Title:
PHENOXIACETIC ACID DERIVATIVES
Document Type and Number:
WIPO Patent Application WO2005018529
Kind Code:
A3
Abstract:
The invention relates to certain 2-substituted phenoxyacetic acid derivatives of formula (I), in which the variables are as defined in the claims, useful in the treatment of diseases or conditions in which modulation of the CRTh2 receptor is beneficial, such as asthma and rhinitis.
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Inventors:
BONNERT ROGER VICTOR (GB)
PATEL ANIL (GB)
THOM STEPHEN (GB)
PATEL ANIL (GB)
THOM STEPHEN (GB)
Application Number:
PCT/GB2004/003551
Publication Date:
April 21, 2005
Filing Date:
August 18, 2004
Export Citation:
Assignee:
ASTRAZENECA AB (SE)
ASTRAZENECA UK LTD (GB)
BONNERT ROGER VICTOR (GB)
PATEL ANIL (GB)
THOM STEPHEN (GB)
ASTRAZENECA UK LTD (GB)
BONNERT ROGER VICTOR (GB)
PATEL ANIL (GB)
THOM STEPHEN (GB)
International Classes:
A61P11/06; C07C205/38; C07C255/54; C07C311/08; C07C311/29; C07C317/22; C07C317/36; C07C323/60; C07C323/65; C07C323/67; C07D215/36; (IPC1-7): C07C205/38; C07C255/54; C07C311/08; C07C311/29; C07C317/22; C07C317/36; C07C323/60; C07C323/65; C07C323/67; C07D213/70; C07D215/20; C07D215/36; C07D239/34; A61K31/192; A61P11/06
Domestic Patent References:
| WO2003066047A1 | 2003-08-14 |
Foreign References:
| GB2031408A | 1980-04-23 | |||
| GB1469687A | 1977-04-06 | |||
| CH432119A | 1967-03-15 | |||
| US3920846A | 1975-11-18 | |||
| GB1585963A | 1981-03-11 |
Other References:
J.H. AMIN, ET AL.: "The Fries reaction: part VI - the rearrangement of aryl p-toluenesulphonates and a convenient method for the synthesis of hydroxy-diarylsulphones", JOURNAL OF SCIENTIFIC & INDUSTRIAL RESEARCH, vol. 13B, 1954, INDIA, pages 181 - 183, XP000600360
R.C. HUSTON, ET AL.: "Chloro derivatives of benzyl phenols. II. Some monochloro, dichloro and trichloro derivatives of ortho and para benzyl phenols", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 55, no. 11, 1 November 1933 (1933-11-01), AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, pages 4639 - 4643, XP000616052, ISSN: 0002-7863
V. BALIAH, ET AL.: "Fries rearrangement of the benzenesulphonates of xylenols", RECUEIL DES TRAVAUX CHIMIQUES DES PAYS-BAS, vol. 80, 1961, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, pages 139 - 148, XP008036925
S.D. MOSHCHITSKII, ET AL.: "Smiles reararangement of tetrachloropyridyl methyl-hydroxyphenyl sulphone", CHEMISTRY OF HETEROCYCLIC COMPOUNDS (TRANSLATION OF KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII), vol. 15, no. 7, October 1979 (1979-10-01), PLENUM PRESS, NEW YORK, NY, US, pages 1085 - 1088, XP008036868
M.T. COCCO, ET AL.: "Annulation of functionalised hexadienones as an efficient regioselective approach to N-aryl-2-(trifluoromethyl)-4-pyridinamines", TETRAHEDRON LETTERS, vol. 40, no. 23, 4 June 1999 (1999-06-04), ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, pages 4407 - 4410, XP004164661, ISSN: 0040-4039
W.B. WHEATLEY, ET AL.: "2-Benzylphenol derivatives. III. Basic ethers", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 71, no. 11, 19 December 1949 (1949-12-19), AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, pages 3795 - 3797, XP002301118
V.V. LITVAK, ET AL.: "Synthesis and SNAr reactions of new dioxins and predioxins", CHEMOSPHERE, vol. 43, no. 4-7, May 2001 (2001-05-01), ELSEVIER SCIENCE, OXFORD, GB, pages 493 - 495, XP002301119
L. MEUNIER, ET AL.: "Photochemical behaviour of dichlorprop [(+/-)-2-(2,4-dichlorophenoxy)propanoic acid] in aqueous solution", PEST MANAGEMENT SCIENCE, vol. 58, no. 8, August 2002 (2002-08-01), JOHN WILEY AND SONS, BOGNOR REGIS, GB, pages 845 - 852, XP002301196
J.P. BROWN, ET AL.: "Some chlorinated hydroxyphenylacetic acids", JOURNAL OF THE CHEMICAL SOCIETY., 1955, ROYAL SOCIETY OF CHEMISTRY, LETCHWORTH, GB, pages 3681 - 3687, XP002236408, ISSN: 0368-1769
J.K. GAUNT, ET AL.: "Metabolism of 4-chloro-2-methylphenoxyacetate by a soil pseudomonad", BIOCHEMICAL JOURNAL, vol. 122, 1971, PORTLAND PRESS, LONDON, GB, pages 519 - 526, XP008036904
G.W.K. CAVIL, ET AL.: "The chemistry of plant-growth regualtors. Part I. 2,4-Dichloro-6-hydroxyphenoxyacetic acid and related compounds", JOURNAL OF THE CHEMICAL SOCIETY, 1954, ROYAL SOCIETY OF CHEMISTRY, LETCHWORTH, GB, pages 565 - 569, XP002301120
G. THUILLIER: "Dérivés des acides aryloxyacétiques à activité neurotrope", CHIMIE THERAPEUTIQUE, vol. 1, no. 2, 1966, EDITIONS DIMEO, ARCUEIL, FR, pages 82 - 86, XP002301121
Y. INUKAI, ET AL.: "ortho-Disubstituted F-benzenes. III. Preparation of (F-benzoheterocyclic compounds from F-benzoic acid and F-phenol, and the reactions of some intermeiary F-benzoyl- and F-phenoxy compounds", BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, vol. 54, no. 11, November 1981 (1981-11-01), JAPAN PUBLICATIONS TRADING, TOKYO, JP, pages 3447 - 3452, XP002301122
G.G. GALLO, ET AL.: "Spirodioxolanonarenones. II. Synthesis of a halogenated 1,4-dioxaspiro[4,5]deca- 7,9-diene-2,6-dione", JOURNAL OF ORGANIC CHEMISTRY, vol. 30, no. 5, May 1965 (1965-05-01), AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, pages 1657 - 1658, XP002301123
S. SELVI, ET AL.: "Vilsmeier cyclisation of 2-aminophenoxyacetic acid", SYNTHETIC COMMUNICATIONS, vol. 31, no. 14, July 2001 (2001-07-01), MARCEL DEKKER, NEW YORK, NY, US, pages 2199 - 2202, XP002301124
DATABASE WPI Section Ch Week 200365, Derwent World Patents Index; Class B03, AN 2003-689635, XP002301315
R.C. HUSTON, ET AL.: "Chloro derivatives of benzyl phenols. II. Some monochloro, dichloro and trichloro derivatives of ortho and para benzyl phenols", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 55, no. 11, 1 November 1933 (1933-11-01), AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, pages 4639 - 4643, XP000616052, ISSN: 0002-7863
V. BALIAH, ET AL.: "Fries rearrangement of the benzenesulphonates of xylenols", RECUEIL DES TRAVAUX CHIMIQUES DES PAYS-BAS, vol. 80, 1961, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, pages 139 - 148, XP008036925
S.D. MOSHCHITSKII, ET AL.: "Smiles reararangement of tetrachloropyridyl methyl-hydroxyphenyl sulphone", CHEMISTRY OF HETEROCYCLIC COMPOUNDS (TRANSLATION OF KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII), vol. 15, no. 7, October 1979 (1979-10-01), PLENUM PRESS, NEW YORK, NY, US, pages 1085 - 1088, XP008036868
M.T. COCCO, ET AL.: "Annulation of functionalised hexadienones as an efficient regioselective approach to N-aryl-2-(trifluoromethyl)-4-pyridinamines", TETRAHEDRON LETTERS, vol. 40, no. 23, 4 June 1999 (1999-06-04), ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, pages 4407 - 4410, XP004164661, ISSN: 0040-4039
W.B. WHEATLEY, ET AL.: "2-Benzylphenol derivatives. III. Basic ethers", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 71, no. 11, 19 December 1949 (1949-12-19), AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, pages 3795 - 3797, XP002301118
V.V. LITVAK, ET AL.: "Synthesis and SNAr reactions of new dioxins and predioxins", CHEMOSPHERE, vol. 43, no. 4-7, May 2001 (2001-05-01), ELSEVIER SCIENCE, OXFORD, GB, pages 493 - 495, XP002301119
L. MEUNIER, ET AL.: "Photochemical behaviour of dichlorprop [(+/-)-2-(2,4-dichlorophenoxy)propanoic acid] in aqueous solution", PEST MANAGEMENT SCIENCE, vol. 58, no. 8, August 2002 (2002-08-01), JOHN WILEY AND SONS, BOGNOR REGIS, GB, pages 845 - 852, XP002301196
J.P. BROWN, ET AL.: "Some chlorinated hydroxyphenylacetic acids", JOURNAL OF THE CHEMICAL SOCIETY., 1955, ROYAL SOCIETY OF CHEMISTRY, LETCHWORTH, GB, pages 3681 - 3687, XP002236408, ISSN: 0368-1769
J.K. GAUNT, ET AL.: "Metabolism of 4-chloro-2-methylphenoxyacetate by a soil pseudomonad", BIOCHEMICAL JOURNAL, vol. 122, 1971, PORTLAND PRESS, LONDON, GB, pages 519 - 526, XP008036904
G.W.K. CAVIL, ET AL.: "The chemistry of plant-growth regualtors. Part I. 2,4-Dichloro-6-hydroxyphenoxyacetic acid and related compounds", JOURNAL OF THE CHEMICAL SOCIETY, 1954, ROYAL SOCIETY OF CHEMISTRY, LETCHWORTH, GB, pages 565 - 569, XP002301120
G. THUILLIER: "Dérivés des acides aryloxyacétiques à activité neurotrope", CHIMIE THERAPEUTIQUE, vol. 1, no. 2, 1966, EDITIONS DIMEO, ARCUEIL, FR, pages 82 - 86, XP002301121
Y. INUKAI, ET AL.: "ortho-Disubstituted F-benzenes. III. Preparation of (F-benzoheterocyclic compounds from F-benzoic acid and F-phenol, and the reactions of some intermeiary F-benzoyl- and F-phenoxy compounds", BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, vol. 54, no. 11, November 1981 (1981-11-01), JAPAN PUBLICATIONS TRADING, TOKYO, JP, pages 3447 - 3452, XP002301122
G.G. GALLO, ET AL.: "Spirodioxolanonarenones. II. Synthesis of a halogenated 1,4-dioxaspiro[4,5]deca- 7,9-diene-2,6-dione", JOURNAL OF ORGANIC CHEMISTRY, vol. 30, no. 5, May 1965 (1965-05-01), AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, pages 1657 - 1658, XP002301123
S. SELVI, ET AL.: "Vilsmeier cyclisation of 2-aminophenoxyacetic acid", SYNTHETIC COMMUNICATIONS, vol. 31, no. 14, July 2001 (2001-07-01), MARCEL DEKKER, NEW YORK, NY, US, pages 2199 - 2202, XP002301124
DATABASE WPI Section Ch Week 200365, Derwent World Patents Index; Class B03, AN 2003-689635, XP002301315
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