Title:
PROPYL-PHENYL-ETHER DERIVATIVE AND MELANOGENESIS INHIBITOR, SKIN-LIGHTENING AGENT, ANTIMICROBIAL AGENT, AND COSMETIC CONTAINING SAID PROPYL-PHENYL-ETHER DERIVATIVE
Document Type and Number:
WIPO Patent Application WO/2014/069555
Kind Code:
A1
Abstract:
Provided is a compound that exhibits an excellent melanogenesis-inhibiting effect (skin-lightening effect), exhibits an excellent antimicrobial effect, excels in terms of temporal stability and the like, and is suitable for use as an ingredient of a cosmetic. Said compound is a propyl-phenyl-ether derivative compound comprising a propyl group that has a substituent such as a hydroxyl group and is bound to the hydroxyl group of a phenol group that has a substituent such as a tert-butyl group. A melanogenesis inhibitor, skin-lightening agent, and antimicrobial agent containing the aforementioned compound as an active ingredient are also provided, as is a cosmetic characterized by containing said compound.
Inventors:
YOSHIOKA MASATO (JP)
TAIRA NORIHISA (JP)
NAKAMURA SAYAKA (JP)
TAIRA NORIHISA (JP)
NAKAMURA SAYAKA (JP)
Application Number:
PCT/JP2013/079498
Publication Date:
May 08, 2014
Filing Date:
October 31, 2013
Export Citation:
Assignee:
SEIWA KASEI CO LTD (JP)
International Classes:
C07C43/23; A01N31/14; A01P3/00; A61K8/34; A61K8/37; A61K8/40; A61K8/41; A61K8/44; A61K8/46; A61K31/085; A61K31/10; A61K31/136; A61K31/192; A61K31/198; A61K31/277; A61P17/00; A61P31/04; A61P43/00; A61Q19/00; A61Q19/02; C07C65/21; C07C205/37; C07C217/30; C07C217/84; C07C229/26; C07C255/54; C07C279/14; C07C323/12
Foreign References:
| JPH0784350A | 1995-03-31 | |||
| US3717611A | 1973-02-20 | |||
| JP2011526250A | 2011-10-06 | |||
| JPH0854716A | 1996-02-27 | |||
| JPS63246311A | 1988-10-13 | |||
| JPH06192062A | 1994-07-12 | |||
| JP4658898B2 | 2011-03-23 | |||
| JP3340930B2 | 2002-11-05 | |||
| JP4828126B2 | 2011-11-30 |
Other References:
YU, T. ET AL.: "3-(4-(tert-Octyl)phenoxy) propane-1,2-diol suppresses inflammatory responses via inhibition of multiple kinases", BIOCHEMICAL PHARMACOLOGY, vol. 83, no. 11, 1 June 2012 (2012-06-01), pages 1540 - 1551, XP055252326
HALL, L. H. ET AL.: "Molecular connectivity and substructure analysis", JOURNAL OF PHARMACEUTICAL SCIENCES, vol. 67, no. 12, 1978, pages 1743 - 1747, XP009064511
YEH, J. L. ET AL.: "Eugenolol and glyceryl- isoeugenol suppress LPS-induced iNOS expression by down-regulating NF-KB and AP-1 through inhibition of MAPKS and AKT/IKBa signaling pathways in macrophages", INTERNATIONAL JOURNAL OF IMMUNOPATHOLOGY AND PHARMACOLOGY, vol. 24, no. 2, 2011, pages 345 - 356, XP008179215
BERGER, F. M. ET AL.: "Antimicrobial action of certain glycerol ethers and related compounds", APPLIED MICROBIOLOGY, vol. 1, 1953, pages 146 - 149, XP008160713
OSANAI, S. ET AL.: "Synthesis of alkoxyl and phenoxyl substituted glycerides and their antimicrobial properties", BOKIN BOBAI, vol. 14, no. 3, 1986, pages 109 - 116, XP001020816
AUZOU, G. ET AL.: "Anxiolytic activity of tert- butyl phenol derivatives. II. Dioxolanones", EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, vol. 10, no. 1, 1975, pages 89 - 90, XP008179197
THEIL, F. ET AL.: "Kinetic resolution of acyclic 1,2-diols using a sequential lipase-catalyzed transesterification in organic solvents", JOURNAL OF ORGANIC CHEMISTRY, vol. 59, no. 2, 1994, pages 388 - 393, XP002173755
THEIL, F. ET AL.: "Lipase-catalyzed resolution of 3-(aryloxy)-1,2-propanediol derivatives. Towards an improved active site model of Pseudomonas cepacia lipase (Amano PS)", TETRAHEDRON: ASYMMETRY, vol. 6, no. 6, 1995, pages 1323 - 1344, XP004048177
AUZOU, G. ET AL.: "Anxiolytic activity derived from a myorelaxant structure. tert-Butylphenol derivatives", EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, vol. 9, no. 5, 1974, pages 548 - 554, XP008179214
JOURNAL OF INVESTIGATIVE DERMATOLOGY, vol. 114, no. L, 2000, pages L57 - 164
See also references of EP 2915796A4
HALL, L. H. ET AL.: "Molecular connectivity and substructure analysis", JOURNAL OF PHARMACEUTICAL SCIENCES, vol. 67, no. 12, 1978, pages 1743 - 1747, XP009064511
YEH, J. L. ET AL.: "Eugenolol and glyceryl- isoeugenol suppress LPS-induced iNOS expression by down-regulating NF-KB and AP-1 through inhibition of MAPKS and AKT/IKBa signaling pathways in macrophages", INTERNATIONAL JOURNAL OF IMMUNOPATHOLOGY AND PHARMACOLOGY, vol. 24, no. 2, 2011, pages 345 - 356, XP008179215
BERGER, F. M. ET AL.: "Antimicrobial action of certain glycerol ethers and related compounds", APPLIED MICROBIOLOGY, vol. 1, 1953, pages 146 - 149, XP008160713
OSANAI, S. ET AL.: "Synthesis of alkoxyl and phenoxyl substituted glycerides and their antimicrobial properties", BOKIN BOBAI, vol. 14, no. 3, 1986, pages 109 - 116, XP001020816
AUZOU, G. ET AL.: "Anxiolytic activity of tert- butyl phenol derivatives. II. Dioxolanones", EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, vol. 10, no. 1, 1975, pages 89 - 90, XP008179197
THEIL, F. ET AL.: "Kinetic resolution of acyclic 1,2-diols using a sequential lipase-catalyzed transesterification in organic solvents", JOURNAL OF ORGANIC CHEMISTRY, vol. 59, no. 2, 1994, pages 388 - 393, XP002173755
THEIL, F. ET AL.: "Lipase-catalyzed resolution of 3-(aryloxy)-1,2-propanediol derivatives. Towards an improved active site model of Pseudomonas cepacia lipase (Amano PS)", TETRAHEDRON: ASYMMETRY, vol. 6, no. 6, 1995, pages 1323 - 1344, XP004048177
AUZOU, G. ET AL.: "Anxiolytic activity derived from a myorelaxant structure. tert-Butylphenol derivatives", EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, vol. 9, no. 5, 1974, pages 548 - 554, XP008179214
JOURNAL OF INVESTIGATIVE DERMATOLOGY, vol. 114, no. L, 2000, pages L57 - 164
See also references of EP 2915796A4
Attorney, Agent or Firm:
JINNO, Naoyoshi et al. (JP)
Naomi Jinno (JP)
Naomi Jinno (JP)
Download PDF: