NO834798L - Medikamenter paa basis av derivater av naftalen- eller aza-naftalencarboxamid, nye slike derivater og deres fremstilling - Google Patents
Medikamenter paa basis av derivater av naftalen- eller aza-naftalencarboxamid, nye slike derivater og deres fremstillingInfo
- Publication number
- NO834798L NO834798L NO834798A NO834798A NO834798L NO 834798 L NO834798 L NO 834798L NO 834798 A NO834798 A NO 834798A NO 834798 A NO834798 A NO 834798A NO 834798 L NO834798 L NO 834798L
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- carbon atoms
- alkyl
- formula
- nitrogen atom
- Prior art date
Links
- 239000003814 drug Substances 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 51
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 44
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 40
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 30
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 24
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 13
- 125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 13
- 125000001424 substituent group Chemical group 0.000 claims abstract description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 6
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 3
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 61
- -1 2-thiazolyl Chemical group 0.000 claims description 54
- 238000000034 method Methods 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 17
- 150000001412 amines Chemical class 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 239000013543 active substance Substances 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 238000006264 debenzylation reaction Methods 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 229940079593 drug Drugs 0.000 claims description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 239000001301 oxygen Chemical group 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 abstract description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 abstract 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
- 208000024172 Cardiovascular disease Diseases 0.000 abstract 1
- 230000002685 pulmonary effect Effects 0.000 abstract 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 108
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 76
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 61
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 54
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 50
- 239000000243 solution Substances 0.000 description 50
- 238000001953 recrystallisation Methods 0.000 description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 44
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
- 239000000155 melt Substances 0.000 description 43
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 34
- 239000012074 organic phase Substances 0.000 description 32
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 29
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 27
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 23
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 22
- 235000019341 magnesium sulphate Nutrition 0.000 description 22
- 238000002844 melting Methods 0.000 description 22
- 230000008018 melting Effects 0.000 description 22
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 19
