LU81814A1 - Derives imidazolylethoxy de pyridine-5-methanols et de quinoleine-3-methanols - Google Patents

Derives imidazolylethoxy de pyridine-5-methanols et de quinoleine-3-methanols Download PDF

Info

Publication number: LU81814A1
Authority: LU; Luxembourg
Prior art keywords: represent; atom; group; formula; halogen atom
Prior art date: 1978-10-25

Application number

LU81814A

Other languages

English (en)

French (fr)

Inventor

H Hoehn

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

1979-10-24

Publication date

1980-01-25

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

1979-10-24 Application filed by Squibb & Sons Inc filed Critical Squibb & Sons Inc

1980-01-25 Publication of LU81814A1 publication Critical patent/LU81814A1/fr

Links

-1 IMIDAZOLYLETHOXY Chemical class 0.000 title description 17
150000001875 compounds Chemical class 0.000 claims description 54
125000005843 halogen group Chemical group 0.000 claims description 41
238000000034 method Methods 0.000 claims description 32
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 29
150000003839 salts Chemical class 0.000 claims description 27
239000002253 acid Substances 0.000 claims description 23
229910052801 chlorine Inorganic materials 0.000 claims description 21
125000000217 alkyl group Chemical group 0.000 claims description 20
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 19
125000001309 chloro group Chemical group Cl* 0.000 claims description 18
125000004432 carbon atom Chemical group C* 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
125000004414 alkyl thio group Chemical group 0.000 claims description 5
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
229910052740 iodine Inorganic materials 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
125000001475 halogen functional group Chemical group 0.000 claims 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 claims 1
239000001257 hydrogen Substances 0.000 claims 1
125000000446 sulfanediyl group Chemical group *S* 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
238000002844 melting Methods 0.000 description 17
230000008018 melting Effects 0.000 description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 14
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 11
239000000203 mixture Substances 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 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
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 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
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 5
239000000284 extract Substances 0.000 description 5
238000001914 filtration Methods 0.000 description 5
239000012458 free base Substances 0.000 description 5
150000007522 mineralic acids Chemical class 0.000 description 5
238000010992 reflux Methods 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
239000002904 solvent Substances 0.000 description 5
238000001816 cooling Methods 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
239000012280 lithium aluminium hydride Substances 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000007858 starting material Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
125000004494 ethyl ester group Chemical group 0.000 description 3
150000004678 hydrides Chemical class 0.000 description 3
239000003921 oil Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
VDXWCRIARMBDOX-UHFFFAOYSA-N (4,6-dichloropyridin-3-yl)methanol Chemical compound OCC1=CN=C(Cl)C=C1Cl VDXWCRIARMBDOX-UHFFFAOYSA-N 0.000 description 2
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 2
KWVNKWCJDAWNAE-UHFFFAOYSA-N 2,3-dichloroquinoline Chemical compound C1=CC=C2N=C(Cl)C(Cl)=CC2=C1 KWVNKWCJDAWNAE-UHFFFAOYSA-N 0.000 description 2
PZHIYZLLIBBPFK-UHFFFAOYSA-N 2,4-dichloro-5-(chloromethyl)pyridine Chemical compound ClCC1=CN=C(Cl)C=C1Cl PZHIYZLLIBBPFK-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
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-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
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000000605 extraction Methods 0.000 description 2
238000007429 general method Methods 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
125000004970 halomethyl group Chemical group 0.000 description 2
238000003306 harvesting Methods 0.000 description 2
PSXRWZBTVAZNSF-UHFFFAOYSA-N hydron;quinoline;chloride Chemical compound Cl.N1=CC=CC2=CC=CC=C21 PSXRWZBTVAZNSF-UHFFFAOYSA-N 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
239000002244 precipitate Substances 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
125000001424 substituent group Chemical group 0.000 description 2
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 1
RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
NJWIMFZLESWFIM-UHFFFAOYSA-N 2-(chloromethyl)pyridine Chemical class ClCC1=CC=CC=N1 NJWIMFZLESWFIM-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
ANKGRWGYCWJARK-UHFFFAOYSA-N 4,6-dichloro-3-[[1-(2,4-dichlorophenyl)-2-imidazol-1-ylethoxy]methyl]-2-methylpyridine Chemical compound CC1=NC(Cl)=CC(Cl)=C1COC(C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 ANKGRWGYCWJARK-UHFFFAOYSA-N 0.000 description 1
ILMIEWNDXAKVNI-UHFFFAOYSA-N 4,6-dichloropyridine-3-carboxylic acid Chemical compound OC(=O)C1=CN=C(Cl)C=C1Cl ILMIEWNDXAKVNI-UHFFFAOYSA-N 0.000 description 1
MLBIOMJMHCNLEL-UHFFFAOYSA-N 4,7-dichloroquinoline-3-carboxylic acid Chemical compound C1=C(Cl)C=CC2=C(Cl)C(C(=O)O)=CN=C21 MLBIOMJMHCNLEL-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
CDPXSMNKRFLXHU-UHFFFAOYSA-N 6-chloro-4-oxo-1h-quinoline-3-carboxylic acid Chemical compound C1=C(Cl)C=C2C(=O)C(C(=O)O)=CNC2=C1 CDPXSMNKRFLXHU-UHFFFAOYSA-N 0.000 description 1
LWCVWGNRFYSORH-UHFFFAOYSA-N BBBBBBB Chemical compound BBBBBBB LWCVWGNRFYSORH-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
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
150000000994 L-ascorbates Chemical class 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
239000007832 Na2SO4 Substances 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 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
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
241000224527 Trichomonas vaginalis Species 0.000 description 1
241001045770 Trichophyton mentagrophytes Species 0.000 description 1
JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
239000013543 active substance Substances 0.000 description 1
238000013019 agitation Methods 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
229940121375 antifungal agent Drugs 0.000 description 1
239000003429 antifungal agent Substances 0.000 description 1
235000010323 ascorbic acid Nutrition 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-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
150000001642 boronic acid derivatives Chemical class 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 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
239000003795 chemical substances by application Substances 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
239000006071 cream Substances 0.000 description 1
CCZOANFFMASREE-UHFFFAOYSA-N cyclohexane;sulfamic acid Chemical class NS(O)(=O)=O.C1CCCCC1 CCZOANFFMASREE-UHFFFAOYSA-N 0.000 description 1
125000004188 dichlorophenyl group Chemical group 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
TZORNSWZUZDUCU-UHFFFAOYSA-N ethyl 2-methylpyridine-3-carboxylate Chemical compound CCOC(=O)C1=CC=CN=C1C TZORNSWZUZDUCU-UHFFFAOYSA-N 0.000 description 1
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 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
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 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
125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
239000007789 gas Substances 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000003840 hydrochlorides Chemical class 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
150000002688 maleic acid derivatives Chemical class 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000003891 oxalate salts Chemical class 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
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
230000001376 precipitating effect Effects 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
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 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
150000003890 succinate salts Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 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

Landscapes

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)

LU81814A 1978-10-25 1979-10-24 Derives imidazolylethoxy de pyridine-5-methanols et de quinoleine-3-methanols LU81814A1 (fr)

Applications Claiming Priority (4)

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

Publications (1)

Publication Number	Publication Date
LU81814A1 true LU81814A1 (fr)	1980-01-25

Family

ID=27130354

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU81814A LU81814A1 (fr)	1978-10-25	1979-10-24	Derives imidazolylethoxy de pyridine-5-methanols et de quinoleine-3-methanols

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 DK DK448379A patent/DK448379A/da unknown
- 1979-10-24 LU LU81814A patent/LU81814A1/fr 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 NO NO793411A patent/NO793411L/no unknown
- 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
GB2033384A (en)	1980-05-21
IT1125592B (it)	1986-05-14
IE49081B1 (en)	1985-07-24
AU5136879A (en)	1980-05-01
SE7908820L (sv)	1980-04-26
IE791894L (en)	1980-04-25
NO793411L (no)	1980-04-28
HU178748B (en)	1982-06-28
DE2943151A1 (de)	1980-05-08
GB2033384B (en)	1982-08-25
IT7926765A0 (it)	1979-10-24
NL7907349A (nl)	1980-04-29
FR2439781A1 (fr)	1980-05-23
DK448379A (da)	1980-04-26

Publication	Publication Date	Title
BE851310A (fr)	1977-08-10	Nouveaux derives de la tetrahydro-equinocandine b
EP0042781B1 (fr)	1985-03-06	Nouveaux dérivés de (quinolyl-4)-1 (pipéridyl ou pyrrolidinyl-2 ou -3)-2 ou -3 éthanone ou propanone, procédés pour leur préparation, et leur utilisation comme médicaments
LU85551A1 (fr)	1985-04-29	Nouveaux composes azoliques,leur preparation et leur utilisation comme antifongiques et fongicides
CH640837A5 (fr)	1984-01-31	Derives de l'imidazole.
MC1769A1 (fr)	1987-07-17	Diphenaylpiperidines n-substituees
EP0662971B1 (fr)	1998-05-13	DERIVES DE 5H,10H-IMIDAZO[1,2-a]INDENO[1,2-e]PYRAZINE-4-ONE, LEUR PREPARATION ET LES MEDICAMENTS LES CONTENANT
EP0031753B1 (fr)	1984-09-19	Nouveaux dérivés de la (pipéridyl-4)-2 (quinolyl-4)-1 éthanone, produits intermédiaires et procédés pour leur préparation, et leur utilisation comme médicaments
MC1286A1 (fr)	1980-07-22	Preparation de composes heterocycliques utilisables en pharmacie et de medicaments contenant ces composes
EP0042322B1 (fr)	1984-04-18	Nouveaux dérivés de l'indène, procédés pour leur préparation et des médicaments les contenant
EP0327455A1 (fr)	1989-08-09	Ethers alkyliques ou benzyliques du phénol, leurs procédés de préparation et leur application en thérapeutique
LU81814A1 (fr)	1980-01-25	Derives imidazolylethoxy de pyridine-5-methanols et de quinoleine-3-methanols
EP0074873A1 (fr)	1983-03-23	Dérivés de phénoxy-3 propanol-2, leur préparation et leur application en thérapeutique
BE854655A (fr)	1977-11-16	9-hydroxyhexahydrobenzo (c) quinoleines et intermediaires de synthese
FR2470770A1 (fr)	1981-06-12	Nouveaux ethers de b-imidazolylethyle de quinoleine-2 ou 4-methanols, utiles notamment comme antimicrobiens, et leur procede de preparation
CH639075A5 (fr)	1983-10-31	Ethers dibenzyliques substitues actifs sur le plan therapeutique.
FR2492821A1 (fr)	1982-04-30	Derives de la pyrimidine, leur procede de preparation et les compositions pharmaceutiques les contenant
EP0038731B1 (fr)	1983-10-26	Dérivés de thiazole, leur préparation et leur application en thérapeutique
FR2465733A1 (fr)	1981-03-27	Nouveaux derives imidazolylethoxymethyliques de 1,3-dioxoloquinoleines utiles notamment comme medicaments antibacteriens et antifongiques, leur procede de preparation et compositions therapeutiques et formes pharmaceutiques les contenant
EP0403318A1 (fr)	1990-12-19	Procédé de préparation d'une nouvelle substance antitumorale, l'amino-3 (amino-2 1H-imidazolyl-4-)-1 chloro-2 propanol-1 et de ses sels sous forme racémique thréo, utilisable comme médicament
EP0065908B1 (fr)	1984-12-05	((Alkyl- et alcényl-3 pipéridyl-4)-2 éthyl)-3 indoles et leur utilisation comme médicaments
FR2475543A1 (fr)	1981-08-14	Derives benzylideniques, leur preparation et leur application en therapeutique
CH648483A5 (fr)	1985-03-29	Composition pharmaceutique contre l'arthrite rhumatoide.
EP0099822B1 (fr)	1986-11-05	Nouveaux 1-(2-carbalkoxy 4-(thiénylalkylamido)phénoxy) 3-amino 2-propanols, leur préparation et leurs applications en thérapeutique
FR2473520A1 (fr)	1981-07-17	Nouveaux derives imidazolylethoxymethyliques du pyrazole, utiles notamment comme agents antimicrobiens, et leur procede de preparation
FR2692894A1 (fr)	1993-12-31	Aryl-1-(o-alcoxy-phényl-4-pipérazinyl-1)-2, 3- ou 4-alcanols, leur procédé de préparation et leur utilisation pour la préparation de médicaments.