NO753718L - - Google Patents
Info
- Publication number
- NO753718L NO753718L NO753718A NO753718A NO753718L NO 753718 L NO753718 L NO 753718L NO 753718 A NO753718 A NO 753718A NO 753718 A NO753718 A NO 753718A NO 753718 L NO753718 L NO 753718L
- Authority
- NO
- Norway
- Prior art keywords
- radical
- amino
- alkoxy
- ethyl
- corresponding compound
- Prior art date
Links
- -1 hydroxy- Chemical class 0.000 claims description 147
- 150000001875 compounds Chemical class 0.000 claims description 74
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 24
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 21
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 11
- 150000003254 radicals Chemical class 0.000 claims description 11
- 125000006413 ring segment Chemical group 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
- 150000001854 cinnolines Chemical class 0.000 claims description 7
- 239000012954 diazonium Substances 0.000 claims description 7
- 150000001989 diazonium salts Chemical class 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 4
- SYXBGRYFXPQNMC-UHFFFAOYSA-N 6-amino-4-oxo-1h-cinnoline-3-carboxylic acid Chemical compound N1=NC(C(O)=O)=C(O)C2=CC(N)=CC=C21 SYXBGRYFXPQNMC-UHFFFAOYSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 claims description 4
- 235000019253 formic acid Nutrition 0.000 claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 2
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 150000002540 isothiocyanates Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 108
- 239000000203 mixture Substances 0.000 description 57
- 239000000243 solution Substances 0.000 description 52
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
- 239000007787 solid Substances 0.000 description 40
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 24
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 23
- SYESXLNLQVNDEV-UHFFFAOYSA-N ethyl 6-amino-4-oxo-1h-cinnoline-3-carboxylate Chemical compound C1=CC(N)=CC2=C(O)C(C(=O)OCC)=NN=C21 SYESXLNLQVNDEV-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 239000000725 suspension Substances 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 150000007942 carboxylates Chemical class 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 238000010828 elution Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 238000003776 cleavage reaction Methods 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 239000000825 pharmaceutical preparation Substances 0.000 description 4
- 230000007017 scission Effects 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 208000006673 asthma Diseases 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000006193 diazotization reaction Methods 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- CQDHMEGGSXPPIN-UHFFFAOYSA-N ethyl 6-nitro-4-oxo-1h-cinnoline-3-carboxylate Chemical compound C1=CC([N+]([O-])=O)=CC2=C(O)C(C(=O)OCC)=NN=C21 CQDHMEGGSXPPIN-UHFFFAOYSA-N 0.000 description 3
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 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
- 150000001340 alkali metals Chemical class 0.000 description 2
