123723-84-2Relevant academic research and scientific papers
Reaction of 2-(halogenomethyl)-quinoxalines and -quinoline with hydroxybenzoic acids and their esters
Sarodnick,Hilfert,Kempter,Kleinpeter
, p. 714 - 720 (2007/10/03)
In the presence of a base the title compounds react to products with ether structure (4, 6), or with ester structure (3), or to structure 5 containing both functionalities in dependence on the mole ratio of the starting substances, on reaction conditions
SUBSTITUTED QUINOLINYL AND NAPHTHALENYLBENZAMIDES OR BENZYLAMINES AND RELATED COMPOUNDS USEFUL AS ANALGESICS
-
, (2008/06/13)
This invention relates to novel quinolinyl-and naphthalenylbenzamides or benylamines and related disclosed compounds of the formula STR1 wherein X is nitrogen, NO or CR 1 ; Y is C(R 1)(R 2)O, OC(R. sup.1)(R 2), C(R 1)(R 2)N(R 3), N(R. sup.3)C(R 1)(R. sup.2) or C(R 1)=C(R 2); wherein R 1, R 2, and R 3 are independently hydrogen or lower alkyl containing 1 to 10 carbon atoms; Z is oxygen or (R 1)(R 2); R 4 is R 1, benzyl, benzyl ring substituted with R 5, benzyl alpha monosubstituted with R. sup.1, benzyl ring substituted with R 5 and alpha monosubstituted with R 1, phenyl, phenylalkyl containing 2 to 10 carbon atoms in the alkyl group or phenylalkyl ring substituted with R. sup.5 and containing 2 to 10 carbon atoms in the alkyl group; wherein R. sup.5 is R 1, lower alkoxy containing 1 to 10 carbon atoms, halogen, trihalomethyl, NO 2, N(R 1)(R 2) or C(O)N(R 1)(R 2); R 6 is R 1 or R. sup.6 is C(O)(R 7) with the proviso that Z is not oxygen; and wherein R 7 is R 1, phenyl, perfluoroalkyl containing 1 to 10 carbon atoms, phenylalkyl containing 1 to 10 carbon atoms in the alkyl group; or a pharmaceutically acceptable acid addition salt thereof, and their use in the treatment of pain mediated by the biological peptide, bradykinin. In particular, the preferred compounds are where X is nitrogen, and Y is CH 2 O of the above structure.
N- Carboxylic Acids, Hydroxamic Acids, Tetrazoles, and Sulfonyl Carboxamides. Potent Orally Active Leukotriene D4 Antagonists of Novel Structure
Musser, John H.,Kreft, Anthony F.,Bender, Reinhold H. W.,Kubrak, Dennis M.,Grimes, David,et al.
, p. 240 - 245 (2007/10/02)
Four series of N- compounds were prepared as leukotriene D4 (LTD4) antagonists.In the hydroxamic acid series, methyl 3-(2-quinolinylmethoxy)benzeneacetohydroxamate (Wy-48,422, 20) was the most potent inhibitor of LTD4-induced bronchoconstriction with an oral ED50 of 7.9 mg/kg.Compound 20 was also orally inhibited ovalbumin-induced bronchoconstriction in the guinea pig with an ED50 of 3.6 mg/kg.In vitro, against LTD4-induced contraction of isolated guinea pig trachea pretreated with indomethacin and 1-cysteine, 20 produced a pKB value of 6.08.In the sulfonyl carboxamide series, N--3-(2-quinolinylmethoxy)-benzamide (Wy-49,353, 30) was the most potent antagonist.Compound 30 orally inhibited both LTD4- and ovalbumin-induced bronchoconstriction with ED50s of 0.4 and 20.2 mg/kg, respectively.In vitro, against LTD4-induced contraction of isolated guinea pig trachea, 30 produced a pKB value of 7.78.In the carboxylic acid series, which served as intermediates for the above two series, 3-(2-quinolinylmethoxy)benzeneacetic acid (Wy-46,016, 5) was the most potent inhibitor of LTD4-induced bronchoconstriction (99percent at 25 mg/kg, intraduodenally); however, the pKB for this compound was disappointing (5.79).In the tetrazole series, the most potent inhibitor was 2-methyl>quinoline (Wy-49,451, 41).The respective inhibitory ED50s were 3.0 mg/kg versus LTD4 and 17.5 mg/kg versus ovalbumin.In the isolated guinea pig trachea, 41 produced a pKB value of 6.70.
