BE581435A - - Google Patents

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Publication number: BE581435A
Authority: BE; Belgium
Prior art keywords: solution; hydrazine; residue; group; acyl
Prior art date

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Other languages

Publication of BE581435A publication Critical patent/BE581435A/fr

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230000002829 reduced Effects 0.000 claims description 36
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 35
150000001875 compounds Chemical class 0.000 claims description 23
125000002252 acyl group Chemical group 0.000 claims description 22
239000001257 hydrogen Substances 0.000 claims description 22
229910052739 hydrogen Inorganic materials 0.000 claims description 22
-1 aliphatic oxo compound Chemical class 0.000 claims description 16
238000006243 chemical reaction Methods 0.000 claims description 15
150000002429 hydrazines Chemical class 0.000 claims description 14
125000001931 aliphatic group Chemical group 0.000 claims description 10
QRXWMOHMRWLFEY-UHFFFAOYSA-N Isoniazid Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 claims description 8
150000007857 hydrazones Chemical class 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 8
125000001118 alkylidene group Chemical group 0.000 claims description 7
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
230000000875 corresponding Effects 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 4
238000000034 method Methods 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
239000011630 iodine Substances 0.000 claims description 3
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
229910052740 iodine Inorganic materials 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
125000004433 nitrogen atoms Chemical group N* 0.000 claims 1
239000000243 solution Substances 0.000 description 153
HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 88
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 70
239000000203 mixture Substances 0.000 description 48
RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 46
LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 46
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 46
VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 42
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 42
238000001816 cooling Methods 0.000 description 40
CSNNHWWHGAXBCP-UHFFFAOYSA-L mgso4 Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 40
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 32
229910052753 mercury Inorganic materials 0.000 description 31
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 29
238000003756 stirring Methods 0.000 description 26
235000011118 potassium hydroxide Nutrition 0.000 description 25
235000015320 potassium carbonate Nutrition 0.000 description 22
XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
229910052943 magnesium sulfate Inorganic materials 0.000 description 20
235000019341 magnesium sulphate Nutrition 0.000 description 20
239000001184 potassium carbonate Substances 0.000 description 20
229910000027 potassium carbonate Inorganic materials 0.000 description 20
238000010992 reflux Methods 0.000 description 19
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
239000000706 filtrate Substances 0.000 description 18
239000000155 melt Substances 0.000 description 18
UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 16
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 16
238000009835 boiling Methods 0.000 description 15
239000000126 substance Substances 0.000 description 15
238000001914 filtration Methods 0.000 description 14
239000002904 solvent Substances 0.000 description 14
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
238000002844 melting Methods 0.000 description 13
239000002253 acid Substances 0.000 description 12
239000003054 catalyst Substances 0.000 description 12
238000001035 drying Methods 0.000 description 12
239000003921 oil Substances 0.000 description 12
WCUXLLCKKVVCTQ-UHFFFAOYSA-M potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 12
239000007789 gas Substances 0.000 description 11
238000000354 decomposition reaction Methods 0.000 description 10
238000004821 distillation Methods 0.000 description 10
239000007788 liquid Substances 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 10
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 10
239000002026 chloroform extract Substances 0.000 description 9
239000012299 nitrogen atmosphere Substances 0.000 description 9
239000011780 sodium chloride Substances 0.000 description 9
235000002639 sodium chloride Nutrition 0.000 description 9
239000007787 solid Substances 0.000 description 9
FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
WETWJCDKMRHUPV-UHFFFAOYSA-N Acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 7
OFLXLNCGODUUOT-UHFFFAOYSA-N acetohydrazonic acid Chemical compound C\C(O)=N\N OFLXLNCGODUUOT-UHFFFAOYSA-N 0.000 description 7
239000012346 acetyl chloride Substances 0.000 description 7
238000002425 crystallisation Methods 0.000 description 7
230000005712 crystallization Effects 0.000 description 7
239000000284 extract Substances 0.000 description 7
238000001953 recrystallisation Methods 0.000 description 7
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
229960000583 Acetic Acid Drugs 0.000 description 6
239000007868 Raney catalyst Substances 0.000 description 6
229910000564 Raney nickel Inorganic materials 0.000 description 6
238000007792 addition Methods 0.000 description 6
238000010438 heat treatment Methods 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
239000001103 potassium chloride Substances 0.000 description 6
235000011164 potassium chloride Nutrition 0.000 description 6
238000001704 evaporation Methods 0.000 description 5
229910052697 platinum Inorganic materials 0.000 description 5
230000000630 rising Effects 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
239000010410 layer Substances 0.000 description 4
HPQVWDOOUQVBTO-UHFFFAOYSA-N lithium aluminium hydride Substances [Li+].[Al-] HPQVWDOOUQVBTO-UHFFFAOYSA-N 0.000 description 4
OCZDCIYGECBNKL-UHFFFAOYSA-N lithium;alumanuide Chemical compound [Li+].[AlH4-] OCZDCIYGECBNKL-UHFFFAOYSA-N 0.000 description 4
150000002829 nitrogen Chemical group 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
JIQXKYSNGXUDJU-UHFFFAOYSA-N propan-2-ylidenehydrazine Chemical compound CC(C)=NN JIQXKYSNGXUDJU-UHFFFAOYSA-N 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
NLHHRLWOUZZQLW-UHFFFAOYSA-N acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
125000004432 carbon atoms Chemical group C* 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
239000012230 colorless oil Substances 0.000 description 3
239000003814 drug Substances 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
239000011707 mineral Substances 0.000 description 3
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 3
239000012071 phase Substances 0.000 description 3
229910003446 platinum oxide Inorganic materials 0.000 description 3
239000000047 product Substances 0.000 description 3
239000001187 sodium carbonate Substances 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
235000011121 sodium hydroxide Nutrition 0.000 description 3
239000005711 Benzoic acid Substances 0.000 description 2
RHXARBUTTQDWBQ-UHFFFAOYSA-N C(C)N(C(CCl)CC(C)C)CC Chemical compound C(C)N(C(CCl)CC(C)C)CC RHXARBUTTQDWBQ-UHFFFAOYSA-N 0.000 description 2
GLNNAGUOJMBJFN-UHFFFAOYSA-N C(C)N(CC)C(C)(C)N(N=C(C)C)C(C)=O Chemical compound C(C)N(CC)C(C)(C)N(N=C(C)C)C(C)=O GLNNAGUOJMBJFN-UHFFFAOYSA-N 0.000 description 2
NKDDWNXOKDWJAK-UHFFFAOYSA-N Dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 2
229940093915 Gynecological Organic acids Drugs 0.000 description 2
YFGPJYNCAPSRRF-UHFFFAOYSA-N N'-(2-cyanoethyl)acetohydrazide Chemical compound CC(=O)NNCCC#N YFGPJYNCAPSRRF-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
230000001476 alcoholic Effects 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
150000001539 azetidines Chemical class 0.000 description 2
239000002585 base Substances 0.000 description 2
WARCRYXKINZHGQ-UHFFFAOYSA-N benzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1 WARCRYXKINZHGQ-UHFFFAOYSA-N 0.000 description 2
235000010233 benzoic acid Nutrition 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
239000001569 carbon dioxide Substances 0.000 description 2
229910002092 carbon dioxide Inorganic materials 0.000 description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
229940079593 drugs Drugs 0.000 description 2
239000012458 free base Substances 0.000 description 2
239000000446 fuel Substances 0.000 description 2
239000011521 glass Substances 0.000 description 2
125000005842 heteroatoms Chemical group 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
239000011261 inert gas Substances 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
238000002156 mixing Methods 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
229940072033 potash Drugs 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000012047 saturated solution Substances 0.000 description 2
