DE2352585A1 - Pyridinderivate - Google Patents
PyridinderivateInfo
- Publication number
- DE2352585A1 DE2352585A1 DE19732352585 DE2352585A DE2352585A1 DE 2352585 A1 DE2352585 A1 DE 2352585A1 DE 19732352585 DE19732352585 DE 19732352585 DE 2352585 A DE2352585 A DE 2352585A DE 2352585 A1 DE2352585 A1 DE 2352585A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- compound
- hydrogen
- methyl
- tetrahydroquinoline
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title description 31
- 150000001875 compounds Chemical class 0.000 claims description 160
- 229910052739 hydrogen Inorganic materials 0.000 claims description 87
- 239000001257 hydrogen Substances 0.000 claims description 85
- 238000000034 method Methods 0.000 claims description 70
- 125000000217 alkyl group Chemical group 0.000 claims description 56
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 40
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 39
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 38
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
- 229910052751 metal Inorganic materials 0.000 claims description 37
- 239000002184 metal Substances 0.000 claims description 37
- 150000003839 salts Chemical class 0.000 claims description 31
- 239000007858 starting material Substances 0.000 claims description 25
- -1 alkyl compound Chemical class 0.000 claims description 24
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 24
- 150000003254 radicals Chemical class 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 238000002360 preparation method Methods 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 20
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 18
- 150000001408 amides Chemical class 0.000 claims description 16
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 16
- 239000011734 sodium Substances 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 16
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 229910052744 lithium Chemical group 0.000 claims description 10
- 150000002825 nitriles Chemical class 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 9
- 229910021529 ammonia Inorganic materials 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 229910052708 sodium Inorganic materials 0.000 claims description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 8
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 8
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 8
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 8
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 8
- 230000018044 dehydration Effects 0.000 claims description 8
- 238000006297 dehydration reaction Methods 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- AIMIAJHGOMWBQG-UHFFFAOYSA-N 3-methyl-5,6,7,8-tetrahydroquinoline-8-carbothioamide Chemical compound NC(=S)C1CCCC2=CC(C)=CN=C21 AIMIAJHGOMWBQG-UHFFFAOYSA-N 0.000 claims description 7
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical class [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 150000002367 halogens Chemical group 0.000 claims description 7
- KDCUJIVABVWMSY-UHFFFAOYSA-N 3-methyl-5,6,7,8-tetrahydroquinoline-8-carboxamide Chemical compound NC(=O)C1CCCC2=CC(C)=CN=C21 KDCUJIVABVWMSY-UHFFFAOYSA-N 0.000 claims description 6
- 229940069428 antacid Drugs 0.000 claims description 6
- 239000003159 antacid agent Substances 0.000 claims description 6
- 150000005840 aryl radicals Chemical class 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 239000008177 pharmaceutical agent Substances 0.000 claims description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 5
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- 230000001458 anti-acid effect Effects 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 150000001721 carbon Chemical group 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims description 5
- 239000011591 potassium Chemical group 0.000 claims description 5
- 229910052700 potassium Inorganic materials 0.000 claims description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
- 239000011575 calcium Substances 0.000 claims description 4
- 229910052791 calcium Inorganic materials 0.000 claims description 4
- 239000001569 carbon dioxide Substances 0.000 claims description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 4
- 239000011777 magnesium Chemical group 0.000 claims description 4
- 229910052749 magnesium Chemical group 0.000 claims description 4
- 150000003141 primary amines Chemical class 0.000 claims description 4
- 150000003335 secondary amines Chemical class 0.000 claims description 4
- 150000007970 thio esters Chemical class 0.000 claims description 4
- BEAGPPIXIZRVES-UHFFFAOYSA-N 2-phenyl-5,6,7,8-tetrahydroquinoline-8-carbonitrile Chemical compound N1=C2C(C#N)CCCC2=CC=C1C1=CC=CC=C1 BEAGPPIXIZRVES-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 3
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 claims description 3
- 150000003222 pyridines Chemical class 0.000 claims description 3
- 229940095064 tartrate Drugs 0.000 claims description 3
- YZUYBEOJTAVBPY-UHFFFAOYSA-N 2-methyl-5,6,7,8-tetrahydroquinoline-8-carbonitrile Chemical compound C1CCC(C#N)C2=NC(C)=CC=C21 YZUYBEOJTAVBPY-UHFFFAOYSA-N 0.000 claims description 2
- VGVJPUVJZCJEAO-UHFFFAOYSA-N 2-tert-butyl-5,6,7,8-tetrahydroquinoline-8-carbothioamide Chemical compound C1CCC(C(N)=S)C2=NC(C(C)(C)C)=CC=C21 VGVJPUVJZCJEAO-UHFFFAOYSA-N 0.000 claims description 2
- ROGNOAZMZCNUEJ-UHFFFAOYSA-N 2-tert-butyl-5,6,7,8-tetrahydroquinoline-8-carboxamide Chemical compound C1CCC(C(N)=O)C2=NC(C(C)(C)C)=CC=C21 ROGNOAZMZCNUEJ-UHFFFAOYSA-N 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 125000005265 dialkylamine group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 9
- HOJOOIORADNBJU-UHFFFAOYSA-N 2-methyl-5,6,7,8-tetrahydroquinoline-8-carbothioamide Chemical compound C1CCC(C(N)=S)C2=NC(C)=CC=C21 HOJOOIORADNBJU-UHFFFAOYSA-N 0.000 claims 1
- ROEGMZJUYFNSCS-UHFFFAOYSA-N 3-methyl-5,6,7,8-tetrahydroquinoline-8-carbothioamide;oxalic acid Chemical compound OC(=O)C(O)=O.NC(=S)C1CCCC2=CC(C)=CN=C21 ROEGMZJUYFNSCS-UHFFFAOYSA-N 0.000 claims 1
- HWVIKBAAKYHVHW-UHFFFAOYSA-N 5,6,7,8-tetrahydroquinoline-2-carbonitrile Chemical compound C1CCCC2=NC(C#N)=CC=C21 HWVIKBAAKYHVHW-UHFFFAOYSA-N 0.000 claims 1
- KORYAMUIXKTLTJ-UHFFFAOYSA-N 5,6,7,8-tetrahydroquinoline-8-carboxamide Chemical compound C1=CN=C2C(C(=O)N)CCCC2=C1 KORYAMUIXKTLTJ-UHFFFAOYSA-N 0.000 claims 1
- YGAZKIVUTUQLGS-UHFFFAOYSA-N CC(CCC1C#N)C2=C1N=CC=C2 Chemical compound CC(CCC1C#N)C2=C1N=CC=C2 YGAZKIVUTUQLGS-UHFFFAOYSA-N 0.000 claims 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims 1
- 150000003857 carboxamides Chemical class 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 claims 1
- WFVSNGIXEIRSCQ-UHFFFAOYSA-N methyl 3-methyl-5,6,7,8-tetrahydroquinoline-8-carboxylate Chemical compound CC1=CN=C2C(C(=O)OC)CCCC2=C1 WFVSNGIXEIRSCQ-UHFFFAOYSA-N 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 152
- 239000000243 solution Substances 0.000 description 78
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 59
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 53
- 239000000203 mixture Substances 0.000 description 44
- 239000000284 extract Substances 0.000 description 41
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- 239000003921 oil Substances 0.000 description 38
- 235000019198 oils Nutrition 0.000 description 38
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 38
- 238000004458 analytical method Methods 0.000 description 36
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 35
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 35
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 35
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 34
- 239000002904 solvent Substances 0.000 description 34
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 28
- 239000011541 reaction mixture Substances 0.000 description 28
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- 239000007789 gas Substances 0.000 description 24
- 229920006395 saturated elastomer Polymers 0.000 description 24
- 239000007787 solid Substances 0.000 description 23
- 239000007864 aqueous solution Substances 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 12
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 12
- 239000013078 crystal Substances 0.000 description 11
- 239000004480 active ingredient Substances 0.000 description 10
- 238000002329 infrared spectrum Methods 0.000 description 10
- 150000003556 thioamides Chemical class 0.000 description 10
- GMMKZUPOLVXWFF-UHFFFAOYSA-N 3-methyl-5,6,7,8-tetrahydroquinoline Chemical compound C1CCCC2=CC(C)=CN=C21 GMMKZUPOLVXWFF-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000012230 colorless oil Substances 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 238000007429 general method Methods 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- YQDGQEKUTLYWJU-UHFFFAOYSA-N 5,6,7,8-tetrahydroquinoline Chemical compound C1=CC=C2CCCCC2=N1 YQDGQEKUTLYWJU-UHFFFAOYSA-N 0.000 description 4
- MUZLJLSOGBHBDC-UHFFFAOYSA-N 5,6,7,8-tetrahydroquinoline-8-carbothioamide Chemical compound C1=CN=C2C(C(=S)N)CCCC2=C1 MUZLJLSOGBHBDC-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 4
- 238000006473 carboxylation reaction Methods 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- DBYQHFPBWKKZAT-UHFFFAOYSA-N lithium;benzene Chemical compound [Li+].C1=CC=[C-]C=C1 DBYQHFPBWKKZAT-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000001525 mentha piperita l. herb oil Substances 0.000 description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 4
- 235000019477 peppermint oil Nutrition 0.000 description 4
- 229940075930 picrate Drugs 0.000 description 4
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- CPKVUHPKYQGHMW-UHFFFAOYSA-N 1-ethenylpyrrolidin-2-one;molecular iodine Chemical compound II.C=CN1CCCC1=O CPKVUHPKYQGHMW-UHFFFAOYSA-N 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000021523 carboxylation Effects 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000006114 decarboxylation reaction Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 3
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- 235000006408 oxalic acid Nutrition 0.000 description 1
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000012057 packaged powder Substances 0.000 description 1
- 239000013618 particulate matter Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- QDZPVHAEVIWJKP-UHFFFAOYSA-N quinoline-8-carbothioamide Chemical compound C1=CN=C2C(C(=S)N)=CC=CC2=C1 QDZPVHAEVIWJKP-UHFFFAOYSA-N 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 229940085605 saccharin sodium Drugs 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000009738 saturating 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
- 238000007086 side reaction Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000010626 work up procedure 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
- C07D215/04—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/02—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with only hydrogen, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine 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 ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4859572 | 1972-10-21 | ||
| GB742473*[A GB1432378A (en) | 1972-10-21 | 1973-02-15 | Fused carbocyclic ring derivatives of pyridine |
| GB3488673 | 1973-07-21 | ||
| GB3870173 | 1973-08-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2352585A1 true DE2352585A1 (de) | 1974-05-09 |
Family
ID=27447589
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732352585 Withdrawn DE2352585A1 (de) | 1972-10-21 | 1973-10-19 | Pyridinderivate |
Country Status (16)
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3963722A (en) * | 1973-11-26 | 1976-06-15 | John Wyeth & Brother Limited | Magnesium halide derivatives of tetrahydroquinolines |
| US3992383A (en) * | 1973-12-17 | 1976-11-16 | John Wyeth & Brother Limited | Process for preparing pyridine derivatives |
| US4000142A (en) * | 1973-12-17 | 1976-12-28 | John Wyeth & Brother Limited | Process for preparing pyridine derivatives |
| US4011228A (en) * | 1973-11-26 | 1977-03-08 | John Wyeth & Brother Limited | Carboxylic acid salts of tetrahydroquinolines and pyridine derivatives |
| US4085110A (en) * | 1972-10-21 | 1978-04-18 | John Wyeth & Brother, Ltd. | 1,2,3,5,6,7-Hexahydrodicyclopenta[b,e]pyridine derivatives |
| US4909454A (en) * | 1986-08-27 | 1990-03-20 | Jagenberg Aktiengesellschaft | Apparatus for inserting a winding sleeve or core into a winding machine |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1561648A (en) | 1976-12-18 | 1980-02-27 | Wyeth John & Brother Ltd | Copper complexes of tetrahydroquinoline 8 - thiocarboxamides and related compounds |
| CA1138464A (en) * | 1980-12-09 | 1982-12-28 | Robin G. Shepherd | Process for preparing pyridine derivatives |
| GB2088860B (en) * | 1980-12-09 | 1984-05-23 | Wyeth John & Brother Ltd | Process for preparing ring-fused pyridine derivatives |
| US4727149A (en) * | 1982-03-11 | 1988-02-23 | John Wyeth & Brother Limited | Preparation of nitriles of fused ring pyridine derivatives |
| GB2122992B (en) * | 1982-06-25 | 1986-12-03 | Wyeth John & Brother Ltd | Preparation of tetrahydroquinolines and related compounds |
| US4577022A (en) * | 1982-06-25 | 1986-03-18 | John Wyeth & Brother, Ltd. | Silyl compounds |
| US4539406A (en) * | 1982-06-25 | 1985-09-03 | John Wyeth & Brother Limited | Preparation of fused carbocyclic ring derivatives of pyridine |
| DE3233089A1 (de) * | 1982-09-07 | 1984-03-08 | Basf Ag, 6700 Ludwigshafen | Chinolinderivate, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung unerwuenschten pflanzenwuchses |
| GB8301377D0 (en) * | 1983-01-19 | 1983-02-23 | Wyeth John & Brother Ltd | Quinoline derivatives |
| IL112566A (en) * | 1994-02-10 | 2000-10-31 | Wyeth John & Brother Ltd | Substituted quinolinones and pharmaceutical compositions containing them |
| IL112567A (en) * | 1994-02-10 | 2000-02-29 | Wyeth John & Brother Ltd | Substituted quinolines their preparation and pharmaceutical compositions containing them |
| IL112568A0 (en) * | 1994-02-10 | 1995-05-26 | Wyeth John & Brother Ltd | Substituted quinolines, their preparation and pharmaceutical compositions containing them |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH46A (de) * | 1889-01-09 | Milovanovitsch Koka Kosta R | Schnellladevorrichtung für Hinterladegewehre | |
| DE2032738A1 (de) * | 1969-07-08 | 1971-01-21 | Takeda Chemical Industries, Ltd , Osaka (Japan) | Neue Pyridinthioacetamiddenvate und Verfahren zu ihrer Herstellung |
-
1973
- 1973-02-15 GB GB742473*[A patent/GB1432378A/en not_active Expired
- 1973-09-17 CY CY996A patent/CY996A/xx unknown
- 1973-10-10 AU AU61205/73A patent/AU474567B2/en not_active Expired
- 1973-10-16 AR AR250561A patent/AR203377A1/es active
- 1973-10-17 CH CH1469173A patent/CH602648A5/xx not_active IP Right Cessation
- 1973-10-17 CH CH75677A patent/CH592627A5/xx not_active IP Right Cessation
- 1973-10-18 NL NLAANVRAGE7314359,A patent/NL180213C/xx active Search and Examination
- 1973-10-19 IN IN2330/CAL/73A patent/IN139235B/en unknown
- 1973-10-19 DE DE19732352585 patent/DE2352585A1/de not_active Withdrawn
- 1973-10-19 FR FR7337467A patent/FR2203634B1/fr not_active Expired
- 1973-10-19 CA CA183,807A patent/CA1011741A/en not_active Expired
- 1973-10-19 FI FI3252/73A patent/FI52977C/fi active
- 1973-10-19 PH PH15130A patent/PH12029A/en unknown
- 1973-10-19 IE IE1873/73A patent/IE38393B1/xx unknown
-
1976
- 1976-03-03 PH PH18165A patent/PH12293A/en unknown
-
1977
- 1977-10-17 CH CH1001577A patent/CH601245A5/xx not_active IP Right Cessation
-
1979
- 1979-02-22 KE KE2922A patent/KE2922A/xx unknown
- 1979-04-04 HK HK244/79A patent/HK24479A/xx unknown
- 1979-12-31 MY MY1979173A patent/MY7900173A/xx unknown
Non-Patent Citations (1)
| Title |
|---|
| EBERHART-RUSCHIG, Arzneimittel, Bd. 2, 1972, S.94, 95 u. 99 * |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4085110A (en) * | 1972-10-21 | 1978-04-18 | John Wyeth & Brother, Ltd. | 1,2,3,5,6,7-Hexahydrodicyclopenta[b,e]pyridine derivatives |
| US3963722A (en) * | 1973-11-26 | 1976-06-15 | John Wyeth & Brother Limited | Magnesium halide derivatives of tetrahydroquinolines |
| US4011228A (en) * | 1973-11-26 | 1977-03-08 | John Wyeth & Brother Limited | Carboxylic acid salts of tetrahydroquinolines and pyridine derivatives |
| US3992383A (en) * | 1973-12-17 | 1976-11-16 | John Wyeth & Brother Limited | Process for preparing pyridine derivatives |
| US4000142A (en) * | 1973-12-17 | 1976-12-28 | John Wyeth & Brother Limited | Process for preparing pyridine derivatives |
| US4909454A (en) * | 1986-08-27 | 1990-03-20 | Jagenberg Aktiengesellschaft | Apparatus for inserting a winding sleeve or core into a winding machine |
| US5000395A (en) * | 1986-08-27 | 1991-03-19 | Jagenberg Aktiengesellschaft | Apparatus for inserting a winding sleeve or core into a winding machine |
Also Published As
| Publication number | Publication date |
|---|---|
| KE2922A (en) | 1979-03-09 |
| NL7314359A (enrdf_load_stackoverflow) | 1974-04-23 |
| FI52977C (enrdf_load_stackoverflow) | 1978-01-10 |
| IE38393L (en) | 1974-04-21 |
| IE38393B1 (en) | 1978-03-01 |
| FI52977B (enrdf_load_stackoverflow) | 1977-09-30 |
| CA1011741A (en) | 1977-06-07 |
| CH602648A5 (enrdf_load_stackoverflow) | 1978-07-31 |
| CY996A (en) | 1979-08-02 |
| AU474567B2 (en) | 1976-07-29 |
| PH12293A (en) | 1978-12-29 |
| FR2203634A1 (enrdf_load_stackoverflow) | 1974-05-17 |
| CH601245A5 (enrdf_load_stackoverflow) | 1978-06-30 |
| PH12029A (en) | 1978-10-16 |
| HK24479A (en) | 1979-04-12 |
| IN139235B (enrdf_load_stackoverflow) | 1976-05-22 |
| AU6120573A (en) | 1975-04-10 |
| NL180213C (nl) | 1987-01-16 |
| FR2203634B1 (enrdf_load_stackoverflow) | 1977-09-09 |
| MY7900173A (en) | 1979-12-31 |
| GB1432378A (en) | 1976-04-14 |
| CH592627A5 (enrdf_load_stackoverflow) | 1977-10-31 |
| AR203377A1 (es) | 1975-09-08 |
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