- 125000005236 alkanoylamino group Chemical group 0.000 description 2
- 229960003116 amyl nitrite Drugs 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229940117975 chromium trioxide Drugs 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical group [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- RABBXBWEHYCWGF-UHFFFAOYSA-N ethyl 4-oxo-6-thiophen-2-yl-1h-cinnoline-3-carboxylate Chemical compound C=1C2=C(O)C(C(=O)OCC)=NN=C2C=CC=1C1=CC=CS1 RABBXBWEHYCWGF-UHFFFAOYSA-N 0.000 description 2
- ZIMKGOWKNXUMNV-UHFFFAOYSA-N ethyl 6-[(2-aminoacetyl)amino]-4-oxo-1h-cinnoline-3-carboxylate;hydrochloride Chemical compound Cl.C1=CC(NC(=O)CN)=CC2=C(O)C(C(=O)OCC)=NN=C21 ZIMKGOWKNXUMNV-UHFFFAOYSA-N 0.000 description 2
- KKLLBLIQRWDFDU-UHFFFAOYSA-N ethyl 6-cyano-4-oxo-1h-cinnoline-3-carboxylate Chemical compound C1=CC(C#N)=CC2=C(O)C(C(=O)OCC)=NN=C21 KKLLBLIQRWDFDU-UHFFFAOYSA-N 0.000 description 2
- 230000004992 fission Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- CSDTZUBPSYWZDX-UHFFFAOYSA-N n-pentyl nitrite Chemical compound CCCCCON=O CSDTZUBPSYWZDX-UHFFFAOYSA-N 0.000 description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
- QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- XBVPWXPXVAFYMW-UHFFFAOYSA-N (2,4,5-trichlorophenyl) 2-(phenylmethoxycarbonylamino)acetate Chemical compound C1=C(Cl)C(Cl)=CC(Cl)=C1OC(=O)CNC(=O)OCC1=CC=CC=C1 XBVPWXPXVAFYMW-UHFFFAOYSA-N 0.000 description 1
- DSGKWFGEUBCEIE-UHFFFAOYSA-N (2-carbonochloridoylphenyl) acetate Chemical compound CC(=O)OC1=CC=CC=C1C(Cl)=O DSGKWFGEUBCEIE-UHFFFAOYSA-N 0.000 description 1
- UFMBERDMCRCVSM-UHFFFAOYSA-N 1h-cinnolin-4-one Chemical class C1=CC=C2C(O)=CN=NC2=C1 UFMBERDMCRCVSM-UHFFFAOYSA-N 0.000 description 1
- BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical compound FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- CXUGAWWYKSOLEL-UHFFFAOYSA-N 2h-cinnolin-3-one Chemical group C1=CC=C2N=NC(O)=CC2=C1 CXUGAWWYKSOLEL-UHFFFAOYSA-N 0.000 description 1
- IYDZNYXIMLOPQV-UHFFFAOYSA-N 6-(dimethylamino)-4-oxo-1h-cinnoline-3-carboxylic acid Chemical compound N1=NC(C(O)=O)=C(O)C2=CC(N(C)C)=CC=C21 IYDZNYXIMLOPQV-UHFFFAOYSA-N 0.000 description 1
- ZLFRBIRNWOHSDM-IBGZPJMESA-N 6-O-benzyl 3-O-ethyl 1-[[(2S)-2-amino-3-methylbutanoyl]amino]-4-hydroxy-2H-cinnoline-3,6-dicarboxylate Chemical compound C=1C=C2N(NC(=O)[C@@H](N)C(C)C)NC(C(=O)OCC)=C(O)C2=CC=1C(=O)OCC1=CC=CC=C1 ZLFRBIRNWOHSDM-IBGZPJMESA-N 0.000 description 1
- IKXRGKNKZPVMKU-UHFFFAOYSA-N 6-[(4-methylphenyl)sulfonylamino]-4-oxo-1h-cinnoline-3-carboxylic acid Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=CC=C(N=NC(C(O)=O)=C2O)C2=C1 IKXRGKNKZPVMKU-UHFFFAOYSA-N 0.000 description 1
- OWUWAXNRUUBMKD-UHFFFAOYSA-N 6-nitro-4-oxo-1h-cinnoline-3-carboxylic acid Chemical compound C1=CC([N+]([O-])=O)=CC2=C(O)C(C(=O)O)=NN=C21 OWUWAXNRUUBMKD-UHFFFAOYSA-N 0.000 description 1
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 206010002198 Anaphylactic reaction Diseases 0.000 description 1
- 229930003347 Atropine Natural products 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- KUVIULQEHSCUHY-XYWKZLDCSA-N Beclometasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COC(=O)CC)(OC(=O)CC)[C@@]1(C)C[C@@H]2O KUVIULQEHSCUHY-XYWKZLDCSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 241000588832 Bordetella pertussis Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241001233242 Lontra Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 206010067482 No adverse event Diseases 0.000 description 1
- 108010058846 Ovalbumin Proteins 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 1
- 201000009961 allergic asthma Diseases 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 239000002160 alpha blocker Substances 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- PECIYKGSSMCNHN-UHFFFAOYSA-N aminophylline Chemical compound NCCN.O=C1N(C)C(=O)N(C)C2=NC=N[C]21.O=C1N(C)C(=O)N(C)C2=NC=N[C]21 PECIYKGSSMCNHN-UHFFFAOYSA-N 0.000 description 1
- 229960003556 aminophylline Drugs 0.000 description 1
- 230000036783 anaphylactic response Effects 0.000 description 1
- 208000003455 anaphylaxis Diseases 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 1
- 229960000396 atropine Drugs 0.000 description 1
- 229950000210 beclometasone dipropionate Drugs 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229960004311 betamethasone valerate Drugs 0.000 description 1
- SNHRLVCMMWUAJD-SUYDQAKGSA-N betamethasone valerate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(OC(=O)CCCC)[C@@]1(C)C[C@@H]2O SNHRLVCMMWUAJD-SUYDQAKGSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 229940124630 bronchodilator Drugs 0.000 description 1
- 239000000168 bronchodilator agent Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
- 229940082638 cardiac stimulant phosphodiesterase inhibitors Drugs 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical class N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
- BLFJCJKTSCOLEY-UHFFFAOYSA-N cinnoline-3-carboxylic acid Chemical compound C1=CC=C2N=NC(C(=O)O)=CC2=C1 BLFJCJKTSCOLEY-UHFFFAOYSA-N 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 229960001334 corticosteroids Drugs 0.000 description 1
- BADXJIPKFRBFOT-UHFFFAOYSA-N dimedone Chemical compound CC1(C)CC(=O)CC(=O)C1 BADXJIPKFRBFOT-UHFFFAOYSA-N 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- MUMAPYJYZAYOND-UHFFFAOYSA-N ethyl 4-(4-hydroxy-2-nitrophenyl)cinnoline-3-carboxylate Chemical compound CCOC(=O)C1=NN=C2C=CC=CC2=C1C1=CC=C(O)C=C1[N+]([O-])=O MUMAPYJYZAYOND-UHFFFAOYSA-N 0.000 description 1
- HLHHNSQWYUPXQL-UHFFFAOYSA-N ethyl 4-oxo-6-(2,2,2-trichloroethoxycarbonylamino)-1h-cinnoline-3-carboxylate Chemical compound C1=CC(NC(=O)OCC(Cl)(Cl)Cl)=CC2=C(O)C(C(=O)OCC)=NN=C21 HLHHNSQWYUPXQL-UHFFFAOYSA-N 0.000 description 1
- ZRXBOXOGGODVBV-UHFFFAOYSA-N ethyl 4-oxo-6-(phenylmethoxycarbonylamino)-1h-cinnoline-3-carboxylate Chemical compound C=1C2=C(O)C(C(=O)OCC)=NN=C2C=CC=1NC(=O)OCC1=CC=CC=C1 ZRXBOXOGGODVBV-UHFFFAOYSA-N 0.000 description 1
- SIWQJAKRGKXNNV-UHFFFAOYSA-N ethyl 4-oxo-6-(propan-2-ylamino)-1h-cinnoline-3-carboxylate Chemical compound C1=CC(NC(C)C)=CC2=C(O)C(C(=O)OCC)=NN=C21 SIWQJAKRGKXNNV-UHFFFAOYSA-N 0.000 description 1
- WYVUBYUDUFRAGP-UHFFFAOYSA-N ethyl 4-oxo-6-[(3,4,5-trimethoxybenzoyl)amino]-1h-cinnoline-3-carboxylate Chemical compound C=1C2=C(O)C(C(=O)OCC)=NN=C2C=CC=1NC(=O)C1=CC(OC)=C(OC)C(OC)=C1 WYVUBYUDUFRAGP-UHFFFAOYSA-N 0.000 description 1
- UYXZYYINJVDGGW-UHFFFAOYSA-N ethyl 4-oxo-6-pyridin-2-yl-1H-cinnoline-3-carboxylate Chemical compound C=1C2=C(O)C(C(=O)OCC)=NN=C2C=CC=1C1=CC=CC=N1 UYXZYYINJVDGGW-UHFFFAOYSA-N 0.000 description 1
- FOBWHFXSPXBQEJ-JOCHJYFZSA-N ethyl 5-[[(2R)-2-amino-2-(2-phenylmethoxycarbonylphenyl)acetyl]amino]-4-oxo-1H-cinnoline-3-carboxylate Chemical compound C(C1=CC=CC=C1)OC(=O)C1=CC=CC=C1[C@@H](N)C(=O)NC1=C2C(=C(N=NC2=CC=C1)C(=O)OCC)O FOBWHFXSPXBQEJ-JOCHJYFZSA-N 0.000 description 1
- VCRVVMLUEFMJDV-UHFFFAOYSA-N ethyl 6-(2-chloropyridin-3-yl)-4-oxo-1h-cinnoline-3-carboxylate Chemical compound C=1C2=C(O)C(C(=O)OCC)=NN=C2C=CC=1C1=CC=CN=C1Cl VCRVVMLUEFMJDV-UHFFFAOYSA-N 0.000 description 1
- LQDVZQBLNJEOJY-UHFFFAOYSA-N ethyl 6-(2-ethoxycarbonylphenyl)-4-oxo-1h-cinnoline-3-carboxylate Chemical compound CCOC(=O)C1=CC=CC=C1C1=CC=C(N=NC(C(=O)OCC)=C2O)C2=C1 LQDVZQBLNJEOJY-UHFFFAOYSA-N 0.000 description 1
- HLBFWXCSHLFSHT-UHFFFAOYSA-N ethyl 6-(4-methylpyridin-2-yl)-4-oxo-1h-cinnoline-3-carboxylate Chemical compound C=1C2=C(O)C(C(=O)OCC)=NN=C2C=CC=1C1=CC(C)=CC=N1 HLBFWXCSHLFSHT-UHFFFAOYSA-N 0.000 description 1
- TZOJZXZHZCVKBA-UHFFFAOYSA-N ethyl 6-(butan-2-ylamino)-4-oxo-1h-cinnoline-3-carboxylate Chemical compound C1=CC(NC(C)CC)=CC2=C(O)C(C(=O)OCC)=NN=C21 TZOJZXZHZCVKBA-UHFFFAOYSA-N 0.000 description 1
- FYIRCEUHCAISIU-UHFFFAOYSA-N ethyl 6-(butylamino)-4-oxo-1h-cinnoline-3-carboxylate Chemical compound N1=NC(C(=O)OCC)=C(O)C2=CC(NCCCC)=CC=C21 FYIRCEUHCAISIU-UHFFFAOYSA-N 0.000 description 1
- VBSKZDKKOIRLOM-UHFFFAOYSA-N ethyl 6-(cyclohexylamino)-4-oxo-1h-cinnoline-3-carboxylate Chemical compound C=1C2=C(O)C(C(=O)OCC)=NN=C2C=CC=1NC1CCCCC1 VBSKZDKKOIRLOM-UHFFFAOYSA-N 0.000 description 1
- UZHYOIAMIPXDMQ-UHFFFAOYSA-N ethyl 6-(cyclopentylamino)-4-oxo-1h-cinnoline-3-carboxylate Chemical compound C=1C2=C(O)C(C(=O)OCC)=NN=C2C=CC=1NC1CCCC1 UZHYOIAMIPXDMQ-UHFFFAOYSA-N 0.000 description 1
- OTNFTJUQJWZGKL-UHFFFAOYSA-N ethyl 6-(furan-2-yl)-4-oxo-1h-cinnoline-3-carboxylate Chemical compound C=1C2=C(O)C(C(=O)OCC)=NN=C2C=CC=1C1=CC=CO1 OTNFTJUQJWZGKL-UHFFFAOYSA-N 0.000 description 1
- XWRVJVYUKXAUCI-UHFFFAOYSA-N ethyl 6-(hexadecanoylamino)-4-oxo-1h-cinnoline-3-carboxylate Chemical compound N1=NC(C(=O)OCC)=C(O)C2=CC(NC(=O)CCCCCCCCCCCCCCC)=CC=C21 XWRVJVYUKXAUCI-UHFFFAOYSA-N 0.000 description 1
- DJFUTSGZOLFXPQ-UHFFFAOYSA-N ethyl 6-(hexanoylamino)-4-oxo-1h-cinnoline-3-carboxylate Chemical compound N1=NC(C(=O)OCC)=C(O)C2=CC(NC(=O)CCCCC)=CC=C21 DJFUTSGZOLFXPQ-UHFFFAOYSA-N 0.000 description 1
- HEBILTLUWGFVRM-UHFFFAOYSA-N ethyl 6-[(2-acetyloxybenzoyl)amino]-4-oxo-1h-cinnoline-3-carboxylate Chemical compound C=1C2=C(O)C(C(=O)OCC)=NN=C2C=CC=1NC(=O)C1=CC=CC=C1OC(C)=O HEBILTLUWGFVRM-UHFFFAOYSA-N 0.000 description 1
- BHICKWJJGJSAAQ-UHFFFAOYSA-N ethyl 6-[(4-nitrobenzoyl)amino]-4-oxo-1h-cinnoline-3-carboxylate Chemical compound C=1C2=C(O)C(C(=O)OCC)=NN=C2C=CC=1NC(=O)C1=CC=C([N+]([O-])=O)C=C1 BHICKWJJGJSAAQ-UHFFFAOYSA-N 0.000 description 1
- ONQWMZGKAJCGMF-OGFXRTJISA-N ethyl 6-[[(2R)-2-aminopropanoyl]amino]-4-oxo-1H-cinnoline-3-carboxylate hydrochloride Chemical compound Cl.C1=CC(NC(=O)[C@@H](C)N)=CC2=C(O)C(C(=O)OCC)=NN=C21 ONQWMZGKAJCGMF-OGFXRTJISA-N 0.000 description 1
- ZLMYHLJEEYNIGR-UHFFFAOYSA-N ethyl 6-acetyl-4-oxo-1h-cinnoline-3-carboxylate Chemical compound C1=CC(C(C)=O)=CC2=C(O)C(C(=O)OCC)=NN=C21 ZLMYHLJEEYNIGR-UHFFFAOYSA-N 0.000 description 1
- TTZDRZNJNDOIFI-UHFFFAOYSA-N ethyl 6-amino-4-oxo-1h-cinnoline-3-carboxylate;hydrochloride Chemical compound Cl.C1=CC(N)=CC2=C(O)C(C(=O)OCC)=NN=C21 TTZDRZNJNDOIFI-UHFFFAOYSA-N 0.000 description 1
- HIYNFFPCYDPGOA-UHFFFAOYSA-N ethyl 6-benzamido-4-oxo-1h-cinnoline-3-carboxylate Chemical compound C=1C2=C(O)C(C(=O)OCC)=NN=C2C=CC=1NC(=O)C1=CC=CC=C1 HIYNFFPCYDPGOA-UHFFFAOYSA-N 0.000 description 1
- YFRDYWWHVBMBEC-UHFFFAOYSA-N ethyl 6-ethyl-4-oxo-1h-cinnoline-3-carboxylate Chemical compound C1=CC(CC)=CC2=C(O)C(C(=O)OCC)=NN=C21 YFRDYWWHVBMBEC-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229960001317 isoprenaline Drugs 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- LMOINURANNBYCM-UHFFFAOYSA-N metaproterenol Chemical compound CC(C)NCC(O)C1=CC(O)=CC(O)=C1 LMOINURANNBYCM-UHFFFAOYSA-N 0.000 description 1
- IZDROVVXIHRYMH-UHFFFAOYSA-N methanesulfonic anhydride Chemical compound CS(=O)(=O)OS(C)(=O)=O IZDROVVXIHRYMH-UHFFFAOYSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- JOTMMIYKEOOTNZ-UHFFFAOYSA-N methyl 2-isocyanato-3-phenylpropanoate Chemical compound COC(=O)C(N=C=O)CC1=CC=CC=C1 JOTMMIYKEOOTNZ-UHFFFAOYSA-N 0.000 description 1
- QXRRTQNLNYMWKD-UHFFFAOYSA-N n-(6-methyl-8-propyl-[1,2,4]triazolo[4,3-a]pyrazin-3-yl)acetamide Chemical compound CCCC1=NC(C)=CN2C(NC(C)=O)=NN=C12 QXRRTQNLNYMWKD-UHFFFAOYSA-N 0.000 description 1
- 239000006199 nebulizer Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 229960002657 orciprenaline Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229960001999 phentolamine Drugs 0.000 description 1
- MRBDMNSDAVCSSF-UHFFFAOYSA-N phentolamine Chemical compound C1=CC(C)=CC=C1N(C=1C=C(O)C=CC=1)CC1=NCCN1 MRBDMNSDAVCSSF-UHFFFAOYSA-N 0.000 description 1
- 229940117953 phenylisothiocyanate Drugs 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 239000002571 phosphodiesterase inhibitor Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- PEEXCRJDFUVJRT-UHFFFAOYSA-M potassium;methoxymethanedithioate Chemical compound [K+].COC([S-])=S PEEXCRJDFUVJRT-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 229960002052 salbutamol Drugs 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 229940087562 sodium acetate trihydrate Drugs 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C07D237/28—Cinnolines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4820574A GB1472766A (en) | 1974-11-07 | 1974-11-07 | Hydroxycinnoline derivatives processes for their preparation and their use in pharmaceutical compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO753718L true NO753718L (da) | 1976-05-10 |
Family
ID=10447753
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO753718A NO753718L (da) | 1974-11-07 | 1975-11-06 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4045439A (da) |
| JP (1) | JPS5170778A (da) |
| BE (1) | BE835165A (da) |
| DD (1) | DD123339A5 (da) |
| DE (1) | DE2550179A1 (da) |
| DK (1) | DK500775A (da) |
| FI (1) | FI753113A (da) |
| FR (1) | FR2290209A1 (da) |
| GB (1) | GB1472766A (da) |
| IL (1) | IL48427A0 (da) |
| IN (1) | IN141110B (da) |
| NL (1) | NL7512958A (da) |
| NO (1) | NO753718L (da) |
| SE (2) | SE7512447L (da) |
| ZA (1) | ZA756710B (da) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4379929A (en) * | 1981-03-19 | 1983-04-12 | Eli Lilly And Company | 4(1H)-Oxocinnoline-3-carboxylic acid derivatives |
| GB8513639D0 (en) * | 1985-05-30 | 1985-07-03 | Ici America Inc | Cinnoline compounds |
| GB8702288D0 (en) * | 1987-02-02 | 1987-03-11 | Erba Farmitalia | Cinnoline-carboxamides |
| US5332716A (en) * | 1988-09-13 | 1994-07-26 | Jeffrey Labovitz | Pollen suppressant comprising a 5-oxy- or amino-substituted cinnoline |
| US5183891A (en) * | 1989-11-09 | 1993-02-02 | Orsan | Method for the preparation of substituted 1,4-dihydro-4-oxo-cinnoline-3-carboxylic acid, esters and salts thereof, and intermediates used in their preparation |
| GB0206876D0 (en) * | 2002-03-22 | 2002-05-01 | Merck Sharp & Dohme | Therapeutic agents |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2797218A (en) * | 1953-08-13 | 1957-06-25 | May & Baker Ltd | Cinnoline derivatives |
| IE35662B1 (en) * | 1970-10-16 | 1976-04-14 | Ici Ltd | Pharmaceutical compositions |
-
1974
- 1974-11-07 GB GB4820574A patent/GB1472766A/en not_active Expired
-
1975
- 1975-10-24 ZA ZA00756710A patent/ZA756710B/xx unknown
- 1975-10-28 IN IN2074/CAL/75A patent/IN141110B/en unknown
- 1975-10-28 US US05/626,531 patent/US4045439A/en not_active Expired - Lifetime
- 1975-10-31 BE BE161513A patent/BE835165A/xx unknown
- 1975-11-05 IL IL48427A patent/IL48427A0/xx unknown
- 1975-11-05 NL NL7512958A patent/NL7512958A/xx not_active Application Discontinuation
- 1975-11-06 NO NO753718A patent/NO753718L/no unknown
- 1975-11-06 FI FI753113A patent/FI753113A/fi not_active Application Discontinuation
- 1975-11-06 DD DD189301A patent/DD123339A5/xx unknown
- 1975-11-06 SE SE7512447A patent/SE7512447L/xx unknown
- 1975-11-06 FR FR7534004A patent/FR2290209A1/fr active Granted
- 1975-11-07 DE DE19752550179 patent/DE2550179A1/de not_active Withdrawn
- 1975-11-07 JP JP50133920A patent/JPS5170778A/ja active Pending
- 1975-11-07 DK DK500775A patent/DK500775A/da unknown
-
1978
- 1978-06-26 SE SE7807225A patent/SE7807225L/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| US4045439A (en) | 1977-08-30 |
| ZA756710B (en) | 1976-10-27 |
| GB1472766A (en) | 1977-05-04 |
| SE7512447L (sv) | 1976-05-10 |
| DK500775A (da) | 1976-05-08 |
| BE835165A (fr) | 1976-04-30 |
| FI753113A (da) | 1976-05-08 |
| DD123339A5 (da) | 1976-12-12 |
| NL7512958A (nl) | 1976-05-11 |
| AU8610175A (en) | 1977-05-05 |
| DE2550179A1 (de) | 1976-05-13 |
| FR2290209A1 (fr) | 1976-06-04 |
| IL48427A0 (en) | 1976-01-30 |
| JPS5170778A (da) | 1976-06-18 |
| SE7807225L (sv) | 1978-06-26 |
| IN141110B (da) | 1977-01-22 |
| FR2290209B1 (da) | 1978-09-22 |
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