GB770411A - Improvements in aminophenoxyalkane derivatives - Google Patents
Improvements in aminophenoxyalkane derivativesInfo
- Publication number
- GB770411A GB770411A GB4765/54A GB476554A GB770411A GB 770411 A GB770411 A GB 770411A GB 4765/54 A GB4765/54 A GB 4765/54A GB 476554 A GB476554 A GB 476554A GB 770411 A GB770411 A GB 770411A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- formula
- compound
- carbon atoms
- compounds
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/32—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
- C07C275/34—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The invention comprises compounds of the formula <FORM:0770411/IV(b)/1> and acid addition salts thereof, in which R1 is a straight or branched chain alkyl group having from 1 to 6 carbon atoms, or a cycloalkyl group, or a group of the general formula <FORM:0770411/IV(b)/2> wherein R4 is hydrogen or an alkyl group of 1 to 3 carbon atoms which may carry an amino group as a substituent, an alkoxy group of 1 to 3 carbon atoms, or a benzyloxy, acyl, carboxy, alkoxycarbonyl, carbamoyl, cyano, nitro, halogen, hydroxy, alkylsulphonyl or N-nitroso-N-alkylamino group or a group NR5R6 in which R5 is an acyl, alkoxycarbonyl, alkylsulphonyl or carbamoyl group and R6 is hydrogen or an alkyl group of 1 to 4 carbon atoms which may optionally carry at least one hydroxyl group on carbon atoms other than that adjacent the nitrogen atom; R2 and R3 are the same or different and are hydrogen or alkyl groups of 1 to 4 carbon atoms which may optionally carry one or more hydroxyl groups on carbon atoms other than that adjacent the nitrogen atom, and M is an aliphatic hydrocarbon chain of 1 to 8 carbon atoms which optionally contains one double or triple bond. Preferred products comprise compounds wherein the group NR5R6 is in the para position and R5 is a methoxy- or ethoxycarbonyl group or an acetyl group, R6 is hydrogen or methyl; NR2R3 is amino, methylamino or dimethylamino and -CH2-M-CH2- is a butane, butene, pentane, hexane, heptane or octane residue. The products are prepared by converting a compound of the formula <FORM:0770411/IV(b)/3> in which R8 is a group convertible into the group NR2R3 and R7 is a group as defined for R1 to give the desired compound. In the above process R7 may or may not be identical with the desired group R1 and in the latter case the synthesis includes the step, for example, of converting one of the groups defined for R4 into another such group. Conversion of the group R8 into the group NR2R3 may be effected by the following methods; (A) when NR2R3 is to be a primary amino group; reduction of nitro, aldimine or azo groups, for example the reduction of a nitro group by means of iron and a dilute acid; removal of a protecting group W from a group -NHW, for example an acyl, toluene-p-sulphonyl or alkoxycarbonyl group may be removed by hydrolysis; and the amination of a halogen atom; (B) when NR2R3 is to be a secondary amino group; the removal of a protecting group W from a group -NR2W, and (C) where NR2R3 is to be a tertiary amino group; pyrolysis or hydrolysis of the corresponding quaternary amino compound. The intermediate compound of the formula III may be made by reacting an a : o -disubstituted compound of the formula <FORM:0770411/IV(b)/4> successively in either order with a compound R7Y and a disubstituted benzene of the formula <FORM:0770411/IV(b)/5> wherein X and Y are groups capable of reacting together to form an ether linkage, for example Y may be a hydroxy group and -X may be halogen, e.g. bromine, alkanesulphonyloxy, such as methanesulphonyloxy, arenesulphonyloxy, such as p-toluene sulphonyloxy or aralkanesulphonyloxy, such as benzylsulphonyloxy. Where the group NR2R3 is to be a tertiary amino group, this group may already be present as the group R1 in the formula V, in which case the desired product is obtained directly by reacting the compound of formula IV successively with the compound R7Y and the compound of formula V. The products are used as therapeutic agents, preferred compounds having therapeutic activity being 1-(4-methoxycarbonylmethylaminophenoxy) - 4 - (4 - methylaminophenoxy) but-2-ene, 1-(4-cyanophenoxy)-4 - (4 - methylaminophenoxy) butane, 1 - (4 - cyanophenoxy) - 4 - (4 - aminophenoxy) butane and 1 - cyclohexyloxy - 5 - (4 - aminophenoxy) pentane. Examples are given of the preparation of many compounds of the formula I wherein R1 is chosen from phenyl, p-acetamidophenyl, p-tolyl, p-chlorophenyl, p-methoxyphenyl, p - carbethoxyphenyl, p - carbamoylphenyl, p - methylsulphonylphenyl, p - valeramidophenyl, p - nitrophenyl, p - cyanophenyl, p - benzyloxyphenyl, p - hydroxyphenyl, hexyl cyclohexyl, p - ethoxycarbonamidophenyl, o-, m- and p-ethoxycarbonmethylamidophenyl, p-pentyloxycarbonamidophenyl, p-bromophenyl, p - acetylphenyl, p - ureidophenyl, methyl, propyl, p - acetmethylamidophenyl, p - N - nitrosomethylaminophenyl, p - carboxyphenyl and p-methanesulphonamidophenyl groups. Starting materials. Phenoxyalkyl bromides, for example p-nitro-, p-acetamido-, p-acetmethylamido-, p - ethoxycarbonamido-, p - ethoxycarbonmethylamido-, p - nitrosomethylamino- and p-cyano-, phenoxyalkyl bromides are made by the reaction of the appropriate substituted phenol with an a : o -dibromoalkane; similarly phenoxyalkenyl bromides such as the p-ethoxycarbonamido-, p-acetamido- and p - N - nitrosomethylamino - derivatives of 1 - bromo-4-phenoxy - but - 2 - ene; 1 - bromo - 6 - (p - ethoxycarbonamidophenoxy) hex - 3 - ene and 1 - bromo - 7 - (p - acetamidophenoxy) hept-3 (or (4)-ene are prepared. By reaction of these bromo compounds with compounds of the formula R7Y or compounds of the formula V as defined above, and more especially with hydroxy derivatives corresponding to the groups specified for R1 in the examples, corresponding intermediate compounds of the formula III are obtained. Intermediates of the formula III, wherein R8 is a quaternary ammonium group are also described. Specifications 749,907, 749,923, 758,382, 765,957 and 770,410 are referred to in the first Provisional Specification.
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BE535847D BE535847A (en) | 1954-02-18 | ||
GB4765/54A GB770411A (en) | 1954-02-18 | 1954-02-18 | Improvements in aminophenoxyalkane derivatives |
ES0220192A ES220192A1 (en) | 1954-02-18 | 1955-02-17 | Improvements in aminophenoxyalkane derivatives |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB4765/54A GB770411A (en) | 1954-02-18 | 1954-02-18 | Improvements in aminophenoxyalkane derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
GB770411A true GB770411A (en) | 1957-03-20 |
Family
ID=9783372
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB4765/54A Expired GB770411A (en) | 1954-02-18 | 1954-02-18 | Improvements in aminophenoxyalkane derivatives |
Country Status (3)
Country | Link |
---|---|
BE (1) | BE535847A (en) |
ES (1) | ES220192A1 (en) |
GB (1) | GB770411A (en) |
Cited By (4)
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 |
US3142703A (en) * | 1962-04-20 | 1964-07-28 | Herbert C Stecker | Trifluoroalkoxy-substituted anilides and germicidal compositions obtained therewith |
FR2405928A1 (en) * | 1977-06-28 | 1979-05-11 | Sumitomo Chemical Co | PROCESS FOR THE PRODUCTION OF N'-PHENYL-N-METHYLUREE DERIVATIVES, NEW PRODUCTS THUS OBTAINED AND THEIR APPLICATION AS HERBICIDES |
GB2271163A (en) * | 1992-10-02 | 1994-04-06 | Latty International Ltd | Compressing a valve stem seal |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3903404A1 (en) * | 1989-02-06 | 1990-08-09 | Hoechst Ag | PYRIMID INTRION DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF, CONTAINERS THEREOF AND THEIR USE AS A PEST CONTROL |
-
0
- BE BE535847D patent/BE535847A/xx unknown
-
1954
- 1954-02-18 GB GB4765/54A patent/GB770411A/en not_active Expired
-
1955
- 1955-02-17 ES ES0220192A patent/ES220192A1/en not_active Expired
Cited By (4)
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 |
US3142703A (en) * | 1962-04-20 | 1964-07-28 | Herbert C Stecker | Trifluoroalkoxy-substituted anilides and germicidal compositions obtained therewith |
FR2405928A1 (en) * | 1977-06-28 | 1979-05-11 | Sumitomo Chemical Co | PROCESS FOR THE PRODUCTION OF N'-PHENYL-N-METHYLUREE DERIVATIVES, NEW PRODUCTS THUS OBTAINED AND THEIR APPLICATION AS HERBICIDES |
GB2271163A (en) * | 1992-10-02 | 1994-04-06 | Latty International Ltd | Compressing a valve stem seal |
Also Published As
Publication number | Publication date |
---|---|
ES220192A1 (en) | 1955-07-01 |
BE535847A (en) | 1900-01-01 |
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