JPH0432827B2 - - Google Patents
Info
- Publication number
- JPH0432827B2 JPH0432827B2 JP59024077A JP2407784A JPH0432827B2 JP H0432827 B2 JPH0432827 B2 JP H0432827B2 JP 59024077 A JP59024077 A JP 59024077A JP 2407784 A JP2407784 A JP 2407784A JP H0432827 B2 JPH0432827 B2 JP H0432827B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- solvent
- methoxyphenyl
- piperazine
- water
- 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 - Lifetime
Links
- 150000003839 salts Chemical class 0.000 claims description 4
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical class C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 claims description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-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
- 239000002253 acid Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- VNZLQLYBRIOLFZ-UHFFFAOYSA-N 1-(2-methoxyphenyl)piperazine Chemical compound COC1=CC=CC=C1N1CCNCC1 VNZLQLYBRIOLFZ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- -1 N-(2-bromoethyl)cyclohexanoylamine Chemical compound 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-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
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000007789 gas Substances 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
- 238000002955 isolation Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- HJFABTUBWNFTBH-UHFFFAOYSA-N n-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]cyclohexanecarboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCNC(=O)C2CCCCC2)CC1 HJFABTUBWNFTBH-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- XHFLOLLMZOTPSM-UHFFFAOYSA-M sodium;hydrogen carbonate;hydrate Chemical compound [OH-].[Na+].OC(O)=O XHFLOLLMZOTPSM-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59024077A JPS60169472A (ja) | 1984-02-10 | 1984-02-10 | 新規なフエニルピペラジン誘導体 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59024077A JPS60169472A (ja) | 1984-02-10 | 1984-02-10 | 新規なフエニルピペラジン誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60169472A JPS60169472A (ja) | 1985-09-02 |
| JPH0432827B2 true JPH0432827B2 (enrdf_load_stackoverflow) | 1992-06-01 |
Family
ID=12128354
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59024077A Granted JPS60169472A (ja) | 1984-02-10 | 1984-02-10 | 新規なフエニルピペラジン誘導体 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60169472A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0434817U (enrdf_load_stackoverflow) * | 1990-07-06 | 1992-03-24 |
-
1984
- 1984-02-10 JP JP59024077A patent/JPS60169472A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60169472A (ja) | 1985-09-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU694569B2 (en) | Process for preparing levobupivacaine and analogues thereof | |
| JP2691442B2 (ja) | 新規なプロリン誘導体 | |
| JPH0251914B2 (enrdf_load_stackoverflow) | ||
| JPH0432827B2 (enrdf_load_stackoverflow) | ||
| SU1250170A3 (ru) | Способ получени дихлоргидрата пирбутерола | |
| 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 | |
| JP2678758B2 (ja) | 新規なプロパン誘導体 | |
| JPS62155268A (ja) | ナイザチジンの合成法 | |
| EP0002401B1 (fr) | Dérivés de naphtalène, leur préparation et leur application en thérapeutique | |
| EP0069527B1 (en) | Cystine derivatives | |
| JPH047345B2 (enrdf_load_stackoverflow) | ||
| GB1580001A (en) | Therapeutically active 1 - phenyl - 1 - methoxy - 2-aminothane derivatives | |
| KR100426534B1 (ko) | 아젤라스틴의 개선된 합성방법 | |
| WO2005075455A2 (en) | Methods for making 4-tetrazolyl-4-phenylpiperidine compounds | |
| JPH0353301B2 (enrdf_load_stackoverflow) | ||
| US4900841A (en) | 1-[4-[(methyl-sulfonyl)amino]benzoyl]aziridine | |
| JPH07165713A (ja) | 化学的方法 | |
| JP4201268B2 (ja) | イミダゾール誘導体およびその塩の製造方法 | |
| JPH0522713B2 (enrdf_load_stackoverflow) | ||
| JPS5852995B2 (ja) | フルフラ−ル誘導体の製造法 | |
| JPH0454175A (ja) | アルキルピペラジン誘導体 | |
| HRP20000490A2 (en) | Process for the preparation of amlodipine besilate | |
| Suh et al. | Synthesis of 3-amino-1, 4-dihydropyridine derivative via an intramolecular rearrangement of 1, 4-dihydropyridine-3-hydroxamate | |
| WO2004048342A1 (ja) | １−[２−(ベンズイミダゾール−２−イルチオ）エチル]ピペラジン又はその塩の製造法 | |
| BE835297A (fr) | Nouvelles diazepines et procede pour les produire |