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United States Patent Office Patented Jan 3,708,589 United States Patent Office Patented Jan. 2, 1973 2 or esterified hydroxy, such as lower alkoxy, e.g. methoxy, 3,708,589 ethoxy, n- or i-propoxy or -butoxy, or halogeno, e.g. HYPOCHOLESTEROELEMIC PHENOXY-AELPHIATEC fluoro, chloro or bromo, or trifluoromethyl. The term ACID COMPOSITIONS William Laszlo Bencze, New Providence, N.J., assignor "lower,” referred to above and hereinafter in connection to Ciba-Geigy Corporation with organic radicals or compounds respectively, defines No Drawing. Continuation-in-part of application Ser. No. such with up to 8, preferably up to 5, carbon atoms. 795,029, Jan. 29, 1969, now Patent No. 3,641,110, Above all, Phi represents 1,2-phenylene, (lower alkyl)- which is a continuation-in-part of application Ser. No. 1,2-phenylene, (5 to 7 ring-membered cycloalkyl)-1,2- 728,871, May 14, 1968, which is a continuation-in-part phenylene, (lower alkoxy)-1,2-phenylene, (halogeno)-1, of application Ser. No. 558,251, June 17, 1966, which O 2-phenylene or (trifluoromethyl)-1,2-phenylene and Ph. in turn is a continuation-in-part of application Ser. represents 1,2-, 1,3- or preferably 1,4-phenylene, (lower No. 323,868, Nov. 15, 1963, now abandoned. This alkyl)-1,2- 1,3- or 1,4-phenylene, (lower alkoxy)-1,2-, application Oct. 31, 1969, Ser. No. 873,107 Int, C. A61k 27/00 1,3- or 1,4-phenylene, (halogeno)-1,2-, 1.3- or 1,4-phenyl U.S. C. 424.317 3 Claims ene or (trifluoromethyl)-1,2-, 1.3- or 1,4-phenylene. 15 The trivalent portion A1, attached to two adjacent posi tions of Phil, may be an unbranched or branched alkylene ABSTRACT OF THE DISCLOSURE chain of preferably 3 to 8, particularly 3 to 5, carbon atoms, which carries at its ring-carbon atoms (a) one or Oxygenated benzcycloalkyl - phenoxy-aliphatic acids, two hydroxy groups or one oxo group and (b) the phenyl e.g. those of the formula 20 ene radical Ph2. It represents, for example, the moieties HOOC-A of the formulae: Phi All-Phe-O -H...--HoH, -ch-oh, - H.--co Ph=a 1,2-phenylene 25 Ph=a 1,2-, 1,3- or 1,4-phenylene --H-I-CHOH-CHOH- o -CH-CHOH-OH A=mono- or dihydroxy-alkylene or alkanoylene forming wherein n is an integer from 2 to 8, preferably from 2 to 5-7 membered ring 5, and m=n-1. Most preferred moieties A1 are the foll A=aliphatic hydrocarbon radical lowing: and functional derivatives thereof are hypocholesterolemic 30 agentS. -R-(CH)-CHOH, -(CH)-R-CHOH CROSS-REFERENCES TO RELATED - R-(CH)-co- -(CH)-r-co- Or APPLICATIONS 35 - R-(CH)-CHOH-CHOH This is a continuation-in-part of application Ser. No. wherein p is an integer from 1 to 3, especially the integer 795,029, filed Jan. 29, 1969, now Pat. No. 3,641,110, 2, q=p-1 and R is hydrogen or lower alkyl, preferably which in turn is a continuation-in-part of application Ser. methyl. No. 728,871, filed May 14, 1968, which in turn is a con The lower aliphatic radical A2 represents, for example, tinuation-in-part of application Ser. No. 558,251, filed 40 lower alkylene, alkenylene or alkynylene, preferably such June 17, 1966, which in turn is a continuation-in-part of having up to 5 carbon atoms, such as methylene, 1,1- or application Ser. No. 323,868, filed Nov. 15, 1963, the 1,2-ethylene, 1,1-, 1,2-, 2,2- or 1,3-propylene, 1,1- 1,2-, latter three of which are now abandoned. 2,3- or 1,4-butylene, 1,1-, 2,2-, 3,3- or 2,4-pentylene; ethylene, 1,2-, 2,3- or 1,3-propenylene, 1,4-butenylene, 1,4- SUMMARY OF THE INVENTION 45 or 2,3-but-2-enylene or 2,3-pent-2-enylene; ethynylene, The present invention concerns and has for its object 1,3-propynylene, 1,3-butynylene, 1,4-but-2-ynylene or 1,4- the provision of new oxygenated benzcycloalkyl-phenoxy pent-2-ynylene. Said radical may also stand for 1,1-cyclo aliphatic acids, preferably of those having the Formula I alkylidene having from 3 to 8, preferably from 5 to 7, 50 ring-carbon atoms, e.g. 1,1-cyclopentylidene, 1,1-cyclo Phi A1-Ph-O-ACOOH hexylidene or 1,1-cycloheptylidene, as well as 1,1-cyclo (I) propylidene, 1,1-cyclo-butylidene or 1,1-cyclooctylidene. in which Phi is a 1,2-phenylene radical, Phi is a 1,2-, 1,3- Functional derivatives of the acids of Formula I are or 1,4-phenylene radical, A is mono- or dihydroxy-lower preferably their esters, for example, their lower alkyl, e.g. alkylene or lower alkanoylene forming with Ph a 5 to 7 55 methyl, ethyl, n- or i-propyl, n-, i-, sec. or tert, butyl esters, membered ring carrying Ph at one ring-carbon atom or substituted lower alkyl, particularly tert. amino-lower thereof and A2 is a lower aliphatic hydrocarbon radical, alkyl, lower alkoxy-lower alkyl or aralkyl, e.g. benzyl or of their functional derivatives, as well as of corresponding 3-pyridylmethyl, esters, in which the tertiary amino group pharmaceutical compositions and of methods for the prep is above all di-lower alkylamino, e.g. dimethylamino or aration and application of these products. Said composi 60 diethylamino, lower alkyleneimino, e.g. pyrrolidino or tions are useful hypocholesterolemic agents in the treat piperidino, or mono-aza- or oxa-lower alkyleneimino, such ment or management of arteriosclerosis. as piperazino or 4-lower alkyl-piperazino, e.g. 4-methyl DESCRIPTION OF THE PREFERRED or ethyl-piperazino, or morpholino. Other functional de EMBODIMENTS rivatives are unsubstituted or substituted amides, e.g. 65 mono- or di-lower alkylamides, mono- or bicyclic lower The phenylene radicals Phi and Ph are unsubstituted alkyleneamides, e.g. the N,N-dimethyl- or diethylamide, or substituted by one or more than one of the same or of N,N-butylene or pentyleneamide or 3 - azabicyclo 3,2,2 different substituents attached to any of the four positions nonyleneamide, or amides of amino-acids, e.g. glycine, available for substitution. Such substituents are, for ex glycyclglycine, taurine, methionine or aspartic acid, as well ample, lower alkyl, e.g. methyl, ethyl, n- or i-propy or 70 as the nitriles, hydroxamic acids and salts. In said ester -butyl, 3- to 8 ring-membered cycloalkyl, e.g. cyclo or amide moieties, two heteroatoms are separated from propyl, cyclopentyl, cyclohexyl or cycloheptyl, etherified each other by at least 2 carbon atoms, preferably by 2 3,708,589 3 4. or 3 carbon atoms, and the tertiary amino group can also caused by arteriosclerosis, e.g. atherosclerosis, and/or as be linked with the lower alkyl chain to form a monoaza anti-inflammatory agents in the treatment or management cycloalkyl or -cycloalkyl-lower alkyl moiety, e.g. 2- or 3 of arthritic and dermatopathologic conditions. Further pyrrollidyl, 1-(methyl or ethyl)-3-pyrrollidyl, 3- or 4-piper more, they can be used as intermediates in the prepara idyl or -piperidyl-methyl. tion of other valuable products, particularly of the phar Salts of the above described compounds are either am macologically active compounds described in the cross-ref monium or metal salts of the acids, or acid addition salts erenced applications. of the compounds with basic character, especially phar Particularly useful are the compounds of Formula I, in maceutically acceptable, non-toxic salts, such as the ann which Phi represents 1,2-phenylene, (lower alkyl)-1,2- monium salts derived from ammonia or amines or, more 10 phenylene, (5 to 7 ring-membered cycloalkyl)-1,2-phenyl particularly metal salts, such as alkali or alkaline earth ene, (lower alkoxy)-1,2-phenylene, (halogeno)-1,2-phen metal, e.g. sodium, potassium, magnesium or calcium ylene or (trifluoromethyl)-1,2-phenylene, Ph. is 1,2-, 1,3- salts. Compounds with basic character are, for example, or 1,4-phenylene, (lower alkyl)-1,2-, 1.3- or 1,4-phenyl the aminoalkyl esters. Such compounds form acid addi ene, (lower alkoxy)-1,2-, 1,3- or 1,4-phenylene, (halo tion salts, such as those of inorganic or organic acids, geno)-1,2-, 1.3- or 1,4-phenylene or (trifluoromethyl)-1, e.g. hydrochloric, hydrobromic, sulfuric, phosphoric, 2-, 1.3- or 1,4-phenylene, A2 is lower alkylene and A is formic, acetic, propionic, pivalic, glycolic, lactic, malonic, one of the moieties Succinic, maleic, hydroxymaleic, malic, tartaric, citric, benzoic, salicylic, 4-aminosalicylic, 2-phenoxybenzoic, 2 - R-(CH)-CHOH- -(CH2)-CR-CHOH acetoxybenzoic, nicotinic, isonicotinic, methane sulfonic, 20 ethane Sulfonic, ethane 1,2-disulfonic, 2-hydroxyethane -CR-(CH2)-CO sulfonic, p-toluene sulfonic or naphthalene 2 - sulfonic acid. Salts, either those of metals or acids, may also be -(CH2)p-CR-CO- or -CR-(CH2)-CHOH-CHOH used as intermediates, for example, in the preparation of Wherein p is an integer from 1 to 3, q is an integer from pharmaceutically acceptable salts, in the purification of 25 0 to 2 and R is hydrogen or lower alkyl; the lower alkyl, the free compounds or for identification or characteriza lower alkoxy-lower alkyl, HPh-lower alkyl, pyridyl-low tion purposes. Functional derivatives of the above com er aikyl, Am-lower alkyl, monoazacycloalkyl or mono pounds are also those of the alcoholic or ketonic func azacycloalkyl-lower alkyl esters thereof, wherein alkoxy, tions, for example, lower alkanoic acid esters or lower An or the aza-nitrogen is separated from the carboxy alkylene or alkylidene ketals, e.g.
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