CH526547A - Verfahren zur Herstellung von Chinolinderivaten - Google Patents
Verfahren zur Herstellung von ChinolinderivatenInfo
- Publication number
- CH526547A CH526547A CH663469A CH663469A CH526547A CH 526547 A CH526547 A CH 526547A CH 663469 A CH663469 A CH 663469A CH 663469 A CH663469 A CH 663469A CH 526547 A CH526547 A CH 526547A
- Authority
- CH
- Switzerland
- Prior art keywords
- carboxylic acid
- benzyloxy
- alkyl
- hydroxy
- carbon atoms
- Prior art date
Links
- 125000001424 substituent group Chemical group 0.000 title claims abstract description 8
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 title claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 title abstract 5
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title abstract 4
- 125000003710 aryl alkyl group Chemical group 0.000 title abstract 2
- 125000003118 aryl group Chemical group 0.000 title abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 230000032050 esterification Effects 0.000 claims description 3
- 238000005886 esterification reaction Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims 1
- 229910052736 halogen Chemical group 0.000 claims 1
- 241000499566 Eimeria brunetti Species 0.000 abstract 1
- 241000499563 Eimeria necatrix Species 0.000 abstract 1
- 241000223932 Eimeria tenella Species 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 239000003224 coccidiostatic agent Substances 0.000 abstract 1
- 239000012141 concentrate Substances 0.000 abstract 1
- -1 alkyl radical Chemical group 0.000 description 67
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 150000003248 quinolines Chemical class 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- ABQKYBVDVAXVNO-UHFFFAOYSA-N 4-oxo-7-phenylmethoxy-1h-quinoline-3-carboxylic acid Chemical compound C=1C=C2C(=O)C(C(=O)O)=CNC2=CC=1OCC1=CC=CC=C1 ABQKYBVDVAXVNO-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- NUQYKYFOZCEHNP-UHFFFAOYSA-N 4-oxo-7-phenylmethoxy-6-propyl-1H-quinoline-3-carboxylic acid Chemical compound C(C1=CC=CC=C1)OC1=C(C=C2C(=C(C=NC2=C1)C(=O)O)O)CCC NUQYKYFOZCEHNP-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- SVKGPBZTZMLGAV-UHFFFAOYSA-N methyl 4-oxo-7-phenylmethoxy-6-propyl-1H-quinoline-3-carboxylate Chemical compound C(C1=CC=CC=C1)OC1=C(C=C2C(=C(C=NC2=C1)C(=O)OC)O)CCC SVKGPBZTZMLGAV-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 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 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LUEZRKHXABYBNM-UHFFFAOYSA-N C(C)ClCC1=CC=CC=C1 Chemical compound C(C)ClCC1=CC=CC=C1 LUEZRKHXABYBNM-UHFFFAOYSA-N 0.000 description 2
- 208000003495 Coccidiosis Diseases 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 206010023076 Isosporiasis Diseases 0.000 description 2
- NNOPDLNHPOLRRE-UHFFFAOYSA-N Nequinate Chemical compound CCCCC1=CC(C(C(C(=O)OC)=CN2)=O)=C2C=C1OCC1=CC=CC=C1 NNOPDLNHPOLRRE-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- AJFAAXMCFXOPOM-UHFFFAOYSA-N ethyl 4-oxo-7-phenylmethoxy-1h-quinoline-3-carboxylate Chemical compound C=1C=C2C(=O)C(C(=O)OCC)=CNC2=CC=1OCC1=CC=CC=C1 AJFAAXMCFXOPOM-UHFFFAOYSA-N 0.000 description 2
- QLJUIUYIMJNBTP-UHFFFAOYSA-N ethyl 4-oxo-7-phenylmethoxy-6-propoxy-1H-quinoline-3-carboxylate Chemical compound C(C1=CC=CC=C1)OC1=C(C=C2C(=C(C=NC2=C1)C(=O)OCC)O)OCCC QLJUIUYIMJNBTP-UHFFFAOYSA-N 0.000 description 2
- FSXCMKNNKQZLCJ-UHFFFAOYSA-N ethyl 4-oxo-7-phenylmethoxy-6-propyl-1H-quinoline-3-carboxylate Chemical compound C(C1=CC=CC=C1)OC1=C(C=C2C(=C(C=NC2=C1)C(=O)OCC)O)CCC FSXCMKNNKQZLCJ-UHFFFAOYSA-N 0.000 description 2
- CHAPUUUBWFGJOR-UHFFFAOYSA-N ethyl 6-ethoxy-4-oxo-7-phenylmethoxy-1H-quinoline-3-carboxylate Chemical compound C(C1=CC=CC=C1)OC1=C(C=C2C(=C(C=NC2=C1)C(=O)OCC)O)OCC CHAPUUUBWFGJOR-UHFFFAOYSA-N 0.000 description 2
- UOKOBWNSJGYHCV-UHFFFAOYSA-N ethyl 7-[(4-chlorophenyl)methoxy]-4-oxo-6-propyl-1H-quinoline-3-carboxylate Chemical compound ClC1=CC=C(COC2=C(C=C3C(=C(C=NC3=C2)C(=O)OCC)O)CCC)C=C1 UOKOBWNSJGYHCV-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- VNZJMWJGRATRTG-UHFFFAOYSA-N methyl 4-oxo-7-phenylmethoxy-1h-quinoline-3-carboxylate Chemical compound C=1C=C2C(=O)C(C(=O)OC)=CNC2=CC=1OCC1=CC=CC=C1 VNZJMWJGRATRTG-UHFFFAOYSA-N 0.000 description 2
- ZZXHVLMRFXURBM-UHFFFAOYSA-N methyl 4-oxo-7-phenylmethoxy-6-propan-2-yloxy-1H-quinoline-3-carboxylate Chemical compound COC(=O)C1=C(O)C2=CC(OC(C)C)=C(OCC3=CC=CC=C3)C=C2N=C1 ZZXHVLMRFXURBM-UHFFFAOYSA-N 0.000 description 2
- JXVVJBXCYPULOQ-UHFFFAOYSA-N methyl 4-oxo-7-phenylmethoxy-6-propoxy-1H-quinoline-3-carboxylate Chemical compound C(C1=CC=CC=C1)OC1=C(C=C2C(=C(C=NC2=C1)C(=O)OC)O)OCCC JXVVJBXCYPULOQ-UHFFFAOYSA-N 0.000 description 2
- FTHKDFUXNUCSDG-UHFFFAOYSA-N methyl 6-ethoxy-4-oxo-7-phenylmethoxy-1H-quinoline-3-carboxylate Chemical compound C(C1=CC=CC=C1)OC1=C(C=C2C(=C(C=NC2=C1)C(=O)OC)O)OCC FTHKDFUXNUCSDG-UHFFFAOYSA-N 0.000 description 2
- JDUKKGYNHVLTNR-UHFFFAOYSA-N methyl 6-methoxy-4-oxo-7-phenylmethoxy-1H-quinoline-3-carboxylate Chemical compound C(C1=CC=CC=C1)OC1=C(C=C2C(=C(C=NC2=C1)C(=O)OC)O)OC JDUKKGYNHVLTNR-UHFFFAOYSA-N 0.000 description 2
- TUJDEASYMVIBDV-UHFFFAOYSA-N methyl 7-[(2,4-dichlorophenyl)methoxy]-4-oxo-6-propyl-1H-quinoline-3-carboxylate Chemical compound ClC1=C(COC2=C(C=C3C(=C(C=NC3=C2)C(=O)OC)O)CCC)C=CC(=C1)Cl TUJDEASYMVIBDV-UHFFFAOYSA-N 0.000 description 2
- VSQBUDAELOTKGK-UHFFFAOYSA-N methyl 7-[(4-chlorophenyl)methoxy]-4-oxo-6-propyl-1H-quinoline-3-carboxylate Chemical compound ClC1=CC=C(COC2=C(C=C3C(=C(C=NC3=C2)C(=O)OC)O)CCC)C=C1 VSQBUDAELOTKGK-UHFFFAOYSA-N 0.000 description 2
- DNIJJUNMFISAFZ-UHFFFAOYSA-N methyl 7-dodecoxy-4-oxo-6-propyl-1H-quinoline-3-carboxylate Chemical compound C(CC)C=1C=C2C(=C(C=NC2=CC1OCCCCCCCCCCCC)C(=O)OC)O DNIJJUNMFISAFZ-UHFFFAOYSA-N 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical group [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 1
- CONKBQPVFMXDOV-QHCPKHFHSA-N 6-[(5S)-5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-2-oxo-1,3-oxazolidin-3-yl]-3H-1,3-benzoxazol-2-one Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C[C@H]1CN(C(O1)=O)C1=CC2=C(NC(O2)=O)C=C1 CONKBQPVFMXDOV-QHCPKHFHSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 description 1
- WGQAWSANCXQVIK-UHFFFAOYSA-N OC1=C(C=NC2=CC(=CC=C12)OCCCC1=CC=CC=C1)C(=O)OC Chemical compound OC1=C(C=NC2=CC(=CC=C12)OCCCC1=CC=CC=C1)C(=O)OC WGQAWSANCXQVIK-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 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
- 150000007942 carboxylates Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- BCXOUBLDUQRWQI-UHFFFAOYSA-N ethyl 4-oxo-7-tetradecoxy-1H-quinoline-3-carboxylate Chemical compound C(CCCCCCCCCCCCC)OC1=CC=C2C(=C(C=NC2=C1)C(=O)OCC)O BCXOUBLDUQRWQI-UHFFFAOYSA-N 0.000 description 1
- KMEYOIWPSGMMHL-UHFFFAOYSA-N ethyl 6-butyl-4-oxo-7-phenylmethoxy-1H-quinoline-3-carboxylate Chemical compound C(C1=CC=CC=C1)OC1=C(C=C2C(=C(C=NC2=C1)C(=O)OCC)O)CCCC KMEYOIWPSGMMHL-UHFFFAOYSA-N 0.000 description 1
- AZRVEXDDDNQYRP-UHFFFAOYSA-N ethyl 6-chloro-4-oxo-7-phenylmethoxy-1H-quinoline-3-carboxylate Chemical compound C(C1=CC=CC=C1)OC1=C(C=C2C(=C(C=NC2=C1)C(=O)OCC)O)Cl AZRVEXDDDNQYRP-UHFFFAOYSA-N 0.000 description 1
- IORJXQFIKYEVFW-UHFFFAOYSA-N ethyl 6-hexyl-4-oxo-7-phenylmethoxy-1H-quinoline-3-carboxylate Chemical compound C(C1=CC=CC=C1)OC1=C(C=C2C(=C(C=NC2=C1)C(=O)OCC)O)CCCCCC IORJXQFIKYEVFW-UHFFFAOYSA-N 0.000 description 1
- SAGPCZIIEIWZRT-UHFFFAOYSA-N ethyl 6-methyl-4-oxo-7-phenylmethoxy-1H-quinoline-3-carboxylate Chemical compound C(C1=CC=CC=C1)OC1=C(C=C2C(=C(C=NC2=C1)C(=O)OCC)O)C SAGPCZIIEIWZRT-UHFFFAOYSA-N 0.000 description 1
- ATRUOBVOENBDBU-UHFFFAOYSA-N ethyl 7-(4-methylphenoxy)-4-oxo-1H-quinoline-3-carboxylate Chemical compound OC1=C(C=NC2=CC(=CC=C12)OC1=CC=C(C=C1)C)C(=O)OCC ATRUOBVOENBDBU-UHFFFAOYSA-N 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 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
- MZXFSZDYVWLOAR-UHFFFAOYSA-N methyl 6-(2-methylpropyl)-4-oxo-7-phenylmethoxy-1H-quinoline-3-carboxylate Chemical compound C(C1=CC=CC=C1)OC1=C(C=C2C(=C(C=NC2=C1)C(=O)OC)O)CC(C)C MZXFSZDYVWLOAR-UHFFFAOYSA-N 0.000 description 1
- YUYKGEIXLVTRHP-UHFFFAOYSA-N methyl 6-ethyl-4-oxo-7-phenylmethoxy-1H-quinoline-3-carboxylate Chemical compound C(C1=CC=CC=C1)OC1=C(C=C2C(=C(C=NC2=C1)C(=O)OC)O)CC YUYKGEIXLVTRHP-UHFFFAOYSA-N 0.000 description 1
- RDINGYLZVSYFGL-UHFFFAOYSA-N methyl 6-methyl-4-oxo-7-phenylmethoxy-1H-quinoline-3-carboxylate Chemical compound C(C1=CC=CC=C1)OC1=C(C=C2C(=C(C=NC2=C1)C(=O)OC)O)C RDINGYLZVSYFGL-UHFFFAOYSA-N 0.000 description 1
- KOXHTALCVSURJN-UHFFFAOYSA-N methyl 7-[(2-chlorophenyl)methoxy]-4-oxo-6-propyl-1H-quinoline-3-carboxylate Chemical compound ClC1=C(COC2=C(C=C3C(=C(C=NC3=C2)C(=O)OC)O)CCC)C=CC=C1 KOXHTALCVSURJN-UHFFFAOYSA-N 0.000 description 1
- IJIPILXMWHLHMG-UHFFFAOYSA-N methyl 7-[(4-methylphenyl)methoxy]-4-oxo-1H-quinoline-3-carboxylate Chemical compound OC1=C(C=NC2=CC(=CC=C12)OCC1=CC=C(C=C1)C)C(=O)OC IJIPILXMWHLHMG-UHFFFAOYSA-N 0.000 description 1
- VUJXRZMEGYOLOT-UHFFFAOYSA-N methyl 7-[(4-nitrophenyl)methoxy]-4-oxo-1H-quinoline-3-carboxylate Chemical compound OC1=C(C=NC2=CC(=CC=C12)OCC1=CC=C(C=C1)[N+](=O)[O-])C(=O)OC VUJXRZMEGYOLOT-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 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
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 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
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- QIWNOVRXWQPVIY-UHFFFAOYSA-N propylbenzene Chemical compound [CH2]CCC1=CC=CC=C1 QIWNOVRXWQPVIY-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9979/65A GB1070223A (en) | 1965-03-09 | 1965-03-09 | Quinoline derivatives |
| GB5123265 | 1965-12-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH526547A true CH526547A (de) | 1972-08-15 |
Family
ID=26243300
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH663469A CH526547A (de) | 1965-03-09 | 1966-03-09 | Verfahren zur Herstellung von Chinolinderivaten |
| CH333666A CH539040A (de) | 1965-03-09 | 1966-03-09 | Verfahren zur Herstellung von Chinolinderivaten |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH333666A CH539040A (de) | 1965-03-09 | 1966-03-09 | Verfahren zur Herstellung von Chinolinderivaten |
Country Status (12)
| Country | Link |
|---|---|
| BE (1) | BE677592A (forum.php) |
| BR (1) | BR6677642D0 (forum.php) |
| CH (2) | CH526547A (forum.php) |
| DE (1) | DE1695231B1 (forum.php) |
| DK (2) | DK114480B (forum.php) |
| ES (4) | ES323905A1 (forum.php) |
| FR (1) | FR1487336A (forum.php) |
| GB (1) | GB1070223A (forum.php) |
| IL (1) | IL25347A (forum.php) |
| MY (1) | MY6800068A (forum.php) |
| NL (1) | NL6602994A (forum.php) |
| SE (1) | SE321225B (forum.php) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3397208A (en) * | 1965-02-24 | 1968-08-13 | Norwich Pharma Co | Method for preparing 4-hydroxy-6, 7-dialkoxy-3-carboalkoxyquinolines and novel 4-chloro-6, 7-dialkoxy-3-carboalkoxyquinolines useful therein |
| US3472859A (en) * | 1966-11-01 | 1969-10-14 | Sterling Drug Inc | 1-alkyl-1,4-dihydro-4-oxo-3 quinoline-carboxylic acids and esters |
| DE1908548A1 (de) * | 1968-02-29 | 1970-11-05 | Warner Lambert Co | Chinolinderivate |
| US3506667A (en) * | 1969-05-01 | 1970-04-14 | Warner Lambert Pharmaceutical | Furo quinoline carboxylates |
| FR2764601B1 (fr) * | 1997-06-16 | 1999-09-03 | Rhone Merieux | Procede de preparation de composes de type 4-(alkyl)-3- alcoxy-anilines |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR6236247D0 (pt) * | 1961-02-08 | 1973-05-24 | Norwich Pharma Co | Processo para preparar composicoes hipotensivas |
| FR1505313A (fr) * | 1962-04-09 | 1967-12-15 | Norwich Pharma Co | Esters d'alkyle inférieur des acides 6, 7-dialkoxy (inférieur)-4-hydroxy-3-quinoléine carboxyliques et leur procédé de préparation |
-
1965
- 1965-03-09 GB GB9979/65A patent/GB1070223A/en not_active Expired
-
1966
- 1966-02-25 DK DK100666AA patent/DK114480B/da unknown
- 1966-03-07 ES ES0323905A patent/ES323905A1/es not_active Expired
- 1966-03-08 BR BR177642/66A patent/BR6677642D0/pt unknown
- 1966-03-08 NL NL6602994A patent/NL6602994A/xx unknown
- 1966-03-09 IL IL25347A patent/IL25347A/xx unknown
- 1966-03-09 CH CH663469A patent/CH526547A/de not_active IP Right Cessation
- 1966-03-09 FR FR52703A patent/FR1487336A/fr not_active Expired
- 1966-03-09 DE DE19661695231 patent/DE1695231B1/de active Pending
- 1966-03-09 BE BE677592D patent/BE677592A/xx not_active IP Right Cessation
- 1966-03-09 CH CH333666A patent/CH539040A/de not_active IP Right Cessation
- 1966-08-13 ES ES0330229A patent/ES330229A1/es not_active Expired
- 1966-08-13 ES ES0330230A patent/ES330230A1/es not_active Expired
- 1966-08-13 ES ES0330228A patent/ES330228A1/es not_active Expired
-
1967
- 1967-04-28 DK DK228367AA patent/DK114410B/da unknown
- 1967-06-27 SE SE9294/67A patent/SE321225B/xx unknown
-
1968
- 1968-12-31 MY MY196868A patent/MY6800068A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MY6800068A (en) | 1968-12-31 |
| IL25347A (en) | 1970-01-29 |
| SE321225B (forum.php) | 1970-03-02 |
| NL6602994A (forum.php) | 1966-09-12 |
| ES330229A1 (es) | 1967-09-01 |
| ES330228A1 (es) | 1967-09-01 |
| DK114410B (da) | 1969-06-30 |
| ES323905A1 (es) | 1967-01-16 |
| FR1487336A (fr) | 1967-07-07 |
| CH539040A (de) | 1973-07-15 |
| DK114480B (da) | 1969-07-07 |
| DE1695231B1 (de) | 1972-05-04 |
| ES330230A1 (es) | 1967-11-01 |
| BR6677642D0 (pt) | 1973-09-06 |
| GB1070223A (en) | 1967-06-01 |
| BE677592A (forum.php) | 1966-09-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |