NO862133L - Amider og deres fremstilling. - Google Patents
Amider og deres fremstilling.Info
- Publication number
- NO862133L NO862133L NO862133A NO862133A NO862133L NO 862133 L NO862133 L NO 862133L NO 862133 A NO862133 A NO 862133A NO 862133 A NO862133 A NO 862133A NO 862133 L NO862133 L NO 862133L
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- acid
- formula
- residue
- reduced pressure
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 46
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 29
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims abstract description 13
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 4
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 3
- 125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 3
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 57
- 239000002253 acid Substances 0.000 claims description 56
- 239000000047 product Substances 0.000 claims description 41
- 125000004432 carbon atom Chemical group C* 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 28
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 17
- 125000004434 sulfur atom Chemical group 0.000 claims description 16
- 150000001412 amines Chemical class 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 239000001301 oxygen Substances 0.000 claims description 13
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 4
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 3
- 239000011593 sulfur Chemical group 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
- GCVJQCBCDZHGOY-UHFFFAOYSA-N methyl-[(2-phenylquinolin-4-yl)methyl]carbamic acid Chemical compound N=1C2=CC=CC=C2C(CN(C)C(O)=O)=CC=1C1=CC=CC=C1 GCVJQCBCDZHGOY-UHFFFAOYSA-N 0.000 claims 1
- 125000003375 sulfoxide group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 abstract description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 abstract description 3
- 229940125681 anticonvulsant agent Drugs 0.000 abstract description 2
- 239000001961 anticonvulsive agent Substances 0.000 abstract description 2
- 239000002249 anxiolytic agent Substances 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract description 2
- 150000002367 halogens Chemical class 0.000 abstract description 2
- 230000000144 pharmacologic effect Effects 0.000 abstract description 2
- GQJPKHSIFUZSGN-UHFFFAOYSA-N (2-phenylquinolin-4-yl) n,n-dimethylcarbamate Chemical compound N=1C2=CC=CC=C2C(OC(=O)N(C)C)=CC=1C1=CC=CC=C1 GQJPKHSIFUZSGN-UHFFFAOYSA-N 0.000 abstract 1
- 230000000949 anxiolytic effect Effects 0.000 abstract 1
- 229940005530 anxiolytics Drugs 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 336
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 213
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 152
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 133
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 129
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 128
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 119
- 239000000243 solution Substances 0.000 description 119
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 119
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 118
- 238000002844 melting Methods 0.000 description 118
- 230000008018 melting Effects 0.000 description 118
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 112
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 91
- 239000000741 silica gel Substances 0.000 description 87
- 229910002027 silica gel Inorganic materials 0.000 description 87
- 229940035423 ethyl ether Drugs 0.000 description 79
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 72
- 239000012074 organic phase Substances 0.000 description 69
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 68
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 66
- 239000003480 eluent Substances 0.000 description 63
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 61
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 59
- 235000019341 magnesium sulphate Nutrition 0.000 description 59
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 57
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 54
- 239000008346 aqueous phase Substances 0.000 description 49
- 238000001953 recrystallisation Methods 0.000 description 47
- 239000002904 solvent Substances 0.000 description 46
- -1 Amide derivatives of quinazoline Chemical class 0.000 description 45
- 229960000583 acetic acid Drugs 0.000 description 45
- 239000000203 mixture Substances 0.000 description 45
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 39
- 238000004587 chromatography analysis Methods 0.000 description 39
- 238000003756 stirring Methods 0.000 description 38
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 35
- 238000010992 reflux Methods 0.000 description 35
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 34
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 31
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 26
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 24
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 24
- APRJFNLVTJWEPP-UHFFFAOYSA-M n,n-diethylcarbamate Chemical compound CCN(CC)C([O-])=O APRJFNLVTJWEPP-UHFFFAOYSA-M 0.000 description 23
- OFCCYDUUBNUJIB-UHFFFAOYSA-N n,n-diethylcarbamoyl chloride Chemical compound CCN(CC)C(Cl)=O OFCCYDUUBNUJIB-UHFFFAOYSA-N 0.000 description 23
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 20
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 19
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- 238000001704 evaporation Methods 0.000 description 18
- 230000008020 evaporation Effects 0.000 description 18
- 239000000706 filtrate Substances 0.000 description 17
- 239000003921 oil Substances 0.000 description 17
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
- 238000002425 crystallisation Methods 0.000 description 16
- 230000008025 crystallization Effects 0.000 description 16
- 239000012362 glacial acetic acid Substances 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 15
- 235000011114 ammonium hydroxide Nutrition 0.000 description 15
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 14
- 238000001816 cooling Methods 0.000 description 14
- 239000000155 melt Substances 0.000 description 13
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- 239000000908 ammonium hydroxide Substances 0.000 description 12
- 238000001914 filtration Methods 0.000 description 12
- 239000012071 phase Substances 0.000 description 12
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 11
- 239000005695 Ammonium acetate Substances 0.000 description 11
- 229940043376 ammonium acetate Drugs 0.000 description 11
- 235000019257 ammonium acetate Nutrition 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 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 8
- 238000009835 boiling Methods 0.000 description 8
- 239000012442 inert solvent Substances 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 8
- 229920000137 polyphosphoric acid Polymers 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 description 8
- 235000017550 sodium carbonate Nutrition 0.000 description 8
- OLUCARQGXSAKLT-UHFFFAOYSA-N 3-(2-phenylquinolin-4-yl)propanoic acid Chemical compound N=1C2=CC=CC=C2C(CCC(=O)O)=CC=1C1=CC=CC=C1 OLUCARQGXSAKLT-UHFFFAOYSA-N 0.000 description 7
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
- 239000012312 sodium hydride Substances 0.000 description 7
- 229910000104 sodium hydride Inorganic materials 0.000 description 7
- JGABMVVOXLQCKZ-UHFFFAOYSA-N 2-phenyl-1h-quinolin-4-one Chemical compound N=1C2=CC=CC=C2C(O)=CC=1C1=CC=CC=C1 JGABMVVOXLQCKZ-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- YTLUXYRVPVELBH-UHFFFAOYSA-N n,n-diethyl-2-(2-phenylquinazolin-4-yl)oxypropanamide Chemical compound N=1C2=CC=CC=C2C(OC(C)C(=O)N(CC)CC)=NC=1C1=CC=CC=C1 YTLUXYRVPVELBH-UHFFFAOYSA-N 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 6
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- OHRMHLAHQBYLPM-UHFFFAOYSA-N 2-(2-phenylquinolin-4-yl)sulfanylacetic acid Chemical compound N=1C2=CC=CC=C2C(SCC(=O)O)=CC=1C1=CC=CC=C1 OHRMHLAHQBYLPM-UHFFFAOYSA-N 0.000 description 5
- CQQUWTMMFMJEFE-UHFFFAOYSA-N 2-chloro-n,n-diethylacetamide Chemical compound CCN(CC)C(=O)CCl CQQUWTMMFMJEFE-UHFFFAOYSA-N 0.000 description 5
- HFINRBDYDZPDKZ-UHFFFAOYSA-N 4-(2-phenylquinolin-4-yl)butanoic acid Chemical compound N=1C2=CC=CC=C2C(CCCC(=O)O)=CC=1C1=CC=CC=C1 HFINRBDYDZPDKZ-UHFFFAOYSA-N 0.000 description 5
- ZAXGSKSVGPIAKN-UHFFFAOYSA-N 4-(2-phenylquinolin-4-yl)oxybutanoic acid Chemical compound N=1C2=CC=CC=C2C(OCCCC(=O)O)=CC=1C1=CC=CC=C1 ZAXGSKSVGPIAKN-UHFFFAOYSA-N 0.000 description 5
- IAKIEFRRBKQXIW-UHFFFAOYSA-N 4-bromo-2-phenylquinoline Chemical compound N=1C2=CC=CC=C2C(Br)=CC=1C1=CC=CC=C1 IAKIEFRRBKQXIW-UHFFFAOYSA-N 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- 235000010755 mineral Nutrition 0.000 description 5
- 239000011707 mineral Substances 0.000 description 5
- AVTWCMDAQCIYSR-UHFFFAOYSA-N (3-phenylnaphthalen-1-yl)methanol Chemical compound C=1C2=CC=CC=C2C(CO)=CC=1C1=CC=CC=C1 AVTWCMDAQCIYSR-UHFFFAOYSA-N 0.000 description 4
- VPSKMQYCSCPAGT-UHFFFAOYSA-N 2-bromo-n,n-diethylpropanamide Chemical compound CCN(CC)C(=O)C(C)Br VPSKMQYCSCPAGT-UHFFFAOYSA-N 0.000 description 4
- VDULOAUXSMYUMG-UHFFFAOYSA-N 2-phenyl-1h-quinazolin-4-one Chemical compound N=1C2=CC=CC=C2C(O)=NC=1C1=CC=CC=C1 VDULOAUXSMYUMG-UHFFFAOYSA-N 0.000 description 4
- QOLQFIRCIQFPNA-UHFFFAOYSA-N 2-phenyl-8-(trifluoromethyl)-1h-quinolin-4-one Chemical compound N=1C2=C(C(F)(F)F)C=CC=C2C(O)=CC=1C1=CC=CC=C1 QOLQFIRCIQFPNA-UHFFFAOYSA-N 0.000 description 4
- SFARODKZVSNGEW-UHFFFAOYSA-N 3-(2-phenylquinazolin-4-yl)propanoic acid Chemical compound N=1C2=CC=CC=C2C(CCC(=O)O)=NC=1C1=CC=CC=C1 SFARODKZVSNGEW-UHFFFAOYSA-N 0.000 description 4
- VZYRBVZOGGKAKY-UHFFFAOYSA-N 3-phenyl-2h-isoquinolin-1-one Chemical compound C=1C2=CC=CC=C2C(O)=NC=1C1=CC=CC=C1 VZYRBVZOGGKAKY-UHFFFAOYSA-N 0.000 description 4
- MAPYOCUYNJWAJW-UHFFFAOYSA-N 3-phenylnaphthalen-1-ol Chemical compound C=1C2=CC=CC=C2C(O)=CC=1C1=CC=CC=C1 MAPYOCUYNJWAJW-UHFFFAOYSA-N 0.000 description 4
- SUBAESQCGKNVQR-UHFFFAOYSA-N 4-(2-aminophenyl)-n,n-diethyl-4-oxobutanamide Chemical compound CCN(CC)C(=O)CCC(=O)C1=CC=CC=C1N SUBAESQCGKNVQR-UHFFFAOYSA-N 0.000 description 4
- GLVDSTVYOFXBKT-UHFFFAOYSA-N 4-chloro-2-phenylquinoline Chemical compound N=1C2=CC=CC=C2C(Cl)=CC=1C1=CC=CC=C1 GLVDSTVYOFXBKT-UHFFFAOYSA-N 0.000 description 4
- FHUBTSLLILWICW-UHFFFAOYSA-N 4-phenyl-1h-quinazolin-2-one Chemical compound C12=CC=CC=C2NC(=O)N=C1C1=CC=CC=C1 FHUBTSLLILWICW-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 4
- UPQZOUHVTJNGFK-UHFFFAOYSA-N diethyl 2-methylpropanedioate Chemical compound CCOC(=O)C(C)C(=O)OCC UPQZOUHVTJNGFK-UHFFFAOYSA-N 0.000 description 4
- AKKZWDPNRFZFEX-UHFFFAOYSA-N ethyl 4-(2-aminophenyl)-4-oxobutanoate Chemical compound CCOC(=O)CCC(=O)C1=CC=CC=C1N AKKZWDPNRFZFEX-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- FJUXXPWWWMLFJY-UHFFFAOYSA-N 1-(bromomethyl)-3-phenylisoquinoline Chemical compound C=1C2=CC=CC=C2C(CBr)=NC=1C1=CC=CC=C1 FJUXXPWWWMLFJY-UHFFFAOYSA-N 0.000 description 3
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- XWIYKUWXGCGHDH-UHFFFAOYSA-N n,n-diethyl-3-(1-phenylisoquinolin-3-yl)propanamide Chemical compound N=1C(CCC(=O)N(CC)CC)=CC2=CC=CC=C2C=1C1=CC=CC=C1 XWIYKUWXGCGHDH-UHFFFAOYSA-N 0.000 description 1
- FUFAVPUOZASCOT-UHFFFAOYSA-N n,n-diethyl-3-(2-phenylquinolin-4-yl)oxypropanamide Chemical compound N=1C2=CC=CC=C2C(OCCC(=O)N(CC)CC)=CC=1C1=CC=CC=C1 FUFAVPUOZASCOT-UHFFFAOYSA-N 0.000 description 1
- ZRUINGGXXBJXRJ-UHFFFAOYSA-N n,n-diethyl-3-(2-phenylquinolin-4-yl)propanamide Chemical compound N=1C2=CC=CC=C2C(CCC(=O)N(CC)CC)=CC=1C1=CC=CC=C1 ZRUINGGXXBJXRJ-UHFFFAOYSA-N 0.000 description 1
- BYHVOXBUYYTBQY-UHFFFAOYSA-N n,n-diethyl-3-(2-phenylquinolin-4-yl)sulfonylpropanamide Chemical compound N=1C2=CC=CC=C2C(S(=O)(=O)CCC(=O)N(CC)CC)=CC=1C1=CC=CC=C1 BYHVOXBUYYTBQY-UHFFFAOYSA-N 0.000 description 1
- YYQCJJRJOHVJIK-UHFFFAOYSA-N n,n-diethyl-3-(2-pyridin-2-ylquinazolin-4-yl)propanamide Chemical compound N=1C2=CC=CC=C2C(CCC(=O)N(CC)CC)=NC=1C1=CC=CC=N1 YYQCJJRJOHVJIK-UHFFFAOYSA-N 0.000 description 1
- WZKHSVGOUMBIBD-UHFFFAOYSA-N n,n-diethyl-3-(6-methoxy-2-phenylquinazolin-4-yl)propanamide Chemical compound N=1C2=CC=C(OC)C=C2C(CCC(=O)N(CC)CC)=NC=1C1=CC=CC=C1 WZKHSVGOUMBIBD-UHFFFAOYSA-N 0.000 description 1
- CDDKIXDZQYFPJZ-UHFFFAOYSA-N n,n-diethyl-3-(7-methyl-1h-indol-3-yl)propanamide Chemical compound C1=CC=C2C(CCC(=O)N(CC)CC)=CNC2=C1C CDDKIXDZQYFPJZ-UHFFFAOYSA-N 0.000 description 1
- WZTUJZUFLAZLST-UHFFFAOYSA-N n,n-diethyl-3-(ethylamino)propanamide Chemical compound CCNCCC(=O)N(CC)CC WZTUJZUFLAZLST-UHFFFAOYSA-N 0.000 description 1
- OFTWVVXOUVUNHA-UHFFFAOYSA-N n,n-diethyl-3-[2-(3-methoxyphenyl)quinazolin-4-yl]propanamide Chemical compound N=1C2=CC=CC=C2C(CCC(=O)N(CC)CC)=NC=1C1=CC=CC(OC)=C1 OFTWVVXOUVUNHA-UHFFFAOYSA-N 0.000 description 1
- DJCMEPQJKJMBFX-UHFFFAOYSA-N n,n-diethyl-3-[2-(4-methylphenyl)quinazolin-4-yl]propanamide Chemical compound N=1C2=CC=CC=C2C(CCC(=O)N(CC)CC)=NC=1C1=CC=C(C)C=C1 DJCMEPQJKJMBFX-UHFFFAOYSA-N 0.000 description 1
- BQGMZRYZDSOMLN-UHFFFAOYSA-N n,n-diethyl-4-(2-phenylquinolin-4-yl)butanamide Chemical compound N=1C2=CC=CC=C2C(CCCC(=O)N(CC)CC)=CC=1C1=CC=CC=C1 BQGMZRYZDSOMLN-UHFFFAOYSA-N 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- AGISYFFNQWEPMW-UHFFFAOYSA-N n-ethylethanamine;toluene Chemical compound CCNCC.CC1=CC=CC=C1 AGISYFFNQWEPMW-UHFFFAOYSA-N 0.000 description 1
- HYDCVYJZTPHAQR-UHFFFAOYSA-N n-methylaniline Chemical compound [CH2]NC1=CC=CC=C1 HYDCVYJZTPHAQR-UHFFFAOYSA-N 0.000 description 1
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 238000007339 nucleophilic aromatic substitution reaction Methods 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
- UVXXJBCXGYMTME-UHFFFAOYSA-N piperidine-1-carboxylic acid;hydrochloride Chemical compound Cl.OC(=O)N1CCCCC1 UVXXJBCXGYMTME-UHFFFAOYSA-N 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000003246 quinazolines Chemical class 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 150000003902 salicylic acid esters Chemical class 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- UNHKSXOTUHOTAB-UHFFFAOYSA-N sodium;sulfane Chemical compound [Na].S UNHKSXOTUHOTAB-UHFFFAOYSA-N 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003900 succinic acid esters Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 238000005406 washing Methods 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
- C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- C07D215/12—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 substituted hydrocarbon radicals attached to ring carbon 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
- C07D215/20—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
- C07D215/36—Sulfur 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
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
-
- 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
- C07D217/24—Oxygen atoms
-
- 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
- C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
-
- 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
- C07D239/78—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
- C07D239/80—Oxygen atoms
- C07D239/82—Oxygen atoms with an aryl radical attached in position 4
-
- 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
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
- C07D239/91—Oxygen atoms with aryl or aralkyl radicals attached in position 2 or 3
-
- 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
-
- 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
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms 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)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (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)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Immunology (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Medicinal Preparation (AREA)
- Quinoline Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pyridine Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR858508111A FR2582514B1 (fr) | 1985-05-30 | 1985-05-30 | Medicaments a base d'amides, nouveaux amides et leur preparation |
Publications (1)
Publication Number | Publication Date |
---|---|
NO862133L true NO862133L (no) | 1986-12-01 |
Family
ID=9319678
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO862134A NO862134L (no) | 1985-05-30 | 1986-05-29 | Amidderivater av kinolin samt deres fremstilling. |
NO862133A NO862133L (no) | 1985-05-30 | 1986-05-29 | Amider og deres fremstilling. |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO862134A NO862134L (no) | 1985-05-30 | 1986-05-29 | Amidderivater av kinolin samt deres fremstilling. |
Country Status (20)
Country | Link |
---|---|
US (3) | US4728647A (hu) |
EP (2) | EP0205375B1 (hu) |
JP (2) | JPS625946A (hu) |
AT (2) | ATE40689T1 (hu) |
AU (2) | AU579472B2 (hu) |
CA (2) | CA1264160A (hu) |
DE (2) | DE3666813D1 (hu) |
DK (2) | DK252286A (hu) |
ES (7) | ES8704732A1 (hu) |
FR (1) | FR2582514B1 (hu) |
GR (2) | GR861369B (hu) |
HU (2) | HU195642B (hu) |
IL (2) | IL78968A (hu) |
MA (2) | MA20697A1 (hu) |
NO (2) | NO862134L (hu) |
NZ (2) | NZ216331A (hu) |
PT (2) | PT82674B (hu) |
SU (7) | SU1440342A3 (hu) |
TN (2) | TNSN86081A1 (hu) |
ZA (2) | ZA863992B (hu) |
Families Citing this family (35)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4876346A (en) * | 1985-05-02 | 1989-10-24 | American Home Products Corporation | Quinoline compounds |
FR2582514B1 (fr) * | 1985-05-30 | 1988-02-19 | Rhone Poulenc Sante | Medicaments a base d'amides, nouveaux amides et leur preparation |
HU199424B (en) * | 1987-04-24 | 1990-02-28 | Egyt Gyogyszervegyeszeti Gyar | Process for producing quinoline thioethers and pharmaceutical compositions comprising such compounds |
HU199423B (en) * | 1987-04-24 | 1990-02-28 | Egyt Gyogyszervegyeszeti Gyar | Process for producing 3-amino-4-/ethylthio/-quinoline and pharmaceutical compositions comprising such compounds |
GB8726735D0 (en) * | 1987-11-14 | 1987-12-16 | Wellcome Found | Pesticidal compounds |
DE68917024D1 (de) * | 1988-05-24 | 1994-09-01 | Kirin Brewery | 4(1H)-Chinolonderivate. |
FR2636327A1 (fr) * | 1988-09-13 | 1990-03-16 | Rhone Poulenc Sante | Derives de quinoleine, leurs procedes de preparation et les medicaments les contenant |
JP2669905B2 (ja) * | 1989-09-01 | 1997-10-29 | ファナック株式会社 | リレーの溶着検出方法 |
FR2665159B1 (fr) * | 1990-07-24 | 1992-11-13 | Rhone Poulenc Sante | Nouveaux derives de la pyridine et de la quinoleine, leur preparation et les compositions pharmaceutiques qui les contiennent. |
NO932130L (no) * | 1992-06-19 | 1993-12-20 | Lilly Co Eli | Hemmere av HIV-protease som er nyttige for behandling av AIDS |
JP3408300B2 (ja) * | 1993-11-10 | 2003-05-19 | シチズン時計株式会社 | プリンタ |
DE4420337A1 (de) * | 1994-06-10 | 1995-12-14 | Bayer Ag | N-Heterocyclyl-heteroaryloxyacetamide |
US5658902A (en) * | 1994-12-22 | 1997-08-19 | Warner-Lambert Company | Quinazolines as inhibitors of endothelin converting enzyme |
IL117659A (en) * | 1995-04-13 | 2000-12-06 | Dainippon Pharmaceutical Co | Substituted 2-phenyl pyrimidino amino acetamide derivative process for preparing the same and a pharmaceutical composition containing same |
US5648448A (en) * | 1995-06-06 | 1997-07-15 | Hitachi Chemical Company, Ltd. | Method of preparation of polyquinolines |
US5776946A (en) * | 1995-08-28 | 1998-07-07 | Mcgeer; Patrick L. | Peripheral benzodiazepine receptor ligands as antiinflammatory agents |
FR2750427B1 (fr) * | 1996-06-28 | 1998-08-07 | Synthelabo | Derives de 1-oxo-1, 2-dihydroisoquinoleine-4-propanamide, leur preparation et leur application en therapeutique |
AU7474998A (en) * | 1997-05-07 | 1998-11-27 | Emory University | Haloisoquinoline carboxamide |
ZA9810490B (en) | 1997-12-03 | 1999-05-20 | Dainippon Pharmaceutical Co | 2-Aryl-8-oxodihydropurine derivative process for the preparation thereof pharmaceutical composition containing the same and intermediate therefor |
FR2778564B1 (fr) * | 1998-05-13 | 2001-07-13 | Sanofi Sa | Utilisation de composes reduisant l'apoptose |
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FR2779963A1 (fr) | 1998-06-22 | 1999-12-24 | Centre Nat Rech Scient | Utilisation d'un compose possedant une affinite pour le recepteur mitochondrial des benzodiazepines en therapie du cancer |
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PE20050159A1 (es) * | 2003-05-27 | 2005-04-19 | Vertex Pharma | Derivados de acido 3-[2-(3-amino-2-oxo-2h-piridin-1-il)-acetilamino]-4-oxo-pentanoico como inhibidores de caspasa |
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Publication number | Priority date | Publication date | Assignee | Title |
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FR964545A (hu) * | 1947-04-11 | 1950-08-18 | ||
US2568037A (en) * | 1947-10-24 | 1951-09-18 | Sterling Drug Inc | Tertiary-aminoalkyl esters and amides of 4-quinolylmercaptoalkanoic acids and their preparation |
US2785165A (en) * | 1953-12-22 | 1957-03-12 | Abbott Lab | Preparation of 4-aminoquinoline |
GB1013224A (en) * | 1962-06-21 | 1965-12-15 | Ici Ltd | Heterocyclic aminoethanols |
GB1064252A (en) * | 1963-09-19 | 1967-04-05 | Ici Ltd | Amides and pharmaceutical compositions containing them |
IL26022A (en) * | 1966-06-23 | 1971-06-23 | Haber R | Nitrofuryl quinoline derivatives |
GB1177548A (en) * | 1967-11-28 | 1970-01-14 | Ici Ltd | Phenoxy-and Anilino-Alkanoic Acid Amides |
US3595861A (en) * | 1967-12-08 | 1971-07-27 | American Home Prod | Novel synthesis of 2-quinazolinepropionic acids and derivatives |
FR8411M (hu) * | 1968-12-31 | 1971-03-31 | ||
DE2361438C3 (de) * | 1973-12-10 | 1979-12-13 | Hoechst Ag, 6000 Frankfurt | 4-Hydroxychinoün- und 4-Hydroxytetrahydrochinolin-N^N-dimethylcarbamate, Verfahren zu ihrer Herstellung und diese enthaltende insektizide Mittel |
DE2411662A1 (de) | 1974-03-12 | 1975-09-25 | Lechler Elring Dichtungswerke | Vorrichtung zum einseitigen anheben und lenkbarmachen einer palette insbesondere einer rollpalette |
GB1574019A (en) * | 1977-01-14 | 1980-09-03 | Joullie International Sa | Therapeutically useful 3,4,5-trimethoxybenzene derivatives |
FR2471981A1 (fr) * | 1979-12-21 | 1981-06-26 | Pharmindustrie | Nouveaux derives de la (piperidyl-4)-2 (quinolyl-4)-1 ethanone, produits intermediaires et procedes pour 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 |
FR2525595A1 (fr) * | 1982-04-27 | 1983-10-28 | Pharmuka Lab | Nouveaux derives d'arene et d'heteroarenecarboxamides et leur utilisation comme medicaments |
FR2538388B1 (fr) * | 1982-12-24 | 1985-06-21 | Pharmuka Lab | Nouveaux derives de naphtalene- ou azanaphtalenecarboxamide, leurs procedes de preparation et leur utilisation comme medicaments |
NZ209710A (en) * | 1983-09-29 | 1988-02-12 | Akzo Nv | Quinazoline and isoquinoline derivatives and pharmaceutical and veterinary compositions containing such |
FR2582514B1 (fr) * | 1985-05-30 | 1988-02-19 | Rhone Poulenc Sante | Medicaments a base d'amides, nouveaux amides et leur preparation |
-
1985
- 1985-05-30 FR FR858508111A patent/FR2582514B1/fr not_active Expired
-
1986
- 1986-05-28 AU AU58030/86A patent/AU579472B2/en not_active Ceased
- 1986-05-28 PT PT82674A patent/PT82674B/pt not_active IP Right Cessation
- 1986-05-28 NZ NZ216331A patent/NZ216331A/xx unknown
- 1986-05-28 NZ NZ216330A patent/NZ216330A/xx unknown
- 1986-05-28 ZA ZA863992A patent/ZA863992B/xx unknown
- 1986-05-28 ZA ZA863993A patent/ZA863993B/xx unknown
- 1986-05-28 AU AU58031/86A patent/AU579473B2/en not_active Ceased
- 1986-05-28 GR GR861369A patent/GR861369B/el unknown
- 1986-05-28 PT PT82673A patent/PT82673B/pt not_active IP Right Cessation
- 1986-05-28 US US06/867,474 patent/US4728647A/en not_active Expired - Fee Related
- 1986-05-28 US US06/867,555 patent/US4788204A/en not_active Expired - Fee Related
- 1986-05-28 GR GR861368A patent/GR861368B/el unknown
- 1986-05-29 SU SU864027526A patent/SU1440342A3/ru active
- 1986-05-29 MA MA20923A patent/MA20697A1/fr unknown
- 1986-05-29 DE DE8686401141T patent/DE3666813D1/de not_active Expired
- 1986-05-29 IL IL78968A patent/IL78968A/xx unknown
- 1986-05-29 HU HU862266A patent/HU195642B/hu unknown
- 1986-05-29 HU HU862265A patent/HU195641B/hu unknown
- 1986-05-29 AT AT86401140T patent/ATE40689T1/de active
- 1986-05-29 MA MA20922A patent/MA20696A1/fr unknown
- 1986-05-29 EP EP86401141A patent/EP0205375B1/fr not_active Expired
- 1986-05-29 DK DK252286A patent/DK252286A/da not_active Application Discontinuation
- 1986-05-29 SU SU864027667A patent/SU1508957A3/ru active
- 1986-05-29 CA CA000510308A patent/CA1264160A/fr not_active Expired - Lifetime
- 1986-05-29 AT AT86401141T patent/ATE47840T1/de not_active IP Right Cessation
- 1986-05-29 CA CA000510311A patent/CA1251206A/fr not_active Expired
- 1986-05-29 EP EP86401140A patent/EP0210084B1/fr not_active Expired
- 1986-05-29 NO NO862134A patent/NO862134L/no unknown
- 1986-05-29 NO NO862133A patent/NO862133L/no unknown
- 1986-05-29 DK DK252386A patent/DK252386A/da not_active Application Discontinuation
- 1986-05-29 IL IL78969A patent/IL78969A/xx unknown
- 1986-05-29 DE DE8686401140T patent/DE3662045D1/de not_active Expired
- 1986-05-30 JP JP61123872A patent/JPS625946A/ja active Pending
- 1986-05-30 JP JP61123873A patent/JPS6264A/ja active Pending
- 1986-05-30 TN TNTNSN86081A patent/TNSN86081A1/fr unknown
- 1986-05-30 ES ES555558A patent/ES8704732A1/es not_active Expired
- 1986-05-30 ES ES555557A patent/ES8704731A1/es not_active Expired
- 1986-05-30 TN TNTNSN86080A patent/TNSN86080A1/fr unknown
- 1986-10-31 ES ES557169A patent/ES8705227A1/es not_active Expired
- 1986-10-31 ES ES557167A patent/ES8800660A1/es not_active Expired
- 1986-10-31 ES ES557170A patent/ES8705228A1/es not_active Expired
- 1986-10-31 ES ES557166A patent/ES8705225A1/es not_active Expired
- 1986-10-31 ES ES557168A patent/ES8705226A1/es not_active Expired
-
1987
- 1987-03-09 SU SU874202112A patent/SU1470183A3/ru active
- 1987-04-06 SU SU874202362A patent/SU1544186A3/ru active
- 1987-04-06 SU SU874202412A patent/SU1614759A3/ru active
- 1987-04-06 SU SU874202398A patent/SU1537135A3/ru active
- 1987-04-06 SU SU874202297A patent/SU1470182A3/ru active
-
1988
- 1988-03-11 US US07/167,126 patent/US4788199A/en not_active Expired - Fee Related
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