FI56529C - Pyridinderivat som aer mellanprodukter vid framstaellning av terapeutiskt aktiva tioamidocykloalkylenpyridinderivat - Google Patents
Pyridinderivat som aer mellanprodukter vid framstaellning av terapeutiskt aktiva tioamidocykloalkylenpyridinderivat Download PDFInfo
- Publication number
- FI56529C FI56529C FI763685A FI763685A FI56529C FI 56529 C FI56529 C FI 56529C FI 763685 A FI763685 A FI 763685A FI 763685 A FI763685 A FI 763685A FI 56529 C FI56529 C FI 56529C
- Authority
- FI
- Finland
- Prior art keywords
- tetrahydroquinoline
- methyl
- ether
- formula
- hydrogen
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 111
- 229910052739 hydrogen Inorganic materials 0.000 claims description 45
- 239000001257 hydrogen Substances 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 11
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 150000003222 pyridines Chemical class 0.000 claims description 4
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims 2
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical group [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 155
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 77
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 59
- 239000000243 solution Substances 0.000 description 59
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 47
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 47
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 41
- 238000000034 method Methods 0.000 description 39
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 36
- 239000000284 extract Substances 0.000 description 34
- 239000000203 mixture Substances 0.000 description 34
- 239000011541 reaction mixture Substances 0.000 description 32
- 239000002904 solvent Substances 0.000 description 32
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 31
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 29
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- 239000007789 gas Substances 0.000 description 27
- 239000007787 solid Substances 0.000 description 25
- 239000003921 oil Substances 0.000 description 21
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 20
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 18
- 229920006395 saturated elastomer Polymers 0.000 description 18
- 239000007864 aqueous solution Substances 0.000 description 17
- -1 cyclohutyl Chemical group 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- 238000010992 reflux Methods 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 229910052751 metal Inorganic materials 0.000 description 15
- 239000002184 metal Substances 0.000 description 15
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 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 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- GMMKZUPOLVXWFF-UHFFFAOYSA-N 3-methyl-5,6,7,8-tetrahydroquinoline Chemical compound C1CCCC2=CC(C)=CN=C21 GMMKZUPOLVXWFF-UHFFFAOYSA-N 0.000 description 10
- 150000001408 amides Chemical class 0.000 description 10
- 239000012230 colorless oil Substances 0.000 description 10
- 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 description 9
- 238000004458 analytical method Methods 0.000 description 9
- 239000012259 ether extract Substances 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 150000002825 nitriles Chemical class 0.000 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 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 239000008346 aqueous phase Substances 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 6
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 239000012267 brine Substances 0.000 description 6
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 229910052744 lithium Chemical group 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- 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 description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 5
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 230000018044 dehydration Effects 0.000 description 5
- 238000006297 dehydration reaction Methods 0.000 description 5
- 238000002329 infrared spectrum Methods 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 150000003556 thioamides Chemical class 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 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
- 239000000460 chlorine Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 230000032050 esterification Effects 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- 238000007429 general method Methods 0.000 description 4
- NSDLEELVPNRYRH-UHFFFAOYSA-N methyl 5,6,7,8-tetrahydroquinoline-8-carboxylate Chemical compound C1=CN=C2C(C(=O)OC)CCCC2=C1 NSDLEELVPNRYRH-UHFFFAOYSA-N 0.000 description 4
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 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
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000003637 basic solution Substances 0.000 description 3
- 150000003857 carboxamides Chemical class 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 230000021523 carboxylation Effects 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000006114 decarboxylation reaction Methods 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- OEZAAXHZEMTBOV-DUXPYHPUSA-N (e)-3-amino-2-methylprop-2-enal Chemical compound N\C=C(/C)C=O OEZAAXHZEMTBOV-DUXPYHPUSA-N 0.000 description 2
- UCRYVFBKCBUURB-UPHRSURJSA-N (z)-3-aminoprop-2-enal Chemical compound N\C=C/C=O UCRYVFBKCBUURB-UPHRSURJSA-N 0.000 description 2
- LLCXJIQXTXEQID-UHFFFAOYSA-N 1,2,3,4,5,6,7,8-octahydroacridine Chemical compound C1CCCC2=C1N=C1CCCCC1=C2 LLCXJIQXTXEQID-UHFFFAOYSA-N 0.000 description 2
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 2
- AUSMPOZTRKHFPG-UHFFFAOYSA-N 2-methyl-5,6,7,8-tetrahydroquinoline Chemical compound C1CCCC2=NC(C)=CC=C21 AUSMPOZTRKHFPG-UHFFFAOYSA-N 0.000 description 2
- RGSIOWMEWWKKNK-UHFFFAOYSA-N 2-methyl-5,6,7,8-tetrahydroquinoline-8-carboxamide Chemical compound C1CCC(C(N)=O)C2=NC(C)=CC=C21 RGSIOWMEWWKKNK-UHFFFAOYSA-N 0.000 description 2
- TYDLLLIJBOGWJA-UHFFFAOYSA-N 2-phenyl-5,6,7,8-tetrahydroquinoline Chemical compound C=1C=C2CCCCC2=NC=1C1=CC=CC=C1 TYDLLLIJBOGWJA-UHFFFAOYSA-N 0.000 description 2
- QXPHVVQSCLXOOZ-UHFFFAOYSA-N 2-phenyl-5,6,7,8-tetrahydroquinoline-8-carbothioamide Chemical compound N1=C2C(C(=S)N)CCCC2=CC=C1C1=CC=CC=C1 QXPHVVQSCLXOOZ-UHFFFAOYSA-N 0.000 description 2
- ATADKLRTGCDSCA-UHFFFAOYSA-N 2-tert-butyl-5,6,7,8-tetrahydroquinoline Chemical compound C1CCCC2=NC(C(C)(C)C)=CC=C21 ATADKLRTGCDSCA-UHFFFAOYSA-N 0.000 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 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- NDMPTWYIVGDYNM-UHFFFAOYSA-N 3-methyl-5,6,7,8-tetrahydroquinoline-8-carbonitrile Chemical compound N#CC1CCCC2=CC(C)=CN=C21 NDMPTWYIVGDYNM-UHFFFAOYSA-N 0.000 description 2
- YQDGQEKUTLYWJU-UHFFFAOYSA-N 5,6,7,8-tetrahydroquinoline Chemical compound C1=CC=C2CCCCC2=N1 YQDGQEKUTLYWJU-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- 241000786363 Rhampholeon spectrum Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- YOPNLHHNSGCXOQ-UHFFFAOYSA-N methyl 2-phenyl-5,6,7,8-tetrahydroquinoline-8-carboxylate Chemical compound N1=C2C(C(=O)OC)CCCC2=CC=C1C1=CC=CC=C1 YOPNLHHNSGCXOQ-UHFFFAOYSA-N 0.000 description 2
- PFBUFIPRGDJOFA-UHFFFAOYSA-N methyl 2-tert-butyl-5,6,7,8-tetrahydroquinoline-8-carboxylate Chemical compound C1=C(C(C)(C)C)N=C2C(C(=O)OC)CCCC2=C1 PFBUFIPRGDJOFA-UHFFFAOYSA-N 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000011591 potassium Chemical group 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000002211 ultraviolet spectrum Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- ZWAJLVLEBYIOTI-OLQVQODUSA-N (1s,6r)-7-oxabicyclo[4.1.0]heptane Chemical compound C1CCC[C@@H]2O[C@@H]21 ZWAJLVLEBYIOTI-OLQVQODUSA-N 0.000 description 1
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- XJQSLJZYZFSHAI-DUXPYHPUSA-N (e)-3-methoxyprop-2-enal Chemical compound CO\C=C\C=O XJQSLJZYZFSHAI-DUXPYHPUSA-N 0.000 description 1
- XHTYQFMRBQUCPX-UHFFFAOYSA-N 1,1,3,3-tetramethoxypropane Chemical compound COC(OC)CC(OC)OC XHTYQFMRBQUCPX-UHFFFAOYSA-N 0.000 description 1
- WFEKFUDZCWEZQO-UHFFFAOYSA-N 1,2,3,5,6,7-hexahydrodicyclopenta[2,1-b:2',1'-f]pyridine Chemical compound N1=C2CCCC2=CC2=C1CCC2 WFEKFUDZCWEZQO-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- ZWTRBKDMAOBJTL-UHFFFAOYSA-N 2,3-dihydroxybutanedioic acid;3-methyl-5,6,7,8-tetrahydroquinoline-8-carbothioamide Chemical compound OC(=O)C(O)C(O)C(O)=O.NC(=S)C1CCCC2=CC(C)=CN=C21 ZWTRBKDMAOBJTL-UHFFFAOYSA-N 0.000 description 1
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- QUGAFXVKYGZLBW-UHFFFAOYSA-N 2-(5,6,7,8-tetrahydroquinolin-2-yl)acetamide Chemical compound C1CCCC2=NC(CC(=O)N)=CC=C21 QUGAFXVKYGZLBW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- RXQSSHJWZNGJHL-UHFFFAOYSA-N 2-butyl-5,6,7,8-tetrahydroquinoline Chemical compound C1CCCC2=NC(CCCC)=CC=C21 RXQSSHJWZNGJHL-UHFFFAOYSA-N 0.000 description 1
- ZBFYHZDSGMEHFJ-UHFFFAOYSA-N 2-butyl-5,6,7,8-tetrahydroquinoline-8-carbothioamide Chemical compound C1CCC(C(N)=S)C2=NC(CCCC)=CC=C21 ZBFYHZDSGMEHFJ-UHFFFAOYSA-N 0.000 description 1
- OCOSFCPHXTYCKT-UHFFFAOYSA-N 2-ethyl-5,6,7,8-tetrahydroquinoline Chemical compound C1CCCC2=NC(CC)=CC=C21 OCOSFCPHXTYCKT-UHFFFAOYSA-N 0.000 description 1
- LCPGSEUWQDGIFE-UHFFFAOYSA-N 2-ethyl-5,6,7,8-tetrahydroquinoline-8-carbothioamide Chemical compound C1CCC(C(N)=S)C2=NC(CC)=CC=C21 LCPGSEUWQDGIFE-UHFFFAOYSA-N 0.000 description 1
- KGNSBBJPUOPJAL-UHFFFAOYSA-N 2-methyl-5,6,7,8-tetrahydroquinoline-8-carbothioamide 2-methyl-5,6,7,8-tetrahydroquinoline-8-carboxamide Chemical compound CC1=NC=2C(CCCC2C=C1)C(=O)N.CC1=NC=2C(CCCC2C=C1)C(N)=S KGNSBBJPUOPJAL-UHFFFAOYSA-N 0.000 description 1
- JNTFXVBDIFJNSJ-UHFFFAOYSA-N 2-phenyl-5,6,7,8-tetrahydroquinoline-8-carboxamide Chemical compound N1=C2C(C(=O)N)CCCC2=CC=C1C1=CC=CC=C1 JNTFXVBDIFJNSJ-UHFFFAOYSA-N 0.000 description 1
- FXVQFONFQPXIEY-UHFFFAOYSA-N 2-phenyl-5,6,7,8-tetrahydroquinoline-8-carboxylic acid;hydrochloride Chemical compound Cl.N1=C2C(C(=O)O)CCCC2=CC=C1C1=CC=CC=C1 FXVQFONFQPXIEY-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- KMEQNTYVSZCYBI-UHFFFAOYSA-N 3,3-dimethyl-5,6,7,8-tetrahydro-2H-quinoline Chemical compound CC1(CN=C2CCCCC2=C1)C KMEQNTYVSZCYBI-UHFFFAOYSA-N 0.000 description 1
- SFZMBPVISPQRGW-UHFFFAOYSA-N 3,5-dimethyl-5,6,7,8-tetrahydroquinoline Chemical compound C1=C(C)C=C2C(C)CCCC2=N1 SFZMBPVISPQRGW-UHFFFAOYSA-N 0.000 description 1
- XSNSOIPVQHVAJL-UHFFFAOYSA-N 3,5-dimethyl-5,6,7,8-tetrahydroquinoline-8-carbothioamide Chemical compound C1=C(C)C=C2C(C)CCC(C(N)=S)C2=N1 XSNSOIPVQHVAJL-UHFFFAOYSA-N 0.000 description 1
- CKANKFXXMJXJDP-UHFFFAOYSA-N 3,6-dimethyl-5,6,7,8-tetrahydroquinoline Chemical compound C1=C(C)C=C2CC(C)CCC2=N1 CKANKFXXMJXJDP-UHFFFAOYSA-N 0.000 description 1
- RHNVDGQZTHHJRU-UHFFFAOYSA-N 3,6-dimethyl-5,6,7,8-tetrahydroquinoline-8-carbothioamide Chemical compound C1=C(C)C=C2CC(C)CC(C(N)=S)C2=N1 RHNVDGQZTHHJRU-UHFFFAOYSA-N 0.000 description 1
- FJRNTKHTMQXFJJ-UHFFFAOYSA-N 3,7,7-trimethyl-6,8-dihydro-5h-quinoline Chemical compound C1C(C)(C)CCC2=CC(C)=CN=C21 FJRNTKHTMQXFJJ-UHFFFAOYSA-N 0.000 description 1
- ZZMRPOAHZITKBV-UHFFFAOYSA-N 3-aminocyclohex-2-en-1-one Chemical compound NC1=CC(=O)CCC1 ZZMRPOAHZITKBV-UHFFFAOYSA-N 0.000 description 1
- KYIUXKQDIWZDEF-UHFFFAOYSA-N 3-methyl-5,6,7,8-tetrahydroquinoline-8-carbothioamide;hydrochloride Chemical compound Cl.NC(=S)C1CCCC2=CC(C)=CN=C21 KYIUXKQDIWZDEF-UHFFFAOYSA-N 0.000 description 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 description 1
- NAVUPLRVXZTTOK-UHFFFAOYSA-N 3-methyl-5,6,7,8-tetrahydroquinoline-8-carboxylic acid Chemical compound OC(=O)C1CCCC2=CC(C)=CN=C21 NAVUPLRVXZTTOK-UHFFFAOYSA-N 0.000 description 1
- LGYCOYCCCKHXGC-UHFFFAOYSA-N 5,6,7,8-tetrahydro-4-methylquinoline Chemical compound C1CCCC2=C1N=CC=C2C LGYCOYCCCKHXGC-UHFFFAOYSA-N 0.000 description 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 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 description 1
- 101100293593 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) nar-1 gene Proteins 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 101000722960 Onchocerca volvulus Onchocystatin Proteins 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- 238000005644 Wolff-Kishner reduction reaction Methods 0.000 description 1
- DVYXIGZUUOODBX-UHFFFAOYSA-N [Cl-].C(N)(=S)C=1C=[NH+]C=CC=1 Chemical compound [Cl-].C(N)(=S)C=1C=[NH+]C=CC=1 DVYXIGZUUOODBX-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- NBIUCDPMOWCGIG-UHFFFAOYSA-N acridine-4-carboxylic acid Chemical compound C1=CC=C2N=C3C(C(=O)O)=CC=CC3=CC2=C1 NBIUCDPMOWCGIG-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 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
- 230000005587 bubbling Effects 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 0.000 description 1
- BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 201000005917 gastric ulcer Diseases 0.000 description 1
- 239000010437 gem Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- OHMBHFSEKCCCBW-UHFFFAOYSA-N hexane-2,5-diol Chemical compound CC(O)CCC(C)O OHMBHFSEKCCCBW-UHFFFAOYSA-N 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000033444 hydroxylation Effects 0.000 description 1
- 238000005805 hydroxylation reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- IBIKHMZPHNKTHM-RDTXWAMCSA-N merck compound 25 Chemical compound C1C[C@@H](C(O)=O)[C@H](O)CN1C(C1=C(F)C=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C1CC1 IBIKHMZPHNKTHM-RDTXWAMCSA-N 0.000 description 1
- DAASTJOPOHVGPP-UHFFFAOYSA-N methyl 2-(5,6,7,8-tetrahydroquinolin-2-yl)acetate Chemical compound C1CCCC2=NC(CC(=O)OC)=CC=C21 DAASTJOPOHVGPP-UHFFFAOYSA-N 0.000 description 1
- IYZRNROPOGFUKE-UHFFFAOYSA-N methyl 3,7,7-trimethyl-6,8-dihydro-5h-quinoline-8-carboxylate Chemical compound C1=C(C)C=C2CCC(C)(C)C(C(=O)OC)C2=N1 IYZRNROPOGFUKE-UHFFFAOYSA-N 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- IMJSVPXADMGVLN-UHFFFAOYSA-N n,n-dimethyl-5,6,7,8-tetrahydroquinoline-8-carboxamide Chemical compound C1=CN=C2C(C(=O)N(C)C)CCCC2=C1 IMJSVPXADMGVLN-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000005152 nicotinamide Nutrition 0.000 description 1
- 239000011570 nicotinamide Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 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
- OFPXSFXSNFPTHF-UHFFFAOYSA-N oxaprozin Chemical compound O1C(CCC(=O)O)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 OFPXSFXSNFPTHF-UHFFFAOYSA-N 0.000 description 1
- 229960002739 oxaprozin Drugs 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 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
- RAIYODFGMLZUDF-UHFFFAOYSA-N piperidin-1-ium;acetate Chemical compound CC([O-])=O.C1CC[NH2+]CC1 RAIYODFGMLZUDF-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 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
- 150000003254 radicals Chemical class 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000007127 saponification reaction Methods 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
- 229910052711 selenium Inorganic materials 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 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
- 239000000126 substance Substances 0.000 description 1
- 229940095064 tartrate Drugs 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4859572 | 1972-10-21 | ||
| GB4859572 | 1972-10-21 | ||
| GB742473 | 1973-02-15 | ||
| GB742473*[A GB1432378A (en) | 1972-10-21 | 1973-02-15 | Fused carbocyclic ring derivatives of pyridine |
| GB3488673 | 1973-07-21 | ||
| GB3488673 | 1973-07-21 | ||
| GB3870173 | 1973-08-16 | ||
| GB3870173 | 1973-08-16 | ||
| FI325273 | 1973-10-19 | ||
| FI3252/73A FI52977C (enrdf_load_stackoverflow) | 1972-10-21 | 1973-10-19 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI763685A7 FI763685A7 (enrdf_load_stackoverflow) | 1976-12-22 |
| FI56529B FI56529B (fi) | 1979-10-31 |
| FI56529C true FI56529C (fi) | 1980-02-11 |
Family
ID=27514589
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI763685A FI56529C (fi) | 1972-10-21 | 1976-12-22 | Pyridinderivat som aer mellanprodukter vid framstaellning av terapeutiskt aktiva tioamidocykloalkylenpyridinderivat |
Country Status (1)
| Country | Link |
|---|---|
| FI (1) | FI56529C (enrdf_load_stackoverflow) |
-
1976
- 1976-12-22 FI FI763685A patent/FI56529C/fi not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FI763685A7 (enrdf_load_stackoverflow) | 1976-12-22 |
| FI56529B (fi) | 1979-10-31 |
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| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: JOHN WYETH & BROTHER LTD |