CA1063114A - Cinnolin-3-yl carboxylic acids, ester and amides - Google Patents
Cinnolin-3-yl carboxylic acids, ester and amidesInfo
- Publication number
- CA1063114A CA1063114A CA232,341A CA232341A CA1063114A CA 1063114 A CA1063114 A CA 1063114A CA 232341 A CA232341 A CA 232341A CA 1063114 A CA1063114 A CA 1063114A
- Authority
- CA
- Canada
- Prior art keywords
- radical
- stated above
- bears
- meaning stated
- ethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- BLFJCJKTSCOLEY-UHFFFAOYSA-N cinnoline-3-carboxylic acid Chemical class C1=CC=C2N=NC(C(=O)O)=CC2=C1 BLFJCJKTSCOLEY-UHFFFAOYSA-N 0.000 title claims abstract description 6
- 150000002148 esters Chemical class 0.000 title claims abstract description 6
- 150000001408 amides Chemical class 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 62
- 238000000034 method Methods 0.000 claims abstract description 24
- -1 hydroxy, methoxy, ethoxy, 2-ethoxy-ethoxy Chemical group 0.000 claims description 87
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 86
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 31
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
- 238000010992 reflux Methods 0.000 claims description 21
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 14
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 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 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- VUXPLVKFGQNRHS-UHFFFAOYSA-N ethyl 6-chlorocinnoline-3-carboxylate Chemical compound ClC1=CC=C2N=NC(C(=O)OCC)=CC2=C1 VUXPLVKFGQNRHS-UHFFFAOYSA-N 0.000 claims description 6
- 125000004494 ethyl ester group Chemical group 0.000 claims description 6
- 150000004820 halides Chemical class 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 150000001854 cinnolines Chemical class 0.000 claims description 5
- 230000003301 hydrolyzing effect Effects 0.000 claims description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910017604 nitric acid Inorganic materials 0.000 claims description 4
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 239000001117 sulphuric acid Substances 0.000 claims description 4
- 235000011149 sulphuric acid Nutrition 0.000 claims description 4
- BKWQKVJYXODDAC-UHFFFAOYSA-N 1,2-dihydropyridazine Chemical group N1NC=CC=C1 BKWQKVJYXODDAC-UHFFFAOYSA-N 0.000 claims description 3
- 125000000872 2-diethylaminoethoxy group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims description 3
- RQPKPZSTIWQUAY-UHFFFAOYSA-N 6-chlorocinnoline-3-carboxylic acid Chemical compound ClC1=CC=C2N=NC(C(=O)O)=CC2=C1 RQPKPZSTIWQUAY-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 230000000397 acetylating effect Effects 0.000 claims description 3
- 150000008065 acid anhydrides Chemical class 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- KQSSATDQUYCRGS-UHFFFAOYSA-N methyl glycinate Chemical compound COC(=O)CN KQSSATDQUYCRGS-UHFFFAOYSA-N 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 230000000802 nitrating effect Effects 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- PHDNOFTVHXOAJB-UHFFFAOYSA-N ethyl 7-chlorocinnoline-3-carboxylate Chemical compound C1=C(Cl)C=C2N=NC(C(=O)OCC)=CC2=C1 PHDNOFTVHXOAJB-UHFFFAOYSA-N 0.000 claims description 2
- 238000006213 oxygenation reaction Methods 0.000 claims description 2
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 2
- 230000000875 corresponding effect Effects 0.000 claims 13
- 125000003118 aryl group Chemical group 0.000 claims 3
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 claims 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 2
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 2
- 239000003086 colorant Substances 0.000 claims 2
- VOLGAXAGEUPBDM-UHFFFAOYSA-N $l^{1}-oxidanylethane Chemical compound CC[O] VOLGAXAGEUPBDM-UHFFFAOYSA-N 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 claims 1
- 125000006413 ring segment Chemical group 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 6
- 238000002360 preparation method Methods 0.000 abstract description 5
- VTSSEBZBUWNJQV-UHFFFAOYSA-N ethyl 6-ethylcinnoline-3-carboxylate Chemical compound CCC1=CC=C2N=NC(C(=O)OCC)=CC2=C1 VTSSEBZBUWNJQV-UHFFFAOYSA-N 0.000 abstract description 4
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 4
- 239000000427 antigen Substances 0.000 abstract description 2
- 102000036639 antigens Human genes 0.000 abstract description 2
- 108091007433 antigens Proteins 0.000 abstract description 2
- 239000003112 inhibitor Substances 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 96
- 239000000203 mixture Substances 0.000 description 79
- 239000000243 solution Substances 0.000 description 62
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 37
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 239000007787 solid Substances 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
- 150000007942 carboxylates Chemical class 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- 239000007858 starting material Substances 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 229960000443 hydrochloric acid Drugs 0.000 description 13
- 239000000706 filtrate Substances 0.000 description 12
- 239000003208 petroleum Substances 0.000 description 11
- 230000002829 reductive effect Effects 0.000 description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- 239000012279 sodium borohydride Substances 0.000 description 8
- 229910000033 sodium borohydride Inorganic materials 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 5
- GDRKMAPTFPYCIN-UHFFFAOYSA-N 6-ethylcinnoline-3-carbonyl chloride Chemical compound N1=NC(C(Cl)=O)=CC2=CC(CC)=CC=C21 GDRKMAPTFPYCIN-UHFFFAOYSA-N 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- CFDSAJBDDOBOED-UHFFFAOYSA-N 6-bromocinnoline-3-carboxylic acid Chemical compound BrC1=CC=C2N=NC(C(=O)O)=CC2=C1 CFDSAJBDDOBOED-UHFFFAOYSA-N 0.000 description 3
- QBJULWPEGLVWGY-UHFFFAOYSA-N 6-phenylcinnoline-3-carboxylic acid Chemical compound C=1C=C2N=NC(C(=O)O)=CC2=CC=1C1=CC=CC=C1 QBJULWPEGLVWGY-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 208000006673 asthma Diseases 0.000 description 3
- 125000000259 cinnolinyl group Chemical class N1=NC(=CC2=CC=CC=C12)* 0.000 description 3
- AEZGOJOZPNPWRI-UHFFFAOYSA-N ethyl 6-nitrocinnoline-3-carboxylate Chemical compound [O-][N+](=O)C1=CC=C2N=NC(C(=O)OCC)=CC2=C1 AEZGOJOZPNPWRI-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- ZIPLRYYWAXPVMG-UHFFFAOYSA-N 4-oxo-1h-cinnoline-3-carboxylic acid Chemical compound C1=CC=C2C(=O)C(C(=O)O)=NNC2=C1 ZIPLRYYWAXPVMG-UHFFFAOYSA-N 0.000 description 2
- XKRKKKYETXBCNZ-UHFFFAOYSA-N 6-bromocinnoline-3-carbonyl chloride Chemical compound BrC1=CC=C2N=NC(C(=O)Cl)=CC2=C1 XKRKKKYETXBCNZ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 235000019759 Maize starch Nutrition 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 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
