Claims
- 1. A polycyclic aromatic compound having the formula ##STR20## wherein X represents O or S,
- R.sub.1 represents hydrogen, branched alkyl having 3-15 carbon atoms, alkoxy having 1-6 carbon atoms or 1-adamantyl,
- R.sub.2 represents hydrogen, hydroxy, linear or branched alkyl having 1-15 carbon atoms or alkoxy having 1-6 carbon atoms, with the proviso that R.sub.1 and R.sub.2 are not simultaneously hydrogen, or R.sub.1 and R.sub.2 together with the adjacent carbon atoms of the naphthalene ring form a 5 or 6 carbon ring optionally substituted by at least one lower alkyl radical, or interrupted by an oxygen atom,
- R.sub.3 represents --CH.sub.2 OH or --COR.sub.4 or R.sub.3 represents --CH.sub.3 when R.sub.1 and R.sub.2 taken together form a 5 or 6 carbon ring,
- R.sub.4 represents ##STR21## R.sub.5 represents hydrogen, alkyl having 1-20 carbon atoms, monohydroxyalkyl, polyhydroxyalkyl, aryl or aralkyl optionally substituted, or the residue of a sugar or the radical ##STR22## p is 1, 2 or 3, r' and r" represent hydrogen, lower alkyl, monohydroxyalkyl, polyhydroxyalkyl, aryl optionally substituted as the residue of an amino acid or the residue of an amino sugar, or taken together form a heterocycle,
- and the salts of said polycyclic aromatic compound of formula I.
- 2. The compound of claim 1 wherein said alkyl having 1-20 carbon atoms is methyl, ethyl, propyl, 2-ethylhexyl, octyl, dodecyl, hexadecyl or octadecyl.
- 3. The compound of claim 1 wherein said monohydroxyalkyl is 2-hydroxyethyl or 2-hydroxypropyl.
- 4. The compound of claim 1 wherein said polyhydroxyalkyl is 2,3-dihydroxypropyl, 2,3,4-trihydroxybutyl, 2,3,4,5-tetrahydroxypentyl or the residue of pentaerythritol.
- 5. The compound of claim 1 wherein said residue of a sugar is a residue derived from glucose, mannose, erythrose or galactose.
- 6. The compound of claim 1 wherein said residue of an amino sugar is a residue derived from glucosamine, galactosamine or mannosamine.
- 7. The compound of claim 1 wherein r' and r" taken together form a heterocycle selected from the group consisting of piperidino, piperazino, morpholino and pyrrolidino.
- 8. The compound of claim 1 selected from the group consisting of
- 5-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthracenyl)-2-furane carboxylic acid,
- the methyl ester of 5-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthracenyl)-2-furane carboxylic acid,
- 5-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthracenyl)-2-thiophene carboxylic acid,
- the methyl ester of 5-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthracenyl)-2-thiophene carboxylic acid,
- the ethylamide of 5-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthracenyl)-2-furane carboxylic acid and
- 2-hydroxyethyl-5-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthracenyl)-2-furane carboxylate.
- 9. The compound of claim 1 having the formula ##STR23## wherein X is O or S and
- R.sub.5 represents hydrogen or alkyl.
- 10. A process for preparing a compound having the formula ##STR24## wherein X represents --CH.dbd.CH--, O or S,
- R.sub.1 represents hydrogen, branched alkyl having 3-15 carbon atoms, alkoxy having 1-6 carbon atoms or 1-adamantyl,
- R.sub.2 represents hydrogen, hydroxy, linear or branched alkyl having 1-15 carbon atoms or alkoxy having 1-6 carbon atoms, with the proviso that R.sub.1 and R.sub.2 are not simultaneously hydrogen, or R.sub.1 and R.sub.2 together with the adjacent carbon atoms of the naphthalene ring form a 5 or 6 carbon ring optionally substituted by at least one lower alkyl radical, or interrupted by an oxygen atom,
- R.sub.3 represents --CH.sub.2 OH or --COR.sub.4 or R.sub.3 represents --CH.sub.3 when R.sub.1 and R.sub.2 taken together form a 5 or 6 carbon ring,
- R.sub.4 represents --OR.sub.5 or ##STR25## represents hydrogen, alkyl having 1-20 carbon atoms, monohydroxyalkyl, polyhydroxyalkyl, aryl or aralkyl optionally substituted, or the residue of a sugar or the radical ##STR26## p is 1, 2 or 3, r' and r" represent hydrogen, lower alkyl, monohydroxyalkyl, polyhydroxyalkyl, aryl optionally substituted as the residue of an amino acid or the residue of an amino sugar, or taken together form a heterocycle,
- said process comprising
- (1) reacting by a coupling reaction of the Wittig or Wittig-Horner type an aromatic aldehyde having the formula ##STR27## wherein R.sub.1 and R.sub.2 have the same meanings given above, with a pentavalent phosphorous derivative having the formula ##STR28## wherein X and R.sub.5 have the same meanings given above,
- A represents (i)--P[X'].sub.3.sup.+ Y.sup.- wherein X' represents aryl and Y represents an anion of an organic or inorganic acid, or (ii) ##STR29## wherein Z represents alkoxy, and R and R' represent lower alkyl or taken together form a dioxane or dioxolane ring, and
- (2) effecting a cyclization-aromatization reaction of the product obtained in step (1), in a chlorinated solvent, in the presence of an acid catalyst, said reaction optionally being effected under UV radiation.
- 11. The process of claim 10 wherein A represents ##STR30## said coupling reaction in step (1) being carried out in the presence of lithium di-isopropylamide in tetrahydrofuran at a temperature of about -80.degree. C.
- 12. The process of claim 10 wherein said cyclization-aromatization reaction of step (2) is carried out in dichloromethane or chloroform in the presence of sulfuric acid, paratoluene sulfonic acid or trifluoromethane sulfonate of trimethylsilyl.
- 13. A process for preparing a compound having the formula ##STR31## wherein X represents --CH.dbd.CH--, O or S,
- R.sub.1 represents hydrogen, branched alkyl having 3-15 carbon atoms, alkoxy having 1-6 carbon atoms or 1-adamantyl,
- R.sub.2 represents hydrogen, hydroxy, linear or branched alkyl having 1-15 carbon atoms or alkoxy having 1-6 carbon atoms, with the proviso that R.sub.1 and R.sub.2 are not simultaneously hydrogen, or R.sub.1 and R.sub.2 together with the adjacent carbon atoms of the naphthalene ring form a 5 or 6 carbon ring optionally substituted by at least one lower alkyl radical, or interrupted by an oxygen atom,
- R.sub.3 represented --CH.sub.2 OH or --COR.sub.4 or R.sub.3 represents --CH.sub.3 when R.sub.1 and R.sub.2 taken together form a 5 or 6 carbon ring,
- R.sub.4 represents --OR.sub.5 or ##STR32## R.sub.5 represents hydrogen, alkyl having 1-20 carbon atoms, monohydroxyalkyl, polyhydroxyalkyl, aryl or aralkyl optionally substituted, or the residue of a sugar or the radical ##STR33## p is 1, 2 or 3, r' and r" present hydrogen, lower alkyl, monohydroxyalkyl, polyhydroxyalkyl, aryl optionally substituted as the residue of an amino acid or the residue of an amino sugar, or taken together form a heterocycle,
- said process comprising
- (1) reacting by a reaction of the Wittig or Wittig-Horner type an aromatic aldehyde of the formula ##STR34## with a pentavalent phosphorus derivative of the formula ##STR35## wherein R.sub.1 and R.sub.2 have the meanings given above,
- A represents (i) --P[X'].sub.3.sup.+ Y- wherein X' represents aryl and Y represents an anion of an organic or inorganic acid, or (ii) ##STR36## wherein Z represents alkoxy, and R and R' represent lower alkyl or taken together form a dioxane or dioxolane ring,
- (2) reacting the intermediate compound resulting from step (1), said intermediate compound having the formula ##STR37## with a halogen-ester of the formula ##STR38## wherein X and R.sub.5 have the meanings given above and
- X.sub.1 represents Cl and Br, and
- (3) effecting a cyclization-aromatization reaction of the product obtained in step (2).
- 14. A pharmaceutical composition comprising in a pharmaceutically acceptable vehicle at least one polycyclic aromatic compound having the formula ##STR39## wherein X represents --CH.dbd.CH--, O or S,
- R.sub.1 represents hydrogen, branched alkyl having 3-15 carbon atoms, alkoxy having 1-6 carbon atoms or 1-adamantyl,
- R.sub.2 represents hydrogen, hydroxy, linear or branched alkyl having 1-15 carbon atoms or alkoxy having 1-6 carbon atoms, with the proviso that R.sub.1 and R.sub.2 are not simultaneously hydrogen, or R.sub.1 and R.sub.2 together with the adjacent carbon atoms of the naphthalene ring form a 5 or 6 carbon ring optionally substituted by at least one lower alkyl radical, or interrupted by an oxygen atom,
- R.sub.3 represents --CH.sub.2 OH or --COR.sub.4 or R.sub.3 represents --CH.sub.3 when R.sub.1 and R.sub.2 taken together form a 5 or 6 carbon ring,
- R.sub.4 represents --OR.sub.5 or ##STR40## R.sub.5 represents hydrogen, alkyl having 1-20 carbon atoms, monohydroxyalkyl, polyhydroxyalkyl, aryl or aralkyl optionally substituted, or the residue of a sugar or the radical ##STR41## p is 1, 2 or 3, r' and r" represent hydrogen, lower alkyl, monohydroxyalkyl, polyhydroxyalkyl, aryl optionally substituted as the residue of an amino acid or the residue of an amino sugar, or taken together form a heterocycle, and the salts of said polycyclic aromatic derivative of Formula I.
- 15. The pharmaceutical composition of claim 14 wherein said polycyclic aromatic compound is present in an amount ranging from 0.00001 to about 5 percent by weight based on the total weight of said composition.
Priority Claims (1)
Number |
Date |
Country |
Kind |
86022 |
Jul 1985 |
LUX |
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Parent Case Info
This is a division of application Ser. No. 07/859,046, filed Mar. 27, 1992, now U.S. Pat. No 5,434,180 which is a division of application Ser. No. 07/580,916, filed Sep. 12, 1990 now U.S. Pat. No. 5,124,475 which is a continuation-in-part of application Ser. No. 06/887,618, filed Jul. 21, 1986, now abandoned
US Referenced Citations (4)
Number |
Name |
Date |
Kind |
2153135 |
Dickey et al. |
Apr 1939 |
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2532515 |
Pines et al. |
Dec 1950 |
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3940502 |
Winter et al. |
Feb 1976 |
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4578522 |
Eaddy, III |
Mar 1986 |
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Non-Patent Literature Citations (3)
Entry |
Chemical Abstract vol. 86 No. 6381, Liebscher et al, "Heterocyclic dyes and intermediates" (1976). |
Chebaane, Societe Chimique de France, BCCFAS (1122) pp. 2521-2526, Jan. 12, 1975. |
Hawley's Condensed Chemical Dictionary, 11 Ed., 1989, pp. 100. |
Divisions (2)
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Number |
Date |
Country |
Parent |
859046 |
Mar 1992 |
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Parent |
580916 |
Sep 1990 |
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Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
887618 |
Jul 1986 |
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