CH431526A - Verfahren zur Herstellung von 3-Sulfanilamido-4-halogen-5-alkylisoxazolen - Google Patents

Verfahren zur Herstellung von 3-Sulfanilamido-4-halogen-5-alkylisoxazolen

Info

Publication number: CH431526A
Authority: CH; Switzerland
Prior art keywords: sep; sulfanilamido; amino; methylisoxazole; water
Prior art date: 1962-08-21

Application number

CH893163A

Other languages

German (de)

English (en)

Inventor

Kano Hideo

Ogata Masaru

Nishimura Haruo

Original Assignee

Shionogi & Co

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.)

1962-08-21

Filing date

1963-07-17

Publication date

1967-03-15

1963-07-17 Application filed by Shionogi & Co filed Critical Shionogi & Co

1967-03-15 Publication of CH431526A publication Critical patent/CH431526A/de

Links

238000000034 method Methods 0.000 title claims description 18
238000002360 preparation method Methods 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims description 16
125000003277 amino group Chemical group 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
238000006460 hydrolysis reaction Methods 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
150000008107 benzenesulfonic acids Chemical class 0.000 claims description 4
230000007062 hydrolysis Effects 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
-1 ester radical Chemical class 0.000 description 46
239000000243 solution Substances 0.000 description 26
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
239000013078 crystal Substances 0.000 description 22
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
229940124530 sulfonamide Drugs 0.000 description 20
150000003456 sulfonamides Chemical class 0.000 description 20
239000000203 mixture Substances 0.000 description 19
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
GRDXCFKBQWDAJH-UHFFFAOYSA-N 4-acetamidobenzenesulfonyl chloride Chemical compound CC(=O)NC1=CC=C(S(Cl)(=O)=O)C=C1 GRDXCFKBQWDAJH-UHFFFAOYSA-N 0.000 description 12
150000002148 esters Chemical class 0.000 description 12
JZEWGLZXVUMQOQ-UHFFFAOYSA-N 3-amino-N-(4-iodo-5-methyl-1,2-oxazol-3-yl)benzenesulfonamide Chemical compound S(=O)(C1=CC(=CC=C1)N)(=O)NC1=NOC(=C1I)C JZEWGLZXVUMQOQ-UHFFFAOYSA-N 0.000 description 11
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238000006243 chemical reaction Methods 0.000 description 9
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238000010531 catalytic reduction reaction Methods 0.000 description 8
238000002844 melting Methods 0.000 description 8
230000008018 melting Effects 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
241000699670 Mus sp. Species 0.000 description 7
230000000844 anti-bacterial effect Effects 0.000 description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
238000001953 recrystallisation Methods 0.000 description 7
238000006722 reduction reaction Methods 0.000 description 7
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239000008280 blood Substances 0.000 description 6
210000004369 blood Anatomy 0.000 description 6
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
239000007858 starting material Substances 0.000 description 6
JLKIGFTWXXRPMT-UHFFFAOYSA-N sulphamethoxazole Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 JLKIGFTWXXRPMT-UHFFFAOYSA-N 0.000 description 6
JEZOZNWEHSNXPQ-UHFFFAOYSA-N 4-bromo-5-methyl-1,2-oxazol-3-amine Chemical compound CC=1ON=C(N)C=1Br JEZOZNWEHSNXPQ-UHFFFAOYSA-N 0.000 description 5
DWVOVXRNQIXUEE-UHFFFAOYSA-N 4-chloro-5-methyl-1,2-oxazol-3-amine Chemical compound CC=1ON=C(N)C=1Cl DWVOVXRNQIXUEE-UHFFFAOYSA-N 0.000 description 5
ABSKCUUMSKWKSW-UHFFFAOYSA-N 4-iodo-5-methyl-1,2-oxazol-3-amine Chemical compound CC=1ON=C(N)C=1I ABSKCUUMSKWKSW-UHFFFAOYSA-N 0.000 description 5
FKPXGNGUVSHWQQ-UHFFFAOYSA-N 5-methyl-1,2-oxazol-3-amine Chemical compound CC1=CC(N)=NO1 FKPXGNGUVSHWQQ-UHFFFAOYSA-N 0.000 description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
229910052783 alkali metal Inorganic materials 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
238000001816 cooling Methods 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
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PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
208000015181 infectious disease Diseases 0.000 description 4
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 4
229910003446 platinum oxide Inorganic materials 0.000 description 4
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
239000002904 solvent Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
JXRGUPLJCCDGKG-UHFFFAOYSA-N 4-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=C(S(Cl)(=O)=O)C=C1 JXRGUPLJCCDGKG-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
241000282412 Homo Species 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
241000607142 Salmonella Species 0.000 description 3
241000607762 Shigella flexneri Species 0.000 description 3
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
230000034994 death Effects 0.000 description 3
231100000517 death Toxicity 0.000 description 3
238000010790 dilution Methods 0.000 description 3
239000012895 dilution Substances 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
230000005923 long-lasting effect Effects 0.000 description 3
229960002523 mercuric chloride Drugs 0.000 description 3
LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
230000036470 plasma concentration Effects 0.000 description 3
238000010992 reflux Methods 0.000 description 3
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 3
238000001228 spectrum Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
AMPDEWUZNPWKKX-UHFFFAOYSA-N 4-(phenylmethoxycarbonylamino)benzenesulfonic acid Chemical compound C(C1=CC=CC=C1)OC(=O)NC1=CC=C(C=C1)S(=O)(=O)O AMPDEWUZNPWKKX-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
244000215068 Acacia senegal Species 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
229920001817 Agar Polymers 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
229920000084 Gum arabic Polymers 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
241000193998 Streptococcus pneumoniae Species 0.000 description 2
NHUHCSRWZMLRLA-UHFFFAOYSA-N Sulfisoxazole Chemical compound CC1=NOC(NS(=O)(=O)C=2C=CC(N)=CC=2)=C1C NHUHCSRWZMLRLA-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000000205 acacia gum Substances 0.000 description 2
235000010489 acacia gum Nutrition 0.000 description 2
PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 2
230000007059 acute toxicity Effects 0.000 description 2
231100000403 acute toxicity Toxicity 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
239000008272 agar Substances 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
239000012736 aqueous medium Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical group OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
239000005457 ice water Substances 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
239000002198 insoluble material Substances 0.000 description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
239000011630 iodine Substances 0.000 description 2
231100000636 lethal dose Toxicity 0.000 description 2
231100000053 low toxicity Toxicity 0.000 description 2
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
231100000668 minimum lethal dose Toxicity 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
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239000002244 precipitate Substances 0.000 description 2
230000002035 prolonged effect Effects 0.000 description 2
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SPXOTSHWBDUUMT-UHFFFAOYSA-N 138-42-1 Chemical compound OS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 SPXOTSHWBDUUMT-UHFFFAOYSA-N 0.000 description 1
AMOYMEBHYUTMKJ-UHFFFAOYSA-N 2-(2-phenylethoxy)ethylbenzene Chemical compound C=1C=CC=CC=1CCOCCC1=CC=CC=C1 AMOYMEBHYUTMKJ-UHFFFAOYSA-N 0.000 description 1
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
NILHACLJODBATD-UHFFFAOYSA-N 4-(propanoylamino)benzenesulfonic acid Chemical compound CCC(=O)NC1=CC=C(S(O)(=O)=O)C=C1 NILHACLJODBATD-UHFFFAOYSA-N 0.000 description 1
ZQPVMSLLKQTRMG-UHFFFAOYSA-N 4-acetamidobenzenesulfonic acid Chemical compound CC(=O)NC1=CC=C(S(O)(=O)=O)C=C1 ZQPVMSLLKQTRMG-UHFFFAOYSA-N 0.000 description 1
BENAOQZABXENIF-UHFFFAOYSA-N 4-benzamidobenzenesulfonic acid Chemical compound C1=CC(S(=O)(=O)O)=CC=C1NC(=O)C1=CC=CC=C1 BENAOQZABXENIF-UHFFFAOYSA-N 0.000 description 1
AGQOIYCTCOEHGR-UHFFFAOYSA-N 5-methyl-1,2-oxazole Chemical compound CC1=CC=NO1 AGQOIYCTCOEHGR-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
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235000014469 Bacillus subtilis Nutrition 0.000 description 1
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238000009631 Broth culture Methods 0.000 description 1
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101800004637 Communis Proteins 0.000 description 1
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ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
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AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 1
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HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
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MHGHMVLMYWTSMK-UHFFFAOYSA-N ethyl 4-nitrobenzenesulfonate Chemical compound CCOS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 MHGHMVLMYWTSMK-UHFFFAOYSA-N 0.000 description 1
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239000002609 medium Substances 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
QKEOZZYXWAIQFO-UHFFFAOYSA-M mercury(1+);iodide Chemical compound [Hg]I QKEOZZYXWAIQFO-UHFFFAOYSA-M 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
XOYGCPYJRMAIEA-UHFFFAOYSA-N n-(4-chloro-5-methyl-1,2-oxazol-3-yl)acetamide Chemical compound CC(=O)NC1=NOC(C)=C1Cl XOYGCPYJRMAIEA-UHFFFAOYSA-N 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
150000002916 oxazoles Chemical class 0.000 description 1
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000006201 parenteral dosage form Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000000047 product Substances 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000011946 reduction process Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical class NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
239000003826 tablet Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000005425 toluyl group Chemical group 0.000 description 1
238000011282 treatment Methods 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
CRUISIDZTHMGJT-UHFFFAOYSA-L zinc;dichloride;hydrochloride Chemical compound Cl.[Cl-].[Cl-].[Zn+2] CRUISIDZTHMGJT-UHFFFAOYSA-L 0.000 description 1

Classifications

- 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
- C07D261/14—Nitrogen 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
- C07D261/14—Nitrogen atoms
- C07D261/16—Benzene-sulfonamido isoxazoles

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)

CH893163A 1962-08-21 1963-07-17 Verfahren zur Herstellung von 3-Sulfanilamido-4-halogen-5-alkylisoxazolen CH431526A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP3603062		1962-08-21

Publications (1)

Publication Number	Publication Date
CH431526A true CH431526A (de)	1967-03-15

Family

ID=12458301

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH893163A CH431526A (de)	1962-08-21	1963-07-17	Verfahren zur Herstellung von 3-Sulfanilamido-4-halogen-5-alkylisoxazolen

Country Status (4)

Country	Link
CH (1)	CH431526A (fr)
DE (1)	DE1263771B (fr)
FR (2)	FR1387009A (fr)
GB (2)	GB1002341A (fr)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2888455A (en) *	1956-09-04	1959-05-26	Shionogi & Co	New sulfonamide and process for producing the same

1963
- 1963-01-22 GB GB2773/63A patent/GB1002341A/en not_active Expired
- 1963-01-22 GB GB26091/64A patent/GB1002342A/en not_active Expired
- 1963-01-24 FR FR922533A patent/FR1387009A/fr not_active Expired
- 1963-01-24 FR FR922534A patent/FR3357M/fr active Active
- 1963-07-17 CH CH893163A patent/CH431526A/de unknown
- 1963-07-18 DE DES86253A patent/DE1263771B/de active Pending

Also Published As

Publication number	Publication date
GB1002342A (en)	1965-08-25
FR1387009A (fr)	1965-01-29
FR3357M (fr)	1965-06-08
DE1263771B (de)	1968-03-21
GB1002341A (en)	1965-08-25

Publication	Publication Date	Title
DE1445154C3 (de)	1974-02-14	1,4-Dihydro-1,8-naphthyridinderi vate und ein Verfahren zu ihrer Herstellung
DE2212268C3 (de)	1979-09-13	N-Halogenacetylanilinoessigsäureester, Verfahren zu deren Herstellung und diese enthaltende herbicide Massen
DE2346034C3 (de)	1976-01-22	Alpha-methyl-2-phenyl-5-benzothiazolylessigsaeure
CH431526A (de)	1967-03-15	Verfahren zur Herstellung von 3-Sulfanilamido-4-halogen-5-alkylisoxazolen
DE1493776C3 (de)	1974-07-25	Substituierte o-Phenoxyphenylester, Verfahren zu deren Herstellung und diese enthaltende Mittel
DE2019504C3 (de)	1980-10-02	Oxim-N-acylcarbamate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Schädlingsbekämpfung
DE1493797C3 (de)	1975-02-13	Verfahren zur Herstellung von neuen substituierten Malonsäuremonohydraziden
DE946804C (de)	1956-08-09	Verfahren zur Herstellung von schwefelhaltigen Abkoemmlingen der Barbitursaeure
DE1804983A1 (de)	1969-05-14	Verfahren zur Herstellung von Cephalosporansaeurederivaten
DE1493618A1 (de)	1969-07-10	Cumarinderivate und ein Verfahren zu ihrer Herstellung
DE896946C (de)	1953-11-16	Verfahren zur Herstellung von 2, 6-Dijoddiphenylaethern
DE1189997B (de)	1965-04-01	Verfahren zur Herstellung von Butadiencarbonsaeurepiperaziden
CH627156A5 (fr)	1981-12-31
DE1542872A1 (de)	1970-07-02	Selektives herbizides Mittel
DE1470283C (de)	1971-04-08	l-Methyl-5-sulfanilamido-pyridazon-(6)-derivate
DE1470244C (de)		5-Sulfanilamido-pyridazon-(6)-derivate
CH449006A (de)	1967-12-31	Verfahren zur Herstellung von Fusidinsäure- und Dihydrofusidinsäurederivaten
DE2017023A1 (de)	1970-10-15	Nitroimidazolyl-nitrone
DE889154C (de)	1953-09-07	Verfahren zur Herstellung substituierter Pteridine
DE1492484A1 (de)	1970-03-19	Neue halogenierte Salicylanilide
AT361500B (de)	1981-03-10	Verfahren zur herstellung von neuen n-methyl-n' -acylaminoaethylbenzolsulfonylharnstoffen
DE2008332A1 (en)	1971-09-02	2-methyl-5-methoxy-3-indolylaceto-hydroxamic acid
AT223324B (de)	1962-09-10	Verfahren zur Herstellung von Nitrilen der Tetracycline
AT337709B (de)	1977-07-11	Verfahren zur herstellung von neuen 1-phthalazonderivaten
DE935667C (de)	1955-11-24	Verfahren zur Herstellung von Phenanthridiniumsalzen