JPS5922708B2 - インダゾ−ル誘導体の製法 - Google Patents
インダゾ−ル誘導体の製法Info
- Publication number
- JPS5922708B2 JPS5922708B2 JP49055000A JP5500074A JPS5922708B2 JP S5922708 B2 JPS5922708 B2 JP S5922708B2 JP 49055000 A JP49055000 A JP 49055000A JP 5500074 A JP5500074 A JP 5500074A JP S5922708 B2 JPS5922708 B2 JP S5922708B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- tables
- formulas
- compound
- chemical
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 125000003453 indazolyl group Chemical class N1N=C(C2=C1C=CC=C2)* 0.000 title claims 3
- 150000001875 compounds Chemical class 0.000 claims description 20
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 229930040373 Paraformaldehyde Natural products 0.000 description 8
- 238000000921 elemental analysis Methods 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 229920002866 paraformaldehyde Polymers 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- -1 phenyl-indazole hydrochloride Chemical compound 0.000 description 2
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- YKRSJYZDKRFJNT-UHFFFAOYSA-N (3-phenylindazol-1-yl)methanol Chemical compound C12=CC=CC=C2N(CO)N=C1C1=CC=CC=C1 YKRSJYZDKRFJNT-UHFFFAOYSA-N 0.000 description 1
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- YFSHKTHMTJZZOF-UHFFFAOYSA-N 2-(4-chlorophenyl)-4-methyl-1,2,3,6-tetrahydropyridine Chemical compound C1C(C)=CCNC1C1=CC=C(Cl)C=C1 YFSHKTHMTJZZOF-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
- 150000001241 acetals Chemical class 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000003874 central nervous system depressant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- KLKFAASOGCDTDT-UHFFFAOYSA-N ethoxymethoxyethane Chemical compound CCOCOCC KLKFAASOGCDTDT-UHFFFAOYSA-N 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229920000642 polymer Polymers 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
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP49055000A JPS5922708B2 (ja) | 1974-05-18 | 1974-05-18 | インダゾ−ル誘導体の製法 |
| US05/541,100 US3994890A (en) | 1974-01-31 | 1975-01-15 | 1-Aminoalkyl, 3-phenyl indazoles |
| GB2247/75A GB1489280A (en) | 1974-01-31 | 1975-01-17 | Indazole derivatives |
| FR7502955A FR2259601B1 (en, 2012) | 1974-01-31 | 1975-01-30 | |
| DE2503815A DE2503815C2 (de) | 1974-01-31 | 1975-01-30 | Indazol-Derivate, Verfahren zu ihrer Herstellung und Arzneimittel |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP49055000A JPS5922708B2 (ja) | 1974-05-18 | 1974-05-18 | インダゾ−ル誘導体の製法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS50148355A JPS50148355A (en, 2012) | 1975-11-27 |
| JPS5922708B2 true JPS5922708B2 (ja) | 1984-05-28 |
Family
ID=12986371
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP49055000A Expired JPS5922708B2 (ja) | 1974-01-31 | 1974-05-18 | インダゾ−ル誘導体の製法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5922708B2 (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62177611U (en, 2012) * | 1986-04-30 | 1987-11-11 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1989003385A1 (en) * | 1987-10-13 | 1989-04-20 | Yoshitomi Pharmaceutical Industries, Ltd. | Fused pyrazole compounds, process for their preparation, and their medicinal use |
-
1974
- 1974-05-18 JP JP49055000A patent/JPS5922708B2/ja not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62177611U (en, 2012) * | 1986-04-30 | 1987-11-11 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS50148355A (en, 2012) | 1975-11-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3994890A (en) | 1-Aminoalkyl, 3-phenyl indazoles | |
| JPS6215546B2 (en, 2012) | ||
| JPS6056143B2 (ja) | アミジン誘導体ならびにその製造法 | |
| JPS5943459B2 (ja) | Ｎ−アルキルピペリジン誘導体 | |
| Goodson et al. | Diphenylethylamines. I. The Preparation of Tertiary Amines by the Grignard Reaction1, 2 | |
| IMMEDIATA et al. | β-Naphthyl derivatives of ethanolamine and n-substituted ethanolamines | |
| JPS6040428B2 (ja) | 新規３−アリ−ル−２−オキサゾリジノン誘導体、その製法及び該誘導体を含有する抗抑うつ剤 | |
| CA1120471A (en) | Adamantylmethyl hydrazines, their preparation and pharmaceutical composition containing them | |
| CA1247101A (en) | 5-alkyl-1-phenyl-2-piperazinoalkylpyrazolin-3-one compounds, intermediates and methods for their preparation, and pharmaceutical compositions containing them | |
| EP0061149B1 (en) | Alkylenedioxybenzene derivatives and acid addition salts thereof and a process for their preparation | |
| JPS5962577A (ja) | 新規ピペラジン誘導体及びその製造法 | |
| JPS596868B2 (ja) | 新規イソキノリン誘導体の製造方法 | |
| US5084456A (en) | Oxazolopyridine compounds | |
| US10053420B2 (en) | Processes for the preparation of compounds, such as 3-arylbutanals, useful in the synthesis of medetomidine | |
| JPS6047255B2 (ja) | ２−アミノ−５−スルフアモイル−安息香酸アミドの製法 | |
| JPS5922708B2 (ja) | インダゾ−ル誘導体の製法 | |
| JPS58152882A (ja) | 新規なピペラジンおよびホモピペラジン誘導体 | |
| JPS5915901B2 (ja) | ｕ↓−アミノアルコ−ルの製造方法 | |
| US3733338A (en) | 1-oxo-isochromenes | |
| JPH0625191B2 (ja) | １−［２−（フエニルメチル）フエニルピペラジン化合物、その製造方法および医薬組成物 | |
| CA1041098A (en) | 1-(3-(naphthyl-1-yl-oxy)-propyl)-piperazine derivatives | |
| US3185705A (en) | 2-phenyl-5, 5-di-esters and di-amides of 2-pyrroline and the corresponding pyrrolidines | |
| KAMAL et al. | Chemistry of Pyrazine and Its Derivatives. V. Acylation and Alkylation of 2, 6-Dimethylpyrazine and Certain Other Pyrazine Derivatives1 | |
| JPH03215488A (ja) | ピリミドベンズイミダゾール誘導体 | |
| JPS63239273A (ja) | フエニルイミダゾ−ル誘導体 |