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Novel Compounds and Compositions for Treatment of Breathing Control Disorders or Diseases

a breathing control disorder and composition technology, applied in the direction of drug compositions, heterocyclic compound active ingredients, biocide, etc., can solve the problems of severe cardiovascular consequences, patient is unable to mount a normal ventilatory response to changes in metabolic demand, and hyponea (decreased breathing), so as to reduce or minimize the open channel fraction of the potassium maxi-k or bk channel

Inactive Publication Date: 2012-11-22
GALLEON PHARMA INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Conversely, low CO2 levels can result in periods of hyponea (decreased breathing) or, in the extreme case, apnea (no breathing) since the stimulation to breathe is diminished.
Thus, the patient is unable to mount a normal ventilatory response to changes in metabolic demand.
Apneic events result in hypoxia (and the associated oxidative stress) and eventually severe cardiovascular consequences (high blood pressure, stroke, heart attack).

Method used

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  • Novel Compounds and Compositions for Treatment of Breathing Control Disorders or Diseases
  • Novel Compounds and Compositions for Treatment of Breathing Control Disorders or Diseases
  • Novel Compounds and Compositions for Treatment of Breathing Control Disorders or Diseases

Examples

Experimental program
Comparison scheme
Effect test

example 1

N-(4,6-Bis-methylamino-[1,3,5]triazin-2-yl)-N,O-dimethyl-hydroxylamine hydrochloride (XX)

[0359]

2-Chloro-N-(4,6-bis-methylamino)-[1,3,5]triazine (XIX)

[0360]2,4,6-Trichloro-1,3,5-triazine (XVIII) (5.0 g, 27 mmol) was dissolved in acetone (35 mL) and poured into ice-water (50 mL) to form a very fine suspension. A solution of N-methylamine hydrochloride (3.66 g, 54 mmol) in water (20 mL) was added and the temperature maintained at approximately 0° C. To this mixture, 2N NaOH (54 mL, 108 mmol) was added in a dropwise manner to keep the temperature between 0° C. and 5° C. The mixture was stirred 30 min at ambient temperature for an additional 60 min at 50° C. The precipitate was filtered and washed with water (3×25 mL). After drying over anhydrous calcium chloride under high vacuum, 2-chloro-N-(4,6-bis-methylamino)-[1,3,5]triazine (XIX) was isolated as a white powder (4.2 g, 89% yield). LCMS (ESI) m / z=174 (M+H)+.

N-(4,6-Bis-methylaminol 1,3,5]triazin-2-yl)-N,O-dimethyl-hydroxylamine hydroc...

example 2

N-(4,6-Bis-ethylamino-[1,3,5]triazin-2-yl)-N,O-dimethyl-hydroxylamine hydrochloride (XXII)

[0362]

2-Chloro-N-(4,6-bis-ethylamino)-[1,3,5]triazine (XXI)

[0363]2,4,6-Trichloro-1,3,5-triazine (XVIII) (5.0 g, 27 mmol) was dissolved in acetone (35 mL) and poured into ice-water (50 mL) to form a very fine suspension. A solution of ethylamine (2.43 g, 54 mmol) in water (20 mL) was added and the temperature maintained at approximately 0° C. To this mixture, 2N NaOH (27 mL, 54 mmol) was added in a dropwise manner to keep the temperature between 0° C. and 5° C. The mixture was stirred for 30 min at ambient temperature, and for additional 60 min at 50° C. The precipitate was filtered off, washed with water (3×25 mL). After drying over anhydrous calcium chloride under high vacuum, 2-chloro-N-(4,6-bis-ethylamino)-[1,3,5]triazine (XXI) was isolated as a white powder (5.0 g, 92% yield). LCMS (ESI) m / z=202 (M+H)+.

N-(4,6-Bis-ethylaminol-[1,3,5]triazin-2-yl)-N,O-dimethyl-hydroxylamine hydrochloride (XXI...

example 3

N-(4-Cyclopropylmethyl)-N-(6-n-propylamino)[1,3,5]triazin-2-yl)-N,O-dimethyl-hydroxylamine (XXV)

[0365]

2,4-Dichloro-N-(6-n-propylamino)-[1,3,5]triazine (XXIII)

[0366]2,4,6-Trichloro-1,3,5-triazine (XVIII) (20 g, 109 mmol) was dissolved in acetone (100 mL) and poured into ice-water (50 mL) to form a very fine suspension. A solution of propan-1-amine (7.1 g, 120 mmol) in water (20 mL) was added and the temperature maintained at approximately 0° C. To this mixture, 2N NaOH (60 mL, 120 mmol) was added in a dropwise manner to keep the temperature between −5° C. and 0° C. The mixture was stirred at 0° C. for 60 min. The precipitate was filtered off and washed with water (3×25 mL). After drying over calcium chloride under high vacuum, 2,4-dichloro-N-(6-n-propylamino)-[1,3,5]triazine (XVIII) was isolated as a white powder (18 g, 80% yield). LCMS (ESI) m / z=208 (M+H)+.

2-Chloro-N-(4-cyclopropylmethyl)-N-(6-n-propylamino)[1,3,5]triazine (XXIV)

[0367]2,4-Dichloro-N-(6-n-propylamino)-[1,3,5]triazine...

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Abstract

The present invention includes compositions that are useful in the treatment of breathing control diseases or disorders in a subject in need thereof. The present invention also includes a method of treating a respiratory disease or disorder in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of a pharmaceutical formulation 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 pharmaceutical formulation of the invention.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS[0001]The present application is a continuation-in-part of and claims priority to U.S. patent application Ser. No. 13 / 306,349, filed Nov. 29, 2011, which is entitled to priority under 35 U.S.C. §119(e) to U.S. Provisional Patent Applications No. 61 / 417,777, filed Nov. 29, 2010, and No. 61 / 494,268, filed Jun. 7, 2011, all of which are hereby incorporated by reference in their entireties herein.BACKGROUND OF THE INVENTION[0002]Normal control of breathing is a complex process that involves, in part, the body's interpretation and response to chemical stimuli such as carbon dioxide, pH and oxygen levels in blood, tissues and the brain. Breathing control is also affected by other factors such as wakefulness (i.e., whether the patient is awake or sleeping), emotion, posture and vocalization. Within the brain medulla, there are respiratory control centers that interpret various feedforward and feedback signals that affect respiration and issues command...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61K31/53A61P11/00A61K31/505A61K31/519C07D251/54C07D239/50
CPCA61K31/505C07D487/04A61K31/522A61K31/53A61K31/5355A61K31/57A61K45/06A61K31/519C07D251/54C07D251/44C07D413/04C07D401/14C07D403/12A61K2300/00A61P11/00
Inventor MANNION, JAMES C.DAX, SCOTT L.MACINTYRE, DUNCAN EUANGOLDER, FRANCIS JOHNMCLEOD, JAMES FRANCIS
Owner GALLEON PHARMA INC
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