NL7907349A - Imidazolylethoxyderivaten van pyridin-5-methanolen en chinoline-3-methanolen. - Google Patents

Imidazolylethoxyderivaten van pyridin-5-methanolen en chinoline-3-methanolen. Download PDF

Info

Publication number: NL7907349A
Authority: NL; Netherlands
Prior art keywords: formula; halogen; compound; chlorine; hydrogen
Prior art date: 1978-10-25

Application number

NL7907349A

Other languages

English (en)

Dutch (nl)

Original Assignee

Squibb & Sons Inc

Priority date (The priority date 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 date listed.)

1978-10-25

Filing date

1979-10-03

Publication date

1980-04-29

1978-10-25 Priority claimed from US05/954,730 external-priority patent/US4191831A/en

1978-10-25 Priority claimed from US05/954,728 external-priority patent/US4202985A/en

1979-10-03 Application filed by Squibb & Sons Inc filed Critical Squibb & Sons Inc

1980-04-29 Publication of NL7907349A publication Critical patent/NL7907349A/nl

Links

-1 IMIDAZOLYLETHOXY Chemical class 0.000 title claims description 17
239000000460 chlorine Substances 0.000 claims description 66
150000001875 compounds Chemical class 0.000 claims description 57
229910052736 halogen Inorganic materials 0.000 claims description 45
150000002367 halogens Chemical class 0.000 claims description 41
229910052801 chlorine Inorganic materials 0.000 claims description 32
229910052739 hydrogen Inorganic materials 0.000 claims description 30
239000001257 hydrogen Substances 0.000 claims description 30
150000003839 salts Chemical class 0.000 claims description 29
238000000034 method Methods 0.000 claims description 28
150000002431 hydrogen Chemical class 0.000 claims description 23
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 19
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 19
239000002253 acid Substances 0.000 claims description 19
125000000217 alkyl group Chemical group 0.000 claims description 16
125000004432 carbon atom Chemical group C* 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
125000004414 alkyl thio group Chemical group 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
229910052794 bromium Inorganic materials 0.000 claims description 5
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
FLGKQMOTLCGOQH-UHFFFAOYSA-N quinolin-3-ylmethanol Chemical class C1=CC=CC2=CC(CO)=CN=C21 FLGKQMOTLCGOQH-UHFFFAOYSA-N 0.000 claims description 3
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
229910052740 iodine Inorganic materials 0.000 claims 1
239000011630 iodine Substances 0.000 claims 1
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
239000000203 mixture Substances 0.000 description 11
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
239000000243 solution Substances 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
239000002585 base Substances 0.000 description 7
125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 7
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
239000012458 free base Substances 0.000 description 5
239000012280 lithium aluminium hydride Substances 0.000 description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
239000002904 solvent Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
VDXWCRIARMBDOX-UHFFFAOYSA-N (4,6-dichloropyridin-3-yl)methanol Chemical compound OCC1=CN=C(Cl)C=C1Cl VDXWCRIARMBDOX-UHFFFAOYSA-N 0.000 description 4
NTWZHQAXJSJOIB-UHFFFAOYSA-N 2-imidazol-1-yl-1-phenylethanol Chemical class C=1C=CC=CC=1C(O)CN1C=CN=C1 NTWZHQAXJSJOIB-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
238000001816 cooling Methods 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
238000010992 reflux Methods 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
UKVLTPAGJIYSGN-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-2-imidazol-1-ylethanol Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(O)CN1C=CN=C1 UKVLTPAGJIYSGN-UHFFFAOYSA-N 0.000 description 3
PZHIYZLLIBBPFK-UHFFFAOYSA-N 2,4-dichloro-5-(chloromethyl)pyridine Chemical compound ClCC1=CN=C(Cl)C=C1Cl PZHIYZLLIBBPFK-UHFFFAOYSA-N 0.000 description 3
ZRYDYTAPOBOBIN-UHFFFAOYSA-N 4,7-dichloro-3-(chloromethyl)quinoline Chemical compound C1=C(Cl)C=CC2=C(Cl)C(CCl)=CN=C21 ZRYDYTAPOBOBIN-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000003610 charcoal Substances 0.000 description 3
PSXRWZBTVAZNSF-UHFFFAOYSA-N hydron;quinoline;chloride Chemical compound Cl.N1=CC=CC2=CC=CC=C21 PSXRWZBTVAZNSF-UHFFFAOYSA-N 0.000 description 3
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 3
239000007858 starting material Substances 0.000 description 3
RWJSYVQOVOFTJQ-UHFFFAOYSA-N (4,6-dichloroquinolin-3-yl)methanol Chemical compound C1=CC(Cl)=CC2=C(Cl)C(CO)=CN=C21 RWJSYVQOVOFTJQ-UHFFFAOYSA-N 0.000 description 2
DMZNIROKRAUMSD-UHFFFAOYSA-N (4,7-dichloroquinolin-3-yl)methanol Chemical compound C1=C(Cl)C=CC2=C(Cl)C(CO)=CN=C21 DMZNIROKRAUMSD-UHFFFAOYSA-N 0.000 description 2
PBIUDEUWYGBHDW-UHFFFAOYSA-N 2-chloro-1-pyridin-3-ylethanone;hydrochloride Chemical compound Cl.ClCC(=O)C1=CC=CN=C1 PBIUDEUWYGBHDW-UHFFFAOYSA-N 0.000 description 2
IHUNVPDCOXWLAH-UHFFFAOYSA-N 4,6-dichloro-3-(chloromethyl)quinoline Chemical compound C1=CC(Cl)=CC2=C(Cl)C(CCl)=CN=C21 IHUNVPDCOXWLAH-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
229910002651 NO3 Inorganic materials 0.000 description 2
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
239000013543 active substance Substances 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
AAUBVINEXCCXOK-UHFFFAOYSA-N ethyl 4,6-dichloropyridine-3-carboxylate Chemical compound CCOC(=O)C1=CN=C(Cl)C=C1Cl AAUBVINEXCCXOK-UHFFFAOYSA-N 0.000 description 2
BSSNTDZRVNQGDF-UHFFFAOYSA-N ethyl 4,6-dichloroquinoline-3-carboxylate Chemical compound C1=CC(Cl)=CC2=C(Cl)C(C(=O)OCC)=CN=C21 BSSNTDZRVNQGDF-UHFFFAOYSA-N 0.000 description 2
KWYQZEQRIMVMTH-UHFFFAOYSA-N ethyl 4,7-dichloroquinoline-3-carboxylate Chemical compound C1=C(Cl)C=CC2=C(Cl)C(C(=O)OCC)=CN=C21 KWYQZEQRIMVMTH-UHFFFAOYSA-N 0.000 description 2
239000000284 extract Substances 0.000 description 2
239000007789 gas Substances 0.000 description 2
150000002366 halogen compounds Chemical class 0.000 description 2
125000004970 halomethyl group Chemical group 0.000 description 2
239000005457 ice water Substances 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
229910052987 metal hydride Inorganic materials 0.000 description 2
150000004681 metal hydrides Chemical class 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
239000003921 oil Substances 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 2
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
CNQCWYFDIQSALX-UHFFFAOYSA-N 3-(chloromethyl)pyridine Chemical class ClCC1=CC=CN=C1 CNQCWYFDIQSALX-UHFFFAOYSA-N 0.000 description 1
MVQVNTPHUGQQHK-UHFFFAOYSA-N 3-pyridinemethanol Chemical class OCC1=CC=CN=C1 MVQVNTPHUGQQHK-UHFFFAOYSA-N 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
241000222122 Candida albicans Species 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
241000700198 Cavia Species 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
241000700159 Rattus Species 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
241000224527 Trichomonas vaginalis Species 0.000 description 1
241001045770 Trichophyton mentagrophytes Species 0.000 description 1
229940022663 acetate Drugs 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
239000003429 antifungal agent Substances 0.000 description 1
229940072107 ascorbate Drugs 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
229910001863 barium hydroxide Inorganic materials 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
229940077388 benzenesulfonate Drugs 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229940095731 candida albicans Drugs 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
229940001468 citrate Drugs 0.000 description 1
239000006071 cream Substances 0.000 description 1
HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
LNIMLSAAPISOEC-UHFFFAOYSA-N ethyl 4,6-dichloro-2-methylpyridine-3-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(Cl)C=C1Cl LNIMLSAAPISOEC-UHFFFAOYSA-N 0.000 description 1
NZELFGGFSIVWAG-UHFFFAOYSA-N ethyl 4,6-dichloroquinoline-5-carboxylate Chemical compound C1=CC(Cl)=C2C(C(=O)OCC)=C(Cl)C=CC2=N1 NZELFGGFSIVWAG-UHFFFAOYSA-N 0.000 description 1
XWMCHSWUDMFGSW-UHFFFAOYSA-N ethyl 7-chloro-4-oxo-1h-quinoline-3-carboxylate Chemical compound ClC1=CC=C2C(=O)C(C(=O)OCC)=CNC2=C1 XWMCHSWUDMFGSW-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
238000007429 general method Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000006210 lotion Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000000155 melt Substances 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
239000002244 precipitate Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-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
150000003254 radicals Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000011833 salt mixture Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
241000894007 species Species 0.000 description 1
229940086735 succinate Drugs 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
229910052717 sulfur Chemical group 0.000 description 1
239000011593 sulfur Chemical group 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
- C07D213/61—Halogen atoms or nitro radicals

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

NL7907349A 1978-10-25 1979-10-03 Imidazolylethoxyderivaten van pyridin-5-methanolen en chinoline-3-methanolen. NL7907349A (nl)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US95472878		1978-10-25
US05/954,730 US4191831A (en)	1978-10-25	1978-10-25	Imidazolylethoxy derivatives of pyridin-5-methanols
US95473078		1978-10-25
US05/954,728 US4202985A (en)	1978-10-25	1978-10-25	Imidazolylethoxy derivatives of quinoline-3-methanols

Publications (1)

Publication Number	Publication Date
NL7907349A true NL7907349A (nl)	1980-04-29

Family

ID=27130354

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL7907349A NL7907349A (nl)	1978-10-25	1979-10-03	Imidazolylethoxyderivaten van pyridin-5-methanolen en chinoline-3-methanolen.

Country Status (12)

Country	Link
AU (1)	AU5136879A (it)
DE (1)	DE2943151A1 (it)
DK (1)	DK448379A (it)
FR (1)	FR2439781A1 (it)
GB (1)	GB2033384B (it)
HU (1)	HU178748B (it)
IE (1)	IE49081B1 (it)
IT (1)	IT1125592B (it)
LU (1)	LU81814A1 (it)
NL (1)	NL7907349A (it)
NO (1)	NO793411L (it)
SE (1)	SE7908820L (it)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4282230A (en) *	1979-11-15	1981-08-04	E. R. Squibb & Sons, Inc.	Imidazolylethoxy derivatives of quinoline-2- or 4-methanols, antimicrobial compositions containing them and method for treating bacterial or fungal infections with them

1979
- 1979-09-28 FR FR7924279A patent/FR2439781A1/fr not_active Withdrawn
- 1979-10-02 AU AU51368/79A patent/AU5136879A/en not_active Abandoned
- 1979-10-03 NL NL7907349A patent/NL7907349A/nl not_active Application Discontinuation
- 1979-10-04 GB GB7934486A patent/GB2033384B/en not_active Expired
- 1979-10-05 IE IE1894/79A patent/IE49081B1/en unknown
- 1979-10-24 LU LU81814A patent/LU81814A1/fr unknown
- 1979-10-24 NO NO793411A patent/NO793411L/no unknown
- 1979-10-24 DK DK448379A patent/DK448379A/da unknown
- 1979-10-24 HU HU79SU1038A patent/HU178748B/hu unknown
- 1979-10-24 SE SE7908820A patent/SE7908820L/xx not_active Application Discontinuation
- 1979-10-24 IT IT26765/79A patent/IT1125592B/it active
- 1979-10-25 DE DE19792943151 patent/DE2943151A1/de not_active Withdrawn

