GB2162173A - Ergoline derivatives - Google Patents
Ergoline derivatives Download PDFInfo
- Publication number
- GB2162173A GB2162173A GB08419150A GB8419150A GB2162173A GB 2162173 A GB2162173 A GB 2162173A GB 08419150 A GB08419150 A GB 08419150A GB 8419150 A GB8419150 A GB 8419150A GB 2162173 A GB2162173 A GB 2162173A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ergoline
- methyl
- formyl
- hydroxyethyl
- general formula
- 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
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
-
- 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
- C07D457/10—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid with hetero atoms directly attached in position 8
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Ergoline derivatives I <IMAGE> (R1 = H or CH3, R2 = C1 - C4 hydrocarbon, R5 = H or OCH3, either R3 + R4 = O or one of R3 and R4 = formyl, 2-oxoethyl or 3-oxopropyl and the other = H, R3 + R4 NOTEQUAL O if R5 = OCH3) are prepared by oxidising ergoline derivatives II <IMAGE> (R1, R2, R5 as above defined, W = hydroxy, hydroxymethyl, 2-hydroxyethyl or 3-hydroxypropyl, W NOTEQUAL OH if R5 =OCH3) with a triethylamine:sulphur trioxide complex.
Description
SPECIFICATION
Ergoline derivatives
The invention relates to ergoline derivatives and to a process for their preparation.
The invention provides a process for the preparation of an ergoline derivative having the general for miii,, I
wherein R, represents a hydrogen atom or a methyl group, R2 represents a hydrocarbon group having from 1 to 4 carbon atoms, R5 represents a hydrogen atom or a methoxy group, and either R3 and R4 together represent an oxygen atom or one of R3 and R4 represents a formyl, 2-oxoethyl or 3-oxopropyl group and the other of R3 and R4 represents a hydrogen atom, with the proviso that if R5 represents a methoxy group then R3 and R4 together do not represent an oxygen atom, which process comprises oxidizing with a triethylamine: sulphur troxide complex an ergoline derivative having the general formula II
wherein R1, R2 and R5 are as above defined and W represents a hydroxy, hydroxymethyl 2-hydroxyethyl or 3-hydroxypropyl group with the proviso that if R5 represents a methoxy group then W does not represent a hydroxy group.
The oxidation is preferably carried out in a mixture of dimethylsulphoxide and triethylamine at a temperature of 15"C to 30"C for a few minutes.
6-Methyl-8ss-formyl-ergoline and 6-methyl-8-oxo-ergoline are known compounds (Swiss Patent Specification No. 459243, Belgian Patent Specification No. 827930). The remaining compounds of the general formula I as above defined as novel and are included in the scope of the invention.
The ergoline derivatives prepared according to the invention are useful intermediates for the synthesis of new 8-substituted ergoline derivatives with good pharmacological activities.
The following Examples illustrate the invention.
Example 1 6-Methyl-8P-/2-oxoethyll-ergoline .
A suspension of 2.7 g of 6-methyl-8ss-(2- hydroxyethyl)-ergoline in 20 ml of dimethylsulphoxide and 20 ml of triethylamine was stirred at 25"C while 5 g of triethylamine:sulphur trioxide complex was added in small portions. The reaction mixture was stirred for 5 minutes and then poured into a solution of 30 ml of acetic acid and 300 ml of water. After 1/2 hours of continuous stirring, the solution was made basic with 5M aqueous sodium hydroxide solution. The resulting precipitate was filtered off, washed several times with water and crystallized from methanol affording 2.3 g of the title compound (m.p. 238-24-"C in 85% yield.
Example 2 6-Allyl-8P-formyl-ergoline Operating as in Example 1, but employing 6-allyl-8ss- hydroxymethyl-ergoline in place of 6-methyl-8p (2- -hydroxyethyl)-ergoline, the title compound (m.p. 132-134 C) was obtained in 45% yield.
Example 3 6-Ethyl-8p-formyl-ergoline Operating as in Example 1, but employing 6-ethyl-8ss- hydroxymethyl-ergoline in place of 6-methyl-8ss- (2- hydroxyethyl)-ergoline the title compound (m.p. 155-157 C) was obtained in 60% yield.
Example 4 6-Proypl-8ss-formyl-ergolíne Operating as in Example 1, but employing 6-propyl-8ss- hydroxymethyl-ergoline in place of 6-methyl 8p-(2- hydroxyethyl)-ergoline, the title compound (m.p. 147-149 C) was obtained in 50% yield.
Example 5 6-Methyl- 10-methoxy-8ss-form yl-ergoline
Operating as in Example 1, but employing 6-methyl-10- methoxy-8ss-hydroxymethyl-ergoline in place of 6- methyl-8ss-2(2-hydroxethyl)-ergoline, the title compound (m.p. 129-131"C) was obtained in 45% yield.
Example 6 6-Methyl-8ss-formyl-ergoline Operating as in Example 1, but employing 6-methyi-8ss- hydroxymethyl-ergoline in place of 6-methyl 8p-(2- hydroxyethyl)-ergoline, the title compound (m.p. 169-172 C) was obtained in 60% yield.
Example 7 1,6-Dimethyl-8ss-formyl-ergoline
Operating as in Example 1, but employing 1,6-dimethyl- 8P-hydroxymethyl-ergoiine in place of 6 methyl-8ss- (2-hydroxyethyl)-ergoline the title compound (m.p. 132-135 C) was obtained in 65% yield.
Example 8 6-methyl-8-oxo-ergoline
Operating as in Example 1, but employing 6-methyl-8ss- hydroxy-ergoline in place of 6-methyl-8p-(2- hydroxyethyl)-ergoline, the title compound (m.p. 210-215"C) was obtained in 65% yield.
Example 9 6-methyl-8ss-(3-oxopropyl)-ergoline
Operating as in Example 1, but employing 6-methyl-8ss- (3-hydroxypropyl)-ergoline in place of 6 methyl-8p- (2-hydroxyethyl)-ergoline, the title compound (m.p. 159-162"C) was obtained in 45% yield.
Claims (11)
1. A process for the preparation of an ergoline derivative having the general formula I as defined herein, the process comprising oxidizing an ergoline derivative having the general formula il as defined herein with a triethylamine:sulphur trioxide complex.
2. A process according to claim 1 which is carried out in a mixture of dimethylsulphoxide and triethylamine at a temperature of from 15"C to 30"C for a few minutes.
3. A process for the preparation of an ergoline derivative having the general formula I as herein defined, the process being substantially as described herein with reference to any of the Examples.
4. An ergoline derivative having the general formula I as herein defined, not being 6-methyl-8p-for- myl- ergoline and not being 6-methyl-8-oxo-ergoline.
5. 6-methyl-8p-(2-oxoethyl)-ergoline
6. 6-Allyl-8ss-formyl-ergoline.
7. 6-Ethyl-8p-formyl-ergoline.
8. 6-Propyl-8p-formyl-ergoline.
9. 6-Methyl-10-methoxy-8ss-formyl-ergoline.
10. 1,6-Dimethyl-8p-formyl-ergoline.
11. 6-Methyl-8ss-(3-oxopropyl)-ergoline.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB08419150A GB2162173B (en) | 1984-07-27 | 1984-07-27 | Ergoline derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB08419150A GB2162173B (en) | 1984-07-27 | 1984-07-27 | Ergoline derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB8419150D0 GB8419150D0 (en) | 1984-08-30 |
| GB2162173A true GB2162173A (en) | 1986-01-29 |
| GB2162173B GB2162173B (en) | 1987-07-29 |
Family
ID=10564535
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08419150A Expired GB2162173B (en) | 1984-07-27 | 1984-07-27 | Ergoline derivatives |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2162173B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2327277A (en) * | 1997-06-16 | 1999-01-20 | Trumpf Gmbh & Co | Device for influencing a laser beam |
-
1984
- 1984-07-27 GB GB08419150A patent/GB2162173B/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2327277A (en) * | 1997-06-16 | 1999-01-20 | Trumpf Gmbh & Co | Device for influencing a laser beam |
Also Published As
| Publication number | Publication date |
|---|---|
| GB8419150D0 (en) | 1984-08-30 |
| GB2162173B (en) | 1987-07-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |