GB836332A - Novel amino-acid hydrazides and a process for the manufacture of same - Google Patents
Novel amino-acid hydrazides and a process for the manufacture of sameInfo
- Publication number
- GB836332A GB836332A GB20164/58A GB2016458A GB836332A GB 836332 A GB836332 A GB 836332A GB 20164/58 A GB20164/58 A GB 20164/58A GB 2016458 A GB2016458 A GB 2016458A GB 836332 A GB836332 A GB 836332A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino
- acid
- acids
- reacting
- hydrogen
- 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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises amino-acid hydrazides of formula <FORM:0836332/IV (b)/1> where R1 is an aralkyl radical or a C1-7, alicyclic or aliphatic hydrocarbon radical, R2 is hydrogen or a hydrocarbon radical which may contain oxygen, nitrogen and/or sulphur atoms, R3 is hydrogen or alkyl and R4 is hydrogen, alkyl or acyl and R2 and R3 and R4 may be linked to form a heterocyclic ring, and salts thereof. A list of salt-forming acids includes ascorbic acid. Preparative methods specified are: (1) reaction of amino-acids with substituted hydrazines in the presence of a carbodiimide, e.g. at room temperature or slightly above, conveniently in aqueous or organic solution; (ii) reacting a reactive amino-acid derivative such as the ester, halide, amide or anhydride with a substituted hydrazine, preferably by heating a mixture under reflux; (iii) heating the substituted-hydrazine salts of the amino-acids to a temperature at which the salts dehydrate, advantageously removing the water formed continuously; (iv) reacting an amino-acid hydrazide with a carbonyl compound and reducing the resulting hydrazone simultaneously or successively e.g. by hydrogenation or with lithium aluminium hydride or by treating the hydrazone with a Grignard reagent and and hydrolysing the resulting product. In the above processes the group R4 may be chosen as an acyl group which is readily removable by alkaline hydrolysis (e.g. trifluoroacetyl) or hydrogenolysis (e.g. carbobenzyloxy). The products act as amine oxidase inhibitors and have therapeutic uses. Starting materials prepared are: in Example 11, DL-allo-carbobenzyloxythreonine and in Example 19, DL-threo-N-carbobenzyloxy-b -phenylserine by carbobenzyloxylation of the corresponding amino-acids; in Example 22, DL-a -dimethylamino propionic acid, which is converted to its ethyl ester, by reacting a -bromopropionic acid with dimethylamine; in Example 23, DL-a -methylaminopropionic acid and its methyl ester are similarly prepared using methylamine.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH836332X | 1957-07-04 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB836332A true GB836332A (en) | 1960-06-01 |
Family
ID=4540767
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB20164/58A Expired GB836332A (en) | 1957-07-04 | 1958-06-24 | Novel amino-acid hydrazides and a process for the manufacture of same |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB836332A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3178476A (en) * | 1961-06-16 | 1965-04-13 | Hoffmann La Roche | Di-or tri-hydroxybenzyl hydrazides |
US3351658A (en) * | 1965-04-06 | 1967-11-07 | Frederick C Bersworth | Amide reaction products of amino acid chelating compounds |
US3429915A (en) * | 1967-10-10 | 1969-02-25 | Frederick C Bersworth | Cyanamide amino acid chelating agents |
WO2012014226A1 (en) * | 2010-07-27 | 2012-02-02 | Indoco Remedies Limited | Process for preparation of lacosamide and some n-benzyl-propanamide intermediate derivatives |
-
1958
- 1958-06-24 GB GB20164/58A patent/GB836332A/en not_active Expired
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3178476A (en) * | 1961-06-16 | 1965-04-13 | Hoffmann La Roche | Di-or tri-hydroxybenzyl hydrazides |
US3351658A (en) * | 1965-04-06 | 1967-11-07 | Frederick C Bersworth | Amide reaction products of amino acid chelating compounds |
US3429915A (en) * | 1967-10-10 | 1969-02-25 | Frederick C Bersworth | Cyanamide amino acid chelating agents |
WO2012014226A1 (en) * | 2010-07-27 | 2012-02-02 | Indoco Remedies Limited | Process for preparation of lacosamide and some n-benzyl-propanamide intermediate derivatives |
US8957252B2 (en) | 2010-07-27 | 2015-02-17 | Indoco Remedies Limited | Process for preparation of lacosamide and some N-benzyl-propanamide intermediate derivatives |
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