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Aryl or heteroaryl substituted 3,4-dihydroanthracene and aryl or heteroaryl substituted benzo[1,2-g]-chrom-3-ene, benzo[1,2-g]-thiochrom-3-ene and benzo [1,2-g]-1,2-dihydroquinoline derivatives having retinoid antagonist or retinoid inverse agonist type biological activity

a technology of aryl or heteroaryl and dihydroanthracene, which is applied in the field of compounds having retinoidlike, retinoid antagonist and/or retinoid inverse agonistlike biological activity, and aryl or heteroaryl substituted 3, 4dihydroanthracene and aryl or heteroaryl substituted, etc., can solve the problems of limiting the acceptability and utility of retinoids for treating diseases, and the number of und

Inactive Publication Date: 2007-11-15
ALLERGAN INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

These compounds effectively treat skin-related diseases, cancers, and cardiovascular conditions while minimizing side effects by selectively binding to retinoid receptors, reducing unwanted activations and preventing toxicity from retinoid overdose.

Problems solved by technology

Although pharmaceutical compositions containing retinoids have well established utility (as is demonstrated by the foregoing citation of patents and publications from the voluminous literature devoted to this subject) retinoids also cause a number of undesired side effects at therapeutic dose levels, including headache, teratogenesis, mucocutaneous toxicity, musculoskeletal toxicity, dyslipidemias, skin irritation, headache and hepatotoxicity.
These side effects limit the acceptability and utility of retinoids for treating disease.

Method used

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  • Aryl or heteroaryl substituted 3,4-dihydroanthracene and aryl or heteroaryl substituted benzo[1,2-g]-chrom-3-ene, benzo[1,2-g]-thiochrom-3-ene and benzo [1,2-g]-1,2-dihydroquinoline derivatives having retinoid antagonist or retinoid inverse agonist type biological activity
  • Aryl or heteroaryl substituted 3,4-dihydroanthracene and aryl or heteroaryl substituted benzo[1,2-g]-chrom-3-ene, benzo[1,2-g]-thiochrom-3-ene and benzo [1,2-g]-1,2-dihydroquinoline derivatives having retinoid antagonist or retinoid inverse agonist type biological activity
  • Aryl or heteroaryl substituted 3,4-dihydroanthracene and aryl or heteroaryl substituted benzo[1,2-g]-chrom-3-ene, benzo[1,2-g]-thiochrom-3-ene and benzo [1,2-g]-1,2-dihydroquinoline derivatives having retinoid antagonist or retinoid inverse agonist type biological activity

Examples

Experimental program
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specific embodiments

[0069] With reference to the symbol Y in Formula 1, the preferred compounds of the invention are those where Y is phenyl, napthyl, pyridyl, thienyl or furyl. Even more preferred are compounds where Y is phenyl. As far as substitutions on the Y (phenyl) and Y (pyridyl) groups are concerned, compounds are preferred where the phenyl group is 1,4 (para) substituted and where the pyridine ring is 2,5 substituted. (Substitution in the 2,5 positions in the “pyridine” nomenclature corresponds to substitution in the 6-position in the “nicotinic acid” nomenclature.) In the presently preferred compounds of the invention there is no R2 substituent on the Y group.

[0070] The A-B group of the preferred compounds is (CH2)qCOOH or (CH2)q—COOR8 where R8 is defined as above. Even more preferably q is zero and R8 is lower alkyl.

[0071] The aromatic carbocyclic portions (B and C rings) of the 3,4-dihydroanthracene moiety, or of the benzo[1,2-g]-chrom-3-ene, benzo[1,2-g]-thiochrom-3-ene and benzo[1,2-g]...

specific examples

1-(Tol-4-yl)3,4-dihydro-4,4-dimethyl-7-bromo-naphthalene (Compound B)

[0090] To a mixture of Mg metal (650 mg, 27 mmol) in THF (20 mL) was added 4-bromotoluene (5.3 g, 31 mmol) in THF (40 mL). The mixture was stirred for 2 hours at ambient temperature and heated to 70° C. for 30 minutes. After cooling to ambient temperature, 3,4-dihydro-4,4-dimethyl-7-bromo-1(2H)-naphthalenone (Compound A) (2.1 g, 8 mmol), in THF (5 mL) was added and heated to 70° C. for 24 hours. The mixture was cooled to ambient temperature and the reaction was quenched by addition of H2O. The mixture was diluted with ether:ethylacetate (1:1, 100 mL) and washed with saturated NH4Cl (15 mL), water (10 mL) and brine (10 mL). The organic layer was dried with MgSO4. Solvent was removed under reduced pressure to afford the crude product as an oil. The product was dissolved in THF (20 mL). To this solution p-toleune sulfonic acid (pTSA) (35 mg) was added and the mixture was refluxed for 16 hours. The mixture was cooled ...

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Abstract

Compounds of the formula where the symbols have the meaning defined in the specification, have retinoid, retinoid antagonist and / or retinoid inverse-agonist-like biological activity.

Description

RELATED APPLICATIONS [0001] This application is a continuation of U.S. application Ser. No. 10 / 336,344, filed Jan. 2, 2003, which is a divisional of U.S. application Ser. No. 09 / 482,700, filed Jan. 13, 2000, now U.S. Pat. No. 6,538,149, which is a divisional of U.S. application Ser. No. 09 / 030,350, filed Feb. 25, 1998, now U.S. Pat. No. 6,087,505, which is a divisional of U.S. application Ser. No. 08 / 764,466, filed Dec. 12, 1996, now U.S. Pat. No. 5,728,846. The entire teachings of the above applications are incorporated herein by reference.BACKGROUND OF THE INVENTION [0002] The present invention relates to novel compounds having retinoid-like, retinoid antagonist and / or retinoid inverse-agonist-like biological activity. More specifically, the present invention relates to aryl or heteroaryl substituted 3,4-dihydroanthracene and aryl or heteroaryl substituted benzo[1,2-g]-chrom-3-ene, benzo[1,2-g]-thiochrom-3-ene and benzo[1,2-g]-1,2-dihydroquinoline derivatives which bind to retinoi...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07D211/06C07C25/22C07C323/56C07C333/08C07D335/08C07D311/92C07C47/546C07C69/78A61K31/192A61K31/235A61K31/352A61K31/381A61K31/382A61K31/44A61P1/00A61P3/06A61P9/00A61P17/00A61P25/28A61P27/00A61P29/00A61P31/12A61P35/00A61P37/00A61P43/00C07C45/00C07C47/548C07C61/08C07C61/29C07C69/00C07C69/74C07C233/00C07D213/55C07D333/24C07D409/06C07D417/02C07F7/02C07F7/08
CPCC07C45/00C07C47/548C07C69/76C07C2103/24C07D213/55C07D311/92C07D409/06C07D333/24C07D335/08C07C2603/24A61P1/00A61P17/00A61P25/28A61P27/00A61P29/00A61P31/12A61P35/00A61P3/06A61P37/00A61P43/00A61P9/00C07C63/66
Inventor VULIGONDA, VIDYASAGARJOHNSON, ALAN T.CHANDRARATNA, ROSHANTHA A.
Owner ALLERGAN INC
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