JPS6330898B2 - - Google Patents
Info
- Publication number
- JPS6330898B2 JPS6330898B2 JP14910279A JP14910279A JPS6330898B2 JP S6330898 B2 JPS6330898 B2 JP S6330898B2 JP 14910279 A JP14910279 A JP 14910279A JP 14910279 A JP14910279 A JP 14910279A JP S6330898 B2 JPS6330898 B2 JP S6330898B2
- Authority
- JP
- Japan
- Prior art keywords
- pyrazole
- melting point
- mol
- yield
- ethyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- YKEKWOJUUNYRIR-UHFFFAOYSA-N methanol;1h-pyrazole Chemical class OC.C=1C=NNC=1 YKEKWOJUUNYRIR-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000000862 absorption spectrum Methods 0.000 description 5
- 238000000921 elemental analysis Methods 0.000 description 5
- -1 lithium aluminum hydride Chemical compound 0.000 description 5
- 238000001819 mass spectrum Methods 0.000 description 5
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- KOPFEFZSAMLEHK-UHFFFAOYSA-N 1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- CJPNOLIZCWDHJK-UHFFFAOYSA-N 2-Pentadecanone Chemical compound CCCCCCCCCCCCCC(C)=O CJPNOLIZCWDHJK-UHFFFAOYSA-N 0.000 description 1
- 238000003512 Claisen condensation reaction Methods 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- NUJSKBKQPLSBSV-UHFFFAOYSA-N ethyl 5-heptyl-1h-pyrazole-3-carboxylate Chemical compound CCCCCCCC1=CC(C(=O)OCC)=NN1 NUJSKBKQPLSBSV-UHFFFAOYSA-N 0.000 description 1
- CAZPQXZJZQFFNG-UHFFFAOYSA-N ethyl 5-nonyl-1h-pyrazole-3-carboxylate Chemical compound CCCCCCCCCC1=CC(C(=O)OCC)=NN1 CAZPQXZJZQFFNG-UHFFFAOYSA-N 0.000 description 1
- ILTUMWMASHHTOQ-UHFFFAOYSA-N ethyl 5-propan-2-yl-1h-pyrazole-3-carboxylate Chemical compound CCOC(=O)C=1C=C(C(C)C)NN=1 ILTUMWMASHHTOQ-UHFFFAOYSA-N 0.000 description 1
- ZCFBTLBKQPNMAR-UHFFFAOYSA-N ethyl 5-undecyl-1h-pyrazole-3-carboxylate Chemical compound CCCCCCCCCCCC1=CC(C(=O)OCC)=NN1 ZCFBTLBKQPNMAR-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- UVIUABLEHDZQSC-UHFFFAOYSA-M sodium;1-ethoxy-1,4-dioxoheptadec-2-en-2-olate Chemical compound [Na+].CCCCCCCCCCCCCC(=O)C=C([O-])C(=O)OCC UVIUABLEHDZQSC-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14910279A JPS5673068A (en) | 1979-11-16 | 1979-11-16 | Pyrazolecarbinol derivative |
| ES497143A ES497143A0 (es) | 1979-11-16 | 1980-11-13 | Procedimiento para la fabricacion de derivados del pirazol |
| EP19800304106 EP0029363A1 (en) | 1979-11-16 | 1980-11-14 | Pyrazole derivatives, process for their preparation and pharmaceutical compositions containing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14910279A JPS5673068A (en) | 1979-11-16 | 1979-11-16 | Pyrazolecarbinol derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5673068A JPS5673068A (en) | 1981-06-17 |
| JPS6330898B2 true JPS6330898B2 (https=) | 1988-06-21 |
Family
ID=15467734
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14910279A Granted JPS5673068A (en) | 1979-11-16 | 1979-11-16 | Pyrazolecarbinol derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5673068A (https=) |
-
1979
- 1979-11-16 JP JP14910279A patent/JPS5673068A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5673068A (en) | 1981-06-17 |
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