DE1907609C3 - Verfahren zum Abtrennen von (-)-6-Phenyl-233,6tetrahydroimidazo [2,1-b] thiazol von racemischem ( + -)-6-Phenyl -233.6-tetrahydroimidazo [2,1-b] thiazol - Google Patents
Verfahren zum Abtrennen von (-)-6-Phenyl-233,6tetrahydroimidazo [2,1-b] thiazol von racemischem ( + -)-6-Phenyl -233.6-tetrahydroimidazo [2,1-b] thiazolInfo
- Publication number
- DE1907609C3 DE1907609C3 DE1907609A DE1907609A DE1907609C3 DE 1907609 C3 DE1907609 C3 DE 1907609C3 DE 1907609 A DE1907609 A DE 1907609A DE 1907609 A DE1907609 A DE 1907609A DE 1907609 C3 DE1907609 C3 DE 1907609C3
- Authority
- DE
- Germany
- Prior art keywords
- tetrahydroimidazo
- thiazole
- phenyl
- tetramisole
- separating
- 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
- 238000000034 method Methods 0.000 title claims description 9
- 239000002253 acid Substances 0.000 claims description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 6
- YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 claims description 4
- NTOIKDYVJIWVSU-UHFFFAOYSA-N 2,3-dihydroxy-2,3-bis(4-methylbenzoyl)butanedioic acid Chemical compound C1=CC(C)=CC=C1C(=O)C(O)(C(O)=O)C(O)(C(O)=O)C(=O)C1=CC=C(C)C=C1 NTOIKDYVJIWVSU-UHFFFAOYSA-N 0.000 claims description 4
- HLFSDGLLUJUHTE-UHFFFAOYSA-N 6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole Chemical compound N1=C2SCCN2CC1C1=CC=CC=C1 HLFSDGLLUJUHTE-UHFFFAOYSA-N 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 150000003557 thiazoles Chemical class 0.000 claims 1
- HLFSDGLLUJUHTE-SNVBAGLBSA-N Levamisole Chemical compound C1([C@H]2CN3CCSC3=N2)=CC=CC=C1 HLFSDGLLUJUHTE-SNVBAGLBSA-N 0.000 description 23
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- 229960001614 levamisole Drugs 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 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 3
- HLFSDGLLUJUHTE-JTQLQIEISA-N dexamisole Chemical compound C1([C@@H]2CN3CCSC3=N2)=CC=CC=C1 HLFSDGLLUJUHTE-JTQLQIEISA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- MIOPJNTWMNEORI-XVKPBYJWSA-N (R)-camphorsulfonic acid Chemical compound C1C[C@]2(CS(O)(=O)=O)C(=O)C[C@H]1C2(C)C MIOPJNTWMNEORI-XVKPBYJWSA-N 0.000 description 1
- PTAPBGKYBVWNJY-UHFFFAOYSA-N 2,3-dibenzoyl-2,3-dihydroxybutanedioic acid;hydrate Chemical compound O.C=1C=CC=CC=1C(=O)C(O)(C(O)=O)C(O)(C(=O)O)C(=O)C1=CC=CC=C1 PTAPBGKYBVWNJY-UHFFFAOYSA-N 0.000 description 1
- KMGUEILFFWDGFV-UHFFFAOYSA-N 2-benzoyl-2-benzoyloxy-3-hydroxybutanedioic acid Chemical compound C=1C=CC=CC=1C(=O)C(C(C(O)=O)O)(C(O)=O)OC(=O)C1=CC=CC=C1 KMGUEILFFWDGFV-UHFFFAOYSA-N 0.000 description 1
- -1 B. des Hydrochloride Chemical class 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical group C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7321/68A GB1183781A (en) | 1968-02-14 | 1968-02-14 | Resolution Process. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1907609A1 DE1907609A1 (de) | 1970-09-03 |
| DE1907609B2 DE1907609B2 (de) | 1980-01-03 |
| DE1907609C3 true DE1907609C3 (de) | 1980-09-04 |
Family
ID=9830899
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1907609A Expired DE1907609C3 (de) | 1968-02-14 | 1969-02-14 | Verfahren zum Abtrennen von (-)-6-Phenyl-233,6tetrahydroimidazo [2,1-b] thiazol von racemischem ( + -)-6-Phenyl -233.6-tetrahydroimidazo [2,1-b] thiazol |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US3580923A (forum.php) |
| AT (1) | AT283355B (forum.php) |
| BE (1) | BE728371A (forum.php) |
| BG (1) | BG19790A3 (forum.php) |
| BR (1) | BR6906377D0 (forum.php) |
| CH (1) | CH508657A (forum.php) |
| DE (1) | DE1907609C3 (forum.php) |
| DK (1) | DK134673B (forum.php) |
| ES (1) | ES363602A1 (forum.php) |
| FR (1) | FR2001916A1 (forum.php) |
| GB (1) | GB1183781A (forum.php) |
| IE (1) | IE32941B1 (forum.php) |
| IL (1) | IL31556A (forum.php) |
| IT (1) | IT1044177B (forum.php) |
| NL (1) | NL6901620A (forum.php) |
| PL (1) | PL80889B1 (forum.php) |
| RO (1) | RO56601A (forum.php) |
| SE (1) | SE371444B (forum.php) |
| YU (1) | YU32397B (forum.php) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA735753B (en) * | 1972-09-14 | 1974-07-31 | American Cyanamid Co | Resolution of 6-substituted amino phenyl-2,3,5,6-tetrahydro(2,1-b)thiadiazoles |
| DE2854010A1 (de) * | 1977-12-21 | 1979-07-05 | Letraset International Ltd | Verfahren zur herstellung von schildern |
| FI800005A7 (fi) * | 1979-01-05 | 1981-01-01 | Ciba Geigy Ag | Menetelmä uuden vasemmalle kiertävän bisyklisen tiadiatsayhdisteen ja sen suolojen valmistamiseksi. |
| US4672126A (en) * | 1983-11-10 | 1987-06-09 | Janssen Pharmaceutica, N.V. | Process for isolating levamisole from tetramisole |
| US6713627B2 (en) * | 1998-03-13 | 2004-03-30 | Aventis Pharmaceuticals Inc. | Processes for the preparation of (R)-α-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol |
| US20050261341A1 (en) * | 1998-03-13 | 2005-11-24 | Aventis Pharmaceuticals Inc. | Novel processes for the preparation of (R)-alpha-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol |
| EP1984368A2 (en) * | 2006-01-17 | 2008-10-29 | Glenmark Pharmaceuticals Limited | Improved process for the preparation of an optically active 5h-pyrrolo [3,4-b]pyrazine derivative |
| WO2008132128A2 (en) * | 2007-04-27 | 2008-11-06 | Solvay (Société Anonyme) | Synthesis of a pharmaceutically active compound |
| WO2009080708A1 (en) * | 2007-12-21 | 2009-07-02 | Solvay (Société Anonyme) | Use of enantiopure n-sulphonyl pyroglutamic acid as resolving agent |
| CN104557979A (zh) * | 2013-10-23 | 2015-04-29 | 丹阳恒安化学科技研究所有限公司 | 盐酸左旋咪唑的制备方法 |
-
1968
- 1968-02-14 GB GB7321/68A patent/GB1183781A/en not_active Expired
-
1969
- 1969-01-17 IE IE67/69A patent/IE32941B1/xx unknown
- 1969-01-20 PL PL1969131273A patent/PL80889B1/pl unknown
- 1969-01-22 US US793157*A patent/US3580923A/en not_active Expired - Lifetime
- 1969-01-24 IT IT11977/69A patent/IT1044177B/it active
- 1969-01-31 YU YU0235/69A patent/YU32397B/xx unknown
- 1969-01-31 NL NL6901620A patent/NL6901620A/xx unknown
- 1969-02-04 IL IL31556A patent/IL31556A/en unknown
- 1969-02-10 DK DK70369AA patent/DK134673B/da not_active IP Right Cessation
- 1969-02-13 SE SE6901994A patent/SE371444B/xx unknown
- 1969-02-13 ES ES363602A patent/ES363602A1/es not_active Expired
- 1969-02-13 BG BG011661A patent/BG19790A3/xx unknown
- 1969-02-13 BE BE728371D patent/BE728371A/xx not_active IP Right Cessation
- 1969-02-13 BR BR206377/69A patent/BR6906377D0/pt unknown
- 1969-02-14 AT AT151469A patent/AT283355B/de not_active IP Right Cessation
- 1969-02-14 FR FR6903748A patent/FR2001916A1/fr not_active Withdrawn
- 1969-02-14 CH CH227169A patent/CH508657A/de not_active IP Right Cessation
- 1969-02-14 DE DE1907609A patent/DE1907609C3/de not_active Expired
- 1969-02-14 RO RO59096A patent/RO56601A/ro unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES363602A1 (es) | 1971-01-01 |
| NL6901620A (forum.php) | 1969-08-18 |
| BG19790A3 (bg) | 1975-10-10 |
| AT283355B (de) | 1970-08-10 |
| DK134673B (da) | 1976-12-20 |
| RO56601A (forum.php) | 1974-04-29 |
| IL31556A (en) | 1972-07-26 |
| CH508657A (de) | 1971-06-15 |
| BR6906377D0 (pt) | 1973-01-16 |
| DK134673C (forum.php) | 1977-05-23 |
| IL31556A0 (en) | 1969-11-12 |
| US3580923A (en) | 1971-05-25 |
| YU32397B (en) | 1974-10-31 |
| FR2001916A1 (forum.php) | 1969-10-03 |
| IE32941B1 (en) | 1974-01-23 |
| BE728371A (forum.php) | 1969-08-13 |
| SE371444B (forum.php) | 1974-11-18 |
| YU23569A (en) | 1974-04-30 |
| GB1183781A (en) | 1970-03-11 |
| PL80889B1 (forum.php) | 1975-08-30 |
| IT1044177B (it) | 1980-03-20 |
| DE1907609B2 (de) | 1980-01-03 |
| IE32941L (en) | 1969-08-14 |
| DE1907609A1 (de) | 1970-09-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |