GB1380882A - Anthelmintic ethers and formulations thereof - Google Patents

Anthelmintic ethers and formulations thereof

Info

Publication number
GB1380882A
GB1380882A GB3466871A GB3466871A GB1380882A GB 1380882 A GB1380882 A GB 1380882A GB 3466871 A GB3466871 A GB 3466871A GB 3466871 A GB3466871 A GB 3466871A GB 1380882 A GB1380882 A GB 1380882A
Authority
GB
United Kingdom
Prior art keywords
bis
reacting
acetamidophenoxy
ether
formula
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
GB3466871A
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.)
Wellcome Foundation Ltd
Original Assignee
Wellcome Foundation 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 Wellcome Foundation Ltd filed Critical Wellcome Foundation Ltd
Priority to GB3466871A priority Critical patent/GB1380882A/en
Priority to US174986A priority patent/US3896235A/en
Priority to BE772033A priority patent/BE772033A/en
Priority to NO713241A priority patent/NO134866C/no
Priority to IE1101/71A priority patent/IE35575B1/en
Priority to IL7137620A priority patent/IL37620A/en
Priority to IT7152589A priority patent/IT1056014B/en
Priority to CA121,845A priority patent/CA995688A/en
Priority to DK426671A priority patent/DK136358B/en
Priority to DE2166359*A priority patent/DE2166359A1/en
Priority to FI2432/71A priority patent/FI55026C/en
Priority to DE2143570A priority patent/DE2143570C3/en
Priority to FR7131600A priority patent/FR2105171B1/fr
Priority to NLAANVRAGE7112023,A priority patent/NL169585C/en
Priority to JP7197094A priority patent/JPS5542966B1/ja
Publication of GB1380882A publication Critical patent/GB1380882A/en
Priority to CA253,179A priority patent/CA1011654A/en
Priority to DK111277A priority patent/DK111277A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms

Landscapes

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

Abstract

1380882 Ethers WELLCOME FOUNDATION Ltd 26 Nov 1971 [1 Sept 1970 (2) 23 July 1971 31 Aug 1971] 41871/70 41872/70 34668/71 and 40496/71 Heading C2C [Also in Division A5] The invention comprises novel ethers of the formula wherein R and R<SP>1</SP> are the same or different and each is H, optionally substituted saturated C 1-7 aliphatic hydrocarbon group, or an unsaturated C 2-4 aliphatic hydrocarbon group, R<SP>2</SP> and R<SP>3</SP> each is H or C 1-4 alkyl and A is -CH 2 -, -CH 2 CH 2 -, -CH 2 -O-CH 2 - or C 2 H 3 (X)-O-C 2 H 3 (X<SP>1</SP>)-, wherein X and X<SP>1</SP> are the same or different and each is H or C 1-3 alkyl, provided that R and R<SP>1</SP> are not both CH 3 when R<SP>2</SP> and R<SP>3</SP> are both H and A is -CH 2 - or -CH 2 CH 2 - or when R<SP>2</SP> and R<SP>3</SP> are either both H or both CH 3 when A is -CH 2 .CH 2 -O-CH 2 .CH 2 - and their preparation. The compounds are obtained by one of the following methods: (a) reacting in liquid mediums ethers of the Formula IV: wherein Z is a reactive nucleophilic atom or group; B is R or R<SP>1</SP>, and E is R<SP>2</SP> or R<SP>3</SP>, with alkali metal salts of p-hydroxyacylanilides of the Formula III: (b) acylating amines of the formula wherein one of R<SP>4</SP> is H and the other is also H or is a group M.CO- where M is one of R and R<SP>1</SP>; or (c) reacting alkali metal salts of phydroxyacylanilides of Formula III above with compounds of the formula Z-A-Z. Bis - [# - (4 - acetamidophenoxy)ethyl] ether is obtained by methods (a) to (c) above. Bis - [# - (N - methyl - 4 - acetamidophenoxy)- ethyl] ether is made by reacting bis-(2-chloroethyl) ether with N-methyl-4-acetamidophenol, resulting in the acetylation of 4-methylaminophenol sulphate. 2 - Chloroethyl - 2<SP>1</SP> - (4 - acetamidophenoxy)- ethyl ether is obtained by reacting bis-(2-chloroethyl) ether with 4-acetamidophenol. 1,2 - Bis - (4 - acetamidophenoxy) ethane is obtained by reacting 4-acetamidophenol with 1,2-dibromoethane. Bis - (4 - acetamidophenoxy) methane is prepared by reacting 4<SP>1</SP>-hydroxyacetanilide with methylene chloride in dimethyl sulphoxide in the presence of potassium t.-butoxide.
GB3466871A 1970-09-01 1971-07-23 Anthelmintic ethers and formulations thereof Expired GB1380882A (en)

Priority Applications (17)

Application Number Priority Date Filing Date Title
GB3466871A GB1380882A (en) 1970-09-01 1971-07-23 Anthelmintic ethers and formulations thereof
US174986A US3896235A (en) 1970-09-01 1971-08-25 Anthelmintic ethers and composition thereof
DE2166359*A DE2166359A1 (en) 1970-09-01 1971-08-31 RECTANGULAR CLIP ON (4-ACYLAMIDOPHENOXY) -ALKYL RECTANGULAR CLIP FOR -AETHER AND A METHOD FOR MAKING IT
DE2143570A DE2143570C3 (en) 1970-09-01 1971-08-31 Medicines to control liver fluke infections in mammals
IE1101/71A IE35575B1 (en) 1970-09-01 1971-08-31 Anthelmintic ethers and formulations thereof
IL7137620A IL37620A (en) 1970-09-01 1971-08-31 Bis(acylamino-phenoxy)alkyl ethers,their preparation and anthelmintic compositions containing them
IT7152589A IT1056014B (en) 1970-09-01 1971-08-31 ETERNAL ANTIELMINTICI AND PROCEDURE FOR THEIR PRODUCTION
CA121,845A CA995688A (en) 1970-09-01 1971-08-31 Anthelmintic ethers and formulations thereof
DK426671A DK136358B (en) 1970-09-01 1971-08-31 Analogous process for the preparation of di- (N-acyl-p-aminophenoxy) -alkylene derivatives or acid addition salts thereof.
BE772033A BE772033A (en) 1970-09-01 1971-08-31 ANTHELMINTIC ETHERS AND COMPOSITIONS CONTAINING
FI2432/71A FI55026C (en) 1970-09-01 1971-08-31 FOER REFRIGERATION FOAM FRAMSTAELLNING AV INAELVSMASK FOERGOERANDE TRIETERFOERENINGAR
NO713241A NO134866C (en) 1970-09-01 1971-08-31
FR7131600A FR2105171B1 (en) 1970-09-01 1971-09-01
NLAANVRAGE7112023,A NL169585C (en) 1970-09-01 1971-09-01 METHOD FOR PREPARING A PHARMACEUTICAL PREPARATION AGAINST LIVER BONE INFECTIONS, DOSED PHARMACEUTICAL PREPARATION AND METHOD FOR PREPARING THE ACTIVE SUBSTANCES
JP7197094A JPS5542966B1 (en) 1970-09-01 1971-12-01
CA253,179A CA1011654A (en) 1970-09-01 1976-05-25 Pharmaceutical formulations containing anthelmintic ethers
DK111277A DK111277A (en) 1970-09-01 1977-03-14 PROCEDURE FOR THE PREPARATION OF A PHARMACEUTICAL PREPARATION FOR THE TREATMENT OF LIVER RATE INFECTIONS IN MAMMALS

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB4187170 1970-09-01
GB4187270 1970-09-01
GB3466871A GB1380882A (en) 1970-09-01 1971-07-23 Anthelmintic ethers and formulations thereof
GB4049671 1971-08-31

Publications (1)

Publication Number Publication Date
GB1380882A true GB1380882A (en) 1975-01-15

Family

ID=27448845

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3466871A Expired GB1380882A (en) 1970-09-01 1971-07-23 Anthelmintic ethers and formulations thereof

Country Status (1)

Country Link
GB (1) GB1380882A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2736507A1 (en) * 1976-08-13 1978-02-16 Wellcome Found ANTIHELMINTHIC PREPARATIONS

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2736507A1 (en) * 1976-08-13 1978-02-16 Wellcome Found ANTIHELMINTHIC PREPARATIONS

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Legal Events

Date Code Title Description
416 Proceeding under section 16 patents act 1949
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee