ES8604957A1 - Preparation of (+/-)14, 15-dihydro-(3 beta, 14 alpha, 16 alpha)-20, 21-dinoreburunamenine-14-ol - Google Patents
Preparation of (+/-)14, 15-dihydro-(3 beta, 14 alpha, 16 alpha)-20, 21-dinoreburunamenine-14-olInfo
- Publication number
- ES8604957A1 ES8604957A1 ES549399A ES549399A ES8604957A1 ES 8604957 A1 ES8604957 A1 ES 8604957A1 ES 549399 A ES549399 A ES 549399A ES 549399 A ES549399 A ES 549399A ES 8604957 A1 ES8604957 A1 ES 8604957A1
- Authority
- ES
- Spain
- Prior art keywords
- alpha
- reaction
- dihydro
- dinoreburunamenine
- beta
- 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
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 abstract 1
- 238000004587 chromatography analysis Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 238000003756 stirring Methods 0.000 abstract 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D461/00—Heterocyclic compounds containing indolo [3,2,1-d,e] pyrido [3,2,1,j] [1,5]-naphthyridine ring systems, e.g. vincamine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
(+-)14,15-Dihydro (3beta,14alpha,16alpha) 20,21-dinoreburnamenine-14 -ol (I) is prepd. by treating (+-)3beta, 16alpha-eburnamenine (II) to a heterogeneous phase oxidn-redn. reaction using hydrogen peroxide and a quat. ammonium reducing salt, such as tetrabutyl ammonium borohydride, in the presence of ethyl bromide. The solvent is a mixt. of dichloromethane and 20% aqs. sodium hydroxide, and the reaction is effected at 20 deg. C for 24 hrs. with vigorous stirring. The reaction is hydrolysed progressively and purified by chromatography.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES549399A ES8604957A1 (en) | 1985-11-28 | 1985-11-28 | Preparation of (+/-)14, 15-dihydro-(3 beta, 14 alpha, 16 alpha)-20, 21-dinoreburunamenine-14-ol |
| JP61283026A JPH0662617B2 (en) | 1985-11-28 | 1986-11-26 | Method for preparing (+/-) 14,15-dihydro- (3β, 14α, 16α) -20,21-dinorebulenamenin-14-ol |
| FR868616623A FR2590572B1 (en) | 1985-11-28 | 1986-11-28 | PROCESS FOR THE PREPARATION OF (+/-) 14, 15-DIHYDRO- (3 B, 14 A, 16 A) -20.21, DINOREBURNAMENINE |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES549399A ES8604957A1 (en) | 1985-11-28 | 1985-11-28 | Preparation of (+/-)14, 15-dihydro-(3 beta, 14 alpha, 16 alpha)-20, 21-dinoreburunamenine-14-ol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES8604957A1 true ES8604957A1 (en) | 1986-03-16 |
| ES549399A0 ES549399A0 (en) | 1986-03-16 |
Family
ID=8490315
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES549399A Expired ES8604957A1 (en) | 1985-11-28 | 1985-11-28 | Preparation of (+/-)14, 15-dihydro-(3 beta, 14 alpha, 16 alpha)-20, 21-dinoreburunamenine-14-ol |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPH0662617B2 (en) |
| ES (1) | ES8604957A1 (en) |
| FR (1) | FR2590572B1 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2623501B1 (en) * | 1987-11-19 | 1990-03-16 | Roussel Uclaf | NOVEL SUBSTITUTED DERIVATIVES OF 20.21-DINOREBURNAMENINE, THEIR PREPARATION PROCESS AND THE NOVEL INTERMEDIATES THUS OBTAINED, THEIR APPLICATION AS DRUGS AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
| FR2623503B1 (en) * | 1987-11-19 | 1991-04-05 | Roussel Uclaf | |
| FR2865649A1 (en) * | 2004-01-30 | 2005-08-05 | Biocortech | Use of 14,15-dihydro-20,21-dinor-14-eburnameninol to prepare a pharmaceutical composition for treating or preventing major depression |
| FR2865650B1 (en) * | 2004-01-30 | 2008-06-13 | Biocortech | USE OF 14,15 DIHYDRO 20,21-DINOREBURNAMENIN14-OL FOR THE TREATMENT AND / OR PREVENTION OF MAJOR LOWERS AND SLEEP-RELIEF CYCLE DISORDERS |
-
1985
- 1985-11-28 ES ES549399A patent/ES8604957A1/en not_active Expired
-
1986
- 1986-11-26 JP JP61283026A patent/JPH0662617B2/en not_active Expired - Lifetime
- 1986-11-28 FR FR868616623A patent/FR2590572B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| FR2590572A1 (en) | 1987-05-29 |
| FR2590572B1 (en) | 1990-05-25 |
| ES549399A0 (en) | 1986-03-16 |
| JPS62145082A (en) | 1987-06-29 |
| JPH0662617B2 (en) | 1994-08-17 |
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