CA1171861A - Procede de preparation d'amino-4 chloro-7 quinoleines - Google Patents
Procede de preparation d'amino-4 chloro-7 quinoleinesInfo
- Publication number
- CA1171861A CA1171861A CA000394273A CA394273A CA1171861A CA 1171861 A CA1171861 A CA 1171861A CA 000394273 A CA000394273 A CA 000394273A CA 394273 A CA394273 A CA 394273A CA 1171861 A CA1171861 A CA 1171861A
- Authority
- CA
- Canada
- Prior art keywords
- chloro
- amino
- quinolinone
- carbon atoms
- general formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- NDRZSRWMMUGOBP-UHFFFAOYSA-N 4-Amino-7-chloroquinoline Chemical compound ClC1=CC=C2C(N)=CC=NC2=C1 NDRZSRWMMUGOBP-UHFFFAOYSA-N 0.000 title 1
- 239000003054 catalyst Substances 0.000 claims abstract description 30
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims abstract description 23
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
- 229910052707 ruthenium Inorganic materials 0.000 claims abstract description 9
- 150000001412 amines Chemical class 0.000 claims abstract description 7
- 238000009833 condensation Methods 0.000 claims abstract description 7
- 230000005494 condensation Effects 0.000 claims abstract description 7
- QVCRGJALYOLXDC-UHFFFAOYSA-N 2-chloroquinolin-4-amine Chemical class C1=CC=C2C(N)=CC(Cl)=NC2=C1 QVCRGJALYOLXDC-UHFFFAOYSA-N 0.000 claims abstract description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 238000005899 aromatization reaction Methods 0.000 claims abstract 4
- -1 halide ions Chemical class 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 13
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 11
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 9
- 229960003677 chloroquine Drugs 0.000 claims description 9
- WHTVZRBIWZFKQO-UHFFFAOYSA-N chloroquine Natural products ClC1=CC=C2C(NC(C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-UHFFFAOYSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- WHTVZRBIWZFKQO-AWEZNQCLSA-N (S)-chloroquine Chemical compound ClC1=CC=C2C(N[C@@H](C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-AWEZNQCLSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- CAPCBAYULRXQAN-UHFFFAOYSA-N 1-n,1-n-diethylpentane-1,4-diamine Chemical compound CCN(CC)CCCC(C)N CAPCBAYULRXQAN-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 238000010533 azeotropic distillation Methods 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 abstract 2
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 2
- QRJMFMFNPROMBS-UHFFFAOYSA-N 1-chloro-2,3-dihydroquinolin-4-one Chemical compound C1=CC=C2N(Cl)CCC(=O)C2=C1 QRJMFMFNPROMBS-UHFFFAOYSA-N 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 40
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 22
- 238000001914 filtration Methods 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- 239000012074 organic phase Substances 0.000 description 14
- 239000012071 phase Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 230000009466 transformation Effects 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000007789 gas Substances 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- 238000004587 chromatography analysis Methods 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 7
- 238000004817 gas chromatography Methods 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 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 3
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000010908 decantation Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical compound ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 229960005038 quinisocaine Drugs 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OVCDSSHSILBFBN-UHFFFAOYSA-N Amodiaquine Chemical compound C1=C(O)C(CN(CC)CC)=CC(NC=2C3=CC=C(Cl)C=C3N=CC=2)=C1 OVCDSSHSILBFBN-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- XKFLQYSVUSNRHA-UHFFFAOYSA-N C1=CC(=CC=C1C2=NC3=C(C=CC(=C3)Cl)C(=C2)N)O Chemical compound C1=CC(=CC=C1C2=NC3=C(C=CC(=C3)Cl)C(=C2)N)O XKFLQYSVUSNRHA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 208000037656 Respiratory Sounds Diseases 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 229960001444 amodiaquine Drugs 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 125000006309 butyl amino group Chemical group 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 229960002050 hydrofluoric acid Drugs 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- IGEIPFLJVCPEKU-UHFFFAOYSA-N pentan-2-amine Chemical compound CCCC(C)N IGEIPFLJVCPEKU-UHFFFAOYSA-N 0.000 description 2
- JZKRBEDKUJKJGS-UHFFFAOYSA-N pentane dihydrate Chemical compound O.O.CCCCC JZKRBEDKUJKJGS-UHFFFAOYSA-N 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
- 150000003254 radicals Chemical class 0.000 description 2
- 206010037833 rales Diseases 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- WIXUZVQMOUIMNP-UHFFFAOYSA-N 2-(3-chloroanilino)propanoic acid Chemical compound OC(=O)C(C)NC1=CC=CC(Cl)=C1 WIXUZVQMOUIMNP-UHFFFAOYSA-N 0.000 description 1
- VMGPYGSLEMLNBZ-UHFFFAOYSA-N 2-chloro-6H-quinolin-7-one Chemical compound ClC1=NC2=CC(CC=C2C=C1)=O VMGPYGSLEMLNBZ-UHFFFAOYSA-N 0.000 description 1
- YMDNODNLFSHHCV-UHFFFAOYSA-N 2-chloro-n,n-diethylethanamine Chemical compound CCN(CC)CCCl YMDNODNLFSHHCV-UHFFFAOYSA-N 0.000 description 1
- GRGNJBKJCVOFEO-UHFFFAOYSA-N 5-(diethylamino)pentan-2-one Chemical compound CCN(CC)CCCC(C)=O GRGNJBKJCVOFEO-UHFFFAOYSA-N 0.000 description 1
- GIOODPXVUBAVRK-UHFFFAOYSA-N 7-chloro-n-phenylquinolin-4-amine Chemical compound C=1C=NC2=CC(Cl)=CC=C2C=1NC1=CC=CC=C1 GIOODPXVUBAVRK-UHFFFAOYSA-N 0.000 description 1
- 235000014066 European mistletoe Nutrition 0.000 description 1
- JQVDAXLFBXTEQA-UHFFFAOYSA-N N-butyl-butylamine Natural products CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 235000012300 Rhipsalis cassutha Nutrition 0.000 description 1
- 241000221012 Viscum Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000078 anti-malarial effect Effects 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229960001701 chloroform Drugs 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- JIDMRNCLMYYMAK-UHFFFAOYSA-N cyclohexatrienecarboxylic acid Chemical group OC(=O)C1=C=CC=C[CH]1 JIDMRNCLMYYMAK-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000005695 dehalogenation reaction Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- GWOFUCIGLDBNKM-UHFFFAOYSA-N glafenine Chemical compound OCC(O)COC(=O)C1=CC=CC=C1NC1=CC=NC2=CC(Cl)=CC=C12 GWOFUCIGLDBNKM-UHFFFAOYSA-N 0.000 description 1
- 229960001650 glafenine Drugs 0.000 description 1
- 125000001145 hydrido group Chemical group *[H] 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N o-aminobenzenecarboxylic acid Natural products NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229940124641 pain reliever Drugs 0.000 description 1
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 1
- 238000003822 preparative gas chromatography Methods 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 229930185107 quinolinone Natural products 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 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
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
-
- 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
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
-
- 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
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
- C07D215/46—Nitrogen atoms attached in position 4 with hydrocarbon radicals, substituted by nitrogen atoms, attached to said nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Quinoline Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8100765A FR2498187A1 (fr) | 1981-01-16 | 1981-01-16 | Procede de preparation d'amino-4 chloro-7 quinoleines |
| FR8100765 | 1981-01-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1171861A true CA1171861A (fr) | 1984-07-31 |
Family
ID=9254223
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000394273A Expired CA1171861A (fr) | 1981-01-16 | 1982-01-15 | Procede de preparation d'amino-4 chloro-7 quinoleines |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4421920A (ref) |
| EP (1) | EP0056766B1 (ref) |
| JP (1) | JPS57171973A (ref) |
| KR (1) | KR870001921B1 (ref) |
| AT (1) | ATE7492T1 (ref) |
| CA (1) | CA1171861A (ref) |
| DE (1) | DE3260150D1 (ref) |
| DK (1) | DK148805C (ref) |
| FR (1) | FR2498187A1 (ref) |
| HU (1) | HU184985B (ref) |
| IE (1) | IE51957B1 (ref) |
| IN (1) | IN158327B (ref) |
| ZA (1) | ZA82277B (ref) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2892298A (en) * | 1957-08-05 | 1959-06-30 | Earl J Chaney | Pickup device |
| GB8426584D0 (en) * | 1984-10-19 | 1984-11-28 | Beecham Group Plc | Compounds |
| EP0222839A4 (en) * | 1985-05-17 | 1988-11-09 | Univ Australian | ANTI-MALARIA COMPOUNDS. |
| US4789678A (en) * | 1986-08-25 | 1988-12-06 | Hoechst-Roussel Pharmaceuticals, Inc. | Memory enhancing α-alkyl-4-amino-3-quinolinemethanols and 1-(4-aralkylamino-3-quinolinyl)alkanones and related compounds |
| CA1340821C (en) * | 1988-10-06 | 1999-11-16 | Nobuyuki Fukazawa | Heterocyclic compounds and anticancer-drug reinforcing agents containing them as effective components |
| PT100905A (pt) * | 1991-09-30 | 1994-02-28 | Eisai Co Ltd | Compostos heterociclicos azotados biciclicos contendo aneis de benzeno, ciclo-hexano ou piridina e de pirimidina, piridina ou imidazol substituidos e composicoes farmaceuticas que os contem |
| CA2133620A1 (en) * | 1993-10-28 | 1995-04-29 | Werner Hofheinz | Aminoquinoline derivatives |
| AU6168296A (en) * | 1995-06-07 | 1996-12-30 | The Administrators Of The Tulane Eductional Fund | Chloroquine analogs and methods of preventing and treating p lasmodial disease |
| US6291455B1 (en) | 1996-03-05 | 2001-09-18 | Zeneca Limited | 4-anilinoquinazoline derivatives |
| KR100567649B1 (ko) * | 1996-09-25 | 2006-04-05 | 아스트라제네카 유케이 리미티드 | 혈관 내피 성장 인자와 같은 성장 인자의 효과를 억제하는 퀴놀린 유도체 |
| GB9910580D0 (en) | 1999-05-08 | 1999-07-07 | Zeneca Ltd | Chemical compounds |
| GB9910579D0 (en) | 1999-05-08 | 1999-07-07 | Zeneca Ltd | Chemical compounds |
| ATE431141T1 (de) | 1999-07-13 | 2009-05-15 | Alpha Res Group Llc | Zusammensetzungen und verfahren zur behandlung der parkinson-krankheit |
| US20040229908A1 (en) * | 1999-07-13 | 2004-11-18 | Jodi Nelson | Compositions and methods for the treatment of Parkinson's disease and tardive dyskinesias |
| ES2267748T3 (es) * | 2000-04-07 | 2007-03-16 | Astrazeneca Ab | Compuestos de quinazolina. |
| EP1337513A1 (en) * | 2000-11-02 | 2003-08-27 | AstraZeneca AB | 4-substituted quinolines as antitumor agents |
| EP1337524A1 (en) * | 2000-11-02 | 2003-08-27 | AstraZeneca AB | Substituted quinolines as antitumor agents |
| US7084157B2 (en) * | 2002-05-17 | 2006-08-01 | Rajeev Raut | Ophthalmic pharmaceutical compositions and methods for treating ocular inflammation |
| US20040002451A1 (en) * | 2002-06-20 | 2004-01-01 | Bruce Kerwin | Compositions of pegylated soluble tumor necrosis factor receptors and methods of preparing |
| GB0215823D0 (en) * | 2002-07-09 | 2002-08-14 | Astrazeneca Ab | Quinazoline derivatives |
| GB0225579D0 (en) * | 2002-11-02 | 2002-12-11 | Astrazeneca Ab | Chemical compounds |
| US6916627B2 (en) * | 2002-11-27 | 2005-07-12 | St. Jude Children's Research Hospital | ATM kinase compositions and methods |
| US7108992B2 (en) * | 2002-11-27 | 2006-09-19 | St. Jude Children's Research Hospital | ATM kinase compositions and methods |
| US8309562B2 (en) * | 2003-07-03 | 2012-11-13 | Myrexis, Inc. | Compounds and therapeutical use thereof |
| NZ544472A (en) | 2003-07-03 | 2009-04-30 | Myriad Genetics Inc | Compounds and therapeutical use thereof |
| EA009994B1 (ru) * | 2003-12-23 | 2008-06-30 | Пфайзер Инк. | Новые хинолиновые производные |
| ES2237332B1 (es) | 2004-01-14 | 2006-11-01 | Consejo Sup. Investig. Cientificas | Derivados de piridinio y quinolinio. |
| US8586613B2 (en) | 2004-01-14 | 2013-11-19 | Universidad De Granada | Pyridinium and quinolinium derivatives |
| US8258145B2 (en) * | 2005-01-03 | 2012-09-04 | Myrexis, Inc. | Method of treating brain cancer |
| CA2592900A1 (en) | 2005-01-03 | 2006-07-13 | Myriad Genetics Inc. | Nitrogen containing bicyclic compounds and therapeutical use thereof |
| US8440695B2 (en) * | 2005-11-09 | 2013-05-14 | St Jude Children's Research Hospital | Use of chloroquine to treat metabolic syndrome |
| CN105693605B (zh) * | 2016-03-09 | 2017-12-22 | 西安科技大学 | 一种光学纯(r)/(s)‑氯喹的不对称合成方法 |
| CN105693606B (zh) * | 2016-03-09 | 2017-12-05 | 西安科技大学 | 一种光学纯(r)/(s)‑羟氯喹的不对称合成方法 |
| US20230416786A1 (en) | 2020-11-30 | 2023-12-28 | Cellectis Sa | Use of aminoquinoline compounds for higher gene integration |
| CN115947684B (zh) * | 2023-01-18 | 2025-01-17 | 贵州医科大学 | 一种钯和铜协同催化氧化芳构化制备4-胺基喹啉类衍生物的方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2653940A (en) * | 1951-01-27 | 1953-09-29 | William S Johnson | Process for preparing 4-quinolyl secondary amines |
-
1981
- 1981-01-16 FR FR8100765A patent/FR2498187A1/fr active Granted
-
1982
- 1982-01-14 JP JP57003535A patent/JPS57171973A/ja active Pending
- 1982-01-15 DK DK16582A patent/DK148805C/da not_active IP Right Cessation
- 1982-01-15 ZA ZA82277A patent/ZA82277B/xx unknown
- 1982-01-15 KR KR8200161A patent/KR870001921B1/ko not_active Expired
- 1982-01-15 US US06/339,722 patent/US4421920A/en not_active Expired - Fee Related
- 1982-01-15 EP EP82400080A patent/EP0056766B1/fr not_active Expired
- 1982-01-15 AT AT82400080T patent/ATE7492T1/de active
- 1982-01-15 CA CA000394273A patent/CA1171861A/fr not_active Expired
- 1982-01-15 HU HU82121A patent/HU184985B/hu not_active IP Right Cessation
- 1982-01-15 DE DE8282400080T patent/DE3260150D1/de not_active Expired
- 1982-01-15 IE IE75/82A patent/IE51957B1/en unknown
- 1982-01-15 IN IN36/DEL/82A patent/IN158327B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE3260150D1 (en) | 1984-06-20 |
| FR2498187A1 (fr) | 1982-07-23 |
| KR870001921B1 (ko) | 1987-10-22 |
| EP0056766B1 (fr) | 1984-05-16 |
| IE51957B1 (en) | 1987-04-29 |
| DK148805C (da) | 1986-04-01 |
| EP0056766A1 (fr) | 1982-07-28 |
| ZA82277B (en) | 1982-11-24 |
| DK16582A (da) | 1982-07-17 |
| JPS57171973A (en) | 1982-10-22 |
| FR2498187B1 (ref) | 1983-09-30 |
| HU184985B (en) | 1984-11-28 |
| IN158327B (ref) | 1986-10-18 |
| ATE7492T1 (de) | 1984-06-15 |
| DK148805B (da) | 1985-10-07 |
| KR830009038A (ko) | 1983-12-17 |
| US4421920A (en) | 1983-12-20 |
| IE820075L (en) | 1982-07-16 |
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