GB770870A - Improvements in or relating to amines and to processes for their preparation - Google Patents

Improvements in or relating to amines and to processes for their preparation

Info

Publication number
GB770870A
GB770870A GB12660/54A GB1266054A GB770870A GB 770870 A GB770870 A GB 770870A GB 12660/54 A GB12660/54 A GB 12660/54A GB 1266054 A GB1266054 A GB 1266054A GB 770870 A GB770870 A GB 770870A
Authority
GB
United Kingdom
Prior art keywords
group
groups
aminophenoxy
compounds
hydroxyalkyl
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
GB12660/54A
Inventor
Julius Nicholson Ashley
Raymond Frederick Collins
Michael Davis
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.)
May and Baker Ltd
Original Assignee
May and Baker Ltd
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 May and Baker Ltd filed Critical May and Baker Ltd
Priority to GB12660/54A priority Critical patent/GB770870A/en
Publication of GB770870A publication Critical patent/GB770870A/en
Expired legal-status Critical Current

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/185Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19Carboxylic acids, e.g. valproic acid
    • A61K31/195Carboxylic acids, e.g. valproic acid having an amino group

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (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

The invention comprises compounds of the formula <FORM:0770870/IV(b)/1> and their acid addition salts, where R1 and R2 are hydrogen atoms, lower alkyl groups of up to 6 carbon atoms or hydroxyalkyl (including polyhydroxyalkyl) or alkoxyalkyl groups, A is a saturated unbranched hydrocarbon chain containing 3 to 9 carbon atoms and R is an alkyl, hydroxyalkyl, aralkyl or phenyl group or a phenyl group substituted by an alkoxy, acyl, hydroxy, nitro, acidylamino or sulphonamido group, such substituent being preferably in the para-position. The invention also comprises sodium formaldehyde bisulphite addition products of the primary amines of the above formula. The compounds are made by reaction of a compound of the formula <FORM:0770870/IV(b)/2> with a compound of the formula Z2, where Z1 and Z2 are respectively a group and a compound capable of reacting together to form the group -O-A1-O-R1, where A1 represents the group A or a corresponding less-saturated hydrocarbon linkage and R1 represents the group R or an atom or group convertible into the group R, and X is a tertiary amino group or a group or atom capable of being converted into a primary, secondary or tertiary amino group. Where necessary the groups X and R1 may then be converted into the groups NR1R2 and R respectively and the group A1 reduced to form the group A. Suitably Z1 may be the group -OM or the group -O-A1-Q or O-A1-O-M, and Z2 may then be the compound Q-A1-OR1 or M-O-R1 or Q-R1 as is appropriate, wherein M is a hydrogen atom or an alkali metal atom and Q is the radical of a reactive ester such as a methane sulphonate group or a halogen atom. Groups which may be represented by X include: (a) as groups convertible to primary amino groups; acylamino, nitro, nitroso carbonamido, anil, alkoxycarbonylamino and arylazo groups; (b) as groups convertible into secondary amino groups; acylalkylamido groups (by hydrolysis) and anil, alkoxycarbonylamino or acylamido groups (by reduction), and (c) tertiary amino groups or groups convertible to tertiary amino groups such as quaternary ammonium groups (by pyrolysis) and acylalkylamino groups (by reduction). The group R1 may be an alkyl, aralkyl, hydroxyalkyl or phenyl group or a group such as nitrophenyl, which may be converted into an acylamido- or sulphonamidophenyl group by reduction followed by acylation or sulphonation, or a hydroxyphenyl group, convertible into an alkoxyphenyl group by alkylation. The products may be used in the treatment of bilharziasis (see Group VI). Examples describe the preparation according to the invention of 1-methoxy-, 1-n-propoxy-, 1-21-hydroxyethoxy-, 1-p-ethoxyphenoxy-, 1-benzyloxy-, 1-p-nitrophenoxy-, 1-phenoxy-, 1-p-methoxyphenoxy-, 1-p-acetylphenoxy-, 1-p-propionamidophenoxy-, 1 - p - benzamidophenoxy and 1 - p - methanesulphonamidophenoxy-5-p-aminophenoxypentanes; 1 - p - aminophenoxy-3 - methoxypropane; 1 - p - aminophenoxy - 3 - phenoxy propane; 1 - p - di - (2 - hydroxyethyl) - aminophenoxy - 5 - p - acetamidophenoxypentane; N - acetyl - 1 - p - ethylaminophenoxy - 5 - p - dimethylaminophenoxypentane and 1-p-methylaminophenoxy-8-phenoxyoctane, and the sodium formaldehyde bisulphate addition product of 1 - p - aminophenoxy - 5 - p - acetamidophenoxypentane. The products are obtained either as the free bases or as acid addition salts such as methanesulphonates. Nitrophenoxyalkane derivatives used as intermediates in the above examples, namely 1-methoxy-, 1-n-propoxy-, 1,21-hydroxyethoxy-, 1 - p - hydroxyphenoxy -, 1 - p - ethoxyphenoxy-, 1-benzyloxy-, 1-p-acetamidophenoxy-, 1-phenoxy-, 1-p-methoxyphenoxy-, 1-p-acetylphenoxy-, 1 - p - propionamidophenoxy-, 1 - p - benzamidophenoxy-and 1-p-methanesulphonamidophenoxy - 5 - p - nitrophenoxypentanes; 1 - p - nitrophenoxy - 3 - methoxypropane and 1 - p - nitrophenoxy - 3 - phenoxypropane are made by various methods. 5-Benzyloxypentyl bromide and 8-phenoxyoctyl bromide are made by reaction of 1 : 5-dibromopentane with benzyl alcohol and 1 : 8-dibromo-octane with phenol respectively, the hydroxy compounds being used in the form of their alkali metal derivatives. Specification 761,888 is referred to.ALSO:Therapeutic compositions for the treatment of bilharziosis comprise compounds of the general formula <FORM:0770870/VI/1> wherein R1 and R2 are each a hydrogen atom or a lower alkyl, hydroxyalkyl or alkoxyalkyl group of not more than 6 carbon atoms, A represents a saturated unbranched hydrocarbon chain of 3 to 9 carbon atoms which may be substituted by one or more alkyl groups of not more than 6 carbon atoms, and R represents an alkyl, aralkyl, hydroxyalkyl or phenyl group or a phenyl group substituted by an alkoxy, acyl, hydroxy, nitro, acylamido or sulphonamido group preferably in the para position, or acid addition salts, or sodium formaldehyde bisulphite addition products of the new substances which contain a primary amino group, admixed with a pharmaceutical diluent. Preferred therapeutic compounds are those wherein R1 and R2 are chosen from hydrogen atoms or methyl, ethyl, propyl, hydroxyethyl or hydroxypropyl groups, A represents a pentamethylene or octamethylene chain and R is a lower alkyl or aralkyl group, a phenyl group or a phenyl group substituted in the para position by an alkoxy, nitro, acylamido or sulphonamido group; specified compounds being the 1-benzyloxy, 1-n-propoxy-, 1-phenoxy- and 1-p-methane-sulphonamidophenoxy- 5- paminophenoxypentanes; N - acetyl - 1 - p - ethylaminophenoxy-5 - p-dimethylaminophenoxypentane; 1-p-methylaminophenoxy-8-phenoxyoctane; 1-p-aminophenoxy - 5-p-acetamidophenoxypentane, 1-p-di (2-hydroxy ethyl) aminophenoxy - 5 - p - acetamidophenoxy pentane and 1-p-aminophenoxy-5-p-ethoxyphenoxy pentane and 1-p-aminophenoxy-5-p-nitrophenoxy pentane. The active compounds are suitably employed as elixirs, tablets, powders, capsules, or injectable solutions. The compositions may contain the active compound in a liquid diluent such as water, or admixed with solid diluents such as starch, lactose, stearic acid, talc magnesium stearate or gums. Examples describe compositions for tablet formation comprising (a) 1-p-aminophenoxy-5-benzyloxypentane methane sulphonate, starch, dextrin, magnesium stearate, stearic acid and sodium carboxymethyl cellulose and (b) 1-p-aminophenoxy-5-n-propoxy pentane methane sulphonate, starch, dextrin, magnesium stearate, stearic acid, alginic acid and sodium lauryl sulphate.
GB12660/54A 1954-04-30 1954-04-30 Improvements in or relating to amines and to processes for their preparation Expired GB770870A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB12660/54A GB770870A (en) 1954-04-30 1954-04-30 Improvements in or relating to amines and to processes for their preparation

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB12660/54A GB770870A (en) 1954-04-30 1954-04-30 Improvements in or relating to amines and to processes for their preparation

Publications (1)

Publication Number Publication Date
GB770870A true GB770870A (en) 1957-03-27

Family

ID=10008788

Family Applications (1)

Application Number Title Priority Date Filing Date
GB12660/54A Expired GB770870A (en) 1954-04-30 1954-04-30 Improvements in or relating to amines and to processes for their preparation

Country Status (1)

Country Link
GB (1) GB770870A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1144290B (en) * 1958-06-24 1963-02-28 May & Baker Ltd Process for the production of new substituted aminophenols

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1144290B (en) * 1958-06-24 1963-02-28 May & Baker Ltd Process for the production of new substituted aminophenols

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