NO852854L - Fenylkinolinderivater. - Google Patents
Fenylkinolinderivater.Info
- Publication number
- NO852854L NO852854L NO852854A NO852854A NO852854L NO 852854 L NO852854 L NO 852854L NO 852854 A NO852854 A NO 852854A NO 852854 A NO852854 A NO 852854A NO 852854 L NO852854 L NO 852854L
- Authority
- NO
- Norway
- Prior art keywords
- quinolinyl
- formula
- piperidinecarboxamide
- chloro
- chlorophenyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 70
- 238000000034 method Methods 0.000 claims description 28
- 239000007858 starting material Substances 0.000 claims description 27
- DPBWFNDFMCCGGJ-UHFFFAOYSA-N 4-Piperidine carboxamide Chemical compound NC(=O)C1CCNCC1 DPBWFNDFMCCGGJ-UHFFFAOYSA-N 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- UVJJTDAJYWUCGX-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)quinolin-4-yl]-n-methylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)NC)CCN1C1=CC(C=2C=CC(Cl)=CC=2)=NC2=CC=CC=C12 UVJJTDAJYWUCGX-UHFFFAOYSA-N 0.000 claims description 6
- LNUSDFDHJXFRAY-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)-6-fluoroquinolin-4-yl]piperidine-4-carboxamide Chemical compound C1CC(C(=O)N)CCN1C1=CC(C=2C=CC(Cl)=CC=2)=NC2=CC=C(F)C=C12 LNUSDFDHJXFRAY-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- AHPSLOYDGFMRKQ-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)quinolin-4-yl]piperidine-4-carboxamide Chemical compound C1CC(C(=O)N)CCN1C1=CC(C=2C=CC(Cl)=CC=2)=NC2=CC=CC=C12 AHPSLOYDGFMRKQ-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- URUHKHGBRNTPGA-UHFFFAOYSA-N 2-phenylquinolin-4-amine Chemical class N=1C2=CC=CC=C2C(N)=CC=1C1=CC=CC=C1 URUHKHGBRNTPGA-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 69
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 66
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 65
- 239000000203 mixture Substances 0.000 description 61
- 239000000243 solution Substances 0.000 description 52
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
- 238000002844 melting Methods 0.000 description 42
- 230000008018 melting Effects 0.000 description 42
- 239000007787 solid Substances 0.000 description 40
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 230000015572 biosynthetic process Effects 0.000 description 30
- 238000003786 synthesis reaction Methods 0.000 description 30
- 239000011541 reaction mixture Substances 0.000 description 28
- 238000001953 recrystallisation Methods 0.000 description 28
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 26
- 239000000047 product Substances 0.000 description 25
- 238000000354 decomposition reaction Methods 0.000 description 23
- 238000010992 reflux Methods 0.000 description 20
- 239000003921 oil Substances 0.000 description 18
- 235000019198 oils Nutrition 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- 239000012043 crude product Substances 0.000 description 17
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 16
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- 238000003756 stirring Methods 0.000 description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical class C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 8
- 230000008025 crystallization Effects 0.000 description 8
- 239000011630 iodine Substances 0.000 description 8
- 229910052740 iodine Inorganic materials 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 238000007790 scraping Methods 0.000 description 7
- IBKWKEIVRXSSFH-UHFFFAOYSA-N 4-chloro-2-(4-chlorophenyl)quinoline Chemical compound C1=CC(Cl)=CC=C1C1=CC(Cl)=C(C=CC=C2)C2=N1 IBKWKEIVRXSSFH-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- QAJOLLVGOSCKGP-UHFFFAOYSA-N n-methylpiperidine-4-carboxamide Chemical compound CNC(=O)C1CCNCC1 QAJOLLVGOSCKGP-UHFFFAOYSA-N 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- KNDOFJFSHZCKGT-UHFFFAOYSA-N 4-chloroquinoline Chemical compound C1=CC=C2C(Cl)=CC=NC2=C1 KNDOFJFSHZCKGT-UHFFFAOYSA-N 0.000 description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- -1 phenyllithium compound Chemical class 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- YSCGSZWWJQWHDJ-UHFFFAOYSA-N 4,6-dichloro-2-(4-fluorophenyl)quinoline Chemical compound C1=CC(F)=CC=C1C1=CC(Cl)=C(C=C(Cl)C=C2)C2=N1 YSCGSZWWJQWHDJ-UHFFFAOYSA-N 0.000 description 4
- CKTQPWIDUQGUGG-UHFFFAOYSA-N 4-chloro-6-fluoroquinoline Chemical compound N1=CC=C(Cl)C2=CC(F)=CC=C21 CKTQPWIDUQGUGG-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- GKKZMYDNDDMXSE-UHFFFAOYSA-N Ethyl 3-oxo-3-phenylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1 GKKZMYDNDDMXSE-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 230000027455 binding Effects 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000000825 pharmaceutical preparation Substances 0.000 description 4
- UNCDPJAXMITIBF-UHFFFAOYSA-N 1-(6-fluoro-2-phenylquinolin-4-yl)piperidine-4-carbonyl chloride Chemical compound C12=CC(F)=CC=C2N=C(C=2C=CC=CC=2)C=C1N1CCC(C(Cl)=O)CC1 UNCDPJAXMITIBF-UHFFFAOYSA-N 0.000 description 3
- POHAJGDSIWENJV-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)quinolin-4-yl]-n-ethylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)NCC)CCN1C1=CC(C=2C=CC(Cl)=CC=2)=NC2=CC=CC=C12 POHAJGDSIWENJV-UHFFFAOYSA-N 0.000 description 3
- ZBTMRBYMKUEVEU-UHFFFAOYSA-N 1-bromo-4-methylbenzene Chemical compound CC1=CC=C(Br)C=C1 ZBTMRBYMKUEVEU-UHFFFAOYSA-N 0.000 description 3
- DZPBPLJACVCNHN-UHFFFAOYSA-N 2-(4-bromophenyl)-4-chloroquinoline Chemical compound N=1C2=CC=CC=C2C(Cl)=CC=1C1=CC=C(Br)C=C1 DZPBPLJACVCNHN-UHFFFAOYSA-N 0.000 description 3
- NBXRIHNRLIKTTF-UHFFFAOYSA-N 2-(4-bromophenyl)quinoline-4-carbonyl chloride Chemical compound N=1C2=CC=CC=C2C(C(=O)Cl)=CC=1C1=CC=C(Br)C=C1 NBXRIHNRLIKTTF-UHFFFAOYSA-N 0.000 description 3
- KUVLLVOLQPRLGV-UHFFFAOYSA-N 4,6-dichloro-2-phenylquinoline Chemical compound C1=C(Cl)C2=CC(Cl)=CC=C2N=C1C1=CC=CC=C1 KUVLLVOLQPRLGV-UHFFFAOYSA-N 0.000 description 3
- JZGUMSTXLPEMFW-UHFFFAOYSA-N 4,6-dichloroquinoline Chemical compound N1=CC=C(Cl)C2=CC(Cl)=CC=C21 JZGUMSTXLPEMFW-UHFFFAOYSA-N 0.000 description 3
- WARKUWHKPUFQBY-UHFFFAOYSA-N 4-chloro-2-(4-chlorophenyl)-6-fluoroquinoline Chemical compound C1=C(Cl)C2=CC(F)=CC=C2N=C1C1=CC=C(Cl)C=C1 WARKUWHKPUFQBY-UHFFFAOYSA-N 0.000 description 3
- KYALELBLCRCOPK-UHFFFAOYSA-N 4-chloro-6-fluoro-2-(4-fluorophenyl)quinoline Chemical compound C1=CC(F)=CC=C1C1=CC(Cl)=C(C=C(F)C=C2)C2=N1 KYALELBLCRCOPK-UHFFFAOYSA-N 0.000 description 3
- QCRHWRDDABONAH-UHFFFAOYSA-N 4-chloro-6-fluoro-2-phenylquinoline Chemical compound C1=C(Cl)C2=CC(F)=CC=C2N=C1C1=CC=CC=C1 QCRHWRDDABONAH-UHFFFAOYSA-N 0.000 description 3
- HZWWPOQFLMUYOX-UHFFFAOYSA-N 4-chloro-6-methylquinoline Chemical compound N1=CC=C(Cl)C2=CC(C)=CC=C21 HZWWPOQFLMUYOX-UHFFFAOYSA-N 0.000 description 3
- KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 3
- QKTGFMIEELHDSD-UHFFFAOYSA-N 6-chloro-2-phenyl-1h-quinolin-4-one Chemical compound C=1C(=O)C2=CC(Cl)=CC=C2NC=1C1=CC=CC=C1 QKTGFMIEELHDSD-UHFFFAOYSA-N 0.000 description 3
- BYZXOYSEYWCLOK-UHFFFAOYSA-N 6-fluoro-1h-quinolin-4-one Chemical compound C1=C(F)C=C2C(O)=CC=NC2=C1 BYZXOYSEYWCLOK-UHFFFAOYSA-N 0.000 description 3
- 206010010904 Convulsion Diseases 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 239000012876 carrier material Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229960003529 diazepam Drugs 0.000 description 3
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 230000002140 halogenating effect Effects 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- QBERHIJABFXGRZ-UHFFFAOYSA-M rhodium;triphenylphosphane;chloride Chemical compound [Cl-].[Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QBERHIJABFXGRZ-UHFFFAOYSA-M 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- WAABQTHIJATPDW-UHFFFAOYSA-N 1-(6-chloro-2-phenylquinolin-4-yl)piperidine-4-carboxamide Chemical compound C1CC(C(=O)N)CCN1C1=CC(C=2C=CC=CC=2)=NC2=CC=C(Cl)C=C12 WAABQTHIJATPDW-UHFFFAOYSA-N 0.000 description 2
- DZVXXIPHSAMNHT-UHFFFAOYSA-N 1-(6-fluoro-2-phenylquinolin-4-yl)piperidine-4-carboxamide Chemical compound C1CC(C(=O)N)CCN1C1=CC(C=2C=CC=CC=2)=NC2=CC=C(F)C=C12 DZVXXIPHSAMNHT-UHFFFAOYSA-N 0.000 description 2
- CCRBMVWIPARRHP-UHFFFAOYSA-N 1-(6-fluoro-2-phenylquinolin-4-yl)piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1C1=CC(C=2C=CC=CC=2)=NC2=CC=C(F)C=C12 CCRBMVWIPARRHP-UHFFFAOYSA-N 0.000 description 2
- VSCSSPMOMMRWCQ-UHFFFAOYSA-N 1-(6-methyl-2-phenylquinolin-4-yl)piperidine-4-carboxamide Chemical compound C12=CC(C)=CC=C2N=C(C=2C=CC=CC=2)C=C1N1CCC(C(N)=O)CC1 VSCSSPMOMMRWCQ-UHFFFAOYSA-N 0.000 description 2
