CH616663A5 - - Google Patents
Download PDFInfo
- Publication number
- CH616663A5 CH616663A5 CH794176A CH794176A CH616663A5 CH 616663 A5 CH616663 A5 CH 616663A5 CH 794176 A CH794176 A CH 794176A CH 794176 A CH794176 A CH 794176A CH 616663 A5 CH616663 A5 CH 616663A5
- Authority
- CH
- Switzerland
- Prior art keywords
- dichloroacetyl
- tetrahydro
- compound
- chloride
- quinolineol
- Prior art date
Links
- -1 3-thenoyl Chemical group 0.000 claims description 74
- 150000001875 compounds Chemical class 0.000 claims description 45
- 238000000034 method Methods 0.000 claims description 28
- OFTKFKYVSBNYEC-UHFFFAOYSA-N 2-furoyl chloride Chemical compound ClC(=O)C1=CC=CO1 OFTKFKYVSBNYEC-UHFFFAOYSA-N 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- QIQITDHWZYEEPA-UHFFFAOYSA-N thiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CS1 QIQITDHWZYEEPA-UHFFFAOYSA-N 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- XAJKVLQIIPSZKK-UHFFFAOYSA-N [5-chloro-1-(2,2-dichloroacetyl)-3,4-dihydro-2h-quinolin-6-yl] furan-2-carboxylate Chemical compound C=1C=C2N(C(=O)C(Cl)Cl)CCCC2=C(Cl)C=1OC(=O)C1=CC=CO1 XAJKVLQIIPSZKK-UHFFFAOYSA-N 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 238000005893 bromination reaction Methods 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 230000031709 bromination Effects 0.000 claims description 2
- 238000005660 chlorination reaction Methods 0.000 claims description 2
- 125000005179 haloacetyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 239000012320 chlorinating reagent Substances 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 150000003855 acyl compounds Chemical class 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 66
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 22
- 241000699800 Cricetinae Species 0.000 description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 14
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 206010001981 Amoebic infections Diseases 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 description 7
- RBWYRAQWXIIIRP-UHFFFAOYSA-N 2,2-dichloro-1-(5-chloro-6-hydroxy-3,4-dihydro-2h-quinolin-1-yl)ethanone Chemical compound ClC(Cl)C(=O)N1CCCC2=C(Cl)C(O)=CC=C21 RBWYRAQWXIIIRP-UHFFFAOYSA-N 0.000 description 7
- OMZBOXOCCLZODD-UHFFFAOYSA-N 2,2-dichloro-1-(6-hydroxy-3,4-dihydro-2h-quinolin-1-yl)ethanone Chemical compound ClC(Cl)C(=O)N1CCCC2=CC(O)=CC=C21 OMZBOXOCCLZODD-UHFFFAOYSA-N 0.000 description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- CTJSPUFGQNVJJP-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinolin-6-ol Chemical compound N1CCCC2=CC(O)=CC=C21 CTJSPUFGQNVJJP-UHFFFAOYSA-N 0.000 description 6
- AJFZAOUNZLCNJE-UHFFFAOYSA-N 1-(5-bromo-6-hydroxy-3,4-dihydro-2h-quinolin-1-yl)-2,2-dichloroethanone Chemical compound ClC(Cl)C(=O)N1CCCC2=C(Br)C(O)=CC=C21 AJFZAOUNZLCNJE-UHFFFAOYSA-N 0.000 description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 125000001246 bromo group Chemical group Br* 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 4
- 238000005917 acylation reaction Methods 0.000 description 4
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- WEPSNBVVWKNNBE-UHFFFAOYSA-N 2,2,2-trichloro-1-(6-hydroxy-3,4-dihydro-2h-quinolin-1-yl)ethanone Chemical compound ClC(Cl)(Cl)C(=O)N1CCCC2=CC(O)=CC=C21 WEPSNBVVWKNNBE-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 230000006179 O-acylation Effects 0.000 description 3
- 238000004061 bleaching Methods 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 230000000968 intestinal effect Effects 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000012258 stirred mixture Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 210000003812 trophozoite Anatomy 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- HKMDGZLOIORFAN-UHFFFAOYSA-N 2,2-dibromo-1-(5-bromo-6-hydroxy-3,4-dihydro-2h-quinolin-1-yl)ethanone Chemical compound BrC(Br)C(=O)N1CCCC2=C(Br)C(O)=CC=C21 HKMDGZLOIORFAN-UHFFFAOYSA-N 0.000 description 2
- LMWJXYVLYFBHTP-UHFFFAOYSA-N 2,2-dibromo-1-(6-hydroxy-3,4-dihydro-2h-quinolin-1-yl)ethanone Chemical compound BrC(Br)C(=O)N1CCCC2=CC(O)=CC=C21 LMWJXYVLYFBHTP-UHFFFAOYSA-N 0.000 description 2
- XNMYNYSCEJBRPZ-UHFFFAOYSA-N 2-[(3-butyl-1-isoquinolinyl)oxy]-N,N-dimethylethanamine Chemical compound C1=CC=C2C(OCCN(C)C)=NC(CCCC)=CC2=C1 XNMYNYSCEJBRPZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 230000006181 N-acylation Effects 0.000 description 2
- IPNQVLKPRLUPKB-UHFFFAOYSA-N [1-(2,2-dichloroacetyl)-3,4-dihydro-2h-quinolin-6-yl] benzoate Chemical compound C=1C=C2N(C(=O)C(Cl)Cl)CCCC2=CC=1OC(=O)C1=CC=CC=C1 IPNQVLKPRLUPKB-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 150000001266 acyl halides Chemical class 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 210000004534 cecum Anatomy 0.000 description 2
- 230000000973 chemotherapeutic effect Effects 0.000 description 2
- BTUIFMCWPFMNRG-UHFFFAOYSA-N furan-3-carbonyl chloride Chemical compound ClC(=O)C=1C=COC=1 BTUIFMCWPFMNRG-UHFFFAOYSA-N 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- QTWBEVAYYDZLQL-UHFFFAOYSA-N thiophene-3-carbonyl chloride Chemical compound ClC(=O)C=1C=CSC=1 QTWBEVAYYDZLQL-UHFFFAOYSA-N 0.000 description 2
- OVPBFYFMPCIKAA-UHFFFAOYSA-N (1-benzoyl-3,4-dihydro-2h-quinolin-6-yl) acetate Chemical compound C1CCC2=CC(OC(=O)C)=CC=C2N1C(=O)C1=CC=CC=C1 OVPBFYFMPCIKAA-UHFFFAOYSA-N 0.000 description 1
- MPBFATFRIBXCNK-UHFFFAOYSA-N (6-hydroxy-3,4-dihydro-2h-quinolin-1-yl)-phenylmethanone Chemical compound C1CCC2=CC(O)=CC=C2N1C(=O)C1=CC=CC=C1 MPBFATFRIBXCNK-UHFFFAOYSA-N 0.000 description 1
- LYUPJHVGLFETDG-UHFFFAOYSA-N 1-phenylbutan-2-ol Chemical compound CCC(O)CC1=CC=CC=C1 LYUPJHVGLFETDG-UHFFFAOYSA-N 0.000 description 1
- VHENKGPMQFCPDF-UHFFFAOYSA-N 2,2,2-tribromo-1-(5-bromo-6-hydroxy-3,4-dihydro-2h-quinolin-1-yl)ethanone Chemical compound BrC(Br)(Br)C(=O)N1CCCC2=C(Br)C(O)=CC=C21 VHENKGPMQFCPDF-UHFFFAOYSA-N 0.000 description 1
- FZLRSCUTFHQERD-UHFFFAOYSA-N 2,2,2-tribromo-1-(6-hydroxy-3,4-dihydro-2h-quinolin-1-yl)ethanone Chemical compound BrC(Br)(Br)C(=O)N1CCCC2=CC(O)=CC=C21 FZLRSCUTFHQERD-UHFFFAOYSA-N 0.000 description 1
- RDBMNMVDVKRYKW-UHFFFAOYSA-N 2,2,2-tribromoacetyl chloride Chemical compound ClC(=O)C(Br)(Br)Br RDBMNMVDVKRYKW-UHFFFAOYSA-N 0.000 description 1
- DPHYNTZHMBDDGB-UHFFFAOYSA-N 2,2,2-trichloro-1-(5-chloro-6-hydroxy-3,4-dihydro-2h-quinolin-1-yl)ethanone Chemical compound ClC(Cl)(Cl)C(=O)N1CCCC2=C(Cl)C(O)=CC=C21 DPHYNTZHMBDDGB-UHFFFAOYSA-N 0.000 description 1
- SCQYFFYVHXLAQV-UHFFFAOYSA-N 2,2-dibromoacetyl bromide Chemical compound BrC(Br)C(Br)=O SCQYFFYVHXLAQV-UHFFFAOYSA-N 0.000 description 1
- LQBBYHUQQRZRLK-UHFFFAOYSA-N 2,2-dibromoacetyl chloride Chemical compound ClC(=O)C(Br)Br LQBBYHUQQRZRLK-UHFFFAOYSA-N 0.000 description 1
- IUVCFHHAEHNCFT-INIZCTEOSA-N 2-[(1s)-1-[4-amino-3-(3-fluoro-4-propan-2-yloxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-6-fluoro-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=C(F)C(OC(C)C)=CC=C1C(C1=C(N)N=CN=C11)=NN1[C@@H](C)C1=C(C=2C=C(F)C=CC=2)C(=O)C2=CC(F)=CC=C2O1 IUVCFHHAEHNCFT-INIZCTEOSA-N 0.000 description 1
- YVUFDPUKVYAZNX-UHFFFAOYSA-N 2-bromo-2-chloroacetyl chloride Chemical compound ClC(Br)C(Cl)=O YVUFDPUKVYAZNX-UHFFFAOYSA-N 0.000 description 1
- LSTRKXWIZZZYAS-UHFFFAOYSA-N 2-bromoacetyl bromide Chemical compound BrCC(Br)=O LSTRKXWIZZZYAS-UHFFFAOYSA-N 0.000 description 1
- JYUWHHHXECHQED-UHFFFAOYSA-N 2-chloro-1-(6-hydroxy-3,4-dihydro-2h-quinolin-1-yl)ethanone Chemical compound ClCC(=O)N1CCCC2=CC(O)=CC=C21 JYUWHHHXECHQED-UHFFFAOYSA-N 0.000 description 1
- NHXMRVLOGGJBAI-UHFFFAOYSA-N 2-chloro-1-(8-methyl-3,4-dihydro-2h-quinolin-1-yl)ethanone Chemical compound C1CCN(C(=O)CCl)C2=C1C=CC=C2C NHXMRVLOGGJBAI-UHFFFAOYSA-N 0.000 description 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 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
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-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
- 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
- 241000224421 Heterolobosea Species 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
- 229930195725 Mannitol Natural products 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- LJBHQXSMSCILAP-UHFFFAOYSA-N [1-(2,2-dichloroacetyl)-3,4-dihydro-2h-quinolin-6-yl] 2,2,2-trichloroacetate Chemical compound ClC(Cl)(Cl)C(=O)OC1=CC=C2N(C(=O)C(Cl)Cl)CCCC2=C1 LJBHQXSMSCILAP-UHFFFAOYSA-N 0.000 description 1
- JYKVJOREDUOMQX-UHFFFAOYSA-N [1-(2,2-dichloroacetyl)-3,4-dihydro-2h-quinolin-6-yl] 2,2-dibromoacetate Chemical compound BrC(Br)C(=O)OC1=CC=C2N(C(=O)C(Cl)Cl)CCCC2=C1 JYKVJOREDUOMQX-UHFFFAOYSA-N 0.000 description 1
- NKAJQHOLRXHOLI-UHFFFAOYSA-N [1-(2,2-dichloroacetyl)-3,4-dihydro-2h-quinolin-6-yl] acetate Chemical compound ClC(Cl)C(=O)N1CCCC2=CC(OC(=O)C)=CC=C21 NKAJQHOLRXHOLI-UHFFFAOYSA-N 0.000 description 1
- YRKGLLSNNQGLCL-UHFFFAOYSA-N [1-(2,2-dichloroacetyl)-3,4-dihydro-2h-quinolin-6-yl] butanoate Chemical compound ClC(Cl)C(=O)N1CCCC2=CC(OC(=O)CCC)=CC=C21 YRKGLLSNNQGLCL-UHFFFAOYSA-N 0.000 description 1
- DHIXDKJXDPYACC-UHFFFAOYSA-N [1-(2,2-dichloroacetyl)-3,4-dihydro-2h-quinolin-6-yl] n-hexylcarbamate Chemical compound ClC(Cl)C(=O)N1CCCC2=CC(OC(=O)NCCCCCC)=CC=C21 DHIXDKJXDPYACC-UHFFFAOYSA-N 0.000 description 1
- GGOZZIDBHRIYLR-UHFFFAOYSA-N [5-bromo-1-(2,2-dibromoacetyl)-3,4-dihydro-2h-quinolin-6-yl] thiophene-2-carboxylate Chemical compound C=1C=C2N(C(=O)C(Br)Br)CCCC2=C(Br)C=1OC(=O)C1=CC=CS1 GGOZZIDBHRIYLR-UHFFFAOYSA-N 0.000 description 1
- FLJRCQFSOBEUNG-UHFFFAOYSA-N [5-bromo-1-(2,2-dichloroacetyl)-3,4-dihydro-2h-quinolin-6-yl] furan-2-carboxylate Chemical compound C=1C=C2N(C(=O)C(Cl)Cl)CCCC2=C(Br)C=1OC(=O)C1=CC=CO1 FLJRCQFSOBEUNG-UHFFFAOYSA-N 0.000 description 1
- DTYKNSLECVTIGL-UHFFFAOYSA-N [5-bromo-1-(2,2-dichloroacetyl)-3,4-dihydro-2h-quinolin-6-yl] thiophene-2-carboxylate Chemical compound C=1C=C2N(C(=O)C(Cl)Cl)CCCC2=C(Br)C=1OC(=O)C1=CC=CS1 DTYKNSLECVTIGL-UHFFFAOYSA-N 0.000 description 1
- PQMAASWUUWNCEG-UHFFFAOYSA-N [5-chloro-1-(2,2,2-trichloroacetyl)-3,4-dihydro-2h-quinolin-6-yl] thiophene-2-carboxylate Chemical compound C1=CC=2N(C(=O)C(Cl)(Cl)Cl)CCCC=2C(Cl)=C1OC(=O)C1=CC=CS1 PQMAASWUUWNCEG-UHFFFAOYSA-N 0.000 description 1
- MUROKZWUMKMIFD-UHFFFAOYSA-N [5-chloro-1-(2,2-dichloroacetyl)-3,4-dihydro-2h-quinolin-6-yl] 2,2,2-trichloroacetate Chemical compound ClC(Cl)(Cl)C(=O)OC1=CC=C2N(C(=O)C(Cl)Cl)CCCC2=C1Cl MUROKZWUMKMIFD-UHFFFAOYSA-N 0.000 description 1
- TZCURQZIQKYOHG-UHFFFAOYSA-N [5-chloro-1-(2,2-dichloroacetyl)-3,4-dihydro-2h-quinolin-6-yl] 2,2-dichloroacetate Chemical compound ClC(Cl)C(=O)N1CCCC2=C(Cl)C(OC(=O)C(Cl)Cl)=CC=C21 TZCURQZIQKYOHG-UHFFFAOYSA-N 0.000 description 1
- MCJUZKZCFPJLQK-UHFFFAOYSA-N [5-chloro-1-(2,2-dichloroacetyl)-3,4-dihydro-2h-quinolin-6-yl] acetate Chemical compound ClC(Cl)C(=O)N1CCCC2=C(Cl)C(OC(=O)C)=CC=C21 MCJUZKZCFPJLQK-UHFFFAOYSA-N 0.000 description 1
- YQKVQKMGWCAEII-UHFFFAOYSA-N [5-chloro-1-(2,2-dichloroacetyl)-3,4-dihydro-2h-quinolin-6-yl] benzoate Chemical compound C=1C=C2N(C(=O)C(Cl)Cl)CCCC2=C(Cl)C=1OC(=O)C1=CC=CC=C1 YQKVQKMGWCAEII-UHFFFAOYSA-N 0.000 description 1
- UQWLIJFJXNGXHG-UHFFFAOYSA-N [5-chloro-1-(2,2-dichloroacetyl)-3,4-dihydro-2h-quinolin-6-yl] formate Chemical compound O=COC1=CC=C2N(C(=O)C(Cl)Cl)CCCC2=C1Cl UQWLIJFJXNGXHG-UHFFFAOYSA-N 0.000 description 1
- XAJOEUFNXXFUGE-UHFFFAOYSA-N [5-chloro-1-(2,2-dichloroacetyl)-3,4-dihydro-2h-quinolin-6-yl] furan-3-carboxylate Chemical compound C=1C=C2N(C(=O)C(Cl)Cl)CCCC2=C(Cl)C=1OC(=O)C=1C=COC=1 XAJOEUFNXXFUGE-UHFFFAOYSA-N 0.000 description 1
- UTEBPELYPXPDPK-UHFFFAOYSA-N [5-chloro-1-(2,2-dichloroacetyl)-3,4-dihydro-2h-quinolin-6-yl] n-methylcarbamate Chemical compound ClC(Cl)C(=O)N1CCCC2=C(Cl)C(OC(=O)NC)=CC=C21 UTEBPELYPXPDPK-UHFFFAOYSA-N 0.000 description 1
- MXUGTQCBBSOOAL-UHFFFAOYSA-N [5-chloro-1-(2,2-dichloroacetyl)-3,4-dihydro-2h-quinolin-6-yl] thiophene-2-carboxylate Chemical compound C=1C=C2N(C(=O)C(Cl)Cl)CCCC2=C(Cl)C=1OC(=O)C1=CC=CS1 MXUGTQCBBSOOAL-UHFFFAOYSA-N 0.000 description 1
- IGGWACUUMSGMOM-UHFFFAOYSA-N [5-chloro-1-(2,2-dichloroacetyl)-3,4-dihydro-2h-quinolin-6-yl] thiophene-3-carboxylate Chemical compound C=1C=C2N(C(=O)C(Cl)Cl)CCCC2=C(Cl)C=1OC(=O)C=1C=CSC=1 IGGWACUUMSGMOM-UHFFFAOYSA-N 0.000 description 1
- XORPVGLBZBAUSQ-UHFFFAOYSA-N [5-chloro-1-(2-chloroacetyl)-3,4-dihydro-2h-quinolin-6-yl] thiophene-2-carboxylate Chemical compound C=1C=C2N(C(=O)CCl)CCCC2=C(Cl)C=1OC(=O)C1=CC=CS1 XORPVGLBZBAUSQ-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 210000003001 amoeba Anatomy 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000003556 assay Methods 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
