Pharmaceutical composition for treating or preventing glaucoma

A pharmaceutical composition, glaucoma technology, applied in the direction of drug combination, pharmaceutical formula, active ingredients of heterocyclic compounds, etc.

Active Publication Date: 2012-05-09
UBE IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no disclosure that the sulfonamide compound having the specific structure of the present invention is useful for

Method used

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  • Pharmaceutical composition for treating or preventing glaucoma
  • Pharmaceutical composition for treating or preventing glaucoma
  • Pharmaceutical composition for treating or preventing glaucoma

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0845] {6-[(6-phenylpyridazin-3-ylmethyl)(pyridin-3-ylsulfonyl)aminomethyl] Pyridin-2-ylamino}acetic acid hydrochloride (Exemplary Compound No. 1397)

[0846] 1-(a) ({5-bromo-6-[(6-phenylpyridazin-3-ylmethyl)(pyridin-3-ylsulfonate Acyl)aminomethyl]pyridin-2-yl}tert-butoxycarbonylamino)tert-butyl acetate

[0847] 1.75 ml of N,N-dimethylformamide of 114 mg (0.349 mmol) of N-(6-phenylpyridazin-3-ylmethyl)pyridin-3-ylsulfonamide obtained in Reference Example 2-(d) In the solution, add [(5-bromo-6-bromomethylpyridin-2-yl) tert-butoxycarbonylamino] tert-butyl acetate 233mg (containing 0.35mmol in terms of pure components) obtained in Reference Example 1-(c). ) and potassium carbonate 98.0mg (0.709mmol), stirred at room temperature for 20 hours. After the reaction, 5.3 ml of water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer after liquid separation was washed with a saturated aqueous sodium chloride solution, dried over anh...

Embodiment 2

[0860] (6-{(pyridin-3-ylsulfonyl)[4-(thiazol-2-yl)benzyl]aminomethyl} Pyridin-2-ylamino)acetic acid (Exemplary Compound No. 985)

[0861] 2-(a) [tert-butoxycarbonyl(6-{(pyridin-3-ylsulfonyl)[4-(thiazole-2 -yl)benzyl]aminomethyl}pyridin-2-yl)amino]tert-butyl acetate

[0862] In the tetrahydrofuran 20ml solution of the N-[4-(thiazol-2-yl) benzyl]pyridin-3-yl sulfonamide 686mg (2.07mmol) obtained in the reference example 4-(e), add the reference example 3-(b ) obtained in [tert-butoxycarbonyl (6-hydroxymethylpyridin-2-yl) amino] tert-butyl acetate 743mg (2.20mmol), tri-n-butylphosphine 980μl (3.92mmol) and N, N, N 562 mg (3.26 mmol) of ', N'-tetramethylazodicarboxamide was stirred at room temperature for 11 hours. After the reaction was completed, saturated aqueous sodium chloride solution was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer after liquid separation was washed with a saturated aqueous sodium chloride solution, ...

Embodiment 3

[0873] (6-{(pyridin-2-ylsulfonyl)[4-(thiazol-2-yl)benzyl]aminomethyl} Pyridin-2-ylamino)acetic acid (Exemplary Compound No. 977)

[0874] 3-(a) [tert-butoxycarbonyl(6-{(pyridin-2-ylsulfonyl)[4-(thiazole-2 -yl)benzyl]aminomethyl}pyridin-2-yl)amino]tert-butyl acetate

[0875] In addition to using 279 mg (0.824 mmol) of [tert-butoxycarbonyl (6-hydroxymethylpyridin-2-yl) amino] tert-butyl acetate obtained in Reference Example 3-(b), and using tert-butyl acetate obtained in Reference Example 5 N-[4-(thiazol-2-yl)benzyl]pyridin-2-ylsulfonamide 275mg (0.830mmol) instead of N-[4-(thiazol-2-yl)benzyl]pyridin-3-ylsulfonamide, The reaction and post-treatment were carried out according to Example 2-(a), to obtain 496 mg of the title compound in the form of white foam (yield: 92%).

[0876] Mass spectrum (FAB, m / z): 652 (M + +1).

[0877] 1 H-NMR spectrum (CDCl 3 , δppm): 8.60 (ddd, J = 4.7, 1.7, 0.9Hz, 1H), 7.85 (d, J = 3.1Hz, 1H), 7.85-7.81 (m, 3H), 7.77 (ddd, J = 7.7, 7.6 ...

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PUM

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Abstract

Provided is a pharmaceutical composition for treating or preventing glaucoma, comprising a pyridylamino acetic acid compound represented by general formula (1) or a pharmacologically acceptable salt thereof as an active ingredient. In formula (1), R1, R2, and R3 each independently represent a hydrogen atom or the like; Y represents a group: -Q1-Q2 (wherein Q1 represents an arylene group or the like; and Q2 represents a group such as an aromatic ring group which may be substituted by a halogen atom or the like) or a dicyclic heteroaromatic ring which may be substituted by a halogen atom or the like; and Z represents a group such as an aromatic ring group which may be substituted by a halogen atom or the like.

Description

technical field [0001] The present invention relates to a compound containing pyridylaminoacetic acid or a compound containing pyridylaminoacetic acid, which can be expected to have a high EP2 receptor selectivity and an excellent intraocular pressure lowering effect due to a potent EP2 agonist action, and which can be used as a drug for the treatment and / or prevention of glaucoma. A pharmaceutical composition comprising a pharmacologically acceptable salt as an active ingredient. Background technique [0002] Glaucoma is an eye disease characterized by the following visual dysfunction: due to the accumulation of aqueous humor due to the circulation disorder of aqueous humor, the intraocular pressure continues to rise, and the optic nerve is compressed, resulting in temporary or permanent visual field defect or low vision. Although the cause of the disease is increased intraocular pressure, hypotension glaucoma, in which the optic nerve is damaged even though the intraocular...

Claims

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Application Information

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IPC IPC(8): C07D213/83A61K31/44A61K31/443A61K31/4439A61K31/444A61K31/501A61K31/506A61P27/06C07D401/12C07D405/14C07D409/14C07D417/12C07D417/14C07D401/14
CPCC07D401/14C07D401/12A61K31/506C07D417/14A61K31/4439C07D405/14A61K31/444C07D417/12A61K31/501C07D409/14A61K31/443A61K31/44A61P27/00A61P27/02A61P27/06A61P43/00C07D213/83
Inventor 萩原昌彦米田健治冈成荣治重富学
Owner UBE IND LTD
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