GB1152544A - Resolution of dl-6-Phenyl-2,3,5,6-Tetrahydroimidazo [2,1-b] Thiazole - Google Patents
Resolution of dl-6-Phenyl-2,3,5,6-Tetrahydroimidazo [2,1-b] ThiazoleInfo
- Publication number
- GB1152544A GB1152544A GB2297767A GB2297767A GB1152544A GB 1152544 A GB1152544 A GB 1152544A GB 2297767 A GB2297767 A GB 2297767A GB 2297767 A GB2297767 A GB 2297767A GB 1152544 A GB1152544 A GB 1152544A
- Authority
- GB
- United Kingdom
- Prior art keywords
- tetrahydroimidazo
- thiazole
- phenyl
- camphersulphonic
- camphersulphonate
- 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
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)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
1,152,544. Resolving dl-6-phenyl-2,3,5,6- tetrahydroimidazo [2,1-6] thiazole. AMERICAN CYANAMID CO. 17 May, 1967 [1 June, 1966], No. 22977/67. Heading C2C. Optically inactive 6 - phenyl - 2,3,5,6 - tetrahydroimidazo [2, 1. b] thiazole is resolved by treating it with chloroform and l- (or d-)-10- camphersulphonic acid, cooling to below 35‹ C., and separating the crystalline chloroform solvate of l(-) (or d(+)) 6-phenyl-2,3,5,6-tetrahydroimidazo [2, 1-b] thiazole l- (or d-)-10-camphersulphonate thus produced from the mother liquor. By treating the residue, obtained by evaporating the above mother liquor, with hot acetone, separating the precipitated dl-6-phenyl- 2,3,5,6 - tetrahydroimidazo [2, 1-b] thiazole d- (or l-)-10-camphersulphonate, cooling the resulting acetone filtrate and separating the precipitate thus produced l(-) (or d( + ))-6- phenyl - 2,3,5,6 - tetrahydroimidazo [2, 1-b] thiazole d- (or l-)-10-camphersulphonate is obtained. The salts thus produced are converted into the corresponding optically active free bases by treating them or an aqueous solution thereof with an amine, ammonia, alkali metal hydroxide or carbonate and recovered by extracting the resulting mixture with chloroform. d- and l-10-camphersulphonic acids are prepared by resolving dl-10-camphersulphonic acid using a modification of the above process and may be isolated as their ammonium salts. The dlbase and the (H-acid can be resolved in the same operation by a further modification of the above process. Therapeutic compositions, useful for the control of helminths in warm-blooded animals, contain l(-) 6-phenyl-2,3,5,6-tetrahydroimidazo [2, 1-b] thiazole, substantially free of the disomer or a hydrogen halide salt thereof and an inert non-toxic carrier.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US55430766A | 1966-06-01 | 1966-06-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1152544A true GB1152544A (en) | 1969-05-21 |
Family
ID=24212863
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2297767A Expired GB1152544A (en) | 1966-06-01 | 1967-05-17 | Resolution of dl-6-Phenyl-2,3,5,6-Tetrahydroimidazo [2,1-b] Thiazole |
Country Status (13)
| Country | Link |
|---|---|
| BE (1) | BE699349A (en) |
| BR (1) | BR6789758D0 (en) |
| CH (1) | CH509337A (en) |
| CY (1) | CY651A (en) |
| DE (1) | DE1645975A1 (en) |
| ES (1) | ES341159A1 (en) |
| FR (1) | FR1601065A (en) |
| GB (1) | GB1152544A (en) |
| IL (1) | IL27916A (en) |
| IT (1) | IT1061206B (en) |
| MY (1) | MY7300023A (en) |
| NL (1) | NL6707116A (en) |
| SE (1) | SE319187B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR3105410B1 (en) | 2019-12-20 | 2022-01-14 | Thales Sa | Radiation detector and associated manufacturing method |
-
1967
- 1967-05-04 IL IL2791667A patent/IL27916A/en unknown
- 1967-05-17 GB GB2297767A patent/GB1152544A/en not_active Expired
- 1967-05-18 IT IT3685267A patent/IT1061206B/en active
- 1967-05-23 BR BR18975867A patent/BR6789758D0/en unknown
- 1967-05-23 NL NL6707116A patent/NL6707116A/xx unknown
- 1967-05-30 ES ES341159A patent/ES341159A1/en not_active Expired
- 1967-06-01 CH CH780267A patent/CH509337A/en not_active IP Right Cessation
- 1967-06-01 BE BE699349D patent/BE699349A/xx not_active IP Right Cessation
- 1967-06-01 SE SE7692/67A patent/SE319187B/xx unknown
- 1967-06-01 DE DE19671645975 patent/DE1645975A1/en active Pending
- 1967-06-01 FR FR1601065D patent/FR1601065A/en not_active Expired
-
1972
- 1972-07-15 CY CY65172A patent/CY651A/en unknown
-
1973
- 1973-12-30 MY MY7300023A patent/MY7300023A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL27916A (en) | 1971-12-29 |
| BR6789758D0 (en) | 1973-09-06 |
| FR1601065A (en) | 1970-08-10 |
| CY651A (en) | 1972-07-15 |
| CH509337A (en) | 1971-06-30 |
| MY7300023A (en) | 1973-12-31 |
| IT1061206B (en) | 1983-02-28 |
| NL6707116A (en) | 1967-12-04 |
| BE699349A (en) | 1967-12-01 |
| ES341159A1 (en) | 1968-10-16 |
| SE319187B (en) | 1970-01-12 |
| DE1645975A1 (en) | 1970-07-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLE | Entries relating assignments, transmissions, licences in the register of patents | ||
| PE | Patent expired |