NO854275L - Fremgangsmaate for fremstilling av benzenkondenserte heterocykliske forbindelser. - Google Patents
Fremgangsmaate for fremstilling av benzenkondenserte heterocykliske forbindelser.Info
- Publication number
- NO854275L NO854275L NO854275A NO854275A NO854275L NO 854275 L NO854275 L NO 854275L NO 854275 A NO854275 A NO 854275A NO 854275 A NO854275 A NO 854275A NO 854275 L NO854275 L NO 854275L
- Authority
- NO
- Norway
- Prior art keywords
- general formula
- ppm
- propionyl
- chloro
- dihydro
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 34
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 title description 41
- 150000002391 heterocyclic compounds Chemical class 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 106
- 125000000217 alkyl group Chemical group 0.000 claims description 60
- 150000003839 salts Chemical class 0.000 claims description 57
- -1 nitro, amino, hydroxy Chemical group 0.000 claims description 50
- 238000002360 preparation method Methods 0.000 claims description 38
- 238000006243 chemical reaction Methods 0.000 claims description 33
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 27
- 125000002252 acyl group Chemical group 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical group 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000001589 carboacyl group Chemical group 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 125000004442 acylamino group Chemical group 0.000 claims description 7
- BGBLDOPZRATPKR-UHFFFAOYSA-N 1-(8-chloro-1-methyl-4h-pyrazolo[4,3-c]quinolin-5-yl)propan-1-one Chemical compound C12=CC(Cl)=CC=C2N(C(=O)CC)CC2=C1N(C)N=C2 BGBLDOPZRATPKR-UHFFFAOYSA-N 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- SVVSUQPPINJGPF-UHFFFAOYSA-N 1-(8-chloro-1,4-dihydropyrazolo[4,3-c]quinolin-5-yl)propan-1-one Chemical compound C12=CC(Cl)=CC=C2N(C(=O)CC)CC2=C1NN=C2 SVVSUQPPINJGPF-UHFFFAOYSA-N 0.000 claims description 4
- UJGFYQFQTLZJRY-UHFFFAOYSA-N 1-(8-chloro-1-propan-2-yl-4h-pyrazolo[4,3-c]quinolin-5-yl)propan-1-one Chemical compound C12=CC(Cl)=CC=C2N(C(=O)CC)CC2=C1N(C(C)C)N=C2 UJGFYQFQTLZJRY-UHFFFAOYSA-N 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- FIMNMHQCRMREPP-UHFFFAOYSA-N 8-chloro-1-methyl-4,5-dihydropyrazolo[4,3-c]quinoline Chemical compound C1NC2=CC=C(Cl)C=C2C2=C1C=NN2C FIMNMHQCRMREPP-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 2
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 125000004996 haloaryloxy group Chemical group 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- 125000001419 myristoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 10
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 1
- 125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 183
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 170
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 138
- 238000002329 infrared spectrum Methods 0.000 description 104
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 93
- 239000000203 mixture Substances 0.000 description 87
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 76
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 67
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 60
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 54
- 238000002844 melting Methods 0.000 description 54
- 230000008018 melting Effects 0.000 description 54
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- 238000004519 manufacturing process Methods 0.000 description 29
- 239000000243 solution Substances 0.000 description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- 239000002904 solvent Substances 0.000 description 23
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 22
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 16
- 235000019341 magnesium sulphate Nutrition 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- 238000003756 stirring Methods 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 238000001816 cooling Methods 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 238000001914 filtration Methods 0.000 description 10
- 239000000843 powder Substances 0.000 description 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
- 235000017557 sodium bicarbonate Nutrition 0.000 description 9
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- 230000002411 adverse Effects 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- KIUJNBDISNDSBG-UHFFFAOYSA-N 6-hydroxy-1-propanoyl-2,3-dihydroquinolin-4-one Chemical compound OC1=CC=C2N(C(=O)CC)CCC(=O)C2=C1 KIUJNBDISNDSBG-UHFFFAOYSA-N 0.000 description 5
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 150000007529 inorganic bases Chemical class 0.000 description 4
- 150000007530 organic bases Chemical class 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 235000019698 starch Nutrition 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
- FVTFXDXNAXPSGW-UHFFFAOYSA-N (8-chloro-1-methyl-4h-pyrazolo[4,3-c]quinolin-5-yl)-cyclopropylmethanone Chemical compound C12=CC=C(Cl)C=C2C=2N(C)N=CC=2CN1C(=O)C1CC1 FVTFXDXNAXPSGW-UHFFFAOYSA-N 0.000 description 3
- GDWQHPUBTAKQSL-UHFFFAOYSA-N 1-(8-chloro-1-ethyl-4h-pyrazolo[4,3-c]quinolin-5-yl)propan-1-one Chemical compound C12=CC(Cl)=CC=C2N(C(=O)CC)CC2=C1N(CC)N=C2 GDWQHPUBTAKQSL-UHFFFAOYSA-N 0.000 description 3
- AUCLDWOKKSRFCQ-UHFFFAOYSA-N 1-(8-chloro-1-methyl-4h-pyrazolo[4,3-c]quinolin-5-yl)-3-methoxypropan-1-one Chemical compound C12=CC(Cl)=CC=C2N(C(=O)CCOC)CC2=C1N(C)N=C2 AUCLDWOKKSRFCQ-UHFFFAOYSA-N 0.000 description 3
- XNMHEKPWFOTROX-UHFFFAOYSA-N 1-(8-nitro-1,4-dihydropyrazolo[4,3-c]quinolin-5-yl)propan-1-one Chemical compound C12=CC([N+]([O-])=O)=CC=C2N(C(=O)CC)CC2=C1NN=C2 XNMHEKPWFOTROX-UHFFFAOYSA-N 0.000 description 3
- WCOPGYLVFHWCDI-UHFFFAOYSA-N 1-[8-chloro-1-[2-(dimethylamino)ethyl]-4h-pyrazolo[4,3-c]quinolin-5-yl]propan-1-one Chemical compound C12=CC(Cl)=CC=C2N(C(=O)CC)CC2=C1N(CCN(C)C)N=C2 WCOPGYLVFHWCDI-UHFFFAOYSA-N 0.000 description 3
- ZKWZWCZIEOGNPY-UHFFFAOYSA-N 3-(dimethylaminomethylidene)-6-nitro-1-propanoyl-2h-quinolin-4-one Chemical compound [O-][N+](=O)C1=CC=C2N(C(=O)CC)CC(=CN(C)C)C(=O)C2=C1 ZKWZWCZIEOGNPY-UHFFFAOYSA-N 0.000 description 3
- WLCSJSHAEPIYEG-UHFFFAOYSA-N 6-amino-1-propanoyl-2,3-dihydroquinolin-4-one Chemical compound NC1=CC=C2N(C(=O)CC)CCC(=O)C2=C1 WLCSJSHAEPIYEG-UHFFFAOYSA-N 0.000 description 3
- WWWUZHMBWBLZBU-UHFFFAOYSA-N 6-chloro-3-(dimethylaminomethylidene)-1-propanoyl-2h-quinolin-4-one Chemical compound ClC1=CC=C2N(C(=O)CC)CC(=CN(C)C)C(=O)C2=C1 WWWUZHMBWBLZBU-UHFFFAOYSA-N 0.000 description 3
- JCCGUZOJHMHZKT-UHFFFAOYSA-N 6-chloro-3-(dimethylaminomethylidene)chromen-4-one Chemical compound C1=C(Cl)C=C2C(=O)C(=CN(C)C)COC2=C1 JCCGUZOJHMHZKT-UHFFFAOYSA-N 0.000 description 3
- SYTCSBYKAVQCBD-UHFFFAOYSA-N 6-nitro-1-propanoyl-2,3-dihydroquinolin-4-one Chemical compound [O-][N+](=O)C1=CC=C2N(C(=O)CC)CCC(=O)C2=C1 SYTCSBYKAVQCBD-UHFFFAOYSA-N 0.000 description 3
- UGCLOPVGZUUXQV-UHFFFAOYSA-N 8-chloro-1-methyl-4h-pyrazolo[4,3-c]quinoline-5-carbaldehyde Chemical compound C1N(C=O)C2=CC=C(Cl)C=C2C2=C1C=NN2C UGCLOPVGZUUXQV-UHFFFAOYSA-N 0.000 description 3
- ATFWUTFABQDBSW-UHFFFAOYSA-N 8-chloro-n-ethyl-1-methyl-4h-pyrazolo[4,3-c]quinoline-5-carboxamide Chemical compound C12=CC(Cl)=CC=C2N(C(=O)NCC)CC2=C1N(C)N=C2 ATFWUTFABQDBSW-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- AKURYHRMXAKKTO-UHFFFAOYSA-N ethyl 2-(8-chloro-5-propanoyl-4h-pyrazolo[4,3-c]quinolin-2-yl)acetate Chemical compound C1=C(Cl)C=C2C3=NN(CC(=O)OCC)C=C3CN(C(=O)CC)C2=C1 AKURYHRMXAKKTO-UHFFFAOYSA-N 0.000 description 3
- WLSLINAFUZZHBE-UHFFFAOYSA-N ethyl 8-chloro-1-methyl-4h-pyrazolo[4,3-c]quinoline-5-carboxylate Chemical compound C12=CC(Cl)=CC=C2N(C(=O)OCC)CC2=C1N(C)N=C2 WLSLINAFUZZHBE-UHFFFAOYSA-N 0.000 description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- AGIVZFHUBSGUDD-UHFFFAOYSA-N methyl 2-[(5-propanoyl-1,4-dihydropyrazolo[4,3-c]quinolin-8-yl)oxy]acetate Chemical compound C12=CC(OCC(=O)OC)=CC=C2N(C(=O)CC)CC2=C1NN=C2 AGIVZFHUBSGUDD-UHFFFAOYSA-N 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 210000002700 urine Anatomy 0.000 description 3
- FWHXGEUIBDIHPA-UHFFFAOYSA-N (8-chloro-1,4-dihydropyrazolo[4,3-c]quinolin-5-yl)-cyclopropylmethanone Chemical compound C1C=2C=NNC=2C2=CC(Cl)=CC=C2N1C(=O)C1CC1 FWHXGEUIBDIHPA-UHFFFAOYSA-N 0.000 description 2
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 2
- RQUOCMJFHXRRLD-UHFFFAOYSA-N 1-(1,4-dihydropyrazolo[4,3-c]quinolin-5-yl)propan-1-one Chemical compound C12=CC=CC=C2N(C(=O)CC)CC2=C1NN=C2 RQUOCMJFHXRRLD-UHFFFAOYSA-N 0.000 description 2
- NDNMZBAAXKNAJF-UHFFFAOYSA-N 1-(1-methyl-8-nitro-4h-pyrazolo[4,3-c]quinolin-5-yl)propan-1-one Chemical compound C12=CC([N+]([O-])=O)=CC=C2N(C(=O)CC)CC2=C1N(C)N=C2 NDNMZBAAXKNAJF-UHFFFAOYSA-N 0.000 description 2
- MHBWSAAEDHUYIW-UHFFFAOYSA-N 1-(2-benzyl-8-chloro-4h-pyrazolo[4,3-c]quinolin-5-yl)propan-1-one Chemical compound N1=C2C3=CC(Cl)=CC=C3N(C(=O)CC)CC2=CN1CC1=CC=CC=C1 MHBWSAAEDHUYIW-UHFFFAOYSA-N 0.000 description 2
