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Pyrazolopyrimidinone derivatives for the treatment of impotence

A technology for pyrazolopyrimidinone and derivatives, which is applied in the field of pyrazolopyrimidinone derivatives, and can solve the problems of poor effect, side effects, high cost, etc.

Inactive Publication Date: 2004-01-28
东亚制药技术株式会社
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But these treatment options are limited in several aspects, such as side effects, high cost and poor efficacy

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 22

[0041] 12) 5-[2-ethoxy-5-(benzylaminosulfonyl)phenyl]-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo(4,3 -d) pyrimidin-7-one (compound of Example 22);

[0042] 13) 5-[2-propoxy-5-(benzylaminosulfonyl)phenyl]-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo(4,3 -d) pyrimidin-7-one (compound of Example 23);

[0043] 14) 5-[2-ethoxy-5-(benzylaminosulfonyl)phenyl]-1-ethyl-3-propyl-1,6-dihydro-7H-pyrazolo(4,3 -d) pyrimidin-7-one (compound of Example 24);

[0044] 15) 5-[2-ethoxy-5-(4-fluorophenylaminosulfonyl) phenyl]-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo( 4,3-d) pyrimidin-7-one (compound of Example 26);

[0045] 16) 5-[2-ethoxy-5-(4-tert-butylphenylaminosulfonyl)phenyl]-1-methyl-3-propyl-1,6-dihydro-7H-pyrazole And (4,3-d) pyrimidin-7-one (Example 28 compound);

[0046] 17) 5-[2-ethoxy-5-(4-tert-butylphenylaminosulfonyl)phenyl]-1-ethyl-3-propyl-1,6-dihydro-7H-pyrazole And (4,3-d) pyrimidin-7-one (compound of Example 29);

[0047] 18) 5-[2-ethoxy-5-(4-isopropylphenylaminosulfonyl)p...

Embodiment 2

[0118] NMR (CDCl 3 ): 0.99(t, 3H), 1.14(d, 6H), 1.61(t, 3H), 1.62(m, 2H), 2.89(t, 2H), 3.54(m, 1H), 4.25(s, 3H) , 4.34 (q, 2H), 4.57 (d, 1H), 7.12 (d, 1H), 7.96 (dd, 1H), 8.93 (d, 1H), 10.83 (br s, 1H). Preparation 5-[2-Ethoxy-5-(benzylaminosulfonyl)phenyl]-1-methyl-3-isobutyl-1,6-dihydro-7H-pyrazolo(4,3- d) Preparation of 2-ethoxy-5-(benzylaminosulfonyl)benzoic acid from pyrimidin-7-one (step 1)

[0119] At 0°C, 6 g of 2-ethoxy-5-chlorosulfonylbenzoic acid in acetone was added to 7.4 ml of benzylamine, and the mixture was stirred at less than 20°C for 3 hours. Acetone was removed by evaporation, the residue was diluted with dichloromethane and extracted with saturated aqueous sodium bicarbonate. After acidifying the extracted aqueous sodium bicarbonate layer with HCl, the product was re-extracted with dichloromethane, and the organic layer was washed with saturated brine, anhydrous MgSO 4 Drying and concentration afforded 5.76 g of the expected product.

[0120] NMR (CD...

Embodiment 3-70

[0126] Compounds of Examples 3-70 were prepared in the same manner as in Example 1 or 2, using appropriate amines corresponding to the respective substituents as starting materials.

[0127]

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PUM

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Abstract

The present invention relates to pyrazolopyrimidinone derivatives of formula (1), their preparation method and pharmaceutical compositions containing the said derivatives. The compounds have efficacy on the treatment of impotence, one of male sexual dysfunctions with the side effects reduced.

Description

technical field [0001] The present invention relates to pyrazolopyrimidinone derivatives of formula 1, their preparation methods and pharmaceutical compositions containing said derivatives. Background technique [0002] Erectile dysfunction in men is one of the most common male sexual dysfunctions. Although erectile dysfunction may initially be primarily psychological, it often accompanies chronic medical conditions such as diabetes, heart disease, high blood pressure, and various neurological disorders. Its incidence is closely related to age, with an estimated incidence of 2% at age 40 rising to 25-30% at age 65. Among men older than 75 years, the prevalence of erectile dysfunction may exceed 50%, although no data are available. [0003] For the treatment of erectile dysfunction, various options are available, such as stimulation, hormone therapy, self-injection or transurethral administration of vasodilators, vacuum devices, implantation of prostheses, and venous / arteri...

Claims

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Application Information

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IPC IPC(8): A61K31/519A61P15/10A61P43/00C07D487/04
CPCC07D487/04A61P15/10A61P43/00
Inventor 刘武熙金源培张民善林重仁金东成金翼渊林泰均安秉玉姜庆求孙美苑都贤美金舜会沈贤珠吴泰宁金与渽金东九
Owner 东亚制药技术株式会社
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