Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1998-09-01
2000-07-18
Rotman, Alan L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
5462684, 546118, 546296, 546303, 514359, 514379, 514188, A61K 31655, A61K 31371, A61K 3141, C07D41310, C07D40710
Patent
active
060908173
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to triaryl compounds, particularly biphenyl pyridines, biphenyl benzamides and biphenyl phenylcarboxy compounds, processes for their production., their use as pharmaceuticals and pharmaceutical compositions comprising them.
Specifically, the invention provides a (4-oxy-3-(aryl)phenyl)-azaryl or -arylcarbonyloxy, compound, in free or pharmaceutically acceptable acid addition salt form, for use as a pharmaceutical, e.g. for use in the treatment or prophylaxis of inflammation, particularly inflammatory or obstructive diseases of the airways, e.g. asthma.
In a further embodiment the invention provides a pharmaceutical composition comprising a (4-oxy-3-(aryl)phenyl)-azaryl or -arylcarbonyloxy compound, in free or pharmaceutically acceptable acid addition salt form, e.g. in combination with a pharmaceutically acceptable diluent or carrier.
In a yet further embodiment the invention includes the use of a (4-oxy-3-(aryl)phenyl)-azaryl or -arylcarbonyloxy compound, in free or pharmaceutically acceptable acid addition salt form, for the preparation of a medicament for treatment or prophylaxis of inflammation, particularly inflammatory or obstructive diseases of the airways, e.g. asthma.
In a still yet further embodiment the invention provides a method for treatment or prophylaxis of inflammation, particularly inflammatory or obstructive diseases of the airways, e.g. asthma, comprising administering an effective amount of a (4-oxy-3-(aryl)phenyl)-azaryl or -arylcarbonyloxy compound, in free or pharmaceutically acceptable acid addition salt form, to a subject in need of such therapy.
The (4-oxy-3-(aryl)phenyl)-azaryl or -arylcarbonyloxy compounds of the invention and their pharmaceutically acceptable acid addition salt forms are hereinafter referred to as AGENTS OF THE INVENTION. In these compounds, the 4-oxy moiety is suitably (optionally fluoro-substituted)alkoxy, e.g., (fluoro.sub.0-3 -)C.sub.1-4 alkoxy, e.g. methyl, ethyl, difluoromethyl, or trifluoromethyl. The 3-aryl moiety is suitably a mono- or bicyclic moiety having at least one aromatic ring, e.g., azaryl, for example pyridyl, C.sub.1-4 alkylpyridyl, or quinolinyl; aromatic 2,5-cyclohexadien-3,4-ylidine-1-yl, e.g., benzofurazanyl or benzofuranyl; or phenyl, preferably suitably substituted, e.g., meta- and/or para-substituted, with (i) one or two substitutents selected from nitro, carbamoyl, halo (e.g., chloro), trifluoromethyl, alkoxy (e.g. C.sub.1-4 alkoxy), thioalkoxy (e.g. thio(C.sub.1-4)alkoxy), alkylsulphoxy (e.g. C.sub.1-4 alkylsulphoxy), alkylsulphonyl (e.g. C.sub.1-4 alkylsulphonyl), cyano, or phenoxy, or (ii) a bridging substituent of 3-5 atoms in length wherein the bridge atoms are selected from C, O, S, and N, e.g. indanyl, benzopyrolidonyl, indanonyl, or benzodioxolanyl. By "azaryl" is meant a nitrogen-containing aromatic group, for example, pyridine, e.g., 3-pyridine or 4-pyridine, quinoline, isoquinoline, imidazopyridine (e.g. imidazo[1,2-a]pyridine or benzamide, e.g., 3- or 4-benzamide. By "arylcarbonyloxy" is meant an aryl moiety, e.g. as defined above for the 3-aryl moiety, bearing at least one carbonyloxy substituent, e.g. in free acid, ester, amide or salt form, preferably a phenylcarboxy moiety, e.g. a phenyl-3- or phenyl-4-carboxy moiety, such as a phenyl carboxylic acid or phenyl carboxylate ester (e.g. lower alkyl phenyl carboxylate ester) or phenylcarboxamido moiety. Halo or halogen as used herein refers to F, Cl, Br or I unless otherwise indicated.
AGENTS OF THE INVENTION include compounds which are known per se but for which no pharmaceutical activity has been described or suggested. Thus Jin et al. (Macromol. Symp. (1995), 96 [International Conference on Liquid Crystal Polymers 1994], 125-134) describe methyl-4'-methoxy-3'-phenylbiphenyl-4-carboxylate and 4'-acetoxy-3'-phenylbiphenyl-4-carboxylic acid as intermediates in the preparation of copolyester liquid crystal materials. Buu-Hoi et al. (J. Org. Chem. 21, [1956], 136-138) describe the preparation of 2-(6-methoxy-biphenyl-3-yl)-quinoline and anolgue
REFERENCES:
patent: 3329503 (1967-07-01), Franke et al.
Buu-Hoi et al., "Fluorine-containing analogs of 4-hydroxypropiophenone", Journal of Organic Chemisty, vol. 18, 1953, pp. 910-914.
Buu-Hoi et al., "Orientation in some Friedel-Crafts acylations of 2,2'-dimethyoxybiphenyl, and the cyclization of the reaction products", Journal of Organic Chemistry, vol. 29, 1964. pp. 762-763.
Buu-Hoi et al., "The Pfitzinger reaction with ketones derived from o-hydroxydiphenyl" Journal of Organic Chemistry, vol. 21, 1956, pp. 136-138.
Gray et al., "Mesomorphism and Chemical constitution. Part VIII. The effect of 3'-substituents on the Mesomorphism of the 4'-n-alkoxydiphenyl-4-carboxylic acids and their alkyl esters", Journal of the Chemical Society, 1957, pp. 393-399.
Jin et al., "Wholly aromatic polyesters derived from 6-hydroxy-5-phenyl-2-naphthoic acid and 4'-hydroxy-3'-phenylbiphenyl-4-carboxylic acid", Macromolecular Symposia, vol. 96, 1996, pp. 125-134.
Desai Rita
Loeschorn Carol A.
Novartis AG
Rotman Alan L.
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