CS248720B2 - Production method of quinolines - Google Patents
Production method of quinolines Download PDFInfo
- Publication number
- CS248720B2 CS248720B2 CS846210A CS621084A CS248720B2 CS 248720 B2 CS248720 B2 CS 248720B2 CS 846210 A CS846210 A CS 846210A CS 621084 A CS621084 A CS 621084A CS 248720 B2 CS248720 B2 CS 248720B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- methyl
- group
- formula
- alkyl
- alkyl group
- Prior art date
Links
- 229940111121 antirheumatic drug quinolines Drugs 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000003248 quinolines Chemical class 0.000 title 1
- -1 cyano, difluoromethoxy, methylsulphinyl Chemical group 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 5
- 150000007660 quinolones Chemical class 0.000 claims abstract description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 3
- 125000005843 halogen group Chemical group 0.000 claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 abstract description 6
- 150000003839 salts Chemical class 0.000 abstract description 5
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 3
- 150000001204 N-oxides Chemical class 0.000 abstract description 2
- 229940030600 antihypertensive agent Drugs 0.000 abstract description 2
- 239000002220 antihypertensive agent Substances 0.000 abstract description 2
- CPEONABTMRSIKA-UHFFFAOYSA-N 1,4$l^{2}-oxazinane Chemical compound C1COCC[N]1 CPEONABTMRSIKA-UHFFFAOYSA-N 0.000 abstract 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical group C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 5
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 241000124008 Mammalia Species 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000012265 solid product Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- HWHNFJYQDMSYAF-UHFFFAOYSA-N 1,5-dimethyltetrazole Chemical compound CC1=NN=NN1C HWHNFJYQDMSYAF-UHFFFAOYSA-N 0.000 description 2
- XZGLNCKSNVGDNX-UHFFFAOYSA-N 5-methyl-2h-tetrazole Chemical compound CC=1N=NNN=1 XZGLNCKSNVGDNX-UHFFFAOYSA-N 0.000 description 2
- AULVVHLFKXNDDC-UHFFFAOYSA-N 7-fluoro-1-methyl-3-(1-methyltetrazol-5-yl)quinolin-4-one Chemical compound CN1N=NN=C1C1=CN(C)C2=CC(F)=CC=C2C1=O AULVVHLFKXNDDC-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000000538 analytical sample Substances 0.000 description 2
- 230000003276 anti-hypertensive effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- VGGRCVDNFAQIKO-UHFFFAOYSA-N formic anhydride Chemical compound O=COC=O VGGRCVDNFAQIKO-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- IOSTYTUPOTYMES-UHFFFAOYSA-N methyl 4-fluoro-2-(methylamino)benzoate Chemical compound CNC1=CC(F)=CC=C1C(=O)OC IOSTYTUPOTYMES-UHFFFAOYSA-N 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 2
- PMZDQRJGMBOQBF-UHFFFAOYSA-N quinolin-4-ol Chemical compound C1=CC=C2C(O)=CC=NC2=C1 PMZDQRJGMBOQBF-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical group COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 2
- CEMAWMOMDPGJMB-UHFFFAOYSA-N (+-)-Oxprenolol Chemical compound CC(C)NCC(O)COC1=CC=CC=C1OCC=C CEMAWMOMDPGJMB-UHFFFAOYSA-N 0.000 description 1
