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-position

Info

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
Application number
GB820666A
Inventor
Rudolf Hiltmann
Hartmund Wollweber
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.)
Bayer AG
Original Assignee
Bayer AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of GB1081245A publication Critical patent/GB1081245A/en
Expired legal-status Critical Current

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

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Emergency 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.
GB820666A 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 Expired GB1081245A (en)

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) AT266160B (en)
CH (1) CH465579A (en)
DE (1) DE1300545B (en)
GB (1) GB1081245A (en)
IL (1) IL25224A (en)
SE (1) SE319467B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

Cited By (2)

* Cited by examiner, † Cited by third party
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
IL25224A (en) 1969-11-30
AT266859B (en) 1968-12-10
AT266858B (en) 1968-12-10
DE1300545B (en) 1969-08-07
CH465579A (en) 1968-11-30
SE319467B (en) 1970-01-19
AT266160B (en) 1968-11-11

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