oxo-3-phenylphthalazine-5-carboxylic acid Chemical class C1(=CC=CC=C1)N1C(C2=C(C=CC=C2C=N1)C(=O)O)=O RDCXJIAWTVQLHJ-UHFFFAOYSA-N 0.000 description 1
- XCJLBNVENUPHEA-UHFFFAOYSA-N 4-phenyl-2h-phthalazin-1-one Chemical compound C12=CC=CC=C2C(=O)NN=C1C1=CC=CC=C1 XCJLBNVENUPHEA-UHFFFAOYSA-N 0.000 description 1
- HSPSRBOGTILTIR-UHFFFAOYSA-N 7-bromo-2,3,11,12-tetrazatricyclo[7.3.1.05,13]trideca-1(13),2,4,6,8,10-hexaene Chemical compound BrC=1C=C2C=NNC=3N=NC=C(C1)C32 HSPSRBOGTILTIR-UHFFFAOYSA-N 0.000 description 1
- UNBPLOGIKNLKSD-UHFFFAOYSA-N 7-methoxy-2,3,11,12-tetrazatricyclo[7.3.1.05,13]trideca-1(13),2,4,6,8,10-hexaene Chemical compound COC=1C=C2C=NNC=3N=NC=C(C1)C32 UNBPLOGIKNLKSD-UHFFFAOYSA-N 0.000 description 1
- JUDLWURQTBTQKW-UHFFFAOYSA-N C(=O)(O)C=1C=C2C=NNC=3N=NC=C(C1)C32 Chemical compound C(=O)(O)C=1C=C2C=NNC=3N=NC=C(C1)C32 JUDLWURQTBTQKW-UHFFFAOYSA-N 0.000 description 1
- SIWIHCLTQPYSHZ-UHFFFAOYSA-N C(CCC)OC=1C=C2C=NNC=3N=NC=C(C1)C32 Chemical compound C(CCC)OC=1C=C2C=NNC=3N=NC=C(C1)C32 SIWIHCLTQPYSHZ-UHFFFAOYSA-N 0.000 description 1
- 239000004128 Copper(II) sulphate Substances 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical class [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 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
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
- 238000010521 absorption reaction Methods 0.000 description 1
- 229940091181 aconitic acid Drugs 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000007853 buffer solution Substances 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
- 239000002775 capsule Substances 0.000 description 1
- GTZCVFVGUGFEME-IWQZZHSRSA-N cis-aconitic acid Chemical compound OC(=O)C\C(C(O)=O)=C\C(O)=O GTZCVFVGUGFEME-IWQZZHSRSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- BWFPGXWASODCHM-UHFFFAOYSA-N copper monosulfide Chemical compound [Cu]=S BWFPGXWASODCHM-UHFFFAOYSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 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
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical group COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- XDJOIMJURHQYDW-UHFFFAOYSA-N phenalene Chemical compound C1=CC(CC=C2)=C3C2=CC=CC3=C1 XDJOIMJURHQYDW-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical class OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/06—Peri-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US58398066A | 1966-10-03 | 1966-10-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO122482B true NO122482B (da) | 1971-07-05 |
Family
ID=24335405
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO16994967A NO122482B (da) | 1966-10-03 | 1967-10-02 |
Country Status (14)
| Country | Link |
|---|---|
| AT (3) | AT273980B (da) |
| BE (2) | BE704585A (da) |
| CH (2) | CH515909A (da) |
| DE (2) | DE1695039A1 (da) |
| DK (2) | DK120755B (da) |
| ES (2) | ES345681A1 (da) |
| FI (2) | FI47770C (da) |
| FR (3) | FR1550404A (da) |
| GB (2) | GB1208114A (da) |
| GR (2) | GR37757B (da) |
| IL (2) | IL28709A (da) |
| NL (2) | NL6713374A (da) |
| NO (1) | NO122482B (da) |
| SE (2) | SE329401B (da) |
-
1967
- 1967-09-30 CH CH1363967A patent/CH515909A/de not_active IP Right Cessation
- 1967-09-30 CH CH1364067A patent/CH486477A/de not_active IP Right Cessation
- 1967-10-02 BE BE704585D patent/BE704585A/xx unknown
- 1967-10-02 DK DK487767A patent/DK120755B/da unknown
- 1967-10-02 IL IL2870967A patent/IL28709A/en unknown
- 1967-10-02 NL NL6713374A patent/NL6713374A/xx unknown
- 1967-10-02 AT AT891467A patent/AT273980B/de active
- 1967-10-02 FR FR1550404D patent/FR1550404A/fr not_active Expired
- 1967-10-02 DE DE19671695039 patent/DE1695039A1/de active Pending
- 1967-10-02 NL NL6713378A patent/NL6713378A/xx unknown
- 1967-10-02 NO NO16994967A patent/NO122482B/no unknown
- 1967-10-02 GB GB4467967A patent/GB1208114A/en not_active Expired
- 1967-10-02 FI FI263267A patent/FI47770C/fi active
- 1967-10-02 SE SE1346067A patent/SE329401B/xx unknown
- 1967-10-02 ES ES345681A patent/ES345681A1/es not_active Expired
- 1967-10-02 DK DK487867A patent/DK123653B/da unknown
- 1967-10-02 AT AT891667A patent/AT273981B/de active
- 1967-10-02 IL IL2871067A patent/IL28710A/en unknown
- 1967-10-02 GR GR670137757A patent/GR37757B/el unknown
- 1967-10-02 FI FI263167A patent/FI47769C/fi active
- 1967-10-02 GR GR670137758A patent/GR37758B/el unknown
- 1967-10-02 ES ES345680A patent/ES345680A1/es not_active Expired
- 1967-10-02 GB GB44680/67A patent/GB1204522A/en not_active Expired
- 1967-10-02 AT AT880368A patent/AT276411B/de active
- 1967-10-02 BE BE704584D patent/BE704584A/xx unknown
- 1967-10-02 SE SE1346167A patent/SE335346B/xx unknown
- 1967-10-02 DE DE19671695038 patent/DE1695038A1/de active Pending
- 1967-12-29 FR FR134300A patent/FR7210M/fr not_active Expired
- 1967-12-29 FR FR134301A patent/FR7211M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GR37757B (el) | 1969-07-11 |
| AT273980B (de) | 1969-09-10 |
| FR1550404A (da) | 1968-12-20 |
| DK123653B (da) | 1972-07-17 |
| GR37758B (el) | 1969-07-11 |
| ES345680A1 (es) | 1968-11-16 |
| DK120755B (da) | 1971-07-12 |
| CH515909A (de) | 1971-11-30 |
| FI47769B (da) | 1973-11-30 |
| DE1695038A1 (de) | 1971-04-08 |
| BE704584A (da) | 1968-04-02 |
| IL28709A (en) | 1973-01-30 |
| FI47770C (fi) | 1974-03-11 |
| DE1695039A1 (de) | 1971-04-08 |
| BE704585A (da) | 1968-04-02 |
| AT273981B (de) | 1969-09-10 |
| GB1204522A (en) | 1970-09-09 |
| ES345681A1 (es) | 1968-11-16 |
| AT276411B (de) | 1969-11-25 |
| FI47769C (fi) | 1974-03-11 |
| NL6713378A (da) | 1968-04-04 |
| NL6713374A (da) | 1968-04-04 |
| GB1208114A (en) | 1970-10-07 |
| CH486477A (de) | 1970-02-28 |
| SE329401B (da) | 1970-10-12 |
| SE335346B (da) | 1971-05-24 |
| FR7211M (da) | 1969-08-25 |
| FI47770B (da) | 1973-11-30 |
| FR7210M (da) | 1969-08-25 |
| IL28710A (en) | 1973-01-30 |
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