- 239000004479 aerosol dispenser Substances 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000001506 calcium phosphate Substances 0.000 description 2
- 229910000389 calcium phosphate Inorganic materials 0.000 description 2
- 235000011010 calcium phosphates Nutrition 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- TUGQSKBCJBVKRY-UHFFFAOYSA-N ethyl 6-(phenylmethoxycarbonylamino)cinnoline-3-carboxylate Chemical compound C=1C=C2N=NC(C(=O)OCC)=CC2=CC=1NC(=O)OCC1=CC=CC=C1 TUGQSKBCJBVKRY-UHFFFAOYSA-N 0.000 description 2
- HVTGTSYFNIEXKG-UHFFFAOYSA-N ethyl 6-aminocinnoline-3-carboxylate Chemical compound NC1=CC=C2N=NC(C(=O)OCC)=CC2=C1 HVTGTSYFNIEXKG-UHFFFAOYSA-N 0.000 description 2
- RPFGEDCRTBJBQQ-UHFFFAOYSA-N ethyl 6-bromocinnoline-3-carboxylate Chemical compound BrC1=CC=C2N=NC(C(=O)OCC)=CC2=C1 RPFGEDCRTBJBQQ-UHFFFAOYSA-N 0.000 description 2
- KOHOPCSEDPEAQQ-UHFFFAOYSA-N ethyl 6-ethyl-1,4-dihydrocinnoline-3-carboxylate Chemical compound C(C)C=1C=C2CC(=NNC2=CC1)C(=O)OCC KOHOPCSEDPEAQQ-UHFFFAOYSA-N 0.000 description 2
- UNCCFELLDGQGCG-UHFFFAOYSA-N ethyl 6-phenylcinnoline-3-carboxylate Chemical compound C=1C=C2N=NC(C(=O)OCC)=CC2=CC=1C1=CC=CC=C1 UNCCFELLDGQGCG-UHFFFAOYSA-N 0.000 description 2
- PNBGALCIMPLCTA-UHFFFAOYSA-N ethyl cinnoline-3-carboxylate Chemical compound C1=CC=C2N=NC(C(=O)OCC)=CC2=C1 PNBGALCIMPLCTA-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000012044 organic layer Substances 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
- 150000003230 pyrimidines Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000003756 stirring Methods 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
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 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
- 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 1
- SLINOLVLQJDNOR-UHFFFAOYSA-N 1,4-dihydrocinnoline Chemical class C1=CC=C2CC=NNC2=C1 SLINOLVLQJDNOR-UHFFFAOYSA-N 0.000 description 1
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical group CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 1
- WKNOIMDWWMTXMF-UHFFFAOYSA-N 2-(diethylamino)ethyl 6-bromocinnoline-3-carboxylate Chemical compound BrC1=CC=C2N=NC(C(=O)OCCN(CC)CC)=CC2=C1 WKNOIMDWWMTXMF-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- 229940013085 2-diethylaminoethanol Drugs 0.000 description 1
- NIVPIWAHGGDIMP-UHFFFAOYSA-N 2-ethoxyethyl 6-bromocinnoline-3-carboxylate Chemical compound BrC1=CC=C2N=NC(C(=O)OCCOCC)=CC2=C1 NIVPIWAHGGDIMP-UHFFFAOYSA-N 0.000 description 1
- PDZZMJAWWUPPDV-UHFFFAOYSA-N 6-(2,3-dinitrophenyl)cinnoline-3-carboxylic acid Chemical compound C=1C=C2N=NC(C(=O)O)=CC2=CC=1C1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O PDZZMJAWWUPPDV-UHFFFAOYSA-N 0.000 description 1
- OWMJPOIYLPPJGE-UHFFFAOYSA-N 6-bromo-4-oxo-1h-cinnoline-3-carboxylic acid Chemical compound C1=C(Br)C=C2C(=O)C(C(=O)O)=NNC2=C1 OWMJPOIYLPPJGE-UHFFFAOYSA-N 0.000 description 1
- NUILLMMTUCMJNA-UHFFFAOYSA-N 6-bromocinnoline Chemical compound N1=NC=CC2=CC(Br)=CC=C21 NUILLMMTUCMJNA-UHFFFAOYSA-N 0.000 description 1
- ATRQMCPOBZZRMQ-UHFFFAOYSA-N 6-butylcinnoline-3-carboxylic acid Chemical compound N1=NC(C(O)=O)=CC2=CC(CCCC)=CC=C21 ATRQMCPOBZZRMQ-UHFFFAOYSA-N 0.000 description 1
- HNBVGOCWUWBFBI-UHFFFAOYSA-N 6-cyclohexylcinnoline-3-carboxylic acid Chemical compound C=1C=C2N=NC(C(=O)O)=CC2=CC=1C1CCCCC1 HNBVGOCWUWBFBI-UHFFFAOYSA-N 0.000 description 1
- RGOCCBWIORWWKV-UHFFFAOYSA-N 6-ethyl-N-(2H-tetrazol-5-yl)cinnoline-3-carboxamide Chemical compound C=1C2=CC(CC)=CC=C2N=NC=1C(=O)NC1=NN=NN1 RGOCCBWIORWWKV-UHFFFAOYSA-N 0.000 description 1
- INDHWXNWRURXIG-UHFFFAOYSA-N 6-ethylcinnoline-3-carboxamide Chemical compound N1=NC(C(N)=O)=CC2=CC(CC)=CC=C21 INDHWXNWRURXIG-UHFFFAOYSA-N 0.000 description 1
- GVZLMHNNWAWJQF-UHFFFAOYSA-N 6-ethylcinnoline-3-carboxylic acid Chemical compound N1=NC(C(O)=O)=CC2=CC(CC)=CC=C21 GVZLMHNNWAWJQF-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 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
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 241000588832 Bordetella pertussis Species 0.000 description 1
- 241000905957 Channa melasoma Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 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
- 206010067482 No adverse event Diseases 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 208000024780 Urticaria Diseases 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000000674 adrenergic antagonist 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
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 201000009961 allergic asthma Diseases 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 159000000013 aluminium salts Chemical class 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
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229960003116 amyl nitrite Drugs 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 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
- SULWBFBEODFBCH-UHFFFAOYSA-N benzyl 6-bromocinnoline-3-carboxylate Chemical compound C=1C2=CC(Br)=CC=C2N=NC=1C(=O)OCC1=CC=CC=C1 SULWBFBEODFBCH-UHFFFAOYSA-N 0.000 description 1
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 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
- 230000015572 biosynthetic process 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
- 229940082638 cardiac stimulant phosphodiesterase inhibitors Drugs 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 229960001334 corticosteroids Drugs 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- FAOQUPHKGVKLME-UHFFFAOYSA-N ethyl 4-chloro-6-ethylcinnoline-3-carboxylate Chemical compound C1=CC(CC)=CC2=C(Cl)C(C(=O)OCC)=NN=C21 FAOQUPHKGVKLME-UHFFFAOYSA-N 0.000 description 1
- IPEZFVLBVZFESN-UHFFFAOYSA-N ethyl 4-chloro-6-nitrocinnoline-3-carboxylate Chemical compound C1=CC([N+]([O-])=O)=CC2=C(Cl)C(C(=O)OCC)=NN=C21 IPEZFVLBVZFESN-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
- AGSPACXVRDJSQX-UHFFFAOYSA-N ethyl 6-(2-methoxyphenyl)-1,4-dihydrocinnoline-3-carboxylate Chemical compound C1=C2CC(C(=O)OCC)=NNC2=CC=C1C1=CC=CC=C1OC AGSPACXVRDJSQX-UHFFFAOYSA-N 0.000 description 1
- DUMHQANNFFHZRO-UHFFFAOYSA-N ethyl 6-acetamidocinnoline-3-carboxylate Chemical compound CC(=O)NC1=CC=C2N=NC(C(=O)OCC)=CC2=C1 DUMHQANNFFHZRO-UHFFFAOYSA-N 0.000 description 1
- 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 1
- RVXPLDLWRBOPQX-UHFFFAOYSA-N ethyl 6-bromo-1,4-dihydrocinnoline-3-carboxylate Chemical compound BrC=1C=C2CC(=NNC2=CC1)C(=O)OCC RVXPLDLWRBOPQX-UHFFFAOYSA-N 0.000 description 1
- TZYWZKIAKPXZQY-UHFFFAOYSA-N ethyl 6-bromo-4-chlorocinnoline-3-carboxylate Chemical compound C1=CC(Br)=CC2=C(Cl)C(C(=O)OCC)=NN=C21 TZYWZKIAKPXZQY-UHFFFAOYSA-N 0.000 description 1
- YSOWMKXBIDUXBA-UHFFFAOYSA-N ethyl 6-bromo-4-oxo-1H-cinnoline-3-carboxylate Chemical compound C1=CC(Br)=CC2=C(O)C(C(=O)OCC)=NN=C21 YSOWMKXBIDUXBA-UHFFFAOYSA-N 0.000 description 1
- DCUVBDYWMKMREV-UHFFFAOYSA-N ethyl 6-butyl-1,4-dihydrocinnoline-3-carboxylate Chemical compound N1N=C(C(=O)OCC)CC2=CC(CCCC)=CC=C21 DCUVBDYWMKMREV-UHFFFAOYSA-N 0.000 description 1
- VJNVSQRAUWCRKY-UHFFFAOYSA-N ethyl 6-butylcinnoline-3-carboxylate Chemical compound N1=NC(C(=O)OCC)=CC2=CC(CCCC)=CC=C21 VJNVSQRAUWCRKY-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
- DCDZPNNKNQAVNH-UHFFFAOYSA-N ethyl 6-nitro-1,4-dihydrocinnoline-3-carboxylate Chemical compound [N+](=O)([O-])C=1C=C2CC(=NNC2=CC1)C(=O)OCC DCDZPNNKNQAVNH-UHFFFAOYSA-N 0.000 description 1
- 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 1
- KYBPERFYKILZCL-UHFFFAOYSA-N ethyl 6-propylcinnoline-3-carboxylate Chemical compound N1=NC(C(=O)OCC)=CC2=CC(CCC)=CC=C21 KYBPERFYKILZCL-UHFFFAOYSA-N 0.000 description 1
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- ATADHKWKHYVBTJ-UHFFFAOYSA-N hydron;4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol;chloride Chemical compound Cl.CNCC(O)C1=CC=C(O)C(O)=C1 ATADHKWKHYVBTJ-UHFFFAOYSA-N 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229960001317 isoprenaline Drugs 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 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
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- HCNJQACRYUZPBQ-UHFFFAOYSA-N methyl 2-[(6-ethylcinnoline-3-carbonyl)amino]acetate Chemical compound N1=NC(C(=O)NCC(=O)OC)=CC2=CC(CC)=CC=C21 HCNJQACRYUZPBQ-UHFFFAOYSA-N 0.000 description 1
- VGGSEGTTZDAXBR-UHFFFAOYSA-N methyl 6-methylcinnoline-3-carboxylate Chemical compound CC1=CC=C2N=NC(C(=O)OC)=CC2=C1 VGGSEGTTZDAXBR-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- CSDTZUBPSYWZDX-UHFFFAOYSA-N n-pentyl nitrite Chemical compound CCCCCON=O CSDTZUBPSYWZDX-UHFFFAOYSA-N 0.000 description 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
- 239000006199 nebulizer Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 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
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient 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
- GIXUBIHZIIGAMF-UHFFFAOYSA-N phenyl 6-ethylcinnoline-3-carboxylate Chemical compound C=1C2=CC(CC)=CC=C2N=NC=1C(=O)OC1=CC=CC=C1 GIXUBIHZIIGAMF-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
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- 229960002052 salbutamol Drugs 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 238000004809 thin layer chromatography Methods 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
-
- 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
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3636074A GB1474399A (en) | 1974-08-19 | 1974-08-19 | Cinnolin-3-yl carboxylic acids and derivatives thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1063114A true CA1063114A (en) | 1979-09-25 |
Family
ID=10387436
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA232,341A Expired CA1063114A (en) | 1974-08-19 | 1975-07-28 | Cinnolin-3-yl carboxylic acids, ester and amides |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US4027023A (en, 2012) |
| JP (1) | JPS5143777A (en, 2012) |
| AR (1) | AR207476A1 (en, 2012) |
| AT (1) | AT344712B (en, 2012) |
| BE (1) | BE832412A (en, 2012) |
| CA (1) | CA1063114A (en, 2012) |
| CH (1) | CH621342A5 (en, 2012) |
| CS (1) | CS192518B2 (en, 2012) |
| DD (1) | DD123338A5 (en, 2012) |
| DE (1) | DE2536913A1 (en, 2012) |
| DK (1) | DK367675A (en, 2012) |
| ES (1) | ES440327A1 (en, 2012) |
| FI (1) | FI62665C (en, 2012) |
| FR (1) | FR2282273A1 (en, 2012) |
| GB (1) | GB1474399A (en, 2012) |
| HU (1) | HU172146B (en, 2012) |
| IE (1) | IE41643B1 (en, 2012) |
| IL (1) | IL47855A (en, 2012) |
| IN (1) | IN140439B (en, 2012) |
| LU (1) | LU73210A1 (en, 2012) |
| NL (1) | NL7509692A (en, 2012) |
| NO (1) | NO146672C (en, 2012) |
| PH (1) | PH14552A (en, 2012) |
| PL (1) | PL101804B1 (en, 2012) |
| SE (1) | SE415658B (en, 2012) |
| SU (1) | SU856382A3 (en, 2012) |
| ZA (1) | ZA754979B (en, 2012) |
Families Citing this family (7)
| 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 |
| US4557934A (en) | 1983-06-21 | 1985-12-10 | The Procter & Gamble Company | Penetrating topical pharmaceutical compositions containing 1-dodecyl-azacycloheptan-2-one |
| FR2549833B1 (fr) * | 1983-07-26 | 1985-11-08 | Roussel Uclaf | Derives de la pyrazolo /4,3-c/ cinnolin-3-one, leurs sels, procede de preparation, application a titre de medicaments, compositions les renfermant et produits intermediaires |
| 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 |
| US4925844A (en) * | 1988-02-09 | 1990-05-15 | Ici Americas Inc. | Antagonizing the pharmacological effects of a benzodiazepine receptor agonist |
| KR20070116060A (ko) | 2005-03-01 | 2007-12-06 | 와이어쓰 | 신놀린 화합물 및 간 ｘ 수용체 조절제로서의 이의 용도 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH96A (de) * | 1889-01-18 | Von Derschau Albert | Vorrichtung an Handfeuerwaffen als Ersatz des Visirs, welche das Abfeuern nur dann gestattet, wenn die Waffe einen bestimmten Winkel mit der Horizontalen bildet | |
| US3657241A (en) * | 1970-03-12 | 1972-04-18 | Dow Chemical Co | Substituted cinnoline compounds |
| IE35662B1 (en) * | 1970-10-16 | 1976-04-14 | Ici Ltd | Pharmaceutical compositions |
-
1974
- 1974-08-19 GB GB3636074A patent/GB1474399A/en not_active Expired
-
1975
- 1975-01-01 AR AR260053A patent/AR207476A1/es active
- 1975-07-28 US US05/599,348 patent/US4027023A/en not_active Expired - Lifetime
- 1975-07-28 IE IE1682/75A patent/IE41643B1/en unknown
- 1975-07-28 IN IN1476/CAL/1975A patent/IN140439B/en unknown
- 1975-07-28 CA CA232,341A patent/CA1063114A/en not_active Expired
- 1975-08-01 ZA ZA00754979A patent/ZA754979B/xx unknown
- 1975-08-03 IL IL47855A patent/IL47855A/xx unknown
- 1975-08-13 DK DK367675A patent/DK367675A/da not_active Application Discontinuation
- 1975-08-13 BE BE159188A patent/BE832412A/xx not_active IP Right Cessation
- 1975-08-14 NL NL7509692A patent/NL7509692A/xx not_active Application Discontinuation
- 1975-08-15 PL PL1975182756A patent/PL101804B1/pl unknown
- 1975-08-18 NO NO752864A patent/NO146672C/no unknown
- 1975-08-18 HU HU75IE00000708A patent/HU172146B/hu unknown
- 1975-08-18 CS CS755649A patent/CS192518B2/cs unknown
- 1975-08-18 FI FI752332A patent/FI62665C/fi not_active IP Right Cessation
- 1975-08-18 SE SE7509209A patent/SE415658B/xx unknown
- 1975-08-18 LU LU73210A patent/LU73210A1/xx unknown
- 1975-08-18 CH CH1073075A patent/CH621342A5/de not_active IP Right Cessation
- 1975-08-18 SU SU752164732A patent/SU856382A3/ru active
- 1975-08-18 DD DD187917A patent/DD123338A5/xx unknown
- 1975-08-18 FR FR7525529A patent/FR2282273A1/fr active Granted
- 1975-08-18 AT AT638275A patent/AT344712B/de not_active IP Right Cessation
- 1975-08-19 JP JP50100571A patent/JPS5143777A/ja active Pending
- 1975-08-19 DE DE19752536913 patent/DE2536913A1/de not_active Ceased
- 1975-08-19 ES ES440327A patent/ES440327A1/es not_active Expired
- 1975-08-30 PH PH17481A patent/PH14552A/en unknown
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