- YAUPJVDSLKIPOP-UHFFFAOYSA-N 1-(2-but-2-ynyl-8-chloro-4h-pyrazolo[4,3-c]quinolin-5-yl)propan-1-one Chemical compound ClC1=CC=C2N(C(=O)CC)CC3=CN(CC#CC)N=C3C2=C1 YAUPJVDSLKIPOP-UHFFFAOYSA-N 0.000 description 2
- YDACANOYIDPQTO-UHFFFAOYSA-N 1-(7,8-dichloro-1,4-dihydropyrazolo[4,3-c]quinolin-5-yl)propan-1-one Chemical compound C12=CC(Cl)=C(Cl)C=C2N(C(=O)CC)CC2=C1NN=C2 YDACANOYIDPQTO-UHFFFAOYSA-N 0.000 description 2
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- TVQFKEMGHNXQLE-UHFFFAOYSA-N 1-(8-chloro-1,4-dihydropyrazolo[4,3-c]quinolin-5-yl)-2,3-dimethylpentan-1-one Chemical compound C12=CC(Cl)=CC=C2N(C(=O)C(C)C(C)CC)CC2=C1NN=C2 TVQFKEMGHNXQLE-UHFFFAOYSA-N 0.000 description 2
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- 239000000314 lubricant Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- CRGZYKWWYNQGEC-UHFFFAOYSA-N magnesium;methanolate Chemical compound [Mg+2].[O-]C.[O-]C CRGZYKWWYNQGEC-UHFFFAOYSA-N 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- KGOPFYBOHSRENV-UHFFFAOYSA-N methyl 2-[(5-chloro-4-oxo-1-propanoyl-2,3-dihydroquinolin-6-yl)oxy]acetate Chemical compound COC(=O)COC1=CC=C2N(C(=O)CC)CCC(=O)C2=C1Cl KGOPFYBOHSRENV-UHFFFAOYSA-N 0.000 description 1
- PBKQRTGCQLKRDL-UHFFFAOYSA-N methyl 2-[[3-(dimethylaminomethylidene)-4-oxo-1-propanoyl-2h-quinolin-6-yl]oxy]acetate Chemical compound COC(=O)COC1=CC=C2N(C(=O)CC)CC(=CN(C)C)C(=O)C2=C1 PBKQRTGCQLKRDL-UHFFFAOYSA-N 0.000 description 1
- DCORIHZOUBTQLS-UHFFFAOYSA-N methyl 2-[[5-chloro-3-(dimethylaminomethylidene)-4-oxo-1-propanoyl-2h-quinolin-6-yl]oxy]acetate Chemical compound COC(=O)COC1=CC=C2N(C(=O)CC)CC(=CN(C)C)C(=O)C2=C1Cl DCORIHZOUBTQLS-UHFFFAOYSA-N 0.000 description 1
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- AMNJSHBFSVFIPJ-UHFFFAOYSA-N n-(4-oxo-1-propanoyl-2,3-dihydroquinolin-6-yl)acetamide Chemical compound CC(=O)NC1=CC=C2N(C(=O)CC)CCC(=O)C2=C1 AMNJSHBFSVFIPJ-UHFFFAOYSA-N 0.000 description 1
- OJZUGRVTDBCBQE-UHFFFAOYSA-N n-[3-(dimethylaminomethylidene)-4-oxo-1-propanoyl-2h-quinolin-6-yl]-n-methylmethanesulfonamide Chemical compound CS(=O)(=O)N(C)C1=CC=C2N(C(=O)CC)CC(=CN(C)C)C(=O)C2=C1 OJZUGRVTDBCBQE-UHFFFAOYSA-N 0.000 description 1
- XOUCFIWRNVVVSQ-UHFFFAOYSA-N n-[3-(dimethylaminomethylidene)-4-oxo-1-propanoyl-2h-quinolin-6-yl]acetamide Chemical compound CC(=O)NC1=CC=C2N(C(=O)CC)CC(=CN(C)C)C(=O)C2=C1 XOUCFIWRNVVVSQ-UHFFFAOYSA-N 0.000 description 1
- KBHFZUUDVJGRKK-UHFFFAOYSA-N n-methylsulfonyl-n-(4-oxo-1-propanoyl-2,3-dihydroquinolin-6-yl)methanesulfonamide Chemical compound CS(=O)(=O)N(S(C)(=O)=O)C1=CC=C2N(C(=O)CC)CCC(=O)C2=C1 KBHFZUUDVJGRKK-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 229960003885 sodium benzoate Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- IHMQNZFRFVYNDS-UHFFFAOYSA-N tert-butyl n-amino-n-methylcarbamate Chemical compound CN(N)C(=O)OC(C)(C)C IHMQNZFRFVYNDS-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 235000013337 tricalcium citrate Nutrition 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 239000003383 uricosuric agent Substances 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003871 white petrolatum Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- 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
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
-
- 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
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/42—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4
- C07D311/56—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 without hydrogen atoms in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/052—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being six-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pyridine Compounds (AREA)
- Quinoline Compounds (AREA)
- Pyrane Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB848427124A GB8427124D0 (en) | 1984-10-26 | 1984-10-26 | Benzene-fused heterocyclic compound |
| GB858513399A GB8513399D0 (en) | 1985-05-28 | 1985-05-28 | Heterocyclic compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO854275L true NO854275L (no) | 1986-04-28 |
Family
ID=26288380
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO854275A NO854275L (no) | 1984-10-26 | 1985-10-25 | Fremgangsmaate for fremstilling av benzenkondenserte heterocykliske forbindelser. |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US4675324A (ja) |
| EP (1) | EP0180352B1 (ja) |
| JP (1) | JPH0649702B2 (ja) |
| KR (1) | KR860003259A (ja) |
| CN (1) | CN85108618A (ja) |
| AT (1) | ATE89825T1 (ja) |
| AU (1) | AU4855185A (ja) |
| DE (1) | DE3587362T2 (ja) |
| DK (1) | DK493185A (ja) |
| ES (2) | ES8702139A1 (ja) |
| FI (1) | FI853757L (ja) |
| GR (1) | GR852593B (ja) |
| HU (1) | HUT40124A (ja) |
| NO (1) | NO854275L (ja) |
| PH (1) | PH21213A (ja) |
| SU (1) | SU1375137A3 (ja) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4839368A (en) * | 1986-05-02 | 1989-06-13 | Mochida Pharmaceutical Co., Ltd. | 1-acyl-2,3-dihydro-4(1H)-quinolinone-4-oxime derivatives |
| US4816467A (en) * | 1987-01-09 | 1989-03-28 | Farmitalia Carlo Erba S.R.L | Heteroaryl 3-oxo-propanenitrile derivatives, pharmaceutical compositions and use |
| ES2061644T3 (es) * | 1987-04-09 | 1994-12-16 | Du Pont | Indazoles sustituidos insecticidas. |
| JP2602037B2 (ja) * | 1987-10-31 | 1997-04-23 | 持田製薬株式会社 | １−アシル−２，３−ジヒドロ−４（１ｈ）−キノリノン−４−オキシム誘導体、その製法およびそれらを主成分とする利尿、降圧、抗浮腫および腹水除去用医薬組成物 |
| US5192768A (en) * | 1990-09-14 | 1993-03-09 | Kyowa Hakko Kogyo Co., Ltd. | Pyrazoloquinoline derivatives |
| CN100384825C (zh) | 1994-06-15 | 2008-04-30 | 大塚制药株式会社 | 苯并杂环衍生物 |
| US5865170A (en) * | 1997-07-23 | 1999-02-02 | Moles; Randall C. | Customizable mouthpiece for scuba-divers |
| US7081456B2 (en) * | 2002-11-22 | 2006-07-25 | Active Biotech Ab | Immunomodulatory compounds |
| EP1667643A4 (en) * | 2003-08-28 | 2008-03-05 | Nitromed Inc | NITROSIS AND NITROSYL CARDIOVASCULAR COMPOUNDS, COMPOSITIONS AND METHODS OF USE THEREOF |
