ES476725A1 - Procedimiento para preparar 1-metil-10-metoxi-lumiliserfol ylos correspondientes esteres con acidos carboxilicos. - Google Patents
Procedimiento para preparar 1-metil-10-metoxi-lumiliserfol ylos correspondientes esteres con acidos carboxilicos.Info
- Publication number
- ES476725A1 ES476725A1 ES476725A ES476725A ES476725A1 ES 476725 A1 ES476725 A1 ES 476725A1 ES 476725 A ES476725 A ES 476725A ES 476725 A ES476725 A ES 476725A ES 476725 A1 ES476725 A1 ES 476725A1
- Authority
- ES
- Spain
- Prior art keywords
- lysergol
- preparing
- derivatives
- acid
- lysergol derivatives
- 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
- BIXJFIJYBLJTMK-MEBBXXQBSA-N lysergol Chemical class C1=CC(C2=C[C@@H](CO)CN([C@@H]2C2)C)=C3C2=CNC3=C1 BIXJFIJYBLJTMK-MEBBXXQBSA-N 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 cycloaliphatic Chemical group 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- BIXJFIJYBLJTMK-UHFFFAOYSA-N Lysergol Natural products C1=CC(C2=CC(CO)CN(C2C2)C)=C3C2=CNC3=C1 BIXJFIJYBLJTMK-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000011987 methylation Effects 0.000 abstract 1
- 238000007069 methylation reaction Methods 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D457/00—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid
- C07D457/02—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid with hydrocarbon or substituted hydrocarbon radicals, attached in position 8
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Procedimiento para la preparación de derivados del 1-metil-10-metoxi-lumilisergol con la fórmula general (I9 y con los significados de R anteriormebnte indicados, prevé las fases de: a) conversión del ligersol (IX) en 10-metoxi-lumilisergol (X) mediante irradiación de una solución de lisergol; b) metilación del compuesto (X) en el nitrógeno indólico con un agente metilante, obteniéndose 1-metil- derivado (XI) c) reacción del alcohol (XI) con un ácido carboxílico R_COOH, en el que R tiene el significado anteriormente definido, en exceso molar respecto al alcohol. El lisergol constituye el substrato inicial de la síntesis y es un producto natural que se puede obtener fácilmente por extracción de la semillas de algunas especies de Ipomoea.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT22011/78A IT1094965B (it) | 1978-04-05 | 1978-04-05 | Procedimento di preparazione di derivati del lisergolo |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES476725A1 true ES476725A1 (es) | 1979-12-16 |
Family
ID=11190149
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES476725A Expired ES476725A1 (es) | 1978-04-05 | 1979-01-10 | Procedimiento para preparar 1-metil-10-metoxi-lumiliserfol ylos correspondientes esteres con acidos carboxilicos. |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4232157A (es) |
| EP (1) | EP0004664B1 (es) |
| AT (1) | AT369366B (es) |
| AU (1) | AU530864B2 (es) |
| CA (1) | CA1124713A (es) |
| DD (1) | DD142713A1 (es) |
| DE (1) | DE2962494D1 (es) |
| DK (1) | DK148259C (es) |
| ES (1) | ES476725A1 (es) |
| FI (1) | FI66376C (es) |
| FR (1) | FR2421901A1 (es) |
| GB (1) | GB2018245B (es) |
| GR (1) | GR66982B (es) |
| HU (1) | HU177591B (es) |
| IT (1) | IT1094965B (es) |
| NO (1) | NO150799C (es) |
| PL (1) | PL115244B1 (es) |
| PT (1) | PT69426A (es) |
| SU (1) | SU884572A3 (es) |
| YU (1) | YU41151B (es) |
| ZA (1) | ZA791609B (es) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4382940A (en) * | 1979-12-06 | 1983-05-10 | Farmitalia Carlo Erba S.P.A. | Ercoline derivatives and therapeutic compositions having CNS affecting activity |
| IT1173489B (it) * | 1984-03-27 | 1987-06-24 | Inverni Della Beffa Spa | Procedimento di preparazione di 1-metil-10alfa-metossilumilisergolo e di suci esteri,e intermedi per la loro preparazione |
| IT1213206B (it) * | 1984-08-07 | 1989-12-14 | Inverni Della Beffa Spa | Procedimento per la preparazione di derivati del lisergolo. |
| HU193782B (en) * | 1985-06-21 | 1987-11-30 | Richter Gedeon Vegyeszet | Process for producing 2-halogeno-nicergoline derivatives and acid additional salts thereof |
| HU193781B (en) * | 1985-06-21 | 1987-11-30 | Richter Gedeon Vegyeszet | Process for producing 10alpha-methoxy-6-methylergoline derivatives and acid additional salts thereof |
| FR2584719B1 (fr) * | 1985-07-11 | 1987-10-02 | Rhone Poulenc Sante | Procede de preparation des derives n-methyles du lysergol et du methoxy-10a lumilysergol |
| FR2584721B1 (fr) * | 1985-07-11 | 1987-10-02 | Rhone Poulenc Sante | Procede de preparation des derives n-methyles du dihydrolysergate de methyle ou du methoxylumilysergate de methyle |
| FR2584720B1 (fr) * | 1985-07-11 | 1987-10-02 | Rhone Poulenc Sante | Procede de preparation de derives n-methyles de l'ergoline |
| CH674367A5 (es) * | 1987-06-16 | 1990-05-31 | Arysearch Arylan Ag | |
| US5120784A (en) * | 1988-09-01 | 1992-06-09 | Basf Aktiengesellschaft | Heat-resistant thermoplastic molding compositions |
| US6060483A (en) * | 1996-06-27 | 2000-05-09 | Pharmacia & Upjohn S.P.A. | Antineurodegenerative ergoline derivatives |
| FR2786099B1 (fr) | 1998-11-24 | 2000-12-29 | Aventis Laboratoire | Nouvelle application therapeutique de la 1,6-dimethyl-8beta- hydroxymethyl-10alpha-methoxyergoline |
| CN111116580B (zh) * | 2019-12-27 | 2022-08-23 | 上海应用技术大学 | 一种尼麦角林的改进制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3228943A (en) * | 1962-06-11 | 1966-01-11 | Lumilysergol derivatives | |
| ES290275A2 (es) * | 1962-07-26 | 1964-03-01 | Farm Italia | Procedimiento para preparar nuevos compuestos de la 6-metil y la 1,6-dimetil-er-golina ii |
| NL7102982A (es) * | 1970-03-20 | 1971-09-22 | Farmaceutici Italia | |
| US3879554A (en) * | 1970-03-20 | 1975-04-22 | Farmaceutici Italia | Use of 1,6-dimethyl-8-{62 -(5-bromonicotinoyloxymethyl)-10 {60 -methoxyergoline in treating cerebral and peripheral metabolic vascular disorders |
| NL159384B (nl) * | 1971-03-13 | 1979-02-15 | Farmaceutici Italia | Werkwijze voor het bereiden van een geneesmiddel met een adrenolytische activiteit, alsmede werkwijze voor het bereiden van een ester van 1-methyl-10-methoxylumilysergol. |
| YU39278B (en) * | 1976-12-22 | 1984-10-31 | Lek Tovarna Farmacevtskih | Process for preparing 5-bromo nicotinic acid esters |
-
1978
- 1978-04-05 IT IT22011/78A patent/IT1094965B/it active
-
1979
- 1979-01-10 ES ES476725A patent/ES476725A1/es not_active Expired
- 1979-03-30 GR GR58730A patent/GR66982B/el unknown
- 1979-04-02 PT PT69426A patent/PT69426A/pt unknown
- 1979-04-03 HU HU79CO367A patent/HU177591B/hu unknown
- 1979-04-03 DE DE7979101015T patent/DE2962494D1/de not_active Expired
- 1979-04-03 AT AT0246679A patent/AT369366B/de not_active IP Right Cessation
- 1979-04-03 US US06/026,685 patent/US4232157A/en not_active Expired - Lifetime
- 1979-04-03 EP EP79101015A patent/EP0004664B1/en not_active Expired
- 1979-04-04 FI FI791110A patent/FI66376C/fi not_active IP Right Cessation
- 1979-04-04 ZA ZA791609A patent/ZA791609B/xx unknown
- 1979-04-04 DK DK138879A patent/DK148259C/da not_active IP Right Cessation
- 1979-04-04 AU AU45713/79A patent/AU530864B2/en not_active Ceased
- 1979-04-04 SU SU792748500A patent/SU884572A3/ru active
- 1979-04-04 YU YU801/79A patent/YU41151B/xx unknown
- 1979-04-04 GB GB7911834A patent/GB2018245B/en not_active Expired
- 1979-04-04 NO NO791139A patent/NO150799C/no unknown
- 1979-04-04 CA CA324,886A patent/CA1124713A/en not_active Expired
- 1979-04-05 FR FR7908608A patent/FR2421901A1/fr active Granted
- 1979-04-05 PL PL1979214713A patent/PL115244B1/pl unknown
- 1979-04-05 DD DD79212043A patent/DD142713A1/de unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA791609B (en) | 1980-04-30 |
| DD142713A1 (de) | 1980-07-09 |
| FR2421901A1 (fr) | 1979-11-02 |
| HU177591B (en) | 1981-11-28 |
| FI791110A7 (fi) | 1979-10-06 |
| GB2018245A (en) | 1979-10-17 |
| IT7822011A0 (it) | 1978-04-05 |
| US4232157A (en) | 1980-11-04 |
| YU80179A (en) | 1983-02-28 |
| DE2962494D1 (en) | 1982-05-27 |
| DK148259B (da) | 1985-05-20 |
| GR66982B (es) | 1981-05-15 |
| EP0004664A1 (en) | 1979-10-17 |
| FI66376B (fi) | 1984-06-29 |
| GB2018245B (en) | 1982-09-02 |
| AU4571379A (en) | 1979-11-01 |
| EP0004664B1 (en) | 1982-04-14 |
| AT369366B (de) | 1982-12-27 |
| NO150799B (no) | 1984-09-10 |
| DK148259C (da) | 1985-10-14 |
| FR2421901B1 (es) | 1983-07-22 |
| PL214713A1 (es) | 1980-01-02 |
| NO791139L (no) | 1979-10-08 |
| CA1124713A (en) | 1982-06-01 |
| NO150799C (no) | 1984-12-27 |
| FI66376C (fi) | 1984-10-10 |
| AU530864B2 (en) | 1983-08-04 |
| SU884572A3 (ru) | 1981-11-23 |
| DK138879A (da) | 1979-10-06 |
| YU41151B (en) | 1986-12-31 |
| PL115244B1 (en) | 1981-03-31 |
| ATA246679A (de) | 1982-05-15 |
| IT1094965B (it) | 1985-08-10 |
| PT69426A (en) | 1979-05-01 |
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