ES2002208A6 - Production of (4s)-2, 6-dimethyl-4-(m-nitrophenyl)-1, 4-dihydropyridine-3, 5-dicarboxylic acid (3s)-3-(1-benzyl-3-pyrrolidinyl) ester 5-methyl ester - Google Patents
Production of (4s)-2, 6-dimethyl-4-(m-nitrophenyl)-1, 4-dihydropyridine-3, 5-dicarboxylic acid (3s)-3-(1-benzyl-3-pyrrolidinyl) ester 5-methyl esterInfo
- Publication number
- ES2002208A6 ES2002208A6 ES8602659A ES8602659A ES2002208A6 ES 2002208 A6 ES2002208 A6 ES 2002208A6 ES 8602659 A ES8602659 A ES 8602659A ES 8602659 A ES8602659 A ES 8602659A ES 2002208 A6 ES2002208 A6 ES 2002208A6
- Authority
- ES
- Spain
- Prior art keywords
- ester
- pyrrolidinyl
- benzyl
- reacting
- dicarboxylic acid
- 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
- VXMOONUMYLCFJD-DHLKQENFSA-N barnidipine Chemical compound C1([C@@H]2C(=C(C)NC(C)=C2C(=O)OC)C(=O)O[C@@H]2CN(CC=3C=CC=CC=3)CC2)=CC=CC([N+]([O-])=O)=C1 VXMOONUMYLCFJD-DHLKQENFSA-N 0.000 title 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 3
- 230000032050 esterification Effects 0.000 abstract 3
- 238000005886 esterification reaction Methods 0.000 abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- 239000000126 substance Substances 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 2
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
PURPOSE:To obtain the titled substance useful as a medicine in high yield and optical purity without varying steric configuration of starting compound, by reacting a methyl esterification reagent to a compound or its salt corresponding to the titled substance provided that the 5-carboxylic acid is in free state. CONSTITUTION:The titled substance can be produced either by reacting a 3, 5-dicarboxylic acid (3S)-3-(1-benzyl-3-pyrrolidinyl) ester derivative of formula (R' is ester residue easily eliminable by alkali hydrolysis treatment) directly with a methyl esterification reagent (e.g. diazomethane, methanol-hydrochloric acid, etc.) or by hydrolyzing the derivative under alkaline condition and reacting with a methyl esterification reagent.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23426885 | 1985-10-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2002208A6 true ES2002208A6 (en) | 1988-07-16 |
Family
ID=16968304
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES8602659A Expired ES2002208A6 (en) | 1985-10-19 | 1986-10-17 | Production of (4s)-2, 6-dimethyl-4-(m-nitrophenyl)-1, 4-dihydropyridine-3, 5-dicarboxylic acid (3s)-3-(1-benzyl-3-pyrrolidinyl) ester 5-methyl ester |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS62174071A (en) |
| KR (1) | KR960016525B1 (en) |
| AT (1) | AT395976B (en) |
| CA (1) | CA1273932A (en) |
| ES (1) | ES2002208A6 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000024716A1 (en) * | 1998-10-23 | 2000-05-04 | Ajinomoto Co., Inc. | Dihydropyridine derivatives and drug compositions containing the same |
| ITMI20130148A1 (en) * | 2013-02-01 | 2014-08-02 | Chemo Iberica Sa | NEW POLYLORPHONE OF BARNIDIPINE CHLORIDRATE AND METHOD FOR ITS PREPARATION |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55301A (en) * | 1978-02-14 | 1980-01-05 | Yamanouchi Pharmaceut Co Ltd | 1,4-dihydropyridine-3,5-dicarboxylic ester derivative and its preparation |
-
1986
- 1986-10-08 AT AT0267686A patent/AT395976B/en active
- 1986-10-15 JP JP61246366A patent/JPS62174071A/en active Pending
- 1986-10-15 KR KR1019860008622A patent/KR960016525B1/en not_active Expired - Lifetime
- 1986-10-16 CA CA000520664A patent/CA1273932A/en not_active Expired - Fee Related
- 1986-10-17 ES ES8602659A patent/ES2002208A6/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62174071A (en) | 1987-07-30 |
| AT395976B (en) | 1993-04-26 |
| ATA267686A (en) | 1992-09-15 |
| KR960016525B1 (en) | 1996-12-14 |
| KR870004020A (en) | 1987-05-06 |
| CA1273932A (en) | 1990-09-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SA6 | Expiration date (snapshot 920101) |
Free format text: 2006-10-17 |
|
| FD1A | Patent lapsed |
Effective date: 20061018 |