- LEWDKQKVAFOMPI-UHFFFAOYSA-N quinoline-4-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=CC=NC2=C1 LEWDKQKVAFOMPI-UHFFFAOYSA-N 0.000 description 19
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 18
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 18
- AOLMGSAMTRTYEX-UHFFFAOYSA-N 2-phenylquinoline-4-carboxamide Chemical compound N=1C2=CC=CC=C2C(C(=O)N)=CC=1C1=CC=CC=C1 AOLMGSAMTRTYEX-UHFFFAOYSA-N 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 239000003480 eluent Substances 0.000 description 17
- 239000000741 silica gel Substances 0.000 description 17
- 229910002027 silica gel Inorganic materials 0.000 description 17
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 238000010992 reflux Methods 0.000 description 14
- 238000003756 stirring Methods 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- QBRGQUCIJZKQAY-UHFFFAOYSA-N 2-(2-chlorophenyl)quinoline-4-carboxylic acid Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=CC=C1Cl QBRGQUCIJZKQAY-UHFFFAOYSA-N 0.000 description 10
- 229960000583 acetic acid Drugs 0.000 description 10
- 229960003529 diazepam Drugs 0.000 description 10
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 9
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
- 239000008346 aqueous phase Substances 0.000 description 9
- 238000004587 chromatography analysis Methods 0.000 description 8
- 238000004821 distillation Methods 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 7
- 230000002093 peripheral effect Effects 0.000 description 7
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 229940049706 benzodiazepine Drugs 0.000 description 6
- 150000001557 benzodiazepines Chemical class 0.000 description 6
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 6
- 239000012442 inert solvent Substances 0.000 description 6
- 210000003734 kidney Anatomy 0.000 description 6
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 5
- YTRMTPPVNRALON-UHFFFAOYSA-N 2-phenyl-4-quinolinecarboxylic acid Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=CC=C1 YTRMTPPVNRALON-UHFFFAOYSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 210000004556 brain Anatomy 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- VQMSRUREDGBWKT-UHFFFAOYSA-N quinoline-4-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=NC2=C1 VQMSRUREDGBWKT-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- PYFSCIWXNSXGNS-RXMQYKEDSA-N (2r)-n-methylbutan-2-amine Chemical compound CC[C@@H](C)NC PYFSCIWXNSXGNS-RXMQYKEDSA-N 0.000 description 4
- MOMFXATYAINJML-UHFFFAOYSA-N 2-Acetylthiazole Chemical compound CC(=O)C1=NC=CS1 MOMFXATYAINJML-UHFFFAOYSA-N 0.000 description 4
- WSYCFYURDIXHNT-UHFFFAOYSA-N 2-pyridin-2-ylquinoline-4-carboxylic acid Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=CC=N1 WSYCFYURDIXHNT-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- PYFSCIWXNSXGNS-UHFFFAOYSA-N N-methyl-sec-butylamine Natural products CCC(C)NC PYFSCIWXNSXGNS-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000012280 lithium aluminium hydride Substances 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- ODWRVCWITIGQHX-UHFFFAOYSA-N 3-phenylnaphthalene-1-carboxylic acid Chemical compound C=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=CC=C1 ODWRVCWITIGQHX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 210000004072 lung Anatomy 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- VUNPWIPIOOMCPT-UHFFFAOYSA-N piperidin-3-ylmethanol Chemical compound OCC1CCCNC1 VUNPWIPIOOMCPT-UHFFFAOYSA-N 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- FGVFTSURYOVMBK-UHFFFAOYSA-N (2-methylpiperidin-1-yl)-(2-phenylquinazolin-4-yl)methanone Chemical compound CC1CCCCN1C(=O)C1=NC(C=2C=CC=CC=2)=NC2=CC=CC=C12 FGVFTSURYOVMBK-UHFFFAOYSA-N 0.000 description 2
- VIDAJEMIAUAFJB-UHFFFAOYSA-N (2-phenylquinazolin-4-yl)-piperidin-1-ylmethanone Chemical compound N=1C(C=2C=CC=CC=2)=NC2=CC=CC=C2C=1C(=O)N1CCCCC1 VIDAJEMIAUAFJB-UHFFFAOYSA-N 0.000 description 2
- WYVMYUWFJJNHAC-UHFFFAOYSA-N (2-phenylquinazolin-4-yl)-pyrrolidin-1-ylmethanone Chemical compound N=1C(C=2C=CC=CC=2)=NC2=CC=CC=C2C=1C(=O)N1CCCC1 WYVMYUWFJJNHAC-UHFFFAOYSA-N 0.000 description 2
- PUMOKWJXDTVVGM-UHFFFAOYSA-N (3-methylpiperidin-1-yl)-(2-phenylquinazolin-4-yl)methanone Chemical compound C1C(C)CCCN1C(=O)C1=NC(C=2C=CC=CC=2)=NC2=CC=CC=C12 PUMOKWJXDTVVGM-UHFFFAOYSA-N 0.000 description 2
- FCAYQHMQCUZOLO-UHFFFAOYSA-N (4-methylpiperidin-1-yl)-(2-phenylquinazolin-4-yl)methanone Chemical compound C1CC(C)CCN1C(=O)C1=NC(C=2C=CC=CC=2)=NC2=CC=CC=C12 FCAYQHMQCUZOLO-UHFFFAOYSA-N 0.000 description 2
- VOSJUAMYFWNMMP-UHFFFAOYSA-N 1-(1-benzylpiperidin-4-yl)-n-ethylethanamine Chemical compound C1CC(C(C)NCC)CCN1CC1=CC=CC=C1 VOSJUAMYFWNMMP-UHFFFAOYSA-N 0.000 description 2
- OOPXZFAKCHHQQT-UHFFFAOYSA-N 1-(1-benzylpiperidin-4-yl)-n-ethylpropan-1-amine Chemical compound C1CC(C(CC)NCC)CCN1CC1=CC=CC=C1 OOPXZFAKCHHQQT-UHFFFAOYSA-N 0.000 description 2
- ZTGMNCCDDKBPML-UHFFFAOYSA-N 1-benzoylpiperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1C(=O)C1=CC=CC=C1 ZTGMNCCDDKBPML-UHFFFAOYSA-N 0.000 description 2
- LJCZNYWLQZZIOS-UHFFFAOYSA-N 2,2,2-trichlorethoxycarbonyl chloride Chemical compound ClC(=O)OCC(Cl)(Cl)Cl LJCZNYWLQZZIOS-UHFFFAOYSA-N 0.000 description 2
- SDGKUVSVPIIUCF-UHFFFAOYSA-N 2,6-dimethylpiperidine Chemical compound CC1CCCC(C)N1 SDGKUVSVPIIUCF-UHFFFAOYSA-N 0.000 description 2
- JOZNSWOXYUTTMZ-UHFFFAOYSA-N 2-(1,3-thiazol-2-yl)quinoline-4-carboxylic acid Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=NC=CS1 JOZNSWOXYUTTMZ-UHFFFAOYSA-N 0.000 description 2
- DKOMWOZFQXNJAQ-UHFFFAOYSA-N 2-(2-fluorophenyl)quinoline-4-carboxylic acid Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=CC=C1F DKOMWOZFQXNJAQ-UHFFFAOYSA-N 0.000 description 2
- METUEFNOMUIMQR-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)quinoline-4-carboxylic acid Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(Cl)C(Cl)=C1 METUEFNOMUIMQR-UHFFFAOYSA-N 0.000 description 2
- QPDXYIKQOBZSGQ-UHFFFAOYSA-N 2-(3-chlorophenyl)quinoline-4-carboxylic acid Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=CC(Cl)=C1 QPDXYIKQOBZSGQ-UHFFFAOYSA-N 0.000 description 2
- FTEWYGPKBUSJTI-UHFFFAOYSA-N 2-(4-chlorophenyl)quinoline-4-carboxylic acid Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(Cl)C=C1 FTEWYGPKBUSJTI-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
- ZCNPYYVKVXSLQF-UHFFFAOYSA-N 2-(4-methoxyphenyl)quinoline-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1=CC(C(O)=O)=C(C=CC=C2)C2=N1 ZCNPYYVKVXSLQF-UHFFFAOYSA-N 0.000 description 2
- CKOMAFAOCHXEQX-UHFFFAOYSA-N 2-(4-methylphenyl)quinoline-4-carboxylic acid Chemical compound C1=CC(C)=CC=C1C1=CC(C(O)=O)=C(C=CC=C2)C2=N1 CKOMAFAOCHXEQX-UHFFFAOYSA-N 0.000 description 2
- QHJQZWPZUQTPAT-UHFFFAOYSA-N 2-[3-(trifluoromethyl)phenyl]quinoline-4-carboxylic acid Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=CC(C(F)(F)F)=C1 QHJQZWPZUQTPAT-UHFFFAOYSA-N 0.000 description 2
- XAFQAVSXMYZKPP-UHFFFAOYSA-N 2-phenyl-8-(trifluoromethyl)quinoline-4-carboxylic acid Chemical compound N=1C2=C(C(F)(F)F)C=CC=C2C(C(=O)O)=CC=1C1=CC=CC=C1 XAFQAVSXMYZKPP-UHFFFAOYSA-N 0.000 description 2
- VHAROPVOPPFUKE-UHFFFAOYSA-N 3,6-dihydro-2h-pyridin-1-yl-(2-phenylquinolin-4-yl)methanone Chemical compound C=1C(C=2C=CC=CC=2)=NC2=CC=CC=C2C=1C(=O)N1CCC=CC1 VHAROPVOPPFUKE-UHFFFAOYSA-N 0.000 description 2
- OBIWFVGKXKGAEW-UHFFFAOYSA-N 3-phenylisoquinoline-1-carboxylic acid Chemical compound C=1C2=CC=CC=C2C(C(=O)O)=NC=1C1=CC=CC=C1 OBIWFVGKXKGAEW-UHFFFAOYSA-N 0.000 description 2
- MLXXXFVCTDCEKZ-UHFFFAOYSA-N 6,7-dimethoxy-2-phenylquinoline-4-carboxylic acid Chemical compound C=1C(C(O)=O)=C2C=C(OC)C(OC)=CC2=NC=1C1=CC=CC=C1 MLXXXFVCTDCEKZ-UHFFFAOYSA-N 0.000 description 2
- QTHANKFZSPYAPO-UHFFFAOYSA-N 6-methyl-2-phenylquinoline-4-carboxylic acid Chemical compound C1=C(C(O)=O)C2=CC(C)=CC=C2N=C1C1=CC=CC=C1 QTHANKFZSPYAPO-UHFFFAOYSA-N 0.000 description 2
- ZPBCZAOGVIOUQA-UHFFFAOYSA-N 8-nitro-2-phenylquinoline-4-carboxylic acid Chemical compound N=1C2=C([N+]([O-])=O)C=CC=C2C(C(=O)O)=CC=1C1=CC=CC=C1 ZPBCZAOGVIOUQA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
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- 241000276498 Pollachius virens Species 0.000 description 2
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
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- 210000000748 cardiovascular system Anatomy 0.000 description 2
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- RNFNDJAIBTYOQL-UHFFFAOYSA-N chloral hydrate Chemical compound OC(O)C(Cl)(Cl)Cl RNFNDJAIBTYOQL-UHFFFAOYSA-N 0.000 description 2
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- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
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- 239000000706 filtrate Substances 0.000 description 2
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- DDRNROHGHSYLHB-UHFFFAOYSA-N methyl 2-(3-chlorophenyl)quinoline-4-carboxylate Chemical compound N=1C2=CC=CC=C2C(C(=O)OC)=CC=1C1=CC=CC(Cl)=C1 DDRNROHGHSYLHB-UHFFFAOYSA-N 0.000 description 2
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- RJXIXZDGMPIGGS-UHFFFAOYSA-N morpholin-4-yl-(2-phenylquinazolin-4-yl)methanone Chemical compound N=1C(C=2C=CC=CC=2)=NC2=CC=CC=C2C=1C(=O)N1CCOCC1 RJXIXZDGMPIGGS-UHFFFAOYSA-N 0.000 description 2
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- PXKZVCOKJFOTQY-UHFFFAOYSA-N n-(1-benzylpiperidin-4-yl)acetamide Chemical compound C1CC(NC(=O)C)CCN1CC1=CC=CC=C1 PXKZVCOKJFOTQY-UHFFFAOYSA-N 0.000 description 2
- BSYAMTMKRGNHEY-UHFFFAOYSA-N n-benzyl-n-methyl-2-phenylquinoline-4-carboxamide Chemical compound C=1C(C=2C=CC=CC=2)=NC2=CC=CC=C2C=1C(=O)N(C)CC1=CC=CC=C1 BSYAMTMKRGNHEY-UHFFFAOYSA-N 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
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- HTSJDCLPNUWZDY-UHFFFAOYSA-N (4-hydroxypiperidin-1-yl)-(2-phenylquinazolin-4-yl)methanone Chemical compound C1CC(O)CCN1C(=O)C1=NC(C=2C=CC=CC=2)=NC2=CC=CC=C12 HTSJDCLPNUWZDY-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical class C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- 125000005943 1,2,3,6-tetrahydropyridyl group Chemical group 0.000 description 1