- SYXKGGATRCNDOQ-UHFFFAOYSA-N (1-methyl-1h-tetrazol-5-yl)methyl lithium Chemical compound [Li+].CN1N=NN=C1[CH2-] SYXKGGATRCNDOQ-UHFFFAOYSA-N 0.000 description 1
- TWBNMYSKRDRHAT-RCWTXCDDSA-N (S)-timolol hemihydrate Chemical compound O.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1 TWBNMYSKRDRHAT-RCWTXCDDSA-N 0.000 description 1
- XTEVRJNKYYTSLF-UHFFFAOYSA-N 1,6-dimethyl-3,1-benzoxazine-2,4-dione Chemical compound CN1C(=O)OC(=O)C2=CC(C)=CC=C21 XTEVRJNKYYTSLF-UHFFFAOYSA-N 0.000 description 1
- QFDCJEWQWGGQLX-UHFFFAOYSA-N 1,6-dimethyl-3-(1-methyltetrazol-5-yl)quinolin-4-one Chemical compound O=C1C2=CC(C)=CC=C2N(C)C=C1C1=NN=NN1C QFDCJEWQWGGQLX-UHFFFAOYSA-N 0.000 description 1
- KNJHGBZGSGBVEU-UHFFFAOYSA-N 1,7-dimethyl-3-(1-methyltetrazol-5-yl)quinolin-4-one Chemical compound C=1C(C)=CC=C(C2=O)C=1N(C)C=C2C1=NN=NN1C KNJHGBZGSGBVEU-UHFFFAOYSA-N 0.000 description 1
- ANZBQVRQOPAZDM-UHFFFAOYSA-N 1-[4-fluoro-2-(methylamino)phenyl]-2-(1-methyltetrazol-5-yl)ethanone Chemical compound CNC1=CC(F)=CC=C1C(=O)CC1=NN=NN1C ANZBQVRQOPAZDM-UHFFFAOYSA-N 0.000 description 1
- IMWCSLSXSSYLMO-UHFFFAOYSA-N 1-methyl-3-(1-methyltetrazol-5-yl)quinolin-4-one Chemical compound CN1N=NN=C1C1=CN(C)C2=CC=CC=C2C1=O IMWCSLSXSSYLMO-UHFFFAOYSA-N 0.000 description 1
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- IIXZSGIPOINDJO-UHFFFAOYSA-N 6-methyl-1h-3,1-benzoxazine-2,4-dione Chemical compound N1C(=O)OC(=O)C2=CC(C)=CC=C21 IIXZSGIPOINDJO-UHFFFAOYSA-N 0.000 description 1
- WQTBUFJMYBSNQY-UHFFFAOYSA-N 7-ethyl-1-methyl-3-(1-methyltetrazol-5-yl)quinolin-4-one Chemical compound C=1C(CC)=CC=C(C2=O)C=1N(C)C=C2C1=NN=NN1C WQTBUFJMYBSNQY-UHFFFAOYSA-N 0.000 description 1
- UXNYABUCCNUIIF-UHFFFAOYSA-N 7-fluoro-1-methyl-3,1-benzoxazine-2,4-dione Chemical compound FC1=CC=C2C(=O)OC(=O)N(C)C2=C1 UXNYABUCCNUIIF-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 125000006519 CCH3 Chemical group 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 229960003515 bendroflumethiazide Drugs 0.000 description 1
- HDWIHXWEUNVBIY-UHFFFAOYSA-N bendroflumethiazidum Chemical compound C1=C(C(F)(F)F)C(S(=O)(=O)N)=CC(S(N2)(=O)=O)=C1NC2CC1=CC=CC=C1 HDWIHXWEUNVBIY-UHFFFAOYSA-N 0.000 description 1
- 239000002876 beta blocker Substances 0.000 description 1
- 229940097320 beta blocking agent Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229940075894 denatured ethanol Drugs 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- SZQUEWJRBJDHSM-UHFFFAOYSA-N iron(3+);trinitrate;nonahydrate Chemical compound O.O.O.O.O.O.O.O.O.[Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O SZQUEWJRBJDHSM-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 208000031225 myocardial ischemia Diseases 0.000 description 1
- HTFVNIFIHYDJTM-UHFFFAOYSA-N n-methylthiophen-2-amine Chemical compound CNC1=CC=CS1 HTFVNIFIHYDJTM-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 229960004570 oxprenolol Drugs 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002831 pharmacologic agent Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229960003712 propranolol Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000012306 spectroscopic technique Methods 0.000 description 1
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 1
- 125000001424 substituent group Chemical group 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
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229960004605 timolol Drugs 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- 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
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/24—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in positions 2 and 4
- C07D265/26—Two oxygen atoms, e.g. isatoic anhydride
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB838322470A GB8322470D0 (en) | 1983-08-20 | 1983-08-20 | Therapeutic agents |
| GB848413535A GB8413535D0 (en) | 1984-05-25 | 1984-05-25 | Therapeutic agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS248720B2 true CS248720B2 (en) | 1987-02-12 |
Family
ID=26286783
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS846210A CS248720B2 (en) | 1983-08-20 | 1984-08-16 | Production method of quinolines |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4659718A (da) |
| EP (1) | EP0135367B1 (da) |
| AU (1) | AU572177B2 (da) |
| CA (1) | CA1244420A (da) |
| CS (1) | CS248720B2 (da) |
| DD (1) | DD223451A5 (da) |
| DE (1) | DE3469898D1 (da) |
| DK (1) | DK395084A (da) |
| ES (3) | ES8701167A1 (da) |
| FI (1) | FI843266A7 (da) |
| GB (1) | GB2147581B (da) |
| GR (1) | GR80122B (da) |
| HU (1) | HUT35665A (da) |
| JO (1) | JO1330B1 (da) |
| NO (1) | NO843292L (da) |
| NZ (1) | NZ209193A (da) |
| PT (1) | PT79031B (da) |
| RO (1) | RO89124A (da) |
| ZW (1) | ZW13484A1 (da) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES8608874A1 (es) * | 1984-05-29 | 1986-09-01 | Pfizer | Un procedimiento para la preparacion de una 2-(1h)-quinolona |
| EP0172004B1 (en) * | 1984-08-15 | 1990-03-21 | The Boots Company PLC | Quinolinones, process for their preparation and pharmaceutical compositions containing them |
| GB8515209D0 (en) * | 1985-06-15 | 1985-07-17 | Boots Co Plc | Therapeutic agents |
| GB8529362D0 (en) * | 1985-11-28 | 1986-01-02 | Pfizer Ltd | Quinolone cardiac stimulants |
| GB8627698D0 (en) * | 1986-11-20 | 1986-12-17 | Boots Co Plc | Therapeutic agents |
| GB8804016D0 (en) * | 1988-02-22 | 1988-03-23 | Boots Co Plc | Therapeutic agents |
| GB9026389D0 (en) * | 1990-12-05 | 1991-01-23 | Merck Sharp & Dohme | Therapeutic agents |
| BR112014016930A8 (pt) | 2012-01-11 | 2017-12-26 | Bayer Ip Gmbh | compostos tetrazol-5-il- e triazol-5-il-arila e uso destes como herbicidas |
| WO2015052173A1 (en) | 2013-10-10 | 2015-04-16 | Basf Se | Tetrazole and triazole compounds and their use as herbicides |
| WO2015052178A1 (en) | 2013-10-10 | 2015-04-16 | Basf Se | 1,2,5-oxadiazole compounds and their use as herbicides |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50106975A (da) * | 1974-02-01 | 1975-08-22 | ||
| US4035368A (en) * | 1975-04-02 | 1977-07-12 | Riker Laboratories, Inc. | Substituted 3-(1H-tetrazol-5-yl)-quinoline compounds |
| US4474787A (en) * | 1977-05-04 | 1984-10-02 | Fisons Limited | 7,6 Dioxo-4H,6H-pyrano[3,2-g]quinoline dicarboxylic acids and anti-allergic use thereof |
| US4259437A (en) * | 1978-09-18 | 1981-03-31 | Ciba-Geigy Ag | Development inhibitor releasing compounds and their use in photographic materials |
| NZ193167A (en) * | 1979-03-27 | 1984-08-24 | Boots Co Plc | Quinoline derivatives and pharmaceutical compositions |
| IE51542B1 (en) * | 1980-09-26 | 1987-01-07 | Boots Co Ltd | Therapeutic agents |
| EP0104018A3 (en) * | 1982-09-21 | 1985-06-26 | FISONS plc | Benzopyran, benzothiapyran and quinoline compounds and pharmaceutical compositions containing them |
| US4735948A (en) * | 1983-03-25 | 1988-04-05 | Merrell Dow Pharmaceuticals Inc. | (1H-tetrazol-5-yl)-2(1H)-quinolinones and-naphthyridones and antiallergic use thereof |
-
1984
- 1984-08-06 PT PT79031A patent/PT79031B/pt unknown
- 1984-08-07 AU AU31667/84A patent/AU572177B2/en not_active Ceased
- 1984-08-13 JO JO19841330A patent/JO1330B1/en active
- 1984-08-13 NZ NZ209193A patent/NZ209193A/en unknown
- 1984-08-15 GB GB08420686A patent/GB2147581B/en not_active Expired
- 1984-08-15 EP EP84305548A patent/EP0135367B1/en not_active Expired
- 1984-08-15 DE DE8484305548T patent/DE3469898D1/de not_active Expired
- 1984-08-16 CS CS846210A patent/CS248720B2/cs unknown
- 1984-08-16 RO RO84115508A patent/RO89124A/ro unknown
- 1984-08-16 GR GR80122A patent/GR80122B/el unknown
- 1984-08-16 DD DD84266334A patent/DD223451A5/de unknown
- 1984-08-17 FI FI843266A patent/FI843266A7/fi not_active Application Discontinuation
- 1984-08-17 ES ES535273A patent/ES8701167A1/es not_active Expired
- 1984-08-17 CA CA000461302A patent/CA1244420A/en not_active Expired
- 1984-08-17 DK DK395084A patent/DK395084A/da unknown
- 1984-08-17 NO NO843292A patent/NO843292L/no unknown
- 1984-08-17 HU HU843128A patent/HUT35665A/hu unknown
- 1984-08-21 ZW ZW134/84A patent/ZW13484A1/xx unknown
-
1985
- 1985-06-26 US US06/749,015 patent/US4659718A/en not_active Expired - Fee Related
- 1985-08-01 ES ES545835A patent/ES8607280A1/es not_active Expired
- 1985-08-01 ES ES545834A patent/ES8607279A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| EP0135367A1 (en) | 1985-03-27 |
| JO1330B1 (en) | 1986-11-30 |
| EP0135367B1 (en) | 1988-03-16 |
| NO843292L (no) | 1985-02-21 |
| FI843266A0 (fi) | 1984-08-17 |
| PT79031B (en) | 1986-08-22 |
| ES535273A0 (es) | 1986-11-16 |
| RO89124A (ro) | 1986-04-30 |
| ES545834A0 (es) | 1986-05-16 |
| DE3469898D1 (en) | 1988-04-21 |
| AU3166784A (en) | 1985-02-21 |
| US4659718A (en) | 1987-04-21 |
| CA1244420A (en) | 1988-11-08 |
| GB2147581A (en) | 1985-05-15 |
| HUT35665A (en) | 1985-07-29 |
| GB8420686D0 (en) | 1984-09-19 |
| ES8607279A1 (es) | 1986-05-16 |
| FI843266A7 (fi) | 1985-02-21 |
| PT79031A (en) | 1984-09-01 |
| ES545835A0 (es) | 1986-05-16 |
| ES8607280A1 (es) | 1986-05-16 |
| GR80122B (en) | 1984-12-13 |
| DK395084D0 (da) | 1984-08-17 |
| GB2147581B (en) | 1987-04-01 |
| NZ209193A (en) | 1987-04-30 |
| AU572177B2 (en) | 1988-05-05 |
| ZW13484A1 (en) | 1985-03-13 |
| DD223451A5 (de) | 1985-06-12 |
| ES8701167A1 (es) | 1986-11-16 |
| DK395084A (da) | 1985-02-21 |
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