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Bicyclic compound and use thereof for medical purposes

A compound and solvate technology, applied in the field of bicyclic compounds and their medical applications, can solve the problems of low stimulant effect, no record or teaching, etc., and achieve a strong effect of lowering intraocular pressure

Active Publication Date: 2012-06-13
ONO PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0051] The compounds of the present invention have low agonistic effects on IP receptors and EP1 receptors and have selective agonistic effects on FP receptors, but no such feature (selectivity) is described or taught in any prior art

Method used

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  • Bicyclic compound and use thereof for medical purposes
  • Bicyclic compound and use thereof for medical purposes
  • Bicyclic compound and use thereof for medical purposes

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0188] [Preparation method of the compound of the present invention]

[0189] The compounds of the invention can be prepared by known methods, for example by Comprehensive Organic Transformations: A Guide to Functional Group Preparations 2 nd Edition (Richard C. Larock, John Wiley & Sons Inc, 1999), or can be prepared by appropriately modifying the methods disclosed in the examples and using in combination.

[0190] Among the compounds represented by the general formula (I), for the compounds represented by the general formula (I-2),

[0191] [chemical formula 26]

[0192]

[0193] As shown below, the α chain represents the β configuration, and the R 1 on behalf of COOR 2 , R 5 represents a hydroxyl group, and R 6 and R 7 One represents hydrogen, the other represents hydroxyl,

[0194] That is the compound shown in general formula (I-2-a):

[0195] [chemical formula 27]

[0196]

[0197] (wherein all symbols represent the same meaning as above)

[0198] Can us...

Embodiment 1

[0295] Example 1: (3aR, 4S, 5R, 6aS)-4-({[dimethyl(2-methyl-2-propyl)silyl]oxy}methyl)-5-(tetrahydro- 2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-one

[0296] Under ice cooling, to (3aR, 4S, 5R, 6aS)-4-(hydroxymethyl)-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H-cyclopentadiene [b] Imidazole (29.22g) and tert-butyldimethylsilyl chloride (30.87g) were successively added to a solution of furan-2-one (50g) in dimethylformamide (hereinafter sometimes abbreviated as DMF) (100mL) , and the mixture was stirred at room temperature for 3.5 hours. After the reaction was completed, a small amount of ethanol was added, the reaction solution was poured into ice water, and extracted with ethyl acetate:hexane (2:3). The extract was washed with 1N hydrochloric acid, saturated aqueous sodium bicarbonate, and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure to obtain the title compound (76.2 g) having the following physical properties:

[0297] TLC: R...

Embodiment 2

[0298] Example 2: (3aR, 4S, 5R, 6aS)-4-({[dimethyl(2-methyl-2-propyl)silyl]oxy}methyl)-5-(tetrahydro- 2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-ol

[0299] Under an argon atmosphere, the anhydrous toluene (390 mL) solution of the compound (76.2 g) prepared in Example 1 was cooled to -70° C., and a toluene solution of 1 mol / L diisobutylaluminum hydride ( 212.4 mL), which was then stirred for 30 minutes. After completion of the reaction, the reaction solution was diluted with tert-butyl methyl ether (hereinafter sometimes abbreviated as MTBE) (400 mL), and a saturated aqueous sodium sulfate solution was added. The precipitated white precipitate was filtered using Celite (trade name), and the solvent was concentrated under reduced pressure to obtain the title compound (80.7 g) having the following physical properties:

[0300] TLC: Rf 0.30 (hexane:ethyl acetate=3:1).

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Abstract

Disclosed is a compound represented by general formula (I) (wherein the definition for each group is as described in the description) or a salt, solvate or prodrug thereof, which has a potent and long-lasting ocular hypotensive activity and has no adverse side effect on eyes such as irritation to eyes (congestion, corneal opacities, etc.) and increased aqueous protein level, and which is therefore highly safe and can be used as an excellent prophylactic and / or therapeutic agent for glaucoma or the like.

Description

technical field [0001] The present invention relates to a compound represented by general formula (I), a salt thereof, a solvate thereof or a prodrug thereof (hereinafter, abbreviated as the compound of the present invention in some cases), [0002] [chemical formula 1] [0003] [0004] All the symbols therein represent the same meanings as described below. Background technique [0005] Glaucoma is an eye disease characterized by functional impairment of vision, resulting in temporary or permanent visual field loss and vision loss. This is due to the accumulation of aqueous humor caused by the circulation disorder of aqueous humor, and the continuous increase of intraocular pressure causes compression of optic nerve. Lowering intraocular pressure is effective for glaucoma treatment, and in order to lower intraocular pressure, treatments such as drug therapy (eye drops, internal therapy, infusion therapy), laser therapy, or surgical therapy are performed. [0006] Conv...

Claims

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Application Information

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IPC IPC(8): C07D313/06A61K31/4427A61K31/558A61P27/02A61P27/06A61P27/10A61P27/12A61P43/00C07D401/06C07D417/04
CPCA61K31/4427C07D417/04C07D401/06A61K31/558C07D313/06A61K31/335C07D405/06C07D407/12A61P27/00A61P27/02A61P27/06A61P27/10A61P27/12A61P43/00Y10S623/905A61K9/0048
Inventor 神户透丸山透山根晋作中山仁志谷耕辅
Owner ONO PHARMA CO LTD
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