CA2536608A1 - New highly selective process for the preparation of enantiomerically pure phenyl-substituted 1,4-dihydropyridine-3,5-dicarboxylic acid derivatives - Google Patents
New highly selective process for the preparation of enantiomerically pure phenyl-substituted 1,4-dihydropyridine-3,5-dicarboxylic acid derivatives Download PDFInfo
- Publication number
- CA2536608A1 CA2536608A1 CA002536608A CA2536608A CA2536608A1 CA 2536608 A1 CA2536608 A1 CA 2536608A1 CA 002536608 A CA002536608 A CA 002536608A CA 2536608 A CA2536608 A CA 2536608A CA 2536608 A1 CA2536608 A1 CA 2536608A1
- Authority
- CA
- Canada
- Prior art keywords
- carbon atoms
- chain
- straight
- branched alkyl
- phenyl
- 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.)
- Granted
Links
- -1 phenyl-substituted 1,4-dihydropyridine-3,5-dicarboxylic acid Chemical class 0.000 title abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 8
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical class C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 abstract 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000006193 alkinyl group Chemical group 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 1
Landscapes
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Use of a derivative of an optically active maleimide of the general formula (VII): (see formula VII) wherein: A represents: (i) H or straight-chain or branched alkyl having up to 8 carbon atoms, or (ii) phenyl or benzyl which are optionally up to trisubstituted by identical or different substituents selected from the group consisting of hydroxyl, nitro, a halogen atom, cyano, carboxyl, trifluoromethyl, trifluoromethoxy, straight-chain or branched alkoxy having up to 6 carbon atoms and a group of the general formula: -NR6R7 or -SO2R8, wherein: R6 and R7 are identical or different and represent H, phenyl or straight-chain or branched alkyl having up to 5 carbon atoms, and R8 represents straight-chain or branched alkyl having up to 4 carbon atoms or phenyl, in the preparation of the diastereomerically pure 1,4-dihydropyridines of the general formulae (IVa) and (IVb): (see formulae IVa and IVb) wherein: A is as defined above; R1 represents: (i) straight-chain or branched alkyl having up to 8 carbon atoms which is optionally substituted by straight-chain or branched alkoxy having up to 6 carbon atoms or hydroxyl, or (ii) cycloalkyl having 3 to 7 carbon atoms; and R2 represents the radical (see formula I) wherein R4 and R5 are identical or different and represent: (i) a halogen atom, cyano, ethinyl, trifluoromethoxy, methylthio, nitro or trifluoromethyl, or (ii) straight-chain or branched alkyl, alkenyl, alkinyl or alkoxy having up to 4 carbon atoms, and one of the substituents optionally represents H; and a salt thereof.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4443168A DE4443168A1 (en) | 1994-12-05 | 1994-12-05 | New highly selective process for the production of enantiomerically pure phenyl-substituted 1,4-dihydropyridine-3,5-dicarboxylic acid derivatives |
| DEP4443168.6 | 1994-12-05 | ||
| CA002164276A CA2164276C (en) | 1994-12-05 | 1995-12-01 | New highly selective process for the preparation of enantiomerically pure phenylsubstituted 1,4-dihydropyridine-3,5-dicarboxylic acid derivatives |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002164276A Division CA2164276C (en) | 1994-12-05 | 1995-12-01 | New highly selective process for the preparation of enantiomerically pure phenylsubstituted 1,4-dihydropyridine-3,5-dicarboxylic acid derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2536608A1 true CA2536608A1 (en) | 1996-06-06 |
| CA2536608C CA2536608C (en) | 2007-11-20 |
Family
ID=36283178
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002536608A Expired - Fee Related CA2536608C (en) | 1994-12-05 | 1995-12-01 | New highly selective process for the preparation of enantiomerically pure phenyl-substituted 1,4-dihydropyridine-3,5-dicarboxylic acid derivatives |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2536608C (en) |
-
1995
- 1995-12-01 CA CA002536608A patent/CA2536608C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2536608C (en) | 2007-11-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20121203 |