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
- AHMXMGBNICXMKU-UHFFFAOYSA-N 1-(dibromomethyl)-3-phenylisoquinoline Chemical compound C=1C2=CC=CC=C2C(C(Br)Br)=NC=1C1=CC=CC=C1 AHMXMGBNICXMKU-UHFFFAOYSA-N 0.000 description 1
- SJWKLNGMIHLOJX-UHFFFAOYSA-N 1-benzyl-n-ethylpiperidin-4-amine Chemical compound C1CC(NCC)CCN1CC1=CC=CC=C1 SJWKLNGMIHLOJX-UHFFFAOYSA-N 0.000 description 1
- YUBDLZGUSSWQSS-UHFFFAOYSA-N 1-benzylpiperidin-4-amine Chemical compound C1CC(N)CCN1CC1=CC=CC=C1 YUBDLZGUSSWQSS-UHFFFAOYSA-N 0.000 description 1
- ZOXOLPGKTSLTFP-UHFFFAOYSA-N 1-methyl-3-phenylisoquinoline Chemical compound C=1C2=CC=CC=C2C(C)=NC=1C1=CC=CC=C1 ZOXOLPGKTSLTFP-UHFFFAOYSA-N 0.000 description 1
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- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
- KXHGWYZKPOTYOL-UHFFFAOYSA-N 2-(1-benzoylpiperidin-4-yl)acetic acid Chemical compound C1CC(CC(=O)O)CCN1C(=O)C1=CC=CC=C1 KXHGWYZKPOTYOL-UHFFFAOYSA-N 0.000 description 1
- SELVPWKBYLFEFE-UHFFFAOYSA-N 2-(1-benzoylpiperidin-4-yl)propanoic acid Chemical compound C1CC(C(C)C(O)=O)CCN1C(=O)C1=CC=CC=C1 SELVPWKBYLFEFE-UHFFFAOYSA-N 0.000 description 1
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- NJBCRXCAPCODGX-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)propan-1-amine Chemical compound CC(C)CNCC(C)C NJBCRXCAPCODGX-UHFFFAOYSA-N 0.000 description 1
- AFHGMYUEOXZDBM-UHFFFAOYSA-N 2-phenylquinoline-4-carbonyl chloride Chemical compound N=1C2=CC=CC=C2C(C(=O)Cl)=CC=1C1=CC=CC=C1 AFHGMYUEOXZDBM-UHFFFAOYSA-N 0.000 description 1
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- FTAHXMZRJCZXDL-UHFFFAOYSA-N 3-piperideine Chemical compound C1CC=CCN1 FTAHXMZRJCZXDL-UHFFFAOYSA-N 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- UZOFELREXGAFOI-UHFFFAOYSA-N 4-methylpiperidine Chemical compound CC1CCNCC1 UZOFELREXGAFOI-UHFFFAOYSA-N 0.000 description 1
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- XUFTWETZBZPRQD-UHFFFAOYSA-N C(=O)=C1C(NC(CC1)C)C Chemical compound C(=O)=C1C(NC(CC1)C)C XUFTWETZBZPRQD-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- NMKSBNZBSLHAKW-UHFFFAOYSA-N Cl.ClO Chemical compound Cl.ClO NMKSBNZBSLHAKW-UHFFFAOYSA-N 0.000 description 1
- NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 1
- PAMIQIKDUOTOBW-UHFFFAOYSA-N N-methylcyclohexylamine Natural products CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 1
- 235000014676 Phragmites communis Nutrition 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000002082 anti-convulsion Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 230000000949 anxiolytic effect Effects 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical group NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 1
- 244000309464 bull Species 0.000 description 1
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- 230000003197 catalytic effect Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
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- 230000001186 cumulative effect Effects 0.000 description 1
- 238000002716 delivery method Methods 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- MSMGXWFHBSCQFB-UHFFFAOYSA-N ethyl cyanoformate Chemical compound CCOC(=O)C#N MSMGXWFHBSCQFB-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- OMRRUNXAWXNVFW-UHFFFAOYSA-N fluoridochlorine Chemical compound ClF OMRRUNXAWXNVFW-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
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- 230000000147 hypnotic effect Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- HJTIBQAZKOGQKW-UHFFFAOYSA-N n,n-diethyl-3-phenylnaphthalene-1-carboxamide Chemical compound C=1C2=CC=CC=C2C(C(=O)N(CC)CC)=CC=1C1=CC=CC=C1 HJTIBQAZKOGQKW-UHFFFAOYSA-N 0.000 description 1
- NPUWCNWUUSYMTF-UHFFFAOYSA-N n-[(1-benzylpiperidin-4-yl)methyl]ethanamine Chemical compound C1CC(CNCC)CCN1CC1=CC=CC=C1 NPUWCNWUUSYMTF-UHFFFAOYSA-N 0.000 description 1
- YGSADUQWAHCUDV-UHFFFAOYSA-N n-benzyl-n-ethylpiperidine-4-carboxamide Chemical compound C1CNCCC1C(=O)N(CC)CC1=CC=CC=C1 YGSADUQWAHCUDV-UHFFFAOYSA-N 0.000 description 1
- TZCRREYQVVELNQ-UHFFFAOYSA-N n-butan-2-yl-2-(2-chlorophenyl)-n-methylquinoline-4-carboxamide Chemical compound N=1C2=CC=CC=C2C(C(=O)N(C)C(C)CC)=CC=1C1=CC=CC=C1Cl TZCRREYQVVELNQ-UHFFFAOYSA-N 0.000 description 1
- OBYVIBDTOCAXSN-UHFFFAOYSA-N n-butan-2-ylbutan-2-amine Chemical compound CCC(C)NC(C)CC OBYVIBDTOCAXSN-UHFFFAOYSA-N 0.000 description 1
- KFYKZKISJBGVMR-UHFFFAOYSA-N n-ethylbutan-2-amine Chemical compound CCNC(C)CC KFYKZKISJBGVMR-UHFFFAOYSA-N 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- CBFHHXZSENSSMA-UHFFFAOYSA-N quinazoline-4-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=NC=NC2=C1 CBFHHXZSENSSMA-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- SMDQFHZIWNYSMR-UHFFFAOYSA-N sulfanylidenemagnesium Chemical compound S=[Mg] SMDQFHZIWNYSMR-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000723 toxicological property Toxicity 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- 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
- C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
-
- 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
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/26—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
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
-
- 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
- C07D401/06—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 linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8221758A FR2538388B1 (fr) | 1982-12-24 | 1982-12-24 | Nouveaux derives de naphtalene- ou azanaphtalenecarboxamide, leurs procedes de preparation et leur utilisation comme medicaments |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO834798L true NO834798L (no) | 1984-06-25 |
Family
ID=9280501
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO834798A NO834798L (no) | 1982-12-24 | 1983-12-23 | Medikamenter paa basis av derivater av naftalen- eller aza-naftalencarboxamid, nye slike derivater og deres fremstilling |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US4711890A (da) |
| EP (1) | EP0112776B1 (da) |
| JP (1) | JPS59219260A (da) |
| AT (1) | ATE28401T1 (da) |
| AU (1) | AU575797B2 (da) |
| CA (1) | CA1225992A (da) |
| DE (1) | DE3372579D1 (da) |
| DK (1) | DK596483A (da) |
| ES (1) | ES528364A0 (da) |
| FR (1) | FR2538388B1 (da) |
| GR (1) | GR82358B (da) |
| HU (1) | HU191745B (da) |
| IL (1) | IL70528A (da) |
| MA (1) | MA19982A1 (da) |
| NO (1) | NO834798L (da) |
| PT (1) | PT77886B (da) |
| SU (1) | SU1255050A3 (da) |
| ZA (1) | ZA839576B (da) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4639454A (en) * | 1985-01-17 | 1987-01-27 | E. I. Du Pont De Nemours And Company | Phenylquinazolinecarboxylic acids and derivatives as cancer chemotherapeutic agents |
| FR2582514B1 (fr) * | 1985-05-30 | 1988-02-19 | Rhone Poulenc Sante | Medicaments a base d'amides, nouveaux amides et leur preparation |
| DK623586A (da) * | 1985-12-27 | 1987-06-28 | Eisai Co Ltd | Piperidinderivater eller salte deraf og farmaceutiske kompositioner indeholdende forbindelserne |
| FI95572C (fi) * | 1987-06-22 | 1996-02-26 | Eisai Co Ltd | Menetelmä lääkeaineena käyttökelpoisen piperidiinijohdannaisten tai sen farmaseuttisen suolan valmistamiseksi |
| US4933447A (en) * | 1987-09-24 | 1990-06-12 | Ss Pharmaceutical Co., Ltd. | Quinoline derivatives |
| PL186075B1 (pl) | 1994-05-27 | 2003-10-31 | Smithkline Beechem Spa | N-(-etylobenzylo)-3-hydroksy-2-fenylochinolino-4-karboksyamid oraz kompozycja farmaceutyczna zawierająca ten związek |
| IT1270615B (it) * | 1994-07-14 | 1997-05-07 | Smithkline Beecham Farma | Uso di derivati di chinolina |
| US5627193A (en) * | 1995-02-09 | 1997-05-06 | Mitsui Toatsu Chemicals, Inc. | Quinoline-4-carbonylguanidine derivatives, process for producing the same and pharmaceutical preparations containing the compounds |
| GB9524104D0 (en) | 1995-11-24 | 1996-01-24 | Smithkline Beecham Spa | Novel compounds |
| AR004735A1 (es) * | 1995-11-24 | 1999-03-10 | Smithkline Beecham Spa | Quinoleina 4-amido sustituida, un procedimiento para su preparacion, una composicion farmaceutica que los contiene y el uso de los mismos para lapreparacion de un medicamento. |
| BR9611820A (pt) * | 1995-11-24 | 1999-07-13 | Smithkline Beecham Spa | Derivados de quinolina |
| KR100225565B1 (ko) * | 1996-12-12 | 1999-10-15 | 유규재 | 초미세 규산 알루미늄염의 제조법 |
| WO1998049900A1 (en) * | 1997-05-07 | 1998-11-12 | Emory University | Haloisoquinoline carboxamide |
| WO1999058117A1 (fr) * | 1998-05-13 | 1999-11-18 | Sanofi-Synthelabo | Utilisation de composes reduisant l'apoptose |
| FR2778564B1 (fr) * | 1998-05-13 | 2001-07-13 | Sanofi Sa | Utilisation de composes reduisant l'apoptose |
| DE10035928A1 (de) | 2000-07-21 | 2002-03-07 | Asta Medica Ag | Neue Heteroaryl-Derivate und deren Verwendung als Arzneimittel |
| DE10035927A1 (de) | 2000-07-21 | 2002-03-07 | Asta Medica Ag | Neue Heteroaryl-Derivate und deren Verwendung als Arzneimittel |
| JP2004506038A (ja) * | 2000-08-16 | 2004-02-26 | ニューロゲン コーポレイション | ２，４−置換ピリジン誘導体 |
| US20040152727A1 (en) * | 2001-05-18 | 2004-08-05 | Hay Douglas William Pierre | Novel use |
| CA2518398A1 (en) * | 2003-03-10 | 2004-09-23 | Schering Corporation | Heterocyclic kinase inhibitors: methods of use and synthesis |
| WO2008023357A1 (en) * | 2006-08-22 | 2008-02-28 | Technion Research And Development Foundation Ltd. | Heterocyclic derivatives binding to the peripheral-type benzodiazepine receptor (pbr) |
| DE102008015033A1 (de) | 2008-03-17 | 2009-09-24 | Aicuris Gmbh & Co. Kg | Substituierte (Pyrazolyl-carbonyl)imidazolidinone und ihre Verwendung |
| DE102008015032A1 (de) | 2008-03-17 | 2009-09-24 | Aicuris Gmbh & Co. Kg | Substituierte Pyrazolamide und ihre Verwendung |
| DE102008062878A1 (de) | 2008-12-17 | 2010-06-24 | Aicuris Gmbh & Co. Kg | Substituierte Furancarboxamide und ihre Verwendung |
| DE102008062863A1 (de) | 2008-12-17 | 2010-06-24 | Aicuris Gmbh & Co. Kg | Substituierte (Thiophenyl-carbonyl)imidazolidinone und ihre Verwendung |
| EP2907806A1 (en) * | 2014-02-14 | 2015-08-19 | Universita Degli Studi Di Genova | New compounds as selective PDE4D inhibitors |
| JP6498695B2 (ja) | 2014-04-23 | 2019-04-10 | テクニオン・リサーチ・アンド・ディベロップメント・ファウンデーション・リミテッド | キナゾリン骨格系の化合物、医薬組成物およびその使用方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB191210352A (en) * | 1912-01-16 | 1913-05-01 | Hoechst Ag | Manufacture of New Derivatives of Phenyl-cinchoninic Acid and of Homologues and Derivatives thereof. |
| FR1364605A (fr) * | 1962-03-01 | 1964-06-26 | Procédé de préparation d'amides des acides carboxyliques | |
| US3812127A (en) * | 1966-10-31 | 1974-05-21 | Pfizer | 4-(quinolin-4-yl)piperazine-1-carboxylic acid esters |
| US3799929A (en) * | 1972-03-17 | 1974-03-26 | Lilly Co Eli | Cinchoninic acid derivatives |
| FR2525595A1 (fr) * | 1982-04-27 | 1983-10-28 | Pharmuka Lab | Nouveaux derives d'arene et d'heteroarenecarboxamides et leur utilisation comme medicaments |
-
1982
- 1982-12-24 FR FR8221758A patent/FR2538388B1/fr not_active Expired
-
1983
- 1983-12-21 AT AT83402501T patent/ATE28401T1/de not_active IP Right Cessation
- 1983-12-21 EP EP83402501A patent/EP0112776B1/fr not_active Expired
- 1983-12-21 DE DE8383402501T patent/DE3372579D1/de not_active Expired
- 1983-12-21 GR GR73304A patent/GR82358B/el unknown
- 1983-12-22 ZA ZA839576A patent/ZA839576B/xx unknown
- 1983-12-22 US US06/564,322 patent/US4711890A/en not_active Expired - Fee Related
- 1983-12-22 MA MA20203A patent/MA19982A1/fr unknown
- 1983-12-22 JP JP58243082A patent/JPS59219260A/ja active Pending
- 1983-12-22 AU AU22776/83A patent/AU575797B2/en not_active Ceased
- 1983-12-22 IL IL70528A patent/IL70528A/xx unknown
- 1983-12-22 HU HU834425A patent/HU191745B/hu unknown
- 1983-12-23 CA CA000444273A patent/CA1225992A/fr not_active Expired
- 1983-12-23 ES ES528364A patent/ES528364A0/es active Granted
- 1983-12-23 NO NO834798A patent/NO834798L/no unknown
- 1983-12-23 PT PT77886A patent/PT77886B/pt not_active IP Right Cessation
- 1983-12-23 SU SU833682598A patent/SU1255050A3/ru active
- 1983-12-23 DK DK596483A patent/DK596483A/da not_active Application Discontinuation
-
1985
- 1985-08-08 US US06/763,660 patent/US4684652A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| GR82358B (da) | 1984-12-13 |
| FR2538388A1 (fr) | 1984-06-29 |
| AU2277683A (en) | 1984-06-28 |
| FR2538388B1 (fr) | 1985-06-21 |
| HU191745B (en) | 1987-04-28 |
| IL70528A0 (en) | 1984-03-30 |
| ZA839576B (en) | 1984-08-29 |
| EP0112776A3 (en) | 1984-09-12 |
| EP0112776A2 (fr) | 1984-07-04 |
| US4711890A (en) | 1987-12-08 |
| MA19982A1 (fr) | 1984-07-01 |
| US4684652A (en) | 1987-08-04 |
| AU575797B2 (en) | 1988-08-11 |
| PT77886B (fr) | 1986-04-09 |
| CA1225992A (fr) | 1987-08-25 |
| PT77886A (fr) | 1984-01-01 |
| DE3372579D1 (en) | 1987-08-27 |
| SU1255050A3 (ru) | 1986-08-30 |
| IL70528A (en) | 1987-01-30 |
| ES8502433A1 (es) | 1985-01-01 |
| ATE28401T1 (de) | 1987-08-15 |
| EP0112776B1 (fr) | 1987-07-22 |
| JPS59219260A (ja) | 1984-12-10 |
| DK596483A (da) | 1984-06-25 |
| DK596483D0 (da) | 1983-12-23 |
| ES528364A0 (es) | 1985-01-01 |
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