- STLWPTKJDZGQSW-UHFFFAOYSA-N 1-[2-(4-bromophenyl)quinolin-4-yl]piperidine-4-carboxamide Chemical compound C1CC(C(=O)N)CCN1C1=CC(C=2C=CC(Br)=CC=2)=NC2=CC=CC=C12 STLWPTKJDZGQSW-UHFFFAOYSA-N 0.000 description 2
- BVUSBNLAPVNEOE-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)-6-methylquinolin-4-yl]piperidine-4-carboxamide Chemical compound C12=CC(C)=CC=C2N=C(C=2C=CC(Cl)=CC=2)C=C1N1CCC(C(N)=O)CC1 BVUSBNLAPVNEOE-UHFFFAOYSA-N 0.000 description 2
- HPMIZXKAGDCTHE-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)-6-methylquinolin-4-yl]piperidine-4-carboxamide Chemical compound C12=CC(C)=CC=C2N=C(C=2C=CC(F)=CC=2)C=C1N1CCC(C(N)=O)CC1 HPMIZXKAGDCTHE-UHFFFAOYSA-N 0.000 description 2
- LRZUGFAHHQOHJI-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)quinolin-4-yl]piperidine-4-carboxamide Chemical compound C1CC(C(=O)N)CCN1C1=CC(C=2C=CC(F)=CC=2)=NC2=CC=CC=C12 LRZUGFAHHQOHJI-UHFFFAOYSA-N 0.000 description 2
- KJDXXFLKZGRBEL-UHFFFAOYSA-N 1-[6-chloro-2-(4-chlorophenyl)quinolin-4-yl]piperidine-4-carboxamide Chemical compound C1CC(C(=O)N)CCN1C1=CC(C=2C=CC(Cl)=CC=2)=NC2=CC=C(Cl)C=C12 KJDXXFLKZGRBEL-UHFFFAOYSA-N 0.000 description 2
- ZGXLGCUJWWOCJE-UHFFFAOYSA-N 1-[6-chloro-2-(4-fluorophenyl)quinolin-4-yl]piperidine-4-carboxamide Chemical compound C1CC(C(=O)N)CCN1C1=CC(C=2C=CC(F)=CC=2)=NC2=CC=C(Cl)C=C12 ZGXLGCUJWWOCJE-UHFFFAOYSA-N 0.000 description 2
- KDWBXKCTAVMBQU-UHFFFAOYSA-N 1-[6-chloro-2-(4-methylphenyl)quinolin-4-yl]piperidine-4-carboxamide Chemical compound C1=CC(C)=CC=C1C1=CC(N2CCC(CC2)C(N)=O)=C(C=C(Cl)C=C2)C2=N1 KDWBXKCTAVMBQU-UHFFFAOYSA-N 0.000 description 2
- SEQRFOYTTXBOTR-UHFFFAOYSA-N 1-[6-fluoro-2-(4-fluorophenyl)quinolin-4-yl]piperidine-4-carboxamide Chemical compound C1CC(C(=O)N)CCN1C1=CC(C=2C=CC(F)=CC=2)=NC2=CC=C(F)C=C12 SEQRFOYTTXBOTR-UHFFFAOYSA-N 0.000 description 2
- NHDODQWIKUYWMW-UHFFFAOYSA-N 1-bromo-4-chlorobenzene Chemical compound ClC1=CC=C(Br)C=C1 NHDODQWIKUYWMW-UHFFFAOYSA-N 0.000 description 2
- AITNMTXHTIIIBB-UHFFFAOYSA-N 1-bromo-4-fluorobenzene Chemical compound FC1=CC=C(Br)C=C1 AITNMTXHTIIIBB-UHFFFAOYSA-N 0.000 description 2
- JEUYPXDMAWIMOG-UHFFFAOYSA-N 2-(4-bromophenyl)quinoline-4-carboxylic acid Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(Br)C=C1 JEUYPXDMAWIMOG-UHFFFAOYSA-N 0.000 description 2
- IAUXYGDRVCGPFN-UHFFFAOYSA-N 2-(4-chlorophenyl)-6-fluoro-1h-quinolin-4-one Chemical compound N=1C2=CC=C(F)C=C2C(O)=CC=1C1=CC=C(Cl)C=C1 IAUXYGDRVCGPFN-UHFFFAOYSA-N 0.000 description 2
- PDMYABNPEHIFBP-UHFFFAOYSA-N 2-(4-fluorophenyl)quinoline-4-carbonyl chloride Chemical compound C1=CC(F)=CC=C1C1=CC(C(Cl)=O)=C(C=CC=C2)C2=N1 PDMYABNPEHIFBP-UHFFFAOYSA-N 0.000 description 2
- OSSAIQFBELCOGQ-UHFFFAOYSA-N 2-(4-fluorophenyl)quinoline-4-carboxylic acid Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(F)C=C1 OSSAIQFBELCOGQ-UHFFFAOYSA-N 0.000 description 2
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
-
- 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
- C07D215/18—Halogen atoms or nitro radicals
-
- 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
-
- 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
- C07D215/52—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4 with aryl radicals attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/631,971 US4560692A (en) | 1984-07-18 | 1984-07-18 | 4-Piperidino-2-phenylquinolines |
Publications (1)
Publication Number | Publication Date |
---|---|
NO852854L true NO852854L (no) | 1986-01-20 |
Family
ID=24533539
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO852854A NO852854L (no) | 1984-07-18 | 1985-07-17 | Fenylkinolinderivater. |
Country Status (18)
Country | Link |
---|---|
US (1) | US4560692A (fi) |
EP (1) | EP0168812A1 (fi) |
JP (1) | JPS6136283A (fi) |
KR (1) | KR860001097A (fi) |
AU (1) | AU4508085A (fi) |
CS (1) | CS252830B2 (fi) |
DK (1) | DK326085A (fi) |
ES (2) | ES8609302A1 (fi) |
FI (1) | FI852790L (fi) |
GR (1) | GR851761B (fi) |
HU (1) | HU194207B (fi) |
IL (1) | IL75825A0 (fi) |
MC (1) | MC1691A1 (fi) |
NO (1) | NO852854L (fi) |
PH (1) | PH21022A (fi) |
PT (1) | PT80824B (fi) |
ZA (1) | ZA854718B (fi) |
ZW (1) | ZW11785A1 (fi) |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3800868A1 (de) * | 1988-01-14 | 1989-07-27 | Thomae Gmbh Dr K | Mittel zur behandlung von bradycardien und bradyarrhythmien |
US5304554A (en) * | 1990-04-27 | 1994-04-19 | Emory University | 4-[(alkyl or dialkyl)amino]quinolines and their method of preparation |
AU2793199A (en) * | 1998-02-26 | 1999-09-15 | Neurogen Corporation | 2-(het-)aryl-4-(cyclic amino substituted) heteroaryl fused pyridine derivatives,their preparation and their use as (ant-)agonists for gaba (a) brain receptors |
WO1999043681A1 (en) | 1998-02-26 | 1999-09-02 | Neurogen Corporation | 4-(4-piperidylmethylamino) substituted heteroaryl fused pyridines: gaba brain receptor ligands |
US6297256B1 (en) * | 1999-06-15 | 2001-10-02 | Neurogen Corporation | Aryl and heteroaryl substituted pyridino derivatives GABA brain receptor ligands |
US6440995B1 (en) | 1999-10-01 | 2002-08-27 | Hoffman-La Roche Inc. | Quinolin-4-yl derivatives |
US6339093B1 (en) * | 1999-10-08 | 2002-01-15 | Hoffmann-La Roche Inc. | Isoquinoline derivatives |
CN100345830C (zh) | 2000-04-27 | 2007-10-31 | 安斯泰来制药有限公司 | 稠合杂芳基衍生物 |
US7825389B2 (en) | 2007-12-04 | 2010-11-02 | Tel Epion Inc. | Method and apparatus for controlling a gas cluster ion beam formed from a gas mixture |
KR20150132192A (ko) * | 2013-03-18 | 2015-11-25 | 제노사이언스 파마 | 신규한 항암제로서의 퀴놀린 유도체 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1510009A (fr) * | 1966-12-02 | 1968-01-19 | Dérivés de l'amino-4 quinoléine | |
PT66682B (pt) * | 1976-06-18 | 1978-11-15 | Ind Biolog Francaise | /(quinolyl-4)-propyl-1/-4 piperidines leur preparation et leur utilisation comme medicaments /(quinolyl-4)-propyl/-4 piperidines leur preparation et leur utilisation comme medicaments |
FR2485014A1 (fr) * | 1980-06-20 | 1981-12-24 | Pharmindustrie | Nouveaux derives de (quinolyl-2, -3 ou -4)-1 (piperidyl ou pyrrolidinyl-2 ou -3)-2 ou -3 ethanone ou propanone, procedes pour leur preparation, et leur utilisation comme medicaments |
HU190796B (en) * | 1981-06-12 | 1986-11-28 | Roussel Uclaf,Fr | Process for producing n-dihydrothiazolyl-3-quinoline-carboxamide derivatives |
-
1984
- 1984-07-18 US US06/631,971 patent/US4560692A/en not_active Expired - Fee Related
-
1985
- 1985-06-17 MC MC851783A patent/MC1691A1/xx unknown
- 1985-06-21 ZA ZA854718A patent/ZA854718B/xx unknown
- 1985-07-16 FI FI852790A patent/FI852790L/fi not_active Application Discontinuation
- 1985-07-16 IL IL75825A patent/IL75825A0/xx unknown
- 1985-07-16 PH PH32528A patent/PH21022A/en unknown
- 1985-07-16 EP EP85108885A patent/EP0168812A1/de not_active Withdrawn
- 1985-07-16 GR GR851761A patent/GR851761B/el unknown
- 1985-07-16 CS CS855274A patent/CS252830B2/cs unknown
- 1985-07-16 ZW ZW117/85A patent/ZW11785A1/xx unknown
- 1985-07-17 HU HU852742A patent/HU194207B/hu unknown
- 1985-07-17 PT PT80824A patent/PT80824B/pt unknown
- 1985-07-17 AU AU45080/85A patent/AU4508085A/en not_active Abandoned
- 1985-07-17 JP JP15617185A patent/JPS6136283A/ja active Pending
- 1985-07-17 NO NO852854A patent/NO852854L/no unknown
- 1985-07-17 DK DK326085A patent/DK326085A/da not_active Application Discontinuation
- 1985-07-17 ES ES545298A patent/ES8609302A1/es not_active Expired
- 1985-07-18 KR KR1019850005110A patent/KR860001097A/ko not_active Application Discontinuation
-
1986
- 1986-02-17 ES ES552402A patent/ES8705421A1/es not_active Expired
Also Published As
Publication number | Publication date |
---|---|
FI852790A0 (fi) | 1985-07-16 |
JPS6136283A (ja) | 1986-02-20 |
MC1691A1 (fr) | 1986-07-18 |
PT80824B (en) | 1987-05-27 |
ES8609302A1 (es) | 1986-09-01 |
ZW11785A1 (en) | 1986-02-12 |
ES8705421A1 (es) | 1987-05-01 |
DK326085A (da) | 1986-01-19 |
IL75825A0 (en) | 1985-11-29 |
HUT38333A (en) | 1986-05-28 |
KR860001097A (ko) | 1986-02-22 |
DK326085D0 (da) | 1985-07-17 |
ES545298A0 (es) | 1986-09-01 |
ES552402A0 (es) | 1987-05-01 |
FI852790L (fi) | 1986-01-19 |
AU4508085A (en) | 1986-01-23 |
HU194207B (en) | 1988-01-28 |
CS527485A2 (en) | 1987-03-12 |
PH21022A (en) | 1987-06-30 |
PT80824A (en) | 1985-08-01 |
US4560692A (en) | 1985-12-24 |
ZA854718B (en) | 1986-03-26 |
CS252830B2 (en) | 1987-10-15 |
GR851761B (fi) | 1985-11-26 |
EP0168812A1 (de) | 1986-01-22 |
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