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United States Patent [191 [11] Patent Number: 4,490,374 Bandurco Et A]

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United States Patent [191 [11] Patent Number: 4,490,374 Bandurco Et A] United States Patent [191 [11] Patent Number: 4,490,374 Bandurco et a]. [45] Date of Patent: Dec. 25, 1984 [54] 5,6-DIALKOXY-3,4-OPTIONALLY [56] References Cited SUBSTITUTED-ZUI-DQUINAZOLINONES COMPOSITION AND METHOD OF USE , U'S' PATENT DOCUMENTS 3,859,237 1/1975 Inaba et al. ....................... .. 424/251 [75] Inventors: victor T. Bandurco, Bridgewater; 3,950,526 4/1976 Inaba et al. ....................... .. 424/251 1 Seymour D. Levine, North F REI N E Brunswick, both of N.J.; Dennis M. o G PATEFT DOCUM NTS Muhey’ New Hope; Alfonso J’ 52717342 1371372 iaelgmm ' 544/286 - - apan ................................. .. T‘ma’ D°ylest°wm b°th °f Pa‘ 7209078 1/1973 Netherlands ...................... .1 544/286 [73] Assignee: Ortho Pharmaceutical Corporation, 2088874 6/1982 Umted Kingdom ' Raritan, NJ. Primary Examiner-Glennon H. Hollrah Assistant Examiner-James H. Turnipseed [21] Appl. No.: 430,552 Attorney, Agent, or Firm-Benjamin F. Lambert [22] Filed: Sep. 30, 19s: [57] ABSIRACI > The synthesis of substituted quinazolinones is described. [51] Int. Cl.3 ................. .. A61K 31/505; C07D 239/80 The novel quinazolinones are renal vasodilators and [52] US. Cl. .................................. .. 424/251; 544/116; thereby increase renal blood ?ow, and are useful as 544/ 118; 544/284; 544/286; 549/451; 549/452; cardiovascular agents. 560/29; 568/425 [58] Field of Search ....................... .. 544/286; 424/251 6 Claims, No Drawings 4,490,374 1 2 provided that when R5 is other than hydrogen the com 5,6-DIALKOXY-3,4-OPTIONALLY SUBSTITUTED-2(1H)QUINAZOLINONES, pound is a quaternary salt when the 3,4-imine linkage is COMPOSITION AND METHOD OF USE unsaturated (the unsaturated imine linkage-between N3 5 and C4 is optional and N3 may or may not be substi The present invention relates to substituted quinazoli nones having functionality at N}. The substituted tuted); Y and Z are hydrogen or hydroxy, provided that quinazolinones which are the subject of this invention at least one of Y and Z is hydroxy; and including the have the following formula alkali metal and alkaline earth metal salts of the pheno 10 lic hydroxyls and the carboxy group at N] and selected Y R] R2 amine salts such as the salts of meglumine, piperazine, sN—Rs N-methylpiperazine, morpholine and aliphatic amines 9 having l-5 carbon atoms; aminoalcohols such as etha N1 §0 nolamine, 2-amino-l,3-propanediol and bis(hydroxyme Z X thyl)methylamine; and amino acids such as arginine, R: lysine and ornithine. When Y and Z are both hydroxy, R4 20 the hydroxyl groups are positioned adjacent to each wherein R1 is hydrogen, amino or nitro; R2 is hydrogen, other and are located at either the 5,6- or the 6,7-posi alkyl having 1-20 carbon atoms, cycloalkyl having 4-8 tion. carbon atoms, cycloalkylalkyl wherein the cycloalkyl Several 6,7-dialkoxy-4-alkyl 2(lI-Dquinazolinones group has 4-8 carbon atoms and the alkyl group has l-3 carbon atoms, haloalkyl having l-3 halogen atoms and 25 have been reported in the literature [Budesinsky et al., l-4 carbon atoms and the halogen is chloro, bromo or Coll. Czech. Chem. Commurt, 37, 2779 (1972); Belgian fluoro, and bicycloalkyl such as norbornyl and norbor Pat. No. 765947 (1971)]. None of the reported substi nylmethyl; R3 and R4 may be the same or different and are hydrogen, lower alkyl having l-6 carbon atoms, tuted quinazolinones have hydroxy groups substituted a.ryl and substituted aryl such as phenyl, 2-, 3-, and 30 on the benzene ring. In addition, the known quinazoli _4-pyridyl, 0-, m-, and p-hydroxyphenyl, halophenyl nones are not similarly substituted at N1. such as p-chlorophenyl, p-?uorophenyl, o-chlorophe nyl, 2,4-di?uorophenyl, lower alkoxyphenyl such as The novel quinazolinones of this invention are renal methoxy, ethoxy, and butoxyphenyl, alkylphenyl vasodilators. As such they increase renal blood ?ow wherein the alkyl group contains 1-6 carbon atoms; X is 35 and are therefore useful as cardiovascular agents. In benzyl, carboxy, carboalkoxy wherein the alkoxy group addition, some of the compounds and some of the inter has 1-3 carbon atoms, cyano, carboxamido, methanesul fonyl, formyl, aroyl, such as benzoyl, substituted ben mediates used to prepare the novel quinazolinones pos zoyl wherein the substituent is an alkyl group having sess cardiotonic activity. l-4 carbon atoms, heteroaryl such as 2-, 3-, and 4-pyri The substituted quinazolinones can be synthesized dyl, and Z-thienyl; heteroaroyl, such as 2-, 3-, and 4 pyridoyl, Z-thienoyl, Z-furoyl and 3-(l,2,5) thiadiazolyl; according to the following schematic diagram. R5 is hydrogen, lower alkyl having l-6 carbons; benzyl or substituted benzyl wherein the substituent is ?uoro, chloro, bromo, alkyl or alkoxy wherein the alkyl group 45 has l-6 carbon atoms; provided that when R5 is other than hydrogen the compound is a quaternary salt when the 3,4-imine linkage is unsaturated; (the presence of an unsaturated imine linkage between N3 and C4 is optional and N3 may or may not be substituted); Y and Z are 50 hydrogen or hydroxy, provided that at least one of Y and Z is hydroxy (when Y and Z are both hydroxy the hydroxyl groups are positioned adjacent to each other at either the 5,6- or the 6,7-position); and including the alkali metal and alkaline earth metal salts of the pheno 55 lic hydroxyls and the carboxy group at N-l and selected amine salts such as the salts of meglumine, piperazine, N-methylpiperazine, morpholine and aliphatic amines having l-5 carbon atoms; aminoalcohols such as etha nolamine, 2-amino-l,3-propanediol and bis(hydroxyme thyl)methylamine; and amino acids such as arginine, lysine and ornithine. The preferred compounds of the present invention are those wherein R1 is hydrogen; R2 is hydrogen, alkyl, cycloalkyl, bicycloalkyl and haloalkyl; R3 and R4 are 65 hydrogen, lower alkyl, aryl and substituted aryl; X is H2 5. R51 carboxy, carboalkoxy, cyano, carboxamido' and formyl; b. HBr R5 is hydrogen, lower alkyl, benzyl, substituted benzyl, 4,490,374 4 priately substituted alkoxyaniline is converted to the corresponding isocyanate. The conversion is carried out with phosgene in'a suitable solvent such as, for example, benzene, toluene or xylene. The isocyanate. is then condensed with the appropriate carboxamide to form the corresponding adduct. The condensation can be carried out either neat or in an inert solvent such vas xylene or toluene. It is preferred to carry out the reac tion at a temperatue between 100°-150° C. The adduct 10 is then cyclized to form a quinazolinone. Suitable cy clizing agents which can be employed include poly phosphoric acid, polyphosphoric ester and a mixture of phosphorous pentoxide and methanesulfonic acid. The ratio of the cyclizing agent to the adduct may vary 15 between 1:1 and 25:1; however, the preferred ratio is 5:1. The reaction is preferably carried out at a tempera ture between 100°-130° C. in an inert atmosphere such as nitrogen. In the second route, an appropriately substi tuted acetophenone is nitrated. After separation of the 20 isomers the substituted o-nitroacetophenone is reduced to the corresponding amine. This is turn is acylated with an alkylhaloformate to give the corresponding ure thane. Cyclization of the urethane so obtained with ammonia gives the corresponding quinazolinone. Ex wherein R1, R2, R3, R4, R5 and X are as de?ned above 25 amples of these transformations are illustrated below. and R is lower alkyl having l-5 carbon atoms. Pharmaceutical compositions containing a compound As can be seen from the diagram, the N1 substituted ' of the present invention as the active ingredient in inti quinazolinone (2) is prepared by reacting a substituted mate admixture with a pharmaceutical carrier can be quinazolinone with an appropriately substituted ole?n, prepared according to conventional pharmaceutical such as methyl cinnamate, methyl acrylate, methyl cro compounding techniques. The carrier may take a wide tonate, acrylonitrile and methyl methacrylate, for exam variety of forms depending on the form of preparation ple. The particular ole?n employed will depend upon desired for administration, e.g., intravenous, oral or the type of substitution desired in the end product. The parenteral. In preparing the compositions in oral dosage reaction is carried out in the presence of a basic catalyst form, any of the usual pharmaceutical media may be such as sodium carbonate, potassium carbonate, potas 35 employed, such as, for example, water, glycols, oils, sium ?uoride, sodium ?uoride, potassium hydroxide, alcohols, ?avoring agents, preservatives, coloring sodium hydroxide, alkali metal alkoxides such as potas agents and the like in the case of oral liquid preparations sium ethoxide, and sodium methoxide, quaternary am such as, for example, suspensions, elixirs and solutions; monium hydroxides such as benzyltrimethylammonium or carriers such as starches, sugars, diluents, granulating hydroxide, quaternary ammonium ?uorides such as 40 agents, lubricants, binders, disintegrating agents and the tetraethylammonium ?uoride and tertiary amines such like in the case of oral solid preparations such as, for as triethylamine. The reaction temperature employed example, powders, capsules and tablets. Because of their can vary between —-l0° C. and 100° C.; the preferred ease in administration, tablets and capsules represent the reaction temperature is about 65° C. most advantageous oral dosage unit form, in which case The N1 substituted quinazolinone (2) can be used to solid pharmaceutical carriers are obviously employed. prepare the other N1 substituted quinazolinones by the If desired, tablets may be sugar coated or enteric coated routes shown in the diagram. For example, the N1 sub by standard techniques. For parenterals, the carrier will stituted quinazolinone (2) can be conveniently alkylated usually comprise sterile water, though other ingredi with an alkyl iodide such as methyl or ethyl iodide or a ents, for example, to aid solubility or for preservative benzyl iodide such as 0-, m-, or p-?uorobenzyl, o-, m-, 50 purposes, may be included.
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