WO2009031202A1 - Cinnamic acid derivatives and use thereof as ultraviolet absorber - Google Patents

Cinnamic acid derivatives and use thereof as ultraviolet absorber Download PDF

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Publication number
WO2009031202A1
WO2009031202A1 PCT/JP2007/067200 JP2007067200W WO2009031202A1 WO 2009031202 A1 WO2009031202 A1 WO 2009031202A1 JP 2007067200 W JP2007067200 W JP 2007067200W WO 2009031202 A1 WO2009031202 A1 WO 2009031202A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
methoxy
hydroxyl
acid derivatives
cinnamic acid
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.)
Ceased
Application number
PCT/JP2007/067200
Other languages
French (fr)
Japanese (ja)
Inventor
Takuya Hiruma
Masaru Suetsugu
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.)
Shiseido Co Ltd
Original Assignee
Shiseido Co Ltd
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 Shiseido Co Ltd filed Critical Shiseido Co Ltd
Priority to PCT/JP2007/067200 priority Critical patent/WO2009031202A1/en
Publication of WO2009031202A1 publication Critical patent/WO2009031202A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C07D295/12—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 or doubly bound nitrogen 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
    • A61K8/42—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
    • A61K8/49—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
    • 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
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C07C235/36—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
    • 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
    • C07D295/16—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 acylated on ring nitrogen atoms
    • C07D295/18—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 acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)

Abstract

The invention provides ultraviolet absorbers which exhibit high solubility in hydrophilic solvents such as water and excellent ultraviolet absorbing power and which do not exhibit absorption in the visible light region and are highly stable and safe; and ultraviolet absorbing compositions, particularly external preparations for the skin, containing the same. The invention relates to cinnamic acid derivatives represented by the general formula (1) or salts thereof which are extremely useful as ultraviolet absorber: (1) wherein R1, R2 and R3 are each H or methoxy; and either of R4 and R5 is -{(CH2)m-O}n-R6 [wherein R6 is H or alkyl of 1 to 4 carbon atoms; m is 2 to 4; and n is 1 to 5], C2-6 alkyl having hydroxyl, C2-6 alkyl having methoxy or morpholino, or C3-6 cycloalkyl having hydroxyl; and the other thereof is H, methyl, or C2-6 alkyl having hydroxyl or methoxy, or NR4R5 forms a five- to seven-membered ring.
PCT/JP2007/067200 2007-09-04 2007-09-04 Cinnamic acid derivatives and use thereof as ultraviolet absorber Ceased WO2009031202A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/JP2007/067200 WO2009031202A1 (en) 2007-09-04 2007-09-04 Cinnamic acid derivatives and use thereof as ultraviolet absorber

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/JP2007/067200 WO2009031202A1 (en) 2007-09-04 2007-09-04 Cinnamic acid derivatives and use thereof as ultraviolet absorber

Publications (1)

Publication Number Publication Date
WO2009031202A1 true WO2009031202A1 (en) 2009-03-12

Family

ID=40428525

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2007/067200 Ceased WO2009031202A1 (en) 2007-09-04 2007-09-04 Cinnamic acid derivatives and use thereof as ultraviolet absorber

Country Status (1)

Country Link
WO (1) WO2009031202A1 (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101181175B1 (en) * 2010-08-17 2012-09-18 연세대학교 산학협력단 Novel cinnamic acid derivative and pharmaceutical composition comprising the same
WO2018080166A3 (en) * 2016-10-26 2018-08-09 (주)아모레퍼시픽 3,4,5-trimethoxycinnamic acid ester derivative, method for preparing same, and skin whitening composition comprising same
WO2020122341A1 (en) * 2018-12-14 2020-06-18 주식회사 엘지생활건강 Novel cinnamic acid derivative and antibacterial composition comprising same

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB906319A (en) * 1959-11-01 1962-09-19 American Cyanamid Co 3,4,5-tri (lower) alkoxycinnamamides and process for preparation
JPS505389A (en) * 1973-01-29 1975-01-21
JPS548666B1 (en) * 1969-04-02 1979-04-17
JPS62502749A (en) * 1985-03-28 1987-10-22 ウニベルシテ　ルイ　パスツ−ル Amides of paramethoxycinnamic acid and urocanic acid, their preparation, their use as solar filters and dermatological, pharmacological and cosmetic compositions containing them
JPH0456949A (en) * 1990-06-26 1992-02-24 Konica Corp Silver halide photographic sensitive material
JP2006131603A (en) * 2004-11-05 2006-05-25 Shiseido Co Ltd Cinnamic acid derivative, its application as ultraviolet absorber, ultraviolet-absorbing composition formulated therewith, and skin care preparation for external use
JP2006131855A (en) * 2004-11-05 2006-05-25 Shiseido Co Ltd Water-soluble ultraviolet absorber and ultraviolet-ray absorbing composition containing the same, skin external preparation
JP2008007443A (en) * 2006-06-28 2008-01-17 Shiseido Co Ltd Cinnamic acid derivatives, their use as UV absorbers, UV-absorbing compositions containing the same, and skin external preparations.
JP2008007444A (en) * 2006-06-28 2008-01-17 Shiseido Co Ltd A novel cinnamic acid derivative, its use as an ultraviolet absorber, and an ultraviolet-absorbing composition and an external preparation for skin containing the same.

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB906319A (en) * 1959-11-01 1962-09-19 American Cyanamid Co 3,4,5-tri (lower) alkoxycinnamamides and process for preparation
JPS548666B1 (en) * 1969-04-02 1979-04-17
JPS505389A (en) * 1973-01-29 1975-01-21
JPS62502749A (en) * 1985-03-28 1987-10-22 ウニベルシテ　ルイ　パスツ−ル Amides of paramethoxycinnamic acid and urocanic acid, their preparation, their use as solar filters and dermatological, pharmacological and cosmetic compositions containing them
JPH0456949A (en) * 1990-06-26 1992-02-24 Konica Corp Silver halide photographic sensitive material
JP2006131603A (en) * 2004-11-05 2006-05-25 Shiseido Co Ltd Cinnamic acid derivative, its application as ultraviolet absorber, ultraviolet-absorbing composition formulated therewith, and skin care preparation for external use
JP2006131855A (en) * 2004-11-05 2006-05-25 Shiseido Co Ltd Water-soluble ultraviolet absorber and ultraviolet-ray absorbing composition containing the same, skin external preparation
JP2008007443A (en) * 2006-06-28 2008-01-17 Shiseido Co Ltd Cinnamic acid derivatives, their use as UV absorbers, UV-absorbing compositions containing the same, and skin external preparations.
JP2008007444A (en) * 2006-06-28 2008-01-17 Shiseido Co Ltd A novel cinnamic acid derivative, its use as an ultraviolet absorber, and an ultraviolet-absorbing composition and an external preparation for skin containing the same.

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101181175B1 (en) * 2010-08-17 2012-09-18 연세대학교 산학협력단 Novel cinnamic acid derivative and pharmaceutical composition comprising the same
WO2018080166A3 (en) * 2016-10-26 2018-08-09 (주)아모레퍼시픽 3,4,5-trimethoxycinnamic acid ester derivative, method for preparing same, and skin whitening composition comprising same
WO2020122341A1 (en) * 2018-12-14 2020-06-18 주식회사 엘지생활건강 Novel cinnamic acid derivative and antibacterial composition comprising same

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