GB1038185A - New diphenyl ethers and processes for their production, and pharmaceutical compositions containing them - Google Patents
New diphenyl ethers and processes for their production, and pharmaceutical compositions containing themInfo
- Publication number
- GB1038185A GB1038185A GB732864A GB732864A GB1038185A GB 1038185 A GB1038185 A GB 1038185A GB 732864 A GB732864 A GB 732864A GB 732864 A GB732864 A GB 732864A GB 1038185 A GB1038185 A GB 1038185A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ether
- hydroxy
- amino
- methoxy
- dichloro
- 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
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
- A01N31/16—Oxygen or sulfur directly attached to an aromatic ring system with two or more oxygen or sulfur atoms directly attached to the same aromatic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
- C08K5/136—Phenols containing halogens
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Environmental Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Biochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Textile Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention relates to compounds of the general formula <FORM:1038185/C2/1> wherein X and Y independently of each other are chlorine or bromine and Z is hydrogen chlorine or bromine. Among many compounds claimed per se are 2-hydroxy-4,41-dichloro- and 2 - hydroxy - 4,21,41, trichlorodiphenyl ether; 2 - hydroxy - 4,41 - dibromo - and 2 - hydroxy-4,21,41 - tribromodiphenyl ether; 2 - hydroxy-4 - chloro - 41 - bromodiphenyl ether; 2 - hydroxy, 4-bromo, 21,41-dichlorodiphenyl ether. The compounds may be prepared by (a) diazotizing and forming the diazonium salt e.g. sulphate of a substituted o-amino diphenyl ether of the general formula <FORM:1038185/C2/2> e.g. by nitrosyl sulphuric acid or sodium nitrite in sulphuric acid and boiling in water, an aqueous acid or 50-80 DEG C. sulphuric acid or in a higher boiling inert organic solvent; or (b) dealkylating by known methods for the cleavage of aryl-alkyl ethers an o-alkoxy diphenyl ether of the general formula <FORM:1038185/C2/3> where R is a low alkyl radical e.g. by treatment with aluminium chloride in an inert solvent, or by heating with concentrated aqueous hydrobromic acid, with hydrogen bromide in glacial acetic acid or a mixture of hydrobromic acid and acetic acid; or (c) by forming a diazonium salt of the compound of the general formula <FORM:1038185/C2/4> and converting it to the corresponding compound containing hydrogen instead of the amino group e.g. by boiling in low alkanol or dilute hydrophosphoric acid or until the evolution of N ceases; (d) by producing from the compounds of the general formula <FORM:1038185/C2/5> in which one or two of the symbols X1, Y1 and Z1 represent the amino group and the remaining symbol(s) have the meaning(s) given for X, Y or Z above, a diazonium salt and converting the latter into the corresponding compound containing chlorine or bromine instead of the original amino groups X1, Y1 or Z1 e.g. by treating the diazonium salt, in particular the chloride or bromide, in aqueous medium with cuprous chloride or cuprous bromide, or with the corresponding halogen hydracids in the presence of copper powder. In an example 2-amino-4,41-dichlorodiphenyl ether is added to nitrosyl sulphuric acid in concentrated sulphuric acid. After stirring, water is poured in while cooling with ice and o-dichlorobenzene added and the mixture boiled until no more diazo compounds can be traced when the upper organic phase is removed, caustic soda added and the o-dichlorobenzene distilled off with steam. The aqueous residue of this steam distillation contains the 2-hydroxy - 4,41 - dichlorodiphenyl ether dissolved therein as the sodium salt from which the 2 - hydroxy - 4,41 - dichlorodiphenyl ether is obtained by treatment with hydrochloric acid. By using instead of 2-amino-,4,41-dichlorodiphenyl ether the following: 2-amino-4,21,41-trichlorodiphenyl ether, 2-amino-4-chloro-41-bromodiphenyl ether, 2 - amino - 4 - bromo - 41-chlorodiphenyl ether, 2 - amino - 4,41 - di-bromodiphenyl ether or 2 - amino - 4,21,41-tribromodiphenyl ether the following substituted diphenyl ethers are respectively obtained: 2-hydroxy-4,21,41-trichloro-, 2-hydroxy-4 - chloro - 41 - bromo - 2 - hydroxy - 4 - bromo - 41 - chloro - 2 - hydroxy - 4,41 - dibromo -, and 2 - hydroxy - 4,21,41 - tribromodiphenyl ether. Other examples are given. Starting material 2-hydroxy - 21 - amino - 4,41 - dichloro diphenyl ether for the preparation of 2-hydroxy-4,41-dichlorodiphenyl ether therefrom by forming the diazo salt is prepared by reacting 2-methoxy - 4 - chlorophenol and 2,5 - dichloro - 1 -nitrobenzene to produce 2-methoxy-21-nitro-4,41-dichlorodiphenyl ether which is reduced to produce the 2-methoxy-21-amino-4,41-dichloro diphenyl ether from which the corresponding 2-hydroxy compound is produced by reaction with hydrobromic acid and NaOH. Another starting material 2-methoxy-4,21,41-trichloro diphenyl ether used to obtain 2-hydroxy-4,21, 41-trichlor diphenyl ether is produced by reacting 4-chloro-2-methoxy phenol with 3,4-dichloro-1-nitrobenzen to produce 2-methoxy-4,21 - dichloro - 41 - nitrodiphenyl which is catalytically hydrogenated to produce 2-methoxy-4,21-dichloro-41-aminodiphenyl ether and which is then diazotized and treated with HCl to yield 2-methoxy-4,21,41-trichlorodiphenyl ether.ALSO:Compounds of the general formula <FORM:1038185/A5-A6/1> wherein X and Y independently of each other are chlorine or bromine and Z is hydrogen chlorine or bromine are used as active ingredients for disinfectants for the hands, cosmetics, ointments for wounds, eye ointments and other agents for external use, as well as active ingredients for internal use e.g. tablets for the disinfection of the mouth and throat and tablets and sugar coated tablets (dragees) for the disinfection of the intestinal system and urinal tract.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH225063A CH406127A (en) | 1963-02-22 | 1963-02-22 | Process for the antimicrobial finishing of textiles |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1038185A true GB1038185A (en) | 1966-08-10 |
Family
ID=4229370
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB732964A Expired GB1022744A (en) | 1963-02-22 | 1964-02-21 | New phenolic antimicrobial compositions |
GB732864A Expired GB1038185A (en) | 1963-02-22 | 1964-02-21 | New diphenyl ethers and processes for their production, and pharmaceutical compositions containing them |
GB739964A Expired GB1024022A (en) | 1963-02-22 | 1964-02-21 | Process and materials for protection of organic materials against micro-organism contamination |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB732964A Expired GB1022744A (en) | 1963-02-22 | 1964-02-21 | New phenolic antimicrobial compositions |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB739964A Expired GB1024022A (en) | 1963-02-22 | 1964-02-21 | Process and materials for protection of organic materials against micro-organism contamination |
Country Status (15)
Country | Link |
---|---|
AT (5) | AT277471B (en) |
AU (1) | AU278661B2 (en) |
BE (2) | BE644154A (en) |
BR (2) | BR6457019D0 (en) |
CH (4) | CH406127A (en) |
DE (2) | DE1492346A1 (en) |
DK (3) | DK109146C (en) |
ES (4) | ES296707A1 (en) |
FI (1) | FI41831B (en) |
FR (3) | FR1386731A (en) |
GB (3) | GB1022744A (en) |
IT (1) | IT1149232B (en) |
MY (2) | MY6900159A (en) |
NL (2) | NL123731C (en) |
SE (3) | SE301324B (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4355189A (en) * | 1980-02-08 | 1982-10-19 | Hoechst Aktiengesellschaft | Process for the preparation of 4-phenoxyphenols |
US4512987A (en) * | 1982-07-15 | 1985-04-23 | Ciba-Geigy Corporation | New pharmaceutical preparations |
US4587262A (en) * | 1982-06-18 | 1986-05-06 | Imperial Chemical Industries Plc | Halogenophenyl glyceride esters for use in the prophylaxis and/or therapy of acne vulgaris |
US5286492A (en) * | 1990-05-03 | 1994-02-15 | Reckitt & Colman Products Limited | Method of treatment of Heliobacter pylori infections with triclosan |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4118332A (en) * | 1965-10-22 | 1978-10-03 | Colgate-Palmolive Company | Synergistic antibacterial composition containing mixtures of certain halogenated diphenyl ethers and trichlorocarbanilides |
CH1085667A4 (en) * | 1967-08-01 | 1969-03-14 | ||
US4057648A (en) | 1970-05-16 | 1977-11-08 | Ciba-Geigy Corporation | Compositions for the control of microorganisms |
BE750969A (en) | 1970-05-26 | 1970-11-03 | Geigy Ag J R | COMPOSITION TO FIGHT MICRO-ORGANISMS, |
US4284828A (en) * | 1978-11-21 | 1981-08-18 | Ciba-Geigy Corporation | Process for the manufacture of 4,5-dichloro-2-(4-chlorophenoxy)phenol |
US4326978A (en) * | 1979-11-16 | 1982-04-27 | Ciba-Geigy Corporation | Soap bar with antimicrobial action |
US4490562A (en) * | 1982-02-11 | 1984-12-25 | Ciba-Geigy Corporation | Process for the preparation of a very pure commercial form of 4,2',4'-trichloro-2-hydroxydiphenyl ether |
JPS611615A (en) * | 1984-06-12 | 1986-01-07 | Yougo Takaoka | External drug for athlete's foot |
WO1995008332A1 (en) * | 1993-09-20 | 1995-03-30 | The Procter & Gamble Company | Use of triclosan phosphates for the treatment of gastrointestinal disorders due to heliobacter infection |
FR2765469B1 (en) * | 1997-07-07 | 1999-09-24 | Elysees Balzac Financiere | MATERIAL BASED ON REGENERATED CELLULOSE HAVING SUSTAINABLE RESISTANCE TO MICROORGANISMS AND PREPARATION THEREOF |
EP0908553A3 (en) * | 1997-10-13 | 2001-03-07 | Ciba SC Holding AG | Process for the treatment of textile materials with an antimicrobial agent |
US5968207A (en) * | 1998-02-20 | 1999-10-19 | Milliken & Company | Esterified triclosan derivatives as improved textile antimicrobial agents |
US6258455B1 (en) * | 1999-03-29 | 2001-07-10 | Sweports Limited | Antimicrobial ultra-microfiber cloth |
JP2007530499A (en) * | 2004-03-23 | 2007-11-01 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | Disinfectant composition |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE569726C (en) * | 1930-05-09 | 1933-02-07 | Ig Farbenindustrie Ag | Process for the preparation of bis (halo-oxyaryl) oxides |
-
1963
- 1963-02-22 CH CH225063A patent/CH406127A/en unknown
- 1963-02-22 CH CH1764066A patent/CH431780A/en unknown
-
1964
- 1964-02-01 BR BR15701964A patent/BR6457019D0/en unknown
- 1964-02-19 CH CH196564A patent/CH450347A/en unknown
- 1964-02-19 CH CH1509564A patent/CH450348A/en unknown
- 1964-02-20 FI FI33364A patent/FI41831B/fi active
- 1964-02-21 FR FR964735A patent/FR1386731A/en not_active Expired
- 1964-02-21 BR BR15701864A patent/BR6457018D0/en unknown
- 1964-02-21 IT IT393764A patent/IT1149232B/en active
- 1964-02-21 ES ES296707A patent/ES296707A1/en not_active Expired
- 1964-02-21 ES ES296708A patent/ES296708A1/en not_active Expired
- 1964-02-21 BE BE644154D patent/BE644154A/xx unknown
- 1964-02-21 DE DE1964G0039915 patent/DE1492346A1/de not_active Ceased
- 1964-02-21 AU AU41194/64A patent/AU278661B2/en not_active Expired
- 1964-02-21 DK DK95966A patent/DK109146C/en active
- 1964-02-21 SE SE215764A patent/SE301324B/xx unknown
- 1964-02-21 NL NL6401661A patent/NL123731C/xx active
- 1964-02-21 ES ES296710A patent/ES296710A1/en not_active Expired
- 1964-02-21 DK DK85864A patent/DK108923C/en active
- 1964-02-21 ES ES296709A patent/ES296709A1/en not_active Expired
- 1964-02-21 AT AT345167A patent/AT277471B/en not_active IP Right Cessation
- 1964-02-21 GB GB732964A patent/GB1022744A/en not_active Expired
- 1964-02-21 GB GB732864A patent/GB1038185A/en not_active Expired
- 1964-02-21 BE BE644153A patent/BE644153A/xx unknown
- 1964-02-21 AT AT357565A patent/AT246725B/en active
- 1964-02-21 GB GB739964A patent/GB1024022A/en not_active Expired
- 1964-02-21 NL NL6401664A patent/NL6401664A/xx unknown
- 1964-02-21 AT AT148164A patent/AT245554B/en active
- 1964-02-21 AT AT148064A patent/AT262512B/en active
- 1964-02-21 DK DK96066A patent/DK109518C/en active
- 1964-02-21 DE DEG39916A patent/DE1216882B/en active Pending
- 1964-02-21 FR FR964734A patent/FR1385825A/en not_active Expired
- 1964-02-21 AT AT357665A patent/AT245555B/en active
- 1964-05-20 FR FR975146A patent/FR3486M/fr not_active Expired
-
1966
- 1966-02-21 SE SE219266A patent/SE309781B/xx unknown
- 1966-02-21 SE SE219166A patent/SE309780B/xx unknown
-
1969
- 1969-12-30 MY MY6900159A patent/MY6900159A/en unknown
- 1969-12-30 MY MY6900160A patent/MY6900160A/en unknown
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4355189A (en) * | 1980-02-08 | 1982-10-19 | Hoechst Aktiengesellschaft | Process for the preparation of 4-phenoxyphenols |
US4587262A (en) * | 1982-06-18 | 1986-05-06 | Imperial Chemical Industries Plc | Halogenophenyl glyceride esters for use in the prophylaxis and/or therapy of acne vulgaris |
US4512987A (en) * | 1982-07-15 | 1985-04-23 | Ciba-Geigy Corporation | New pharmaceutical preparations |
US5286492A (en) * | 1990-05-03 | 1994-02-15 | Reckitt & Colman Products Limited | Method of treatment of Heliobacter pylori infections with triclosan |
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