FI83518C - Foerfarande foer framstaellning av farmakologiskt vaerdefulla kinolizinonfoereningar. - Google Patents
Foerfarande foer framstaellning av farmakologiskt vaerdefulla kinolizinonfoereningar. Download PDFInfo
- Publication number
- FI83518C FI83518C FI853731A FI853731A FI83518C FI 83518 C FI83518 C FI 83518C FI 853731 A FI853731 A FI 853731A FI 853731 A FI853731 A FI 853731A FI 83518 C FI83518 C FI 83518C
- Authority
- FI
- Finland
- Prior art keywords
- salt
- compound
- quinolizin
- nmr
- nujol
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 152
- 150000003839 salts Chemical class 0.000 claims description 133
- -1 carboxy, carbamoyl Chemical group 0.000 claims description 100
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 76
- 238000000034 method Methods 0.000 claims description 58
- 238000002360 preparation method Methods 0.000 claims description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 125000006239 protecting group Chemical group 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 239000004305 biphenyl Chemical group 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 78
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 60
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 52
- 239000000203 mixture Substances 0.000 description 37
- 239000000243 solution Substances 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 31
- 239000002904 solvent Substances 0.000 description 31
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 239000002253 acid Substances 0.000 description 30
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 238000010438 heat treatment Methods 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 238000001816 cooling Methods 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 13
- 235000019341 magnesium sulphate Nutrition 0.000 description 13
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 10
- 235000011054 acetic acid Nutrition 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 230000002411 adverse Effects 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
- 235000017557 sodium bicarbonate Nutrition 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 8
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 8
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 150000002148 esters Chemical group 0.000 description 7
- 230000001590 oxidative effect Effects 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 6
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 6
- VWYXYILJGHBAMC-UHFFFAOYSA-N 4-oxoquinolizine-3-carboxylic acid Chemical compound C1=CC=CN2C(=O)C(C(=O)O)=CC=C21 VWYXYILJGHBAMC-UHFFFAOYSA-N 0.000 description 6
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 239000002026 chloroform extract Substances 0.000 description 5
- 238000003379 elimination reaction Methods 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000007800 oxidant agent Substances 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 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 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000006798 ring closing metathesis reaction Methods 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- 239000002841 Lewis acid Substances 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 108010058846 Ovalbumin Proteins 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 3
- 150000008041 alkali metal carbonates Chemical class 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 239000002168 alkylating agent Substances 0.000 description 3
- 229940100198 alkylating agent Drugs 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 3
- 238000010511 deprotection reaction Methods 0.000 description 3
- CCPCKLDLCGDBJZ-UHFFFAOYSA-N diethyl 4-oxoquinolizine-1,3-dicarboxylate Chemical compound C1=CC=CC2=C(C(=O)OCC)C=C(C(=O)OCC)C(=O)N21 CCPCKLDLCGDBJZ-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- 239000002024 ethyl acetate extract Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 150000007529 inorganic bases Chemical class 0.000 description 3
- 150000007517 lewis acids Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 229940092253 ovalbumin Drugs 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
- 239000012286 potassium permanganate Substances 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- CMOWTMJLGLWFES-UHFFFAOYSA-N 4-oxo-n-pyrimidin-2-ylquinolizine-3-carboxamide Chemical compound C=1C=C2C=CC=CN2C(=O)C=1C(=O)NC1=NC=CC=N1 CMOWTMJLGLWFES-UHFFFAOYSA-N 0.000 description 2
- GJIGPZDJINCCSP-UHFFFAOYSA-N 4-oxoquinolizine-3-carbonitrile Chemical compound C1=CC=CN2C(=O)C(C#N)=CC=C21 GJIGPZDJINCCSP-UHFFFAOYSA-N 0.000 description 2
- SJTHSVCPUADFJZ-UHFFFAOYSA-N 4-oxoquinolizine-3-carboxamide Chemical compound C1=CC=CN2C(=O)C(C(=O)N)=CC=C21 SJTHSVCPUADFJZ-UHFFFAOYSA-N 0.000 description 2
- NEJIHRUPBZTOEM-UHFFFAOYSA-N 6-[(1-hydroxycyclohexyl)methyl]pyridin-3-ol Chemical compound N1=CC(O)=CC=C1CC1(O)CCCCC1 NEJIHRUPBZTOEM-UHFFFAOYSA-N 0.000 description 2
- DHLUJPLHLZJUBW-UHFFFAOYSA-N 6-methylpyridin-3-ol Chemical compound CC1=CC=C(O)C=N1 DHLUJPLHLZJUBW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 206010002198 Anaphylactic reaction Diseases 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 229910000316 alkaline earth metal phosphate Inorganic materials 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 230000002862 amidating effect Effects 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 230000036783 anaphylactic response Effects 0.000 description 2
- 208000003455 anaphylaxis Diseases 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000000427 antigen Substances 0.000 description 2
- 102000036639 antigens Human genes 0.000 description 2
- 108091007433 antigens Proteins 0.000 description 2
- 125000003435 aroyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- ABFLNRKDHDZUFW-UHFFFAOYSA-N ethyl 1-[tert-butyl(dimethyl)silyl]oxy-4-oxoquinolizine-3-carboxylate Chemical compound C1=CC=CN2C(=O)C(C(=O)OCC)=CC(O[Si](C)(C)C(C)(C)C)=C21 ABFLNRKDHDZUFW-UHFFFAOYSA-N 0.000 description 2
- ZQEIWFUZGXVRDP-UHFFFAOYSA-N ethyl 4-oxo-1-phenylsulfanylquinolizine-3-carboxylate Chemical compound C=12C=CC=CN2C(=O)C(C(=O)OCC)=CC=1SC1=CC=CC=C1 ZQEIWFUZGXVRDP-UHFFFAOYSA-N 0.000 description 2
- DCAYKKLFVXUIQZ-UHFFFAOYSA-N ethyl 4-oxo-3-(2h-tetrazol-5-ylcarbamoyl)quinolizine-1-carboxylate Chemical compound O=C1N2C=CC=CC2=C(C(=O)OCC)C=C1C(=O)NC1=NN=NN1 DCAYKKLFVXUIQZ-UHFFFAOYSA-N 0.000 description 2
- GBDJVIYRDRPISB-UHFFFAOYSA-N ethyl 4-oxoquinolizine-3-carboxylate Chemical compound C1=CC=CN2C(=O)C(C(=O)OCC)=CC=C21 GBDJVIYRDRPISB-UHFFFAOYSA-N 0.000 description 2
- HOIDVBZJIXIUMR-UHFFFAOYSA-N ethyl 7-hydroxy-4-oxo-1-phenylquinolizine-3-carboxylate Chemical compound C=12C=CC(O)=CN2C(=O)C(C(=O)OCC)=CC=1C1=CC=CC=C1 HOIDVBZJIXIUMR-UHFFFAOYSA-N 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 125000006606 n-butoxy group Chemical group 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 150000003016 phosphoric acids Chemical class 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
- 235000015497 potassium bicarbonate Nutrition 0.000 description 2
- 239000011736 potassium bicarbonate Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- 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 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
- 235000019345 sodium thiosulphate Nutrition 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- KQDQZEZWWRPNQH-UHFFFAOYSA-N 1,3-diazabicyclo[2.2.2]octane Chemical compound C1CC2CCN1CN2 KQDQZEZWWRPNQH-UHFFFAOYSA-N 0.000 description 1
- OGFAWKRXZLGJSK-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenyl)ethanone Chemical compound OC1=CC(O)=CC=C1C(=O)CC1=CC=C([N+]([O-])=O)C=C1 OGFAWKRXZLGJSK-UHFFFAOYSA-N 0.000 description 1
- OFJUSUAAJCIREH-UHFFFAOYSA-N 1-(2-methylphenyl)-4-oxoquinolizine-3-carboxylic acid Chemical compound CC1=CC=CC=C1C1=C2C=CC=CN2C(=O)C(C(O)=O)=C1 OFJUSUAAJCIREH-UHFFFAOYSA-N 0.000 description 1
- NAPSJFSCGCKKRD-UHFFFAOYSA-N 1-(3-methoxyphenyl)-4-oxoquinolizine-3-carboxylic acid Chemical compound COC1=CC=CC(C2=C3C=CC=CN3C(=O)C(C(O)=O)=C2)=C1 NAPSJFSCGCKKRD-UHFFFAOYSA-N 0.000 description 1
- SUUMOYOITFQPRZ-UHFFFAOYSA-N 1-(3-methylphenyl)-4-oxoquinolizine-3-carboxylic acid Chemical compound CC1=CC=CC(C2=C3C=CC=CN3C(=O)C(C(O)=O)=C2)=C1 SUUMOYOITFQPRZ-UHFFFAOYSA-N 0.000 description 1
- BQPRXVQLWMTXKQ-UHFFFAOYSA-N 1-(4-chlorophenyl)-4-oxo-n-(2h-tetrazol-5-yl)quinolizine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=C2C=CC=CN2C(=O)C(C(=O)NC=2NN=NN=2)=C1 BQPRXVQLWMTXKQ-UHFFFAOYSA-N 0.000 description 1
- QDDPNZFRZVGJLU-UHFFFAOYSA-N 1-(4-chlorophenyl)-4-oxoquinolizine-3-carboxylic acid Chemical compound C=12C=CC=CN2C(=O)C(C(=O)O)=CC=1C1=CC=C(Cl)C=C1 QDDPNZFRZVGJLU-UHFFFAOYSA-N 0.000 description 1
- ZGEWCBQGIGQOQQ-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-oxoquinolizine-3-carboxylic acid Chemical compound C=12C=CC=CN2C(=O)C(C(=O)O)=CC=1S(=O)(=O)C1=CC=CC=C1 ZGEWCBQGIGQOQQ-UHFFFAOYSA-N 0.000 description 1
- UWHSZPFXJANAMK-UHFFFAOYSA-N 1-(n-methylanilino)-4-oxoquinolizine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)N2C=CC=CC2=C1N(C)C1=CC=CC=C1 UWHSZPFXJANAMK-UHFFFAOYSA-N 0.000 description 1
- ZGWXKZOCDJGUEF-UHFFFAOYSA-N 1-benzoyl-7-butoxy-4-oxoquinolizine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)N2C=C(OCCCC)C=CC2=C1C(=O)C1=CC=CC=C1 ZGWXKZOCDJGUEF-UHFFFAOYSA-N 0.000 description 1
- LFOTZNLDSBVCJH-UHFFFAOYSA-N 1-benzyl-4-oxoquinolizine-3-carboxylic acid Chemical compound C=12C=CC=CN2C(=O)C(C(=O)O)=CC=1CC1=CC=CC=C1 LFOTZNLDSBVCJH-UHFFFAOYSA-N 0.000 description 1
- INOGLHRUEYDAHX-UHFFFAOYSA-N 1-chlorobenzotriazole Chemical compound C1=CC=C2N(Cl)N=NC2=C1 INOGLHRUEYDAHX-UHFFFAOYSA-N 0.000 description 1
- LIUUGIAVOIOGBV-UHFFFAOYSA-N 1-ethoxycarbonyl-4-oxoquinolizine-3-carboxylic acid Chemical compound C1=CC=CC2=C(C(=O)OCC)C=C(C(O)=O)C(=O)N21 LIUUGIAVOIOGBV-UHFFFAOYSA-N 0.000 description 1
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 1
- HKHAAGGBBNUFPK-UHFFFAOYSA-N 1-hydroxy-4-oxoquinolizine-3-carboxylic acid Chemical compound C1=CC=CN2C(=O)C(C(=O)O)=CC(O)=C21 HKHAAGGBBNUFPK-UHFFFAOYSA-N 0.000 description 1
- SNUSZUYTMHKCPM-UHFFFAOYSA-N 1-hydroxypyridin-2-one Chemical compound ON1C=CC=CC1=O SNUSZUYTMHKCPM-UHFFFAOYSA-N 0.000 description 1
- QYQQTZFOFMPYCA-UHFFFAOYSA-N 1-iodoprop-1-ene Chemical compound CC=CI QYQQTZFOFMPYCA-UHFFFAOYSA-N 0.000 description 1
- JKHKBBRSFACETN-UHFFFAOYSA-N 1-methoxy-4-oxoquinolizine-3-carboxylic acid Chemical compound C1=CC=CC2=C(OC)C=C(C(O)=O)C(=O)N21 JKHKBBRSFACETN-UHFFFAOYSA-N 0.000 description 1
- XYUJWSKSKOIHRA-UHFFFAOYSA-N 1-methyl-4-oxoquinolizine-3-carboxylic acid Chemical compound C1=CC=CC2=C(C)C=C(C(O)=O)C(=O)N21 XYUJWSKSKOIHRA-UHFFFAOYSA-N 0.000 description 1
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
- OHNVZUQWMCFYKK-UHFFFAOYSA-N 1-naphthalen-1-yl-4-oxoquinolizine-3-carboxylic acid Chemical compound C1=CC=CN2C(=O)C(C(=O)O)=CC(C=3C4=CC=CC=C4C=CC=3)=C21 OHNVZUQWMCFYKK-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- NKYUYSHKHYJDRP-UHFFFAOYSA-N 1-oxo-4-phenylbenzo[c]quinolizine-2-carboxylic acid Chemical compound C=12C=CC3=CC=CC=C3N2C(=O)C(C(=O)O)=CC=1C1=CC=CC=C1 NKYUYSHKHYJDRP-UHFFFAOYSA-N 0.000 description 1
- UTXSHOIHNAOXAJ-UHFFFAOYSA-N 1-oxobenzo[c]quinolizine-2-carboxylic acid Chemical compound C1=CC2=CC=CC=C2N2C1=CC=C(C(=O)O)C2=O UTXSHOIHNAOXAJ-UHFFFAOYSA-N 0.000 description 1
- CMOXTMGJZNCXEI-UHFFFAOYSA-N 1-phenyl-2-pyridin-2-ylethanone Chemical compound C=1C=CC=CC=1C(=O)CC1=CC=CC=N1 CMOXTMGJZNCXEI-UHFFFAOYSA-N 0.000 description 1
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
- XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 description 1
- QFWCYNPOPKQOKV-UHFFFAOYSA-N 2-(2-amino-3-methoxyphenyl)chromen-4-one Chemical compound COC1=CC=CC(C=2OC3=CC=CC=C3C(=O)C=2)=C1N QFWCYNPOPKQOKV-UHFFFAOYSA-N 0.000 description 1
- 125000006385 2-(3-methylpyridyl) group Chemical group [H]C1=C([H])C([H])=C(C(*)=N1)C([H])([H])[H] 0.000 description 1
- NJWIMFZLESWFIM-UHFFFAOYSA-N 2-(chloromethyl)pyridine Chemical compound ClCC1=CC=CC=N1 NJWIMFZLESWFIM-UHFFFAOYSA-N 0.000 description 1
- OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-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
- JSQPGNJFQUOEPA-UHFFFAOYSA-N 2-chloroethaneperoxoic acid Chemical compound OOC(=O)CCl JSQPGNJFQUOEPA-UHFFFAOYSA-N 0.000 description 1
- PBKLWSFQZYSSAJ-UHFFFAOYSA-N 2-hydroxy-4-oxoquinolizine-3-carboxylic acid Chemical compound C1=CC=CN2C(=O)C(C(=O)O)=C(O)C=C21 PBKLWSFQZYSSAJ-UHFFFAOYSA-N 0.000 description 1
- CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 1
- MQVISALTZUNQSK-UHFFFAOYSA-N 2-pyridin-2-ylacetic acid;hydrochloride Chemical compound Cl.OC(=O)CC1=CC=CC=N1 MQVISALTZUNQSK-UHFFFAOYSA-N 0.000 description 1
- ULRPISSMEBPJLN-UHFFFAOYSA-N 2h-tetrazol-5-amine Chemical compound NC1=NN=NN1 ULRPISSMEBPJLN-UHFFFAOYSA-N 0.000 description 1
- LLPBUXODFQZPFH-UHFFFAOYSA-N 3,3-dimethyl-1h-benzo[g]indole-2,4,5-trione Chemical compound O=C1C(=O)C2=CC=CC=C2C2=C1C(C)(C)C(=O)N2 LLPBUXODFQZPFH-UHFFFAOYSA-N 0.000 description 1
- SDXAWLJRERMRKF-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazole Chemical compound CC=1C=C(C)NN=1 SDXAWLJRERMRKF-UHFFFAOYSA-N 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-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
- UTVVZGKEAKOXII-UHFFFAOYSA-N 4-oxo-1-(4-phenylphenyl)quinolizine-3-carboxylic acid Chemical compound C=12C=CC=CN2C(=O)C(C(=O)O)=CC=1C(C=C1)=CC=C1C1=CC=CC=C1 UTVVZGKEAKOXII-UHFFFAOYSA-N 0.000 description 1
- FHGZDBGEEJXFPK-UHFFFAOYSA-N 4-oxo-1-phenoxyquinolizine-3-carboxylic acid Chemical compound C=12C=CC=CN2C(=O)C(C(=O)O)=CC=1OC1=CC=CC=C1 FHGZDBGEEJXFPK-UHFFFAOYSA-N 0.000 description 1
- OXXRZMDRIHNASB-UHFFFAOYSA-N 4-oxo-1-phenyl-n-pyridin-2-ylquinolizine-3-carboxamide Chemical compound C=1C(C=2C=CC=CC=2)=C2C=CC=CN2C(=O)C=1C(=O)NC1=CC=CC=N1 OXXRZMDRIHNASB-UHFFFAOYSA-N 0.000 description 1
- UNEXBUJCNQGKQM-UHFFFAOYSA-N 4-oxo-1-phenylquinolizine-3-carboxylic acid Chemical compound C=12C=CC=CN2C(=O)C(C(=O)O)=CC=1C1=CC=CC=C1 UNEXBUJCNQGKQM-UHFFFAOYSA-N 0.000 description 1
- PIGPUTDIYDKQLI-UHFFFAOYSA-N 4-oxo-1-phenylsulfanylquinolizine-3-carboxylic acid Chemical compound C=12C=CC=CN2C(=O)C(C(=O)O)=CC=1SC1=CC=CC=C1 PIGPUTDIYDKQLI-UHFFFAOYSA-N 0.000 description 1
- GIKZUSNXAGVZNT-UHFFFAOYSA-N 4-oxo-3-(2h-tetrazol-5-ylcarbamoyl)quinolizine-1-carboxylic acid Chemical compound O=C1N2C=CC=CC2=C(C(=O)O)C=C1C(=O)NC1=NN=NN1 GIKZUSNXAGVZNT-UHFFFAOYSA-N 0.000 description 1
- YIHYDEWVDDYLIA-UHFFFAOYSA-N 4-oxo-7-propan-2-yloxyquinolizine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)N2C=C(OC(C)C)C=CC2=C1 YIHYDEWVDDYLIA-UHFFFAOYSA-N 0.000 description 1
- UFNQSEODLHVKCG-UHFFFAOYSA-N 4-oxo-n-(1,3-thiazol-2-yl)quinolizine-3-carboxamide Chemical compound C=1C=C2C=CC=CN2C(=O)C=1C(=O)NC1=NC=CS1 UFNQSEODLHVKCG-UHFFFAOYSA-N 0.000 description 1
- UGXBHAFCEBJJTK-UHFFFAOYSA-N 4-oxo-n-pyrazin-2-ylquinolizine-3-carboxamide Chemical compound C=1C=C2C=CC=CN2C(=O)C=1C(=O)NC1=CN=CC=N1 UGXBHAFCEBJJTK-UHFFFAOYSA-N 0.000 description 1
- DAHIMZJSWBILHU-UHFFFAOYSA-N 4-oxo-n-pyridin-2-ylquinolizine-3-carboxamide Chemical compound C=1C=C2C=CC=CN2C(=O)C=1C(=O)NC1=CC=CC=N1 DAHIMZJSWBILHU-UHFFFAOYSA-N 0.000 description 1
- XHZASLJUASIAJI-UHFFFAOYSA-N 4-oxobenzo[a]quinolizine-3-carboxylic acid Chemical compound C12=CC=CC=C2C=CN2C1=CC=C(C(=O)O)C2=O XHZASLJUASIAJI-UHFFFAOYSA-N 0.000 description 1
- FQFAMOXDRNNCBO-UHFFFAOYSA-N 4-oxoquinolizine-1,3-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(=O)O)C=C(C(O)=O)C(=O)N21 FQFAMOXDRNNCBO-UHFFFAOYSA-N 0.000 description 1
- CJMRUZLKISYQCE-UHFFFAOYSA-N 4-oxoquinolizine-1-carboxylic acid Chemical compound C1=CC=CC2=C(C(=O)O)C=CC(=O)N21 CJMRUZLKISYQCE-UHFFFAOYSA-N 0.000 description 1
- DETMHQYXDHDQMC-UHFFFAOYSA-N 4-oxoquinolizine-3-carbothioamide Chemical compound C1=CC=CN2C(=O)C(C(=S)N)=CC=C21 DETMHQYXDHDQMC-UHFFFAOYSA-N 0.000 description 1
- SSMQDOOSQWULCT-UHFFFAOYSA-N 6-benzylpyridin-3-ol Chemical compound N1=CC(O)=CC=C1CC1=CC=CC=C1 SSMQDOOSQWULCT-UHFFFAOYSA-N 0.000 description 1
- TZCYLJGNWDVJRA-UHFFFAOYSA-N 6-chloro-1-hydroxybenzotriazole Chemical compound C1=C(Cl)C=C2N(O)N=NC2=C1 TZCYLJGNWDVJRA-UHFFFAOYSA-N 0.000 description 1
- DMNNPBZKXGDWJZ-UHFFFAOYSA-N 6-methyl-4-oxoquinolizine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)N2C(C)=CC=CC2=C1 DMNNPBZKXGDWJZ-UHFFFAOYSA-N 0.000 description 1
- DKQMNBILGHLJQS-UHFFFAOYSA-N 7-butoxy-4-oxo-1-phenylquinolizine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)N2C=C(OCCCC)C=CC2=C1C1=CC=CC=C1 DKQMNBILGHLJQS-UHFFFAOYSA-N 0.000 description 1
- DAESPKNDNPWXHW-UHFFFAOYSA-N 7-butoxy-4-oxoquinolizine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)N2C=C(OCCCC)C=CC2=C1 DAESPKNDNPWXHW-UHFFFAOYSA-N 0.000 description 1
- LIXBIFQJQUGMLD-UHFFFAOYSA-N 7-ethyl-4-oxoquinolizine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)N2C=C(CC)C=CC2=C1 LIXBIFQJQUGMLD-UHFFFAOYSA-N 0.000 description 1
- ZDWBZEAAYTYREV-UHFFFAOYSA-N 7-hydroxy-4-oxoquinolizine-3-carboxylic acid Chemical compound C1=CC(O)=CN2C(=O)C(C(=O)O)=CC=C21 ZDWBZEAAYTYREV-UHFFFAOYSA-N 0.000 description 1
- ULYOZGSWLTXTLH-UHFFFAOYSA-N 7-methoxy-4-oxoquinolizine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)N2C=C(OC)C=CC2=C1 ULYOZGSWLTXTLH-UHFFFAOYSA-N 0.000 description 1
- FKEYCZRQRSWEJI-UHFFFAOYSA-N 7-methyl-4-oxoquinolizine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)N2C=C(C)C=CC2=C1 FKEYCZRQRSWEJI-UHFFFAOYSA-N 0.000 description 1
- AORPVUURJHZTOJ-UHFFFAOYSA-N 8-methyl-4-oxoquinolizine-3-carboxylic acid Chemical compound C1=C(C)C=CN2C1=CC=C(C(O)=O)C2=O AORPVUURJHZTOJ-UHFFFAOYSA-N 0.000 description 1
- OSGHCNBIPCSKSB-UHFFFAOYSA-N 9-methyl-4-oxoquinolizine-3-carboxylic acid Chemical compound CC1=CC=CN2C1=CC=C(C(O)=O)C2=O OSGHCNBIPCSKSB-UHFFFAOYSA-N 0.000 description 1
- 244000291564 Allium cepa Species 0.000 description 1
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 229910000497 Amalgam Inorganic materials 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- BIMDPCNECSBGIO-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)C=1C=C(C(N2C(=CC=CC12)OCCCC)=O)C(=O)NC1=NN=NN1 Chemical compound C(C1=CC=CC=C1)(=O)C=1C=C(C(N2C(=CC=CC12)OCCCC)=O)C(=O)NC1=NN=NN1 BIMDPCNECSBGIO-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- HDFFVHSMHLDSLO-UHFFFAOYSA-N Dibenzyl phosphate Chemical compound C=1C=CC=CC=1COP(=O)(O)OCC1=CC=CC=C1 HDFFVHSMHLDSLO-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- ASMQGLCHMVWBQR-UHFFFAOYSA-N Diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(O)OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 101100448208 Human herpesvirus 6B (strain Z29) U69 gene Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 102000011782 Keratins Human genes 0.000 description 1
- 108010076876 Keratins Proteins 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
- XNPOFXIBHOVFFH-UHFFFAOYSA-N N-cyclohexyl-N'-(2-(4-morpholinyl)ethyl)carbodiimide Chemical compound C1CCCCC1N=C=NCCN1CCOCC1 XNPOFXIBHOVFFH-UHFFFAOYSA-N 0.000 description 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 206010040914 Skin reaction Diseases 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- HEMHJVSKTPXQMS-DYCDLGHISA-M Sodium hydroxide-d Chemical compound [Na+].[2H][O-] HEMHJVSKTPXQMS-DYCDLGHISA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 206010042220 Stress ulcer Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 229910021623 Tin(IV) bromide Inorganic materials 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- LCQUGNMENZYPMX-UHFFFAOYSA-N [Na].C(C1=CC=CC=C1)(=O)C=1C=C(C(N2C=C(C=CC12)OCCCC)=O)C(=O)NC1=NN=NN1 Chemical compound [Na].C(C1=CC=CC=C1)(=O)C=1C=C(C(N2C=C(C=CC12)OCCCC)=O)C(=O)NC1=NN=NN1 LCQUGNMENZYPMX-UHFFFAOYSA-N 0.000 description 1
- YMBGBZHUDLRCFV-UHFFFAOYSA-N [Na].C(CCC)OC1=CN2C(C(=CC(=C2C=C1)C1=CC=CC=C1)C(=O)NC1=NN=NN1)=O Chemical compound [Na].C(CCC)OC1=CN2C(C(=CC(=C2C=C1)C1=CC=CC=C1)C(=O)NC1=NN=NN1)=O YMBGBZHUDLRCFV-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 230000000767 anti-ulcer Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 239000000022 bacteriostatic agent Substances 0.000 description 1
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 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
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 150000001845 chromium compounds Chemical class 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- FXCTZFMSAHZQTR-KAMYIIQDSA-N cpccoet Chemical compound O\N=C/1C2=CC=CC=C2OC2(C(=O)OCC)C\1C2 FXCTZFMSAHZQTR-KAMYIIQDSA-N 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000012217 deletion Methods 0.000 description 1
- 230000037430 deletion Effects 0.000 description 1
- KTOXTZMYMCIESP-UHFFFAOYSA-N diethyl 2-(1-ethoxy-2-pyridin-2-ylethyl)propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)C(OCC)CC1=CC=CC=N1 KTOXTZMYMCIESP-UHFFFAOYSA-N 0.000 description 1
- IECINXBBTAYKEU-UHFFFAOYSA-N diethyl 2-[1-ethoxy-2-(3-methoxyphenyl)-2-pyridin-2-ylethyl]propanedioate Chemical compound C=1C=CC=NC=1C(C(C(C(=O)OCC)C(=O)OCC)OCC)C1=CC=CC(OC)=C1 IECINXBBTAYKEU-UHFFFAOYSA-N 0.000 description 1
- UIFBGOGNCPAGON-UHFFFAOYSA-N diethyl 2-[2-(4-chlorophenyl)-1-ethoxy-2-pyridin-2-ylethyl]propanedioate Chemical compound C=1C=CC=NC=1C(C(C(C(=O)OCC)C(=O)OCC)OCC)C1=CC=C(Cl)C=C1 UIFBGOGNCPAGON-UHFFFAOYSA-N 0.000 description 1
- NORDXVQLXAZNKA-UHFFFAOYSA-N diethyl 2-[2-[tert-butyl(dimethyl)silyl]oxy-1-ethoxy-2-pyridin-2-ylethyl]propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)C(OCC)C(O[Si](C)(C)C(C)(C)C)C1=CC=CC=N1 NORDXVQLXAZNKA-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- GXGAKHNRMVGRPK-UHFFFAOYSA-N dimagnesium;dioxido-bis[[oxido(oxo)silyl]oxy]silane Chemical compound [Mg+2].[Mg+2].[O-][Si](=O)O[Si]([O-])([O-])O[Si]([O-])=O GXGAKHNRMVGRPK-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 208000000718 duodenal ulcer Diseases 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- RCRARFPGXGOVGC-UHFFFAOYSA-N ethyl 1-(2-methylphenyl)-4-oxoquinolizine-3-carboxylate Chemical compound C=12C=CC=CN2C(=O)C(C(=O)OCC)=CC=1C1=CC=CC=C1C RCRARFPGXGOVGC-UHFFFAOYSA-N 0.000 description 1
- DCLMUWIYZSZZIL-UHFFFAOYSA-N ethyl 1-(3-methoxyphenyl)-4-oxoquinolizine-3-carboxylate Chemical compound C=12C=CC=CN2C(=O)C(C(=O)OCC)=CC=1C1=CC=CC(OC)=C1 DCLMUWIYZSZZIL-UHFFFAOYSA-N 0.000 description 1
- GQXTZOVRUHHUDD-UHFFFAOYSA-N ethyl 1-(3-methylphenyl)-4-oxoquinolizine-3-carboxylate Chemical compound C=12C=CC=CN2C(=O)C(C(=O)OCC)=CC=1C1=CC=CC(C)=C1 GQXTZOVRUHHUDD-UHFFFAOYSA-N 0.000 description 1
- KQOMLBCDAHWQBE-UHFFFAOYSA-N ethyl 1-(4-chlorophenyl)-4-oxoquinolizine-3-carboxylate Chemical compound C=12C=CC=CN2C(=O)C(C(=O)OCC)=CC=1C1=CC=C(Cl)C=C1 KQOMLBCDAHWQBE-UHFFFAOYSA-N 0.000 description 1
- VAZAHHXWERHKAO-UHFFFAOYSA-N ethyl 1-(benzenesulfonyl)-4-oxoquinolizine-3-carboxylate Chemical compound C=12C=CC=CN2C(=O)C(C(=O)OCC)=CC=1S(=O)(=O)C1=CC=CC=C1 VAZAHHXWERHKAO-UHFFFAOYSA-N 0.000 description 1
- JUMLQPKSPNIOGK-UHFFFAOYSA-N ethyl 1-(n-methylanilino)-4-oxoquinolizine-3-carboxylate Chemical compound C=12C=CC=CN2C(=O)C(C(=O)OCC)=CC=1N(C)C1=CC=CC=C1 JUMLQPKSPNIOGK-UHFFFAOYSA-N 0.000 description 1
- MOLYZNZCFPRIQN-UHFFFAOYSA-N ethyl 1-benzoyl-4-oxoquinolizine-3-carboxylate Chemical compound C=12C=CC=CN2C(=O)C(C(=O)OCC)=CC=1C(=O)C1=CC=CC=C1 MOLYZNZCFPRIQN-UHFFFAOYSA-N 0.000 description 1
- BZKQHRYBVPFKJQ-UHFFFAOYSA-N ethyl 1-benzoyl-7-butoxy-4-oxoquinolizine-3-carboxylate Chemical compound C1=C(C(=O)OCC)C(=O)N2C=C(OCCCC)C=CC2=C1C(=O)C1=CC=CC=C1 BZKQHRYBVPFKJQ-UHFFFAOYSA-N 0.000 description 1
- IIESJTYJGCRBQO-UHFFFAOYSA-N ethyl 1-benzoyl-7-hydroxy-4-oxoquinolizine-3-carboxylate Chemical compound C=12C=CC(O)=CN2C(=O)C(C(=O)OCC)=CC=1C(=O)C1=CC=CC=C1 IIESJTYJGCRBQO-UHFFFAOYSA-N 0.000 description 1
- WAUHTLSKOPNHBS-UHFFFAOYSA-N ethyl 1-benzyl-4-oxoquinolizine-3-carboxylate Chemical compound C=12C=CC=CN2C(=O)C(C(=O)OCC)=CC=1CC1=CC=CC=C1 WAUHTLSKOPNHBS-UHFFFAOYSA-N 0.000 description 1
- XLJMZAIHXQRTLW-UHFFFAOYSA-N ethyl 1-hydroxy-4-oxoquinolizine-3-carboxylate Chemical compound C1=CC=CN2C(=O)C(C(=O)OCC)=CC(O)=C21 XLJMZAIHXQRTLW-UHFFFAOYSA-N 0.000 description 1
- WHTXJGALXGRBOG-UHFFFAOYSA-N ethyl 1-methoxy-4-oxoquinolizine-3-carboxylate Chemical compound C1=CC=CN2C(=O)C(C(=O)OCC)=CC(OC)=C21 WHTXJGALXGRBOG-UHFFFAOYSA-N 0.000 description 1
- SFOHGYQSJRALLO-UHFFFAOYSA-N ethyl 1-naphthalen-1-yl-4-oxoquinolizine-3-carboxylate Chemical compound C1=CC=CN2C(=O)C(C(=O)OCC)=CC(C=3C4=CC=CC=C4C=CC=3)=C21 SFOHGYQSJRALLO-UHFFFAOYSA-N 0.000 description 1
- NDYHGYRYEYAKJK-UHFFFAOYSA-N ethyl 1-oxo-4-phenylbenzo[c]quinolizine-2-carboxylate Chemical compound C=12C=CC3=CC=CC=C3N2C(=O)C(C(=O)OCC)=CC=1C1=CC=CC=C1 NDYHGYRYEYAKJK-UHFFFAOYSA-N 0.000 description 1
- YISZIUALHMRHMU-UHFFFAOYSA-N ethyl 1-oxobenzo[c]quinolizine-2-carboxylate Chemical compound C1=CC2=CC=CC=C2N2C1=CC=C(C(=O)OCC)C2=O YISZIUALHMRHMU-UHFFFAOYSA-N 0.000 description 1
- WXMSGMOIAQWILS-UHFFFAOYSA-N ethyl 2-ethoxyprop-2-enoate Chemical compound CCOC(=C)C(=O)OCC WXMSGMOIAQWILS-UHFFFAOYSA-N 0.000 description 1
- IUDKTVXSXWAKJO-UHFFFAOYSA-N ethyl 2-pyridin-2-ylacetate Chemical compound CCOC(=O)CC1=CC=CC=N1 IUDKTVXSXWAKJO-UHFFFAOYSA-N 0.000 description 1
- AVZKBXLEJHDBDY-UHFFFAOYSA-N ethyl 4-oxo-1-(4-phenylphenyl)quinolizine-3-carboxylate Chemical compound C=12C=CC=CN2C(=O)C(C(=O)OCC)=CC=1C(C=C1)=CC=C1C1=CC=CC=C1 AVZKBXLEJHDBDY-UHFFFAOYSA-N 0.000 description 1
- GOIICNMUGIQACW-UHFFFAOYSA-N ethyl 4-oxo-1-phenoxyquinolizine-3-carboxylate Chemical compound C=12C=CC=CN2C(=O)C(C(=O)OCC)=CC=1OC1=CC=CC=C1 GOIICNMUGIQACW-UHFFFAOYSA-N 0.000 description 1
- GVVHRCCZRYSENG-UHFFFAOYSA-N ethyl 4-oxo-1-phenylquinolizine-3-carboxylate Chemical compound C=12C=CC=CN2C(=O)C(C(=O)OCC)=CC=1C1=CC=CC=C1 GVVHRCCZRYSENG-UHFFFAOYSA-N 0.000 description 1
- UITNJVPSUUFXOR-UHFFFAOYSA-N ethyl 4-oxo-7-propan-2-yloxyquinolizine-3-carboxylate Chemical compound C1=CC(OC(C)C)=CN2C(=O)C(C(=O)OCC)=CC=C21 UITNJVPSUUFXOR-UHFFFAOYSA-N 0.000 description 1
- NMUNWALZPICBOX-UHFFFAOYSA-N ethyl 4-oxobenzo[a]quinolizine-3-carboxylate Chemical compound C12=CC=CC=C2C=CN2C1=CC=C(C(=O)OCC)C2=O NMUNWALZPICBOX-UHFFFAOYSA-N 0.000 description 1
- LRYIQNJLUHCZLL-UHFFFAOYSA-N ethyl 4-oxoquinolizine-1-carboxylate Chemical compound C1=CC=CC2=C(C(=O)OCC)C=CC(=O)N21 LRYIQNJLUHCZLL-UHFFFAOYSA-N 0.000 description 1
- DQAYZVOYUWQVJM-UHFFFAOYSA-N ethyl 6-methyl-4-oxoquinolizine-3-carboxylate Chemical compound C1=CC=C(C)N2C(=O)C(C(=O)OCC)=CC=C21 DQAYZVOYUWQVJM-UHFFFAOYSA-N 0.000 description 1
- NGWXVBOMSLTNCQ-UHFFFAOYSA-N ethyl 7-butoxy-4-oxo-1-phenylquinolizine-3-carboxylate Chemical compound C1=C(C(=O)OCC)C(=O)N2C=C(OCCCC)C=CC2=C1C1=CC=CC=C1 NGWXVBOMSLTNCQ-UHFFFAOYSA-N 0.000 description 1
- JMBCNLPFNKTPNN-UHFFFAOYSA-N ethyl 7-ethyl-4-oxoquinolizine-3-carboxylate Chemical compound C1=CC(CC)=CN2C(=O)C(C(=O)OCC)=CC=C21 JMBCNLPFNKTPNN-UHFFFAOYSA-N 0.000 description 1
- IFQCUPWNTONNQC-UHFFFAOYSA-N ethyl 7-hydroxy-4-oxoquinolizine-3-carboxylate Chemical compound C1=CC(O)=CN2C(=O)C(C(=O)OCC)=CC=C21 IFQCUPWNTONNQC-UHFFFAOYSA-N 0.000 description 1
- BMRWYXCVICOZJK-UHFFFAOYSA-N ethyl 7-methoxy-4-oxoquinolizine-3-carboxylate Chemical compound C1=CC(OC)=CN2C(=O)C(C(=O)OCC)=CC=C21 BMRWYXCVICOZJK-UHFFFAOYSA-N 0.000 description 1
- KHQVEBRYAOLUFD-UHFFFAOYSA-N ethyl 7-methyl-4-oxoquinolizine-3-carboxylate Chemical compound C1=CC(C)=CN2C(=O)C(C(=O)OCC)=CC=C21 KHQVEBRYAOLUFD-UHFFFAOYSA-N 0.000 description 1
- AKGIHCKXCHEWPH-UHFFFAOYSA-N ethyl 8-hydroxy-4-oxoquinolizine-3-carboxylate Chemical compound C1=C(O)C=CN2C(=O)C(C(=O)OCC)=CC=C21 AKGIHCKXCHEWPH-UHFFFAOYSA-N 0.000 description 1
- LJJOTYXTVQMADR-UHFFFAOYSA-N ethyl 8-methyl-4-oxoquinolizine-3-carboxylate Chemical compound C1=C(C)C=CN2C(=O)C(C(=O)OCC)=CC=C21 LJJOTYXTVQMADR-UHFFFAOYSA-N 0.000 description 1
- KIVVHZVNDCYHIH-UHFFFAOYSA-N ethyl 9-methyl-4-oxoquinolizine-3-carboxylate Chemical compound CC1=CC=CN2C(=O)C(C(=O)OCC)=CC=C21 KIVVHZVNDCYHIH-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 150000004966 inorganic peroxy acids Chemical class 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229940099273 magnesium trisilicate Drugs 0.000 description 1
- 229910000386 magnesium trisilicate Inorganic materials 0.000 description 1
- 235000019793 magnesium trisilicate Nutrition 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
- OHZZTXYKLXZFSZ-UHFFFAOYSA-I manganese(3+) 5,10,15-tris(1-methylpyridin-1-ium-4-yl)-20-(1-methylpyridin-4-ylidene)porphyrin-22-ide pentachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mn+3].C1=CN(C)C=CC1=C1C(C=C2)=NC2=C(C=2C=C[N+](C)=CC=2)C([N-]2)=CC=C2C(C=2C=C[N+](C)=CC=2)=C(C=C2)N=C2C(C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 OHZZTXYKLXZFSZ-UHFFFAOYSA-I 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- GXHFUVWIGNLZSC-UHFFFAOYSA-N meldrum's acid Chemical compound CC1(C)OC(=O)CC(=O)O1 GXHFUVWIGNLZSC-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical compound COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- CPFUTAJYANNERZ-UHFFFAOYSA-N n-(2-hydroxyphenyl)-4-oxoquinolizine-3-carboxamide Chemical compound OC1=CC=CC=C1NC(=O)C(C1=O)=CC=C2N1C=CC=C2 CPFUTAJYANNERZ-UHFFFAOYSA-N 0.000 description 1
- XOLSIGGJYPHQCQ-UHFFFAOYSA-N n-methyl-n-(pyridin-2-ylmethyl)aniline Chemical compound C=1C=CC=CC=1N(C)CC1=CC=CC=N1 XOLSIGGJYPHQCQ-UHFFFAOYSA-N 0.000 description 1
- 125000004971 nitroalkyl group Chemical group 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 150000004967 organic peroxy acids Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- CFSVEFLOHSULPY-UHFFFAOYSA-N pyridin-2-yl butanoate Chemical compound CCCC(=O)OC1=CC=CC=N1 CFSVEFLOHSULPY-UHFFFAOYSA-N 0.000 description 1
- SHNUBALDGXWUJI-UHFFFAOYSA-N pyridin-2-ylmethanol Chemical compound OCC1=CC=CC=N1 SHNUBALDGXWUJI-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000006894 reductive elimination reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 230000035483 skin reaction Effects 0.000 description 1
- 231100000430 skin reaction Toxicity 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
- OYXRAJQQRHZBEK-UHFFFAOYSA-N tert-butyl-dimethyl-(pyridin-2-ylmethoxy)silane Chemical compound CC(C)(C)[Si](C)(C)OCC1=CC=CC=N1 OYXRAJQQRHZBEK-UHFFFAOYSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- LTSUHJWLSNQKIP-UHFFFAOYSA-J tin(iv) bromide Chemical compound Br[Sn](Br)(Br)Br LTSUHJWLSNQKIP-UHFFFAOYSA-J 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- UBZYKBZMAMTNKW-UHFFFAOYSA-J titanium tetrabromide Chemical compound Br[Ti](Br)(Br)Br UBZYKBZMAMTNKW-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8429710 | 1984-11-23 | ||
| GB848429710A GB8429710D0 (en) | 1984-11-23 | 1984-11-23 | Pharmaceutical composition |
| US71243585 | 1985-03-18 | ||
| US06/712,435 US4650804A (en) | 1984-03-30 | 1985-03-18 | Quinolizinone compounds and pharmaceutical composition comprising the same, useful as anti-ulcerative and anti-allergic agents |
| US77095385 | 1985-08-30 | ||
| US06/770,953 US4698349A (en) | 1984-03-30 | 1985-08-30 | Quinolizinone compounds, and pharmaceutical composition comprising the same, useful as anti-ulcerative and anti-allergic agents |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI853731A0 FI853731A0 (fi) | 1985-09-27 |
| FI853731L FI853731L (fi) | 1986-05-24 |
| FI83518B FI83518B (fi) | 1991-04-15 |
| FI83518C true FI83518C (fi) | 1991-07-25 |
Family
ID=27262528
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI853731A FI83518C (fi) | 1984-11-23 | 1985-09-27 | Foerfarande foer framstaellning av farmakologiskt vaerdefulla kinolizinonfoereningar. |
Country Status (8)
| Country | Link |
|---|---|
| AU (1) | AU598446B2 (enrdf_load_stackoverflow) |
| CA (1) | CA1268458A (enrdf_load_stackoverflow) |
| DK (1) | DK165554C (enrdf_load_stackoverflow) |
| FI (1) | FI83518C (enrdf_load_stackoverflow) |
| GR (1) | GR852368B (enrdf_load_stackoverflow) |
| HU (1) | HU206710B (enrdf_load_stackoverflow) |
| NO (1) | NO162285C (enrdf_load_stackoverflow) |
| PH (1) | PH23064A (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZW17385A1 (en) * | 1984-11-06 | 1986-02-19 | Hoffmann La Roche | Tricyclic pyridine derivatives |
| AU616916B2 (en) * | 1987-11-20 | 1991-11-14 | Kissei Pharmaceutical Co. Ltd. | 4h-quinolizin-4-one compounds exhibiting therapeutic activities |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZW17385A1 (en) * | 1984-11-06 | 1986-02-19 | Hoffmann La Roche | Tricyclic pyridine derivatives |
-
1985
- 1985-09-09 NO NO853525A patent/NO162285C/no unknown
- 1985-09-11 AU AU47341/85A patent/AU598446B2/en not_active Ceased
- 1985-09-19 PH PH32807A patent/PH23064A/en unknown
- 1985-09-25 DK DK434185A patent/DK165554C/da not_active IP Right Cessation
- 1985-09-25 CA CA000491534A patent/CA1268458A/en not_active Expired - Fee Related
- 1985-09-27 FI FI853731A patent/FI83518C/fi not_active IP Right Cessation
- 1985-09-27 HU HU374085A patent/HU206710B/hu unknown
- 1985-09-30 GR GR852368A patent/GR852368B/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO162285C (no) | 1989-12-06 |
| DK434185A (da) | 1986-05-24 |
| DK165554C (da) | 1993-04-26 |
| FI853731A0 (fi) | 1985-09-27 |
| CA1268458A (en) | 1990-05-01 |
| GR852368B (enrdf_load_stackoverflow) | 1985-12-12 |
| NO162285B (no) | 1989-08-28 |
| FI853731L (fi) | 1986-05-24 |
| DK165554B (da) | 1992-12-14 |
| AU4734185A (en) | 1986-05-29 |
| HUT38931A (en) | 1986-07-28 |
| NO853525L (no) | 1986-05-26 |
| PH23064A (en) | 1989-03-27 |
| DK434185D0 (da) | 1985-09-25 |
| HU206710B (en) | 1992-12-28 |
| FI83518B (fi) | 1991-04-15 |
| AU598446B2 (en) | 1990-06-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4650804A (en) | Quinolizinone compounds and pharmaceutical composition comprising the same, useful as anti-ulcerative and anti-allergic agents | |
| CA1103246A (en) | Thiazine derivatives | |
| RU2238937C2 (ru) | Производные имидазола, фармацевтическая композиция и способ профилактики и/или лечения на их основе | |
| NO874904L (no) | Fremgangsmaate for fremstilling av nye imidazopyridin-forbindelser. | |
| EP0737193A1 (en) | Pyrazolopyridine adenosine antagonists | |
| EP0120589A1 (en) | Imidazo-heterocyclic compounds, processes for preparation thereof and pharmaceutical composition comprising the same | |
| JPH1087629A (ja) | 新規イソキノリン誘導体、およびその医薬用途 | |
| JPH11508267A (ja) | ピラゾール化合物および医薬組成物 | |
| US4831030A (en) | Diphenylpyridine compounds, processes for the preparation thereof and composition comprising the same | |
| JP4825387B2 (ja) | 新規な１，８−ナフチリジン−２（１ｈ）−オン誘導体 | |
| KR19980064040A (ko) | 피리딘 유도체, 피리딘 유도체의 제조 방법 및 그를 위한 중간체 | |
| Shatsauskas et al. | Synthesis of benzo [c][1, 7] naphthyridine derivatives | |
| CH645384A5 (de) | 3-phosphonocephalosporansaeure-derivate, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische mittel. | |
| FI83518C (fi) | Foerfarande foer framstaellning av farmakologiskt vaerdefulla kinolizinonfoereningar. | |
| AU769890B2 (en) | Sulfonamide compounds and uses thereof as medicines | |
| JPS6110584A (ja) | イミダゾイソキノリン化合物およびその製造方法 | |
| SU1362402A3 (ru) | Способ получени производных имидазола или их солей с кислотами | |
| KR930001413B1 (ko) | 퀴놀리지논 화합물의 제조방법 | |
| AU670708B2 (en) | Palladium catalyzed vinylic substitution reactions with 2-substituted-pyridines | |
| JPS60222482A (ja) | キノリジノン化合物またはその塩を含有する抗アレルギー剤 | |
| JPS62135473A (ja) | イミダゾ−ル縮合複素環化合物 | |
| FI63401C (fi) | Nytt foerfarande foer framstaellning av 4-oxo-4h-pyrido(1,2-a)pyrimidin-3-karboxylsyra- och 1-oxo-1h-pyrimido(1,2-a)kinolin-2-karboxylsyraderivat | |
| JPS63225375A (ja) | キノリジノン誘導体 | |
| KR19990011423A (ko) | 신규한 세펨 유도체, 그의 제조방법 및 그의 항균제로서의 용도 | |
| KR19980054708A (ko) | N-니트로구아니딘 유도체 및 이의 제조방법 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: FUJISAWA PHARMACEUTICAL CO., LTD |