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Tetrahydroquinoline derivatives

A technology of tetrahydroquinoline and its derivatives, applied in the field of tetrahydroquinoline derivatives or their salts, can solve the problems of no compound being created, central nervous system and reproductive system, etc.

Inactive Publication Date: 2002-11-06
KAKEN PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] In recent years, such non-steroidal AR antagonists that have little effect on the central nervous system and reproductive system and have strong AR antagonist activity are being developed, but no globally recognized compound has been created yet.

Method used

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Examples

Experimental program
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Effect test

Embodiment approach

[0016] The substituents in the aforementioned formula (I) will be described below.

[0017]Specific examples of the "alkyl group having 1 to 9 carbon atoms" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, n-pentyl Base, tert-pentyl, 3-methylbutyl, neopentyl, n-hexyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 2-methylhexyl, n-octyl , 2-propylpentyl and n-nonyl and other straight-chain or branched-chain alkyl groups.

[0018] Specific examples of the "alkoxy group having 1 to 9 carbon atoms" include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy Base, sec-butoxy, n-pentyloxy, tert-pentyloxy, 3-methylbutoxy, neopentyloxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutyl Linear or branched alkoxy groups such as oxy, n-heptyloxy, 2-methylhexyloxy, n-octyloxy, 2-propylpentyloxy and n-nonyloxy.

[0019] Specific examples of the "halogen atom" include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. ...

Embodiment 1

[0084] 9.8 g of 4-nitroaniline, 6.5 ml of cyclopentadiene and 5.5 ml of trifluoroacetic acid were dissolved in 70 ml of acetonitrile, and 10.0 g of hydroxytrimethylacetaldehyde was added at 0°C. After stirring at room temperature for 30 minutes, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate=1:1) to obtain 4.8 g of the title compound. Physical data are shown below.

[0085] 1 H-NMR (CDCl 3 )δ values: 7.85 (s, 1H), 7.84 (d, J = 8.9Hz, 1H), 6.47 (d, J = 8.9Hz, 1H), 5.96 (brs, 1H), 5.78 (brs, 1H), 3.98 (d, J=9.9Hz, 1H), 3.64(d, J=10.6Hz, 1H), 3.55(d, J=10.6Hz, 1H), 3.54(d, J=2.3Hz, 1H), 2.87(ddt , J=2.3, 8.2, 9.9Hz, 1H), 2.48(dd, J=9.9, 15.5Hz, 1H), 2.26(dd, J=8.2, 15.5Hz, 1H), 1.11(s, 3H), 0.96( s, 3H).

[0086] Compounds shown in Examples 2 to 34 were produced in the same manner as in Example 1. The physical data of the obtained compound are shown in Tables 1-4.

...

Embodiment 50

[0101] 1 H-NMR (CDCl 3 )δ values: 8.01 (brs, 1H), 7.81-7.77 (m, 2H), 7.45 (s, 1H), 6.90 (d, J=9.9Hz, 1H), 6.38 (brs, 1H), 5.97-5.95 ( m, 1H), 5.74-5.72(m, 1H), 4.00(d, J=8.6Hz, 1H), 3.52(brs, 1H), 3.47(dd, J=7.3, 14.2Hz, 1H), 2.47-2.37 (m, 1H), 2.27-2.22 (m, 1H), 1.24 (s, 3H), 1.17 (s, 3H). [Example 50] 2-(8-nitro-3a, 4, 5, 9b- Preparation of tetrahydro-3H-cyclopentadieno[c]quinolin-4-yl)-propylamine

[0102] Using 65 mg of the compound of Example 24, the same procedure as in Example 49 was carried out to obtain 32 mg of the title compound. Its physical data are shown below.

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PUM

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Abstract

Tetrahydroquinoline derivatives of general formula (I) or salts thereof, having a specific and strong binding affinity for AR and exhibiting AR agonism or antagonism; and pharmaceutical compositions containing the derivatives or the salts. <CHEM>

Description

technical field [0001] The present invention relates to tetrahydroquinoline derivatives or salts thereof, which have specific and strong binding affinity to androgen receptor and exhibit androgen receptor agonist or antagonist action, and medicaments containing them. Background technique [0002] Androgen is a general term for C19 steroids, and it is a sex hormone that plays an important role in normal male sexual differentiation and development, puberty virilization, activation of early spermatogenesis in testes, and maintenance of male function. About 90% of androgens are produced by the Leydig cells of the testes, and the remaining 10% are produced by the adrenal glands, mainly in the form of testosterone, which is secreted into the blood. Testosterone is taken up by target cells and converted to the biologically active dihydrotestosterone (DHT) by 5α-reductase. Together with testosterone, DHT plays a role in the development of male secondary sexual characteristics (seba...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61P5/26A61P7/06A61P15/08A61P15/10A61P19/10A61P35/00A61P43/00C07D221/16C07D491/048C07D491/052
CPCC07D221/16A61P15/00A61P15/08A61P15/10A61P19/10A61P35/00A61P43/00A61P5/26A61P5/28A61P7/06
Inventor 花田敬吾古屋和行井口潔宫川基则永田尚也
Owner KAKEN PHARMA CO LTD
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