ES289117A1 - A PROCEDURE FOR THE PREPARATION OF NEW DERIVATIVES OF 6-METHYL AND 1,6-DIMETHYL-8-AMINO-METHYL-ERGOLINE I - Google Patents
A PROCEDURE FOR THE PREPARATION OF NEW DERIVATIVES OF 6-METHYL AND 1,6-DIMETHYL-8-AMINO-METHYL-ERGOLINE IInfo
- Publication number
- ES289117A1 ES289117A1 ES289117A ES289117A ES289117A1 ES 289117 A1 ES289117 A1 ES 289117A1 ES 289117 A ES289117 A ES 289117A ES 289117 A ES289117 A ES 289117A ES 289117 A1 ES289117 A1 ES 289117A1
- Authority
- ES
- Spain
- Prior art keywords
- methyl
- dihydro
- cycloalkyl
- carbon atoms
- ergoline
- 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
- MLGFPIFELHMSGJ-KQSHLBLPSA-N (6aR,10aR)-4,7,9-trimethyl-6a,8,10,10a-tetrahydro-6H-indolo[4,3-fg]quinolin-9-amine Chemical compound CN1C=C2C[C@H]3N(CC(C[C@@H]3C=3C=CC=C1C=32)(N)C)C MLGFPIFELHMSGJ-KQSHLBLPSA-N 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- IGFREZYZHZYUFF-HUFXEGEASA-N (6aR,9R)-4,7-dimethyl-5,5a,6,6a,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide Chemical compound C([C@H](CN(C)[C@@H]1C2)C(N)=O)=C1C1=CC=CC3=C1C2CN3C IGFREZYZHZYUFF-HUFXEGEASA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000003368 amide group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 150000005840 aryl radicals Chemical class 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- -1 cycloaliphatic Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/48—Ergoline derivatives, e.g. lysergic acid, ergotamine
-
- 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
- C07D457/04—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 8
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
A process for the preparation of new derivatives of 6-methyl- and 1,6-dimethyl-8-amino-methyl-ergoline I, of the following structural formula: ** (See formula) ** where R is hydrogen or methyl R 'is an alkyl, cycloalkyl or aryl radical with 1 to 9 carbon atoms, and R "is a radical of an aliphatic, cycloaliphatic, aromatic or heterocyclic organic carboxylic acid with 1 to 10 carbon atoms, characterized in that a monosubstituted alkyl, cycloalkyl or aryl derivative in the amide nitrogen of a compound taken in the group consisting of dihydro-D-lysergamide and 1-methyl-dihydro-D-lysergamide is reduced by means of a reducing agent capable of converting the amide group to amine group, and the monosubstituted alkyl, cycloalkyl or aryl derivative in the amine nitrogen of the dihydro-D-lyssegamine or of the 1-methyl-dihydro-D-lysergamine thus obtained is acylated with the anhydride or the chloride of an organic carboxylic acid with 1 to 10 carbon atoms. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1215862 | 1962-06-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES289117A1 true ES289117A1 (en) | 1963-12-16 |
Family
ID=11139484
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES289117A Expired ES289117A1 (en) | 1962-06-18 | 1963-06-17 | A PROCEDURE FOR THE PREPARATION OF NEW DERIVATIVES OF 6-METHYL AND 1,6-DIMETHYL-8-AMINO-METHYL-ERGOLINE I |
Country Status (7)
| Country | Link |
|---|---|
| AT (1) | AT258482B (en) |
| BE (1) | BE633683A (en) |
| BR (1) | BR6349887D0 (en) |
| CH (1) | CH441354A (en) |
| DK (1) | DK104680C (en) |
| ES (1) | ES289117A1 (en) |
| GB (1) | GB985004A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2753947A1 (en) * | 1976-12-16 | 1978-06-29 | Sandoz Ag | NEW ERGOT DERIVATIVES, THEIR PRODUCTION AND USE |
-
1963
- 1963-06-13 GB GB23627/63A patent/GB985004A/en not_active Expired
- 1963-06-14 BR BR149887/63A patent/BR6349887D0/en unknown
- 1963-06-14 AT AT478463A patent/AT258482B/en active
- 1963-06-17 BE BE633683A patent/BE633683A/en unknown
- 1963-06-17 ES ES289117A patent/ES289117A1/en not_active Expired
- 1963-06-17 CH CH751363A patent/CH441354A/en unknown
- 1963-06-17 DK DK285463AA patent/DK104680C/en active
Also Published As
| Publication number | Publication date |
|---|---|
| BR6349887D0 (en) | 1973-07-03 |
| CH441354A (en) | 1967-08-15 |
| DK104680C (en) | 1966-06-20 |
| BE633683A (en) | 1963-07-15 |
| GB985004A (en) | 1965-03-03 |
| AT258482B (en) | 1967-11-27 |
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