- 230000037396 body weight Effects 0.000 description 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- VGGRCVDNFAQIKO-UHFFFAOYSA-N formic anhydride Chemical compound O=COC=O VGGRCVDNFAQIKO-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- ARBOVOVUTSQWSS-UHFFFAOYSA-N hexadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCC(Cl)=O ARBOVOVUTSQWSS-UHFFFAOYSA-N 0.000 description 1
- ANJPRQPHZGHVQB-UHFFFAOYSA-N hexyl isocyanate Chemical compound CCCCCCN=C=O ANJPRQPHZGHVQB-UHFFFAOYSA-N 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000037230 mobility Effects 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
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003960 organic solvent Substances 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
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229960005038 quinisocaine Drugs 0.000 description 1
- OVYWMEWYEJLIER-UHFFFAOYSA-N quinolin-6-ol Chemical compound N1=CC=CC2=CC(O)=CC=C21 OVYWMEWYEJLIER-UHFFFAOYSA-N 0.000 description 1
- RZHZJLAPZGYKLY-UHFFFAOYSA-N quinolin-6-yl n-hexylcarbamate Chemical compound N1=CC=CC2=CC(OC(=O)NCCCCCC)=CC=C21 RZHZJLAPZGYKLY-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 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
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000725 suspension 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/589,195 US3997542A (en) | 1975-06-23 | 1975-06-23 | 1-(Halogenated-acetyl)-1,2,3,4-tetrahydro-6-quinolinols and esters thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH616663A5 true CH616663A5 (en:Method) | 1980-04-15 |
Family
ID=24357017
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH794176A CH616663A5 (en:Method) | 1975-06-23 | 1976-06-22 |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US3997542A (en:Method) |
| JP (1) | JPS523078A (en:Method) |
| AU (1) | AU504124B2 (en:Method) |
| BE (1) | BE843237A (en:Method) |
| CH (1) | CH616663A5 (en:Method) |
| DE (1) | DE2627994A1 (en:Method) |
| DK (1) | DK280376A (en:Method) |
| EG (1) | EG12277A (en:Method) |
| ES (2) | ES449094A1 (en:Method) |
| FI (1) | FI761805A7 (en:Method) |
| FR (1) | FR2315275A1 (en:Method) |
| GB (1) | GB1497004A (en:Method) |
| IE (1) | IE43580B1 (en:Method) |
| IL (1) | IL49823A (en:Method) |
| IT (1) | IT1066971B (en:Method) |
| LU (1) | LU75220A1 (en:Method) |
| NL (1) | NL7606624A (en:Method) |
| NO (1) | NO762150L (en:Method) |
| PH (1) | PH11508A (en:Method) |
| PT (1) | PT65256B (en:Method) |
| SE (1) | SE7607175L (en:Method) |
| ZA (1) | ZA763622B (en:Method) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6706751B2 (en) * | 2000-12-21 | 2004-03-16 | Hoffman-La Roche Inc. | Dihydroindole and tetrahydroquinoline derivatives |
| US7655801B2 (en) * | 2004-12-28 | 2010-02-02 | Council Of Scientific And Industrial Research | Substituted carbamic acid quinolin-6-yl esters useful as acetylcholinesterase inhibitors |
| EP1831172B1 (en) * | 2004-12-28 | 2009-02-18 | Council of Scientific and Industrial Research | Substituted carbamic acid quinolin-6-yl esters useful as acetylcholinesterase inhibitors |
| CN108912101A (zh) * | 2018-07-20 | 2018-11-30 | 上海裕英生物医药科技有限公司 | 一种喹法米特的晶型 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2666058A (en) * | 1950-05-16 | 1954-01-12 | Ciba Pharm Prod Inc | Undecylenic acid esters of 8-hydroxyquinolines |
| IL33560A (en) * | 1969-02-10 | 1973-04-30 | Recordati Chem Pharm | Therapeutically active esters of 8-hydroxy-quinolines and a method for their preparation |
-
1975
- 1975-06-23 US US05/589,195 patent/US3997542A/en not_active Expired - Lifetime
-
1976
- 1976-06-07 GB GB23506/76A patent/GB1497004A/en not_active Expired
- 1976-06-16 PH PH18578A patent/PH11508A/en unknown
- 1976-06-17 AU AU14999/76A patent/AU504124B2/en not_active Expired
- 1976-06-17 IL IL49823A patent/IL49823A/xx unknown
- 1976-06-18 NL NL7606624A patent/NL7606624A/xx not_active Application Discontinuation
- 1976-06-18 ZA ZA763622A patent/ZA763622B/xx unknown
- 1976-06-21 NO NO762150A patent/NO762150L/no unknown
- 1976-06-22 BE BE1007469A patent/BE843237A/xx unknown
- 1976-06-22 FR FR7618943A patent/FR2315275A1/fr active Granted
- 1976-06-22 DK DK280376A patent/DK280376A/da not_active Application Discontinuation
- 1976-06-22 IE IE1344/76A patent/IE43580B1/en unknown
- 1976-06-22 LU LU75220A patent/LU75220A1/xx unknown
- 1976-06-22 CH CH794176A patent/CH616663A5/fr not_active IP Right Cessation
- 1976-06-22 FI FI761805A patent/FI761805A7/fi not_active Application Discontinuation
- 1976-06-22 IT IT24586/76A patent/IT1066971B/it active
- 1976-06-22 ES ES449094A patent/ES449094A1/es not_active Expired
- 1976-06-22 SE SE7607175A patent/SE7607175L/xx not_active Application Discontinuation
- 1976-06-22 PT PT65256A patent/PT65256B/pt unknown
- 1976-06-23 JP JP51074280A patent/JPS523078A/ja active Pending
- 1976-06-23 EG EG374/76A patent/EG12277A/xx active
- 1976-06-23 DE DE19762627994 patent/DE2627994A1/de not_active Withdrawn
-
1977
- 1977-07-09 ES ES460597A patent/ES460597A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NO762150L (en:Method) | 1976-12-27 |
| ES449094A1 (es) | 1977-11-16 |
| LU75220A1 (en:Method) | 1977-03-15 |
| PT65256A (en) | 1976-07-01 |
| AU1499976A (en) | 1977-12-22 |
| JPS523078A (en) | 1977-01-11 |
| IT1066971B (it) | 1985-03-12 |
| BE843237A (fr) | 1976-12-22 |
| FR2315275A1 (fr) | 1977-01-21 |
| EG12277A (en) | 1978-09-30 |
| FR2315275B1 (en:Method) | 1978-12-15 |
| ZA763622B (en) | 1977-05-25 |
| DK280376A (da) | 1976-12-24 |
| IL49823A (en) | 1979-09-30 |
| AU504124B2 (en) | 1979-10-04 |
| PH11508A (en) | 1978-02-01 |
| US3997542A (en) | 1976-12-14 |
| GB1497004A (en) | 1978-01-05 |
| SE7607175L (sv) | 1976-12-24 |
| IE43580B1 (en) | 1981-04-08 |
| NL7606624A (nl) | 1976-12-27 |
| PT65256B (en) | 1977-12-07 |
| DE2627994A1 (de) | 1977-01-20 |
| IL49823A0 (en) | 1976-08-31 |
| IE43580L (en) | 1976-12-23 |
| ES460597A1 (es) | 1978-05-01 |
| FI761805A7 (en:Method) | 1976-12-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| LU86406A1 (fr) | Imidazoquinoleines antithrombogenes cardiotoniques | |
| EP0376849A1 (fr) | Nouveaux dérivés de la 2,4-dioxo 2,3,4,5-tétrahydro 1H-1,5-benzodiazépine, leur procédé et les intermédiaires de préparation, leur application comme médicaments et les compositions les renfermant | |
| RU2125569C1 (ru) | Производные полизамещенных 2-амидо-4-фенилтиазолов, способ их получения, промежуточные соединения синтеза и фармацевтическая композиция на их основе | |
| EP0340064B1 (fr) | Benzodiazépines, leur procédé et intermédiaires de préparation et leurs applications en thérapeutique | |
| EP0463945A1 (fr) | Nouvelles chalcones, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent | |
| FR2663935A1 (fr) | Nouveaux 1,2,3,4,5,6-hexahydroazepino [4,5-b] indoles et 1,2,3,4-tetrahydrobethacarbolines, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent. | |
| JPH0471073B2 (en:Method) | ||
| FR2601016A1 (fr) | Nouveaux derives du 1h,3h-pyrrolo (1,2-c) thiazole, leur preparation et les compositions pharmaceutiques qui les contiennent | |
| EP0446141B1 (fr) | Nouveaux dérivés d'imidazo [1,2-C] quinazoline leur procédé de préparation et les compositions pharmaceutiques les renfermant | |
| FR2833261A1 (fr) | Nouveaux composes inhibiteurs specifiques de la phospholipase a2 secretee non pancreatique humaine du groupe ii | |
| HU209645B (en) | Process for producing heteroaryl-sulphonamido-carbazole derivatives | |
| CA1195333A (fr) | Procede de preparation de nouveaux derives du 2-oxo- pyrid 3-yl ou piperidin 3-yl indole et de leurs sels | |
| CH616663A5 (en:Method) | ||
| SU1282818A3 (ru) | Способ получени ортоконденсированных производных пиррола | |
| US5185360A (en) | Dihydroindenoindole compounds and methods for using the same | |
| FR2623808A1 (fr) | Nouveaux derives flavonoides (benzyl-4 piperazinyl-1)-2 oxo-2 ethylene substitues, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent | |
| EP0635002B1 (fr) | Nouveaux derives de perhydroisoindole, et leur preparation | |
| FR2722195A1 (fr) | Nouveaux derives de 1,3-dihydro-2h-pyrrolo(2,3-b) pyridin-2-ones et oxazolo(4,5-b) pyridin-2(3h)-ones, leur procede de preparation et les compositions pharmaceutiques qui les contiennent | |
| BE897208A (fr) | Composes de carbostyryle | |
| SU1685264A3 (ru) | Способ получени производных пиррола | |
| JPH0560478B2 (en:Method) | ||
| FR2742151A1 (fr) | Utilisation de derives de bicycles mono ou dicetoniques, nouveaux composes obtenus et leur application en therapeutique | |
| FR2565980A1 (fr) | Nouveaux esters de 1,1-dioxydes de n-heteroaryl-4-hydroxy-2-methyl- 2h -1,2-benzothiazine- (ou thieno(2,3-e)-1,2-thiazine)-3-carboxamide precurseurs de medicaments et composition pharmaceutiques les contenant | |
| LU82950A1 (fr) | 1-oxo-1h-thiazolo-(3,2-a)-pyrimidine-2-carboxamides,anti-allergiques et anti-ulcereux,medicament les contenant et composes intermediaires permettant de les obtenir | |
| BRPI0707423A2 (pt) | composto, sal, uso de um composto, método de tratamento de distúrbios, composição farmacêutica, enantiÈmero, uso de um enantiÈmero, e, processos para a preparação de um enantiÈmero, e para a preparação de um composto |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |