IE46671B1 - Preparation of isobutyramide derivatives - Google Patents
Preparation of isobutyramide derivativesInfo
- Publication number
- IE46671B1 IE46671B1 IE483/78A IE48378A IE46671B1 IE 46671 B1 IE46671 B1 IE 46671B1 IE 483/78 A IE483/78 A IE 483/78A IE 48378 A IE48378 A IE 48378A IE 46671 B1 IE46671 B1 IE 46671B1
- Authority
- IE
- Ireland
- Prior art keywords
- isobutyramide
- formula
- derivatives
- preparation
- general formula
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Abstract
The derivatives of isobutyramide represented by the formula (I) in which R1 is a halogen atom and n is an integer from 2 to 6, are prepared by reacting, in dioxane, the substituted phenoxyisobutyramide of formula: with the N-cyanoalkylene of formula CH2=CH-(CH2)p-CN, in which p is an integer from 0 to 4, in the presence of a basic agent and at a temperature of between 50 and 65 DEG C. The compounds of formula (I) can be used as active substances, in combination with an excipient suited for the method of administration, in medicinal compositions, especially those having hypolipaemiating and hypotriglyceridaemiating and hypocholesterolaemiating actions.
Description
The invention relates to a process for the preparation of isobutyramide derivatives having the general formula I:
fH3
0-c —CO —NH-(CH2)n— CN (I)
CH wherein R represents a halogen atom and n is an integer from 5 2 to 6.
The above compounds, their preparation, and compositions containing them have been described and claimed in British Patent Specification No. 1,518,764.
The above compounds may be prepared according to the present 10 invention by reacting the corresponding substituted phenoxy isobutyramide of the general formula
—C -CO - NH,
CH, ch3 and the appropriate N-cyanoalkylene of the general formula
CH2 = CH — (CH2)n_2-CN (in which formulae R and n are as above defined) in a non-polar solvent, preferably dioxan, in the presence of a basic agent at from 50°C to 65°C.
The basic agent us^d in the process of the invention may be any of the basic reagents generally used in the chemical industry, for example solutions of sodium carbonate, potassium carbonate or alkali metal hydroxide^.
The reaction scheme is as follows:
The usefulness of the products is described and illustrated in the British Patent Specifiqption referred to above.
The invention is illustrated by the following Examples
Example 1
N-cyanoethyl ^-chlorophenoxy isobutyramide.
In a 5-liter reactor fitted with warming, cooling and stirring means there was prepared, at 60°C, a solution of 1,220 g (5.71 mol) of ^-chlorophenoxy isobutyramide in 1.81 of dioxan. There were then added 23 g of powdered sodium carbonate and slowly (in 15 minutes), while maintaining the temperature between 6Q°C and 65°C , 394 ml of acrylonitrile. The reaction mixture was stirred for 15 minutes at the same temperature, ’then’treated with 60 g of carbon black, and filtered.
1.6 litres of dioxan-were then added to the filtrate and after stirring, there were slowly pdded^ 10 litres of demineralized water. Stirring was maintained for 2 hours and the reaction mixture was then allowed to stand for 12 hours. After separation of the precipitate, washing with water and drying at 40°C, there was obtained 1.380 g of a beige ., product which, after recrystallization from isopropanol and water provided
l.OOlg (yield 73%) of. a white crystalline product melting at 71°C, analysis of which showed a very good correspondence with the formula C13H15°2N2C1·
Example 2
N-cyanoethyl jr-fluorophenoxy isobutyramide.
The procedure of Example 1 was repeated, but the ])-chlorophenoxy isobutyramide was replaced by £-fluorophenoxy isobutyramide. The yield was 64% of a white crystalline product melting at 75°C, analysis of which showed a good correspondence with the formula C13H15°2N2FExample 3
N-cyanobiityl £-chlorophenoxy isobutyramide.
The procedure of Example 1 was repeated, but the acrylonitrile was replaced by pentylenonitrile. The yield was 77% of a white crystalline product melting at 88°C, analysis of which shows a good correspondence with the formula gH^gN202Cl.
Claims (4)
- I. A process for the preparation of an isobutyramide derivative having the general formula I herein which comprises reacting the corresponding substituted phenoxy isobutyramide of the general formula in which R represents a halogen atom, with the appropriate N-cyanoalkylene of the general formula CH 2 = CH- (CH 2 ) n _ 2 —CN in which n is an integer from
- 2. To 6, in a non-polar solvent in the presence of a basic agent at from 50°C to 65°C. 10 2. A process according to claim 1, wherein the non-polar solvent is dioxan.
- 3. A process according to claim 1, substantially as disclosed in any of the Examples herein.
- 4. An isobutyramide derivative prepared by a process according 15 to ahy of the preceding claims.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB10069/77A GB1557420A (en) | 1977-03-10 | 1977-03-10 | Preparation of isobutyramide derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE780483L IE780483L (en) | 1978-09-10 |
| IE46671B1 true IE46671B1 (en) | 1983-08-24 |
Family
ID=9960874
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE483/78A IE46671B1 (en) | 1977-03-10 | 1978-03-09 | Preparation of isobutyramide derivatives |
Country Status (26)
| Country | Link |
|---|---|
| JP (1) | JPS53112823A (en) |
| AR (1) | AR214560A1 (en) |
| AT (1) | AT352104B (en) |
| AU (1) | AU517807B2 (en) |
| BE (1) | BE864075A (en) |
| CH (1) | CH628321A5 (en) |
| DE (1) | DE2810505C3 (en) |
| DK (1) | DK105078A (en) |
| EG (1) | EG13580A (en) |
| ES (1) | ES467566A1 (en) |
| FI (1) | FI780472A (en) |
| FR (1) | FR2383167A1 (en) |
| GB (1) | GB1557420A (en) |
| HK (1) | HK28880A (en) |
| IE (1) | IE46671B1 (en) |
| IN (1) | IN147801B (en) |
| LU (1) | LU79195A1 (en) |
| MX (1) | MX4826E (en) |
| MY (1) | MY8100067A (en) |
| NL (1) | NL7802024A (en) |
| NO (1) | NO143969C (en) |
| NZ (1) | NZ186388A (en) |
| OA (1) | OA05902A (en) |
| PT (1) | PT67667B (en) |
| SE (1) | SE431202B (en) |
| ZA (1) | ZA78618B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE496032T1 (en) | 1999-02-24 | 2011-02-15 | Hoffmann La Roche | 4-PHENYLPYRIDINE DERIVATIVES AND THEIR USE AS NK-1 RECEPTOR ANTAGONISTS |
| TWI280239B (en) | 2003-07-15 | 2007-05-01 | Hoffmann La Roche | Process for preparation of pyridine derivatives |
| DK1928427T3 (en) | 2005-09-23 | 2010-03-08 | Hoffmann La Roche | Hitherto unknown dosage formulation |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE734725C (en) * | 1940-04-17 | 1943-04-30 | Ig Farbenindustrie Ag | Process for the preparation of formylamino-ª ‰ -propionitriles |
| GB1064252A (en) * | 1963-09-19 | 1967-04-05 | Ici Ltd | Amides and pharmaceutical compositions containing them |
| GB1041982A (en) * | 1963-09-30 | 1966-09-07 | Boots Pure Drug Co Ltd | Herbicidal compounds and compositions |
-
1977
- 1977-03-10 GB GB10069/77A patent/GB1557420A/en not_active Expired
-
1978
- 1978-02-01 ZA ZA00780618A patent/ZA78618B/en unknown
- 1978-02-06 IN IN94/DEL/78A patent/IN147801B/en unknown
- 1978-02-07 NZ NZ186388A patent/NZ186388A/en unknown
- 1978-02-14 FI FI780472A patent/FI780472A/en not_active Application Discontinuation
- 1978-02-16 PT PT67667A patent/PT67667B/en unknown
- 1978-02-17 BE BE185268A patent/BE864075A/en not_active IP Right Cessation
- 1978-02-21 AU AU33459/78A patent/AU517807B2/en not_active Expired
- 1978-02-23 NL NL7802024A patent/NL7802024A/en unknown
- 1978-02-24 CH CH200778A patent/CH628321A5/en not_active IP Right Cessation
- 1978-02-28 JP JP2168278A patent/JPS53112823A/en active Granted
- 1978-03-02 AT AT148978A patent/AT352104B/en not_active IP Right Cessation
- 1978-03-04 ES ES467566A patent/ES467566A1/en not_active Expired
- 1978-03-06 OA OA56427A patent/OA05902A/en unknown
- 1978-03-07 EG EG156/78A patent/EG13580A/en active
- 1978-03-08 AR AR271358A patent/AR214560A1/en active
- 1978-03-08 LU LU79195A patent/LU79195A1/en unknown
- 1978-03-09 IE IE483/78A patent/IE46671B1/en unknown
- 1978-03-09 MX MX786923U patent/MX4826E/en unknown
- 1978-03-09 NO NO780834A patent/NO143969C/en unknown
- 1978-03-09 SE SE7802694A patent/SE431202B/en unknown
- 1978-03-09 DK DK105078A patent/DK105078A/en not_active Application Discontinuation
- 1978-03-10 FR FR7806912A patent/FR2383167A1/en active Granted
- 1978-03-10 DE DE2810505A patent/DE2810505C3/en not_active Expired
-
1980
- 1980-05-22 HK HK288/80A patent/HK28880A/en unknown
-
1981
- 1981-12-30 MY MY67/81A patent/MY8100067A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IN147801B (en) | 1980-06-28 |
| OA05902A (en) | 1981-05-31 |
| SE431202B (en) | 1984-01-23 |
| PT67667A (en) | 1978-03-01 |
| NZ186388A (en) | 1979-04-26 |
| HK28880A (en) | 1980-05-30 |
| ATA148978A (en) | 1979-02-15 |
| MX4826E (en) | 1982-10-21 |
| FR2383167A1 (en) | 1978-10-06 |
| AR214560A1 (en) | 1979-06-29 |
| AU517807B2 (en) | 1981-08-27 |
| NO143969B (en) | 1981-02-09 |
| JPS5715831B2 (en) | 1982-04-01 |
| FI780472A (en) | 1978-09-11 |
| AT352104B (en) | 1979-09-10 |
| NO143969C (en) | 1981-06-03 |
| NO780834L (en) | 1978-09-12 |
| ES467566A1 (en) | 1978-10-16 |
| MY8100067A (en) | 1981-12-31 |
| NL7802024A (en) | 1978-09-12 |
| BE864075A (en) | 1978-06-16 |
| FR2383167B1 (en) | 1980-04-25 |
| SE7802694L (en) | 1978-09-11 |
| EG13580A (en) | 1981-12-31 |
| AU3345978A (en) | 1979-08-30 |
| CH628321A5 (en) | 1982-02-26 |
| JPS53112823A (en) | 1978-10-02 |
| DK105078A (en) | 1978-09-11 |
| ZA78618B (en) | 1978-12-27 |
| DE2810505B2 (en) | 1979-08-30 |
| IE780483L (en) | 1978-09-10 |
| DE2810505C3 (en) | 1980-05-08 |
| GB1557420A (en) | 1979-12-12 |
| LU79195A1 (en) | 1978-06-28 |
| PT67667B (en) | 1979-07-20 |
| DE2810505A1 (en) | 1978-09-14 |
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