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Novel tetrahydrobenzindolone derivatives

A compound, hydrogen atom technology, applied in the direction of active ingredients of heterocyclic compounds, organic chemistry, etc.

Inactive Publication Date: 2000-01-05
MEIJI SEIKA KAISHA LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Nevertheless, all of the above agents have a steroid skeleton, and thus have been pointed out to have steroid-specific side effects; therefore, in order to solve the above problems, what is required in the prior art is a progesterone receptor binding inhibitory agent. Reagents that are active without a steroidal backbone

Method used

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  • Novel tetrahydrobenzindolone derivatives
  • Novel tetrahydrobenzindolone derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 2

[0321] The compound prepared in Example 1 (100 mg = 0.36 mmol) was dissolved in acetonitrile (5 ml), to the solution was added acetic acid (200 µl = 3.30 mmol), and the mixture was stirred at room temperature for 20 hr. Dichloromethane (20ml) was added to the reaction solution, the mixture was washed with saturated aqueous sodium bicarbonate (20ml×2) and saturated brine (20ml), and the organic phase was dried over sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by preparative TLC to give the title compound (85 mg, 74%). 1 H NMR (CDCl 3 )δ1.14(3H, s, 4a-CH 3 ), 1.20 (3H, d, J=7.2Hz, 5-CH 3 ), 1.88 (3H, d, J=2.0Hz, 3-CH 3 ), 1.90 (1H, dq, J=7.2, 2.9Hz, 5-H), 2.06 (3H, s, OCOCH 3 ), 2.16 (1H, br d, J=16.0Hz, 4-H), 2.82 (1H, d, J=16.0Hz, 4-H), 3.10 (3H, s, N-CH 3 ), 3.84 (1H, m, 6-H), 5.20 (1H, dd, J=4.8, 1.7Hz, 7-H), 5.70 (1H, d, J=4.8Hz, 8-H), 5.75 (1H , s, 9-H); MS (EI) m / z 317 (M) + ;[α] 18 D -608 ° (c 1.0, MeOH); mp50-55 °...

Embodiment 3

[0321] The compound prepared in Example 1 (100 mg = 0.36 mmol) was dissolved in acetonitrile (5 ml), to the solution was added acetic acid (200 µl = 3.30 mmol), and the mixture was stirred at room temperature for 20 hr. Dichloromethane (20ml) was added to the reaction solution, the mixture was washed with saturated aqueous sodium bicarbonate (20ml×2) and saturated brine (20ml), and the organic phase was dried over sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by preparative TLC to give the title compound (85 mg, 74%). 1 H NMR (CDCl 3 )δ1.14(3H, s, 4a-CH 3 ), 1.20 (3H, d, J=7.2Hz, 5-CH 3 ), 1.88 (3H, d, J=2.0Hz, 3-CH 3 ), 1.90 (1H, dq, J=7.2, 2.9Hz, 5-H), 2.06 (3H, s, OCOCH 3 ), 2.16 (1H, br d, J=16.0Hz, 4-H), 2.82 (1H, d, J=16.0Hz, 4-H), 3.10 (3H, s, N-CH 3 ), 3.84 (1H, m, 6-H), 5.20 (1H, dd, J=4.8, 1.7Hz, 7-H), 5.70 (1H, d, J=4.8Hz, 8-H), 5.75 (1H , s, 9-H); MS (EI) m / z 317 (M) + ;[α] 18 D -608 ° (c 1.0, MeOH); mp50-55 °...

Embodiment 5

[0323] In the same manner as in Example, the compound prepared in Example 2 (10 mg=0.03 mmol) was dissolved in pyridine (1 ml), 2-furoyl chloride (9 μl=0.09 mmol) was added to the solution, and the mixture was Stir at room temperature for 15 hours. Dichloromethane (20ml) was added to the reaction solution, the mixture was washed with saturated aqueous sodium bicarbonate solution (20ml×2) and saturated brine (20ml), and the solvent was removed under reduced pressure. The organic phase was dried over sodium sulfate. The residue was purified by preparative TLC to give the title compound (6 mg, 49%). 1 H NMR (CDCl 3 ) δ1.15 (3H, d, J=7.2Hz, 5-CH 3 ), 1.21 (3H, s, 4a-CH 3 ), 1.89 (3H, d, J=1.9Hz, 3-CH 3 ), 2.07 (3H, s, OCOCH 3 ), 2.20 (1H, dq, J=7.2, 2.8Hz, 5-H), 2.21 (1H, br d, J=15.9Hz, 4-H), 2.86 (1H, d, J=15.9Hz, 4-H H), 3.11 (3H, s, N-CH 3 ), 5.26 (1H, dd, J = 4.7, 1.6Hz, 7-H), 5.29 (1H, m, 6-H), 5.76 (1H, s, 9-H), 5.80 (1H, d, J = 4.7Hz, 8-H), 6.49(1H, dd, J=3.5, 1.7...

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Abstract

Compounds represented by the following formula (I) or pharmaceutically acceptable salts thereof and a process for producing the same are disclosed. The compounds have progesterone receptor binding inhibitory activity and, hence, can be used as therapeutic and prophylactic agents for progesterone-related diseases. Specifically, they are useful as carcinostatic agents for breast cancer and ovarian cancer, therapeutic agents for hysteromyoma, endometriosis, meningioma, and myeloma, abortifacients, oral contraceptive pills, and therapeutic and prophylactic agents for osteoporosis and climacteric disturbance. wherein R<1> represents alkyl or aralkyl; R<2> represents a hydrogen atom, alkylcarbonyl, cycloalkylcarbonyl, aromatic acyl, heteroaromatic acyl, saturated heterocyclic acyl, alkyl, alkenyl, aralkyl, carbamoyl, alkylcarbamoyl, aromatic carbamoyl, aralkylcarbamoyl, alkylaminocarbonyl, cycloalkylcarbamoyl, alkoxycarbonyl, aryloxycarbonyl, heteroaromatic thiocarbonyl, saturated heterocyclic thiocarbonyl, or alkyl-thiocarbamoyl; and R<3> represents a hydrogen atom, a hydroxyl group, alkyloxy, alkylcarbonyloxy, alkylthio, or arylthio.

Description

field of invention [0001] The present invention relates to compounds as progesterone receptor binding inhibitors and pharmaceutical compositions containing the compounds. Background technique [0002] In recent years, even in Japan, the number of breast cancer patients has been increasing, and thus it is expected that the number of breast cancer patients will be the largest among female malignant tumor diseases in the 21st century. Initially, oophorectomy was used as endocrine therapy for breast cancer; then, adrenalectomy and pituitary resection were reported as treatments for breast cancer; and since then surgical endocrine therapy has become the main treatment for breast cancer and has achieved made progress. In surgical endocrine therapy, organs involved in estrogen secretion are removed to regress symptoms of estrogen-dependent breast cancer; however, this results in a decrease not only in estrogen but also in life-sustaining hormones ), resulting in many problems tha...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/40A61K31/415A61K31/44A61K31/445C07D209/60C07D401/12C07D403/12C07D405/12C07D409/12
Inventor 栗原健一新荣丽英仓田靖田端祐二田边洁小此木恒夫
Owner MEIJI SEIKA KAISHA LTD
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