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Cyclopentane heptan(ene) oic acid, 2-heteroarylalkenyl derivatives as therapeutic agents

A kind of heteroaryl, cyclopentyl technology, applied in the field of treatment of glaucoma, smooth muscle relaxant, can solve problems such as the limitation of clinical potential of prostaglandin

Inactive Publication Date: 2004-01-07
ALLERGAN INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The clinical potential of prostaglandins in the treatment of conditions associated with increased intraocular pressure, such as glaucoma, is greatly limited by these side effects

Method used

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  • Cyclopentane heptan(ene) oic acid, 2-heteroarylalkenyl derivatives as therapeutic agents
  • Cyclopentane heptan(ene) oic acid, 2-heteroarylalkenyl derivatives as therapeutic agents
  • Cyclopentane heptan(ene) oic acid, 2-heteroarylalkenyl derivatives as therapeutic agents

Examples

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Embodiment Construction

[0054] The invention is further illustrated by the following non-limiting examples, in Figure 1-4 These examples are summarized in the reaction scheme of, where these compounds are identified by the same indicator in the example and the figure. Compound 5a7-[3α,5α-Dihydroxy-2-(3α-hydroxy-5-(2-(3-chloro)benzothienyl-1E-pentenyl)cyclopentyl]-5Z-heptenoic acid step 1: Preparation of enone 2a

[0055] Add 4-(2-(3-chloro)benzothienyl-2-oxo-butyl phosphoric acid to a suspension of sodium hydride (27mg, 1.15mmol) in tetrahydrofuran (THF) (2.0ml) cooled to 0°C A solution of dimethyl ester (363mg, 1.15mmol) in THF (2.2ml). (In this example, benzothienyl is an example of heteroaryl represented by R in the open specification and claims and Ar in the figure) After 0.25 hours, a solution of aldehyde I (507mg, 1.04mmol) in THF (2.0ml) was added, and the reaction was slowly heated to 23°C within 8 hours. (THP stands for tetrahydropyranyl in Figure 1) 。Add saturated NH 4 The reaction was terminat...

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Abstract

The present invention provides to cyclopentane heptanoic acid, 2 heteroaryl alkyl or alkenyl derivatives which may be substituted in the 1-position with hydroxyl, alkyloxy, amino and amino groups, e.g. 1-OH cyclopentane heptanoic acid, 2 heteroarylalkenyl derivatives. In particular, these derivatives are 7-[5-hydroxy-2-(heteroatom-substituted hydroxyhydrocarbyl)-3-hydroxycyclopentyl] heptanoic or heptenoic acids and amine, amide, ether, ester and alcohol derivatives of said acids wherein one or more of said hydroxy groups are replaced with an ether group. These compounds are potent ocular hypotensive and are particularly suited for the management of glaucoma. Moreover, the compounds of this invention are smooth muscle relaxants with broad application in systemic hypertensive and pulmonary diseases; with additional application in gastrointestinal disease, reproduction, fertility, incontinence, shock, inflammation, immune regulation, disorder of bone metabolism, renal dysfunction, cancer and other hypoproliferative diseases.

Description

Technical field [0001] The present invention provides cyclopentane heptanoic acid, 2-heteroarylalkyl or alkenyl derivatives which can be substituted by hydroxyl, alkoxy, amino and amido at its 1-position, such as 1-OH cyclopentane Heptanoic acid, 2-heteroarylalkenyl derivatives. In particular, these derivatives are 7-[5-hydroxy-2-(heteroatom-substituted hydroxyhydrocarbyl)-3-hydroxycyclopentyl]heptanoic acid or heptenoic acid and the amines, amides, ethers, and esters of the acids. And alcohol derivatives, wherein one or more of the hydroxyl groups may be substituted by ether groups. These compounds are effective anti-hypertensive agents and are particularly suitable for the treatment of glaucoma. In addition, the compound of the present invention is a smooth muscle relaxant, which is widely used in systemic hypertension and lung diseases; in addition, it is used in gastrointestinal diseases, regeneration, fertility, incontinence, shock, inflammation, immune regulation, bone metab...

Claims

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Application Information

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IPC IPC(8): C07D333/28A61K9/08A61K31/00A61K31/34A61K31/38A61K31/40A61K31/41A61K31/557A61K31/558A61K31/5585A61K31/559A61P1/00A61P9/00A61P9/12A61P13/00A61P15/00A61P19/00A61P19/08A61P27/00A61P27/02A61P27/06A61P29/00A61P35/00A61P37/00C07D307/44C07D333/62
CPCA61K31/5585A61K31/559A61P1/00A61P13/00A61P15/00A61P19/00A61P19/08A61P27/00A61P27/02A61P27/06A61P29/00A61P35/00A61P37/00A61P9/00A61P9/12A61K31/557
Inventor R·M·布尔克
Owner ALLERGAN INC
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