IE61517B1 - A process for the preparation of an N-acetyl-6-aminohexano acid derivative - Google Patents
A process for the preparation of an N-acetyl-6-aminohexano acid derivativeInfo
- Publication number
- IE61517B1 IE61517B1 IE110089A IE110089A IE61517B1 IE 61517 B1 IE61517 B1 IE 61517B1 IE 110089 A IE110089 A IE 110089A IE 110089 A IE110089 A IE 110089A IE 61517 B1 IE61517 B1 IE 61517B1
- Authority
- IE
- Ireland
- Prior art keywords
- acetyl
- acid derivative
- preparation
- aminohexanoic acid
- solvent
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 10
- 238000002360 preparation method Methods 0.000 title claims abstract description 5
- 239000002253 acid Substances 0.000 title description 2
- WDSCBUNMANHPFH-UHFFFAOYSA-N acexamic acid Chemical compound CC(=O)NCCCCCC(O)=O WDSCBUNMANHPFH-UHFFFAOYSA-N 0.000 claims abstract description 11
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000002798 polar solvent Substances 0.000 claims abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000003751 zinc Chemical class 0.000 claims abstract description 5
- 239000011787 zinc oxide Substances 0.000 claims abstract description 5
- 239000002904 solvent Substances 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 4
- 238000002425 crystallisation Methods 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 abstract description 3
- 239000011701 zinc Substances 0.000 abstract description 3
- 230000000767 anti-ulcer Effects 0.000 abstract description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Peptides Or Proteins (AREA)
- Steroid Compounds (AREA)
Abstract
A process for the preparation of the zinc salt of N-acetyl-6-aminohexanoic acid having formula [CH3-CONH-(CH2)5- COO]2 Zn comprises reacting zinc oxide with N-acetyl-6-aminohexanoic acid in a polar solvent (e.g. water). This salt has antiulcer properties.
Description
/ The present invention relates to a process for the preparation of an N-acetyl-6-aminohexanoic acid derivative, particularly the zinc salt of said acid.
This salt, of formula; /OH3-C0NH-(CH2)5 - COQ72Zn has antiulcer properties.
The process of the present invention is characterised in that zinc oxide, cheaper to obtain than other derivatives, is reacted with N-acetyl-6-aminohexanoic acid in a polar solvent or mixture of such solvents, preferably water.
The temperature used may reach the boiling point of the solvent; preferably a temperature of about 80°C is used The salt may be isolated by crystallisation from the 15 same solvent of a further solvent in which it is less soluble may be added to increase the yield, followed by filtration and drying.
To facilitate the explanation, the invention is illustrated by the following examples, while not being limited thereto.
EXAMPLE 1 2.0 g of N-acetyl-6-aminohexanoic acid were dissolved in 6 ml of distilled water. The temperature of the solution was raised to 80°C and 0.47 g of zinc oxide were added gradually. Once the addition had ended, the reaction mixture «as stirred at the above temperature for 15 minutes, after which it was allowed to cool. When the temperature had dropped to between 40 and 50°C, 6 ml of acetone were added and the mixture was cooled to -5°C. It was allowed to rest at that temperature for 12 hours, was filtered, washed in acetone and dried at 60°C.
A white crystalline powder which is the zinc salt of N-acetyl-6-aminohexanoic acid was thus obtained.
Melting point: 193-196°C.
Elementary analysis: Calculated (%) for Ο^Η^Ν^ΟθΖη C: 45.94; H: 6.84; N: 6.84; 0: 23.41; and Zn; 15.96 Found (%): C: 46.90; H: 6.67; N: 6.79; and Zn: 15.88 EXAMPLE 2 2.0 g of N-acetyl-6-aminohexanoic acid and 0.47 g of zinc oxide were poured into a reactor of appropriate capacity and 6 ml of distilled water were added. The temperature was raised, under stirring, to 90°C and held for 30 minutes. The mixture was allowed to cooled to room temperature and thereafter was cooled to 08C. It was allowed to rest for 12 hours at 0°C, was filtered, washed with acetone and dried at 60°C.
A white crystalline compound having the same characteristics as that of Example 1 was thus obtained.