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000000725 suspension Substances 0.000 description 2
238000002560 therapeutic procedure Methods 0.000 description 2
ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical class O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
VFPKIWATTACVJR-UHFFFAOYSA-N 1-(dimethylamino)propan-2-one Chemical compound CN(C)CC(C)=O VFPKIWATTACVJR-UHFFFAOYSA-N 0.000 description 1
YMDNODNLFSHHCV-UHFFFAOYSA-N 2-chloro-N,N-diethylethanamine Chemical compound CCN(CC)CCCl YMDNODNLFSHHCV-UHFFFAOYSA-N 0.000 description 1
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
JRSKFKZAKLAAMS-UHFFFAOYSA-N 4-[methyl(propan-2-yl)amino]butan-2-one Chemical compound CC(C)N(C)CCC(C)=O JRSKFKZAKLAAMS-UHFFFAOYSA-N 0.000 description 1
125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
QIRAYNIFEOXSPW-UHFFFAOYSA-N 6-(dimethylamino)-4,4-diphenylheptan-3-ol Chemical compound C=1C=CC=CC=1C(CC(C)N(C)C)(C(O)CC)C1=CC=CC=C1 QIRAYNIFEOXSPW-UHFFFAOYSA-N 0.000 description 1
210000000941 Bile Anatomy 0.000 description 1
GYQSOLKGKZOBFO-UHFFFAOYSA-N C(C)N(CC)N(N)C(C)C Chemical compound C(C)N(CC)N(N)C(C)C GYQSOLKGKZOBFO-UHFFFAOYSA-N 0.000 description 1
GJVNDTVCGIGRNN-UHFFFAOYSA-N CN(C)C(C)(C)N(N=C(C)C)C(C)=O Chemical compound CN(C)C(C)(C)N(N=C(C)C)C(C)=O GJVNDTVCGIGRNN-UHFFFAOYSA-N 0.000 description 1
101710040910 CRAT Proteins 0.000 description 1
240000002989 Euphorbia neriifolia Species 0.000 description 1
241000157848 Haldina cordifolia Species 0.000 description 1
108020005203 Oxidases Proteins 0.000 description 1
DHHVAGZRUROJKS-UHFFFAOYSA-N Phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 description 1
229960002895 Phenylbutazone Drugs 0.000 description 1
101700082113 RMT2 Proteins 0.000 description 1
206010072736 Rheumatic disease Diseases 0.000 description 1
241000220317 Rosa Species 0.000 description 1
241001426756 Senna tora Species 0.000 description 1
240000003670 Sesamum indicum Species 0.000 description 1
108010009740 Vp16-Jazz protein Proteins 0.000 description 1
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
238000006640 acetylation reaction Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
BRWIZMBXBAOCCF-UHFFFAOYSA-N aminothiourea Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
230000000202 analgesic Effects 0.000 description 1
230000001741 anti-phlogistic Effects 0.000 description 1
230000001754 anti-pyretic Effects 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
150000007514 bases Chemical class 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
238000002485 combustion reaction Methods 0.000 description 1
229950004655 dimepheptanol Drugs 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
KVXNKFYSHAUJIA-UHFFFAOYSA-M ethoxyethane;acetate Chemical compound CC([O-])=O.CCOCC KVXNKFYSHAUJIA-UHFFFAOYSA-M 0.000 description 1
239000003502 gasoline Substances 0.000 description 1
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
229910052737 gold Inorganic materials 0.000 description 1
239000010931 gold Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
LIAWOTKNAVAKCX-UHFFFAOYSA-N hydrazine;dihydrochloride Chemical compound Cl.Cl.NN LIAWOTKNAVAKCX-UHFFFAOYSA-N 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000000977 initiatory Effects 0.000 description 1
KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
230000000670 limiting Effects 0.000 description 1
150000002690 malonic acid derivatives Chemical class 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
XTEGVFVZDVNBPF-UHFFFAOYSA-L naphthalene-1,5-disulfonate(2-) Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1S([O-])(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-L 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
229940075930 picrate Drugs 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
239000011148 porous material Substances 0.000 description 1
230000002035 prolonged Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
WTKZEGDFNFYCGP-UHFFFAOYSA-N pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
150000003218 pyrazolidines Chemical class 0.000 description 1
239000003638 reducing agent Substances 0.000 description 1
238000002633 shock therapy Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
230000001629 suppression Effects 0.000 description 1
230000001225 therapeutic Effects 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1

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Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

BE581435D BE581435A (es)

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Publication Number	Publication Date
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