Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1992-05-29
1998-06-02
Ramsuer, Robert W.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
514212, 514300, 540597, 544427, 546122, A61K 3144, A61K 31535, C07D47104
Patent
active
057600341
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
The present invention relates to certain heterocyclic substituted naphthyridinones and to methods and compositions using such compounds.
European published application No. 0 231 709 discloses phenyl naphthyridinones of the formula: ##STR1## wherein Z is, for example, an amine functional group and X and Y are, for example, H, a halogen atom, a lower alkyl group, a trifluoromethyl, an alkoxy, a methylthio, a nitro or a cyano. Among the amine functional groups described are ##STR2## where n is 0 to 5 and it is possible for R.sub.1 and R.sub.2 to form a piperazine ring substituted by an alkyl or an aromatic nucleus which may or may not be substituted, or alternatively to form an imidazole ring. These compounds are disclosed as ulcer-inhibiting drugs.
U.S. Pat. No. 4,684,727 discloses zwitterionic bicyclic compounds of the formula: ##STR3## wherein the substitutents can be among those exemplified below: W and X may be the same or different and each independently represents --CH.dbd. or --N.dbd.; represents --O-- or --S--; and each may be independently selected from the group consisting of, for example, H, alkyl having from 1 to 12 carbon atoms, alkenyl having from 3 to 8 carbon atoms, alkynyl having from 3 to 8 carbon atoms, etc.; represent a ring which can contain from 2 to 8 carbon atoms, such as a pyrrole, piperidine or morpholine ring; be substituted with 1 to 3 substituents Y; and for example, hydroxy, alkyl having from 1 to 6 carbon atoms, halogen, NO.sub.2, alkoxy having from 1 to 6 carbon atoms trifluoromethyl, cyano, etc. These compounds are disclosed as being anti-allergic, anti-inflammatory and/or cytoprotective agents.
SUMMARY OF THE INVENTION
We have now surprisingly found that compounds having the structural formula I ##STR4## or a pharmaceutically acceptable salt thereof have activity useful in the treatment of allergy, inflammation, hyperproliferative skin disease and peptic ulcers, wherein: ##STR5## R.sup.1 represents alkanediyl; R.sup.2 represents a covalent bond or -alkanediyl-O--; hydroxyalkyl having 2 to 6 carbon atoms between the N atom and the OH group; or 1-, 2-, 3-, 4-, 5-, 6- or 7-indanyl, each of which may optionally be substituted with 1 to 3 Y groups as defined below; and alkylthio, --CF.sub.3, --CN, cycloalkyl, alkylsulfinyl or alkylsulfonyl.
Preferably, W is the group ##STR6## A is preferably O and Q is preferably phenyl or substituted phenyl. W is preferably ##STR7## more preferably ##STR8##
Particularly preferred compounds include: ##STR9## or a pharmaceutically acceptable salt thereof.
Other aspects of the invention involve a pharmaceutical composition comprising a compound of formula I above in combination with a pharmaceutically acceptable carrier and methods of treating allergic reactions, inflammation, inflammatory bowel disease, peptic ulcers and hyperproliferative skin disease in a mammal comprising administering to said mammal an effective amount of a compound of formula I for such purpose.
DETAILED DESCRIPTION OF THE INVENTION
Certain compounds of this invention may exist in isomeric forms. The invention contemplates all such isomers both in pure form and in admixture, including racemic mixtures.
Certain compounds of the invention of formula I can exist in unsolvated as well as solvated forms, including hydrated forms, e.g., hemihydrate. In general, the solvated forms, with pharmaceutically acceptable solvents such as water, ethanol and the like, are equivalent to the unsolvated forms for purposes of the invention.
Certain compounds of the invention e.g., those with a strongly basic amine group, also form pharmaceutically acceptable sails with organic and inorganic acids. Examples of suitable acids for such salt formation are hydrochloric, sulfuric, phosphoric, acetic, citric, oxalic malonic, salicylic, malic, fumaric, succinic, ascorbic, maleic, methanesulfonic and other mineral, sulfonic and carboxylic acids well known to those skilled in the art. The salts are prepared by contacting the free base form with a sufficient amount of the
REFERENCES:
patent: 4596809 (1986-06-01), Sherlock
patent: 4684727 (1987-08-01), Blythin et al.
patent: 4786642 (1988-11-01), Teulon
patent: 4794116 (1988-12-01), Blythin
Chemical Abstract, vol. 105: 208847a for FR. 2,567,520 (1986).
Derwent Abstract, 87-222774/32 for EP 231709.
Teulon, Chemical Abstracts, vol. 105:2 088479 (1986).
Jeanette Henry C.
Ramsuer Robert W.
Schering Corporation
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