CA2121060A1 - Preparation of lignan analogues - Google Patents
Preparation of lignan analoguesInfo
- Publication number
- CA2121060A1 CA2121060A1 CA 2121060 CA2121060A CA2121060A1 CA 2121060 A1 CA2121060 A1 CA 2121060A1 CA 2121060 CA2121060 CA 2121060 CA 2121060 A CA2121060 A CA 2121060A CA 2121060 A1 CA2121060 A1 CA 2121060A1
- Authority
- CA
- Canada
- Prior art keywords
- formula
- lower alkyl
- iii
- compounds
- preparation
- 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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyrane Compounds (AREA)
Abstract
This invention relates to a process for preparing the compounds of lignan series in a selective manner in terms of the positions, and to intermediates thereof. This invention provides a process for preparing compounds of the formula (I):
(See formula I) which is characterized by that a lactone compound of the formula (II):
(See formula II) is reacted with an unsaturated ketone represented by the formula (III):
(See formula III) and the resulting compound is subjected to dehydration in which, R1 is alkyl, cycloalkyl, cycloalkyl (lower alkyl), or aralkyl;
R2 and R3 each is lower alkyl or R2 and R3 are combined together to form an alkylenedioxy; R4 is lower alkoxy or hydrogen; R5 and R6 each is lower alkyl; and R7 is lower alkyl. The invention also provides the compounds of the formulas (II) and (III).
(See formula I) which is characterized by that a lactone compound of the formula (II):
(See formula II) is reacted with an unsaturated ketone represented by the formula (III):
(See formula III) and the resulting compound is subjected to dehydration in which, R1 is alkyl, cycloalkyl, cycloalkyl (lower alkyl), or aralkyl;
R2 and R3 each is lower alkyl or R2 and R3 are combined together to form an alkylenedioxy; R4 is lower alkoxy or hydrogen; R5 and R6 each is lower alkyl; and R7 is lower alkyl. The invention also provides the compounds of the formulas (II) and (III).
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002443310A CA2443310A1 (en) | 1993-04-16 | 1994-04-12 | Unsaturated ketones |
| CA002444833A CA2444833A1 (en) | 1993-04-16 | 1994-04-12 | Lactone compounds |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8994693 | 1993-04-16 | ||
| JP089946/1993 | 1993-04-16 |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002443310A Division CA2443310A1 (en) | 1993-04-16 | 1994-04-12 | Unsaturated ketones |
| CA002444833A Division CA2444833A1 (en) | 1993-04-16 | 1994-04-12 | Lactone compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2121060A1 true CA2121060A1 (en) | 1994-10-17 |
| CA2121060C CA2121060C (en) | 2004-04-06 |
Family
ID=13984877
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2121060 Expired - Fee Related CA2121060C (en) | 1993-04-16 | 1994-04-12 | Preparation of lignan analogues |
Country Status (6)
| Country | Link |
|---|---|
| CN (2) | CN1104622A (en) |
| AU (2) | AU672095B2 (en) |
| CA (1) | CA2121060C (en) |
| HU (1) | HU211086B (en) |
| NO (2) | NO302815B1 (en) |
| TW (1) | TW420661B (en) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NO170760C (en) * | 1985-01-10 | 1992-12-02 | Tanabe Seiyaku Co | ANALOGY PROCEDURE FOR THE PREPARATION OF THERAPEUTICALLY ACTIVE NAPHENSE DERIVATIVES |
| ZA9076B (en) * | 1989-02-03 | 1990-10-31 | Tanabe Seiyaku Co Limited | A process for preparing a naphthalene derivative and a synthetic intermediate thereof |
| CA2138264C (en) * | 1993-04-16 | 2004-04-06 | Sachio Mori | Preparation of compounds of lignan series |
-
1994
- 1994-04-12 CA CA 2121060 patent/CA2121060C/en not_active Expired - Fee Related
- 1994-04-13 TW TW83103282A patent/TW420661B/en active
- 1994-04-14 AU AU59481/94A patent/AU672095B2/en not_active Ceased
- 1994-04-15 HU HU9401085A patent/HU211086B/en not_active IP Right Cessation
- 1994-04-15 CN CN 94105557 patent/CN1104622A/en active Pending
- 1994-04-15 NO NO941382A patent/NO302815B1/en unknown
-
1996
- 1996-12-13 AU AU75339/96A patent/AU685716B2/en not_active Ceased
-
1998
- 1998-01-09 NO NO19980102A patent/NO317062B1/en unknown
-
2000
- 2000-07-25 CN CN 00122210 patent/CN1285352A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| NO302815B1 (en) | 1998-04-27 |
| CA2121060C (en) | 2004-04-06 |
| CN1285352A (en) | 2001-02-28 |
| AU7533996A (en) | 1997-02-13 |
| HU211086B (en) | 1995-10-30 |
| AU5948194A (en) | 1994-10-20 |
| AU685716B2 (en) | 1998-01-22 |
| NO941382L (en) | 1994-10-17 |
| NO941382D0 (en) | 1994-04-15 |
| AU672095B2 (en) | 1996-09-19 |
| TW420661B (en) | 2001-02-01 |
| NO317062B1 (en) | 2004-08-02 |
| HU9401085D0 (en) | 1994-07-28 |
| HUT66861A (en) | 1995-01-30 |
| CN1104622A (en) | 1995-07-05 |
| NO980102L (en) | 1998-01-09 |
| NO980102D0 (en) | 1998-01-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |