WO2005030713B1 - Resolution of a narwedine amide derivative - Google Patents
Resolution of a narwedine amide derivativeInfo
- Publication number
- WO2005030713B1 WO2005030713B1 PCT/US2004/031936 US2004031936W WO2005030713B1 WO 2005030713 B1 WO2005030713 B1 WO 2005030713B1 US 2004031936 W US2004031936 W US 2004031936W WO 2005030713 B1 WO2005030713 B1 WO 2005030713B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- bromoamide
- mixed solution
- enantiomer
- alcohol
- producing
- 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.)
- Ceased
Links
Abstract
The present invention provides for an efficient method of effecting the resolution of a narwedine amide, and the synthesis of galantamine.
Claims
AMENDED CLAIMS Received by the International Bureau on 10 January 2006 (10.01.06)
We claim:
1. A method of producing a (-) enantiomer from racemic bromoamide (I) by the steps of (a) dissolving the racemic bromoamide in an organic solvent containing a soluble base to form a mixed solution (b) seeding the mixed solution with a seed crystal of an optically active material and (c) crystallizing the seeded mixed solution to produce (-) bromoamide (I) with substantially enhanced optical purity.
2. The method of claim 1 in which the organic solvent is selected from the group consisting of acetonitrile, alcohol, acetone and THF.
3. The method of claim 1 in which the soluble base is an amine.
4. The method of claim 3 wherein the amine is trialkyl amine.
5. The method in claim 1 in which the seed crystal is selected from the group consisting of (+) bromoamide alcohol (III) , (+) galantamine and (-) bromoamide (I) .
6. The chiral compounds:
7. A method of producing a (-) enantiomer from racemic bromoamide (I) by the steps of (a) dissolving the racemic bromoamide in an organic solvent containing a soluble chiral amine base to form a mixed solution, (b) crystallizing the mixed solution to produce (-) bromoamide (I) with substantially enhanced optical purity.
8. The method of claim 7, wherein the chiral base amine is selected from the group consisting of α-phenyl ethylamine, cinchonine, cinchonidine, ephredrine, and N- methylglucamine.
9. The method of claim 7 in which a seed crystal of an optically active material is added to the mixed solution to crystallize the (-) bromoamide (I) .
10. The method of producing (-) -galantamine comprising the steps of claim 1, converting the (-) bromoamide (I) to the alcohol, and reducing the alcohol to (-) -galantamine.
11. The method of producing (-) -galantamine comprising the steps of claim 7, converting the (-) bromoamide (I) to the alcohol, and reducing the alcohol to (-) -galantamine.
13. The method of producing a (-) enantiomer from the racemic compound having the formula of
wherein R is selected from the group consisting of H, alkyl, aryl and arylalkyl; A1, A2, are, together, O; B1 and B2 are H; Y is H or Me; and Z is a blocking group by the steps of (a) dissolving the racemic compound in an organic solvent containing a soluble base to form a mixed solution (b) seeding the mixed solution with a seed crystal of an optically active material and (c) crystallizing the seeded mixed solution to produce the (- ) enantiomer with substantially enhanced optical purity.
14. The method of producing a (-) enantiomer from racemic compound having the formula of
wherein R is selected from the group consisting of H, alkyl, aryl and arylalkyl; A1, A2, are, together, 0; B1 and B2 are H; Y is H or Me; and Z is a blocking group by the steps of (a) dissolving the racemic compound in an organic solvent containing a soluble chiral amine base to form a mixed solution, (b) crystallizing the mixed solution to produce the (-) enantiomer with substantially enhanced optical purity.
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NZ546768A NZ546768A (en) | 2003-09-26 | 2004-09-27 | Resolution of a narwedine amide derivative and the synthesis of galantamine |
| EP04789228.6A EP1670767B2 (en) | 2003-09-26 | 2004-09-27 | Resolution of a narwedine amide derivative |
| JP2006528320A JP5020633B2 (en) | 2003-09-26 | 2004-09-27 | Resolution of nalwedinamide derivatives |
| CN2004800276266A CN1875004B (en) | 2003-09-26 | 2004-09-27 | Resolution of narwedine amide derivatives |
| CA2540248A CA2540248C (en) | 2003-09-26 | 2004-09-27 | Resolution of a narwedine amide derivative |
| AU2004276354A AU2004276354B2 (en) | 2003-09-26 | 2004-09-27 | Resolution of a narwedine amide derivative |
| IL174551A IL174551A0 (en) | 2003-09-26 | 2006-03-26 | Resolution of a narwedine amide derivative |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US50646903P | 2003-09-26 | 2003-09-26 | |
| US60/506,469 | 2003-09-26 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| WO2005030713A2 WO2005030713A2 (en) | 2005-04-07 |
| WO2005030713A3 WO2005030713A3 (en) | 2006-01-26 |
| WO2005030713B1 true WO2005030713B1 (en) | 2006-04-27 |
Family
ID=34393160
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US2004/031936 Ceased WO2005030713A2 (en) | 2003-09-26 | 2004-09-27 | Resolution of a narwedine amide derivative |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7307162B2 (en) |
| EP (1) | EP1670767B2 (en) |
| JP (1) | JP5020633B2 (en) |
| CN (1) | CN1875004B (en) |
| AU (1) | AU2004276354B2 (en) |
| CA (1) | CA2540248C (en) |
| IL (1) | IL174551A0 (en) |
| NZ (1) | NZ546768A (en) |
| WO (1) | WO2005030713A2 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090253654A1 (en) | 2005-09-22 | 2009-10-08 | Galantos Pharma Gmbh | Cholinergic enhancers with improved blood-brain barrier permeability for the treatment of diseases accompanied by cognitive impairment |
| US7985879B2 (en) * | 2007-04-12 | 2011-07-26 | Scinopharm Taiwan Ltd. | Process for making galantamine |
| ES2463715T3 (en) | 2008-04-14 | 2014-05-29 | Neurodyn Life Sciences Inc. | Galantamine derivatives as prodrugs for the treatment of human brain diseases |
| WO2011151359A1 (en) | 2010-06-02 | 2011-12-08 | Noscira, S.A. | Combined treatment with a cholinesterase inhibitor and a thiadiazolidinedione derivative |
| BG66818B1 (en) | 2013-03-07 | 2019-01-31 | Berbee Beheer B. V. | Composition of hippeastrum papilio extract for the production of medicines and nutritional supplements |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BG28325A1 (en) * | 1978-11-21 | 1980-04-15 | Vlakhov | Method of obtaining of enons navedine type and their derivatives |
| US4290862A (en) * | 1979-11-14 | 1981-09-22 | Edinen Centar P Chimia | Method for the preparation of narwedine-type enones |
| US5428159A (en) | 1994-04-08 | 1995-06-27 | Ciba-Geigy Corporation | Method of manufacture of (-)-galanthamine in high yield and purity substantially free of epigalanthamine |
| US6407229B1 (en) * | 1994-10-21 | 2002-06-18 | Sanochemia Pharmazeutika Ag | Processes for the preparation of derivatives of 4a,5,9,10,11,12-hexahydro-6H-benzofuro-[3a,3,2-ef][2] benzazapine |
| GB9506843D0 (en) * | 1995-04-03 | 1995-05-24 | Chiroscience Ltd | Oxidative process and products thereof |
| US6018043A (en) * | 1995-04-06 | 2000-01-25 | Janssen Pharmaceutica, N.V. | Process for preparing galanthamine derivatives by asymmetric reduction |
| GB9707413D0 (en) * | 1997-04-11 | 1997-05-28 | Chiroscience Ltd | Process |
-
2004
- 2004-09-27 AU AU2004276354A patent/AU2004276354B2/en not_active Ceased
- 2004-09-27 JP JP2006528320A patent/JP5020633B2/en not_active Expired - Fee Related
- 2004-09-27 CN CN2004800276266A patent/CN1875004B/en not_active Expired - Fee Related
- 2004-09-27 WO PCT/US2004/031936 patent/WO2005030713A2/en not_active Ceased
- 2004-09-27 CA CA2540248A patent/CA2540248C/en not_active Expired - Fee Related
- 2004-09-27 US US10/951,748 patent/US7307162B2/en not_active Expired - Lifetime
- 2004-09-27 EP EP04789228.6A patent/EP1670767B2/en not_active Expired - Lifetime
- 2004-09-27 NZ NZ546768A patent/NZ546768A/en not_active IP Right Cessation
-
2006
- 2006-03-26 IL IL174551A patent/IL174551A0/en active IP Right Grant
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