CH412887A - Verfahren zur Herstellung von Additionssalzen des 1-Methyl-3-(di-2-thienylmethylen)-piperidins - Google Patents
Verfahren zur Herstellung von Additionssalzen des 1-Methyl-3-(di-2-thienylmethylen)-piperidinsInfo
- Publication number
- CH412887A CH412887A CH1422861A CH1422861A CH412887A CH 412887 A CH412887 A CH 412887A CH 1422861 A CH1422861 A CH 1422861A CH 1422861 A CH1422861 A CH 1422861A CH 412887 A CH412887 A CH 412887A
- Authority
- CH
- Switzerland
- Prior art keywords
- thienylmethylene
- methyl
- piperidine
- carboxylic acid
- benzophenone
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims description 16
- JWIXXNLOKOAAQT-UHFFFAOYSA-N tipepidine Chemical class C1N(C)CCCC1=C(C=1SC=CC=1)C1=CC=CS1 JWIXXNLOKOAAQT-UHFFFAOYSA-N 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 5
- YGTUPRIZNBMOFV-UHFFFAOYSA-N 2-(4-hydroxybenzoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=C(O)C=C1 YGTUPRIZNBMOFV-UHFFFAOYSA-N 0.000 claims description 8
- FGTYTUFKXYPTML-UHFFFAOYSA-N 2-benzoylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 FGTYTUFKXYPTML-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- -1 di-2-thienylmethylene Chemical group 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 239000012458 free base Substances 0.000 claims description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000013078 crystal Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WQOYJMWVNIGIQR-UHFFFAOYSA-N 3-(dithiophen-2-ylmethylidene)-1-methylpiperidine;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C1N(C)CCCC1=C(C=1SC=CC=1)C1=CC=CS1 WQOYJMWVNIGIQR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000003434 antitussive agent Substances 0.000 description 1
- 229940124584 antitussives Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 235000019658 bitter taste Nutrition 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000003172 expectorant agent Substances 0.000 description 1
- 230000003419 expectorant effect Effects 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000020075 ouzo Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5010860 | 1960-12-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH412887A true CH412887A (de) | 1966-05-15 |
Family
ID=12849873
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1422861A CH412887A (de) | 1960-12-19 | 1961-12-08 | Verfahren zur Herstellung von Additionssalzen des 1-Methyl-3-(di-2-thienylmethylen)-piperidins |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE610531A (fr) |
| BR (1) | BR6135119D0 (fr) |
| CH (1) | CH412887A (fr) |
| ES (1) | ES271829A1 (fr) |
| FR (1) | FR1656M (fr) |
| GB (1) | GB924544A (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1107738A4 (fr) * | 1998-08-27 | 2003-01-22 | Bristol Myers Squibb Co | Nouvelle forme saline pharmaceutique |
-
1961
- 1961-11-08 ES ES0271829A patent/ES271829A1/es not_active Expired
- 1961-11-20 BE BE610531A patent/BE610531A/fr unknown
- 1961-12-07 GB GB43821/61A patent/GB924544A/en not_active Expired
- 1961-12-08 CH CH1422861A patent/CH412887A/de unknown
- 1961-12-14 FR FR882020A patent/FR1656M/fr not_active Expired
- 1961-12-19 BR BR135119/61A patent/BR6135119D0/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES271829A1 (es) | 1962-03-01 |
| GB924544A (en) | 1963-04-24 |
| BE610531A (fr) | 1962-03-16 |
| BR6135119D0 (pt) | 1973-07-03 |
| FR1656M (fr) | 1963-01-14 |
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