GB1057131A - New antibacterial and antifungal compositions - Google Patents
New antibacterial and antifungal compositionsInfo
- Publication number
- GB1057131A GB1057131A GB7064/63A GB706463A GB1057131A GB 1057131 A GB1057131 A GB 1057131A GB 7064/63 A GB7064/63 A GB 7064/63A GB 706463 A GB706463 A GB 706463A GB 1057131 A GB1057131 A GB 1057131A
- Authority
- GB
- United Kingdom
- Prior art keywords
- preparations
- nitrobutan
- bromo
- nitro
- methyl
- 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
- 230000000844 anti-bacterial effect Effects 0.000 title abstract 3
- 239000012871 anti-fungal composition Substances 0.000 title 1
- 239000000203 mixture Substances 0.000 abstract 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 6
- 239000003242 anti bacterial agent Substances 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- 238000002360 preparation method Methods 0.000 abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 229940121375 antifungal agent Drugs 0.000 abstract 3
- 239000003429 antifungal agent Substances 0.000 abstract 3
- 159000000000 sodium salts Chemical class 0.000 abstract 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- 239000000443 aerosol Substances 0.000 abstract 2
- POJWUDADGALRAB-UHFFFAOYSA-N allantoin Chemical compound NC(=O)NC1NC(=O)NC1=O POJWUDADGALRAB-UHFFFAOYSA-N 0.000 abstract 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 abstract 2
- 229910021502 aluminium hydroxide Inorganic materials 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- 239000006071 cream Substances 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 abstract 2
- 239000006210 lotion Substances 0.000 abstract 2
- 239000000843 powder Substances 0.000 abstract 2
- 239000003755 preservative agent Substances 0.000 abstract 2
- 230000002335 preservative effect Effects 0.000 abstract 2
- -1 rednisolone Chemical class 0.000 abstract 2
- 239000002453 shampoo Substances 0.000 abstract 2
- 239000000606 toothpaste Substances 0.000 abstract 2
- JFQABSZKSOQZTG-UHFFFAOYSA-N 1,1-dibromo-3-methyl-1-nitrobutan-2-ol Chemical compound CC(C)C(O)C(Br)(Br)[N+]([O-])=O JFQABSZKSOQZTG-UHFFFAOYSA-N 0.000 abstract 1
- GWNCZMMMYVYUCI-UHFFFAOYSA-N 1-bromo-1-nitrooctan-2-ol Chemical compound CCCCCCC(O)C(Br)[N+]([O-])=O GWNCZMMMYVYUCI-UHFFFAOYSA-N 0.000 abstract 1
- NIAKTRXGTZHZMK-UHFFFAOYSA-N 1-bromo-3-methyl-1-nitrobutan-2-ol Chemical compound CC(C)C(O)C(Br)[N+]([O-])=O NIAKTRXGTZHZMK-UHFFFAOYSA-N 0.000 abstract 1
- UHUZCPVKBAPSSA-UHFFFAOYSA-N 1-nitrooctan-2-ol Chemical compound CCCCCCC(O)C[N+]([O-])=O UHUZCPVKBAPSSA-UHFFFAOYSA-N 0.000 abstract 1
- KJTQHXTUICAYHG-UHFFFAOYSA-N 3-methyl-1-nitrobutan-2-ol Chemical compound CC(C)C(O)C[N+]([O-])=O KJTQHXTUICAYHG-UHFFFAOYSA-N 0.000 abstract 1
- POJWUDADGALRAB-PVQJCKRUSA-N Allantoin Natural products NC(=O)N[C@@H]1NC(=O)NC1=O POJWUDADGALRAB-PVQJCKRUSA-N 0.000 abstract 1
- 239000005995 Aluminium silicate Substances 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- LVDKZNITIUWNER-UHFFFAOYSA-N Bronopol Chemical compound OCC(Br)(CO)[N+]([O-])=O LVDKZNITIUWNER-UHFFFAOYSA-N 0.000 abstract 1
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 abstract 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 abstract 1
- 239000004150 EU approved colour Substances 0.000 abstract 1
- BALXUFOVQVENIU-GNAZCLTHSA-N Ephedrine hydrochloride Chemical compound Cl.CN[C@@H](C)[C@H](O)C1=CC=CC=C1 BALXUFOVQVENIU-GNAZCLTHSA-N 0.000 abstract 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 abstract 1
- 240000007472 Leucaena leucocephala Species 0.000 abstract 1
- MMBILEWCGWTAOV-UHFFFAOYSA-N N-(2-Hydroxypropyl)dodecanamide Chemical compound CCCCCCCCCCCC(=O)NCC(C)O MMBILEWCGWTAOV-UHFFFAOYSA-N 0.000 abstract 1
- 229930193140 Neomycin Natural products 0.000 abstract 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 abstract 1
- 239000004141 Sodium laurylsulphate Substances 0.000 abstract 1
- 229960000458 allantoin Drugs 0.000 abstract 1
- 235000012211 aluminium silicate Nutrition 0.000 abstract 1
- 230000000843 anti-fungal effect Effects 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 235000012411 boiled sweets Nutrition 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 239000001506 calcium phosphate Substances 0.000 abstract 1
- 229960002798 cetrimide Drugs 0.000 abstract 1
- 229960001927 cetylpyridinium chloride Drugs 0.000 abstract 1
- YMKDRGPMQRFJGP-UHFFFAOYSA-M cetylpyridinium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 YMKDRGPMQRFJGP-UHFFFAOYSA-M 0.000 abstract 1
- 235000005687 corn oil Nutrition 0.000 abstract 1
- 239000002537 cosmetic Substances 0.000 abstract 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 abstract 1
- 229940038472 dicalcium phosphate Drugs 0.000 abstract 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- JZKFHQMONDVVNF-UHFFFAOYSA-N dodecyl sulfate;tris(2-hydroxyethyl)azanium Chemical compound OCCN(CCO)CCO.CCCCCCCCCCCCOS(O)(=O)=O JZKFHQMONDVVNF-UHFFFAOYSA-N 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 238000010410 dusting Methods 0.000 abstract 1
- 239000003221 ear drop Substances 0.000 abstract 1
- 229940047652 ear drops Drugs 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 229960002534 ephedrine hydrochloride Drugs 0.000 abstract 1
- 239000000706 filtrate Substances 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 238000009472 formulation Methods 0.000 abstract 1
- 229910001679 gibbsite Inorganic materials 0.000 abstract 1
- 208000014617 hemorrhoid Diseases 0.000 abstract 1
- ACGUYXCXAPNIKK-UHFFFAOYSA-N hexachlorophene Chemical compound OC1=C(Cl)C=C(Cl)C(Cl)=C1CC1=C(O)C(Cl)=CC(Cl)=C1Cl ACGUYXCXAPNIKK-UHFFFAOYSA-N 0.000 abstract 1
- 229960004068 hexachlorophene Drugs 0.000 abstract 1
- 235000015110 jellies Nutrition 0.000 abstract 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000008141 laxative Substances 0.000 abstract 1
- 229940125722 laxative agent Drugs 0.000 abstract 1
- YECIFGHRMFEPJK-UHFFFAOYSA-N lidocaine hydrochloride monohydrate Chemical compound O.[Cl-].CC[NH+](CC)CC(=O)NC1=C(C)C=CC=C1C YECIFGHRMFEPJK-UHFFFAOYSA-N 0.000 abstract 1
- 229940057995 liquid paraffin Drugs 0.000 abstract 1
- 239000007937 lozenge Substances 0.000 abstract 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 abstract 1
- 239000000347 magnesium hydroxide Substances 0.000 abstract 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 abstract 1
- 235000012254 magnesium hydroxide Nutrition 0.000 abstract 1
- 239000003595 mist Substances 0.000 abstract 1
- 239000002324 mouth wash Substances 0.000 abstract 1
- 229960004927 neomycin Drugs 0.000 abstract 1
- 239000002674 ointment Substances 0.000 abstract 1
- 229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 abstract 1
- 235000010603 pastilles Nutrition 0.000 abstract 1
- 239000002304 perfume Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000003380 propellant Substances 0.000 abstract 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 150000003431 steroids Chemical class 0.000 abstract 1
- 239000000829 suppository Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 229940124597 therapeutic agent Drugs 0.000 abstract 1
- 229940034610 toothpaste Drugs 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/13—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups
- C07C205/26—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups and being further substituted by halogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/418—Amines containing nitro groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/005—Antimicrobial preparations
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Aerosol compositions comprise a nitroalkanol of the general formula <FORM:1057131/C4-C5/1> in which R1 is H, C1-12 alkyl and R3 is H, or R1 and R3 together with the shared carbon atom form a cycloalkyl ring having 5 to 7 carbon atoms, and R2 is H, Me, Et, hydroxymethyl or bromine dissolved in a suitable solvent in admixture with a volatile propellant, e.g. a chloro-fluoro alkane mixture. A shampoo composition may comprise one of the above nitroalkanols as an antifungal or antibacterial agent or as a preservative. A typical shampoo formulation comprises triethanolamine lauryl sulphate, lauric isopropanolamide, 2 - bromo - 2 - nitro - propane-1,3-diol, and water with perfume and colouring agents.ALSO:1- Bromo - 1 - nitro - octan - 2 - ol is prepared by forming the sodium salt of 1-nitro-octan-2-ol, brominating the latter in ether, filtering the resultant suspension, distilling ether from the filtrate and distilling the residue under reduced pressure. 1,1 - Dibromo - 3 - methyl - 1 - nitrobutan - 2 - ol is prepared by converting 3-methyl-1-nitrobutan-2-ol to its sodium salt, and brominating the latter as above to give 1-bromo-3-methyl-1-nitrobutan-2-ol. The latter is added to sodium methoxide in methanol and the mixture is diluted with ether to precipitate the sodium salt, which is brominated as above to yield the product.ALSO:Pharmaceutical, cosmetic and toilet preparations comprise as an antibacterial or antifungal agent or as a preservative a nitroalkanol of the general formula: <FORM:1057131/A5-A6/1> in which R1 is H or C1-12 alkyl; R3 is H; or R1 and R3 together with the shared carbon atom form a cycloalkyl ring having 5-7 carbon atoms, and R2 is H, Me, Et, hydroxymethyl or Br, in admixture with a diluent or carrier. The preparations may be formulated as lotions, creams, ointments, jellies, powders, solid sticks, suppositories, ear drops, aerosol preparations, lozenges, pastilles, boiled sweets, mouthwashes, toothpastes, hair creams or hair lotions, with appropriate conventional excipients. Other therapeutic agents, such as steroids, e.g. rednisolone, antibiotics, e.g. neomycin, other anti-bacterial or antifungal agents, e.g. hexachlorophene, cetrimide or cetylpyridinium chloride, may be included in the preparations. The nitroalkanols of the invention may be added for example, to laxatives based on Mg(OH)2 and/or Al(OH)3, e.g. Emulsion of liquid paraffin and Mist. Mag. Hydrox. B.P.; compositions for the treatment of haemorrhoids containing ephedrine hydrochloride, allantoin, and lignocaine hydrochloride; compositions comprising (a) maize oil and acacia and (b) aluminium hydroxide and kaolin; dusting powders comprising Mgo; and a toothpaste comprising dicalcium phosphate and sodium lauryl sulphate.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7064/63A GB1057131A (en) | 1963-02-21 | 1963-02-21 | New antibacterial and antifungal compositions |
| US434615A US3558788A (en) | 1963-02-21 | 1965-02-23 | New antibacterial and antifungal compositions |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7064/63A GB1057131A (en) | 1963-02-21 | 1963-02-21 | New antibacterial and antifungal compositions |
| US43461565A | 1965-02-23 | 1965-02-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1057131A true GB1057131A (en) | 1967-02-01 |
Family
ID=26241152
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7064/63A Expired GB1057131A (en) | 1963-02-21 | 1963-02-21 | New antibacterial and antifungal compositions |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US3558788A (en) |
| GB (1) | GB1057131A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3541162A (en) * | 1967-12-14 | 1970-11-17 | Texaco Inc | Preparation of halonitroalcohols |
| JPS51151321A (en) * | 1975-06-17 | 1976-12-25 | Green Cross Corp:The | Method for preservation of human immune globulin from decay |
| US4049830A (en) | 1974-11-13 | 1977-09-20 | Milmark Research, Inc. | Bovine teat dip |
| FR2407946A1 (en) * | 1977-11-03 | 1979-06-01 | Ici Ltd | PROCESS FOR PREPARING POLYMERIC BIOCIDES DERIVED FROM 2-BROMO-2-NITROPROPANE-1,3-DIOL |
| WO1984002923A1 (en) * | 1983-01-28 | 1984-08-02 | Dairyland Food Lab | Preservative composition having color indicator |
| EP0373759A1 (en) * | 1988-11-30 | 1990-06-20 | Imperial Chemical Industries Plc | Compound, composition, process and use |
| US5196344A (en) * | 1990-02-27 | 1993-03-23 | D & F Control Systems, Inc. | Milk sample preservative |
| JP2579541B2 (en) | 1988-12-08 | 1997-02-05 | 日本曹達株式会社 | Deodorizing composition for night soil |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2042400A1 (en) * | 1970-08-27 | 1972-03-09 | Henkel & Cie. GmbH, 4000 Düsseldorf | Freshness preservative for cut flowers |
| CA969479A (en) * | 1971-03-18 | 1975-06-17 | Henkel And Cie. G.M.B.H. | Processes for preserving cut flowers using 2-bromo-2-nitropropanediol-(1,3) |
| US4199602A (en) * | 1978-02-23 | 1980-04-22 | Economics Laboratory, Inc. | Control of mastitis and compositions therefor |
| IE54761B1 (en) * | 1982-12-14 | 1990-01-31 | Boots Co Plc | Preserving agent |
| US5055493A (en) * | 1988-09-30 | 1991-10-08 | Union Carbide Chemicals And Plastics Technology Corporation | Antimicrobial composition and method of use in oil well flooding |
| DE69026138T2 (en) * | 1989-05-17 | 1996-08-01 | Katayama Chemical, Inc., Osaka | Aqueous isothiazolone formulation |
| CN102802411B (en) * | 2009-06-11 | 2015-02-04 | 陶氏环球技术有限责任公司 | Brominated nitroalkanol compositions and their use as biocides |
| EP2624817A1 (en) * | 2010-10-08 | 2013-08-14 | Helperby Therapeutics Limited | Novel composition |
-
1963
- 1963-02-21 GB GB7064/63A patent/GB1057131A/en not_active Expired
-
1965
- 1965-02-23 US US434615A patent/US3558788A/en not_active Expired - Lifetime
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3541162A (en) * | 1967-12-14 | 1970-11-17 | Texaco Inc | Preparation of halonitroalcohols |
| US4049830A (en) | 1974-11-13 | 1977-09-20 | Milmark Research, Inc. | Bovine teat dip |
| JPS51151321A (en) * | 1975-06-17 | 1976-12-25 | Green Cross Corp:The | Method for preservation of human immune globulin from decay |
| FR2407946A1 (en) * | 1977-11-03 | 1979-06-01 | Ici Ltd | PROCESS FOR PREPARING POLYMERIC BIOCIDES DERIVED FROM 2-BROMO-2-NITROPROPANE-1,3-DIOL |
| US4263424A (en) | 1977-11-03 | 1981-04-21 | Imperial Chemical Industries Limited | Anti-fungal and anti-bacterial polyurethanes |
| WO1984002923A1 (en) * | 1983-01-28 | 1984-08-02 | Dairyland Food Lab | Preservative composition having color indicator |
| AU573203B2 (en) * | 1983-01-28 | 1988-06-02 | Dairy and Foods Labs.Inc. | Preservative composition with colour indicator |
| EP0373759A1 (en) * | 1988-11-30 | 1990-06-20 | Imperial Chemical Industries Plc | Compound, composition, process and use |
| AU617552B2 (en) * | 1988-11-30 | 1991-11-28 | Zeneca Limited | Compound, composition, process and use |
| US5112871A (en) * | 1988-11-30 | 1992-05-12 | Imperial Chemical Industries Plc | Anti-microbial bromo-nitro compounds |
| JP2579541B2 (en) | 1988-12-08 | 1997-02-05 | 日本曹達株式会社 | Deodorizing composition for night soil |
| US5196344A (en) * | 1990-02-27 | 1993-03-23 | D & F Control Systems, Inc. | Milk sample preservative |
Also Published As
| Publication number | Publication date |
|---|---|
| US3558788A (en) | 1971-01-26 |
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