IL39890A - Xanthone carboxylic acids and derivatives thereof,their preparation and pharmaceutical compositions containing them - Google Patents

Xanthone carboxylic acids and derivatives thereof,their preparation and pharmaceutical compositions containing them

Info

Publication number
IL39890A
IL39890A IL3989072A IL3989072A IL39890A IL 39890 A IL39890 A IL 39890A IL 3989072 A IL3989072 A IL 3989072A IL 3989072 A IL3989072 A IL 3989072A IL 39890 A IL39890 A IL 39890A
Authority
IL
Israel
Prior art keywords
compound according
carboxylic acid
xanthone
hydrogen
alkyl
Prior art date
Application number
IL3989072A
Original Assignee
Syntex Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US217383A external-priority patent/US3873714A/en
Priority claimed from US00259853A external-priority patent/US3818042A/en
Application filed by Syntex Corp filed Critical Syntex Corp
Publication of IL39890A publication Critical patent/IL39890A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
    • C07D311/82—Xanthenes
    • C07D311/84—Xanthenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 9
    • C07D311/86—Oxygen atoms, e.g. xanthones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
    • C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Claims (1)

  1. CLAIMS 1. A compound selected from those represented by following formulas: and the pharmaceutically acceptable, non-toxic alkyl esters, unsubstituted amides and salts thereof; wherein each R is a group selected from those of the formulas in which R' is hydrogen, lower alkyl, tetrahydropyran-2-yl, tetrahydropyran-4-yl, 4-alkoxytetrahydropyran-4-yl, or alkanoyl containing up to 12 carbon atoms; R1 is hydrogen or lower 2 alkyl; and R is hydrogen, lower alkyl, cycloalkyl, phenyl, furyl or thienyl.- 2. The compound* according to Claim 1 of formula (A). 3. The compound according to Claim 2 wherein R i the group C-R' . ΐη which R ' is hydrogen, methyl, or acet I ^ 39890/2 4. The compound according to Claim 3 wherein R is hydrogen. 5. The compound according to Claim 4 wherein R is x lower' alkyl. 6. The compound according to Claim 5 wherein R 2 ' hydrogen and R is methyl; 5- (l-hydroxy?thyl).-xanthone-2 carboxylic acid. 7. The compound according to Claim 3 wherein ea 1 - 2 of R and is lower alkyl. 8. The' compound according to Claim 7 wherein R' is 1 2 hydrogen and each of R and R is methyl; 5- ( 1-hydroxy-l-methylethyl) -xanthone-2-carboxylic acid. 9. The compound according to Claim 2 wherein R is the group in which R has the same meaning as in Claim 1. 10. The compound according to Claim 9 wherein R is lower alkyl. 11. The compound according' to Claim 9. wherein R is hydrogen; 5-formylxanthone-2-carboxylic acid. 39890/2 2 ' 12. The compound according to Claim 9 wherein R is. methyl; 5-acetylxanthone-2-carboxylic acid. ' 13· j The compound according to Claim 1 of formula (B) 14·; The compound according to Claiml3 wherein R is the group hydrogen, methyl, or acetyl. f 15·: The compound according to Claim <' 4·.where in R^" is hydrogen. 2 16* The compound according to. Claim 1 . wherein R lower alkyl 17.' The compound according to . Claim 16 ■ wherein R' is hydrooggeenn aanndd RR2 is methyl; '7-(l-hydroxyethyl.) -xanthone-2-carboxylic acid. . '·' ' 18. The compound according to Claim17 , wherein each 1 2 of R and R is lower alkyl; 19.' The compound according to Claim118 wherein R hydrogen and each of R and R is methyl; 7- (1-hydroxy methylethyl) -xanthone-2-carboxylic acid. Ί 20. (' The compound according to Claim 13 wherein R is the. group ■„-R2 . 39890/2 21. ! The compound according to Claim' 20. wherein. R s lower a kyl. ¾ ' 2 ' . '22. ',' The compound according to Claim' 20 wherein R s hydrogen; 7-formylxanthone-2--carboxylic acid. • I · 2 23.. The compound according to Claim; 20 wherein R' is methyl; .7-acetylxanthone-2~carboxylic acid. 24· · The sodium salts of the compounds according ;to Claim 1. 25 The salts according to Claim; 2 of formula (B) . 26. The compound according to Claim; 25 which is sodium 7-acetylxanthone-2-carboxylate.. 1 · ·' . . , • 27.'· The compound according to Claim^25 which is sodium 7- (.I-hydroxyethyl) -xanthone-2-'carboxylate . 2Θ. A method useful for inhibiting the effects of the allergic reaction in non-human animals, which comprises administering an effective amount of a compound as claimed in Claim 1, or a pharmaceutically acceptable non-toxic compo sition incorporating said compounds, esters, or salts as an essential ingredient. 29. A composition useful for inhibiting the effects of the allergic reaction comprising an effective amount of a compound as claimed in Claim 1, in admixture with a pharmaceutically acceptable non-toxic carrier. corresponding 1 , 3-dimethyl-4- (o- or p-acylphenyloxy) -benzene, oxidizing the latter to give the corresponding 1, 3-dicarboxy-4-(o- or p-acylphenyloxy) -benzene, and cyclizing the latter to give the corresponding 5- or 7-acylxanthone-2-carboxylic acid; or 3) oxidizing a compound represented by the formula (9) (9) 2 ' 2 3 wherein R is R exclusive of hydrogen and R is lower alkyl, optionally followed by hydrolysis, to give the corresponding 7-acylxanthone-2-carboxylic acids or the alkyl esters thereof; or 4) treating a 5- or 7- (1, 2-oxidoethyl) -xanthone-2-carboxylic acid alkyl ester with periodic .acid or with perchloric acid and sodium periodate optionally followed by hydrolysis to give the corresponding 5- or 7-formylxanthone-2-carboxylic acid or the alkyl esters thereof; or 5) oxidizing a 5- or 7-alkylxanthone-2-carboxylic acid or its alkyl ester with chromium trioxide in acetic acid-acetic anhydride optionally followed by hydrolysis to give the corresponding 5- or 7-acylxanthone-2-carboxylic acid or the alkyl esters thereof; or 6) reducing a 5- or 7-acylxanthone-2-carboxylic acid ester of steps 1), 2), 3), 4), and 5) optionally followed by hydrolysis to give the corresponding 7- (secondary hydroxyalkyl) xanthone-2-carboxylic acids or the alkyl esters thereof; or 7) treating an appropriate 5- or 7-acylxanthone-2- alkyl or cycloalkyl Grignard reagent optionally followed by hydrolysis to give the corresponding 7- (tertiary hydroxyalkyl) -xanthone-2-carboxylic acids or the alkyl esters thereof; and 8) optionally esterifying a hydroxyalkyl product of steps 6) and 7) to give the corresponding 5- or 7-acyloxyalkyl-xanthone-2-carboxylic acid; and 9) optionally etherifying a hydroxyalkyl product of steps 6) and 7) to give the corresponding 5- or 7-etherified-hydroxyalkylxanthone-2-carboxylic acid; and 10) optionally converting a product of steps 1), 2), 3), 4), 5), 6), 7)/ 8) , and 9) to its pharmaceutically acceptable non-toxic esters , amides and salts. 31 30 ^3*. The process according to Claim ffl whe: 1) the starting compounds of step 3) of formula (9) are prepared by the process which comprises reducing xanthone-2-carboxylic acid to give the corresponding xanthene-2-carboxylic acid, esterifying the latter to the corresponding acid alkyl_ esters, and acylating the latter with an acid chloride in the presence of aluminum chloride, said xanthone-2-carboxylic acid being optionally prepared by condensing phenol with a 1,3-di-carboalkoxy-4-halobenzene in the presence of cuprous oxide, base hydrolyzing the product thereof, and cyclizing the hydrolyzed product; and 2) the starting compounds of step 4) are prepared by the process which comprises acylating a xanthene-2-carboxylic acid alkyl ester with chloroacetyl chloride, oxidizing the acylated product to the corresponding xanthone compound, reducing the latter to give the 5- or 7- (2-chloro-l-hydroxyethyl) -xanthone-2-carboxylic acid alkyl ester, and treating the latter I 3) the starting compounds of step 5) are prepared by the process which comprises condensing a o- or p-alkylphenol with a 1, 3-dicarboalkoxy-4-halobenzene in the presence of cuprous oxide, base hydrolyzing the product thereof to give the corresponding 1, 3-dicarboxy-4- (o- or p-alkylphenyloxy) -benzene, and cyclizing the latter. For the flpMcarits DR. REI; D AlfD PAWNERS By:
IL3989072A 1971-07-14 1972-07-12 Xanthone carboxylic acids and derivatives thereof,their preparation and pharmaceutical compositions containing them IL39890A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US16269671A 1971-07-14 1971-07-14
US217383A US3873714A (en) 1971-07-14 1972-01-12 Xanthone carboxylic acids and derivatives
US00259853A US3818042A (en) 1972-01-12 1972-06-05 Xanthone carboxylic acids and derivatives

Publications (1)

Publication Number Publication Date
IL39890A true IL39890A (en) 1976-02-29

Family

ID=27388786

Family Applications (1)

Application Number Title Priority Date Filing Date
IL3989072A IL39890A (en) 1971-07-14 1972-07-12 Xanthone carboxylic acids and derivatives thereof,their preparation and pharmaceutical compositions containing them

Country Status (11)

Country Link
AT (1) AT326121B (en)
BE (1) BE786169A (en)
CH (1) CH580093A5 (en)
DE (1) DE2234256A1 (en)
DK (1) DK141096B (en)
ES (6) ES404786A1 (en)
FR (1) FR2145654B1 (en)
GB (1) GB1386436A (en)
IL (1) IL39890A (en)
NL (1) NL7209628A (en)
SE (1) SE388421B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4585876A (en) * 1982-11-25 1986-04-29 Ciba-Geigy Corporation Novel xanthones and thioxanthones

Also Published As

Publication number Publication date
NL7209628A (en) 1973-01-16
ES404786A1 (en) 1976-01-01
CH580093A5 (en) 1976-09-30
BE786169A (en) 1973-01-12
DK141096B (en) 1980-01-14
AU4445672A (en) 1974-01-17
ES435669A1 (en) 1977-05-01
ES435671A1 (en) 1977-05-01
AT326121B (en) 1975-11-25
DE2234256A1 (en) 1973-01-25
ES435672A1 (en) 1977-05-01
ES435673A1 (en) 1977-07-01
DK141096C (en) 1980-07-14
FR2145654B1 (en) 1975-06-20
ATA599372A (en) 1975-02-15
FR2145654A1 (en) 1973-02-23
SE388421B (en) 1976-10-04
ES435670A1 (en) 1977-05-01
GB1386436A (en) 1975-03-05

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