US3700719A
Expired / Lapsed
US
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Processes for the preparation of n-(diethylaminoethyl)-4-amino-5-chloro-2-methoxybenzamide
Assignee: Astellas Pharma Inc
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Filing: 1969-11-17
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Granted: 1972-10-24
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Expires: 1989-11-17
Abstract
Abstract Improved processes for obtaining N-(diethylaminoethyl)-4-amino5-chloro-2-methoxybenzamide from p-aminosalycylic acid as starting material, each of which comprises only three or four steps.
Inventors
- 👤 Masuo Murakami
- 👤 Noriyoshi Inukai
- 👤 Akio Koda
- 👤 Koji Nakano
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 17:56
CPC Classifications
A; A61; A61K; A61K31/00; A61K31/16; A61K31/165; B; B65; B65G; B65G19/00; B65G19/18; B65G19/28; C; C07; C07C; C07C233/00; C07C233/01; C07C233/12; E; E21; E21F; E21F13/00; E21F13/06; F; F02; F02B; F02B77/00; F02B77/08; G; G05; G05D; G05D13/00; G05D13/08; G05D13/10; G05D13/12
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
59 words
A process for the preparation of N-(diethylaminoethyl)-4-amino-5-chloro-2-methoxybenzamide which comprises reacting p-aminosalicylic acid with a methylating agent selected from the group consisting of dimethylsulfate, monomethyl sulfate, methyl halide and methyl p-toluenesulfonate under alkaline and anhydrous conditions to yield methyl 4-amino-2-methoxybenzoate (II), reacting compound II with N,N-diethyl ethylenediamine to give N-(diethylaminoethyl)-4-amino-2-methoxybenzamide (III) and reacting compound III with iodobenzene dichloride under cooling.
Claim 2
Dependent Claim
75 words
A process for the preparation of N-(diethylaminoethyl)-4-amino-5-chloro-2-methoxybenzamide which comprises reacting p-aminosalicylic acid with a methylating agent selected from the group consisting of dimethylsulfate, monomethyl sulfate, methyl halide and methyl p-toluenesulfonate under alkaline and anhydrous conditions to yield methyl 4-amino-2-methoxybenzoate (II), reacting compound II with a basic agent to yield 4-amino-2-methoxybenzoic acid (II''), reacting compound II'' with N,N-diethyl ethylenediamine in the presence of phosphorous trichloride and reacting the N-(diethylaminoethyl)-4-amino-2-methoxybenzamide thus obtained with iodobenzene dichloride under cooling.
Claim 3
Dependent Claim
77 words
A process for the preparation of N-(diethylaminoethyl)-5-chloro- 4-amino-2-methoxybenzamide which comprises reacting p-aminosalicylic acid with a methylating agent selected from the group consisting of dimethylsulfate, monomethyl sulfate, methyl halide and methyl p-toluenesulfonate under alkaline and anhydrous conditions to yield methyl 4-amino-2-methoxybenzoate (II), reacting compound II with a basic agent to yield 4-amino-2-methoxybenzoic acid (II''), reacting compound II'' with iodobenzene dichloride under cooling and reacting the 5-chloro-4-amino-2-methoxybenzoic acid thus obtained with N,N-diethyl ethylenediamine in the presence of phosphorous trichloride.
Claim 4
Dependent Claim
36 words
A process for the preparation of methyl 4-amino-2-methoxybenzoate which comprises reacting p-amino-salicylic acid with a methylating agent selected from the group consisting of dimethylsulfate, monomethyl sulfate, methyl halide and methyl p-toluenesulfonate under alkaline and anhydrous conditions.
Claim 5
Dependent Claim
18 words
A process for the preparation of methyl 5-chloro-4-amino-2-methoxybenzoate which comprises reacting methyl 4-amino-2-methoxybenzoate with iodobenzene dichloride under cooling.
Claim 6
Dependent Claim
16 words
A process for the preparation of N-(diethylaminoethyl)-5-chloro-4-amino-2-methoxybenzamide which comprises reacting N-(diethylaminoethyl)-4-amino-2-methoxybenzamide with iodobenzene dichloride under cooling.
Claim 7
Dependent Claim
18 words
A process for the preparation of 5-chloro-4-amino-2-methoxybenzoic acid which comprises reacting 4-amino-2-methoxybenzoic acid with iodobenzene dichloride under cooling.
Claim 8
Dependent Claim
21 words
A process for the preparation of N-(diethylaminoethyl)-4-amino-2-methoxybenzamide which comprises reacting 4-amino-2-methoxybenzoic acid with N,N-diethyl ethylenediamine in the presence of phosphoRus trichloride.
Claim 9
Dependent Claim
21 words
A process for the preparation of N-(diethylaminoethyl)-5-chloro-4-amino-2-methoxybenzamide which comprises reacting 5-chloro-4-amino-2-methoxybenzoic acid with N,N-diethyl ethylenediamine in the presence of phosphorus trichloride.
References Cited (Backward Citations)
FR1407055A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1975-10-24 | 1976-04-24 | 1976-10-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1979-10-24 | 1980-04-24 | 1980-10-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1983-10-24 | 1984-04-24 | 1984-10-24 | $7700.00 | Window Closed / Lapsed |