GB946029A - Salicylic acid derivatives and compositions containing them - Google Patents

Salicylic acid derivatives and compositions containing them

Info

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
Application number
GB1369161A
Inventor
Matthew Joseph Brunner
Paul Finkelstein
Herbert Elmer Hibnick
Elliot Norris Schubert
Stephen Sichak
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Gillette Co LLC
Original Assignee
Gillette Co LLC
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Gillette Co LLC filed Critical Gillette Co LLC
Priority to GB1369161A priority Critical patent/GB946029A/en
Publication of GB946029A publication Critical patent/GB946029A/en
Expired legal-status Critical Current

Links

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.
GB1369161A 1961-04-17 1961-04-17 Salicylic acid derivatives and compositions containing them Expired GB946029A (en)

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)

* Cited by examiner, † Cited by third party
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
EP0105484A2 (en) * 1982-09-30 1984-04-18 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

Cited By (6)

* Cited by examiner, † Cited by third party
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
EP0105484A2 (en) * 1982-09-30 1984-04-18 Yamamoto Chemical Industrial Company, Limited 3-Propionylsalicyclic acid derivatives and process for the preparation of the same
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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