HU184985B - Process for producing 4-amino-chloroquinolines - Google Patents
Process for producing 4-amino-chloroquinolines Download PDFInfo
- Publication number
- HU184985B HU184985B HU82121A HU12182A HU184985B HU 184985 B HU184985 B HU 184985B HU 82121 A HU82121 A HU 82121A HU 12182 A HU12182 A HU 12182A HU 184985 B HU184985 B HU 184985B
- Authority
- HU
- Hungary
- Prior art keywords
- chloro
- mmol
- quinolinone
- tetrahydro
- diethylamino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 25
- QVCRGJALYOLXDC-UHFFFAOYSA-N 2-chloroquinolin-4-amine Chemical class C1=CC=C2C(N)=CC(Cl)=NC2=C1 QVCRGJALYOLXDC-UHFFFAOYSA-N 0.000 title abstract description 4
- 239000003054 catalyst Substances 0.000 claims abstract description 34
- 238000006243 chemical reaction Methods 0.000 claims abstract description 30
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229910052707 ruthenium Inorganic materials 0.000 claims abstract description 16
- 150000001412 amines Chemical class 0.000 claims abstract description 9
- 238000005899 aromatization reaction Methods 0.000 claims abstract description 5
- 238000009833 condensation Methods 0.000 claims abstract description 4
- 230000005494 condensation Effects 0.000 claims abstract description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 4
- HOLTZTRNTRXTNX-UHFFFAOYSA-N 7-chloro-2,3-dihydro-1h-quinolin-4-one Chemical compound O=C1CCNC2=CC(Cl)=CC=C21 HOLTZTRNTRXTNX-UHFFFAOYSA-N 0.000 claims description 35
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 26
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 24
- -1 halide ions Chemical class 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 12
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- SURLGNKAQXKNSP-DBLYXWCISA-N chlorin Chemical compound C\1=C/2\N/C(=C\C3=N/C(=C\C=4NC(/C=C\5/C=CC/1=N/5)=CC=4)/C=C3)/CC\2 SURLGNKAQXKNSP-DBLYXWCISA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 238000010533 azeotropic distillation Methods 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229940111121 antirheumatic drug quinolines Drugs 0.000 claims 1
- KYCIUIVANPKXLW-UHFFFAOYSA-N dimethyl-(2-phenoxyethyl)-(thiophen-2-ylmethyl)azanium Chemical compound C=1C=CSC=1C[N+](C)(C)CCOC1=CC=CC=C1 KYCIUIVANPKXLW-UHFFFAOYSA-N 0.000 claims 1
- 230000007717 exclusion Effects 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 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 description 3
- 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
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 28
- CAPCBAYULRXQAN-UHFFFAOYSA-N 1-n,1-n-diethylpentane-1,4-diamine Chemical compound CCN(CC)CCCC(C)N CAPCBAYULRXQAN-UHFFFAOYSA-N 0.000 description 23
- 239000000243 solution Substances 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 239000012074 organic phase Substances 0.000 description 16
- 239000007789 gas Substances 0.000 description 14
- 239000012071 phase Substances 0.000 description 14
- 229910000029 sodium carbonate Inorganic materials 0.000 description 14
- 239000007858 starting material Substances 0.000 description 14
- 238000004587 chromatography analysis Methods 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- 238000001816 cooling Methods 0.000 description 9
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- CAUPTGHSTDHRCZ-UHFFFAOYSA-N 1-n,1-n-diethyl-4-n-quinolin-4-ylpentane-1,4-diamine Chemical compound C1=CC=C2C(NC(C)CCCN(CC)CC)=CC=NC2=C1 CAUPTGHSTDHRCZ-UHFFFAOYSA-N 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 6
- DUQIMDPEIHBKCJ-UHFFFAOYSA-N 7-chloro-3h-quinolin-4-one Chemical compound O=C1CC=NC2=CC(Cl)=CC=C21 DUQIMDPEIHBKCJ-UHFFFAOYSA-N 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- KLOOQIJVAVCASC-UHFFFAOYSA-N 4-(2-amino-7-chloroquinolin-4-yl)phenol Chemical compound OC1=CC=C(C=C1)C1=CC(=NC2=CC(=CC=C12)Cl)N KLOOQIJVAVCASC-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- HETSDWRDICBRSQ-UHFFFAOYSA-N 3h-quinolin-4-one Chemical compound C1=CC=C2C(=O)CC=NC2=C1 HETSDWRDICBRSQ-UHFFFAOYSA-N 0.000 description 4
- 229910015900 BF3 Inorganic materials 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- WHTVZRBIWZFKQO-UHFFFAOYSA-N chloroquine Natural products ClC1=CC=C2C(NC(C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-UHFFFAOYSA-N 0.000 description 4
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 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 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229960003677 chloroquine Drugs 0.000 description 3
- 238000010908 decantation Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- BUWPZNOVIHAWHW-UHFFFAOYSA-N 2,3-dihydro-1h-quinolin-4-one Chemical compound C1=CC=C2C(=O)CCNC2=C1 BUWPZNOVIHAWHW-UHFFFAOYSA-N 0.000 description 2
- 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
- HTKGKUISLUERQX-UHFFFAOYSA-N 2-[(7-chloroquinolin-4-yl)amino]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=NC2=CC(Cl)=CC=C12 HTKGKUISLUERQX-UHFFFAOYSA-N 0.000 description 2
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 2
- GRGNJBKJCVOFEO-UHFFFAOYSA-N 5-(diethylamino)pentan-2-one Chemical compound CCN(CC)CCCC(C)=O GRGNJBKJCVOFEO-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-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
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 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
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 229910000040 hydrogen fluoride Inorganic materials 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
- 150000003839 salts Chemical class 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YMDNODNLFSHHCV-UHFFFAOYSA-N 2-chloro-n,n-diethylethanamine Chemical compound CCN(CC)CCCl YMDNODNLFSHHCV-UHFFFAOYSA-N 0.000 description 1
- YHXKNYLHVMSFKC-UHFFFAOYSA-N 3-(3-chloroanilino)propanoic acid Chemical compound OC(=O)CCNC1=CC=CC(Cl)=C1 YHXKNYLHVMSFKC-UHFFFAOYSA-N 0.000 description 1
- XMFXTXKSWIDMER-UHFFFAOYSA-N 7-chloro-1h-quinolin-4-one Chemical compound ClC1=CC=C2C(O)=CC=NC2=C1 XMFXTXKSWIDMER-UHFFFAOYSA-N 0.000 description 1
- UNBAKFOJVCOWDA-UHFFFAOYSA-N 7-chloro-n-methyl-n-phenylquinolin-4-amine Chemical compound C=1C=NC2=CC(Cl)=CC=C2C=1N(C)C1=CC=CC=C1 UNBAKFOJVCOWDA-UHFFFAOYSA-N 0.000 description 1
- VMXVICSRKCDAEF-UHFFFAOYSA-N ClO.CNC1=CC=CC=C1 Chemical compound ClO.CNC1=CC=CC=C1 VMXVICSRKCDAEF-UHFFFAOYSA-N 0.000 description 1
- JBCSOBKDUKAJHR-UHFFFAOYSA-N ClO.NC1=CC=CC=C1 Chemical compound ClO.NC1=CC=CC=C1 JBCSOBKDUKAJHR-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- UBADKKCCQHYPIX-UHFFFAOYSA-N aluminum oxygen(2-) ruthenium(3+) Chemical compound [O-2].[Al+3].[Ru+3].[O-2].[O-2] UBADKKCCQHYPIX-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000078 anti-malarial effect Effects 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 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
- 239000012259 ether extract Substances 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
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- WASDHUGJPMZUGU-UHFFFAOYSA-N n,n-dibutyl-7-chloroquinolin-4-amine Chemical compound ClC1=CC=C2C(N(CCCC)CCCC)=CC=NC2=C1 WASDHUGJPMZUGU-UHFFFAOYSA-N 0.000 description 1
- KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical compound ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000003380 propellant Substances 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
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000005406 washing 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
- C07D215/38—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 (1)
| 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU184985B true HU184985B (en) | 1984-11-28 |
Family
ID=9254223
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU82121A HU184985B (en) | 1981-01-16 | 1982-01-15 | Process for producing 4-amino-chloroquinolines |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4421920A (enExample) |
| EP (1) | EP0056766B1 (enExample) |
| JP (1) | JPS57171973A (enExample) |
| KR (1) | KR870001921B1 (enExample) |
| AT (1) | ATE7492T1 (enExample) |
| CA (1) | CA1171861A (enExample) |
| DE (1) | DE3260150D1 (enExample) |
| DK (1) | DK148805C (enExample) |
| FR (1) | FR2498187A1 (enExample) |
| HU (1) | HU184985B (enExample) |
| IE (1) | IE51957B1 (enExample) |
| IN (1) | IN158327B (enExample) |
| ZA (1) | ZA82277B (enExample) |
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 |
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| GB9910580D0 (en) | 1999-05-08 | 1999-07-07 | Zeneca Ltd | Chemical compounds |
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| US20040229908A1 (en) * | 1999-07-13 | 2004-11-18 | Jodi Nelson | Compositions and methods for the treatment of Parkinson's disease and tardive dyskinesias |
| PT1274692E (pt) * | 2000-04-07 | 2006-11-30 | Astrazeneca Ab | Compostos de quinazolina |
| EP1337524A1 (en) * | 2000-11-02 | 2003-08-27 | AstraZeneca AB | Substituted quinolines as antitumor agents |
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| 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 |
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| GEP20084572B (en) * | 2003-12-23 | 2008-12-25 | Pfizer | Novel quinoline derivatives |
| 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 |
| EP1833482A4 (en) | 2005-01-03 | 2011-02-16 | Myriad Genetics Inc | COMPOUNDS AND ITS THERAPEUTIC USE |
| US8258145B2 (en) * | 2005-01-03 | 2012-09-04 | Myrexis, Inc. | Method of treating brain cancer |
| WO2007059372A2 (en) * | 2005-11-09 | 2007-05-24 | 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 |
| EP4251746A1 (en) | 2020-11-30 | 2023-10-04 | 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 |
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| 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 KR KR8200161A patent/KR870001921B1/ko not_active Expired
- 1982-01-15 HU HU82121A patent/HU184985B/hu not_active IP Right Cessation
- 1982-01-15 AT AT82400080T patent/ATE7492T1/de active
- 1982-01-15 EP EP82400080A patent/EP0056766B1/fr not_active Expired
- 1982-01-15 CA CA000394273A patent/CA1171861A/fr not_active Expired
- 1982-01-15 IN IN36/DEL/82A patent/IN158327B/en unknown
- 1982-01-15 ZA ZA82277A patent/ZA82277B/xx unknown
- 1982-01-15 US US06/339,722 patent/US4421920A/en not_active Expired - Fee Related
- 1982-01-15 DK DK16582A patent/DK148805C/da 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
Also Published As
| Publication number | Publication date |
|---|---|
| ZA82277B (en) | 1982-11-24 |
| EP0056766A1 (fr) | 1982-07-28 |
| FR2498187A1 (fr) | 1982-07-23 |
| CA1171861A (fr) | 1984-07-31 |
| FR2498187B1 (enExample) | 1983-09-30 |
| IN158327B (enExample) | 1986-10-18 |
| DK16582A (da) | 1982-07-17 |
| IE51957B1 (en) | 1987-04-29 |
| KR870001921B1 (ko) | 1987-10-22 |
| IE820075L (en) | 1982-07-16 |
| ATE7492T1 (de) | 1984-06-15 |
| DE3260150D1 (en) | 1984-06-20 |
| KR830009038A (ko) | 1983-12-17 |
| DK148805C (da) | 1986-04-01 |
| US4421920A (en) | 1983-12-20 |
| DK148805B (da) | 1985-10-07 |
| JPS57171973A (en) | 1982-10-22 |
| EP0056766B1 (fr) | 1984-05-16 |
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Legal Events
| Date | Code | Title | Description |
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| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |