US2459062A - Quaternary ammonium compounds - Google Patents
Quaternary ammonium compounds Download PDFInfo
- Publication number
- US2459062A US2459062A US521588A US52158844A US2459062A US 2459062 A US2459062 A US 2459062A US 521588 A US521588 A US 521588A US 52158844 A US52158844 A US 52158844A US 2459062 A US2459062 A US 2459062A
- Authority
- US
- United States
- Prior art keywords
- parts
- quaternary ammonium
- chloride
- benzene
- ammonium 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 - Lifetime
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/24—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton
Definitions
- the present invention is concerned with the production of new organic ammonium compounds which are adapted for various uses, more particularly as germicidal agents, wetting agents, and softening agents for textiles and the like.
- quaternary ammonium salts may be prepared by treating a tertiary amine of the formulain whichR, R1 and R2 represent the molecular groups above referred to, with an alkylating agent such as an alkyl halide, dialkyl sulfate, aralkyl chloride, etc.
- an alkylating agent such as an alkyl halide, dialkyl sulfate, aralkyl chloride, etc.
- 'ymyri'stamidopropyldimethylamine treated with benzyl chloride produces the ammonium salt
- '1 myrlstamidopropyldimethylbenzylammonium chloride according to the reaction Reactions which may be involved in the preparation of the tertiary amine may be outlined as follows:
- step (3) the acid chloride
- Ri E-Cl may be used in place of the acid.
- Example 1 Into 545 parts of a 25% aqueous solution of dimethyl amine, cooled with ice and water, there were added from a dropping funnel 170 parts of acrylonltrile. The rate of addition of the nitrile was controlled so that the temperature in the reaction vessel remained below 20 C. After the cold reaction mixture had stood for one hour, it
- This compound is an a excellent germicidal agent. It has been found effective against Staphylococcus aureus in a dilution of one part in 25,000 at 37 C. during a test of five minutes.
- the phenol coefficient of the compound is in the range of 277 to 333.
- This product is also particularly suitable as a wetting agent for cotton fabrics.
- Example II A mixture consisting of 30 parts of benzene. 8.1 parts of y-capyrylamidopropyldimethyiamine and 5 parts of benzyl chloride was heated at reflux temperature for six hours. After removing the benzene, the -caprylamidopropyldimethylbenzylammonium chloride was obtained as a viscous syrup.
- Example II Two parts of benzyl chloride were gradually added to a solution of 4.5 parts of 'y-palmitamidopropyldimethylamine dissolved in 30 parts of benzene. The resulting solution was refluxed for about four hours. The benzene was removed by vacuum distillation, leaving the quaternary ammonium salt, 1-palmitamidopropyidimethylbenzylammonium chloride, as an opaque solid, readily soluble in water. This product is an effective germicide, and also a good softening and wetting agent for textile fabrics.
- Example IV A solution of 6.9 parts of y-lauramidopropyl.
- quaternary ammonium salts can be prepared according to the procedure followed in the above examples, such as the 'y-myristamidopropyldimethyl a-naphthylmethylammonium chloride, 'y-oleamidopropyldimethylbenzylammonium chloride, -lauramidopropyldiethylmethylammonium bromide, 'y-stearamidopropyldimethylbenzylammonium chloride and 'y-myristamidopropyldimethylailyiammonium bromide.
- the y-steararnidopropyldimethylbenzylammonium chloride is an excellent softening agent for rayon and cotton fibers, and acts as a permanent re-wetting agent on fabrics.
- a germicidal composition containing as an effective germicidal agent a compound of the formula OH; CH: R.CO.NH.CHQCHIOHJIf-CHIR1 CH: CH;
- wnich R. is an alkyl radical of 11-13 carbon atoms inclusive and Hal is a halogen.
- a germicidal composition comprisinz, as an effective germicidal agent, an aqueous solution of a compound of the formula H2O CH:
Description
Patented Jan. 11, 1949 UNITED STATES PATENT OFFICE QUATERNARY AMMONIUM COMPOUNDS Elmer W. Cook, New York, N. Y., and Philip B. Moss, Greenwich, Conn., assignors to American Cyanamid Company, New York, N. Y., a corporation of Maine No Drawing. Application February 8, 1944,
Serial No. 521,588
Claims. 1
The present invention is concerned with the production of new organic ammonium compounds which are adapted for various uses, more particularly as germicidal agents, wetting agents, and softening agents for textiles and the like.
These compounds are of the quaternary ammonium type which conform to the general formula The new products are in part crystalline, in-
part thickly liquid, viscous substances which in general dissolve readily in water and form stable aqueous solutions. In view of their dispersing and disinfecting properties, they exert a remarkable action as wetting and emulsifying agents and also as antiseptics. They are practically odorless and relatively non-toxic to man.
Representative compounds which fall within the scope of this invention are:
( CIHI 09H;
These quaternary ammonium salts may be prepared by treating a tertiary amine of the formulain whichR, R1 and R2 represent the molecular groups above referred to, with an alkylating agent such as an alkyl halide, dialkyl sulfate, aralkyl chloride, etc. Thus, -for example, 'ymyri'stamidopropyldimethylamine treated with benzyl chloride produces the ammonium salt, '1 myrlstamidopropyldimethylbenzylammonium chloride according to the reaction Reactions which may be involved in the preparation of the tertiary amine may be outlined as follows:
CH:=CHCN As an alternative method for step (3), the acid chloride,
Ri E-Cl may be used in place of the acid.
The invention is further illustrated by the following examples, the parts being by weight unless otherwise stated.
Example 1 Into 545 parts of a 25% aqueous solution of dimethyl amine, cooled with ice and water, there were added from a dropping funnel 170 parts of acrylonltrile. The rate of addition of the nitrile was controlled so that the temperature in the reaction vessel remained below 20 C. After the cold reaction mixture had stood for one hour, it
.vacuum distilled. 204.5 parts of N,N-dimethylpropylenediamine were collected, B. P. 134 C. at atmospheric pressure.
38 parts of myristyl chloride were added dropwise to a solution of 15.5 parts of N,N-dimethylpropylenediamine in 160 parts of benzene. After one hour of stirring, the benzene solution was washed with aqueous sodium hydroxide. The benzene layer was then washed once with water and the solvent removed by vacuum distillation. The residue was distilled at 208-215" C./1-2 mm, giving a solid distillate of y-myristamidopropyldimethylamine.
A solution of 6.2 parts of Y-myristamidopropyldimethylamine and 8.4 parts of benzyl chloride in 30 parts of benzene was refluxed during a period of four hours. The benzene was removed under vacuum, giving a light-colored, amorphous semi-solid at room temperature, which melts at about 54 C. to a clear, straw-colored liquid. This quaternary ammonium salt, 'y-myristamidopropyldimethylbenzylammonium chloride, is soluble in most organic solvents and forms a clear 25% solution in water.
This compound is an a excellent germicidal agent. It has been found effective against Staphylococcus aureus in a dilution of one part in 25,000 at 37 C. during a test of five minutes. The phenol coefficient of the compound is in the range of 277 to 333.
This product is also particularly suitable as a wetting agent for cotton fabrics.
Example II A mixture consisting of 30 parts of benzene. 8.1 parts of y-capyrylamidopropyldimethyiamine and 5 parts of benzyl chloride was heated at reflux temperature for six hours. After removing the benzene, the -caprylamidopropyldimethylbenzylammonium chloride was obtained as a viscous syrup.
Example II! Two parts of benzyl chloride were gradually added to a solution of 4.5 parts of 'y-palmitamidopropyldimethylamine dissolved in 30 parts of benzene. The resulting solution was refluxed for about four hours. The benzene was removed by vacuum distillation, leaving the quaternary ammonium salt, 1-palmitamidopropyidimethylbenzylammonium chloride, as an opaque solid, readily soluble in water. This product is an effective germicide, and also a good softening and wetting agent for textile fabrics.
Example IV A solution of 6.9 parts of y-lauramidopropyl.
dimethylamine and 4.5 parts of benzyl chloride in parts of benzene was refluxed during a period of four hours. After removing the solvent, the 'y-lauramidopropyldimethylbenzylammonium chloride was obtained as a colorless viscous mass, soluble in water. This product is a good germicide, and may be advantageously used for various disinfecting purposes.
Other quaternary ammonium salts can be prepared according to the procedure followed in the above examples, such as the 'y-myristamidopropyldimethyl a-naphthylmethylammonium chloride, 'y-oleamidopropyldimethylbenzylammonium chloride, -lauramidopropyldiethylmethylammonium bromide, 'y-stearamidopropyldimethylbenzylammonium chloride and 'y-myristamidopropyldimethylailyiammonium bromide.
The y-steararnidopropyldimethylbenzylammonium chloride is an excellent softening agent for rayon and cotton fibers, and acts as a permanent re-wetting agent on fabrics.
While the invention has been described with particular reference to specific embodiments, it is to be understood that it is not to be limited thereto but is to be construed broadly and restricted solely by the scope of the appended claims.
We claim:
l. A germicidal composition containing as an effective germicidal agent the quaternary ammonium compound of the following formula 2. A germicidal composition containing as an eifective germicidal agent the quaternary ammonium compound of the following formula CH; CH:
3. A germicidal composition containing as an effective germicidal agent a compound of the formula OH; CH: R.CO.NH.CHQCHIOHJIf-CHIR1 CH: CH;
in wnich R. is an alkyl radical of 11-13 carbon atoms inclusive and Hal is a halogen.
5. A germicidal composition comprisinz, as an effective germicidal agent, an aqueous solution of a compound of the formula H2O CH:
11.0 O.NH.C HaQHiCHnI-C H 5 in which R is an alkyl radical of 11-13 carbon atoms.
ELMER W. COOK. PHILIP H. MOSS.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PA'I'ENTS Number" Name Date 1,860,563 Wayne May 31, 1932 1,737,458 ,Hartmann et al. Nov. 26, 1939 20 2,262,741 De Groote Nov. 11, 1941 2,345,570 Bley Apr. 4, 1944 2,362,760 Maxwell Nov. 14, 1944
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US521588A US2459062A (en) | 1944-02-08 | 1944-02-08 | Quaternary ammonium compounds |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US521588A US2459062A (en) | 1944-02-08 | 1944-02-08 | Quaternary ammonium compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
US2459062A true US2459062A (en) | 1949-01-11 |
Family
ID=24077306
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US521588A Expired - Lifetime US2459062A (en) | 1944-02-08 | 1944-02-08 | Quaternary ammonium compounds |
Country Status (1)
Country | Link |
---|---|
US (1) | US2459062A (en) |
Cited By (36)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2589674A (en) * | 1947-05-24 | 1952-03-18 | American Cyanamid Co | Aliphatic amido propyl quaternary ammonium salts |
US2644003A (en) * | 1950-02-24 | 1953-06-30 | Geigy Ag J R | Quaternary ammonium compounds and their manufacture |
US2737509A (en) * | 1953-11-19 | 1956-03-06 | Jelling Murray | Carboxylic acid salts of n-dialkylaminoalkylamides |
US2785092A (en) * | 1953-08-11 | 1957-03-12 | Ciba Ltd | Condensation product and textile material softened therewith |
DE1031270B (en) * | 1951-08-17 | 1958-06-04 | American Cyanamid Co | Process for making structures made of vinyl resins antistatic |
US2862009A (en) * | 1952-12-12 | 1958-11-25 | Ciba Ltd | New water soluble quaternary ammonium salts |
US2950253A (en) * | 1953-07-29 | 1960-08-23 | Bohme Fettchemie Gmbh | Methods of washing textile fabrics |
US3060185A (en) * | 1958-04-30 | 1962-10-23 | Ciba Geigy Corp | Hydroxamic acid esters of alkanolamines |
US3082227A (en) * | 1961-09-27 | 1963-03-19 | American Cyanamid Co | Method of preparing a quaternary ammonium compound |
US3145137A (en) * | 1961-05-12 | 1964-08-18 | Monsanto Co | Alkanoylamidoalkyleneamines and their quaternary ammonium salts as fungicides |
US3260671A (en) * | 1962-11-23 | 1966-07-12 | Emery Industries Inc | Amide oxidation inhibitor for lubricants |
US3270039A (en) * | 1962-04-14 | 1966-08-30 | Henkel & Cie Gmbh | Addition compounds of surface active sulfuric acid semiester salts and sulfobetainesand the production thereof |
US3390158A (en) * | 1963-12-05 | 1968-06-25 | Spofa Vereinigte Pharma Werke | Aromatic quaternary ammonium salts with disinfectant activity |
US3410880A (en) * | 1963-10-30 | 1968-11-12 | Procter & Gamble | N-trialkylammonium imides of higher fatty acids |
US3492324A (en) * | 1963-04-26 | 1970-01-27 | I C I Organics Inc | Quaternary salts of tertiary amines |
US4012398A (en) * | 1975-09-16 | 1977-03-15 | Van Dyk & Company, Incorporated | Quaternary halides of mink oil amides |
US4168302A (en) * | 1976-03-29 | 1979-09-18 | The Richardson Company | Hair conditioning compositions containing a non-irritating cationic surfactant |
US4185098A (en) * | 1976-04-15 | 1980-01-22 | Hoechst Aktiengesellschaft | Disinfectant |
US4228042A (en) * | 1978-06-26 | 1980-10-14 | The Procter & Gamble Company | Biodegradable cationic surface-active agents containing ester or amide and polyalkoxy group |
US4239660A (en) * | 1978-12-13 | 1980-12-16 | The Procter & Gamble Company | Detergent composition comprising a hydrolyzable cationic surfactant and specific alkalinity source |
EP0327379A2 (en) * | 1988-02-05 | 1989-08-09 | CRODA INTERNATIONAL plc | Humectants |
US4965362A (en) * | 1988-07-23 | 1990-10-23 | Franz Merger | Joint preparation of 3-dialkylaminopropionitriles, bis-(2-cyanoethyl) ether and, if desired, ethylene-cyanohydrin |
WO1993002042A1 (en) * | 1991-07-18 | 1993-02-04 | Eastman Kodak Company | Amide-containing quaternary ammonium salts |
US5783604A (en) * | 1992-07-02 | 1998-07-21 | Garcia Nunez; Maria Rosalia | Germicidal compositions containing iodine compounds |
JP2004083562A (en) * | 2002-07-03 | 2004-03-18 | Asahi Denka Kogyo Kk | Antibacterial agent |
WO2004108125A1 (en) * | 2003-06-04 | 2004-12-16 | Megainpharm Gmbh | Coronavirus inactivating agent |
WO2007075101A1 (en) * | 2005-12-28 | 2007-07-05 | Obschestvo S Organichennoi Otvetstvennostyu Naucho-Proizvodstvennaya Firma 'flobi' | Method for determining concentration of c26h47cin2o in an aqueous medium |
US20090092648A1 (en) * | 2007-10-09 | 2009-04-09 | Ethicon, Inc. | Antimicrobial polymer compositions and the use thereof |
DE102008039254A1 (en) * | 2008-08-20 | 2010-02-25 | Megainpharm Gmbh | Medicament, useful e.g. for treating infectious- and purulent inflammatory diseases of e.g. eyes, comprises benzyl-dimethyl-(3-(myristoylamino)-propyl)-ammonium chloride, dimethyl-(3-(myristoylamino)-propyl)-amine oxide and solvent |
CN101100432B (en) * | 2006-07-04 | 2010-08-04 | 中国人民解放军军事医学科学院毒物药物研究所 | Method for synthesizing benzyldimethyl[3-(myristamide)propyl]ammonium chloride |
WO2011100994A1 (en) | 2010-02-19 | 2011-08-25 | Megainpharm Gmbh | Pharmaceutical comprising myramistin |
RU2626877C1 (en) * | 2016-04-07 | 2017-08-02 | Олег Ростиславович Михайлов | Crystalline b-modification of benzyldimethyl[3- (myristoylamino)propyl]ammonium of monohydrate chloride, method for its production and pharmaceutical composition based thereon |
RU2653597C1 (en) * | 2017-04-20 | 2018-05-16 | Юлия Александровна Корнева | Method for preparation of n-benzyl [1-(dodecinoylamino)-3-(dimethylamino)]propane ammonium chloride monohydrate |
RU2655603C1 (en) * | 2016-06-28 | 2018-05-29 | Юлия Александровна Корнева | Antiseptic on the basis of dodecanic acid |
RU2678093C1 (en) * | 2018-07-10 | 2019-01-23 | Федеральное государственное унитарное предприятие "Государственный научный центр "Научно-исследовательский институт органических полупродуктов и красителей" | Method for producing benzyldimethyl[3-(myristoylamino)-propyl]ammonium chloride monohydrate and pharmaceutical substance based thereon |
RU2776367C2 (en) * | 2020-03-30 | 2022-07-19 | Акционерное общество "Бофарм" | Drug |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1737458A (en) * | 1927-07-26 | 1929-11-26 | Chem Ind Basel | Quaternary ammonium compound and process of making same |
US1860563A (en) * | 1931-05-21 | 1932-05-31 | Truman B Wayne | Method of resolving petroleum emulsions |
US2262741A (en) * | 1940-10-11 | 1941-11-11 | Petrolite Corp | Composition of matter and process for preventing water-in-oil type emulsions resulting from acidization of calcareous oil-bearing strata |
US2345570A (en) * | 1938-10-07 | 1944-04-04 | North American Rayon Corp | Coagulating bath containing cationactive inhibitors |
US2362760A (en) * | 1943-01-12 | 1944-11-14 | Shell Dev | Insecticidal compositions |
-
1944
- 1944-02-08 US US521588A patent/US2459062A/en not_active Expired - Lifetime
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1737458A (en) * | 1927-07-26 | 1929-11-26 | Chem Ind Basel | Quaternary ammonium compound and process of making same |
US1860563A (en) * | 1931-05-21 | 1932-05-31 | Truman B Wayne | Method of resolving petroleum emulsions |
US2345570A (en) * | 1938-10-07 | 1944-04-04 | North American Rayon Corp | Coagulating bath containing cationactive inhibitors |
US2262741A (en) * | 1940-10-11 | 1941-11-11 | Petrolite Corp | Composition of matter and process for preventing water-in-oil type emulsions resulting from acidization of calcareous oil-bearing strata |
US2362760A (en) * | 1943-01-12 | 1944-11-14 | Shell Dev | Insecticidal compositions |
Cited By (47)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2589674A (en) * | 1947-05-24 | 1952-03-18 | American Cyanamid Co | Aliphatic amido propyl quaternary ammonium salts |
US2644003A (en) * | 1950-02-24 | 1953-06-30 | Geigy Ag J R | Quaternary ammonium compounds and their manufacture |
DE1031270B (en) * | 1951-08-17 | 1958-06-04 | American Cyanamid Co | Process for making structures made of vinyl resins antistatic |
US2862009A (en) * | 1952-12-12 | 1958-11-25 | Ciba Ltd | New water soluble quaternary ammonium salts |
US2950253A (en) * | 1953-07-29 | 1960-08-23 | Bohme Fettchemie Gmbh | Methods of washing textile fabrics |
US2785092A (en) * | 1953-08-11 | 1957-03-12 | Ciba Ltd | Condensation product and textile material softened therewith |
US2737509A (en) * | 1953-11-19 | 1956-03-06 | Jelling Murray | Carboxylic acid salts of n-dialkylaminoalkylamides |
US3060185A (en) * | 1958-04-30 | 1962-10-23 | Ciba Geigy Corp | Hydroxamic acid esters of alkanolamines |
US3145137A (en) * | 1961-05-12 | 1964-08-18 | Monsanto Co | Alkanoylamidoalkyleneamines and their quaternary ammonium salts as fungicides |
US3082227A (en) * | 1961-09-27 | 1963-03-19 | American Cyanamid Co | Method of preparing a quaternary ammonium compound |
US3270039A (en) * | 1962-04-14 | 1966-08-30 | Henkel & Cie Gmbh | Addition compounds of surface active sulfuric acid semiester salts and sulfobetainesand the production thereof |
US3260671A (en) * | 1962-11-23 | 1966-07-12 | Emery Industries Inc | Amide oxidation inhibitor for lubricants |
US3492324A (en) * | 1963-04-26 | 1970-01-27 | I C I Organics Inc | Quaternary salts of tertiary amines |
US3410880A (en) * | 1963-10-30 | 1968-11-12 | Procter & Gamble | N-trialkylammonium imides of higher fatty acids |
US3390158A (en) * | 1963-12-05 | 1968-06-25 | Spofa Vereinigte Pharma Werke | Aromatic quaternary ammonium salts with disinfectant activity |
US4012398A (en) * | 1975-09-16 | 1977-03-15 | Van Dyk & Company, Incorporated | Quaternary halides of mink oil amides |
US4168302A (en) * | 1976-03-29 | 1979-09-18 | The Richardson Company | Hair conditioning compositions containing a non-irritating cationic surfactant |
US4185098A (en) * | 1976-04-15 | 1980-01-22 | Hoechst Aktiengesellschaft | Disinfectant |
US4228042A (en) * | 1978-06-26 | 1980-10-14 | The Procter & Gamble Company | Biodegradable cationic surface-active agents containing ester or amide and polyalkoxy group |
US4239660A (en) * | 1978-12-13 | 1980-12-16 | The Procter & Gamble Company | Detergent composition comprising a hydrolyzable cationic surfactant and specific alkalinity source |
EP0327379A3 (en) * | 1988-02-05 | 1991-01-09 | CRODA INTERNATIONAL plc | Humectants |
EP0327379A2 (en) * | 1988-02-05 | 1989-08-09 | CRODA INTERNATIONAL plc | Humectants |
US4965362A (en) * | 1988-07-23 | 1990-10-23 | Franz Merger | Joint preparation of 3-dialkylaminopropionitriles, bis-(2-cyanoethyl) ether and, if desired, ethylene-cyanohydrin |
WO1993002042A1 (en) * | 1991-07-18 | 1993-02-04 | Eastman Kodak Company | Amide-containing quaternary ammonium salts |
US5783604A (en) * | 1992-07-02 | 1998-07-21 | Garcia Nunez; Maria Rosalia | Germicidal compositions containing iodine compounds |
JP2004083562A (en) * | 2002-07-03 | 2004-03-18 | Asahi Denka Kogyo Kk | Antibacterial agent |
WO2004108125A1 (en) * | 2003-06-04 | 2004-12-16 | Megainpharm Gmbh | Coronavirus inactivating agent |
WO2007075101A1 (en) * | 2005-12-28 | 2007-07-05 | Obschestvo S Organichennoi Otvetstvennostyu Naucho-Proizvodstvennaya Firma 'flobi' | Method for determining concentration of c26h47cin2o in an aqueous medium |
CN101100432B (en) * | 2006-07-04 | 2010-08-04 | 中国人民解放军军事医学科学院毒物药物研究所 | Method for synthesizing benzyldimethyl[3-(myristamide)propyl]ammonium chloride |
US20090092648A1 (en) * | 2007-10-09 | 2009-04-09 | Ethicon, Inc. | Antimicrobial polymer compositions and the use thereof |
US8691899B2 (en) * | 2007-10-09 | 2014-04-08 | Ethicon, Inc. | Antimicrobial polymer compositions and the use thereof |
CN101820931B (en) * | 2007-10-09 | 2014-04-02 | 伊西康公司 | Antimicrobial polymer compositions and the use thereof |
DE102008039254A1 (en) * | 2008-08-20 | 2010-02-25 | Megainpharm Gmbh | Medicament, useful e.g. for treating infectious- and purulent inflammatory diseases of e.g. eyes, comprises benzyl-dimethyl-(3-(myristoylamino)-propyl)-ammonium chloride, dimethyl-(3-(myristoylamino)-propyl)-amine oxide and solvent |
CN102869354A (en) * | 2010-02-19 | 2013-01-09 | 梅根医药股份有限公司 | Pharmaceutical comprising myramistin |
AU2011217530B2 (en) * | 2010-02-19 | 2014-01-16 | Megainpharm Gmbh | Pharmaceutical comprising myramistin |
WO2011101113A1 (en) | 2010-02-19 | 2011-08-25 | Megainpharm Gmbh | Pharmaceutical comprising myramistin |
WO2011100994A1 (en) | 2010-02-19 | 2011-08-25 | Megainpharm Gmbh | Pharmaceutical comprising myramistin |
CN102869354B (en) * | 2010-02-19 | 2015-12-16 | 梅根医药股份有限公司 | Comprise the pharmaceutical preparation of myramistin |
EA022283B1 (en) * | 2010-02-19 | 2015-12-30 | Мегаинфарм Гмбх | Pharmaceutical comprising benzyldimethyl[3-(myristoylamino)propyl]ammonium chloride |
MD4411C1 (en) * | 2010-02-19 | 2016-11-30 | Megainpharm Gmbh | Pharmaceutical including benzyldimethyl(3-[myristoylamino]propyl)-ammonium chloride and its use for the treatment and prevention of infectious and pyoinflammatory diseases of different etiology and localization |
RU2626877C1 (en) * | 2016-04-07 | 2017-08-02 | Олег Ростиславович Михайлов | Crystalline b-modification of benzyldimethyl[3- (myristoylamino)propyl]ammonium of monohydrate chloride, method for its production and pharmaceutical composition based thereon |
RU2655603C1 (en) * | 2016-06-28 | 2018-05-29 | Юлия Александровна Корнева | Antiseptic on the basis of dodecanic acid |
RU2653597C1 (en) * | 2017-04-20 | 2018-05-16 | Юлия Александровна Корнева | Method for preparation of n-benzyl [1-(dodecinoylamino)-3-(dimethylamino)]propane ammonium chloride monohydrate |
RU2678093C1 (en) * | 2018-07-10 | 2019-01-23 | Федеральное государственное унитарное предприятие "Государственный научный центр "Научно-исследовательский институт органических полупродуктов и красителей" | Method for producing benzyldimethyl[3-(myristoylamino)-propyl]ammonium chloride monohydrate and pharmaceutical substance based thereon |
RU2776367C2 (en) * | 2020-03-30 | 2022-07-19 | Акционерное общество "Бофарм" | Drug |
RU2802627C1 (en) * | 2022-07-19 | 2023-08-30 | Общество с ограниченной ответственностью "Цитера" | Method for producing benzyldimethyl[3-(myristoylamino)propyl]ammonium chloride monohydrate |
RU2812562C1 (en) * | 2023-02-03 | 2024-01-30 | Общество с ограниченной ответственностью "БратскХимСинтез" (ООО "БХС") | Method for producing benzyldimethyl[3-(myristoylamino)propyl]ammonium chloride monohydrate |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US2459062A (en) | Quaternary ammonium compounds | |
US2170111A (en) | Manufacture of amines | |
US2933529A (en) | Symmetrical diquaternary ammonium compounds | |
US2719156A (en) | Methylolated quaternary ammonium compounds | |
DE2424502A1 (en) | STYLE CONNECTIONS | |
JP4750499B2 (en) | Ionic liquid and antibacterial agent and antibacterial fiber using the same | |
US4118324A (en) | Fabric softeners | |
US2426891A (en) | N, n'-dioctadecyl-beta-amino-propionamide | |
US2302805A (en) | Composition for mothproofing | |
US2459088A (en) | Aliphatic amide-substituted propyl quaternary ammonium compounds | |
US2864866A (en) | Process for preparing surface-active materials | |
US2489363A (en) | Chlorinated derivatives of alkylene polyamines | |
US2253773A (en) | Treating, especially softening, cellulosic textile materials | |
US2313741A (en) | Organic compound and process of making the same | |
US2907791A (en) | Amphoteric surface-active organic compounds | |
US2520275A (en) | Aromatic diquaternary ammonium compounds | |
US4417895A (en) | Treatment of textiles with antimicrobial agents | |
US2411428A (en) | Aromatic substituted methyl alkyl ethers as insecticides | |
US2306185A (en) | Organic compounds and process of preparing the same | |
US2293844A (en) | Process of treating textile fiber | |
US3501467A (en) | Organic triazinone compound | |
US2809912A (en) | N-ethylene trichloromethyl sulfenamide | |
US3179686A (en) | Mixed sulfite esters of alkynyl alcohols and glycol ethers | |
US2609393A (en) | Dodecyl, dimethyl, -cinnamylammonium halides | |
US2348795A (en) | Cleaning and disinfecting composition |