GB1081245A - 2-(n,n-dialkyl-and n-alkoxy-n-alkyl-carbamoyl-methoxy)-benzoic acid esters substituted in the 5-position - Google Patents
2-(n,n-dialkyl-and n-alkoxy-n-alkyl-carbamoyl-methoxy)-benzoic acid esters substituted in the 5-positionInfo
- Publication number
- GB1081245A GB1081245A GB820666A GB820666A GB1081245A GB 1081245 A GB1081245 A GB 1081245A GB 820666 A GB820666 A GB 820666A GB 820666 A GB820666 A GB 820666A GB 1081245 A GB1081245 A GB 1081245A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- aliphatic
- radical
- acid
- reacting
- 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
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/27—Esters, e.g. nitroglycerine, selenocyanates of carbamic or thiocarbamic acids, meprobamate, carbachol, neostigmine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/90—Carboxylic acid amides having nitrogen atoms of carboxamide groups further acylated
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Emergency Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Novel compounds of Formula I <FORM:1081245/C2/1> wherein R is an alkyl radical having up to 6 carbon atoms, and R1 is an alkyl or alkoxy radical having up to 6 carbon atoms, or R and R1 together with the nitrogen atom and possibly also an oxygen atom form a saturated heterocyclic ring, R11 is an alkyl or alkenyl radical having up to 6 carbon atoms, and R111 is a saturated or unsaturated aliphatic, aliphatic-oxy, aliphatic-oxy-aliphatic, hydroxy-aliphatic or oxo-aliphatic radical having up to 6 carbon atoms, may be prepared (1) by reacting a 5-substituted salicylic acid ester in the presence of condensation agents with a glycollic acid amide of formula HO-CH2-CONRR1 or a reactive ester thereof, (2) by reacting a 5-substituted 2 - carboxymethoxybenzoic acid ester or a reactive functional derivative thereof with an amine of formula R-NH-R1 or a reactive derivative thereof, (3) when R111 represents an alkyl group, by alkylation of the corresponding hydroxy compound, or (4) by reducing the corresponding carboxyaldehyde to give compounds in which R111 represents a hydroxymethyl or methyl radical, or by reacting the aldehyde with a lower aliphatic ketone to give compounds in which R111 represents an oxoalkenyl radical, which may be converted into an oxoalkyl, hydroxyalkenyl, hydroxyalkyl or alkyl radical. The esters of the invention may also be obtained by esterification of the corresponding acid, acid chloride, mixed anhydride or salt, or by transesterification of other esters. Methyl 5-n-propyloxysalicylate may be obtained by treating hydroquinone mono-n-propyl ether with carbon dioxide under pressure and esterifying the 5-n-propylsalicylic acid obtained. Methyl 5-acetylsalicylate is obtained by esterification of the free acid. Other alkyl 5-propionylsalicylates may be obtained by Frie's rearrangement of the alkyl O-propionylsalicylate. n-Propyl 2-carboxymethoxy-5-ethoxy-benzoate is made by reacting n-propyl 5-ethoxysalicylate with sodium chloroacetate and releasing the free acid from the sodium salt obtained.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF45338A DE1300545B (en) | 1965-02-24 | 1965-02-24 | Process for the preparation of 2- (N, N-dialkyl- or N-alkyl-N-alkoxy-carbamoyl-methoxy) -benzoic acid esters substituted in the 5-position |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1081245A true GB1081245A (en) | 1967-08-31 |
Family
ID=7100446
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB820666A Expired GB1081245A (en) | 1965-02-24 | 1966-02-24 | 2-(n,n-dialkyl-and n-alkoxy-n-alkyl-carbamoyl-methoxy)-benzoic acid esters substituted in the 5-position |
Country Status (6)
Country | Link |
---|---|
AT (3) | AT266858B (en) |
CH (1) | CH465579A (en) |
DE (1) | DE1300545B (en) |
GB (1) | GB1081245A (en) |
IL (1) | IL25224A (en) |
SE (1) | SE319467B (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2081588A1 (en) * | 1970-03-26 | 1971-12-10 | Bruneau & Cie Lab | 2-carboxy and 2-carboxyalkyl-phenoxyacetamide esters - - as short acting narcotics |
WO1987004152A1 (en) * | 1985-12-30 | 1987-07-16 | The Wellcome Foundation Ltd. | New aryl derivatives |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1134981B (en) * | 1960-05-06 | 1962-08-23 | Bayer Ag | Process for the preparation of N-substituted 3-methoxy-4-carbamidomethoxyphenyl acetic acid alkyl and alkenyl esters |
-
1965
- 1965-02-24 DE DEF45338A patent/DE1300545B/en active Pending
-
1966
- 1966-02-16 CH CH224466A patent/CH465579A/en unknown
- 1966-02-22 SE SE2277/66A patent/SE319467B/xx unknown
- 1966-02-22 IL IL2522466A patent/IL25224A/en unknown
- 1966-02-24 AT AT1054467A patent/AT266858B/en active
- 1966-02-24 AT AT170166A patent/AT266160B/en active
- 1966-02-24 AT AT1054567A patent/AT266859B/en active
- 1966-02-24 GB GB820666A patent/GB1081245A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2081588A1 (en) * | 1970-03-26 | 1971-12-10 | Bruneau & Cie Lab | 2-carboxy and 2-carboxyalkyl-phenoxyacetamide esters - - as short acting narcotics |
WO1987004152A1 (en) * | 1985-12-30 | 1987-07-16 | The Wellcome Foundation Ltd. | New aryl derivatives |
Also Published As
Publication number | Publication date |
---|---|
DE1300545B (en) | 1969-08-07 |
AT266859B (en) | 1968-12-10 |
CH465579A (en) | 1968-11-30 |
AT266160B (en) | 1968-11-11 |
IL25224A (en) | 1969-11-30 |
SE319467B (en) | 1970-01-19 |
AT266858B (en) | 1968-12-10 |
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