CH624395A5 - - Google Patents
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- CH624395A5 CH624395A5 CH16176A CH16176A CH624395A5 CH 624395 A5 CH624395 A5 CH 624395A5 CH 16176 A CH16176 A CH 16176A CH 16176 A CH16176 A CH 16176A CH 624395 A5 CH624395 A5 CH 624395A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- group
- compounds
- salts
- acid
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 64
- 150000003839 salts Chemical class 0.000 claims description 55
- -1 alkaline earth metal carbonate Chemical class 0.000 claims description 33
- 239000002253 acid Substances 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 14
- 239000007858 starting material Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000001589 carboacyl group Chemical group 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 125000003700 epoxy group Chemical group 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 37
- 239000000243 solution Substances 0.000 description 33
- 239000000203 mixture Substances 0.000 description 32
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 24
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 238000010992 reflux Methods 0.000 description 14
- 239000002904 solvent Substances 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 9
- 238000009835 boiling Methods 0.000 description 8
- 150000001721 carbon Chemical group 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 235000011181 potassium carbonates Nutrition 0.000 description 5
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 150000007522 mineralic acids Chemical class 0.000 description 4
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 4
- 235000015497 potassium bicarbonate Nutrition 0.000 description 4
- 239000011736 potassium bicarbonate Substances 0.000 description 4
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 4
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 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 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 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
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
- 238000005406 washing Methods 0.000 description 3
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 2
- ZKZBABQTHVJCTO-UHFFFAOYSA-N (2-hydroxy-6-nitrophenyl)methyl acetate Chemical compound CC(=O)OCC1=C(O)C=CC=C1[N+]([O-])=O ZKZBABQTHVJCTO-UHFFFAOYSA-N 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
- AAEZMHSWRQVQEK-UHFFFAOYSA-N 2-methylideneoxirane Chemical group C=C1CO1 AAEZMHSWRQVQEK-UHFFFAOYSA-N 0.000 description 2
- OWAHKQHIXLFRDT-UHFFFAOYSA-N 2-nitro-6-(oxan-2-yloxy)phenol Chemical compound C1=CC=C([N+]([O-])=O)C(O)=C1OC1OCCCC1 OWAHKQHIXLFRDT-UHFFFAOYSA-N 0.000 description 2
- MNUOZFHYBCRUOD-UHFFFAOYSA-N 3-hydroxyphthalic acid Chemical compound OC(=O)C1=CC=CC(O)=C1C(O)=O MNUOZFHYBCRUOD-UHFFFAOYSA-N 0.000 description 2
- OLZIELUHRIZTHI-UHFFFAOYSA-N 4-prop-2-enoxy-2-benzofuran-1,3-dione Chemical compound C=CCOC1=CC=CC2=C1C(=O)OC2=O OLZIELUHRIZTHI-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 208000001871 Tachycardia Diseases 0.000 description 2
- 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 2
- 239000004480 active ingredient Substances 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 125000005336 allyloxy group Chemical group 0.000 description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 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
- 239000003054 catalyst Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 2
- BQGDDMMXPRJQHZ-UHFFFAOYSA-N dimethyl 3-hydroxybenzene-1,2-dicarboxylate Chemical compound COC(=O)C1=CC=CC(O)=C1C(=O)OC BQGDDMMXPRJQHZ-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- GGSLRCGXAQNFTH-UHFFFAOYSA-N ethyl 2-[2-nitro-6-(oxan-2-yloxy)phenoxy]acetate Chemical compound C1=CC=C([N+]([O-])=O)C(OCC(=O)OCC)=C1OC1OCCCC1 GGSLRCGXAQNFTH-UHFFFAOYSA-N 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 229940039009 isoproterenol Drugs 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000001630 malic acid Substances 0.000 description 2
- 235000011090 malic acid Nutrition 0.000 description 2
- 239000000594 mannitol Substances 0.000 description 2
- 235000010355 mannitol Nutrition 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 230000006794 tachycardia Effects 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 2
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical compound O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- WLXGQMVCYPUOLM-UHFFFAOYSA-N 1-hydroxyethanesulfonic acid Chemical compound CC(O)S(O)(=O)=O WLXGQMVCYPUOLM-UHFFFAOYSA-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
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- QWZQICKUZAGVFN-UHFFFAOYSA-N 2-(bromomethyl)-1-methoxy-3-nitrobenzene Chemical compound COC1=CC=CC([N+]([O-])=O)=C1CBr QWZQICKUZAGVFN-UHFFFAOYSA-N 0.000 description 1
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- 239000008107 starch Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000025033 vasoconstriction Effects 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing 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
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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 in position 2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/26—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/78—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
- C07D239/80—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
- C07D239/96—Two oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines 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 hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/18—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/36—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings condensed with one six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/10—1,2,5-Thiadiazoles; Hydrogenated 1,2,5-thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/24—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Cardiology (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (43)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH16176A CH624395A5 (fi) | 1976-01-08 | 1976-01-08 | |
US05/751,233 US4140789A (en) | 1976-01-08 | 1976-12-16 | Etherified hydroxy-benzodiheterocyclic compounds |
AR265940A AR214869A1 (es) | 1976-01-08 | 1976-12-21 | Procedimiento para la elaboracion de compuestos sustituidos por(3-amino-2-hidroxi-propiloxi)de la benzimidazol-2-ona,2-(3h)-benzoxazolona,(1h)(3h)-quinazolin-2,4-diona,3,4-dihidro-1h-quinazolin-2-ona,1,2,3,4-tetrahidro-2,3-dioxo-quinazolina,2,3-dihidro-4h-benze(5,6)oxazin-3-ona y 4h-1,3-benzoxazin-2(1h)-ona |
GB53633/76A GB1549945A (en) | 1976-01-08 | 1976-12-22 | Etherified hydroxy-benzodiheterocyclic compounds |
NZ182963A NZ182963A (en) | 1976-01-08 | 1976-12-22 | C-(3-alkylamino-2-hydroxypropoxy)benz(diaza or azaoxa)-cycloalkan-2-ones |
DE19772700193 DE2700193A1 (de) | 1976-01-08 | 1977-01-04 | Veraetherte hydroxy-benzodiheterocyclen |
ES454779A ES454779A1 (es) | 1976-01-08 | 1977-01-04 | Procedimiento para la obtencion de hidroxidiheterociclos eterados. |
SE7700056A SE7700056L (sv) | 1976-01-08 | 1977-01-04 | Foretrade hydroxibensidiheterocykler |
PL1977195154A PL110654B1 (en) | 1976-01-08 | 1977-01-06 | Method of producing new ethers of hydroxy-benzodiheterocyclic compounds |
AU21105/77A AU507884B2 (en) | 1976-01-08 | 1977-01-06 | Etherified hydroxy-benzodiheterocyclic compounds |
CA269,205A CA1083150A (en) | 1976-01-08 | 1977-01-06 | Process for the manufacture of etherified hydroxy- benzodiheterocyclic compounds |
PL1977214709A PL112441B1 (en) | 1976-01-08 | 1977-01-06 | Process for preparing novel ethers of hydroxy-benzodiheterocyclic compounds |
PL1977214710A PL112442B1 (en) | 1976-01-08 | 1977-01-06 | Process for preparing novel ethers of hydroxy-benzodiheterocyclic compounds |
FR7700232A FR2337718A1 (fr) | 1976-01-08 | 1977-01-06 | Nouveaux hydroxy-benzodiheterocycles etherifies, leur procede de preparation et leur application en tant que medicaments |
PT6603677A PT66036A1 (en) | 1976-01-08 | 1977-01-06 | Process for preparation of etherified hydroxibenzodiheterocyclic compounds |
DD7700196843A DD129444A5 (de) | 1976-01-08 | 1977-01-06 | Veraetherte hydroxy-benzodiheterocyclen |
IL51222A IL51222A (en) | 1976-01-08 | 1977-01-06 | Etherified hydroxy-benzodiheterocyclic compounds,their prearation and pharmaceutical compositions containing them |
PL1977214708A PL112491B1 (en) | 1976-01-08 | 1977-01-06 | Process for preparing novel ethers of hydroxy-benzodiheterocyclic compounds |
FI770036A FI770036A (fi) | 1976-01-08 | 1977-01-06 | |
NL7700141A NL7700141A (nl) | 1976-01-08 | 1977-01-07 | Heterocyclische benzoverbindingen met een ver- etherde hydroxylgroep. |
AT4677A AT355564B (de) | 1976-01-08 | 1977-01-07 | Verfahren zur herstellung von neuen veraetherten hydroxy-benzimidazolonen,-benzoxazolonen,- benzoxazinonen,-chinozolinonen und-chino- xalinonen |
IE31/77A IE44246B1 (en) | 1976-01-08 | 1977-01-07 | Etherified hydroxy-benzodiheterocyclic compounds |
CS77117A CS201040B2 (en) | 1976-01-08 | 1977-01-07 | Method of producing etherified hydroxy-benzo-diheterocyclic compounds |
BE173895A BE850166A (fr) | 1976-01-08 | 1977-01-07 | Nouveaux hydroxy-benzodiheterocycles etherifies |
DK6177A DK6177A (da) | 1976-01-08 | 1977-01-07 | Foretherede hydroxy-benzodiheterocycler eller salte deraf og fremgangsmade til fremstilling deraf |
NO770061A NO770061L (no) | 1976-01-08 | 1977-01-07 | Foretrede hydroksy-benzodiheterocykler. |
ZA770087A ZA7787B (en) | 1976-01-08 | 1977-01-07 | Etherified hydroxy-benzodiheterocyclic compounds |
SU772435952A SU648091A3 (ru) | 1976-01-08 | 1977-01-07 | Способ получени этерифицированных окси-бензодигетероциклов или их солей, или рацематов, или оптически активных антиподов |
JP55977A JPS5285166A (en) | 1976-01-08 | 1977-01-08 | Production of etherified hydroxyybenzodiheterocyclic compound and pharmaceutical composition |
GR52536A GR73132B (fi) | 1976-01-08 | 1977-01-08 | |
AR268660A AR214746A1 (es) | 1976-01-08 | 1977-08-02 | Procedimiento para la elaboracion de 4-(3-amino-2-hidroxi-propiloxi)-benzimidazol-2-onas y 5-(3-amino-2-hidroxi-propiloxi)-1,2,3,4-tetrahidro-2,3-dioxo-quinoxazolinas |
AR268661A AR215643A1 (es) | 1976-01-08 | 1977-08-02 | Procedimiento para la elaboracion de compuestos de 4-(3-amino-2-hidroxi-propiloxi)-benzimidazol-2-ona,5-(3-amino-2-hidroxi-propiloxi)-3,4-dihidro-1h-quinazolin-2-ona,5-(3-amino-2-hideoxi-propiloxi)-(1h)(3h)-quina-zolin-2,4-diona,7-(3-amino-2-hidroxi-propiloxi)-2(3h)-benzoxazolona,5-(3-amino-2-hidroxi-propiloxi)-1,2,3,4-tetrahidro-2,3-dioxo-quinoxazolina,8-(3-amino-2-hidroxi-propiloxi)-2,3-dihidro-4-h-benz(5,6)oxazin-3-ona y 7-(3-amino-2-hidroxi-propiloxi)-4h-1,3-benzoxazin-2(1h)ona |
AR268662A AR217258A1 (es) | 1976-01-08 | 1977-08-02 | Procedimiento para la elaboracion de compuestos(3-amino-2-hidroxi-propiloxi)-benzimidazol-2-ona,2(3h)-benzoxazolona,(1h)(3h)-quinazolin-2,4-dional,3,4-dihidro-1h-quinazolin-2-ona 1,2,3,4-tetra-dihidro-2,3-dioxo-quinazolina,2,3-hidro-4h-benz(5,6)oxazin-3-ona y 4h-1,3-benzoxazin-2(1h)-(ona) |
SU772526202A SU645568A3 (ru) | 1976-01-08 | 1977-09-29 | Способ получени этерифицированных окси-бензодигетероциклов или их солей, или рацематов или оптически активных антиподов |
SU772525901A SU651695A3 (ru) | 1976-01-08 | 1977-09-29 | Способ получени этерифицированных оксибензодигетероциклов или их солей, или рацематов, или оптически активных антиподов |
SU772525452A SU648092A3 (ru) | 1976-01-08 | 1977-09-29 | Способ получени этерифицированных оксибензодигетероциклов или их солей, или рацематов или оптически активных антиподов |
CS791289A CS201041B2 (cs) | 1976-01-08 | 1979-02-26 | Způsob výroby etherifikovaných hydroxybenzodiheterocyklických sloučenin |
CS791291A CS201043B2 (cs) | 1976-01-08 | 1979-02-26 | Způsob výroby etherifikovaných hydroxybenzodiheterocyklických sloučenin |
CS791290A CS201042B2 (cs) | 1976-01-08 | 1979-02-26 | Způsob výroby etherifikovaných hydroxybenzodiheterocyklických sloučenin |
US06/018,397 US4310527A (en) | 1976-01-08 | 1979-03-08 | Etherified hydroxy quinazolone compounds |
AT194579A AT355039B (de) | 1976-01-08 | 1979-03-15 | Verfahren zur herstellung von neuen veraetherten hydroxy-benzimidazolonen, - benzoxazolonen, -benzoxazinonen,- china- zolinonen und -chinoxazolinonen |
AT194479A AT355038B (de) | 1976-01-08 | 1979-03-15 | Verfahren zur herstellung von neuen veraetherten hydroxy-benzimidazolonen, -benzoxazolonen, - -benzoxazinonen, -chinazolinonen und- chino- xazolinonen |
AT194679A AT355040B (de) | 1976-01-08 | 1979-03-15 | Verfahren zur herstellung von neuen veraetherten hydroxy-benzimidazolonen, - -benzoxazolonen, -benzoxazinonen, - chinazolinonen und-chinoxazolinonen |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH16176A CH624395A5 (fi) | 1976-01-08 | 1976-01-08 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH624395A5 true CH624395A5 (fi) | 1981-07-31 |
Family
ID=4180641
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH16176A CH624395A5 (fi) | 1976-01-08 | 1976-01-08 |
Country Status (26)
Country | Link |
---|---|
US (2) | US4140789A (fi) |
JP (1) | JPS5285166A (fi) |
AR (4) | AR214869A1 (fi) |
AT (1) | AT355564B (fi) |
AU (1) | AU507884B2 (fi) |
BE (1) | BE850166A (fi) |
CA (1) | CA1083150A (fi) |
CH (1) | CH624395A5 (fi) |
CS (1) | CS201040B2 (fi) |
DD (1) | DD129444A5 (fi) |
DE (1) | DE2700193A1 (fi) |
DK (1) | DK6177A (fi) |
ES (1) | ES454779A1 (fi) |
FI (1) | FI770036A (fi) |
FR (1) | FR2337718A1 (fi) |
GB (1) | GB1549945A (fi) |
GR (1) | GR73132B (fi) |
IE (1) | IE44246B1 (fi) |
IL (1) | IL51222A (fi) |
NL (1) | NL7700141A (fi) |
NO (1) | NO770061L (fi) |
NZ (1) | NZ182963A (fi) |
PL (4) | PL112491B1 (fi) |
SE (1) | SE7700056L (fi) |
SU (4) | SU648091A3 (fi) |
ZA (1) | ZA7787B (fi) |
Families Citing this family (44)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH624395A5 (fi) * | 1976-01-08 | 1981-07-31 | Ciba Geigy Ag | |
DE2644833A1 (de) * | 1976-10-05 | 1978-04-20 | Boehringer Sohn Ingelheim | Neue 1-aryloxy-2-hydroxy-3-alkylenaminopropane und verfahren zu ihrer herstellung |
NZ187066A (en) * | 1977-05-03 | 1981-02-11 | Hoffmann La Roche | 4-(3-substitutedamino-2-hydroxypropoxy)-benzimidazolidin-2-(ones or thiones) |
CA1108619A (en) * | 1977-08-12 | 1981-09-08 | Carl H. Ross | 4-hydroxy-2-benzimidazolinone derivatives and the preparation thereof |
DE2801980A1 (de) * | 1978-01-18 | 1979-07-19 | Boehringer Mannheim Gmbh | 4-hydroxy-2-benzimidazolin-thion- derivate, verfahren zu ihrer herstellung sowie diese verbindungen enthaltende arzneimittel |
EP0003758A1 (de) * | 1978-02-09 | 1979-09-05 | Ciba-Geigy Ag | Verätherte Hydroxy-benzodiheterocyclen und ihre Säureadditionssalze, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Präparate |
DE2905877A1 (de) | 1979-02-16 | 1980-08-28 | Boehringer Mannheim Gmbh | Neue aminopropanolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
DD150456A5 (de) * | 1979-03-01 | 1981-09-02 | Ciba Geigy Ag | Verfahren zur herstellung von derivaten des 3-amino-1,2-propandiols |
DK187880A (da) | 1979-05-04 | 1980-11-05 | Continental Pharma | Fremgangsmaade til fremstilling af fenyl tylaminderivater |
DE2922084A1 (de) | 1979-05-31 | 1980-12-11 | Boehringer Mannheim Gmbh | Neue aminopropanol-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
US4349673A (en) * | 1980-12-23 | 1982-09-14 | Merck & Co., Inc. | Benzoxazines |
US4331679A (en) * | 1980-12-23 | 1982-05-25 | Merck Sharp & Dohme (I.A.) Corp. | (3-Aralkylamino-2-or-propoxy) heterocyclic compounds |
US4656168A (en) * | 1980-12-23 | 1987-04-07 | Merck & Co., Inc. | (3-aralkylamino-2-or-propoxy)heterocyclic compounds in method of effecting bronchodilation |
US4442094A (en) * | 1980-12-23 | 1984-04-10 | Merck & Co., Inc. | (3-Aralkylamino-2-or-propoxy)heterocyclic compounds |
DE3217012A1 (de) * | 1982-05-06 | 1983-11-10 | Dr. Karl Thomae Gmbh, 7950 Biberach | Benzoxazin-2-one, deren herstellung und diese verbindungen enthaltende arzneimittel |
IT1212552B (it) * | 1982-10-20 | 1989-11-30 | Italo Britannica L Manet Ti H | Alcanolaminossi derivati di 3,4-diidro-2h-1.4-benzotiazin-3-one, loro procedimento di produzione e loro utilizzazione farmaceutica |
GB8419797D0 (en) * | 1984-08-03 | 1984-09-05 | Beecham Group Plc | Compounds |
DE3800096A1 (de) * | 1988-01-05 | 1989-07-13 | Bayer Ag | Verwendung von benzimidazolderivaten als leistungsfoerderer |
