GB779829A - Polyglycol ethers and their manufacture - Google Patents

Polyglycol ethers and their manufacture

Info

Publication number
GB779829A
GB779829A GB33816/54A GB3381654A GB779829A GB 779829 A GB779829 A GB 779829A GB 33816/54 A GB33816/54 A GB 33816/54A GB 3381654 A GB3381654 A GB 3381654A GB 779829 A GB779829 A GB 779829A
Authority
GB
United Kingdom
Prior art keywords
ether
acid
glycol monomethyl
monomethyl ether
dimethylphenylamide
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
GB33816/54A
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.)
BASF Schweiz AG
Original Assignee
Ciba 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 Ciba AG filed Critical Ciba AG
Publication of GB779829A publication Critical patent/GB779829A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00Carboxylic acid amides

Landscapes

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

Abstract

The invention comprises polyglycol ethers of the formula: <FORM:0779829/IV(b)/1> in which n represents a whole number from 2 to 20, R represents hydrogen or a hydrocarbon radical containing at most 7 carbon atoms, and R1 and R11 each represent a hydrogen atom or an alkyl or alkoxy-alkyl group containing at most 4 carbon atoms provided that R1 and R11 represent hydrogen in at least n/2 of the residues <FORM:0779829/IV(b)/2> x represents hydrogen or a hydrocarbon radical containing at most 7 carbon atoms, "Aryl" represents an alkyl- or alkoxy-substituted phenyl residue and Y represents hydrogen, an aliphatic or cycloaliphatic hydrocarbon radical or the residue "Aryl". Such compounds are obtained by reacting a reactive ester (e.g. a hydrohalic acid or an organic sulphonic acid ester) of a hydroxy-carboxylic acid arylide of the formula: <FORM:0779829/IV(b)/3> with a polyglycol, if desired in the form of a metal alcoholate, or in the presence of a metal alcoholate. The reaction may be formed in stages, such as by first forming a glycol ether of an aliphatic hydroxycarboxylic acid arylide and converting the product or its alcoholate into a polyglycol ether. Alternatively a reactive carboxyl derivative of a polyglycol ether of an aliphatic hydroxy carboxylic acid is reacted with the appropriate arylamine, suitably in the presence of an acid-binding agent. Mixtures of final products with n having different values may be formed. The products have therapeutic properties. In Example (1) the acid chloride obtained by treating the ether of pentaethylene glycol monomethyl ether with glycollic acid of the formula CH3(OCH2CH2)5OCH2COOH is reacted with N-n-butyl-2 : 6-dimethylaniline to form the ether of pentaethylene glycol monomethyl ether with glycollic acid N-n-2 : 6-N-dimethylphenylamide. Similarly obtained are (2) the ether of octaethylene glycol monomethyl ether with glycollic acid-N-butyl-N-2 : 6-dimethylphenylamide; (3) a similar compound having 6 to 8 ethylenoxy groups; (4) the ether of diethylene glycol monomethyl ether with glycollic acid N-2 : 6-dimethylphenyl amide, and the corresponding compound with 6 to 8 ethylenoxy groups; (5) the ether of the polyethylene glycol monomethyl ether with a -hydroxycaproic acid of the formula: <FORM:0779829/IV(b)/4> in which n has the average value of about 6 to 8 ; (6) the ether of hepta-ethylene glycol monomethyl ether with glycollic acid N-p-ethoxyphenyl amide; (9) the ehters of penta- and hexaethylene glycol monomethyl ethers of glycollic acid N - 2:6 - dimethyl - 4 - n - butoxyphenylamide. In Example (7) hepta-ethylene glycol monomethyl ether is reacted with sodium and the product with a -chloracetic acid-N-n-butylN:2:6-dimethylphenylamide to give the ether of hepta-ethylene glycol monomethyl ether with glycollic acid - N - n - butyl - N - 2:6 - dimethylphenylamide. Analogously produced are similar tetra- and hexaethylene glycol derivatives and compounds with N-n-hexyl and n-heptyl substituents. Similarly obtained are (10) the same product as in Example (1); (13) the ether of hexa-ethylene glycol monomethyl ether with glycollic acid-N:N-di-o-tolylamide. In Example (8) a -chloracetic acid-N-n-butyl 2:6 - dimethyl - phenyl - amide is reacted with the sodium derivatives of di- and tri-ethylene glycol respectively to give the corresponding ethers. In Example (11) the ether of 1:2-propylene glycol with glycollic acid N-butyl-N-2:6-dimethylphenylamide is heated in a sealed tube with ethylene oxide in the presence of sodium hydroxide to give a mixture of ethers of the formula: <FORM:0779829/IV(b)/5> where n has an average value of 7 which can be fractionated by countercurrent extraction between two liquid phases. In Example (12) the sodium derivative of octa-ethylene glycol-o - methyl ether - o 1 - [2 - hydroxy - 3 - ethoxypropyl ether-(1)] is reacted with a -chloracetic acid N-n-heptyl-2:6-dimethylphenylamide to give the corresponding ether.ALSO:Polyglycol ethers of the formula <FORM:0779829/VI/1> in which n represents a whole number from 2 to 20, R represents hydrogen or a hydrocarbon radical containing at most 7 carbon atoms and R1 and R11 each represent a hydrogen atom or an alkyl or alkoxy-alkyl group containing at most 4 carbon atoms, provided that R1 and R11 represent hydrogen in at least <FORM:0779829/VI/2> of the residues -(OCHR1 - CHR11)-, X represents hydrogen or a hydrocarbon radical containing at most 7 carbon atoms, "Aryl" represents an alkyl- or alkoxy-substituted phenyl residue and Y represents hydrogen, an aliphatic or cycloaliphatic hydrocarbon radical or the residue "Aryl" have pharmacoligical, especially local anaesthetic action and may be formed into pharmaceutical preparations with an organic or inorganic carrier for enteral, parenteral or oral application. Specified carriers are water, gelatin, lactose, starch, magnesium stearate, talc, vegetable oils, benzyl alcohol, gums, polyalkylene gylcols, petroleum jelly, and cholesterol, or other therapeutically active substances, preservatives, stabilizing, wetting or emulsifying agents, salts which vary the osmotic pressure or buffer substances may be added. The compositions may be formed into tablets, dragees, salves, creams, solutions, suspension or emulsions. The preparation of the glycol ethers is described (see Group IV(b)).
GB33816/54A 1953-11-20 1954-11-22 Polyglycol ethers and their manufacture Expired GB779829A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH779829X 1953-11-20

Publications (1)

Publication Number Publication Date
GB779829A true GB779829A (en) 1957-07-24

Family

ID=4536102

Family Applications (1)

Application Number Title Priority Date Filing Date
GB33816/54A Expired GB779829A (en) 1953-11-20 1954-11-22 Polyglycol ethers and their manufacture

Country Status (1)

Country Link
GB (1) GB779829A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011045232A2 (en) 2009-10-13 2011-04-21 F. Hoffmann-La Roche Ag Neuropeptide-2 receptor (y-2r) agonists

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011045232A2 (en) 2009-10-13 2011-04-21 F. Hoffmann-La Roche Ag Neuropeptide-2 receptor (y-2r) agonists

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