HU189236B - Process for producing new type isoxazoles - Google Patents
Process for producing new type isoxazoles Download PDFInfo
- Publication number
- HU189236B HU189236B HU83661A HU66183A HU189236B HU 189236 B HU189236 B HU 189236B HU 83661 A HU83661 A HU 83661A HU 66183 A HU66183 A HU 66183A HU 189236 B HU189236 B HU 189236B
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- Hungary
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- 150000002545 isoxazoles Chemical class 0.000 title claims abstract description 6
- 238000000034 method Methods 0.000 title claims description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 60
- 125000002560 nitrile group Chemical group 0.000 claims abstract description 10
- 150000008064 anhydrides Chemical group 0.000 claims abstract description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 2
- -1 alkyl chloroformate Chemical compound 0.000 claims description 18
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 150000004820 halides Chemical class 0.000 claims description 5
- 239000012024 dehydrating agents Substances 0.000 claims description 4
- 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 description 4
- 150000008065 acid anhydrides Chemical class 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 239000011574 phosphorus Substances 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical group CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims description 2
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- WKDDRNSBRWANNC-ATRFCDNQSA-N Thienamycin Chemical compound C1C(SCCN)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 WKDDRNSBRWANNC-ATRFCDNQSA-N 0.000 abstract description 3
- WKDDRNSBRWANNC-UHFFFAOYSA-N Thienamycin Natural products C1C(SCCN)=C(C(O)=O)N2C(=O)C(C(O)C)C21 WKDDRNSBRWANNC-UHFFFAOYSA-N 0.000 abstract description 3
- 230000003115 biocidal effect Effects 0.000 abstract description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 abstract description 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 24
- 238000005160 1H NMR spectroscopy Methods 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 238000010992 reflux Methods 0.000 description 7
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- OFAJKJYAXWKZSZ-UHFFFAOYSA-N 2-(4-cyano-5-methyl-1,2-oxazol-3-yl)acetic acid Chemical compound CC=1ON=C(CC(O)=O)C=1C#N OFAJKJYAXWKZSZ-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 150000002825 nitriles Chemical group 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 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 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000012190 activator Substances 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 3
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 3
- 235000015497 potassium bicarbonate Nutrition 0.000 description 3
- 239000011736 potassium bicarbonate Substances 0.000 description 3
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
- MGUQYZSKPMBDBI-UHFFFAOYSA-N 1,2,3,5a,6,7,8,9-octahydropyrido[1,2-b]diazepine Chemical compound N1CCC=CC2CCCCN21 MGUQYZSKPMBDBI-UHFFFAOYSA-N 0.000 description 2
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 2
- UIGKHPGXCZMBHY-UHFFFAOYSA-N 2-(4-cyano-5-methyl-1,2-oxazol-3-yl)-N-phenylacetamide Chemical compound N#CC1=C(C)ON=C1CC(=O)NC1=CC=CC=C1 UIGKHPGXCZMBHY-UHFFFAOYSA-N 0.000 description 2
- WMURHLWUBPCKKX-UHFFFAOYSA-N 5-methyl-3-(2-morpholin-4-yl-2-oxoethyl)-1,2-oxazole-4-carbonitrile Chemical compound N#CC1=C(C)ON=C1CC(=O)N1CCOCC1 WMURHLWUBPCKKX-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 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 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- FWMOCVHNWVZETC-UHFFFAOYSA-N ethyl 3-[2-(benzylamino)-2-oxoethyl]-5-methyl-1,2-oxazole-4-carboxylate Chemical compound C(C)OC(=O)C=1C(=NOC1C)CC(=O)NCC1=CC=CC=C1 FWMOCVHNWVZETC-UHFFFAOYSA-N 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- RMPKWCFHPRKUDX-QXMHVHEDSA-N (Z)-3-amino-4-cyano-5-oxo-N-phenylhex-3-enamide Chemical compound CC(=O)C(\C#N)=C(/N)CC(=O)Nc1ccccc1 RMPKWCFHPRKUDX-QXMHVHEDSA-N 0.000 description 1
- MLXDUYUQINCFFV-UHFFFAOYSA-N 2-acetyloxyacetic acid Chemical class CC(=O)OCC(O)=O MLXDUYUQINCFFV-UHFFFAOYSA-N 0.000 description 1
- NUJNTWROJOXVNY-UHFFFAOYSA-N 3-(5-methyl-1,2-oxazol-4-yl)-4h-1,2-oxazol-5-one Chemical compound O1N=CC(C=2CC(=O)ON=2)=C1C NUJNTWROJOXVNY-UHFFFAOYSA-N 0.000 description 1
- UPVVZCLEAHDZFZ-UHFFFAOYSA-N 3-(carboxymethyl)-5-methyl-1,2-oxazole-4-carboxylic acid Chemical compound CC=1ON=C(CC(O)=O)C=1C(O)=O UPVVZCLEAHDZFZ-UHFFFAOYSA-N 0.000 description 1
- UBNWPQXLFRMMEI-GQCTYLIASA-N 5-[3-[(e)-3-(3-hydroxy-2-methoxycarbonylphenoxy)prop-1-enyl]phenyl]-1,2-oxazole-3-carboxylic acid Chemical compound COC(=O)C1=C(O)C=CC=C1OC\C=C\C1=CC=CC(C=2ON=C(C=2)C(O)=O)=C1 UBNWPQXLFRMMEI-GQCTYLIASA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- CULFARIRKDSMQV-CSKARUKUSA-N C(C)(=O)/C(/C(=O)OCC)=C(/CC(=O)OCC)N Chemical compound C(C)(=O)/C(/C(=O)OCC)=C(/CC(=O)OCC)N CULFARIRKDSMQV-CSKARUKUSA-N 0.000 description 1
- GTIKWULBXBBVQR-SEYXRHQNSA-N C(C1=CC=CC=C1)NC(C/C(=C(/C(C)=O)\C#N)/N)=O Chemical compound C(C1=CC=CC=C1)NC(C/C(=C(/C(C)=O)\C#N)/N)=O GTIKWULBXBBVQR-SEYXRHQNSA-N 0.000 description 1
- ZNAYYHOLNOZZSH-UHFFFAOYSA-N CC1=C(C=NO1)C1=NOC(=C1C(=O)OCC)O Chemical compound CC1=C(C=NO1)C1=NOC(=C1C(=O)OCC)O ZNAYYHOLNOZZSH-UHFFFAOYSA-N 0.000 description 1
- 241000283073 Equus caballus Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- KSXDGWMADBQCBT-UHFFFAOYSA-N NC(CC(=O)N1CCOCC1)=C(/C(C)=O)C#N Chemical compound NC(CC(=O)N1CCOCC1)=C(/C(C)=O)C#N KSXDGWMADBQCBT-UHFFFAOYSA-N 0.000 description 1
- 125000004018 acid anhydride group Chemical group 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- RAMQAMYGQDRQKW-UHFFFAOYSA-N benzene;butan-1-ol Chemical group CCCCO.C1=CC=CC=C1 RAMQAMYGQDRQKW-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000005065 mining Methods 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
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members 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
- C07D261/12—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members 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
- C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D309/30—Oxygen atoms, e.g. delta-lactones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU83661A HU189236B (en) | 1983-02-28 | 1983-02-28 | Process for producing new type isoxazoles |
| DE19843405422 DE3405422A1 (de) | 1983-02-28 | 1984-02-15 | Isoxazolderivate, verfahren zu ihrer herstellung sowie deren verwendung |
| NL8400575A NL8400575A (nl) | 1983-02-28 | 1984-02-24 | Nieuwe isoxazolen en werkwijze voor de bereiding ervan. |
| BE1/10966A BE899007A (fr) | 1983-02-28 | 1984-02-27 | Nouveaux isoxazoles et procede pour leur preparation |
| GB08405001A GB2135996B (en) | 1983-02-28 | 1984-02-27 | New isoxazoles and process for the preparation thereof |
| SE8401064A SE8401064L (sv) | 1983-02-28 | 1984-02-27 | Nya isoxazoler och forfarande for framstellning derav |
| CH935/84A CH658655A5 (de) | 1983-02-28 | 1984-02-27 | Neue isoxazole und verfahren zu ihrer herstellung. |
| JP59034477A JPS59164784A (ja) | 1983-02-28 | 1984-02-27 | イソキサゾ−ル誘導体及びその製造方法 |
| FR8402947A FR2541678A1 (fr) | 1983-02-28 | 1984-02-27 | Nouveaux isoxazoles et procede pour leur fabrication |
| IT19806/84A IT1174498B (it) | 1983-02-28 | 1984-02-27 | Isossazoli e procedimento per la loro preparazione |
| PT78157A PT78157B (de) | 1983-02-28 | 1984-02-27 | Neue isoxazole und verfahren zu ihrer herstellung |
| ES530121A ES8601935A1 (es) | 1983-02-28 | 1984-02-28 | Procedimiento para la obtencion de isoxazoles |
| ES544191A ES8604174A1 (es) | 1983-02-28 | 1985-06-14 | Procedimiento para la obtencion de isoxazoles |
| ES544192A ES8604175A1 (es) | 1983-02-28 | 1985-06-14 | Procedimiento para la obtencion de isoxazoles |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU83661A HU189236B (en) | 1983-02-28 | 1983-02-28 | Process for producing new type isoxazoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU189236B true HU189236B (en) | 1986-06-30 |
Family
ID=10950718
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU83661A HU189236B (en) | 1983-02-28 | 1983-02-28 | Process for producing new type isoxazoles |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS59164784A (fr) |
| BE (1) | BE899007A (fr) |
| CH (1) | CH658655A5 (fr) |
| DE (1) | DE3405422A1 (fr) |
| ES (3) | ES8601935A1 (fr) |
| FR (1) | FR2541678A1 (fr) |
| GB (1) | GB2135996B (fr) |
| HU (1) | HU189236B (fr) |
| IT (1) | IT1174498B (fr) |
| NL (1) | NL8400575A (fr) |
| PT (1) | PT78157B (fr) |
| SE (1) | SE8401064L (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5366987A (en) * | 1991-08-22 | 1994-11-22 | Warner-Lambert Company | Isoxazolyl-substituted alkyl amide ACAT inhibitors |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4163057A (en) * | 1977-12-27 | 1979-07-31 | Sandoz, Inc. | Isoxazole-4-carboxamides as tranquilizers, sleep-inducers and muscle relaxants |
-
1983
- 1983-02-28 HU HU83661A patent/HU189236B/hu not_active IP Right Cessation
-
1984
- 1984-02-15 DE DE19843405422 patent/DE3405422A1/de not_active Withdrawn
- 1984-02-24 NL NL8400575A patent/NL8400575A/nl not_active Application Discontinuation
- 1984-02-27 BE BE1/10966A patent/BE899007A/fr not_active IP Right Cessation
- 1984-02-27 IT IT19806/84A patent/IT1174498B/it active
- 1984-02-27 GB GB08405001A patent/GB2135996B/en not_active Expired
- 1984-02-27 CH CH935/84A patent/CH658655A5/de not_active IP Right Cessation
- 1984-02-27 SE SE8401064A patent/SE8401064L/xx not_active Application Discontinuation
- 1984-02-27 PT PT78157A patent/PT78157B/pt unknown
- 1984-02-27 FR FR8402947A patent/FR2541678A1/fr active Pending
- 1984-02-27 JP JP59034477A patent/JPS59164784A/ja active Pending
- 1984-02-28 ES ES530121A patent/ES8601935A1/es not_active Expired
-
1985
- 1985-06-14 ES ES544192A patent/ES8604175A1/es not_active Expired
- 1985-06-14 ES ES544191A patent/ES8604174A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES544191A0 (es) | 1986-01-16 |
| NL8400575A (nl) | 1984-09-17 |
| SE8401064D0 (sv) | 1984-02-27 |
| FR2541678A1 (fr) | 1984-08-31 |
| IT8419806A0 (it) | 1984-02-27 |
| ES530121A0 (es) | 1985-11-16 |
| JPS59164784A (ja) | 1984-09-17 |
| DE3405422A1 (de) | 1984-08-30 |
| GB8405001D0 (en) | 1984-04-04 |
| PT78157B (de) | 1986-05-19 |
| SE8401064L (sv) | 1984-08-29 |
| IT1174498B (it) | 1987-07-01 |
| BE899007A (fr) | 1984-08-27 |
| GB2135996A (en) | 1984-09-12 |
| ES8601935A1 (es) | 1985-11-16 |
| PT78157A (de) | 1984-03-01 |
| CH658655A5 (de) | 1986-11-28 |
| ES8604174A1 (es) | 1986-01-16 |
| GB2135996B (en) | 1986-09-10 |
| ES544192A0 (es) | 1986-01-16 |
| ES8604175A1 (es) | 1986-01-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |