ES2546362B1 - PROCEDURE FOR OBTAINING THE ACID (S) -2 BENCIL 4 - ((3aR, 7aS) -HEXAHIDRO-1H-ISOINDOL-2 (3H) IL) -4-OXOBUTANOIC AND ITS SALTS - Google Patents
PROCEDURE FOR OBTAINING THE ACID (S) -2 BENCIL 4 - ((3aR, 7aS) -HEXAHIDRO-1H-ISOINDOL-2 (3H) IL) -4-OXOBUTANOIC AND ITS SALTS Download PDFInfo
- Publication number
- ES2546362B1 ES2546362B1 ES201490131A ES201490131A ES2546362B1 ES 2546362 B1 ES2546362 B1 ES 2546362B1 ES 201490131 A ES201490131 A ES 201490131A ES 201490131 A ES201490131 A ES 201490131A ES 2546362 B1 ES2546362 B1 ES 2546362B1
- Authority
- ES
- Spain
- Prior art keywords
- compound
- iii
- isoindol
- salts
- procedure
- 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 - Fee Related
Links
- 238000000034 method Methods 0.000 title abstract 3
- 150000003839 salts Chemical class 0.000 title abstract 2
- 239000002253 acid Substances 0.000 title 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 9
- 150000001875 compounds Chemical class 0.000 abstract 7
- 229960003365 mitiglinide Drugs 0.000 abstract 3
- 239000012452 mother liquor Substances 0.000 abstract 3
- 239000006227 byproduct Substances 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- 239000007787 solid Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 238000010992 reflux Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
Abstract
Procedimiento de obtención del ácido (S)-2 bencil4 -((3aR, 7aS) hexahidro-1H-isoindol-2(3H)il)-4-oxobutanoico y sus sales.#Hacer reaccionar el compuesto (IV) con el compuesto (V) en un disolvente para dar (S)-mitiglinida (II) y el compuesto (III) como un subproducto; eliminar el disolvente y añadir acetato de etilo para precipitar el compuesto (III); recoger el sólido y aplicar al menos un ciclo de proceso que comprende: someter a reflujo la solución del compuesto (III) con un disolvente orgánico para dar (S)-mitiglinida (II) y otro compuesto (III) como un subproducto, eliminar del disolvente orgánico y añadir acetato de etilo para precipitar el compuesto (III); y separar las aguas madre del sólido, y mezclar las aguas madre; retirar el acetato de etilo de las aguas madre para obtener (S)-mitiglinida.Procedure for obtaining (S) -2 benzyl4 - ((3aR, 7aS) hexahydro-1H-isoindol-2 (3H) yl) -4-oxobutanoic acid and its salts. # React compound (IV) with compound ( V) in a solvent to give (S) -mitiglinide (II) and compound (III) as a byproduct; remove the solvent and add ethyl acetate to precipitate the compound (III); collect the solid and apply at least one process cycle comprising: refluxing the solution of compound (III) with an organic solvent to give (S) -mitiglinide (II) and another compound (III) as a byproduct, remove from organic solvent and add ethyl acetate to precipitate compound (III); and separate the mother liquor from the solid, and mix the mother liquor; remove ethyl acetate from the mother liquor to obtain (S) -mitiglinide.
Description
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12173115 | 2012-06-22 | ||
| EP12173115 | 2012-06-22 | ||
| PCT/EP2013/062272 WO2013189829A1 (en) | 2012-06-22 | 2013-06-13 | Process for obtaining (s)-2-benzyl-4-((3ar,7as)-hexahydro-1 h-isoindol- 2(3h)-yl)-4-oxobutanoic acid and salts thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| ES2546362A2 ES2546362A2 (en) | 2015-09-22 |
| ES2546362R1 ES2546362R1 (en) | 2015-09-30 |
| ES2546362B1 true ES2546362B1 (en) | 2016-07-07 |
Family
ID=48874992
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES201490131A Expired - Fee Related ES2546362B1 (en) | 2012-06-22 | 2013-06-13 | PROCEDURE FOR OBTAINING THE ACID (S) -2 BENCIL 4 - ((3aR, 7aS) -HEXAHIDRO-1H-ISOINDOL-2 (3H) IL) -4-OXOBUTANOIC AND ITS SALTS |
Country Status (2)
| Country | Link |
|---|---|
| ES (1) | ES2546362B1 (en) |
| WO (1) | WO2013189829A1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105330585B (en) * | 2015-11-05 | 2018-03-06 | 常州大学 | A kind of preparation method of Mitiglinide Calcium |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU654331B2 (en) | 1991-03-30 | 1994-11-03 | Kissei Pharmaceutical Co. Ltd. | Succinic acid compounds |
| FR2765578B1 (en) * | 1997-07-03 | 1999-09-10 | Adir | PROCESS FOR THE PREPARATION OF A SUBSTITUTED PERHYDROISOINDOLE |
-
2013
- 2013-06-13 ES ES201490131A patent/ES2546362B1/en not_active Expired - Fee Related
- 2013-06-13 WO PCT/EP2013/062272 patent/WO2013189829A1/en active Application Filing
Also Published As
| Publication number | Publication date |
|---|---|
| ES2546362A2 (en) | 2015-09-22 |
| WO2013189829A1 (en) | 2013-12-27 |
| ES2546362R1 (en) | 2015-09-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG2A | Definitive protection |
Ref document number: 2546362 Country of ref document: ES Kind code of ref document: B1 Effective date: 20160707 |
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| PC2A | Transfer of patent |
Owner name: INKE S.A. Effective date: 20220606 |
|
| FD2A | Announcement of lapse in spain |
Effective date: 20240729 |