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Potassium channel modulators

A kind of technology of solvate and compound, applied in the field of potassium channel modulator

Inactive Publication Date: 2012-09-12
ABBVIE INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Thus, there is a need for a KCNQ opener that has efficacy in one or more of the aforementioned disorders, states, or conditions, but without the side effects of flupirtine or retigabine

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0412] 2-(4-Chlorophenyl)-N-(4-isopropyl-1-oxo-2,3-naphthyridine-2(1H)-yl)acetamide

Embodiment 1A

[0414] 4-Isopropyl 2,3-phthalazin-1(2H)-one

[0415] At 0°C, isopropylmagnesium bromide / THF (1M, 6.4ml, 6.4mmol) solution was added to 2-methylisoindoline-1,3-dione (0.793g, 4.92mmol) / THF ( 15 mL) was stirred for 15 min, concentrated and dissolved in EtOH (12 mL) along with a catalytic amount of conc. HCl. Hydrazine hydrate (0.58ml, 15mmol) was added, and the mixture was microwaved at 180°C for 30 minutes, concentrated, and heated on SiO 2 Chromatography (33% EtOAc / hexanes) gave the title compound as a white solid (0.591 g, 3.14 mmol). 1 H NMR (300 MHz, DMSO-d 6 ) δ 12.47 (s, 1H), 8.28 (dd, 1H), 8.06 (d, 1H), 7.94 (ddd, 1H), 7.85 (ddd, 1H), 3.57 (quin, 1H), 1.27 (d, 6H) ; LC / MS (APCI) M / Z 189.1 (M+H) + .

Embodiment 1B

[0417] 2-Amino-4-isopropyl-2,3-naphthyridine-1(2H)-one

[0418] A mixture of the product of Example 1A (30.0 mg, 0.159 mmol) and KOtBu (1 M in THF, 0.32 ml, 0.32 mmol) / THF (1 ml) was stirred for 45 minutes, and O-(diphenylphosphoryl)hydroxylamine was added (57.6 mg, 0.247 mmol) [Klotzer, W.; Stadlwieser, J.; Raneburger, J. Organic Syntheses 1986, 64, 96-103] and stirred overnight. The mixture was diluted with EtOAc and washed with saturated NaHCO 3 Washed with aqueous solution and brine, dried (Na 2 SO 4 ), and concentrated to give 35.3 mg of crude product as a tan solid, which was used without purification. 1 H NMR (300 MHz, DMSO-d 6 ) δ 8.31 (dd, 1H), 8.09 (d, 1H), 7.92 (ddd, 1H), 7.84 (ddd, 1H), 6.31 (s, 2H), 3.63 (quin, 1H), 1.30 (d, 6H) ; LC / MS (APCI) M / Z 204.1 (M+H) + .

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Abstract

Disclosed herein are KCNQ potassium channels modulators of formula (I) wherein ring Z1, R1, p, R3, and R4 are as defined in the specification. Compositions comprising such compounds; and methods for treating conditions and disorders using such compounds and compositions are also described.

Description

[0001] Cross References to Related Applications [0002] This application claims priority to US Patent Application Serial No. 61 / 264,337, filed November 25, 2009, which is incorporated herein by reference in its entirety. technical field [0003] Potassium channel modulators, compositions comprising such compounds, and methods of treating conditions and disorders using such compounds and compositions are disclosed. Background technique [0004] Potassium channels are membrane-bound proteins responsible for regulating the flow of potassium ions across cell membranes. KCNQ (or K v The 7) family is an important class of potassium channels that play a key role in the process of neuronal excitability. There are five recognized subtypes of KCNQ channels: KCNQ1, KCNQ2, KCNQ3, KCNQ4, and KCNQ5. KCNQ2-KCNQ5 subtypes represent neuronal KCNQ subtypes. Miceli, Curr. Op. Pharmacol., 2008, 8, 65. Functional KCNQ channels are formed by the assembly of four individual subunits into hom...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D237/24C07D401/12C07D405/04C07D471/04C07D495/04A61K31/502A61P29/00
CPCC07D237/24C07D401/12C07D405/04C07D471/04C07D495/04A61P13/10A61P25/00A61P25/06A61P25/08A61P25/18A61P25/22A61P25/30A61P29/00A61P43/00
Inventor B.S.布朗李彤梅A.佩雷斯-梅德拉诺S.佩迪
Owner ABBVIE INC
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