WO2009116077A2 - Préparations injectables et leur procédé de préparation - Google Patents

Préparations injectables et leur procédé de préparation Download PDF

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Publication number
WO2009116077A2
WO2009116077A2 PCT/IN2009/000114 IN2009000114W WO2009116077A2 WO 2009116077 A2 WO2009116077 A2 WO 2009116077A2 IN 2009000114 W IN2009000114 W IN 2009000114W WO 2009116077 A2 WO2009116077 A2 WO 2009116077A2
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WO
WIPO (PCT)
Prior art keywords
formulation
pharmaceutically acceptable
injection
trimethylpyridine
hydroxy
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/IN2009/000114
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English (en)
Other versions
WO2009116077A3 (fr
Inventor
Ashok Vasantray Vyas
Ravindra Tukaram Jadhav
Subhash Trimbak Phad
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Mjbiopharm Pvt Ltd
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Mjbiopharm Pvt Ltd
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Filing date
Publication date
Application filed by Mjbiopharm Pvt Ltd filed Critical Mjbiopharm Pvt Ltd
Priority to EP09721586A priority Critical patent/EP2252265A4/fr
Priority to EA201001327A priority patent/EA201001327A1/ru
Publication of WO2009116077A2 publication Critical patent/WO2009116077A2/fr
Publication of WO2009116077A3 publication Critical patent/WO2009116077A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner

Definitions

  • the present invention relates to a pharmaceutically acceptable injectable formulation.
  • the present invention relates to a pharmaceutically acceptable injectable formulation used in the treatment of ischemia, intraocular hemorrhage and macular degeneration.
  • Ischemia is restriction in blood supply due to factors in the blood vessels, with resultant damage or dysfunction of tissue. Ischemia is absolute or relative shortage of the blood supply to an organ. Relative shortage means mismatch between blood supply (oxygen delivery) and blood requirement for adequate oxygenation of tissue. Ischemia results in tissue damage because of lack of oxygen and nutrients.
  • Ischemia can also be described as an inadequate flow of blood to a part of the body, caused by constriction or blockage of the blood vessels supplying it.
  • ischemia can be broadly classified in to the following categories:
  • Cardiac ischemia Ischemia of heart muscle produces angina pectoris.
  • Bowel ischemia An ischemia in the large bowel caused by an inflammation results in ischemic colitis and ischemia in the small bowel, caused by an inflammation results in mesenteric ischemia.
  • Cutaneous ischemia Reduced blood flow to the skin layers may result in mottling or uneven, patchy discoloration of the skin.
  • Intraocular hemorrhage hemophthalmos or hemophthalmia
  • Intraocular hemorrhage is a condition in which bleeding occurs in the eyeball. It may be the result of physical trauma (direct injury to the eye) and/or medical illness. Severe hemorrhage, particularly when leading to rising pressure inside the eye, may lead to blindness.
  • intraocular hemorrhage such as subconjunctival hemorrhage, hyphema, vitreous hemorrhage, subretinal hemorrhage and submacular hemorrhage.
  • terson's syndrome as a result of subarachnoid hemorrhage
  • hemophilia a severe bleeding disorder, usually hereditary
  • anticoagulants and thrombolysis (medication to reduce blood clotting tendency Or 1 to disperse blood clots, respectively).
  • hemophthalmia is always accompanied by activation of free radical oxidation processes and proceeded as chain reactions and involves accumulation of oxidation products of molecules in vitreous body and retina.
  • Application of antioxidant preparations in early conservative therapy of intraocular hemorrhages essentially allows to speed up the resorption processes and thus reduces the risk of development of serious complications such as fibrosis of vitreous body and retinal detachment.
  • 3-Hydroxy-2,4,6-trimethylpyridine succinate and other such salts belong to a new biologically active compounds that exhibit important pharmacological activities such as anti oxidant for the vascular and inflammatory eye pathology.
  • 3-Hydroxy- 2,4,6-trimethylpyridine succinate and other such salts also posses geroprotective action and can be used to treat conditions, diseases or disorders of the cornea, retina, lens, sclera and anterior and posterior segments of the eye.
  • Another critical indication where the aforementioned compound finds its use is macular degeneration (degenerative disease of the eye). In macular degeneration, lipofuscin accumulation is implicated as a major risk factor.
  • Lipofuscin is finely granular yellow brown pigment granules composed of lipid-containing residues of lysosomal digestion. It is considered one of the aging or "wear and tear" pigments. It appears to be the product of the oxidation of unsaturated fatty acids and may be symptomatic of membrane damage or damage to mitochondria and lysosomes.
  • 3-Hydroxy-2,4,6-trimethylpyridine has been found to be an active inhibitor of peroxide oxidation of lipids. Thus, it is capable of neutralizing toxic activity of lipofuscin granules to have geroprotective action.
  • PCT/IB2005/003636 discloses a method of preparing 2,4,6-trimethyl-3- hydroxypyridine derivatives and salts thereof having antioxidant, geroprotective and anti-ischemic activity.
  • a pharmaceutically acceptable injection formulation comprising a compound of formula-I, pharmaceutically acceptable salts, esters, derivatives and polymorphs thereof in an amount of about 0.5 % to about 10 % of the mass of the formulation, preservative in an amount of about 0.001 % to about 0.5 % of the mass of the formulation and water for injection, wherein pH of said injection formulation is in the range of about 2.5 to 6.5.
  • the pharmaceutically acceptable injection formulation in accordance with this invention comprises a pharmaceutically acceptable salt of a compound of formula-I, selected from a group of pharmaceutically acceptable salts consisting of succinate, maleate, tartrate, oxalate, fumarate, citrate, hydrochloride, salicylate, pamoate, hydrogen sulfate, sulfate methanesulphonate and benzenesulfonate.
  • a pharmaceutically acceptable salt of a compound of formula-I selected from a group of pharmaceutically acceptable salts consisting of succinate, maleate, tartrate, oxalate, fumarate, citrate, hydrochloride, salicylate, pamoate, hydrogen sulfate, sulfate methanesulphonate and benzenesulfonate.
  • the concentration of 3-hydroxy-2,4,6-trimethylpyridine is in the range of about 0.5 % to about 5 % of the mass of the formulation.
  • the preservative is at least one selected from a group consisting of benzalkonium chloride, benzyl alcohol, methyl paraben, propyl paraben, butyl paraben, chlorobutanol, metacresol, phenylmercuric nitrate, thiomersal, myristylgamma picolonium chloride and phenol.
  • the pharmaceutically acceptable injection formulation in accordance with this invention further comprises a tonicity agent.
  • the tonicity agent is at least one selected from a group consisting of glycerin, lactose, mannitol, dextrose, sodium chloride, sodium sulfate and sorbitol.
  • a pharmaceutically acceptable injection formulation comprising a compound of formula-I , pharmaceutically acceptable salts, esters, derivatives and polymorphs thereof in an amount of about 0.5 % to about 10 % of the mass of the formulation, preservative in an amount of about 0.001 % to about 0.5 % of the mass of the formulation and water for injection, wherein pH of said injection formulation is in the range of about 2.5 to about 6.5.
  • the pharmaceutically acceptable injection formulation comprises pharmaceutically acceptable salt of 3-hydroxy -2,4,6 trimethylpyridine, selected from a group of salts consisting of succinate, maleate, tartrate, oxalate, fumarate, citrate, hydrochloride, salicylate pamoate, hydrogen sulfate, sulfate methanesulphonate and benzenesulfonate.
  • the concentration of 3-hydroxy-2,4,6-trimethylpyridine used in the formulation prepared in accordance with the present invention is in the range of about 0.5 % to about 5 % of the mass of the formulation.
  • the preservative used in the formulation prepared in accordance with the present invention is at least one selected from a group consisting of benzalkonium chloride, benzyl alcohol, methyl paraben, propyl paraben, butyl paraben, chlorobutanol, metacresol, phenylmercuric nitrate, thiomersal, myristylgamma picolonium chloride and phenol.
  • the pharmaceutically acceptable injection formulation further comprises a tonicity agent.
  • the tonicity agent used in the formulation is at least one selected from a group consisting of glycerin, lactose, mannitol, dextrose, sodium chloride, sodium sulfate and sorbitol.
  • the pH of the injection formulation prepared in accordance with the present invention is adjusted in the range of about 2.5 to about 6.5 to prevent eye irritation.
  • the pH adjusting agent is selected from a group consisting of sodium hydroxide, hydrochloric acid, triethanolamine, ammonia and mixtures thereof.
  • 3-hydroxy-2,4,6-trimethylpyridine succinate was dissolved in water for injection with continuous stirring under inert gas.
  • the pH of the solution was adjusted to 2.9 with 10% aqueous solution of hydrochloric acid.
  • the solution was diluted with sterile water for injection to achieve required concentration of 10 mg per ml. Further, the resultant solution was sterilized by sterile filtration and autoclaving. The sterile formulation was aseptically filled into ampoule.
  • 3-hydroxy-2, 4, 6-trimethylpyridine succinate was dissolved in water for injection with continuous stirring under inert gas.
  • the pH of the solution was adjusted to 2.9 with 10% aqueous solution of hydrochloric acid.
  • the solution was diluted with sterile water for injection to achieve required concentration of 50 mg per ml. Further, the resultant solution was sterilized by sterile filtration and autoclaving. The sterile formulation was aseptically filled into the ampoule.
  • 3-hydroxy-2,4,6-trimethylpyridine succinate was dissolved in water for injection with continuous stirring under inert gas.
  • the pH of the solution was adjusted to 4.8 with 10% aqueous solution of hydrochloric acid.
  • the solution was diluted with sterile water for injection to achieve required concentration of 10 mg per ml. Further, the resultant solution was sterilized by sterile filtration and autoclaving. The sterile formulation was aseptically filled into the ampoule.
  • 3-hydroxy-2,4,6-trimethylpyridine succinate 50.0 mg/ml 10% aqueous solution of hydrochloric acid QS water for injection upto 1 ml
  • 3-hydroxy-2,4,6-trimethylpyridine succinate was dissolved in water for injection with continuous stirring under inert gas.
  • the pH of the solution was adjusted to 4.7 with 10% aqueous solution of hydrochloric acid.
  • the solution was diluted with sterile water for injection to achieve required concentration of 50 mg per ml. Further the resultant solution was sterilized by sterile filtration and autoclaving. The sterile formulation was aseptically filled into the ampoule.
  • 3-hydroxy-2, 4, 6-trimethylpyridine succinate and benzalkonium chloride was dissolved in water for injection with continuous stirring under inert gas.
  • the pH of the solution was adjusted to 4.7 with 10% aqueous solution of hydrochloric acid.
  • the solution was diluted with sterile water for injection to achieve required concentration of 10 mg per ml. Further, the resultant solution was sterilized by sterile filtration and autoclaving. The sterile formulation was aseptically filled into the ampoule.
  • 3-hydroxy-2,4,6-trimethylpyridine succinate and benzalkonium chloride was dissolved in water for injection with continuous stirring under inert gas.
  • the pH of the solution was adjusted to 4.7 with 10% aqueous solution of hydrochloric acid.
  • the solution was diluted with sterile water for injection to achieve required concentration of 10 mg per ml. Further, the resultant solution was sterilized by sterile filtration and autoclaving. The sterile formulation was aseptically filled into the ampoule.
  • 3-hydroxy-2,4,6-trimethylpyridine tartarate and benzalkonium chloride was dissolved in water for injection with continuous stirring under inert gas.
  • the pH of the solution was adjusted to 4.7 with 10% aqueous solution of sodium hydroxide.
  • the solution was diluted with sterile water for injection to achieve required concentration of 10 mg per ml. Further, the resultant solution was sterilized by sterile filtration and autoclaving. The sterile formulation was aseptically filled into the ampoule.
  • the formulations prepared in accordance with the present inventions were stored at temperatures ranging from 5° C to 60° C for 12 months. At various time intervals, the samples were examined for colour change and development of insoluble material. The pH of the formulations was measured and chemical assays were performed to ascertain whether any significant chemical loss had occurred and to assure maintenance of potency. The formulations of the invention demonstrated acceptable storage stability.
  • a traumatic hemophthalmia was modeled by introduction of 0.5 to 0.7 ml of autoblood into a vitreous body through a puncture in a sclera on distance of 5 mm from a limbus, under a local anaesthesia.
  • the basic group made with 6 rabbits (12 eyes), daily received a formulation prepared in accordance with the present invention parabulbarly (0.5 ml of 1 % solution).
  • a high (100 - 50 SUD), medium (50 - 25 SUD) and low (less than 25 SUD) densities were distinguished.
  • the area measurement in sm was used.
  • the volume of the intraocular hemorrhage was studied with the help of 3D modelling in the B-regimen of a grey scale and measurement in sm .
  • the average volume of vitreous body (1.0 ⁇ 0.9 sm 3 ) and the average area of a vitreous body (1.04 ⁇ 0.8 sm 2 ) were fixed. Proceeding from the obtained data, the total hemophthalmia (from 100 up to 50 % of the vitreous body volume) was equated to the volume of 0.5-1.0 sm 3 and of 0.5-1.0 sm 2 , a wide-spread hemophthalmia (50 - 25 % of volume of a vitreous) corresponded to the area of 0.5-0.25 sm 3 , both 0.5-0.25 sm 2 , and the partial hemophthalmia occupied up to 0.25 sm 3 and 0.25 sm 2 (up to 25 % of the vitreous volume).
  • Capability of the eyeground ophthalmoscopy was estimated by a 3-mark(point) scale depending on the image sharpness (0 - ophthalmoscopy is impossible (not capable), 3 - details of an eyeground are clearly visible).
  • the materials used for biochemical examination were as follows: blood, liquid of the anterior chamber, tear liquid, tunics of eyeglobe ( retina, a vitreous body).
  • the blood was taken from the aural vein in an amount of 3 ml.
  • Sampling of tear liquid was carried out by a microcapillary after instillation of distilled water into the conjunctival cavity.
  • Liquid of the anterior chamber was obtained by paracentesis.
  • the blood sampling as well as liquid of the anterior chamber and teat liquid were carried out on the 1 st , 7 th and 14 th day of the experiment.
  • the animals were killed (pithed) by air embolism and both the eyes were enucleated.
  • the eyes were prepared by tunic separation. Retina and vitreous body were obtained.
  • the concentration of products of the free radical oxidation, active in the reaction with thiobarbituric acid (TBA-active products), protein concentration, and the antioxidant activity (AOA) were determined.
  • Table 1 Dynamics of parameters of preclinical and ultrasonic examination at the experimental hemophthalmia in the basic (A) and control (B) groups.
  • the parameters of ultrasonic and clinical examination were practically identical in all groups: the density of hemophthalmia in average made from 81 up to 85 SUD, the area - 0.52-0.55 sm 2 , the volume 0.47-0.5 sm 3 , the capability of ophthalmoscopy of an eyeground was corresponded to 1-2 points.
  • the intraocular hemorrhage which complicated the capability of ophthalmoscopy of an eyeground was marked rather small in volume, but essential in density.
  • the difference of preclinical and ultrasonic parameters of a hemophthalmia became more noticeable.
  • the area of a hemophthalmia was decreased up to 0.51 ⁇ 0.6 sm 2 , volume up to 0.47 ⁇ 0.4 sm 3 , density up to 49 ⁇ 1.4 SUD; capability of the eyeground ophthalmoscopy was equal to 1.5 points.
  • the wide-spread hemophthalmia of average density was observed.
  • the tendency to resorption of a hemorrhage was less expressed: the area of a hemophthalmia was 0.7 ⁇ 0.1 sm 2 , volume 0.68 ⁇ 0.9 sm 3 , density 65 ⁇ 2.1 SUD, capability of the eyeground ophthalmoscopy was 1 point. Thus, in animals of the control group the clinical picture practically did not changed.
  • the hemophthalmia was completely resolved in two animals, in other cases marked a noticeable decrease of the area (0.24 ⁇ 0,lsm 2 ), volume (0.2 ⁇ 0.1 sm 3 ) and density (23 ⁇ 1.1 SUD) of hemorrhage, the eyeground (2.2 points) was well seen.
  • the intraocular hemorrhage corresponded to a partial hemophthalmia with a low density.
  • the effect of treatment was less expressed: the area of a hemophthalmia averaged to 0.53 ⁇ 0.4 sm 2 , volume 0.5 ⁇ 0.2 sm 3 , density 48 ⁇ 1.5 SUD, capability of the eyeground ophthalmoscopy was equal to 1.8 points.
  • Table No.2 shows biochemical parameters in blood serum (BS), tear liquid (TL) and the anterior chamber liquid (ACL) at an experimental hemophthalmia in the basic (A) and the control (B) groups.
  • Table 2 Biochemical parameters
  • concentration of TBA-active products was grown in the control group (2.4 ⁇ 0.09 nmol/ml in the blood serum, 0.46 ⁇ 0.07 nmol/ml in the tear liquid, 2.2 ⁇ 0.4 nmol/ml in the anterior chamber liquid), and was reduced in the basic group (1.17 ⁇ 0.05 nmol/ml in the blood serum, 0.13 ⁇ 0.05 nmol/ml in the tear liquid, 0.8 ⁇ 0.5 nmol/ml in the anterior chamber liquid). Similar changes were observed at examination of protein concentration in the blood serum in rabbits of the control (103.0 ⁇ 5.0 mg / ml) and the basic (82.4 ⁇ 1.3 mg / ml) groups. In all animals the protein concentration was grown in the tear and the anterior chamber liquid on the l x day.
  • Concentration of TBA-active products was also decreased in all rabbits, thus in the basic group their values were lower, than in the control group (0.9 ⁇ 0.15 - 1.6 ⁇ 0.2 nmol/ml in the blood serum, 0.04 ⁇ 0.07 - 0.3 ⁇ 0.2 nmol/ml in the tear liquid, 0.6 ⁇ 0.2 - 2.2 ⁇ 0.3 nmol/ml in the anterior chamber liquid, accordingly). Similar changes were marked at the examination of parameters of protein concentration in both the groups of animals. In AOA studies the augmentation of the given parameter was observed in 2 times in the eye tunics, a retina and a vitreous body, in rabbits of the basic group in comparison with the control group.
  • the injection formulation prepared in accordance with the present invention renders a positive effect on the resorptive processes in a vitreous body at the experimental traumatic hemophthalmia.
  • the experiment was done on non-linear male rats weighing about 250-300 g.
  • the animals were anesthetized with sodium ethaminale (40 mg/kg intraperitoneally).
  • a myocardial infarction was modeled for the animals.
  • the animals were then transferred to controlled breathing by ligation of a descending branch of the left- hand coronary artery at a level of the lower edge of an auricula atrii.
  • the sizes of a necrosis zone and ischemia zones were detected in 4 hours after occlusion of a coronary artery by a differential indicator method, which is founded on separate quantitative determination of Evans' blue (indicator of a ischemia zone) and red phormazane (indicator of a necrosis zone).

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Pyridine Compounds (AREA)

Abstract

L'invention concerne une préparation d'injection pharmaceutiquement acceptable comprenant 3-hydroxy 2,4,6 triméthylpyridine, des sels pharmaceutiquement acceptables, des esters, des dérivés et des polymorphes de celle-ci pour traiter une ischémie, une hémorragie intraoculaire et la dégénérescence maculaire.
PCT/IN2009/000114 2008-02-19 2009-02-19 Préparations injectables et leur procédé de préparation Ceased WO2009116077A2 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP09721586A EP2252265A4 (fr) 2008-02-19 2009-02-19 Préparations injectables et leur procédé de préparation
EA201001327A EA201001327A1 (ru) 2008-02-19 2009-02-19 Инъецируемые составы и способ их получения

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN356MU2008 2008-02-19
IN356/MUM/2008 2008-02-19

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WO2009116077A2 true WO2009116077A2 (fr) 2009-09-24
WO2009116077A3 WO2009116077A3 (fr) 2009-12-23

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EA (1) EA201001327A1 (fr)
WO (1) WO2009116077A2 (fr)

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2276138C2 (ru) * 2004-05-12 2006-05-10 Марвел Лайф Сайнсез Лтд. Вещество, обладающее антиоксидантной, геропротекторной и противоишемической активностью, и способ его получения
EP2265252A2 (fr) * 2008-02-19 2010-12-29 Marvel Lifesciences Limited Preparation ophtalmique contenant un derive pypidinole
WO2009116078A2 (fr) * 2008-02-19 2009-09-24 M. J. Biopharm Pvt. Ltd. Formulations de dosage orales et leur procédé de préparation

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of EP2252265A4 *

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Publication number Publication date
EP2252265A2 (fr) 2010-11-24
WO2009116077A3 (fr) 2009-12-23
EA201001327A1 (ru) 2011-04-29
EP2252265A4 (fr) 2011-04-20

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