Non-steroid progestogen receptor regulator, preparation thereof, pharmaceutical compositions and uses

A progesterone receptor, non-steroidal technology, applied in the field of medicinal chemistry, can solve the problems of poor prognosis of breast cancer and reduce the adhesion of breast cancer cells

Inactive Publication Date: 2013-02-27
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

If overexpression of hPR-A in T47D cell line can reduce the adhesion of breast cancer cells and inhibit the effect of progesterone, it may be related to the poor prognosis of breast cancer

Method used

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  • Non-steroid progestogen receptor regulator, preparation thereof, pharmaceutical compositions and uses
  • Non-steroid progestogen receptor regulator, preparation thereof, pharmaceutical compositions and uses
  • Non-steroid progestogen receptor regulator, preparation thereof, pharmaceutical compositions and uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] Synthesis of 3-cyclohexyl-3-(4-nitroanilino)-1-(4-methylphenyl)-1-propanone

[0073] Specific preparation method: dissolve 1 mmol of 4-nitroaniline in 1 to 3 ml of absolute ethanol, add 1 mmol of cyclohexanal and 1 mmol of 4-methylacetophenone, stir and dissolve at room temperature, and add 20 to 100 μL (catalytic amount) of concentrated hydrochloric acid or saturated ethanol solution of hydrochloric acid, precipitation occurs, stir at 0°C to 55°C for 8 to 48 hours, place in the refrigerator overnight, filter with suction, wash the solid with a small amount of ethanol to obtain a crude product. Pure product can be obtained by recrystallization with ethanol or acetone. The yield is 50%~99%.

[0074] 1 HNMR (DMSO-d 6 , 400MHz): δ7.95 (2H, d, J = 8.5), 7.87 (2H, d, J = 8.1), 7.33 (2H, d, J = 8.2), 7.15 (1H, d, J = 9.2, NH ), 6.64 (2H, d, J=9.5), 4.06 (1H, d, J=8.6), 3.24 (2H, t), 2.07 (3H, s), 1.54~1.80 (6H, m), 1.03~1.21 (5H, m); orange solid with a melting point of ...

Embodiment 2

[0076] Synthesis of 3-cyclohexyl-3-(4-nitroanilino)-1-(4-bromophenyl)-1-propanone

[0077] Specific preparation method: prepare according to the same method as in Example 1 except that 4-bromoacetophenone is used instead of 4-methylacetophenone.

[0078] 1 HNMR (DMSO-d 6 , 400MHz): δ7.95 (2H, d, J=8.7), 7.90 (2H, d, J=8.7), 7.73 (2H, d, J=8.3), 6.64 (2H, d, J=9.1), 4.02 (1H, q, J=11.7, 5.9), 3.26 (2H, d, J=6.3), 1.56~1.79 (6H, m), 1.03~1.20 (5H, m); yellow solid, melting point: 161~ 162°C (159°C).

Embodiment 3

[0080] Synthesis of 3-cyclohexyl-3-(4-nitroanilino)-1-(3-fluorophenyl)-1-propanone

[0081] Specific preparation method: except that 4-methylacetophenone was replaced with 3-fluoroacetophenone, the preparation was carried out in the same manner as in Example 1.

[0082] 1 HNMR (DMSO-d 6 , 400MHz): δ7.95(2H, d, J=8.4), 7.83(1H, d, J=7.3), 7.75(1H, d, J=9.2), 7.48~7.62(2H, m), 7.13( d, NH), 6.65 (2H, d, J=9.0), 4.05 (1H, d, J=4.4), 3.30 (2H, d, J=5.9), 1.60~1.80 (6H, m), 1.06~1.22 (5H, m); orange solid, melting point: 131-133°C (105°C).

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Abstract

The invention relates to a modulator of nonsteroidal progesterone receptor with a structure of the general formula I or an acceptable salt on pharmacy and a preparation method thereof. The invention also relates to drug combination including compounds of the general formula I or an acceptable salt on pharmacy thereof and the antagonist activity of progesterone receptor which is provided by the compounds of the general formula I or the acceptable salt on pharmacy thereof; therefore, the invention can be used for preparing nonsteroidal drugs to prevent and (or) or treat symptoms or diseases such as secondary amenorrhea, functional bleeding disorder, uterine fibroids, endometriosis, polycystic ovary syndrome, breast cancer, contraceptive, induced labor, and termination of pregnancy, etc.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and relates to a non-steroidal progesterone receptor modulator, a preparation method thereof, a pharmaceutical composition and the preparation method for stopping early and mid-term pregnancy, emergency contraception, preventing and / or treating uterine fibroids and endometrium Use in medicine for symptoms or diseases such as atopy and breast cancer. Background technique [0002] Nuclear receptors (NR) form a class of structurally related regulators of gene expression called "ligand-dependent transcription factors" (R.M. Evans, Science, 240, 889, 1988). Steroid hormone receptors are members of the nuclear receptor family that includes the progesterone receptor (PR), estrogen receptor (ER), androgen receptor (AR), glucocorticoid receptor (GR), and mineralocorticoid Hormone receptors (MRs). [0003] For the progesterone receptor (PR), the natural hormone or ligand is the steroid progesterone, in...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C225/22C07C225/04C07D333/20C07D295/04A61K31/136A61K31/381A61K31/535A61P5/36
Inventor 沈竞康王明伟杜永丽冯杨李群益
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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