Claims (3)
1. CLAIMS; 1.- A process for the preparation of an N-acetyl-6aminohexanoic acid derivative, namely the zinc salt thereof of formula /CH^-CONH-lCH^)- COO/^Xn,, characterised in
2. 5 that N-acetyl-6-aminohexanoic acid is reacted with zinc oxide in a polar solvent or a mixture of polar solvents. 2.- The process of claim 1, characterised in that said polar solvent is water. 3.- The process of claim 1, characterised in that the reaction temp 'βnature is equal to or less than the boili ng point of the solvent. 4.- The process of claim 1 characterised in that said zinc salt is isolated by cryst all isation from the same solvent, followed by filtration and drying. 15 5.- A process according to claim 1 for the preparation of an N-acetyl-6-aminohexanoic acid derivative of the formula given therein, substantially as hereinbefore described and exemplified.
3. 6.- An N-acetyl-6-aminohexanoic acid derivative of 2q the formula given in claim 1, whenever prepared by a process claimed in a preceding claim.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES8801281A ES2009266A6 (en) | 1988-04-27 | 1988-04-27 | Preparation of the zinc salt of N-acetyl-6-aminohexanoic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE891100L IE891100L (en) | 1989-10-27 |
| IE61517B1 true IE61517B1 (en) | 1994-11-16 |
Family
ID=8256036
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE110089A IE61517B1 (en) | 1988-04-27 | 1989-04-06 | A process for the preparation of an N-acetyl-6-aminohexano acid derivative |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JP2588018B2 (en) |
| BE (1) | BE1002546A3 (en) |
| DE (1) | DE3913627C2 (en) |
| DK (1) | DK201589A (en) |
| ES (1) | ES2009266A6 (en) |
| FR (1) | FR2630737B1 (en) |
| GB (1) | GB2218090B (en) |
| IE (1) | IE61517B1 (en) |
| IT (1) | IT1229653B (en) |
| NL (1) | NL8900901A (en) |
| PT (1) | PT90372B (en) |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1311466A (en) * | 1968-12-23 | 1973-03-28 | Herbert Ltd A | Vertical spindle lathe for use in a machining complex |
| FR2062873B1 (en) * | 1969-09-25 | 1973-07-13 | Choay Sa | |
| FR2147822B1 (en) * | 1971-07-30 | 1974-10-18 | Centre Etd Ind Pharma | |
| ES466455A1 (en) * | 1978-01-30 | 1978-10-16 | Vinas Lab | Procedure for the preparation of a new caprolactama derivative. (Machine-translation by Google Translate, not legally binding) |
-
1988
- 1988-04-27 ES ES8801281A patent/ES2009266A6/en not_active Expired
-
1989
- 1989-04-06 IE IE110089A patent/IE61517B1/en not_active IP Right Cessation
- 1989-04-11 NL NL8900901A patent/NL8900901A/en active Search and Examination
- 1989-04-11 GB GB8908095A patent/GB2218090B/en not_active Expired - Fee Related
- 1989-04-17 JP JP1098613A patent/JP2588018B2/en not_active Expired - Fee Related
- 1989-04-21 IT IT8920252A patent/IT1229653B/en active
- 1989-04-25 DE DE3913627A patent/DE3913627C2/en not_active Expired - Fee Related
- 1989-04-25 FR FR898905461A patent/FR2630737B1/en not_active Expired - Fee Related
- 1989-04-26 DK DK201589A patent/DK201589A/en not_active Application Discontinuation
- 1989-04-26 PT PT90372A patent/PT90372B/en active IP Right Grant
- 1989-04-26 BE BE8900464A patent/BE1002546A3/en active
Also Published As
| Publication number | Publication date |
|---|---|
| DE3913627C2 (en) | 1997-12-11 |
| IT8920252A0 (en) | 1989-04-21 |
| ES2009266A6 (en) | 1989-09-16 |
| NL8900901A (en) | 1989-11-16 |
| JP2588018B2 (en) | 1997-03-05 |
| DK201589A (en) | 1989-10-28 |
| PT90372B (en) | 1995-03-31 |
| DE3913627A1 (en) | 1989-11-16 |
| DK201589D0 (en) | 1989-04-26 |
| IE891100L (en) | 1989-10-27 |
| GB2218090B (en) | 1991-12-11 |
| FR2630737B1 (en) | 1991-11-08 |
| GB2218090A (en) | 1989-11-08 |
| FR2630737A1 (en) | 1989-11-03 |
| BE1002546A3 (en) | 1991-03-19 |
| GB8908095D0 (en) | 1989-05-24 |
| JPH02180859A (en) | 1990-07-13 |
| IT1229653B (en) | 1991-09-06 |
| PT90372A (en) | 1989-11-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed |