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Novel orally bioavailable breathing control modulating compounds, and methods of using same

A compound and chemical bond technology, applied in the direction of active ingredients of heterocyclic compounds, drug combinations, respiratory diseases, etc.

Inactive Publication Date: 2015-09-16
GALLEON PHARMA INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As a result, the patient is unable to respond normally to changes in metabolic demand

Method used

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  • Novel orally bioavailable breathing control modulating compounds, and methods of using same
  • Novel orally bioavailable breathing control modulating compounds, and methods of using same
  • Novel orally bioavailable breathing control modulating compounds, and methods of using same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0544] Example 1: O, N-dimethyl-N-[4(n-propylamino)-6-(prop-2-ynylamino)-[1,3,5]triazin-2-yl]- Hydroxylamine (4), and corresponding salts: hydrochloride (5a) and bisulfate (5b) (Scheme 10)

Embodiment 1A

[0545] Example 1A, stage 1: 2,4-dichloro-N-(6-n-propylamino)-[1,3,5]triazine (2); process and purity Method 3M-8 (In-Process and Purity Analysis, Method 3M-D):

[0546] To a 2 liter jacketed glass reactor with bottom drain valve, stirrer (three-bladed impeller), thermometer and dropping funnel (with pressure equalizing arm) was charged powdered cyanuric chloride (1) (120 g, 0.651 mol , 1 equiv) and THF (540 mL). The temperature in the jacket was set at -25°C.

[0547] Separately, n-propylamine (53.4 mL, 0.651 mol, 1 eq) and DIPEA (113.3 mL, 0.651 mol, 1 eq) were dissolved in THF (960 mL). This mixture was added dropwise to the stirred solution of (1) within 4 h at -25°C. After this time, the reaction mixture was allowed to warm to room temperature and stirred for 16 h. The volatiles were removed in vacuo and the resulting oily residue was partitioned between EtOAc (1000 mL) and water (300 mL). The organic layer was washed with water (2x300 mL), then brine solution (500...

Embodiment 1B

[0548] Example 1B, Stage 2: 6-Chloro-N 2 -(prop-2-ynylamino)-N 4 -n-Propylamino-1,3,5-triazine (3):

[0549] 4,6-Dichloro-[1,3,5]triazin-2-yl)-n-propyl-amine (2) (3.00g, 14.49mmol), propargylamine hydrochloride (1.46g, 15.94mmol ) and N,N-diisopropylethylamine (5.3 mL, 31.88 mmol) in 1,4-dioxane (25 mL) was stirred at 55° C. for 2 h. The mixture was cooled to room temperature. The resulting precipitate was filtered, washed with water and dried to give 6-chloro-N 2 -(prop-2-ynylamino)-N 4 - n-Propylamino-1,3,5-triazine-2,4-diamine (3) (2.98 g, 91%). 400MHz 1 H NMR (DMSO-d 6 , ppm): δ8.16-7.83 (2H, m), 4.01-3.93 (2H, m), 3.22-3.08 (2H, m), 3.08-3.03 (1H, m), 1.57-1.43 (2H, m) , 0.90-0.81 (3H, m). ESI-MS (m / z): 226, 228 [M+H] + .

[0550] Example 1C, Stage 3, Method 1: O,N-Dimethyl-N-[4-(n-propylamino)-6-(prop-2-ynylamino)-[1,3,5] Triazin-2-yl]-hydroxylamine (4); Process and Purity Method 3M-D:

[0551] 6-Chloro-N 2 -(prop-2-ynylamino)-N 4 - n-propylam...

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Abstract

The present invention includes compositions that are useful in the prevention and / or treatment of breathing control diseases or disorders in a subject in need thereof. The present invention also includes a method of preventing and / or treating a respiratory disease or disorder in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of a composition of the invention. The present invention further includes a method of preventing destabilization or stabilizing breathing rhythm in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of a composition of the invention.

Description

[0001] Cross References to Related Applications [0002] This application claims priority to US Provisional Application Nos. 61 / 726,823, filed November 15, 2012, and 61 / 783,451, filed March 14, 2013, all of which are hereby incorporated by reference in their entirety. Background of the invention [0003] Normal breathing control is a complex process, part of which involves the body's interpretation and response to chemical stimuli such as carbon dioxide, pH and oxygen levels in the blood, tissues and brain. Normal breathing control is also affected by other factors such as wakefulness (eg, whether the patient is awake or asleep), mood, posture, and vocalization. Within the medulla of the brain, there is a breath control center that interprets the various feed-forward and feedback signals that affect respiration by sending commands to the muscles that perform the work of respiration. Key muscle groups are located in the abdomen, diaphragm, pharynx and chest. Centrally and per...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D251/54
CPCC07D487/04C07D473/16C07D251/70A61K31/519A61K31/53C07D251/54A61P11/00A61P21/00A61P23/00A61P25/00A61P25/16A61P25/20A61P25/28A61P9/00A61P9/10A61K45/06
Inventor J·C·曼尼恩S·L·戴克斯F·J·高德D·E·麦金太尔J·迈克罗德V·奥佐拉E·苏娜K·舒宾J·J·门塞尔S·X·彭
Owner GALLEON PHARMA INC
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