Also Published As

Publication number	Publication date
IT7926765A0 (it)	1979-10-24
FR2439781A1 (fr)	1980-05-23
LU81814A1 (fr)	1980-01-25
HU178748B (en)	1982-06-28
DK448379A (da)	1980-04-26
IT1125592B (it)	1986-05-14
NO793411L (no)	1980-04-28
SE7908820L (sv)	1980-04-26
GB2033384A (en)	1980-05-21
AU5136879A (en)	1980-05-01
DE2943151A1 (de)	1980-05-08
GB2033384B (en)	1982-08-25
IE791894L (en)	1980-04-25
IE49081B1 (en)	1985-07-24

Legal Events

Date	Code	Title	Description
1983-06-01	BV	The patent application has lapsed

Publication	Publication Date	Title
US4620007A (en)	1986-10-28	6-fluoro-7-chloro-1-cyclopropyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid
US4670444A (en)	1987-06-02	7-amino-1-cyclopropyl-4-oxo-1, 4-dihydro-quinoline-and naphthyridine-3-carboxylic acids and antibacterial agents containing these compounds
US4284629A (en)	1981-08-18	Process for the preparation of 4-pyridone-3-carboxylic acids and/or derivatives thereof
JPS6322075A (ja)	1988-01-29	１―シクロプロピル―６―フルオロ―１，４―ジヒドロ―４―オキソ―７―ピペラジノ―キノリン―３―カルボン酸類の製造方法
US7671080B2 (en)	2010-03-02	1-benzylindole-2-carboxamide derivatives
JPH0314811B2 (it)	1991-02-27
DE69217312T2 (de)	1997-05-22	Tricyclische Heterocyclen als PGE2-Antagonisten
IE56460B1 (en)	1991-08-14	1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(alkyl-1-piperazinyl)-3-quinoline-carboxylic acids,processes for their preparation and antibacterial agents containing them
HU192112B (en)	1987-05-28	Process for preparing new 4-oxo-4h-/1/-benzo-pyran-8-yl-alkanecarboxylic acids
EP0113092A1 (de)	1984-07-11	1-Cyclopropyl-6-fluor-1,4-dihydro-4-oxo-7-(4-(oxoalkyl)-1-piperazinyl)-3-chinolincarbonsäuren und ihre Derivate, Verfahren zu ihrer Herstellung sowie diese enthaltende antibakterielle Mittel
EP0387802A2 (en)	1990-09-19	5-Substituted-1,4-dihydro-4-oxonaphthyridine-3-carboxylate antibacterial agents
US4282230A (en)	1981-08-04	Imidazolylethoxy derivatives of quinoline-2- or 4-methanols, antimicrobial compositions containing them and method for treating bacterial or fungal infections with them
EP0151477B1 (en)	1990-09-12	1h-imidazole derivatives, a process for preparing them and pharmaceutical compositions containing them
US4273776A (en)	1981-06-16	Antibacterial and antifungal derivatives of 3-(1H-imidazol-1-yl)-2-propen-1-ones
NL7907349A (nl)	1980-04-29	Imidazolylethoxyderivaten van pyridin-5-methanolen en chinoline-3-methanolen.
EP0198235B1 (en)	1989-08-23	Imidazole derivatives having antimycotic and antibacterial activities, a process for the preparation thereof and pharmaceutical compositions containing them
US4234589A (en)	1980-11-18	Imidazolylethoxymethyl derivatives of 1,3-dioxolo quinolines
EP0055068A1 (en)	1982-06-30	Quinolone derivatives and their use as pharmaceuticals
US4202985A (en)	1980-05-13	Imidazolylethoxy derivatives of quinoline-3-methanols
NL8002024A (nl)	1980-10-07	6-gesubstitueerde pyranonverbindingen en hun toepassing in de farmacie.
US4159380A (en)	1979-06-26	Imidazolylethoxy derivatives of pyrazolo[3,4-b]pyridine-5-methanols
US4191831A (en)	1980-03-04	Imidazolylethoxy derivatives of pyridin-5-methanols
PL116688B1 (en)	1981-06-30	Process for the preparation of trinuclear compounds with nitrogen atom in nodal position
EP0362299A1 (en)	1990-04-11	Bicyclic compounds, their use as pharmaceuticals, their preparation, and intermediates useful in their preparation
FI80451C (fi)	1990-06-11	Foerfarande foer framstaellning av nya terapeutiskt anvaenbara as-triazino/6,1-a/isokinolinium-derivat och isomerer daerav.