GB946029A - Salicylic acid derivatives and compositions containing them - Google Patents
Salicylic acid derivatives and compositions containing themInfo
- Publication number
- GB946029A GB946029A GB1369161A GB1369161A GB946029A GB 946029 A GB946029 A GB 946029A GB 1369161 A GB1369161 A GB 1369161A GB 1369161 A GB1369161 A GB 1369161A GB 946029 A GB946029 A GB 946029A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenyl
- give
- hydrogen
- acid
- 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
- 239000000203 mixture Substances 0.000 title abstract 3
- 229940058287 salicylic acid derivative anticestodals Drugs 0.000 title 1
- 150000003872 salicylic acid derivatives Chemical class 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 8
- 239000001257 hydrogen Substances 0.000 abstract 8
- -1 trifluoromethylmethoxycarbonyl Chemical group 0.000 abstract 7
- LGERKUYJCZOBTB-UHFFFAOYSA-N 2-hydroxy-5-phenylbenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(C=2C=CC=CC=2)=C1 LGERKUYJCZOBTB-UHFFFAOYSA-N 0.000 abstract 6
- 125000004432 carbon atom Chemical group C* 0.000 abstract 6
- 150000002431 hydrogen Chemical group 0.000 abstract 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 4
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 3
- ANCWLMBYNOSXQA-UHFFFAOYSA-N methyl 2-hydroxy-5-phenylbenzoate Chemical compound C1=C(O)C(C(=O)OC)=CC(C=2C=CC=CC=2)=C1 ANCWLMBYNOSXQA-UHFFFAOYSA-N 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 abstract 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- 125000005907 alkyl ester group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- 229940088710 antibiotic agent Drugs 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 abstract 1
- FCFDBQQKNCOOHU-UHFFFAOYSA-N 2,2,2-trifluoroethyl 2-hydroxy-5-phenylbenzoate Chemical compound FC(COC(C=1C(O)=CC=C(C1)C1=CC=CC=C1)=O)(F)F FCFDBQQKNCOOHU-UHFFFAOYSA-N 0.000 abstract 1
- MDDJDQPZGOGYRZ-UHFFFAOYSA-N 2-acetyloxy-5-phenylbenzoic acid Chemical compound C1=C(C(O)=O)C(OC(=O)C)=CC=C1C1=CC=CC=C1 MDDJDQPZGOGYRZ-UHFFFAOYSA-N 0.000 abstract 1
- HBXBUWSUUCYRGC-UHFFFAOYSA-N 2-hydroxy-3-nitro-5-phenylbenzoic acid Chemical compound [O-][N+](=O)C1=C(O)C(C(=O)O)=CC(C=2C=CC=CC=2)=C1 HBXBUWSUUCYRGC-UHFFFAOYSA-N 0.000 abstract 1
- AKHDIUNHOLQWKU-UHFFFAOYSA-N 2-hydroxy-5-phenylbenzoyl chloride Chemical compound C1(=CC=CC=C1)C1=CC=C(C(C(=O)Cl)=C1)O AKHDIUNHOLQWKU-UHFFFAOYSA-N 0.000 abstract 1
- NBODSWALXVAROK-UHFFFAOYSA-N 3-acetyl-2-hydroxy-5-phenylbenzoic acid Chemical compound C(C)(=O)C1=C(C(C(=O)O)=CC(=C1)C1=CC=CC=C1)O NBODSWALXVAROK-UHFFFAOYSA-N 0.000 abstract 1
- FNJSAYWTLIANOH-UHFFFAOYSA-N 3-amino-2-hydroxy-5-phenylbenzoic acid Chemical compound OC(=O)C1=C(O)C(N)=CC(C=2C=CC=CC=2)=C1 FNJSAYWTLIANOH-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- SFLMCPPVPVBWKZ-UHFFFAOYSA-N N-(2-aminophenyl)-2-hydroxy-5-phenylbenzamide Chemical compound NC1=C(C=CC=C1)NC(C=1C(O)=CC=C(C1)C1=CC=CC=C1)=O SFLMCPPVPVBWKZ-UHFFFAOYSA-N 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 206010042496 Sunburn Diseases 0.000 abstract 1
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 abstract 1
- 150000001414 amino alcohols Chemical class 0.000 abstract 1
- 230000003444 anaesthetic effect Effects 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 230000002421 anti-septic effect Effects 0.000 abstract 1
- 239000003963 antioxidant agent Substances 0.000 abstract 1
- 229940064004 antiseptic throat preparations Drugs 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000000872 buffer Substances 0.000 abstract 1
- FARIJXYNRVNAEL-UHFFFAOYSA-N butyl 2-hydroxy-5-phenylbenzoate Chemical compound C(CCC)OC(C=1C(O)=CC=C(C1)C1=CC=CC=C1)=O FARIJXYNRVNAEL-UHFFFAOYSA-N 0.000 abstract 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003995 emulsifying agent Substances 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 235000015110 jellies Nutrition 0.000 abstract 1
- 239000006210 lotion Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- KZTHPJSHACQMJQ-UHFFFAOYSA-N methyl 2-acetyloxy-5-phenylbenzoate Chemical compound COC(C1=C(C=CC(=C1)C1=CC=CC=C1)OC(C)=O)=O KZTHPJSHACQMJQ-UHFFFAOYSA-N 0.000 abstract 1
- PLWCPEJTHPQFST-UHFFFAOYSA-N methyl 2-methoxy-5-phenylbenzoate Chemical compound C1=C(OC)C(C(=O)OC)=CC(C=2C=CC=CC=2)=C1 PLWCPEJTHPQFST-UHFFFAOYSA-N 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 239000002674 ointment Substances 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 239000006072 paste Substances 0.000 abstract 1
- 239000002304 perfume Substances 0.000 abstract 1
- KJJPCJANXLOVPY-UHFFFAOYSA-N phenyl 2-hydroxy-5-phenylbenzoate Chemical compound C1(=CC=CC=C1)C1=CC=C(C(C(=O)OC2=CC=CC=C2)=C1)O KJJPCJANXLOVPY-UHFFFAOYSA-N 0.000 abstract 1
- 229960000969 phenyl salicylate Drugs 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 239000003755 preservative agent Substances 0.000 abstract 1
- 230000002265 prevention Effects 0.000 abstract 1
- 230000002035 prolonged effect Effects 0.000 abstract 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000001302 tertiary amino group Chemical group 0.000 abstract 1
- 230000000699 topical effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
- A61K8/368—Carboxylic acids; Salts or anhydrides thereof with carboxyl groups directly bound to carbon atoms of aromatic rings
-
- 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
- A61K8/42—Amides
-
- 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
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
- A61K8/447—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof containing sulfur
-
- 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
-
- 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
-
- 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
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
- C07C65/105—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/32—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups
- C07C65/40—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups containing singly bound oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Emergency Medicine (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises compounds of the formula: <FORM:0946029/C2/1> (wherein X is hydrogen, acetyl, amino or allyl, Y is hydrogen, alkyl of at most 5 carbon atoms, or acyl of at most 5 carbon atoms, and Z is carboxy, carbaltoxy of at most 6 carbon atoms, carbaryloxy, b -dimethylaminoethoxycarbonyl, b -tertiary-butylaminoethoxycarbonyl, b -morpholinoethoxycarbonyl, trifluoromethylmethoxycarbonyl, o-aminophenylcarbamoyl, or 2-benzimidazolyl, with the limitations that when X is hydrogen and Z is carboxy, Y is not hydrogen, methyl or acetyl, and that when X and Y are both hydrogen, Z is not carbomethoxy) and acid-addition salts of the amino compounds; and the preparation of the compounds in which Z is b - dimethylaminoethoxycarbonyl, b - tertiary -butylaminoethoxycarbonyl or b -morpholinoethoxycarbonyl and X and Y are hydrogen by reacting a lower alkyl ester of 5-phenylsalicylic acid with the appropriate secondary or tertiary amino alcohol. In examples (1) 2-acetoxy-5-phenyl-benzoic acid is heated in nitrobenzene with aluminium chloride to give 3-acetyl-5-phenyl-salicylic acid; (2) 5-phenyl-salicylic acid is nitrated to 3-nitro-5-phenyl-salicylic acid and this is reduced to 3-amino-5-phenyl-salicylic acid; (3) methyl 5-phenyl-salicylate and allyl bromide give methyl 3-allyl-5-phenylsalicylate and other esters are prepared similarly; (4) methyl 5-phenyl-salicylate and dimethyl sulphate give methyl 2-methoxy-5-phenylbenzoate and other esters are prepared similarly; (5) methyl 5-phenyl-salicylate is acetylated to give methyl 2-acetoxy-5-phenylbenzoate and other 2-esters are prepared similarly; (6) 5-phenylsalicylic acid and phenol in the presence of phosphorus oxychloride give phenyl 5-phenylsalicylate; (7) 5-phenylsalicylic acid and n-butanol give butyl 5-phenyl-salicylate and other alkyl esters are prepared similarly; 5-phenylsalicyloyl chloride and trifluoroethanol give trifluoroethyl 5-phenylsalicylate; (8) 5-phenylsalicylic acid and o-phenylenediamine give N-(o-aminophenyl)-5-phenylsalicylamide; and (9) the starting materials of (8) heated for a prolonged time give 21-(2-hydroxy-5-phenyl)-phenylbenzimidazole. Other examples describe esterifications with aminoalcohols as referred to above. Salts with organic and inorganic acids are described or referred to.ALSO:Dermatological compositions comprise an acceptable dermatological base and 0.001% to about 10% by weight of a 5-phenyl-salicylic acid derivative of the formula <FORM:0946029/A5-A6/1> (wherein X is hydrogen, acetyl, amino or allyl, Y is hydrogen, alkyl of at most 5 carbon atoms, or aryl of at most 5 carbon atoms, and Z is carboxy, carbalkoxy of at most 6 carbon atoms, carbaryloxy, b - dimethylaminoethoxycarbonyl, b - tertiarybutyl aminoethoxycarbonyl, b - morpholinoethoxycarbonyl, trifluoromethylmethoxycarbonyl, o - aminophenylcarbamoyl, or 2 - benzimidazolyl) or an acid-addition salt of the amino compounds. They may take the form of ointments, lotions, pastes, jellies or powders, and may include local or topical anaesthetic, antibacterials, antibiotics, antiseptics, emulsifying agents, solvents, antioxidants, preservatives, buffers, perfumes and bodying materials. Examples are given. The compositions may be used for the prevention and treatment of sunburn.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1369161A GB946029A (en) | 1961-04-17 | 1961-04-17 | Salicylic acid derivatives and compositions containing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1369161A GB946029A (en) | 1961-04-17 | 1961-04-17 | Salicylic acid derivatives and compositions containing them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB946029A true GB946029A (en) | 1964-01-08 |
Family
ID=10027649
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1369161A Expired GB946029A (en) | 1961-04-17 | 1961-04-17 | Salicylic acid derivatives and compositions containing them |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB946029A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2370469A1 (en) * | 1976-11-15 | 1978-06-09 | Basf Ag | LIGHT PROTECTION AGENTS CONTAINING 4-DIALKYLAMINODIPHTHALATES |
| FR2385685A1 (en) * | 1977-04-01 | 1978-10-27 | Mundipharma Ag | PROCESS FOR OBTAINING CERTAIN ESTERS OF AN AMINO-SALICYLIC ACID AND THEIR APPLICATION TO THE FILTRATION OF ULTRAVIOLET RAYS |
| EP0038192A1 (en) * | 1980-04-14 | 1981-10-21 | The Research Foundation Of State University Of New York | 5-Alkylsalicylanilides derivatives and method for inhibiting the growth of microorganisms |
| EP0105484A3 (en) * | 1982-09-30 | 1984-08-22 | Yamamoto Chemical Industrial Company, Limited | 3-propionylsalicyclic acid derivatives and process for the preparation of the same |
| US4939132A (en) * | 1985-04-15 | 1990-07-03 | The Research Foundation Of State University Of New York | Novel 5-alkylsulfonylsalicylanilides and microbiocidal compositions for controlling the growth of microorganisms |
-
1961
- 1961-04-17 GB GB1369161A patent/GB946029A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2370469A1 (en) * | 1976-11-15 | 1978-06-09 | Basf Ag | LIGHT PROTECTION AGENTS CONTAINING 4-DIALKYLAMINODIPHTHALATES |
| FR2385685A1 (en) * | 1977-04-01 | 1978-10-27 | Mundipharma Ag | PROCESS FOR OBTAINING CERTAIN ESTERS OF AN AMINO-SALICYLIC ACID AND THEIR APPLICATION TO THE FILTRATION OF ULTRAVIOLET RAYS |
| EP0038192A1 (en) * | 1980-04-14 | 1981-10-21 | The Research Foundation Of State University Of New York | 5-Alkylsalicylanilides derivatives and method for inhibiting the growth of microorganisms |
| EP0105484A3 (en) * | 1982-09-30 | 1984-08-22 | Yamamoto Chemical Industrial Company, Limited | 3-propionylsalicyclic acid derivatives and process for the preparation of the same |
| US4939132A (en) * | 1985-04-15 | 1990-07-03 | The Research Foundation Of State University Of New York | Novel 5-alkylsulfonylsalicylanilides and microbiocidal compositions for controlling the growth of microorganisms |
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