| EP1855688A4 (en) * | 2005-02-24 | 2011-09-14 | Nicox Sa | NON-STAINED OXIDE DIURETIC COMPOUNDS, COMPOSITIONS AND USE PROCESSES |
| RU2485114C2 (ru) | 2006-12-29 | 2013-06-20 | Эбботт Гмбх Унд Ко.Кг | Карбоксамидные соединения и их применение в качестве ингибиторов кальпаинов |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2009079A1 (ja) * | 1968-05-22 | 1970-01-30 | Sandoz Sa | |
| US3624102A (en) * | 1969-05-21 | 1971-11-30 | Warner Lambert Co | Substituted benzopyranopyrazoles |
| CY1357A (en) * | 1979-06-21 | 1987-08-07 | Ciba Geigy Ag | Pyrazolo-quinolines, processes for their production, pharmaceutical compositions containing them and their therapeutical use |
| US4524146A (en) * | 1982-12-08 | 1985-06-18 | Ciba-Geigy Corporation | Certain -2-heterocycle substituted pyrazoloquinolines |
-
1985
- 1985-09-24 PH PH32840A patent/PH21213A/en unknown
- 1985-09-26 US US06/780,582 patent/US4675324A/en not_active Expired - Fee Related
- 1985-09-30 FI FI853757A patent/FI853757L/fi not_active Application Discontinuation
- 1985-10-08 AT AT85307200T patent/ATE89825T1/de not_active IP Right Cessation
- 1985-10-08 EP EP85307200A patent/EP0180352B1/en not_active Expired - Lifetime
- 1985-10-08 DE DE8585307200T patent/DE3587362T2/de not_active Expired - Fee Related
- 1985-10-14 AU AU48551/85A patent/AU4855185A/en not_active Abandoned
- 1985-10-23 KR KR1019850007824A patent/KR860003259A/ko not_active Application Discontinuation
- 1985-10-24 JP JP60239205A patent/JPH0649702B2/ja not_active Expired - Lifetime
- 1985-10-25 CN CN198585108618A patent/CN85108618A/zh active Pending
- 1985-10-25 SU SU853967801A patent/SU1375137A3/ru active
- 1985-10-25 ES ES548205A patent/ES8702139A1/es not_active Expired
- 1985-10-25 NO NO854275A patent/NO854275L/no unknown
- 1985-10-25 HU HU854120A patent/HUT40124A/hu unknown
- 1985-10-25 DK DK493185A patent/DK493185A/da not_active Application Discontinuation
- 1985-10-29 GR GR852593A patent/GR852593B/el unknown
-
1986
- 1986-09-01 ES ES557041A patent/ES8801266A1/es not_active Expired
-
1987
- 1987-04-24 US US07/042,299 patent/US4767780A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DK493185A (da) | 1986-04-27 |
| CN85108618A (zh) | 1986-08-27 |
| EP0180352A3 (en) | 1988-03-30 |
| US4675324A (en) | 1987-06-23 |
| EP0180352B1 (en) | 1993-05-26 |
| ES8702139A1 (es) | 1986-12-16 |
| US4767780A (en) | 1988-08-30 |
| FI853757L (fi) | 1986-04-27 |
| SU1375137A3 (ru) | 1988-02-15 |
| DE3587362T2 (de) | 1993-09-09 |
| ATE89825T1 (de) | 1993-06-15 |
| ES548205A0 (es) | 1986-12-16 |
| FI853757A0 (fi) | 1985-09-30 |
| ES557041A0 (es) | 1987-12-16 |
| DE3587362D1 (de) | 1993-07-01 |
| KR860003259A (ko) | 1986-05-21 |
| ES8801266A1 (es) | 1987-12-16 |
| AU4855185A (en) | 1986-05-01 |
| HUT40124A (en) | 1986-11-28 |
| GR852593B (ja) | 1985-12-24 |
| JPH0649702B2 (ja) | 1994-06-29 |
| DK493185D0 (da) | 1985-10-25 |
| JPS61112076A (ja) | 1986-05-30 |
| PH21213A (en) | 1987-08-21 |
| EP0180352A2 (en) | 1986-05-07 |
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