GB2218090A - Preparation of the zinc salt of N-acetyl-6-aminohexanoic acid - Google Patents

Preparation of the zinc salt of N-acetyl-6-aminohexanoic acid Download PDF

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Publication number
GB2218090A
GB2218090A GB8908095A GB8908095A GB2218090A GB 2218090 A GB2218090 A GB 2218090A GB 8908095 A GB8908095 A GB 8908095A GB 8908095 A GB8908095 A GB 8908095A GB 2218090 A GB2218090 A GB 2218090A
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GB
United Kingdom
Prior art keywords
acetyl
zinc salt
preparation
aminohexanoic acid
solvent
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
Application number
GB8908095A
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GB2218090B (en
GB8908095D0 (en
Inventor
As Antonio Buxade Vi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Vi As S A Lab
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Vi As S A Lab
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Filing date
Publication date
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Publication of GB8908095D0 publication Critical patent/GB8908095D0/en
Publication of GB2218090A publication Critical patent/GB2218090A/en
Application granted granted Critical
Publication of GB2218090B publication Critical patent/GB2218090B/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Steroid Compounds (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)

Description

0 1 k r n 4 1 2 ' 18090 1 - A PROC-.SS FOR THE PREPARATION OF AN
N-ACETYL-6-AMINOHEXANOIC ACID DERIVATIVE.
The present invention relates to a process for the preparation of an Nacetyl-6-aminohexanoic acid derivative, particularly the zinc salt of said acid.
This salt, of formula:
[CH 3 -CONB-(CH 2)5 - CO(72 Zn 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-6aminohexanoic 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 0 C is used.
The salt may be isolated by crystallisation from the 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 0 C and 0.47 g of zinc oxide were added gradually. Once the addition had ended, the reaction - 2 mixture was 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 0 C, 6 ml of acetone were added and the mixture was cooled to -5 0 C. it was allowed to rest at that temperature for 12 hours, was filtered, washed in acetone and dried at 60 0 C.
A white crystalline powder which is the zinc salt of N-acetyl-6aminohexanoic acid was thus obtained.
Melting point: 193-196 0 C.
Elementary analysis:
Calculated (%) for C 16 H 28 N 2 0 6 Zn C: 46.94; 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 0 C and held for 30 minutes. The mixture was allowed to cooled to room temperature and thereafter was cooled to 02C. It was allowed to rest for 12 hours at 0 0 C, was filtered, washed with acetone and dried at 60 0 C.
A white crystalline compound having the same characteristics as that of Example 1 was thus obtained.

Claims (5)

What I claim is: I- 1 1 1 i 1 CLAIMS:
1.- A process for the preparation of an N-acetyl-6aminohexanoic acid derivative, namely the zinc salt thereof of formula úC-H COM-(CH) - 3- 2 5 - C0072 Zn, characterised in that N-acetyl-6-aminohexanoic acid is reacted with zinc oxide in a polar solvent.
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 temperature is equal to or less than the boiling point of the solvent.
4.- The process of claim 1, characterised in that said zinc salt is isolated by crystallisation from the same solvent, followed by filtration and drying.
5. A process as claimed in Claim 1 and substantially as described in the Examples.
Publirhed 1989 atThe Patent Office, State House. 66.71 High Halloern, London WC1R4TP. Further coples maybe obtainedfromThe Patent Offtce-
GB8908095A 1988-04-27 1989-04-11 A process for the preparation of an n-acetyl-6-aminohexanoic acid derivative Expired - Fee Related GB2218090B (en)

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 (3)

Publication Number Publication Date
GB8908095D0 GB8908095D0 (en) 1989-05-24
GB2218090A true GB2218090A (en) 1989-11-08
GB2218090B GB2218090B (en) 1991-12-11

Family

ID=8256036

Family Applications (1)

Application Number Title Priority Date Filing Date
GB8908095A Expired - Fee Related GB2218090B (en) 1988-04-27 1989-04-11 A process for the preparation of an n-acetyl-6-aminohexanoic 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)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1321466A (en) * 1969-09-25 1973-06-27 Choay Sa N-acetyl-6-amino-hexanoic acid derivative process for its production and pharmaceutical compositions containing the derivative
GB1357300A (en) * 1971-07-30 1974-06-19 Etd Ind Pharma Centre Magnesium salts

Family Cites Families (2)

* Cited by examiner, † Cited by third party
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
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)

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1321466A (en) * 1969-09-25 1973-06-27 Choay Sa N-acetyl-6-amino-hexanoic acid derivative process for its production and pharmaceutical compositions containing the derivative
GB1357300A (en) * 1971-07-30 1974-06-19 Etd Ind Pharma Centre Magnesium salts

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Chemical Abstracts,Vol.5 *
Chemical Abstracts,Vol.9 *

Also Published As

Publication number Publication date
DE3913627A1 (en) 1989-11-16
DE3913627C2 (en) 1997-12-11
PT90372B (en) 1995-03-31
NL8900901A (en) 1989-11-16
DK201589A (en) 1989-10-28
IT1229653B (en) 1991-09-06
GB2218090B (en) 1991-12-11
DK201589D0 (en) 1989-04-26
JP2588018B2 (en) 1997-03-05
ES2009266A6 (en) 1989-09-16
IE891100L (en) 1989-10-27
FR2630737B1 (en) 1991-11-08
IT8920252A0 (en) 1989-04-21
IE61517B1 (en) 1994-11-16
BE1002546A3 (en) 1991-03-19
GB8908095D0 (en) 1989-05-24
PT90372A (en) 1989-11-10
JPH02180859A (en) 1990-07-13
FR2630737A1 (en) 1989-11-03

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PCNP Patent ceased through non-payment of renewal fee

Effective date: 20050411