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United States Patent (19) 11) Patent Number: 4,585,788 Helsley Et Al

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United States Patent (19) 11) Patent Number: 4,585,788 Helsley Et Al United States Patent (19) 11) Patent Number: 4,585,788 Helsley et al. 45) Date of Patent: Apr. 29, 1986 54 6,11-DIHYDRODIBENZB,EOXEPIN ACETIC ACIDS AND DERVATIVES FOREIGN PATENT DOCUMENTS 48-389 6/1972 Japan . 75 Inventors: Grover C. Helsley, Pottersville; 000425 7/1972 Japan. Arthur R. McFadden, East Brunswick, both of N.J.; David Primary Examiner-Norma S. Milestone Hoffman, North Kingstown, R.I. Attorney, Agent, or Firm-Curtis, Morris & Safford 57 ABSTRACT (73) Assignee: American Hoechst Corporation, 6,11-Dihydrodibenzb,eoxepin-acetic acids and deriva Somerville, N.J. tives having the general formula 21 Appl. No.: 459,774 1 22 Fied: Apr. 10, 1974 210 X Yn C-Z Related U.S. Application Data St. 5 k 63 Continuation-in-part of Ser. No. 394,801, Sep. 6, 1973, abandoned. (51) Int. Cl." .................. C07D 313/12; A61K 31/335 are prepared by multi-step sequences. X is C=O, CHCl, 52) U.S. C. ..................................... 514/450; 549/354 CHBr, CH2 or CHOR; Y is alkyl or alkoxy of 1 to 4 (58) Field of Search ........................ 260/333; 549/354; carbon atoms, halogen or trifluoromethyl; n is 0, 1, 2 or 514/450 3; Z is COOR5, CH2OR5, CONR25 or CONHOR5; and Rl-Rs are hydrogen or alkyl of 1 to 4 carbon atoms. 56) References Cited These compounds and the physiologically tolerable U.S. PATENT DOCUMENTS salts thereof are useful as antiinflammatory and analge 3,702,852 11/1972 Yale et al. ........................... 260/333 sic agents. 3,714,201 1/1973 Yale et al. ........................... 260/333 3,758,528 9/1973 Malen et al. ........................ 260/404 21 Claims, No Drawings 4,585,788 1. 2 phenylacetic acid (III), which is then saponified with a 6,11-DIHYDRODIBENZB.EOXEPIN-ACETIC base such as sodium or potassium hydroxide in a solvent ACDS AND DERVATIVES such as ethanol or water for a time of from 15 minutes to 24 hours at a temperature 25 C. to 125 C. to provide This is a continuation in part of Application Ser. No. 5 a substituted carboxybenzyloxyphenylacetic acid (IV). 394,801 filed Sept. 6, 1973, now abandoned. This dicarboxylic acid is cyclized by treatment with a This invention relates to 6,11-dihydrodibenzb,eloxe dehydrating medium such as polyphosphoric acid, etha pin-acetic acids and derivatives thereof having antin nol phosphorus pentoxide, or sulfuric acid with or with flammatory and analgesic activity. out a solvent such as tetramethylenesulfone or acetic To the best of our knowledge, the compounds of this 10 acid at a temperature of 50 to 125 C. for a time of 15 invention have not heretofore been described. Analo minutes to 12 hours to provide a 6,11-dihydro-1 1 gous sulfur compounds: oxodibenzb,eoxepin-acetic acid (V). A 6,11-dihydro-11-oxodibnezb,eloxepin-acetic acid O (V) is allowed to react with an alcohol as methanol or I 15 ethanol in the presence of an acid, such as sulfuric, hydrochloric, or p-toluenesulfonic acid, at a tempera ture of 50 to 90° C. for a time of 15 minutes to 15 hours y-O to provide a 6,11-dihydro-11-oxodibenzb,eloxepin 20 acetic acid ester (VI). This ester is reduced with sodium H H borohydride in a solvent, such as ethanol or 2-propanol, to a 6,11-dihydro-1 1-hydroxy-dibenzb,eoxepin-acetic are mentioned in Japanese Patent Publication No. 7200 acid ester (VII). The hydroxyester is converted to a 425, published Jan. 7, 1972, as having analgesic, antipy bromoester with acetyl bromide or hydrobromic acid in retic and antiinflammatory activity. a solvent such as benzene or toluene at a temperature of The compounds of thc, invention have the formula: 25 35 to 120° C. for a time of 5 minutes to 2 hours to provide a 6,11-dihydro-11-bromo-dibenzb,eoxepin acetic acid ester (VIII). This bromoester is reduced with sodium borohydride in a solvent such as diglyme 30 (CH3OCH2CH2OCH2CH2OCH3) at a temperature of 25 to 80 C. for a time of 10 minutes to 3 hours to provide a 6,11-dihydro-dibenzb,eloxepin-acetic acid ester (IX), which is then saponified with a base such as sodium hydroxide for a time of 15 minutes to 24 hours in which X is C=O, CHCl, CHBr. CH2 or CHOR; Y 35 at a temperature of 25 to 125 C. to provide a 6,11 is alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon dihydro-dibenzb,eoxepin-acetic acid (X). atoms, halogen or trifluoromethyl; n is 0, 1, 2 or 3; Z is A 6,11-dihydro-11-oxodibenzb,eoxepin-acetic acid COOR5, CHOR5, CONHR5, CONR25, or CON (V) may also be allowed to react with thiony chloride HOR5; and R1 to R5 are hydrogen or alkyl of 1 to 4 or phosphorus oxychloride in a solvent such as chloro carbon atoms. The physiologically tolerable salts form, benzene, or dimethylformamide at a temperature thereof are also included. A preferred compound is one of 25 to 85 for a time of 5 minutes to 4 hours to pro ln which R, R2 and R3 are hydrogen; X is C=O, Z is vide a substituted 6,11-dihydro-11-oxodibenzb,eloxe COOH; and n is 0. pin-acetyl chloride (XI). This acid chloride is reacted Another preferred compound is the compound in with ammonia, alkylamine, or dialkylamine in a solvent which RI is CH3; R2 and R3 are H; X is C-O, Z is 45 such as chloroform, benzene, or ether at a temperature COOH, and n is 0. Halogen is intended to mean F, Clor of 10 to 80° C. for a time of 10 minutes to 3 hours to Br. provide a substituted 6,11-dihydro-11-oxodibenz Another very suitable compound of the invention is beloxepin-acetamide (XII). methyl 6,11-dihydro-1 1-oxodibenzb,eoxepin-2-acetate A 6,11-dihydro-11-oxodibenzb,eloxepin-acetic acid in which R, R2 and R3 are hydrogen, X is C-O, Z is 50 ester (VI) in which R1 and R2 are hydrogen may also be COOCH3, and n is zero. Still another important com allowed to react with lithium aluminum hydride in a pound of the invention is 6, 11-dihydro-9-trifluorometh solvent such as ether or tetrahydrofuran at a tempera yl-11-oxodibenzb,e)oxepin-2-acetic acid, in which R, ture of 25 to 70° C. for a time of 10 minutes to 4 hours R2 and R3 are H, X is C=O, Y is CF3 in position 9, Z is to provide a 6,11-dihydro-11-hydroxydibenzb,eloxe COOH and n is 1. 55 pin-ethanol (XIII) or with sodium borohydride in an The compounds of the present invention are prepared alcohol at a temperature of 10 to 70° C. for a time of 30 by a multi-step sequence of reactions as described below minutes to 12 hours to provide a 6,11-dihydro-1 1-alkox and illustrated in the attached flow sheet, in which Y, n, ydibenzb,eloxepin-acetic acid ester (XIV). R1, R2 and R3 are as defined earlier and R is alkyl. As well known to those skilled in the art, the reaction A lower alkyl ester (I), i.e., an ester with 1 to 4 carbon 60 times are correlated to the reaction temperatures in the atoms in the alcoholic unit, of a substituted C sense that shorter times are needed when using higher bromotoluic acid is allowed to react with a lower alkyl temperatures. ester of a hydroxyphenylacetic acid (II) which may be The compounds of the present invention are useful as substituted in a solvent such as acetone, butanone, etha antiinflammatory agents due to their ability to suppress noi, or dimethylformamide with a base such as potas 65 inflammation in mammals. The activity of the com sium carbonate or sodium hydride at a temperature of 0 pounds is demonstrated in the carrageenin induced rat C. to 120° C. for a time of 5 minutes to 12 hours to paw edema antiinflammatory assay Proc. Soc. Exptl. provide a diester of a substituted carboxybenzyloxy Biol. Med., III, 544 (1962); J. Pharmacol. Exp. Ther., 4,585,788 3 4 141, 369 (1963). For example, at doses of 6.5, 10, 17, gun tragacanth or gelatin; an excipient such as starch or and 25 mg/kg of body weight, 6,11-dihydro-11 lactose, a disintegrating agent such as alginic acid, po oxodibenzb,eloxepin-2-acetic acid, 6,11-dihydro-a- tato starch and the like; a lubricant such as magnesium methyl-11-oxodibenzb,eoxepin-2-acetic acid, methyl stearate; and a sweetening agent such as sucrose or 6,11-dihydro-11-oxodibensb,eoxepin-2-acetate, and 5 saccharin may be added or a flavoring agent such as 8-chloro-6,11-dihydro-11-oxodibenzb,eloxepin-2- peppermint, methyl salicylate, or orange flavoring. acetic acid, respectively, exhibit an approximately 50% When the dosage unit form is a capsule, it may contain, inhibition of edema. in addition to materials of the above type, a liquid car Compounds of the present invention are also useful as rier such as fatty oil. Other dosage unit forms may con analgesic agents due to their ability to alleviate pain in 10 tain other various materials which modify the physical mammals. The activity of the compounds is demon form of the dosage unit, for example, as coatings. Thus, strated in the 2-phenyl-1,4-benzoquinone-induced tablets or pills may be coated with sugar, shellac, or writhing test in mice, a standard assay for analgesia both.
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