FR2653430B1 (fr) * | 1989-10-23 | 1991-12-20 | Pf Medicament | Nouveaux derives de dihydro-1,2 oxo-2 quinoxalines, leur preparation et leur application en therapeutique. |
ZA967892B (en) * | 1995-09-21 | 1998-03-18 | Lilly Co Eli | Selective β3 adrenergic agonists. |
ATE215369T1 (de) * | 1996-09-05 | 2002-04-15 | Lilly Co Eli | Carbazolanaloge als selektive beta3-adrenergische agonisten |
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CA726737A (en) * | 1966-01-25 | C. Scarborough Homer | 4-substituted quinolines and quinazolines | |
US3686176A (en) * | 1970-03-09 | 1972-08-22 | Frosst & Co Charles E | 1-morpholino phenoxy-3-alkylamino-2-propanols |
US3763153A (en) * | 1972-02-22 | 1973-10-02 | Squibb & Sons Inc | Benzothiazines |
GB1488330A (en) * | 1973-12-19 | 1977-10-12 | Smith Kline French Lab | Dihydropyridazinones |
CH624395A5 (fi) * | 1976-01-08 | 1981-07-31 | Ciba Geigy Ag |
-
1976
- 1976-01-08 CH CH16176A patent/CH624395A5/de not_active IP Right Cessation
- 1976-12-16 US US05/751,233 patent/US4140789A/en not_active Expired - Lifetime
- 1976-12-21 AR AR265940A patent/AR214869A1/es active
- 1976-12-22 GB GB53633/76A patent/GB1549945A/en not_active Expired
- 1976-12-22 NZ NZ182963A patent/NZ182963A/xx unknown
-
1977
- 1977-01-04 ES ES454779A patent/ES454779A1/es not_active Expired
- 1977-01-04 DE DE19772700193 patent/DE2700193A1/de not_active Withdrawn
- 1977-01-04 SE SE7700056A patent/SE7700056L/xx unknown
- 1977-01-06 DD DD7700196843A patent/DD129444A5/xx unknown
- 1977-01-06 AU AU21105/77A patent/AU507884B2/en not_active Expired
- 1977-01-06 FR FR7700232A patent/FR2337718A1/fr active Granted
- 1977-01-06 PL PL1977214708A patent/PL112491B1/pl unknown
- 1977-01-06 PL PL1977214710A patent/PL112442B1/pl unknown
- 1977-01-06 PL PL1977214709A patent/PL112441B1/pl unknown
- 1977-01-06 PL PL1977195154A patent/PL110654B1/pl unknown
- 1977-01-06 CA CA269,205A patent/CA1083150A/en not_active Expired
- 1977-01-06 FI FI770036A patent/FI770036A/fi not_active Application Discontinuation
- 1977-01-06 IL IL51222A patent/IL51222A/xx unknown
- 1977-01-07 IE IE31/77A patent/IE44246B1/en unknown
- 1977-01-07 BE BE173895A patent/BE850166A/xx unknown
- 1977-01-07 DK DK6177A patent/DK6177A/da unknown
- 1977-01-07 NL NL7700141A patent/NL7700141A/xx not_active Application Discontinuation
- 1977-01-07 NO NO770061A patent/NO770061L/no unknown
- 1977-01-07 SU SU772435952A patent/SU648091A3/ru active
- 1977-01-07 AT AT4677A patent/AT355564B/de not_active IP Right Cessation
- 1977-01-07 CS CS77117A patent/CS201040B2/cs unknown
- 1977-01-07 ZA ZA770087A patent/ZA7787B/xx unknown
- 1977-01-08 JP JP55977A patent/JPS5285166A/ja active Pending
- 1977-01-08 GR GR52536A patent/GR73132B/el unknown
- 1977-08-02 AR AR268661A patent/AR215643A1/es active
- 1977-08-02 AR AR268662A patent/AR217258A1/es active
- 1977-08-02 AR AR268660A patent/AR214746A1/es active
- 1977-09-29 SU SU772526202A patent/SU645568A3/ru active
- 1977-09-29 SU SU772525901A patent/SU651695A3/ru active
- 1977-09-29 SU SU772525452A patent/SU648092A3/ru active
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1979
- 1979-03-08 US US06/018,397 patent/US4310527A/en not_active Expired - Lifetime
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